!Compound_common_name Compound_synonyms Molecular_weight Chemical_formula Smiles Links EC Reaction_equation Pathway pyropheophorbide a 536.672 C33 H36 N4 O3 C13(C(=C(C(N=1)=CC2(NC6(=C(C=2C)C(CC(C5(N=C(C=C4(NC(C=3)C(=C4C)C=C))C(C5CCC(O)=O)C))=6)=O)))CC)C) LIGAND-CPD:C18064:*CHEBI:48398:*PUBCHEM:5489042: 3.1.1.82 pheophorbide a + H2O = pyropheophorbide a + methanol + CO2 chlorophyll a degradation 5-phosphoribosyl-N-formylglycineamidine 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine*5'-phosphoribosyl-N-formyl glycineamidine*FGAM*5-phosphoribosyl-N-formylglycineamidine*5'-phosphoribosylformylglycinamidine 312.196 C8 H15 N3 O8 P1 C(NC1(C(C(C(COP([O-])(=O)[O-])O1)O)O))(=[N+])CNC=O PUBCHEM:440417:*PUBCHEM:25244446:*LIGAND-CPD:C04640: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis II 5-phosphoribosyl-N-formylglycineamidine 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine*5'-phosphoribosyl-N-formyl glycineamidine*FGAM*5-phosphoribosyl-N-formylglycineamidine*5'-phosphoribosylformylglycinamidine 312.196 C8 H15 N3 O8 P1 C(NC1(C(C(C(COP([O-])(=O)[O-])O1)O)O))(=[N+])CNC=O PUBCHEM:440417:*PUBCHEM:25244446:*LIGAND-CPD:C04640: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis I 5-phosphoribosyl-N-formylglycineamidine 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine*5'-phosphoribosyl-N-formyl glycineamidine*FGAM*5-phosphoribosyl-N-formylglycineamidine*5'-phosphoribosylformylglycinamidine 312.196 C8 H15 N3 O8 P1 C(NC1(C(C(C(COP([O-])(=O)[O-])O1)O)O))(=[N+])CNC=O PUBCHEM:440417:*PUBCHEM:25244446:*LIGAND-CPD:C04640: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine superpathway of 5-aminoimidazole ribonucleotide biosynthesis 5-phosphoribosyl-N-formylglycineamidine 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine*5'-phosphoribosyl-N-formyl glycineamidine*FGAM*5-phosphoribosyl-N-formylglycineamidine*5'-phosphoribosylformylglycinamidine 312.196 C8 H15 N3 O8 P1 C(NC1(C(C(C(COP([O-])(=O)[O-])O1)O)O))(=[N+])CNC=O PUBCHEM:440417:*PUBCHEM:25244446:*LIGAND-CPD:C04640: 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = H+ + ADP + 5-aminoimidazole ribonucleotide 5-aminoimidazole ribonucleotide biosynthesis II 5-phosphoribosyl-N-formylglycineamidine 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine*5'-phosphoribosyl-N-formyl glycineamidine*FGAM*5-phosphoribosyl-N-formylglycineamidine*5'-phosphoribosylformylglycinamidine 312.196 C8 H15 N3 O8 P1 C(NC1(C(C(C(COP([O-])(=O)[O-])O1)O)O))(=[N+])CNC=O PUBCHEM:440417:*PUBCHEM:25244446:*LIGAND-CPD:C04640: 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = H+ + ADP + 5-aminoimidazole ribonucleotide 5-aminoimidazole ribonucleotide biosynthesis I 5-phosphoribosyl-N-formylglycineamidine 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine*5'-phosphoribosyl-N-formyl glycineamidine*FGAM*5-phosphoribosyl-N-formylglycineamidine*5'-phosphoribosylformylglycinamidine 312.196 C8 H15 N3 O8 P1 C(NC1(C(C(C(COP([O-])(=O)[O-])O1)O)O))(=[N+])CNC=O PUBCHEM:440417:*PUBCHEM:25244446:*LIGAND-CPD:C04640: 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = H+ + ADP + 5-aminoimidazole ribonucleotide superpathway of 5-aminoimidazole ribonucleotide biosynthesis UDP-α-D-xylose udp-xylose*UDP-α-D-xylose 534.263 C14 H20 N2 O16 P2 O=C1(C=CN(C(=O)N1)C3(OC(COP(=O)([O-])OP(=O)([O-])OC2(OCC(O)C(O)C(O)2))C(O)C(O)3)) CHEBI:16082:*PUBCHEM:16667349:*LIGAND-CPD:C00190:*CAS:3616-06-6 2.4.2.24 UDP-α-D-xylose = UDP xylan biosynthesis UDP-α-D-xylose udp-xylose*UDP-α-D-xylose 534.263 C14 H20 N2 O16 P2 O=C1(C=CN(C(=O)N1)C3(OC(COP(=O)([O-])OP(=O)([O-])OC2(OCC(O)C(O)C(O)2))C(O)C(O)3)) CHEBI:16082:*PUBCHEM:16667349:*LIGAND-CPD:C00190:*CAS:3616-06-6 UDP-α-D-xylose = UDP xyloglucan biosynthesis UDP-α-D-xylose udp-xylose*UDP-α-D-xylose 534.263 C14 H20 N2 O16 P2 O=C1(C=CN(C(=O)N1)C3(OC(COP(=O)([O-])OP(=O)([O-])OC2(OCC(O)C(O)C(O)2))C(O)C(O)3)) CHEBI:16082:*PUBCHEM:16667349:*LIGAND-CPD:C00190:*CAS:3616-06-6 5.1.3.5 UDP-L-arabinose biosynthesis I (from UDP-xylose) UDP-α-D-xylose udp-xylose*UDP-α-D-xylose 534.263 C14 H20 N2 O16 P2 O=C1(C=CN(C(=O)N1)C3(OC(COP(=O)([O-])OP(=O)([O-])OC2(OCC(O)C(O)C(O)2))C(O)C(O)3)) CHEBI:16082:*PUBCHEM:16667349:*LIGAND-CPD:C00190:*CAS:3616-06-6 4.1.1.35 H+ + UDP-D-glucuronate = UDP-α-D-xylose + CO2 UDP-D-xylose and UDP-D-glucuronate biosynthesis quercetin 3,3',7-trissulfate 539.391 C15 H7 O16 S3 O=C1(C(OS(=O)(=O)[O-])=C(OC2(C=C(C=C(O)C1=2)OS(=O)(=O)[O-]))C3(=CC=C(O)C(=C3)OS(=O)(=O)[O-])) PUBCHEM:21676177:*CHEBI:57813:*PUBCHEM:21676177:*LIGAND-CPD:C03897: 2.8.2.28 quercetin-3,3'-bissulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + quercetin 3,3',7-trissulfate quercetinsulphates biosynthesis quercetin 3,3',7-trissulfate 539.391 C15 H7 O16 S3 O=C1(C(OS(=O)(=O)[O-])=C(OC2(C=C(C=C(O)C1=2)OS(=O)(=O)[O-]))C3(=CC=C(O)C(=C3)OS(=O)(=O)[O-])) PUBCHEM:21676177:*CHEBI:57813:*PUBCHEM:21676177:*LIGAND-CPD:C03897: quercetin 3,3',7-trissulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin 3, 7, 3', 4'-tetrasulphate quercetinsulphates biosynthesis petroselinate 6Z-octadecenoic acid*cis-6-Octadecenoic acid*petroselinic acid*6Z-octadecenoate 281.457 C18 H33 O2 [O-]C(=O)CCCCC=CCCCCCCCCCCC PUBCHEM:5281125:*PUBCHEM:5461010:*CHEBI:32375:*LIGAND-CPD:C08363: 3.1.2.14 H2O = petroselinate petroselinate biosynthesis L-isoleucine I*ile*iso-leucine 131.174 C6 H13 N1 O2 C([N+])(C(=O)[O-])C(C)CC CHEBI:17191:*PUBCHEM:7043901:*KNAPSACK:C00001374:*PUBCHEM:25244449:*CAS:7004-09-3*CAS:73-32-5:*LIGAND-CPD:C00407: 2.6.1.42 L-isoleucine + 2-oxoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine degradation I L-isoleucine I*ile*iso-leucine 131.174 C6 H13 N1 O2 C([N+])(C(=O)[O-])C(C)CC CHEBI:17191:*PUBCHEM:7043901:*KNAPSACK:C00001374:*PUBCHEM:25244449:*CAS:7004-09-3*CAS:73-32-5:*LIGAND-CPD:C00407: 2.6.1.42 L-isoleucine + 2-oxoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine biosynthesis I (from threonine) L-isoleucine I*ile*iso-leucine 131.174 C6 H13 N1 O2 C([N+])(C(=O)[O-])C(C)CC CHEBI:17191:*PUBCHEM:7043901:*KNAPSACK:C00001374:*PUBCHEM:25244449:*CAS:7004-09-3*CAS:73-32-5:*LIGAND-CPD:C00407: 6.1.1.5 H+ + L-isoleucine + ATP = diphosphate + AMP tRNA charging pathway OPC6-3-hydroxyacyl-CoA 1027.866 C37 H56 N7 O19 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)C(O)CCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237226: 1.1.1.35 NAD+ + OPC6-3-hydroxyacyl-CoA = NADH + H+ + OPC6-3-ketoacyl-CoA jasmonic acid biosynthesis OPC6-3-hydroxyacyl-CoA 1027.866 C37 H56 N7 O19 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)C(O)CCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237226: 4.2.1.17 OPC6-3-hydroxyacyl-CoA = OPC6-trans-2-enoyl-CoA + H2O jasmonic acid biosynthesis miraxanthin V 344.323 C17 H16 N2 O6 C1(C(C=C(NC1C([O-])=O)C(=O)[O-])=CC=NCCC2(C=C(C(=CC=2)O)O)) PUBCHEM:25245691:*LIGAND-CPD:C08557: dopamine + betalamic acid = H+ + miraxanthin V + H2O betaxanthin biosynthesis (via dopamine) N-(5'-phosphoribosyl)-anthranilate N-(5-phosphoribosyl)-anthranilate*N-(5-phospho-β-D-ribosyl)-anthranilate*N-(5-Phospho-D-ribosyl)anthranilate*N-(5-phospho-D-ribosyl)-anthranilate*N-(5-phospho-β-D-ribosyl)-anthranilate*5-phosphoribosyl-anthranilate*5-P-ribosyl-anthranilate*5'-phosphoribosyl-anthranilate*5'-P-ribosyl-anthranilate*N-(5-phosphoribosyl)-anthranilate 346.21 C12 H13 N1 O9 P1 C2(C(NC1(C(C(C(O1)COP(=O)([O-])[O-])O)O))=C(C(=O)[O-])C=CC=2) PUBCHEM:25245690:*LIGAND-CPD:C04302: 2.4.2.18 N-(5'-phosphoribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-α-D-ribose 1-diphosphate tryptophan biosynthesis N-(5'-phosphoribosyl)-anthranilate N-(5-phosphoribosyl)-anthranilate*N-(5-phospho-β-D-ribosyl)-anthranilate*N-(5-Phospho-D-ribosyl)anthranilate*N-(5-phospho-D-ribosyl)-anthranilate*N-(5-phospho-β-D-ribosyl)-anthranilate*5-phosphoribosyl-anthranilate*5-P-ribosyl-anthranilate*5'-phosphoribosyl-anthranilate*5'-P-ribosyl-anthranilate*N-(5-phosphoribosyl)-anthranilate 346.21 C12 H13 N1 O9 P1 C2(C(NC1(C(C(C(O1)COP(=O)([O-])[O-])O)O))=C(C(=O)[O-])C=CC=2) PUBCHEM:25245690:*LIGAND-CPD:C04302: 5.3.1.24 N-(5'-phosphoribosyl)-anthranilate = 1-(o-carboxyphenylamino)-1'-deoxyribulose-5'-phosphate tryptophan biosynthesis dimethylsulfoniopropionate S,S-dimethyl-β-propiothetin*DMPT*DMSP*dimethylpropiothetin*S-dimethylsulfonium propionic acid 134.193 C5 H10 O2 S1 C(C[S+](C)C)C(=O)[O-] PUBCHEM:23736:*CHEBI:16457:*LIGAND-CPD:C04022:*CAS:7314-30-9 1.2.1.3 3-dimethylsulfoniopropionaldehyde + H2O + NAD+ = dimethylsulfoniopropionate + NADH + H+ dimethylsulfoniopropionate biosynthesis II (Spartina) dimethylsulfoniopropionate S,S-dimethyl-β-propiothetin*DMPT*DMSP*dimethylpropiothetin*S-dimethylsulfonium propionic acid 134.193 C5 H10 O2 S1 C(C[S+](C)C)C(=O)[O-] PUBCHEM:23736:*CHEBI:16457:*LIGAND-CPD:C04022:*CAS:7314-30-9 1.2.1.3 3-dimethylsulfoniopropionaldehyde + H2O + NAD+ = dimethylsulfoniopropionate + NADH + H+ dimethylsulfoniopropionate biosynthesis I (Wollastonia) pyridoxine-5'-phosphate pyridoxol-5'-phosphate*pyridoxine-5-phosphate*pyridoxine-phosphate*pyridoxine-5P*pyridoxine-P 247.144 C8 H10 N1 O6 P1 O(P([O-])(=O)[O-])CC1(C(=C(O)C(=NC=1)C)CO) CHEBI:58589:*PUBCHEM:24794348:*CAS:447-05-2:*LIGAND-CPD:C00627: 2.7.1.- ATP + pyridoxine = H+ + ADP + pyridoxine-5'-phosphate pyridoxal 5'-phosphate salvage pathway pyridoxine-5'-phosphate pyridoxol-5'-phosphate*pyridoxine-5-phosphate*pyridoxine-phosphate*pyridoxine-5P*pyridoxine-P 247.144 C8 H10 N1 O6 P1 O(P([O-])(=O)[O-])CC1(C(=C(O)C(=NC=1)C)CO) CHEBI:58589:*PUBCHEM:24794348:*CAS:447-05-2:*LIGAND-CPD:C00627: 1.4.3.5 oxygen + pyridoxine-5'-phosphate = hydrogen peroxide + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway 2-hydroxycaffeate 2-hydroxy caffeic acid 210.186 C10 H10 O5 COC1(=C(C=C(C(=C1)C=CC(=O)O)O)O) simplecoumarins biosynthesis 2-hydroxycaffeate 2-hydroxy caffeic acid 210.186 C10 H10 O5 COC1(=C(C=C(C(=C1)C=CC(=O)O)O)O) 2-hydroxycaffeate = esculetin simplecoumarins biosynthesis red chlorophyll catabolite (7S,8S,101R)-8-(2-carboxyethyl)-17-ethyl-19-formyl-101-(methoxycarbonyl)-3,7,13,18-tetramethyl-2-vinyl-8,23-dihydro-7H-10,12-ethanobiladiene-ab-1,102(21H)-dione*RCC*red chlorophyll catabolite*red bilin 626.708 C35 H38 N4 O7 C1(=C(C(=C(N1)CC2(NC5(=C(C2C)C([C-](C(=C4(N=C(C=C3(NC(C(=C3C)C=C)=O))C(C4CCC([O-])=O)C))5)C(OC)=O)=O)))CC)C)C=O PUBCHEM:25244455: 1.3.1.80 H+ + primary fluorescent chlorophyll catabolite + NADP+ = red chlorophyll catabolite + NADPH chlorophyll a degradation red chlorophyll catabolite (7S,8S,101R)-8-(2-carboxyethyl)-17-ethyl-19-formyl-101-(methoxycarbonyl)-3,7,13,18-tetramethyl-2-vinyl-8,23-dihydro-7H-10,12-ethanobiladiene-ab-1,102(21H)-dione*RCC*red chlorophyll catabolite*red bilin 626.708 C35 H38 N4 O7 C1(=C(C(=C(N1)CC2(NC5(=C(C2C)C([C-](C(=C4(N=C(C=C3(NC(C(=C3C)C=C)=O))C(C4CCC([O-])=O)C))5)C(OC)=O)=O)))CC)C)C=O PUBCHEM:25244455: 1.14.12.20 pheophorbide a + oxygen + NADPH = H+ + red chlorophyll catabolite + NADP+ chlorophyll a degradation 7-hydroxy-chlorophyll a 7-OH-chlorophyll a 909.502 C55 H72 N4 O6 MG1 C24(C=C9(C(C)C(CCC(=O)OCC=C(C)CCCC(C)CCCC(C)CCCC(C)C)C5(=N([Mg]36(N1(=C(C(CC)=C(CO)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) PUBCHEM:25245059: 1.1.1.294 7-hydroxy-chlorophyll a = chlorophyll b + H+ chlorophyll cycle 7-hydroxy-chlorophyll a 7-OH-chlorophyll a 909.502 C55 H72 N4 O6 MG1 C24(C=C9(C(C)C(CCC(=O)OCC=C(C)CCCC(C)CCCC(C)CCCC(C)C)C5(=N([Mg]36(N1(=C(C(CC)=C(CO)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) PUBCHEM:25245059: 7-hydroxy-chlorophyll a + H2O + NADP+ = H+ + chlorophyll a + oxygen + NADPH chlorophyll cycle 3-ureido-isobutyrate N-carbamyl-β-aminoisobutyric acid*N-carbamyl-β-aminoisobutyrate 145.138 C5 H9 N2 O3 C(C(C([O-])=O)C)NC(N)=O PUBCHEM:21123869:*LIGAND-CPD:C05100: 3.5.2.2 5,6-dihydrothymine + H2O = 3-ureido-isobutyrate + H+ thymine degradation 3-ureido-isobutyrate N-carbamyl-β-aminoisobutyric acid*N-carbamyl-β-aminoisobutyrate 145.138 C5 H9 N2 O3 C(C(C([O-])=O)C)NC(N)=O PUBCHEM:21123869:*LIGAND-CPD:C05100: 3.5.1.6 3-ureido-isobutyrate + H2O + H+ = (R)-3-amino-2-methylpropanoate + ammonia + CO2 thymine degradation 3-dehydrosphinganine 3-dehydro-D-sphinganine*3-dehydrosphinganine*KDHS 300.504 C18 H38 N1 O2 CCCCCCCCCCCCCCCC(=O)C([N+])CO PUBCHEM:25245061:*LIGAND-CPD:C02934: 2.3.1.50 H+ + L-serine + palmitoyl-CoA = CO2 + 3-dehydrosphinganine + coenzyme A sphingolipid biosynthesis (plants) 3-dehydrosphinganine 3-dehydro-D-sphinganine*3-dehydrosphinganine*KDHS 300.504 C18 H38 N1 O2 CCCCCCCCCCCCCCCC(=O)C([N+])CO PUBCHEM:25245061:*LIGAND-CPD:C02934: 1.1.1.102 NADP+ + sphinganine = H+ + NADPH + 3-dehydrosphinganine sphingolipid biosynthesis (plants) 7,8-dihydrofolate monoglutamate 7,8-dihydropteroyl monoglutamate*H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 441.402 C19 H19 N7 O6 NC3(=NC(C1(=C(NCC(=N1)CNC2(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C2))N3))=O) PUBCHEM:45479259:*CHEBI:15633:*LIGAND-CPD:C00415:*CAS:4033-27-6 1.5.1.3 NADP+ + tetrahydrofolate = H+ + NADPH + 7,8-dihydrofolate monoglutamate folate transformations II (plants) 7,8-dihydrofolate monoglutamate 7,8-dihydropteroyl monoglutamate*H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 441.402 C19 H19 N7 O6 NC3(=NC(C1(=C(NCC(=N1)CNC2(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C2))N3))=O) PUBCHEM:45479259:*CHEBI:15633:*LIGAND-CPD:C00415:*CAS:4033-27-6 1.5.1.3 NADP+ + tetrahydrofolate = H+ + NADPH + 7,8-dihydrofolate monoglutamate tetrahydrofolate biosynthesis 7,8-dihydrofolate monoglutamate 7,8-dihydropteroyl monoglutamate*H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 441.402 C19 H19 N7 O6 NC3(=NC(C1(=C(NCC(=N1)CNC2(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C2))N3))=O) PUBCHEM:45479259:*CHEBI:15633:*LIGAND-CPD:C00415:*CAS:4033-27-6 6.3.2.12 L-glutamate + 7,8-dihydropteroate + ATP = H+ + 7,8-dihydrofolate monoglutamate + ADP tetrahydrofolate biosynthesis 7,8-dihydrofolate monoglutamate 7,8-dihydropteroyl monoglutamate*H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 441.402 C19 H19 N7 O6 NC3(=NC(C1(=C(NCC(=N1)CNC2(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C2))N3))=O) PUBCHEM:45479259:*CHEBI:15633:*LIGAND-CPD:C00415:*CAS:4033-27-6 2.1.1.45 5,10-methylenetetrahydropteroyl mono-L-glutamate + dUMP = dTMP + 7,8-dihydrofolate monoglutamate pyrimidine deoxyribonucleotides de novo biosynthesis I 7,8-dihydrofolate monoglutamate 7,8-dihydropteroyl monoglutamate*H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 441.402 C19 H19 N7 O6 NC3(=NC(C1(=C(NCC(=N1)CNC2(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C2))N3))=O) PUBCHEM:45479259:*CHEBI:15633:*LIGAND-CPD:C00415:*CAS:4033-27-6 2.1.1.45 5,10-methylenetetrahydropteroyl mono-L-glutamate + dUMP = dTMP + 7,8-dihydrofolate monoglutamate folate transformations II (plants) sinapyl-alcohol 210.229 C11 H14 O4 O(C)C1(=CC(C=CCO)=CC(=C1O)OC) PUBCHEM:5280507:*CHEBI:28813:*LIGAND-CPD:C02325: 2.4.1.111 sinapyl-alcohol = H+ + syringin + UDP monolignol glucosides biosynthesis sinapyl-alcohol 210.229 C11 H14 O4 O(C)C1(=CC(C=CCO)=CC(=C1O)OC) PUBCHEM:5280507:*CHEBI:28813:*LIGAND-CPD:C02325: 1.1.1.195 H+ + sinapaldehyde + NADPH = sinapyl-alcohol + NADP+ phenylpropanoid biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.7.2.2 ammonia + CO2 + ATP = H+ + carbamoyl-phosphate + ADP citrulline degradation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.7.2.2 ammonia + CO2 + ATP = H+ + carbamoyl-phosphate + ADP allantoin degradation IV (anaerobic) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- GA34 + 2-oxoglutarate + oxygen = H+ + GA34-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2-oxoglutarate + coenzyme A + NAD+ = succinyl-CoA + CO2 + NADH TCA cycle variation III (eukaryotic) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.- H+ + 3-methoxy-4-hydroxy-5-all-trans-decaprenylbenzoate = 2-decaprenyl-6-methoxyphenol + CO2 ubiquinol-10 biosynthesis (eukaryotic) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.41 palmitate biosynthesis II (bacteria and plants) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2-oxoadipate + NAD+ + coenzyme A = CO2 + NADH + glutaryl-CoA lysine degradation II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- GA51 + 2-oxoglutarate + oxygen = H+ + GA51-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.13.- H+ + N,N-dihydroxy-L-tryptophan = (E)-indol-3-ylacetaldoxime + CO2 + H2O IAA biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 3.5.1.5 urea + H2O = ammonia + CO2 urea degradation II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 p-dihydrocoumaroyl-CoA + malonyl-CoA = naringenin + coenzyme A + CO2 phloridzin biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.1.1.38 (S)-malate + NAD+ = NADH + CO2 + pyruvate gluconeogenesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 H+ + S-methyl-L-methionine = DMSP-amine + CO2 dimethylsulfoniopropionate biosynthesis II (Spartina) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- gibberellin A8 + 2-oxoglutarate + oxygen = H+ + GA8-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4-methyl-2-oxopentanoate + coenzyme A + NAD+ = isovaleryl-CoA + CO2 + NADH leucine degradation I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 3.5.3.9 H+ + allantoate + H2O = S-ureidoglycine + ammonia + CO2 allantoin degradation to ureidoglycolate II (ammonia producing) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.1.1.42 D-threo-isocitrate + NADP+ = 2-oxoglutarate + CO2 + NADPH glutamine biosynthesis III CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.17 H+ + L-ornithine = CO2 + putrescine putrescine biosynthesis IV CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.22 naringenin + 2-oxoglutarate + oxygen = apigenin + succinate + CO2 + H2O luteolin biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.65 H+ = CO2 phosphatidylethanolamine biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- GA53 + 2-oxoglutarate + oxygen = GA97 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.48 H+ + 1-(o-carboxyphenylamino)-1'-deoxyribulose-5'-phosphate = (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + CO2 + H2O tryptophan biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.170 H+ + 4-coumaroyl-CoA + malonyl-CoA + NADPH = isoliquiritigenin + coenzyme A + CO2 + NADP+ + H2O flavonoid biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.179 cis-vaccenate biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.41 palmitate biosynthesis II (bacteria and plants) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.2.1.7 H+ + pyruvate + D-glyceraldehyde-3-phosphate = 1-deoxy-D-xylulose 5-phosphate + CO2 methylerythritol phosphate pathway CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- GA29 + 2-oxoglutarate + oxygen = H+ + GA29-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.2.1.104 carbamate + H+ = ammonia + CO2 cyanate degradation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.13.12.1 oxygen + L-arginine = 4-guanidinobutyramide + H2O + CO2 arginine degradation X (arginine monooxygenase pathway) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.23 dihydrokaempferol + 2-oxoglutarate + oxygen = kaempferol + succinate + CO2 + H2O flavonol biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.- p-dihydrocoumaroyl-CoA + malonyl-CoA + H+ = phloretin + coenzyme A + CO2 phloridzin biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.- H+ + 3-methoxy-4-hydroxy-5-all-trans-nonaprenylbenzoate = 2-nonaprenyl-6-methoxyphenol + CO2 ubiquinol-9 biosynthesis (eukaryotic) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.2.1.6 H+ + pyruvate + 2-oxobutanoate = 2-aceto-2-hydroxy-butanoate + CO2 isoleucine biosynthesis I (from threonine) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 petroselinate biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.- H+ + 4-coumaroyl-CoA + H2O + malonyl-CoA = coenzyme A + CO2 + p-coumaroyltriacetate resveratrol biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- gibberellin A4 + 2-oxoglutarate + oxygen = GA34 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.18 H+ + L-lysine = CO2 + cadaverine lysine degradation I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.41 palmitate biosynthesis II (bacteria and plants) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- GA19 + oxygen + 2-oxoglutarate = H+ + gibberellin A20 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.37 uroporphyrinogen-III + H+ = coproporphyrinogen III + CO2 chlorophyllide a biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.37 uroporphyrinogen-III + H+ = coproporphyrinogen III + CO2 heme biosynthesis from uroporphyrinogen-III I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.1.1.- 4α-carboxy-4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ = cycloeucalenone + NADH + CO2 plant sterol biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.- H+ + 4-coumaroyl-CoA + malonyl-CoA = p-coumaroyltriacetic acid lactone + coenzyme A + CO2 aromatic polyketides biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.12 GA44 (open lactone form) + 2-oxoglutarate + oxygen = GA19 + succinate + CO2 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 L-phenylalanine + oxygen + H2O = phenylacetaldehyde + ammonia + hydrogen peroxide + CO2 phenylethanol biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.36 H+ + R-4'-phosphopantothenoyl-L-cysteine = 4'-phosphopantetheine + CO2 coenzyme A biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.2.4.2 2-oxoglutarate = CO2 2-ketoglutarate dehydrogenase complex CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- leucocyanidin + 2-oxoglutarate + oxygen = H+ + cyanidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.20 H+ + meso-diaminopimelate = CO2 + L-lysine lysine biosynthesis VI CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- gibberellin A20 + 2-oxoglutarate + oxygen = GA29 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.22 eriodictyol + 2-oxoglutarate + oxygen = luteolin + succinate + CO2 + H2O luteolin biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- GA19 + oxygen + 2-oxoglutarate = H+ + GA17 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.23 dihydromyricetin + 2-oxoglutarate + oxygen = myricetin + succinate + CO2 + H2O syringetin biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.9 (2S)-pinocembrin + oxygen + 2-oxoglutarate = (2R,3R)-pinobanksin + CO2 + succinate pinobanksin biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.19 leucocyanidin + 2-oxoglutarate + oxygen = succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.28 H+ + L-dopa = dopamine + CO2 betaxanthin biosynthesis (via dopamine) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.2.1.51 H+ + prephenate = keto-phenylpyruvate + H2O + CO2 phenylalanine biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.95 H+ + 4-coumaroyl-CoA + malonyl-CoA = resveratrol + coenzyme A + CO2 resveratrol biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.28 H+ + L-tryptophan = CO2 + tryptamine IAA biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.28 H+ + L-tryptophan = CO2 + tryptamine camptothecin biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.2.1.2 formate + NAD+ = CO2 + NADH formate oxidation to CO2 CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.1.1.44 6-phospho-D-gluconate = D-ribulose-5-phosphate + CO2 pentose phosphate pathway (oxidative branch) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.49 oxaloacetate + ATP = CO2 + phosphoenolpyruvate + ADP gluconeogenesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.49 oxaloacetate + ATP = CO2 + phosphoenolpyruvate + ADP superpathway of glyoxylate cycle CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.15 gibberellin A20 + 2-oxoglutarate + oxygen = gibberellin A1 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.2.1.91 H+ + L-arogenate = CO2 + H2O + L-phenylalanine phenylalanine biosynthesis II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 3.5.1.6 3-ureidopropionate + H2O + H+ = β-alanine + ammonia + CO2 uracil degradation II (reductive) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.33 mevalonate-diphosphate + ATP = isopentenyl diphosphate + CO2 + ADP mevalonate pathway I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.23 H+ + orotidine-5'-phosphate = CO2 + uridine-5'-phosphate uridine-5'-phosphate biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.4.2.19 H+ + 5-phospho-α-D-ribose 1-diphosphate + quinolinate = CO2 + diphosphate + nicotinate mononucleotide NAD biosynthesis I (from aspartate) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.41 palmitate biosynthesis II (bacteria and plants) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- H+ + GA44 + 2-oxoglutarate + oxygen = GA98 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 H+ + homogentisate + phytyl diphosphate = 2-methyl-6-phytyl-1,4-benzoquinol + CO2 + diphosphate vitamin E biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- gibberellin A12 + 2-oxoglutarate + oxygen = GA110 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.3.3.3 coproporphyrinogen III + oxygen + H+ = protoporphyrinogen IX + CO2 + H2O chlorophyllide a biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.3.3.3 coproporphyrinogen III + oxygen + H+ = protoporphyrinogen IX + CO2 + H2O heme biosynthesis from uroporphyrinogen-III I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.74 H+ + indole-3-pyruvate = CO2 + indole acetaldehyde IAA biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.41 palmitate biosynthesis II (bacteria and plants) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- gibberellin A9 + 2-oxoglutarate + oxygen = GA51 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 3',4',5'-pentahydroxyflavanone + 2-oxoglutarate + oxygen = dihydromyricetin + succinate + CO2 leucodelphinidin biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2-keto-3-methyl-valerate + NAD+ + coenzyme A = 2-methylbutanoyl-CoA + NADH + CO2 isoleucine degradation I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.15 H+ + L-glutamate = CO2 + 4-aminobutyrate glutamate degradation III (via 4-aminobutyrate) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.15 H+ + L-glutamate = CO2 + 4-aminobutyrate glutamate degradation IX (via 4-aminobutyrate) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.15 H+ + L-glutamate = CO2 + 4-aminobutyrate glutamate dependent acid resistance CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.19 H+ + L-arginine = CO2 + agmatine arginine degradation III (arginine decarboxylase/agmatinase pathway) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.19 H+ + L-arginine = CO2 + agmatine arginine dependent acid resistance CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.19 H+ + L-arginine = CO2 + agmatine putrescine biosynthesis IV CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.19 H+ + L-arginine = CO2 + agmatine putrescine biosynthesis II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.19 H+ + L-arginine = CO2 + agmatine arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.1.1.40 (S)-malate + NADP+ = NADPH + CO2 + pyruvate gluconeogenesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.1.1.40 (S)-malate + NADP+ = NADPH + CO2 + pyruvate C4 photosynthetic carbon assimilation cycle CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.50 H+ + L-serine + palmitoyl-CoA = CO2 + 3-dehydrosphinganine + coenzyme A sphingolipid biosynthesis (plants) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 3.5.1.53 H+ + N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia putrescine biosynthesis II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 3.5.1.53 H+ + N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.- H+ + 2-oxo-3-carboxy-4,5-cyclopropylhex-5-enoate = beta-methylenecyclopropyl pyruvate + CO2 hypoglycin biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.13.11.27 4-hydroxyphenylpyruvate + oxygen = CO2 + homogentisate vitamin E biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.1 H+ + 4-methyl-2-oxopentanoate = 3-methylbutanal + CO2 leucine degradation III CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.2.1.25 2-oxoisovalerate + coenzyme A + NAD+ = isobutyryl-CoA + CO2 + NADH valine degradation I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 gluconeogenesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 glutamine biosynthesis III CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 CO2 fixation into oxaloacetate CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 C4 photosynthetic carbon assimilation cycle CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.- H+ + L-serine = ethanolamine + CO2 choline biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.74 H+ + 4-coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A flavonoid biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.74 H+ + 4-coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A aromatic polyketides biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.13 gibberellin A1 + 2-oxoglutarate + oxygen = gibberellin A8 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.23 trans dihydroquercetin + 2-oxoglutarate + oxygen = quercetin + succinate + CO2 + H2O flavonol biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 6.3.4.16 ammonia + H2O + CO2 + ATP = H+ + carbamoyl-phosphate + ADP urea cycle CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.- malonyl-CoA = CO2 + coenzyme A very long chain fatty acid biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 strictosidine = strictosamide + H2O + CO2 camptothecin biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.41 malonyl-CoA = CO2 + coenzyme A stearate biosynthesis II (plants) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.9 eriodictyol + oxygen + 2-oxoglutarate = trans dihydroquercetin + CO2 + succinate leucopelargonidin and leucocyanidin biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.9 eriodictyol + oxygen + 2-oxoglutarate = trans dihydroquercetin + CO2 + succinate leucodelphinidin biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.35 H+ + UDP-D-glucuronate = UDP-α-D-xylose + CO2 UDP-D-xylose and UDP-D-glucuronate biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.- H+ + malonyl-CoA + (E)-cinnamoyl-CoA = pinocembrin chalcone + coenzyme A + CO2 pinobanksin biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 3.1.1.82 pheophorbide a + H2O = pyropheophorbide a + methanol + CO2 chlorophyll a degradation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 H+ + (2S)-2-isopropyl-3-oxosuccinate = 4-methyl-2-oxopentanoate + CO2 leucine biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.180 acetyl-CoA = coenzyme A + CO2 fatty acid biosynthesis initiation I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.3.1.78 L-arogenate + NADP+ = L-tyrosine + CO2 + NADPH tyrosine biosynthesis II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.1 H+ + 2-oxoisovalerate = isobutanal + CO2 valine degradation II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.17.4 H+ + L-ascorbate + 1-aminocyclopropane-1-carboxylate + oxygen = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.2.1.104 cyanate + bicarbonate + H+ = carbamate + CO2 cyanate degradation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.41 fatty acid elongation -- saturated CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.53 H+ + L-phenylalanine = 2-phenylethylamine + CO2 phenylethanol biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- GA53 + oxygen + 2-oxoglutarate = GA44 (open lactone form) + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.1.1.- 4α-carboxy-ergosta-7,24(241)-dien-3β-ol + NAD+ = episterone + NADH + CO2 plant sterol biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations II (plants) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH photorespiration CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.1 H+ + pyruvate = acetaldehyde + CO2 acetaldehyde biosynthesis II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.1 H+ + pyruvate = acetaldehyde + CO2 acetaldehyde biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.1 H+ + pyruvate = acetaldehyde + CO2 pyruvate fermentation to ethanol II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.39 D-ribulose-1,5-bisphosphate + CO2 + H2O = 3-phospho-D-glycerate + H+ Rubisco shunt CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.39 D-ribulose-1,5-bisphosphate + CO2 + H2O = 3-phospho-D-glycerate + H+ Calvin-Benson-Bassham cycle CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 3.5.1.6 3-ureido-isobutyrate + H2O + H+ = (R)-3-amino-2-methylpropanoate + ammonia + CO2 thymine degradation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.50 H+ + S-adenosyl-L-methionine = CO2 + S-adenosyl-L-methioninamine spermine biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.50 H+ + S-adenosyl-L-methionine = CO2 + S-adenosyl-L-methioninamine spermidine biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.9 naringenin + oxygen + 2-oxoglutarate = CO2 + succinate + dihydrokaempferol flavonoid biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.41 palmitate biosynthesis II (bacteria and plants) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- H+ + GA44 (open lactone form) + 2-oxoglutarate + oxygen = GA38 + succinate + CO2 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- leucodelphinidin + oxygen + 2-oxoglutarate = H+ + delphinidin + H2O + CO2 + succinate anthocyanin biosynthesis (delphinidin 3-O-glucoside) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 3.5.1.20 H+ + L-citrulline + H2O = L-ornithine + CO2 + ammonia proline biosynthesis II (from arginine) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.3.1.- H+ + 4-coumaroyl-CoA + malonyl-CoA = bis-noryangonin + coenzyme A + CO2 resveratrol biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.1.1.41 D-threo-isocitrate + NAD+ = 2-oxoglutarate + CO2 + NADH TCA cycle variation III (eukaryotic) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.1.1.41 D-threo-isocitrate + NAD+ = 2-oxoglutarate + CO2 + NADH glutamine biosynthesis III CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 H+ + 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate = S-allantoin + CO2 urate degradation to allantoin CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.1.1.- 4α-carboxy-stigmasta-7,24(241)-dien-3β-ol + NAD+ = avenastenone + NADH + CO2 plant sterol biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = H+ + dethiobiotin + ADP biotin biosynthesis from 7-keto-8-aminopelargonate CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.1.1.21 H+ + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate = 5-aminoimidazole ribonucleotide + CO2 inosine-5'-phosphate biosynthesis II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.2.4.1 pyruvate = CO2 acetyl-CoA biosynthesis (from pyruvate) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 4.2.1.1 bicarbonate + H+ = CO2 + H2O cyanate degradation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.4.4.2 glycine = CO2 glycine cleavage complex CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.2.1.9 H+ + isochorismate + 2-oxoglutarate = 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + CO2 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 2.2.1.6 H+ + pyruvate = (S)-2-acetolactate + CO2 valine biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 S-methyl-L-methionine = 3-dimethylsulfoniopropionaldehyde + CO2 dimethylsulfoniopropionate biosynthesis I (Wollastonia) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*PUBCHEM:280*CHEBI:16526:*PUBCHEM:280:*PUBCHEM:280:*CHEBI:16526*LIGAND-CPD:C00011*CAS:124-38-9 1.14.11.- H+ + leucopelargonidin + 2-oxoglutarate + oxygen = pelargonidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) strictosidine 3-α(S)-strictosidine 531.581 C27 H35 N2 O9 C1(=CC=CC2(NC3(C([H])([N+]CCC(C1=2)=3)CC5([H])(C([H])(C(OC4(OC(C(C(C4O)O)O)CO))OC=C5C(=O)OC)C=C)))) PUBCHEM:44123291:*LIGAND-CPD:C03470:*CAS:20824-29-7 4.3.3.2 tryptamine + secologanin = strictosidine + H2O camptothecin biosynthesis strictosidine 3-α(S)-strictosidine 531.581 C27 H35 N2 O9 C1(=CC=CC2(NC3(C([H])([N+]CCC(C1=2)=3)CC5([H])(C([H])(C(OC4(OC(C(C(C4O)O)O)CO))OC=C5C(=O)OC)C=C)))) PUBCHEM:44123291:*LIGAND-CPD:C03470:*CAS:20824-29-7 strictosidine = strictosamide + H2O + CO2 camptothecin biosynthesis gibberellin A4 GA4*GA4*gibberellin A4*gibberellin A4 331.388 C19 H23 O5 C1(CC(C2(C4(C1(OC2=O)C5(CCC3(CC(CC3=C)(C4C([O-])=O)5))))(C))O) PUBCHEM:25245706:*LIGAND-CPD:C11864: 1.14.11.- gibberellin A4 + 2-oxoglutarate + oxygen = GA34 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) arabinoxylan C5 H7 O5 R1 R21 R11 C1(O[R2])(C(O)C(O[R])C(O[R1])CO1) LIGAND-CPD:C07397:*CHEBI:8707:*PUBCHEM:5002: 2.4.2.- xylan biosynthesis 10-formyl-tetrahydrofolate N10-formyl-THF*N10-formyl-tetrahydrofolate*10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 471.429 C20 H21 N7 O7 NC3(NC2(NCC(CN(C=O)C1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N=3)) CAS:692-29-5:*PUBCHEM:6326742:*CHEBI:15637:*LIGAND-CPD:C00234:*CAS:2800-34-2 2.1.2.3 10-formyl-tetrahydrofolate + aminoimidazole carboxamide ribonucleotide = tetrahydrofolate + phosphoribosyl-formamido-carboxamide inosine-5'-phosphate biosynthesis II 10-formyl-tetrahydrofolate N10-formyl-THF*N10-formyl-tetrahydrofolate*10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 471.429 C20 H21 N7 O7 NC3(NC2(NCC(CN(C=O)C1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N=3)) CAS:692-29-5:*PUBCHEM:6326742:*CHEBI:15637:*LIGAND-CPD:C00234:*CAS:2800-34-2 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate folate transformations I 10-formyl-tetrahydrofolate N10-formyl-THF*N10-formyl-tetrahydrofolate*10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 471.429 C20 H21 N7 O7 NC3(NC2(NCC(CN(C=O)C1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N=3)) CAS:692-29-5:*PUBCHEM:6326742:*CHEBI:15637:*LIGAND-CPD:C00234:*CAS:2800-34-2 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate folate transformations II (plants) 10-formyl-tetrahydrofolate N10-formyl-THF*N10-formyl-tetrahydrofolate*10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 471.429 C20 H21 N7 O7 NC3(NC2(NCC(CN(C=O)C1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N=3)) CAS:692-29-5:*PUBCHEM:6326742:*CHEBI:15637:*LIGAND-CPD:C00234:*CAS:2800-34-2 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate formaldehyde oxidation V (tetrahydrofolate pathway) 10-formyl-tetrahydrofolate N10-formyl-THF*N10-formyl-tetrahydrofolate*10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 471.429 C20 H21 N7 O7 NC3(NC2(NCC(CN(C=O)C1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N=3)) CAS:692-29-5:*PUBCHEM:6326742:*CHEBI:15637:*LIGAND-CPD:C00234:*CAS:2800-34-2 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate folate polyglutamylation 10-formyl-tetrahydrofolate N10-formyl-THF*N10-formyl-tetrahydrofolate*10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 471.429 C20 H21 N7 O7 NC3(NC2(NCC(CN(C=O)C1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N=3)) CAS:692-29-5:*PUBCHEM:6326742:*CHEBI:15637:*LIGAND-CPD:C00234:*CAS:2800-34-2 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate folate transformations I 10-formyl-tetrahydrofolate N10-formyl-THF*N10-formyl-tetrahydrofolate*10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 471.429 C20 H21 N7 O7 NC3(NC2(NCC(CN(C=O)C1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N=3)) CAS:692-29-5:*PUBCHEM:6326742:*CHEBI:15637:*LIGAND-CPD:C00234:*CAS:2800-34-2 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate 10-formyl-tetrahydrofolate N10-formyl-THF*N10-formyl-tetrahydrofolate*10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 471.429 C20 H21 N7 O7 NC3(NC2(NCC(CN(C=O)C1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N=3)) CAS:692-29-5:*PUBCHEM:6326742:*CHEBI:15637:*LIGAND-CPD:C00234:*CAS:2800-34-2 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate folate transformations II (plants) 10-formyl-tetrahydrofolate N10-formyl-THF*N10-formyl-tetrahydrofolate*10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 471.429 C20 H21 N7 O7 NC3(NC2(NCC(CN(C=O)C1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N=3)) CAS:692-29-5:*PUBCHEM:6326742:*CHEBI:15637:*LIGAND-CPD:C00234:*CAS:2800-34-2 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate formaldehyde oxidation V (tetrahydrofolate pathway) 10-formyl-tetrahydrofolate N10-formyl-THF*N10-formyl-tetrahydrofolate*10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 471.429 C20 H21 N7 O7 NC3(NC2(NCC(CN(C=O)C1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N=3)) CAS:692-29-5:*PUBCHEM:6326742:*CHEBI:15637:*LIGAND-CPD:C00234:*CAS:2800-34-2 2.1.2.2 10-formyl-tetrahydrofolate + 5-phospho-ribosyl-glycineamide = H+ + tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate 10-formyl-tetrahydrofolate N10-formyl-THF*N10-formyl-tetrahydrofolate*10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 471.429 C20 H21 N7 O7 NC3(NC2(NCC(CN(C=O)C1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N=3)) CAS:692-29-5:*PUBCHEM:6326742:*CHEBI:15637:*LIGAND-CPD:C00234:*CAS:2800-34-2 2.1.2.2 10-formyl-tetrahydrofolate + 5-phospho-ribosyl-glycineamide = H+ + tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide 5-aminoimidazole ribonucleotide biosynthesis I 10-formyl-tetrahydrofolate N10-formyl-THF*N10-formyl-tetrahydrofolate*10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 471.429 C20 H21 N7 O7 NC3(NC2(NCC(CN(C=O)C1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N=3)) CAS:692-29-5:*PUBCHEM:6326742:*CHEBI:15637:*LIGAND-CPD:C00234:*CAS:2800-34-2 3.5.1.10 H2O + 10-formyl-tetrahydrofolate = H+ + tetrahydrofolate + formate folate transformations I 3-methylbutanal isovaleraldehyde*isoamylaldehyde*isopentaldehyde 86.133 C5 H10 O1 C(C=O)C(C)C CHEBI:16638:*PUBCHEM:11552:*LIGAND-CPD:C07329: 4.1.1.1 H+ + 4-methyl-2-oxopentanoate = 3-methylbutanal + CO2 leucine degradation III 3-methylbutanal isovaleraldehyde*isoamylaldehyde*isopentaldehyde 86.133 C5 H10 O1 C(C=O)C(C)C CHEBI:16638:*PUBCHEM:11552:*LIGAND-CPD:C07329: 1.1.1.1 H+ + 3-methylbutanal + NADH = 3-methylbutanol + NAD+ leucine degradation III S-scoulerine (13as)-5, 8,13,13a-tetrahydro-3,10-dimethoxy-6H-dibenzo[a,g]quinolizine-2,9-diol 327.379 C19 H21 N1 O4 COC4(=C(C1(=C(CC2(N(C1)CCC3(=C2C=C(C(OC)=C3)O)))C=C4))O) PUBCHEM:1152279:*LIGAND-CPD:C02106:*CAS:6451-73-6 1.21.3.- S-scoulerine + FAD = dehydroscoulerine + FADH2 dehydroscoulerine biosynthesis S-scoulerine (13as)-5, 8,13,13a-tetrahydro-3,10-dimethoxy-6H-dibenzo[a,g]quinolizine-2,9-diol 327.379 C19 H21 N1 O4 COC4(=C(C1(=C(CC2(N(C1)CCC3(=C2C=C(C(OC)=C3)O)))C=C4))O) PUBCHEM:1152279:*LIGAND-CPD:C02106:*CAS:6451-73-6 1.21.3.3 oxygen + (S)-reticuline = H+ + hydrogen peroxide + S-scoulerine dehydroscoulerine biosynthesis GDP-α-D-glucose GDP-glucose 603.329 C16 H23 N5 O16 P2 C2(C(O)C(O)C(COP([O-])(=O)OP([O-])(=O)OC1(OC(CO)C(O)C(O)C(O)1))O2)N3(C=NC4(=C3N=C(N)NC(=O)4)) PUBCHEM:25244464:*LIGAND-CPD:C00394: 2.7.7.34 H+ + α-D-glucose 1-phosphate + GTP = GDP-α-D-glucose + diphosphate GDP-glucose biosynthesis coumarin coumarin*cumarin*1,2-Benzopyrone 146.145 C9 H6 O2 C1(C=CC=C2(C=1C=CC(O2)=O)) PUBCHEM:323:*PUBCHEM:323:*CHEBI:28794:*LIGAND-CPD:C05851: H+ + coumarinate = coumarin + H2O coumarin biosynthesis (via 2-coumarate) ent-7-α-hydroxykaurenoate ent-7α-hydroxykaur-16-en-19-oate*ent-7-α-hydroxykaurenoic acid*7-hydroxy-kaurenoic acid 317.447 C20 H29 O3 C1(CCC(C2(C1(C3(CCC4(CC(C(C2)O)3CC4=C)))C))(C)C([O-])=O) PUBCHEM:25200352:*LIGAND-CPD:C11875: 1.14.13.79 H+ + ent-kaurenoate + oxygen + NADPH = ent-7-α-hydroxykaurenoate + H2O + NADP+ GA12 biosynthesis ent-7-α-hydroxykaurenoate ent-7α-hydroxykaur-16-en-19-oate*ent-7-α-hydroxykaurenoic acid*7-hydroxy-kaurenoic acid 317.447 C20 H29 O3 C1(CCC(C2(C1(C3(CCC4(CC(C(C2)O)3CC4=C)))C))(C)C([O-])=O) PUBCHEM:25200352:*LIGAND-CPD:C11875: 1.14.13.79 ent-7-α-hydroxykaurenoate + NADPH + H+ + oxygen = GA12-aldehyde + NADP+ + H2O GA12 biosynthesis orotate orotic acid 155.09 C5 H3 N2 O4 [O-]C(=O)C1(=CC(=O)NC(N1)=O) PUBCHEM:1492348:*CHEBI:30839:*LIGAND-CPD:C00295:*CAS:65-86-1 2.4.2.10 orotidine-5'-phosphate + diphosphate = 5-phospho-α-D-ribose 1-diphosphate + orotate uridine-5'-phosphate biosynthesis orotate orotic acid 155.09 C5 H3 N2 O4 [O-]C(=O)C1(=CC(=O)NC(N1)=O) PUBCHEM:1492348:*CHEBI:30839:*LIGAND-CPD:C00295:*CAS:65-86-1 1.3.5.2 (S)-dihydroorotate = orotate uridine-5'-phosphate biosynthesis GA34 gibberellin A34*gibberellin A34*GA34 347.387 C19 H23 O6 C1(C(C(C2(C4(C1(OC2=O)C5(CCC3(CC(CC3=C)(C4C([O-])=O)5))))(C))O)O) PUBCHEM:25245079:*LIGAND-CPD:C11868: 1.14.11.- gibberellin A4 + 2-oxoglutarate + oxygen = GA34 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) GA34 gibberellin A34*gibberellin A34*GA34 347.387 C19 H23 O6 C1(C(C(C2(C4(C1(OC2=O)C5(CCC3(CC(CC3=C)(C4C([O-])=O)5))))(C))O)O) PUBCHEM:25245079:*LIGAND-CPD:C11868: 1.14.11.- GA34 + 2-oxoglutarate + oxygen = H+ + GA34-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) 1-(3-aminopropyl)-4-aminobutanal 3-aminopropyl-4-aminobutyraldehyde 146.232 C7 H18 N2 O1 C([N+])CC[N+]CCCC=O CHEBI:58869:*PUBCHEM:25203056: 1-(3-aminopropyl)-4-aminobutanal = 1-(3-aminopropyl)-pyrrolinium + H2O spermine and spermidine degradation II 1-(3-aminopropyl)-4-aminobutanal 3-aminopropyl-4-aminobutyraldehyde 146.232 C7 H18 N2 O1 C([N+])CC[N+]CCCC=O CHEBI:58869:*PUBCHEM:25203056: 1.5.3.14 spermine + oxygen + H2O = 1-(3-aminopropyl)-4-aminobutanal + propane-1,3-diamine + hydrogen peroxide spermine and spermidine degradation II malonate semialdehyde 3-oxopropanoate*malonate-S-ald*malonic semialdehyde 87.055 C3 H3 O3 C([O-])(CC=O)=O PUBCHEM:9543142:*CHEBI:33190:*LIGAND-CPD:C00222:*CAS:926-61-4 1.1.1.59 3-hydroxypropionate + NAD+ = malonate semialdehyde + NADH + H+ β-alanine biosynthesis II malonate semialdehyde 3-oxopropanoate*malonate-S-ald*malonic semialdehyde 87.055 C3 H3 O3 C([O-])(CC=O)=O PUBCHEM:9543142:*CHEBI:33190:*LIGAND-CPD:C00222:*CAS:926-61-4 2.6.1.18 malonate semialdehyde + L-alanine = β-alanine + pyruvate β-alanine biosynthesis II sucrose-6-phosphate sucrose-6F-P*sucrose 6F-phosphate*sucrose-6-P 420.263 C12 H21 O14 P1 O=P([O-])([O-])OCC2(OC(CO)(OC1(OC(CO)C(O)C(O)C(O)1))C(O)C(O)2) PUBCHEM:439762:*CHEBI:57723:*PUBCHEM:25245080:*LIGAND-CPD:C02591: 3.2.1.26 sucrose-6-phosphate + H2O = β-D-glucose-6-phosphate + β-D-fructofuranose sucrose degradation I sucrose-6-phosphate sucrose-6F-P*sucrose 6F-phosphate*sucrose-6-P 420.263 C12 H21 O14 P1 O=P([O-])([O-])OCC2(OC(CO)(OC1(OC(CO)C(O)C(O)C(O)1))C(O)C(O)2) PUBCHEM:439762:*CHEBI:57723:*PUBCHEM:25245080:*LIGAND-CPD:C02591: 2.4.1.14 D-fructose-6-phosphate = H+ + sucrose-6-phosphate + UDP sucrose biosynthesis sucrose-6-phosphate sucrose-6F-P*sucrose 6F-phosphate*sucrose-6-P 420.263 C12 H21 O14 P1 O=P([O-])([O-])OCC2(OC(CO)(OC1(OC(CO)C(O)C(O)C(O)1))C(O)C(O)2) PUBCHEM:439762:*CHEBI:57723:*PUBCHEM:25245080:*LIGAND-CPD:C02591: 3.1.3.24 sucrose-6-phosphate + H2O = sucrose sucrose biosynthesis L-arogenate L-arogenic acid*pretyrosine 226.208 C10 H12 N1 O5 C1(CC(C([O-])=O)[N+])(C=CC(C=C1)O)C([O-])=O PUBCHEM:25244469:*LIGAND-CPD:C00826:*CAS:53078-86-7 1.3.1.78 L-arogenate + NADP+ = L-tyrosine + CO2 + NADPH tyrosine biosynthesis II L-arogenate L-arogenic acid*pretyrosine 226.208 C10 H12 N1 O5 C1(CC(C([O-])=O)[N+])(C=CC(C=C1)O)C([O-])=O PUBCHEM:25244469:*LIGAND-CPD:C00826:*CAS:53078-86-7 2.6.1.79 prephenate + L-glutamate = L-arogenate + 2-oxoglutarate tyrosine biosynthesis II L-arogenate L-arogenic acid*pretyrosine 226.208 C10 H12 N1 O5 C1(CC(C([O-])=O)[N+])(C=CC(C=C1)O)C([O-])=O PUBCHEM:25244469:*LIGAND-CPD:C00826:*CAS:53078-86-7 2.6.1.79 prephenate + L-glutamate = L-arogenate + 2-oxoglutarate phenylalanine biosynthesis II L-arogenate L-arogenic acid*pretyrosine 226.208 C10 H12 N1 O5 C1(CC(C([O-])=O)[N+])(C=CC(C=C1)O)C([O-])=O PUBCHEM:25244469:*LIGAND-CPD:C00826:*CAS:53078-86-7 4.2.1.91 H+ + L-arogenate = CO2 + H2O + L-phenylalanine phenylalanine biosynthesis II 1D-myo-inositol (1,2,3,4,6)-pentakisphosphate 1D-myo-inositol (1,2,3,4,6)-pentakisphosphate*Ins(1,2,3,4,6)P5*D-myo-inositol (1,2,3,4,6)-pentakisphosphate*inositol (1,2,3,4,6)-pentakisphosphate 569.977 C6 H7 O21 P5 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:23615305: 2.7.1.- D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + 1D-myo-inositol (1,2,3,4,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) 1D-myo-inositol (1,2,3,4,6)-pentakisphosphate 1D-myo-inositol (1,2,3,4,6)-pentakisphosphate*Ins(1,2,3,4,6)P5*D-myo-inositol (1,2,3,4,6)-pentakisphosphate*inositol (1,2,3,4,6)-pentakisphosphate 569.977 C6 H7 O21 P5 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:23615305: 2.7.1.140 1D-myo-inositol (1,2,3,4,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) 2-methyl-3-hydroxybutyryl-CoA (2S,3S)-3-hydroxy-2-methylbutanoyl-CoA*(2S,3S)-3-hydroxy-2-methylbutyryl-CoA*(S)-3-hydroxy-2-methylbutyryl-CoA*3-hydroxy-2-methylbutyryl-CoA 863.619 C26 H40 N7 O18 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(O)C(NCCC(NCCSC(=O)C(C(C)O)C)=O)=O)[O-])O1)OP([O-])([O-])=O)(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25245081:*LIGAND-CPD:C04405: 1.1.1.178 NAD+ + 2-methyl-3-hydroxybutyryl-CoA = H+ + NADH + 2-methylacetoacetyl-CoA isoleucine degradation I 2-methyl-3-hydroxybutyryl-CoA (2S,3S)-3-hydroxy-2-methylbutanoyl-CoA*(2S,3S)-3-hydroxy-2-methylbutyryl-CoA*(S)-3-hydroxy-2-methylbutyryl-CoA*3-hydroxy-2-methylbutyryl-CoA 863.619 C26 H40 N7 O18 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(O)C(NCCC(NCCSC(=O)C(C(C)O)C)=O)=O)[O-])O1)OP([O-])([O-])=O)(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25245081:*LIGAND-CPD:C04405: 4.2.1.17 2-methyl-3-hydroxybutyryl-CoA = 2-methyl-crotonyl-CoA + H2O isoleucine degradation I palmitoleate palmitoleic acid*(9Z)-Hexadecenoic acid*cis-9-Hexadecenoic acid 253.404 C16 H29 O2 [O-]C(=O)CCCCCCCC=CCCCCCC LIGAND-CPD:C08362:*CAS:373-49-9:*PUBCHEM:5461012:*CHEBI:32372: 3.1.2.14 H2O = palmitoleate palmitoleate biosynthesis II chlorophyll b chlorophyll b 907.486 C55 H70 N4 O6 MG1 C24(C=C9(C(C)C(CCC(=O)OCC=C(C)CCCC(C)CCCC(C)CCCC(C)C)C5(=N([Mg]36(N1(=C(C(CC)=C(C([H])=O)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) PUBCHEM:25244471:*LIGAND-CPD:C05307: 1.1.1.294 7-hydroxy-chlorophyll a = chlorophyll b + H+ chlorophyll cycle chlorophyll b chlorophyll b 907.486 C55 H70 N4 O6 MG1 C24(C=C9(C(C)C(CCC(=O)OCC=C(C)CCCC(C)CCCC(C)CCCC(C)C)C5(=N([Mg]36(N1(=C(C(CC)=C(C([H])=O)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) PUBCHEM:25244471:*LIGAND-CPD:C05307: 2.5.1.- H+ + chlorophyllide b + phytyl diphosphate = chlorophyll b + diphosphate chlorophyll cycle campesterol cholest 5-en-3-ol, 24-methyl*ergost-5-en-3β-ol, (24R)-*(24R)-24-methylcholest-5-en-3β-ol*24(R)-methylcholesterol*campesterin 400.687 C28 H48 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CCC(C(C)C)C)C)C(CC3)(C)4)))C))O) PUBCHEM:23424736:*LIGAND-CPD:C01789:*CHEBI:28623: 1.3.1.- campesterol + NADP+ = H+ + crinosterol + NADPH plant sterol biosynthesis campesterol cholest 5-en-3-ol, 24-methyl*ergost-5-en-3β-ol, (24R)-*(24R)-24-methylcholest-5-en-3β-ol*24(R)-methylcholesterol*campesterin 400.687 C28 H48 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CCC(C(C)C)C)C)C(CC3)(C)4)))C))O) PUBCHEM:23424736:*LIGAND-CPD:C01789:*CHEBI:28623: 1.14.13.- H+ + campesterol + oxygen + NADPH = (22α)-hydroxy-campesterol + H2O + NADP+ brassinosteroid biosynthesis II campesterol cholest 5-en-3-ol, 24-methyl*ergost-5-en-3β-ol, (24R)-*(24R)-24-methylcholest-5-en-3β-ol*24(R)-methylcholesterol*campesterin 400.687 C28 H48 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CCC(C(C)C)C)C)C(CC3)(C)4)))C))O) PUBCHEM:23424736:*LIGAND-CPD:C01789:*CHEBI:28623: 1.3.-.- H+ + 24-methyldesmosterol + NADPH = campesterol + NADP+ plant sterol biosynthesis campesterol cholest 5-en-3-ol, 24-methyl*ergost-5-en-3β-ol, (24R)-*(24R)-24-methylcholest-5-en-3β-ol*24(R)-methylcholesterol*campesterin 400.687 C28 H48 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CCC(C(C)C)C)C)C(CC3)(C)4)))C))O) PUBCHEM:23424736:*LIGAND-CPD:C01789:*CHEBI:28623: 5.3.3.1 campesterol = campest-4-en-3β-ol brassinosteroid biosynthesis II benzoyl-CoA S-benzoate coenzyme A*benzoyl-S-CoA 867.61 C28 H36 N7 O17 P3 S1 C4(C=CC=CC(C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=4) PUBCHEM:45266596:*CHEBI:57369:*LIGAND-CPD:C00512:*CHEBI:15515:*PUBCHEM:25245721:*PUBCHEM:25200800:*CAS:102185-37-5 2.3.1.144 anthranilate + benzoyl-CoA = N-benzoylanthranilate + coenzyme A benzoylanthranilate biosynthesis OPC8-CoA oxopentenyl-cyclopentane-octanoyl-CoA*8-[(1R,2R)-3-oxo-2-{(Z)-pent-2-enyl}cyclopentyl]octanoyl-CoA*OPC-8:0-CoA*3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoyl-CoA 1039.92 C39 H60 N7 O18 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)CCCCCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237325: 6.2.1.- 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate + coenzyme A + ATP = OPC8-CoA + AMP + diphosphate jasmonic acid biosynthesis OPC8-CoA oxopentenyl-cyclopentane-octanoyl-CoA*8-[(1R,2R)-3-oxo-2-{(Z)-pent-2-enyl}cyclopentyl]octanoyl-CoA*OPC-8:0-CoA*3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoyl-CoA 1039.92 C39 H60 N7 O18 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)CCCCCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237325: 1.3.3.6 OPC8-CoA + oxygen = OPC8-trans-2-enoyl-CoA + hydrogen peroxide jasmonic acid biosynthesis L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine methionine degradation I (to homocysteine) L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine 2'-deoxymugineic acid phytosiderophore biosynthesis L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine ethylene biosynthesis from methionine L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine S-adenosyl-L-methionine cycle II L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine S-adenosyl-L-methionine biosynthesis L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.10 L-homocysteine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + L-methionine methionine biosynthesis II L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 4.4.1.11 L-methionine + H2O = H+ + methanethiol + ammonia + 2-oxobutanoate methionine degradation II L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.8.1.8 S-adenosyl-L-methionine + S2- = 5'-deoxyadenosine + L-methionine lipoate biosynthesis and incorporation I L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.10 S-methyl-L-methionine + L-homocysteine = H+ + L-methionine methionine biosynthesis II L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.10 S-methyl-L-methionine + L-homocysteine = H+ + L-methionine S-methylmethionine cycle L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyl tri-L-glutamate + L-methionine methionine biosynthesis II L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyl tri-L-glutamate + L-methionine S-adenosyl-L-methionine cycle I L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyl tri-L-glutamate + L-methionine S-adenosyl-L-methionine cycle II L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.6.1.5 2-oxo-4-methylthiobutanoate = L-methionine methionine salvage I L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 6.1.1.10 H+ + L-methionine + ATP = diphosphate + AMP tRNA charging pathway L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 4.1.99.- 5-aminoimidazole ribonucleotide + S-adenosyl-L-methionine = hydroxymethylpyrimidine phosphate + 5'-deoxyadenosine + L-methionine + formate + carbon monoxide + H+ thiamine biosynthesis II L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.13 L-homocysteine + 5-methyl-tetrahydrofolate = L-methionine + tetrahydrofolate folate transformations I L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.13 L-homocysteine + 5-methyl-tetrahydrofolate = L-methionine + tetrahydrofolate folate transformations II (plants) L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.8.1.6 dethiobiotin + S-adenosyl-L-methionine = biotin + 5'-deoxyadenosine + L-methionine biotin biosynthesis from 7-keto-8-aminopelargonate L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.12 L-methionine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine dimethylsulfoniopropionate biosynthesis II (Spartina) L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.12 L-methionine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine dimethylsulfoniopropionate biosynthesis I (Wollastonia) L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C([N+])(CCSC)C(=O)[O-] PUBCHEM:6992087:*PUBCHEM:84815:*CHEBI:16643:*KNAPSACK:C00001379:*PUBCHEM:5255805:*CAS:7005-18-7*LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.12 L-methionine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine S-methylmethionine cycle L-histidine L-histidine*glyoxaline-5-alanine*α-amino-4-imidazoleproprionic acid*(S)-α-amino-1H-imidazole-4-propanoic acid*H*histidine*his 155.156 C6 H9 N3 O2 C1(=CNC=N1)CC(C([O-])=O)[N+] CHEBI:108612:*PUBCHEM:3651426:*PUBCHEM:3651426:*CAS:7006-35-1*LIGAND-CPD:C00135:*CAS:71-00-1 1.1.1.23 histidinal + NAD+ + H2O = H+ + L-histidine + NADH histidine biosynthesis L-histidine L-histidine*glyoxaline-5-alanine*α-amino-4-imidazoleproprionic acid*(S)-α-amino-1H-imidazole-4-propanoic acid*H*histidine*his 155.156 C6 H9 N3 O2 C1(=CNC=N1)CC(C([O-])=O)[N+] CHEBI:108612:*PUBCHEM:3651426:*PUBCHEM:3651426:*CAS:7006-35-1*LIGAND-CPD:C00135:*CAS:71-00-1 6.1.1.21 H+ + L-histidine + ATP = diphosphate + AMP tRNA charging pathway (R)-pantoate (R)-pantoate*pantoate*L-pantoate 147.15 C6 H11 O4 C(C(C)(C)C(C([O-])=O)O)O KNAPSACK:C00007622:*PUBCHEM:5289105:*CHEBI:15980:*CAS:470-29-1:*LIGAND-CPD:C00522: 6.3.2.1 β-alanine + (R)-pantoate + ATP = H+ + (R)-pantothenate + diphosphate + AMP phosphopantothenate biosynthesis I (R)-pantoate (R)-pantoate*pantoate*L-pantoate 147.15 C6 H11 O4 C(C(C)(C)C(C([O-])=O)O)O KNAPSACK:C00007622:*PUBCHEM:5289105:*CHEBI:15980:*CAS:470-29-1:*LIGAND-CPD:C00522: 6.3.2.1 β-alanine + (R)-pantoate + ATP = H+ + (R)-pantothenate + diphosphate + AMP pantothenate biosynthesis I (R)-pantoate (R)-pantoate*pantoate*L-pantoate 147.15 C6 H11 O4 C(C(C)(C)C(C([O-])=O)O)O KNAPSACK:C00007622:*PUBCHEM:5289105:*CHEBI:15980:*CAS:470-29-1:*LIGAND-CPD:C00522: 1.1.1.169 (R)-pantoate + NADP+ = H+ + 2-dehydropantoate + NADPH phosphopantothenate biosynthesis I (R)-pantoate (R)-pantoate*pantoate*L-pantoate 147.15 C6 H11 O4 C(C(C)(C)C(C([O-])=O)O)O KNAPSACK:C00007622:*PUBCHEM:5289105:*CHEBI:15980:*CAS:470-29-1:*LIGAND-CPD:C00522: 1.1.1.169 (R)-pantoate + NADP+ = H+ + 2-dehydropantoate + NADPH pantothenate biosynthesis I dihydroxyphenyl-5-methyloxazoline-VibF C11 H10 N1 O4 |VibF|1 S1 2,3-dihydroxybenzoate-VibB + L-threonine = dihydroxyphenyl-5-methyloxazoline-VibF + H2O vibriobactin biosynthesis dihydroxyphenyl-5-methyloxazoline-VibF C11 H10 N1 O4 |VibF|1 S1 dihydroxyphenyl-5-methyloxazoline-norspermidine-2,3-dihydroxybenzoate + dihydroxyphenyl-5-methyloxazoline-VibF = vibriobactin vibriobactin biosynthesis dihydroxyphenyl-5-methyloxazoline-VibF C11 H10 N1 O4 |VibF|1 S1 norspermidine-2,3-dihydroxybenzoate + dihydroxyphenyl-5-methyloxazoline-VibF = dihydroxyphenyl-5-methyloxazoline-norspermidine-2,3-dihydroxybenzoate vibriobactin biosynthesis monovinyl protochlorophyllide a protochlorophyllide*monovinyl protochlrophyllide a 611.959 C35 H31 N4 O5 MG1 C17(N9(C2(=C(C=1C)C(=O)C(C(OC)=O)([H])C2=C3(C(=C(C8(=N3[Mg]6(N4(C(C(=C(C4=CC5(C(=C(C(N=56)=C7)CC)C))C=C)C)=C8))9))C)CCC(=O)[O-])))) PUBCHEM:44229077:*CAS:14751-08-7*LIGAND-CPD:C02880: 1.3.1.75 H+ + divinyl protochlorophyllide a + NADPH = monovinyl protochlorophyllide a + NADP+ chlorophyllide a biosynthesis I monovinyl protochlorophyllide a protochlorophyllide*monovinyl protochlrophyllide a 611.959 C35 H31 N4 O5 MG1 C17(N9(C2(=C(C=1C)C(=O)C(C(OC)=O)([H])C2=C3(C(=C(C8(=N3[Mg]6(N4(C(C(=C(C4=CC5(C(=C(C(N=56)=C7)CC)C))C=C)C)=C8))9))C)CCC(=O)[O-])))) PUBCHEM:44229077:*CAS:14751-08-7*LIGAND-CPD:C02880: 1.3.1.33 chlorophyllide a + NADP+ = H+ + monovinyl protochlorophyllide a + NADPH chlorophyllide a biosynthesis I monodehydroascorbate monodehydroascorbic acid*semidehydroascorbic acid*semidehydroascorbate 175.118 C6 H7 O6 O=C1(OC(C(=C1O)[O-])C(O)CO) PUBCHEM:25243880:*LIGAND-CPD:C01041:*CHEBI:16504: 1.6.5.4 monodehydroascorbate + NADPH = H+ + L-ascorbate + NADP+ ascorbate glutathione cycle monodehydroascorbate monodehydroascorbic acid*semidehydroascorbic acid*semidehydroascorbate 175.118 C6 H7 O6 O=C1(OC(C(=C1O)[O-])C(O)CO) PUBCHEM:25243880:*LIGAND-CPD:C01041:*CHEBI:16504: 1.11.1.11 H+ + L-ascorbate + hydrogen peroxide = monodehydroascorbate + H2O ascorbate glutathione cycle monodehydroascorbate monodehydroascorbic acid*semidehydroascorbic acid*semidehydroascorbate 175.118 C6 H7 O6 O=C1(OC(C(=C1O)[O-])C(O)CO) PUBCHEM:25243880:*LIGAND-CPD:C01041:*CHEBI:16504: monodehydroascorbate = H+ + L-ascorbate + L-dehydro-ascorbate ascorbate glutathione cycle brassicasterol 398.671 C28 H46 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CC3)4C)C(C=CC(C)C(C)C)C)))C))O) PUBCHEM:25244475:*LIGAND-CPD:C08813: 1.3.1.- 24-epi-campesterol + NADPH + H+ + oxygen = brassicasterol + NADP+ + H2O plant sterol biosynthesis H2 hydrogen*hydrogen molecule 2.016 H2 [H][H] PUBCHEM:783:*CHEBI:33251:*LIGAND-CPD:C00282:*CAS:1333-74-0: 1.18.6.1 H+ + N2 + ATP + H2O = H2 + ammonia + ADP nitrogen fixation 1-kestotriose 1-kestose 504.441 C18 H32 O16 C1(OC(C(O)C(O)1)CO)(COC2(OC(C(C2O)O)CO)CO)OC3(C(O)C(C(O)C(CO)O3)O) LIGAND-CPD:C03661:*PUBCHEM:440080: 2.4.1.99 sucrose + sucrose = 1-kestotriose + β-D-glucose fructan biosynthesis 1-kestotriose 1-kestose 504.441 C18 H32 O16 C1(OC(C(O)C(O)1)CO)(COC2(OC(C(C2O)O)CO)CO)OC3(C(O)C(C(O)C(CO)O3)O) LIGAND-CPD:C03661:*PUBCHEM:440080: 2.4.1.- 1-kestotriose + sucrose = 6G-kestotriose + sucrose fructan biosynthesis 1-kestotriose 1-kestose 504.441 C18 H32 O16 C1(OC(C(O)C(O)1)CO)(COC2(OC(C(C2O)O)CO)CO)OC3(C(O)C(C(O)C(CO)O3)O) LIGAND-CPD:C03661:*PUBCHEM:440080: 3.2.1.80 1-kestotriose + H2O = sucrose fructan degradation 1-kestotriose 1-kestose 504.441 C18 H32 O16 C1(OC(C(O)C(O)1)CO)(COC2(OC(C(C2O)O)CO)CO)OC3(C(O)C(C(O)C(CO)O3)O) LIGAND-CPD:C03661:*PUBCHEM:440080: 2.4.1.100 1-kestotriose + 1-kestotriose = 1,1-kestotetraose + sucrose fructan biosynthesis 1-kestotriose 1-kestose 504.441 C18 H32 O16 C1(OC(C(O)C(O)1)CO)(COC2(OC(C(C2O)O)CO)CO)OC3(C(O)C(C(O)C(CO)O3)O) LIGAND-CPD:C03661:*PUBCHEM:440080: 2.4.1.10 1-kestotriose + sucrose = 1,6-kestotetraose + β-D-glucose fructan biosynthesis 3-hydroxy-3-phenylpropionate 3-hydroxy-3-phenyl propionic acid*3-hydroxy-3-phenylpropanoate*beta-hydroxyphenylpropionic acid*Propanoic acid, 3-hydroxy-3-phenyl*3-hydroxy-3-phenylpropanoic acid 165.168 C9 H9 O3 C1(C=C(C(O)CC([O-])=O)C=CC=1) PUBCHEM:22328018:*CHEBI:19929:*PUBCHEM:92959:*PUBCHEM:22328018: 3-hydroxy-3-phenylpropionate = benzaldehyde + acetate benzoate biosynthesis II (CoA-independent, non-β-oxidative) 3-hydroxy-3-phenylpropionate 3-hydroxy-3-phenyl propionic acid*3-hydroxy-3-phenylpropanoate*beta-hydroxyphenylpropionic acid*Propanoic acid, 3-hydroxy-3-phenyl*3-hydroxy-3-phenylpropanoic acid 165.168 C9 H9 O3 C1(C=C(C(O)CC([O-])=O)C=CC=1) PUBCHEM:22328018:*CHEBI:19929:*PUBCHEM:92959:*PUBCHEM:22328018: trans-cinnamate + H2O = 3-hydroxy-3-phenylpropionate benzoate biosynthesis II (CoA-independent, non-β-oxidative) N2 nitrogen molecule*nitrogen 28.013 N2 N#N PUBCHEM:947:*CHEBI:17997:*LIGAND-CPD:C00697:*CAS:7727-37-9 1.18.6.1 H+ + N2 + ATP + H2O = H2 + ammonia + ADP nitrogen fixation pseudouridine 244.204 C9 H12 N2 O6 O=C1(C(=CNC(=O)N1)C2(OC(CO)C(O)C(O)2)) PUBCHEM:15047:*CHEBI:17802:*LIGAND-CPD:C02067:*CAS:1445-07-4 2.7.1.83 pseudouridine + ATP = H+ + pseudouridine 5'-phosphate + ADP pseudouridine degradation DMSP-amine dimethylsulfoniopropionate-amine 121.24 C5 H15 N1 S1 [S+](C)(C)CCC[N+] PUBCHEM:25202166: H+ + S-methyl-L-methionine = DMSP-amine + CO2 dimethylsulfoniopropionate biosynthesis II (Spartina) DMSP-amine dimethylsulfoniopropionate-amine 121.24 C5 H15 N1 S1 [S+](C)(C)CCC[N+] PUBCHEM:25202166: DMSP-amine + oxygen + H2O = H+ + 3-dimethylsulfoniopropionaldehyde + ammonia + hydrogen peroxide dimethylsulfoniopropionate biosynthesis II (Spartina) L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 4.1.1.19 H+ + L-arginine = CO2 + agmatine arginine degradation III (arginine decarboxylase/agmatinase pathway) L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 4.1.1.19 H+ + L-arginine = CO2 + agmatine arginine dependent acid resistance L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 4.1.1.19 H+ + L-arginine = CO2 + agmatine putrescine biosynthesis IV L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 4.1.1.19 H+ + L-arginine = CO2 + agmatine putrescine biosynthesis II L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 4.1.1.19 H+ + L-arginine = CO2 + agmatine arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 3.5.3.1 H2O + L-arginine = urea + L-ornithine urea cycle L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 3.5.3.1 H2O + L-arginine = urea + L-ornithine arginine degradation VI (arginase 2 pathway) L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 3.5.3.1 H2O + L-arginine = urea + L-ornithine putrescine biosynthesis IV L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 3.5.3.1 H2O + L-arginine = urea + L-ornithine arginine degradation I (arginase pathway) L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 3.5.3.1 H2O + L-arginine = urea + L-ornithine citrulline biosynthesis L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 3.5.3.6 H2O + L-arginine = H+ + ammonia + L-citrulline proline biosynthesis II (from arginine) L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 1.14.13.39 oxygen + NADPH + L-arginine = L-citrulline + NADP+ + nitric oxide citrulline-nitric oxide cycle L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 1.13.12.1 oxygen + L-arginine = 4-guanidinobutyramide + H2O + CO2 arginine degradation X (arginine monooxygenase pathway) L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 6.1.1.19 H+ + L-arginine + ATP = diphosphate + AMP tRNA charging pathway L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 4.3.2.1 L-arginino-succinate = L-arginine + fumarate urea cycle L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 4.3.2.1 L-arginino-succinate = L-arginine + fumarate arginine biosynthesis II (acetyl cycle) L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 4.3.2.1 L-arginino-succinate = L-arginine + fumarate citrulline-nitric oxide cycle L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 175.21 C6 H15 N4 O2 C(C([N+])C(=O)[O-])CCNC(=[N+])N PUBCHEM:5231987:*CHEBI:32696:*PUBCHEM:5231987:*CHEBI:32696:*KNAPSACK:C00001340:*CAS:7004-12-8*LIGAND-CPD:C00062:*CAS:74-79-3 4.3.2.1 L-arginino-succinate = L-arginine + fumarate arginine biosynthesis I episterol 398.671 C28 H46 O1 C1(CC(CC2(C1(C3(C(=CC2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))O) PUBCHEM:25200387:*CHEBI:50586:*LIGAND-CPD:C15777: 1.3.3.- episterol = H+ + 5-dehydro episterol plant sterol biosynthesis episterol 398.671 C28 H46 O1 C1(CC(CC2(C1(C3(C(=CC2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))O) PUBCHEM:25200387:*CHEBI:50586:*LIGAND-CPD:C15777: 1.1.1.- episterone + NADPH + H+ = episterol + NADP+ plant sterol biosynthesis beta-methylenecyclopropyl pyruvate 3-(2-methylidenecyclopropyl)-2-oxopropanoic acid*ketohypoglycin*2-methylene-alpha-oxocyclopropanepropanoic acid*methylenecyclopropylpyruvate 139.13 C7 H7 O3 C1(CC(CC(=O)C(=O)[O-])1)(=C) PUBCHEM:193412:*PUBCHEM:25201294: 4.1.1.- H+ + 2-oxo-3-carboxy-4,5-cyclopropylhex-5-enoate = beta-methylenecyclopropyl pyruvate + CO2 hypoglycin biosynthesis beta-methylenecyclopropyl pyruvate 3-(2-methylidenecyclopropyl)-2-oxopropanoic acid*ketohypoglycin*2-methylene-alpha-oxocyclopropanepropanoic acid*methylenecyclopropylpyruvate 139.13 C7 H7 O3 C1(CC(CC(=O)C(=O)[O-])1)(=C) PUBCHEM:193412:*PUBCHEM:25201294: 2.6.1.- beta-methylenecyclopropyl pyruvate + L-alanine = hypoglycin A + pyruvate hypoglycin biosynthesis GDP-L-fucose guanosine diphosphate fucose*guanosine 5'-(trihydrogen diphosphate), P'-(6-deoxy-β-L- galactopyranosyl) ester*2-amino-9-[3,4-dihydroxy-5-[[hydroxy-[hydroxy-(3,4,5-trihydroxy- 6-methyl-tetrahydropyran-2-yl)oxy-phosphinoyl]oxy-phosphinoyl] oxymethyl]tetrahydrofuran-2-yl]-1,9-dihydropurin-6-one 587.33 C16 H23 N5 O15 P2 NC4(NC(C3(=C(N(C1(C(C(C(O1)COP(OP(OC2(C(C(C(C(O2)C)O)O)O))([O-])=O)([O-])=O)O)O))C=N3)N=4))=O) PUBCHEM:25244478:*LIGAND-CPD:C00325:*CAS:15839-70-0 1.1.1.271 NADP+ + GDP-L-fucose = H+ + NADPH + GDP-4-dehydro-6-deoxy-D-mannose GDP-L-fucose biosynthesis I (from GDP-D-mannose) GDP-L-fucose guanosine diphosphate fucose*guanosine 5'-(trihydrogen diphosphate), P'-(6-deoxy-β-L- galactopyranosyl) ester*2-amino-9-[3,4-dihydroxy-5-[[hydroxy-[hydroxy-(3,4,5-trihydroxy- 6-methyl-tetrahydropyran-2-yl)oxy-phosphinoyl]oxy-phosphinoyl] oxymethyl]tetrahydrofuran-2-yl]-1,9-dihydropurin-6-one 587.33 C16 H23 N5 O15 P2 NC4(NC(C3(=C(N(C1(C(C(C(O1)COP(OP(OC2(C(C(C(C(O2)C)O)O)O))([O-])=O)([O-])=O)O)O))C=N3)N=4))=O) PUBCHEM:25244478:*LIGAND-CPD:C00325:*CAS:15839-70-0 2.7.7.30 H+ + β-L-fucose 1-phosphate + GTP = GDP-L-fucose + diphosphate GDP-L-fucose biosynthesis II (from L-fucose) GDP-L-fucose guanosine diphosphate fucose*guanosine 5'-(trihydrogen diphosphate), P'-(6-deoxy-β-L- galactopyranosyl) ester*2-amino-9-[3,4-dihydroxy-5-[[hydroxy-[hydroxy-(3,4,5-trihydroxy- 6-methyl-tetrahydropyran-2-yl)oxy-phosphinoyl]oxy-phosphinoyl] oxymethyl]tetrahydrofuran-2-yl]-1,9-dihydropurin-6-one 587.33 C16 H23 N5 O15 P2 NC4(NC(C3(=C(N(C1(C(C(C(O1)COP(OP(OC2(C(C(C(C(O2)C)O)O)O))([O-])=O)([O-])=O)O)O))C=N3)N=4))=O) PUBCHEM:25244478:*LIGAND-CPD:C00325:*CAS:15839-70-0 GDP-L-fucose + GDP-L-galactose = GDP xyloglucan biosynthesis ubiquinol-10 ubiquinol-10*ubiquinol(10) 865.373 C59 H92 O4 COC1(C(OC)=C(O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C(O)=1) PUBCHEM:9962735: 2.1.1.64 3-demethylubiquinol-10 + S-adenosyl-L-methionine = H+ + ubiquinol-10 + S-adenosyl-L-homocysteine ubiquinol-10 biosynthesis (eukaryotic) maltotriose Amylotriose 504.441 C18 H32 O16 OC1(C(C(C(OC1OC2(C(OC(C(C2O)O)OC3(C(OC(C(C3O)O)O)CO))CO))CO)O)O) CHEBI:15444:*PUBCHEM:439586:*LIGAND-CPD:C01835:*CAS:1109-28-0 2.4.1.25 maltotriose + maltose = maltotetraose + β-D-glucose glycogen degradation I maltotriose Amylotriose 504.441 C18 H32 O16 OC1(C(C(C(OC1OC2(C(OC(C(C2O)O)OC3(C(OC(C(C3O)O)O)CO))CO))CO)O)O) CHEBI:15444:*PUBCHEM:439586:*LIGAND-CPD:C01835:*CAS:1109-28-0 3.2.1.20 maltotriose + H2O = maltose + α-D-glucose glycogen degradation I maltotriose Amylotriose 504.441 C18 H32 O16 OC1(C(C(C(OC1OC2(C(OC(C(C2O)O)OC3(C(OC(C(C3O)O)O)CO))CO))CO)O)O) CHEBI:15444:*PUBCHEM:439586:*LIGAND-CPD:C01835:*CAS:1109-28-0 2.4.1.1 maltotetraose = maltotriose + α-D-glucose 1-phosphate glycogen degradation I carbamate 60.032 C1 H2 N1 O2 C(=O)([O-])N PUBCHEM:276:*LIGAND-CPD:C01563:*CHEBI:13941: 4.2.1.104 carbamate + H+ = ammonia + CO2 cyanate degradation carbamate 60.032 C1 H2 N1 O2 C(=O)([O-])N PUBCHEM:276:*LIGAND-CPD:C01563:*CHEBI:13941: 4.2.1.104 cyanate + bicarbonate + H+ = carbamate + CO2 cyanate degradation (Z)-β-ocimene cis-β-ocimene 136.236 C10 H16 C(=CCC=C(C)C)(C=C)C PUBCHEM:5320250: 4.2.3.- geranyl diphosphate = (Z)-β-ocimene + diphosphate monoterpene biosynthesis ayapin 6,7-(methylenedioxy)coumarin 190.155 C10 H6 O4 C1(OC2(=C(O1)C=C3(C(=C2)C=CC(=O)O3))) scopoletin = ayapin simplecoumarins biosynthesis ayapin 6,7-(methylenedioxy)coumarin 190.155 C10 H6 O4 C1(OC2(=C(O1)C=C3(C(=C2)C=CC(=O)O3))) isoscopoletin = ayapin simplecoumarins biosynthesis heptadecane 240.471 C17 H36 C(CCCCCCC)CCCCCCCCC PUBCHEM:12398:*CHEBI:16148:*LIGAND-CPD:C01816:*CAS:629-78-7 4.1.99.5 octadecanal = heptadecane + carbon monoxide heptadecane biosynthesis 2-(3-carboxy-3-aminopropyl)-L-histidine in eEF-2 diphthine intermediate in eEF-2*2-amino-4-[[4-(2-amino-2-carboxy-ethyl)-1H-imidazol-2-yl]] butanoic acid*2-(3-carboxy-3-aminopropyl)-L-histidine 256.261 C10 H14 N4 O3 |eEF-2|2 PUBCHEM:25203075:*LIGAND-CPD:C04441: 2.1.1.98 2-(3-carboxy-3-aminopropyl)-L-histidine in eEF-2 + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine diphthamide biosynthesis 2-(3-carboxy-3-aminopropyl)-L-histidine in eEF-2 diphthine intermediate in eEF-2*2-amino-4-[[4-(2-amino-2-carboxy-ethyl)-1H-imidazol-2-yl]] butanoic acid*2-(3-carboxy-3-aminopropyl)-L-histidine 256.261 C10 H14 N4 O3 |eEF-2|2 PUBCHEM:25203075:*LIGAND-CPD:C04441: S-adenosyl-L-methionine = 2-(3-carboxy-3-aminopropyl)-L-histidine in eEF-2 + S-methyl-5'-thioadenosine diphthamide biosynthesis (S)-reticuline 1-[(3-hydroxy-4-methoxy-phenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol 330.403 C19 H24 N1 O4 COC3(=C(C=C(CC1([N+](CCC2(=C1C=C(C(OC)=C2)O))C))C=C3)O) PUBCHEM:25203074:*LIGAND-CPD:C02105:*PUBCHEM:439653:*CHEBI:16718: 1.21.3.3 oxygen + (S)-reticuline = H+ + hydrogen peroxide + S-scoulerine dehydroscoulerine biosynthesis 2,3-dihydroxybenzoate-VibB C7 H5 O3 |VibB|1 S1 2,3-dihydroxybenzoyl-AMP = 2,3-dihydroxybenzoate-VibB + AMP vibriobactin biosynthesis 2,3-dihydroxybenzoate-VibB C7 H5 O3 |VibB|1 S1 2,3-dihydroxybenzoate-VibB + L-threonine = dihydroxyphenyl-5-methyloxazoline-VibF + H2O vibriobactin biosynthesis 2,3-dihydroxybenzoate-VibB C7 H5 O3 |VibB|1 S1 2,3-dihydroxybenzoate-VibB + norspermidine = norspermidine-2,3-dihydroxybenzoate + H2O vibriobactin biosynthesis trans-cinnamate trans-cinnamic acid*β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 147.153 C9 H7 O2 C1(C=C(C=CC(=O)[O-])C=CC=1) CHEBI:15669:*PUBCHEM:5957728:*LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 1.14.13.14 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 2-coumarate coumarin biosynthesis (via 2-coumarate) trans-cinnamate trans-cinnamic acid*β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 147.153 C9 H7 O2 C1(C=C(C=CC(=O)[O-])C=CC=1) CHEBI:15669:*PUBCHEM:5957728:*LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ suberin biosynthesis trans-cinnamate trans-cinnamic acid*β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 147.153 C9 H7 O2 C1(C=C(C=CC(=O)[O-])C=CC=1) CHEBI:15669:*PUBCHEM:5957728:*LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ phenylpropanoid biosynthesis, initial reactions trans-cinnamate trans-cinnamic acid*β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 147.153 C9 H7 O2 C1(C=C(C=CC(=O)[O-])C=CC=1) CHEBI:15669:*PUBCHEM:5957728:*LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ trans-cinnamoyl-CoA biosynthesis trans-cinnamate trans-cinnamic acid*β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 147.153 C9 H7 O2 C1(C=C(C=CC(=O)[O-])C=CC=1) CHEBI:15669:*PUBCHEM:5957728:*LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ benzoate biosynthesis II (CoA-independent, non-β-oxidative) trans-cinnamate trans-cinnamic acid*β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 147.153 C9 H7 O2 C1(C=C(C=CC(=O)[O-])C=CC=1) CHEBI:15669:*PUBCHEM:5957728:*LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 6.2.1.- trans-cinnamate + coenzyme A + ATP = (E)-cinnamoyl-CoA + AMP + diphosphate trans-cinnamoyl-CoA biosynthesis trans-cinnamate trans-cinnamic acid*β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 147.153 C9 H7 O2 C1(C=C(C=CC(=O)[O-])C=CC=1) CHEBI:15669:*PUBCHEM:5957728:*LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 trans-cinnamate + H2O = 3-hydroxy-3-phenylpropionate benzoate biosynthesis II (CoA-independent, non-β-oxidative) trans-cinnamate trans-cinnamic acid*β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 147.153 C9 H7 O2 C1(C=C(C=CC(=O)[O-])C=CC=1) CHEBI:15669:*PUBCHEM:5957728:*LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 1.14.13.11 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 4-coumarate suberin biosynthesis trans-cinnamate trans-cinnamic acid*β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 147.153 C9 H7 O2 C1(C=C(C=CC(=O)[O-])C=CC=1) CHEBI:15669:*PUBCHEM:5957728:*LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 1.14.13.11 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 4-coumarate phenylpropanoid biosynthesis, initial reactions isorhamnetin 3, 4'-bisulphate 473.359 C16 H9 O13 S2 O=C1(C(OS(=O)(=O)[O-])=C(OC2(C=C([O-])C=C(O)C1=2))C3(=CC=C(OS(=O)(=O)[O-])C(OC)=C3)) PUBCHEM:45479344: isorhamnetin 3-sulphate + phosphoadenosine-5'-phosphosulfate = H+ + adenosine 3',5'-bisphosphate + isorhamnetin 3, 4'-bisulphate quercetinsulphates biosynthesis strictosamide 498.532 C26 H30 N2 O8 C4(N3(C([H])C2(NC1(C(=CC=CC=1)C=2CC3CC6(C([H])4C([H])(C(OC5(OC(C(C(C5O)O)O)CO))OC=6)C=C)))))(=O) PUBCHEM:45479597: strictosidine = strictosamide + H2O + CO2 camptothecin biosynthesis strictosamide 498.532 C26 H30 N2 O8 C4(N3(C([H])C2(NC1(C(=CC=CC=1)C=2CC3CC6(C([H])4C([H])(C(OC5(OC(C(C(C5O)O)O)CO))OC=6)C=C)))))(=O) PUBCHEM:45479597: strictosamide = camptothecin camptothecin biosynthesis (S)-3-amino-2-methylpropanoate L-3-amino-isobutanoate 103.121 C4 H9 N1 O2 C(C(C([O-])=O)C)[N+] PUBCHEM:6971062:*CHEBI:18188:*LIGAND-CPD:C03284: 2.6.1.22 2-oxoglutarate + (S)-3-amino-2-methylpropanoate = L-glutamate + (S)-methylmalonate-semialdehyde valine degradation I cytidine 243.219 C9 H13 N3 O5 C1(C(O)C(OC1CO)N2(C=CC(N)=NC2=O))O CHEBI:106687:*PUBCHEM:596:*LIGAND-CPD:C00475:*CAS:65-46-3 3.5.4.5 H2O + cytidine = uridine + ammonia salvage pathways of pyrimidine ribonucleotides cytidine 243.219 C9 H13 N3 O5 C1(C(O)C(OC1CO)N2(C=CC(N)=NC2=O))O CHEBI:106687:*PUBCHEM:596:*LIGAND-CPD:C00475:*CAS:65-46-3 3.5.4.5 H2O + cytidine = uridine + ammonia pyrimidine ribonucleosides degradation II cytidine 243.219 C9 H13 N3 O5 C1(C(O)C(OC1CO)N2(C=CC(N)=NC2=O))O CHEBI:106687:*PUBCHEM:596:*LIGAND-CPD:C00475:*CAS:65-46-3 2.7.1.- cytidine + GTP = H+ + CMP + GDP salvage pathways of pyrimidine ribonucleotides 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA 2-(3'-carboxypropionyl)benzoyl-CoA*succinylbenzoyl-CoA*2-succinylbenzoyl-CoA*o-succinylbenzoyl-CoA*4-(2'-carboxyphenyl)-4-oxobutyryl-CoA 966.676 C32 H39 N7 O20 P3 S1 C2(C(O)C(C(COP([O-])(=O)OP([O-])(OCC(C)(C)C(C(NCCC(NCCSC(CCC(C1(C=CC=CC(C([O-])=O)=1))=O)=O)=O)=O)O)=O)O2)OP([O-])(=O)[O-])(N4(C=NC3(C(=NC=NC=34)N))) PUBCHEM:25245100:*LIGAND-CPD:C03160:*PUBCHEM:11966131:*PUBCHEM:11953819: 6.2.1.26 ATP + o-succinylbenzoate + coenzyme A = 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA + ADP 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA 2-(3'-carboxypropionyl)benzoyl-CoA*succinylbenzoyl-CoA*2-succinylbenzoyl-CoA*o-succinylbenzoyl-CoA*4-(2'-carboxyphenyl)-4-oxobutyryl-CoA 966.676 C32 H39 N7 O20 P3 S1 C2(C(O)C(C(COP([O-])(=O)OP([O-])(OCC(C)(C)C(C(NCCC(NCCSC(CCC(C1(C=CC=CC(C([O-])=O)=1))=O)=O)=O)=O)O)=O)O2)OP([O-])(=O)[O-])(N4(C=NC3(C(=NC=NC=34)N))) PUBCHEM:25245100:*LIGAND-CPD:C03160:*PUBCHEM:11966131:*PUBCHEM:11953819: 4.1.3.36 H+ + 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA = 1,4-dihydroxy-2-naphthoyl-CoA + H2O 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) D-myo-inositol (3,4)-bisphosphate 1D-myo-inositol (3,4)-bisphosphate*inositol (3,4)-bisphosphate*(2,3,4,5)-tetrahydroxy-6-phosphonooxy-cyclohexoxy)phosphonic acid*Ins(3,4)P2*I(3,4)P2 336.085 C6 H10 O12 P2 O=P([O-])([O-])OC1(C(O)C(O)C(O)C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:21120281:*LIGAND-CPD:C04063: 1D-myo-inositol (3)-monophosphate + ATP = H+ + D-myo-inositol (3,4)-bisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) D-myo-inositol (3,4)-bisphosphate 1D-myo-inositol (3,4)-bisphosphate*inositol (3,4)-bisphosphate*(2,3,4,5)-tetrahydroxy-6-phosphonooxy-cyclohexoxy)phosphonic acid*Ins(3,4)P2*I(3,4)P2 336.085 C6 H10 O12 P2 O=P([O-])([O-])OC1(C(O)C(O)C(O)C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:21120281:*LIGAND-CPD:C04063: D-myo-inositol (3,4)-bisphosphate + ATP = H+ + D-myo-inositol (3,4,6)-trisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) 6-deoxoteasterone deoxoteasterone 434.701 C28 H50 O3 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(C(C(C(C(C)C)C)O)O)C)C(CC3)(C)4)))C))O) PUBCHEM:25202174:*LIGAND-CPD:C15799: 1.14.-.- H+ + 6-deoxocathasterone + oxygen = 6-deoxoteasterone + H2O brassinosteroid biosynthesis II 6-deoxoteasterone deoxoteasterone 434.701 C28 H50 O3 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(C(C(C(C(C)C)C)O)O)C)C(CC3)(C)4)))C))O) PUBCHEM:25202174:*LIGAND-CPD:C15799: 6-deoxoteasterone = H+ + 3-dehydro-6-deoxoteasterone brassinosteroid biosynthesis II α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.27 H+ + α-D-glucose 1-phosphate + ATP = ADP-α-D-glucose + diphosphate glycogen biosynthesis I (from ADP-D-Glucose) α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.27 H+ + α-D-glucose 1-phosphate + ATP = ADP-α-D-glucose + diphosphate starch biosynthesis α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate sucrose degradation III α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate GDP-glucose biosynthesis α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate glycogen degradation II α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate UDP-glucose biosynthesis (from glucose 6-phosphate) α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate starch degradation α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate glycogen degradation I α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate starch biosynthesis α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate glucose and glucose-1-phosphate degradation α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate sucrose biosynthesis α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 3.1.3.10 glucose and glucose-1-phosphate degradation α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.4.1.1 glycogen degradation II α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.4.1.1 maltotetraose = maltotriose + α-D-glucose 1-phosphate glycogen degradation I α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: α-D-glucose 1-phosphate = β-D-glucose 1-phosphate galactose degradation I (Leloir pathway) α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.4.1.1 starch degradation α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.34 H+ + α-D-glucose 1-phosphate + GTP = GDP-α-D-glucose + diphosphate GDP-glucose biosynthesis α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate glycogen biosynthesis II (from UDP-D-Glucose) α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate sucrose degradation III α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate stachyose degradation α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate UDP-glucose biosynthesis (from glucose 6-phosphate) α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate colanic acid building blocks biosynthesis α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate galactose degradation III α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate sucrose biosynthesis α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.4.1.1 glycogen degradation II α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.4.1.1 glycogen degradation I α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.12 α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-D-galactose galactose degradation I (Leloir pathway) α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.12 α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-D-galactose stachyose degradation α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.12 α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-D-galactose colanic acid building blocks biosynthesis α-D-glucose 1-phosphate glucose 1-phosphate*cori ester*D-glucose 1-phosphate*glucose-1P*α-glucose-1-phosphate*D-glucose-α-1-phosphate*α-D-glucose-1-P*D-glucose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) CHEBI:58601:*PUBCHEM:7091266:*CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.12 α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-D-galactose UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) ω-hydroxylaurate ω-hydroxylauric acid*12-hydroxydodecanoic acid*12-hydroxylauric acid*omega-hydroxydodecanoic acid 215.312 C12 H23 O3 OCCCCCCCCCCCC(=O)[O-] PUBCHEM:79034:*CHEBI:36204:*PUBCHEM:9548810: 1.14.13.- laurate + oxygen + NADPH + H+ = ω-hydroxylaurate + NADP+ + H2O ω-hydroxylation of caprate and laurate trehalose α,α-trehalose 342.299 C12 H22 O11 C2(CO)(C(O)C(O)C(O)C(OC1(OC(CO)C(O)C(O)C(O)1))O2) PUBCHEM:7427:*CHEBI:16551:*LIGAND-CPD:C01083:*CAS:99-20-7 3.1.3.12 trehalose 6-phosphate + H2O = trehalose trehalose biosynthesis I trehalose α,α-trehalose 342.299 C12 H22 O11 C2(CO)(C(O)C(O)C(O)C(OC1(OC(CO)C(O)C(O)C(O)1))O2) PUBCHEM:7427:*CHEBI:16551:*LIGAND-CPD:C01083:*CAS:99-20-7 3.2.1.28 trehalose + H2O = β-D-glucose trehalose degradation II (trehalase) 9,15,9'-tri-cis-ζ-carotene 9,15,9'-cis-ζ-carotene 540.914 C40 H60 CC(=CCCC(C)=CCCC(C)=CC=CC(=CC=CC=C(C=CC=C(CCC=C(CCC=C(C)C)C)C)C)C)C PUBCHEM:24755586:*CHEBI:48717: 1.14.99.- 15-cis-phytoene + oxygen = 9,15,9'-tri-cis-ζ-carotene + H2O trans-lycopene biosynthesis II (plants) 9,15,9'-tri-cis-ζ-carotene 9,15,9'-cis-ζ-carotene 540.914 C40 H60 CC(=CCCC(C)=CCCC(C)=CC=CC(=CC=CC=C(C=CC=C(CCC=C(CCC=C(C)C)C)C)C)C)C PUBCHEM:24755586:*CHEBI:48717: 9,15,9'-tri-cis-ζ-carotene = 9,9'-di-cis-ζ-carotene trans-lycopene biosynthesis II (plants) (S)-methylmalonate-semialdehyde (S)-ch3-malonate-semialdehyde*(S)-2-methyl-3-oxopropanoate*2-methyl-3-oxopropanoate*CH3-malonate-S-ald*ch3-malonate-semialdehyde 101.082 C4 H5 O3 C(C(C=O)C)(=O)[O-] LIGAND-CPD:C00349:*LIGAND-CPD:C06002:*CHEBI:27821:*PUBCHEM:46173457:*CAS:6236-08-4 1.2.1.27 (S)-methylmalonate-semialdehyde + coenzyme A + NAD+ + H2O = propanoyl-CoA + bicarbonate + NADH + H+ valine degradation I (S)-methylmalonate-semialdehyde (S)-ch3-malonate-semialdehyde*(S)-2-methyl-3-oxopropanoate*2-methyl-3-oxopropanoate*CH3-malonate-S-ald*ch3-malonate-semialdehyde 101.082 C4 H5 O3 C(C(C=O)C)(=O)[O-] LIGAND-CPD:C00349:*LIGAND-CPD:C06002:*CHEBI:27821:*PUBCHEM:46173457:*CAS:6236-08-4 1.1.1.31 (S)-3-hydroxy-isobutyrate + NAD+ = H+ + NADH + (S)-methylmalonate-semialdehyde valine degradation I (S)-methylmalonate-semialdehyde (S)-ch3-malonate-semialdehyde*(S)-2-methyl-3-oxopropanoate*2-methyl-3-oxopropanoate*CH3-malonate-S-ald*ch3-malonate-semialdehyde 101.082 C4 H5 O3 C(C(C=O)C)(=O)[O-] LIGAND-CPD:C00349:*LIGAND-CPD:C06002:*CHEBI:27821:*PUBCHEM:46173457:*CAS:6236-08-4 2.6.1.22 2-oxoglutarate + (S)-3-amino-2-methylpropanoate = L-glutamate + (S)-methylmalonate-semialdehyde valine degradation I 7,8-dihydro-D-neopterin 2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine*dihydroneopterin*2-amino-4-hydroxy-6-(D-erythro)-trihydroxypropyldihydropteridin*dihydro-neo-pterin*DHN*7,8-dihydroneopterin 255.233 C9 H13 N5 O4 NC2(=NC1(NCC(=NC=1C(=O)N2)C(O)C(O)CO)) PUBCHEM:65074:*CHEBI:17001:*LIGAND-CPD:C04874: 3.6.1.- 7,8-dihydroneopterin phosphate + H2O = 7,8-dihydro-D-neopterin 6-hydroxymethyl-dihydropterin diphosphate biosynthesis 7,8-dihydro-D-neopterin 2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine*dihydroneopterin*2-amino-4-hydroxy-6-(D-erythro)-trihydroxypropyldihydropteridin*dihydro-neo-pterin*DHN*7,8-dihydroneopterin 255.233 C9 H13 N5 O4 NC2(=NC1(NCC(=NC=1C(=O)N2)C(O)C(O)CO)) PUBCHEM:65074:*CHEBI:17001:*LIGAND-CPD:C04874: 4.1.2.25 7,8-dihydro-D-neopterin = glycolaldehyde + 6-hydroxymethyl-7,8-dihydropterin 6-hydroxymethyl-dihydropterin diphosphate biosynthesis D-myo-inositol (2,4) bisphosphate 1D-myo-inositol (2,4) bisphosphate*myo-inositol (2,4) bisphosphate*Ins(2,4)P2*I(2,4)P2 336.085 C6 H10 O12 P2 O=P([O-])([O-])OC1(C(O)C(O)C(O)C(OP(=O)([O-])[O-])C(O)1) PUBCHEM:25203091:*PUBCHEM:25245743: D-myo-inositol (2,4) bisphosphate + H2O = 1D-myo-inositol (2) monophosphate phytate degradation II D-myo-inositol (2,4) bisphosphate 1D-myo-inositol (2,4) bisphosphate*myo-inositol (2,4) bisphosphate*Ins(2,4)P2*I(2,4)P2 336.085 C6 H10 O12 P2 O=P([O-])([O-])OC1(C(O)C(O)C(O)C(OP(=O)([O-])[O-])C(O)1) PUBCHEM:25203091:*PUBCHEM:25245743: D-myo-inositol (2,3,4) trisphosphate + H2O = D-myo-inositol (2,4) bisphosphate phytate degradation II GA29 gibberellin A29*gibberellin A29*GA29 347.387 C19 H23 O6 C1(C(CC2(C4(C1(OC2=O)C5(CCC3(CC(CC3=C)(C4C([O-])=O)5)O)))(C))O) PUBCHEM:25200412:*LIGAND-CPD:C06096: 1.14.11.- gibberellin A20 + 2-oxoglutarate + oxygen = GA29 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) GA29 gibberellin A29*gibberellin A29*GA29 347.387 C19 H23 O6 C1(C(CC2(C4(C1(OC2=O)C5(CCC3(CC(CC3=C)(C4C([O-])=O)5)O)))(C))O) PUBCHEM:25200412:*LIGAND-CPD:C06096: 1.14.11.- GA29 + 2-oxoglutarate + oxygen = H+ + GA29-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) trans-zeatin riboside ZR*zeatin riboside 351.361 C15 H21 N5 O5 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(NCC=C(C)CO)2)))OC(CO)3) PUBCHEM:6440982:*LIGAND-CPD:C16431: 1.5.99.12 H+ + trans-zeatin riboside + H2O + FAD = adenosine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 2.4.1.99 sucrose + sucrose = 1-kestotriose + β-D-glucose fructan biosynthesis β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 2.4.1.25 maltotriose + maltose = maltotetraose + β-D-glucose glycogen degradation I β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 2.3.1.72 myo-inositol + indole-3-acetyl-β-1-D-glucose = indol-3-yl-acetyl-myo-inositol + β-D-glucose IAA conjugate biosynthesis I β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 3.2.1.3 H2O = β-D-glucose glycogen degradation III β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 2.4.1.10 sucrose + sucrose = 6-kestotriose + β-D-glucose fructan biosynthesis β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 3.2.1.21 cis-coumarinic acid-β-D-glucoside + H2O = coumarinate + β-D-glucose coumarin biosynthesis (via 2-coumarate) β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP GDP-glucose biosynthesis β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP glycolysis III β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP trehalose degradation II (trehalase) β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP glucose and glucose-1-phosphate degradation β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP glycogen degradation I β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 1.1.5.2 β-D-glucose = D-glucono-1,5-lactone glucose and glucose-1-phosphate degradation β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 3.2.1.28 trehalose + H2O = β-D-glucose trehalose degradation II (trehalase) β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 3.2.1.126 H2O + coniferin = coniferyl alcohol + β-D-glucose coniferin metabolism β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 3.2.1.33 H2O = β-D-glucose glycogen degradation II β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 2.4.1.10 1-kestotriose + sucrose = 1,6-kestotetraose + β-D-glucose fructan biosynthesis β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 3.2.1.22 H2O + melibiose = α-D-galactose + β-D-glucose melibiose degradation β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 3.2.1.23 H2O + lactose = β-D-galactose + β-D-glucose lactose degradation III β-D-glucose glucose*dextrose*glc*glc-ring*D-glucose-ring*D-glucose*glucoside*β-D-glucopyranose*β-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:64689:*LIGAND-CPD:C00221:*CHEBI:15903:*CAS:50-99-7:*PUBCHEM:64689:*CHEBI:15903:*LIGAND-CPD:C00221:*PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 3.2.1.21 DIMBOA-Glc + H2O = DIMBOA + β-D-glucose DIMBOA-glucoside degradation xanthosine-5-phosphate xanthosine-5-phosphate*(9-D-ribosylxanthine)-5'-phosphate*XMP*xanthosine-5'-phosphate*xanthosine-5-P*xanthosine-5'-P*9-(5-phospho-β-D-ribosyl)xanthine 362.192 C10 H11 N4 O9 P1 O=C2(C1(N=CN(C=1NC(=O)N2)C3(OC(COP(=O)([O-])[O-])C(O)C(O)3))) PUBCHEM:4670739:*CAS:523-98-8:*LIGAND-CPD:C00655: 3.1.3.5 xanthosine-5-phosphate + H2O = xanthosine adenosine nucleotides degradation I xanthosine-5-phosphate xanthosine-5-phosphate*(9-D-ribosylxanthine)-5'-phosphate*XMP*xanthosine-5'-phosphate*xanthosine-5-P*xanthosine-5'-P*9-(5-phospho-β-D-ribosyl)xanthine 362.192 C10 H11 N4 O9 P1 O=C2(C1(N=CN(C=1NC(=O)N2)C3(OC(COP(=O)([O-])[O-])C(O)C(O)3))) PUBCHEM:4670739:*CAS:523-98-8:*LIGAND-CPD:C00655: 1.1.1.205 inosine-5'-phosphate + H2O + NAD+ = xanthosine-5-phosphate + NADH + H+ adenosine nucleotides degradation I xanthosine-5-phosphate xanthosine-5-phosphate*(9-D-ribosylxanthine)-5'-phosphate*XMP*xanthosine-5'-phosphate*xanthosine-5-P*xanthosine-5'-P*9-(5-phospho-β-D-ribosyl)xanthine 362.192 C10 H11 N4 O9 P1 O=C2(C1(N=CN(C=1NC(=O)N2)C3(OC(COP(=O)([O-])[O-])C(O)C(O)3))) PUBCHEM:4670739:*CAS:523-98-8:*LIGAND-CPD:C00655: 1.1.1.205 inosine-5'-phosphate + H2O + NAD+ = xanthosine-5-phosphate + NADH + H+ purine nucleotides de novo biosynthesis II xanthosine-5-phosphate xanthosine-5-phosphate*(9-D-ribosylxanthine)-5'-phosphate*XMP*xanthosine-5'-phosphate*xanthosine-5-P*xanthosine-5'-P*9-(5-phospho-β-D-ribosyl)xanthine 362.192 C10 H11 N4 O9 P1 O=C2(C1(N=CN(C=1NC(=O)N2)C3(OC(COP(=O)([O-])[O-])C(O)C(O)3))) PUBCHEM:4670739:*CAS:523-98-8:*LIGAND-CPD:C00655: 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = H+ + L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis II 5-hydroxyisourate 184.111 C5 H4 N4 O4 C1(O)(NC2(C(NC(=O)N=C(N=1)2)=O)O) PUBCHEM:250388:*LIGAND-CPD:C11821:*CHEBI:18072: 3.5.2.17 5-hydroxyisourate + H2O = H+ + 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate urate degradation to allantoin 5-hydroxyisourate 184.111 C5 H4 N4 O4 C1(O)(NC2(C(NC(=O)N=C(N=1)2)=O)O) PUBCHEM:250388:*LIGAND-CPD:C11821:*CHEBI:18072: 1.7.3.3 urate + oxygen + H2O = 5-hydroxyisourate + hydrogen peroxide urate degradation to allantoin sphinganine 1-phosphate Dihydrosphingosine 1-phosphate*Sphinganine 1-phosphate*DHS-1-P 380.484 C18 H39 N1 O5 P1 C([N+])(COP([O-])([O-])=O)C(O)CCCCCCCCCCCCCCC PUBCHEM:25202187:*LIGAND-CPD:C01120: 2.7.1.91 sphinganine + ATP = H+ + sphinganine 1-phosphate + ADP sphingolipid biosynthesis (plants) (-)-jasmonate (-)-jasmonic acid*jasmonic acid*(3R,7R)-(-)-jasmonate 209.264 C12 H17 O3 C(CC)=CCC1(C(CC(=O)[O-])CCC(=O)1) PUBCHEM:25245750:*LIGAND-CPD:C08491: (+)-7-iso-jasmonate = (-)-jasmonate jasmonic acid biosynthesis eriodictyol 287.248 C15 H11 O6 C1(C(=CC(=C2(C=1OC(CC2=O)C3(C=C(C(=CC=3)O)O)))O)[O-]) PUBCHEM:25200419:*LIGAND-CPD:C05631: 1.14.13.21 H+ + naringenin + NADPH + oxygen = eriodictyol + NADP+ + H2O luteolin biosynthesis eriodictyol 287.248 C15 H11 O6 C1(C(=CC(=C2(C=1OC(CC2=O)C3(C=C(C(=CC=3)O)O)))O)[O-]) PUBCHEM:25200419:*LIGAND-CPD:C05631: 1.14.11.22 eriodictyol + 2-oxoglutarate + oxygen = luteolin + succinate + CO2 + H2O luteolin biosynthesis eriodictyol 287.248 C15 H11 O6 C1(C(=CC(=C2(C=1OC(CC2=O)C3(C=C(C(=CC=3)O)O)))O)[O-]) PUBCHEM:25200419:*LIGAND-CPD:C05631: 1.14.13.88 H+ + eriodictyol + NADPH + oxygen = 3',4',5'-pentahydroxyflavanone + NADP+ + H2O leucodelphinidin biosynthesis eriodictyol 287.248 C15 H11 O6 C1(C(=CC(=C2(C=1OC(CC2=O)C3(C=C(C(=CC=3)O)O)))O)[O-]) PUBCHEM:25200419:*LIGAND-CPD:C05631: H+ + eriodictyol + NADPH + oxygen = luteolin + NADP+ + H2O luteolin biosynthesis eriodictyol 287.248 C15 H11 O6 C1(C(=CC(=C2(C=1OC(CC2=O)C3(C=C(C(=CC=3)O)O)))O)[O-]) PUBCHEM:25200419:*LIGAND-CPD:C05631: 1.14.11.9 eriodictyol + oxygen + 2-oxoglutarate = trans dihydroquercetin + CO2 + succinate leucopelargonidin and leucocyanidin biosynthesis eriodictyol 287.248 C15 H11 O6 C1(C(=CC(=C2(C=1OC(CC2=O)C3(C=C(C(=CC=3)O)O)))O)[O-]) PUBCHEM:25200419:*LIGAND-CPD:C05631: 1.14.11.9 eriodictyol + oxygen + 2-oxoglutarate = trans dihydroquercetin + CO2 + succinate leucodelphinidin biosynthesis (22S,24R)-22-hydroxy-5α-ergostan-3-one (22α)-hydroxy-5α-campestan-3-one*(22S)-22-hydroxy-5α-campestan-3-one*(22S,24R)-22-hydroxy-5α-ergostan-3-one 416.686 C28 H48 O2 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))=O) PUBCHEM:25202189:*LIGAND-CPD:C15797: H+ + (22S,24R)-22-hydroxy-5α-ergostan-3-one = 6-deoxocathasterone brassinosteroid biosynthesis II (22S,24R)-22-hydroxy-5α-ergostan-3-one (22α)-hydroxy-5α-campestan-3-one*(22S)-22-hydroxy-5α-campestan-3-one*(22S,24R)-22-hydroxy-5α-ergostan-3-one 416.686 C28 H48 O2 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))=O) PUBCHEM:25202189:*LIGAND-CPD:C15797: 1.14.13.112 (22S,24R)-22-hydroxy-5α-ergostan-3-one + oxygen + NADPH + H+ = 3-dehydro-6-deoxoteasterone + NADP+ + H2O brassinosteroid biosynthesis II (22S,24R)-22-hydroxy-5α-ergostan-3-one (22α)-hydroxy-5α-campestan-3-one*(22S)-22-hydroxy-5α-campestan-3-one*(22S,24R)-22-hydroxy-5α-ergostan-3-one 416.686 C28 H48 O2 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))=O) PUBCHEM:25202189:*LIGAND-CPD:C15797: 1.3.99.- H+ + (22α)-hydroxy-campest-4-en-3-one + NADPH = (22S,24R)-22-hydroxy-5α-ergostan-3-one + NADP+ brassinosteroid biosynthesis II (22S,24R)-22-hydroxy-5α-ergostan-3-one (22α)-hydroxy-5α-campestan-3-one*(22S)-22-hydroxy-5α-campestan-3-one*(22S,24R)-22-hydroxy-5α-ergostan-3-one 416.686 C28 H48 O2 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))=O) PUBCHEM:25202189:*LIGAND-CPD:C15797: H+ + (22S,24R)-22-hydroxy-5α-ergostan-3-one = 3-epi-6-deoxocathasterone brassinosteroid biosynthesis II (22S,24R)-22-hydroxy-5α-ergostan-3-one (22α)-hydroxy-5α-campestan-3-one*(22S)-22-hydroxy-5α-campestan-3-one*(22S,24R)-22-hydroxy-5α-ergostan-3-one 416.686 C28 H48 O2 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))=O) PUBCHEM:25202189:*LIGAND-CPD:C15797: 1.14.13.- H+ + (5α)-campestan-3-one + oxygen + NADPH = (22S,24R)-22-hydroxy-5α-ergostan-3-one + H2O + NADP+ brassinosteroid biosynthesis II epiafzelechin 2,3-cis-epiafzelechin 274.273 C15 H14 O5 C1(C=CC(O)=CC=1)(C2(C(O)CC3(C(O2)=CC(O)=CC(O)=3))) PUBCHEM:443639:*LIGAND-CPD:C12128: 1.3.1.77 H+ + pelargonidin = epiafzelechin 2,3-cis-flavanols biosynthesis meso-diaminopimelate meso-2,6-diaminopimelate*meso-A2pm*meso-diaminoheptanedioate*meso-2,6-diaminoheptanedioate*meso-1-α,ε-diaminopimelate*D,L-diaminopimelate*D,L-DAP*D,L-meso-diaminoheptanedioate*M-DAP 190.199 C7 H14 N2 O4 C(C(C([O-])=O)[N+])CCC(C([O-])=O)[N+] CHEBI:57791:*PUBCHEM:1549101:*LIGAND-CPD:C00680:*CAS:922-54-3 4.1.1.20 H+ + meso-diaminopimelate = CO2 + L-lysine lysine biosynthesis VI meso-diaminopimelate meso-2,6-diaminopimelate*meso-A2pm*meso-diaminoheptanedioate*meso-2,6-diaminoheptanedioate*meso-1-α,ε-diaminopimelate*D,L-diaminopimelate*D,L-DAP*D,L-meso-diaminoheptanedioate*M-DAP 190.199 C7 H14 N2 O4 C(C(C([O-])=O)[N+])CCC(C([O-])=O)[N+] CHEBI:57791:*PUBCHEM:1549101:*LIGAND-CPD:C00680:*CAS:922-54-3 5.1.1.7 L,L-diaminopimelate = meso-diaminopimelate lysine biosynthesis VI 4-coumaroylshikimate trans-5-O-(4-Coumaroyl)shikimate*trans-(p-coumaroyl)-shikimate 319.29 C16 H15 O7 O=C([O-])C1(=CC(O)C(O)C(C1)OC(=O)C=CC2(=CC=C(O)C=C2)) CHEBI:57768:*PUBCHEM:25245116:*LIGAND-CPD:C02947: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O chlorogenic acid biosynthesis I 4-coumaroylshikimate trans-5-O-(4-Coumaroyl)shikimate*trans-(p-coumaroyl)-shikimate 319.29 C16 H15 O7 O=C([O-])C1(=CC(O)C(O)C(C1)OC(=O)C=CC2(=CC=C(O)C=C2)) CHEBI:57768:*PUBCHEM:25245116:*LIGAND-CPD:C02947: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O chlorogenic acid biosynthesis II 4-coumaroylshikimate trans-5-O-(4-Coumaroyl)shikimate*trans-(p-coumaroyl)-shikimate 319.29 C16 H15 O7 O=C([O-])C1(=CC(O)C(O)C(C1)OC(=O)C=CC2(=CC=C(O)C=C2)) CHEBI:57768:*PUBCHEM:25245116:*LIGAND-CPD:C02947: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O simplecoumarins biosynthesis 4-coumaroylshikimate trans-5-O-(4-Coumaroyl)shikimate*trans-(p-coumaroyl)-shikimate 319.29 C16 H15 O7 O=C([O-])C1(=CC(O)C(O)C(C1)OC(=O)C=CC2(=CC=C(O)C=C2)) CHEBI:57768:*PUBCHEM:25245116:*LIGAND-CPD:C02947: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O phenylpropanoid biosynthesis 4-coumaroylshikimate trans-5-O-(4-Coumaroyl)shikimate*trans-(p-coumaroyl)-shikimate 319.29 C16 H15 O7 O=C([O-])C1(=CC(O)C(O)C(C1)OC(=O)C=CC2(=CC=C(O)C=C2)) CHEBI:57768:*PUBCHEM:25245116:*LIGAND-CPD:C02947: 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A chlorogenic acid biosynthesis I 4-coumaroylshikimate trans-5-O-(4-Coumaroyl)shikimate*trans-(p-coumaroyl)-shikimate 319.29 C16 H15 O7 O=C([O-])C1(=CC(O)C(O)C(C1)OC(=O)C=CC2(=CC=C(O)C=C2)) CHEBI:57768:*PUBCHEM:25245116:*LIGAND-CPD:C02947: 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A chlorogenic acid biosynthesis II 4-coumaroylshikimate trans-5-O-(4-Coumaroyl)shikimate*trans-(p-coumaroyl)-shikimate 319.29 C16 H15 O7 O=C([O-])C1(=CC(O)C(O)C(C1)OC(=O)C=CC2(=CC=C(O)C=C2)) CHEBI:57768:*PUBCHEM:25245116:*LIGAND-CPD:C02947: 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A simplecoumarins biosynthesis 4-coumaroylshikimate trans-5-O-(4-Coumaroyl)shikimate*trans-(p-coumaroyl)-shikimate 319.29 C16 H15 O7 O=C([O-])C1(=CC(O)C(O)C(C1)OC(=O)C=CC2(=CC=C(O)C=C2)) CHEBI:57768:*PUBCHEM:25245116:*LIGAND-CPD:C02947: 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A phenylpropanoid biosynthesis delphinidin 3-O-glucosyl-5-O-caffeoylglucoside 788.668 C36 H36 O20 C6(C3(=C(C=C(OC1(OC(CO)C(O)C(O)C(O)1))C(C2(C=C(O)C(O)=C(O)C=2))=[O+]3)C(OC5(C(O)C(O)C(O)C(COC(=O)C=CC4(C=CC(O)=C(O)C=4))O5))=CC([O-])=6)) PUBCHEM:25244498:*LIGAND-CPD:C16313: 2.3.1.153 delphinidin-3,5-diglucoside + caffeoyl-CoA = delphinidin 3-O-glucosyl-5-O-caffeoylglucoside + coenzyme A gentiodelphin biosynthesis delphinidin 3-O-glucosyl-5-O-caffeoylglucoside 788.668 C36 H36 O20 C6(C3(=C(C=C(OC1(OC(CO)C(O)C(O)C(O)1))C(C2(C=C(O)C(O)=C(O)C=2))=[O+]3)C(OC5(C(O)C(O)C(O)C(COC(=O)C=CC4(C=CC(O)=C(O)C=4))O5))=CC([O-])=6)) PUBCHEM:25244498:*LIGAND-CPD:C16313: 2.4.1.- delphinidin 3-O-glucosyl-5-O-caffeoylglucoside = H+ + delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + UDP gentiodelphin biosynthesis 3''-deamino-3''-oxonicotianamine 301.275 C12 H17 N2 O7 [N+]1(CCC(C([O-])=O)[N+]CCC(C([O-])=O)=O)(C(CC1)C([O-])=O) CHEBI:58685:*PUBCHEM:25201327:*LIGAND-CPD:C15486: 1.1.1.285 2'-deoxymugineic acid = 3''-deamino-3''-oxonicotianamine + H+ 2'-deoxymugineic acid phytosiderophore biosynthesis 3''-deamino-3''-oxonicotianamine 301.275 C12 H17 N2 O7 [N+]1(CCC(C([O-])=O)[N+]CCC(C([O-])=O)=O)(C(CC1)C([O-])=O) CHEBI:58685:*PUBCHEM:25201327:*LIGAND-CPD:C15486: 2.6.1.80 nicotianamine + 2-oxoglutarate = L-glutamate + 3''-deamino-3''-oxonicotianamine 2'-deoxymugineic acid phytosiderophore biosynthesis dimethylallyl diphosphate dimethylallyl-diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 243.069 C5 H9 O7 P2 CC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:57623:*PUBCHEM:15983958:*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.- H+ + dimethylallyl diphosphate + ATP = N6-(Δ2-isopentenyl)-adenosine 5'-triphosphate + diphosphate trans-zeatin biosynthesis dimethylallyl diphosphate dimethylallyl-diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 243.069 C5 H9 O7 P2 CC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:57623:*PUBCHEM:15983958:*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.1 dimethylallyl diphosphate + isopentenyl diphosphate = geranyl diphosphate + diphosphate geranyl diphosphate biosynthesis dimethylallyl diphosphate dimethylallyl-diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 243.069 C5 H9 O7 P2 CC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:57623:*PUBCHEM:15983958:*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.1 dimethylallyl diphosphate + isopentenyl diphosphate = geranyl diphosphate + diphosphate trans, trans-farnesyl diphosphate biosynthesis dimethylallyl diphosphate dimethylallyl-diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 243.069 C5 H9 O7 P2 CC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:57623:*PUBCHEM:15983958:*LIGAND-CPD:C00235:*CAS:358-71-4: 1.17.1.2 dimethylallyl diphosphate + H2O = 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H+ methylerythritol phosphate pathway dimethylallyl diphosphate dimethylallyl-diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 243.069 C5 H9 O7 P2 CC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:57623:*PUBCHEM:15983958:*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.- dimethylallyl diphosphate + ADP = N6-(Δ2-isopentenyl)-adenosine 5'-diphosphate + diphosphate trans-zeatin biosynthesis dimethylallyl diphosphate dimethylallyl-diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 243.069 C5 H9 O7 P2 CC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:57623:*PUBCHEM:15983958:*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.75 dimethylallyl diphosphate = diphosphate cis-zeatin biosynthesis dimethylallyl diphosphate dimethylallyl-diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 243.069 C5 H9 O7 P2 CC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:57623:*PUBCHEM:15983958:*LIGAND-CPD:C00235:*CAS:358-71-4: 5.3.3.2 isopentenyl diphosphate = dimethylallyl diphosphate mevalonate pathway I dimethylallyl diphosphate dimethylallyl-diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 243.069 C5 H9 O7 P2 CC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:57623:*PUBCHEM:15983958:*LIGAND-CPD:C00235:*CAS:358-71-4: 5.3.3.2 isopentenyl diphosphate = dimethylallyl diphosphate trans, trans-farnesyl diphosphate biosynthesis dimethylallyl diphosphate dimethylallyl-diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 243.069 C5 H9 O7 P2 CC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:57623:*PUBCHEM:15983958:*LIGAND-CPD:C00235:*CAS:358-71-4: 5.3.3.2 isopentenyl diphosphate = dimethylallyl diphosphate methylerythritol phosphate pathway dimethylallyl diphosphate dimethylallyl-diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 243.069 C5 H9 O7 P2 CC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:57623:*PUBCHEM:15983958:*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.27 dimethylallyl diphosphate + AMP = N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate + diphosphate trans-zeatin biosynthesis 24-methylenecycloartanol 24(28)-methylenecycloartanol*24(28)-methylenecycloartenol 440.751 C31 H52 O1 C1(CC(C(C2(C51(C3(C(CC2)C4(C)(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4))C5)))(C)C)O) PUBCHEM:25245118:*LIGAND-CPD:C08830: 1.14.13.- 24-methylenecycloartanol + NADH + oxygen = 4α-hydroxymethyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis 24-methylenecycloartanol 24(28)-methylenecycloartanol*24(28)-methylenecycloartenol 440.751 C31 H52 O1 C1(CC(C(C2(C51(C3(C(CC2)C4(C)(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4))C5)))(C)C)O) PUBCHEM:25245118:*LIGAND-CPD:C08830: 2.1.1.41 S-adenosyl-L-methionine + cycloartenol = H+ + S-adenosyl-L-homocysteine + 24-methylenecycloartanol plant sterol biosynthesis β-alanine β-alanine*3-aminopropanoate 89.094 C3 H7 N1 O2 C([O-])(CC[N+])=O PUBCHEM:4755801:*KNAPSACK:C00001333:*PUBCHEM:4755801:*LIGAND-CPD:C00099:*CAS:107-95-9 3.5.1.6 3-ureidopropionate + H2O + H+ = β-alanine + ammonia + CO2 uracil degradation II (reductive) β-alanine β-alanine*3-aminopropanoate 89.094 C3 H7 N1 O2 C([O-])(CC[N+])=O PUBCHEM:4755801:*KNAPSACK:C00001333:*PUBCHEM:4755801:*LIGAND-CPD:C00099:*CAS:107-95-9 1.2.1.3 3-aminopropanal + H2O = β-alanine β-alanine biosynthesis I β-alanine β-alanine*3-aminopropanoate 89.094 C3 H7 N1 O2 C([O-])(CC[N+])=O PUBCHEM:4755801:*KNAPSACK:C00001333:*PUBCHEM:4755801:*LIGAND-CPD:C00099:*CAS:107-95-9 6.3.2.1 β-alanine + (R)-pantoate + ATP = H+ + (R)-pantothenate + diphosphate + AMP phosphopantothenate biosynthesis I β-alanine β-alanine*3-aminopropanoate 89.094 C3 H7 N1 O2 C([O-])(CC[N+])=O PUBCHEM:4755801:*KNAPSACK:C00001333:*PUBCHEM:4755801:*LIGAND-CPD:C00099:*CAS:107-95-9 6.3.2.1 β-alanine + (R)-pantoate + ATP = H+ + (R)-pantothenate + diphosphate + AMP pantothenate biosynthesis I β-alanine β-alanine*3-aminopropanoate 89.094 C3 H7 N1 O2 C([O-])(CC[N+])=O PUBCHEM:4755801:*KNAPSACK:C00001333:*PUBCHEM:4755801:*LIGAND-CPD:C00099:*CAS:107-95-9 2.6.1.18 malonate semialdehyde + L-alanine = β-alanine + pyruvate β-alanine biosynthesis II L-quinate (-)-quinate*(-)-quinic acid*L-quinate*quinic acid 191.16 C7 H11 O6 C1(C([O-])=O)(O)(CC(O)C(O)C(O)C1) PUBCHEM:1560034:*CHEBI:29751:*LIGAND-CPD:C00296:*CAS:77-95-2 3.1.2.- trans-5-O-caffeoyl-D-quinate + coenzyme A = caffeoyl-CoA + L-quinate chlorogenic acid biosynthesis I L-quinate (-)-quinate*(-)-quinic acid*L-quinate*quinic acid 191.16 C7 H11 O6 C1(C([O-])=O)(O)(CC(O)C(O)C(O)C1) PUBCHEM:1560034:*CHEBI:29751:*LIGAND-CPD:C00296:*CAS:77-95-2 3.1.2.- trans-5-O-caffeoyl-D-quinate + coenzyme A = caffeoyl-CoA + L-quinate phenylpropanoid biosynthesis L-quinate (-)-quinate*(-)-quinic acid*L-quinate*quinic acid 191.16 C7 H11 O6 C1(C([O-])=O)(O)(CC(O)C(O)C(O)C1) PUBCHEM:1560034:*CHEBI:29751:*LIGAND-CPD:C00296:*CAS:77-95-2 2.3.1.133 4-coumaroyl-CoA + L-quinate = trans-5-O-(4-coumaroyl)-D-quinate + coenzyme A chlorogenic acid biosynthesis I L-quinate (-)-quinate*(-)-quinic acid*L-quinate*quinic acid 191.16 C7 H11 O6 C1(C([O-])=O)(O)(CC(O)C(O)C(O)C1) PUBCHEM:1560034:*CHEBI:29751:*LIGAND-CPD:C00296:*CAS:77-95-2 2.3.1.133 4-coumaroyl-CoA + L-quinate = trans-5-O-(4-coumaroyl)-D-quinate + coenzyme A chlorogenic acid biosynthesis II L-quinate (-)-quinate*(-)-quinic acid*L-quinate*quinic acid 191.16 C7 H11 O6 C1(C([O-])=O)(O)(CC(O)C(O)C(O)C1) PUBCHEM:1560034:*CHEBI:29751:*LIGAND-CPD:C00296:*CAS:77-95-2 2.3.1.133 4-coumaroyl-CoA + L-quinate = trans-5-O-(4-coumaroyl)-D-quinate + coenzyme A phenylpropanoid biosynthesis 6-methoxy-5-methyl-2-all-trans-nonaprenyl-1,4-benzoquinol 2-nonaprenyl-3-methyl-6-methoxy-1,4-benzoquinol*6-methoxy-5-methyl-2-nonaprenyl-1,4-benzoquinol 767.229 C53 H82 O3 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(=C(C(OC)=CC(=C1C)O)O))C)C)C)C)C)C)C)CCC=C(C)C PUBCHEM:25244499: 2.1.1.- 2-methoxy-6-all trans-nonaprenyl-2-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine = H+ + 6-methoxy-5-methyl-2-all-trans-nonaprenyl-1,4-benzoquinol + S-adenosyl-L-homocysteine ubiquinol-9 biosynthesis (eukaryotic) 6-methoxy-5-methyl-2-all-trans-nonaprenyl-1,4-benzoquinol 2-nonaprenyl-3-methyl-6-methoxy-1,4-benzoquinol*6-methoxy-5-methyl-2-nonaprenyl-1,4-benzoquinol 767.229 C53 H82 O3 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(=C(C(OC)=CC(=C1C)O)O))C)C)C)C)C)C)C)CCC=C(C)C PUBCHEM:25244499: 1.14.-.- 6-methoxy-5-methyl-2-all-trans-nonaprenyl-1,4-benzoquinol + oxygen = 3-demethylubiquinol-9 + H2O ubiquinol-9 biosynthesis (eukaryotic) 5,6-dihydrouracil dihydrouracil*5,6-dihydrouracil*DI-H-uracil*4,5-dihydrouracil 114.104 C4 H6 N2 O2 N1(C(CCNC1=O)=O) PUBCHEM:649:*LIGAND-CPD:C00429:*CHEBI:15901:*CAS:504-07-4 1.3.1.2 5,6-dihydrouracil + NADP+ = uracil + NADPH + H+ uracil degradation II (reductive) 5,6-dihydrouracil dihydrouracil*5,6-dihydrouracil*DI-H-uracil*4,5-dihydrouracil 114.104 C4 H6 N2 O2 N1(C(CCNC1=O)=O) PUBCHEM:649:*LIGAND-CPD:C00429:*CHEBI:15901:*CAS:504-07-4 3.5.2.2 H2O + 5,6-dihydrouracil = H+ + 3-ureidopropionate uracil degradation II (reductive) 18-hydroxyoleate 18-hydroxyoctadec-9-enoic acid*18-hydroxy-9Z-octadecenoate*ω-hydroxy-9Z-octadecenoate*omega-hydroxy oleate 297.457 C18 H33 O3 C(O)CCCCCCCC=CCCCCCCCC([O-])=O PUBCHEM:25245753: 1.1.1.- 18-hydroxyoleate + NADP+ = H+ + 18-oxo-oleate + NADPH suberin biosynthesis 18-hydroxyoleate 18-hydroxyoctadec-9-enoic acid*18-hydroxy-9Z-octadecenoate*ω-hydroxy-9Z-octadecenoate*omega-hydroxy oleate 297.457 C18 H33 O3 C(O)CCCCCCCC=CCCCCCCCC([O-])=O PUBCHEM:25245753: 1.14.13.- oleate + NADPH + oxygen = 18-hydroxyoleate + NADP+ + H2O suberin biosynthesis 4-guanidinobutyrate 4-guanido-butyrate*γ-guanidinobutyrate*4-guanidinobutanoate 145.161 C5 H11 N3 O2 N(C(=[N+])N)CCCC([O-])=O CHEBI:57486:*PUBCHEM:25200642:*LIGAND-CPD:C01035: 3.5.1.4 4-guanidinobutyramide + H2O = H+ + ammonia + 4-guanidinobutyrate arginine degradation X (arginine monooxygenase pathway) 4-guanidinobutyrate 4-guanido-butyrate*γ-guanidinobutyrate*4-guanidinobutanoate 145.161 C5 H11 N3 O2 N(C(=[N+])N)CCCC([O-])=O CHEBI:57486:*PUBCHEM:25200642:*LIGAND-CPD:C01035: 3.5.3.7 H2O + 4-guanidinobutyrate = urea + 4-aminobutyrate arginine degradation X (arginine monooxygenase pathway) dihydrozeatin-O-glucoside 383.403 C16 H25 N5 O6 C1(C2(=C(N=CN=1)NC=N2))NCCC(COC3(C(C(C(C(O3)CO)O)O)O))C PUBCHEM:25200430:*LIGAND-CPD:C16448: 2.4.1.- dihydrozeatin = H+ + dihydrozeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis dUMP U*deoxyurdine-phosphate*2'-deoxyuridine-5-monophosphate*deoxyuridine-phosphate*2'-deoxyuridine-5'-phosphate*2'-deoxyuridylic acid*2'-deoxy-5'-uridylic acid 306.168 C9 H11 N2 O8 P1 O=C1(C=CN(C(=O)N1)C2(CC(O)C(COP(=O)([O-])[O-])O2)) CHEBI:246422:*PUBCHEM:18601100:*LIGAND-CPD:C00365:*CAS:964-26-1 2.1.1.45 5,10-methylenetetrahydropteroyl mono-L-glutamate + dUMP = dTMP + 7,8-dihydrofolate monoglutamate pyrimidine deoxyribonucleotides de novo biosynthesis I dUMP U*deoxyurdine-phosphate*2'-deoxyuridine-5-monophosphate*deoxyuridine-phosphate*2'-deoxyuridine-5'-phosphate*2'-deoxyuridylic acid*2'-deoxy-5'-uridylic acid 306.168 C9 H11 N2 O8 P1 O=C1(C=CN(C(=O)N1)C2(CC(O)C(COP(=O)([O-])[O-])O2)) CHEBI:246422:*PUBCHEM:18601100:*LIGAND-CPD:C00365:*CAS:964-26-1 2.1.1.45 5,10-methylenetetrahydropteroyl mono-L-glutamate + dUMP = dTMP + 7,8-dihydrofolate monoglutamate folate transformations II (plants) dUMP U*deoxyurdine-phosphate*2'-deoxyuridine-5-monophosphate*deoxyuridine-phosphate*2'-deoxyuridine-5'-phosphate*2'-deoxyuridylic acid*2'-deoxy-5'-uridylic acid 306.168 C9 H11 N2 O8 P1 O=C1(C=CN(C(=O)N1)C2(CC(O)C(COP(=O)([O-])[O-])O2)) CHEBI:246422:*PUBCHEM:18601100:*LIGAND-CPD:C00365:*CAS:964-26-1 3.6.1.23 dUTP + H2O = H+ + dUMP + diphosphate pyrimidine deoxyribonucleotides de novo biosynthesis I 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole (S)-2-[5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate*(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate*1-(5-phosphoribosyl)-4-(N-succino-carboxamide)-5-aminoimidazole*5'-P-ribosyl-4-(N-succinocarboxamide)-5-aminoimidazole*5'-p-Ribosyl-4-(N-succinocarboxamide)-5-amino imidazole*1-(5'-phosphoribosyl)-4-(N-succino-carboxamide)-5-aminoimidazole*SAICAR 450.255 C13 H15 N4 O12 P1 O2(C(N1(C(N)=C(C(=O)NC(C([O-])=O)CC([O-])=O)N=C1))C(O)C(O)C(COP([O-])([O-])=O)2) PUBCHEM:25244502:*LIGAND-CPD:C04823: 4.3.2.2 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole = fumarate + aminoimidazole carboxamide ribonucleotide inosine-5'-phosphate biosynthesis II 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole (S)-2-[5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate*(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate*1-(5-phosphoribosyl)-4-(N-succino-carboxamide)-5-aminoimidazole*5'-P-ribosyl-4-(N-succinocarboxamide)-5-aminoimidazole*5'-p-Ribosyl-4-(N-succinocarboxamide)-5-amino imidazole*1-(5'-phosphoribosyl)-4-(N-succino-carboxamide)-5-aminoimidazole*SAICAR 450.255 C13 H15 N4 O12 P1 O2(C(N1(C(N)=C(C(=O)NC(C([O-])=O)CC([O-])=O)N=C1))C(O)C(O)C(COP([O-])([O-])=O)2) PUBCHEM:25244502:*LIGAND-CPD:C04823: 6.3.2.6 ATP + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-aspartate = H+ + ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole inosine-5'-phosphate biosynthesis II indole-3-acetyl-alanine IAA-Ala*indole-3-acetyl-ala*indole-3-acetyl-alanine 245.257 C13 H13 N2 O3 C(C(NC(C([O-])=O)C)=O)C2(C1(C=CC=CC=1NC=2)) PUBCHEM:25245124: 3.5.1.- indole-3-acetyl-alanine + H2O = indole-3-acetate + L-alanine IAA biosynthesis II L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 2.6.1.1 L-aspartate + 2-oxoglutarate = L-glutamate + oxaloacetate aspartate biosynthesis L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 2.6.1.1 L-aspartate + 2-oxoglutarate = L-glutamate + oxaloacetate aspartate degradation II L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 6.3.2.6 ATP + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-aspartate = H+ + ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole inosine-5'-phosphate biosynthesis II L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 3.5.1.1 L-asparagine + H2O = L-aspartate + ammonia + H+ asparagine degradation I L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 2.1.3.2 L-aspartate + carbamoyl-phosphate = H+ + N-carbamoyl-L-aspartate uridine-5'-phosphate biosynthesis L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 6.1.1.12 H+ + L-aspartate + ATP = diphosphate + AMP tRNA charging pathway L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 2.7.2.4 L-aspartate + ATP = L-aspartyl-4-phosphate + ADP lysine biosynthesis VI L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 2.7.2.4 L-aspartate + ATP = L-aspartyl-4-phosphate + ADP homoserine biosynthesis L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP urea cycle L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP arginine biosynthesis II (acetyl cycle) L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP citrulline-nitric oxide cycle L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP arginine biosynthesis I L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 1.4.3.16 L-aspartate + oxygen = H+ + α-iminosuccinate + hydrogen peroxide NAD biosynthesis I (from aspartate) L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 3.5.5.4 H2O + 3-cyano-L-alanine = ammonia + L-aspartate cyanide detoxification L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = H+ + adenylo-succinate + GDP purine nucleotides de novo biosynthesis II L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = H+ + adenylo-succinate + GDP adenosine nucleotides de novo biosynthesis L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 6.3.1.1 ammonia + L-aspartate + ATP = L-asparagine + diphosphate + AMP asparagine biosynthesis II L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 132.096 C4 H6 N1 O4 O=C(C(CC([O-])=O)[N+])[O-] PUBCHEM:5460542:*KNAPSACK:C00001342:*CHEBI:35391:*PUBCHEM:5460542:*LIGAND-CPD:C00049:*CAS:56-84-8 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = H+ + L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis I 5-amino-6-(5-phospho-D-ribitylamino)uracil 5-amino-6-(5'-phosphoribitylamino)uracil*5-amino-6-(5-phosphoribitylamino)uracil*5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione 5'-phosphate 354.213 C9 H15 N4 O9 P1 N(CC(O)C(O)C(O)COP(=O)([O-])[O-])C1(NC(=O)NC(=O)C(N)=1) PUBCHEM:25245125:*LIGAND-CPD:C04454: 1.1.1.193 5-amino-6-(5-phospho-D-ribitylamino)uracil + NADP+ = 5-amino-6-(5-phospho-D-ribosylamino)uracil + NADPH + H+ flavin biosynthesis I (bacteria and plants) 5-amino-6-(5-phospho-D-ribitylamino)uracil 5-amino-6-(5'-phosphoribitylamino)uracil*5-amino-6-(5-phosphoribitylamino)uracil*5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione 5'-phosphate 354.213 C9 H15 N4 O9 P1 N(CC(O)C(O)C(O)COP(=O)([O-])[O-])C1(NC(=O)NC(=O)C(N)=1) PUBCHEM:25245125:*LIGAND-CPD:C04454: 5-amino-6-(5-phospho-D-ribitylamino)uracil + H2O = 5-amino-6-(D-ribitylamino)uracil flavin biosynthesis I (bacteria and plants) D-myo-inositol (3,4,5,6)-tetrakisphosphate Ins(3,4,5,6)P4*Inositol 3,4,5,6-tetrakisphosphate*1D-myo-inositol 3,4,5,6-tetrakisphosphate*I(3,4,5,6)P4 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) CHEBI:57539:*PUBCHEM:25201333:*LIGAND-CPD:C04520: 2.7.1.134 D-myo-inositol (3,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis D-myo-inositol (3,4,5,6)-tetrakisphosphate Ins(3,4,5,6)P4*Inositol 3,4,5,6-tetrakisphosphate*1D-myo-inositol 3,4,5,6-tetrakisphosphate*I(3,4,5,6)P4 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) CHEBI:57539:*PUBCHEM:25201333:*LIGAND-CPD:C04520: 2.7.1.134 D-myo-inositol (3,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) D-myo-inositol (3,4,5,6)-tetrakisphosphate Ins(3,4,5,6)P4*Inositol 3,4,5,6-tetrakisphosphate*1D-myo-inositol 3,4,5,6-tetrakisphosphate*I(3,4,5,6)P4 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) CHEBI:57539:*PUBCHEM:25201333:*LIGAND-CPD:C04520: 3.1.3.- D-myo-inositol (1,3,4,5,6)-pentakisphosphate + H2O = D-myo-inositol (3,4,5,6)-tetrakisphosphate D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis D-myo-inositol (3,4,5,6)-tetrakisphosphate Ins(3,4,5,6)P4*Inositol 3,4,5,6-tetrakisphosphate*1D-myo-inositol 3,4,5,6-tetrakisphosphate*I(3,4,5,6)P4 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) CHEBI:57539:*PUBCHEM:25201333:*LIGAND-CPD:C04520: D-myo-inositol (3,4,6)-trisphosphate + ATP = H+ + D-myo-inositol (3,4,5,6)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) 24-epi-campesterol ergost-5-en-3β-ol*(24S)-methylcholest-5-en-3β-ol*Δ22-dihydrobrassicasterol*Δ5-campesterol*24-methyl-5-cholestene-3β-ol*(3β)-ergost-5-en-3-ol 400.687 C28 H48 O1 CC(C(CCC(C3(C2(C)(CCC4(C1(C)(CCC(O)CC1=CCC(C2CC3)4)))))C)C)C PUBCHEM:173183: 1.3.-.- H+ + 24-methyldesmosterol = 24-epi-campesterol plant sterol biosynthesis 24-epi-campesterol ergost-5-en-3β-ol*(24S)-methylcholest-5-en-3β-ol*Δ22-dihydrobrassicasterol*Δ5-campesterol*24-methyl-5-cholestene-3β-ol*(3β)-ergost-5-en-3-ol 400.687 C28 H48 O1 CC(C(CCC(C3(C2(C)(CCC4(C1(C)(CCC(O)CC1=CCC(C2CC3)4)))))C)C)C PUBCHEM:173183: 1.3.1.- 24-epi-campesterol + NADPH + H+ + oxygen = brassicasterol + NADP+ + H2O plant sterol biosynthesis D-myo-inositol (1,3,4,6)-tetrakisphosphate Ins(1,3,4,6)P4*inositol (1,3,4,6)-tetrakisphosphate*1D-myo -inositol 1,3,4,6-tetrakisphosphate 492.013 C6 H8 O18 P4 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) CHEBI:57660:*PUBCHEM:25201336:*LIGAND-CPD:C04477: 2.7.1.- D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + 1D-myo-inositol (1,2,3,4,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) D-myo-inositol (1,3,4,6)-tetrakisphosphate Ins(1,3,4,6)P4*inositol (1,3,4,6)-tetrakisphosphate*1D-myo -inositol 1,3,4,6-tetrakisphosphate 492.013 C6 H8 O18 P4 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) CHEBI:57660:*PUBCHEM:25201336:*LIGAND-CPD:C04477: 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) D-myo-inositol (1,3,4,6)-tetrakisphosphate Ins(1,3,4,6)P4*inositol (1,3,4,6)-tetrakisphosphate*1D-myo -inositol 1,3,4,6-tetrakisphosphate 492.013 C6 H8 O18 P4 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) CHEBI:57660:*PUBCHEM:25201336:*LIGAND-CPD:C04477: 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis D-myo-inositol (1,3,4,6)-tetrakisphosphate Ins(1,3,4,6)P4*inositol (1,3,4,6)-tetrakisphosphate*1D-myo -inositol 1,3,4,6-tetrakisphosphate 492.013 C6 H8 O18 P4 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) CHEBI:57660:*PUBCHEM:25201336:*LIGAND-CPD:C04477: 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) D-myo-inositol (1,3,4,6)-tetrakisphosphate Ins(1,3,4,6)P4*inositol (1,3,4,6)-tetrakisphosphate*1D-myo -inositol 1,3,4,6-tetrakisphosphate 492.013 C6 H8 O18 P4 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) CHEBI:57660:*PUBCHEM:25201336:*LIGAND-CPD:C04477: 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis D-myo-inositol (1,3,4,6)-tetrakisphosphate Ins(1,3,4,6)P4*inositol (1,3,4,6)-tetrakisphosphate*1D-myo -inositol 1,3,4,6-tetrakisphosphate 492.013 C6 H8 O18 P4 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) CHEBI:57660:*PUBCHEM:25201336:*LIGAND-CPD:C04477: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) D-myo-inositol (1,3,4,6)-tetrakisphosphate Ins(1,3,4,6)P4*inositol (1,3,4,6)-tetrakisphosphate*1D-myo -inositol 1,3,4,6-tetrakisphosphate 492.013 C6 H8 O18 P4 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) CHEBI:57660:*PUBCHEM:25201336:*LIGAND-CPD:C04477: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis D-myo-inositol (1,3,4,6)-tetrakisphosphate Ins(1,3,4,6)P4*inositol (1,3,4,6)-tetrakisphosphate*1D-myo -inositol 1,3,4,6-tetrakisphosphate 492.013 C6 H8 O18 P4 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) CHEBI:57660:*PUBCHEM:25201336:*LIGAND-CPD:C04477: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) D-myo-inositol (1,3,4,6)-tetrakisphosphate Ins(1,3,4,6)P4*inositol (1,3,4,6)-tetrakisphosphate*1D-myo -inositol 1,3,4,6-tetrakisphosphate 492.013 C6 H8 O18 P4 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) CHEBI:57660:*PUBCHEM:25201336:*LIGAND-CPD:C04477: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis quercetin 3-sulfate 380.282 C15 H8 O10 S1 C3(C(O)=C2(C(OC(C1(C=CC(O)=C(C=1)O))=C(OS(=O)(=O)[O-])C(=O)2)=CC([O-])=3)) PUBCHEM:25203115:*LIGAND-CPD:C00616: 2.8.2.26 quercetin 3-sulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin-3,3'-bissulfate quercetinsulphates biosynthesis quercetin 3-sulfate 380.282 C15 H8 O10 S1 C3(C(O)=C2(C(OC(C1(C=CC(O)=C(C=1)O))=C(OS(=O)(=O)[O-])C(=O)2)=CC([O-])=3)) PUBCHEM:25203115:*LIGAND-CPD:C00616: 2.8.2.27 quercetin 3-sulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin-3,4'-bissulfate quercetinsulphates biosynthesis quercetin 3-sulfate 380.282 C15 H8 O10 S1 C3(C(O)=C2(C(OC(C1(C=CC(O)=C(C=1)O))=C(OS(=O)(=O)[O-])C(=O)2)=CC([O-])=3)) PUBCHEM:25203115:*LIGAND-CPD:C00616: 2.8.2.25 quercetin + phosphoadenosine-5'-phosphosulfate = H+ + adenosine 3',5'-bisphosphate + quercetin 3-sulfate quercetinsulphates biosynthesis phenylacetaldehyde 120.151 C8 H8 O1 C1(C=C(C=CC=1)CC=O) PUBCHEM:998:*CHEBI:16424:*CAS:122-78-1:*LIGAND-CPD:C00601: 1.1.1.1 H+ + phenylacetaldehyde + NADH = 2-phenylethanol + NAD+ phenylethanol biosynthesis phenylacetaldehyde 120.151 C8 H8 O1 C1(C=C(C=CC=1)CC=O) PUBCHEM:998:*CHEBI:16424:*CAS:122-78-1:*LIGAND-CPD:C00601: 1.4.3.21 2-phenylethylamine + oxygen + H2O = H+ + phenylacetaldehyde + ammonia + hydrogen peroxide phenylethanol biosynthesis phenylacetaldehyde 120.151 C8 H8 O1 C1(C=C(C=CC=1)CC=O) PUBCHEM:998:*CHEBI:16424:*CAS:122-78-1:*LIGAND-CPD:C00601: L-phenylalanine + oxygen + H2O = phenylacetaldehyde + ammonia + hydrogen peroxide + CO2 phenylethanol biosynthesis 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol 428.697 C29 H48 O2 C1(CC(C(C2(C1(C3(C(=CC2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))CO)O) 1.14.13.- 24-methylenelophenol + oxygen + NADH = 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol 428.697 C29 H48 O2 C1(CC(C(C2(C1(C3(C(=CC2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))CO)O) 1.14.13.- 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol + oxygen + NADH = 4α-formyl-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis (3S)-linalool (S)-(+)-linalool*linalool*(+)-linalool 154.252 C10 H18 O1 CC(C)=CCCC(C=C)(O)C LIGAND-CPD:C11388:*CHEBI:28:*PUBCHEM:443158: 4.2.3.25 geranyl diphosphate + H2O = (3S)-linalool + diphosphate linalool biosynthesis (Z)-indol-3-ylacetaldoxime (Z)-3-indoleacetaldoxime*(Z)-indole-3-acetaldehyde oxime*(Z)-indole-3-acetaldoxime 174.202 C10 H10 N2 O1 C2(=CC=CC1(=C(NC=C(CC=NO)1)2)) (E)-indol-3-ylacetaldoxime = (Z)-indol-3-ylacetaldoxime IAA biosynthesis I (Z)-indol-3-ylacetaldoxime (Z)-3-indoleacetaldoxime*(Z)-indole-3-acetaldehyde oxime*(Z)-indole-3-acetaldoxime 174.202 C10 H10 N2 O1 C2(=CC=CC1(=C(NC=C(CC=NO)1)2)) 4.99.1.6 (Z)-indol-3-ylacetaldoxime = indole-3-acetonitrile + H2O IAA biosynthesis I p-aminobenzoate pABA*p-aminobenzoate*para-aminobenzoic acid*p-aminobenzoic acid*para-aminobenzoate*4-aminobenzoate*4-aminobenzoic acid 136.13 C7 H6 N1 O2 C1(C=CC(=CC=1)N)C(=O)[O-] CHEBI:17836:*PUBCHEM:4876:*CAS:150-13-0:*LIGAND-CPD:C00568: 2.5.1.15 p-aminobenzoate + 6-hydroxymethyl-dihydropterin diphosphate = 7,8-dihydropteroate + diphosphate tetrahydrofolate biosynthesis p-aminobenzoate pABA*p-aminobenzoate*para-aminobenzoic acid*p-aminobenzoic acid*para-aminobenzoate*4-aminobenzoate*4-aminobenzoic acid 136.13 C7 H6 N1 O2 C1(C=CC(=CC=1)N)C(=O)[O-] CHEBI:17836:*PUBCHEM:4876:*CAS:150-13-0:*LIGAND-CPD:C00568: 4.1.3.38 4-amino-4-deoxychorismate = H+ + p-aminobenzoate + pyruvate p-aminobenzoate biosynthesis (2S)-pinocembrin 255.249 C15 H11 O4 C1(C(=CC(=C2(C=1OC(CC2=O)C3(C=CC=CC=3)))O)[O-]) PUBCHEM:25200438:*LIGAND-CPD:C09827: (2S)-pinocembrin + S-adenosyl-L-methionine = pinostrobin + S-adenosyl-L-homocysteine pinobanksin biosynthesis (2S)-pinocembrin 255.249 C15 H11 O4 C1(C(=CC(=C2(C=1OC(CC2=O)C3(C=CC=CC=3)))O)[O-]) PUBCHEM:25200438:*LIGAND-CPD:C09827: 5.5.1.6 pinocembrin chalcone = H+ + (2S)-pinocembrin pinobanksin biosynthesis (2S)-pinocembrin 255.249 C15 H11 O4 C1(C(=CC(=C2(C=1OC(CC2=O)C3(C=CC=CC=3)))O)[O-]) PUBCHEM:25200438:*LIGAND-CPD:C09827: 1.14.11.9 (2S)-pinocembrin + oxygen + 2-oxoglutarate = (2R,3R)-pinobanksin + CO2 + succinate pinobanksin biosynthesis cycloeucalenol 426.724 C30 H50 O1 C1(CC(C(C2(C51(C3(C(CC2)C4(C)(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4))C5)))C)O) PUBCHEM:25244508:*LIGAND-CPD:C02141:*CAS:469-39-6 5.5.1.9 cycloeucalenol = obtusifoliol plant sterol biosynthesis cycloeucalenol 426.724 C30 H50 O1 C1(CC(C(C2(C51(C3(C(CC2)C4(C)(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4))C5)))C)O) PUBCHEM:25244508:*LIGAND-CPD:C02141:*CAS:469-39-6 1.1.1.- cycloeucalenone + NADPH + H+ = cycloeucalenol + NADP+ plant sterol biosynthesis all-trans-geranyl-geranyl diphosphate ω,E,E,E-geranylgeranyl diphosphate*(2E,6E,10E)-geranylgeranyl diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl-diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl diphosphate*geranylgeranyl-PP*GGPP 447.424 C20 H33 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] KNAPSACK:C00000908:*PUBCHEM:5497105:*PUBCHEM:447277:*CHEBI:15831:*LIGAND-CPD:C00353: 2.5.1.85 all-trans-geranyl-geranyl diphosphate + isopentenyl diphosphate = all-trans-nonaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis II all-trans-geranyl-geranyl diphosphate ω,E,E,E-geranylgeranyl diphosphate*(2E,6E,10E)-geranylgeranyl diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl-diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl diphosphate*geranylgeranyl-PP*GGPP 447.424 C20 H33 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] KNAPSACK:C00000908:*PUBCHEM:5497105:*PUBCHEM:447277:*CHEBI:15831:*LIGAND-CPD:C00353: all-trans-geranyl-geranyl diphosphate = ent-kaurene + diphosphate ent -kaurene biosynthesis II all-trans-geranyl-geranyl diphosphate ω,E,E,E-geranylgeranyl diphosphate*(2E,6E,10E)-geranylgeranyl diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl-diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl diphosphate*geranylgeranyl-PP*GGPP 447.424 C20 H33 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] KNAPSACK:C00000908:*PUBCHEM:5497105:*PUBCHEM:447277:*CHEBI:15831:*LIGAND-CPD:C00353: 2.5.1.32 all-trans-geranyl-geranyl diphosphate = prephytoene diphosphate + diphosphate trans-lycopene biosynthesis II (plants) all-trans-geranyl-geranyl diphosphate ω,E,E,E-geranylgeranyl diphosphate*(2E,6E,10E)-geranylgeranyl diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl-diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl diphosphate*geranylgeranyl-PP*GGPP 447.424 C20 H33 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] KNAPSACK:C00000908:*PUBCHEM:5497105:*PUBCHEM:447277:*CHEBI:15831:*LIGAND-CPD:C00353: 2.5.1.- H+ + chlorophyllide a + all-trans-geranyl-geranyl diphosphate = geranylgeranyl-chlorophyll a + diphosphate chlorophyll a biosynthesis II all-trans-geranyl-geranyl diphosphate ω,E,E,E-geranylgeranyl diphosphate*(2E,6E,10E)-geranylgeranyl diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl-diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl diphosphate*geranylgeranyl-PP*GGPP 447.424 C20 H33 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] KNAPSACK:C00000908:*PUBCHEM:5497105:*PUBCHEM:447277:*CHEBI:15831:*LIGAND-CPD:C00353: 2.5.1.81 isopentenyl diphosphate + all-trans-geranyl-geranyl diphosphate = H+ + geranylfarnesyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III all-trans-geranyl-geranyl diphosphate ω,E,E,E-geranylgeranyl diphosphate*(2E,6E,10E)-geranylgeranyl diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl-diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl diphosphate*geranylgeranyl-PP*GGPP 447.424 C20 H33 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] KNAPSACK:C00000908:*PUBCHEM:5497105:*PUBCHEM:447277:*CHEBI:15831:*LIGAND-CPD:C00353: 2.5.1.29 (2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-geranyl-geranyl diphosphate + diphosphate geranylgeranyldiphosphate biosynthesis all-trans-geranyl-geranyl diphosphate ω,E,E,E-geranylgeranyl diphosphate*(2E,6E,10E)-geranylgeranyl diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl-diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl diphosphate*geranylgeranyl-PP*GGPP 447.424 C20 H33 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] KNAPSACK:C00000908:*PUBCHEM:5497105:*PUBCHEM:447277:*CHEBI:15831:*LIGAND-CPD:C00353: 2.5.1.29 (2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-geranyl-geranyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III all-trans-geranyl-geranyl diphosphate ω,E,E,E-geranylgeranyl diphosphate*(2E,6E,10E)-geranylgeranyl diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl-diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl diphosphate*geranylgeranyl-PP*GGPP 447.424 C20 H33 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] KNAPSACK:C00000908:*PUBCHEM:5497105:*PUBCHEM:447277:*CHEBI:15831:*LIGAND-CPD:C00353: 5.5.1.13 all-trans-geranyl-geranyl diphosphate = ent-copalyl diphosphate ent-kaurene biosynthesis I all-trans-geranyl-geranyl diphosphate ω,E,E,E-geranylgeranyl diphosphate*(2E,6E,10E)-geranylgeranyl diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl-diphosphate*all-trans-geranyl-geranyl-pp*geranylgeranyl diphosphate*geranylgeranyl-PP*GGPP 447.424 C20 H33 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] KNAPSACK:C00000908:*PUBCHEM:5497105:*PUBCHEM:447277:*CHEBI:15831:*LIGAND-CPD:C00353: all-trans-geranyl-geranyl diphosphate + H2O = ent-16-a-hydroxy-kaurene + diphosphate ent -kaurene biosynthesis II methanol MetOH*carbinol*MeOH*methyl alcohol*wood alcohol 32.042 C1 H4 O1 OC CHEBI:17790:*PUBCHEM:887:*LIGAND-CPD:C00132:*CAS:67-56-1 3.1.1.11 H2O = methanol homogalacturonan degradation methanol MetOH*carbinol*MeOH*methyl alcohol*wood alcohol 32.042 C1 H4 O1 OC CHEBI:17790:*PUBCHEM:887:*LIGAND-CPD:C00132:*CAS:67-56-1 3.1.1.82 pheophorbide a + H2O = pyropheophorbide a + methanol + CO2 chlorophyll a degradation methanol MetOH*carbinol*MeOH*methyl alcohol*wood alcohol 32.042 C1 H4 O1 OC CHEBI:17790:*PUBCHEM:887:*LIGAND-CPD:C00132:*CAS:67-56-1 3.1.1.1 methyl indole-3-acetate + H2O = H+ + indole-3-acetate + methanol methyl indole-3-acetate interconversion methanol MetOH*carbinol*MeOH*methyl alcohol*wood alcohol 32.042 C1 H4 O1 OC CHEBI:17790:*PUBCHEM:887:*LIGAND-CPD:C00132:*CAS:67-56-1 1.1.1.244 methanol + NAD+ = H+ + formaldehyde + NADH methanol oxidation to formaldehyde II spermine gerontine*musculamine*neuridine*diaminopropyl-tetramethylenediamine 206.374 C10 H30 N4 C([N+]CCCC[N+]CCC[N+])CC[N+] PUBCHEM:446718:*LIGAND-CPD:C00750:*CAS:71-44-3 2.5.1.22 spermidine + S-adenosyl-L-methioninamine = H+ + spermine + S-methyl-5'-thioadenosine spermine biosynthesis spermine gerontine*musculamine*neuridine*diaminopropyl-tetramethylenediamine 206.374 C10 H30 N4 C([N+]CCCC[N+]CCC[N+])CC[N+] PUBCHEM:446718:*LIGAND-CPD:C00750:*CAS:71-44-3 1.5.3.14 spermine + oxygen + H2O = 1-(3-aminopropyl)-4-aminobutanal + propane-1,3-diamine + hydrogen peroxide spermine and spermidine degradation II 12-oxo-cis-9-dodecenoate 12-oxo-c-9-dodecenoate 211.28 C12 H19 O3 C(=O)CC=CCCCCCCCC(=O)[O-] PUBCHEM:543432:*PUBCHEM:25243932:*LIGAND-CPD:C16311: 12-oxo-cis-9-dodecenoate = traumatin traumatin and (Z)-3-hexen-1-yl acetate biosynthesis 12-oxo-cis-9-dodecenoate 12-oxo-c-9-dodecenoate 211.28 C12 H19 O3 C(=O)CC=CCCCCCCCC(=O)[O-] PUBCHEM:543432:*PUBCHEM:25243932:*LIGAND-CPD:C16311: 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate = 12-oxo-cis-9-dodecenoate + cis-3-hexenal traumatin and (Z)-3-hexen-1-yl acetate biosynthesis 12-oxo-cis-9-dodecenoate 12-oxo-c-9-dodecenoate 211.28 C12 H19 O3 C(=O)CC=CCCCCCCCC(=O)[O-] PUBCHEM:543432:*PUBCHEM:25243932:*LIGAND-CPD:C16311: (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate = 12-oxo-cis-9-dodecenoate + hexanal traumatin and (Z)-3-hexen-1-yl acetate biosynthesis shikimate shikimic acid 173.145 C7 H9 O5 O=C(C1(CC(C(O)C(O)C=1)O))[O-] PUBCHEM:7057976:*CHEBI:36208:*PUBCHEM:21872888:*LIGAND-CPD:C00493:*CAS:138-59-0 1.1.1.25 shikimate + NADP+ = H+ + 3-dehydroshikimate + NADPH chorismate biosynthesis I shikimate shikimic acid 173.145 C7 H9 O5 O=C(C1(CC(C(O)C(O)C=1)O))[O-] PUBCHEM:7057976:*CHEBI:36208:*PUBCHEM:21872888:*LIGAND-CPD:C00493:*CAS:138-59-0 1.1.1.282 shikimate = 3-dehydroshikimate + H+ chorismate biosynthesis I shikimate shikimic acid 173.145 C7 H9 O5 O=C(C1(CC(C(O)C(O)C=1)O))[O-] PUBCHEM:7057976:*CHEBI:36208:*PUBCHEM:21872888:*LIGAND-CPD:C00493:*CAS:138-59-0 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A chlorogenic acid biosynthesis I shikimate shikimic acid 173.145 C7 H9 O5 O=C(C1(CC(C(O)C(O)C=1)O))[O-] PUBCHEM:7057976:*CHEBI:36208:*PUBCHEM:21872888:*LIGAND-CPD:C00493:*CAS:138-59-0 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A chlorogenic acid biosynthesis II shikimate shikimic acid 173.145 C7 H9 O5 O=C(C1(CC(C(O)C(O)C=1)O))[O-] PUBCHEM:7057976:*CHEBI:36208:*PUBCHEM:21872888:*LIGAND-CPD:C00493:*CAS:138-59-0 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A simplecoumarins biosynthesis shikimate shikimic acid 173.145 C7 H9 O5 O=C(C1(CC(C(O)C(O)C=1)O))[O-] PUBCHEM:7057976:*CHEBI:36208:*PUBCHEM:21872888:*LIGAND-CPD:C00493:*CAS:138-59-0 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A phenylpropanoid biosynthesis shikimate shikimic acid 173.145 C7 H9 O5 O=C(C1(CC(C(O)C(O)C=1)O))[O-] PUBCHEM:7057976:*CHEBI:36208:*PUBCHEM:21872888:*LIGAND-CPD:C00493:*CAS:138-59-0 2.7.1.71 shikimate + ATP = H+ + shikimate-3-phosphate + ADP chorismate biosynthesis I shikimate shikimic acid 173.145 C7 H9 O5 O=C(C1(CC(C(O)C(O)C=1)O))[O-] PUBCHEM:7057976:*CHEBI:36208:*PUBCHEM:21872888:*LIGAND-CPD:C00493:*CAS:138-59-0 3.1.2.- caffeoylshikimate + coenzyme A = caffeoyl-CoA + shikimate chlorogenic acid biosynthesis I shikimate shikimic acid 173.145 C7 H9 O5 O=C(C1(CC(C(O)C(O)C=1)O))[O-] PUBCHEM:7057976:*CHEBI:36208:*PUBCHEM:21872888:*LIGAND-CPD:C00493:*CAS:138-59-0 3.1.2.- caffeoylshikimate + coenzyme A = caffeoyl-CoA + shikimate phenylpropanoid biosynthesis biliverdin-IX-α dehydrobilirubin*uteroverdine*biliverdine*biliverdin 580.639 C33 H32 N4 O6 C1(=C(C(NC1=CC2(=C(C(=C(N2)C=C3(N=C(C(=C3CCC(=O)[O-])C)C=C4(NC(C(=C4C)C=C)=O)))CCC(=O)[O-])C))=O)C)C=C PUBCHEM:25245769:*LIGAND-CPD:C00500: 1.3.1.24 bilirubin = biliverdin-IX-α heme degradation biliverdin-IX-α dehydrobilirubin*uteroverdine*biliverdine*biliverdin 580.639 C33 H32 N4 O6 C1(=C(C(NC1=CC2(=C(C(=C(N2)C=C3(N=C(C(=C3CCC(=O)[O-])C)C=C4(NC(C(=C4C)C=C)=O)))CCC(=O)[O-])C))=O)C)C=C PUBCHEM:25245769:*LIGAND-CPD:C00500: 1.14.99.3 protoheme IX + oxygen = biliverdin-IX-α + Fe2+ + carbon monoxide + H2O heme degradation divinyl protochlorophyllide a divinylprotochlorophyllide*divinyl protochlrophyllide a 609.943 C35 H29 N4 O5 MG1 C17(N9(C2(=C(C=1C)C(=O)C(C(OC)=O)([H])C2=C3(C(=C(C8(=N3[Mg]6(N4(C(C(=C(C4=CC5(C(=C(C(N=56)=C7)C=C)C))C=C)C)=C8))9))C)CCC(=O)[O-])))) PUBCHEM:44229214:*LIGAND-CPD:C11831: 1.14.13.81 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + oxygen + NADPH + H+ = divinyl protochlorophyllide a + NADP+ + H2O chlorophyllide a biosynthesis I divinyl protochlorophyllide a divinylprotochlorophyllide*divinyl protochlrophyllide a 609.943 C35 H29 N4 O5 MG1 C17(N9(C2(=C(C=1C)C(=O)C(C(OC)=O)([H])C2=C3(C(=C(C8(=N3[Mg]6(N4(C(C(=C(C4=CC5(C(=C(C(N=56)=C7)C=C)C))C=C)C)=C8))9))C)CCC(=O)[O-])))) PUBCHEM:44229214:*LIGAND-CPD:C11831: 1.3.1.75 H+ + divinyl protochlorophyllide a + NADPH = monovinyl protochlorophyllide a + NADP+ chlorophyllide a biosynthesis I pyridoxal 167.164 C8 H9 N1 O3 C1(C(=NC=C(C=1C=O)CO)C)O PUBCHEM:1050:*CHEBI:17310:*LIGAND-CPD:C00250:*CAS:66-72-8 2.7.1.35 ATP + pyridoxal = H+ + ADP + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway N-acetyl-L-ornithine N2-acetyl-ornithine*N-α-acetylornithine*N-acetylornithine*acetylornithine*N2-acetyl-L-ornithine 174.199 C7 H14 N2 O3 CC(=O)NC(CCC[N+])C(=O)[O-] CHEBI:57805:*PUBCHEM:6992102:*LIGAND-CPD:C00437:*CAS:2185-16-2 2.3.1.35 L-glutamate + N-acetyl-L-ornithine = N-acetyl-L-glutamate + L-ornithine arginine biosynthesis II (acetyl cycle) N-acetyl-L-ornithine N2-acetyl-ornithine*N-α-acetylornithine*N-acetylornithine*acetylornithine*N2-acetyl-L-ornithine 174.199 C7 H14 N2 O3 CC(=O)NC(CCC[N+])C(=O)[O-] CHEBI:57805:*PUBCHEM:6992102:*LIGAND-CPD:C00437:*CAS:2185-16-2 2.6.1.11 N-acetyl-L-ornithine + 2-oxoglutarate = L-glutamate + N-acetyl-L-glutamate 5-semialdehyde arginine biosynthesis II (acetyl cycle) N-acetyl-L-ornithine N2-acetyl-ornithine*N-α-acetylornithine*N-acetylornithine*acetylornithine*N2-acetyl-L-ornithine 174.199 C7 H14 N2 O3 CC(=O)NC(CCC[N+])C(=O)[O-] CHEBI:57805:*PUBCHEM:6992102:*LIGAND-CPD:C00437:*CAS:2185-16-2 2.6.1.11 N-acetyl-L-ornithine + 2-oxoglutarate = L-glutamate + N-acetyl-L-glutamate 5-semialdehyde ornithine biosynthesis N-acetyl-L-ornithine N2-acetyl-ornithine*N-α-acetylornithine*N-acetylornithine*acetylornithine*N2-acetyl-L-ornithine 174.199 C7 H14 N2 O3 CC(=O)NC(CCC[N+])C(=O)[O-] CHEBI:57805:*PUBCHEM:6992102:*LIGAND-CPD:C00437:*CAS:2185-16-2 3.5.1.16 N-acetyl-L-ornithine + H2O = L-ornithine + acetate ornithine biosynthesis 4-guanidinobutyramide 4-guanidinobutanamide*4-guanidobutanamide*4-guanido-butyramide*γ-guanidinobutyramide 145.184 C5 H13 N4 O1 C(CCNC(N)=[N+])C(=O)N PUBCHEM:25243936:*LIGAND-CPD:C03078: 3.5.1.4 4-guanidinobutyramide + H2O = H+ + ammonia + 4-guanidinobutyrate arginine degradation X (arginine monooxygenase pathway) 4-guanidinobutyramide 4-guanidinobutanamide*4-guanidobutanamide*4-guanido-butyramide*γ-guanidinobutyramide 145.184 C5 H13 N4 O1 C(CCNC(N)=[N+])C(=O)N PUBCHEM:25243936:*LIGAND-CPD:C03078: 1.13.12.1 oxygen + L-arginine = 4-guanidinobutyramide + H2O + CO2 arginine degradation X (arginine monooxygenase pathway) S-ribosyl-L-homocysteine S-Ribosylhomocysteine*Ribose-5-S-homocysteine*S-Ribosyl-L-homocysteine*S-D-ribosyl-L-homocysteine*ribose-5-S-homocysteine*S-ribosylhomocysteine*S-(5-deoxy-D-ribos-5-yl)-L-homocysteine 267.296 C9 H17 N1 O6 S1 [N+]C(CCSCC1(OC(O)C(O)C(O)1))C(=O)[O-] PUBCHEM:25245776:*CAS:37558-16-0:*LIGAND-CPD:C03539: 4.4.1.21 S-ribosyl-L-homocysteine = L-homocysteine + 4,5-dihydroxy-2,3-pentanedione S-adenosyl-L-methionine cycle I S-ribosyl-L-homocysteine S-Ribosylhomocysteine*Ribose-5-S-homocysteine*S-Ribosyl-L-homocysteine*S-D-ribosyl-L-homocysteine*ribose-5-S-homocysteine*S-ribosylhomocysteine*S-(5-deoxy-D-ribos-5-yl)-L-homocysteine 267.296 C9 H17 N1 O6 S1 [N+]C(CCSCC1(OC(O)C(O)C(O)1))C(=O)[O-] PUBCHEM:25245776:*CAS:37558-16-0:*LIGAND-CPD:C03539: 3.2.2.9 S-adenosyl-L-homocysteine + H2O = S-ribosyl-L-homocysteine + adenine S-adenosyl-L-methionine cycle I imidazole acetol-phosphate imidazole acetol-P*3-(imidazol-4-yl)-2-oxopropyl phosphate 218.105 C6 H7 N2 O5 P1 C1(NC=NC=1CC(COP([O-])(=O)[O-])=O) CHEBI:57766:*PUBCHEM:25244516:*LIGAND-CPD:C01267:*CAS:99979-59-6 2.6.1.9 imidazole acetol-phosphate + L-glutamate = L-histidinol-phosphate + 2-oxoglutarate histidine biosynthesis imidazole acetol-phosphate imidazole acetol-P*3-(imidazol-4-yl)-2-oxopropyl phosphate 218.105 C6 H7 N2 O5 P1 C1(NC=NC=1CC(COP([O-])(=O)[O-])=O) CHEBI:57766:*PUBCHEM:25244516:*LIGAND-CPD:C01267:*CAS:99979-59-6 4.2.1.19 D-erythro-imidazole-glycerol-phosphate = imidazole acetol-phosphate + H2O histidine biosynthesis N-hydroxy-L-tryptophan 219.219 C11 H11 N2 O3 C2(CC(NO)C([O-])=O)(C1(C=CC=CC=1NC=2)) 1.14.13.- N-hydroxy-L-tryptophan + oxygen + NADPH + H+ = N,N-dihydroxy-L-tryptophan + NADP+ + H2O IAA biosynthesis I N-hydroxy-L-tryptophan 219.219 C11 H11 N2 O3 C2(CC(NO)C([O-])=O)(C1(C=CC=CC=1NC=2)) 1.14.13.- L-tryptophan + oxygen + NADPH = N-hydroxy-L-tryptophan + NADP+ + H2O IAA biosynthesis I N-acetyl-α-D-glucosamine 1-phosphate N-acetyl-D-glucosamine 1-phosphate*N-acetyl-α-D-glucosamine 1-phosphate 299.174 C8 H14 N1 O9 P1 CC(=O)NC1(C(O)C(O)C(CO)OC(OP(=O)([O-])[O-])1) CHEBI:57776:*PUBCHEM:25243937:*LIGAND-CPD:C04256: 5.4.2.3 N-acetyl-α-D-glucosamine 1-phosphate = N-acetyl-D-glucosamine-6-phosphate UDP-N-acetyl-D-glucosamine biosynthesis II N-acetyl-α-D-glucosamine 1-phosphate N-acetyl-D-glucosamine 1-phosphate*N-acetyl-α-D-glucosamine 1-phosphate 299.174 C8 H14 N1 O9 P1 CC(=O)NC1(C(O)C(O)C(CO)OC(OP(=O)([O-])[O-])1) CHEBI:57776:*PUBCHEM:25243937:*LIGAND-CPD:C04256: 2.7.7.23 H+ + N-acetyl-α-D-glucosamine 1-phosphate + UTP = UDP-α-N-acetyl-D-glucosamine + diphosphate UDP-N-acetyl-D-glucosamine biosynthesis II D-myo-inositol (1,3,4,5)-tetrakisphosphate Ins(1,3,4,5)P4*inositol (1,3,4,5)-tetrakisphosphate*1D-myo-inositol (1,3,4,5)-tetrakisphosphate 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(O)C(OP([O-])([O-])=O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:24742076:*LIGAND-CPD:C01272: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) D-myo-inositol (1,3,4,5)-tetrakisphosphate Ins(1,3,4,5)P4*inositol (1,3,4,5)-tetrakisphosphate*1D-myo-inositol (1,3,4,5)-tetrakisphosphate 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(O)C(OP([O-])([O-])=O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:24742076:*LIGAND-CPD:C01272: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) D-myo-inositol (1,3,4,5)-tetrakisphosphate Ins(1,3,4,5)P4*inositol (1,3,4,5)-tetrakisphosphate*1D-myo-inositol (1,3,4,5)-tetrakisphosphate 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(O)C(OP([O-])([O-])=O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:24742076:*LIGAND-CPD:C01272: 2.7.1.127 D-myo-inositol (1,4,5)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) D-myo-inositol (1,3,4,5)-tetrakisphosphate Ins(1,3,4,5)P4*inositol (1,3,4,5)-tetrakisphosphate*1D-myo-inositol (1,3,4,5)-tetrakisphosphate 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(O)C(OP([O-])([O-])=O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:24742076:*LIGAND-CPD:C01272: 2.7.1.151 D-myo-inositol (1,3,4,5)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) D-myo-inositol (1,3,4,5)-tetrakisphosphate Ins(1,3,4,5)P4*inositol (1,3,4,5)-tetrakisphosphate*1D-myo-inositol (1,3,4,5)-tetrakisphosphate 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(O)C(OP([O-])([O-])=O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:24742076:*LIGAND-CPD:C01272: 2.7.1.151 D-myo-inositol (1,3,4,5)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) D-myo-inositol (1,3,4,5)-tetrakisphosphate Ins(1,3,4,5)P4*inositol (1,3,4,5)-tetrakisphosphate*1D-myo-inositol (1,3,4,5)-tetrakisphosphate 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(O)C(OP([O-])([O-])=O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:24742076:*LIGAND-CPD:C01272: 2.7.1.151 D-myo-inositol (1,3,4,5)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) succinyl-CoA suc-coa*succ-coenzyme-A*succ-S-coenzyme-A*succinyl-S-coenzyme-A*succ-S-CoA*succinylcoenzyme-A*succ-CoA*suc-co-A*succinyl-S-CoA 862.568 C25 H35 N7 O19 P3 S1 C1(C(O)C(C(COP(=O)([O-])OP(OCC(C)(C)C(C(NCCC(=O)NCCSC(CCC(=O)[O-])=O)=O)O)(=O)[O-])O1)OP([O-])([O-])=O)(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25245777:*PUBCHEM:25245777:*LIGAND-CPD:C00091:*CAS:604-98-8 2-oxoglutarate + coenzyme A + NAD+ = succinyl-CoA + CO2 + NADH TCA cycle variation III (eukaryotic) succinyl-CoA suc-coa*succ-coenzyme-A*succ-S-coenzyme-A*succinyl-S-coenzyme-A*succ-S-CoA*succinylcoenzyme-A*succ-CoA*suc-co-A*succinyl-S-CoA 862.568 C25 H35 N7 O19 P3 S1 C1(C(O)C(C(COP(=O)([O-])OP(OCC(C)(C)C(C(NCCC(=O)NCCSC(CCC(=O)[O-])=O)=O)O)(=O)[O-])O1)OP([O-])([O-])=O)(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25245777:*PUBCHEM:25245777:*LIGAND-CPD:C00091:*CAS:604-98-8 6.2.1.5 succinate + coenzyme A + ATP = succinyl-CoA + ADP TCA cycle variation III (eukaryotic) succinyl-CoA suc-coa*succ-coenzyme-A*succ-S-coenzyme-A*succinyl-S-coenzyme-A*succ-S-CoA*succinylcoenzyme-A*succ-CoA*suc-co-A*succinyl-S-CoA 862.568 C25 H35 N7 O19 P3 S1 C1(C(O)C(C(COP(=O)([O-])OP(OCC(C)(C)C(C(NCCC(=O)NCCSC(CCC(=O)[O-])=O)=O)O)(=O)[O-])O1)OP([O-])([O-])=O)(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25245777:*PUBCHEM:25245777:*LIGAND-CPD:C00091:*CAS:604-98-8 2.3.1.61 succinyl-CoA = coenzyme A 2-ketoglutarate dehydrogenase complex ferulate ferulate*ferulic acid*3-methoxy-4-hydroxycinnamic acid*caffeic acid 3-methyl ether*4-hydroxy-3-methoxycinnamic acid*3-methoxy-4-hydroxy-trans-cinnamate 193.179 C10 H9 O4 C1(C=CC([O-])=O)(=CC(OC)=C(O)C=C1) PUBCHEM:5460310:*CHEBI:29749:*CAS:1135-24-6*LIGAND-CPD:C01494: 6.2.1.34 ferulate + ATP + coenzyme A = feruloyl-CoA + AMP + diphosphate suberin biosynthesis ferulate ferulate*ferulic acid*3-methoxy-4-hydroxycinnamic acid*caffeic acid 3-methyl ether*4-hydroxy-3-methoxycinnamic acid*3-methoxy-4-hydroxy-trans-cinnamate 193.179 C10 H9 O4 C1(C=CC([O-])=O)(=CC(OC)=C(O)C=C1) PUBCHEM:5460310:*CHEBI:29749:*CAS:1135-24-6*LIGAND-CPD:C01494: 2.1.1.68 trans-caffeate + S-adenosyl-L-methionine = H+ + ferulate + S-adenosyl-L-homocysteine suberin biosynthesis ferulate ferulate*ferulic acid*3-methoxy-4-hydroxycinnamic acid*caffeic acid 3-methyl ether*4-hydroxy-3-methoxycinnamic acid*3-methoxy-4-hydroxy-trans-cinnamate 193.179 C10 H9 O4 C1(C=CC([O-])=O)(=CC(OC)=C(O)C=C1) PUBCHEM:5460310:*CHEBI:29749:*CAS:1135-24-6*LIGAND-CPD:C01494: 2.1.1.68 trans-caffeate + S-adenosyl-L-methionine = H+ + ferulate + S-adenosyl-L-homocysteine free phenylpropanoid acid biosynthesis ferulate ferulate*ferulic acid*3-methoxy-4-hydroxycinnamic acid*caffeic acid 3-methyl ether*4-hydroxy-3-methoxycinnamic acid*3-methoxy-4-hydroxy-trans-cinnamate 193.179 C10 H9 O4 C1(C=CC([O-])=O)(=CC(OC)=C(O)C=C1) PUBCHEM:5460310:*CHEBI:29749:*CAS:1135-24-6*LIGAND-CPD:C01494: 2.1.1.68 trans-caffeate + S-adenosyl-L-methionine = H+ + ferulate + S-adenosyl-L-homocysteine simplecoumarins biosynthesis ferulate ferulate*ferulic acid*3-methoxy-4-hydroxycinnamic acid*caffeic acid 3-methyl ether*4-hydroxy-3-methoxycinnamic acid*3-methoxy-4-hydroxy-trans-cinnamate 193.179 C10 H9 O4 C1(C=CC([O-])=O)(=CC(OC)=C(O)C=C1) PUBCHEM:5460310:*CHEBI:29749:*CAS:1135-24-6*LIGAND-CPD:C01494: 1.2.1.68 coniferaldehyde + H2O = ferulate + H+ ferulate and sinapate biosynthesis ferulate ferulate*ferulic acid*3-methoxy-4-hydroxycinnamic acid*caffeic acid 3-methyl ether*4-hydroxy-3-methoxycinnamic acid*3-methoxy-4-hydroxy-trans-cinnamate 193.179 C10 H9 O4 C1(C=CC([O-])=O)(=CC(OC)=C(O)C=C1) PUBCHEM:5460310:*CHEBI:29749:*CAS:1135-24-6*LIGAND-CPD:C01494: H+ + ferulate + NADPH + oxygen = 5-hydroxyferulate + H2O + NADP+ free phenylpropanoid acid biosynthesis ferulate ferulate*ferulic acid*3-methoxy-4-hydroxycinnamic acid*caffeic acid 3-methyl ether*4-hydroxy-3-methoxycinnamic acid*3-methoxy-4-hydroxy-trans-cinnamate 193.179 C10 H9 O4 C1(C=CC([O-])=O)(=CC(OC)=C(O)C=C1) PUBCHEM:5460310:*CHEBI:29749:*CAS:1135-24-6*LIGAND-CPD:C01494: ferulate = 2-hydroxyferulate simplecoumarins biosynthesis ubiquinol-9 ubiquinol(9) 797.255 C54 H84 O4 C(C=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(C)C)C)C)C)C)C)C)C)C)C1(C(O)=C(OC)C(OC)=C(C=1C)O) PUBCHEM:45281170: 2.1.1.64 3-demethylubiquinol-9 + S-adenosyl-L-methionine = H+ + ubiquinol-9 + S-adenosyl-L-homocysteine ubiquinol-9 biosynthesis (eukaryotic) 3-methyl-4-trans-hydroxy-2-butenal 100.117 C5 H8 O2 O=CC=C(C)CO PUBCHEM:22841439: 1.5.99.12 H+ + trans-zeatin + H2O + FAD = adenine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation 3-methyl-4-trans-hydroxy-2-butenal 100.117 C5 H8 O2 O=CC=C(C)CO PUBCHEM:22841439: 1.5.99.12 H+ + trans-zeatin riboside + H2O + FAD = adenosine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation sirohydrochlorin Precorrin 854.779 C42 H38 N4 O16 CC2(CC(=O)[O-])(C1(=CC5(NC(C=C4(N=C(C=C3(NC(=CC(=N1)C(CCC(=O)[O-])2)C(C)(CC(=O)[O-])C(CCC(=O)[O-])3))C(CC(=O)[O-])=C(CCC(=O)[O-])4))=C(CCC(=O)[O-])C(CC(=O)[O-])=5))) CHEBI:58351:*PUBCHEM:25245154:*LIGAND-CPD:C05778:*CAS:65207-12-7 1.3.1.76 precorrin-2 + NAD+ = H+ + sirohydrochlorin + NADH siroheme biosynthesis sirohydrochlorin Precorrin 854.779 C42 H38 N4 O16 CC2(CC(=O)[O-])(C1(=CC5(NC(C=C4(N=C(C=C3(NC(=CC(=N1)C(CCC(=O)[O-])2)C(C)(CC(=O)[O-])C(CCC(=O)[O-])3))C(CC(=O)[O-])=C(CCC(=O)[O-])4))=C(CCC(=O)[O-])C(CC(=O)[O-])=5))) CHEBI:58351:*PUBCHEM:25245154:*LIGAND-CPD:C05778:*CAS:65207-12-7 4.99.1.4 H+ + sirohydrochlorin + Fe2+ = siroheme siroheme biosynthesis GA44 (open lactone form) gibberellin A44 open lactone*GA44 diacid*gibberellin A44 diacid*GA44 open lactone 362.422 C20 H26 O6 C4(C([O-])=O)(C)(CCCC3(CO)(C(C(C([O-])=O)C12(CC(=C)C(O)(C1)CCC23))4)) CHEBI:27531:*PUBCHEM:25243940:*LIGAND-CPD:C06095: 1.14.11.- H+ + GA44 (open lactone form) + 2-oxoglutarate + oxygen = GA38 + succinate + CO2 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) GA44 (open lactone form) gibberellin A44 open lactone*GA44 diacid*gibberellin A44 diacid*GA44 open lactone 362.422 C20 H26 O6 C4(C([O-])=O)(C)(CCCC3(CO)(C(C(C([O-])=O)C12(CC(=C)C(O)(C1)CCC23))4)) CHEBI:27531:*PUBCHEM:25243940:*LIGAND-CPD:C06095: 1.14.11.- GA53 + oxygen + 2-oxoglutarate = GA44 (open lactone form) + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) GA44 (open lactone form) gibberellin A44 open lactone*GA44 diacid*gibberellin A44 diacid*GA44 open lactone 362.422 C20 H26 O6 C4(C([O-])=O)(C)(CCCC3(CO)(C(C(C([O-])=O)C12(CC(=C)C(O)(C1)CCC23))4)) CHEBI:27531:*PUBCHEM:25243940:*LIGAND-CPD:C06095: 1.14.11.12 GA44 (open lactone form) + 2-oxoglutarate + oxygen = GA19 + succinate + CO2 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.1.3.15 glycolate + oxygen = glyoxylate + hydrogen peroxide photorespiration hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.15.1.1 superoxide + H+ = hydrogen peroxide + oxygen superoxide radicals degradation hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.2.3.1 oxygen + H2O = hydrogen peroxide aldehyde oxidation I hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.11.1.7 betanidin + hydrogen peroxide = betanidin + betanidin quinone + H2O betanidin degradation hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.3.3.6 OPC4-CoA + oxygen = OPC4-trans-2-enoyl-CoA + hydrogen peroxide jasmonic acid biosynthesis hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.11.1.11 H+ + L-ascorbate + hydrogen peroxide = monodehydroascorbate + H2O ascorbate glutathione cycle hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.11.1.6 ethanol + hydrogen peroxide = H2O + acetaldehyde ethanol degradation IV (peroxisomal) hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.2.3.14 abscisic aldehyde + H2O + oxygen = H+ + 2-cis-abscisic acid + hydrogen peroxide abscisic acid biosynthesis hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.2.3.14 abscisic aldehyde + H2O + oxygen = H+ + 2-cis-abscisic acid + hydrogen peroxide aldehyde oxidation I hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 DMSP-amine + oxygen + H2O = H+ + 3-dimethylsulfoniopropionaldehyde + ammonia + hydrogen peroxide dimethylsulfoniopropionate biosynthesis II (Spartina) hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 L-phenylalanine + oxygen + H2O = phenylacetaldehyde + ammonia + hydrogen peroxide + CO2 phenylethanol biosynthesis hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.8.3.1 sulfite + oxygen + H2O = hydrogen peroxide + sulfate sulfite oxidation IV hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.3.3.4 protoporphyrinogen IX + oxygen = protoporphyrin IX + hydrogen peroxide chlorophyllide a biosynthesis I hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.3.3.4 protoporphyrinogen IX + oxygen = protoporphyrin IX + hydrogen peroxide heme biosynthesis from uroporphyrinogen-III I hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.4.3.22 propane-1,3-diamine + H2O + oxygen = H+ + 3-aminopropanal + ammonia + hydrogen peroxide β-alanine biosynthesis I hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.4.3.5 oxygen + H2O + pyridoxamine 5'-phosphate = H+ + ammonia + hydrogen peroxide + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.5.3.14 spermidine + oxygen + H2O = propane-1,3-diamine + 4-aminobutanal + hydrogen peroxide spermine and spermidine degradation II hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.21.3.3 oxygen + (S)-reticuline = H+ + hydrogen peroxide + S-scoulerine dehydroscoulerine biosynthesis hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.11.1.9 hydrogen peroxide + glutathione = glutathione disulfide + H2O glutathione redox reactions I hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.4.3.5 oxygen + pyridoxine-5'-phosphate = hydrogen peroxide + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.4.3.21 2-phenylethylamine + oxygen + H2O = H+ + phenylacetaldehyde + ammonia + hydrogen peroxide phenylethanol biosynthesis hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.4.3.10 oxygen + H2O + putrescine = H+ + ammonia + hydrogen peroxide + 4-aminobutanal putrescine degradation IV hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.2.3.9 benzaldehyde + oxygen + H2O = H+ + benzoate + hydrogen peroxide aldehyde oxidation I hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.3.3.6 OPC6-CoA + oxygen = OPC6-trans-2-enoyl-CoA + hydrogen peroxide jasmonic acid biosynthesis hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.2.3.7 indole acetaldehyde + oxygen + H2O = H+ + indole-3-acetate + hydrogen peroxide IAA biosynthesis I hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.7.3.3 urate + oxygen + H2O = 5-hydroxyisourate + hydrogen peroxide urate degradation to allantoin hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.4.3.16 L-aspartate + oxygen = H+ + α-iminosuccinate + hydrogen peroxide NAD biosynthesis I (from aspartate) hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.5.3.14 spermine + oxygen + H2O = 1-(3-aminopropyl)-4-aminobutanal + propane-1,3-diamine + hydrogen peroxide spermine and spermidine degradation II hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.3.3.6 oxygen = hydrogen peroxide fatty acid β-oxidation II (core pathway) hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.11.1.6 hydrogen peroxide = H2O + oxygen superoxide radicals degradation hydrogen peroxide hydrogen peroxide*hydroperoxide*perhydrol*H2O2 34.015 H2 O2 OO PUBCHEM:784:*CHEBI:16240:*LIGAND-CPD:C00027:*CAS:7722-84-1 1.3.3.6 OPC8-CoA + oxygen = OPC8-trans-2-enoyl-CoA + hydrogen peroxide jasmonic acid biosynthesis β-D-fructofuranose β-D-fructofuranose*β-D-fructose*β-fruit sugar*β-Levulose*β-D-arabino-Hexulose 180.157 C6 H12 O6 OCC1(OC(O)(CO)C(O)C(O)1) CHEBI:28645:*PUBCHEM:439709:*LIGAND-CPD:C02336: 3.2.1.26 sucrose + H2O = α-D-glucose + β-D-fructofuranose sucrose degradation III β-D-fructofuranose β-D-fructofuranose*β-D-fructose*β-fruit sugar*β-Levulose*β-D-arabino-Hexulose 180.157 C6 H12 O6 OCC1(OC(O)(CO)C(O)C(O)1) CHEBI:28645:*PUBCHEM:439709:*LIGAND-CPD:C02336: 3.2.1.26 sucrose-6-phosphate + H2O = β-D-glucose-6-phosphate + β-D-fructofuranose sucrose degradation I β-D-fructofuranose β-D-fructofuranose*β-D-fructose*β-fruit sugar*β-Levulose*β-D-arabino-Hexulose 180.157 C6 H12 O6 OCC1(OC(O)(CO)C(O)C(O)1) CHEBI:28645:*PUBCHEM:439709:*LIGAND-CPD:C02336: 2.7.1.4 β-D-fructofuranose + ATP = H+ + D-fructose-6-phosphate + ADP sucrose degradation III β-D-fructofuranose β-D-fructofuranose*β-D-fructose*β-fruit sugar*β-Levulose*β-D-arabino-Hexulose 180.157 C6 H12 O6 OCC1(OC(O)(CO)C(O)C(O)1) CHEBI:28645:*PUBCHEM:439709:*LIGAND-CPD:C02336: 2.7.1.4 β-D-fructofuranose + ATP = H+ + D-fructose-6-phosphate + ADP sucrose degradation I β-D-fructofuranose β-D-fructofuranose*β-D-fructose*β-fruit sugar*β-Levulose*β-D-arabino-Hexulose 180.157 C6 H12 O6 OCC1(OC(O)(CO)C(O)C(O)1) CHEBI:28645:*PUBCHEM:439709:*LIGAND-CPD:C02336: 2.4.1.13 β-D-fructofuranose = sucrose + UDP sucrose degradation III β-D-fructofuranose β-D-fructofuranose*β-D-fructose*β-fruit sugar*β-Levulose*β-D-arabino-Hexulose 180.157 C6 H12 O6 OCC1(OC(O)(CO)C(O)C(O)1) CHEBI:28645:*PUBCHEM:439709:*LIGAND-CPD:C02336: 2.4.1.13 β-D-fructofuranose = sucrose + UDP galactose degradation III β-D-fructofuranose β-D-fructofuranose*β-D-fructose*β-fruit sugar*β-Levulose*β-D-arabino-Hexulose 180.157 C6 H12 O6 OCC1(OC(O)(CO)C(O)C(O)1) CHEBI:28645:*PUBCHEM:439709:*LIGAND-CPD:C02336: 2.4.1.13 β-D-fructofuranose = sucrose + UDP sucrose biosynthesis 3-methyl-2-butenal 3-methylbut-2-enal*3,3-dimethyl-acrylaldehyde*prenal*3-methylcrotonaldehyde 84.118 C5 H8 O1 O=CC=C(C)C LIGAND-CPD:C07330:*PUBCHEM:61020:*LIGAND-CPD:C07330:*CHEBI:15825: 1.5.99.12 N6-dimethylallyladenine + H+ + FAD + H2O = 3-methyl-2-butenal + adenine + FADH2 cytokinins degradation 3-methyl-2-butenal 3-methylbut-2-enal*3,3-dimethyl-acrylaldehyde*prenal*3-methylcrotonaldehyde 84.118 C5 H8 O1 O=CC=C(C)C LIGAND-CPD:C07330:*PUBCHEM:61020:*LIGAND-CPD:C07330:*CHEBI:15825: 1.5.99.12 H+ + isopentenyl adenosine + H2O + FAD = adenosine + 3-methyl-2-butenal + FADH2 cytokinins degradation cis-caffeate 3,4-dihydroxycinnamic acid*caffeic acid*cis-caffeic acid*3,4-dihydroxy-cis-cinnamate*cis-caffeic acid*3,4-dihydroxy-cis-cinnamic acid*(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid 179.152 C9 H7 O4 C1(O)(C(O)=CC(C=CC([O-])=O)=CC=1) PUBCHEM:1549110:*CHEBI:17395:*LIGAND-CPD:C01481: 1.10.3.1 cis-caffeate + oxygen = 3-(2-propenoic acid)-o-benzoquinone + H2O esculetin biosynthesis cis-caffeate 3,4-dihydroxycinnamic acid*caffeic acid*cis-caffeic acid*3,4-dihydroxy-cis-cinnamate*cis-caffeic acid*3,4-dihydroxy-cis-cinnamic acid*(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid 179.152 C9 H7 O4 C1(O)(C(O)=CC(C=CC([O-])=O)=CC=1) PUBCHEM:1549110:*CHEBI:17395:*LIGAND-CPD:C01481: 5.2.1.- trans-caffeate = cis-caffeate esculetin biosynthesis nicotinamide mononucleotide β-nicotinamide D-ribonucleotide*nicotinamide ribonucleotide*nicotinamide nucleotide*NMN*nicotinamide D-ribonucleotide 333.214 C11 H14 N2 O8 P1 C1(C(O)C(C(COP([O-])(=O)[O-])O1)O)[N+]2(C=CC=C(C(=O)N)C=2) PUBCHEM:25245788:*LIGAND-CPD:C00455:*CAS:1094-61-7 3.2.2.14 nicotinamide mononucleotide + H2O = H+ + D-ribose-5-phosphate + nicotinamide pyridine nucleotide cycling (plants) nicotinamide mononucleotide β-nicotinamide D-ribonucleotide*nicotinamide ribonucleotide*nicotinamide nucleotide*NMN*nicotinamide D-ribonucleotide 333.214 C11 H14 N2 O8 P1 C1(C(O)C(C(COP([O-])(=O)[O-])O1)O)[N+]2(C=CC=C(C(=O)N)C=2) PUBCHEM:25245788:*LIGAND-CPD:C00455:*CAS:1094-61-7 3.1.3.5 nicotinamide mononucleotide + H2O = nicotinamide riboside pyridine nucleotide cycling (plants) nicotinamide mononucleotide β-nicotinamide D-ribonucleotide*nicotinamide ribonucleotide*nicotinamide nucleotide*NMN*nicotinamide D-ribonucleotide 333.214 C11 H14 N2 O8 P1 C1(C(O)C(C(COP([O-])(=O)[O-])O1)O)[N+]2(C=CC=C(C(=O)N)C=2) PUBCHEM:25245788:*LIGAND-CPD:C00455:*CAS:1094-61-7 3.6.1.22 H2O + NAD+ = H+ + nicotinamide mononucleotide + AMP pyridine nucleotide cycling (plants) 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: formaldehyde + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H2O formaldehyde oxidation V (tetrahydrofolate pathway) 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 1.5.1.15 5,10-methylenetetrahydropteroyl mono-L-glutamate + NAD+ = 5,10-methenyltetrahydrofolate + NADH folate transformations I 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 2.1.2.11 5,10-methylenetetrahydropteroyl mono-L-glutamate + 2-oxoisovalerate + H2O = H+ + 2-dehydropantoate + tetrahydrofolate phosphopantothenate biosynthesis I 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 2.1.2.11 5,10-methylenetetrahydropteroyl mono-L-glutamate + 2-oxoisovalerate + H2O = H+ + 2-dehydropantoate + tetrahydrofolate pantothenate biosynthesis I 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 2.1.2.10 tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia glycine cleavage complex 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations I 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations II (plants) 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH photorespiration 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O glycine biosynthesis I 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O folate transformations I 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O folate transformations II (plants) 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O folate polyglutamylation 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O photorespiration 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 1.5.1.5 5,10-methylenetetrahydropteroyl mono-L-glutamate + NADP+ = NADPH + 5,10-methenyltetrahydrofolate folate transformations I 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 1.5.1.5 5,10-methylenetetrahydropteroyl mono-L-glutamate + NADP+ = NADPH + 5,10-methenyltetrahydrofolate folate transformations II (plants) 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 1.5.1.5 5,10-methylenetetrahydropteroyl mono-L-glutamate + NADP+ = NADPH + 5,10-methenyltetrahydrofolate formaldehyde oxidation V (tetrahydrofolate pathway) 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 1.5.7.1 5-methyl-tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H+ folate transformations I 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 2.1.1.45 5,10-methylenetetrahydropteroyl mono-L-glutamate + dUMP = dTMP + 7,8-dihydrofolate monoglutamate pyrimidine deoxyribonucleotides de novo biosynthesis I 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 2.1.1.45 5,10-methylenetetrahydropteroyl mono-L-glutamate + dUMP = dTMP + 7,8-dihydrofolate monoglutamate folate transformations II (plants) 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 1.5.1.20 5-methyl-tetrahydrofolate + NAD+ = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H+ + NADH folate transformations I 5,10-methylenetetrahydropteroyl mono-L-glutamate 5,10-methylene-THF*N5,N10-methylenetetrahydrofolate*5,10-methylenetetrahydrofolate 455.429 C20 H21 N7 O6 C23([H])(CN(CN(C1(=C(NC(N)=NC(=O)1)NC2))3)C4(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=4)) KNAPKSACK:C00007250*KNAPSACK:C00007250:*CHEBI:1989:*PUBCHEM:445117:*LIGAND-CPD:C00143: 1.5.1.20 5-methyl-tetrahydrofolate + NAD+ = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H+ + NADH folate transformations II (plants) palmitoyl-CoA palmitoyl CoA*Palmitoyl-CoA (n-C16:0CoA)*hexadecanoyl CoA*palmityl-CoA*palmitoyl coenzyme A*palmitoyl-CoA 1001.915 C37 H62 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(CCCCCCCCCCCCCCC)=O PUBCHEM:25243942:*CHEBI:57379:*PUBCHEM:45266605:*LIGAND-CPD:C00154:*CAS:1763-10-6 2.3.1.50 H+ + L-serine + palmitoyl-CoA = CO2 + 3-dehydrosphinganine + coenzyme A sphingolipid biosynthesis (plants) jasmonoyl-CoA 955.76 C33 H48 N7 O18 P3 S1 C(C4(C(=O)CCC(CC(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)4))C=CCC PUBCHEM:44237154: 2.3.1.16 OPC4-3-ketoacyl-CoA + coenzyme A = acetyl-CoA + jasmonoyl-CoA jasmonic acid biosynthesis jasmonoyl-CoA 955.76 C33 H48 N7 O18 P3 S1 C(C4(C(=O)CCC(CC(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)4))C=CCC PUBCHEM:44237154: 3.1.2.20 jasmonoyl-CoA + H2O = H+ + (+)-7-iso-jasmonate + coenzyme A jasmonic acid biosynthesis keto-phenylpyruvate phenylpyruvate*phenylpyruvic acid*α-ketohydrocinnamic acid*3-phenyl-2-oxopropanoate*keto-phenylpyruvate*2-keto-phenyl-pyruvate 163.152 C9 H7 O3 C(C(=O)C(=O)[O-])C1(=CC=CC=C1) CHEBI:18005:*PUBCHEM:4592697:*PUBCHEM:997:*LIGAND-CPD:C00166:*CAS:156-06-9 2.6.1.57 keto-phenylpyruvate + L-glutamate = L-phenylalanine + 2-oxoglutarate phenylalanine biosynthesis I keto-phenylpyruvate phenylpyruvate*phenylpyruvic acid*α-ketohydrocinnamic acid*3-phenyl-2-oxopropanoate*keto-phenylpyruvate*2-keto-phenyl-pyruvate 163.152 C9 H7 O3 C(C(=O)C(=O)[O-])C1(=CC=CC=C1) CHEBI:18005:*PUBCHEM:4592697:*PUBCHEM:997:*LIGAND-CPD:C00166:*CAS:156-06-9 4.2.1.51 H+ + prephenate = keto-phenylpyruvate + H2O + CO2 phenylalanine biosynthesis I β-elemene elemene*2,4-diisopropenyl-1-methyl-1-vinylcyclohexane*1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)-cyclohexane 204.355 C15 H24 CC1(C(CC(CC1)C(C)=C)C(C)=C)C=C PUBCHEM:10583: 4.2.3.- (2E,6E)-farnesyl diphosphate = β-elemene + diphosphate β-caryophyllene biosynthesis 2-methyl-6-phytyl-1,4-benzoquinol 402.659 C27 H46 O2 C(CCCC(C)CCCC(CCCC(C)C)C)(C)=CCC1(C=C(C=C(C)C=1O)O) KNAPSACK:C00007590:*PUBCHEM:23724601:*LIGAND-CPD:C15882: 2-methyl-6-phytyl-1,4-benzoquinol = δ-tocopherol vitamin E biosynthesis 2-methyl-6-phytyl-1,4-benzoquinol 402.659 C27 H46 O2 C(CCCC(C)CCCC(CCCC(C)C)C)(C)=CCC1(C=C(C=C(C)C=1O)O) KNAPSACK:C00007590:*PUBCHEM:23724601:*LIGAND-CPD:C15882: 2.1.1.- 2-methyl-6-phytyl-1,4-benzoquinol + S-adenosyl-L-methionine = H+ + 2,3-dimethyl-6-phytyl-1,4-benzoquinol + S-adenosyl-L-homocysteine vitamin E biosynthesis 2-methyl-6-phytyl-1,4-benzoquinol 402.659 C27 H46 O2 C(CCCC(C)CCCC(CCCC(C)C)C)(C)=CCC1(C=C(C=C(C)C=1O)O) KNAPSACK:C00007590:*PUBCHEM:23724601:*LIGAND-CPD:C15882: H+ + homogentisate + phytyl diphosphate = 2-methyl-6-phytyl-1,4-benzoquinol + CO2 + diphosphate vitamin E biosynthesis caffeoyl-CoA 925.647 C30 H38 N7 O19 P3 S1 N(C(=O)CCNC(=O)C(O)C(C)(COP(OP(=O)(OCC3(C(C(C(N2(C1(=C(C(N)=NC=N1)N=C2)))O3)O)OP([O-])(=O)[O-]))[O-])(=O)[O-])C)CCSC(=O)C=CC4(=CC=C(O)C(=C4)O) PUBCHEM:25243946:*LIGAND-CPD:C00323: 2.3.1.153 delphinidin-3,5-diglucoside + caffeoyl-CoA = delphinidin 3-O-glucosyl-5-O-caffeoylglucoside + coenzyme A gentiodelphin biosynthesis caffeoyl-CoA 925.647 C30 H38 N7 O19 P3 S1 N(C(=O)CCNC(=O)C(O)C(C)(COP(OP(=O)(OCC3(C(C(C(N2(C1(=C(C(N)=NC=N1)N=C2)))O3)O)OP([O-])(=O)[O-]))[O-])(=O)[O-])C)CCSC(=O)C=CC4(=CC=C(O)C(=C4)O) PUBCHEM:25243946:*LIGAND-CPD:C00323: 3.1.2.- trans-5-O-caffeoyl-D-quinate + coenzyme A = caffeoyl-CoA + L-quinate chlorogenic acid biosynthesis I caffeoyl-CoA 925.647 C30 H38 N7 O19 P3 S1 N(C(=O)CCNC(=O)C(O)C(C)(COP(OP(=O)(OCC3(C(C(C(N2(C1(=C(C(N)=NC=N1)N=C2)))O3)O)OP([O-])(=O)[O-]))[O-])(=O)[O-])C)CCSC(=O)C=CC4(=CC=C(O)C(=C4)O) PUBCHEM:25243946:*LIGAND-CPD:C00323: 3.1.2.- trans-5-O-caffeoyl-D-quinate + coenzyme A = caffeoyl-CoA + L-quinate phenylpropanoid biosynthesis caffeoyl-CoA 925.647 C30 H38 N7 O19 P3 S1 N(C(=O)CCNC(=O)C(O)C(C)(COP(OP(=O)(OCC3(C(C(C(N2(C1(=C(C(N)=NC=N1)N=C2)))O3)O)OP([O-])(=O)[O-]))[O-])(=O)[O-])C)CCSC(=O)C=CC4(=CC=C(O)C(=C4)O) PUBCHEM:25243946:*LIGAND-CPD:C00323: 6.2.1.12 trans-caffeate + coenzyme A + ATP = caffeoyl-CoA + AMP + diphosphate suberin biosynthesis caffeoyl-CoA 925.647 C30 H38 N7 O19 P3 S1 N(C(=O)CCNC(=O)C(O)C(C)(COP(OP(=O)(OCC3(C(C(C(N2(C1(=C(C(N)=NC=N1)N=C2)))O3)O)OP([O-])(=O)[O-]))[O-])(=O)[O-])C)CCSC(=O)C=CC4(=CC=C(O)C(=C4)O) PUBCHEM:25243946:*LIGAND-CPD:C00323: 2.3.1.- delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + caffeoyl-CoA = gentiodelphin + coenzyme A gentiodelphin biosynthesis caffeoyl-CoA 925.647 C30 H38 N7 O19 P3 S1 N(C(=O)CCNC(=O)C(O)C(C)(COP(OP(=O)(OCC3(C(C(C(N2(C1(=C(C(N)=NC=N1)N=C2)))O3)O)OP([O-])(=O)[O-]))[O-])(=O)[O-])C)CCSC(=O)C=CC4(=CC=C(O)C(=C4)O) PUBCHEM:25243946:*LIGAND-CPD:C00323: 2.3.1.- delphinidin 3,5,3'-triglucoside + caffeoyl-CoA = delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + coenzyme A gentiodelphin biosynthesis caffeoyl-CoA 925.647 C30 H38 N7 O19 P3 S1 N(C(=O)CCNC(=O)C(O)C(C)(COP(OP(=O)(OCC3(C(C(C(N2(C1(=C(C(N)=NC=N1)N=C2)))O3)O)OP([O-])(=O)[O-]))[O-])(=O)[O-])C)CCSC(=O)C=CC4(=CC=C(O)C(=C4)O) PUBCHEM:25243946:*LIGAND-CPD:C00323: 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = H+ + feruloyl-CoA + S-adenosyl-L-homocysteine chlorogenic acid biosynthesis I caffeoyl-CoA 925.647 C30 H38 N7 O19 P3 S1 N(C(=O)CCNC(=O)C(O)C(C)(COP(OP(=O)(OCC3(C(C(C(N2(C1(=C(C(N)=NC=N1)N=C2)))O3)O)OP([O-])(=O)[O-]))[O-])(=O)[O-])C)CCSC(=O)C=CC4(=CC=C(O)C(=C4)O) PUBCHEM:25243946:*LIGAND-CPD:C00323: 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = H+ + feruloyl-CoA + S-adenosyl-L-homocysteine suberin biosynthesis caffeoyl-CoA 925.647 C30 H38 N7 O19 P3 S1 N(C(=O)CCNC(=O)C(O)C(C)(COP(OP(=O)(OCC3(C(C(C(N2(C1(=C(C(N)=NC=N1)N=C2)))O3)O)OP([O-])(=O)[O-]))[O-])(=O)[O-])C)CCSC(=O)C=CC4(=CC=C(O)C(=C4)O) PUBCHEM:25243946:*LIGAND-CPD:C00323: 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = H+ + feruloyl-CoA + S-adenosyl-L-homocysteine phenylpropanoid biosynthesis caffeoyl-CoA 925.647 C30 H38 N7 O19 P3 S1 N(C(=O)CCNC(=O)C(O)C(C)(COP(OP(=O)(OCC3(C(C(C(N2(C1(=C(C(N)=NC=N1)N=C2)))O3)O)OP([O-])(=O)[O-]))[O-])(=O)[O-])C)CCSC(=O)C=CC4(=CC=C(O)C(=C4)O) PUBCHEM:25243946:*LIGAND-CPD:C00323: 3.1.2.- caffeoylshikimate + coenzyme A = caffeoyl-CoA + shikimate chlorogenic acid biosynthesis I caffeoyl-CoA 925.647 C30 H38 N7 O19 P3 S1 N(C(=O)CCNC(=O)C(O)C(C)(COP(OP(=O)(OCC3(C(C(C(N2(C1(=C(C(N)=NC=N1)N=C2)))O3)O)OP([O-])(=O)[O-]))[O-])(=O)[O-])C)CCSC(=O)C=CC4(=CC=C(O)C(=C4)O) PUBCHEM:25243946:*LIGAND-CPD:C00323: 3.1.2.- caffeoylshikimate + coenzyme A = caffeoyl-CoA + shikimate phenylpropanoid biosynthesis α-D-galactose α-galactose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) LIGAND-CPD:C00984:*CHEBI:28061:*PUBCHEM:439357: 3.2.1.- raffinose + H2O = α-D-galactose + sucrose stachyose degradation α-D-galactose α-galactose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) LIGAND-CPD:C00984:*CHEBI:28061:*PUBCHEM:439357: 3.2.1.22 stachyose + H2O = raffinose + α-D-galactose stachyose degradation α-D-galactose α-galactose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) LIGAND-CPD:C00984:*CHEBI:28061:*PUBCHEM:439357: 5.1.3.3 β-D-galactose = α-D-galactose galactose degradation I (Leloir pathway) α-D-galactose α-galactose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) LIGAND-CPD:C00984:*CHEBI:28061:*PUBCHEM:439357: 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP galactose degradation I (Leloir pathway) α-D-galactose α-galactose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) LIGAND-CPD:C00984:*CHEBI:28061:*PUBCHEM:439357: 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP stachyose degradation α-D-galactose α-galactose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) LIGAND-CPD:C00984:*CHEBI:28061:*PUBCHEM:439357: 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP colanic acid building blocks biosynthesis α-D-galactose α-galactose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) LIGAND-CPD:C00984:*CHEBI:28061:*PUBCHEM:439357: 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) α-D-galactose α-galactose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) LIGAND-CPD:C00984:*CHEBI:28061:*PUBCHEM:439357: 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP galactose degradation III α-D-galactose α-galactose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) LIGAND-CPD:C00984:*CHEBI:28061:*PUBCHEM:439357: 3.2.1.22 H2O + melibiose = α-D-galactose + β-D-glucose melibiose degradation AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ pyridine nucleotide cycling (plants) AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.9.2 H2O + pyruvate + ATP = H+ + phosphoenolpyruvate + AMP gluconeogenesis I AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.9.2 H2O + pyruvate + ATP = H+ + phosphoenolpyruvate + AMP glycolysis I AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP acetate conversion to acetyl-CoA AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP ethanol degradation II (cytosol) AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP ethanol degradation IV (peroxisomal) AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.4 H+ + L-leucine + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.6.3 6-hydroxymethyl-7,8-dihydropterin + ATP = H+ + 6-hydroxymethyl-dihydropterin diphosphate + AMP 6-hydroxymethyl-dihydropterin diphosphate biosynthesis AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.2 H+ + L-tryptophan + ATP = AMP + diphosphate tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid activation AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.- trans-cinnamate + coenzyme A + ATP = (E)-cinnamoyl-CoA + AMP + diphosphate trans-cinnamoyl-CoA biosynthesis AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.6 H+ + L-lysine + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2-carboxylate-4-methyl-5-beta-(ethyl adenosine 5-diphosphate) thiazole = AMP + 4-methyl-5-(2-phosphonooxyethyl)thiazole thiamine biosynthesis II AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.5.1.27 dimethylallyl diphosphate + AMP = N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate + diphosphate trans-zeatin biosynthesis AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 1.8.99.2 sulfite + AMP = adenosine 5'-phosphosulfate sulfite oxidation III AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 1.8.99.2 sulfite + AMP = adenosine 5'-phosphosulfate sulfite oxidation II AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.6.2 thiamin + ATP = H+ + thiamine diphosphate + AMP thiamine biosynthesis II AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.4.3 AMP + ATP = ADP adenosine nucleotides de novo biosynthesis AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.11 H+ + L-serine + ATP = diphosphate + AMP selenocysteine biosynthesis II (archaea and eukaryotes) AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.9.3 H2O + hydrogen selenide + ATP = selenophosphate + AMP selenocysteine biosynthesis II (archaea and eukaryotes) AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.21 H+ + L-histidine + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.4.2.7 AMP + diphosphate = adenine + 5-phospho-α-D-ribose 1-diphosphate adenine and adenosine salvage II AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.1.1 ammonia + L-aspartate + ATP = L-asparagine + diphosphate + AMP asparagine biosynthesis II AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.3 oleate + coenzyme A + ATP = oleoyl-CoA + AMP + diphosphate linoleate biosynthesis I (plants) AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 L-glutamate + ATP = AMP + diphosphate L-glutamine biosynthesis II (tRNA-dependent) AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.15 H+ + L-proline + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.14 H+ + glycine + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.17 coenzyme A + propionate + ATP = propanoyl-CoA + diphosphate + AMP β-alanine biosynthesis II AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.12 trans-caffeate + coenzyme A + ATP = caffeoyl-CoA + AMP + diphosphate suberin biosynthesis AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.18 H+ + L-glutamine + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.12 H+ + L-aspartate + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.1 H+ + L-tyrosine + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 3.6.1.22 H2O + NAD+ = H+ + nicotinamide mononucleotide + AMP pyridine nucleotide cycling (plants) AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.4.15 biotin + ATP = diphosphate + AMP biotin-carboxyl carrier protein assembly AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.22 H+ + L-asparagine + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.1.20 adenosine + ATP = H+ + AMP + ADP adenine and adenosine salvage VI AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.2.1 β-alanine + (R)-pantoate + ATP = H+ + (R)-pantothenate + diphosphate + AMP phosphopantothenate biosynthesis I AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.2.1 β-alanine + (R)-pantoate + ATP = H+ + (R)-pantothenate + diphosphate + AMP pantothenate biosynthesis I AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.5.1.- ATP = diphosphate + AMP tRNA splicing AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.9.1 pyruvate + ATP = H+ + phosphoenolpyruvate + AMP + diphosphate glutamine biosynthesis III AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.9.1 pyruvate + ATP = H+ + phosphoenolpyruvate + AMP + diphosphate C4 photosynthetic carbon assimilation cycle AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.6.1 ATP + D-ribose-5-phosphate = H+ + 5-phospho-α-D-ribose 1-diphosphate + AMP PRPP biosynthesis I AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ flavonoid biosynthesis AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ simplecoumarins biosynthesis AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ phenylpropanoid biosynthesis AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ 4-hydroxybenzoate biosynthesis V AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.7 H+ + L-alanine + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.1.5 ammonia + ATP + nicotinate adenine dinucleotide = AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.20 H+ + L-phenylalanine + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.- 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate + coenzyme A + ATP = OPC8-CoA + AMP + diphosphate jasmonic acid biosynthesis AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 3.1.3.5 AMP + H2O = adenosine adenosine nucleotides degradation II AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP urea cycle AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP arginine biosynthesis II (acetyl cycle) AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP citrulline-nitric oxide cycle AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP arginine biosynthesis I AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.10 H+ + L-methionine + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 3.5.4.6 AMP + H2O = inosine-5'-phosphate + ammonia adenosine nucleotides degradation I AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.34 ferulate + ATP + coenzyme A = feruloyl-CoA + AMP + diphosphate suberin biosynthesis AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.16 H+ + L-cysteine + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2,3-dihydroxybenzoyl-AMP = 2,3-dihydroxybenzoate-VibB + AMP vibriobactin biosynthesis AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.17 L-glutamate + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.17 L-glutamate + ATP = diphosphate + AMP tetrapyrrole biosynthesis I AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.11 H+ + L-serine + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 1.8.4.9 H+ + sulfite + AMP + glutathione disulfide = adenosine 5'-phosphosulfate + glutathione sulfate reduction II (assimilatory) AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 4.3.2.2 adenylo-succinate = fumarate + AMP purine nucleotides de novo biosynthesis II AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 4.3.2.2 adenylo-succinate = fumarate + AMP adenosine nucleotides de novo biosynthesis AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.19 H+ + L-arginine + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid β-oxidation II (core pathway) AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.9 H+ + L-valine + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.3 H+ + L-threonine + ATP = diphosphate + AMP tRNA charging pathway AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = H+ + L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis II AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = H+ + L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis I AMP AMP*A*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*adenosine-5'-phosphate*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 345.208 C10 H12 N5 O7 P1 O=P([O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:456215:*PUBCHEM:15938965:*LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.5 H+ + L-isoleucine + ATP = diphosphate + AMP tRNA charging pathway (5α)-campestan-3-one methylcholestanone*(24R)-24-methyl-5α-cholestan-3-one*3-dehydro-campestanol 400.687 C28 H48 O1 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(CCC(C(C)C)C)C)C(CC3)(C)4)))C))=O) PUBCHEM:25201374:*LIGAND-CPD:C15786: H+ + (5α)-campestan-3-one = campestanol brassinosteroid biosynthesis II (5α)-campestan-3-one methylcholestanone*(24R)-24-methyl-5α-cholestan-3-one*3-dehydro-campestanol 400.687 C28 H48 O1 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(CCC(C(C)C)C)C)C(CC3)(C)4)))C))=O) PUBCHEM:25201374:*LIGAND-CPD:C15786: 1.3.99.- H+ + campest-4-en-3-one + NADPH = (5α)-campestan-3-one + NADP+ brassinosteroid biosynthesis II (5α)-campestan-3-one methylcholestanone*(24R)-24-methyl-5α-cholestan-3-one*3-dehydro-campestanol 400.687 C28 H48 O1 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(CCC(C(C)C)C)C)C(CC3)(C)4)))C))=O) PUBCHEM:25201374:*LIGAND-CPD:C15786: 1.14.13.- H+ + (5α)-campestan-3-one + oxygen + NADPH = (22S,24R)-22-hydroxy-5α-ergostan-3-one + H2O + NADP+ brassinosteroid biosynthesis II ADP-ribose ADP-D-ribose*adenosine diphosphate ribose 557.303 C15 H21 N5 O14 P2 O=P(OP(=O)([O-])OC1(C(C(C(O1)CO)O)O))(OCC4(C(C(C(N3(C2(=C(C(=NC=N2)N)N=C3)))O4)O)O))[O-] PUBCHEM:25243947:*LIGAND-CPD:C00301:*CAS:20762-30-5 3.1.3.- ADP ribose 1''-phosphate + H2O = ADP-ribose tRNA splicing 2-aminoadipate 2-aminoadipate*L-aminoadipic acid*L-aminoadipate*L-2-aminohexanedioate*2-aminoadipic acid*hexanedioic acid, 2-amino-*α-aminoadipate*L-α-aminoadipate*L-α-aminoadipic acid*L-2-aminoadipic acid*L-2-aminoadipate 160.149 C6 H10 N1 O4 [N+]C(CCCC([O-])=O)C([O-])=O CHEBI:58672:*LIGAND-CPD:C00956:*PUBCHEM:6992111:*CAS:542-32-5 2.6.1.39 2-aminoadipate + 2-oxoglutarate = L-glutamate + 2-oxoadipate lysine degradation II 2-aminoadipate 2-aminoadipate*L-aminoadipic acid*L-aminoadipate*L-2-aminohexanedioate*2-aminoadipic acid*hexanedioic acid, 2-amino-*α-aminoadipate*L-α-aminoadipate*L-α-aminoadipic acid*L-2-aminoadipic acid*L-2-aminoadipate 160.149 C6 H10 N1 O4 [N+]C(CCCC([O-])=O)C([O-])=O CHEBI:58672:*LIGAND-CPD:C00956:*PUBCHEM:6992111:*CAS:542-32-5 1.2.1.31 Δ1-piperideine-6-carboxylate + NAD+ + H2O = 2-aminoadipate + NADH + H+ lysine degradation II 2-phosphoglycolate 2-P-glycolate*phosphoglycolate*Phosphoglycolic acid 153.008 C2 H2 O6 P1 C(OP([O-])(=O)[O-])C([O-])=O PUBCHEM:24916760:*LIGAND-CPD:C00988: 4.1.1.- D-ribulose-1,5-bisphosphate + oxygen = 2-phosphoglycolate + 3-phospho-D-glycerate + H+ photorespiration 2-phosphoglycolate 2-P-glycolate*phosphoglycolate*Phosphoglycolic acid 153.008 C2 H2 O6 P1 C(OP([O-])(=O)[O-])C([O-])=O PUBCHEM:24916760:*LIGAND-CPD:C00988: 3.1.3.18 H2O + 2-phosphoglycolate = glycolate photorespiration UDP-D-glucuronate (UDP-GlcA)1*UDP-D-glucuronic acid*UDP-glucuronic acid*udp-glcua*UDP-glucuronate*uridine diphosphate glucuronate*uridine diphosphate glucuronic acid 577.265 C15 H19 N2 O18 P2 C1(C(C(C(C(O1)OP([O-])(OP(=O)(OCC2(OC(C(C2O)O)N3(C=CC(NC3=O)=O)))[O-])=O)O)O)O)C([O-])=O PUBCHEM:25202620:*LIGAND-CPD:C00167:*CAS:2616-64-0 2.7.7.44 H+ + α-D-glucuronate 1-phosphate + UTP = UDP-D-glucuronate + diphosphate UDP-D-glucuronate biosynthesis (from myo-inositol) UDP-D-glucuronate (UDP-GlcA)1*UDP-D-glucuronic acid*UDP-glucuronic acid*udp-glcua*UDP-glucuronate*uridine diphosphate glucuronate*uridine diphosphate glucuronic acid 577.265 C15 H19 N2 O18 P2 C1(C(C(C(C(O1)OP([O-])(OP(=O)(OCC2(OC(C(C2O)O)N3(C=CC(NC3=O)=O)))[O-])=O)O)O)O)C([O-])=O PUBCHEM:25202620:*LIGAND-CPD:C00167:*CAS:2616-64-0 5.1.3.6 UDP-D-glucuronate = UDP-D-galacturonate UDP-D-galacturonate biosynthesis I (from UDP-D-glucuronate) UDP-D-glucuronate (UDP-GlcA)1*UDP-D-glucuronic acid*UDP-glucuronic acid*udp-glcua*UDP-glucuronate*uridine diphosphate glucuronate*uridine diphosphate glucuronic acid 577.265 C15 H19 N2 O18 P2 C1(C(C(C(C(O1)OP([O-])(OP(=O)(OCC2(OC(C(C2O)O)N3(C=CC(NC3=O)=O)))[O-])=O)O)O)O)C([O-])=O PUBCHEM:25202620:*LIGAND-CPD:C00167:*CAS:2616-64-0 1.1.1.22 H2O + NAD+ = H+ + UDP-D-glucuronate + NADH UDP-D-xylose and UDP-D-glucuronate biosynthesis UDP-D-glucuronate (UDP-GlcA)1*UDP-D-glucuronic acid*UDP-glucuronic acid*udp-glcua*UDP-glucuronate*uridine diphosphate glucuronate*uridine diphosphate glucuronic acid 577.265 C15 H19 N2 O18 P2 C1(C(C(C(C(O1)OP([O-])(OP(=O)(OCC2(OC(C(C2O)O)N3(C=CC(NC3=O)=O)))[O-])=O)O)O)O)C([O-])=O PUBCHEM:25202620:*LIGAND-CPD:C00167:*CAS:2616-64-0 1.1.1.22 H2O + NAD+ = H+ + UDP-D-glucuronate + NADH colanic acid building blocks biosynthesis UDP-D-glucuronate (UDP-GlcA)1*UDP-D-glucuronic acid*UDP-glucuronic acid*udp-glcua*UDP-glucuronate*uridine diphosphate glucuronate*uridine diphosphate glucuronic acid 577.265 C15 H19 N2 O18 P2 C1(C(C(C(C(O1)OP([O-])(OP(=O)(OCC2(OC(C(C2O)O)N3(C=CC(NC3=O)=O)))[O-])=O)O)O)O)C([O-])=O PUBCHEM:25202620:*LIGAND-CPD:C00167:*CAS:2616-64-0 1.1.1.22 H2O + NAD+ = H+ + UDP-D-glucuronate + NADH galactose degradation III UDP-D-glucuronate (UDP-GlcA)1*UDP-D-glucuronic acid*UDP-glucuronic acid*udp-glcua*UDP-glucuronate*uridine diphosphate glucuronate*uridine diphosphate glucuronic acid 577.265 C15 H19 N2 O18 P2 C1(C(C(C(C(O1)OP([O-])(OP(=O)(OCC2(OC(C(C2O)O)N3(C=CC(NC3=O)=O)))[O-])=O)O)O)O)C([O-])=O PUBCHEM:25202620:*LIGAND-CPD:C00167:*CAS:2616-64-0 4.1.1.35 H+ + UDP-D-glucuronate = UDP-α-D-xylose + CO2 UDP-D-xylose and UDP-D-glucuronate biosynthesis UDP-D-glucuronate (UDP-GlcA)1*UDP-D-glucuronic acid*UDP-glucuronic acid*udp-glcua*UDP-glucuronate*uridine diphosphate glucuronate*uridine diphosphate glucuronic acid 577.265 C15 H19 N2 O18 P2 C1(C(C(C(C(O1)OP([O-])(OP(=O)(OCC2(OC(C(C2O)O)N3(C=CC(NC3=O)=O)))[O-])=O)O)O)O)C([O-])=O PUBCHEM:25202620:*LIGAND-CPD:C00167:*CAS:2616-64-0 2.4.1.- UDP-D-glucuronate = UDP xylan biosynthesis 1,1-kestotetraose nystose 666.583 C24 H42 O21 C2(OC1(OC(C(O)C(C1O)O)CO))(C(C(O)C(O2)CO)O)(COC4(COC3(OC(CO)C(O)C3O)(CO))(C(O)C(O)C(CO)O4)) PUBCHEM:166775: 2.4.1.100 1-kestotriose + 1-kestotriose = 1,1-kestotetraose + sucrose fructan biosynthesis L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 6.1.1.11 H+ + L-serine + ATP = diphosphate + AMP tRNA charging pathway L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.3.1.50 H+ + L-serine + palmitoyl-CoA = CO2 + 3-dehydrosphinganine + coenzyme A sphingolipid biosynthesis (plants) L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 5.1.1.18 L-serine = D-serine serine racemization L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.7.8.8 L-serine = CMP + H+ phospholipid biosynthesis II L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.7.8.8 L-serine = CMP + H+ phosphatidylethanolamine biosynthesis I L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 4.2.1.22 L-homocysteine + L-serine = H2O + L-cystathionine homocysteine and cysteine interconversion L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.7.8.29 L-serine = ethanolamine phospholipid biosynthesis II L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O glycine biosynthesis I L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O folate transformations I L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O folate transformations II (plants) L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O folate polyglutamylation L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O photorespiration L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.3.1.30 L-serine + acetyl-CoA = O-acetyl-L-serine + coenzyme A cysteine biosynthesis I L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 6.1.1.11 H+ + L-serine + ATP = diphosphate + AMP selenocysteine biosynthesis II (archaea and eukaryotes) L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 4.1.1.- H+ + L-serine = ethanolamine + CO2 choline biosynthesis I L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.6.1.45 glyoxylate + L-serine = hydroxypyruvate + glycine photorespiration L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 4.2.1.- indole + L-serine = L-tryptophan + H2O tryptophan biosynthesis L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C([N+])(CO)C(=O)[O-] PUBCHEM:6857581:*CHEBI:33384:*PUBCHEM:6857552:*KNAPSACK:C00001393:*CHEBI:35243:*PUBCHEM:6857552:*KNAPKSACK:C00001393*LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 3.1.3.3 3-phospho-L-serine + H2O = L-serine serine biosynthesis phlorizin floridzin*phloretin 2'-glucoside*phlorhizin*phloridzin*phlorizoside 435.407 C21 H23 O10 O3(C(OC2(C(C(CCC1(C=CC(O)=CC=1))=O)=C(O)C=C([O-])C=2))C(O)C(O)C(O)C(CO)3) CHEBI:8113:*PUBCHEM:44123564: phloretin = phlorizin + UDP phloridzin biosynthesis N-acetyl-D-glucosamine-6-phosphate N-acetylglucosamine-6-P*GlcNAc-6-P*N-acetyl-D-glucosamine-6-P*N-acetyl-glucosamine-6-phosphate*N-acetyl-glucosamine-6-P 299.174 C8 H14 N1 O9 P1 CC(=O)NC1(C(O)OC(COP(=O)([O-])[O-])C(O)C(O)1) CHEBI:57513:*PUBCHEM:25243963:*LIGAND-CPD:C00357:*CAS:102029-88-9 5.4.2.3 N-acetyl-α-D-glucosamine 1-phosphate = N-acetyl-D-glucosamine-6-phosphate UDP-N-acetyl-D-glucosamine biosynthesis II N-acetyl-D-glucosamine-6-phosphate N-acetylglucosamine-6-P*GlcNAc-6-P*N-acetyl-D-glucosamine-6-P*N-acetyl-glucosamine-6-phosphate*N-acetyl-glucosamine-6-P 299.174 C8 H14 N1 O9 P1 CC(=O)NC1(C(O)OC(COP(=O)([O-])[O-])C(O)C(O)1) CHEBI:57513:*PUBCHEM:25243963:*LIGAND-CPD:C00357:*CAS:102029-88-9 2.3.1.4 D-glucosamine-6-phosphate + acetyl-CoA = H+ + N-acetyl-D-glucosamine-6-phosphate + coenzyme A UDP-N-acetyl-D-glucosamine biosynthesis II caffeoylshikimate 335.29 C16 H15 O8 O=C([O-])C1(=CC(O)C(O)C(C1)OC(=O)C=CC2(=CC=C(O)C(O)=C2)) PUBCHEM:25243950:*LIGAND-CPD:C10434: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O chlorogenic acid biosynthesis I caffeoylshikimate 335.29 C16 H15 O8 O=C([O-])C1(=CC(O)C(O)C(C1)OC(=O)C=CC2(=CC=C(O)C(O)=C2)) PUBCHEM:25243950:*LIGAND-CPD:C10434: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O chlorogenic acid biosynthesis II caffeoylshikimate 335.29 C16 H15 O8 O=C([O-])C1(=CC(O)C(O)C(C1)OC(=O)C=CC2(=CC=C(O)C(O)=C2)) PUBCHEM:25243950:*LIGAND-CPD:C10434: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O simplecoumarins biosynthesis caffeoylshikimate 335.29 C16 H15 O8 O=C([O-])C1(=CC(O)C(O)C(C1)OC(=O)C=CC2(=CC=C(O)C(O)=C2)) PUBCHEM:25243950:*LIGAND-CPD:C10434: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O phenylpropanoid biosynthesis caffeoylshikimate 335.29 C16 H15 O8 O=C([O-])C1(=CC(O)C(O)C(C1)OC(=O)C=CC2(=CC=C(O)C(O)=C2)) PUBCHEM:25243950:*LIGAND-CPD:C10434: simplecoumarins biosynthesis caffeoylshikimate 335.29 C16 H15 O8 O=C([O-])C1(=CC(O)C(O)C(C1)OC(=O)C=CC2(=CC=C(O)C(O)=C2)) PUBCHEM:25243950:*LIGAND-CPD:C10434: 3.1.2.- caffeoylshikimate + coenzyme A = caffeoyl-CoA + shikimate chlorogenic acid biosynthesis I caffeoylshikimate 335.29 C16 H15 O8 O=C([O-])C1(=CC(O)C(O)C(C1)OC(=O)C=CC2(=CC=C(O)C(O)=C2)) PUBCHEM:25243950:*LIGAND-CPD:C10434: 3.1.2.- caffeoylshikimate + coenzyme A = caffeoyl-CoA + shikimate phenylpropanoid biosynthesis D-ribose-5-phosphate D-ribose 5'-phosphate*D-ribose-5-phosphate*D-ribose-5-phosphoric acid*ribose-5-phosphoric acid*ribose-5P*D-ribose-5-P*ribose-5-P*ribose-5-phosphate*α-D-ribose-5-phosphate 228.095 C5 H9 O8 P1 O1(C(O)C(O)C(O)C(COP([O-])(=O)[O-])1) PUBCHEM:24794349:*PUBCHEM:25244540:*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: trans-zeatin riboside monophosphate + H2O = trans-zeatin + D-ribose-5-phosphate trans-zeatin biosynthesis D-ribose-5-phosphate D-ribose 5'-phosphate*D-ribose-5-phosphate*D-ribose-5-phosphoric acid*ribose-5-phosphoric acid*ribose-5P*D-ribose-5-P*ribose-5-P*ribose-5-phosphate*α-D-ribose-5-phosphate 228.095 C5 H9 O8 P1 O1(C(O)C(O)C(O)C(COP([O-])(=O)[O-])1) PUBCHEM:24794349:*PUBCHEM:25244540:*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 3.2.2.14 nicotinamide mononucleotide + H2O = H+ + D-ribose-5-phosphate + nicotinamide pyridine nucleotide cycling (plants) D-ribose-5-phosphate D-ribose 5'-phosphate*D-ribose-5-phosphate*D-ribose-5-phosphoric acid*ribose-5-phosphoric acid*ribose-5P*D-ribose-5-P*ribose-5-P*ribose-5-phosphate*α-D-ribose-5-phosphate 228.095 C5 H9 O8 P1 O1(C(O)C(O)C(O)C(COP([O-])(=O)[O-])1) PUBCHEM:24794349:*PUBCHEM:25244540:*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 3.2.2.- nicotinate mononucleotide + H2O = H+ + nicotinate + D-ribose-5-phosphate pyridine nucleotide cycling (plants) D-ribose-5-phosphate D-ribose 5'-phosphate*D-ribose-5-phosphate*D-ribose-5-phosphoric acid*ribose-5-phosphoric acid*ribose-5P*D-ribose-5-P*ribose-5-P*ribose-5-phosphate*α-D-ribose-5-phosphate 228.095 C5 H9 O8 P1 O1(C(O)C(O)C(O)C(COP([O-])(=O)[O-])1) PUBCHEM:24794349:*PUBCHEM:25244540:*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 2.7.6.1 ATP + D-ribose-5-phosphate = H+ + 5-phospho-α-D-ribose 1-diphosphate + AMP PRPP biosynthesis I D-ribose-5-phosphate D-ribose 5'-phosphate*D-ribose-5-phosphate*D-ribose-5-phosphoric acid*ribose-5-phosphoric acid*ribose-5P*D-ribose-5-P*ribose-5-P*ribose-5-phosphate*α-D-ribose-5-phosphate 228.095 C5 H9 O8 P1 O1(C(O)C(O)C(O)C(COP([O-])(=O)[O-])1) PUBCHEM:24794349:*PUBCHEM:25244540:*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 3.2.2.- N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate + H2O = N6-dimethylallyladenine + D-ribose-5-phosphate trans-zeatin biosynthesis D-ribose-5-phosphate D-ribose 5'-phosphate*D-ribose-5-phosphate*D-ribose-5-phosphoric acid*ribose-5-phosphoric acid*ribose-5P*D-ribose-5-P*ribose-5-P*ribose-5-phosphate*α-D-ribose-5-phosphate 228.095 C5 H9 O8 P1 O1(C(O)C(O)C(O)C(COP([O-])(=O)[O-])1) PUBCHEM:24794349:*PUBCHEM:25244540:*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate pentose phosphate pathway (partial) D-ribose-5-phosphate D-ribose 5'-phosphate*D-ribose-5-phosphate*D-ribose-5-phosphoric acid*ribose-5-phosphoric acid*ribose-5P*D-ribose-5-P*ribose-5-P*ribose-5-phosphate*α-D-ribose-5-phosphate 228.095 C5 H9 O8 P1 O1(C(O)C(O)C(O)C(COP([O-])(=O)[O-])1) PUBCHEM:24794349:*PUBCHEM:25244540:*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate Rubisco shunt D-ribose-5-phosphate D-ribose 5'-phosphate*D-ribose-5-phosphate*D-ribose-5-phosphoric acid*ribose-5-phosphoric acid*ribose-5P*D-ribose-5-P*ribose-5-P*ribose-5-phosphate*α-D-ribose-5-phosphate 228.095 C5 H9 O8 P1 O1(C(O)C(O)C(O)C(COP([O-])(=O)[O-])1) PUBCHEM:24794349:*PUBCHEM:25244540:*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate pentose phosphate pathway (non-oxidative branch) D-ribose-5-phosphate D-ribose 5'-phosphate*D-ribose-5-phosphate*D-ribose-5-phosphoric acid*ribose-5-phosphoric acid*ribose-5P*D-ribose-5-P*ribose-5-P*ribose-5-phosphate*α-D-ribose-5-phosphate 228.095 C5 H9 O8 P1 O1(C(O)C(O)C(O)C(COP([O-])(=O)[O-])1) PUBCHEM:24794349:*PUBCHEM:25244540:*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate Calvin-Benson-Bassham cycle D-ribose-5-phosphate D-ribose 5'-phosphate*D-ribose-5-phosphate*D-ribose-5-phosphoric acid*ribose-5-phosphoric acid*ribose-5P*D-ribose-5-P*ribose-5-P*ribose-5-phosphate*α-D-ribose-5-phosphate 228.095 C5 H9 O8 P1 O1(C(O)C(O)C(O)C(COP([O-])(=O)[O-])1) PUBCHEM:24794349:*PUBCHEM:25244540:*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 4.2.1.70 D-ribose-5-phosphate + uracil = H2O + pseudouridine 5'-phosphate pseudouridine degradation D-ribose-5-phosphate D-ribose 5'-phosphate*D-ribose-5-phosphate*D-ribose-5-phosphoric acid*ribose-5-phosphoric acid*ribose-5P*D-ribose-5-P*ribose-5-P*ribose-5-phosphate*α-D-ribose-5-phosphate 228.095 C5 H9 O8 P1 O1(C(O)C(O)C(O)C(COP([O-])(=O)[O-])1) PUBCHEM:24794349:*PUBCHEM:25244540:*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 5.3.1.6 D-ribose-5-phosphate = D-ribulose-5-phosphate Rubisco shunt D-ribose-5-phosphate D-ribose 5'-phosphate*D-ribose-5-phosphate*D-ribose-5-phosphoric acid*ribose-5-phosphoric acid*ribose-5P*D-ribose-5-P*ribose-5-P*ribose-5-phosphate*α-D-ribose-5-phosphate 228.095 C5 H9 O8 P1 O1(C(O)C(O)C(O)C(COP([O-])(=O)[O-])1) PUBCHEM:24794349:*PUBCHEM:25244540:*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 5.3.1.6 D-ribose-5-phosphate = D-ribulose-5-phosphate pentose phosphate pathway (non-oxidative branch) D-ribose-5-phosphate D-ribose 5'-phosphate*D-ribose-5-phosphate*D-ribose-5-phosphoric acid*ribose-5-phosphoric acid*ribose-5P*D-ribose-5-P*ribose-5-P*ribose-5-phosphate*α-D-ribose-5-phosphate 228.095 C5 H9 O8 P1 O1(C(O)C(O)C(O)C(COP([O-])(=O)[O-])1) PUBCHEM:24794349:*PUBCHEM:25244540:*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 5.3.1.6 D-ribose-5-phosphate = D-ribulose-5-phosphate Calvin-Benson-Bassham cycle 7,8-dihydroneopterin phosphate 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphate*dihydroneopterin-p*Dihydroneopterin monophosphate*dihydroneopterin monophosphate*dihydroneopterin-P*2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphate*dihydroneopterin phosphate 333.197 C9 H12 N5 O7 P1 NC2(=NC1(NCC(=NC=1C(=O)N2)C(O)C(O)COP(=O)([O-])[O-])) CHEBI:58762:*PUBCHEM:25245170:*LIGAND-CPD:C05925: 3.6.1.- 7,8-dihydroneopterin phosphate + H2O = 7,8-dihydro-D-neopterin 6-hydroxymethyl-dihydropterin diphosphate biosynthesis 7,8-dihydroneopterin phosphate 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphate*dihydroneopterin-p*Dihydroneopterin monophosphate*dihydroneopterin monophosphate*dihydroneopterin-P*2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphate*dihydroneopterin phosphate 333.197 C9 H12 N5 O7 P1 NC2(=NC1(NCC(=NC=1C(=O)N2)C(O)C(O)COP(=O)([O-])[O-])) CHEBI:58762:*PUBCHEM:25245170:*LIGAND-CPD:C05925: 3.6.1.- 7,8-dihydroneopterin triphosphate + H2O = H+ + 7,8-dihydroneopterin phosphate + diphosphate 6-hydroxymethyl-dihydropterin diphosphate biosynthesis D-sorbitol L-gulitol*D-glucitol*meglumine*iso-sorbide*glucitol*sorbitol 182.173 C6 H14 O6 C(O)C(C(C(C(CO)O)O)O)O PUBCHEM:5780:*CHEBI:17924:*PUBCHEM:5780:*LIGAND-CPD:C00794:*CAS:50-70-4 1.1.1.14 D-sorbitol + NAD+ = NADH + H+ sorbitol degradation I 2-methylacetoacetyl-CoA 2-methyl-3-acetoacetyl-CoA*2-methylacetoacetyl coenzyme A 861.604 C26 H38 N7 O18 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(O)C(NCCC(NCCSC(C(C(=O)C)C)=O)=O)=O)[O-])O1)OP([O-])([O-])=O)(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25244541:*LIGAND-CPD:C03344:*CAS:6712-01-2 2.3.1.9 2-methylacetoacetyl-CoA + coenzyme A = propanoyl-CoA + acetyl-CoA isoleucine degradation I 2-methylacetoacetyl-CoA 2-methyl-3-acetoacetyl-CoA*2-methylacetoacetyl coenzyme A 861.604 C26 H38 N7 O18 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(O)C(NCCC(NCCSC(C(C(=O)C)C)=O)=O)=O)[O-])O1)OP([O-])([O-])=O)(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25244541:*LIGAND-CPD:C03344:*CAS:6712-01-2 1.1.1.178 NAD+ + 2-methyl-3-hydroxybutyryl-CoA = H+ + NADH + 2-methylacetoacetyl-CoA isoleucine degradation I sinapaldehyde glucoside sinapyl aldehyde-4-O-β-D-glucopyranoside 370.355 C17 H22 O9 C1(C(=CC(=C(C=1OC)OC2(C(C(C(C(O2)CO)O)O)O))OC)C=CC=O) PUBCHEM:25244544: 2.4.1.- sinapaldehyde = H+ + sinapaldehyde glucoside + UDP monolignol glucosides biosynthesis thiocyanate thiocyanic acid*thiocyanate*hydrogen thiocyanate 58.078 C1 N1 S1 C(#N)[S-] PUBCHEM:9322:*CHEBI:18022:*CAS:463-56-9:*LIGAND-CPD:C01755: 2.8.1.1 thiosulfate + hydrogen cyanide = H+ + sulfite + thiocyanate thiosulfate disproportionation III (rhodanese) ADP ribose 1''-phosphate adenosine diphosphate ribose 1'' phosphate 635.268 C15 H20 N5 O17 P3 OC1(C(OC(C1O)COP(OP(OCC2(C(O)C(O)C(O2)OP(=O)([O-])[O-]))(=O)[O-])([O-])=O)N4(C3(C(=C(N=CN=3)N)N=C4))) PUBCHEM:44123525: 3.1.4.- ADP ribose 1'',2''-cyclic phosphate + H2O = H+ + ADP ribose 1''-phosphate tRNA splicing ADP ribose 1''-phosphate adenosine diphosphate ribose 1'' phosphate 635.268 C15 H20 N5 O17 P3 OC1(C(OC(C1O)COP(OP(OCC2(C(O)C(O)C(O2)OP(=O)([O-])[O-]))(=O)[O-])([O-])=O)N4(C3(C(=C(N=CN=3)N)N=C4))) PUBCHEM:44123525: 3.1.3.- ADP ribose 1''-phosphate + H2O = ADP-ribose tRNA splicing 5-phospho-β-D-ribosyl-amine 5-phospho-β-D-ribosyl-amine*5-P-β-D-ribosyl-amine*PRA*5-phosphoribosylamine 228.118 C5 H11 N1 O7 P1 C(C1(OC([N+])C(O)C(O)1))OP([O-])([O-])=O PUBCHEM:25245171:*LIGAND-CPD:C03090: 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide 5-aminoimidazole ribonucleotide biosynthesis II 5-phospho-β-D-ribosyl-amine 5-phospho-β-D-ribosyl-amine*5-P-β-D-ribosyl-amine*PRA*5-phosphoribosylamine 228.118 C5 H11 N1 O7 P1 C(C1(OC([N+])C(O)C(O)1))OP([O-])([O-])=O PUBCHEM:25245171:*LIGAND-CPD:C03090: 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide 5-aminoimidazole ribonucleotide biosynthesis I 5-phospho-β-D-ribosyl-amine 5-phospho-β-D-ribosyl-amine*5-P-β-D-ribosyl-amine*PRA*5-phosphoribosylamine 228.118 C5 H11 N1 O7 P1 C(C1(OC([N+])C(O)C(O)1))OP([O-])([O-])=O PUBCHEM:25245171:*LIGAND-CPD:C03090: 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide superpathway of 5-aminoimidazole ribonucleotide biosynthesis 5-phospho-β-D-ribosyl-amine 5-phospho-β-D-ribosyl-amine*5-P-β-D-ribosyl-amine*PRA*5-phosphoribosylamine 228.118 C5 H11 N1 O7 P1 C(C1(OC([N+])C(O)C(O)1))OP([O-])([O-])=O PUBCHEM:25245171:*LIGAND-CPD:C03090: 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O 5-aminoimidazole ribonucleotide biosynthesis II 5-phospho-β-D-ribosyl-amine 5-phospho-β-D-ribosyl-amine*5-P-β-D-ribosyl-amine*PRA*5-phosphoribosylamine 228.118 C5 H11 N1 O7 P1 C(C1(OC([N+])C(O)C(O)1))OP([O-])([O-])=O PUBCHEM:25245171:*LIGAND-CPD:C03090: 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O 5-aminoimidazole ribonucleotide biosynthesis I 5-phospho-β-D-ribosyl-amine 5-phospho-β-D-ribosyl-amine*5-P-β-D-ribosyl-amine*PRA*5-phosphoribosylamine 228.118 C5 H11 N1 O7 P1 C(C1(OC([N+])C(O)C(O)1))OP([O-])([O-])=O PUBCHEM:25245171:*LIGAND-CPD:C03090: 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O superpathway of 5-aminoimidazole ribonucleotide biosynthesis p-dihydrocoumaroyl-CoA 4-hydroxydihydrocinnamoyl-CoA 911.663 C30 H40 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)CCC4(=CC=C(O)C=C4) 4-coumaroyl-CoA + NADPH + FADH2 = p-dihydrocoumaroyl-CoA + NADP+ + FAD + H+ phloridzin biosynthesis p-dihydrocoumaroyl-CoA 4-hydroxydihydrocinnamoyl-CoA 911.663 C30 H40 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)CCC4(=CC=C(O)C=C4) p-dihydrocoumaroyl-CoA + malonyl-CoA = naringenin + coenzyme A + CO2 phloridzin biosynthesis p-dihydrocoumaroyl-CoA 4-hydroxydihydrocinnamoyl-CoA 911.663 C30 H40 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)CCC4(=CC=C(O)C=C4) 2.3.1.- p-dihydrocoumaroyl-CoA + malonyl-CoA + H+ = phloretin + coenzyme A + CO2 phloridzin biosynthesis stachyose α-D-Galp-(1->6)-α-D-Galp-(1->6)-α-D-Glcp-(1->2)-β-D-Fruf*(2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-[(2S,3S,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxy-oxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol*α-D-Galp-(1->6)-α-D-Galp-(1->6)-α-D-Glcp-(1<->2)-β-D-Fruf 666.583 C24 H42 O21 C4(O)(C(O)C(CO)OC(OC3(C(O)C(O)C(O)C(COC2(C(O)C(O)C(O)C(COC1(OC(CO)C(O)C(O)C(O)1))O2))O3))(CO)4) PUBCHEM:439531:*CHEBI:17164:*LIGAND-CPD:C01613:*CAS:10094-58-3 2.4.1.67 galactinol + raffinose = myo-inositol + stachyose stachyose biosynthesis stachyose α-D-Galp-(1->6)-α-D-Galp-(1->6)-α-D-Glcp-(1->2)-β-D-Fruf*(2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-[(2S,3S,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxy-oxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol*α-D-Galp-(1->6)-α-D-Galp-(1->6)-α-D-Glcp-(1<->2)-β-D-Fruf 666.583 C24 H42 O21 C4(O)(C(O)C(CO)OC(OC3(C(O)C(O)C(O)C(COC2(C(O)C(O)C(O)C(COC1(OC(CO)C(O)C(O)C(O)1))O2))O3))(CO)4) PUBCHEM:439531:*CHEBI:17164:*LIGAND-CPD:C01613:*CAS:10094-58-3 3.2.1.22 stachyose + H2O = raffinose + α-D-galactose stachyose degradation camptothecin camptothecine*d-camptothecine*(+)-camptothecine*(s)-camptothecine 348.357 C20 H16 N2 O4 C5(C4(=C(N=C3(C2(=CC1(C(CC)(O)C(=O)OCC=1C(=O)N2CC3=C4))))C=CC=5)) LIGAND-CPD:C01897:*CHEBI:27656:*PUBCHEM:24360: strictosamide = camptothecin camptothecin biosynthesis 3-O-methylquercetin 3-methoxy-5,7,3',4'-tetrahydroxyflavone*3-methoxyluteolin*3',4',5,7-tetrahydroxy-3-methoxyflavone 315.259 C16 H11 O7 COC3(C(=O)C1(C(=CC([O-])=CC(O)=1)OC(C2(C=C(O)C(O)=CC=2))=3)) PUBCHEM:5280681:*PUBCHEM:25202270:*CHEBI:16860:*LIGAND-CPD:C04443: 2.1.1.76 quercetin + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + 3-O-methylquercetin methylquercetin biosynthesis 3-O-methylquercetin 3-methoxy-5,7,3',4'-tetrahydroxyflavone*3-methoxyluteolin*3',4',5,7-tetrahydroxy-3-methoxyflavone 315.259 C16 H11 O7 COC3(C(=O)C1(C(=CC([O-])=CC(O)=1)OC(C2(C=C(O)C(O)=CC=2))=3)) PUBCHEM:5280681:*PUBCHEM:25202270:*CHEBI:16860:*LIGAND-CPD:C04443: 2.1.1.82 3-O-methylquercetin + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + 3,7-di-O-methylquercetin methylquercetin biosynthesis β-D-galactose β-D-galactopyranose*galactose*galactopyranoside*galactopyranose*D-galactose*cerebrose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) CAS:59-23-4*LIGAND-CPD:C00124:*LIGAND-CPD:C01582:*CAS:33419-42-0:*CAS:7296-64-2:*LIGAND-CPD:C00962:*CHEBI:28034:*PUBCHEM:439353: 3.2.1.23 H2O + lactose = β-D-galactose + β-D-glucose lactose degradation III β-D-galactose β-D-galactopyranose*galactose*galactopyranoside*galactopyranose*D-galactose*cerebrose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OCC1(OC(O)C(O)C(O)C(O)1) CAS:59-23-4*LIGAND-CPD:C00124:*LIGAND-CPD:C01582:*CAS:33419-42-0:*CAS:7296-64-2:*LIGAND-CPD:C00962:*CHEBI:28034:*PUBCHEM:439353: 5.1.3.3 β-D-galactose = α-D-galactose galactose degradation I (Leloir pathway) GA110 gibberellin A110*gibberellin A110*GA110 346.422 C20 H26 O5 C1(C(CC(C2(C(C34(CC(CCC(C1(C)2)3)C(C4)=C))C([O-])=O))(C)C([O-])=O)O) PUBCHEM:25243953: 1.14.11.- gibberellin A12 + 2-oxoglutarate + oxygen = GA110 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) inosine-5'-phosphate inosine-5'-phosphate*5'-IMP*ribosylhypoxanthine monophosphate*IMP*inosinate*inosine monophosphate*inosine 5'-monophosphate*inosine 5'-phosphate*5'-inosinate*5'-inosinic acid*5'-inosine monophosphate 346.193 C10 H11 N4 O8 P1 O=C1(C2(N=CN(C(N=CN1)=2)C3(OC(COP(=O)([O-])[O-])C(O)C(O)3))) PUBCHEM:7140378:*CAS:131-99-7*LIGAND-CPD:C00130: 1.1.1.205 inosine-5'-phosphate + H2O + NAD+ = xanthosine-5-phosphate + NADH + H+ adenosine nucleotides degradation I inosine-5'-phosphate inosine-5'-phosphate*5'-IMP*ribosylhypoxanthine monophosphate*IMP*inosinate*inosine monophosphate*inosine 5'-monophosphate*inosine 5'-phosphate*5'-inosinate*5'-inosinic acid*5'-inosine monophosphate 346.193 C10 H11 N4 O8 P1 O=C1(C2(N=CN(C(N=CN1)=2)C3(OC(COP(=O)([O-])[O-])C(O)C(O)3))) PUBCHEM:7140378:*CAS:131-99-7*LIGAND-CPD:C00130: 1.1.1.205 inosine-5'-phosphate + H2O + NAD+ = xanthosine-5-phosphate + NADH + H+ purine nucleotides de novo biosynthesis II inosine-5'-phosphate inosine-5'-phosphate*5'-IMP*ribosylhypoxanthine monophosphate*IMP*inosinate*inosine monophosphate*inosine 5'-monophosphate*inosine 5'-phosphate*5'-inosinate*5'-inosinic acid*5'-inosine monophosphate 346.193 C10 H11 N4 O8 P1 O=C1(C2(N=CN(C(N=CN1)=2)C3(OC(COP(=O)([O-])[O-])C(O)C(O)3))) PUBCHEM:7140378:*CAS:131-99-7*LIGAND-CPD:C00130: 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = H+ + adenylo-succinate + GDP purine nucleotides de novo biosynthesis II inosine-5'-phosphate inosine-5'-phosphate*5'-IMP*ribosylhypoxanthine monophosphate*IMP*inosinate*inosine monophosphate*inosine 5'-monophosphate*inosine 5'-phosphate*5'-inosinate*5'-inosinic acid*5'-inosine monophosphate 346.193 C10 H11 N4 O8 P1 O=C1(C2(N=CN(C(N=CN1)=2)C3(OC(COP(=O)([O-])[O-])C(O)C(O)3))) PUBCHEM:7140378:*CAS:131-99-7*LIGAND-CPD:C00130: 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = H+ + adenylo-succinate + GDP adenosine nucleotides de novo biosynthesis inosine-5'-phosphate inosine-5'-phosphate*5'-IMP*ribosylhypoxanthine monophosphate*IMP*inosinate*inosine monophosphate*inosine 5'-monophosphate*inosine 5'-phosphate*5'-inosinate*5'-inosinic acid*5'-inosine monophosphate 346.193 C10 H11 N4 O8 P1 O=C1(C2(N=CN(C(N=CN1)=2)C3(OC(COP(=O)([O-])[O-])C(O)C(O)3))) PUBCHEM:7140378:*CAS:131-99-7*LIGAND-CPD:C00130: 3.5.4.10 inosine-5'-phosphate + H2O = phosphoribosyl-formamido-carboxamide inosine-5'-phosphate biosynthesis II inosine-5'-phosphate inosine-5'-phosphate*5'-IMP*ribosylhypoxanthine monophosphate*IMP*inosinate*inosine monophosphate*inosine 5'-monophosphate*inosine 5'-phosphate*5'-inosinate*5'-inosinic acid*5'-inosine monophosphate 346.193 C10 H11 N4 O8 P1 O=C1(C2(N=CN(C(N=CN1)=2)C3(OC(COP(=O)([O-])[O-])C(O)C(O)3))) PUBCHEM:7140378:*CAS:131-99-7*LIGAND-CPD:C00130: 3.1.3.5 inosine-5'-phosphate + H2O = inosine adenosine nucleotides degradation I inosine-5'-phosphate inosine-5'-phosphate*5'-IMP*ribosylhypoxanthine monophosphate*IMP*inosinate*inosine monophosphate*inosine 5'-monophosphate*inosine 5'-phosphate*5'-inosinate*5'-inosinic acid*5'-inosine monophosphate 346.193 C10 H11 N4 O8 P1 O=C1(C2(N=CN(C(N=CN1)=2)C3(OC(COP(=O)([O-])[O-])C(O)C(O)3))) PUBCHEM:7140378:*CAS:131-99-7*LIGAND-CPD:C00130: 3.5.4.6 AMP + H2O = inosine-5'-phosphate + ammonia adenosine nucleotides degradation I bis-noryangonin BNY 230.22 C13 H9 O4 C1(C(O)=CC=C(C=1)C=CC2(OC(=O)C=C([O-])C=2)) PUBCHEM:25245184:*LIGAND-CPD:C12085: 2.3.1.- H+ + 4-coumaroyl-CoA + malonyl-CoA = bis-noryangonin + coenzyme A + CO2 resveratrol biosynthesis 2,3-dihydroxy-isovalerate 2,3-dihydroxy-3-methylbutanoate*(R)-2,3-dihydroxy-3-methylbutanoate*α,β-dihydroxy-isovalerate 133.124 C5 H9 O4 C(C(C)(C)O)(C(=O)[O-])O PUBCHEM:21933884:*CHEBI:11424:*LIGAND-CPD:C04272: 1.1.1.86 2,3-dihydroxy-isovalerate + NADP+ = (S)-2-acetolactate + NADPH + H+ valine biosynthesis 2,3-dihydroxy-isovalerate 2,3-dihydroxy-3-methylbutanoate*(R)-2,3-dihydroxy-3-methylbutanoate*α,β-dihydroxy-isovalerate 133.124 C5 H9 O4 C(C(C)(C)O)(C(=O)[O-])O PUBCHEM:21933884:*CHEBI:11424:*LIGAND-CPD:C04272: 4.2.1.9 2,3-dihydroxy-isovalerate = 2-oxoisovalerate + H2O valine biosynthesis mevalonate-5-phosphate mevalonate-5P*(R)-5-Phosphomevalonic acid*mevalonate-5-phosphate*(R)-5-Phosphomevalonate*(R)-Mevalonic acid 5-phosphate*(R)-5-Phosphomevaloonic acid*mevalonate-5-P*mevalonate-P*P-mevalonate*5-phosphomevalonate 225.115 C6 H10 O7 P1 CC(O)(CCOP(=O)([O-])[O-])CC(=O)[O-] PUBCHEM:25244548:*LIGAND-CPD:C01107:*CAS:73566-35-5 2.7.1.36 (R)-mevalonate + ATP = H+ + mevalonate-5-phosphate + ADP mevalonate pathway I mevalonate-5-phosphate mevalonate-5P*(R)-5-Phosphomevalonic acid*mevalonate-5-phosphate*(R)-5-Phosphomevalonate*(R)-Mevalonic acid 5-phosphate*(R)-5-Phosphomevaloonic acid*mevalonate-5-P*mevalonate-P*P-mevalonate*5-phosphomevalonate 225.115 C6 H10 O7 P1 CC(O)(CCOP(=O)([O-])[O-])CC(=O)[O-] PUBCHEM:25244548:*LIGAND-CPD:C01107:*CAS:73566-35-5 2.7.4.2 mevalonate-5-phosphate + ATP = mevalonate-diphosphate + ADP mevalonate pathway I D-myo-inositol (1,4,5)-trisphosphate inositol (1,4,5)-trisphosphate*1D-myo-inositol (1,4,5)-trisphosphate*Ins(1,4,5)P3*I(1,4,5)P3*InsP3*IP3*triphosphoinositol 414.049 C6 H9 O15 P3 O=P([O-])([O-])OC1(C(O)C(OP([O-])([O-])=O)C(O)C(O)C(OP(=O)([O-])[O-])1) CHEBI:203600:*PUBCHEM:21761708:*|Wikipedia|:Inositol_triphosphate:*LIGAND-CPD:C01245:*CAS:85166-31-0:*CAS:88269-39-0: 2.7.1.151 D-myo-inositol (1,4,5)-trisphosphate + ATP = H+ + D-myo-inositol (1,4,5,6)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) D-myo-inositol (1,4,5)-trisphosphate inositol (1,4,5)-trisphosphate*1D-myo-inositol (1,4,5)-trisphosphate*Ins(1,4,5)P3*I(1,4,5)P3*InsP3*IP3*triphosphoinositol 414.049 C6 H9 O15 P3 O=P([O-])([O-])OC1(C(O)C(OP([O-])([O-])=O)C(O)C(O)C(OP(=O)([O-])[O-])1) CHEBI:203600:*PUBCHEM:21761708:*|Wikipedia|:Inositol_triphosphate:*LIGAND-CPD:C01245:*CAS:85166-31-0:*CAS:88269-39-0: 2.7.1.151 D-myo-inositol (1,4,5)-trisphosphate + ATP = H+ + D-myo-inositol (1,4,5,6)-tetrakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) D-myo-inositol (1,4,5)-trisphosphate inositol (1,4,5)-trisphosphate*1D-myo-inositol (1,4,5)-trisphosphate*Ins(1,4,5)P3*I(1,4,5)P3*InsP3*IP3*triphosphoinositol 414.049 C6 H9 O15 P3 O=P([O-])([O-])OC1(C(O)C(OP([O-])([O-])=O)C(O)C(O)C(OP(=O)([O-])[O-])1) CHEBI:203600:*PUBCHEM:21761708:*|Wikipedia|:Inositol_triphosphate:*LIGAND-CPD:C01245:*CAS:85166-31-0:*CAS:88269-39-0: 3.1.3.56 H2O + D-myo-inositol (1,4,5)-trisphosphate = D-myo-inositol (1,4)-bisphosphate D-myo-inositol (1,4,5)-trisphosphate degradation D-myo-inositol (1,4,5)-trisphosphate inositol (1,4,5)-trisphosphate*1D-myo-inositol (1,4,5)-trisphosphate*Ins(1,4,5)P3*I(1,4,5)P3*InsP3*IP3*triphosphoinositol 414.049 C6 H9 O15 P3 O=P([O-])([O-])OC1(C(O)C(OP([O-])([O-])=O)C(O)C(O)C(OP(=O)([O-])[O-])1) CHEBI:203600:*PUBCHEM:21761708:*|Wikipedia|:Inositol_triphosphate:*LIGAND-CPD:C01245:*CAS:85166-31-0:*CAS:88269-39-0: 2.7.1.127 D-myo-inositol (1,4,5)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) D-myo-inositol (1,4,5)-trisphosphate inositol (1,4,5)-trisphosphate*1D-myo-inositol (1,4,5)-trisphosphate*Ins(1,4,5)P3*I(1,4,5)P3*InsP3*IP3*triphosphoinositol 414.049 C6 H9 O15 P3 O=P([O-])([O-])OC1(C(O)C(OP([O-])([O-])=O)C(O)C(O)C(OP(=O)([O-])[O-])1) CHEBI:203600:*PUBCHEM:21761708:*|Wikipedia|:Inositol_triphosphate:*LIGAND-CPD:C01245:*CAS:85166-31-0:*CAS:88269-39-0: 3.1.4.11 H2O = D-myo-inositol (1,4,5)-trisphosphate phospholipases D-myo-inositol (1,4,5)-trisphosphate inositol (1,4,5)-trisphosphate*1D-myo-inositol (1,4,5)-trisphosphate*Ins(1,4,5)P3*I(1,4,5)P3*InsP3*IP3*triphosphoinositol 414.049 C6 H9 O15 P3 O=P([O-])([O-])OC1(C(O)C(OP([O-])([O-])=O)C(O)C(O)C(OP(=O)([O-])[O-])1) CHEBI:203600:*PUBCHEM:21761708:*|Wikipedia|:Inositol_triphosphate:*LIGAND-CPD:C01245:*CAS:85166-31-0:*CAS:88269-39-0: 3.1.4.11 H2O = D-myo-inositol (1,4,5)-trisphosphate D-myo-inositol (1,4,5)-trisphosphate biosynthesis ent-kaurene ent-kaur-16-ene*ent-kaurene 272.473 C20 H32 C1(CCC(C2(C1(C3(CCC4(CC(CC2)3CC4=C)))C))(C)C) PUBCHEM:11966109:*LIGAND-CPD:C06090:*CHEBI:15415: 4.2.3.19 ent-copalyl diphosphate = diphosphate + ent-kaurene ent-kaurene biosynthesis I ent-kaurene ent-kaur-16-ene*ent-kaurene 272.473 C20 H32 C1(CCC(C2(C1(C3(CCC4(CC(CC2)3CC4=C)))C))(C)C) PUBCHEM:11966109:*LIGAND-CPD:C06090:*CHEBI:15415: all-trans-geranyl-geranyl diphosphate = ent-kaurene + diphosphate ent -kaurene biosynthesis II ent-kaurene ent-kaur-16-ene*ent-kaurene 272.473 C20 H32 C1(CCC(C2(C1(C3(CCC4(CC(CC2)3CC4=C)))C))(C)C) PUBCHEM:11966109:*LIGAND-CPD:C06090:*CHEBI:15415: 1.14.13.78 H+ + ent-kaurene + oxygen + NADPH = H2O + NADP+ + ent-kaurenol GA12 biosynthesis linoleate omega-6 fatty acid*ω-6 fatty acid*cis,cis-9,12-octadecadienoate*9-cis,12-cis-octadecadienoate*linoleic acid*linoleate*9,12-linoleic acid*(9Z,12Z)-octadeca-9,12-dienoate 279.442 C18 H31 O2 C(CCCCCCC=CCC=CCCCCC)C([O-])=O PUBCHEM:5460332:*CHEBI:30245:*LIGAND-CPD:C01595:*NCI:281243*CAS:60-33-3 1.13.11.12 linoleate + oxygen = (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate traumatin and (Z)-3-hexen-1-yl acetate biosynthesis linoleate omega-6 fatty acid*ω-6 fatty acid*cis,cis-9,12-octadecadienoate*9-cis,12-cis-octadecadienoate*linoleic acid*linoleate*9,12-linoleic acid*(9Z,12Z)-octadeca-9,12-dienoate 279.442 C18 H31 O2 C(CCCCCCC=CCC=CCCCCC)C([O-])=O PUBCHEM:5460332:*CHEBI:30245:*LIGAND-CPD:C01595:*NCI:281243*CAS:60-33-3 1.13.11.12 linoleate + oxygen = (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate divinyl ether biosynthesis II carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 139.004 C1 H2 N1 O5 P1 NC(OP([O-])(=O)[O-])=O PUBCHEM:3423467:*LIGAND-CPD:C00169:*CAS:590-55-6 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis II (acetyl cycle) carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 139.004 C1 H2 N1 O5 P1 NC(OP([O-])(=O)[O-])=O PUBCHEM:3423467:*LIGAND-CPD:C00169:*CAS:590-55-6 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate uridine-5'-phosphate biosynthesis carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 139.004 C1 H2 N1 O5 P1 NC(OP([O-])(=O)[O-])=O PUBCHEM:3423467:*LIGAND-CPD:C00169:*CAS:590-55-6 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis I carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 139.004 C1 H2 N1 O5 P1 NC(OP([O-])(=O)[O-])=O PUBCHEM:3423467:*LIGAND-CPD:C00169:*CAS:590-55-6 6.3.4.16 ammonia + H2O + CO2 + ATP = H+ + carbamoyl-phosphate + ADP urea cycle carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 139.004 C1 H2 N1 O5 P1 NC(OP([O-])(=O)[O-])=O PUBCHEM:3423467:*LIGAND-CPD:C00169:*CAS:590-55-6 2.7.2.2 ammonia + CO2 + ATP = H+ + carbamoyl-phosphate + ADP citrulline degradation carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 139.004 C1 H2 N1 O5 P1 NC(OP([O-])(=O)[O-])=O PUBCHEM:3423467:*LIGAND-CPD:C00169:*CAS:590-55-6 2.7.2.2 ammonia + CO2 + ATP = H+ + carbamoyl-phosphate + ADP allantoin degradation IV (anaerobic) carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 139.004 C1 H2 N1 O5 P1 NC(OP([O-])(=O)[O-])=O PUBCHEM:3423467:*LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.2 L-aspartate + carbamoyl-phosphate = H+ + N-carbamoyl-L-aspartate uridine-5'-phosphate biosynthesis carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 139.004 C1 H2 N1 O5 P1 NC(OP([O-])(=O)[O-])=O PUBCHEM:3423467:*LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline urea cycle carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 139.004 C1 H2 N1 O5 P1 NC(OP([O-])(=O)[O-])=O PUBCHEM:3423467:*LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline arginine biosynthesis II (acetyl cycle) carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 139.004 C1 H2 N1 O5 P1 NC(OP([O-])(=O)[O-])=O PUBCHEM:3423467:*LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline proline biosynthesis II (from arginine) carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 139.004 C1 H2 N1 O5 P1 NC(OP([O-])(=O)[O-])=O PUBCHEM:3423467:*LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline citrulline degradation carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 139.004 C1 H2 N1 O5 P1 NC(OP([O-])(=O)[O-])=O PUBCHEM:3423467:*LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline arginine biosynthesis I carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 139.004 C1 H2 N1 O5 P1 NC(OP([O-])(=O)[O-])=O PUBCHEM:3423467:*LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline citrulline biosynthesis carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 139.004 C1 H2 N1 O5 P1 NC(OP([O-])(=O)[O-])=O PUBCHEM:3423467:*LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.5 oxamate + carbamoyl-phosphate = oxalurate allantoin degradation IV (anaerobic) 2-C-methyl-D-erythritol-2,4-cyclodiphosphate ME-2,4cPP 276.076 C5 H10 O9 P2 CC1(CO)(OP(=O)([O-])OP(=O)([O-])OCC(O)1) CHEBI:58483:*PUBCHEM:21605869:*LIGAND-CPD:C11453: 1.17.7.1 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H2O = 2-C-methyl-D-erythritol-2,4-cyclodiphosphate methylerythritol phosphate pathway 2-C-methyl-D-erythritol-2,4-cyclodiphosphate ME-2,4cPP 276.076 C5 H10 O9 P2 CC1(CO)(OP(=O)([O-])OP(=O)([O-])OCC(O)1) CHEBI:58483:*PUBCHEM:21605869:*LIGAND-CPD:C11453: 4.6.1.12 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol = 2-C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP methylerythritol phosphate pathway 3,7-di-methylquercetagetin 3',4',5,6-tetrahydroxy-3,7-dimethoxyflavone 346.293 C17 H14 O8 COC2(C=C3(OC(C1(=CC=C(O)C(O)=C1))=C(OC)C(=O)C(=C(O)C(O)=2)3)) CHEBI:27767:*PUBCHEM:148856:*LIGAND-CPD:C04581: 3,7-di-methylquercetagetin + S-adenosyl-L-methionine = H+ + 3,7,3'-tri-methylquercetagetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ pyridine nucleotide cycling (plants) L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP glutamine biosynthesis III L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP nitrate reduction II (assimilatory) L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP ammonia assimilation cycle II L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 3.5.1.2 L-glutamine + H2O = H+ + L-glutamate + ammonia glutamine degradation I L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 3.5.1.2 L-glutamine + H2O = H+ + L-glutamate + ammonia citrulline biosynthesis L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 2.6.1.85 chorismate + L-glutamine = 4-amino-4-deoxychorismate + L-glutamate p-aminobenzoate biosynthesis L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis II L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis I L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine superpathway of 5-aminoimidazole ribonucleotide biosynthesis L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 2.6.1.16 D-fructose-6-phosphate + L-glutamine = L-glutamate + D-glucosamine-6-phosphate UDP-N-acetyl-D-glucosamine biosynthesis II L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.1.1.18 H+ + L-glutamine + ATP = diphosphate + AMP tRNA charging pathway L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 1.4.1.14 NAD+ + L-glutamate = H+ + NADH + 2-oxoglutarate + L-glutamine ammonia assimilation cycle II L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 1.4.1.14 NAD+ + L-glutamate = H+ + NADH + 2-oxoglutarate + L-glutamine glutamate biosynthesis IV L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O 5-aminoimidazole ribonucleotide biosynthesis II L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O 5-aminoimidazole ribonucleotide biosynthesis I L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O superpathway of 5-aminoimidazole ribonucleotide biosynthesis L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 1.4.7.1 L-glutamate = 2-oxoglutarate + L-glutamine glutamate biosynthesis V L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 1.4.7.1 L-glutamate = 2-oxoglutarate + L-glutamine glutamine biosynthesis III L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 1.4.7.1 L-glutamate = 2-oxoglutarate + L-glutamine ammonia assimilation cycle II L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis II (acetyl cycle) L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate uridine-5'-phosphate biosynthesis L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis I L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 2.4.2.- phosphoribulosylformimino-AICAR-P + L-glutamine = H+ + L-glutamate + D-erythro-imidazole-glycerol-phosphate + aminoimidazole carboxamide ribonucleotide histidine biosynthesis L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = H+ + L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis II L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.4.2 ATP + UTP + L-glutamine + H2O = H+ + ADP + CTP + L-glutamate pyrimidine ribonucleotides interconversion L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 4.1.3.27 chorismate + L-glutamine = H+ + anthranilate + L-glutamate + pyruvate tryptophan biosynthesis L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = H+ + L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis I L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C([N+])(C(=O)[O-])CCC(=O)N PUBCHEM:25244553:*KNAPSACK:C00001359:*PUBCHEM:25244553:*LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.7 L-glutamine + ATP = L-glutamate + ADP L-glutamine biosynthesis II (tRNA-dependent) 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate SEPHCHC*5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate 326.259 C14 H14 O9 O=C([O-])CCC(=O)C1(=CCC(OC(C(O)=[O-])=C)C(O)C(C(=O)[O-])1) CHEBI:50271:*LIGAND-CPD:C16519:*PUBCHEM:24883454: 2.2.1.9 H+ + isochorismate + 2-oxoglutarate = 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + CO2 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate SEPHCHC*5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate 326.259 C14 H14 O9 O=C([O-])CCC(=O)C1(=CCC(OC(C(O)=[O-])=C)C(O)C(C(=O)[O-])1) CHEBI:50271:*LIGAND-CPD:C16519:*PUBCHEM:24883454: 4.2.99.20 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate = H+ + (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + pyruvate 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) D-sedoheptulose-7-phosphate D-Sedoheptulose-7-P*sedoheptulose-7-phosphate*heptulose-7-phosphate*sedoheptulose-7-P 288.147 C7 H13 O10 P1 C(CO)(C(O)C(C(O)C(COP(=O)([O-])[O-])O)O)=O PUBCHEM:165007:*PUBCHEM:25243964:*CHEBI:15721:*LIGAND-CPD:C00281:*CAS:2646-35-7 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = D-fructose-6-phosphate + D-erythrose-4-phosphate Rubisco shunt D-sedoheptulose-7-phosphate D-Sedoheptulose-7-P*sedoheptulose-7-phosphate*heptulose-7-phosphate*sedoheptulose-7-P 288.147 C7 H13 O10 P1 C(CO)(C(O)C(C(O)C(COP(=O)([O-])[O-])O)O)=O PUBCHEM:165007:*PUBCHEM:25243964:*CHEBI:15721:*LIGAND-CPD:C00281:*CAS:2646-35-7 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = D-fructose-6-phosphate + D-erythrose-4-phosphate pentose phosphate pathway (non-oxidative branch) D-sedoheptulose-7-phosphate D-Sedoheptulose-7-P*sedoheptulose-7-phosphate*heptulose-7-phosphate*sedoheptulose-7-P 288.147 C7 H13 O10 P1 C(CO)(C(O)C(C(O)C(COP(=O)([O-])[O-])O)O)=O PUBCHEM:165007:*PUBCHEM:25243964:*CHEBI:15721:*LIGAND-CPD:C00281:*CAS:2646-35-7 3.1.3.37 H2O + D-sedoheptulose-1,7-bisphosphate = D-sedoheptulose-7-phosphate Calvin-Benson-Bassham cycle D-sedoheptulose-7-phosphate D-Sedoheptulose-7-P*sedoheptulose-7-phosphate*heptulose-7-phosphate*sedoheptulose-7-P 288.147 C7 H13 O10 P1 C(CO)(C(O)C(C(O)C(COP(=O)([O-])[O-])O)O)=O PUBCHEM:165007:*PUBCHEM:25243964:*CHEBI:15721:*LIGAND-CPD:C00281:*CAS:2646-35-7 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate pentose phosphate pathway (partial) D-sedoheptulose-7-phosphate D-Sedoheptulose-7-P*sedoheptulose-7-phosphate*heptulose-7-phosphate*sedoheptulose-7-P 288.147 C7 H13 O10 P1 C(CO)(C(O)C(C(O)C(COP(=O)([O-])[O-])O)O)=O PUBCHEM:165007:*PUBCHEM:25243964:*CHEBI:15721:*LIGAND-CPD:C00281:*CAS:2646-35-7 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate Rubisco shunt D-sedoheptulose-7-phosphate D-Sedoheptulose-7-P*sedoheptulose-7-phosphate*heptulose-7-phosphate*sedoheptulose-7-P 288.147 C7 H13 O10 P1 C(CO)(C(O)C(C(O)C(COP(=O)([O-])[O-])O)O)=O PUBCHEM:165007:*PUBCHEM:25243964:*CHEBI:15721:*LIGAND-CPD:C00281:*CAS:2646-35-7 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate pentose phosphate pathway (non-oxidative branch) D-sedoheptulose-7-phosphate D-Sedoheptulose-7-P*sedoheptulose-7-phosphate*heptulose-7-phosphate*sedoheptulose-7-P 288.147 C7 H13 O10 P1 C(CO)(C(O)C(C(O)C(COP(=O)([O-])[O-])O)O)=O PUBCHEM:165007:*PUBCHEM:25243964:*CHEBI:15721:*LIGAND-CPD:C00281:*CAS:2646-35-7 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate Calvin-Benson-Bassham cycle (S)-malate malate*L-malic acid*L-apple acid*(S)-malic acid*hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 132.073 C4 H4 O5 O=C(C(O)CC(=O)[O-])[O-] KNAPSACK:C00001192:*CHEBI:15589:*PUBCHEM:5459792:*CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 2.3.3.9 acetyl-CoA + H2O + glyoxylate = H+ + (S)-malate + coenzyme A glyoxylate cycle (S)-malate malate*L-malic acid*L-apple acid*(S)-malic acid*hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 132.073 C4 H4 O5 O=C(C(O)CC(=O)[O-])[O-] KNAPSACK:C00001192:*CHEBI:15589:*PUBCHEM:5459792:*CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 2.3.3.9 acetyl-CoA + H2O + glyoxylate = H+ + (S)-malate + coenzyme A glycolate and glyoxylate degradation II (S)-malate malate*L-malic acid*L-apple acid*(S)-malic acid*hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 132.073 C4 H4 O5 O=C(C(O)CC(=O)[O-])[O-] KNAPSACK:C00001192:*CHEBI:15589:*PUBCHEM:5459792:*CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 4.2.1.2 (S)-malate = fumarate + H2O TCA cycle variation III (eukaryotic) (S)-malate malate*L-malic acid*L-apple acid*(S)-malic acid*hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 132.073 C4 H4 O5 O=C(C(O)CC(=O)[O-])[O-] KNAPSACK:C00001192:*CHEBI:15589:*PUBCHEM:5459792:*CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 4.2.1.2 (S)-malate = fumarate + H2O superpathway of glyoxylate cycle (S)-malate malate*L-malic acid*L-apple acid*(S)-malic acid*hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 132.073 C4 H4 O5 O=C(C(O)CC(=O)[O-])[O-] KNAPSACK:C00001192:*CHEBI:15589:*PUBCHEM:5459792:*CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.38 (S)-malate + NAD+ = NADH + CO2 + pyruvate gluconeogenesis I (S)-malate malate*L-malic acid*L-apple acid*(S)-malic acid*hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 132.073 C4 H4 O5 O=C(C(O)CC(=O)[O-])[O-] KNAPSACK:C00001192:*CHEBI:15589:*PUBCHEM:5459792:*CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH superpathway of glyoxylate cycle (S)-malate malate*L-malic acid*L-apple acid*(S)-malic acid*hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 132.073 C4 H4 O5 O=C(C(O)CC(=O)[O-])[O-] KNAPSACK:C00001192:*CHEBI:15589:*PUBCHEM:5459792:*CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.40 (S)-malate + NADP+ = NADPH + CO2 + pyruvate gluconeogenesis I (S)-malate malate*L-malic acid*L-apple acid*(S)-malic acid*hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 132.073 C4 H4 O5 O=C(C(O)CC(=O)[O-])[O-] KNAPSACK:C00001192:*CHEBI:15589:*PUBCHEM:5459792:*CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.40 (S)-malate + NADP+ = NADPH + CO2 + pyruvate C4 photosynthetic carbon assimilation cycle (S)-malate malate*L-malic acid*L-apple acid*(S)-malic acid*hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 132.073 C4 H4 O5 O=C(C(O)CC(=O)[O-])[O-] KNAPSACK:C00001192:*CHEBI:15589:*PUBCHEM:5459792:*CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH glyoxylate cycle (S)-malate malate*L-malic acid*L-apple acid*(S)-malic acid*hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 132.073 C4 H4 O5 O=C(C(O)CC(=O)[O-])[O-] KNAPSACK:C00001192:*CHEBI:15589:*PUBCHEM:5459792:*CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH gluconeogenesis I (S)-malate malate*L-malic acid*L-apple acid*(S)-malic acid*hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 132.073 C4 H4 O5 O=C(C(O)CC(=O)[O-])[O-] KNAPSACK:C00001192:*CHEBI:15589:*PUBCHEM:5459792:*CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH TCA cycle variation III (eukaryotic) (S)-malate malate*L-malic acid*L-apple acid*(S)-malic acid*hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 132.073 C4 H4 O5 O=C(C(O)CC(=O)[O-])[O-] KNAPSACK:C00001192:*CHEBI:15589:*PUBCHEM:5459792:*CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH aspartate degradation II (S)-malate malate*L-malic acid*L-apple acid*(S)-malic acid*hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 132.073 C4 H4 O5 O=C(C(O)CC(=O)[O-])[O-] KNAPSACK:C00001192:*CHEBI:15589:*PUBCHEM:5459792:*CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.82 (S)-malate + NADP+ = H+ + NADPH + oxaloacetate C4 photosynthetic carbon assimilation cycle (2E,6E)-farnesyl diphosphate 2-trans,6-trans-farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*FPP*trans, trans-farnesyl diphosphate*farnesyl-PP*farnesyl pyrophosphate*ω,E,E-farnesyl diphosphate*farnesyl diphosphate*(E,E)-farnesyl diphosphate*all-trans-farnesyl diphosphate 379.306 C15 H25 O7 P2 CC(=CCCC(=CCCC(=CCOP(OP([O-])(=O)[O-])(=O)[O-])C)C)C CHEBI:175763:*KNAPSACK:C00007268:*PUBCHEM:15983959:*LIGAND-CPD:C00448:*CAS:13058-04-3 2.5.1.31 (2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = di-trans,octa-cis-undecaprenyl diphosphate + diphosphate di-trans,poly-cis-undecaprenyl phosphate biosynthesis (2E,6E)-farnesyl diphosphate 2-trans,6-trans-farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*FPP*trans, trans-farnesyl diphosphate*farnesyl-PP*farnesyl pyrophosphate*ω,E,E-farnesyl diphosphate*farnesyl diphosphate*(E,E)-farnesyl diphosphate*all-trans-farnesyl diphosphate 379.306 C15 H25 O7 P2 CC(=CCCC(=CCCC(=CCOP(OP([O-])(=O)[O-])(=O)[O-])C)C)C CHEBI:175763:*KNAPSACK:C00007268:*PUBCHEM:15983959:*LIGAND-CPD:C00448:*CAS:13058-04-3 2.5.1.10 geranyl diphosphate + isopentenyl diphosphate = (2E,6E)-farnesyl diphosphate + diphosphate linalool biosynthesis (2E,6E)-farnesyl diphosphate 2-trans,6-trans-farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*FPP*trans, trans-farnesyl diphosphate*farnesyl-PP*farnesyl pyrophosphate*ω,E,E-farnesyl diphosphate*farnesyl diphosphate*(E,E)-farnesyl diphosphate*all-trans-farnesyl diphosphate 379.306 C15 H25 O7 P2 CC(=CCCC(=CCCC(=CCOP(OP([O-])(=O)[O-])(=O)[O-])C)C)C CHEBI:175763:*KNAPSACK:C00007268:*PUBCHEM:15983959:*LIGAND-CPD:C00448:*CAS:13058-04-3 2.5.1.10 geranyl diphosphate + isopentenyl diphosphate = (2E,6E)-farnesyl diphosphate + diphosphate trans, trans-farnesyl diphosphate biosynthesis (2E,6E)-farnesyl diphosphate 2-trans,6-trans-farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*FPP*trans, trans-farnesyl diphosphate*farnesyl-PP*farnesyl pyrophosphate*ω,E,E-farnesyl diphosphate*farnesyl diphosphate*(E,E)-farnesyl diphosphate*all-trans-farnesyl diphosphate 379.306 C15 H25 O7 P2 CC(=CCCC(=CCCC(=CCOP(OP([O-])(=O)[O-])(=O)[O-])C)C)C CHEBI:175763:*KNAPSACK:C00007268:*PUBCHEM:15983959:*LIGAND-CPD:C00448:*CAS:13058-04-3 4.2.3.- (2E,6E)-farnesyl diphosphate = β-elemene + diphosphate β-caryophyllene biosynthesis (2E,6E)-farnesyl diphosphate 2-trans,6-trans-farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*FPP*trans, trans-farnesyl diphosphate*farnesyl-PP*farnesyl pyrophosphate*ω,E,E-farnesyl diphosphate*farnesyl diphosphate*(E,E)-farnesyl diphosphate*all-trans-farnesyl diphosphate 379.306 C15 H25 O7 P2 CC(=CCCC(=CCCC(=CCOP(OP([O-])(=O)[O-])(=O)[O-])C)C)C CHEBI:175763:*KNAPSACK:C00007268:*PUBCHEM:15983959:*LIGAND-CPD:C00448:*CAS:13058-04-3 2.5.1.21 (2E,6E)-farnesyl diphosphate = presqualene diphosphate + diphosphate epoxysqualene biosynthesis (2E,6E)-farnesyl diphosphate 2-trans,6-trans-farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*FPP*trans, trans-farnesyl diphosphate*farnesyl-PP*farnesyl pyrophosphate*ω,E,E-farnesyl diphosphate*farnesyl diphosphate*(E,E)-farnesyl diphosphate*all-trans-farnesyl diphosphate 379.306 C15 H25 O7 P2 CC(=CCCC(=CCCC(=CCOP(OP([O-])(=O)[O-])(=O)[O-])C)C)C CHEBI:175763:*KNAPSACK:C00007268:*PUBCHEM:15983959:*LIGAND-CPD:C00448:*CAS:13058-04-3 4.2.3.- (2E,6E)-farnesyl diphosphate = α-humulene + diphosphate β-caryophyllene biosynthesis (2E,6E)-farnesyl diphosphate 2-trans,6-trans-farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*FPP*trans, trans-farnesyl diphosphate*farnesyl-PP*farnesyl pyrophosphate*ω,E,E-farnesyl diphosphate*farnesyl diphosphate*(E,E)-farnesyl diphosphate*all-trans-farnesyl diphosphate 379.306 C15 H25 O7 P2 CC(=CCCC(=CCCC(=CCOP(OP([O-])(=O)[O-])(=O)[O-])C)C)C CHEBI:175763:*KNAPSACK:C00007268:*PUBCHEM:15983959:*LIGAND-CPD:C00448:*CAS:13058-04-3 2.5.1.29 (2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-geranyl-geranyl diphosphate + diphosphate geranylgeranyldiphosphate biosynthesis (2E,6E)-farnesyl diphosphate 2-trans,6-trans-farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*FPP*trans, trans-farnesyl diphosphate*farnesyl-PP*farnesyl pyrophosphate*ω,E,E-farnesyl diphosphate*farnesyl diphosphate*(E,E)-farnesyl diphosphate*all-trans-farnesyl diphosphate 379.306 C15 H25 O7 P2 CC(=CCCC(=CCCC(=CCOP(OP([O-])(=O)[O-])(=O)[O-])C)C)C CHEBI:175763:*KNAPSACK:C00007268:*PUBCHEM:15983959:*LIGAND-CPD:C00448:*CAS:13058-04-3 2.5.1.29 (2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-geranyl-geranyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III (2E,6E)-farnesyl diphosphate 2-trans,6-trans-farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*FPP*trans, trans-farnesyl diphosphate*farnesyl-PP*farnesyl pyrophosphate*ω,E,E-farnesyl diphosphate*farnesyl diphosphate*(E,E)-farnesyl diphosphate*all-trans-farnesyl diphosphate 379.306 C15 H25 O7 P2 CC(=CCCC(=CCCC(=CCOP(OP([O-])(=O)[O-])(=O)[O-])C)C)C CHEBI:175763:*KNAPSACK:C00007268:*PUBCHEM:15983959:*LIGAND-CPD:C00448:*CAS:13058-04-3 4.2.3.49 (2E,6E)-farnesyl diphosphate + H2O = (3R,6E)-nerolidol + diphosphate (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis (2E,6E)-farnesyl diphosphate 2-trans,6-trans-farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*FPP*trans, trans-farnesyl diphosphate*farnesyl-PP*farnesyl pyrophosphate*ω,E,E-farnesyl diphosphate*farnesyl diphosphate*(E,E)-farnesyl diphosphate*all-trans-farnesyl diphosphate 379.306 C15 H25 O7 P2 CC(=CCCC(=CCCC(=CCOP(OP([O-])(=O)[O-])(=O)[O-])C)C)C CHEBI:175763:*KNAPSACK:C00007268:*PUBCHEM:15983959:*LIGAND-CPD:C00448:*CAS:13058-04-3 4.2.3.48 (2E,6E)-farnesyl diphosphate + H2O = (3S,6E)-nerolidol + diphosphate (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis (2E,6E)-farnesyl diphosphate 2-trans,6-trans-farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*FPP*trans, trans-farnesyl diphosphate*farnesyl-PP*farnesyl pyrophosphate*ω,E,E-farnesyl diphosphate*farnesyl diphosphate*(E,E)-farnesyl diphosphate*all-trans-farnesyl diphosphate 379.306 C15 H25 O7 P2 CC(=CCCC(=CCCC(=CCOP(OP([O-])(=O)[O-])(=O)[O-])C)C)C CHEBI:175763:*KNAPSACK:C00007268:*PUBCHEM:15983959:*LIGAND-CPD:C00448:*CAS:13058-04-3 4.2.3.- (2E,6E)-farnesyl diphosphate = (E)-β-caryophyllene + diphosphate β-caryophyllene biosynthesis tyramine 4-(2-aminoethyl)phenol*2-(p-hydroxyphenyl)ethylamine*p-hydroxyphenethylamine*tyrosamine*4-(2-Aminoethyl)phenol*p-Hydroxyphenethylamine*2-(p-Hydroxyphenyl)ethylamine 138.189 C8 H12 N1 O1 C1(C=C(O)C=CC(CC[N+])=1) PUBCHEM:5249538:*CHEBI:327995:*PUBCHEM:5249538:*CAS:51-67-2:*LIGAND-CPD:C00483:*PUBCHEM:5610: 2.3.1.110 feruloyl-CoA + tyramine = H+ + N-feruloyltyramine + coenzyme A suberin biosynthesis cis-3-hexenal (3Z)-hexenal 98.144 C6 H10 O1 CCC=CCC=O PUBCHEM:643941:*LIGAND-CPD:C16310:*CAS:6789-80-6 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate = 12-oxo-cis-9-dodecenoate + cis-3-hexenal traumatin and (Z)-3-hexen-1-yl acetate biosynthesis cis-3-hexenal (3Z)-hexenal 98.144 C6 H10 O1 CCC=CCC=O PUBCHEM:643941:*LIGAND-CPD:C16310:*CAS:6789-80-6 (3Z)-hex-3-en-ol + NAD+ = cis-3-hexenal + NADH + H+ traumatin and (Z)-3-hexen-1-yl acetate biosynthesis 5-amino-6-(5-phospho-D-ribosylamino)uracil 5-amino-6-(ribosylamino)-2,4-(1H,3H)-pyrimidinedione 5'-phosphate*5-amino-6-(5'-phosphoribosylamino)uracil 352.197 C9 H13 N4 O9 P1 NC2(=C(NC1(OC(COP(=O)([O-])[O-])C(O)C(O)1))NC(=O)NC(=O)2) CHEBI:58453:*PUBCHEM:25245199:*LIGAND-CPD:C01268: 1.1.1.193 5-amino-6-(5-phospho-D-ribitylamino)uracil + NADP+ = 5-amino-6-(5-phospho-D-ribosylamino)uracil + NADPH + H+ flavin biosynthesis I (bacteria and plants) 5-amino-6-(5-phospho-D-ribosylamino)uracil 5-amino-6-(ribosylamino)-2,4-(1H,3H)-pyrimidinedione 5'-phosphate*5-amino-6-(5'-phosphoribosylamino)uracil 352.197 C9 H13 N4 O9 P1 NC2(=C(NC1(OC(COP(=O)([O-])[O-])C(O)C(O)1))NC(=O)NC(=O)2) CHEBI:58453:*PUBCHEM:25245199:*LIGAND-CPD:C01268: 3.5.4.26 H2O + 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one = 5-amino-6-(5-phospho-D-ribosylamino)uracil + ammonia flavin biosynthesis I (bacteria and plants) (22α)-hydroxy-campesterol (22S)-22-hydroxy-campesterol 416.686 C28 H48 O2 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))O) PUBCHEM:11133505:*LIGAND-CPD:C15795: 1.14.13.- H+ + campesterol + oxygen + NADPH = (22α)-hydroxy-campesterol + H2O + NADP+ brassinosteroid biosynthesis II (22α)-hydroxy-campesterol (22S)-22-hydroxy-campesterol 416.686 C28 H48 O2 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))O) PUBCHEM:11133505:*LIGAND-CPD:C15795: 1.14.13.- H+ + (22α)-hydroxy-campesterol + NADPH + oxygen = (22R,23R)-22,23-dihydroxycampesterol + NADP+ + H2O brassinosteroid biosynthesis II (22α)-hydroxy-campesterol (22S)-22-hydroxy-campesterol 416.686 C28 H48 O2 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))O) PUBCHEM:11133505:*LIGAND-CPD:C15795: (22α)-hydroxy-campesterol = H+ + (22α)-hydroxy-campest-4-en-3-one brassinosteroid biosynthesis II dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 2.5.1.72 α-iminosuccinate + dihydroxyacetone phosphate = quinolinate + H2O NAD biosynthesis I (from aspartate) dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 4.1.2.- dihydroxyacetone phosphate + D-erythrose-4-phosphate = D-sedoheptulose-1,7-bisphosphate Calvin-Benson-Bassham cycle dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 1.1.5.3 sn-glycerol-3-phosphate = dihydroxyacetone phosphate glycerol-3-phosphate shuttle dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 1.1.5.3 sn-glycerol-3-phosphate = dihydroxyacetone phosphate glycerol degradation IV dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 1.1.5.3 sn-glycerol-3-phosphate + ubiquinone-8 = ubiquinol-8 + dihydroxyacetone phosphate glycerol degradation I dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 4.1.2.13 fructose-1,6-bisphosphate = dihydroxyacetone phosphate + D-glyceraldehyde-3-phosphate gluconeogenesis I dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 4.1.2.13 fructose-1,6-bisphosphate = dihydroxyacetone phosphate + D-glyceraldehyde-3-phosphate glycolysis III dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 4.1.2.13 fructose-1,6-bisphosphate = dihydroxyacetone phosphate + D-glyceraldehyde-3-phosphate glycolysis IV (plant cytosol) dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 4.1.2.13 fructose-1,6-bisphosphate = dihydroxyacetone phosphate + D-glyceraldehyde-3-phosphate glycolysis I dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 4.1.2.13 fructose-1,6-bisphosphate = dihydroxyacetone phosphate + D-glyceraldehyde-3-phosphate Calvin-Benson-Bassham cycle dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxyacetone phosphate glycolysis III dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxyacetone phosphate glycolysis IV (plant cytosol) dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxyacetone phosphate glycolysis I dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxyacetone phosphate Calvin-Benson-Bassham cycle dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 1.1.1.94 sn-glycerol-3-phosphate = dihydroxyacetone phosphate + H+ CDP-diacylglycerol biosynthesis II dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 1.1.1.94 sn-glycerol-3-phosphate = dihydroxyacetone phosphate + H+ CDP-diacylglycerol biosynthesis I dihydroxyacetone phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxy-acetone-phosphate*dihydroxyacetone-phosphate*dihydroxy-acetone phosphate 168.043 C3 H5 O6 P1 [O-]P(OCC(=O)CO)([O-])=O CHEBI:57642:*PUBCHEM:4643300:*PUBCHEM:4643300:*LIGAND-CPD:C00111:*CAS:57-04-5 1.1.1.8 sn-glycerol-3-phosphate + NAD+ = dihydroxyacetone phosphate + NADH + H+ glycerol-3-phosphate shuttle 4-aminobutanal 4-aminobutanal*4-amino-butyraldehyde*γ-aminobutyraldehyde*4-aminobutyraldehyde 88.129 C4 H10 N1 O1 C(CCC[N+])=O PUBCHEM:25245200:*LIGAND-CPD:C00555:*CAS:4390-05-0 1.4.3.10 oxygen + H2O + putrescine = H+ + ammonia + hydrogen peroxide + 4-aminobutanal putrescine degradation IV 4-aminobutanal 4-aminobutanal*4-amino-butyraldehyde*γ-aminobutyraldehyde*4-aminobutyraldehyde 88.129 C4 H10 N1 O1 C(CCC[N+])=O PUBCHEM:25245200:*LIGAND-CPD:C00555:*CAS:4390-05-0 1.2.1.19 4-aminobutanal + NAD+ + H2O = 4-aminobutyrate + NADH + H+ putrescine degradation IV 4-aminobutanal 4-aminobutanal*4-amino-butyraldehyde*γ-aminobutyraldehyde*4-aminobutyraldehyde 88.129 C4 H10 N1 O1 C(CCC[N+])=O PUBCHEM:25245200:*LIGAND-CPD:C00555:*CAS:4390-05-0 1.5.3.14 spermidine + oxygen + H2O = propane-1,3-diamine + 4-aminobutanal + hydrogen peroxide spermine and spermidine degradation II 4-aminobutanal 4-aminobutanal*4-amino-butyraldehyde*γ-aminobutyraldehyde*4-aminobutyraldehyde 88.129 C4 H10 N1 O1 C(CCC[N+])=O PUBCHEM:25245200:*LIGAND-CPD:C00555:*CAS:4390-05-0 4-aminobutanal = 1-pyrroline + H2O putrescine degradation IV 4-aminobutanal 4-aminobutanal*4-amino-butyraldehyde*γ-aminobutyraldehyde*4-aminobutyraldehyde 88.129 C4 H10 N1 O1 C(CCC[N+])=O PUBCHEM:25245200:*LIGAND-CPD:C00555:*CAS:4390-05-0 4-aminobutanal = 1-pyrroline + H2O spermine and spermidine degradation II OPC4-trans-2-enoyl-CoA 981.797 C35 H50 N7 O18 P3 S1 C(C4(C(=O)CCC(CC=CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])4))C=CCC PUBCHEM:44237329: 1.3.3.6 OPC4-CoA + oxygen = OPC4-trans-2-enoyl-CoA + hydrogen peroxide jasmonic acid biosynthesis OPC4-trans-2-enoyl-CoA 981.797 C35 H50 N7 O18 P3 S1 C(C4(C(=O)CCC(CC=CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])4))C=CCC PUBCHEM:44237329: 4.2.1.17 OPC4-3-hydroxyacyl-CoA = OPC4-trans-2-enoyl-CoA + H2O jasmonic acid biosynthesis succinate semialdehyde succinyl semialdehyde*succ-S-ald*succinic semialdehyde 101.082 C4 H5 O3 C(CCC=O)(=O)[O-] PUBCHEM:9543238:*CHEBI:57706:*CHEBI:16265*PUBCHEM:1112*LIGAND-CPD:C00232*CAS:692-29-5:*LIGAND-CPD:C00232: 1.2.1.24 succinate semialdehyde + H2O + NAD+ = succinate + NADH + H+ glutamate degradation III (via 4-aminobutyrate) succinate semialdehyde succinyl semialdehyde*succ-S-ald*succinic semialdehyde 101.082 C4 H5 O3 C(CCC=O)(=O)[O-] PUBCHEM:9543238:*CHEBI:57706:*CHEBI:16265*PUBCHEM:1112*LIGAND-CPD:C00232*CAS:692-29-5:*LIGAND-CPD:C00232: 1.2.1.24 succinate semialdehyde + H2O + NAD+ = succinate + NADH + H+ 4-aminobutyrate degradation I succinate semialdehyde succinyl semialdehyde*succ-S-ald*succinic semialdehyde 101.082 C4 H5 O3 C(CCC=O)(=O)[O-] PUBCHEM:9543238:*CHEBI:57706:*CHEBI:16265*PUBCHEM:1112*LIGAND-CPD:C00232*CAS:692-29-5:*LIGAND-CPD:C00232: 1.2.1.79 succinate semialdehyde + NADP+ + H2O = succinate + NADPH + H+ 4-aminobutyrate degradation II succinate semialdehyde succinyl semialdehyde*succ-S-ald*succinic semialdehyde 101.082 C4 H5 O3 C(CCC=O)(=O)[O-] PUBCHEM:9543238:*CHEBI:57706:*CHEBI:16265*PUBCHEM:1112*LIGAND-CPD:C00232*CAS:692-29-5:*LIGAND-CPD:C00232: 2.6.1.19 4-aminobutyrate + 2-oxoglutarate = succinate semialdehyde + L-glutamate glutamate degradation III (via 4-aminobutyrate) succinate semialdehyde succinyl semialdehyde*succ-S-ald*succinic semialdehyde 101.082 C4 H5 O3 C(CCC=O)(=O)[O-] PUBCHEM:9543238:*CHEBI:57706:*CHEBI:16265*PUBCHEM:1112*LIGAND-CPD:C00232*CAS:692-29-5:*LIGAND-CPD:C00232: 2.6.1.19 4-aminobutyrate + 2-oxoglutarate = succinate semialdehyde + L-glutamate 4-aminobutyrate degradation II succinate semialdehyde succinyl semialdehyde*succ-S-ald*succinic semialdehyde 101.082 C4 H5 O3 C(CCC=O)(=O)[O-] PUBCHEM:9543238:*CHEBI:57706:*CHEBI:16265*PUBCHEM:1112*LIGAND-CPD:C00232*CAS:692-29-5:*LIGAND-CPD:C00232: 2.6.1.19 4-aminobutyrate + 2-oxoglutarate = succinate semialdehyde + L-glutamate 4-aminobutyrate degradation I 4-aminobutyrate 4-NH2-but*4-NH3-but*GABA*4-aminobutyric acid*4-aminobutanoate*γ-aminobutyrate*4-amino-n-butyric acid*γ-amino-n-butyric acid 103.121 C4 H9 N1 O2 C(=O)([O-])CCC[N+] PUBCHEM:6992099:*PUBCHEM:6992099:*CHEBI:30566*PUBCHEM:119*LIGAND-CPD:C00334*LIGAND-CPD:C00334:*CAS:56-12-2 1.2.1.19 4-aminobutanal + NAD+ + H2O = 4-aminobutyrate + NADH + H+ putrescine degradation IV 4-aminobutyrate 4-NH2-but*4-NH3-but*GABA*4-aminobutyric acid*4-aminobutanoate*γ-aminobutyrate*4-amino-n-butyric acid*γ-amino-n-butyric acid 103.121 C4 H9 N1 O2 C(=O)([O-])CCC[N+] PUBCHEM:6992099:*PUBCHEM:6992099:*CHEBI:30566*PUBCHEM:119*LIGAND-CPD:C00334*LIGAND-CPD:C00334:*CAS:56-12-2 2.6.1.19 4-aminobutyrate + 2-oxoglutarate = succinate semialdehyde + L-glutamate glutamate degradation III (via 4-aminobutyrate) 4-aminobutyrate 4-NH2-but*4-NH3-but*GABA*4-aminobutyric acid*4-aminobutanoate*γ-aminobutyrate*4-amino-n-butyric acid*γ-amino-n-butyric acid 103.121 C4 H9 N1 O2 C(=O)([O-])CCC[N+] PUBCHEM:6992099:*PUBCHEM:6992099:*CHEBI:30566*PUBCHEM:119*LIGAND-CPD:C00334*LIGAND-CPD:C00334:*CAS:56-12-2 2.6.1.19 4-aminobutyrate + 2-oxoglutarate = succinate semialdehyde + L-glutamate 4-aminobutyrate degradation II 4-aminobutyrate 4-NH2-but*4-NH3-but*GABA*4-aminobutyric acid*4-aminobutanoate*γ-aminobutyrate*4-amino-n-butyric acid*γ-amino-n-butyric acid 103.121 C4 H9 N1 O2 C(=O)([O-])CCC[N+] PUBCHEM:6992099:*PUBCHEM:6992099:*CHEBI:30566*PUBCHEM:119*LIGAND-CPD:C00334*LIGAND-CPD:C00334:*CAS:56-12-2 2.6.1.19 4-aminobutyrate + 2-oxoglutarate = succinate semialdehyde + L-glutamate 4-aminobutyrate degradation I 4-aminobutyrate 4-NH2-but*4-NH3-but*GABA*4-aminobutyric acid*4-aminobutanoate*γ-aminobutyrate*4-amino-n-butyric acid*γ-amino-n-butyric acid 103.121 C4 H9 N1 O2 C(=O)([O-])CCC[N+] PUBCHEM:6992099:*PUBCHEM:6992099:*CHEBI:30566*PUBCHEM:119*LIGAND-CPD:C00334*LIGAND-CPD:C00334:*CAS:56-12-2 4.1.1.15 H+ + L-glutamate = CO2 + 4-aminobutyrate glutamate degradation III (via 4-aminobutyrate) 4-aminobutyrate 4-NH2-but*4-NH3-but*GABA*4-aminobutyric acid*4-aminobutanoate*γ-aminobutyrate*4-amino-n-butyric acid*γ-amino-n-butyric acid 103.121 C4 H9 N1 O2 C(=O)([O-])CCC[N+] PUBCHEM:6992099:*PUBCHEM:6992099:*CHEBI:30566*PUBCHEM:119*LIGAND-CPD:C00334*LIGAND-CPD:C00334:*CAS:56-12-2 4.1.1.15 H+ + L-glutamate = CO2 + 4-aminobutyrate glutamate degradation IX (via 4-aminobutyrate) 4-aminobutyrate 4-NH2-but*4-NH3-but*GABA*4-aminobutyric acid*4-aminobutanoate*γ-aminobutyrate*4-amino-n-butyric acid*γ-amino-n-butyric acid 103.121 C4 H9 N1 O2 C(=O)([O-])CCC[N+] PUBCHEM:6992099:*PUBCHEM:6992099:*CHEBI:30566*PUBCHEM:119*LIGAND-CPD:C00334*LIGAND-CPD:C00334:*CAS:56-12-2 4.1.1.15 H+ + L-glutamate = CO2 + 4-aminobutyrate glutamate dependent acid resistance 4-aminobutyrate 4-NH2-but*4-NH3-but*GABA*4-aminobutyric acid*4-aminobutanoate*γ-aminobutyrate*4-amino-n-butyric acid*γ-amino-n-butyric acid 103.121 C4 H9 N1 O2 C(=O)([O-])CCC[N+] PUBCHEM:6992099:*PUBCHEM:6992099:*CHEBI:30566*PUBCHEM:119*LIGAND-CPD:C00334*LIGAND-CPD:C00334:*CAS:56-12-2 3.5.3.7 H2O + 4-guanidinobutyrate = urea + 4-aminobutyrate arginine degradation X (arginine monooxygenase pathway) delphinidin delfinidin 301.232 C15 H9 O7 C3(C2(=C(C=C([O-])C(C1(C=C(O)C(O)=C(O)C=1))=[O+]2)C([O-])=CC(O)=3)) PUBCHEM:25203213:*LIGAND-CPD:C05908: 1.14.11.- leucodelphinidin + oxygen + 2-oxoglutarate = H+ + delphinidin + H2O + CO2 + succinate anthocyanin biosynthesis (delphinidin 3-O-glucoside) delphinidin delfinidin 301.232 C15 H9 O7 C3(C2(=C(C=C([O-])C(C1(C=C(O)C(O)=C(O)C=1))=[O+]2)C([O-])=CC(O)=3)) PUBCHEM:25203213:*LIGAND-CPD:C05908: 2.4.1.115 delphinidin = UDP + delphinidin-3-O-β-D-glucoside anthocyanin biosynthesis (delphinidin 3-O-glucoside) delphinidin delfinidin 301.232 C15 H9 O7 C3(C2(=C(C=C([O-])C(C1(C=C(O)C(O)=C(O)C=1))=[O+]2)C([O-])=CC(O)=3)) PUBCHEM:25203213:*LIGAND-CPD:C05908: 1.3.1.77 H+ + delphinidin = epigallocatechin 2,3-cis-flavanols biosynthesis ent-copalyl diphosphate CDP*CPP*ent-copalyl diphosphate*ent-CPP*ent-CDP*(-)-CPP*(-)-CDP*(-)-copalyl diphosphate 447.424 C20 H33 O7 P2 C1(CCC(C2(C1(C(C(CC2)=C)CCC(C)=CCOP(OP([O-])([O-])=O)([O-])=O)C))(C)C) CHEBI:58553:*PUBCHEM:25243968:*LIGAND-CPD:C06089: 4.2.3.19 ent-copalyl diphosphate = diphosphate + ent-kaurene ent-kaurene biosynthesis I ent-copalyl diphosphate CDP*CPP*ent-copalyl diphosphate*ent-CPP*ent-CDP*(-)-CPP*(-)-CDP*(-)-copalyl diphosphate 447.424 C20 H33 O7 P2 C1(CCC(C2(C1(C(C(CC2)=C)CCC(C)=CCOP(OP([O-])([O-])=O)([O-])=O)C))(C)C) CHEBI:58553:*PUBCHEM:25243968:*LIGAND-CPD:C06089: 5.5.1.13 all-trans-geranyl-geranyl diphosphate = ent-copalyl diphosphate ent-kaurene biosynthesis I orotidine-5'-phosphate 365.17 C10 H10 N2 O11 P1 O=C1(C=C(C(=O)[O-])N(C(N1)=O)C2(C(O)C(C(COP([O-])([O-])=O)O2)O)) PUBCHEM:25245207:*LIGAND-CPD:C01103:*CAS:2149-82-8 2.4.2.10 orotidine-5'-phosphate + diphosphate = 5-phospho-α-D-ribose 1-diphosphate + orotate uridine-5'-phosphate biosynthesis orotidine-5'-phosphate 365.17 C10 H10 N2 O11 P1 O=C1(C=C(C(=O)[O-])N(C(N1)=O)C2(C(O)C(C(COP([O-])([O-])=O)O2)O)) PUBCHEM:25245207:*LIGAND-CPD:C01103:*CAS:2149-82-8 4.1.1.23 H+ + orotidine-5'-phosphate = CO2 + uridine-5'-phosphate uridine-5'-phosphate biosynthesis 3-phospho-L-serine 3-phospho-serine*O-phospho-L-serine*serine phosphate*phosphorylserine*seryl phosphate*3-P-serine*serine-3-p*serine-3-phosphate*phosphoserine*P-serine*3-phospho-1-serine*P-ser*3-phosphoserine 183.057 C3 H6 N1 O6 P1 P(=O)([O-])([O-])OCC([N+])C(=O)[O-] PUBCHEM:7059387:*CHEBI:57524:*PUBCHEM:7059387:*CAS:407-41-0:*LIGAND-CPD:C01005:*CAS:17885-08-4: 2.6.1.52 3-phospho-L-serine + 2-oxoglutarate = L-glutamate + 3-phospho-hydroxypyruvate serine biosynthesis 3-phospho-L-serine 3-phospho-serine*O-phospho-L-serine*serine phosphate*phosphorylserine*seryl phosphate*3-P-serine*serine-3-p*serine-3-phosphate*phosphoserine*P-serine*3-phospho-1-serine*P-ser*3-phosphoserine 183.057 C3 H6 N1 O6 P1 P(=O)([O-])([O-])OCC([N+])C(=O)[O-] PUBCHEM:7059387:*CHEBI:57524:*PUBCHEM:7059387:*CAS:407-41-0:*LIGAND-CPD:C01005:*CAS:17885-08-4: 3.1.3.3 3-phospho-L-serine + H2O = L-serine serine biosynthesis gibberellin A12 GA12*GA12*gibberellin A12*gibberellin A12 330.423 C20 H26 O4 C1(CCC(C2([H])(C(C34(CC(CCC(C1(C)2)3)C(C4)=C))C([O-])=O))(C)C([O-])=O) PUBCHEM:44229165:*CHEBI:30088:*LIGAND-CPD:C11857: H+ + gibberellin A12 + oxygen = GA53 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) gibberellin A12 GA12*GA12*gibberellin A12*gibberellin A12 330.423 C20 H26 O4 C1(CCC(C2([H])(C(C34(CC(CCC(C1(C)2)3)C(C4)=C))C([O-])=O))(C)C([O-])=O) PUBCHEM:44229165:*CHEBI:30088:*LIGAND-CPD:C11857: 1.14.13.79 GA12-aldehyde + NADPH + oxygen = gibberellin A12 + NADP+ + H2O GA12 biosynthesis gibberellin A12 GA12*GA12*gibberellin A12*gibberellin A12 330.423 C20 H26 O4 C1(CCC(C2([H])(C(C34(CC(CCC(C1(C)2)3)C(C4)=C))C([O-])=O))(C)C([O-])=O) PUBCHEM:44229165:*CHEBI:30088:*LIGAND-CPD:C11857: 1.14.11.- gibberellin A12 + 2-oxoglutarate + oxygen = GA110 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) D-myo-inositol (1,2) bisphosphate 1D-myo-inositol (1,2) bisphosphate*1D-myo-inositol (1,2) biphosphate*Ins(1,2)P2*D-myo-inositol (1,2) biphosphate*I(1,2)P2 336.085 C6 H10 O12 P2 [O-]P([O-])(=O)OC1(C(O)C(O)C(O)C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:25203218:*PUBCHEM:25245835: D-myo-inositol (1,2,6) trisphosphate + H2O = D-myo-inositol (1,2) bisphosphate phytate degradation I D-myo-inositol (1,2) bisphosphate 1D-myo-inositol (1,2) bisphosphate*1D-myo-inositol (1,2) biphosphate*Ins(1,2)P2*D-myo-inositol (1,2) biphosphate*I(1,2)P2 336.085 C6 H10 O12 P2 [O-]P([O-])(=O)OC1(C(O)C(O)C(O)C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:25203218:*PUBCHEM:25245835: D-myo-inositol (1,2) bisphosphate + H2O = 1D-myo-inositol (2) monophosphate phytate degradation II D-myo-inositol (1,2) bisphosphate 1D-myo-inositol (1,2) bisphosphate*1D-myo-inositol (1,2) biphosphate*Ins(1,2)P2*D-myo-inositol (1,2) biphosphate*I(1,2)P2 336.085 C6 H10 O12 P2 [O-]P([O-])(=O)OC1(C(O)C(O)C(O)C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:25203218:*PUBCHEM:25245835: D-myo-inositol (1,2) bisphosphate + H2O = 1D-myo-inositol (2) monophosphate phytate degradation I D-myo-inositol (1,2) bisphosphate 1D-myo-inositol (1,2) bisphosphate*1D-myo-inositol (1,2) biphosphate*Ins(1,2)P2*D-myo-inositol (1,2) biphosphate*I(1,2)P2 336.085 C6 H10 O12 P2 [O-]P([O-])(=O)OC1(C(O)C(O)C(O)C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:25203218:*PUBCHEM:25245835: D-myo-inositol (1,2,3) trisphosphate + H2O = D-myo-inositol (1,2) bisphosphate phytate degradation II D-myo-inositol (1,2) bisphosphate 1D-myo-inositol (1,2) bisphosphate*1D-myo-inositol (1,2) biphosphate*Ins(1,2)P2*D-myo-inositol (1,2) biphosphate*I(1,2)P2 336.085 C6 H10 O12 P2 [O-]P([O-])(=O)OC1(C(O)C(O)C(O)C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:25203218:*PUBCHEM:25245835: D-myo-inositol (1,2,3) trisphosphate + H2O = D-myo-inositol (1,2) bisphosphate phytate degradation I D-myo-inositol (1,2) bisphosphate 1D-myo-inositol (1,2) bisphosphate*1D-myo-inositol (1,2) biphosphate*Ins(1,2)P2*D-myo-inositol (1,2) biphosphate*I(1,2)P2 336.085 C6 H10 O12 P2 [O-]P([O-])(=O)OC1(C(O)C(O)C(O)C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:25203218:*PUBCHEM:25245835: D-myo-inositol (1,2) bisphosphate + H2O = 1D-myo-inositol (1)-monophosphate phytate degradation I 3-hydroxy-3-phenylpropionyl-CoA hydroxycinnamoyl-CoA*β-hydroxyphenyl-propionyl-CoA*3-hydroxy-3-phenylpropionyl-coenzyme A 911.663 C30 H40 N7 O18 P3 S1 [O-]P([O-])(OC2(C(COP([O-])(OP(OCC(C)(C)C(C(=O)NCCC(NCCSC(=O)CC(O)C1(C=CC=CC=1))=O)O)([O-])=O)=O)OC(C(O)2)N3(C=NC4(=C3N=CN=C(N)4))))=O PUBCHEM:25244147:*LIGAND-CPD:C06362: 3-hydroxy-3-phenylpropionyl-CoA = benzaldehyde + acetyl-CoA benzoate biosynthesis III (CoA-dependent, non-β-oxidative) 3-hydroxy-3-phenylpropionyl-CoA hydroxycinnamoyl-CoA*β-hydroxyphenyl-propionyl-CoA*3-hydroxy-3-phenylpropionyl-coenzyme A 911.663 C30 H40 N7 O18 P3 S1 [O-]P([O-])(OC2(C(COP([O-])(OP(OCC(C)(C)C(C(=O)NCCC(NCCSC(=O)CC(O)C1(C=CC=CC=1))=O)O)([O-])=O)=O)OC(C(O)2)N3(C=NC4(=C3N=CN=C(N)4))))=O PUBCHEM:25244147:*LIGAND-CPD:C06362: (E)-cinnamoyl-CoA + H2O = 3-hydroxy-3-phenylpropionyl-CoA benzoate biosynthesis III (CoA-dependent, non-β-oxidative) propane-1,3-diamine 1,3-propanediamine*trimethylenediamine*1,3-diaminopropane*Trimethylenediamine*1,3-Propanediamine*Propane-1,3-diamine*1,3-DAP 76.141 C3 H12 N2 [N+]CCC[N+] CHEBI:57484:*PUBCHEM:4030255:*LIGAND-CPD:C00986:*CAS:109-76-2 2.5.1.46 spermidine = propane-1,3-diamine hypusine biosynthesis propane-1,3-diamine 1,3-propanediamine*trimethylenediamine*1,3-diaminopropane*Trimethylenediamine*1,3-Propanediamine*Propane-1,3-diamine*1,3-DAP 76.141 C3 H12 N2 [N+]CCC[N+] CHEBI:57484:*PUBCHEM:4030255:*LIGAND-CPD:C00986:*CAS:109-76-2 1.4.3.22 propane-1,3-diamine + H2O + oxygen = H+ + 3-aminopropanal + ammonia + hydrogen peroxide β-alanine biosynthesis I propane-1,3-diamine 1,3-propanediamine*trimethylenediamine*1,3-diaminopropane*Trimethylenediamine*1,3-Propanediamine*Propane-1,3-diamine*1,3-DAP 76.141 C3 H12 N2 [N+]CCC[N+] CHEBI:57484:*PUBCHEM:4030255:*LIGAND-CPD:C00986:*CAS:109-76-2 1.5.3.14 spermidine + oxygen + H2O = propane-1,3-diamine + 4-aminobutanal + hydrogen peroxide spermine and spermidine degradation II propane-1,3-diamine 1,3-propanediamine*trimethylenediamine*1,3-diaminopropane*Trimethylenediamine*1,3-Propanediamine*Propane-1,3-diamine*1,3-DAP 76.141 C3 H12 N2 [N+]CCC[N+] CHEBI:57484:*PUBCHEM:4030255:*LIGAND-CPD:C00986:*CAS:109-76-2 1.5.3.14 spermine + oxygen + H2O = 1-(3-aminopropyl)-4-aminobutanal + propane-1,3-diamine + hydrogen peroxide spermine and spermidine degradation II UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.7.4.14 ATP + uridine-5'-phosphate = ADP + UDP pyrimidine ribonucleotides interconversion UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.91 kaempferol = kaempferol-3-glucoside + UDP + H+ flavonol glucosylation I UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.117 dolichyl-diphosphooligosaccharide biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.15 α-D-glucose 6-phosphate = H+ + UDP + trehalose 6-phosphate trehalose biosynthesis I UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 phloretin = phlorizin + UDP phloridzin biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 UDP-D-galactose = UDP xyloglucan biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.11 glycogen biosynthesis II (from UDP-D-Glucose) UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.123 myo-inositol + UDP-D-galactose = H+ + galactinol + UDP stachyose biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- dihydrozeatin = H+ + dihydrozeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 1.17.4.- UDP = dUDP + H2O pyrimidine deoxyribonucleotides de novo biosynthesis I UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.12 cellulose biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.2.34 indol-3-yl-acetyl-myo-inositol = H+ + UDP + indole-3-yl-acetyl-myo-inositol L-arabinoside IAA conjugate biosynthesis I UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.13 β-D-fructofuranose = sucrose + UDP sucrose degradation III UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.13 β-D-fructofuranose = sucrose + UDP galactose degradation III UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.13 β-D-fructofuranose = sucrose + UDP sucrose biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.114 2-coumarate = H+ + trans-β-D-Glucosyl-2-hydroxycinnamate + UDP coumarin biosynthesis (via 2-coumarate) UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.115 pelargonidin = H+ + UDP + pelargonidin-3-O-β-D-glucoside anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.186 glycogen biosynthesis II (from UDP-D-Glucose) UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.14 D-fructose-6-phosphate = H+ + sucrose-6-phosphate + UDP sucrose biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.115 delphinidin = UDP + delphinidin-3-O-β-D-glucoside anthocyanin biosynthesis (delphinidin 3-O-glucoside) UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.2.24 UDP-α-D-xylose = UDP xylan biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.141 UDP-α-N-acetyl-D-glucosamine = H+ + UDP dolichyl-diphosphooligosaccharide biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.2.- xylan biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.111 coniferyl alcohol = H+ + coniferin + UDP coniferin metabolism UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.43 UDP-D-galacturonate = UDP homogalacturonan biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.186 glycogen biosynthesis II (from UDP-D-Glucose) UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.91 quercetin = UDP + quercetin-3-glucoside flavonol glucosylation I UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 UDP-α-D-xylose = UDP xyloglucan biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- coniferaldehyde = H+ + coniferaldehyde glucoside + UDP monolignol glucosides biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.238 delphinidin-3,5-diglucoside = H+ + delphinidin 3,5,3'-triglucoside + UDP gentiodelphin biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 UDP-α-D-sulfoquinovopyranose = sulfoquinovosyldiacylglycerol + UDP sulfolipid biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- sinapaldehyde = H+ + sinapaldehyde glucoside + UDP monolignol glucosides biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.241 UDP-D-galactose = UDP glycolipid biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 1.17.4.1 dUDP + H2O = UDP pyrimidine deoxyribonucleotides de novo biosynthesis I UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- delphinidin 3-O-glucosyl-5-O-caffeoylglucoside = H+ + delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + UDP gentiodelphin biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- dihydroconiferyl alcohol = H+ + dihydroconiferyl alcohol glucoside + UDP monolignol glucosides biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.203 trans-zeatin = H+ + trans-zeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.215 cis-zeatin = cis-zeatin-O-glucoside + H+ + UDP cytokinins-O-glucoside biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- dihydrozeatin-9-N-glucoside = H+ + dihydrozeatin-9-N-glucoside-O-glucoside + UDP cytokinins-O-glucoside biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- UDP-D-glucuronate = UDP xylan biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.80 sphingolipid biosynthesis (plants) UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.121 indole-3-acetate = indole-3-acetyl-β-1-D-glucose + UDP IAA conjugate biosynthesis I UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.115 cyanidin = cyanidin-3-O-β-D-glucoside + UDP anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.156 indol-3-yl-acetyl-myo-inositol + UDP-D-galactose = H+ + 5-O-(indol-3-ylacetyl-myo-inositol) D-galactoside + UDP IAA conjugate biosynthesis I UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.111 sinapyl-alcohol = H+ + syringin + UDP monolignol glucosides biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- delphinidin-3-O-β-D-glucoside = H+ + delphinidin-3,5-diglucoside + UDP gentiodelphin biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.46 UDP-D-galactose = UDP glycolipid biosynthesis UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.7.4.22 ATP + uridine-5'-phosphate = ADP + UDP pyrimidine ribonucleotides interconversion UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.91 flavonol glucosylation I UDP UDP*uridine-diphosphate*uridine-5'-diphosphate 401.14 C9 H11 N2 O12 P2 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:20056717:*KNAPSACK:C00007313:*LIGAND-CPD:C00015:*CAS:58-98-0 2.7.4.6 UDP + ATP = UTP + ADP pyrimidine ribonucleotides interconversion siroheme 908.611 C42 H36 N4 O16 FE1 C46(=CC8(=C(CC([O-])=O)C(CCC(=O)[O-])=C7(N([Fe]25(N1(C(C(CCC([O-])=O)=C(CC(=O)[O-])C=1C=C3(C(C)(CC(=O)[O-])C(CCC(=O)[O-])C(N23)=CC(C(C)(CC(=O)[O-])C(CCC(=O)[O-])4)=N56))=C7)))8))) CHEBI:28599:*PUBCHEM:9548568:*LIGAND-CPD:C00748: 4.99.1.4 H+ + sirohydrochlorin + Fe2+ = siroheme siroheme biosynthesis L-threonine T*thr*thre*L-thr*threonine*2-amino-3-hydroxybutyric acid 119.12 C4 H9 N1 O3 [O-]C(=O)C([N+])C(O)C PUBCHEM:6995276:*KNAPSACK:C00001394:*CHEBI:16857:*PUBCHEM:6995276:*LIGAND-CPD:C00188:*CAS:72-19-5 4.3.1.19 L-threonine = H+ + 2-oxobutanoate + ammonia isoleucine biosynthesis I (from threonine) L-threonine T*thr*thre*L-thr*threonine*2-amino-3-hydroxybutyric acid 119.12 C4 H9 N1 O3 [O-]C(=O)C([N+])C(O)C PUBCHEM:6995276:*KNAPSACK:C00001394:*CHEBI:16857:*PUBCHEM:6995276:*LIGAND-CPD:C00188:*CAS:72-19-5 4.3.1.19 L-threonine = H+ + 2-oxobutanoate + ammonia hypoglycin biosynthesis L-threonine T*thr*thre*L-thr*threonine*2-amino-3-hydroxybutyric acid 119.12 C4 H9 N1 O3 [O-]C(=O)C([N+])C(O)C PUBCHEM:6995276:*KNAPSACK:C00001394:*CHEBI:16857:*PUBCHEM:6995276:*LIGAND-CPD:C00188:*CAS:72-19-5 2,3-dihydroxybenzoate-VibB + L-threonine = dihydroxyphenyl-5-methyloxazoline-VibF + H2O vibriobactin biosynthesis L-threonine T*thr*thre*L-thr*threonine*2-amino-3-hydroxybutyric acid 119.12 C4 H9 N1 O3 [O-]C(=O)C([N+])C(O)C PUBCHEM:6995276:*KNAPSACK:C00001394:*CHEBI:16857:*PUBCHEM:6995276:*LIGAND-CPD:C00188:*CAS:72-19-5 6.1.1.3 H+ + L-threonine + ATP = diphosphate + AMP tRNA charging pathway L-threonine T*thr*thre*L-thr*threonine*2-amino-3-hydroxybutyric acid 119.12 C4 H9 N1 O3 [O-]C(=O)C([N+])C(O)C PUBCHEM:6995276:*KNAPSACK:C00001394:*CHEBI:16857:*PUBCHEM:6995276:*LIGAND-CPD:C00188:*CAS:72-19-5 4.2.3.1 O-phospho-L-homoserine + H2O = L-threonine threonine biosynthesis from homoserine L-threonine T*thr*thre*L-thr*threonine*2-amino-3-hydroxybutyric acid 119.12 C4 H9 N1 O3 [O-]C(=O)C([N+])C(O)C PUBCHEM:6995276:*KNAPSACK:C00001394:*CHEBI:16857:*PUBCHEM:6995276:*LIGAND-CPD:C00188:*CAS:72-19-5 4.1.2.5 L-threonine = acetaldehyde + glycine glycine biosynthesis IV 2-cis-abscisic acid abscisic acid*ABA*abscisate*(+)-ABA*(+)-S-ABA*abscisin II*2-cis-ABA*(+)-abscisate 263.313 C15 H19 O4 C1(C(C(C(=CC1=O)C)(O)C=CC(=CC([O-])=O)C)(C)C) PUBCHEM:7251168:*CHEBI:37569:*LIGAND-CPD:C06082: 1.2.3.14 abscisic aldehyde + H2O + oxygen = H+ + 2-cis-abscisic acid + hydrogen peroxide abscisic acid biosynthesis 2-cis-abscisic acid abscisic acid*ABA*abscisate*(+)-ABA*(+)-S-ABA*abscisin II*2-cis-ABA*(+)-abscisate 263.313 C15 H19 O4 C1(C(C(C(=CC1=O)C)(O)C=CC(=CC([O-])=O)C)(C)C) PUBCHEM:7251168:*CHEBI:37569:*LIGAND-CPD:C06082: 1.2.3.14 abscisic aldehyde + H2O + oxygen = H+ + 2-cis-abscisic acid + hydrogen peroxide aldehyde oxidation I 2-cis-abscisic acid abscisic acid*ABA*abscisate*(+)-ABA*(+)-S-ABA*abscisin II*2-cis-ABA*(+)-abscisate 263.313 C15 H19 O4 C1(C(C(C(=CC1=O)C)(O)C=CC(=CC([O-])=O)C)(C)C) PUBCHEM:7251168:*CHEBI:37569:*LIGAND-CPD:C06082: 1.14.13.93 H+ + 2-cis-abscisic acid + NADPH + oxygen = 8'-hydroxyabscisate + NADP+ + H2O phaseic acid biosynthesis dimethylsulfide reduced dimethyl sulfoxide*dimethyl sulphide*dimethylsulphide*DMS*dimethyl sulfide 62.129 C2 H6 S1 CSC PUBCHEM:1068:*PUBCHEM:1068:*CHEBI:17437:*LIGAND-CPD:C00580:*CAS:75-18-3 2.1.1.19 tetrahydrofolate + trimethyl sulfonium = H+ + dimethylsulfide + 5-methyl-tetrahydrofolate folate transformations I 1D-myo-inositol (4)-monophosphate D-myo-inositol (4)-phosphate*D-myo-inositol (4)-monophosphate*inositol 4-phosphate*1D-myo-inositol (4)-phosphate*Ins(4)P1*Ins(4)P*Ins4P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(C(O)C(O)C(O)C(O)C(O)1) CHEBI:58469:*PUBCHEM:25200523:*LIGAND-CPD:C03546:*CAS:46495-39-0 3.1.3.57 D-myo-inositol (1,4)-bisphosphate + H2O = 1D-myo-inositol (4)-monophosphate D-myo-inositol (1,4,5)-trisphosphate degradation 1D-myo-inositol (4)-monophosphate D-myo-inositol (4)-phosphate*D-myo-inositol (4)-monophosphate*inositol 4-phosphate*1D-myo-inositol (4)-phosphate*Ins(4)P1*Ins(4)P*Ins4P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(C(O)C(O)C(O)C(O)C(O)1) CHEBI:58469:*PUBCHEM:25200523:*LIGAND-CPD:C03546:*CAS:46495-39-0 3.1.3.25 1D-myo-inositol (4)-monophosphate + H2O = myo-inositol D-myo-inositol (1,4,5)-trisphosphate degradation 2-oxopentenoate 2-oxo-4-pentenoate*2-oxopent-4-enoate*2-keto-4-pentenoate*oxopent-4-enoate*2-keto-4-pentenoic acid*2-ketopent-4-enoic acid 113.093 C5 H5 O3 C(=O)(C(=O)[O-])CC=C LIGAND-CPD:c00596:*CAS:159694-16-3*LIGAND-CPD:C00596:*LIGAND-CPD:C00596:*PUBCHEM:9543147:*CHEBI:11641:*UM-BBD-CPD:c0102: 5-hydroxy-2-oxopentanoate = 2-oxopentenoate + H2O hypoglycin biosynthesis 2-oxopentenoate 2-oxo-4-pentenoate*2-oxopent-4-enoate*2-keto-4-pentenoate*oxopent-4-enoate*2-keto-4-pentenoic acid*2-ketopent-4-enoic acid 113.093 C5 H5 O3 C(=O)(C(=O)[O-])CC=C LIGAND-CPD:c00596:*CAS:159694-16-3*LIGAND-CPD:C00596:*LIGAND-CPD:C00596:*PUBCHEM:9543147:*CHEBI:11641:*UM-BBD-CPD:c0102: 1.-.-.- 2-oxopentenoate = H+ + 2-oxopenta-3,4-dienoate hypoglycin biosynthesis betaine aldehyde glycine betaine aldehyde 102.156 C5 H12 N1 O1 [N+](C)(CC=O)(C)C PUBCHEM:249:*CHEBI:15710:*LIGAND-CPD:C00576:*CAS:7418-61-3 betaine aldehyde hydrate = betaine aldehyde + H2O glycine betaine biosynthesis III (plants) betaine aldehyde glycine betaine aldehyde 102.156 C5 H12 N1 O1 [N+](C)(CC=O)(C)C PUBCHEM:249:*CHEBI:15710:*LIGAND-CPD:C00576:*CAS:7418-61-3 1.2.1.8 betaine aldehyde + NAD+ + H2O = H+ + glycine betaine + NADH glycine betaine biosynthesis III (plants) (3R,6E)-nerolidol (E)-nerolidol*(3R)-(E)-nerolidol 222.37 C15 H26 O1 C(CCC(=CCCC(C=C)(O)C)C)=C(C)C CHEBI:59959:*PUBCHEM:5284507:*LIGAND-CPD:C09704: 4.2.3.49 (2E,6E)-farnesyl diphosphate + H2O = (3R,6E)-nerolidol + diphosphate (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis (3R,6E)-nerolidol (E)-nerolidol*(3R)-(E)-nerolidol 222.37 C15 H26 O1 C(CCC(=CCCC(C=C)(O)C)C)=C(C)C CHEBI:59959:*PUBCHEM:5284507:*LIGAND-CPD:C09704: 1.14.13.- H+ + (3R,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis 4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol 442.724 C30 H50 O2 CC=C(CCC(C)C2(CCC1(C3(=CCC4(C(CO)C(O)CCC(C)(C(CCC(C)12)3)4)))))C(C)C 1.14.13.- 4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol + NADH + oxygen = 4α-formyl-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis 4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol 442.724 C30 H50 O2 CC=C(CCC(C)C2(CCC1(C3(=CCC4(C(CO)C(O)CCC(C)(C(CCC(C)12)3)4)))))C(C)C 1.14.13.- 24-ethylidenelophenol + NADH + oxygen = 4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis 9'-cis-neoxanthin 9cNeox*9c-neoxanthin*9'-cis-neoxanthin 600.88 C40 H56 O4 C(=CC(=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C([H])=C=C1(C(O)(C)CC(O)CC(C)(C)1))C)C23(C(C)(C)CC(O)CC(C)(O2)3) PUBCHEM:5282217:*CHEBI:35306:*LIGAND-CPD:C13431: 1.13.11.51 9'-cis-neoxanthin + oxygen = xanthoxin + C25-allenic-apo-aldehyde abscisic acid biosynthesis 9'-cis-neoxanthin 9cNeox*9c-neoxanthin*9'-cis-neoxanthin 600.88 C40 H56 O4 C(=CC(=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C([H])=C=C1(C(O)(C)CC(O)CC(C)(C)1))C)C23(C(C)(C)CC(O)CC(C)(O2)3) PUBCHEM:5282217:*CHEBI:35306:*LIGAND-CPD:C13431: trans-neoxanthin = 9'-cis-neoxanthin abscisic acid biosynthesis O-phospho-L-homoserine o-phosphohomoserine 197.084 C4 H8 N1 O6 P1 [O-]C(=O)C([N+])CCOP([O-])(=O)[O-] CHEBI:15961:*PUBCHEM:25243978:*LIGAND-CPD:C01102: 2.7.1.39 L-homoserine + ATP = H+ + O-phospho-L-homoserine + ADP threonine biosynthesis from homoserine O-phospho-L-homoserine o-phosphohomoserine 197.084 C4 H8 N1 O6 P1 [O-]C(=O)C([N+])CCOP([O-])(=O)[O-] CHEBI:15961:*PUBCHEM:25243978:*LIGAND-CPD:C01102: 2.7.1.39 L-homoserine + ATP = H+ + O-phospho-L-homoserine + ADP methionine biosynthesis II O-phospho-L-homoserine o-phosphohomoserine 197.084 C4 H8 N1 O6 P1 [O-]C(=O)C([N+])CCOP([O-])(=O)[O-] CHEBI:15961:*PUBCHEM:25243978:*LIGAND-CPD:C01102: 4.2.3.1 O-phospho-L-homoserine + H2O = L-threonine threonine biosynthesis from homoserine O-phospho-L-homoserine o-phosphohomoserine 197.084 C4 H8 N1 O6 P1 [O-]C(=O)C([N+])CCOP([O-])(=O)[O-] CHEBI:15961:*PUBCHEM:25243978:*LIGAND-CPD:C01102: 2.5.1.- L-cysteine + O-phospho-L-homoserine = L-cystathionine methionine biosynthesis II GDP-4-dehydro-6-deoxy-D-mannose GDP-4-keto-6-deoxymannose*GDP-4-keto-6-deoxy-D-mannose*GDP-4-dehydro-6-deoxy-D-talose*GDP-4-oxo-6-deoxy-D-mannose*GDP-4-oxo-6-deoxymannose*GDP-4-keto-6-deoxy-α-D-mannose 585.314 C16 H21 N5 O15 P2 CC4(OC(OP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N3(C=NC2(C(=O)NC(N)=NC=23))))C(O)C(O)C(=O)4) PUBCHEM:25243979:*LIGAND-CPD:C01222: 4.2.1.47 GDP-α-D-mannose = GDP-4-dehydro-6-deoxy-D-mannose + H2O GDP-L-fucose biosynthesis I (from GDP-D-mannose) GDP-4-dehydro-6-deoxy-D-mannose GDP-4-keto-6-deoxymannose*GDP-4-keto-6-deoxy-D-mannose*GDP-4-dehydro-6-deoxy-D-talose*GDP-4-oxo-6-deoxy-D-mannose*GDP-4-oxo-6-deoxymannose*GDP-4-keto-6-deoxy-α-D-mannose 585.314 C16 H21 N5 O15 P2 CC4(OC(OP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N3(C=NC2(C(=O)NC(N)=NC=23))))C(O)C(O)C(=O)4) PUBCHEM:25243979:*LIGAND-CPD:C01222: 1.1.1.271 NADP+ + GDP-L-fucose = H+ + NADPH + GDP-4-dehydro-6-deoxy-D-mannose GDP-L-fucose biosynthesis I (from GDP-D-mannose) tetrahydropteroyl tri-L-glutamate 703.664 C29 H37 N9 O12 NC2(=NC(C1(NC(CNC=1N2)CNC3(=CC=C(C(NC(C(O)=O)CCC(NC(C(O)=O)CCC(NC(C(O)=O)CCC(O)=O)=O)=O)=O)C=C3)))=O) PUBCHEM:16722112:*CHEBI:17420:*LIGAND-CPD:C04144: 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyl tri-L-glutamate + L-methionine methionine biosynthesis II tetrahydropteroyl tri-L-glutamate 703.664 C29 H37 N9 O12 NC2(=NC(C1(NC(CNC=1N2)CNC3(=CC=C(C(NC(C(O)=O)CCC(NC(C(O)=O)CCC(NC(C(O)=O)CCC(O)=O)=O)=O)=O)C=C3)))=O) PUBCHEM:16722112:*CHEBI:17420:*LIGAND-CPD:C04144: 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyl tri-L-glutamate + L-methionine S-adenosyl-L-methionine cycle I tetrahydropteroyl tri-L-glutamate 703.664 C29 H37 N9 O12 NC2(=NC(C1(NC(CNC=1N2)CNC3(=CC=C(C(NC(C(O)=O)CCC(NC(C(O)=O)CCC(NC(C(O)=O)CCC(O)=O)=O)=O)=O)C=C3)))=O) PUBCHEM:16722112:*CHEBI:17420:*LIGAND-CPD:C04144: 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyl tri-L-glutamate + L-methionine S-adenosyl-L-methionine cycle II hydrogen cyanide cyanide*hydrocyanic acid 27.026 C1 H1 N1 C#N CHEBI:18407:*PUBCHEM:768:*CAS:74-90-8:*KNAPSACK:C00007569:*PUBCHEM:768:*CHEBI:18407:*CAS:57-12-5:*LIGAND-CPD:C01326: 1.14.17.4 H+ + L-ascorbate + 1-aminocyclopropane-1-carboxylate + oxygen = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine hydrogen cyanide cyanide*hydrocyanic acid 27.026 C1 H1 N1 C#N CHEBI:18407:*PUBCHEM:768:*CAS:74-90-8:*KNAPSACK:C00007569:*PUBCHEM:768:*CHEBI:18407:*CAS:57-12-5:*LIGAND-CPD:C01326: 4.4.1.9 L-cysteine + hydrogen cyanide = hydrogen sulfide + 3-cyano-L-alanine + H+ cyanide detoxification hydrogen cyanide cyanide*hydrocyanic acid 27.026 C1 H1 N1 C#N CHEBI:18407:*PUBCHEM:768:*CAS:74-90-8:*KNAPSACK:C00007569:*PUBCHEM:768:*CHEBI:18407:*CAS:57-12-5:*LIGAND-CPD:C01326: 4.4.1.9 L-cysteine + hydrogen cyanide = hydrogen sulfide + 3-cyano-L-alanine + H+ cyanide degradation hydrogen cyanide cyanide*hydrocyanic acid 27.026 C1 H1 N1 C#N CHEBI:18407:*PUBCHEM:768:*CAS:74-90-8:*KNAPSACK:C00007569:*PUBCHEM:768:*CHEBI:18407:*CAS:57-12-5:*LIGAND-CPD:C01326: 2.8.1.1 thiosulfate + hydrogen cyanide = H+ + sulfite + thiocyanate thiosulfate disproportionation III (rhodanese) 5-phospho-ribosyl-glycineamide N1-(5-Phospho-D-ribosyl)glycinamide*5'-phosphoribosylglycinamide*5'-phosphoribosylglycineamide*5'-p-ribosylglycinamide*5'-p-ribosylglycineamide*GAR 285.17 C7 H14 N2 O8 P1 O1(C(C(O)C(C1COP([O-])([O-])=O)O)NC(C[N+])=O) PUBCHEM:25244572:*LIGAND-CPD:C03838: 2.1.2.2 10-formyl-tetrahydrofolate + 5-phospho-ribosyl-glycineamide = H+ + tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate 5-phospho-ribosyl-glycineamide N1-(5-Phospho-D-ribosyl)glycinamide*5'-phosphoribosylglycinamide*5'-phosphoribosylglycineamide*5'-p-ribosylglycinamide*5'-p-ribosylglycineamide*GAR 285.17 C7 H14 N2 O8 P1 O1(C(C(O)C(C1COP([O-])([O-])=O)O)NC(C[N+])=O) PUBCHEM:25244572:*LIGAND-CPD:C03838: 2.1.2.2 10-formyl-tetrahydrofolate + 5-phospho-ribosyl-glycineamide = H+ + tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide 5-aminoimidazole ribonucleotide biosynthesis I 5-phospho-ribosyl-glycineamide N1-(5-Phospho-D-ribosyl)glycinamide*5'-phosphoribosylglycinamide*5'-phosphoribosylglycineamide*5'-p-ribosylglycinamide*5'-p-ribosylglycineamide*GAR 285.17 C7 H14 N2 O8 P1 O1(C(C(O)C(C1COP([O-])([O-])=O)O)NC(C[N+])=O) PUBCHEM:25244572:*LIGAND-CPD:C03838: 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = H+ + 5'-phosphoribosyl-N-formylglycineamide + ADP 5-aminoimidazole ribonucleotide biosynthesis II 5-phospho-ribosyl-glycineamide N1-(5-Phospho-D-ribosyl)glycinamide*5'-phosphoribosylglycinamide*5'-phosphoribosylglycineamide*5'-p-ribosylglycinamide*5'-p-ribosylglycineamide*GAR 285.17 C7 H14 N2 O8 P1 O1(C(C(O)C(C1COP([O-])([O-])=O)O)NC(C[N+])=O) PUBCHEM:25244572:*LIGAND-CPD:C03838: 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = H+ + 5'-phosphoribosyl-N-formylglycineamide + ADP superpathway of 5-aminoimidazole ribonucleotide biosynthesis 5-phospho-ribosyl-glycineamide N1-(5-Phospho-D-ribosyl)glycinamide*5'-phosphoribosylglycinamide*5'-phosphoribosylglycineamide*5'-p-ribosylglycinamide*5'-p-ribosylglycineamide*GAR 285.17 C7 H14 N2 O8 P1 O1(C(C(O)C(C1COP([O-])([O-])=O)O)NC(C[N+])=O) PUBCHEM:25244572:*LIGAND-CPD:C03838: 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide 5-aminoimidazole ribonucleotide biosynthesis II 5-phospho-ribosyl-glycineamide N1-(5-Phospho-D-ribosyl)glycinamide*5'-phosphoribosylglycinamide*5'-phosphoribosylglycineamide*5'-p-ribosylglycinamide*5'-p-ribosylglycineamide*GAR 285.17 C7 H14 N2 O8 P1 O1(C(C(O)C(C1COP([O-])([O-])=O)O)NC(C[N+])=O) PUBCHEM:25244572:*LIGAND-CPD:C03838: 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide 5-aminoimidazole ribonucleotide biosynthesis I 5-phospho-ribosyl-glycineamide N1-(5-Phospho-D-ribosyl)glycinamide*5'-phosphoribosylglycinamide*5'-phosphoribosylglycineamide*5'-p-ribosylglycinamide*5'-p-ribosylglycineamide*GAR 285.17 C7 H14 N2 O8 P1 O1(C(C(O)C(C1COP([O-])([O-])=O)O)NC(C[N+])=O) PUBCHEM:25244572:*LIGAND-CPD:C03838: 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide superpathway of 5-aminoimidazole ribonucleotide biosynthesis 4-methyl-2-oxopentanoate 2-ketoisocaproate*2-keto-isocaproate*2-oxoisocaproate*2-keto-4-methyl-pentanoate*4-methyl-2-oxopentanoate*2-oxo-4-methylpentanoate*α-ketoisocaproate*α-oxoisocaproate 129.135 C6 H9 O3 CC(C)CC(C([O-])=O)=O PUBCHEM:3527278:*CHEBI:17865:*LIGAND-CPD:C00233:*CAS:816-66-0 4.1.1.1 H+ + 4-methyl-2-oxopentanoate = 3-methylbutanal + CO2 leucine degradation III 4-methyl-2-oxopentanoate 2-ketoisocaproate*2-keto-isocaproate*2-oxoisocaproate*2-keto-4-methyl-pentanoate*4-methyl-2-oxopentanoate*2-oxo-4-methylpentanoate*α-ketoisocaproate*α-oxoisocaproate 129.135 C6 H9 O3 CC(C)CC(C([O-])=O)=O PUBCHEM:3527278:*CHEBI:17865:*LIGAND-CPD:C00233:*CAS:816-66-0 H+ + (2S)-2-isopropyl-3-oxosuccinate = 4-methyl-2-oxopentanoate + CO2 leucine biosynthesis 4-methyl-2-oxopentanoate 2-ketoisocaproate*2-keto-isocaproate*2-oxoisocaproate*2-keto-4-methyl-pentanoate*4-methyl-2-oxopentanoate*2-oxo-4-methylpentanoate*α-ketoisocaproate*α-oxoisocaproate 129.135 C6 H9 O3 CC(C)CC(C([O-])=O)=O PUBCHEM:3527278:*CHEBI:17865:*LIGAND-CPD:C00233:*CAS:816-66-0 4-methyl-2-oxopentanoate + coenzyme A + NAD+ = isovaleryl-CoA + CO2 + NADH leucine degradation I 4-methyl-2-oxopentanoate 2-ketoisocaproate*2-keto-isocaproate*2-oxoisocaproate*2-keto-4-methyl-pentanoate*4-methyl-2-oxopentanoate*2-oxo-4-methylpentanoate*α-ketoisocaproate*α-oxoisocaproate 129.135 C6 H9 O3 CC(C)CC(C([O-])=O)=O PUBCHEM:3527278:*CHEBI:17865:*LIGAND-CPD:C00233:*CAS:816-66-0 2.6.1.42 L-leucine + 2-oxoglutarate = L-glutamate + 4-methyl-2-oxopentanoate leucine degradation III 4-methyl-2-oxopentanoate 2-ketoisocaproate*2-keto-isocaproate*2-oxoisocaproate*2-keto-4-methyl-pentanoate*4-methyl-2-oxopentanoate*2-oxo-4-methylpentanoate*α-ketoisocaproate*α-oxoisocaproate 129.135 C6 H9 O3 CC(C)CC(C([O-])=O)=O PUBCHEM:3527278:*CHEBI:17865:*LIGAND-CPD:C00233:*CAS:816-66-0 2.6.1.42 L-leucine + 2-oxoglutarate = L-glutamate + 4-methyl-2-oxopentanoate leucine biosynthesis 4-methyl-2-oxopentanoate 2-ketoisocaproate*2-keto-isocaproate*2-oxoisocaproate*2-keto-4-methyl-pentanoate*4-methyl-2-oxopentanoate*2-oxo-4-methylpentanoate*α-ketoisocaproate*α-oxoisocaproate 129.135 C6 H9 O3 CC(C)CC(C([O-])=O)=O PUBCHEM:3527278:*CHEBI:17865:*LIGAND-CPD:C00233:*CAS:816-66-0 2.6.1.42 L-leucine + 2-oxoglutarate = L-glutamate + 4-methyl-2-oxopentanoate leucine degradation I quercetin 3,5,7,3',4'-pentahydroxyflavone*quercetin*3,5,7,3',4'-pentahydroflavone*3,5,7,3',4'-Pentahydroxyflavone 301.232 C15 H9 O7 [O-]C3(C(=O)C1(C(=CC(O)=CC(O)=1)OC(C2(C=C(O)C(O)=CC=2))=3)) CHEBI:16243:*|Wikipedia|:Quercetin:*CAS:117-39-5*NCI:9219*PUBCHEM:5280343:*LIGAND-CPD:C00389: 1.14.11.23 trans dihydroquercetin + 2-oxoglutarate + oxygen = quercetin + succinate + CO2 + H2O flavonol biosynthesis quercetin 3,5,7,3',4'-pentahydroxyflavone*quercetin*3,5,7,3',4'-pentahydroflavone*3,5,7,3',4'-Pentahydroxyflavone 301.232 C15 H9 O7 [O-]C3(C(=O)C1(C(=CC(O)=CC(O)=1)OC(C2(C=C(O)C(O)=CC=2))=3)) CHEBI:16243:*|Wikipedia|:Quercetin:*CAS:117-39-5*NCI:9219*PUBCHEM:5280343:*LIGAND-CPD:C00389: 2.4.1.91 quercetin = UDP + quercetin-3-glucoside flavonol glucosylation I quercetin 3,5,7,3',4'-pentahydroxyflavone*quercetin*3,5,7,3',4'-pentahydroflavone*3,5,7,3',4'-Pentahydroxyflavone 301.232 C15 H9 O7 [O-]C3(C(=O)C1(C(=CC(O)=CC(O)=1)OC(C2(C=C(O)C(O)=CC=2))=3)) CHEBI:16243:*|Wikipedia|:Quercetin:*CAS:117-39-5*NCI:9219*PUBCHEM:5280343:*LIGAND-CPD:C00389: 2.1.1.76 quercetin + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + 3-O-methylquercetin methylquercetin biosynthesis quercetin 3,5,7,3',4'-pentahydroxyflavone*quercetin*3,5,7,3',4'-pentahydroflavone*3,5,7,3',4'-Pentahydroxyflavone 301.232 C15 H9 O7 [O-]C3(C(=O)C1(C(=CC(O)=CC(O)=1)OC(C2(C=C(O)C(O)=CC=2))=3)) CHEBI:16243:*|Wikipedia|:Quercetin:*CAS:117-39-5*NCI:9219*PUBCHEM:5280343:*LIGAND-CPD:C00389: 2.8.2.25 quercetin + phosphoadenosine-5'-phosphosulfate = H+ + adenosine 3',5'-bisphosphate + quercetin 3-sulfate quercetinsulphates biosynthesis quercetin 3,5,7,3',4'-pentahydroxyflavone*quercetin*3,5,7,3',4'-pentahydroflavone*3,5,7,3',4'-Pentahydroxyflavone 301.232 C15 H9 O7 [O-]C3(C(=O)C1(C(=CC(O)=CC(O)=1)OC(C2(C=C(O)C(O)=CC=2))=3)) CHEBI:16243:*|Wikipedia|:Quercetin:*CAS:117-39-5*NCI:9219*PUBCHEM:5280343:*LIGAND-CPD:C00389: 2.1.1.- quercetin + S-adenosyl-L-methionine = H+ + isorhamnetin + S-adenosyl-L-homocysteine quercetinsulphates biosynthesis quercetin 3,5,7,3',4'-pentahydroxyflavone*quercetin*3,5,7,3',4'-pentahydroflavone*3,5,7,3',4'-Pentahydroxyflavone 301.232 C15 H9 O7 [O-]C3(C(=O)C1(C(=CC(O)=CC(O)=1)OC(C2(C=C(O)C(O)=CC=2))=3)) CHEBI:16243:*|Wikipedia|:Quercetin:*CAS:117-39-5*NCI:9219*PUBCHEM:5280343:*LIGAND-CPD:C00389: 2.1.1.- quercetin + S-adenosyl-L-methionine = H+ + isorhamnetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis sitosterol 414.713 C29 H50 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CCC(C(C)C)CC)C)C(CC3)(C)4)))C))O) LIGAND-CPD:C01753:*PUBCHEM:25201437:*CHEBI:27693: 1.3.1.- sitosterol + NADPH + H+ + oxygen = stigmasterol + NADP+ + H2O plant sterol biosynthesis sitosterol 414.713 C29 H50 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CCC(C(C)C)CC)C)C(CC3)(C)4)))C))O) LIGAND-CPD:C01753:*PUBCHEM:25201437:*CHEBI:27693: H+ + Δ24-25-sitosterol + NADPH = sitosterol + NADP+ plant sterol biosynthesis 4α-methyl-5α-ergosta-8,14,24(28)-dien-3β-ol 4α-methyl-5α-ergosta-8,24-dien-3β-ol*4α-methylfecosterol 412.698 C29 H48 O1 C1(CC(C(C2(C1(C3(=C(CC2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))C)O) PUBCHEM:25202325:*LIGAND-CPD:C15776: 5.3.3.5 4α-methyl-5α-ergosta-8,14,24(28)-dien-3β-ol = 24-methylenelophenol plant sterol biosynthesis 4α-methyl-5α-ergosta-8,14,24(28)-dien-3β-ol 4α-methyl-5α-ergosta-8,24-dien-3β-ol*4α-methylfecosterol 412.698 C29 H48 O1 C1(CC(C(C2(C1(C3(=C(CC2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))C)O) PUBCHEM:25202325:*LIGAND-CPD:C15776: 1.3.1.70 4α-methyl-5α-ergosta-8,14,24(28)-dien-3β-ol + NADP+ = 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol + NADPH + H+ plant sterol biosynthesis 3-hydroxypropionate Hydracrylic acid*3-Hydropropionic acid*3-Hydroxypropanoic acid*3-Hydroxypropanoate*hydroxypropionate*3-hydroxypropanoate*β-hydroxypropionate*3-hydroxypropanoic acid*3-hydropropionic acid*hydracrylic acid 89.071 C3 H5 O3 C([O-])(CCO)=O PUBCHEM:5459847:*PUBCHEM:5459847:*CHEBI:16510:*LIGAND-CPD:C01013:*CAS:96-26-4*CAS:503-66-2 1.1.1.59 3-hydroxypropionate + NAD+ = malonate semialdehyde + NADH + H+ β-alanine biosynthesis II 3-hydroxypropionate Hydracrylic acid*3-Hydropropionic acid*3-Hydroxypropanoic acid*3-Hydroxypropanoate*hydroxypropionate*3-hydroxypropanoate*β-hydroxypropionate*3-hydroxypropanoic acid*3-hydropropionic acid*hydracrylic acid 89.071 C3 H5 O3 C([O-])(CCO)=O PUBCHEM:5459847:*PUBCHEM:5459847:*CHEBI:16510:*LIGAND-CPD:C01013:*CAS:96-26-4*CAS:503-66-2 3.1.2.4 3-hydroxypropanoyl-CoA + H2O = H+ + 3-hydroxypropionate + coenzyme A β-alanine biosynthesis II pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.9.2 H2O + pyruvate + ATP = H+ + phosphoenolpyruvate + AMP gluconeogenesis I pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.9.2 H2O + pyruvate + ATP = H+ + phosphoenolpyruvate + AMP glycolysis I pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.6.1.2 2-oxoglutarate + L-alanine = L-glutamate + pyruvate alanine biosynthesis II pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.6.1.2 2-oxoglutarate + L-alanine = L-glutamate + pyruvate alanine degradation II (to D-lactate) pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 3.3.2.1 H2O + isochorismate = pyruvate + 2,3-dihydro-2,3-dihydroxybenzoate 2,3-dihydroxybenzoate biosynthesis pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.9.1 pyruvate + ATP = H+ + phosphoenolpyruvate + AMP + diphosphate glutamine biosynthesis III pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.9.1 pyruvate + ATP = H+ + phosphoenolpyruvate + AMP + diphosphate C4 photosynthetic carbon assimilation cycle pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.2.99.20 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate = H+ + (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + pyruvate 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.1.1.40 (S)-malate + NADP+ = NADPH + CO2 + pyruvate gluconeogenesis I pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.1.1.40 (S)-malate + NADP+ = NADPH + CO2 + pyruvate C4 photosynthetic carbon assimilation cycle pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.2.1.7 H+ + pyruvate + D-glyceraldehyde-3-phosphate = 1-deoxy-D-xylulose 5-phosphate + CO2 methylerythritol phosphate pathway pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.1.1.27 (S)-lactate + NAD+ = pyruvate + NADH + H+ pyruvate fermentation to lactate pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.4.1.8 L-cystathionine + H2O = H+ + ammonia + pyruvate + L-homocysteine methionine biosynthesis II pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.4.1.8 L-cystathionine + H2O = H+ + ammonia + pyruvate + L-homocysteine homocysteine and cysteine interconversion pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.6.1.- beta-methylenecyclopropyl pyruvate + L-alanine = hypoglycin A + pyruvate hypoglycin biosynthesis pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.1.3.27 chorismate + L-glutamine = H+ + anthranilate + L-glutamate + pyruvate tryptophan biosynthesis pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.2.1.52 pyruvate + L-aspartate-semialdehyde = H+ + H2O + L-2,3-dihydrodipicolinate lysine biosynthesis VI pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.2.4.1 pyruvate = CO2 acetyl-CoA biosynthesis (from pyruvate) pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.2.1.23 methylglyoxal + NAD+ + H2O = H+ + pyruvate + NADH methylglyoxal degradation VII pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.1.1.38 (S)-malate + NAD+ = NADH + CO2 + pyruvate gluconeogenesis I pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.1.3.38 4-amino-4-deoxychorismate = H+ + p-aminobenzoate + pyruvate p-aminobenzoate biosynthesis pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.1.1.28 (R)-lactate + NAD+ = pyruvate + NADH + H+ alanine degradation II (to D-lactate) pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.1.1.1 H+ + pyruvate = acetaldehyde + CO2 acetaldehyde biosynthesis II pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.1.1.1 H+ + pyruvate = acetaldehyde + CO2 acetaldehyde biosynthesis I pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.1.1.1 H+ + pyruvate = acetaldehyde + CO2 pyruvate fermentation to ethanol II pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP Rubisco shunt pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP glycolysis III pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP glycolysis IV (plant cytosol) pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP glycolysis I pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.6.1.18 malonate semialdehyde + L-alanine = β-alanine + pyruvate β-alanine biosynthesis II pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.3.1.18 D-serine = H+ + pyruvate + ammonia serine racemization pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.2.1.6 H+ + pyruvate + 2-oxobutanoate = 2-aceto-2-hydroxy-butanoate + CO2 isoleucine biosynthesis I (from threonine) pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.2.1.6 H+ + pyruvate = (S)-2-acetolactate + CO2 valine biosynthesis pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 87.055 C3 H3 O3 C(C(C)=O)(=O)[O-] PUBCHEM:107735:*PUBCHEM:107735:*CHEBI:15361:*PUBCHEM:1060:*KNAPSACK:C00001200:*KNAPKSACK:C00001200*LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.6.1.- L-tryptophan + pyruvate = L-alanine + indole-3-pyruvate IAA biosynthesis I formaldehyde formalin*methanal*formol 30.026 C1 H2 O1 O=C CHEBI:16842:*PUBCHEM:712:*LIGAND-CPD:C00067:*CAS:50-00-0 formaldehyde + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H2O formaldehyde oxidation V (tetrahydrofolate pathway) formaldehyde formalin*methanal*formol 30.026 C1 H2 O1 O=C CHEBI:16842:*PUBCHEM:712:*LIGAND-CPD:C00067:*CAS:50-00-0 1.1.1.244 methanol + NAD+ = H+ + formaldehyde + NADH methanol oxidation to formaldehyde II GDP-L-galactose 603.329 C16 H23 N5 O16 P2 NC4(NC(C3(=C(N(C1(C(C(C(O1)COP(OP(OC2(C(C(C(C(O2)CO)O)O)O))([O-])=O)([O-])=O)O)O))C=N3)N=4))=O) PUBCHEM:25200538:*LIGAND-CPD:C02280: 2.7.7.69 GDP-L-galactose = H+ + GDP + α-L-galactose-1-phosphate ascorbate biosynthesis I (L-galactose pathway) GDP-L-galactose 603.329 C16 H23 N5 O16 P2 NC4(NC(C3(=C(N(C1(C(C(C(O1)COP(OP(OC2(C(C(C(C(O2)CO)O)O)O))([O-])=O)([O-])=O)O)O))C=N3)N=4))=O) PUBCHEM:25200538:*LIGAND-CPD:C02280: GDP-L-fucose + GDP-L-galactose = GDP xyloglucan biosynthesis GDP-L-galactose 603.329 C16 H23 N5 O16 P2 NC4(NC(C3(=C(N(C1(C(C(C(O1)COP(OP(OC2(C(C(C(C(O2)CO)O)O)O))([O-])=O)([O-])=O)O)O))C=N3)N=4))=O) PUBCHEM:25200538:*LIGAND-CPD:C02280: 5.1.3.18 GDP-α-D-mannose = GDP-L-galactose ascorbate biosynthesis I (L-galactose pathway) (2S)-2-isopropylmalate 3-hydroxy-4-methyl-3-carboxypentanoate*3-carboxy-3-hydroxy-4-methylpentanoate*3-carboxy-3-hydroxy-isocaproate*α-isopropylmalate*(2S)-2-isopropylmalate 174.153 C7 H10 O5 OC(CC(=O)[O-])(C(C)C)C([O-])=O PUBCHEM:6419726:*CHEBI:35129:*LIGAND-CPD:C02504: 2.3.3.13 2-oxoisovalerate + acetyl-CoA + H2O = H+ + (2S)-2-isopropylmalate + coenzyme A leucine biosynthesis (2S)-2-isopropylmalate 3-hydroxy-4-methyl-3-carboxypentanoate*3-carboxy-3-hydroxy-4-methylpentanoate*3-carboxy-3-hydroxy-isocaproate*α-isopropylmalate*(2S)-2-isopropylmalate 174.153 C7 H10 O5 OC(CC(=O)[O-])(C(C)C)C([O-])=O PUBCHEM:6419726:*CHEBI:35129:*LIGAND-CPD:C02504: 4.2.1.33 (2S)-2-isopropylmalate = 2-isopropylmaleate + H2O leucine biosynthesis 4-coumarate 4-hydroxycinnamic acid*4-hydroxycinnamate*trans-4-coumarate*trans-4-hydroxycinnamate*trans-p-hydroxycinnamate*p-coumarate*trans-4-hydroxycinnamate*p-coumaric acid*4-Hydroxycinnamic acid*4-Hydroxycinnamate*coumarate 163.152 C9 H7 O3 C1(C=CC(=O)[O-])(=CC=C(O)C=C1) PUBCHEM:5288519:*CHEBI:32373:*LIGAND-CPD:C00811:*CAS:7400-08-0 4-coumarate = 2,4-dihydroxycinnamate simplecoumarins biosynthesis 4-coumarate 4-hydroxycinnamic acid*4-hydroxycinnamate*trans-4-coumarate*trans-4-hydroxycinnamate*trans-p-hydroxycinnamate*p-coumarate*trans-4-hydroxycinnamate*p-coumaric acid*4-Hydroxycinnamic acid*4-Hydroxycinnamate*coumarate 163.152 C9 H7 O3 C1(C=CC(=O)[O-])(=CC=C(O)C=C1) PUBCHEM:5288519:*CHEBI:32373:*LIGAND-CPD:C00811:*CAS:7400-08-0 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ flavonoid biosynthesis 4-coumarate 4-hydroxycinnamic acid*4-hydroxycinnamate*trans-4-coumarate*trans-4-hydroxycinnamate*trans-p-hydroxycinnamate*p-coumarate*trans-4-hydroxycinnamate*p-coumaric acid*4-Hydroxycinnamic acid*4-Hydroxycinnamate*coumarate 163.152 C9 H7 O3 C1(C=CC(=O)[O-])(=CC=C(O)C=C1) PUBCHEM:5288519:*CHEBI:32373:*LIGAND-CPD:C00811:*CAS:7400-08-0 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ simplecoumarins biosynthesis 4-coumarate 4-hydroxycinnamic acid*4-hydroxycinnamate*trans-4-coumarate*trans-4-hydroxycinnamate*trans-p-hydroxycinnamate*p-coumarate*trans-4-hydroxycinnamate*p-coumaric acid*4-Hydroxycinnamic acid*4-Hydroxycinnamate*coumarate 163.152 C9 H7 O3 C1(C=CC(=O)[O-])(=CC=C(O)C=C1) PUBCHEM:5288519:*CHEBI:32373:*LIGAND-CPD:C00811:*CAS:7400-08-0 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ phenylpropanoid biosynthesis 4-coumarate 4-hydroxycinnamic acid*4-hydroxycinnamate*trans-4-coumarate*trans-4-hydroxycinnamate*trans-p-hydroxycinnamate*p-coumarate*trans-4-hydroxycinnamate*p-coumaric acid*4-Hydroxycinnamic acid*4-Hydroxycinnamate*coumarate 163.152 C9 H7 O3 C1(C=CC(=O)[O-])(=CC=C(O)C=C1) PUBCHEM:5288519:*CHEBI:32373:*LIGAND-CPD:C00811:*CAS:7400-08-0 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ 4-hydroxybenzoate biosynthesis V 4-coumarate 4-hydroxycinnamic acid*4-hydroxycinnamate*trans-4-coumarate*trans-4-hydroxycinnamate*trans-p-hydroxycinnamate*p-coumarate*trans-4-hydroxycinnamate*p-coumaric acid*4-Hydroxycinnamic acid*4-Hydroxycinnamate*coumarate 163.152 C9 H7 O3 C1(C=CC(=O)[O-])(=CC=C(O)C=C1) PUBCHEM:5288519:*CHEBI:32373:*LIGAND-CPD:C00811:*CAS:7400-08-0 H+ + 4-coumarate + NADPH + oxygen = trans-caffeate + H2O + NADP+ suberin biosynthesis 4-coumarate 4-hydroxycinnamic acid*4-hydroxycinnamate*trans-4-coumarate*trans-4-hydroxycinnamate*trans-p-hydroxycinnamate*p-coumarate*trans-4-hydroxycinnamate*p-coumaric acid*4-Hydroxycinnamic acid*4-Hydroxycinnamate*coumarate 163.152 C9 H7 O3 C1(C=CC(=O)[O-])(=CC=C(O)C=C1) PUBCHEM:5288519:*CHEBI:32373:*LIGAND-CPD:C00811:*CAS:7400-08-0 H+ + 4-coumarate + NADPH + oxygen = trans-caffeate + H2O + NADP+ free phenylpropanoid acid biosynthesis 4-coumarate 4-hydroxycinnamic acid*4-hydroxycinnamate*trans-4-coumarate*trans-4-hydroxycinnamate*trans-p-hydroxycinnamate*p-coumarate*trans-4-hydroxycinnamate*p-coumaric acid*4-Hydroxycinnamic acid*4-Hydroxycinnamate*coumarate 163.152 C9 H7 O3 C1(C=CC(=O)[O-])(=CC=C(O)C=C1) PUBCHEM:5288519:*CHEBI:32373:*LIGAND-CPD:C00811:*CAS:7400-08-0 1.14.13.11 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 4-coumarate suberin biosynthesis 4-coumarate 4-hydroxycinnamic acid*4-hydroxycinnamate*trans-4-coumarate*trans-4-hydroxycinnamate*trans-p-hydroxycinnamate*p-coumarate*trans-4-hydroxycinnamate*p-coumaric acid*4-Hydroxycinnamic acid*4-Hydroxycinnamate*coumarate 163.152 C9 H7 O3 C1(C=CC(=O)[O-])(=CC=C(O)C=C1) PUBCHEM:5288519:*CHEBI:32373:*LIGAND-CPD:C00811:*CAS:7400-08-0 1.14.13.11 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 4-coumarate phenylpropanoid biosynthesis, initial reactions trans-caffeate trans-caffeic acid*caffeic acid*3,4-dihydroxy-trans-cinnamate*(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid 179.152 C9 H7 O4 [O-]C(=O)C=CC1(C=C(O)C(O)=CC=1) PUBCHEM:5288055:*CHEBI:57770:*PUBCHEM:6950105:*LIGAND-CPD:C01197:*CHEBI:16433: 2.1.1.68 trans-caffeate + S-adenosyl-L-methionine = H+ + ferulate + S-adenosyl-L-homocysteine suberin biosynthesis trans-caffeate trans-caffeic acid*caffeic acid*3,4-dihydroxy-trans-cinnamate*(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid 179.152 C9 H7 O4 [O-]C(=O)C=CC1(C=C(O)C(O)=CC=1) PUBCHEM:5288055:*CHEBI:57770:*PUBCHEM:6950105:*LIGAND-CPD:C01197:*CHEBI:16433: 2.1.1.68 trans-caffeate + S-adenosyl-L-methionine = H+ + ferulate + S-adenosyl-L-homocysteine free phenylpropanoid acid biosynthesis trans-caffeate trans-caffeic acid*caffeic acid*3,4-dihydroxy-trans-cinnamate*(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid 179.152 C9 H7 O4 [O-]C(=O)C=CC1(C=C(O)C(O)=CC=1) PUBCHEM:5288055:*CHEBI:57770:*PUBCHEM:6950105:*LIGAND-CPD:C01197:*CHEBI:16433: 2.1.1.68 trans-caffeate + S-adenosyl-L-methionine = H+ + ferulate + S-adenosyl-L-homocysteine simplecoumarins biosynthesis trans-caffeate trans-caffeic acid*caffeic acid*3,4-dihydroxy-trans-cinnamate*(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid 179.152 C9 H7 O4 [O-]C(=O)C=CC1(C=C(O)C(O)=CC=1) PUBCHEM:5288055:*CHEBI:57770:*PUBCHEM:6950105:*LIGAND-CPD:C01197:*CHEBI:16433: 6.2.1.12 trans-caffeate + coenzyme A + ATP = caffeoyl-CoA + AMP + diphosphate suberin biosynthesis trans-caffeate trans-caffeic acid*caffeic acid*3,4-dihydroxy-trans-cinnamate*(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid 179.152 C9 H7 O4 [O-]C(=O)C=CC1(C=C(O)C(O)=CC=1) PUBCHEM:5288055:*CHEBI:57770:*PUBCHEM:6950105:*LIGAND-CPD:C01197:*CHEBI:16433: 5.2.1.- trans-caffeate = cis-caffeate esculetin biosynthesis trans-caffeate trans-caffeic acid*caffeic acid*3,4-dihydroxy-trans-cinnamate*(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid 179.152 C9 H7 O4 [O-]C(=O)C=CC1(C=C(O)C(O)=CC=1) PUBCHEM:5288055:*CHEBI:57770:*PUBCHEM:6950105:*LIGAND-CPD:C01197:*CHEBI:16433: H+ + 4-coumarate + NADPH + oxygen = trans-caffeate + H2O + NADP+ suberin biosynthesis trans-caffeate trans-caffeic acid*caffeic acid*3,4-dihydroxy-trans-cinnamate*(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid 179.152 C9 H7 O4 [O-]C(=O)C=CC1(C=C(O)C(O)=CC=1) PUBCHEM:5288055:*CHEBI:57770:*PUBCHEM:6950105:*LIGAND-CPD:C01197:*CHEBI:16433: H+ + 4-coumarate + NADPH + oxygen = trans-caffeate + H2O + NADP+ free phenylpropanoid acid biosynthesis avenasterol 412.698 C29 H48 O1 C1(CC(CC2(C1(C3(C(=CC2)C4(CCC(C(CCC(C(C)C)=CC)C)C(CC3)(C)4)))C))O) PUBCHEM:25245230:*LIGAND-CPD:C15782: 1.3.3.- avenasterol = H+ + 5-dehydroavenasterol plant sterol biosynthesis avenasterol 412.698 C29 H48 O1 C1(CC(CC2(C1(C3(C(=CC2)C4(CCC(C(CCC(C(C)C)=CC)C)C(CC3)(C)4)))C))O) PUBCHEM:25245230:*LIGAND-CPD:C15782: 1.1.1.- avenastenone + NADPH + H+ = avenasterol + NADP+ plant sterol biosynthesis trans-zeatin riboside monophosphate ZMP*tZRMP 429.325 C15 H20 N5 O8 P1 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(NCC=C(C)CO)2)))OC(COP(=O)([O-])[O-])3) PUBCHEM:25245853:*LIGAND-CPD:C16430: trans-zeatin riboside monophosphate + H2O = trans-zeatin + D-ribose-5-phosphate trans-zeatin biosynthesis trans-zeatin riboside monophosphate ZMP*tZRMP 429.325 C15 H20 N5 O8 P1 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(NCC=C(C)CO)2)))OC(COP(=O)([O-])[O-])3) PUBCHEM:25245853:*LIGAND-CPD:C16430: trans-zeatin riboside diphosphate + H2O = H+ + trans-zeatin riboside monophosphate trans-zeatin biosynthesis trans-zeatin riboside monophosphate ZMP*tZRMP 429.325 C15 H20 N5 O8 P1 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(NCC=C(C)CO)2)))OC(COP(=O)([O-])[O-])3) PUBCHEM:25245853:*LIGAND-CPD:C16430: N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate + NADPH + H2O = H+ + trans-zeatin riboside monophosphate + NADP+ trans-zeatin biosynthesis 6G-kestotriose kestotriose 504.441 C18 H32 O16 C1(OC(C(O)C(O)1)CO)(CO)OC3(C(O)C(C(O)C(COC2(OC(C(C2O)O)CO)CO)O3)O) PUBCHEM:14282017: 3.2.1.- 6G,6-kestotetraose + H2O = 6G-kestotriose fructan degradation 6G-kestotriose kestotriose 504.441 C18 H32 O16 C1(OC(C(O)C(O)1)CO)(CO)OC3(C(O)C(C(O)C(COC2(OC(C(C2O)O)CO)CO)O3)O) PUBCHEM:14282017: 2.4.1.- 1-kestotriose + sucrose = 6G-kestotriose + sucrose fructan biosynthesis FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 782.533 C27 H30 N9 O15 P2 [N-]1(C(N=C5(C(C1=O)=NC6(=CC(=C(C)C=C(N(CC(O)C(C(COP(=O)(OP(=O)(OCC4(OC(N3(C2(=NC=NC(=C2N=C3)N)))C(C4O)O))[O-])[O-])O)O)5)6)C)))=O) PUBCHEM:25245854:*PUBCHEM:25245854:*LIGAND-CPD:C00016:*CAS:146-14-5 1.5.99.12 H+ + trans-zeatin + H2O + FAD = adenine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 782.533 C27 H30 N9 O15 P2 [N-]1(C(N=C5(C(C1=O)=NC6(=CC(=C(C)C=C(N(CC(O)C(C(COP(=O)(OP(=O)(OCC4(OC(N3(C2(=NC=NC(=C2N=C3)N)))C(C4O)O))[O-])[O-])O)O)5)6)C)))=O) PUBCHEM:25245854:*PUBCHEM:25245854:*LIGAND-CPD:C00016:*CAS:146-14-5 1.21.3.- S-scoulerine + FAD = dehydroscoulerine + FADH2 dehydroscoulerine biosynthesis FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 782.533 C27 H30 N9 O15 P2 [N-]1(C(N=C5(C(C1=O)=NC6(=CC(=C(C)C=C(N(CC(O)C(C(COP(=O)(OP(=O)(OCC4(OC(N3(C2(=NC=NC(=C2N=C3)N)))C(C4O)O))[O-])[O-])O)O)5)6)C)))=O) PUBCHEM:25245854:*PUBCHEM:25245854:*LIGAND-CPD:C00016:*CAS:146-14-5 1.5.99.12 N6-dimethylallyladenine + H+ + FAD + H2O = 3-methyl-2-butenal + adenine + FADH2 cytokinins degradation FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 782.533 C27 H30 N9 O15 P2 [N-]1(C(N=C5(C(C1=O)=NC6(=CC(=C(C)C=C(N(CC(O)C(C(COP(=O)(OP(=O)(OCC4(OC(N3(C2(=NC=NC(=C2N=C3)N)))C(C4O)O))[O-])[O-])O)O)5)6)C)))=O) PUBCHEM:25245854:*PUBCHEM:25245854:*LIGAND-CPD:C00016:*CAS:146-14-5 1.5.99.12 H+ + cis-zeatin + H2O + FAD = 3-methyl-4-cis-hydroxy-2-butenal + adenine + FADH2 cytokinins degradation FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 782.533 C27 H30 N9 O15 P2 [N-]1(C(N=C5(C(C1=O)=NC6(=CC(=C(C)C=C(N(CC(O)C(C(COP(=O)(OP(=O)(OCC4(OC(N3(C2(=NC=NC(=C2N=C3)N)))C(C4O)O))[O-])[O-])O)O)5)6)C)))=O) PUBCHEM:25245854:*PUBCHEM:25245854:*LIGAND-CPD:C00016:*CAS:146-14-5 1.3.99.12 H+ + isobutyryl-CoA + FAD = methylacrylyl-CoA + FADH2 valine degradation I FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 782.533 C27 H30 N9 O15 P2 [N-]1(C(N=C5(C(C1=O)=NC6(=CC(=C(C)C=C(N(CC(O)C(C(COP(=O)(OP(=O)(OCC4(OC(N3(C2(=NC=NC(=C2N=C3)N)))C(C4O)O))[O-])[O-])O)O)5)6)C)))=O) PUBCHEM:25245854:*PUBCHEM:25245854:*LIGAND-CPD:C00016:*CAS:146-14-5 4-coumaroyl-CoA + NADPH + FADH2 = p-dihydrocoumaroyl-CoA + NADP+ + FAD + H+ phloridzin biosynthesis FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 782.533 C27 H30 N9 O15 P2 [N-]1(C(N=C5(C(C1=O)=NC6(=CC(=C(C)C=C(N(CC(O)C(C(COP(=O)(OP(=O)(OCC4(OC(N3(C2(=NC=NC(=C2N=C3)N)))C(C4O)O))[O-])[O-])O)O)5)6)C)))=O) PUBCHEM:25245854:*PUBCHEM:25245854:*LIGAND-CPD:C00016:*CAS:146-14-5 1.3.99.12 H+ + 2-methylbutanoyl-CoA + FAD = 2-methyl-crotonyl-CoA + FADH2 isoleucine degradation I FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 782.533 C27 H30 N9 O15 P2 [N-]1(C(N=C5(C(C1=O)=NC6(=CC(=C(C)C=C(N(CC(O)C(C(COP(=O)(OP(=O)(OCC4(OC(N3(C2(=NC=NC(=C2N=C3)N)))C(C4O)O))[O-])[O-])O)O)5)6)C)))=O) PUBCHEM:25245854:*PUBCHEM:25245854:*LIGAND-CPD:C00016:*CAS:146-14-5 1.5.99.12 H+ + trans-zeatin riboside + H2O + FAD = adenosine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 782.533 C27 H30 N9 O15 P2 [N-]1(C(N=C5(C(C1=O)=NC6(=CC(=C(C)C=C(N(CC(O)C(C(COP(=O)(OP(=O)(OCC4(OC(N3(C2(=NC=NC(=C2N=C3)N)))C(C4O)O))[O-])[O-])O)O)5)6)C)))=O) PUBCHEM:25245854:*PUBCHEM:25245854:*LIGAND-CPD:C00016:*CAS:146-14-5 2.7.7.2 H+ + FMN + ATP = FAD + diphosphate flavin biosynthesis I (bacteria and plants) FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 782.533 C27 H30 N9 O15 P2 [N-]1(C(N=C5(C(C1=O)=NC6(=CC(=C(C)C=C(N(CC(O)C(C(COP(=O)(OP(=O)(OCC4(OC(N3(C2(=NC=NC(=C2N=C3)N)))C(C4O)O))[O-])[O-])O)O)5)6)C)))=O) PUBCHEM:25245854:*PUBCHEM:25245854:*LIGAND-CPD:C00016:*CAS:146-14-5 1.5.99.12 H+ + isopentenyl adenosine + H2O + FAD = adenosine + 3-methyl-2-butenal + FADH2 cytokinins degradation FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 782.533 C27 H30 N9 O15 P2 [N-]1(C(N=C5(C(C1=O)=NC6(=CC(=C(C)C=C(N(CC(O)C(C(COP(=O)(OP(=O)(OCC4(OC(N3(C2(=NC=NC(=C2N=C3)N)))C(C4O)O))[O-])[O-])O)O)5)6)C)))=O) PUBCHEM:25245854:*PUBCHEM:25245854:*LIGAND-CPD:C00016:*CAS:146-14-5 1.14.14.8 anthranilate + oxygen + FADH2 = 3-hydroxyanthranilate + H2O + FAD + H+ anthranilate degradation IV (aerobic) trans-zeatin riboside triphosphate ZTP*zeatin triphosphate*tZRTP 588.277 C15 H21 N5 O14 P3 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(NCC=C(C)CO)2)))OC(COP(=O)([O-])OP(=O)([O-])OP(=O)(O)[O-])3) PUBCHEM:25245231:*LIGAND-CPD:C16428: trans-zeatin riboside triphosphate + H2O = H+ + trans-zeatin riboside diphosphate trans-zeatin biosynthesis trans-zeatin riboside triphosphate ZTP*zeatin triphosphate*tZRTP 588.277 C15 H21 N5 O14 P3 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(NCC=C(C)CO)2)))OC(COP(=O)([O-])OP(=O)([O-])OP(=O)(O)[O-])3) PUBCHEM:25245231:*LIGAND-CPD:C16428: N6-(Δ2-isopentenyl)-adenosine 5'-triphosphate + NADPH + H2O = H+ + trans-zeatin riboside triphosphate + NADP+ trans-zeatin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.29 oxygen = H2O hypusine biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- H+ + coniferaldehyde + NADPH + oxygen = 5-hydroxy-coniferaldehyde + NADP+ + H2O phenylpropanoid biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- H+ + coniferaldehyde + NADPH + oxygen = 5-hydroxy-coniferaldehyde + NADP+ + H2O ferulate and sinapate biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA34 + 2-oxoglutarate + oxygen = H+ + GA34-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.2.3.1 oxygen + H2O = hydrogen peroxide aldehyde oxidation I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.21 H+ + apigenin + NADPH + oxygen = luteolin + NADP+ + H2O luteolin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.6 OPC4-CoA + oxygen = OPC4-trans-2-enoyl-CoA + hydrogen peroxide jasmonic acid biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- 24-methylenelophenol + oxygen + NADH = 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.88 H+ + dihydrokaempferol + NADPH + oxygen = dihydromyricetin + NADP+ + H2O leucodelphinidin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.88 H+ + dihydrokaempferol + NADPH + oxygen = dihydromyricetin + NADP+ + H2O syringetin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 4.1.1.- D-ribulose-1,5-bisphosphate + oxygen = 2-phosphoglycolate + 3-phospho-D-glycerate + H+ photorespiration oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- 24-ethylidenelophenol + NADH + oxygen = 4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA51 + 2-oxoglutarate + oxygen = H+ + GA51-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- 4α-formyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NADH + oxygen = 4α-carboxy-4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.79 H+ + ent-kaurenoate + oxygen + NADPH = ent-7-α-hydroxykaurenoate + H2O + NADP+ GA12 biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.-.- H+ + 6-deoxocathasterone + oxygen = 6-deoxoteasterone + H2O brassinosteroid biosynthesis II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 9'-cis-neurosporene + oxygen = 7',9'-cis-lycopene + H2O trans-lycopene biosynthesis II (plants) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- gibberellin A8 + 2-oxoglutarate + oxygen = H+ + GA8-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.4.3.5 oxygen + pyridoxine-5'-phosphate = hydrogen peroxide + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.- 15-cis-phytoene + oxygen = 9,15,9'-tri-cis-ζ-carotene + H2O trans-lycopene biosynthesis II (plants) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.22 naringenin + 2-oxoglutarate + oxygen = apigenin + succinate + CO2 + H2O luteolin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.7.3.3 urate + oxygen + H2O = 5-hydroxyisourate + hydrogen peroxide urate degradation to allantoin oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.12 oxygen + α-linolenate = 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate traumatin and (Z)-3-hexen-1-yl acetate biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.12 oxygen + α-linolenate = 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate jasmonic acid biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA53 + 2-oxoglutarate + oxygen = GA97 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- L-tryptophan + oxygen + NADPH = N-hydroxy-L-tryptophan + NADP+ + H2O IAA biosynthesis I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- laurate + oxygen + NADPH + H+ = ω-hydroxylaurate + NADP+ + H2O ω-hydroxylation of caprate and laurate oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O leucopelargonidin and leucocyanidin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O leucodelphinidin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O flavonol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA29 + 2-oxoglutarate + oxygen = H+ + GA29-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.11 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 4-coumarate suberin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.11 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 4-coumarate phenylpropanoid biosynthesis, initial reactions oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.12.1 oxygen + L-arginine = 4-guanidinobutyramide + H2O + CO2 arginine degradation X (arginine monooxygenase pathway) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.23 dihydrokaempferol + 2-oxoglutarate + oxygen = kaempferol + succinate + CO2 + H2O flavonol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- 4α-hydroxymethyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NADH + oxygen = 4α-formyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- 4α-formyl-ergosta-7,24(241)-dien-3β-ol + oxygen + NADH = 4α-carboxy-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.4.3.22 propane-1,3-diamine + H2O + oxygen = H+ + 3-aminopropanal + ammonia + hydrogen peroxide β-alanine biosynthesis I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.5.3.14 spermidine + oxygen + H2O = propane-1,3-diamine + 4-aminobutanal + hydrogen peroxide spermine and spermidine degradation II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.1.- sitosterol + NADPH + H+ + oxygen = stigmasterol + NADP+ + H2O plant sterol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.9 H+ + oxygen + NADPH + loganin = H2O + NADP+ + secologanin camptothecin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.3.- H+ + 2-nonaprenyl-6-methoxyphenol + oxygen = 2-methoxy-6-all trans-nonaprenyl-2-methoxy-1,4-benzoquinol + H2O ubiquinol-9 biosynthesis (eukaryotic) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- gibberellin A4 + 2-oxoglutarate + oxygen = GA34 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA19 + oxygen + 2-oxoglutarate = H+ + gibberellin A20 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.- β-cryptoxanthin + oxygen = zeaxanthin + H2O zeaxanthin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- H+ + (3R,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.12 GA44 (open lactone form) + 2-oxoglutarate + oxygen = GA19 + succinate + CO2 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 L-phenylalanine + oxygen + H2O = phenylacetaldehyde + ammonia + hydrogen peroxide + CO2 phenylethanol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- H+ + (22α)-hydroxy-campest-4-en-3-one + NADPH + oxygen = (22R,23R)-22,23-dihydroxy-campest-4-en-3-one + NADP+ + H2O brassinosteroid biosynthesis II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- 7-hydroxy-chlorophyllide a + oxygen + NADPH = chlorophyllide b + H2O + NADP+ chlorophyll cycle oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.4.3.5 oxygen + H2O + pyridoxamine 5'-phosphate = H+ + ammonia + hydrogen peroxide + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- oleate + NADPH + oxygen = 18-hydroxyoleate + NADP+ + H2O suberin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- leucocyanidin + 2-oxoglutarate + oxygen = H+ + cyanidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- H+ + (22α)-hydroxy-campesterol + NADPH + oxygen = (22R,23R)-22,23-dihydroxycampesterol + NADP+ + H2O brassinosteroid biosynthesis II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- gibberellin A20 + 2-oxoglutarate + oxygen = GA29 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.22 eriodictyol + 2-oxoglutarate + oxygen = luteolin + succinate + CO2 + H2O luteolin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA19 + oxygen + 2-oxoglutarate = H+ + GA17 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol + oxygen + NADH = 4α-formyl-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.11.1.6 hydrogen peroxide = H2O + oxygen superoxide radicals degradation oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- H+ + (5α)-campestan-3-one + oxygen + NADPH = (22S,24R)-22-hydroxy-5α-ergostan-3-one + H2O + NADP+ brassinosteroid biosynthesis II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.23 dihydromyricetin + 2-oxoglutarate + oxygen = myricetin + succinate + CO2 + H2O syringetin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.9 (2S)-pinocembrin + oxygen + 2-oxoglutarate = (2R,3R)-pinobanksin + CO2 + succinate pinobanksin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.1.3.15 glycolate + oxygen = glyoxylate + hydrogen peroxide photorespiration oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.19 leucocyanidin + 2-oxoglutarate + oxygen = succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.19.2 oxygen = H2O oleate biosynthesis I (plants) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.21 H+ + naringenin + NADPH + oxygen = eriodictyol + NADP+ + H2O luteolin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- H+ + campestanol + oxygen + NADPH = 6-deoxocathasterone + H2O + NADP+ brassinosteroid biosynthesis II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.- β-carotene + oxygen = β-cryptoxanthin + H2O zeaxanthin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 9,9'-di-cis-ζ-carotene + oxygen = 7,9,9'-cis-neurosporene + H2O trans-lycopene biosynthesis II (plants) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- 4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol + NADH + oxygen = 4α-formyl-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.81 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + oxygen + NADPH + H+ = divinyl protochlorophyllide a + NADP+ + H2O chlorophyllide a biosynthesis I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- 24-methylenecycloartanol + NADH + oxygen = 4α-hydroxymethyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.54 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one + oxygen = H+ + 2-oxo-4-methylthiobutanoate + formate methionine salvage I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.15 gibberellin A20 + 2-oxoglutarate + oxygen = gibberellin A1 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.4.3.10 oxygen + H2O + putrescine = H+ + ammonia + hydrogen peroxide + 4-aminobutanal putrescine degradation IV oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.39 oxygen + NADPH + L-arginine = L-citrulline + NADP+ + nitric oxide citrulline-nitric oxide cycle oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ chlorogenic acid biosynthesis I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ chlorogenic acid biosynthesis II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ phenylpropanoid biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.88 H+ + eriodictyol + NADPH + oxygen = 3',4',5'-pentahydroxyflavanone + NADP+ + H2O leucodelphinidin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.6 oxygen = hydrogen peroxide fatty acid β-oxidation II (core pathway) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.15.1.1 superoxide + H+ = hydrogen peroxide + oxygen superoxide radicals degradation oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- H+ + GA44 + 2-oxoglutarate + oxygen = GA98 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- gibberellin A12 + 2-oxoglutarate + oxygen = GA110 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.79 GA12-aldehyde + NADPH + oxygen = gibberellin A12 + NADP+ + H2O GA12 biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.78 ent-kaurenol + NADPH + H+ + oxygen = ent-kaurenal + NADP+ + H2O GA12 biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.3 coproporphyrinogen III + oxygen + H+ = protoporphyrinogen IX + CO2 + H2O chlorophyllide a biosynthesis I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.3 coproporphyrinogen III + oxygen + H+ = protoporphyrinogen IX + CO2 + H2O heme biosynthesis from uroporphyrinogen-III I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.15.7 choline + oxygen + H+ = betaine aldehyde hydrate + H2O glycine betaine biosynthesis III (plants) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- N-hydroxy-L-tryptophan + oxygen + NADPH + H+ = N,N-dihydroxy-L-tryptophan + NADP+ + H2O IAA biosynthesis I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.2.3.14 abscisic aldehyde + H2O + oxygen = H+ + 2-cis-abscisic acid + hydrogen peroxide abscisic acid biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.2.3.14 abscisic aldehyde + H2O + oxygen = H+ + 2-cis-abscisic acid + hydrogen peroxide aldehyde oxidation I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.1.- 24-epi-campesterol + NADPH + H+ + oxygen = brassicasterol + NADP+ + H2O plant sterol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.8.3.1 sulfite + oxygen + H2O = hydrogen peroxide + sulfate sulfite oxidation IV oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.4 protoporphyrinogen IX + oxygen = protoporphyrin IX + hydrogen peroxide chlorophyllide a biosynthesis I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.4 protoporphyrinogen IX + oxygen = protoporphyrin IX + hydrogen peroxide heme biosynthesis from uroporphyrinogen-III I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.-.- 6-methoxy-5-methyl-2-all-trans-decaprenyl-1,4-benzoquinol + oxygen = 3-demethylubiquinol-10 + H2O ubiquinol-10 biosynthesis (eukaryotic) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 H+ + eriodictyol + NADPH + oxygen = luteolin + NADP+ + H2O luteolin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- nonaprenyl-4-hydroxybenzoate + oxygen + NADPH + H+ = 3,4-dihydroxy-5-all-trans-nonaprenylbenzoate + H2O + NADP+ ubiquinol-9 biosynthesis (eukaryotic) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.99.1 oxygen + myo-inositol = H+ + H2O UDP-D-glucuronate biosynthesis (from myo-inositol) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- gibberellin A9 + 2-oxoglutarate + oxygen = GA51 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 3',4',5'-pentahydroxyflavanone + 2-oxoglutarate + oxygen = dihydromyricetin + succinate + CO2 leucodelphinidin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.6 OPC6-CoA + oxygen = OPC6-trans-2-enoyl-CoA + hydrogen peroxide jasmonic acid biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 H+ + naringenin + NADPH + oxygen = apigenin + NADP+ + H2O luteolin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.3 protoheme IX + oxygen = biliverdin-IX-α + Fe2+ + carbon monoxide + H2O heme degradation oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.70 NADPH + oxygen + obtusifoliol + H+ = H2O + NADP+ + formate + 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol plant sterol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.4.3.16 L-aspartate + oxygen = H+ + α-iminosuccinate + hydrogen peroxide NAD biosynthesis I (from aspartate) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 tryptamine + oxygen + NADPH = N-hydroxyl-tryptamine + H2O + NADP+ IAA biosynthesis I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.14.8 anthranilate + oxygen + FADH2 = 3-hydroxyanthranilate + H2O + FAD + H+ anthranilate degradation IV (aerobic) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.- oxygen = H2O palmitoleate biosynthesis II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 H+ + gibberellin A12 + oxygen = GA53 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.-.- H+ + sphinganine + oxygen + NADPH = 4-hydroxysphinganine + H2O + NADP+ sphingolipid biosynthesis (plants) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 H+ + ferulate + NADPH + oxygen = 5-hydroxyferulate + H2O + NADP+ free phenylpropanoid acid biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.27 4-hydroxyphenylpyruvate + oxygen = CO2 + homogentisate vitamin E biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- H+ + campesterol + oxygen + NADPH = (22α)-hydroxy-campesterol + H2O + NADP+ brassinosteroid biosynthesis II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.112 (22S,24R)-22-hydroxy-5α-ergostan-3-one + oxygen + NADPH + H+ = 3-dehydro-6-deoxoteasterone + NADP+ + H2O brassinosteroid biosynthesis II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.90 zeaxanthin + H+ + oxygen = antheraxanthin + H2O antheraxanthin and violaxanthin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.90 zeaxanthin + H+ + oxygen = antheraxanthin + H2O xanthophyll cycle oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 7-hydroxy-chlorophyll a + H2O + NADP+ = H+ + chlorophyll a + oxygen + NADPH chlorophyll cycle oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.13 gibberellin A1 + 2-oxoglutarate + oxygen = gibberellin A8 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 DMSP-amine + oxygen + H2O = H+ + 3-dimethylsulfoniopropionaldehyde + ammonia + hydrogen peroxide dimethylsulfoniopropionate biosynthesis II (Spartina) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- H+ + 3-epi-6-deoxocathasterone + NADPH + oxygen = 6-deoxotyphasterol + NADP+ + H2O brassinosteroid biosynthesis II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.78 ent-kaurenal + NADPH + oxygen = ent-kaurenoate + NADP+ + H2O GA12 biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.23 trans dihydroquercetin + 2-oxoglutarate + oxygen = quercetin + succinate + CO2 + H2O flavonol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.9 eriodictyol + oxygen + 2-oxoglutarate = trans dihydroquercetin + CO2 + succinate leucopelargonidin and leucocyanidin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.9 eriodictyol + oxygen + 2-oxoglutarate = trans dihydroquercetin + CO2 + succinate leucodelphinidin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.79 ent-7-α-hydroxykaurenoate + NADPH + H+ + oxygen = GA12-aldehyde + NADP+ + H2O GA12 biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.2.3.9 benzaldehyde + oxygen + H2O = H+ + benzoate + hydrogen peroxide aldehyde oxidation I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.2.3.7 indole acetaldehyde + oxygen + H2O = H+ + indole-3-acetate + hydrogen peroxide IAA biosynthesis I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.6 OPC8-CoA + oxygen = OPC8-trans-2-enoyl-CoA + hydrogen peroxide jasmonic acid biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.81 magnesium-protoporphyrin IX 13-monomethyl ester + oxygen + NADPH + H+ = 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.14 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 2-coumarate coumarin biosynthesis (via 2-coumarate) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- H+ + chlorophyllide a + oxygen + NADPH = 7-hydroxy-chlorophyllide a + H2O + NADP+ chlorophyll cycle oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.10.3.- H+ + oxygen = H+ + H2O NADH to cytochrome bd oxidase electron transfer oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.10.3.- H+ + oxygen = H+ + H2O succinate to cytochrome bd oxidase electron transfer oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.12 linoleate + oxygen = (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate traumatin and (Z)-3-hexen-1-yl acetate biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.12 linoleate + oxygen = (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate divinyl ether biosynthesis II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.78 H+ + ent-kaurene + oxygen + NADPH = H2O + NADP+ + ent-kaurenol GA12 biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- 4α-formyl-stigmasta-7,24(241)-dien-3β-ol + NADH + oxygen = 4α-carboxy-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.51 9'-cis-neoxanthin + oxygen = xanthoxin + C25-allenic-apo-aldehyde abscisic acid biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.17.4 H+ + L-ascorbate + 1-aminocyclopropane-1-carboxylate + oxygen = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- H+ + campest-4-en-3-one + oxygen + NADPH = (22α)-hydroxy-campest-4-en-3-one + H2O + NADP+ brassinosteroid biosynthesis II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA53 + oxygen + 2-oxoglutarate = GA44 (open lactone form) + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.9.3.1 oxygen = H2O aerobic respiration -- electron donor II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.7 squalene + oxygen = (S)-2,3-epoxysqualene + H2O epoxysqualene biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.4.3.21 2-phenylethylamine + oxygen + H2O = H+ + phenylacetaldehyde + ammonia + hydrogen peroxide phenylethanol biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- 2-decaprenyl-6-methoxyphenol + oxygen + NADPH + H+ = 2-methoxy-6-all trans-decaprenyl-2-methoxy-1,4-benzoquinol + H2O + NADP+ ubiquinol-10 biosynthesis (eukaryotic) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.19.6 oxygen = H2O linoleate biosynthesis I (plants) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- H+ + (3S,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.9 naringenin + oxygen + 2-oxoglutarate = CO2 + succinate + dihydrokaempferol flavonoid biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- H+ + GA44 (open lactone form) + 2-oxoglutarate + oxygen = GA38 + succinate + CO2 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- leucodelphinidin + oxygen + 2-oxoglutarate = H+ + delphinidin + H2O + CO2 + succinate anthocyanin biosynthesis (delphinidin 3-O-glucoside) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 H+ + 4-coumarate + NADPH + oxygen = trans-caffeate + H2O + NADP+ suberin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 H+ + 4-coumarate + NADPH + oxygen = trans-caffeate + H2O + NADP+ free phenylpropanoid acid biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 7,9,9'-cis-neurosporene + oxygen = prolycopene + H2O trans-lycopene biosynthesis II (plants) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.90 antheraxanthin + H+ + oxygen = violaxanthin + H2O antheraxanthin and violaxanthin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.90 antheraxanthin + H+ + oxygen = violaxanthin + H2O xanthophyll cycle oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.10.3.- H2O = oxygen photosynthesis light reactions oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.93 H+ + 2-cis-abscisic acid + NADPH + oxygen = 8'-hydroxyabscisate + NADP+ + H2O phaseic acid biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.12.20 pheophorbide a + oxygen + NADPH = H+ + red chlorophyll catabolite + NADP+ chlorophyll a degradation oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- 3-decaprenyl-4-hydroxybenzoate + oxygen + NADPH + H+ = 3,4-dihydroxy-5-all-trans-decaprenylbenzoate + H2O + NADP+ ubiquinol-10 biosynthesis (eukaryotic) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O chlorogenic acid biosynthesis I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O chlorogenic acid biosynthesis II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O simplecoumarins biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O phenylpropanoid biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.-.- 6-methoxy-5-methyl-2-all-trans-nonaprenyl-1,4-benzoquinol + oxygen = 3-demethylubiquinol-9 + H2O ubiquinol-9 biosynthesis (eukaryotic) oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.21.3.3 oxygen + (S)-reticuline = H+ + hydrogen peroxide + S-scoulerine dehydroscoulerine biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.81 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + oxygen = 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis I oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.10.3.1 cis-caffeate + oxygen = 3-(2-propenoic acid)-o-benzoquinone + H2O esculetin biosynthesis oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.5.3.14 spermine + oxygen + H2O = 1-(3-aminopropyl)-4-aminobutanal + propane-1,3-diamine + hydrogen peroxide spermine and spermidine degradation II oxygen oxygen*oxygen molecule 31.999 O2 O=O PUBCHEM:977:*CHEBI:15379:*LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- H+ + leucopelargonidin + 2-oxoglutarate + oxygen = pelargonidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) 4α-carboxy-ergosta-7,24(241)-dien-3β-ol 441.673 C29 H45 O3 C1(CC(C(C2(C1(C3(C(=CC2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))C([O-])=O)O) 1.14.13.- 4α-formyl-ergosta-7,24(241)-dien-3β-ol + oxygen + NADH = 4α-carboxy-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis 4α-carboxy-ergosta-7,24(241)-dien-3β-ol 441.673 C29 H45 O3 C1(CC(C(C2(C1(C3(C(=CC2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))C([O-])=O)O) 1.1.1.- 4α-carboxy-ergosta-7,24(241)-dien-3β-ol + NAD+ = episterone + NADH + CO2 plant sterol biosynthesis 6-phospho-D-gluconate 6-p-gluconate*6-phospho-gluconate*6-phosphogluconic acid 273.113 C6 H10 O10 P1 C(C(C(C(C(C([O-])=O)O)O)O)O)OP([O-])([O-])=O PUBCHEM:5459869:*KNAPKSACK:C00007481*CHEBI:48928:*PUBCHEM:25243986:*LIGAND-CPD:C00345: 3.1.1.31 6-phospho-D-glucono-1,5-lactone + H2O = H+ + 6-phospho-D-gluconate pentose phosphate pathway (oxidative branch) 6-phospho-D-gluconate 6-p-gluconate*6-phospho-gluconate*6-phosphogluconic acid 273.113 C6 H10 O10 P1 C(C(C(C(C(C([O-])=O)O)O)O)O)OP([O-])([O-])=O PUBCHEM:5459869:*KNAPKSACK:C00007481*CHEBI:48928:*PUBCHEM:25243986:*LIGAND-CPD:C00345: 1.1.1.44 6-phospho-D-gluconate = D-ribulose-5-phosphate + CO2 pentose phosphate pathway (oxidative branch) cyanidin-3-O-β-D-glucoside cyanidin-3-O-glucoside*Chrysanthemin 448.382 C21 H20 O11 C4(C3(=C(C=C(OC1(C(O)C(O)C(O)C(CO)O1))C(C2(C=CC(O)=C(O)C=2))=[O+]3)C([O-])=CC(O)=4)) CHEBI:28426:*PUBCHEM:25244576:*LIGAND-CPD:C08604: 2.4.1.115 cyanidin = cyanidin-3-O-β-D-glucoside + UDP anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) stearate octadecanoate (n-C18:0)*stearic acid 283.473 C18 H35 O2 C(CCCCCCCCC(=O)[O-])CCCCCCCC PUBCHEM:3033836:*CHEBI:25629:*LIGAND-CPD:C01530:*CAS:57-11-4 3.1.2.14 H2O = stearate stearate biosynthesis II (plants) (S)-1-pyrroline-5-carboxylate pyrroline 5-carboxylate*L-Δ1-pyrroline-5-carboxylate*(S)-1-pyrroline-5-carboxylate*1-pyrroline-5-carboxylate*L-1-pyrroline-5-carboxylate*δ-1-pyrroline-5-carboxylic acid*δ-1-pyrroline-5-carboxylate 112.108 C5 H6 N1 O2 O=C([O-])C1(CCC=N1) PUBCHEM:11966181:*CHEBI:17388:*LIGAND-CPD:C03912:*CAS:2906-39-0 1.5.1.2 L-proline = (S)-1-pyrroline-5-carboxylate + H+ arginine degradation VI (arginase 2 pathway) (S)-1-pyrroline-5-carboxylate pyrroline 5-carboxylate*L-Δ1-pyrroline-5-carboxylate*(S)-1-pyrroline-5-carboxylate*1-pyrroline-5-carboxylate*L-1-pyrroline-5-carboxylate*δ-1-pyrroline-5-carboxylic acid*δ-1-pyrroline-5-carboxylate 112.108 C5 H6 N1 O2 O=C([O-])C1(CCC=N1) PUBCHEM:11966181:*CHEBI:17388:*LIGAND-CPD:C03912:*CAS:2906-39-0 1.5.1.2 L-proline = (S)-1-pyrroline-5-carboxylate + H+ proline biosynthesis II (from arginine) (S)-1-pyrroline-5-carboxylate pyrroline 5-carboxylate*L-Δ1-pyrroline-5-carboxylate*(S)-1-pyrroline-5-carboxylate*1-pyrroline-5-carboxylate*L-1-pyrroline-5-carboxylate*δ-1-pyrroline-5-carboxylic acid*δ-1-pyrroline-5-carboxylate 112.108 C5 H6 N1 O2 O=C([O-])C1(CCC=N1) PUBCHEM:11966181:*CHEBI:17388:*LIGAND-CPD:C03912:*CAS:2906-39-0 1.5.1.2 L-proline = (S)-1-pyrroline-5-carboxylate + H+ proline biosynthesis I (S)-1-pyrroline-5-carboxylate pyrroline 5-carboxylate*L-Δ1-pyrroline-5-carboxylate*(S)-1-pyrroline-5-carboxylate*1-pyrroline-5-carboxylate*L-1-pyrroline-5-carboxylate*δ-1-pyrroline-5-carboxylic acid*δ-1-pyrroline-5-carboxylate 112.108 C5 H6 N1 O2 O=C([O-])C1(CCC=N1) PUBCHEM:11966181:*CHEBI:17388:*LIGAND-CPD:C03912:*CAS:2906-39-0 L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate arginine degradation VI (arginase 2 pathway) (S)-1-pyrroline-5-carboxylate pyrroline 5-carboxylate*L-Δ1-pyrroline-5-carboxylate*(S)-1-pyrroline-5-carboxylate*1-pyrroline-5-carboxylate*L-1-pyrroline-5-carboxylate*δ-1-pyrroline-5-carboxylic acid*δ-1-pyrroline-5-carboxylate 112.108 C5 H6 N1 O2 O=C([O-])C1(CCC=N1) PUBCHEM:11966181:*CHEBI:17388:*LIGAND-CPD:C03912:*CAS:2906-39-0 L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate arginine degradation I (arginase pathway) (S)-1-pyrroline-5-carboxylate pyrroline 5-carboxylate*L-Δ1-pyrroline-5-carboxylate*(S)-1-pyrroline-5-carboxylate*1-pyrroline-5-carboxylate*L-1-pyrroline-5-carboxylate*δ-1-pyrroline-5-carboxylic acid*δ-1-pyrroline-5-carboxylate 112.108 C5 H6 N1 O2 O=C([O-])C1(CCC=N1) PUBCHEM:11966181:*CHEBI:17388:*LIGAND-CPD:C03912:*CAS:2906-39-0 L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate proline biosynthesis II (from arginine) (S)-1-pyrroline-5-carboxylate pyrroline 5-carboxylate*L-Δ1-pyrroline-5-carboxylate*(S)-1-pyrroline-5-carboxylate*1-pyrroline-5-carboxylate*L-1-pyrroline-5-carboxylate*δ-1-pyrroline-5-carboxylic acid*δ-1-pyrroline-5-carboxylate 112.108 C5 H6 N1 O2 O=C([O-])C1(CCC=N1) PUBCHEM:11966181:*CHEBI:17388:*LIGAND-CPD:C03912:*CAS:2906-39-0 L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate proline biosynthesis I (S)-1-pyrroline-5-carboxylate pyrroline 5-carboxylate*L-Δ1-pyrroline-5-carboxylate*(S)-1-pyrroline-5-carboxylate*1-pyrroline-5-carboxylate*L-1-pyrroline-5-carboxylate*δ-1-pyrroline-5-carboxylic acid*δ-1-pyrroline-5-carboxylate 112.108 C5 H6 N1 O2 O=C([O-])C1(CCC=N1) PUBCHEM:11966181:*CHEBI:17388:*LIGAND-CPD:C03912:*CAS:2906-39-0 L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate citrulline biosynthesis (S)-1-pyrroline-5-carboxylate pyrroline 5-carboxylate*L-Δ1-pyrroline-5-carboxylate*(S)-1-pyrroline-5-carboxylate*1-pyrroline-5-carboxylate*L-1-pyrroline-5-carboxylate*δ-1-pyrroline-5-carboxylic acid*δ-1-pyrroline-5-carboxylate 112.108 C5 H6 N1 O2 O=C([O-])C1(CCC=N1) PUBCHEM:11966181:*CHEBI:17388:*LIGAND-CPD:C03912:*CAS:2906-39-0 1.5.99.8 L-proline = (S)-1-pyrroline-5-carboxylate proline degradation (S)-1-pyrroline-5-carboxylate pyrroline 5-carboxylate*L-Δ1-pyrroline-5-carboxylate*(S)-1-pyrroline-5-carboxylate*1-pyrroline-5-carboxylate*L-1-pyrroline-5-carboxylate*δ-1-pyrroline-5-carboxylic acid*δ-1-pyrroline-5-carboxylate 112.108 C5 H6 N1 O2 O=C([O-])C1(CCC=N1) PUBCHEM:11966181:*CHEBI:17388:*LIGAND-CPD:C03912:*CAS:2906-39-0 1.5.99.8 L-proline = (S)-1-pyrroline-5-carboxylate citrulline biosynthesis (S)-1-pyrroline-5-carboxylate pyrroline 5-carboxylate*L-Δ1-pyrroline-5-carboxylate*(S)-1-pyrroline-5-carboxylate*1-pyrroline-5-carboxylate*L-1-pyrroline-5-carboxylate*δ-1-pyrroline-5-carboxylic acid*δ-1-pyrroline-5-carboxylate 112.108 C5 H6 N1 O2 O=C([O-])C1(CCC=N1) PUBCHEM:11966181:*CHEBI:17388:*LIGAND-CPD:C03912:*CAS:2906-39-0 1.5.1.12 (S)-1-pyrroline-5-carboxylate + NAD+ + H2O = H+ + L-glutamate + NADH proline degradation (S)-1-pyrroline-5-carboxylate pyrroline 5-carboxylate*L-Δ1-pyrroline-5-carboxylate*(S)-1-pyrroline-5-carboxylate*1-pyrroline-5-carboxylate*L-1-pyrroline-5-carboxylate*δ-1-pyrroline-5-carboxylic acid*δ-1-pyrroline-5-carboxylate 112.108 C5 H6 N1 O2 O=C([O-])C1(CCC=N1) PUBCHEM:11966181:*CHEBI:17388:*LIGAND-CPD:C03912:*CAS:2906-39-0 1.5.1.12 (S)-1-pyrroline-5-carboxylate + NAD+ + H2O = H+ + L-glutamate + NADH arginine degradation I (arginase pathway) pseudouridine 5'-phosphate 322.168 C9 H11 N2 O9 P1 O=C1(C(=CNC(=O)N1)C2(OC(COP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:25245232:*LIGAND-CPD:C01168:*CAS:1157-60-4 4.2.1.70 D-ribose-5-phosphate + uracil = H2O + pseudouridine 5'-phosphate pseudouridine degradation pseudouridine 5'-phosphate 322.168 C9 H11 N2 O9 P1 O=C1(C(=CNC(=O)N1)C2(OC(COP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:25245232:*LIGAND-CPD:C01168:*CAS:1157-60-4 2.7.1.83 pseudouridine + ATP = H+ + pseudouridine 5'-phosphate + ADP pseudouridine degradation (3R)-linalool (R)-(-)-linalool*(-)-linalool 154.252 C10 H18 O1 CC(C)=CCCC(C)(O)C=C PUBCHEM:14718455:*CHEBI:98:*LIGAND-CPD:C11389:*PUBCHEM:67179: 4.2.3.26 geranyl diphosphate + H2O = (3R)-linalool + diphosphate linalool biosynthesis 2-nonaprenyl-6-methoxyphenol 2-nonaprenyl-6-methoxyphenol 737.203 C52 H80 O2 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(C=CC=C(OC)C=1O))C)C)C)C)C)C)C)CCC=C(C)C PUBCHEM:5372355: 4.1.1.- H+ + 3-methoxy-4-hydroxy-5-all-trans-nonaprenylbenzoate = 2-nonaprenyl-6-methoxyphenol + CO2 ubiquinol-9 biosynthesis (eukaryotic) 2-nonaprenyl-6-methoxyphenol 2-nonaprenyl-6-methoxyphenol 737.203 C52 H80 O2 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(C=CC=C(OC)C=1O))C)C)C)C)C)C)C)CCC=C(C)C PUBCHEM:5372355: 1.14.3.- H+ + 2-nonaprenyl-6-methoxyphenol + oxygen = 2-methoxy-6-all trans-nonaprenyl-2-methoxy-1,4-benzoquinol + H2O ubiquinol-9 biosynthesis (eukaryotic) L-galactose 180.157 C6 H12 O6 C1(OC(C(C(C1O)O)O)O)CO PUBCHEM:6971007:*LIGAND-CPD:C01825:*CHEBI:37620: 3.1.3.- α-L-galactose-1-phosphate + H2O = L-galactose ascorbate biosynthesis I (L-galactose pathway) L-galactose 180.157 C6 H12 O6 C1(OC(C(C(C1O)O)O)O)CO PUBCHEM:6971007:*LIGAND-CPD:C01825:*CHEBI:37620: 1.1.1.- L-galactose + NAD+ = H+ + L-galactono-1,4-lactone + NADH ascorbate biosynthesis I (L-galactose pathway) bicarbonate carbonate*CO3-2*CO32-*bicarbonate*HCO3-*HCO3 61.017 C1 H1 O3 C([O-])(=O)O PUBCHEM:769:*CHEBI:17544:*CAS:71-52-3:*LIGAND-CPD:C00288:*CAS:144-55-8 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis II (acetyl cycle) bicarbonate carbonate*CO3-2*CO32-*bicarbonate*HCO3-*HCO3 61.017 C1 H1 O3 C([O-])(=O)O PUBCHEM:769:*CHEBI:17544:*CAS:71-52-3:*LIGAND-CPD:C00288:*CAS:144-55-8 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate uridine-5'-phosphate biosynthesis bicarbonate carbonate*CO3-2*CO32-*bicarbonate*HCO3-*HCO3 61.017 C1 H1 O3 C([O-])(=O)O PUBCHEM:769:*CHEBI:17544:*CAS:71-52-3:*LIGAND-CPD:C00288:*CAS:144-55-8 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis I bicarbonate carbonate*CO3-2*CO32-*bicarbonate*HCO3-*HCO3 61.017 C1 H1 O3 C([O-])(=O)O PUBCHEM:769:*CHEBI:17544:*CAS:71-52-3:*LIGAND-CPD:C00288:*CAS:144-55-8 1.2.1.27 (S)-methylmalonate-semialdehyde + coenzyme A + NAD+ + H2O = propanoyl-CoA + bicarbonate + NADH + H+ valine degradation I bicarbonate carbonate*CO3-2*CO32-*bicarbonate*HCO3-*HCO3 61.017 C1 H1 O3 C([O-])(=O)O PUBCHEM:769:*CHEBI:17544:*CAS:71-52-3:*LIGAND-CPD:C00288:*CAS:144-55-8 6.4.1.4 ATP + 3-methylcrotonyl-CoA + bicarbonate = H+ + ADP + 3-methylglutaconyl-CoA leucine degradation I bicarbonate carbonate*CO3-2*CO32-*bicarbonate*HCO3-*HCO3 61.017 C1 H1 O3 C([O-])(=O)O PUBCHEM:769:*CHEBI:17544:*CAS:71-52-3:*LIGAND-CPD:C00288:*CAS:144-55-8 4.2.1.104 cyanate + bicarbonate + H+ = carbamate + CO2 cyanate degradation bicarbonate carbonate*CO3-2*CO32-*bicarbonate*HCO3-*HCO3 61.017 C1 H1 O3 C([O-])(=O)O PUBCHEM:769:*CHEBI:17544:*CAS:71-52-3:*LIGAND-CPD:C00288:*CAS:144-55-8 6.4.1.2 ATP + acetyl-CoA + bicarbonate = H+ + malonyl-CoA + ADP fatty acid biosynthesis initiation I bicarbonate carbonate*CO3-2*CO32-*bicarbonate*HCO3-*HCO3 61.017 C1 H1 O3 C([O-])(=O)O PUBCHEM:769:*CHEBI:17544:*CAS:71-52-3:*LIGAND-CPD:C00288:*CAS:144-55-8 6.3.4.14 bicarbonate + ATP = ADP biotin-carboxyl carrier protein assembly bicarbonate carbonate*CO3-2*CO32-*bicarbonate*HCO3-*HCO3 61.017 C1 H1 O3 C([O-])(=O)O PUBCHEM:769:*CHEBI:17544:*CAS:71-52-3:*LIGAND-CPD:C00288:*CAS:144-55-8 4.2.1.1 bicarbonate + H+ = CO2 + H2O cyanate degradation S2- sulfanediide*sulfide(2-)*sulfur(2-) 32.06 S1 [S--] PUBCHEM:29109:*CHEBI:15138: 2.8.1.8 S-adenosyl-L-methionine + S2- = 5'-deoxyadenosine + L-methionine lipoate biosynthesis and incorporation I OPC4-3-hydroxyacyl-CoA 999.813 C35 H52 N7 O19 P3 S1 C(C4(C(=O)CCC(CC(O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])4))C=CCC PUBCHEM:44237301: 4.2.1.17 OPC4-3-hydroxyacyl-CoA = OPC4-trans-2-enoyl-CoA + H2O jasmonic acid biosynthesis OPC4-3-hydroxyacyl-CoA 999.813 C35 H52 N7 O19 P3 S1 C(C4(C(=O)CCC(CC(O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])4))C=CCC PUBCHEM:44237301: 1.1.1.35 NAD+ + OPC4-3-hydroxyacyl-CoA = NADH + H+ + OPC4-3-ketoacyl-CoA jasmonic acid biosynthesis GA17 GA17*gibberellin A17*gibberellin A17 375.397 C20 H23 O7 C1(CCC(C2(C(C34(CC(CCC(C12C([O-])=O)3)(C(C4)=C)O))C([O-])=O))(C)C([O-])=O) PUBCHEM:25200552: 1.14.11.- GA19 + oxygen + 2-oxoglutarate = H+ + GA17 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) acrylyl-CoA acryloyl-CoA*acryloyl-coenzyme A*acrylyl-CoA 817.551 C24 H34 N7 O17 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)C=C)O)(=O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25244583:*CHEBI:15513:*PUBCHEM:25244583:*LIGAND-CPD:C00894:*CAS:5776-58-9 1.3.99.3 propanoyl-CoA = acrylyl-CoA β-alanine biosynthesis II acrylyl-CoA acryloyl-CoA*acryloyl-coenzyme A*acrylyl-CoA 817.551 C24 H34 N7 O17 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)C=C)O)(=O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25244583:*CHEBI:15513:*PUBCHEM:25244583:*LIGAND-CPD:C00894:*CAS:5776-58-9 4.2.1.116 3-hydroxypropanoyl-CoA = acrylyl-CoA + H2O β-alanine biosynthesis II isobutyryl-CoA 2-methylpropanoyl-CoA*isobutyryl-coenzyme A*2-methylpropionyl-CoA*S-(2-methylpropanoyl)-CoA 833.593 C25 H38 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(C(C)C)=O PUBCHEM:25245234:*CHEBI:57338:*PUBCHEM:45266570:*LIGAND-CPD:C00630:*CAS:15621-60-0 1.3.99.12 H+ + isobutyryl-CoA + FAD = methylacrylyl-CoA + FADH2 valine degradation I isobutyryl-CoA 2-methylpropanoyl-CoA*isobutyryl-coenzyme A*2-methylpropionyl-CoA*S-(2-methylpropanoyl)-CoA 833.593 C25 H38 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(C(C)C)=O PUBCHEM:25245234:*CHEBI:57338:*PUBCHEM:45266570:*LIGAND-CPD:C00630:*CAS:15621-60-0 1.2.1.25 2-oxoisovalerate + coenzyme A + NAD+ = isobutyryl-CoA + CO2 + NADH valine degradation I (R)-lactate D-lactate*(R)-2-hydroxypropanate*(R)-2-hydroxypropanate*(R)-lactate*lactate 89.071 C3 H5 O3 C(C(C)O)(=O)[O-] PUBCHEM:5460179:*CHEBI:16004:*LIGAND-CPD:C00256:*CAS:10326-41-7 1.1.1.28 (R)-lactate + NAD+ = pyruvate + NADH + H+ alanine degradation II (to D-lactate) naringenin 5,7,4'-trihydroxyflavone*4,5',7-trihydroxyflavanone*pelargidanon*salipurpol*naringetol*4;,5',7-trihydroxyflavanone*4',5,7-Trihydroxyflavanone*flavanone naringenin 271.249 C15 H11 O5 O=C2(C3(C(OC(C1(=CC=C(C=C1)O))C2)=CC(=CC=3O)[O-])) PUBCHEM:25244584:*LIGAND-CPD:C00509:*CAS:480-41-1 p-dihydrocoumaroyl-CoA + malonyl-CoA = naringenin + coenzyme A + CO2 phloridzin biosynthesis naringenin 5,7,4'-trihydroxyflavone*4,5',7-trihydroxyflavanone*pelargidanon*salipurpol*naringetol*4;,5',7-trihydroxyflavanone*4',5,7-Trihydroxyflavanone*flavanone naringenin 271.249 C15 H11 O5 O=C2(C3(C(OC(C1(=CC=C(C=C1)O))C2)=CC(=CC=3O)[O-])) PUBCHEM:25244584:*LIGAND-CPD:C00509:*CAS:480-41-1 1.14.11.22 naringenin + 2-oxoglutarate + oxygen = apigenin + succinate + CO2 + H2O luteolin biosynthesis naringenin 5,7,4'-trihydroxyflavone*4,5',7-trihydroxyflavanone*pelargidanon*salipurpol*naringetol*4;,5',7-trihydroxyflavanone*4',5,7-Trihydroxyflavanone*flavanone naringenin 271.249 C15 H11 O5 O=C2(C3(C(OC(C1(=CC=C(C=C1)O))C2)=CC(=CC=3O)[O-])) PUBCHEM:25244584:*LIGAND-CPD:C00509:*CAS:480-41-1 1.14.13.21 H+ + naringenin + NADPH + oxygen = eriodictyol + NADP+ + H2O luteolin biosynthesis naringenin 5,7,4'-trihydroxyflavone*4,5',7-trihydroxyflavanone*pelargidanon*salipurpol*naringetol*4;,5',7-trihydroxyflavanone*4',5,7-Trihydroxyflavanone*flavanone naringenin 271.249 C15 H11 O5 O=C2(C3(C(OC(C1(=CC=C(C=C1)O))C2)=CC(=CC=3O)[O-])) PUBCHEM:25244584:*LIGAND-CPD:C00509:*CAS:480-41-1 H+ + naringenin + NADPH + oxygen = apigenin + NADP+ + H2O luteolin biosynthesis naringenin 5,7,4'-trihydroxyflavone*4,5',7-trihydroxyflavanone*pelargidanon*salipurpol*naringetol*4;,5',7-trihydroxyflavanone*4',5,7-Trihydroxyflavanone*flavanone naringenin 271.249 C15 H11 O5 O=C2(C3(C(OC(C1(=CC=C(C=C1)O))C2)=CC(=CC=3O)[O-])) PUBCHEM:25244584:*LIGAND-CPD:C00509:*CAS:480-41-1 1.14.11.9 naringenin + oxygen + 2-oxoglutarate = CO2 + succinate + dihydrokaempferol flavonoid biosynthesis naringenin 5,7,4'-trihydroxyflavone*4,5',7-trihydroxyflavanone*pelargidanon*salipurpol*naringetol*4;,5',7-trihydroxyflavanone*4',5,7-Trihydroxyflavanone*flavanone naringenin 271.249 C15 H11 O5 O=C2(C3(C(OC(C1(=CC=C(C=C1)O))C2)=CC(=CC=3O)[O-])) PUBCHEM:25244584:*LIGAND-CPD:C00509:*CAS:480-41-1 5.5.1.6 naringenin chalcone = H+ + naringenin flavonoid biosynthesis dopamine deoxyepinephrine*hydroxytyramine*3,4-dihydroxyphenethylamine*intropin*2-(3,4-dihydroxyphenyl)ethylamine*4-(2-aminoethyl)benzene-1,2-diol*3-hydroxytyramine 154.188 C8 H12 N1 O2 C1(C(=C(C=CC=1CC[N+])O)O) PUBCHEM:3713609:*PUBCHEM:3713609:*PUBCHEM:681:*LIGAND-CPD:C03758:*CAS:51-61-6 dopamine + betalamic acid = H+ + miraxanthin V + H2O betaxanthin biosynthesis (via dopamine) dopamine deoxyepinephrine*hydroxytyramine*3,4-dihydroxyphenethylamine*intropin*2-(3,4-dihydroxyphenyl)ethylamine*4-(2-aminoethyl)benzene-1,2-diol*3-hydroxytyramine 154.188 C8 H12 N1 O2 C1(C(=C(C=CC=1CC[N+])O)O) PUBCHEM:3713609:*PUBCHEM:3713609:*PUBCHEM:681:*LIGAND-CPD:C03758:*CAS:51-61-6 4.1.1.28 H+ + L-dopa = dopamine + CO2 betaxanthin biosynthesis (via dopamine) L-homoserine L-homoserine*homo-ser*homoserine*2-amino-4-hydroxybutanoic acid*2-amino-4-hydroxybutanoate 119.12 C4 H9 N1 O3 OCCC([N+])C(=O)[O-] CAS:498-19-1*CHEBI:15699:*PUBCHEM:12647:*CAS:672-15-1:*LIGAND-CPD:C00263: 2.7.1.39 L-homoserine + ATP = H+ + O-phospho-L-homoserine + ADP threonine biosynthesis from homoserine L-homoserine L-homoserine*homo-ser*homoserine*2-amino-4-hydroxybutanoic acid*2-amino-4-hydroxybutanoate 119.12 C4 H9 N1 O3 OCCC([N+])C(=O)[O-] CAS:498-19-1*CHEBI:15699:*PUBCHEM:12647:*CAS:672-15-1:*LIGAND-CPD:C00263: 2.7.1.39 L-homoserine + ATP = H+ + O-phospho-L-homoserine + ADP methionine biosynthesis II L-homoserine L-homoserine*homo-ser*homoserine*2-amino-4-hydroxybutanoic acid*2-amino-4-hydroxybutanoate 119.12 C4 H9 N1 O3 OCCC([N+])C(=O)[O-] CAS:498-19-1*CHEBI:15699:*PUBCHEM:12647:*CAS:672-15-1:*LIGAND-CPD:C00263: 1.1.1.3 L-homoserine = L-aspartate-semialdehyde + H+ homoserine biosynthesis L-cystathionine cystathionine*DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(C([O-])=O)(CSCCC([N+])C(=O)[O-])[N+] LIGAND-CPD:C00542:*LIGAND-CPD:C02291:*CHEBI:17482:*LIGAND-CPD:C02291:*PUBCHEM:25243997:*CAS:56-88-2 4.4.1.8 L-cystathionine + H2O = H+ + ammonia + pyruvate + L-homocysteine methionine biosynthesis II L-cystathionine cystathionine*DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(C([O-])=O)(CSCCC([N+])C(=O)[O-])[N+] LIGAND-CPD:C00542:*LIGAND-CPD:C02291:*CHEBI:17482:*LIGAND-CPD:C02291:*PUBCHEM:25243997:*CAS:56-88-2 4.4.1.8 L-cystathionine + H2O = H+ + ammonia + pyruvate + L-homocysteine homocysteine and cysteine interconversion L-cystathionine cystathionine*DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(C([O-])=O)(CSCCC([N+])C(=O)[O-])[N+] LIGAND-CPD:C00542:*LIGAND-CPD:C02291:*CHEBI:17482:*LIGAND-CPD:C02291:*PUBCHEM:25243997:*CAS:56-88-2 4.4.1.1 L-cystathionine + H2O = H+ + ammonia + 2-oxobutanoate + L-cysteine homocysteine and cysteine interconversion L-cystathionine cystathionine*DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(C([O-])=O)(CSCCC([N+])C(=O)[O-])[N+] LIGAND-CPD:C00542:*LIGAND-CPD:C02291:*CHEBI:17482:*LIGAND-CPD:C02291:*PUBCHEM:25243997:*CAS:56-88-2 2.5.1.- L-cysteine + O-phospho-L-homoserine = L-cystathionine methionine biosynthesis II L-cystathionine cystathionine*DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(C([O-])=O)(CSCCC([N+])C(=O)[O-])[N+] LIGAND-CPD:C00542:*LIGAND-CPD:C02291:*CHEBI:17482:*LIGAND-CPD:C02291:*PUBCHEM:25243997:*CAS:56-88-2 4.2.1.22 L-homocysteine + L-serine = H2O + L-cystathionine homocysteine and cysteine interconversion L-cystathionine cystathionine*DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(C([O-])=O)(CSCCC([N+])C(=O)[O-])[N+] LIGAND-CPD:C00542:*LIGAND-CPD:C02291:*CHEBI:17482:*LIGAND-CPD:C02291:*PUBCHEM:25243997:*CAS:56-88-2 O-acetyl-L-homoserine + L-cysteine = H+ + L-cystathionine + acetate homocysteine and cysteine interconversion D-4'-phosphopantothenate 4'-phosphopantothenate*4'-P-Pantothenate*(R)-4'-phosphopantothenate 296.193 C9 H15 N1 O8 P1 C(OP([O-])([O-])=O)C(C(C(=O)NCCC(=O)[O-])O)(C)C PUBCHEM:16755653:*CHEBI:10986:*LIGAND-CPD:C03492: 6.3.2.5 D-4'-phosphopantothenate + L-cysteine + CTP = H+ + R-4'-phosphopantothenoyl-L-cysteine + diphosphate + CMP coenzyme A biosynthesis D-4'-phosphopantothenate 4'-phosphopantothenate*4'-P-Pantothenate*(R)-4'-phosphopantothenate 296.193 C9 H15 N1 O8 P1 C(OP([O-])([O-])=O)C(C(C(=O)NCCC(=O)[O-])O)(C)C PUBCHEM:16755653:*CHEBI:10986:*LIGAND-CPD:C03492: 2.7.1.33 (R)-pantothenate + ATP = H+ + D-4'-phosphopantothenate + ADP phosphopantothenate biosynthesis I 3,4,6-trihydroxy-cis-cinnamate 3,4,6-trihydroxy-cis-cinnamic acid 195.151 C9 H7 O5 OC1(C(O)=CC(=C(C=1)O)C=CC([O-])=O) PUBCHEM:25243999: H+ + 3,4,6-trihydroxy-cis-cinnamate = esculetin + H2O esculetin biosynthesis 3,4,6-trihydroxy-cis-cinnamate 3,4,6-trihydroxy-cis-cinnamic acid 195.151 C9 H7 O5 OC1(C(O)=CC(=C(C=1)O)C=CC([O-])=O) PUBCHEM:25243999: 5.3.-.- H+ + 3-(2-propenoic acid)-4,6-hydroxy cyclohexa-2,5-dienone = 3,4,6-trihydroxy-cis-cinnamate esculetin biosynthesis acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP acetate conversion to acetyl-CoA acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP ethanol degradation II (cytosol) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP ethanol degradation IV (peroxisomal) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.180 acetyl-CoA = coenzyme A + CO2 fatty acid biosynthesis initiation I acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 6.4.1.2 acetyl-CoA = malonyl-CoA biotin-carboxyl carrier protein assembly acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.9 2-methylacetoacetyl-CoA + coenzyme A = propanoyl-CoA + acetyl-CoA isoleucine degradation I acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.16 acetyl-CoA = coenzyme A fatty acid β-oxidation II (core pathway) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.4 D-glucosamine-6-phosphate + acetyl-CoA = H+ + N-acetyl-D-glucosamine-6-phosphate + coenzyme A UDP-N-acetyl-D-glucosamine biosynthesis II acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 6.4.1.2 ATP + acetyl-CoA + bicarbonate = H+ + malonyl-CoA + ADP fatty acid biosynthesis initiation I acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.16 3-(4-hydroxyphenyl)-3-oxo-propionyl-CoA + coenzyme A = acetyl-CoA + 4-hydroxybenzoyl-CoA 4-hydroxybenzoate biosynthesis V acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.13 2-oxoisovalerate + acetyl-CoA + H2O = H+ + (2S)-2-isopropylmalate + coenzyme A leucine biosynthesis acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 3-hydroxy-3-phenylpropionyl-CoA = benzaldehyde + acetyl-CoA benzoate biosynthesis III (CoA-dependent, non-β-oxidative) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.-.- 2-oxohexa-4,5-cyclopropyl-5-enoate + acetyl-CoA + H2O = H+ + 3-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate + coenzyme A hypoglycin biosynthesis acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.10 acetoacetyl-CoA + H2O + acetyl-CoA = H+ + coenzyme A + (S)-3-hydroxy-3-methylglutaryl-CoA mevalonate pathway I acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.12 acetyl-CoA = coenzyme A acetyl-CoA biosynthesis (from pyruvate) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.- acetyl-CoA + (3Z)-hex-3-en-ol = (3Z)-hex-3-en-1-yl acetate + coenzyme A traumatin and (Z)-3-hexen-1-yl acetate biosynthesis acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 4.1.3.4 (S)-3-hydroxy-3-methylglutaryl-CoA = acetoacetate + acetyl-CoA leucine degradation I acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.8 oxaloacetate + acetyl-CoA + ADP = citrate + coenzyme A + ATP acetyl-CoA biosynthesis (from citrate) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.16 OPC4-3-ketoacyl-CoA + coenzyme A = acetyl-CoA + jasmonoyl-CoA jasmonic acid biosynthesis acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.9 acetyl-CoA + H2O + glyoxylate = H+ + (S)-malate + coenzyme A glyoxylate cycle acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.9 acetyl-CoA + H2O + glyoxylate = H+ + (S)-malate + coenzyme A glycolate and glyoxylate degradation II acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.16 OPC8-3-ketoacyl-CoA + coenzyme A = acetyl-CoA + OPC6-CoA jasmonic acid biosynthesis acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.30 L-serine + acetyl-CoA = O-acetyl-L-serine + coenzyme A cysteine biosynthesis I acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.1 L-glutamate + acetyl-CoA = H+ + N-acetyl-L-glutamate + coenzyme A arginine biosynthesis II (acetyl cycle) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.1 L-glutamate + acetyl-CoA = H+ + N-acetyl-L-glutamate + coenzyme A ornithine biosynthesis acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A glyoxylate cycle acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A TCA cycle variation III (eukaryotic) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A glutamine biosynthesis III acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.16 OPC6-3-ketoacyl-CoA + coenzyme A = acetyl-CoA + OPC4-CoA jasmonic acid biosynthesis acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 805.54 C23 H34 N7 O17 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(=O)C PUBCHEM:25244586:*PUBCHEM:25244586:*KNAPSACK:C00007259:*CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.9 acetyl-CoA = acetoacetyl-CoA + coenzyme A mevalonate pathway I N-hydroxyl-tryptamine 176.218 C10 H12 N2 O1 N(O)CCC1(=CNC2(=C1C=CC=C2)) PUBCHEM:13571630:*LIGAND-CPD:C17203: tryptamine + oxygen + NADPH = N-hydroxyl-tryptamine + H2O + NADP+ IAA biosynthesis I N-hydroxyl-tryptamine 176.218 C10 H12 N2 O1 N(O)CCC1(=CNC2(=C1C=CC=C2)) PUBCHEM:13571630:*LIGAND-CPD:C17203: N-hydroxyl-tryptamine = H+ + (E)-indol-3-ylacetaldoxime IAA biosynthesis I 3-phospho-hydroxypyruvate phosphohydroxypyruvate*3-phosphonooxypyruvate*3-P-hydroxypyruvate*3-p-OH-pyr*3-phosphohydroxypyruvate*3-p-OH-pyruvate*3-p-hydroxy-pyr*3-phosphohydroxy-pyr*phosphohydroxypyruate 181.018 C3 H2 O7 P1 O=C(C(COP([O-])(=O)[O-])=O)[O-] PUBCHEM:5460375:*CHEBI:18110:*LIGAND-CPD:C03232:*CAS:3913-50-6 1.1.1.95 3-phospho-D-glycerate + NAD+ = H+ + 3-phospho-hydroxypyruvate + NADH serine biosynthesis 3-phospho-hydroxypyruvate phosphohydroxypyruvate*3-phosphonooxypyruvate*3-P-hydroxypyruvate*3-p-OH-pyr*3-phosphohydroxypyruvate*3-p-OH-pyruvate*3-p-hydroxy-pyr*3-phosphohydroxy-pyr*phosphohydroxypyruate 181.018 C3 H2 O7 P1 O=C(C(COP([O-])(=O)[O-])=O)[O-] PUBCHEM:5460375:*CHEBI:18110:*LIGAND-CPD:C03232:*CAS:3913-50-6 2.6.1.52 3-phospho-L-serine + 2-oxoglutarate = L-glutamate + 3-phospho-hydroxypyruvate serine biosynthesis UDP-D-galacturonate UDP-galacturonate 577.265 C15 H19 N2 O18 P2 O=C([O-])C3(OC(OP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(=O)NC(=O)2)))C(O)C(O)C(O)3) PUBCHEM:15592253:*CHEBI:57635:*PUBCHEM:25244587:*LIGAND-CPD:C00617: 2.4.1.43 UDP-D-galacturonate = UDP homogalacturonan biosynthesis UDP-D-galacturonate UDP-galacturonate 577.265 C15 H19 N2 O18 P2 O=C([O-])C3(OC(OP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(=O)NC(=O)2)))C(O)C(O)C(O)3) PUBCHEM:15592253:*CHEBI:57635:*PUBCHEM:25244587:*LIGAND-CPD:C00617: 5.1.3.6 UDP-D-glucuronate = UDP-D-galacturonate UDP-D-galacturonate biosynthesis I (from UDP-D-glucuronate) tetrahydrogeranylgeranyl-chlorophyll a tetrahydroGG-chlorophyll a*tetrahydroGG-chl a*tetrahydrogeranylgeranyl-chl a 891.487 C55 H70 N4 O5 MG1 C24(C=C9(C(C)C(CCC(=O)OCC=C(C)CCCC(C)CCCC(C)CCC=C(C)C)C5(=N([Mg]36(N1(=C(C(CC)=C(C)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) PUBCHEM:25245863: 1.3.1.- H+ + dihydrogeranylgeranyl-chlorophyll a + NADPH = tetrahydrogeranylgeranyl-chlorophyll a + NADP+ chlorophyll a biosynthesis II tetrahydrogeranylgeranyl-chlorophyll a tetrahydroGG-chlorophyll a*tetrahydroGG-chl a*tetrahydrogeranylgeranyl-chl a 891.487 C55 H70 N4 O5 MG1 C24(C=C9(C(C)C(CCC(=O)OCC=C(C)CCCC(C)CCCC(C)CCC=C(C)C)C5(=N([Mg]36(N1(=C(C(CC)=C(C)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) PUBCHEM:25245863: 1.3.1.- H+ + tetrahydrogeranylgeranyl-chlorophyll a + NADPH = chlorophyll a + NADP+ chlorophyll a biosynthesis II hydrogen selenide dihydridoselenium*H2Se*selane*dihydrogen selenide*[SeH2] 78.96 SE1 [Se] CHEBI:16503:*PUBCHEM:6326970:*CAS:7783-07-5:*LIGAND-CPD:C01528: 2.7.9.3 H2O + hydrogen selenide + ATP = selenophosphate + AMP selenocysteine biosynthesis II (archaea and eukaryotes) violaxanthin 5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-β,β-carotene-3,3'-diol 600.88 C40 H56 O4 C1(C(C2(C(CC1O)(C)O2)(C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC34(C(CC(CC3(C)C)O)(C)O4))C)C))(C)C) PUBCHEM:12358664:*LIGAND-CPD:C08614: 1.14.13.90 antheraxanthin + H+ + oxygen = violaxanthin + H2O antheraxanthin and violaxanthin biosynthesis violaxanthin 5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-β,β-carotene-3,3'-diol 600.88 C40 H56 O4 C1(C(C2(C(CC1O)(C)O2)(C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC34(C(CC(CC3(C)C)O)(C)O4))C)C))(C)C) PUBCHEM:12358664:*LIGAND-CPD:C08614: 1.14.13.90 antheraxanthin + H+ + oxygen = violaxanthin + H2O xanthophyll cycle violaxanthin 5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-β,β-carotene-3,3'-diol 600.88 C40 H56 O4 C1(C(C2(C(CC1O)(C)O2)(C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC34(C(CC(CC3(C)C)O)(C)O4))C)C))(C)C) PUBCHEM:12358664:*LIGAND-CPD:C08614: 1.10.99.3 H+ + violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O antheraxanthin and violaxanthin biosynthesis violaxanthin 5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-β,β-carotene-3,3'-diol 600.88 C40 H56 O4 C1(C(C2(C(CC1O)(C)O2)(C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC34(C(CC(CC3(C)C)O)(C)O4))C)C))(C)C) PUBCHEM:12358664:*LIGAND-CPD:C08614: 1.10.99.3 H+ + violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle violaxanthin 5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-β,β-carotene-3,3'-diol 600.88 C40 H56 O4 C1(C(C2(C(CC1O)(C)O2)(C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC34(C(CC(CC3(C)C)O)(C)O4))C)C))(C)C) PUBCHEM:12358664:*LIGAND-CPD:C08614: 5.3.99.9 violaxanthin = trans-neoxanthin abscisic acid biosynthesis (E)-β-caryophyllene caryophyllene*L-caryophyllene*(E)-β-caryophylene*8-methylene-4,11,11-(trimethyl)bicyclo[7.2.0]undec-4-ene*trans-β-caryophyllene 204.355 C15 H24 C1(CCC2(C(CC(C(CCC=1)=C)2)(C)C))C PUBCHEM:5354499:*LIGAND-CPD:C09629: 4.2.3.- (2E,6E)-farnesyl diphosphate = (E)-β-caryophyllene + diphosphate β-caryophyllene biosynthesis 2-keto-3-methyl-valerate (3S)-3-Methyl-2-oxopentanoate*α-keto-methylvalerate*2-oxo-3-methylvalerate*(S)-2-oxo-3-methylpentanoate*(S)-3-methyl-2-oxopentanoate*2-oxo-3-methylpentanoate*3-methyl-2-oxopentanoate*α-keto-β-methyl-valerate 129.135 C6 H9 O3 CCC(C(C([O-])=O)=O)C CHEBI:35146:*PUBCHEM:6857401:*LIGAND-CPD:C00671:*CAS:1460-34-0 2.6.1.42 L-isoleucine + 2-oxoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine degradation I 2-keto-3-methyl-valerate (3S)-3-Methyl-2-oxopentanoate*α-keto-methylvalerate*2-oxo-3-methylvalerate*(S)-2-oxo-3-methylpentanoate*(S)-3-methyl-2-oxopentanoate*2-oxo-3-methylpentanoate*3-methyl-2-oxopentanoate*α-keto-β-methyl-valerate 129.135 C6 H9 O3 CCC(C(C([O-])=O)=O)C CHEBI:35146:*PUBCHEM:6857401:*LIGAND-CPD:C00671:*CAS:1460-34-0 2.6.1.42 L-isoleucine + 2-oxoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine biosynthesis I (from threonine) 2-keto-3-methyl-valerate (3S)-3-Methyl-2-oxopentanoate*α-keto-methylvalerate*2-oxo-3-methylvalerate*(S)-2-oxo-3-methylpentanoate*(S)-3-methyl-2-oxopentanoate*2-oxo-3-methylpentanoate*3-methyl-2-oxopentanoate*α-keto-β-methyl-valerate 129.135 C6 H9 O3 CCC(C(C([O-])=O)=O)C CHEBI:35146:*PUBCHEM:6857401:*LIGAND-CPD:C00671:*CAS:1460-34-0 4.2.1.9 2,3-dihydroxy-3-methylvalerate = 2-keto-3-methyl-valerate + H2O isoleucine biosynthesis I (from threonine) 2-keto-3-methyl-valerate (3S)-3-Methyl-2-oxopentanoate*α-keto-methylvalerate*2-oxo-3-methylvalerate*(S)-2-oxo-3-methylpentanoate*(S)-3-methyl-2-oxopentanoate*2-oxo-3-methylpentanoate*3-methyl-2-oxopentanoate*α-keto-β-methyl-valerate 129.135 C6 H9 O3 CCC(C(C([O-])=O)=O)C CHEBI:35146:*PUBCHEM:6857401:*LIGAND-CPD:C00671:*CAS:1460-34-0 2-keto-3-methyl-valerate + NAD+ + coenzyme A = 2-methylbutanoyl-CoA + NADH + CO2 isoleucine degradation I nicotinamide 6-aminonicotinamide*vitamin PP*niacinamide 122.126 C6 H6 N2 O1 O=C(N)C1(C=NC=CC=1) CHEBI:17154:*PUBCHEM:936:*KNAPSACK:C00000209:*LIGAND-CPD:C00153:*CAS:98-92-0 3.2.2.14 nicotinamide mononucleotide + H2O = H+ + D-ribose-5-phosphate + nicotinamide pyridine nucleotide cycling (plants) nicotinamide 6-aminonicotinamide*vitamin PP*niacinamide 122.126 C6 H6 N2 O1 O=C(N)C1(C=NC=CC=1) CHEBI:17154:*PUBCHEM:936:*KNAPSACK:C00000209:*LIGAND-CPD:C00153:*CAS:98-92-0 2.7.1.160 NAD+ = ADP ribose 1'',2''-cyclic phosphate + nicotinamide + H2O tRNA splicing nicotinamide 6-aminonicotinamide*vitamin PP*niacinamide 122.126 C6 H6 N2 O1 O=C(N)C1(C=NC=CC=1) CHEBI:17154:*PUBCHEM:936:*KNAPSACK:C00000209:*LIGAND-CPD:C00153:*CAS:98-92-0 glycine + L-cysteine + NAD+ = 2-carboxylate-4-methyl-5-beta-(ethyl adenosine 5-diphosphate) thiazole + nicotinamide thiamine biosynthesis II nicotinamide 6-aminonicotinamide*vitamin PP*niacinamide 122.126 C6 H6 N2 O1 O=C(N)C1(C=NC=CC=1) CHEBI:17154:*PUBCHEM:936:*KNAPSACK:C00000209:*LIGAND-CPD:C00153:*CAS:98-92-0 3.2.2.- nicotinamide riboside + H2O = nicotinamide pyridine nucleotide cycling (plants) nicotinamide 6-aminonicotinamide*vitamin PP*niacinamide 122.126 C6 H6 N2 O1 O=C(N)C1(C=NC=CC=1) CHEBI:17154:*PUBCHEM:936:*KNAPSACK:C00000209:*LIGAND-CPD:C00153:*CAS:98-92-0 3.5.1.19 nicotinamide + H2O = H+ + ammonia + nicotinate pyridine nucleotide cycling (plants) (+)-7-iso-jasmonate (+)-7-iso-jasmonic acid*iso-jasmonic acid*(3R,7S)-(+)-7-iso-jasmonate 209.264 C12 H17 O3 C(=CCC)CC1(C(=O)CCC1CC([O-])=O) PUBCHEM:7251182:*PUBCHEM:7251182:*LIGAND-CPD:C16317: (+)-7-iso-jasmonate = (-)-jasmonate jasmonic acid biosynthesis (+)-7-iso-jasmonate (+)-7-iso-jasmonic acid*iso-jasmonic acid*(3R,7S)-(+)-7-iso-jasmonate 209.264 C12 H17 O3 C(=CCC)CC1(C(=O)CCC1CC([O-])=O) PUBCHEM:7251182:*PUBCHEM:7251182:*LIGAND-CPD:C16317: 3.1.2.20 jasmonoyl-CoA + H2O = H+ + (+)-7-iso-jasmonate + coenzyme A jasmonic acid biosynthesis 12,13(S)-epoxylinolenate 12,13(S)-epoxylinolenic acid*epoxylinolenic acid*12,13-epoxy-octadecatrienoic acid*(9Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate*(9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate*12,13-EOT 291.409 C18 H27 O3 C(=CCC1(OC1=CC=CCCCCCCCC(=O)[O-]))CC PUBCHEM:25244010:*PUBCHEM:25244010:*LIGAND-CPD:C04672: 5.3.99.6 12,13(S)-epoxylinolenate = 12-oxo-cis-10,15-phytodienoate jasmonic acid biosynthesis 12,13(S)-epoxylinolenate 12,13(S)-epoxylinolenic acid*epoxylinolenic acid*12,13-epoxy-octadecatrienoic acid*(9Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate*(9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate*12,13-EOT 291.409 C18 H27 O3 C(=CCC1(OC1=CC=CCCCCCCCC(=O)[O-]))CC PUBCHEM:25244010:*PUBCHEM:25244010:*LIGAND-CPD:C04672: 4.2.1.92 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate = H2O + 12,13(S)-epoxylinolenate jasmonic acid biosynthesis D-glycerate D-glycerate*D-glycerate*(R)-glycerate*glycerate 106.078 C3 H5 O4 OCC(O)C(=O)[O-] KNAPKSACK:C00001185*CHEBI:16659:*PUBCHEM:5460358:*CAS:473-81-4:*LIGAND-CPD:C00258:*CAS:6000-40-4 2.7.1.31 D-glycerate + ATP = H+ + 3-phospho-D-glycerate + ADP photorespiration D-glycerate D-glycerate*D-glycerate*(R)-glycerate*glycerate 106.078 C3 H5 O4 OCC(O)C(=O)[O-] KNAPKSACK:C00001185*CHEBI:16659:*PUBCHEM:5460358:*CAS:473-81-4:*LIGAND-CPD:C00258:*CAS:6000-40-4 1.1.1.29 D-glycerate + NAD+ = H+ + hydroxypyruvate + NADH photorespiration methylacrylyl-CoA methacrylyl-CoA*2-methylprop-2-enoyl-CoA*methacrylyl-coenzyme A 831.577 C25 H36 N7 O17 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(NCCC(NCCSC(=O)C(=C)C)=O)=O)O)[O-])O1)OP(=O)([O-])[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25245875:*LIGAND-CPD:C03460:*CAS:6008-91-9 4.2.1.17 (S)-3-hydroxy-isobutyryl-CoA = methylacrylyl-CoA + H2O valine degradation I methylacrylyl-CoA methacrylyl-CoA*2-methylprop-2-enoyl-CoA*methacrylyl-coenzyme A 831.577 C25 H36 N7 O17 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(NCCC(NCCSC(=O)C(=C)C)=O)=O)O)[O-])O1)OP(=O)([O-])[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25245875:*LIGAND-CPD:C03460:*CAS:6008-91-9 1.3.99.12 H+ + isobutyryl-CoA + FAD = methylacrylyl-CoA + FADH2 valine degradation I CMP-3-deoxy-D-manno-octulosonate CMP-2-dehydro-3-deoxy-D-octonate*CMP-KDO 541.361 C17 H24 N3 O15 P1 OC1(C(C(OC1N2(C(N=C(C=C2)N)=O))COP(OC3(C(=O)[O-])(OC(C(O)CO)C(O)C(O)C3))(=O)[O-])O) PUBCHEM:25245873:*LIGAND-CPD:C04121: 2.7.7.38 3-deoxy-D-manno-octulosonate + CTP = CMP-3-deoxy-D-manno-octulosonate + diphosphate CMP-KDO biosynthesis II (from D-arabinose 5-phosphate) quinolinate 2,3-pyridinedicarboxylic acid*2,3-pyridinedicarboxylate*quinolinic acid*pyridine-2,3-dicarboxylic acid*pyridine-2,3-dicarboxylate 165.105 C7 H3 N1 O4 [O-]C(=O)C1(C(C([O-])=O)=NC=CC=1) PUBCHEM:5460301:*CHEBI:29959:*LIGAND-CPD:C03722:*CAS:89-00-9 2.5.1.72 α-iminosuccinate + dihydroxyacetone phosphate = quinolinate + H2O NAD biosynthesis I (from aspartate) quinolinate 2,3-pyridinedicarboxylic acid*2,3-pyridinedicarboxylate*quinolinic acid*pyridine-2,3-dicarboxylic acid*pyridine-2,3-dicarboxylate 165.105 C7 H3 N1 O4 [O-]C(=O)C1(C(C([O-])=O)=NC=CC=1) PUBCHEM:5460301:*CHEBI:29959:*LIGAND-CPD:C03722:*CAS:89-00-9 2.4.2.19 H+ + 5-phospho-α-D-ribose 1-diphosphate + quinolinate = CO2 + diphosphate + nicotinate mononucleotide NAD biosynthesis I (from aspartate) 3-demethylubiquinol-9 783.228 C53 H82 O4 C(C1(C(=C(C(OC)=C(O)C(O)=1)O)C))C=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C PUBCHEM:25245254: 1.14.-.- 6-methoxy-5-methyl-2-all-trans-nonaprenyl-1,4-benzoquinol + oxygen = 3-demethylubiquinol-9 + H2O ubiquinol-9 biosynthesis (eukaryotic) 3-demethylubiquinol-9 783.228 C53 H82 O4 C(C1(C(=C(C(OC)=C(O)C(O)=1)O)C))C=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C PUBCHEM:25245254: 2.1.1.64 3-demethylubiquinol-9 + S-adenosyl-L-methionine = H+ + ubiquinol-9 + S-adenosyl-L-homocysteine ubiquinol-9 biosynthesis (eukaryotic) sulfoquinovosyldiacylglycerol SQDG C11 H16 O12 R11 R21 S1 C(=O)([R1])OCC(COC1(OC(C(C(O)C1O)O)CS(O)(=O)=O))OC(=O)[R2] PUBCHEM:448048:*PUBCHEM:25244599:*LIGAND-CPD:C13508: UDP-α-D-sulfoquinovopyranose = sulfoquinovosyldiacylglycerol + UDP sulfolipid biosynthesis (S)-3-hydroxy-3-methylglutaryl-CoA (S)-3-hydroxy-3-methylglutaryl-CoA*3-hydroxy-3-methyl-glutaryl-CoA*HMG-CoA*hydroxymethylglutaryl-CoA*3-hydroxy-3-methylglutaryl-coenzyme A*3-Hydroxy-3-methylglutaryl-CoA 906.621 C27 H39 N7 O20 P3 S1 C1(C(O)C(C(COP(=O)(OP([O-])(OCC(C(O)C(=O)NCCC(=O)NCCSC(=O)CC(C)(O)CC(=O)[O-])(C)C)=O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) CHEBI:15467:*PUBCHEM:3617:*LIGAND-CPD:C00356:*CAS:1553-55-5 1.1.1.34 NADP+ + coenzyme A + (R)-mevalonate = H+ + NADPH + (S)-3-hydroxy-3-methylglutaryl-CoA mevalonate pathway I (S)-3-hydroxy-3-methylglutaryl-CoA (S)-3-hydroxy-3-methylglutaryl-CoA*3-hydroxy-3-methyl-glutaryl-CoA*HMG-CoA*hydroxymethylglutaryl-CoA*3-hydroxy-3-methylglutaryl-coenzyme A*3-Hydroxy-3-methylglutaryl-CoA 906.621 C27 H39 N7 O20 P3 S1 C1(C(O)C(C(COP(=O)(OP([O-])(OCC(C(O)C(=O)NCCC(=O)NCCSC(=O)CC(C)(O)CC(=O)[O-])(C)C)=O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) CHEBI:15467:*PUBCHEM:3617:*LIGAND-CPD:C00356:*CAS:1553-55-5 4.2.1.18 (S)-3-hydroxy-3-methylglutaryl-CoA = H2O + 3-methylglutaconyl-CoA leucine degradation I (S)-3-hydroxy-3-methylglutaryl-CoA (S)-3-hydroxy-3-methylglutaryl-CoA*3-hydroxy-3-methyl-glutaryl-CoA*HMG-CoA*hydroxymethylglutaryl-CoA*3-hydroxy-3-methylglutaryl-coenzyme A*3-Hydroxy-3-methylglutaryl-CoA 906.621 C27 H39 N7 O20 P3 S1 C1(C(O)C(C(COP(=O)(OP([O-])(OCC(C(O)C(=O)NCCC(=O)NCCSC(=O)CC(C)(O)CC(=O)[O-])(C)C)=O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) CHEBI:15467:*PUBCHEM:3617:*LIGAND-CPD:C00356:*CAS:1553-55-5 2.3.3.10 acetoacetyl-CoA + H2O + acetyl-CoA = H+ + coenzyme A + (S)-3-hydroxy-3-methylglutaryl-CoA mevalonate pathway I (S)-3-hydroxy-3-methylglutaryl-CoA (S)-3-hydroxy-3-methylglutaryl-CoA*3-hydroxy-3-methyl-glutaryl-CoA*HMG-CoA*hydroxymethylglutaryl-CoA*3-hydroxy-3-methylglutaryl-coenzyme A*3-Hydroxy-3-methylglutaryl-CoA 906.621 C27 H39 N7 O20 P3 S1 C1(C(O)C(C(COP(=O)(OP([O-])(OCC(C(O)C(=O)NCCC(=O)NCCSC(=O)CC(C)(O)CC(=O)[O-])(C)C)=O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) CHEBI:15467:*PUBCHEM:3617:*LIGAND-CPD:C00356:*CAS:1553-55-5 4.1.3.4 (S)-3-hydroxy-3-methylglutaryl-CoA = acetoacetate + acetyl-CoA leucine degradation I leucodelphinidin leucoefdin*leucodelfinidin 322.271 C15 H14 O8 C1(C(=CC(=C2(C=1OC(C(C2O)O)C3(C=C(C(=C(C=3)O)O)O)))O)O) PUBCHEM:3081374:*LIGAND-CPD:C05909: 1.14.11.- leucodelphinidin + oxygen + 2-oxoglutarate = H+ + delphinidin + H2O + CO2 + succinate anthocyanin biosynthesis (delphinidin 3-O-glucoside) leucodelphinidin leucoefdin*leucodelfinidin 322.271 C15 H14 O8 C1(C(=CC(=C2(C=1OC(C(C2O)O)C3(C=C(C(=C(C=3)O)O)O)))O)O) PUBCHEM:3081374:*LIGAND-CPD:C05909: 1.1.1.219 H+ + dihydromyricetin + NADPH = leucodelphinidin + NADP+ leucodelphinidin biosynthesis leucodelphinidin leucoefdin*leucodelfinidin 322.271 C15 H14 O8 C1(C(=CC(=C2(C=1OC(C(C2O)O)C3(C=C(C(=C(C=3)O)O)O)))O)O) PUBCHEM:3081374:*LIGAND-CPD:C05909: 1.17.1.3 gallocatechin + NADP+ + H2O = leucodelphinidin + NADPH + H+ 2,3-trans-flavanols biosynthesis 2-methoxy-6-all trans-nonaprenyl-2-methoxy-1,4-benzoquinol 2-nonaprenyl-6-methoxy-1,4-benzoquinol*2-methoxy-6-nonaprenyl-2-methoxy-1,4-benzoquinol 753.202 C52 H80 O3 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(C=C(O)C=C(OC)C=1O))C)C)C)C)C)C)C)CCC=C(C)C PUBCHEM:25245880: 2.1.1.- 2-methoxy-6-all trans-nonaprenyl-2-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine = H+ + 6-methoxy-5-methyl-2-all-trans-nonaprenyl-1,4-benzoquinol + S-adenosyl-L-homocysteine ubiquinol-9 biosynthesis (eukaryotic) 2-methoxy-6-all trans-nonaprenyl-2-methoxy-1,4-benzoquinol 2-nonaprenyl-6-methoxy-1,4-benzoquinol*2-methoxy-6-nonaprenyl-2-methoxy-1,4-benzoquinol 753.202 C52 H80 O3 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(C=C(O)C=C(OC)C=1O))C)C)C)C)C)C)C)CCC=C(C)C PUBCHEM:25245880: 1.14.3.- H+ + 2-nonaprenyl-6-methoxyphenol + oxygen = 2-methoxy-6-all trans-nonaprenyl-2-methoxy-1,4-benzoquinol + H2O ubiquinol-9 biosynthesis (eukaryotic) (3Z)-hex-3-en-1-yl acetate 142.197 C8 H14 O2 CCC=CCCOC(=O)C 2.3.1.- acetyl-CoA + (3Z)-hex-3-en-ol = (3Z)-hex-3-en-1-yl acetate + coenzyme A traumatin and (Z)-3-hexen-1-yl acetate biosynthesis prolycopene 7,9,9',7'-tetra-cis-lycopene*9,9'-di-cis-ζ-carotene 536.882 C40 H56 CC(=CCCC(=CC=CC(C)=CC=CC(=CC=CC=C(C=CC=C(C)C=CC=C(CCC=C(C)C)C)C)C)C)C PUBCHEM:10918539:*LIGAND-CPD:C15858: 7,9,9'-cis-neurosporene + oxygen = prolycopene + H2O trans-lycopene biosynthesis II (plants) prolycopene 7,9,9',7'-tetra-cis-lycopene*9,9'-di-cis-ζ-carotene 536.882 C40 H56 CC(=CCCC(=CC=CC(C)=CC=CC(=CC=CC=C(C=CC=C(C)C=CC=C(CCC=C(C)C)C)C)C)C)C PUBCHEM:10918539:*LIGAND-CPD:C15858: 5.2.1.- prolycopene = all-trans-lycopene trans-lycopene biosynthesis II (plants) 2,3-dimethyl-6-phytyl-1,4-benzoquinol 416.686 C28 H48 O2 CC(CCCC(CCCC(=CCC1(C=C(O)C(C)=C(C(O)=1)C))C)C)CCCC(C)C PUBCHEM:23724602:*LIGAND-CPD:C15883: 2.1.1.- 2-methyl-6-phytyl-1,4-benzoquinol + S-adenosyl-L-methionine = H+ + 2,3-dimethyl-6-phytyl-1,4-benzoquinol + S-adenosyl-L-homocysteine vitamin E biosynthesis 2,3-dimethyl-6-phytyl-1,4-benzoquinol 416.686 C28 H48 O2 CC(CCCC(CCCC(=CCC1(C=C(O)C(C)=C(C(O)=1)C))C)C)CCCC(C)C PUBCHEM:23724602:*LIGAND-CPD:C15883: 2,3-dimethyl-6-phytyl-1,4-benzoquinol = γ-tocopherol vitamin E biosynthesis GA97 gibberellin A97*gibberellin A97*GA97 362.422 C20 H26 O6 C1(C(CC(C2(C(C34(CC(CCC(C1(C)2)3)(C(C4)=C)O))C([O-])=O))(C)C([O-])=O)O) PUBCHEM:25203277: 1.14.11.- GA53 + 2-oxoglutarate + oxygen = GA97 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) all-trans-nonaprenyl diphosphate solanyl pyrophosphate*all-trans-nonaprenyl diphosphate*nonaprenyl diphosphate*all-trans-nonaprenyl diphosphate*solanesyl diphosphate*(hydroxy-(3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaenoxy)phosphinoyl)oxyphosphonic acid*solanesyl pyrophosphate 788.015 C45 H73 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] PUBCHEM:25244603:*LIGAND-CPD:C04145:*KNAPSACK:C00007289:*PUBCHEM:25244603: 2.5.1.85 all-trans-geranyl-geranyl diphosphate + isopentenyl diphosphate = all-trans-nonaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis II all-trans-nonaprenyl diphosphate solanyl pyrophosphate*all-trans-nonaprenyl diphosphate*nonaprenyl diphosphate*all-trans-nonaprenyl diphosphate*solanesyl diphosphate*(hydroxy-(3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaenoxy)phosphinoyl)oxyphosphonic acid*solanesyl pyrophosphate 788.015 C45 H73 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] PUBCHEM:25244603:*LIGAND-CPD:C04145:*KNAPSACK:C00007289:*PUBCHEM:25244603: 2.5.1.84 all-trans-octaprenyl diphosphate + isopentenyl diphosphate = H+ + all-trans-nonaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III all-trans-nonaprenyl diphosphate solanyl pyrophosphate*all-trans-nonaprenyl diphosphate*nonaprenyl diphosphate*all-trans-nonaprenyl diphosphate*solanesyl diphosphate*(hydroxy-(3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaenoxy)phosphinoyl)oxyphosphonic acid*solanesyl pyrophosphate 788.015 C45 H73 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] PUBCHEM:25244603:*LIGAND-CPD:C04145:*KNAPSACK:C00007289:*PUBCHEM:25244603: 2.5.1.39 all-trans-nonaprenyl diphosphate = nonaprenyl-4-hydroxybenzoate + diphosphate ubiquinol-9 biosynthesis (eukaryotic) all-trans-heptaprenyl diphosphate 651.779 C35 H57 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] PUBCHEM:25245257:*LIGAND-CPD:C04216: 2.5.1.90 all-trans-heptaprenyl diphosphate + isopentenyl diphosphate = H+ + diphosphate + all-trans-octaprenyl diphosphate nonaprenyl diphosphate biosynthesis III all-trans-heptaprenyl diphosphate 651.779 C35 H57 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] PUBCHEM:25245257:*LIGAND-CPD:C04216: 2.5.1.30 all-trans-hexaprenyl diphosphate + isopentenyl diphosphate = H+ + all-trans-heptaprenyl diphosphate + diphosphate heptaprenyl diphosphate biosynthesis all-trans-heptaprenyl diphosphate 651.779 C35 H57 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] PUBCHEM:25245257:*LIGAND-CPD:C04216: 2.5.1.30 all-trans-hexaprenyl diphosphate + isopentenyl diphosphate = H+ + all-trans-heptaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III L-2,3-dihydrodipicolinate 2,3-dihydrodipicolinate*dihydrodipicolinate*2,3-di-H-dipicolinate 167.121 C7 H5 N1 O4 O=C([O-])C1(C=CCC(N=1)C(=O)[O-]) CHEBI:30620:*PUBCHEM:5460228:*LIGAND-CPD:C03340: 1.3.1.26 tetrahydrodipicolinate = L-2,3-dihydrodipicolinate + H+ lysine biosynthesis VI L-2,3-dihydrodipicolinate 2,3-dihydrodipicolinate*dihydrodipicolinate*2,3-di-H-dipicolinate 167.121 C7 H5 N1 O4 O=C([O-])C1(C=CCC(N=1)C(=O)[O-]) CHEBI:30620:*PUBCHEM:5460228:*LIGAND-CPD:C03340: 4.2.1.52 pyruvate + L-aspartate-semialdehyde = H+ + H2O + L-2,3-dihydrodipicolinate lysine biosynthesis VI Fe3+ ferric iron*Fe3+*Fe+++*Fe+3*ferric ion*fe(iii) 55.847 FE1 [Fe+++] PUBCHEM:29936:*LIGAND-CPD:C14819:*CHEBI:29034: 1.16.1.7 Fe3+ + NADH = H+ + Fe2+ + NAD+ Fe(III)-reduction and Fe(II) transport 5-dehydroavenasterol 410.682 C29 H46 O1 C1(CC(CC2(C1(C3(C(=CC=2)C4(CCC(C(CCC(C(C)C)=CC)C)C(CC3)(C)4)))C))O) PUBCHEM:23724575:*LIGAND-CPD:C15783: 1.3.3.- avenasterol = H+ + 5-dehydroavenasterol plant sterol biosynthesis 5-dehydroavenasterol 410.682 C29 H46 O1 C1(CC(CC2(C1(C3(C(=CC=2)C4(CCC(C(CCC(C(C)C)=CC)C)C(CC3)(C)4)))C))O) PUBCHEM:23724575:*LIGAND-CPD:C15783: 1.3.1.21 5-dehydroavenasterol + NADPH = isofucosterol + NADP+ plant sterol biosynthesis 4-hydroxybenzoyl-CoA p-hydroxybenzoyl-CoA 883.61 C28 H36 N7 O18 P3 S1 N4(C=NC3(N(C2(C(O)C(OP(=O)([O-])[O-])C(COP(OP([O-])(=O)OCC(C)(C)C(O)C(NCCC(=O)NCCSC(C1(=CC=C(O)C=C1))=O)=O)(=O)[O-])O2))C=NC=3C(N)=4)) PUBCHEM:25244604:*LIGAND-CPD:C02949: 3.1.2.23 4-hydroxybenzoyl-CoA + H2O = H+ + coenzyme A 4-hydroxybenzoate biosynthesis V 4-hydroxybenzoyl-CoA p-hydroxybenzoyl-CoA 883.61 C28 H36 N7 O18 P3 S1 N4(C=NC3(N(C2(C(O)C(OP(=O)([O-])[O-])C(COP(OP([O-])(=O)OCC(C)(C)C(O)C(NCCC(=O)NCCSC(C1(=CC=C(O)C=C1))=O)=O)(=O)[O-])O2))C=NC=3C(N)=4)) PUBCHEM:25244604:*LIGAND-CPD:C02949: 2.3.1.16 3-(4-hydroxyphenyl)-3-oxo-propionyl-CoA + coenzyme A = acetyl-CoA + 4-hydroxybenzoyl-CoA 4-hydroxybenzoate biosynthesis V propionate propionic acid*ethylformic acid*methylacetic acid*propanoate 73.071 C3 H5 O2 C(CC)(=O)[O-] PUBCHEM:104745:*CHEBI:17272:*LIGAND-CPD:C00163:*CAS:79-09-4: 6.2.1.17 coenzyme A + propionate + ATP = propanoyl-CoA + diphosphate + AMP β-alanine biosynthesis II S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- S-adenosyl-L-methionine = S-adenosyl-L-homocysteine homogalacturonan biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- 2-methyl-6-phytyl-1,4-benzoquinol + S-adenosyl-L-methionine = H+ + 2,3-dimethyl-6-phytyl-1,4-benzoquinol + S-adenosyl-L-homocysteine vitamin E biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.8.1.8 S-adenosyl-L-methionine + S2- = 5'-deoxyadenosine + L-methionine lipoate biosynthesis and incorporation I S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.11 Mg-protoporphyrin + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + magnesium-protoporphyrin IX 13-monomethyl ester chlorophyllide a biosynthesis I S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- 2-methoxy-6-all trans-decaprenyl-2-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine = H+ + 6-methoxy-5-methyl-2-all-trans-decaprenyl-1,4-benzoquinol + S-adenosyl-L-homocysteine ubiquinol-10 biosynthesis (eukaryotic) S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.64 3-demethylubiquinol-10 + S-adenosyl-L-methionine = H+ + ubiquinol-10 + S-adenosyl-L-homocysteine ubiquinol-10 biosynthesis (eukaryotic) S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.95 δ-tocopherol + S-adenosyl-L-methionine = H+ + β-tocopherol + S-adenosyl-L-homocysteine vitamin E biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.98 2-(3-carboxy-3-aminopropyl)-L-histidine in eEF-2 + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine diphthamide biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.149 myricetin + S-adenosyl-L-methionine = H+ + laricitrin + S-adenosyl-L-homocysteine syringetin biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.76 quercetin + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + 3-O-methylquercetin methylquercetin biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.64 3-demethylubiquinol-9 + S-adenosyl-L-methionine = H+ + ubiquinol-9 + S-adenosyl-L-homocysteine ubiquinol-9 biosynthesis (eukaryotic) S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.79 S-adenosyl-L-methionine = S-adenosyl-L-homocysteine cyclopropane fatty acid (CFA) biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.79 oleate + S-adenosyl-L-methionine = H+ + dihydrosterculate + S-adenosyl-L-homocysteine cyclopropane and cyclopropene fatty acid biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- 2-methoxy-6-all trans-nonaprenyl-2-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine = H+ + 6-methoxy-5-methyl-2-all-trans-nonaprenyl-1,4-benzoquinol + S-adenosyl-L-homocysteine ubiquinol-9 biosynthesis (eukaryotic) S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.68 trans-caffeate + S-adenosyl-L-methionine = H+ + ferulate + S-adenosyl-L-homocysteine suberin biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.68 trans-caffeate + S-adenosyl-L-methionine = H+ + ferulate + S-adenosyl-L-homocysteine free phenylpropanoid acid biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.68 trans-caffeate + S-adenosyl-L-methionine = H+ + ferulate + S-adenosyl-L-homocysteine simplecoumarins biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.107 S-adenosyl-L-methionine + uroporphyrinogen-III = H+ + S-adenosyl-L-homocysteine + precorrin-1 siroheme biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 S-adenosyl-L-methionine = 2-(3-carboxy-3-aminopropyl)-L-histidine in eEF-2 + S-methyl-5'-thioadenosine diphthamide biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.68 5-hydroxyferulate + S-adenosyl-L-methionine = H+ + sinapate + S-adenosyl-L-homocysteine free phenylpropanoid acid biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.114 3,4-dihydroxy-5-all-trans-nonaprenylbenzoate + S-adenosyl-L-methionine = H+ + 3-methoxy-4-hydroxy-5-all-trans-nonaprenylbenzoate + S-adenosyl-L-homocysteine ubiquinol-9 biosynthesis (eukaryotic) S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.5.1.43 S-adenosyl-L-methionine = H+ + nicotianamine + S-methyl-5'-thioadenosine 2'-deoxymugineic acid phytosiderophore biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.5.1.43 S-adenosyl-L-methionine = H+ + nicotianamine + S-methyl-5'-thioadenosine nicotianamine biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 4.1.1.50 H+ + S-adenosyl-L-methionine = CO2 + S-adenosyl-L-methioninamine spermine biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 4.1.1.50 H+ + S-adenosyl-L-methionine = CO2 + S-adenosyl-L-methioninamine spermidine biosynthesis I S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.41 S-adenosyl-L-methionine + cycloartenol = H+ + S-adenosyl-L-homocysteine + 24-methylenecycloartanol plant sterol biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 4.4.1.14 S-adenosyl-L-methionine = H+ + S-methyl-5'-thioadenosine + 1-aminocyclopropane-1-carboxylate ethylene biosynthesis from methionine S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.107 S-adenosyl-L-methionine + precorrin-1 = S-adenosyl-L-homocysteine + precorrin-2 siroheme biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.95 γ-tocopherol + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + α-tocopherol vitamin E biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 (2S)-pinocembrin + S-adenosyl-L-methionine = pinostrobin + S-adenosyl-L-homocysteine pinobanksin biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.10 L-homocysteine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + L-methionine methionine biosynthesis II S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = H+ + N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis IV S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = H+ + N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine choline biosynthesis I S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = H+ + N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis II S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.68 5-hydroxy-coniferaldehyde + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + sinapaldehyde phenylpropanoid biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.68 5-hydroxy-coniferaldehyde + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + sinapaldehyde ferulate and sinapate biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.82 3-O-methylquercetin + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + 3,7-di-O-methylquercetin methylquercetin biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.114 3,4-dihydroxy-5-all-trans-decaprenylbenzoate + S-adenosyl-L-methionine = H+ + 3-methoxy-4-hydroxy-5-all-trans-decaprenylbenzoate + S-adenosyl-L-homocysteine ubiquinol-10 biosynthesis (eukaryotic) S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.103 N-dimethylethanolamine phosphate + S-adenosyl-L-methionine = H+ + phosphoryl-choline + S-adenosyl-L-homocysteine choline biosynthesis I S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.103 N-dimethylethanolamine phosphate + S-adenosyl-L-methionine = H+ + phosphoryl-choline + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis II S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 3,7,3'-tri-methylquercetagetin + S-adenosyl-L-methionine = H+ + 3,6,7,3'-tetra-methylquercetagetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.12 L-methionine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine dimethylsulfoniopropionate biosynthesis II (Spartina) S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.12 L-methionine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine dimethylsulfoniopropionate biosynthesis I (Wollastonia) S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.12 L-methionine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine S-methylmethionine cycle S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.143 24-methylenelophenol + S-adenosyl-L-methionine = H+ + 24-ethylidenelophenol + S-adenosyl-L-homocysteine plant sterol biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine methionine degradation I (to homocysteine) S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine 2'-deoxymugineic acid phytosiderophore biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine ethylene biosynthesis from methionine S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine S-adenosyl-L-methionine cycle II S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine S-adenosyl-L-methionine biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.98 S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + H+ diphthamide biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.98 S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + H+ diphthamide biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 3,7-di-methylquercetagetin + S-adenosyl-L-methionine = H+ + 3,7,3'-tri-methylquercetagetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.6.1.62 S-adenosyl-L-methionine + 7-keto-8-aminopelargonate = S-adenosyl-4-methylthio-2-oxobutanoate + 7,8-diaminopelargonate biotin biosynthesis from 7-keto-8-aminopelargonate S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- indole-3-acetate + S-adenosyl-L-methionine = methyl indole-3-acetate + S-adenosyl-L-homocysteine methyl indole-3-acetate interconversion S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.71 S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis III S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- quercetin + S-adenosyl-L-methionine = H+ + isorhamnetin + S-adenosyl-L-homocysteine quercetinsulphates biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- quercetin + S-adenosyl-L-methionine = H+ + isorhamnetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.71 S-adenosyl-L-methionine = S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis IV S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.71 S-adenosyl-L-methionine = S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis III S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate phosphatidylcholine biosynthesis IV S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate choline biosynthesis I S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate phosphatidylcholine biosynthesis III S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate phosphatidylcholine biosynthesis II S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.149 laricitrin + S-adenosyl-L-methionine = H+ + syringetin + S-adenosyl-L-homocysteine syringetin biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.83 3,7-di-O-methylquercetin + S-adenosyl-L-methionine = H+ + 3,7,4'-tri-O-methylquercetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 4.1.99.- 5-aminoimidazole ribonucleotide + S-adenosyl-L-methionine = hydroxymethylpyrimidine phosphate + 5'-deoxyadenosine + L-methionine + formate + carbon monoxide + H+ thiamine biosynthesis II S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = H+ + feruloyl-CoA + S-adenosyl-L-homocysteine chlorogenic acid biosynthesis I S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = H+ + feruloyl-CoA + S-adenosyl-L-homocysteine suberin biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = H+ + feruloyl-CoA + S-adenosyl-L-homocysteine phenylpropanoid biosynthesis S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- S-adenosyl-L-methionine = S-adenosyl-L-homocysteine S-adenosyl-L-methionine cycle I S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- S-adenosyl-L-methionine = S-adenosyl-L-homocysteine methionine degradation I (to homocysteine) S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- S-adenosyl-L-methionine = S-adenosyl-L-homocysteine S-adenosyl-L-methionine cycle II S-adenosyl-L-methionine AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(C[S+](CCC(C([O-])=O)[N+])C)C(O)C(O)1))C(N=2)=3)) CHEBI:59789:*PUBCHEM:44229224:*KNAPSACK:C00007347:*PUBCHEM:24762165:*PUBCHEM:25203285:*LIGAND-CPD:C00019:*CAS:29908-03-0 2.8.1.6 dethiobiotin + S-adenosyl-L-methionine = biotin + 5'-deoxyadenosine + L-methionine biotin biosynthesis from 7-keto-8-aminopelargonate 2-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate 2-hydroxy-3-(2-methylidenecyclopropyl)butanedioic acid 184.148 C8 H8 O5 C1(C(C(C(=O)[O-])C(C([O-])=O)O)C1)(=C) PUBCHEM:25200592: 2-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate = H+ + 2-oxo-3-carboxy-4,5-cyclopropylhex-5-enoate hypoglycin biosynthesis 2-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate 2-hydroxy-3-(2-methylidenecyclopropyl)butanedioic acid 184.148 C8 H8 O5 C1(C(C(C(=O)[O-])C(C([O-])=O)O)C1)(=C) PUBCHEM:25200592: 5.-.-.- 3-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate = 2-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate hypoglycin biosynthesis phosphoribosyl-ATP 1-(5-Phosphoribosyl)-ATP*N1-(5-phospho-D-ribosyl)-ATP*5-phosphoribosyl-ATP*1-(5-phospho-D-ribosyl)-ATP 713.232 C15 H19 N5 O20 P4 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC4(C(C(C(N3(C1(=C(C(N(C=N1)C2(OC(C(C2O)O)COP([O-])([O-])=O))=N)N=C3)))O4)O)O))[O-] PUBCHEM:25245261:*LIGAND-CPD:C02739: 2.4.2.17 phosphoribosyl-ATP + diphosphate = ATP + 5-phospho-α-D-ribose 1-diphosphate histidine biosynthesis phosphoribosyl-ATP 1-(5-Phosphoribosyl)-ATP*N1-(5-phospho-D-ribosyl)-ATP*5-phosphoribosyl-ATP*1-(5-phospho-D-ribosyl)-ATP 713.232 C15 H19 N5 O20 P4 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC4(C(C(C(N3(C1(=C(C(N(C=N1)C2(OC(C(C2O)O)COP([O-])([O-])=O))=N)N=C3)))O4)O)O))[O-] PUBCHEM:25245261:*LIGAND-CPD:C02739: 3.6.1.31 phosphoribosyl-ATP + H2O = 1-(5-phospho-D-ribosyl)-AMP + diphosphate + H+ histidine biosynthesis sterculate sterculic acid 293.468 C19 H33 O2 CCCCCCCCC1(CC(CCCCCCCC(=O)[O-])=1) PUBCHEM:25202397:*LIGAND-CPD:C08366: dihydrosterculate = H+ + sterculate cyclopropane and cyclopropene fatty acid biosynthesis 3-(2-propenoic acid)-4,6-hydroxy cyclohexa-2,5-dienone 194.143 C9 H6 O5 [O-]C1(C(=O)C=C(C(C=1)O)C=CC([O-])=O) PUBCHEM:25245891: 3-(2-propenoic acid)-o-benzoquinone + H2O = H+ + 3-(2-propenoic acid)-4,6-hydroxy cyclohexa-2,5-dienone esculetin biosynthesis 3-(2-propenoic acid)-4,6-hydroxy cyclohexa-2,5-dienone 194.143 C9 H6 O5 [O-]C1(C(=O)C=C(C(C=1)O)C=CC([O-])=O) PUBCHEM:25245891: 5.3.-.- H+ + 3-(2-propenoic acid)-4,6-hydroxy cyclohexa-2,5-dienone = 3,4,6-trihydroxy-cis-cinnamate esculetin biosynthesis acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 O=CC CHEBI:15343:*PUBCHEM:177:*LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 1.11.1.6 ethanol + hydrogen peroxide = H2O + acetaldehyde ethanol degradation IV (peroxisomal) acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 O=CC CHEBI:15343:*PUBCHEM:177:*LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 4.1.2.5 L-threonine = acetaldehyde + glycine glycine biosynthesis IV acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 O=CC CHEBI:15343:*PUBCHEM:177:*LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 1.1.1.1 ethanol + NAD+ = acetaldehyde + NADH + H+ acetaldehyde biosynthesis I acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 O=CC CHEBI:15343:*PUBCHEM:177:*LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 1.1.1.1 ethanol + NAD+ = acetaldehyde + NADH + H+ ethanol degradation II (cytosol) acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 O=CC CHEBI:15343:*PUBCHEM:177:*LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 1.1.1.1 ethanol + NAD+ = acetaldehyde + NADH + H+ pyruvate fermentation to ethanol II acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 O=CC CHEBI:15343:*PUBCHEM:177:*LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 4.1.1.1 H+ + pyruvate = acetaldehyde + CO2 acetaldehyde biosynthesis II acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 O=CC CHEBI:15343:*PUBCHEM:177:*LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 4.1.1.1 H+ + pyruvate = acetaldehyde + CO2 acetaldehyde biosynthesis I acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 O=CC CHEBI:15343:*PUBCHEM:177:*LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 4.1.1.1 H+ + pyruvate = acetaldehyde + CO2 pyruvate fermentation to ethanol II acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 O=CC CHEBI:15343:*PUBCHEM:177:*LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 1.2.1.3 acetaldehyde + H2O + NAD+ = acetate + NADH + H+ ethanol degradation II (cytosol) acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 O=CC CHEBI:15343:*PUBCHEM:177:*LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 1.2.1.3 acetaldehyde + H2O + NAD+ = acetate + NADH + H+ ethanol degradation IV (peroxisomal) (2S)-2-isopropyl-3-oxosuccinate (2S)-2-isopropyl-3-oxosuccinate*2-isopropyl-3-oxosuccinate 172.137 C7 H8 O5 C(=O)(C(=O)[O-])C(C(C)C)C(=O)[O-] PUBCHEM:25245894:*LIGAND-CPD:C04236: H+ + (2S)-2-isopropyl-3-oxosuccinate = 4-methyl-2-oxopentanoate + CO2 leucine biosynthesis (2S)-2-isopropyl-3-oxosuccinate (2S)-2-isopropyl-3-oxosuccinate*2-isopropyl-3-oxosuccinate 172.137 C7 H8 O5 C(=O)(C(=O)[O-])C(C(C)C)C(=O)[O-] PUBCHEM:25245894:*LIGAND-CPD:C04236: 1.1.1.85 (2R,3S)-3-isopropylmalate + NAD+ = (2S)-2-isopropyl-3-oxosuccinate + NADH + H+ leucine biosynthesis cis-zeatin (Z)-2-methyl-4-(1H-purin-6-ylamino)but-2-en-1-ol*cZ 219.246 C10 H13 N5 O1 CC(CO)=CCNC2(=C1(C(NC=N1)=NC=N2)) PUBCHEM:688597:*CHEBI:46570:*LIGAND-CPD:C15545: cis-zeatin riboside + H2O = cis-zeatin cis-zeatin biosynthesis cis-zeatin (Z)-2-methyl-4-(1H-purin-6-ylamino)but-2-en-1-ol*cZ 219.246 C10 H13 N5 O1 CC(CO)=CCNC2(=C1(C(NC=N1)=NC=N2)) PUBCHEM:688597:*CHEBI:46570:*LIGAND-CPD:C15545: 2.4.1.215 cis-zeatin = cis-zeatin-O-glucoside + H+ + UDP cytokinins-O-glucoside biosynthesis cis-zeatin (Z)-2-methyl-4-(1H-purin-6-ylamino)but-2-en-1-ol*cZ 219.246 C10 H13 N5 O1 CC(CO)=CCNC2(=C1(C(NC=N1)=NC=N2)) PUBCHEM:688597:*CHEBI:46570:*LIGAND-CPD:C15545: 1.5.99.12 H+ + cis-zeatin + H2O + FAD = 3-methyl-4-cis-hydroxy-2-butenal + adenine + FADH2 cytokinins degradation 1D-myo-inositol (1)-monophosphate 1D-myo-inositol 1-phosphate*1D-myo-inositol (1)-monophosphate*1D-myo-Inositol 1-phosphate*D-myo-inositol (1)-monophosphate*Ins(1)P1*1-D-myo-inositol-1-p*Ins(1)P*1D-myo-inositol 1-phosphate*Ins1P 258.121 C6 H11 O9 P1 C1(OP([O-])([O-])=O)(C(O)C(O)C(O)C(O)C(O)1) CHEBI:58433:*KNAPSACK:C00007483:*PUBCHEM:5288642:*LIGAND-CPD:C01177: 3.1.3.25 H2O + 1D-myo-inositol (1)-monophosphate = myo-inositol phytate degradation I 1D-myo-inositol (1)-monophosphate 1D-myo-inositol 1-phosphate*1D-myo-inositol (1)-monophosphate*1D-myo-Inositol 1-phosphate*D-myo-inositol (1)-monophosphate*Ins(1)P1*1-D-myo-inositol-1-p*Ins(1)P*1D-myo-inositol 1-phosphate*Ins1P 258.121 C6 H11 O9 P1 C1(OP([O-])([O-])=O)(C(O)C(O)C(O)C(O)C(O)1) CHEBI:58433:*KNAPSACK:C00007483:*PUBCHEM:5288642:*LIGAND-CPD:C01177: D-myo-inositol (1,2) bisphosphate + H2O = 1D-myo-inositol (1)-monophosphate phytate degradation I 2-carboxylate-4-methyl-5-beta-(ethyl adenosine 5-diphosphate) thiazole AHZ*adenosine diphosphate 5-(beta-ethyl)-4-methyl-thiazole-2-carboxylic acid*2-carboxylate-4-methyl-5-β-(ethyl adenosine 5-diphosphate) thiazole*ADT*adenylated thiazole 593.378 C17 H19 N6 O12 P2 S1 CC4(N=C(C([O-])=O)SC(CCOP(OP(OCC3(OC(N2(C1(N=CN=C(N)C=1N=C2)))C(O)C(O)3))([O-])=O)([O-])=O)=4) PUBCHEM:5287651:*PUBCHEM:23644411: 2-carboxylate-4-methyl-5-beta-(ethyl adenosine 5-diphosphate) thiazole = AMP + 4-methyl-5-(2-phosphonooxyethyl)thiazole thiamine biosynthesis II 2-carboxylate-4-methyl-5-beta-(ethyl adenosine 5-diphosphate) thiazole AHZ*adenosine diphosphate 5-(beta-ethyl)-4-methyl-thiazole-2-carboxylic acid*2-carboxylate-4-methyl-5-β-(ethyl adenosine 5-diphosphate) thiazole*ADT*adenylated thiazole 593.378 C17 H19 N6 O12 P2 S1 CC4(N=C(C([O-])=O)SC(CCOP(OP(OCC3(OC(N2(C1(N=CN=C(N)C=1N=C2)))C(O)C(O)3))([O-])=O)([O-])=O)=4) PUBCHEM:5287651:*PUBCHEM:23644411: glycine + L-cysteine + NAD+ = 2-carboxylate-4-methyl-5-beta-(ethyl adenosine 5-diphosphate) thiazole + nicotinamide thiamine biosynthesis II zeaxanthin β,β-carotene-3,3'-diol 568.881 C40 H56 O2 C1(C(C(=C(CC1O)C)C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC2(=C(CC(CC2(C)C)O)C))C)C)(C)C) PUBCHEM:5280899:*CHEBI:27547:*LIGAND-CPD:C06098: 1.14.99.- β-cryptoxanthin + oxygen = zeaxanthin + H2O zeaxanthin biosynthesis zeaxanthin β,β-carotene-3,3'-diol 568.881 C40 H56 O2 C1(C(C(=C(CC1O)C)C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC2(=C(CC(CC2(C)C)O)C))C)C)(C)C) PUBCHEM:5280899:*CHEBI:27547:*LIGAND-CPD:C06098: 1.14.13.90 zeaxanthin + H+ + oxygen = antheraxanthin + H2O antheraxanthin and violaxanthin biosynthesis zeaxanthin β,β-carotene-3,3'-diol 568.881 C40 H56 O2 C1(C(C(=C(CC1O)C)C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC2(=C(CC(CC2(C)C)O)C))C)C)(C)C) PUBCHEM:5280899:*CHEBI:27547:*LIGAND-CPD:C06098: 1.14.13.90 zeaxanthin + H+ + oxygen = antheraxanthin + H2O xanthophyll cycle zeaxanthin β,β-carotene-3,3'-diol 568.881 C40 H56 O2 C1(C(C(=C(CC1O)C)C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC2(=C(CC(CC2(C)C)O)C))C)C)(C)C) PUBCHEM:5280899:*CHEBI:27547:*LIGAND-CPD:C06098: 1.10.99.3 H+ + antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O antheraxanthin and violaxanthin biosynthesis zeaxanthin β,β-carotene-3,3'-diol 568.881 C40 H56 O2 C1(C(C(=C(CC1O)C)C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC2(=C(CC(CC2(C)C)O)C))C)C)(C)C) PUBCHEM:5280899:*CHEBI:27547:*LIGAND-CPD:C06098: 1.10.99.3 H+ + antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle isochorismate Isochorismic acid 224.17 C10 H8 O6 C1(=C(C(C(C=C1)OC(=C)C(=O)[O-])O)C([O-])=O) PUBCHEM:5460580:*CHEBI:29780:*LIGAND-CPD:C00885:*CAS:22642-82-6 2.2.1.9 H+ + isochorismate + 2-oxoglutarate = 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + CO2 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) isochorismate Isochorismic acid 224.17 C10 H8 O6 C1(=C(C(C(C=C1)OC(=C)C(=O)[O-])O)C([O-])=O) PUBCHEM:5460580:*CHEBI:29780:*LIGAND-CPD:C00885:*CAS:22642-82-6 3.3.2.1 H2O + isochorismate = pyruvate + 2,3-dihydro-2,3-dihydroxybenzoate 2,3-dihydroxybenzoate biosynthesis isochorismate Isochorismic acid 224.17 C10 H8 O6 C1(=C(C(C(C=C1)OC(=C)C(=O)[O-])O)C([O-])=O) PUBCHEM:5460580:*CHEBI:29780:*LIGAND-CPD:C00885:*CAS:22642-82-6 5.4.4.2 chorismate = isochorismate 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) isochorismate Isochorismic acid 224.17 C10 H8 O6 C1(=C(C(C(C=C1)OC(=C)C(=O)[O-])O)C([O-])=O) PUBCHEM:5460580:*CHEBI:29780:*LIGAND-CPD:C00885:*CAS:22642-82-6 5.4.4.2 chorismate = isochorismate 2,3-dihydroxybenzoate biosynthesis 7-keto-8-aminopelargonate 8-amino-7-oxononanoate*7-KAP*7-keto-8-aminopelargonate*KAPA 187.238 C9 H17 N1 O3 C(C(CCCCCC([O-])=O)=O)([N+])C CHEBI:57532:*PUBCHEM:25244029:*LIGAND-CPD:C01092: 2.6.1.62 S-adenosyl-L-methionine + 7-keto-8-aminopelargonate = S-adenosyl-4-methylthio-2-oxobutanoate + 7,8-diaminopelargonate biotin biosynthesis from 7-keto-8-aminopelargonate 2-methylbutanoyl-CoA 2-methylbutanoyl-CoA*2-methylbutyryl-CoA*α-methylbutyryl-CoA*α-methylbutanoyl-CoA*S-2-methyl-butyryl-CoA 847.62 C26 H40 N7 O17 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP([O-])(OCC(C)(C)C(C(NCCC(=O)NCCSC(=O)C(C)CC)=O)O)=O)O1)OP([O-])(=O)[O-])(N3(C=NC2(C(=NC=NC=23)N))) CHEBI:15477:*PUBCHEM:25245899:*LIGAND-CPD:C01033: 1.3.99.12 H+ + 2-methylbutanoyl-CoA + FAD = 2-methyl-crotonyl-CoA + FADH2 isoleucine degradation I 2-methylbutanoyl-CoA 2-methylbutanoyl-CoA*2-methylbutyryl-CoA*α-methylbutyryl-CoA*α-methylbutanoyl-CoA*S-2-methyl-butyryl-CoA 847.62 C26 H40 N7 O17 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP([O-])(OCC(C)(C)C(C(NCCC(=O)NCCSC(=O)C(C)CC)=O)O)=O)O1)OP([O-])(=O)[O-])(N3(C=NC2(C(=NC=NC=23)N))) CHEBI:15477:*PUBCHEM:25245899:*LIGAND-CPD:C01033: 2-keto-3-methyl-valerate + NAD+ + coenzyme A = 2-methylbutanoyl-CoA + NADH + CO2 isoleucine degradation I L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(C([N+])C(=O)[O-])CC=O PUBCHEM:25245270:*LIGAND-CPD:C01165: L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate arginine degradation VI (arginase 2 pathway) L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(C([N+])C(=O)[O-])CC=O PUBCHEM:25245270:*LIGAND-CPD:C01165: L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate arginine degradation I (arginase pathway) L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(C([N+])C(=O)[O-])CC=O PUBCHEM:25245270:*LIGAND-CPD:C01165: L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate proline biosynthesis II (from arginine) L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(C([N+])C(=O)[O-])CC=O PUBCHEM:25245270:*LIGAND-CPD:C01165: L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate proline biosynthesis I L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(C([N+])C(=O)[O-])CC=O PUBCHEM:25245270:*LIGAND-CPD:C01165: L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate citrulline biosynthesis L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(C([N+])C(=O)[O-])CC=O PUBCHEM:25245270:*LIGAND-CPD:C01165: 1.2.1.41 L-glutamate γ-semialdehyde + NADP+ = L-glutamate-5-phosphate + NADPH + H+ proline biosynthesis I L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(C([N+])C(=O)[O-])CC=O PUBCHEM:25245270:*LIGAND-CPD:C01165: 1.2.1.41 L-glutamate γ-semialdehyde + NADP+ = L-glutamate-5-phosphate + NADPH + H+ citrulline biosynthesis L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(C([N+])C(=O)[O-])CC=O PUBCHEM:25245270:*LIGAND-CPD:C01165: 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde arginine degradation VI (arginase 2 pathway) L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(C([N+])C(=O)[O-])CC=O PUBCHEM:25245270:*LIGAND-CPD:C01165: 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde arginine degradation I (arginase pathway) L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(C([N+])C(=O)[O-])CC=O PUBCHEM:25245270:*LIGAND-CPD:C01165: 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde proline biosynthesis II (from arginine) L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(C([N+])C(=O)[O-])CC=O PUBCHEM:25245270:*LIGAND-CPD:C01165: 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde citrulline biosynthesis L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 [N+]C(C([O-])=O)CS PUBCHEM:5260155:*CHEBI:35237:*KNAPSACK:C00001351:*CAS:4371-52-2*LIGAND-CPD:C00097:*CAS:52-90-4 6.1.1.16 H+ + L-cysteine + ATP = diphosphate + AMP tRNA charging pathway L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 [N+]C(C([O-])=O)CS PUBCHEM:5260155:*CHEBI:35237:*KNAPSACK:C00001351:*CAS:4371-52-2*LIGAND-CPD:C00097:*CAS:52-90-4 4.4.1.9 L-cysteine + hydrogen cyanide = hydrogen sulfide + 3-cyano-L-alanine + H+ cyanide detoxification L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 [N+]C(C([O-])=O)CS PUBCHEM:5260155:*CHEBI:35237:*KNAPSACK:C00001351:*CAS:4371-52-2*LIGAND-CPD:C00097:*CAS:52-90-4 4.4.1.9 L-cysteine + hydrogen cyanide = hydrogen sulfide + 3-cyano-L-alanine + H+ cyanide degradation L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 [N+]C(C([O-])=O)CS PUBCHEM:5260155:*CHEBI:35237:*KNAPSACK:C00001351:*CAS:4371-52-2*LIGAND-CPD:C00097:*CAS:52-90-4 6.3.2.5 D-4'-phosphopantothenate + L-cysteine + CTP = H+ + R-4'-phosphopantothenoyl-L-cysteine + diphosphate + CMP coenzyme A biosynthesis L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 [N+]C(C([O-])=O)CS PUBCHEM:5260155:*CHEBI:35237:*KNAPSACK:C00001351:*CAS:4371-52-2*LIGAND-CPD:C00097:*CAS:52-90-4 3.4.11.2 cysteinylglycine + H2O = L-cysteine + glycine γ-glutamyl cycle (plant pathway) L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 [N+]C(C([O-])=O)CS PUBCHEM:5260155:*CHEBI:35237:*KNAPSACK:C00001351:*CAS:4371-52-2*LIGAND-CPD:C00097:*CAS:52-90-4 3.4.11.2 cysteinylglycine + H2O = L-cysteine + glycine glutathione degradation L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 [N+]C(C([O-])=O)CS PUBCHEM:5260155:*CHEBI:35237:*KNAPSACK:C00001351:*CAS:4371-52-2*LIGAND-CPD:C00097:*CAS:52-90-4 3.4.11.2 cysteinylglycine + H2O = L-cysteine + glycine γ-glutamyl cycle L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 [N+]C(C([O-])=O)CS PUBCHEM:5260155:*CHEBI:35237:*KNAPSACK:C00001351:*CAS:4371-52-2*LIGAND-CPD:C00097:*CAS:52-90-4 2.8.1.7 L-cysteine = L-alanine alanine biosynthesis III L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 [N+]C(C([O-])=O)CS PUBCHEM:5260155:*CHEBI:35237:*KNAPSACK:C00001351:*CAS:4371-52-2*LIGAND-CPD:C00097:*CAS:52-90-4 2.5.1.- L-cysteine + O-phospho-L-homoserine = L-cystathionine methionine biosynthesis II L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 [N+]C(C([O-])=O)CS PUBCHEM:5260155:*CHEBI:35237:*KNAPSACK:C00001351:*CAS:4371-52-2*LIGAND-CPD:C00097:*CAS:52-90-4 glycine + L-cysteine + NAD+ = 2-carboxylate-4-methyl-5-beta-(ethyl adenosine 5-diphosphate) thiazole + nicotinamide thiamine biosynthesis II L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 [N+]C(C([O-])=O)CS PUBCHEM:5260155:*CHEBI:35237:*KNAPSACK:C00001351:*CAS:4371-52-2*LIGAND-CPD:C00097:*CAS:52-90-4 6.3.2.2 L-cysteine + L-glutamate + ATP = H+ + L-γ-glutamylcysteine + ADP γ-glutamyl cycle (plant pathway) L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 [N+]C(C([O-])=O)CS PUBCHEM:5260155:*CHEBI:35237:*KNAPSACK:C00001351:*CAS:4371-52-2*LIGAND-CPD:C00097:*CAS:52-90-4 6.3.2.2 L-cysteine + L-glutamate + ATP = H+ + L-γ-glutamylcysteine + ADP glutathione biosynthesis L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 [N+]C(C([O-])=O)CS PUBCHEM:5260155:*CHEBI:35237:*KNAPSACK:C00001351:*CAS:4371-52-2*LIGAND-CPD:C00097:*CAS:52-90-4 2.5.1.47 O-acetyl-L-serine + hydrogen sulfide = H+ + L-cysteine + acetate cysteine biosynthesis I L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 [N+]C(C([O-])=O)CS PUBCHEM:5260155:*CHEBI:35237:*KNAPSACK:C00001351:*CAS:4371-52-2*LIGAND-CPD:C00097:*CAS:52-90-4 4.4.1.1 L-cystathionine + H2O = H+ + ammonia + 2-oxobutanoate + L-cysteine homocysteine and cysteine interconversion L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 [N+]C(C([O-])=O)CS PUBCHEM:5260155:*CHEBI:35237:*KNAPSACK:C00001351:*CAS:4371-52-2*LIGAND-CPD:C00097:*CAS:52-90-4 O-acetyl-L-homoserine + L-cysteine = H+ + L-cystathionine + acetate homocysteine and cysteine interconversion campest-4-en-3-one methylcholestenone*(24R)-24-methyl-cholest-4-en-3-one*3-dehydro-Δ4-5-campesterol 398.671 C28 H46 O1 C1(CC(C=C2(C1(C3(C(CC2)C4(CCC(C(CCC(C(C)C)C)C)C(CC3)(C)4)))C))=O) PUBCHEM:25200612:*LIGAND-CPD:C15785: 1.1.1.145 campest-4-en-3β-ol = H+ + campest-4-en-3-one brassinosteroid biosynthesis II campest-4-en-3-one methylcholestenone*(24R)-24-methyl-cholest-4-en-3-one*3-dehydro-Δ4-5-campesterol 398.671 C28 H46 O1 C1(CC(C=C2(C1(C3(C(CC2)C4(CCC(C(CCC(C(C)C)C)C)C(CC3)(C)4)))C))=O) PUBCHEM:25200612:*LIGAND-CPD:C15785: 1.14.13.- H+ + campest-4-en-3-one + oxygen + NADPH = (22α)-hydroxy-campest-4-en-3-one + H2O + NADP+ brassinosteroid biosynthesis II campest-4-en-3-one methylcholestenone*(24R)-24-methyl-cholest-4-en-3-one*3-dehydro-Δ4-5-campesterol 398.671 C28 H46 O1 C1(CC(C=C2(C1(C3(C(CC2)C4(CCC(C(CCC(C(C)C)C)C)C(CC3)(C)4)))C))=O) PUBCHEM:25200612:*LIGAND-CPD:C15785: 1.3.99.- H+ + campest-4-en-3-one + NADPH = (5α)-campestan-3-one + NADP+ brassinosteroid biosynthesis II isorhamnetin 3'-methoxyquercetin*3-methylquercetin 315.259 C16 H11 O7 C3([O-])(C(=O)C1(C(=CC(O)=CC(O)=1)OC(C2(C=C(OC)C(O)=CC=2))=3)) PUBCHEM:25202413:*PUBCHEM:5281654:*LIGAND-CPD:C10084:*PUBCHEM:5281654: isorhamnetin + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + isorhamnetin 3-sulphate quercetinsulphates biosynthesis isorhamnetin 3'-methoxyquercetin*3-methylquercetin 315.259 C16 H11 O7 C3([O-])(C(=O)C1(C(=CC(O)=CC(O)=1)OC(C2(C=C(OC)C(O)=CC=2))=3)) PUBCHEM:25202413:*PUBCHEM:5281654:*LIGAND-CPD:C10084:*PUBCHEM:5281654: 2.1.1.- quercetin + S-adenosyl-L-methionine = H+ + isorhamnetin + S-adenosyl-L-homocysteine quercetinsulphates biosynthesis isorhamnetin 3'-methoxyquercetin*3-methylquercetin 315.259 C16 H11 O7 C3([O-])(C(=O)C1(C(=CC(O)=CC(O)=1)OC(C2(C=C(OC)C(O)=CC=2))=3)) PUBCHEM:25202413:*PUBCHEM:5281654:*LIGAND-CPD:C10084:*PUBCHEM:5281654: 2.1.1.- quercetin + S-adenosyl-L-methionine = H+ + isorhamnetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis δ-tocopherol 8-methyltocol 402.659 C27 H46 O2 CC2(C=C(C=C1(CCC(C)(CCCC(C)CCCC(C)CCCC(C)C)OC1=2))O) PUBCHEM:92094:*CHEBI:47772:*LIGAND-CPD:C14151: 2-methyl-6-phytyl-1,4-benzoquinol = δ-tocopherol vitamin E biosynthesis δ-tocopherol 8-methyltocol 402.659 C27 H46 O2 CC2(C=C(C=C1(CCC(C)(CCCC(C)CCCC(C)CCCC(C)C)OC1=2))O) PUBCHEM:92094:*CHEBI:47772:*LIGAND-CPD:C14151: 2.1.1.95 δ-tocopherol + S-adenosyl-L-methionine = H+ + β-tocopherol + S-adenosyl-L-homocysteine vitamin E biosynthesis nonaprenyl-4-hydroxybenzoate 4-hydroxybenzoic acid*nonaprenyl-4-hydroxybenzoic acid*3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaenyl ester 750.178 C52 H77 O3 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C=C(C([O-])=O)C=CC(O)=1) CHEBI:18162:*PUBCHEM:25244030:*LIGAND-CPD:C03885: 2.5.1.39 all-trans-nonaprenyl diphosphate = nonaprenyl-4-hydroxybenzoate + diphosphate ubiquinol-9 biosynthesis (eukaryotic) nonaprenyl-4-hydroxybenzoate 4-hydroxybenzoic acid*nonaprenyl-4-hydroxybenzoic acid*3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaenyl ester 750.178 C52 H77 O3 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C=C(C([O-])=O)C=CC(O)=1) CHEBI:18162:*PUBCHEM:25244030:*LIGAND-CPD:C03885: 1.14.13.- nonaprenyl-4-hydroxybenzoate + oxygen + NADPH + H+ = 3,4-dihydroxy-5-all-trans-nonaprenylbenzoate + H2O + NADP+ ubiquinol-9 biosynthesis (eukaryotic) nicotinate mononucleotide nicotinate nucleotide*nicotinate dinucleotide*β-nicotinate-D-nucleotide*NaMN*nicotinic acid nucleotide*nicotinic acid mononucleotide*nicotinic acid ribonucleotide*nicotinate-D-ribonucleotide*nicotinate ribonucleotide*nicotinate mononucleotide*deamido-nicotinamide mononucleotide*deamido-NMN*β-nicotinate D-ribonucleotide 333.191 C11 H12 N1 O9 P1 C2(C(C([N+]1(C=C(C=CC=1)C([O-])=O))OC(COP([O-])([O-])=O)2)O)O PUBCHEM:25245903:*LIGAND-CPD:C01185:*CAS:321-02-8 2.7.1.- nicotinate riboside + ATP = H+ + nicotinate mononucleotide + ADP pyridine nucleotide cycling (plants) nicotinate mononucleotide nicotinate nucleotide*nicotinate dinucleotide*β-nicotinate-D-nucleotide*NaMN*nicotinic acid nucleotide*nicotinic acid mononucleotide*nicotinic acid ribonucleotide*nicotinate-D-ribonucleotide*nicotinate ribonucleotide*nicotinate mononucleotide*deamido-nicotinamide mononucleotide*deamido-NMN*β-nicotinate D-ribonucleotide 333.191 C11 H12 N1 O9 P1 C2(C(C([N+]1(C=C(C=CC=1)C([O-])=O))OC(COP([O-])([O-])=O)2)O)O PUBCHEM:25245903:*LIGAND-CPD:C01185:*CAS:321-02-8 2.4.2.11 nicotinate mononucleotide + diphosphate = H+ + nicotinate + 5-phospho-α-D-ribose 1-diphosphate pyridine nucleotide cycling (plants) nicotinate mononucleotide nicotinate nucleotide*nicotinate dinucleotide*β-nicotinate-D-nucleotide*NaMN*nicotinic acid nucleotide*nicotinic acid mononucleotide*nicotinic acid ribonucleotide*nicotinate-D-ribonucleotide*nicotinate ribonucleotide*nicotinate mononucleotide*deamido-nicotinamide mononucleotide*deamido-NMN*β-nicotinate D-ribonucleotide 333.191 C11 H12 N1 O9 P1 C2(C(C([N+]1(C=C(C=CC=1)C([O-])=O))OC(COP([O-])([O-])=O)2)O)O PUBCHEM:25245903:*LIGAND-CPD:C01185:*CAS:321-02-8 2.7.7.18 H+ + ATP + nicotinate mononucleotide = diphosphate + nicotinate adenine dinucleotide NAD biosynthesis I (from aspartate) nicotinate mononucleotide nicotinate nucleotide*nicotinate dinucleotide*β-nicotinate-D-nucleotide*NaMN*nicotinic acid nucleotide*nicotinic acid mononucleotide*nicotinic acid ribonucleotide*nicotinate-D-ribonucleotide*nicotinate ribonucleotide*nicotinate mononucleotide*deamido-nicotinamide mononucleotide*deamido-NMN*β-nicotinate D-ribonucleotide 333.191 C11 H12 N1 O9 P1 C2(C(C([N+]1(C=C(C=CC=1)C([O-])=O))OC(COP([O-])([O-])=O)2)O)O PUBCHEM:25245903:*LIGAND-CPD:C01185:*CAS:321-02-8 2.7.7.18 H+ + ATP + nicotinate mononucleotide = diphosphate + nicotinate adenine dinucleotide pyridine nucleotide cycling (plants) nicotinate mononucleotide nicotinate nucleotide*nicotinate dinucleotide*β-nicotinate-D-nucleotide*NaMN*nicotinic acid nucleotide*nicotinic acid mononucleotide*nicotinic acid ribonucleotide*nicotinate-D-ribonucleotide*nicotinate ribonucleotide*nicotinate mononucleotide*deamido-nicotinamide mononucleotide*deamido-NMN*β-nicotinate D-ribonucleotide 333.191 C11 H12 N1 O9 P1 C2(C(C([N+]1(C=C(C=CC=1)C([O-])=O))OC(COP([O-])([O-])=O)2)O)O PUBCHEM:25245903:*LIGAND-CPD:C01185:*CAS:321-02-8 3.2.2.- nicotinate mononucleotide + H2O = H+ + nicotinate + D-ribose-5-phosphate pyridine nucleotide cycling (plants) nicotinate mononucleotide nicotinate nucleotide*nicotinate dinucleotide*β-nicotinate-D-nucleotide*NaMN*nicotinic acid nucleotide*nicotinic acid mononucleotide*nicotinic acid ribonucleotide*nicotinate-D-ribonucleotide*nicotinate ribonucleotide*nicotinate mononucleotide*deamido-nicotinamide mononucleotide*deamido-NMN*β-nicotinate D-ribonucleotide 333.191 C11 H12 N1 O9 P1 C2(C(C([N+]1(C=C(C=CC=1)C([O-])=O))OC(COP([O-])([O-])=O)2)O)O PUBCHEM:25245903:*LIGAND-CPD:C01185:*CAS:321-02-8 2.4.2.19 H+ + 5-phospho-α-D-ribose 1-diphosphate + quinolinate = CO2 + diphosphate + nicotinate mononucleotide NAD biosynthesis I (from aspartate) (E)-β-ocimene trans-β-ocimene 136.236 C10 H16 C(=CCC=C(C)C)(C)C=C PUBCHEM:5281553:*LIGAND-CPD:C09873: 4.2.3.- geranyl diphosphate = (E)-β-ocimene + diphosphate monoterpene biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ pyridine nucleotide cycling (plants) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH gluconeogenesis I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH glycolysis III NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH glycolysis IV (plant cytosol) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH glycolysis I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.1 ethanol + NAD+ = acetaldehyde + NADH + H+ acetaldehyde biosynthesis I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.1 ethanol + NAD+ = acetaldehyde + NADH + H+ ethanol degradation II (cytosol) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.1 ethanol + NAD+ = acetaldehyde + NADH + H+ pyruvate fermentation to ethanol II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.27 (S)-lactate + NAD+ = pyruvate + NADH + H+ pyruvate fermentation to lactate NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 2-oxoglutarate + coenzyme A + NAD+ = succinyl-CoA + CO2 + NADH TCA cycle variation III (eukaryotic) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.14.13.- 24-methylenelophenol + oxygen + NADH = 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 2-oxoadipate + NAD+ + coenzyme A = CO2 + NADH + glutaryl-CoA lysine degradation II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.14.13.- 24-ethylidenelophenol + NADH + oxygen = 4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.5.1.12 (S)-1-pyrroline-5-carboxylate + NAD+ + H2O = H+ + L-glutamate + NADH proline degradation NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.5.1.12 (S)-1-pyrroline-5-carboxylate + NAD+ + H2O = H+ + L-glutamate + NADH arginine degradation I (arginase pathway) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.8 betaine aldehyde + NAD+ + H2O = H+ + glycine betaine + NADH glycine betaine biosynthesis III (plants) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.16.1.7 Fe3+ + NADH = H+ + Fe2+ + NAD+ Fe(III)-reduction and Fe(II) transport NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.5.1.15 5,10-methylenetetrahydropteroyl mono-L-glutamate + NAD+ = 5,10-methenyltetrahydrofolate + NADH folate transformations I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.38 (S)-malate + NAD+ = NADH + CO2 + pyruvate gluconeogenesis I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.14.13.- 4α-formyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NADH + oxygen = 4α-carboxy-4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 4-methyl-2-oxopentanoate + coenzyme A + NAD+ = isovaleryl-CoA + CO2 + NADH leucine degradation I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.3.1.76 precorrin-2 + NAD+ = H+ + sirohydrochlorin + NADH siroheme biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 2.7.1.23 NAD+ + ATP = H+ + NADP+ + ADP NAD/NADH phosphorylation and dephosphorylation NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ adenosine nucleotides degradation II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ adenosine nucleotides degradation I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ guanosine nucleotides degradation II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 glycine + L-cysteine + NAD+ = 2-carboxylate-4-methyl-5-beta-(ethyl adenosine 5-diphosphate) thiazole + nicotinamide thiamine biosynthesis II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.5.1.9 L-saccharopine + H2O + NAD+ = L-glutamate + 2-aminoadipate-6-semialdehyde + NADH + H+ lysine degradation II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.6.5.3 H+ + NADH = NAD+ NADH to cytochrome bd oxidase electron transfer NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.6.5.3 H+ + NADH = NAD+ aerobic respiration -- electron donor II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.6.5.3 H+ + NADH = NAD+ NAD/NADH phosphorylation and dephosphorylation NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 2-keto-3-methyl-valerate + NAD+ + coenzyme A = 2-methylbutanoyl-CoA + NADH + CO2 isoleucine degradation I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.27 (S)-methylmalonate-semialdehyde + coenzyme A + NAD+ + H2O = propanoyl-CoA + bicarbonate + NADH + H+ valine degradation I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.1 H+ + 3-methylbutanal + NADH = 3-methylbutanol + NAD+ leucine degradation III NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.22 H2O + NAD+ = H+ + UDP-D-glucuronate + NADH UDP-D-xylose and UDP-D-glucuronate biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.22 H2O + NAD+ = H+ + UDP-D-glucuronate + NADH colanic acid building blocks biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.22 H2O + NAD+ = H+ + UDP-D-glucuronate + NADH galactose degradation III NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.- L-galactose + NAD+ = H+ + L-galactono-1,4-lactone + NADH ascorbate biosynthesis I (L-galactose pathway) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.3.1.28 NAD+ + 2,3-dihydro-2,3-dihydroxybenzoate = H+ + NADH + 2,3-dihydroxybenzoate 2,3-dihydroxybenzoate biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 3.1.3.2 NADP+ + H2O = NAD+ NAD/NADH phosphorylation and dephosphorylation NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.5.1.20 5-methyl-tetrahydrofolate + NAD+ = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H+ + NADH folate transformations I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.5.1.20 5-methyl-tetrahydrofolate + NAD+ = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H+ + NADH folate transformations II (plants) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.4.1.2 H2O + NAD+ + L-glutamate = H+ + ammonia + NADH + 2-oxoglutarate glutamate degradation I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.4.1.2 H2O + NAD+ + L-glutamate = H+ + ammonia + NADH + 2-oxoglutarate alanine degradation II (to D-lactate) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 (3Z)-hex-3-en-ol + NAD+ = cis-3-hexenal + NADH + H+ traumatin and (Z)-3-hexen-1-yl acetate biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.25 2-oxoisovalerate + coenzyme A + NAD+ = isobutyryl-CoA + CO2 + NADH valine degradation I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.85 (2R,3S)-3-isopropylmalate + NAD+ = (2S)-2-isopropyl-3-oxosuccinate + NADH + H+ leucine biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.14.13.- 4α-hydroxymethyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NADH + oxygen = 4α-formyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.14.13.- 4α-formyl-ergosta-7,24(241)-dien-3β-ol + oxygen + NADH = 4α-carboxy-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 2.7.1.160 NAD+ = ADP ribose 1'',2''-cyclic phosphate + nicotinamide + H2O tRNA splicing NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.35 NAD+ = NADH + H+ fatty acid β-oxidation II (core pathway) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.3.1.9 NAD+ = NADH + H+ fatty acid elongation -- saturated NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.244 methanol + NAD+ = H+ + formaldehyde + NADH methanol oxidation to formaldehyde II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.7.1.1 nitrite + H2O + NAD+ = H+ + nitrate + NADH nitrate reduction II (assimilatory) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.178 NAD+ + 2-methyl-3-hydroxybutyryl-CoA = H+ + NADH + 2-methylacetoacetyl-CoA isoleucine degradation I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.31 (S)-3-hydroxy-isobutyrate + NAD+ = H+ + NADH + (S)-methylmalonate-semialdehyde valine degradation I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.1 H+ + isobutanal + NADH = isobutanol + NAD+ valine degradation II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.8.1.4 NAD+ = NADH + H+ acetyl-CoA biosynthesis (from pyruvate) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.24 succinate semialdehyde + H2O + NAD+ = succinate + NADH + H+ glutamate degradation III (via 4-aminobutyrate) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.24 succinate semialdehyde + H2O + NAD+ = succinate + NADH + H+ 4-aminobutyrate degradation I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.29 D-glycerate + NAD+ = H+ + hydroxypyruvate + NADH photorespiration NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.4.1.14 NAD+ + L-glutamate = H+ + NADH + 2-oxoglutarate + L-glutamine ammonia assimilation cycle II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.4.1.14 NAD+ + L-glutamate = H+ + NADH + 2-oxoglutarate + L-glutamine glutamate biosynthesis IV NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.8.1.4 NAD+ = NADH + H+ glycine cleavage complex NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.14.13.- 4α-formyl-stigmasta-7,24(241)-dien-3β-ol + NADH + oxygen = 4α-carboxy-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.35 NAD+ + OPC8-3-hydroxyacyl-CoA = NADH + H+ + OPC8-3-ketoacyl-CoA jasmonic acid biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.23 histidinal + NAD+ + H2O = H+ + L-histidine + NADH histidine biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.1 H+ + phenylacetaldehyde + NADH = 2-phenylethanol + NAD+ phenylethanol biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ adenosine nucleotides degradation II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ adenosine nucleotides degradation I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.31 Δ1-piperideine-6-carboxylate + NAD+ + H2O = 2-aminoadipate + NADH + H+ lysine degradation II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.- 4α-carboxy-4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ = cycloeucalenone + NADH + CO2 plant sterol biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.14 D-sorbitol + NAD+ = NADH + H+ sorbitol degradation I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.255 NAD+ + D-mannitol = H+ + NADH mannitol degradation II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.23 methylglyoxal + NAD+ + H2O = H+ + pyruvate + NADH methylglyoxal degradation VII NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.19 4-aminobutanal + NAD+ + H2O = 4-aminobutyrate + NADH + H+ putrescine degradation IV NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.288 xanthoxin + NAD+ = abscisic aldehyde + NADH + H+ abscisic acid biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.28 benzaldehyde + H2O + NAD+ = benzoate + NADH + H+ benzoate biosynthesis III (CoA-dependent, non-β-oxidative) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.28 benzaldehyde + H2O + NAD+ = benzoate + NADH + H+ benzoate biosynthesis II (CoA-independent, non-β-oxidative) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.3 3-dimethylsulfoniopropionaldehyde + H2O + NAD+ = dimethylsulfoniopropionate + NADH + H+ dimethylsulfoniopropionate biosynthesis II (Spartina) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.3 3-dimethylsulfoniopropionaldehyde + H2O + NAD+ = dimethylsulfoniopropionate + NADH + H+ dimethylsulfoniopropionate biosynthesis I (Wollastonia) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.- 4α-carboxy-ergosta-7,24(241)-dien-3β-ol + NAD+ = episterone + NADH + CO2 plant sterol biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations II (plants) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH photorespiration NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 3.6.1.22 H2O + NAD+ = H+ + nicotinamide mononucleotide + AMP pyridine nucleotide cycling (plants) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.23 histidinol + NAD+ = H+ + histidinal + NADH histidine biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.35 NAD+ + OPC4-3-hydroxyacyl-CoA = NADH + H+ + OPC4-3-ketoacyl-CoA jasmonic acid biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.14.13.- 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol + oxygen + NADH = 4α-formyl-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.205 inosine-5'-phosphate + H2O + NAD+ = xanthosine-5-phosphate + NADH + H+ adenosine nucleotides degradation I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.205 inosine-5'-phosphate + H2O + NAD+ = xanthosine-5-phosphate + NADH + H+ purine nucleotides de novo biosynthesis II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.59 3-hydroxypropionate + NAD+ = malonate semialdehyde + NADH + H+ β-alanine biosynthesis II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 6.3.1.5 ammonia + ATP + nicotinate adenine dinucleotide = AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.35 3-(4-hydroxyphenyl)-3-hydroxy-propionyl-CoA + NAD+ = 3-(4-hydroxyphenyl)-3-oxo-propionyl-CoA + NADH + H+ 4-hydroxybenzoate biosynthesis V NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.41 D-threo-isocitrate + NAD+ = 2-oxoglutarate + CO2 + NADH TCA cycle variation III (eukaryotic) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.41 D-threo-isocitrate + NAD+ = 2-oxoglutarate + CO2 + NADH glutamine biosynthesis III NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.35 NAD+ + OPC6-3-hydroxyacyl-CoA = NADH + H+ + OPC6-3-ketoacyl-CoA jasmonic acid biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.- 4α-carboxy-stigmasta-7,24(241)-dien-3β-ol + NAD+ = avenastenone + NADH + CO2 plant sterol biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH superpathway of glyoxylate cycle NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.3.1.9 NAD+ = NADH + H+ stearate biosynthesis II (plants) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH glyoxylate cycle NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH gluconeogenesis I NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH TCA cycle variation III (eukaryotic) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH aspartate degradation II NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.2 formate + NAD+ = CO2 + NADH formate oxidation to CO2 NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.3.1.9 NADH + H+ = NAD+ palmitate biosynthesis II (bacteria and plants) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.14.13.- 4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol + NADH + oxygen = 4α-formyl-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.14.13.- 24-methylenecycloartanol + NADH + oxygen = 4α-hydroxymethyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.6.1.1 NAD+ + NADPH = NADH + NADP+ NAD/NADH phosphorylation and dephosphorylation NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.28 (R)-lactate + NAD+ = pyruvate + NADH + H+ alanine degradation II (to D-lactate) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.3 acetaldehyde + H2O + NAD+ = acetate + NADH + H+ ethanol degradation II (cytosol) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.3 acetaldehyde + H2O + NAD+ = acetate + NADH + H+ ethanol degradation IV (peroxisomal) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.8.1.4 NAD+ = NADH + H+ 2-ketoglutarate dehydrogenase complex NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.95 3-phospho-D-glycerate + NAD+ = H+ + 3-phospho-hydroxypyruvate + NADH serine biosynthesis NAD+ beta-nicotinamide adenine dinucleotide*coenzyme I*diphosphopyridine nucleotide*diphosphopyridine nucleotide oxidized*nicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide oxidized*NAD-oxidized*NAD-ox*NAD+*DPN+*DPN-ox*DPN*β-nicotinamide adenine dinucleotide*NAD 662.422 C21 H26 N7 O14 P2 NC(=O)C1(=CC=C[N+](=C1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CHEBI:57540:*PUBCHEM:15938971:*PUBCHEM:15938971:*LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.8 sn-glycerol-3-phosphate + NAD+ = dihydroxyacetone phosphate + NADH + H+ glycerol-3-phosphate shuttle 4'-phosphopantetheine pantetheine 4'-phosphate*phosphopantotheine*pantotheine-4'-phosphate*4'-phosphopantetheine*phosphopantetheine 356.33 C11 H21 N2 O7 P1 S1 C(C(O)C(=O)NCCC(NCCS)=O)(C)(C)COP([O-])(=O)[O-] KNAPSACK:C00007448:*PUBCHEM:25245905:*LIGAND-CPD:C01134: 4.1.1.36 H+ + R-4'-phosphopantothenoyl-L-cysteine = 4'-phosphopantetheine + CO2 coenzyme A biosynthesis 4'-phosphopantetheine pantetheine 4'-phosphate*phosphopantotheine*pantotheine-4'-phosphate*4'-phosphopantetheine*phosphopantetheine 356.33 C11 H21 N2 O7 P1 S1 C(C(O)C(=O)NCCC(NCCS)=O)(C)(C)COP([O-])(=O)[O-] KNAPSACK:C00007448:*PUBCHEM:25245905:*LIGAND-CPD:C01134: 3.1.4.14 H2O = 4'-phosphopantetheine acyl carrier protein metabolism 4'-phosphopantetheine pantetheine 4'-phosphate*phosphopantotheine*pantotheine-4'-phosphate*4'-phosphopantetheine*phosphopantetheine 356.33 C11 H21 N2 O7 P1 S1 C(C(O)C(=O)NCCC(NCCS)=O)(C)(C)COP([O-])(=O)[O-] KNAPSACK:C00007448:*PUBCHEM:25245905:*LIGAND-CPD:C01134: 2.7.7.3 H+ + 4'-phosphopantetheine + ATP = dephospho-CoA + diphosphate coenzyme A biosynthesis trans-5-O-caffeoyl-D-quinate caffeoylquinate*chlorogenate*chlorogenic acid*3-O-caffeoyl-D-quinic acid 353.305 C16 H17 O9 O=C(C=CC1(=CC=C(O)C(O)=C1))OC2(CC(O)(CC(O)C(O)2)C(=O)[O-]) CAS:327-97-9*NCI:407296*PUBCHEM:25245364:*CHEBI:16112:*CHEBI:57754:*PUBCHEM:25244622:*LIGAND-CPD:C00852: 3.1.2.- trans-5-O-caffeoyl-D-quinate + coenzyme A = caffeoyl-CoA + L-quinate chlorogenic acid biosynthesis I trans-5-O-caffeoyl-D-quinate caffeoylquinate*chlorogenate*chlorogenic acid*3-O-caffeoyl-D-quinic acid 353.305 C16 H17 O9 O=C(C=CC1(=CC=C(O)C(O)=C1))OC2(CC(O)(CC(O)C(O)2)C(=O)[O-]) CAS:327-97-9*NCI:407296*PUBCHEM:25245364:*CHEBI:16112:*CHEBI:57754:*PUBCHEM:25244622:*LIGAND-CPD:C00852: 3.1.2.- trans-5-O-caffeoyl-D-quinate + coenzyme A = caffeoyl-CoA + L-quinate phenylpropanoid biosynthesis trans-5-O-caffeoyl-D-quinate caffeoylquinate*chlorogenate*chlorogenic acid*3-O-caffeoyl-D-quinic acid 353.305 C16 H17 O9 O=C(C=CC1(=CC=C(O)C(O)=C1))OC2(CC(O)(CC(O)C(O)2)C(=O)[O-]) CAS:327-97-9*NCI:407296*PUBCHEM:25245364:*CHEBI:16112:*CHEBI:57754:*PUBCHEM:25244622:*LIGAND-CPD:C00852: 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ chlorogenic acid biosynthesis I trans-5-O-caffeoyl-D-quinate caffeoylquinate*chlorogenate*chlorogenic acid*3-O-caffeoyl-D-quinic acid 353.305 C16 H17 O9 O=C(C=CC1(=CC=C(O)C(O)=C1))OC2(CC(O)(CC(O)C(O)2)C(=O)[O-]) CAS:327-97-9*NCI:407296*PUBCHEM:25245364:*CHEBI:16112:*CHEBI:57754:*PUBCHEM:25244622:*LIGAND-CPD:C00852: 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ chlorogenic acid biosynthesis II trans-5-O-caffeoyl-D-quinate caffeoylquinate*chlorogenate*chlorogenic acid*3-O-caffeoyl-D-quinic acid 353.305 C16 H17 O9 O=C(C=CC1(=CC=C(O)C(O)=C1))OC2(CC(O)(CC(O)C(O)2)C(=O)[O-]) CAS:327-97-9*NCI:407296*PUBCHEM:25245364:*CHEBI:16112:*CHEBI:57754:*PUBCHEM:25244622:*LIGAND-CPD:C00852: 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ phenylpropanoid biosynthesis 24-methylenecholesterol 398.671 C28 H46 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))O) PUBCHEM:23724573:*LIGAND-CPD:C15781: 24-methylenecholesterol = 24-methyldesmosterol plant sterol biosynthesis 24-methylenecholesterol 398.671 C28 H46 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))O) PUBCHEM:23724573:*LIGAND-CPD:C15781: 1.3.1.21 5-dehydro episterol + NADPH = 24-methylenecholesterol + NADP+ plant sterol biosynthesis 7-hydroxy-chlorophyllide a 7-OH-chlorophyllide a 630.982 C35 H34 N4 O6 MG1 C24(C=C9(C(C)C(CCC(=O)O)C5(=N([Mg]36(N1(=C(C(CC)=C(CO)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) PUBCHEM:25244035:*LIGAND-CPD:C16540: 1.14.13.- H+ + chlorophyllide a + oxygen + NADPH = 7-hydroxy-chlorophyllide a + H2O + NADP+ chlorophyll cycle 7-hydroxy-chlorophyllide a 7-OH-chlorophyllide a 630.982 C35 H34 N4 O6 MG1 C24(C=C9(C(C)C(CCC(=O)O)C5(=N([Mg]36(N1(=C(C(CC)=C(CO)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) PUBCHEM:25244035:*LIGAND-CPD:C16540: 1.14.13.- 7-hydroxy-chlorophyllide a + oxygen + NADPH = chlorophyllide b + H2O + NADP+ chlorophyll cycle guanosine nucleoside Q 283.243 C10 H13 N5 O5 C3(C2(N=CN(C1(C(O)C(O)C(CO)O1))C=2N=C(N)N3))=O CHEBI:121093:*PUBCHEM:765:*LIGAND-CPD:C00387:*CAS:118-00-3 3.2.2.1 guanosine + H2O = guanine guanosine nucleotides degradation II guanosine nucleoside Q 283.243 C10 H13 N5 O5 C3(C2(N=CN(C1(C(O)C(O)C(CO)O1))C=2N=C(N)N3))=O CHEBI:121093:*PUBCHEM:765:*LIGAND-CPD:C00387:*CAS:118-00-3 3.2.2.1 guanosine + H2O = guanine guanine and guanosine salvage II guanosine nucleoside Q 283.243 C10 H13 N5 O5 C3(C2(N=CN(C1(C(O)C(O)C(CO)O1))C=2N=C(N)N3))=O CHEBI:121093:*PUBCHEM:765:*LIGAND-CPD:C00387:*CAS:118-00-3 3.1.3.5 GMP + H2O = guanosine guanosine nucleotides degradation II UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 diphosphate = UTP + H+ stachyose degradation UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 UTP = dUTP + H2O pyrimidine deoxyribonucleotides de novo biosynthesis I UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.64 UTP = diphosphate stachyose degradation UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.23 H+ + N-acetyl-α-D-glucosamine 1-phosphate + UTP = UDP-α-N-acetyl-D-glucosamine + diphosphate UDP-N-acetyl-D-glucosamine biosynthesis II UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.10 H+ + α-D-galactose 1-phosphate + UTP = UDP-D-galactose + diphosphate stachyose degradation UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.10 H+ + α-D-galactose 1-phosphate + UTP = UDP-D-galactose + diphosphate galactose degradation III UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.37 H+ + β-L-arabinose 1-phosphate + UTP = diphosphate UDP-L-arabinose biosynthesis II (from L-arabinose) UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.44 H+ + α-D-glucuronate 1-phosphate + UTP = UDP-D-glucuronate + diphosphate UDP-D-glucuronate biosynthesis (from myo-inositol) UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate glycogen biosynthesis II (from UDP-D-Glucose) UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate sucrose degradation III UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate stachyose degradation UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate UDP-glucose biosynthesis (from glucose 6-phosphate) UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate colanic acid building blocks biosynthesis UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate galactose degradation III UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate sucrose biosynthesis UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 6.3.4.2 ATP + UTP + L-glutamine + H2O = H+ + ADP + CTP + L-glutamate pyrimidine ribonucleotides interconversion UTP uridine-triphosphate*uridine-5'-triphosphate 480.112 C9 H11 N2 O15 P3 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058168:*PUBCHEM:7058168:*PUBCHEM:7058168:*CHEBI:46398:*PUBCHEM:6133:*LIGAND-CPD:C00075:*CAS:63-39-8 2.7.4.6 UDP + ATP = UTP + ADP pyrimidine ribonucleotides interconversion Mg-protoporphyrin Mg-protoporphyrin IX*Mg-protoporphyrin*magnesium protoporphyrin*MgP 582.94 C34 H30 N4 O4 MG1 C16(N8(C(=C(C=1C)CCC([O-])=O)C=C2(C(=C(C7(=N2[Mg]5(N3(C(C(=C(C3=CC4(C(=C(C(N=45)=C6)C=C)C))C=C)C)=C7))8))C)CCC(=O)[O-]))) KNAPSACK:C00007369:*PUBCHEM:44229120:*LIGAND-CPD:C03516: 6.6.1.1 ATP + protoporphyrin IX + Mg2+ + H2O = H+ + Mg-protoporphyrin + ADP chlorophyllide a biosynthesis I Mg-protoporphyrin Mg-protoporphyrin IX*Mg-protoporphyrin*magnesium protoporphyrin*MgP 582.94 C34 H30 N4 O4 MG1 C16(N8(C(=C(C=1C)CCC([O-])=O)C=C2(C(=C(C7(=N2[Mg]5(N3(C(C(=C(C3=CC4(C(=C(C(N=45)=C6)C=C)C))C=C)C)=C7))8))C)CCC(=O)[O-]))) KNAPSACK:C00007369:*PUBCHEM:44229120:*LIGAND-CPD:C03516: 2.1.1.11 Mg-protoporphyrin + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + magnesium-protoporphyrin IX 13-monomethyl ester chlorophyllide a biosynthesis I α-L-galactose-1-phosphate 258.121 C6 H11 O9 P1 C1(O)(C(O)C(OP([O-])([O-])=O)OC(CO)C(O)1) CHEBI:60389:*PUBCHEM:46173227:*LIGAND-CPD:C15926: 2.7.7.69 GDP-L-galactose = H+ + GDP + α-L-galactose-1-phosphate ascorbate biosynthesis I (L-galactose pathway) α-L-galactose-1-phosphate 258.121 C6 H11 O9 P1 C1(O)(C(O)C(OP([O-])([O-])=O)OC(CO)C(O)1) CHEBI:60389:*PUBCHEM:46173227:*LIGAND-CPD:C15926: 3.1.3.- α-L-galactose-1-phosphate + H2O = L-galactose ascorbate biosynthesis I (L-galactose pathway) adenine 2-aminopurine*6-aminopurine 135.128 C5 H5 N5 C1(C2(=C(N=CN=1)N=CN2))N CHEBI:16708:*PUBCHEM:190:*LIGAND-CPD:C00147:*CAS:73-24-5 1.5.99.12 H+ + trans-zeatin + H2O + FAD = adenine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation adenine 2-aminopurine*6-aminopurine 135.128 C5 H5 N5 C1(C2(=C(N=CN=1)N=CN2))N CHEBI:16708:*PUBCHEM:190:*LIGAND-CPD:C00147:*CAS:73-24-5 3.2.2.16 S-methyl-5'-thioadenosine + H2O = S-methyl-5-thio-D-ribose + adenine methylthioadenosine degradation adenine 2-aminopurine*6-aminopurine 135.128 C5 H5 N5 C1(C2(=C(N=CN=1)N=CN2))N CHEBI:16708:*PUBCHEM:190:*LIGAND-CPD:C00147:*CAS:73-24-5 3.2.2.16 S-methyl-5'-thioadenosine + H2O = S-methyl-5-thio-D-ribose + adenine methionine salvage I adenine 2-aminopurine*6-aminopurine 135.128 C5 H5 N5 C1(C2(=C(N=CN=1)N=CN2))N CHEBI:16708:*PUBCHEM:190:*LIGAND-CPD:C00147:*CAS:73-24-5 1.5.99.12 N6-dimethylallyladenine + H+ + FAD + H2O = 3-methyl-2-butenal + adenine + FADH2 cytokinins degradation adenine 2-aminopurine*6-aminopurine 135.128 C5 H5 N5 C1(C2(=C(N=CN=1)N=CN2))N CHEBI:16708:*PUBCHEM:190:*LIGAND-CPD:C00147:*CAS:73-24-5 1.5.99.12 H+ + cis-zeatin + H2O + FAD = 3-methyl-4-cis-hydroxy-2-butenal + adenine + FADH2 cytokinins degradation adenine 2-aminopurine*6-aminopurine 135.128 C5 H5 N5 C1(C2(=C(N=CN=1)N=CN2))N CHEBI:16708:*PUBCHEM:190:*LIGAND-CPD:C00147:*CAS:73-24-5 3.2.2.9 S-adenosyl-L-homocysteine + H2O = S-ribosyl-L-homocysteine + adenine S-adenosyl-L-methionine cycle I adenine 2-aminopurine*6-aminopurine 135.128 C5 H5 N5 C1(C2(=C(N=CN=1)N=CN2))N CHEBI:16708:*PUBCHEM:190:*LIGAND-CPD:C00147:*CAS:73-24-5 2.4.2.7 AMP + diphosphate = adenine + 5-phospho-α-D-ribose 1-diphosphate adenine and adenosine salvage II adenine 2-aminopurine*6-aminopurine 135.128 C5 H5 N5 C1(C2(=C(N=CN=1)N=CN2))N CHEBI:16708:*PUBCHEM:190:*LIGAND-CPD:C00147:*CAS:73-24-5 3.2.2.7 H2O + adenosine = adenine adenine and adenosine salvage II 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol CDP-ME*CDP-methyl-D-erythritol*4-diphosphocytidyl-2C-methyl-D-erythritol*4-diphosphocytidyl-2-C-methylerythritol 519.295 C14 H23 N3 O14 P2 CC(O)(CO)C(O)COP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(N)=NC(=O)2)) PUBCHEM:25244630:*LIGAND-CPD:C11435: 2.7.1.148 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + ATP = H+ + 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + ADP methylerythritol phosphate pathway 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol CDP-ME*CDP-methyl-D-erythritol*4-diphosphocytidyl-2C-methyl-D-erythritol*4-diphosphocytidyl-2-C-methylerythritol 519.295 C14 H23 N3 O14 P2 CC(O)(CO)C(O)COP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(N)=NC(=O)2)) PUBCHEM:25244630:*LIGAND-CPD:C11435: 2.7.7.60 H+ + 2-C-methyl-D-erythritol-4-phosphate + CTP = 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + diphosphate methylerythritol phosphate pathway α-maltose 342.299 C12 H22 O11 C1(OC(C(C(C1O)O)O)OC2(C(OC(C(C2O)O)O)CO))CO LIGAND-CPD:C00897:*CHEBI:18167:*PUBCHEM:439341: 3.2.1.2 H2O = α-maltose starch degradation α-maltose 342.299 C12 H22 O11 C1(OC(C(C(C1O)O)O)OC2(C(OC(C(C2O)O)O)CO))CO LIGAND-CPD:C00897:*CHEBI:18167:*PUBCHEM:439341: 3.2.1.20 α-maltose + H2O = α-D-glucose starch degradation D-arabinose 5-phosphate D-arabinose-5-P*arabinose-5P*D-A-5-P*arabinose 5-phosphate*arabinose-5-P 228.095 C5 H9 O8 P1 C(C(C(C(COP([O-])([O-])=O)O)O)O)=O PUBCHEM:21880554:*PUBCHEM:23615240:*LIGAND-CPD:C01112:*CAS:13137-52-5 2.5.1.55 D-arabinose 5-phosphate + H2O + phosphoenolpyruvate = 3-deoxy-D-manno-octulosonate 8-P CMP-KDO biosynthesis II (from D-arabinose 5-phosphate) sulfite sulfite*HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])([O-])=O CHEBI:17359:*PUBCHEM:1099:*CAS:14265-45-3:*LIGAND-CPD:C00094:*CAS:7782-99-2: 1.8.3.1 sulfite + oxygen + H2O = hydrogen peroxide + sulfate sulfite oxidation IV sulfite sulfite*HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])([O-])=O CHEBI:17359:*PUBCHEM:1099:*CAS:14265-45-3:*LIGAND-CPD:C00094:*CAS:7782-99-2: 1.8.4.9 H+ + sulfite + AMP + glutathione disulfide = adenosine 5'-phosphosulfate + glutathione sulfate reduction II (assimilatory) sulfite sulfite*HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])([O-])=O CHEBI:17359:*PUBCHEM:1099:*CAS:14265-45-3:*LIGAND-CPD:C00094:*CAS:7782-99-2: 2.8.1.1 thiosulfate + hydrogen cyanide = H+ + sulfite + thiocyanate thiosulfate disproportionation III (rhodanese) sulfite sulfite*HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])([O-])=O CHEBI:17359:*PUBCHEM:1099:*CAS:14265-45-3:*LIGAND-CPD:C00094:*CAS:7782-99-2: 1.8.99.2 sulfite + AMP = adenosine 5'-phosphosulfate sulfite oxidation III sulfite sulfite*HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])([O-])=O CHEBI:17359:*PUBCHEM:1099:*CAS:14265-45-3:*LIGAND-CPD:C00094:*CAS:7782-99-2: 1.8.99.2 sulfite + AMP = adenosine 5'-phosphosulfate sulfite oxidation II sulfite sulfite*HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])([O-])=O CHEBI:17359:*PUBCHEM:1099:*CAS:14265-45-3:*LIGAND-CPD:C00094:*CAS:7782-99-2: 1.8.7.1 hydrogen sulfide + H2O = sulfite sulfate reduction II (assimilatory) sulfite sulfite*HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])([O-])=O CHEBI:17359:*PUBCHEM:1099:*CAS:14265-45-3:*LIGAND-CPD:C00094:*CAS:7782-99-2: 1.8.4.8 adenosine 3',5'-bisphosphate + sulfite = phosphoadenosine-5'-phosphosulfate sulfate reduction I (assimilatory) sulfite sulfite*HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])([O-])=O CHEBI:17359:*PUBCHEM:1099:*CAS:14265-45-3:*LIGAND-CPD:C00094:*CAS:7782-99-2: 1.8.1.2 H2O + NADP+ + hydrogen sulfide = H+ + sulfite + NADPH sulfate reduction I (assimilatory) sulfite sulfite*HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])([O-])=O CHEBI:17359:*PUBCHEM:1099:*CAS:14265-45-3:*LIGAND-CPD:C00094:*CAS:7782-99-2: 3.13.1.1 UDP-α-D-glucose + H+ + sulfite = UDP-α-D-sulfoquinovopyranose + H2O sulfolipid biosynthesis 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 2.3.1.170 H+ + 4-coumaroyl-CoA + malonyl-CoA + NADPH = isoliquiritigenin + coenzyme A + CO2 + NADP+ + H2O flavonoid biosynthesis 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 1.2.1.44 4-coumaroyl-CoA + NADPH + H+ = coumaraldehyde + coenzyme A + NADP+ phenylpropanoid biosynthesis 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ flavonoid biosynthesis 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ simplecoumarins biosynthesis 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ phenylpropanoid biosynthesis 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ 4-hydroxybenzoate biosynthesis V 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 2.3.1.133 4-coumaroyl-CoA + L-quinate = trans-5-O-(4-coumaroyl)-D-quinate + coenzyme A chlorogenic acid biosynthesis I 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 2.3.1.133 4-coumaroyl-CoA + L-quinate = trans-5-O-(4-coumaroyl)-D-quinate + coenzyme A chlorogenic acid biosynthesis II 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 2.3.1.133 4-coumaroyl-CoA + L-quinate = trans-5-O-(4-coumaroyl)-D-quinate + coenzyme A phenylpropanoid biosynthesis 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A chlorogenic acid biosynthesis I 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A chlorogenic acid biosynthesis II 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A simplecoumarins biosynthesis 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A phenylpropanoid biosynthesis 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 2.3.1.- H+ + 4-coumaroyl-CoA + malonyl-CoA = bis-noryangonin + coenzyme A + CO2 resveratrol biosynthesis 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 4-coumaroyl-CoA + NADPH + FADH2 = p-dihydrocoumaroyl-CoA + NADP+ + FAD + H+ phloridzin biosynthesis 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 2.3.1.95 H+ + 4-coumaroyl-CoA + malonyl-CoA = resveratrol + coenzyme A + CO2 resveratrol biosynthesis 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 4.2.1.17 3-(4-hydroxyphenyl)-3-hydroxy-propionyl-CoA = 4-coumaroyl-CoA + H2O 4-hydroxybenzoate biosynthesis V 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 2.3.1.74 H+ + 4-coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A flavonoid biosynthesis 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 2.3.1.74 H+ + 4-coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A aromatic polyketides biosynthesis 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 2.3.1.- H+ + 4-coumaroyl-CoA + malonyl-CoA = p-coumaroyltriacetic acid lactone + coenzyme A + CO2 aromatic polyketides biosynthesis 4-coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA*coumaroyl-CoA*p-coumaroyl-CoA 909.648 C30 H38 N7 O18 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC4(=CC=C(O)C=C4) PUBCHEM:25244633:*PUBCHEM:25244633:*LIGAND-CPD:C00223:*CHEBI:15499*CHEBI:15346*PUBCHEM:6816*LIGAND-CPD:C00010 2.3.1.- H+ + 4-coumaroyl-CoA + H2O + malonyl-CoA = coenzyme A + CO2 + p-coumaroyltriacetate resveratrol biosynthesis 7',9'-cis-lycopene 536.882 C40 H56 CC(=CCCC(=CC=CC(C)=CC=CC(=CC=CC=C(C=CC=C(C)C=CC=C(CCC=C(C)C)C)C)C)C)C 9'-cis-neurosporene + oxygen = 7',9'-cis-lycopene + H2O trans-lycopene biosynthesis II (plants) 7',9'-cis-lycopene 536.882 C40 H56 CC(=CCCC(=CC=CC(C)=CC=CC(=CC=CC=C(C=CC=C(C)C=CC=C(CCC=C(C)C)C)C)C)C)C 5.2.1.- 7',9'-cis-lycopene = all-trans-lycopene trans-lycopene biosynthesis II (plants) acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C(C)([O-])=O PUBCHEM:175:*PUBCHEM:175:*CHEBI:30089:*LIGAND-CPD:c00033:*PUBCHEM:176:*CAS:64-19-7:*LIGAND-CPD:C00033:*CAS:71-50-1 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP acetate conversion to acetyl-CoA acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C(C)([O-])=O PUBCHEM:175:*PUBCHEM:175:*CHEBI:30089:*LIGAND-CPD:c00033:*PUBCHEM:176:*CAS:64-19-7:*LIGAND-CPD:C00033:*CAS:71-50-1 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP ethanol degradation II (cytosol) acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C(C)([O-])=O PUBCHEM:175:*PUBCHEM:175:*CHEBI:30089:*LIGAND-CPD:c00033:*PUBCHEM:176:*CAS:64-19-7:*LIGAND-CPD:C00033:*CAS:71-50-1 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP ethanol degradation IV (peroxisomal) acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C(C)([O-])=O PUBCHEM:175:*PUBCHEM:175:*CHEBI:30089:*LIGAND-CPD:c00033:*PUBCHEM:176:*CAS:64-19-7:*LIGAND-CPD:C00033:*CAS:71-50-1 2.5.1.47 O-acetyl-L-serine + hydrogen sulfide = H+ + L-cysteine + acetate cysteine biosynthesis I acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C(C)([O-])=O PUBCHEM:175:*PUBCHEM:175:*CHEBI:30089:*LIGAND-CPD:c00033:*PUBCHEM:176:*CAS:64-19-7:*LIGAND-CPD:C00033:*CAS:71-50-1 3-hydroxy-3-phenylpropionate = benzaldehyde + acetate benzoate biosynthesis II (CoA-independent, non-β-oxidative) acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C(C)([O-])=O PUBCHEM:175:*PUBCHEM:175:*CHEBI:30089:*LIGAND-CPD:c00033:*PUBCHEM:176:*CAS:64-19-7:*LIGAND-CPD:C00033:*CAS:71-50-1 indole + acetate = H+ + indole-3-acetate IAA biosynthesis I acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C(C)([O-])=O PUBCHEM:175:*PUBCHEM:175:*CHEBI:30089:*LIGAND-CPD:c00033:*PUBCHEM:176:*CAS:64-19-7:*LIGAND-CPD:C00033:*CAS:71-50-1 1.2.1.3 acetaldehyde + H2O + NAD+ = acetate + NADH + H+ ethanol degradation II (cytosol) acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C(C)([O-])=O PUBCHEM:175:*PUBCHEM:175:*CHEBI:30089:*LIGAND-CPD:c00033:*PUBCHEM:176:*CAS:64-19-7:*LIGAND-CPD:C00033:*CAS:71-50-1 1.2.1.3 acetaldehyde + H2O + NAD+ = acetate + NADH + H+ ethanol degradation IV (peroxisomal) acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C(C)([O-])=O PUBCHEM:175:*PUBCHEM:175:*CHEBI:30089:*LIGAND-CPD:c00033:*PUBCHEM:176:*CAS:64-19-7:*LIGAND-CPD:C00033:*CAS:71-50-1 O-acetyl-L-homoserine + L-cysteine = H+ + L-cystathionine + acetate homocysteine and cysteine interconversion acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C(C)([O-])=O PUBCHEM:175:*PUBCHEM:175:*CHEBI:30089:*LIGAND-CPD:c00033:*PUBCHEM:176:*CAS:64-19-7:*LIGAND-CPD:C00033:*CAS:71-50-1 3.5.1.16 N-acetyl-L-ornithine + H2O = L-ornithine + acetate ornithine biosynthesis 5-enolpyruvyl-shikimate-3-phosphate EPSP*3-enolpyruvyl-shikimate-5-phosphate*3-enolpyruvyl-shikimate-5-P*5-O-(1-carboxyvinyl)-3-phosphoshikimate 320.149 C10 H9 O10 P1 C1(OP(=O)([O-])[O-])(C=C(C(=O)[O-])CC(OC(=C)C(=O)[O-])C(O)1) CHEBI:57701:*PUBCHEM:14506801:*LIGAND-CPD:C01269: 4.2.3.5 5-enolpyruvyl-shikimate-3-phosphate = chorismate chorismate biosynthesis I 5-enolpyruvyl-shikimate-3-phosphate EPSP*3-enolpyruvyl-shikimate-5-phosphate*3-enolpyruvyl-shikimate-5-P*5-O-(1-carboxyvinyl)-3-phosphoshikimate 320.149 C10 H9 O10 P1 C1(OP(=O)([O-])[O-])(C=C(C(=O)[O-])CC(OC(=C)C(=O)[O-])C(O)1) CHEBI:57701:*PUBCHEM:14506801:*LIGAND-CPD:C01269: 2.5.1.19 shikimate-3-phosphate + phosphoenolpyruvate = 5-enolpyruvyl-shikimate-3-phosphate chorismate biosynthesis I p-coumaroyltriacetate p-coumaroyltriacetic acid 290.272 C15 H13 O6 C(C=CC1(C=CC(=CC=1)O))(CC(CC(CC([O-])=O)=O)=O)=O PUBCHEM:25245921: p-coumaroyltriacetate = p-coumaroyltriacetic acid lactone + H2O resveratrol biosynthesis p-coumaroyltriacetate p-coumaroyltriacetic acid 290.272 C15 H13 O6 C(C=CC1(C=CC(=CC=1)O))(CC(CC(CC([O-])=O)=O)=O)=O PUBCHEM:25245921: 2.3.1.- H+ + 4-coumaroyl-CoA + H2O + malonyl-CoA = coenzyme A + CO2 + p-coumaroyltriacetate resveratrol biosynthesis presqualene diphosphate 583.66 C30 H49 O7 P2 CC(=CCCC(=CCCC(=CC1(C(CCC=C(CCC=C(C)C)C)(C1COP(OP([O-])([O-])=O)([O-])=O)C))C)C)C PUBCHEM:25244634:*LIGAND-CPD:C03428: 2.5.1.21 presqualene diphosphate = squalene + diphosphate epoxysqualene biosynthesis presqualene diphosphate 583.66 C30 H49 O7 P2 CC(=CCCC(=CCCC(=CC1(C(CCC=C(CCC=C(C)C)C)(C1COP(OP([O-])([O-])=O)([O-])=O)C))C)C)C PUBCHEM:25244634:*LIGAND-CPD:C03428: 2.5.1.21 (2E,6E)-farnesyl diphosphate = presqualene diphosphate + diphosphate epoxysqualene biosynthesis sn-glycerol-3-phosphate L-glycerol 3-phosphate*L-G3P*sn-glycerol-3-phosphate*α-glycerophosphoric acid*glycerol-3-P*glycerol-1-phosphate*α-glycerophosphate*D-glycerol-3-phosphate*rac-Glycerol 3-phosphate*glycerol-3-phosphate 170.058 C3 H7 O6 P1 OCC(O)COP([O-])(=O)[O-] CHEBI:57597:*PUBCHEM:7048685:*CHEBI:15978:*PUBCHEM:7048686:*LIGAND-CPD:C00093:*CAS:57-03-4 2.7.8.5 sn-glycerol-3-phosphate = CMP + H+ phosphatidylglycerol biosynthesis I (plastidic) sn-glycerol-3-phosphate L-glycerol 3-phosphate*L-G3P*sn-glycerol-3-phosphate*α-glycerophosphoric acid*glycerol-3-P*glycerol-1-phosphate*α-glycerophosphate*D-glycerol-3-phosphate*rac-Glycerol 3-phosphate*glycerol-3-phosphate 170.058 C3 H7 O6 P1 OCC(O)COP([O-])(=O)[O-] CHEBI:57597:*PUBCHEM:7048685:*CHEBI:15978:*PUBCHEM:7048686:*LIGAND-CPD:C00093:*CAS:57-03-4 2.7.8.5 sn-glycerol-3-phosphate = CMP + H+ phosphatidylglycerol biosynthesis II (non-plastidic) sn-glycerol-3-phosphate L-glycerol 3-phosphate*L-G3P*sn-glycerol-3-phosphate*α-glycerophosphoric acid*glycerol-3-P*glycerol-1-phosphate*α-glycerophosphate*D-glycerol-3-phosphate*rac-Glycerol 3-phosphate*glycerol-3-phosphate 170.058 C3 H7 O6 P1 OCC(O)COP([O-])(=O)[O-] CHEBI:57597:*PUBCHEM:7048685:*CHEBI:15978:*PUBCHEM:7048686:*LIGAND-CPD:C00093:*CAS:57-03-4 2.7.8.5 sn-glycerol-3-phosphate = CMP + H+ cardiolipin biosynthesis II sn-glycerol-3-phosphate L-glycerol 3-phosphate*L-G3P*sn-glycerol-3-phosphate*α-glycerophosphoric acid*glycerol-3-P*glycerol-1-phosphate*α-glycerophosphate*D-glycerol-3-phosphate*rac-Glycerol 3-phosphate*glycerol-3-phosphate 170.058 C3 H7 O6 P1 OCC(O)COP([O-])(=O)[O-] CHEBI:57597:*PUBCHEM:7048685:*CHEBI:15978:*PUBCHEM:7048686:*LIGAND-CPD:C00093:*CAS:57-03-4 2.3.1.15 sn-glycerol-3-phosphate = coenzyme A CDP-diacylglycerol biosynthesis I sn-glycerol-3-phosphate L-glycerol 3-phosphate*L-G3P*sn-glycerol-3-phosphate*α-glycerophosphoric acid*glycerol-3-P*glycerol-1-phosphate*α-glycerophosphate*D-glycerol-3-phosphate*rac-Glycerol 3-phosphate*glycerol-3-phosphate 170.058 C3 H7 O6 P1 OCC(O)COP([O-])(=O)[O-] CHEBI:57597:*PUBCHEM:7048685:*CHEBI:15978:*PUBCHEM:7048686:*LIGAND-CPD:C00093:*CAS:57-03-4 2.3.1.15 sn-glycerol-3-phosphate = coenzyme A triacylglycerol biosynthesis sn-glycerol-3-phosphate L-glycerol 3-phosphate*L-G3P*sn-glycerol-3-phosphate*α-glycerophosphoric acid*glycerol-3-P*glycerol-1-phosphate*α-glycerophosphate*D-glycerol-3-phosphate*rac-Glycerol 3-phosphate*glycerol-3-phosphate 170.058 C3 H7 O6 P1 OCC(O)COP([O-])(=O)[O-] CHEBI:57597:*PUBCHEM:7048685:*CHEBI:15978:*PUBCHEM:7048686:*LIGAND-CPD:C00093:*CAS:57-03-4 1.1.5.3 sn-glycerol-3-phosphate = dihydroxyacetone phosphate glycerol-3-phosphate shuttle sn-glycerol-3-phosphate L-glycerol 3-phosphate*L-G3P*sn-glycerol-3-phosphate*α-glycerophosphoric acid*glycerol-3-P*glycerol-1-phosphate*α-glycerophosphate*D-glycerol-3-phosphate*rac-Glycerol 3-phosphate*glycerol-3-phosphate 170.058 C3 H7 O6 P1 OCC(O)COP([O-])(=O)[O-] CHEBI:57597:*PUBCHEM:7048685:*CHEBI:15978:*PUBCHEM:7048686:*LIGAND-CPD:C00093:*CAS:57-03-4 1.1.5.3 sn-glycerol-3-phosphate = dihydroxyacetone phosphate glycerol degradation IV sn-glycerol-3-phosphate L-glycerol 3-phosphate*L-G3P*sn-glycerol-3-phosphate*α-glycerophosphoric acid*glycerol-3-P*glycerol-1-phosphate*α-glycerophosphate*D-glycerol-3-phosphate*rac-Glycerol 3-phosphate*glycerol-3-phosphate 170.058 C3 H7 O6 P1 OCC(O)COP([O-])(=O)[O-] CHEBI:57597:*PUBCHEM:7048685:*CHEBI:15978:*PUBCHEM:7048686:*LIGAND-CPD:C00093:*CAS:57-03-4 1.1.5.3 sn-glycerol-3-phosphate + ubiquinone-8 = ubiquinol-8 + dihydroxyacetone phosphate glycerol degradation I sn-glycerol-3-phosphate L-glycerol 3-phosphate*L-G3P*sn-glycerol-3-phosphate*α-glycerophosphoric acid*glycerol-3-P*glycerol-1-phosphate*α-glycerophosphate*D-glycerol-3-phosphate*rac-Glycerol 3-phosphate*glycerol-3-phosphate 170.058 C3 H7 O6 P1 OCC(O)COP([O-])(=O)[O-] CHEBI:57597:*PUBCHEM:7048685:*CHEBI:15978:*PUBCHEM:7048686:*LIGAND-CPD:C00093:*CAS:57-03-4 2.3.1.15 CDP-diacylglycerol biosynthesis II sn-glycerol-3-phosphate L-glycerol 3-phosphate*L-G3P*sn-glycerol-3-phosphate*α-glycerophosphoric acid*glycerol-3-P*glycerol-1-phosphate*α-glycerophosphate*D-glycerol-3-phosphate*rac-Glycerol 3-phosphate*glycerol-3-phosphate 170.058 C3 H7 O6 P1 OCC(O)COP([O-])(=O)[O-] CHEBI:57597:*PUBCHEM:7048685:*CHEBI:15978:*PUBCHEM:7048686:*LIGAND-CPD:C00093:*CAS:57-03-4 3.1.4.46 H2O = sn-glycerol-3-phosphate + H+ glycerol degradation I sn-glycerol-3-phosphate L-glycerol 3-phosphate*L-G3P*sn-glycerol-3-phosphate*α-glycerophosphoric acid*glycerol-3-P*glycerol-1-phosphate*α-glycerophosphate*D-glycerol-3-phosphate*rac-Glycerol 3-phosphate*glycerol-3-phosphate 170.058 C3 H7 O6 P1 OCC(O)COP([O-])(=O)[O-] CHEBI:57597:*PUBCHEM:7048685:*CHEBI:15978:*PUBCHEM:7048686:*LIGAND-CPD:C00093:*CAS:57-03-4 2.7.1.30 glycerol + ATP = H+ + sn-glycerol-3-phosphate + ADP glycerol degradation IV sn-glycerol-3-phosphate L-glycerol 3-phosphate*L-G3P*sn-glycerol-3-phosphate*α-glycerophosphoric acid*glycerol-3-P*glycerol-1-phosphate*α-glycerophosphate*D-glycerol-3-phosphate*rac-Glycerol 3-phosphate*glycerol-3-phosphate 170.058 C3 H7 O6 P1 OCC(O)COP([O-])(=O)[O-] CHEBI:57597:*PUBCHEM:7048685:*CHEBI:15978:*PUBCHEM:7048686:*LIGAND-CPD:C00093:*CAS:57-03-4 2.7.1.30 glycerol + ATP = H+ + sn-glycerol-3-phosphate + ADP glycerol degradation I sn-glycerol-3-phosphate L-glycerol 3-phosphate*L-G3P*sn-glycerol-3-phosphate*α-glycerophosphoric acid*glycerol-3-P*glycerol-1-phosphate*α-glycerophosphate*D-glycerol-3-phosphate*rac-Glycerol 3-phosphate*glycerol-3-phosphate 170.058 C3 H7 O6 P1 OCC(O)COP([O-])(=O)[O-] CHEBI:57597:*PUBCHEM:7048685:*CHEBI:15978:*PUBCHEM:7048686:*LIGAND-CPD:C00093:*CAS:57-03-4 1.1.1.94 sn-glycerol-3-phosphate = dihydroxyacetone phosphate + H+ CDP-diacylglycerol biosynthesis II sn-glycerol-3-phosphate L-glycerol 3-phosphate*L-G3P*sn-glycerol-3-phosphate*α-glycerophosphoric acid*glycerol-3-P*glycerol-1-phosphate*α-glycerophosphate*D-glycerol-3-phosphate*rac-Glycerol 3-phosphate*glycerol-3-phosphate 170.058 C3 H7 O6 P1 OCC(O)COP([O-])(=O)[O-] CHEBI:57597:*PUBCHEM:7048685:*CHEBI:15978:*PUBCHEM:7048686:*LIGAND-CPD:C00093:*CAS:57-03-4 1.1.1.94 sn-glycerol-3-phosphate = dihydroxyacetone phosphate + H+ CDP-diacylglycerol biosynthesis I sn-glycerol-3-phosphate L-glycerol 3-phosphate*L-G3P*sn-glycerol-3-phosphate*α-glycerophosphoric acid*glycerol-3-P*glycerol-1-phosphate*α-glycerophosphate*D-glycerol-3-phosphate*rac-Glycerol 3-phosphate*glycerol-3-phosphate 170.058 C3 H7 O6 P1 OCC(O)COP([O-])(=O)[O-] CHEBI:57597:*PUBCHEM:7048685:*CHEBI:15978:*PUBCHEM:7048686:*LIGAND-CPD:C00093:*CAS:57-03-4 1.1.1.8 sn-glycerol-3-phosphate + NAD+ = dihydroxyacetone phosphate + NADH + H+ glycerol-3-phosphate shuttle loganin 390.386 C17 H26 O10 COC(=O)C2(=COC(OC1(OC(CO)C(O)C(O)C(O)1))C3(C(C)C(O)CC23)) PUBCHEM:354446:*CHEBI:15771:*LIGAND-CPD:C01433:*NCI:606403*CAS:18524-94-2 1.3.3.9 H+ + oxygen + NADPH + loganin = H2O + NADP+ + secologanin camptothecin biosynthesis L-arginino-succinate N-(L-arginino)-succinate*arginino-succinate 289.267 C10 H17 N4 O6 [N+]=C(NC(CC(=O)[O-])C(=O)[O-])NCCCC(C(=O)[O-])[N+] PUBCHEM:25245925:*PUBCHEM:25245925:*PUBCHEM:828:*LIGAND-CPD:C03406: 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP urea cycle L-arginino-succinate N-(L-arginino)-succinate*arginino-succinate 289.267 C10 H17 N4 O6 [N+]=C(NC(CC(=O)[O-])C(=O)[O-])NCCCC(C(=O)[O-])[N+] PUBCHEM:25245925:*PUBCHEM:25245925:*PUBCHEM:828:*LIGAND-CPD:C03406: 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP arginine biosynthesis II (acetyl cycle) L-arginino-succinate N-(L-arginino)-succinate*arginino-succinate 289.267 C10 H17 N4 O6 [N+]=C(NC(CC(=O)[O-])C(=O)[O-])NCCCC(C(=O)[O-])[N+] PUBCHEM:25245925:*PUBCHEM:25245925:*PUBCHEM:828:*LIGAND-CPD:C03406: 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP citrulline-nitric oxide cycle L-arginino-succinate N-(L-arginino)-succinate*arginino-succinate 289.267 C10 H17 N4 O6 [N+]=C(NC(CC(=O)[O-])C(=O)[O-])NCCCC(C(=O)[O-])[N+] PUBCHEM:25245925:*PUBCHEM:25245925:*PUBCHEM:828:*LIGAND-CPD:C03406: 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP arginine biosynthesis I L-arginino-succinate N-(L-arginino)-succinate*arginino-succinate 289.267 C10 H17 N4 O6 [N+]=C(NC(CC(=O)[O-])C(=O)[O-])NCCCC(C(=O)[O-])[N+] PUBCHEM:25245925:*PUBCHEM:25245925:*PUBCHEM:828:*LIGAND-CPD:C03406: 4.3.2.1 L-arginino-succinate = L-arginine + fumarate urea cycle L-arginino-succinate N-(L-arginino)-succinate*arginino-succinate 289.267 C10 H17 N4 O6 [N+]=C(NC(CC(=O)[O-])C(=O)[O-])NCCCC(C(=O)[O-])[N+] PUBCHEM:25245925:*PUBCHEM:25245925:*PUBCHEM:828:*LIGAND-CPD:C03406: 4.3.2.1 L-arginino-succinate = L-arginine + fumarate arginine biosynthesis II (acetyl cycle) L-arginino-succinate N-(L-arginino)-succinate*arginino-succinate 289.267 C10 H17 N4 O6 [N+]=C(NC(CC(=O)[O-])C(=O)[O-])NCCCC(C(=O)[O-])[N+] PUBCHEM:25245925:*PUBCHEM:25245925:*PUBCHEM:828:*LIGAND-CPD:C03406: 4.3.2.1 L-arginino-succinate = L-arginine + fumarate citrulline-nitric oxide cycle L-arginino-succinate N-(L-arginino)-succinate*arginino-succinate 289.267 C10 H17 N4 O6 [N+]=C(NC(CC(=O)[O-])C(=O)[O-])NCCCC(C(=O)[O-])[N+] PUBCHEM:25245925:*PUBCHEM:25245925:*PUBCHEM:828:*LIGAND-CPD:C03406: 4.3.2.1 L-arginino-succinate = L-arginine + fumarate arginine biosynthesis I afzelechin 3,5,7,4'-tetrahydroxyflavan 274.273 C15 H14 O5 C1(C=CC(O)=CC=1)(C2(C(O)CC3(C(O2)=CC(O)=CC(O)=3))) PUBCHEM:9943440:*LIGAND-CPD:C09320: 1.17.1.3 afzelechin + NADP+ + H2O = leucopelargonidin + NADPH + H+ 2,3-trans-flavanols biosynthesis UDP-α-N-acetyl-D-glucosamine UDP-acetyl-D-glucosamine*UDP-GlcNAc*UDP-N-acetyl-glucosamine*uridine diphosphate N-acetylglucosamine*N-[2-[[[5-[(2,4-dioxo-1H-pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy-phosphinoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide*UDP-2-acetamido-2-deoxy-α-D-glucose*UDP-N-acetyl-D-glucosamine*UDP-N-acetyl-α-D-glucosamine 605.342 C17 H25 N3 O17 P2 OC3(C(C(C(OP(OP(OCC1(C(C(C(O1)N2(C=CC(NC2=O)=O))O)O))([O-])=O)([O-])=O)OC3CO)NC(C)=O)O) CHEBI:57705:*PUBCHEM:16667373:*LIGAND-CPD:C00043:*CAS:528-04-1 2.4.1.141 UDP-α-N-acetyl-D-glucosamine = H+ + UDP dolichyl-diphosphooligosaccharide biosynthesis UDP-α-N-acetyl-D-glucosamine UDP-acetyl-D-glucosamine*UDP-GlcNAc*UDP-N-acetyl-glucosamine*uridine diphosphate N-acetylglucosamine*N-[2-[[[5-[(2,4-dioxo-1H-pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy-phosphinoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide*UDP-2-acetamido-2-deoxy-α-D-glucose*UDP-N-acetyl-D-glucosamine*UDP-N-acetyl-α-D-glucosamine 605.342 C17 H25 N3 O17 P2 OC3(C(C(C(OP(OP(OCC1(C(C(C(O1)N2(C=CC(NC2=O)=O))O)O))([O-])=O)([O-])=O)OC3CO)NC(C)=O)O) CHEBI:57705:*PUBCHEM:16667373:*LIGAND-CPD:C00043:*CAS:528-04-1 2.7.7.23 H+ + N-acetyl-α-D-glucosamine 1-phosphate + UTP = UDP-α-N-acetyl-D-glucosamine + diphosphate UDP-N-acetyl-D-glucosamine biosynthesis II UDP-α-N-acetyl-D-glucosamine UDP-acetyl-D-glucosamine*UDP-GlcNAc*UDP-N-acetyl-glucosamine*uridine diphosphate N-acetylglucosamine*N-[2-[[[5-[(2,4-dioxo-1H-pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy-phosphinoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide*UDP-2-acetamido-2-deoxy-α-D-glucose*UDP-N-acetyl-D-glucosamine*UDP-N-acetyl-α-D-glucosamine 605.342 C17 H25 N3 O17 P2 OC3(C(C(C(OP(OP(OCC1(C(C(C(O1)N2(C=CC(NC2=O)=O))O)O))([O-])=O)([O-])=O)OC3CO)NC(C)=O)O) CHEBI:57705:*PUBCHEM:16667373:*LIGAND-CPD:C00043:*CAS:528-04-1 2.7.8.15 UDP-α-N-acetyl-D-glucosamine = uridine-5'-phosphate dolichyl-diphosphooligosaccharide biosynthesis galactinol 1-O-α-D-galactosyl-D-myo-inositol*1-α-D-galactosyl-myo-inositol*α-D-galactosyl-(1->3)-1D-myo-inositol 342.299 C12 H22 O11 OC1(C(C(C(C(C1O)OC2(OC(C(C(C2O)O)O)CO))O)O)O) PUBCHEM:25202439:*LIGAND-CPD:C01235: 2.4.1.67 galactinol + raffinose = myo-inositol + stachyose stachyose biosynthesis galactinol 1-O-α-D-galactosyl-D-myo-inositol*1-α-D-galactosyl-myo-inositol*α-D-galactosyl-(1->3)-1D-myo-inositol 342.299 C12 H22 O11 OC1(C(C(C(C(C1O)OC2(OC(C(C(C2O)O)O)CO))O)O)O) PUBCHEM:25202439:*LIGAND-CPD:C01235: 2.4.1.82 galactinol + sucrose = myo-inositol + raffinose stachyose biosynthesis galactinol 1-O-α-D-galactosyl-D-myo-inositol*1-α-D-galactosyl-myo-inositol*α-D-galactosyl-(1->3)-1D-myo-inositol 342.299 C12 H22 O11 OC1(C(C(C(C(C1O)OC2(OC(C(C(C2O)O)O)CO))O)O)O) PUBCHEM:25202439:*LIGAND-CPD:C01235: 2.4.1.123 myo-inositol + UDP-D-galactose = H+ + galactinol + UDP stachyose biosynthesis L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 3.5.3.1 H2O + L-arginine = urea + L-ornithine urea cycle L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 3.5.3.1 H2O + L-arginine = urea + L-ornithine arginine degradation VI (arginase 2 pathway) L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 3.5.3.1 H2O + L-arginine = urea + L-ornithine putrescine biosynthesis IV L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 3.5.3.1 H2O + L-arginine = urea + L-ornithine arginine degradation I (arginase pathway) L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 3.5.3.1 H2O + L-arginine = urea + L-ornithine citrulline biosynthesis L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 2.3.1.35 L-glutamate + N-acetyl-L-ornithine = N-acetyl-L-glutamate + L-ornithine arginine biosynthesis II (acetyl cycle) L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde arginine degradation VI (arginase 2 pathway) L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde arginine degradation I (arginase pathway) L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde proline biosynthesis II (from arginine) L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde citrulline biosynthesis L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 3.5.1.20 H+ + L-citrulline + H2O = L-ornithine + CO2 + ammonia proline biosynthesis II (from arginine) L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline urea cycle L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline arginine biosynthesis II (acetyl cycle) L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline proline biosynthesis II (from arginine) L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline citrulline degradation L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline arginine biosynthesis I L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline citrulline biosynthesis L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 4.1.1.17 H+ + L-ornithine = CO2 + putrescine putrescine biosynthesis IV L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 133.17 C5 H13 N2 O2 [N+]CCCC([N+])C(=O)[O-] PUBCHEM:6992088:*LIGAND-CPD:C00077:*CHEBI:46911:*PUBCHEM:6992088:*CHEBI:46911:*CAS:7006-33-9*LIGAND-CPD:C01602:*CAS:70-26-8 3.5.1.16 N-acetyl-L-ornithine + H2O = L-ornithine + acetate ornithine biosynthesis ent-kaurenol ent-kaur-16-en-19-ol 288.472 C20 H32 O1 C=C3(CC24(CCC1(C(C)(CO)CCCC(C)1C(CCC(C2)3)4))) CHEBI:475923:*PUBCHEM:463724:*LIGAND-CPD:C11872: 1.14.13.78 ent-kaurenol + NADPH + H+ + oxygen = ent-kaurenal + NADP+ + H2O GA12 biosynthesis ent-kaurenol ent-kaur-16-en-19-ol 288.472 C20 H32 O1 C=C3(CC24(CCC1(C(C)(CO)CCCC(C)1C(CCC(C2)3)4))) CHEBI:475923:*PUBCHEM:463724:*LIGAND-CPD:C11872: 1.14.13.78 H+ + ent-kaurene + oxygen + NADPH = H2O + NADP+ + ent-kaurenol GA12 biosynthesis 3-ureidopropionate β-ureidopropionic acid*3-ureidopropanoate*N-carbamoyl-β-alanine*3-Ureidopropanoate*β-Ureidopropionic acid*N-Carbamoyl-β-alanine 131.111 C4 H7 N2 O3 C(NC(=O)N)CC([O-])=O PUBCHEM:6971254:*CHEBI:11892:*LIGAND-CPD:C02642: 3.5.1.6 3-ureidopropionate + H2O + H+ = β-alanine + ammonia + CO2 uracil degradation II (reductive) 3-ureidopropionate β-ureidopropionic acid*3-ureidopropanoate*N-carbamoyl-β-alanine*3-Ureidopropanoate*β-Ureidopropionic acid*N-Carbamoyl-β-alanine 131.111 C4 H7 N2 O3 C(NC(=O)N)CC([O-])=O PUBCHEM:6971254:*CHEBI:11892:*LIGAND-CPD:C02642: 3.5.2.2 H2O + 5,6-dihydrouracil = H+ + 3-ureidopropionate uracil degradation II (reductive) chlorophyll a chlorophyll a 893.503 C55 H72 N4 O5 MG1 C24(C=C9(C(C)C(CCC(=O)OCC=C(C)CCCC(C)CCCC(C)CCCC(C)C)C5(=N([Mg]36(N1(=C(C(CC)=C(C)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) KNAPSACK:C00001528:*CHEBI:18230:*CAS:479-61-8:*LIGAND-CPD:C05306:*PUBCHEM:25245296: 3.1.1.14 chlorophyll a + H2O = H+ + chlorophyllide a + phytol chlorophyll a degradation chlorophyll a chlorophyll a 893.503 C55 H72 N4 O5 MG1 C24(C=C9(C(C)C(CCC(=O)OCC=C(C)CCCC(C)CCCC(C)CCCC(C)C)C5(=N([Mg]36(N1(=C(C(CC)=C(C)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) KNAPSACK:C00001528:*CHEBI:18230:*CAS:479-61-8:*LIGAND-CPD:C05306:*PUBCHEM:25245296: 1.3.1.- H+ + tetrahydrogeranylgeranyl-chlorophyll a + NADPH = chlorophyll a + NADP+ chlorophyll a biosynthesis II chlorophyll a chlorophyll a 893.503 C55 H72 N4 O5 MG1 C24(C=C9(C(C)C(CCC(=O)OCC=C(C)CCCC(C)CCCC(C)CCCC(C)C)C5(=N([Mg]36(N1(=C(C(CC)=C(C)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) KNAPSACK:C00001528:*CHEBI:18230:*CAS:479-61-8:*LIGAND-CPD:C05306:*PUBCHEM:25245296: 7-hydroxy-chlorophyll a + H2O + NADP+ = H+ + chlorophyll a + oxygen + NADPH chlorophyll cycle chlorophyll a chlorophyll a 893.503 C55 H72 N4 O5 MG1 C24(C=C9(C(C)C(CCC(=O)OCC=C(C)CCCC(C)CCCC(C)CCCC(C)C)C5(=N([Mg]36(N1(=C(C(CC)=C(C)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) KNAPSACK:C00001528:*CHEBI:18230:*CAS:479-61-8:*LIGAND-CPD:C05306:*PUBCHEM:25245296: 2.5.1.62 H+ + chlorophyllide a + phytyl diphosphate = chlorophyll a + diphosphate chlorophyll cycle chlorophyll a chlorophyll a 893.503 C55 H72 N4 O5 MG1 C24(C=C9(C(C)C(CCC(=O)OCC=C(C)CCCC(C)CCCC(C)CCCC(C)C)C5(=N([Mg]36(N1(=C(C(CC)=C(C)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) KNAPSACK:C00001528:*CHEBI:18230:*CAS:479-61-8:*LIGAND-CPD:C05306:*PUBCHEM:25245296: 2.5.1.62 H+ + chlorophyllide a + phytyl diphosphate = chlorophyll a + diphosphate chlorophyll a biosynthesis I pinostrobin (S)-2,3-Dihydro-5-hydroxy-7-methoxy-2-phenyl-4-benzopyrone 270.284 C16 H14 O4 C1(C(=CC(=C2(C=1OC(CC2=O)C3(C=CC=CC=3)))O)OC) PUBCHEM:6950539:*LIGAND-CPD:C16419: (2S)-pinocembrin + S-adenosyl-L-methionine = pinostrobin + S-adenosyl-L-homocysteine pinobanksin biosynthesis L,L-diaminopimelate L,L-A2pm*L,L-DAP*L,L-2,6-diaminopimelate*L,L-2,6-diaminoheptanedioate 190.199 C7 H14 N2 O4 C(C(C([O-])=O)[N+])CCC(C([O-])=O)[N+] PUBCHEM:1549100:*CAS:583-93-7:*LIGAND-CPD:C00666:*CAS:14289-34-0 5.1.1.7 L,L-diaminopimelate = meso-diaminopimelate lysine biosynthesis VI L,L-diaminopimelate L,L-A2pm*L,L-DAP*L,L-2,6-diaminopimelate*L,L-2,6-diaminoheptanedioate 190.199 C7 H14 N2 O4 C(C(C([O-])=O)[N+])CCC(C([O-])=O)[N+] PUBCHEM:1549100:*CAS:583-93-7:*LIGAND-CPD:C00666:*CAS:14289-34-0 2.6.1.83 L,L-diaminopimelate + 2-oxoglutarate = tetrahydrodipicolinate + L-glutamate + H2O + H+ lysine biosynthesis VI (S)-lactate lactic acid*L(+)-lactate*(S)-lactate*L-lactate*lactasol*lac*2-hydroxypropanoic acid*2-hydroxypropionic acid 89.071 C3 H5 O3 O=C(C(O)C)[O-] CAS:598-82-3:*CAS:50-21-5:*PUBCHEM:5460161:*CHEBI:16651:*CAS:79-33-4:*LIGAND-CPD:C00186: 1.1.1.27 (S)-lactate + NAD+ = pyruvate + NADH + H+ pyruvate fermentation to lactate 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate 13(S)-hydroperoxylinolenic acid*hydroperoxylinolenic acid*13S-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid*13-HPOT*(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate*13(S)-hydroperoxylinolenate 309.425 C18 H29 O4 C(CCCCCCC([O-])=O)C=CC=CC(CC=CCC)OO PUBCHEM:25244639: 1.13.11.12 oxygen + α-linolenate = 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate traumatin and (Z)-3-hexen-1-yl acetate biosynthesis 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate 13(S)-hydroperoxylinolenic acid*hydroperoxylinolenic acid*13S-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid*13-HPOT*(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate*13(S)-hydroperoxylinolenate 309.425 C18 H29 O4 C(CCCCCCC([O-])=O)C=CC=CC(CC=CCC)OO PUBCHEM:25244639: 1.13.11.12 oxygen + α-linolenate = 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate jasmonic acid biosynthesis 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate 13(S)-hydroperoxylinolenic acid*hydroperoxylinolenic acid*13S-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid*13-HPOT*(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate*13(S)-hydroperoxylinolenate 309.425 C18 H29 O4 C(CCCCCCC([O-])=O)C=CC=CC(CC=CCC)OO PUBCHEM:25244639: 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate = 12-oxo-cis-9-dodecenoate + cis-3-hexenal traumatin and (Z)-3-hexen-1-yl acetate biosynthesis 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate 13(S)-hydroperoxylinolenic acid*hydroperoxylinolenic acid*13S-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid*13-HPOT*(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate*13(S)-hydroperoxylinolenate 309.425 C18 H29 O4 C(CCCCCCC([O-])=O)C=CC=CC(CC=CCC)OO PUBCHEM:25244639: 4.2.1.92 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate = H2O + 12,13(S)-epoxylinolenate jasmonic acid biosynthesis 3-aminopropanal 3-aminopropionaldehyde*3-aminopropanal*3-amino-propanal*3-APA 74.102 C3 H8 N1 O1 C([N+])CC=O PUBCHEM:21286229:*LIGAND-CPD:C02229: 1.2.1.3 3-aminopropanal + H2O = β-alanine β-alanine biosynthesis I 3-aminopropanal 3-aminopropionaldehyde*3-aminopropanal*3-amino-propanal*3-APA 74.102 C3 H8 N1 O1 C([N+])CC=O PUBCHEM:21286229:*LIGAND-CPD:C02229: 1.4.3.22 propane-1,3-diamine + H2O + oxygen = H+ + 3-aminopropanal + ammonia + hydrogen peroxide β-alanine biosynthesis I CDP-N-dimethylethanolamine 473.292 C13 H23 N4 O11 P2 C[N+](C)CCOP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(N)=NC(=O)2)) PUBCHEM:25244049: 2.7.8.- CDP-N-dimethylethanolamine = CMP phosphatidylcholine biosynthesis IV CDP-N-dimethylethanolamine 473.292 C13 H23 N4 O11 P2 C[N+](C)CCOP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(N)=NC(=O)2)) PUBCHEM:25244049: 2.7.7.- H+ + N-dimethylethanolamine phosphate + CTP = CDP-N-dimethylethanolamine + diphosphate phosphatidylcholine biosynthesis IV ethylene ethylene*olefiant gas*elayl*ethene 28.054 C2 H4 C=C PUBCHEM:6325:*CHEBI:18153:*LIGAND-CPD:C06547: 1.14.17.4 H+ + L-ascorbate + 1-aminocyclopropane-1-carboxylate + oxygen = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine 5-phospho-α-D-ribose 1-diphosphate 5-phosphoribosyl 1-pyrophosphate*5-phosphoribosyl diphosphate*5-phospho-α-D-ribose 1-diphosphate*PRPP*5-phosphoribosyl-1-PP*5-phosphoribosyl-PP*5-phosphoribosyl-1-pyrophosphate*5-phosphoribosylpyrophosphate*phosphoribosylpyrophosphate*5-phospho-ribosyl-pyrophosphate*α-D-5-phosphoribosylPP*α-D-5-P-RibosylPP*5-phospho-α-D-ribose-1-diphosphate 385.031 C5 H8 O14 P3 O=P([O-])([O-])OCC1(OC(OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:20848918:*LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.8 GMP + diphosphate = guanine + 5-phospho-α-D-ribose 1-diphosphate guanine and guanosine salvage II 5-phospho-α-D-ribose 1-diphosphate 5-phosphoribosyl 1-pyrophosphate*5-phosphoribosyl diphosphate*5-phospho-α-D-ribose 1-diphosphate*PRPP*5-phosphoribosyl-1-PP*5-phosphoribosyl-PP*5-phosphoribosyl-1-pyrophosphate*5-phosphoribosylpyrophosphate*phosphoribosylpyrophosphate*5-phospho-ribosyl-pyrophosphate*α-D-5-phosphoribosylPP*α-D-5-P-RibosylPP*5-phospho-α-D-ribose-1-diphosphate 385.031 C5 H8 O14 P3 O=P([O-])([O-])OCC1(OC(OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:20848918:*LIGAND-CPD:C00119:*CAS:13270-65-0 2.7.6.1 ATP + D-ribose-5-phosphate = H+ + 5-phospho-α-D-ribose 1-diphosphate + AMP PRPP biosynthesis I 5-phospho-α-D-ribose 1-diphosphate 5-phosphoribosyl 1-pyrophosphate*5-phosphoribosyl diphosphate*5-phospho-α-D-ribose 1-diphosphate*PRPP*5-phosphoribosyl-1-PP*5-phosphoribosyl-PP*5-phosphoribosyl-1-pyrophosphate*5-phosphoribosylpyrophosphate*phosphoribosylpyrophosphate*5-phospho-ribosyl-pyrophosphate*α-D-5-phosphoribosylPP*α-D-5-P-RibosylPP*5-phospho-α-D-ribose-1-diphosphate 385.031 C5 H8 O14 P3 O=P([O-])([O-])OCC1(OC(OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:20848918:*LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O 5-aminoimidazole ribonucleotide biosynthesis II 5-phospho-α-D-ribose 1-diphosphate 5-phosphoribosyl 1-pyrophosphate*5-phosphoribosyl diphosphate*5-phospho-α-D-ribose 1-diphosphate*PRPP*5-phosphoribosyl-1-PP*5-phosphoribosyl-PP*5-phosphoribosyl-1-pyrophosphate*5-phosphoribosylpyrophosphate*phosphoribosylpyrophosphate*5-phospho-ribosyl-pyrophosphate*α-D-5-phosphoribosylPP*α-D-5-P-RibosylPP*5-phospho-α-D-ribose-1-diphosphate 385.031 C5 H8 O14 P3 O=P([O-])([O-])OCC1(OC(OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:20848918:*LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O 5-aminoimidazole ribonucleotide biosynthesis I 5-phospho-α-D-ribose 1-diphosphate 5-phosphoribosyl 1-pyrophosphate*5-phosphoribosyl diphosphate*5-phospho-α-D-ribose 1-diphosphate*PRPP*5-phosphoribosyl-1-PP*5-phosphoribosyl-PP*5-phosphoribosyl-1-pyrophosphate*5-phosphoribosylpyrophosphate*phosphoribosylpyrophosphate*5-phospho-ribosyl-pyrophosphate*α-D-5-phosphoribosylPP*α-D-5-P-RibosylPP*5-phospho-α-D-ribose-1-diphosphate 385.031 C5 H8 O14 P3 O=P([O-])([O-])OCC1(OC(OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:20848918:*LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O superpathway of 5-aminoimidazole ribonucleotide biosynthesis 5-phospho-α-D-ribose 1-diphosphate 5-phosphoribosyl 1-pyrophosphate*5-phosphoribosyl diphosphate*5-phospho-α-D-ribose 1-diphosphate*PRPP*5-phosphoribosyl-1-PP*5-phosphoribosyl-PP*5-phosphoribosyl-1-pyrophosphate*5-phosphoribosylpyrophosphate*phosphoribosylpyrophosphate*5-phospho-ribosyl-pyrophosphate*α-D-5-phosphoribosylPP*α-D-5-P-RibosylPP*5-phospho-α-D-ribose-1-diphosphate 385.031 C5 H8 O14 P3 O=P([O-])([O-])OCC1(OC(OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:20848918:*LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.9 diphosphate + uridine-5'-phosphate = 5-phospho-α-D-ribose 1-diphosphate + uracil salvage pathways of pyrimidine ribonucleotides 5-phospho-α-D-ribose 1-diphosphate 5-phosphoribosyl 1-pyrophosphate*5-phosphoribosyl diphosphate*5-phospho-α-D-ribose 1-diphosphate*PRPP*5-phosphoribosyl-1-PP*5-phosphoribosyl-PP*5-phosphoribosyl-1-pyrophosphate*5-phosphoribosylpyrophosphate*phosphoribosylpyrophosphate*5-phospho-ribosyl-pyrophosphate*α-D-5-phosphoribosylPP*α-D-5-P-RibosylPP*5-phospho-α-D-ribose-1-diphosphate 385.031 C5 H8 O14 P3 O=P([O-])([O-])OCC1(OC(OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:20848918:*LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.18 N-(5'-phosphoribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-α-D-ribose 1-diphosphate tryptophan biosynthesis 5-phospho-α-D-ribose 1-diphosphate 5-phosphoribosyl 1-pyrophosphate*5-phosphoribosyl diphosphate*5-phospho-α-D-ribose 1-diphosphate*PRPP*5-phosphoribosyl-1-PP*5-phosphoribosyl-PP*5-phosphoribosyl-1-pyrophosphate*5-phosphoribosylpyrophosphate*phosphoribosylpyrophosphate*5-phospho-ribosyl-pyrophosphate*α-D-5-phosphoribosylPP*α-D-5-P-RibosylPP*5-phospho-α-D-ribose-1-diphosphate 385.031 C5 H8 O14 P3 O=P([O-])([O-])OCC1(OC(OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:20848918:*LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.11 nicotinate mononucleotide + diphosphate = H+ + nicotinate + 5-phospho-α-D-ribose 1-diphosphate pyridine nucleotide cycling (plants) 5-phospho-α-D-ribose 1-diphosphate 5-phosphoribosyl 1-pyrophosphate*5-phosphoribosyl diphosphate*5-phospho-α-D-ribose 1-diphosphate*PRPP*5-phosphoribosyl-1-PP*5-phosphoribosyl-PP*5-phosphoribosyl-1-pyrophosphate*5-phosphoribosylpyrophosphate*phosphoribosylpyrophosphate*5-phospho-ribosyl-pyrophosphate*α-D-5-phosphoribosylPP*α-D-5-P-RibosylPP*5-phospho-α-D-ribose-1-diphosphate 385.031 C5 H8 O14 P3 O=P([O-])([O-])OCC1(OC(OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:20848918:*LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.10 orotidine-5'-phosphate + diphosphate = 5-phospho-α-D-ribose 1-diphosphate + orotate uridine-5'-phosphate biosynthesis 5-phospho-α-D-ribose 1-diphosphate 5-phosphoribosyl 1-pyrophosphate*5-phosphoribosyl diphosphate*5-phospho-α-D-ribose 1-diphosphate*PRPP*5-phosphoribosyl-1-PP*5-phosphoribosyl-PP*5-phosphoribosyl-1-pyrophosphate*5-phosphoribosylpyrophosphate*phosphoribosylpyrophosphate*5-phospho-ribosyl-pyrophosphate*α-D-5-phosphoribosylPP*α-D-5-P-RibosylPP*5-phospho-α-D-ribose-1-diphosphate 385.031 C5 H8 O14 P3 O=P([O-])([O-])OCC1(OC(OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:20848918:*LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.17 phosphoribosyl-ATP + diphosphate = ATP + 5-phospho-α-D-ribose 1-diphosphate histidine biosynthesis 5-phospho-α-D-ribose 1-diphosphate 5-phosphoribosyl 1-pyrophosphate*5-phosphoribosyl diphosphate*5-phospho-α-D-ribose 1-diphosphate*PRPP*5-phosphoribosyl-1-PP*5-phosphoribosyl-PP*5-phosphoribosyl-1-pyrophosphate*5-phosphoribosylpyrophosphate*phosphoribosylpyrophosphate*5-phospho-ribosyl-pyrophosphate*α-D-5-phosphoribosylPP*α-D-5-P-RibosylPP*5-phospho-α-D-ribose-1-diphosphate 385.031 C5 H8 O14 P3 O=P([O-])([O-])OCC1(OC(OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:20848918:*LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.19 H+ + 5-phospho-α-D-ribose 1-diphosphate + quinolinate = CO2 + diphosphate + nicotinate mononucleotide NAD biosynthesis I (from aspartate) 5-phospho-α-D-ribose 1-diphosphate 5-phosphoribosyl 1-pyrophosphate*5-phosphoribosyl diphosphate*5-phospho-α-D-ribose 1-diphosphate*PRPP*5-phosphoribosyl-1-PP*5-phosphoribosyl-PP*5-phosphoribosyl-1-pyrophosphate*5-phosphoribosylpyrophosphate*phosphoribosylpyrophosphate*5-phospho-ribosyl-pyrophosphate*α-D-5-phosphoribosylPP*α-D-5-P-RibosylPP*5-phospho-α-D-ribose-1-diphosphate 385.031 C5 H8 O14 P3 O=P([O-])([O-])OCC1(OC(OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:20848918:*LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.7 AMP + diphosphate = adenine + 5-phospho-α-D-ribose 1-diphosphate adenine and adenosine salvage II (-)-(4S)-limonene L-limonene*(-)-limonene*(-)-(4S)-limonene*(-)-(S)-limonene 136.236 C10 H16 C1(CCC(CC=1)C(C)=C)C PUBCHEM:439250:*CHEBI:15383:*LIGAND-CPD:C00521: 4.2.3.16 geranyl diphosphate = (-)-(4S)-limonene + diphosphate monoterpene biosynthesis geranylfarnesyl diphosphate all-trans-pentaprenyl diphosphate*geranylfarnesyl-PP*GFPP*geranylfarnesyl-diphosphate*all-trans-pentaprenyl diphosphate*2,6,10,14-trans-pentaprenyl diphosphate*(2E,6E,10E,14E)-geranylfarnesyl diphosphate 515.542 C25 H41 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:57907:*PUBCHEM:25244051:*LIGAND-CPD:C04217: 2.5.1.83 geranylfarnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-hexaprenyl diphosphate + diphosphate hexaprenyl diphosphate biosynthesis geranylfarnesyl diphosphate all-trans-pentaprenyl diphosphate*geranylfarnesyl-PP*GFPP*geranylfarnesyl-diphosphate*all-trans-pentaprenyl diphosphate*2,6,10,14-trans-pentaprenyl diphosphate*(2E,6E,10E,14E)-geranylfarnesyl diphosphate 515.542 C25 H41 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:57907:*PUBCHEM:25244051:*LIGAND-CPD:C04217: 2.5.1.83 geranylfarnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-hexaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III geranylfarnesyl diphosphate all-trans-pentaprenyl diphosphate*geranylfarnesyl-PP*GFPP*geranylfarnesyl-diphosphate*all-trans-pentaprenyl diphosphate*2,6,10,14-trans-pentaprenyl diphosphate*(2E,6E,10E,14E)-geranylfarnesyl diphosphate 515.542 C25 H41 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:57907:*PUBCHEM:25244051:*LIGAND-CPD:C04217: 2.5.1.81 isopentenyl diphosphate + all-trans-geranyl-geranyl diphosphate = H+ + geranylfarnesyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III maltose β-maltose 342.299 C12 H22 O11 C1(OC(C(C(C1O)O)O)OC2(C(OC(C(C2O)O)O)CO))CO LIGAND-CPD:C01971:*CHEBI:18147:*PUBCHEM:6255:*CAS:69-79-4 2.4.1.25 maltotriose + maltose = maltotetraose + β-D-glucose glycogen degradation I maltose β-maltose 342.299 C12 H22 O11 C1(OC(C(C(C1O)O)O)OC2(C(OC(C(C2O)O)O)CO))CO LIGAND-CPD:C01971:*CHEBI:18147:*PUBCHEM:6255:*CAS:69-79-4 3.2.1.20 maltotriose + H2O = maltose + α-D-glucose glycogen degradation I naringenin chalcone 2'44'6-tetrahydroxychalcone*2'44'6'-tetrahydroxychalcone 272.257 C15 H12 O5 C2(C(O)=C(C(C=CC1(C=CC(=CC=1)O))=O)C(=CC=2O)O) CAS:520-36-5*CHEBI:15413:*PUBCHEM:5280960:*CHEBI:15413:*CAS:73692-50-9:*PUBCHEM:5280960:*LIGAND-CPD:C06561: 2.3.1.74 H+ + 4-coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A flavonoid biosynthesis naringenin chalcone 2'44'6-tetrahydroxychalcone*2'44'6'-tetrahydroxychalcone 272.257 C15 H12 O5 C2(C(O)=C(C(C=CC1(C=CC(=CC=1)O))=O)C(=CC=2O)O) CAS:520-36-5*CHEBI:15413:*PUBCHEM:5280960:*CHEBI:15413:*CAS:73692-50-9:*PUBCHEM:5280960:*LIGAND-CPD:C06561: 2.3.1.74 H+ + 4-coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A aromatic polyketides biosynthesis naringenin chalcone 2'44'6-tetrahydroxychalcone*2'44'6'-tetrahydroxychalcone 272.257 C15 H12 O5 C2(C(O)=C(C(C=CC1(C=CC(=CC=1)O))=O)C(=CC=2O)O) CAS:520-36-5*CHEBI:15413:*PUBCHEM:5280960:*CHEBI:15413:*CAS:73692-50-9:*PUBCHEM:5280960:*LIGAND-CPD:C06561: 5.5.1.6 naringenin chalcone = H+ + naringenin flavonoid biosynthesis stigmasterol 412.698 C29 H48 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(C=CC(C(C)C)CC)C)C(CC3)(C)4)))C))O) PUBCHEM:25245939:*LIGAND-CPD:C05442: 1.3.1.- sitosterol + NADPH + H+ + oxygen = stigmasterol + NADP+ + H2O plant sterol biosynthesis 3,7,4'-tri-O-methylquercetin 35-dihydroxy-347-trimethoxyflavone*3,7,4'-trimethylquercetin 344.32 C18 H16 O7 COC3(C(=O)C1(C(=CC(OC)=CC(O)=1)OC(C2(C=C(O)C(OC)=CC=2))=3)) CHEBI:27825:*PUBCHEM:5280682:*LIGAND-CPD:C04444: 2.1.1.83 3,7-di-O-methylquercetin + S-adenosyl-L-methionine = H+ + 3,7,4'-tri-O-methylquercetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis 3-dehydroshikimate 3-dehydroshikimic acid*5-dehydroshikimic acid*5-dehydroshikimate 171.129 C7 H7 O5 C1(C(O)C(O)C(=O)C=C(C([O-])=O)1) CAS:2922-42-1*CAS:10457-99-5:*CHEBI:16630:*PUBCHEM:5460360:*LIGAND-CPD:C02637: 1.1.1.25 shikimate + NADP+ = H+ + 3-dehydroshikimate + NADPH chorismate biosynthesis I 3-dehydroshikimate 3-dehydroshikimic acid*5-dehydroshikimic acid*5-dehydroshikimate 171.129 C7 H7 O5 C1(C(O)C(O)C(=O)C=C(C([O-])=O)1) CAS:2922-42-1*CAS:10457-99-5:*CHEBI:16630:*PUBCHEM:5460360:*LIGAND-CPD:C02637: 4.2.1.10 3-dehydroquinate = H2O + 3-dehydroshikimate chorismate biosynthesis I 3-dehydroshikimate 3-dehydroshikimic acid*5-dehydroshikimic acid*5-dehydroshikimate 171.129 C7 H7 O5 C1(C(O)C(O)C(=O)C=C(C([O-])=O)1) CAS:2922-42-1*CAS:10457-99-5:*CHEBI:16630:*PUBCHEM:5460360:*LIGAND-CPD:C02637: 1.1.1.282 shikimate = 3-dehydroshikimate + H+ chorismate biosynthesis I phosphoryl-ethanolamine O-Phosphoethanolamine*O-Phosphorylethanolamine*phosphoethanolamine*ethanolamine phosphate*O-phosphorylethanolamine*O-phosphoethanolamine 140.055 C2 H7 N1 O4 P1 [N+]CCOP([O-])([O-])=O PUBCHEM:7059434:*LIGAND-CPD:C00346:*CAS:1071-23-4 2.7.1.82 ethanolamine + ATP = H+ + phosphoryl-ethanolamine + ADP phosphatidylethanolamine biosynthesis II phosphoryl-ethanolamine O-Phosphoethanolamine*O-Phosphorylethanolamine*phosphoethanolamine*ethanolamine phosphate*O-phosphorylethanolamine*O-phosphoethanolamine 140.055 C2 H7 N1 O4 P1 [N+]CCOP([O-])([O-])=O PUBCHEM:7059434:*LIGAND-CPD:C00346:*CAS:1071-23-4 2.7.1.82 ethanolamine + ATP = H+ + phosphoryl-ethanolamine + ADP choline biosynthesis I phosphoryl-ethanolamine O-Phosphoethanolamine*O-Phosphorylethanolamine*phosphoethanolamine*ethanolamine phosphate*O-phosphorylethanolamine*O-phosphoethanolamine 140.055 C2 H7 N1 O4 P1 [N+]CCOP([O-])([O-])=O PUBCHEM:7059434:*LIGAND-CPD:C00346:*CAS:1071-23-4 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate phosphatidylcholine biosynthesis IV phosphoryl-ethanolamine O-Phosphoethanolamine*O-Phosphorylethanolamine*phosphoethanolamine*ethanolamine phosphate*O-phosphorylethanolamine*O-phosphoethanolamine 140.055 C2 H7 N1 O4 P1 [N+]CCOP([O-])([O-])=O PUBCHEM:7059434:*LIGAND-CPD:C00346:*CAS:1071-23-4 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate choline biosynthesis I phosphoryl-ethanolamine O-Phosphoethanolamine*O-Phosphorylethanolamine*phosphoethanolamine*ethanolamine phosphate*O-phosphorylethanolamine*O-phosphoethanolamine 140.055 C2 H7 N1 O4 P1 [N+]CCOP([O-])([O-])=O PUBCHEM:7059434:*LIGAND-CPD:C00346:*CAS:1071-23-4 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate phosphatidylcholine biosynthesis III phosphoryl-ethanolamine O-Phosphoethanolamine*O-Phosphorylethanolamine*phosphoethanolamine*ethanolamine phosphate*O-phosphorylethanolamine*O-phosphoethanolamine 140.055 C2 H7 N1 O4 P1 [N+]CCOP([O-])([O-])=O PUBCHEM:7059434:*LIGAND-CPD:C00346:*CAS:1071-23-4 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate phosphatidylcholine biosynthesis II phosphoryl-ethanolamine O-Phosphoethanolamine*O-Phosphorylethanolamine*phosphoethanolamine*ethanolamine phosphate*O-phosphorylethanolamine*O-phosphoethanolamine 140.055 C2 H7 N1 O4 P1 [N+]CCOP([O-])([O-])=O PUBCHEM:7059434:*LIGAND-CPD:C00346:*CAS:1071-23-4 2.7.7.14 H+ + phosphoryl-ethanolamine + CTP = CDP-ethanolamine + diphosphate phosphatidylethanolamine biosynthesis II allantoate 175.124 C4 H7 N4 O4 O=C(NC(C(=O)[O-])NC(=O)N)N CHEBI:17536:*PUBCHEM:5287444:*LIGAND-CPD:C00499:*CAS:99-16-1 3.5.3.9 H+ + allantoate + H2O = S-ureidoglycine + ammonia + CO2 allantoin degradation to ureidoglycolate II (ammonia producing) allantoate 175.124 C4 H7 N4 O4 O=C(NC(C(=O)[O-])NC(=O)N)N CHEBI:17536:*PUBCHEM:5287444:*LIGAND-CPD:C00499:*CAS:99-16-1 3.5.3.4 H2O + allantoate = S-(-)-ureidoglycolate + urea allantoin degradation to ureidoglycolate I (urea producing) allantoate 175.124 C4 H7 N4 O4 O=C(NC(C(=O)[O-])NC(=O)N)N CHEBI:17536:*PUBCHEM:5287444:*LIGAND-CPD:C00499:*CAS:99-16-1 3.5.2.5 S-allantoin + H2O = H+ + allantoate allantoin degradation to ureidoglycolate I (urea producing) allantoate 175.124 C4 H7 N4 O4 O=C(NC(C(=O)[O-])NC(=O)N)N CHEBI:17536:*PUBCHEM:5287444:*LIGAND-CPD:C00499:*CAS:99-16-1 3.5.2.5 S-allantoin + H2O = H+ + allantoate allantoin degradation to ureidoglycolate II (ammonia producing) (-)-β-pinene (-)-(1S,5S)-β-pinene 136.236 C10 H16 C1(CCC2(CC1C2(C)C))=C PUBCHEM:440967:*CHEBI:28359:*LIGAND-CPD:C06307: 4.2.3.14 geranyl diphosphate = (-)-β-pinene + diphosphate monoterpene biosynthesis coniferaldehyde coniferyl aldehyde*4-hydroxy-3-methoxycinnamaldehyde*4-hydroxy-3-methoxycinnamic aldehyde*coniferaldehyde 178.187 C10 H10 O3 C(=CC=O)C1(C=CC(=C(C=1)OC)O) CHEBI:16547:*PUBCHEM:5280536:*LIGAND-CPD:C02666:*CAS:458-36-6 1.2.1.68 coniferaldehyde + H2O = ferulate + H+ ferulate and sinapate biosynthesis coniferaldehyde coniferyl aldehyde*4-hydroxy-3-methoxycinnamaldehyde*4-hydroxy-3-methoxycinnamic aldehyde*coniferaldehyde 178.187 C10 H10 O3 C(=CC=O)C1(C=CC(=C(C=1)OC)O) CHEBI:16547:*PUBCHEM:5280536:*LIGAND-CPD:C02666:*CAS:458-36-6 1.14.13.- H+ + coniferaldehyde + NADPH + oxygen = 5-hydroxy-coniferaldehyde + NADP+ + H2O phenylpropanoid biosynthesis coniferaldehyde coniferyl aldehyde*4-hydroxy-3-methoxycinnamaldehyde*4-hydroxy-3-methoxycinnamic aldehyde*coniferaldehyde 178.187 C10 H10 O3 C(=CC=O)C1(C=CC(=C(C=1)OC)O) CHEBI:16547:*PUBCHEM:5280536:*LIGAND-CPD:C02666:*CAS:458-36-6 1.14.13.- H+ + coniferaldehyde + NADPH + oxygen = 5-hydroxy-coniferaldehyde + NADP+ + H2O ferulate and sinapate biosynthesis coniferaldehyde coniferyl aldehyde*4-hydroxy-3-methoxycinnamaldehyde*4-hydroxy-3-methoxycinnamic aldehyde*coniferaldehyde 178.187 C10 H10 O3 C(=CC=O)C1(C=CC(=C(C=1)OC)O) CHEBI:16547:*PUBCHEM:5280536:*LIGAND-CPD:C02666:*CAS:458-36-6 1.1.1.195 coniferyl alcohol + NADP+ = coniferaldehyde + NADPH + H+ phenylpropanoid biosynthesis coniferaldehyde coniferyl aldehyde*4-hydroxy-3-methoxycinnamaldehyde*4-hydroxy-3-methoxycinnamic aldehyde*coniferaldehyde 178.187 C10 H10 O3 C(=CC=O)C1(C=CC(=C(C=1)OC)O) CHEBI:16547:*PUBCHEM:5280536:*LIGAND-CPD:C02666:*CAS:458-36-6 1.2.1.44 H+ + feruloyl-CoA + NADPH = coniferaldehyde + NADP+ + coenzyme A phenylpropanoid biosynthesis coniferaldehyde coniferyl aldehyde*4-hydroxy-3-methoxycinnamaldehyde*4-hydroxy-3-methoxycinnamic aldehyde*coniferaldehyde 178.187 C10 H10 O3 C(=CC=O)C1(C=CC(=C(C=1)OC)O) CHEBI:16547:*PUBCHEM:5280536:*LIGAND-CPD:C02666:*CAS:458-36-6 2.4.1.- coniferaldehyde = H+ + coniferaldehyde glucoside + UDP monolignol glucosides biosynthesis cytosine 4-amino-2-oxo-1,2-dihydropyrimidine 111.103 C4 H5 N3 O1 O=C1(N=C(N)C=CN1) PUBCHEM:597:*CHEBI:16040:*LIGAND-CPD:C00380:*CAS:71-30-7 3.5.4.1 H2O + cytosine = ammonia + uracil salvage pathways of pyrimidine ribonucleotides dihydrozeatin 2-Methyl-4-(1H-purin-6-ylamino)butan-1-ol*N6-(4-Hydroxyisopentanyl)adenine 221.261 C10 H15 N5 O1 CC(CO)CCNC2(=NC=NC1(=C(N=CN1)2)) PUBCHEM:439631:*LIGAND-CPD:C02029:*CAS:23599-75-9 2.4.1.- dihydrozeatin = H+ + dihydrozeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis syringetin 345.285 C17 H13 O8 COC1(=CC(=CC(OC)=C(O)1)C2(OC3(C=C(O)C=C(O)C(C(=O)C([O-])=2)=3))) PUBCHEM:25202456:*CHEBI:58412:*PUBCHEM:25202456:*LIGAND-CPD:C11620: 2.1.1.149 laricitrin + S-adenosyl-L-methionine = H+ + syringetin + S-adenosyl-L-homocysteine syringetin biosynthesis isoscopoletin 7-methoxyesculetin*7-methyl esculetin*6-hydroxy-7-methoxycoumarin 192.171 C10 H8 O4 COC2(=C(C=C1(C=CC(=O)OC1=C2))O) herniarin = isoscopoletin simplecoumarins biosynthesis isoscopoletin 7-methoxyesculetin*7-methyl esculetin*6-hydroxy-7-methoxycoumarin 192.171 C10 H8 O4 COC2(=C(C=C1(C=CC(=O)OC1=C2))O) esculetin = isoscopoletin simplecoumarins biosynthesis isoscopoletin 7-methoxyesculetin*7-methyl esculetin*6-hydroxy-7-methoxycoumarin 192.171 C10 H8 O4 COC2(=C(C=C1(C=CC(=O)OC1=C2))O) isoscopoletin = scoparone simplecoumarins biosynthesis isoscopoletin 7-methoxyesculetin*7-methyl esculetin*6-hydroxy-7-methoxycoumarin 192.171 C10 H8 O4 COC2(=C(C=C1(C=CC(=O)OC1=C2))O) isoscopoletin = ayapin simplecoumarins biosynthesis GA51-catabolite gibberellin A51-catabolite*gibberellin A51-catabolite*GA51-catabolite 328.364 C19 H20 O5 C1(C(CC(C2(C(C34(CC(CCC(C=12)3)C(C4)=C))C([O-])=O))(C)C([O-])=O)=O) PUBCHEM:25201559:*LIGAND-CPD:C11854: 1.14.11.- GA51 + 2-oxoglutarate + oxygen = H+ + GA51-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) GA98 gibberellin A98*gibberellin A98*GA98 363.43 C20 H27 O6 C1(C(CC(C2(C(C34(CC(CCC(C1(CO)2)3)(C(C4)=C)O))C([O-])=O))(C)C=O)O) PUBCHEM:25200670: 1.14.11.- H+ + GA44 + 2-oxoglutarate + oxygen = GA98 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) S-ureidoglycine 133.107 C3 H7 N3 O3 C(=O)(N)NC([N+])C([O-])=O CHEBI:59947:*PUBCHEM:46173475: 3.5.3.9 H+ + allantoate + H2O = S-ureidoglycine + ammonia + CO2 allantoin degradation to ureidoglycolate II (ammonia producing) S-ureidoglycine 133.107 C3 H7 N3 O3 C(=O)(N)NC([N+])C([O-])=O CHEBI:59947:*PUBCHEM:46173475: 3.5.3.- S-ureidoglycine + H2O = H+ + ammonia + S-(-)-ureidoglycolate allantoin degradation to ureidoglycolate II (ammonia producing) 5-amino-levulinate 5-Amino-4-oxopentanoate*5-amino-4-oxo-pentanoic acid*5-amino-levulinic acid*5-amino-4-oxopentanoic acid*γ-aminolevulinic acid*5-aminolevulinic acid*5-aminolevulinate*ALA*δ-aminolevulinic acid 131.131 C5 H9 N1 O3 [N+]CC(CCC([O-])=O)=O CAS:5451-09-2:*PUBCHEM:137:*CHEBI:356416:*PUBCHEM:7048523:*LIGAND-CPD:C00430:*CAS:106-60-5 4.2.1.24 5-amino-levulinate = H+ + H2O + porphobilinogen tetrapyrrole biosynthesis I 5-amino-levulinate 5-Amino-4-oxopentanoate*5-amino-4-oxo-pentanoic acid*5-amino-levulinic acid*5-amino-4-oxopentanoic acid*γ-aminolevulinic acid*5-aminolevulinic acid*5-aminolevulinate*ALA*δ-aminolevulinic acid 131.131 C5 H9 N1 O3 [N+]CC(CCC([O-])=O)=O CAS:5451-09-2:*PUBCHEM:137:*CHEBI:356416:*PUBCHEM:7048523:*LIGAND-CPD:C00430:*CAS:106-60-5 5.4.3.8 glutamate-1-semialdehyde = 5-amino-levulinate tetrapyrrole biosynthesis I cis-zeatin riboside monophosphate cZRMP 429.325 C15 H20 N5 O8 P1 C1(C(OC(C1O)N3(C2(N=CN=C(C=2N=C3)NCC=C(C)CO)))COP([O-])([O-])=O)O PUBCHEM:25244062:*LIGAND-CPD:C16441: cis-zeatin riboside monophosphate + H2O = cis-zeatin riboside cis-zeatin biosynthesis cis-zeatin riboside monophosphate cZRMP 429.325 C15 H20 N5 O8 P1 C1(C(OC(C1O)N3(C2(N=CN=C(C=2N=C3)NCC=C(C)CO)))COP([O-])([O-])=O)O PUBCHEM:25244062:*LIGAND-CPD:C16441: cis-zeatin biosynthesis precorrin-1 842.768 C41 H38 N4 O16 C3(C5(C(C(C(=CC4(=C(C(CCC([O-])=O)=C(CC1(=C(CCC([O-])=O)C(CC(=O)[O-])=C(N1)CC2(NC(=C(CC([O-])=O)C=2CCC([O-])=O)3)))N4)CC([O-])=O))N=5)(C)CC([O-])=O)CCC(=O)[O-])) PUBCHEM:11954200:*CHEBI:58893:*PUBCHEM:25245954:*LIGAND-CPD:C15527: 2.1.1.107 S-adenosyl-L-methionine + uroporphyrinogen-III = H+ + S-adenosyl-L-homocysteine + precorrin-1 siroheme biosynthesis precorrin-1 842.768 C41 H38 N4 O16 C3(C5(C(C(C(=CC4(=C(C(CCC([O-])=O)=C(CC1(=C(CCC([O-])=O)C(CC(=O)[O-])=C(N1)CC2(NC(=C(CC([O-])=O)C=2CCC([O-])=O)3)))N4)CC([O-])=O))N=5)(C)CC([O-])=O)CCC(=O)[O-])) PUBCHEM:11954200:*CHEBI:58893:*PUBCHEM:25245954:*LIGAND-CPD:C15527: 2.1.1.107 S-adenosyl-L-methionine + precorrin-1 = S-adenosyl-L-homocysteine + precorrin-2 siroheme biosynthesis histidinal L-histidinal 140.164 C6 H10 N3 O1 C1(=CNC=N1)CC(C=O)[N+] PUBCHEM:25244065:*LIGAND-CPD:C01929: 1.1.1.23 histidinol + NAD+ = H+ + histidinal + NADH histidine biosynthesis histidinal L-histidinal 140.164 C6 H10 N3 O1 C1(=CNC=N1)CC(C=O)[N+] PUBCHEM:25244065:*LIGAND-CPD:C01929: 1.1.1.23 histidinal + NAD+ + H2O = H+ + L-histidine + NADH histidine biosynthesis quercetin-3-glucoside quercetin-3-O-β-D-glucoside*isoquercetin*isoquercitrin*isotrifoliin*glucosyl 3-quercetin 463.374 C21 H19 O12 O=C2(C(OC1(OC(CO)C(O)C(O)C(O)1))=C(OC3(C=C([O-])C=C(O)C2=3))C4(=CC=C(O)C(O)=C4)) PUBCHEM:25203368:*LIGAND-CPD:C05623:*PUBCHEM:25203368:*PUBCHEM:5280804: 2.4.1.91 quercetin = UDP + quercetin-3-glucoside flavonol glucosylation I sinapaldehyde 208.213 C11 H12 O4 OC1(=C(C=C(C=CC=O)C=C(OC)1)OC) CHEBI:27949:*PUBCHEM:5280802:*LIGAND-CPD:C05610: 2.4.1.- sinapaldehyde = H+ + sinapaldehyde glucoside + UDP monolignol glucosides biosynthesis sinapaldehyde 208.213 C11 H12 O4 OC1(=C(C=C(C=CC=O)C=C(OC)1)OC) CHEBI:27949:*PUBCHEM:5280802:*LIGAND-CPD:C05610: 1.1.1.195 H+ + sinapaldehyde + NADPH = sinapyl-alcohol + NADP+ phenylpropanoid biosynthesis sinapaldehyde 208.213 C11 H12 O4 OC1(=C(C=C(C=CC=O)C=C(OC)1)OC) CHEBI:27949:*PUBCHEM:5280802:*LIGAND-CPD:C05610: 2.1.1.68 5-hydroxy-coniferaldehyde + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + sinapaldehyde phenylpropanoid biosynthesis sinapaldehyde 208.213 C11 H12 O4 OC1(=C(C=C(C=CC=O)C=C(OC)1)OC) CHEBI:27949:*PUBCHEM:5280802:*LIGAND-CPD:C05610: 2.1.1.68 5-hydroxy-coniferaldehyde + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + sinapaldehyde ferulate and sinapate biosynthesis sinapaldehyde 208.213 C11 H12 O4 OC1(=C(C=C(C=CC=O)C=C(OC)1)OC) CHEBI:27949:*PUBCHEM:5280802:*LIGAND-CPD:C05610: 1.2.1.68 sinapaldehyde + NADP+ + H2O = H+ + sinapate + NADPH ferulate and sinapate biosynthesis GA8-catabolite gibberellin A8-catabolite*gibberellin A8-catabolite*GA8-catabolite 360.363 C19 H20 O7 C1(C(C(C(C2(C(C34(CC(CCC(C=12)3)(C(C4)=C)O))C([O-])=O))(C)C([O-])=O)O)=O) PUBCHEM:25202462:*LIGAND-CPD:C11870: 1.14.11.- gibberellin A8 + 2-oxoglutarate + oxygen = H+ + GA8-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.1.4 4-guanidinobutyramide + H2O = H+ + ammonia + 4-guanidinobutyrate arginine degradation X (arginine monooxygenase pathway) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.4.5 H2O + cytidine = uridine + ammonia salvage pathways of pyrimidine ribonucleotides ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.4.5 H2O + cytidine = uridine + ammonia pyrimidine ribonucleosides degradation II ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 2.7.2.2 ammonia + CO2 + ATP = H+ + carbamoyl-phosphate + ADP citrulline degradation ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 2.7.2.2 ammonia + CO2 + ATP = H+ + carbamoyl-phosphate + ADP allantoin degradation IV (anaerobic) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 4.4.1.8 L-cystathionine + H2O = H+ + ammonia + pyruvate + L-homocysteine methionine biosynthesis II ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 4.4.1.8 L-cystathionine + H2O = H+ + ammonia + pyruvate + L-homocysteine homocysteine and cysteine interconversion ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.3.- S-ureidoglycine + H2O = H+ + ammonia + S-(-)-ureidoglycolate allantoin degradation to ureidoglycolate II (ammonia producing) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 6.3.1.1 ammonia + L-aspartate + ATP = L-asparagine + diphosphate + AMP asparagine biosynthesis II ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 L-phenylalanine + oxygen + H2O = phenylacetaldehyde + ammonia + hydrogen peroxide + CO2 phenylethanol biosynthesis ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.1.5 urea + H2O = ammonia + CO2 urea degradation II ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP glutamine biosynthesis III ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP nitrate reduction II (assimilatory) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP ammonia assimilation cycle II ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 2.5.1.61 H2O + porphobilinogen = H+ + ammonia + hydroxymethylbilane tetrapyrrole biosynthesis I ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 1.18.6.1 H+ + N2 + ATP + H2O = H2 + ammonia + ADP nitrogen fixation ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.1.2 L-glutamine + H2O = H+ + L-glutamate + ammonia glutamine degradation I ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.1.2 L-glutamine + H2O = H+ + L-glutamate + ammonia citrulline biosynthesis ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.4.13 H2O + dCTP = ammonia + dUTP pyrimidine deoxyribonucleotides de novo biosynthesis I ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 1.4.3.5 oxygen + H2O + pyridoxamine 5'-phosphate = H+ + ammonia + hydrogen peroxide + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.3.9 H+ + allantoate + H2O = S-ureidoglycine + ammonia + CO2 allantoin degradation to ureidoglycolate II (ammonia producing) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 1.4.3.21 2-phenylethylamine + oxygen + H2O = H+ + phenylacetaldehyde + ammonia + hydrogen peroxide phenylethanol biosynthesis ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 1.7.7.1 ammonia + H2O = nitrite + H+ nitrate reduction II (assimilatory) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations I ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations II (plants) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH photorespiration ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 6.3.1.14 ammonia + ATP = H+ + ADP diphthamide biosynthesis ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.3.6 H2O + L-arginine = H+ + ammonia + L-citrulline proline biosynthesis II (from arginine) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ suberin biosynthesis ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ phenylpropanoid biosynthesis, initial reactions ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ trans-cinnamoyl-CoA biosynthesis ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ benzoate biosynthesis II (CoA-independent, non-β-oxidative) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 4.4.1.1 L-cystathionine + H2O = H+ + ammonia + 2-oxobutanoate + L-cysteine homocysteine and cysteine interconversion ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.4.3 H2O + guanine = ammonia + xanthine guanosine nucleotides degradation II ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.1.6 3-ureido-isobutyrate + H2O + H+ = (R)-3-amino-2-methylpropanoate + ammonia + CO2 thymine degradation ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 1.4.1.3 H2O + L-glutamate = ammonia + 2-oxoglutarate glutamate degradation X ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 1.4.1.3 H2O + L-glutamate = ammonia + 2-oxoglutarate glutamate biosynthesis II ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.5.1 indole-3-acetonitrile + H2O = H+ + ammonia + indole-3-acetate IAA biosynthesis I ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 1.4.1.2 H2O + NAD+ + L-glutamate = H+ + ammonia + NADH + 2-oxoglutarate glutamate degradation I ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 1.4.1.2 H2O + NAD+ + L-glutamate = H+ + ammonia + NADH + 2-oxoglutarate alanine degradation II (to D-lactate) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 6.3.1.5 ammonia + ATP + nicotinate adenine dinucleotide = AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.1.53 H+ + N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia putrescine biosynthesis II ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.1.53 H+ + N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 2.1.2.10 tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia glycine cleavage complex ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.1.20 H+ + L-citrulline + H2O = L-ornithine + CO2 + ammonia proline biosynthesis II (from arginine) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 4.3.1.19 L-threonine = H+ + 2-oxobutanoate + ammonia isoleucine biosynthesis I (from threonine) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 4.3.1.19 L-threonine = H+ + 2-oxobutanoate + ammonia hypoglycin biosynthesis ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.4.1 H2O + cytosine = ammonia + uracil salvage pathways of pyrimidine ribonucleotides ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 4.2.1.104 carbamate + H+ = ammonia + CO2 cyanate degradation ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.4.4 H2O + adenosine = ammonia + inosine adenosine nucleotides degradation II ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.5.4 H2O + 3-cyano-L-alanine = ammonia + L-aspartate cyanide detoxification ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 DMSP-amine + oxygen + H2O = H+ + 3-dimethylsulfoniopropionaldehyde + ammonia + hydrogen peroxide dimethylsulfoniopropionate biosynthesis II (Spartina) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.1.19 nicotinamide + H2O = H+ + ammonia + nicotinate pyridine nucleotide cycling (plants) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.4.6 AMP + H2O = inosine-5'-phosphate + ammonia adenosine nucleotides degradation I ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 6.3.4.16 ammonia + H2O + CO2 + ATP = H+ + carbamoyl-phosphate + ADP urea cycle ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 1.4.3.22 propane-1,3-diamine + H2O + oxygen = H+ + 3-aminopropanal + ammonia + hydrogen peroxide β-alanine biosynthesis I ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 4.4.1.11 L-methionine + H2O = H+ + methanethiol + ammonia + 2-oxobutanoate methionine degradation II ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.3.12 H2O + agmatine = H+ + ammonia + N-carbamoylputrescine putrescine biosynthesis II ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.3.12 H2O + agmatine = H+ + ammonia + N-carbamoylputrescine arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.1.1 L-asparagine + H2O = L-aspartate + ammonia + H+ asparagine degradation I ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 1.4.3.10 oxygen + H2O + putrescine = H+ + ammonia + hydrogen peroxide + 4-aminobutanal putrescine degradation IV ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.1.6 3-ureidopropionate + H2O + H+ = β-alanine + ammonia + CO2 uracil degradation II (reductive) ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.1.4 indole-3-acetamide + H2O = H+ + indole-3-acetate + ammonia IAA biosynthesis I ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 4.3.1.18 D-serine = H+ + pyruvate + ammonia serine racemization ammonia NH3 17.03 H3 N1 [H]N([H])[H] PUBCHEM:222:*PUBCHEM:222:*CHEBI:32863:*KNAPSACK:C00007267:*KNAPKSACK:C00007267*LIGAND-CPD:C00014:*CAS:7664-41-7 3.5.4.26 H2O + 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one = 5-amino-6-(5-phospho-D-ribosylamino)uracil + ammonia flavin biosynthesis I (bacteria and plants) 3-hydroxyanthranilate 3-hydroxyanthranilic acid 152.129 C7 H6 N1 O3 C1(C(=C(N)C(O)=CC=1)C([O-])=O) PUBCHEM:9543318:*CHEBI:36559:*LIGAND-CPD:C00632:*CAS:548-93-6 1.14.14.8 anthranilate + oxygen + FADH2 = 3-hydroxyanthranilate + H2O + FAD + H+ anthranilate degradation IV (aerobic) 2-methoxy-6-all trans-decaprenyl-2-methoxy-1,4-benzoquinol 2-methoxy-6-decaprenyl-2-methoxy-1,4-benzoquinol 821.32 C57 H88 O3 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(C=C(O)C=C(OC)C=1O))C)C)C)C)C)C)C)CCC=C(C)CCC=C(C)C PUBCHEM:25245957: 1.14.13.- 2-decaprenyl-6-methoxyphenol + oxygen + NADPH + H+ = 2-methoxy-6-all trans-decaprenyl-2-methoxy-1,4-benzoquinol + H2O + NADP+ ubiquinol-10 biosynthesis (eukaryotic) 2-methoxy-6-all trans-decaprenyl-2-methoxy-1,4-benzoquinol 2-methoxy-6-decaprenyl-2-methoxy-1,4-benzoquinol 821.32 C57 H88 O3 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(C=C(O)C=C(OC)C=1O))C)C)C)C)C)C)C)CCC=C(C)CCC=C(C)C PUBCHEM:25245957: 2.1.1.- 2-methoxy-6-all trans-decaprenyl-2-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine = H+ + 6-methoxy-5-methyl-2-all-trans-decaprenyl-1,4-benzoquinol + S-adenosyl-L-homocysteine ubiquinol-10 biosynthesis (eukaryotic) putrescine diaminobutane*1,4-diaminobutane*1,4-butanediamine*tetramethylenediamine*putrescine 90.168 C4 H14 N2 [N+]CCCC[N+] CHEBI:326268:*PUBCHEM:3452892:*LIGAND-CPD:C00134:*CAS:110-60-1 1.4.3.10 oxygen + H2O + putrescine = H+ + ammonia + hydrogen peroxide + 4-aminobutanal putrescine degradation IV putrescine diaminobutane*1,4-diaminobutane*1,4-butanediamine*tetramethylenediamine*putrescine 90.168 C4 H14 N2 [N+]CCCC[N+] CHEBI:326268:*PUBCHEM:3452892:*LIGAND-CPD:C00134:*CAS:110-60-1 3.5.3.11 H2O + agmatine = urea + putrescine arginine degradation III (arginine decarboxylase/agmatinase pathway) putrescine diaminobutane*1,4-diaminobutane*1,4-butanediamine*tetramethylenediamine*putrescine 90.168 C4 H14 N2 [N+]CCCC[N+] CHEBI:326268:*PUBCHEM:3452892:*LIGAND-CPD:C00134:*CAS:110-60-1 3.5.3.11 H2O + agmatine = urea + putrescine putrescine biosynthesis IV putrescine diaminobutane*1,4-diaminobutane*1,4-butanediamine*tetramethylenediamine*putrescine 90.168 C4 H14 N2 [N+]CCCC[N+] CHEBI:326268:*PUBCHEM:3452892:*LIGAND-CPD:C00134:*CAS:110-60-1 3.5.1.53 H+ + N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia putrescine biosynthesis II putrescine diaminobutane*1,4-diaminobutane*1,4-butanediamine*tetramethylenediamine*putrescine 90.168 C4 H14 N2 [N+]CCCC[N+] CHEBI:326268:*PUBCHEM:3452892:*LIGAND-CPD:C00134:*CAS:110-60-1 3.5.1.53 H+ + N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) putrescine diaminobutane*1,4-diaminobutane*1,4-butanediamine*tetramethylenediamine*putrescine 90.168 C4 H14 N2 [N+]CCCC[N+] CHEBI:326268:*PUBCHEM:3452892:*LIGAND-CPD:C00134:*CAS:110-60-1 2.5.1.16 putrescine + S-adenosyl-L-methioninamine = H+ + spermidine + S-methyl-5'-thioadenosine spermidine biosynthesis I putrescine diaminobutane*1,4-diaminobutane*1,4-butanediamine*tetramethylenediamine*putrescine 90.168 C4 H14 N2 [N+]CCCC[N+] CHEBI:326268:*PUBCHEM:3452892:*LIGAND-CPD:C00134:*CAS:110-60-1 4.1.1.17 H+ + L-ornithine = CO2 + putrescine putrescine biosynthesis IV 4α-formyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol 9,19-cycloanostan-28-one-3-hydroxy-24-methylene-, (3β, 4α)- 454.735 C31 H50 O2 C1(CC(C(C2(C51(C3(C(CC2)C4(C)(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4))C5)))(C)C=O)O) 1.14.13.- 4α-formyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NADH + oxygen = 4α-carboxy-4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis 4α-formyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol 9,19-cycloanostan-28-one-3-hydroxy-24-methylene-, (3β, 4α)- 454.735 C31 H50 O2 C1(CC(C(C2(C51(C3(C(CC2)C4(C)(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4))C5)))(C)C=O)O) 1.14.13.- 4α-hydroxymethyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NADH + oxygen = 4α-formyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis 2,3-dihydroxy-3-methylvalerate (R)-2,3-Dihydroxy-3-methylpentanoate*(R)-2,3-Dihydroxy-3-methylvalerate*2,3-dihydroxy-3-methylpentanoate 147.15 C6 H11 O4 C(C(C)(O)C(C([O-])=O)O)C PUBCHEM:21263701:*LIGAND-CPD:C06007: 4.2.1.9 2,3-dihydroxy-3-methylvalerate = 2-keto-3-methyl-valerate + H2O isoleucine biosynthesis I (from threonine) 2,3-dihydroxy-3-methylvalerate (R)-2,3-Dihydroxy-3-methylpentanoate*(R)-2,3-Dihydroxy-3-methylvalerate*2,3-dihydroxy-3-methylpentanoate 147.15 C6 H11 O4 C(C(C)(O)C(C([O-])=O)O)C PUBCHEM:21263701:*LIGAND-CPD:C06007: 1.1.1.86 H+ + 2-aceto-2-hydroxy-butanoate + NADPH = 2,3-dihydroxy-3-methylvalerate + NADP+ isoleucine biosynthesis I (from threonine) 3-epi-6-deoxocathasterone 418.702 C28 H50 O2 C1(CC(CC2([H])(C1(C3(C(CC2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))O) H+ + (22S,24R)-22-hydroxy-5α-ergostan-3-one = 3-epi-6-deoxocathasterone brassinosteroid biosynthesis II 3-epi-6-deoxocathasterone 418.702 C28 H50 O2 C1(CC(CC2([H])(C1(C3(C(CC2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))O) 1.14.13.- H+ + 3-epi-6-deoxocathasterone + NADPH + oxygen = 6-deoxotyphasterol + NADP+ + H2O brassinosteroid biosynthesis II trans-zeatin zeatin*cytokinin*(2E)-2-methyl-4-(1H-purin-6-ylamino)-2-buten-1-ol*t-zeatin 219.246 C10 H13 N5 O1 C1(C2(=C(N=CN=1)NC=N2))NCC=C(CO)C CHEBI:16522:*PUBCHEM:449093:*LIGAND-CPD:C00371: trans-zeatin riboside monophosphate + H2O = trans-zeatin + D-ribose-5-phosphate trans-zeatin biosynthesis trans-zeatin zeatin*cytokinin*(2E)-2-methyl-4-(1H-purin-6-ylamino)-2-buten-1-ol*t-zeatin 219.246 C10 H13 N5 O1 C1(C2(=C(N=CN=1)NC=N2))NCC=C(CO)C CHEBI:16522:*PUBCHEM:449093:*LIGAND-CPD:C00371: N6-dimethylallyladenine + H2O = trans-zeatin + H+ trans-zeatin biosynthesis trans-zeatin zeatin*cytokinin*(2E)-2-methyl-4-(1H-purin-6-ylamino)-2-buten-1-ol*t-zeatin 219.246 C10 H13 N5 O1 C1(C2(=C(N=CN=1)NC=N2))NCC=C(CO)C CHEBI:16522:*PUBCHEM:449093:*LIGAND-CPD:C00371: 1.5.99.12 H+ + trans-zeatin + H2O + FAD = adenine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation trans-zeatin zeatin*cytokinin*(2E)-2-methyl-4-(1H-purin-6-ylamino)-2-buten-1-ol*t-zeatin 219.246 C10 H13 N5 O1 C1(C2(=C(N=CN=1)NC=N2))NCC=C(CO)C CHEBI:16522:*PUBCHEM:449093:*LIGAND-CPD:C00371: 2.4.1.203 trans-zeatin = H+ + trans-zeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis 6-hydroxymethyl-dihydropterin diphosphate 6-hydroxymethyl-dihydropterin pyrophosphate*2-amino-7,8-dihydro-4-hydroxy-6-(diphosphooxymethyl)-pteridine*dihydropterin-CH2OH-diphosphate*dihydropterin-CH2OH-pp*(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate 352.116 C7 H8 N5 O8 P2 C2(C(COP(=O)([O-])OP(=O)([O-])[O-])=NC1(C(=O)NC(N)=NC=1N2)) CHEBI:57602:*PUBCHEM:25244074:*LIGAND-CPD:C04807: 2.7.6.3 6-hydroxymethyl-7,8-dihydropterin + ATP = H+ + 6-hydroxymethyl-dihydropterin diphosphate + AMP 6-hydroxymethyl-dihydropterin diphosphate biosynthesis 6-hydroxymethyl-dihydropterin diphosphate 6-hydroxymethyl-dihydropterin pyrophosphate*2-amino-7,8-dihydro-4-hydroxy-6-(diphosphooxymethyl)-pteridine*dihydropterin-CH2OH-diphosphate*dihydropterin-CH2OH-pp*(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate 352.116 C7 H8 N5 O8 P2 C2(C(COP(=O)([O-])OP(=O)([O-])[O-])=NC1(C(=O)NC(N)=NC=1N2)) CHEBI:57602:*PUBCHEM:25244074:*LIGAND-CPD:C04807: 2.5.1.15 p-aminobenzoate + 6-hydroxymethyl-dihydropterin diphosphate = 7,8-dihydropteroate + diphosphate tetrahydrofolate biosynthesis L-homocysteine L-Homocysteine*homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(C(=O)[O-])[N+] PUBCHEM:6971015:*CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.10 L-homocysteine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + L-methionine methionine biosynthesis II L-homocysteine L-Homocysteine*homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(C(=O)[O-])[N+] PUBCHEM:6971015:*CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 4.2.1.22 L-homocysteine + L-serine = H2O + L-cystathionine homocysteine and cysteine interconversion L-homocysteine L-Homocysteine*homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(C(=O)[O-])[N+] PUBCHEM:6971015:*CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 3.3.1.1 S-adenosyl-L-homocysteine + H2O = L-homocysteine + adenosine methionine degradation I (to homocysteine) L-homocysteine L-Homocysteine*homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(C(=O)[O-])[N+] PUBCHEM:6971015:*CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 3.3.1.1 S-adenosyl-L-homocysteine + H2O = L-homocysteine + adenosine S-adenosyl-L-methionine cycle II L-homocysteine L-Homocysteine*homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(C(=O)[O-])[N+] PUBCHEM:6971015:*CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.10 S-methyl-L-methionine + L-homocysteine = H+ + L-methionine methionine biosynthesis II L-homocysteine L-Homocysteine*homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(C(=O)[O-])[N+] PUBCHEM:6971015:*CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.10 S-methyl-L-methionine + L-homocysteine = H+ + L-methionine S-methylmethionine cycle L-homocysteine L-Homocysteine*homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(C(=O)[O-])[N+] PUBCHEM:6971015:*CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 4.4.1.8 L-cystathionine + H2O = H+ + ammonia + pyruvate + L-homocysteine methionine biosynthesis II L-homocysteine L-Homocysteine*homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(C(=O)[O-])[N+] PUBCHEM:6971015:*CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 4.4.1.8 L-cystathionine + H2O = H+ + ammonia + pyruvate + L-homocysteine homocysteine and cysteine interconversion L-homocysteine L-Homocysteine*homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(C(=O)[O-])[N+] PUBCHEM:6971015:*CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyl tri-L-glutamate + L-methionine methionine biosynthesis II L-homocysteine L-Homocysteine*homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(C(=O)[O-])[N+] PUBCHEM:6971015:*CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyl tri-L-glutamate + L-methionine S-adenosyl-L-methionine cycle I L-homocysteine L-Homocysteine*homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(C(=O)[O-])[N+] PUBCHEM:6971015:*CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyl tri-L-glutamate + L-methionine S-adenosyl-L-methionine cycle II L-homocysteine L-Homocysteine*homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(C(=O)[O-])[N+] PUBCHEM:6971015:*CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 4.4.1.21 S-ribosyl-L-homocysteine = L-homocysteine + 4,5-dihydroxy-2,3-pentanedione S-adenosyl-L-methionine cycle I L-homocysteine L-Homocysteine*homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(C(=O)[O-])[N+] PUBCHEM:6971015:*CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.13 L-homocysteine + 5-methyl-tetrahydrofolate = L-methionine + tetrahydrofolate folate transformations I L-homocysteine L-Homocysteine*homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(C(=O)[O-])[N+] PUBCHEM:6971015:*CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.13 L-homocysteine + 5-methyl-tetrahydrofolate = L-methionine + tetrahydrofolate folate transformations II (plants) dihydroxyphenyl-5-methyloxazoline-norspermidine-2,3-dihydroxybenzoate DHP-mOx-NS-DHB 486.524 C24 H30 N4 O7 C1(O)(C(=C(C=CC=1)C(=O)NCCCNCCCNC(C3(C(C)OC(C2(C=CC(O)=C(O)C=2))=N3))=O)O) PUBCHEM:46173161: dihydroxyphenyl-5-methyloxazoline-norspermidine-2,3-dihydroxybenzoate + dihydroxyphenyl-5-methyloxazoline-VibF = vibriobactin vibriobactin biosynthesis dihydroxyphenyl-5-methyloxazoline-norspermidine-2,3-dihydroxybenzoate DHP-mOx-NS-DHB 486.524 C24 H30 N4 O7 C1(O)(C(=C(C=CC=1)C(=O)NCCCNCCCNC(C3(C(C)OC(C2(C=CC(O)=C(O)C=2))=N3))=O)O) PUBCHEM:46173161: norspermidine-2,3-dihydroxybenzoate + dihydroxyphenyl-5-methyloxazoline-VibF = dihydroxyphenyl-5-methyloxazoline-norspermidine-2,3-dihydroxybenzoate vibriobactin biosynthesis D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate pentose phosphate pathway (partial) D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate Rubisco shunt D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate pentose phosphate pathway (non-oxidative branch) D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate Calvin-Benson-Bassham cycle D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = D-fructose-6-phosphate + D-erythrose-4-phosphate Rubisco shunt D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = D-fructose-6-phosphate + D-erythrose-4-phosphate pentose phosphate pathway (non-oxidative branch) D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.11 ATP + D-fructose-6-phosphate = H+ + ADP + fructose-1,6-bisphosphate glycolysis III D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.11 ATP + D-fructose-6-phosphate = H+ + ADP + fructose-1,6-bisphosphate glycolysis IV (plant cytosol) D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.11 ATP + D-fructose-6-phosphate = H+ + ADP + fructose-1,6-bisphosphate glycolysis I D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 2.6.1.16 D-fructose-6-phosphate + L-glutamine = L-glutamate + D-glucosamine-6-phosphate UDP-N-acetyl-D-glucosamine biosynthesis II D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.8 D-mannose 6-phosphate = D-fructose-6-phosphate ascorbate biosynthesis I (L-galactose pathway) D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.8 D-mannose 6-phosphate = D-fructose-6-phosphate GDP-mannose biosynthesis D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.8 D-mannose 6-phosphate = D-fructose-6-phosphate mannitol degradation II D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.8 D-mannose 6-phosphate = D-fructose-6-phosphate D-mannose degradation D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.90 D-fructose-6-phosphate + diphosphate = H+ + fructose-1,6-bisphosphate glycolysis IV (plant cytosol) D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.9 β-D-glucose-6-phosphate = D-fructose-6-phosphate sucrose degradation III D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.9 β-D-glucose-6-phosphate = D-fructose-6-phosphate gluconeogenesis I D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.9 β-D-glucose-6-phosphate = D-fructose-6-phosphate GDP-mannose biosynthesis D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.9 β-D-glucose-6-phosphate = D-fructose-6-phosphate starch biosynthesis D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.9 β-D-glucose-6-phosphate = D-fructose-6-phosphate glycolysis III D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.9 β-D-glucose-6-phosphate = D-fructose-6-phosphate glycolysis I D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 3.1.3.11 fructose-1,6-bisphosphate + H2O = D-fructose-6-phosphate gluconeogenesis I D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 3.1.3.11 fructose-1,6-bisphosphate + H2O = D-fructose-6-phosphate glycolysis I D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 3.1.3.11 fructose-1,6-bisphosphate + H2O = D-fructose-6-phosphate Calvin-Benson-Bassham cycle D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.4 β-D-fructofuranose + ATP = H+ + D-fructose-6-phosphate + ADP sucrose degradation III D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.4 β-D-fructofuranose + ATP = H+ + D-fructose-6-phosphate + ADP sucrose degradation I D-fructose-6-phosphate D-fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)(CO)C(O)C(O)1) KNAPSACK:C00007305*CHEBI:57634:*PUBCHEM:21604863:*KNAPKSACK:C00007305*LIGAND-CPD:C00085:*CAS:643-13-0 2.4.1.14 D-fructose-6-phosphate = H+ + sucrose-6-phosphate + UDP sucrose biosynthesis β-carotene all-trans-beta-carotene 536.882 C40 H56 C1(C(C(=C(CC1)C)C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC2(=C(CCCC2(C)C)C))C)C)(C)C) PUBCHEM:5280489:*CHEBI:17579:*LIGAND-CPD:C02094:*CAS:7235-40-7 5.5.1.- γ-carotene = β-carotene β-carotene biosynthesis β-carotene all-trans-beta-carotene 536.882 C40 H56 C1(C(C(=C(CC1)C)C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC2(=C(CCCC2(C)C)C))C)C)(C)C) PUBCHEM:5280489:*CHEBI:17579:*LIGAND-CPD:C02094:*CAS:7235-40-7 1.14.99.- β-carotene + oxygen = β-cryptoxanthin + H2O zeaxanthin biosynthesis 2-isopropylmaleate 2-Isopropylmaleate*β-isopropylmaleate*2-isopropylmaleic acid 156.138 C7 H8 O4 C(=C(C(=O)[O-])C(C)C)C(=O)[O-] PUBCHEM:5280533:*PUBCHEM:21954611:*LIGAND-CPD:C02631: 4.2.1.33 (2R,3S)-3-isopropylmalate = 2-isopropylmaleate + H2O leucine biosynthesis 2-isopropylmaleate 2-Isopropylmaleate*β-isopropylmaleate*2-isopropylmaleic acid 156.138 C7 H8 O4 C(=C(C(=O)[O-])C(C)C)C(=O)[O-] PUBCHEM:5280533:*PUBCHEM:21954611:*LIGAND-CPD:C02631: 4.2.1.33 (2S)-2-isopropylmalate = 2-isopropylmaleate + H2O leucine biosynthesis dCTP 2'-deoxycytidine-5'-triphosphate*deoxycytidine-triphosphate*deoxy-CTP 463.127 C9 H12 N3 O13 P3 NC2(=NC(N(C1(OC(C(C1)O)COP(OP(OP([O-])([O-])=O)([O-])=O)([O-])=O))C=C2)=O) PUBCHEM:25244665:*LIGAND-CPD:C00458:*CAS:2056-98-6 3.5.4.13 H2O + dCTP = ammonia + dUTP pyrimidine deoxyribonucleotides de novo biosynthesis I dCTP 2'-deoxycytidine-5'-triphosphate*deoxycytidine-triphosphate*deoxy-CTP 463.127 C9 H12 N3 O13 P3 NC2(=NC(N(C1(OC(C(C1)O)COP(OP(OP([O-])([O-])=O)([O-])=O)([O-])=O))C=C2)=O) PUBCHEM:25244665:*LIGAND-CPD:C00458:*CAS:2056-98-6 CTP = dCTP + H2O pyrimidine deoxyribonucleotides de novo biosynthesis I dCTP 2'-deoxycytidine-5'-triphosphate*deoxycytidine-triphosphate*deoxy-CTP 463.127 C9 H12 N3 O13 P3 NC2(=NC(N(C1(OC(C(C1)O)COP(OP(OP([O-])([O-])=O)([O-])=O)([O-])=O))C=C2)=O) PUBCHEM:25244665:*LIGAND-CPD:C00458:*CAS:2056-98-6 2.7.4.6 dCDP + ATP = dCTP + ADP pyrimidine deoxyribonucleotides de novo biosynthesis I trans-zeatin riboside diphosphate ZDP*zeatin diphosphate*tZRDP 508.297 C15 H20 N5 O11 P2 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(NCC=C(C)CO)2)))OC(COP(=O)([O-])OP(=O)([O-])[O-])3) PUBCHEM:25244664:*LIGAND-CPD:C16429: N6-(Δ2-isopentenyl)-adenosine 5'-diphosphate + NADPH + H2O = H+ + trans-zeatin riboside diphosphate + NADP+ trans-zeatin biosynthesis trans-zeatin riboside diphosphate ZDP*zeatin diphosphate*tZRDP 508.297 C15 H20 N5 O11 P2 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(NCC=C(C)CO)2)))OC(COP(=O)([O-])OP(=O)([O-])[O-])3) PUBCHEM:25244664:*LIGAND-CPD:C16429: trans-zeatin riboside triphosphate + H2O = H+ + trans-zeatin riboside diphosphate trans-zeatin biosynthesis trans-zeatin riboside diphosphate ZDP*zeatin diphosphate*tZRDP 508.297 C15 H20 N5 O11 P2 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(NCC=C(C)CO)2)))OC(COP(=O)([O-])OP(=O)([O-])[O-])3) PUBCHEM:25244664:*LIGAND-CPD:C16429: trans-zeatin riboside diphosphate + H2O = H+ + trans-zeatin riboside monophosphate trans-zeatin biosynthesis 1,5-diazabicyclononane 1,5-diazabicyclo[4.3.0]nonane 127.209 C7 H15 N2 C1(C2([N+]CCCN(CC1)2)) PUBCHEM:25203381: 1-(3-aminopropyl)-pyrrolinium = H+ + 1,5-diazabicyclononane spermine and spermidine degradation II OPC6-CoA 1011.867 C37 H56 N7 O18 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)CCCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237133: 2.3.1.16 OPC8-3-ketoacyl-CoA + coenzyme A = acetyl-CoA + OPC6-CoA jasmonic acid biosynthesis OPC6-CoA 1011.867 C37 H56 N7 O18 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)CCCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237133: 1.3.3.6 OPC6-CoA + oxygen = OPC6-trans-2-enoyl-CoA + hydrogen peroxide jasmonic acid biosynthesis 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoic acid*oxopentenyl-cyclopentane-octanoic acid*8-[(1R,2R)-3-oxo-2-{(Z)-pent-2-enyl}cyclopentyl]octanoate*3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate*OPC8*OPC-8:0 293.425 C18 H29 O3 C(C([O-])=O)CCCCCCC1(CCC(=O)C(CC=CCC)1) PUBCHEM:25244083:*PUBCHEM:25244083:*LIGAND-CPD:C04780: 6.2.1.- 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate + coenzyme A + ATP = OPC8-CoA + AMP + diphosphate jasmonic acid biosynthesis 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoic acid*oxopentenyl-cyclopentane-octanoic acid*8-[(1R,2R)-3-oxo-2-{(Z)-pent-2-enyl}cyclopentyl]octanoate*3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate*OPC8*OPC-8:0 293.425 C18 H29 O3 C(C([O-])=O)CCCCCCC1(CCC(=O)C(CC=CCC)1) PUBCHEM:25244083:*PUBCHEM:25244083:*LIGAND-CPD:C04780: 1.3.1.42 NADP+ + 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate = H+ + NADPH + 12-oxo-cis-10,15-phytodienoate jasmonic acid biosynthesis raffinose α-D-galactopyranosyl-(1->6)-α-D-glucopyranosyl-(1->2)-β-D-fructofuranoside*α-D-Galp-(1->6)-α-D-Glcp-(1->2)-β-D-Fruf*melitose*melitriose*gossypose*6G-α-D-galactosylsucrose*(2S,3R,4S,5S,6R)-2-[[(2R,3R,4S,5R,6R)-6-[(2S,3S,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxy-oxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol*α-D-Galp-(1->6)-α-D-Glcp-(1<->2)-β-D-Fruf*α-D-galactopyranosyl-(1->6)-α-D-glucopyranosyl-(1<->2)-β-D-fructofuranoside 504.441 C18 H32 O16 C3(O)(C(O)C(CO)OC(OC2(C(O)C(O)C(O)C(COC1(C(O)C(O)C(O)C(CO)O1))O2))(CO)3) PUBCHEM:439242:*CHEBI:16634:*LIGAND-CPD:C00492:*CAS:512-69-6 2.4.1.67 galactinol + raffinose = myo-inositol + stachyose stachyose biosynthesis raffinose α-D-galactopyranosyl-(1->6)-α-D-glucopyranosyl-(1->2)-β-D-fructofuranoside*α-D-Galp-(1->6)-α-D-Glcp-(1->2)-β-D-Fruf*melitose*melitriose*gossypose*6G-α-D-galactosylsucrose*(2S,3R,4S,5S,6R)-2-[[(2R,3R,4S,5R,6R)-6-[(2S,3S,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxy-oxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol*α-D-Galp-(1->6)-α-D-Glcp-(1<->2)-β-D-Fruf*α-D-galactopyranosyl-(1->6)-α-D-glucopyranosyl-(1<->2)-β-D-fructofuranoside 504.441 C18 H32 O16 C3(O)(C(O)C(CO)OC(OC2(C(O)C(O)C(O)C(COC1(C(O)C(O)C(O)C(CO)O1))O2))(CO)3) PUBCHEM:439242:*CHEBI:16634:*LIGAND-CPD:C00492:*CAS:512-69-6 3.2.1.- raffinose + H2O = α-D-galactose + sucrose stachyose degradation raffinose α-D-galactopyranosyl-(1->6)-α-D-glucopyranosyl-(1->2)-β-D-fructofuranoside*α-D-Galp-(1->6)-α-D-Glcp-(1->2)-β-D-Fruf*melitose*melitriose*gossypose*6G-α-D-galactosylsucrose*(2S,3R,4S,5S,6R)-2-[[(2R,3R,4S,5R,6R)-6-[(2S,3S,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxy-oxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol*α-D-Galp-(1->6)-α-D-Glcp-(1<->2)-β-D-Fruf*α-D-galactopyranosyl-(1->6)-α-D-glucopyranosyl-(1<->2)-β-D-fructofuranoside 504.441 C18 H32 O16 C3(O)(C(O)C(CO)OC(OC2(C(O)C(O)C(O)C(COC1(C(O)C(O)C(O)C(CO)O1))O2))(CO)3) PUBCHEM:439242:*CHEBI:16634:*LIGAND-CPD:C00492:*CAS:512-69-6 2.4.1.82 galactinol + sucrose = myo-inositol + raffinose stachyose biosynthesis raffinose α-D-galactopyranosyl-(1->6)-α-D-glucopyranosyl-(1->2)-β-D-fructofuranoside*α-D-Galp-(1->6)-α-D-Glcp-(1->2)-β-D-Fruf*melitose*melitriose*gossypose*6G-α-D-galactosylsucrose*(2S,3R,4S,5S,6R)-2-[[(2R,3R,4S,5R,6R)-6-[(2S,3S,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxy-oxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol*α-D-Galp-(1->6)-α-D-Glcp-(1<->2)-β-D-Fruf*α-D-galactopyranosyl-(1->6)-α-D-glucopyranosyl-(1<->2)-β-D-fructofuranoside 504.441 C18 H32 O16 C3(O)(C(O)C(CO)OC(OC2(C(O)C(O)C(O)C(COC1(C(O)C(O)C(O)C(CO)O1))O2))(CO)3) PUBCHEM:439242:*CHEBI:16634:*LIGAND-CPD:C00492:*CAS:512-69-6 3.2.1.22 stachyose + H2O = raffinose + α-D-galactose stachyose degradation oleate omega fatty acid*ω-3 fatty acid*oleinic acid*(9Z)-octadec-9-enoate*cis-9-Octadecenoic acid*octadecenoate (n-C18:1)*oleic acid*9-octadecenoic acid 281.457 C18 H33 O2 C(CCCCCCCC)=CCCCCCCCC([O-])=O PUBCHEM:5460221:*KNAPSACK:C00001232:*PUBCHEM:5460221:*CHEBI:30823:*CHEBI:30823:*PUBCHEM:445639:*LIGAND-CPD:C00712:*CAS:112-80-1 2.1.1.79 oleate + S-adenosyl-L-methionine = H+ + dihydrosterculate + S-adenosyl-L-homocysteine cyclopropane and cyclopropene fatty acid biosynthesis oleate omega fatty acid*ω-3 fatty acid*oleinic acid*(9Z)-octadec-9-enoate*cis-9-Octadecenoic acid*octadecenoate (n-C18:1)*oleic acid*9-octadecenoic acid 281.457 C18 H33 O2 C(CCCCCCCC)=CCCCCCCCC([O-])=O PUBCHEM:5460221:*KNAPSACK:C00001232:*PUBCHEM:5460221:*CHEBI:30823:*CHEBI:30823:*PUBCHEM:445639:*LIGAND-CPD:C00712:*CAS:112-80-1 1.14.13.- oleate + NADPH + oxygen = 18-hydroxyoleate + NADP+ + H2O suberin biosynthesis oleate omega fatty acid*ω-3 fatty acid*oleinic acid*(9Z)-octadec-9-enoate*cis-9-Octadecenoic acid*octadecenoate (n-C18:1)*oleic acid*9-octadecenoic acid 281.457 C18 H33 O2 C(CCCCCCCC)=CCCCCCCCC([O-])=O PUBCHEM:5460221:*KNAPSACK:C00001232:*PUBCHEM:5460221:*CHEBI:30823:*CHEBI:30823:*PUBCHEM:445639:*LIGAND-CPD:C00712:*CAS:112-80-1 3.1.2.14 H2O = oleate oleate biosynthesis I (plants) oleate omega fatty acid*ω-3 fatty acid*oleinic acid*(9Z)-octadec-9-enoate*cis-9-Octadecenoic acid*octadecenoate (n-C18:1)*oleic acid*9-octadecenoic acid 281.457 C18 H33 O2 C(CCCCCCCC)=CCCCCCCCC([O-])=O PUBCHEM:5460221:*KNAPSACK:C00001232:*PUBCHEM:5460221:*CHEBI:30823:*CHEBI:30823:*PUBCHEM:445639:*LIGAND-CPD:C00712:*CAS:112-80-1 6.2.1.3 oleate + coenzyme A + ATP = oleoyl-CoA + AMP + diphosphate linoleate biosynthesis I (plants) DIMBOA-Glc DIMBOA-glucoside*2-(2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one)-β-D-glucopyranose 372.308 C15 H18 N1 O10 C1(C=CC2(=C(C=1)OC(C(N2[O-])=O)OC3(C(C(C(C(O3)CO)O)O)O)))OC PUBCHEM:441563:*PUBCHEM:25245969:*LIGAND-CPD:C15768: 3.2.1.21 DIMBOA-Glc + H2O = DIMBOA + β-D-glucose DIMBOA-glucoside degradation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.2 ammonia + CO2 + ATP = H+ + carbamoyl-phosphate + ADP citrulline degradation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.2 ammonia + CO2 + ATP = H+ + carbamoyl-phosphate + ADP allantoin degradation IV (anaerobic) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.- trans-cinnamate + coenzyme A + ATP = (E)-cinnamoyl-CoA + AMP + diphosphate trans-cinnamoyl-CoA biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.12 L-glutamate + 7,8-dihydropteroate + ATP = H+ + 7,8-dihydrofolate monoglutamate + ADP tetrahydrofolate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.3 AMP + ATP = ADP adenosine nucleotides de novo biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.6 dADP + ATP = dATP + ADP adenosine nucleotides de novo biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.71 shikimate + ATP = H+ + shikimate-3-phosphate + ADP chorismate biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.1.1 ammonia + L-aspartate + ATP = L-asparagine + diphosphate + AMP asparagine biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.33 (R)-pantothenate + ATP = H+ + D-4'-phosphopantothenate + ADP phosphopantothenate biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.- nicotinate riboside + ATP = H+ + nicotinate mononucleotide + ADP pyridine nucleotide cycling (plants) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.153 ATP = ADP 3-phosphoinositide biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 L-glutamate + ATP = AMP + diphosphate L-glutamine biosynthesis II (tRNA-dependent) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.15 H+ + L-proline + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.- ATP + pyridoxine = H+ + ADP + pyridoxine-5'-phosphate pyridoxal 5'-phosphate salvage pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.23 NAD+ + ATP = H+ + NADP+ + ADP NAD/NADH phosphorylation and dephosphorylation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.3.3.8 oxaloacetate + acetyl-CoA + ADP = citrate + coenzyme A + ATP acetyl-CoA biosynthesis (from citrate) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.1.14 ammonia + ATP = H+ + ADP diphthamide biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis II (acetyl cycle) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate uridine-5'-phosphate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.15 biotin + ATP = diphosphate + AMP biotin-carboxyl carrier protein assembly ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = H+ + 5'-phosphoribosyl-N-formylglycineamide + ADP 5-aminoimidazole ribonucleotide biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = H+ + 5'-phosphoribosyl-N-formylglycineamide + ADP superpathway of 5-aminoimidazole ribonucleotide biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 D-myo-inositol (3,4,6)-trisphosphate + ATP = H+ + D-myo-inositol (3,4,5,6)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.2 H+ + FMN + ATP = FAD + diphosphate flavin biosynthesis I (bacteria and plants) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.11 L-glutamate + ATP = L-glutamate-5-phosphate + ADP proline biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.11 L-glutamate + ATP = L-glutamate-5-phosphate + ADP citrulline biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.5.1.- ATP = diphosphate + AMP tRNA splicing ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.150 ATP = ADP 3-phosphoinositide biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.11 ATP + D-fructose-6-phosphate = H+ + ADP + fructose-1,6-bisphosphate glycolysis III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.11 ATP + D-fructose-6-phosphate = H+ + ADP + fructose-1,6-bisphosphate glycolysis IV (plant cytosol) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.11 ATP + D-fructose-6-phosphate = H+ + ADP + fructose-1,6-bisphosphate glycolysis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.26 ATP + o-succinylbenzoate + coenzyme A = 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA + ADP 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.6 dCDP + ATP = dCTP + ADP pyrimidine deoxyribonucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.- 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate + coenzyme A + ATP = OPC8-CoA + AMP + diphosphate jasmonic acid biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.3.2 5-formyl-tetrahydrofolate + ATP = 5,10-methenyltetrahydrofolate + ADP folate transformations I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.3.2 5-formyl-tetrahydrofolate + ATP = 5,10-methenyltetrahydrofolate + ADP folate transformations II (plants) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.2 ATP + UTP + L-glutamine + H2O = H+ + ADP + CTP + L-glutamate pyrimidine ribonucleotides interconversion ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.17 D-xylulose + ATP = H+ + D-xylulose-5-phosphate + ADP xylose degradation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.10 H+ + L-methionine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.140 1D-myo-inositol (1,2,3,4,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.16 H+ + L-cysteine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.11 H+ + L-serine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 3.6.3.- Cu2+ + H2O + ATP = Cu2+ + ADP copper transport I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP Rubisco shunt ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP glycolysis III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP glycolysis IV (plant cytosol) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP glycolysis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.64 myo-inositol + ATP = H+ + 1D-myo-inositol (3)-monophosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.39 L-homoserine + ATP = H+ + O-phospho-L-homoserine + ADP threonine biosynthesis from homoserine ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.39 L-homoserine + ATP = H+ + O-phospho-L-homoserine + ADP methionine biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.9 H+ + L-valine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.4.2.17 phosphoribosyl-ATP + diphosphate = ATP + 5-phospho-α-D-ribose 1-diphosphate histidine biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = H+ + L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.7 ATP = H+ + D-mannose 6-phosphate + ADP mannitol degradation II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.22 ATP + uridine-5'-phosphate = ADP + UDP pyrimidine ribonucleotides interconversion ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.7 L-glutamine + ATP = L-glutamate + ADP L-glutamine biosynthesis II (tRNA-dependent) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.5 H+ + L-isoleucine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP acetate conversion to acetyl-CoA ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP ethanol degradation II (cytosol) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP ethanol degradation IV (peroxisomal) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.27 H+ + α-D-glucose 1-phosphate + ATP = ADP-α-D-glucose + diphosphate glycogen biosynthesis I (from ADP-D-Glucose) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.27 H+ + α-D-glucose 1-phosphate + ATP = ADP-α-D-glucose + diphosphate starch biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.18 H+ + ATP + nicotinate mononucleotide = diphosphate + nicotinate adenine dinucleotide NAD biosynthesis I (from aspartate) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.18 H+ + ATP + nicotinate mononucleotide = diphosphate + nicotinate adenine dinucleotide pyridine nucleotide cycling (plants) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.4.1.4 ATP + 3-methylcrotonyl-CoA + bicarbonate = H+ + ADP + 3-methylglutaconyl-CoA leucine degradation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.24 dephospho-CoA + ATP = H+ + coenzyme A + ADP coenzyme A biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.6 H+ + L-lysine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.6.2 thiamin + ATP = H+ + thiamine diphosphate + AMP thiamine biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.4 L-aspartate + ATP = L-aspartyl-4-phosphate + ADP lysine biosynthesis VI ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.4 L-aspartate + ATP = L-aspartyl-4-phosphate + ADP homoserine biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate folate transformations I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate folate transformations II (plants) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate formaldehyde oxidation V (tetrahydrofolate pathway) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate folate polyglutamylation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.6 dUDP + ATP = dUTP + ADP pyrimidine deoxyribonucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.9.3 H2O + hydrogen selenide + ATP = selenophosphate + AMP selenocysteine biosynthesis II (archaea and eukaryotes) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.32 choline + ATP = H+ + phosphoryl-choline + ADP phosphatidylcholine biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 1.18.6.1 H+ + N2 + ATP + H2O = H2 + ammonia + ADP nitrogen fixation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.127 D-myo-inositol (1,4,5)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.17 coenzyme A + propionate + ATP = propanoyl-CoA + diphosphate + AMP β-alanine biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.12 trans-caffeate + coenzyme A + ATP = caffeoyl-CoA + AMP + diphosphate suberin biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.134 D-myo-inositol (3,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.134 D-myo-inositol (3,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.18 H+ + L-glutamine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.86 NADH + ATP = H+ + NADPH + ADP NAD/NADH phosphorylation and dephosphorylation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.- D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,2,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.8 N-acetyl-L-glutamate + ATP = N-acetylglutamyl-phosphate + ADP arginine biosynthesis II (acetyl cycle) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.8 N-acetyl-L-glutamate + ATP = N-acetylglutamyl-phosphate + ADP ornithine biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.149 ATP = ADP D-myo-inositol (1,4,5)-trisphosphate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.22 H+ + L-asparagine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.1 β-alanine + (R)-pantoate + ATP = H+ + (R)-pantothenate + diphosphate + AMP phosphopantothenate biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.1 β-alanine + (R)-pantoate + ATP = H+ + (R)-pantothenate + diphosphate + AMP pantothenate biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.164 ATP = ADP selenocysteine biosynthesis II (archaea and eukaryotes) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.151 D-myo-inositol (1,4,5)-trisphosphate + ATP = H+ + D-myo-inositol (1,4,5,6)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.151 D-myo-inositol (1,4,5)-trisphosphate + ATP = H+ + D-myo-inositol (1,4,5,6)-tetrakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.1.5 ammonia + ATP + nicotinate adenine dinucleotide = AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 D-myo-inositol (3,4)-bisphosphate + ATP = H+ + D-myo-inositol (3,4,6)-trisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.43 ATP = H+ + α-D-glucuronate 1-phosphate + ADP UDP-D-glucuronate biosynthesis (from myo-inositol) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.9 ATP + dTMP = ADP + dTDP pyrimidine deoxyribonucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.2 mevalonate-5-phosphate + ATP = mevalonate-diphosphate + ADP mevalonate pathway I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.35 ATP + pyridoxamine = H+ + ADP + pyridoxamine 5'-phosphate pyridoxal 5'-phosphate salvage pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.83 pseudouridine + ATP = H+ + pseudouridine 5'-phosphate + ADP pseudouridine degradation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP gluconeogenesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP glycolysis III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP glycolysis IV (plant cytosol) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP glycolysis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP Calvin-Benson-Bassham cycle ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine methionine degradation I (to homocysteine) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine 2'-deoxymugineic acid phytosiderophore biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine ethylene biosynthesis from methionine ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine S-adenosyl-L-methionine cycle II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine S-adenosyl-L-methionine biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 4.1.1.49 oxaloacetate + ATP = CO2 + phosphoenolpyruvate + ADP gluconeogenesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 4.1.1.49 oxaloacetate + ATP = CO2 + phosphoenolpyruvate + ADP superpathway of glyoxylate cycle ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.6.1.1 ATP + protoporphyrin IX + Mg2+ + H2O = H+ + Mg-protoporphyrin + ADP chlorophyllide a biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.35 ATP + pyridoxal = H+ + ADP + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 4.1.1.33 mevalonate-diphosphate + ATP = isopentenyl diphosphate + CO2 + ADP mevalonate pathway I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.3 H+ + L-threonine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 ATP = dATP + H2O adenosine nucleotides de novo biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = H+ + L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.4 H+ + L-leucine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ pyridine nucleotide cycling (plants) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.6.3 6-hydroxymethyl-7,8-dihydropterin + ATP = H+ + 6-hydroxymethyl-dihydropterin diphosphate + AMP 6-hydroxymethyl-dihydropterin diphosphate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.6 ATP + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-aspartate = H+ + ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole inosine-5'-phosphate biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid activation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.14 ATP + uridine-5'-phosphate = ADP + UDP pyrimidine ribonucleotides interconversion ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine superpathway of 5-aminoimidazole ribonucleotide biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 3.6.3.4 Cu2+ + H2O + ATP = Cu2+ + ADP copper transport II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.3 oleate + coenzyme A + ATP = oleoyl-CoA + AMP + diphosphate linoleate biosynthesis I (plants) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 3.6.3.14 H+ + H2O + ATP = H+ + ADP adenosine nucleotides de novo biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.5.1.- H+ + dimethylallyl diphosphate + ATP = N6-(Δ2-isopentenyl)-adenosine 5'-triphosphate + diphosphate trans-zeatin biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP glutamine biosynthesis III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP nitrate reduction II (assimilatory) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP ammonia assimilation cycle II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.68 ATP = ADP 3-phosphoinositide biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.68 ATP = ADP D-myo-inositol (1,4,5)-trisphosphate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.14 H+ + glycine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.49 ATP + hydroxymethylpyrimidine = H+ + ADP + hydroxymethylpyrimidine phosphate thiamine biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.20 adenosine + ATP = H+ + AMP + ADP adenine and adenosine salvage VI ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.30 glycerol + ATP = H+ + sn-glycerol-3-phosphate + ADP glycerol degradation IV ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.30 glycerol + ATP = H+ + sn-glycerol-3-phosphate + ADP glycerol degradation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.52 ATP = β-L-fucose 1-phosphate + ADP GDP-L-fucose biosynthesis II (from L-fucose) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.5 succinate + coenzyme A + ATP = succinyl-CoA + ADP TCA cycle variation III (eukaryotic) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.6.1 ATP + D-ribose-5-phosphate = H+ + 5-phospho-α-D-ribose 1-diphosphate + AMP PRPP biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.9.1 pyruvate + ATP = H+ + phosphoenolpyruvate + AMP + diphosphate glutamine biosynthesis III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.9.1 pyruvate + ATP = H+ + phosphoenolpyruvate + AMP + diphosphate C4 photosynthetic carbon assimilation cycle ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP GDP-glucose biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP glycolysis III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP trehalose degradation II (trehalase) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP glucose and glucose-1-phosphate degradation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP glycogen degradation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.67 ATP = ADP 3-phosphoinositide biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.67 ATP = ADP D-myo-inositol (1,4,5)-trisphosphate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.20 H+ + L-phenylalanine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide 5-aminoimidazole ribonucleotide biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide 5-aminoimidazole ribonucleotide biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide superpathway of 5-aminoimidazole ribonucleotide biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.6 CDP + ATP = CTP + ADP pyrimidine ribonucleotides interconversion ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.6 CDP + ATP = CTP + ADP salvage pathways of pyrimidine ribonucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.31 D-glycerate + ATP = H+ + 3-phospho-D-glycerate + ADP photorespiration ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP urea cycle ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP arginine biosynthesis II (acetyl cycle) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP citrulline-nitric oxide cycle ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP arginine biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.4 β-D-fructofuranose + ATP = H+ + D-fructose-6-phosphate + ADP sucrose degradation III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.4 β-D-fructofuranose + ATP = H+ + D-fructose-6-phosphate + ADP sucrose degradation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.91 sphinganine + ATP = H+ + sphinganine 1-phosphate + ADP sphingolipid biosynthesis (plants) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.- D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + 1D-myo-inositol (1,2,3,4,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.82 ethanolamine + ATP = H+ + phosphoryl-ethanolamine + ADP phosphatidylethanolamine biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.82 ethanolamine + ATP = H+ + phosphoryl-ethanolamine + ADP choline biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.16 ammonia + H2O + CO2 + ATP = H+ + carbamoyl-phosphate + ADP urea cycle ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = H+ + glutathione + ADP γ-glutamyl cycle (plant pathway) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = H+ + glutathione + ADP glutathione biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.148 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + ATP = H+ + 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + ADP methylerythritol phosphate pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.138 ATP = ADP sphingolipid biosynthesis (plants) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP galactose degradation I (Leloir pathway) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP stachyose degradation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP colanic acid building blocks biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP galactose degradation III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.19 H+ + L-arginine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.6 dTDP + ATP = dTTP + ADP pyrimidine deoxyribonucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.1 α-D-glucose + ATP = H+ + α-D-glucose 6-phosphate + ADP sucrose degradation III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.1 α-D-glucose + ATP = H+ + α-D-glucose 6-phosphate + ADP starch degradation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.46 ATP = β-L-arabinose 1-phosphate + ADP UDP-L-arabinose biosynthesis II (from L-arabinose) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid β-oxidation II (core pathway) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.9.2 H2O + pyruvate + ATP = H+ + phosphoenolpyruvate + AMP gluconeogenesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.9.2 H2O + pyruvate + ATP = H+ + phosphoenolpyruvate + AMP glycolysis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.2 H+ + L-tryptophan + ATP = AMP + diphosphate tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 3.5.2.9 5-oxoproline + H2O + ATP = H+ + L-glutamate + ADP γ-glutamyl cycle (plant pathway) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 3.5.2.9 5-oxoproline + H2O + ATP = H+ + L-glutamate + ADP γ-glutamyl cycle ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.11 H+ + L-serine + ATP = diphosphate + AMP selenocysteine biosynthesis II (archaea and eukaryotes) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 3.6.3.- Cu2+ + H2O + ATP = Cu2+ + ADP copper transport I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.21 H+ + L-histidine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = H+ + ADP + 5-aminoimidazole ribonucleotide 5-aminoimidazole ribonucleotide biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = H+ + ADP + 5-aminoimidazole ribonucleotide 5-aminoimidazole ribonucleotide biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = H+ + ADP + 5-aminoimidazole ribonucleotide superpathway of 5-aminoimidazole ribonucleotide biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.3 H+ + 4'-phosphopantetheine + ATP = dephospho-CoA + diphosphate coenzyme A biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.19 D-ribulose-5-phosphate + ATP = H+ + D-ribulose-1,5-bisphosphate + ADP Rubisco shunt ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.19 D-ribulose-5-phosphate + ATP = H+ + D-ribulose-1,5-bisphosphate + ADP Calvin-Benson-Bassham cycle ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.36 (R)-mevalonate + ATP = H+ + mevalonate-5-phosphate + ADP mevalonate pathway I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.12 H+ + L-aspartate + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.1 H+ + L-tyrosine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.151 D-myo-inositol (1,3,4,5)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.151 D-myo-inositol (1,3,4,5)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.151 D-myo-inositol (1,3,4,5)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.100 ATP + S-methyl-5-thio-D-ribose = H+ + ADP + 5-methylthioribose-1-phosphate methionine salvage I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.25 adenosine 5'-phosphosulfate + ATP = H+ + phosphoadenosine-5'-phosphosulfate + ADP sulfate activation for sulfonation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 1D-myo-inositol (3)-monophosphate + ATP = H+ + D-myo-inositol (3,4)-bisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.4.1.2 ATP + acetyl-CoA + bicarbonate = H+ + malonyl-CoA + ADP fatty acid biosynthesis initiation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.7 H+ + L-alanine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ flavonoid biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ simplecoumarins biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ phenylpropanoid biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ 4-hydroxybenzoate biosynthesis V ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.58 H+ + 2,3-dihydroxybenzoate + ATP = 2,3-dihydroxybenzoyl-AMP + diphosphate vibriobactin biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.2 L-cysteine + L-glutamate + ATP = H+ + L-γ-glutamylcysteine + ADP γ-glutamyl cycle (plant pathway) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.2 L-cysteine + L-glutamate + ATP = H+ + L-γ-glutamylcysteine + ADP glutathione biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = H+ + dethiobiotin + ADP biotin biosynthesis from 7-keto-8-aminopelargonate ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.14 bicarbonate + ATP = ADP biotin-carboxyl carrier protein assembly ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.25 ATP + CMP = ADP + CDP salvage pathways of pyrimidine ribonucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.7 hydroxymethylpyrimidine phosphate + ATP = 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate + ADP thiamine biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.34 ferulate + ATP + coenzyme A = feruloyl-CoA + AMP + diphosphate suberin biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.17 L-glutamate + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.17 L-glutamate + ATP = diphosphate + AMP tetrapyrrole biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.151 D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.151 D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.151 D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.154 ATP = ADP 3-phosphoinositide biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.26 riboflavin + ATP = H+ + FMN + ADP flavin biosynthesis I (bacteria and plants) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.4 H+ + sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate reduction II (assimilatory) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.4 H+ + sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfite oxidation III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.4 H+ + sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate activation for sulfonation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.137 ATP = ADP 3-phosphoinositide biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 503.152 C10 H12 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] CHEBI:15422:*PUBCHEM:9870745:*PUBCHEM:9870745:*PUBCHEM:5957:*LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.6 UDP + ATP = UTP + ADP pyrimidine ribonucleotides interconversion geranyl diphosphate geranyl-diphosphate*geranyl-pyrophosphate*GPP*geranyl-PP*geranyl pyrophosphate*ω,E-geranyl diphosphate 311.188 C10 H17 O7 P2 O(P([O-])(OP(=O)([O-])[O-])=O)CC=C(C)CCC=C(C)C KNAPSACK:C00000846:*PUBCHEM:19379894:*LIGAND-CPD:C00341: 4.2.3.- geranyl diphosphate = (E)-β-ocimene + diphosphate monoterpene biosynthesis geranyl diphosphate geranyl-diphosphate*geranyl-pyrophosphate*GPP*geranyl-PP*geranyl pyrophosphate*ω,E-geranyl diphosphate 311.188 C10 H17 O7 P2 O(P([O-])(OP(=O)([O-])[O-])=O)CC=C(C)CCC=C(C)C KNAPSACK:C00000846:*PUBCHEM:19379894:*LIGAND-CPD:C00341: 4.2.3.16 geranyl diphosphate = (-)-(4S)-limonene + diphosphate monoterpene biosynthesis geranyl diphosphate geranyl-diphosphate*geranyl-pyrophosphate*GPP*geranyl-PP*geranyl pyrophosphate*ω,E-geranyl diphosphate 311.188 C10 H17 O7 P2 O(P([O-])(OP(=O)([O-])[O-])=O)CC=C(C)CCC=C(C)C KNAPSACK:C00000846:*PUBCHEM:19379894:*LIGAND-CPD:C00341: 2.5.1.10 geranyl diphosphate + isopentenyl diphosphate = (2E,6E)-farnesyl diphosphate + diphosphate linalool biosynthesis geranyl diphosphate geranyl-diphosphate*geranyl-pyrophosphate*GPP*geranyl-PP*geranyl pyrophosphate*ω,E-geranyl diphosphate 311.188 C10 H17 O7 P2 O(P([O-])(OP(=O)([O-])[O-])=O)CC=C(C)CCC=C(C)C KNAPSACK:C00000846:*PUBCHEM:19379894:*LIGAND-CPD:C00341: 2.5.1.10 geranyl diphosphate + isopentenyl diphosphate = (2E,6E)-farnesyl diphosphate + diphosphate trans, trans-farnesyl diphosphate biosynthesis geranyl diphosphate geranyl-diphosphate*geranyl-pyrophosphate*GPP*geranyl-PP*geranyl pyrophosphate*ω,E-geranyl diphosphate 311.188 C10 H17 O7 P2 O(P([O-])(OP(=O)([O-])[O-])=O)CC=C(C)CCC=C(C)C KNAPSACK:C00000846:*PUBCHEM:19379894:*LIGAND-CPD:C00341: 4.2.3.14 geranyl diphosphate = (-)-β-pinene + diphosphate monoterpene biosynthesis geranyl diphosphate geranyl-diphosphate*geranyl-pyrophosphate*GPP*geranyl-PP*geranyl pyrophosphate*ω,E-geranyl diphosphate 311.188 C10 H17 O7 P2 O(P([O-])(OP(=O)([O-])[O-])=O)CC=C(C)CCC=C(C)C KNAPSACK:C00000846:*PUBCHEM:19379894:*LIGAND-CPD:C00341: 4.2.3.- geranyl diphosphate = sabinene + diphosphate monoterpene biosynthesis geranyl diphosphate geranyl-diphosphate*geranyl-pyrophosphate*GPP*geranyl-PP*geranyl pyrophosphate*ω,E-geranyl diphosphate 311.188 C10 H17 O7 P2 O(P([O-])(OP(=O)([O-])[O-])=O)CC=C(C)CCC=C(C)C KNAPSACK:C00000846:*PUBCHEM:19379894:*LIGAND-CPD:C00341: 4.2.3.- geranyl diphosphate = (Z)-β-ocimene + diphosphate monoterpene biosynthesis geranyl diphosphate geranyl-diphosphate*geranyl-pyrophosphate*GPP*geranyl-PP*geranyl pyrophosphate*ω,E-geranyl diphosphate 311.188 C10 H17 O7 P2 O(P([O-])(OP(=O)([O-])[O-])=O)CC=C(C)CCC=C(C)C KNAPSACK:C00000846:*PUBCHEM:19379894:*LIGAND-CPD:C00341: 2.5.1.1 dimethylallyl diphosphate + isopentenyl diphosphate = geranyl diphosphate + diphosphate geranyl diphosphate biosynthesis geranyl diphosphate geranyl-diphosphate*geranyl-pyrophosphate*GPP*geranyl-PP*geranyl pyrophosphate*ω,E-geranyl diphosphate 311.188 C10 H17 O7 P2 O(P([O-])(OP(=O)([O-])[O-])=O)CC=C(C)CCC=C(C)C KNAPSACK:C00000846:*PUBCHEM:19379894:*LIGAND-CPD:C00341: 2.5.1.1 dimethylallyl diphosphate + isopentenyl diphosphate = geranyl diphosphate + diphosphate trans, trans-farnesyl diphosphate biosynthesis geranyl diphosphate geranyl-diphosphate*geranyl-pyrophosphate*GPP*geranyl-PP*geranyl pyrophosphate*ω,E-geranyl diphosphate 311.188 C10 H17 O7 P2 O(P([O-])(OP(=O)([O-])[O-])=O)CC=C(C)CCC=C(C)C KNAPSACK:C00000846:*PUBCHEM:19379894:*LIGAND-CPD:C00341: 4.2.3.26 geranyl diphosphate + H2O = (3R)-linalool + diphosphate linalool biosynthesis geranyl diphosphate geranyl-diphosphate*geranyl-pyrophosphate*GPP*geranyl-PP*geranyl pyrophosphate*ω,E-geranyl diphosphate 311.188 C10 H17 O7 P2 O(P([O-])(OP(=O)([O-])[O-])=O)CC=C(C)CCC=C(C)C KNAPSACK:C00000846:*PUBCHEM:19379894:*LIGAND-CPD:C00341: 4.2.3.14 geranyl diphosphate = (-)-α-pinene + diphosphate monoterpene biosynthesis geranyl diphosphate geranyl-diphosphate*geranyl-pyrophosphate*GPP*geranyl-PP*geranyl pyrophosphate*ω,E-geranyl diphosphate 311.188 C10 H17 O7 P2 O(P([O-])(OP(=O)([O-])[O-])=O)CC=C(C)CCC=C(C)C KNAPSACK:C00000846:*PUBCHEM:19379894:*LIGAND-CPD:C00341: 4.2.3.15 geranyl diphosphate = β-myrcene + diphosphate monoterpene biosynthesis geranyl diphosphate geranyl-diphosphate*geranyl-pyrophosphate*GPP*geranyl-PP*geranyl pyrophosphate*ω,E-geranyl diphosphate 311.188 C10 H17 O7 P2 O(P([O-])(OP(=O)([O-])[O-])=O)CC=C(C)CCC=C(C)C KNAPSACK:C00000846:*PUBCHEM:19379894:*LIGAND-CPD:C00341: 4.2.3.- geranyl diphosphate + H2O = (-)-α-terpineol + diphosphate monoterpene biosynthesis geranyl diphosphate geranyl-diphosphate*geranyl-pyrophosphate*GPP*geranyl-PP*geranyl pyrophosphate*ω,E-geranyl diphosphate 311.188 C10 H17 O7 P2 O(P([O-])(OP(=O)([O-])[O-])=O)CC=C(C)CCC=C(C)C KNAPSACK:C00000846:*PUBCHEM:19379894:*LIGAND-CPD:C00341: 4.2.3.- geranyl diphosphate = terpinolene + diphosphate monoterpene biosynthesis geranyl diphosphate geranyl-diphosphate*geranyl-pyrophosphate*GPP*geranyl-PP*geranyl pyrophosphate*ω,E-geranyl diphosphate 311.188 C10 H17 O7 P2 O(P([O-])(OP(=O)([O-])[O-])=O)CC=C(C)CCC=C(C)C KNAPSACK:C00000846:*PUBCHEM:19379894:*LIGAND-CPD:C00341: 4.2.3.25 geranyl diphosphate + H2O = (3S)-linalool + diphosphate linalool biosynthesis (22R,23R)-22,23-dihydroxy-campest-4-en-3-one 430.67 C28 H46 O3 C1(CC(C=C2(C1(C3(C(CC2)C4(CCC(C(C(C(O)C(C(C)C)C)O)C)C(CC3)(C)4)))C))=O) 1.14.13.- H+ + (22α)-hydroxy-campest-4-en-3-one + NADPH + oxygen = (22R,23R)-22,23-dihydroxy-campest-4-en-3-one + NADP+ + H2O brassinosteroid biosynthesis II (22R,23R)-22,23-dihydroxy-campest-4-en-3-one 430.67 C28 H46 O3 C1(CC(C=C2(C1(C3(C(CC2)C4(CCC(C(C(C(O)C(C(C)C)C)O)C)C(CC3)(C)4)))C))=O) (22R,23R)-22,23-dihydroxycampesterol = H+ + (22R,23R)-22,23-dihydroxy-campest-4-en-3-one brassinosteroid biosynthesis II (22R,23R)-22,23-dihydroxy-campest-4-en-3-one 430.67 C28 H46 O3 C1(CC(C=C2(C1(C3(C(CC2)C4(CCC(C(C(C(O)C(C(C)C)C)O)C)C(CC3)(C)4)))C))=O) H+ + (22R,23R)-22,23-dihydroxy-campest-4-en-3-one = 3-dehydro-6-deoxoteasterone brassinosteroid biosynthesis II GA44 GA44 (closed lactone form)*gibberellin A44 (closed lactone form)*gibberellin A44 (closed lactone form)*GA44 (closed lactone form)*gibberellin A44*gibberellin A44*GA44*GA44 open lactone form*GA44 free alcohol form*gibberellin A44 free alcohol form 345.414 C20 H25 O5 C15(C)(C(=O)OCC4(CCC1)(C(C(C([O-])=O)C23(CC(=C)C(O)(C2)CCC34))5)) LIGAND-CPD:C12308:*CHEBI:28211:*PUBCHEM:443756:*CHEBI:58554:*PUBCHEM:25244669:*LIGAND-CPD:C12308: 1.14.11.- H+ + GA44 + 2-oxoglutarate + oxygen = GA98 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = H+ + glutathione + ADP γ-glutamyl cycle (plant pathway) glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = H+ + glutathione + ADP glutathione biosynthesis glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 3.4.11.2 cysteinylglycine + H2O = L-cysteine + glycine γ-glutamyl cycle (plant pathway) glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 3.4.11.2 cysteinylglycine + H2O = L-cysteine + glycine glutathione degradation glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 3.4.11.2 cysteinylglycine + H2O = L-cysteine + glycine γ-glutamyl cycle glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 6.1.1.14 H+ + glycine + ATP = diphosphate + AMP tRNA charging pathway glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 2.6.1.4 2-oxoglutarate + glycine = L-glutamate + glyoxylate photorespiration glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide 5-aminoimidazole ribonucleotide biosynthesis II glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide 5-aminoimidazole ribonucleotide biosynthesis I glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide superpathway of 5-aminoimidazole ribonucleotide biosynthesis glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations I glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations II (plants) glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH photorespiration glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 glycine + L-cysteine + NAD+ = 2-carboxylate-4-methyl-5-beta-(ethyl adenosine 5-diphosphate) thiazole + nicotinamide thiamine biosynthesis II glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 1.4.4.2 glycine = CO2 glycine cleavage complex glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O glycine biosynthesis I glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O folate transformations I glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O folate transformations II (plants) glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O folate polyglutamylation glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O photorespiration glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 4.1.2.5 L-threonine = acetaldehyde + glycine glycine biosynthesis IV glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)([O-])C[N+] CHEBI:15428:*PUBCHEM:5257127:*KNAPSACK:C00001361:*PUBCHEM:5257127:*KNAPKSACK:C00001361*LIGAND-CPD:C00037:*CAS:56-40-6 2.6.1.45 glyoxylate + L-serine = hydroxypyruvate + glycine photorespiration (2R,3S)-3-isopropylmalate (2R,3S)-3-isopropylmalate*2-D-threo-hydroxy-3-carboxy-isocaproate*3-carboxy-2-hydroxy-4-methylpentanoate*β-isopropylmalate*3-isopropylmalate 174.153 C7 H10 O5 [O-]C(=O)C(O)C(C(C)C)C([O-])=O PUBCHEM:6857402:*CHEBI:35121:*LIGAND-CPD:C04411: 4.2.1.33 (2R,3S)-3-isopropylmalate = 2-isopropylmaleate + H2O leucine biosynthesis (2R,3S)-3-isopropylmalate (2R,3S)-3-isopropylmalate*2-D-threo-hydroxy-3-carboxy-isocaproate*3-carboxy-2-hydroxy-4-methylpentanoate*β-isopropylmalate*3-isopropylmalate 174.153 C7 H10 O5 [O-]C(=O)C(O)C(C(C)C)C([O-])=O PUBCHEM:6857402:*CHEBI:35121:*LIGAND-CPD:C04411: 1.1.1.85 (2R,3S)-3-isopropylmalate + NAD+ = (2S)-2-isopropyl-3-oxosuccinate + NADH + H+ leucine biosynthesis (E)-indol-3-ylacetaldoxime (E)-indole-3-acetaldoxime*(E)-indole-3-acetaldehyde oxime*(E)-3-indoleacetaldoxime*3-indoleacetaldoxime*indole-3-acetaldehyde oxime 174.202 C10 H10 N2 O1 C2(=CC=CC1(=C(NC=C(CC=NO)1)2)) PUBCHEM:5371769:*CHEBI:17545:*LIGAND-CPD:C02937: (E)-indol-3-ylacetaldoxime = (Z)-indol-3-ylacetaldoxime IAA biosynthesis I (E)-indol-3-ylacetaldoxime (E)-indole-3-acetaldoxime*(E)-indole-3-acetaldehyde oxime*(E)-3-indoleacetaldoxime*3-indoleacetaldoxime*indole-3-acetaldehyde oxime 174.202 C10 H10 N2 O1 C2(=CC=CC1(=C(NC=C(CC=NO)1)2)) PUBCHEM:5371769:*CHEBI:17545:*LIGAND-CPD:C02937: N-hydroxyl-tryptamine = H+ + (E)-indol-3-ylacetaldoxime IAA biosynthesis I (E)-indol-3-ylacetaldoxime (E)-indole-3-acetaldoxime*(E)-indole-3-acetaldehyde oxime*(E)-3-indoleacetaldoxime*3-indoleacetaldoxime*indole-3-acetaldehyde oxime 174.202 C10 H10 N2 O1 C2(=CC=CC1(=C(NC=C(CC=NO)1)2)) PUBCHEM:5371769:*CHEBI:17545:*LIGAND-CPD:C02937: 1.14.13.- H+ + N,N-dihydroxy-L-tryptophan = (E)-indol-3-ylacetaldoxime + CO2 + H2O IAA biosynthesis I DIMBOA 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 210.166 C9 H8 N1 O5 C1(C=CC2(=C(C=1)OC(C(N2[O-])=O)O))OC PUBCHEM:25200838:*LIGAND-CPD:C04720: 3.2.1.21 DIMBOA-Glc + H2O = DIMBOA + β-D-glucose DIMBOA-glucoside degradation ethanolamine 2-aminoethanol*monoethanolamine*colamine*ethanol-amine 62.091 C2 H8 N1 O1 [N+]CCO PUBCHEM:444693:*CHEBI:57603:*KNAPSACK:C00007279:*PUBCHEM:700:*LIGAND:C00189:*LIGAND-CPD:C00189:*CAS:141-43-5 2.7.1.82 ethanolamine + ATP = H+ + phosphoryl-ethanolamine + ADP phosphatidylethanolamine biosynthesis II ethanolamine 2-aminoethanol*monoethanolamine*colamine*ethanol-amine 62.091 C2 H8 N1 O1 [N+]CCO PUBCHEM:444693:*CHEBI:57603:*KNAPSACK:C00007279:*PUBCHEM:700:*LIGAND:C00189:*LIGAND-CPD:C00189:*CAS:141-43-5 2.7.1.82 ethanolamine + ATP = H+ + phosphoryl-ethanolamine + ADP choline biosynthesis I ethanolamine 2-aminoethanol*monoethanolamine*colamine*ethanol-amine 62.091 C2 H8 N1 O1 [N+]CCO PUBCHEM:444693:*CHEBI:57603:*KNAPSACK:C00007279:*PUBCHEM:700:*LIGAND:C00189:*LIGAND-CPD:C00189:*CAS:141-43-5 4.1.1.- H+ + L-serine = ethanolamine + CO2 choline biosynthesis I ethanolamine 2-aminoethanol*monoethanolamine*colamine*ethanol-amine 62.091 C2 H8 N1 O1 [N+]CCO PUBCHEM:444693:*CHEBI:57603:*KNAPSACK:C00007279:*PUBCHEM:700:*LIGAND:C00189:*LIGAND-CPD:C00189:*CAS:141-43-5 2.7.8.29 L-serine = ethanolamine phospholipid biosynthesis II isovaleryl-CoA 3-methylbutyryl-CoA*3-methylbutanoyl-CoA*isovaleryl-coenzyme A*iso-valeryl-CoA 847.62 C26 H40 N7 O17 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP([O-])(OCC(C)(C)C(C(NCCC(=O)NCCSC(=O)CC(C)C)=O)O)=O)O1)OP([O-])(=O)[O-])(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25244093:*LIGAND-CPD:C02939:*CAS:6244-91-3 4-methyl-2-oxopentanoate + coenzyme A + NAD+ = isovaleryl-CoA + CO2 + NADH leucine degradation I isovaleryl-CoA 3-methylbutyryl-CoA*3-methylbutanoyl-CoA*isovaleryl-coenzyme A*iso-valeryl-CoA 847.62 C26 H40 N7 O17 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP([O-])(OCC(C)(C)C(C(NCCC(=O)NCCSC(=O)CC(C)C)=O)O)=O)O1)OP([O-])(=O)[O-])(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25244093:*LIGAND-CPD:C02939:*CAS:6244-91-3 1.3.99.10 isovaleryl-CoA = 3-methylcrotonyl-CoA leucine degradation I superoxide O2-*superoxide anion*Superoxide anion*peroxide radical*O2(.-)*superoxide 31.999 O2 O=[O-] PUBCHEM:25202496:*LIGAND-CPD:C00704: 1.15.1.1 superoxide + H+ = hydrogen peroxide + oxygen superoxide radicals degradation 9'-cis-neurosporene 538.898 C40 H58 CC(=CCCC(=CC=CC(C)=CC=CC(=CC=CC=C(C=CC=C(C)CCC=C(CCC=C(C)C)C)C)C)C)C PUBCHEM:21606092: 9'-cis-neurosporene + oxygen = 7',9'-cis-lycopene + H2O trans-lycopene biosynthesis II (plants) 9'-cis-neurosporene 538.898 C40 H58 CC(=CCCC(=CC=CC(C)=CC=CC(=CC=CC=C(C=CC=C(C)CCC=C(CCC=C(C)C)C)C)C)C)C PUBCHEM:21606092: 5.2.1.- 7,9,9'-cis-neurosporene = 9'-cis-neurosporene trans-lycopene biosynthesis II (plants) all-trans-octaprenyl diphosphate all-trans-octaprenyl diphosphate*farnesylfarnesylgeranyl-PP*octaprenyl pyrophosphate*OPP*farnesylfarnesylgeraniol*octaprenyl diphosphate 719.897 C40 H65 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:57711:*PUBCHEM:25245331:*LIGAND-CPD:C04146: 2.5.1.90 all-trans-heptaprenyl diphosphate + isopentenyl diphosphate = H+ + diphosphate + all-trans-octaprenyl diphosphate nonaprenyl diphosphate biosynthesis III all-trans-octaprenyl diphosphate all-trans-octaprenyl diphosphate*farnesylfarnesylgeranyl-PP*octaprenyl pyrophosphate*OPP*farnesylfarnesylgeraniol*octaprenyl diphosphate 719.897 C40 H65 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:57711:*PUBCHEM:25245331:*LIGAND-CPD:C04146: 2.5.1.84 all-trans-octaprenyl diphosphate + isopentenyl diphosphate = H+ + all-trans-nonaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III coproporphyrinogen III coproporphyrinogen 656.734 C36 H40 N4 O8 CC1(=C2(CC5(=C(CCC(=O)[O-])C(C)=C(CC4(=C(CCC([O-])=O)C(C)=C(CC3(=C(C)C(CCC([O-])=O)=C(CC(=C(CCC([O-])=O)1)N2)N3))N4))N5))) CHEBI:57309:*PUBCHEM:20849114:*LIGAND-CPD:C03263:*CAS:2624-63-7 4.1.1.37 uroporphyrinogen-III + H+ = coproporphyrinogen III + CO2 chlorophyllide a biosynthesis I coproporphyrinogen III coproporphyrinogen 656.734 C36 H40 N4 O8 CC1(=C2(CC5(=C(CCC(=O)[O-])C(C)=C(CC4(=C(CCC([O-])=O)C(C)=C(CC3(=C(C)C(CCC([O-])=O)=C(CC(=C(CCC([O-])=O)1)N2)N3))N4))N5))) CHEBI:57309:*PUBCHEM:20849114:*LIGAND-CPD:C03263:*CAS:2624-63-7 4.1.1.37 uroporphyrinogen-III + H+ = coproporphyrinogen III + CO2 heme biosynthesis from uroporphyrinogen-III I coproporphyrinogen III coproporphyrinogen 656.734 C36 H40 N4 O8 CC1(=C2(CC5(=C(CCC(=O)[O-])C(C)=C(CC4(=C(CCC([O-])=O)C(C)=C(CC3(=C(C)C(CCC([O-])=O)=C(CC(=C(CCC([O-])=O)1)N2)N3))N4))N5))) CHEBI:57309:*PUBCHEM:20849114:*LIGAND-CPD:C03263:*CAS:2624-63-7 1.3.3.3 coproporphyrinogen III + oxygen + H+ = protoporphyrinogen IX + CO2 + H2O chlorophyllide a biosynthesis I coproporphyrinogen III coproporphyrinogen 656.734 C36 H40 N4 O8 CC1(=C2(CC5(=C(CCC(=O)[O-])C(C)=C(CC4(=C(CCC([O-])=O)C(C)=C(CC3(=C(C)C(CCC([O-])=O)=C(CC(=C(CCC([O-])=O)1)N2)N3))N4))N5))) CHEBI:57309:*PUBCHEM:20849114:*LIGAND-CPD:C03263:*CAS:2624-63-7 1.3.3.3 coproporphyrinogen III + oxygen + H+ = protoporphyrinogen IX + CO2 + H2O heme biosynthesis from uroporphyrinogen-III I 6,7-dimethyl-8-(1-D-ribityl)lumazine 325.3 C13 H17 N4 O6 C2(C)(=C(C)N=C1(C(=NC([N-]C(=O)1)=O)N(CC(O)C(O)C(O)CO)2)) PUBCHEM:25244683:*LIGAND-CPD:C04332: 2.5.1.78 5-amino-6-(D-ribitylamino)uracil + 1-deoxy-L-glycero-tetrulose 4-phosphate = H+ + 6,7-dimethyl-8-(1-D-ribityl)lumazine + H2O flavin biosynthesis I (bacteria and plants) 6,7-dimethyl-8-(1-D-ribityl)lumazine 325.3 C13 H17 N4 O6 C2(C)(=C(C)N=C1(C(=NC([N-]C(=O)1)=O)N(CC(O)C(O)C(O)CO)2)) PUBCHEM:25244683:*LIGAND-CPD:C04332: 2.5.1.9 H+ + 6,7-dimethyl-8-(1-D-ribityl)lumazine = 5-amino-6-(D-ribitylamino)uracil + riboflavin flavin biosynthesis I (bacteria and plants) glutamate-1-semialdehyde (S)-4-amino-5-oxopentanoate*L-Glutamate 1-semialdehyde 131.131 C5 H9 N1 O3 C(C(CCC([O-])=O)[N+])=O CHEBI:57501:*PUBCHEM:25244684:*LIGAND-CPD:C03741: 1.2.1.70 glutamate-1-semialdehyde + NADP+ = NADPH tetrapyrrole biosynthesis I glutamate-1-semialdehyde (S)-4-amino-5-oxopentanoate*L-Glutamate 1-semialdehyde 131.131 C5 H9 N1 O3 C(C(CCC([O-])=O)[N+])=O CHEBI:57501:*PUBCHEM:25244684:*LIGAND-CPD:C03741: 5.4.3.8 glutamate-1-semialdehyde = 5-amino-levulinate tetrapyrrole biosynthesis I glyoxylate glyoxalate*glyox*glyoxylic acid 73.028 C2 H1 O3 C(C=O)(=O)[O-] PUBCHEM:3614358:*KNAPSACK:C00001186*PUBCHEM:3614358:*CHEBI:35179:*KNAPKSACK:C00001186*LIGAND-CPD:C00048:*CAS:298-12-4 1.1.3.15 glycolate + oxygen = glyoxylate + hydrogen peroxide photorespiration glyoxylate glyoxalate*glyox*glyoxylic acid 73.028 C2 H1 O3 C(C=O)(=O)[O-] PUBCHEM:3614358:*KNAPSACK:C00001186*PUBCHEM:3614358:*CHEBI:35179:*KNAPKSACK:C00001186*LIGAND-CPD:C00048:*CAS:298-12-4 2.3.3.9 acetyl-CoA + H2O + glyoxylate = H+ + (S)-malate + coenzyme A glyoxylate cycle glyoxylate glyoxalate*glyox*glyoxylic acid 73.028 C2 H1 O3 C(C=O)(=O)[O-] PUBCHEM:3614358:*KNAPSACK:C00001186*PUBCHEM:3614358:*CHEBI:35179:*KNAPKSACK:C00001186*LIGAND-CPD:C00048:*CAS:298-12-4 2.3.3.9 acetyl-CoA + H2O + glyoxylate = H+ + (S)-malate + coenzyme A glycolate and glyoxylate degradation II glyoxylate glyoxalate*glyox*glyoxylic acid 73.028 C2 H1 O3 C(C=O)(=O)[O-] PUBCHEM:3614358:*KNAPSACK:C00001186*PUBCHEM:3614358:*CHEBI:35179:*KNAPKSACK:C00001186*LIGAND-CPD:C00048:*CAS:298-12-4 1.1.99.14 glycolate = glyoxylate glycolate and glyoxylate degradation II glyoxylate glyoxalate*glyox*glyoxylic acid 73.028 C2 H1 O3 C(C=O)(=O)[O-] PUBCHEM:3614358:*KNAPSACK:C00001186*PUBCHEM:3614358:*CHEBI:35179:*KNAPKSACK:C00001186*LIGAND-CPD:C00048:*CAS:298-12-4 2.6.1.4 2-oxoglutarate + glycine = L-glutamate + glyoxylate photorespiration glyoxylate glyoxalate*glyox*glyoxylic acid 73.028 C2 H1 O3 C(C=O)(=O)[O-] PUBCHEM:3614358:*KNAPSACK:C00001186*PUBCHEM:3614358:*CHEBI:35179:*KNAPKSACK:C00001186*LIGAND-CPD:C00048:*CAS:298-12-4 4.1.3.1 D-threo-isocitrate = glyoxylate + succinate glyoxylate cycle glyoxylate glyoxalate*glyox*glyoxylic acid 73.028 C2 H1 O3 C(C=O)(=O)[O-] PUBCHEM:3614358:*KNAPSACK:C00001186*PUBCHEM:3614358:*CHEBI:35179:*KNAPKSACK:C00001186*LIGAND-CPD:C00048:*CAS:298-12-4 2.6.1.45 glyoxylate + L-serine = hydroxypyruvate + glycine photorespiration glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 306.313 C10 H16 N3 O6 S1 [N+]C(C(=O)[O-])CCC(NC(CS)C(NCC(=O)[O-])=O)=O PUBCHEM:20756463:*KNAPSACK:C00001518:*LIGAND-CPD:C00051:*CAS:70-18-8 glutathione = 5-oxoproline + cysteinylglycine γ-glutamyl cycle (plant pathway) glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 306.313 C10 H16 N3 O6 S1 [N+]C(C(=O)[O-])CCC(NC(CS)C(NCC(=O)[O-])=O)=O PUBCHEM:20756463:*KNAPSACK:C00001518:*LIGAND-CPD:C00051:*CAS:70-18-8 2.3.2.2 hypoglycin A + glutathione = hypoglycin B + cysteinylglycine hypoglycin biosynthesis glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 306.313 C10 H16 N3 O6 S1 [N+]C(C(=O)[O-])CCC(NC(CS)C(NCC(=O)[O-])=O)=O PUBCHEM:20756463:*KNAPSACK:C00001518:*LIGAND-CPD:C00051:*CAS:70-18-8 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = H+ + glutathione + ADP γ-glutamyl cycle (plant pathway) glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 306.313 C10 H16 N3 O6 S1 [N+]C(C(=O)[O-])CCC(NC(CS)C(NCC(=O)[O-])=O)=O PUBCHEM:20756463:*KNAPSACK:C00001518:*LIGAND-CPD:C00051:*CAS:70-18-8 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = H+ + glutathione + ADP glutathione biosynthesis glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 306.313 C10 H16 N3 O6 S1 [N+]C(C(=O)[O-])CCC(NC(CS)C(NCC(=O)[O-])=O)=O PUBCHEM:20756463:*KNAPSACK:C00001518:*LIGAND-CPD:C00051:*CAS:70-18-8 2.3.2.2 glutathione + H2O = cysteinylglycine + L-glutamate glutathione degradation glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 306.313 C10 H16 N3 O6 S1 [N+]C(C(=O)[O-])CCC(NC(CS)C(NCC(=O)[O-])=O)=O PUBCHEM:20756463:*KNAPSACK:C00001518:*LIGAND-CPD:C00051:*CAS:70-18-8 1.8.1.7 glutathione + NADP+ = glutathione disulfide + NADPH + H+ glutathione redox reactions I glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 306.313 C10 H16 N3 O6 S1 [N+]C(C(=O)[O-])CCC(NC(CS)C(NCC(=O)[O-])=O)=O PUBCHEM:20756463:*KNAPSACK:C00001518:*LIGAND-CPD:C00051:*CAS:70-18-8 1.8.1.7 glutathione + NADP+ = glutathione disulfide + NADPH + H+ glutathione redox reactions II glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 306.313 C10 H16 N3 O6 S1 [N+]C(C(=O)[O-])CCC(NC(CS)C(NCC(=O)[O-])=O)=O PUBCHEM:20756463:*KNAPSACK:C00001518:*LIGAND-CPD:C00051:*CAS:70-18-8 1.8.4.9 H+ + sulfite + AMP + glutathione disulfide = adenosine 5'-phosphosulfate + glutathione sulfate reduction II (assimilatory) glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 306.313 C10 H16 N3 O6 S1 [N+]C(C(=O)[O-])CCC(NC(CS)C(NCC(=O)[O-])=O)=O PUBCHEM:20756463:*KNAPSACK:C00001518:*LIGAND-CPD:C00051:*CAS:70-18-8 1.8.4.2 glutathione = glutathione disulfide glutathione redox reactions II glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 306.313 C10 H16 N3 O6 S1 [N+]C(C(=O)[O-])CCC(NC(CS)C(NCC(=O)[O-])=O)=O PUBCHEM:20756463:*KNAPSACK:C00001518:*LIGAND-CPD:C00051:*CAS:70-18-8 1.11.1.9 hydrogen peroxide + glutathione = glutathione disulfide + H2O glutathione redox reactions I glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 306.313 C10 H16 N3 O6 S1 [N+]C(C(=O)[O-])CCC(NC(CS)C(NCC(=O)[O-])=O)=O PUBCHEM:20756463:*KNAPSACK:C00001518:*LIGAND-CPD:C00051:*CAS:70-18-8 glutathione = L-γ-glutamylcysteine γ-glutamyl cycle (plant pathway) glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 306.313 C10 H16 N3 O6 S1 [N+]C(C(=O)[O-])CCC(NC(CS)C(NCC(=O)[O-])=O)=O PUBCHEM:20756463:*KNAPSACK:C00001518:*LIGAND-CPD:C00051:*CAS:70-18-8 1.8.5.1 L-dehydro-ascorbate + glutathione = H+ + glutathione disulfide + L-ascorbate ascorbate glutathione cycle glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 306.313 C10 H16 N3 O6 S1 [N+]C(C(=O)[O-])CCC(NC(CS)C(NCC(=O)[O-])=O)=O PUBCHEM:20756463:*KNAPSACK:C00001518:*LIGAND-CPD:C00051:*CAS:70-18-8 1.11.1.12 glutathione = glutathione disulfide + H2O glutathione redox reactions I glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 306.313 C10 H16 N3 O6 S1 [N+]C(C(=O)[O-])CCC(NC(CS)C(NCC(=O)[O-])=O)=O PUBCHEM:20756463:*KNAPSACK:C00001518:*LIGAND-CPD:C00051:*CAS:70-18-8 2.3.2.2 cysteinylglycine = glutathione γ-glutamyl cycle dATP 2'-deoxyATP*2'-deoxyadenosine triphosphate*deoxy-ATP*deoxyadenosine-triphosphate*2'-deoxyadenosine-5'-triphosphate 487.152 C10 H12 N5 O12 P3 O=P(OP(OP(=O)([O-])[O-])([O-])=O)(OCC3(C(CC(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O))[O-] PUBCHEM:25320183:*CHEBI:16284:*CHEBI:16284:*PUBCHEM:25244444:*LIGAND-CPD:C00131:*CAS:1927-31-7 ATP = dATP + H2O adenosine nucleotides de novo biosynthesis dATP 2'-deoxyATP*2'-deoxyadenosine triphosphate*deoxy-ATP*deoxyadenosine-triphosphate*2'-deoxyadenosine-5'-triphosphate 487.152 C10 H12 N5 O12 P3 O=P(OP(OP(=O)([O-])[O-])([O-])=O)(OCC3(C(CC(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O))[O-] PUBCHEM:25320183:*CHEBI:16284:*CHEBI:16284:*PUBCHEM:25244444:*LIGAND-CPD:C00131:*CAS:1927-31-7 2.7.4.6 dADP + ATP = dATP + ADP adenosine nucleotides de novo biosynthesis gibberellin A1 gibberellin 1*GA1*gibberellin A1*GA1*gibberellin A1 347.387 C19 H23 O6 C1(CC(C2(C4(C1(OC2=O)C5(CCC3(CC(CC3=C)(C4C([O-])=O)5)O)))(C))O) PUBCHEM:25202506:*LIGAND-CPD:C00859: 1.14.11.15 gibberellin A20 + 2-oxoglutarate + oxygen = gibberellin A1 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) gibberellin A1 gibberellin 1*GA1*gibberellin A1*GA1*gibberellin A1 347.387 C19 H23 O6 C1(CC(C2(C4(C1(OC2=O)C5(CCC3(CC(CC3=C)(C4C([O-])=O)5)O)))(C))O) PUBCHEM:25202506:*LIGAND-CPD:C00859: 1.14.11.13 gibberellin A1 + 2-oxoglutarate + oxygen = gibberellin A8 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) OPC8-3-hydroxyacyl-CoA 1055.92 C39 H60 N7 O19 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)C(O)CCCCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237307: 4.2.1.17 OPC8-3-hydroxyacyl-CoA = OPC8-trans-2-enoyl-CoA + H2O jasmonic acid biosynthesis OPC8-3-hydroxyacyl-CoA 1055.92 C39 H60 N7 O19 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)C(O)CCCCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237307: 1.1.1.35 NAD+ + OPC8-3-hydroxyacyl-CoA = NADH + H+ + OPC8-3-ketoacyl-CoA jasmonic acid biosynthesis CDP-choline citicoline*citicholine*cidifos*cyticholine*cytidine 5'-diphosphocholine*cytidine diphosphate choline 487.319 C14 H25 N4 O11 P2 [O-]P(=O)(OCC1(OC(C(O)C(O)1)N2(C=CC(=NC2=O)N)))OP(OCC[N+](C)(C)C)([O-])=O KNAPSACK:C00007231:*CHEBI:58779:*PUBCHEM:25202509:*LIGAND-CPD:C00307:*CAS:987-78-0 2.7.8.2 CDP-choline = CMP + H+ phosphatidylcholine biosynthesis I CDP-choline citicoline*citicholine*cidifos*cyticholine*cytidine 5'-diphosphocholine*cytidine diphosphate choline 487.319 C14 H25 N4 O11 P2 [O-]P(=O)(OCC1(OC(C(O)C(O)1)N2(C=CC(=NC2=O)N)))OP(OCC[N+](C)(C)C)([O-])=O KNAPSACK:C00007231:*CHEBI:58779:*PUBCHEM:25202509:*LIGAND-CPD:C00307:*CAS:987-78-0 2.7.8.2 CDP-choline = CMP + H+ choline biosynthesis III CDP-choline citicoline*citicholine*cidifos*cyticholine*cytidine 5'-diphosphocholine*cytidine diphosphate choline 487.319 C14 H25 N4 O11 P2 [O-]P(=O)(OCC1(OC(C(O)C(O)1)N2(C=CC(=NC2=O)N)))OP(OCC[N+](C)(C)C)([O-])=O KNAPSACK:C00007231:*CHEBI:58779:*PUBCHEM:25202509:*LIGAND-CPD:C00307:*CAS:987-78-0 2.7.8.2 CDP-choline = CMP + H+ phosphatidylcholine biosynthesis II CDP-choline citicoline*citicholine*cidifos*cyticholine*cytidine 5'-diphosphocholine*cytidine diphosphate choline 487.319 C14 H25 N4 O11 P2 [O-]P(=O)(OCC1(OC(C(O)C(O)1)N2(C=CC(=NC2=O)N)))OP(OCC[N+](C)(C)C)([O-])=O KNAPSACK:C00007231:*CHEBI:58779:*PUBCHEM:25202509:*LIGAND-CPD:C00307:*CAS:987-78-0 2.7.7.15 H+ + phosphoryl-choline + CTP = CDP-choline + diphosphate phosphatidylcholine biosynthesis I CDP-choline citicoline*citicholine*cidifos*cyticholine*cytidine 5'-diphosphocholine*cytidine diphosphate choline 487.319 C14 H25 N4 O11 P2 [O-]P(=O)(OCC1(OC(C(O)C(O)1)N2(C=CC(=NC2=O)N)))OP(OCC[N+](C)(C)C)([O-])=O KNAPSACK:C00007231:*CHEBI:58779:*PUBCHEM:25202509:*LIGAND-CPD:C00307:*CAS:987-78-0 2.7.7.15 H+ + phosphoryl-choline + CTP = CDP-choline + diphosphate choline biosynthesis III CDP-choline citicoline*citicholine*cidifos*cyticholine*cytidine 5'-diphosphocholine*cytidine diphosphate choline 487.319 C14 H25 N4 O11 P2 [O-]P(=O)(OCC1(OC(C(O)C(O)1)N2(C=CC(=NC2=O)N)))OP(OCC[N+](C)(C)C)([O-])=O KNAPSACK:C00007231:*CHEBI:58779:*PUBCHEM:25202509:*LIGAND-CPD:C00307:*CAS:987-78-0 2.7.7.15 H+ + phosphoryl-choline + CTP = CDP-choline + diphosphate phosphatidylcholine biosynthesis II dTTP thymidine triphosphate*thymidine 5'-triphosphate*TTP 478.139 C10 H13 N2 O14 P3 CC1(=CN(C(=O)NC(=O)1)C2(CC(O)C(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])O2)) PUBCHEM:11988283:*CHEBI:37568:*LIGAND-CPD:C00459:*CAS:365-08-2: 2.7.4.6 dTDP + ATP = dTTP + ADP pyrimidine deoxyribonucleotides de novo biosynthesis I secologanin (-)-secologanin 388.371 C17 H24 O10 C=CC1(C(OC=C(C(=O)OC)C(CC=O)1)OC2(OC(CO)C(O)C(O)C(O)2)) PUBCHEM:161276:*CHEBI:18002:*LIGAND-CPD:C01852: 1.3.3.9 H+ + oxygen + NADPH + loganin = H2O + NADP+ + secologanin camptothecin biosynthesis secologanin (-)-secologanin 388.371 C17 H24 O10 C=CC1(C(OC=C(C(=O)OC)C(CC=O)1)OC2(OC(CO)C(O)C(O)C(O)2)) PUBCHEM:161276:*CHEBI:18002:*LIGAND-CPD:C01852: 4.3.3.2 tryptamine + secologanin = strictosidine + H2O camptothecin biosynthesis β-L-fucose 1-phosphate β-L-fucose 1-phosphate*L-Fucose 1-phosphate*6-deoxy-L-galactose 1-phosphate*L-fucopyranose 1-(dihydrogen phosphate) 242.122 C6 H11 O8 P1 CC1(OC(OP(=O)([O-])[O-])C(O)C(O)C(O)1) CAS:526-31-8:*CHEBI:28319:*PUBCHEM:25203409:*LIGAND-CPD:C02985: 2.7.7.30 H+ + β-L-fucose 1-phosphate + GTP = GDP-L-fucose + diphosphate GDP-L-fucose biosynthesis II (from L-fucose) β-L-fucose 1-phosphate β-L-fucose 1-phosphate*L-Fucose 1-phosphate*6-deoxy-L-galactose 1-phosphate*L-fucopyranose 1-(dihydrogen phosphate) 242.122 C6 H11 O8 P1 CC1(OC(OP(=O)([O-])[O-])C(O)C(O)C(O)1) CAS:526-31-8:*CHEBI:28319:*PUBCHEM:25203409:*LIGAND-CPD:C02985: 2.7.1.52 ATP = β-L-fucose 1-phosphate + ADP GDP-L-fucose biosynthesis II (from L-fucose) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH gluconeogenesis I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH glycolysis III NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH glycolysis IV (plant cytosol) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH glycolysis I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.1 ethanol + NAD+ = acetaldehyde + NADH + H+ acetaldehyde biosynthesis I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.1 ethanol + NAD+ = acetaldehyde + NADH + H+ ethanol degradation II (cytosol) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.1 ethanol + NAD+ = acetaldehyde + NADH + H+ pyruvate fermentation to ethanol II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.27 (S)-lactate + NAD+ = pyruvate + NADH + H+ pyruvate fermentation to lactate NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 2-oxoglutarate + coenzyme A + NAD+ = succinyl-CoA + CO2 + NADH TCA cycle variation III (eukaryotic) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.14.13.- 24-methylenelophenol + oxygen + NADH = 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 2-oxoadipate + NAD+ + coenzyme A = CO2 + NADH + glutaryl-CoA lysine degradation II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.14.13.- 24-ethylidenelophenol + NADH + oxygen = 4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.5.1.12 (S)-1-pyrroline-5-carboxylate + NAD+ + H2O = H+ + L-glutamate + NADH proline degradation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.5.1.12 (S)-1-pyrroline-5-carboxylate + NAD+ + H2O = H+ + L-glutamate + NADH arginine degradation I (arginase pathway) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.8 betaine aldehyde + NAD+ + H2O = H+ + glycine betaine + NADH glycine betaine biosynthesis III (plants) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.16.1.7 Fe3+ + NADH = H+ + Fe2+ + NAD+ Fe(III)-reduction and Fe(II) transport NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.5.1.15 5,10-methylenetetrahydropteroyl mono-L-glutamate + NAD+ = 5,10-methenyltetrahydrofolate + NADH folate transformations I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.38 (S)-malate + NAD+ = NADH + CO2 + pyruvate gluconeogenesis I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.14.13.- 4α-formyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NADH + oxygen = 4α-carboxy-4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 4-methyl-2-oxopentanoate + coenzyme A + NAD+ = isovaleryl-CoA + CO2 + NADH leucine degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.3.1.76 precorrin-2 + NAD+ = H+ + sirohydrochlorin + NADH siroheme biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ adenosine nucleotides degradation II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ adenosine nucleotides degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ guanosine nucleotides degradation II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.5.1.9 L-saccharopine + H2O + NAD+ = L-glutamate + 2-aminoadipate-6-semialdehyde + NADH + H+ lysine degradation II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.6.5.3 H+ + NADH = NAD+ NADH to cytochrome bd oxidase electron transfer NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.6.5.3 H+ + NADH = NAD+ aerobic respiration -- electron donor II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.6.5.3 H+ + NADH = NAD+ NAD/NADH phosphorylation and dephosphorylation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 2-keto-3-methyl-valerate + NAD+ + coenzyme A = 2-methylbutanoyl-CoA + NADH + CO2 isoleucine degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.27 (S)-methylmalonate-semialdehyde + coenzyme A + NAD+ + H2O = propanoyl-CoA + bicarbonate + NADH + H+ valine degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.1 H+ + 3-methylbutanal + NADH = 3-methylbutanol + NAD+ leucine degradation III NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.22 H2O + NAD+ = H+ + UDP-D-glucuronate + NADH UDP-D-xylose and UDP-D-glucuronate biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.22 H2O + NAD+ = H+ + UDP-D-glucuronate + NADH colanic acid building blocks biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.22 H2O + NAD+ = H+ + UDP-D-glucuronate + NADH galactose degradation III NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.- L-galactose + NAD+ = H+ + L-galactono-1,4-lactone + NADH ascorbate biosynthesis I (L-galactose pathway) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.3.1.28 NAD+ + 2,3-dihydro-2,3-dihydroxybenzoate = H+ + NADH + 2,3-dihydroxybenzoate 2,3-dihydroxybenzoate biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.5.1.20 5-methyl-tetrahydrofolate + NAD+ = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H+ + NADH folate transformations I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.5.1.20 5-methyl-tetrahydrofolate + NAD+ = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H+ + NADH folate transformations II (plants) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.4.1.2 H2O + NAD+ + L-glutamate = H+ + ammonia + NADH + 2-oxoglutarate glutamate degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.4.1.2 H2O + NAD+ + L-glutamate = H+ + ammonia + NADH + 2-oxoglutarate alanine degradation II (to D-lactate) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: (3Z)-hex-3-en-ol + NAD+ = cis-3-hexenal + NADH + H+ traumatin and (Z)-3-hexen-1-yl acetate biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.25 2-oxoisovalerate + coenzyme A + NAD+ = isobutyryl-CoA + CO2 + NADH valine degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.85 (2R,3S)-3-isopropylmalate + NAD+ = (2S)-2-isopropyl-3-oxosuccinate + NADH + H+ leucine biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.14.13.- 4α-hydroxymethyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NADH + oxygen = 4α-formyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.14.13.- 4α-formyl-ergosta-7,24(241)-dien-3β-ol + oxygen + NADH = 4α-carboxy-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.35 NAD+ = NADH + H+ fatty acid β-oxidation II (core pathway) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.3.1.9 NAD+ = NADH + H+ fatty acid elongation -- saturated NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.244 methanol + NAD+ = H+ + formaldehyde + NADH methanol oxidation to formaldehyde II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.7.1.1 nitrite + H2O + NAD+ = H+ + nitrate + NADH nitrate reduction II (assimilatory) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.178 NAD+ + 2-methyl-3-hydroxybutyryl-CoA = H+ + NADH + 2-methylacetoacetyl-CoA isoleucine degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.31 (S)-3-hydroxy-isobutyrate + NAD+ = H+ + NADH + (S)-methylmalonate-semialdehyde valine degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.1 H+ + isobutanal + NADH = isobutanol + NAD+ valine degradation II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.8.1.4 NAD+ = NADH + H+ acetyl-CoA biosynthesis (from pyruvate) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.24 succinate semialdehyde + H2O + NAD+ = succinate + NADH + H+ glutamate degradation III (via 4-aminobutyrate) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.24 succinate semialdehyde + H2O + NAD+ = succinate + NADH + H+ 4-aminobutyrate degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.29 D-glycerate + NAD+ = H+ + hydroxypyruvate + NADH photorespiration NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.4.1.14 NAD+ + L-glutamate = H+ + NADH + 2-oxoglutarate + L-glutamine ammonia assimilation cycle II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.4.1.14 NAD+ + L-glutamate = H+ + NADH + 2-oxoglutarate + L-glutamine glutamate biosynthesis IV NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.8.1.4 NAD+ = NADH + H+ glycine cleavage complex NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.14.13.- 4α-formyl-stigmasta-7,24(241)-dien-3β-ol + NADH + oxygen = 4α-carboxy-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.35 NAD+ + OPC8-3-hydroxyacyl-CoA = NADH + H+ + OPC8-3-ketoacyl-CoA jasmonic acid biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.23 histidinal + NAD+ + H2O = H+ + L-histidine + NADH histidine biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.1 H+ + phenylacetaldehyde + NADH = 2-phenylethanol + NAD+ phenylethanol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ adenosine nucleotides degradation II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ adenosine nucleotides degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.31 Δ1-piperideine-6-carboxylate + NAD+ + H2O = 2-aminoadipate + NADH + H+ lysine degradation II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.- 4α-carboxy-4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ = cycloeucalenone + NADH + CO2 plant sterol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.14 D-sorbitol + NAD+ = NADH + H+ sorbitol degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.255 NAD+ + D-mannitol = H+ + NADH mannitol degradation II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.23 methylglyoxal + NAD+ + H2O = H+ + pyruvate + NADH methylglyoxal degradation VII NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.19 4-aminobutanal + NAD+ + H2O = 4-aminobutyrate + NADH + H+ putrescine degradation IV NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.288 xanthoxin + NAD+ = abscisic aldehyde + NADH + H+ abscisic acid biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.28 benzaldehyde + H2O + NAD+ = benzoate + NADH + H+ benzoate biosynthesis III (CoA-dependent, non-β-oxidative) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.28 benzaldehyde + H2O + NAD+ = benzoate + NADH + H+ benzoate biosynthesis II (CoA-independent, non-β-oxidative) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.3 3-dimethylsulfoniopropionaldehyde + H2O + NAD+ = dimethylsulfoniopropionate + NADH + H+ dimethylsulfoniopropionate biosynthesis II (Spartina) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.3 3-dimethylsulfoniopropionaldehyde + H2O + NAD+ = dimethylsulfoniopropionate + NADH + H+ dimethylsulfoniopropionate biosynthesis I (Wollastonia) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.- 4α-carboxy-ergosta-7,24(241)-dien-3β-ol + NAD+ = episterone + NADH + CO2 plant sterol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 2.7.1.86 NADH + ATP = H+ + NADPH + ADP NAD/NADH phosphorylation and dephosphorylation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations II (plants) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH photorespiration NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.23 histidinol + NAD+ = H+ + histidinal + NADH histidine biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.35 NAD+ + OPC4-3-hydroxyacyl-CoA = NADH + H+ + OPC4-3-ketoacyl-CoA jasmonic acid biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.14.13.- 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol + oxygen + NADH = 4α-formyl-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 3.1.3.- NADPH + H2O = NADH NAD/NADH phosphorylation and dephosphorylation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.205 inosine-5'-phosphate + H2O + NAD+ = xanthosine-5-phosphate + NADH + H+ adenosine nucleotides degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.205 inosine-5'-phosphate + H2O + NAD+ = xanthosine-5-phosphate + NADH + H+ purine nucleotides de novo biosynthesis II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.59 3-hydroxypropionate + NAD+ = malonate semialdehyde + NADH + H+ β-alanine biosynthesis II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.35 3-(4-hydroxyphenyl)-3-hydroxy-propionyl-CoA + NAD+ = 3-(4-hydroxyphenyl)-3-oxo-propionyl-CoA + NADH + H+ 4-hydroxybenzoate biosynthesis V NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.41 D-threo-isocitrate + NAD+ = 2-oxoglutarate + CO2 + NADH TCA cycle variation III (eukaryotic) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.41 D-threo-isocitrate + NAD+ = 2-oxoglutarate + CO2 + NADH glutamine biosynthesis III NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.35 NAD+ + OPC6-3-hydroxyacyl-CoA = NADH + H+ + OPC6-3-ketoacyl-CoA jasmonic acid biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.- 4α-carboxy-stigmasta-7,24(241)-dien-3β-ol + NAD+ = avenastenone + NADH + CO2 plant sterol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH superpathway of glyoxylate cycle NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.3.1.9 NAD+ = NADH + H+ stearate biosynthesis II (plants) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH glyoxylate cycle NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH gluconeogenesis I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH TCA cycle variation III (eukaryotic) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH aspartate degradation II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.2 formate + NAD+ = CO2 + NADH formate oxidation to CO2 NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.3.1.9 NADH + H+ = NAD+ palmitate biosynthesis II (bacteria and plants) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.14.13.- 4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol + NADH + oxygen = 4α-formyl-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.14.13.- 24-methylenecycloartanol + NADH + oxygen = 4α-hydroxymethyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.6.1.1 NAD+ + NADPH = NADH + NADP+ NAD/NADH phosphorylation and dephosphorylation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.28 (R)-lactate + NAD+ = pyruvate + NADH + H+ alanine degradation II (to D-lactate) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.3 acetaldehyde + H2O + NAD+ = acetate + NADH + H+ ethanol degradation II (cytosol) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.3 acetaldehyde + H2O + NAD+ = acetate + NADH + H+ ethanol degradation IV (peroxisomal) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.8.1.4 NAD+ = NADH + H+ 2-ketoglutarate dehydrogenase complex NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.95 3-phospho-D-glycerate + NAD+ = H+ + 3-phospho-hydroxypyruvate + NADH serine biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 663.43 C21 H27 N7 O14 P2 NC(=O)C1(CC=CN(C=1)C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5)) CAS:58-68-4:*PUBCHEM:4349538:*PUBCHEM:4349538:*PUBCHEM:439153:*CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.8 sn-glycerol-3-phosphate + NAD+ = dihydroxyacetone phosphate + NADH + H+ glycerol-3-phosphate shuttle 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol 4α-methyl-5α-ergosta-8,14,24(241)-trien-3β-ol 410.682 C29 H46 O1 C1(CC(C(C2(C1(C3(=C(CC2)C4(=CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))C)O) PUBCHEM:25203414:*LIGAND-CPD:C11508: 1.14.13.70 NADPH + oxygen + obtusifoliol + H+ = H2O + NADP+ + formate + 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol plant sterol biosynthesis 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol 4α-methyl-5α-ergosta-8,14,24(241)-trien-3β-ol 410.682 C29 H46 O1 C1(CC(C(C2(C1(C3(=C(CC2)C4(=CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))C)O) PUBCHEM:25203414:*LIGAND-CPD:C11508: 1.3.1.70 4α-methyl-5α-ergosta-8,14,24(28)-dien-3β-ol + NADP+ = 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol + NADPH + H+ plant sterol biosynthesis 2-phenylethanol benzeneethanol*phenethanol 122.166 C8 H10 O1 C1(C=C(C=CC=1)CCO) PUBCHEM:6054:*CHEBI:49000:*LIGAND-CPD:C05853: 1.1.1.1 H+ + phenylacetaldehyde + NADH = 2-phenylethanol + NAD+ phenylethanol biosynthesis protoheme IX ferroprotoporphyrin IX*protoheme IX*heme b*heme*hemin*ferroprotoporphyrin*protoheme*heme b*hematin*haemin 614.482 C34 H30 N4 O4 FE1 CC7(C(=C8(N6([Fe++]24(N1(C(C(=C(C=1C=C3(N2C(C(=C3C)C=C)=CC5(=N4C(C(=C5C)C=C)=CC6=7)))C)CCC(=O)[O-])=C8)))))CCC(=O)[O-]) PUBCHEM:44229124:*CHEBI:17627:*LIGAND-CPD:C00032:*CAS:14875-96-8 4.99.1.1 protoporphyrin IX + Fe2+ = protoheme IX + H+ heme biosynthesis from uroporphyrinogen-III I protoheme IX ferroprotoporphyrin IX*protoheme IX*heme b*heme*hemin*ferroprotoporphyrin*protoheme*heme b*hematin*haemin 614.482 C34 H30 N4 O4 FE1 CC7(C(=C8(N6([Fe++]24(N1(C(C(=C(C=1C=C3(N2C(C(=C3C)C=C)=CC5(=N4C(C(=C5C)C=C)=CC6=7)))C)CCC(=O)[O-])=C8)))))CCC(=O)[O-]) PUBCHEM:44229124:*CHEBI:17627:*LIGAND-CPD:C00032:*CAS:14875-96-8 1.14.99.3 protoheme IX + oxygen = biliverdin-IX-α + Fe2+ + carbon monoxide + H2O heme degradation α-linolenate linolenate*linolenic acid*(9,12,15)-linolenic acid*α-linolenic acid*9Z,12Z,15Z-octadecatrienoate*9Z,12Z,15Z-octadecatrienoic acid*(9,12,15)-linolenate 277.426 C18 H29 O2 [O-]C(CCCCCCCC=CCC=CCC=CCC)=O PUBCHEM:5461005:*CHEBI:32387:*LIGAND-CPD:C06427:*CAS:463-40-1 1.13.11.12 oxygen + α-linolenate = 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate traumatin and (Z)-3-hexen-1-yl acetate biosynthesis α-linolenate linolenate*linolenic acid*(9,12,15)-linolenic acid*α-linolenic acid*9Z,12Z,15Z-octadecatrienoate*9Z,12Z,15Z-octadecatrienoic acid*(9,12,15)-linolenate 277.426 C18 H29 O2 [O-]C(CCCCCCCC=CCC=CCC=CCC)=O PUBCHEM:5461005:*CHEBI:32387:*LIGAND-CPD:C06427:*CAS:463-40-1 1.13.11.12 oxygen + α-linolenate = 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate jasmonic acid biosynthesis 2-oxo-4-methylthiobutanoate 2-keto-methyl-thio-butyrate*2-keto-4-methylthiobutyrate*4-methylthio-2-oxobutanoate*α-keto-4-methylthiobutyrate*4-methylthio-2-ketobutyrate*4-methylthio-2-ketobutanoate*4-methylthio-2-oxobutyrate*2-ketomethiobutyrate*KMTB*α-ketomethiobutyrate*2-keto-4-methylthiobutyric acid*α-ketomethiobutyric acid*α-keto-γ-methylthiobutyrate*α-keto-γ-methylthiobutyric acid*2-oxo-4-methylthiobutanoic acid*2-oxomethionine 147.168 C5 H7 O3 S1 C(CC(C([O-])=O)=O)SC PUBCHEM:4584184:*LIGAND-CPD:C01180:*CHEBI:16723: 2.6.1.5 2-oxo-4-methylthiobutanoate = L-methionine methionine salvage I 2-oxo-4-methylthiobutanoate 2-keto-methyl-thio-butyrate*2-keto-4-methylthiobutyrate*4-methylthio-2-oxobutanoate*α-keto-4-methylthiobutyrate*4-methylthio-2-ketobutyrate*4-methylthio-2-ketobutanoate*4-methylthio-2-oxobutyrate*2-ketomethiobutyrate*KMTB*α-ketomethiobutyrate*2-keto-4-methylthiobutyric acid*α-ketomethiobutyric acid*α-keto-γ-methylthiobutyrate*α-keto-γ-methylthiobutyric acid*2-oxo-4-methylthiobutanoic acid*2-oxomethionine 147.168 C5 H7 O3 S1 C(CC(C([O-])=O)=O)SC PUBCHEM:4584184:*LIGAND-CPD:C01180:*CHEBI:16723: 1.13.11.54 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one + oxygen = H+ + 2-oxo-4-methylthiobutanoate + formate methionine salvage I 1-deoxy-D-xylulose 5-phosphate DXP*deoxyxylulose-5-phosphate*D-1-deoxyxylulose-5-P*1-deoxy-D-threo-pentulose 5-phosphate*DOXP 212.096 C5 H9 O7 P1 CC(=O)C(O)C(O)COP([O-])(=O)[O-] CHEBI:57792:*PUBCHEM:23420274:*LIGAND-CPD:C11437: 1.1.1.267 2-C-methyl-D-erythritol-4-phosphate + NADP+ = 1-deoxy-D-xylulose 5-phosphate + NADPH + H+ methylerythritol phosphate pathway 1-deoxy-D-xylulose 5-phosphate DXP*deoxyxylulose-5-phosphate*D-1-deoxyxylulose-5-P*1-deoxy-D-threo-pentulose 5-phosphate*DOXP 212.096 C5 H9 O7 P1 CC(=O)C(O)C(O)COP([O-])(=O)[O-] CHEBI:57792:*PUBCHEM:23420274:*LIGAND-CPD:C11437: 2.2.1.7 H+ + pyruvate + D-glyceraldehyde-3-phosphate = 1-deoxy-D-xylulose 5-phosphate + CO2 methylerythritol phosphate pathway tetrahydrodipicolinate 2,3,4,5-Tetrahydrodipicolinate*2,3,4,5-tetrahydrodipicolinate*L-2,3,4,5-tetrahydrodipicolinate*Δ1-piperideine-2,6-dicarboxylate*(S)-2,3,4,5-tetrahydropyridine-2,6-dicarboxylate*tetrahydropyridine-2,6-dicarboxylate 169.137 C7 H7 N1 O4 [O-]C(=O)C1(=NC(CCC1)C([O-])=O) PUBCHEM:440179:*PUBCHEM:5460758:*CHEBI:11408:*CAS:52-52-8:*LIGAND-CPD:C03972: 1.3.1.26 tetrahydrodipicolinate = L-2,3-dihydrodipicolinate + H+ lysine biosynthesis VI tetrahydrodipicolinate 2,3,4,5-Tetrahydrodipicolinate*2,3,4,5-tetrahydrodipicolinate*L-2,3,4,5-tetrahydrodipicolinate*Δ1-piperideine-2,6-dicarboxylate*(S)-2,3,4,5-tetrahydropyridine-2,6-dicarboxylate*tetrahydropyridine-2,6-dicarboxylate 169.137 C7 H7 N1 O4 [O-]C(=O)C1(=NC(CCC1)C([O-])=O) PUBCHEM:440179:*PUBCHEM:5460758:*CHEBI:11408:*CAS:52-52-8:*LIGAND-CPD:C03972: 2.6.1.83 L,L-diaminopimelate + 2-oxoglutarate = tetrahydrodipicolinate + L-glutamate + H2O + H+ lysine biosynthesis VI precorrin-2 dihydrosirohydrochlorin 857.803 C42 H41 N4 O16 C15(=NC(C(C)(CC(=O)[O-])C(CCC(=O)[O-])1)=CC2(NC(=C(CCC(=O)[O-])C(CC(=O)[O-])=2)CC3(=C(CCC(=O)[O-])C(CC(=O)[O-])=C(N3)C=C4(C(CCC(=O)[O-])C(C)(CC(=O)[O-])C([N+]4)=C5)))) CAS:65207-12-7:*CHEBI:58827:*PUBCHEM:25245987:*CAS:82542-92-5:*LIGAND-CPD:C02463: 1.3.1.76 precorrin-2 + NAD+ = H+ + sirohydrochlorin + NADH siroheme biosynthesis precorrin-2 dihydrosirohydrochlorin 857.803 C42 H41 N4 O16 C15(=NC(C(C)(CC(=O)[O-])C(CCC(=O)[O-])1)=CC2(NC(=C(CCC(=O)[O-])C(CC(=O)[O-])=2)CC3(=C(CCC(=O)[O-])C(CC(=O)[O-])=C(N3)C=C4(C(CCC(=O)[O-])C(C)(CC(=O)[O-])C([N+]4)=C5)))) CAS:65207-12-7:*CHEBI:58827:*PUBCHEM:25245987:*CAS:82542-92-5:*LIGAND-CPD:C02463: 2.1.1.107 S-adenosyl-L-methionine + precorrin-1 = S-adenosyl-L-homocysteine + precorrin-2 siroheme biosynthesis 6-deoxocathasterone deoxocathasterone 418.702 C28 H50 O2 C1(CC(CC2([H])(C1(C3(C(CC2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))O) PUBCHEM:25202530:*LIGAND-CPD:C15798: 1.14.-.- H+ + 6-deoxocathasterone + oxygen = 6-deoxoteasterone + H2O brassinosteroid biosynthesis II 6-deoxocathasterone deoxocathasterone 418.702 C28 H50 O2 C1(CC(CC2([H])(C1(C3(C(CC2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))O) PUBCHEM:25202530:*LIGAND-CPD:C15798: H+ + (22S,24R)-22-hydroxy-5α-ergostan-3-one = 6-deoxocathasterone brassinosteroid biosynthesis II 6-deoxocathasterone deoxocathasterone 418.702 C28 H50 O2 C1(CC(CC2([H])(C1(C3(C(CC2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))O) PUBCHEM:25202530:*LIGAND-CPD:C15798: 1.14.13.- H+ + campestanol + oxygen + NADPH = 6-deoxocathasterone + H2O + NADP+ brassinosteroid biosynthesis II ADP ribose 1'',2''-cyclic phosphate ADP ribose 1'',2''-phosphate*adenosine diphosphate ribose 1'',2''-cyclic phosphate*Appr>p 618.26 C15 H19 N5 O16 P3 OC1(C(OC(C1O)COP(OP(OCC2(C(O)C3(OP(=O)([O-])OC(O2)3)))(=O)[O-])([O-])=O)N5(C4(C(=C(N=CN=4)N)N=C5))) PUBCHEM:25245989: 3.1.4.- ADP ribose 1'',2''-cyclic phosphate + H2O = H+ + ADP ribose 1''-phosphate tRNA splicing ADP ribose 1'',2''-cyclic phosphate ADP ribose 1'',2''-phosphate*adenosine diphosphate ribose 1'',2''-cyclic phosphate*Appr>p 618.26 C15 H19 N5 O16 P3 OC1(C(OC(C1O)COP(OP(OCC2(C(O)C3(OP(=O)([O-])OC(O2)3)))(=O)[O-])([O-])=O)N5(C4(C(=C(N=CN=4)N)N=C5))) PUBCHEM:25245989: 2.7.1.160 NAD+ = ADP ribose 1'',2''-cyclic phosphate + nicotinamide + H2O tRNA splicing glutathione disulfide glutathione oxidized*glutathione ox*GSSG*glutathione*GSH*ox. glutathione*oxidized glutathione 610.61 C20 H30 N6 O12 S2 O=C(CCC(C([O-])=O)[N+])NC(CSSCC(NC(=O)CCC([N+])C(=O)[O-])C(=O)NCC(=O)[O-])C(=O)NCC(=O)[O-] PUBCHEM:25245992:*LIGAND-CPD:C00127:*CAS:27025-41-8 1.8.5.1 L-dehydro-ascorbate + glutathione = H+ + glutathione disulfide + L-ascorbate ascorbate glutathione cycle glutathione disulfide glutathione oxidized*glutathione ox*GSSG*glutathione*GSH*ox. glutathione*oxidized glutathione 610.61 C20 H30 N6 O12 S2 O=C(CCC(C([O-])=O)[N+])NC(CSSCC(NC(=O)CCC([N+])C(=O)[O-])C(=O)NCC(=O)[O-])C(=O)NCC(=O)[O-] PUBCHEM:25245992:*LIGAND-CPD:C00127:*CAS:27025-41-8 1.8.1.7 glutathione + NADP+ = glutathione disulfide + NADPH + H+ glutathione redox reactions I glutathione disulfide glutathione oxidized*glutathione ox*GSSG*glutathione*GSH*ox. glutathione*oxidized glutathione 610.61 C20 H30 N6 O12 S2 O=C(CCC(C([O-])=O)[N+])NC(CSSCC(NC(=O)CCC([N+])C(=O)[O-])C(=O)NCC(=O)[O-])C(=O)NCC(=O)[O-] PUBCHEM:25245992:*LIGAND-CPD:C00127:*CAS:27025-41-8 1.8.1.7 glutathione + NADP+ = glutathione disulfide + NADPH + H+ glutathione redox reactions II glutathione disulfide glutathione oxidized*glutathione ox*GSSG*glutathione*GSH*ox. glutathione*oxidized glutathione 610.61 C20 H30 N6 O12 S2 O=C(CCC(C([O-])=O)[N+])NC(CSSCC(NC(=O)CCC([N+])C(=O)[O-])C(=O)NCC(=O)[O-])C(=O)NCC(=O)[O-] PUBCHEM:25245992:*LIGAND-CPD:C00127:*CAS:27025-41-8 1.8.4.9 H+ + sulfite + AMP + glutathione disulfide = adenosine 5'-phosphosulfate + glutathione sulfate reduction II (assimilatory) glutathione disulfide glutathione oxidized*glutathione ox*GSSG*glutathione*GSH*ox. glutathione*oxidized glutathione 610.61 C20 H30 N6 O12 S2 O=C(CCC(C([O-])=O)[N+])NC(CSSCC(NC(=O)CCC([N+])C(=O)[O-])C(=O)NCC(=O)[O-])C(=O)NCC(=O)[O-] PUBCHEM:25245992:*LIGAND-CPD:C00127:*CAS:27025-41-8 1.8.4.2 glutathione = glutathione disulfide glutathione redox reactions II glutathione disulfide glutathione oxidized*glutathione ox*GSSG*glutathione*GSH*ox. glutathione*oxidized glutathione 610.61 C20 H30 N6 O12 S2 O=C(CCC(C([O-])=O)[N+])NC(CSSCC(NC(=O)CCC([N+])C(=O)[O-])C(=O)NCC(=O)[O-])C(=O)NCC(=O)[O-] PUBCHEM:25245992:*LIGAND-CPD:C00127:*CAS:27025-41-8 1.11.1.9 hydrogen peroxide + glutathione = glutathione disulfide + H2O glutathione redox reactions I glutathione disulfide glutathione oxidized*glutathione ox*GSSG*glutathione*GSH*ox. glutathione*oxidized glutathione 610.61 C20 H30 N6 O12 S2 O=C(CCC(C([O-])=O)[N+])NC(CSSCC(NC(=O)CCC([N+])C(=O)[O-])C(=O)NCC(=O)[O-])C(=O)NCC(=O)[O-] PUBCHEM:25245992:*LIGAND-CPD:C00127:*CAS:27025-41-8 1.11.1.12 glutathione = glutathione disulfide + H2O glutathione redox reactions I nitrite nitrite*NO2*NO2- 46.005 N1 O2 N([O-])=O PUBCHEM:946:*CHEBI:16301:*CAS:7697-37-2:*LIGAND-CPD:C00088:*CAS:14797-65-0 1.7.1.1 nitrite + H2O + NAD+ = H+ + nitrate + NADH nitrate reduction II (assimilatory) nitrite nitrite*NO2*NO2- 46.005 N1 O2 N([O-])=O PUBCHEM:946:*CHEBI:16301:*CAS:7697-37-2:*LIGAND-CPD:C00088:*CAS:14797-65-0 1.7.7.1 ammonia + H2O = nitrite + H+ nitrate reduction II (assimilatory) L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C1(CC([N+])C(=O)[O-])(C=CC=CC=1) PUBCHEM:6925665:*KNAPSACK:C00001386:*PUBCHEM:6925665:*CAS:3617-44-5*LIGAND-CPD:C00079:*CAS:63-91-2 2.6.1.57 keto-phenylpyruvate + L-glutamate = L-phenylalanine + 2-oxoglutarate phenylalanine biosynthesis I L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C1(CC([N+])C(=O)[O-])(C=CC=CC=1) PUBCHEM:6925665:*KNAPSACK:C00001386:*PUBCHEM:6925665:*CAS:3617-44-5*LIGAND-CPD:C00079:*CAS:63-91-2 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ suberin biosynthesis L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C1(CC([N+])C(=O)[O-])(C=CC=CC=1) PUBCHEM:6925665:*KNAPSACK:C00001386:*PUBCHEM:6925665:*CAS:3617-44-5*LIGAND-CPD:C00079:*CAS:63-91-2 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ phenylpropanoid biosynthesis, initial reactions L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C1(CC([N+])C(=O)[O-])(C=CC=CC=1) PUBCHEM:6925665:*KNAPSACK:C00001386:*PUBCHEM:6925665:*CAS:3617-44-5*LIGAND-CPD:C00079:*CAS:63-91-2 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ trans-cinnamoyl-CoA biosynthesis L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C1(CC([N+])C(=O)[O-])(C=CC=CC=1) PUBCHEM:6925665:*KNAPSACK:C00001386:*PUBCHEM:6925665:*CAS:3617-44-5*LIGAND-CPD:C00079:*CAS:63-91-2 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ benzoate biosynthesis II (CoA-independent, non-β-oxidative) L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C1(CC([N+])C(=O)[O-])(C=CC=CC=1) PUBCHEM:6925665:*KNAPSACK:C00001386:*PUBCHEM:6925665:*CAS:3617-44-5*LIGAND-CPD:C00079:*CAS:63-91-2 4.1.1.53 H+ + L-phenylalanine = 2-phenylethylamine + CO2 phenylethanol biosynthesis L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C1(CC([N+])C(=O)[O-])(C=CC=CC=1) PUBCHEM:6925665:*KNAPSACK:C00001386:*PUBCHEM:6925665:*CAS:3617-44-5*LIGAND-CPD:C00079:*CAS:63-91-2 6.1.1.20 H+ + L-phenylalanine + ATP = diphosphate + AMP tRNA charging pathway L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C1(CC([N+])C(=O)[O-])(C=CC=CC=1) PUBCHEM:6925665:*KNAPSACK:C00001386:*PUBCHEM:6925665:*CAS:3617-44-5*LIGAND-CPD:C00079:*CAS:63-91-2 L-phenylalanine + oxygen + H2O = phenylacetaldehyde + ammonia + hydrogen peroxide + CO2 phenylethanol biosynthesis L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C1(CC([N+])C(=O)[O-])(C=CC=CC=1) PUBCHEM:6925665:*KNAPSACK:C00001386:*PUBCHEM:6925665:*CAS:3617-44-5*LIGAND-CPD:C00079:*CAS:63-91-2 4.2.1.91 H+ + L-arogenate = CO2 + H2O + L-phenylalanine phenylalanine biosynthesis II squalene 410.725 C30 H50 C(C=C(CCC=C(C)CCC=C(C)C)C)CC=C(C)CCC=C(CCC=C(C)C)C PUBCHEM:25244109:*LIGAND-CPD:C00751:*CAS:111-02-4 1.14.99.7 squalene + oxygen = (S)-2,3-epoxysqualene + H2O epoxysqualene biosynthesis squalene 410.725 C30 H50 C(C=C(CCC=C(C)CCC=C(C)C)C)CC=C(C)CCC=C(CCC=C(C)C)C PUBCHEM:25244109:*LIGAND-CPD:C00751:*CAS:111-02-4 2.5.1.21 presqualene diphosphate = squalene + diphosphate epoxysqualene biosynthesis OPC8-3-ketoacyl-CoA 1053.904 C39 H58 N7 O19 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)C(=O)CCCCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237200: 2.3.1.16 OPC8-3-ketoacyl-CoA + coenzyme A = acetyl-CoA + OPC6-CoA jasmonic acid biosynthesis OPC8-3-ketoacyl-CoA 1053.904 C39 H58 N7 O19 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)C(=O)CCCCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237200: 1.1.1.35 NAD+ + OPC8-3-hydroxyacyl-CoA = NADH + H+ + OPC8-3-ketoacyl-CoA jasmonic acid biosynthesis 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol CDP-ME-2P*CDP-methyl-D-erylthritol 2-phosphate*4-diphosphocytidyl-2C-methyl-D-erythritol 2-phosphate*4-diphosphocytidyl-2-C-methylerythritol 2-phosphate 597.259 C14 H22 N3 O17 P3 CC(CO)(OP(=O)([O-])[O-])C(O)COP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(N)=NC(=O)2)) PUBCHEM:25244700:*LIGAND-CPD:C11436: 2.7.1.148 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + ATP = H+ + 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + ADP methylerythritol phosphate pathway 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol CDP-ME-2P*CDP-methyl-D-erylthritol 2-phosphate*4-diphosphocytidyl-2C-methyl-D-erythritol 2-phosphate*4-diphosphocytidyl-2-C-methylerythritol 2-phosphate 597.259 C14 H22 N3 O17 P3 CC(CO)(OP(=O)([O-])[O-])C(O)COP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(N)=NC(=O)2)) PUBCHEM:25244700:*LIGAND-CPD:C11436: 4.6.1.12 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol = 2-C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP methylerythritol phosphate pathway L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ pyridine nucleotide cycling (plants) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.1 L-aspartate + 2-oxoglutarate = L-glutamate + oxaloacetate aspartate biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.1 L-aspartate + 2-oxoglutarate = L-glutamate + oxaloacetate aspartate degradation II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.3.2.2 glutathione + H2O = cysteinylglycine + L-glutamate glutathione degradation L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.85 chorismate + L-glutamine = 4-amino-4-deoxychorismate + L-glutamate p-aminobenzoate biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine superpathway of 5-aminoimidazole ribonucleotide biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 1.4.1.14 NAD+ + L-glutamate = H+ + NADH + 2-oxoglutarate + L-glutamine ammonia assimilation cycle II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 1.4.1.14 NAD+ + L-glutamate = H+ + NADH + 2-oxoglutarate + L-glutamine glutamate biosynthesis IV L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.12 L-glutamate + 7,8-dihydropteroate + ATP = H+ + 7,8-dihydrofolate monoglutamate + ADP tetrahydrofolate biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 3.5.2.9 5-oxoproline + H2O + ATP = H+ + L-glutamate + ADP γ-glutamyl cycle (plant pathway) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 3.5.2.9 5-oxoproline + H2O + ATP = H+ + L-glutamate + ADP γ-glutamyl cycle L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O 5-aminoimidazole ribonucleotide biosynthesis II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O 5-aminoimidazole ribonucleotide biosynthesis I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O superpathway of 5-aminoimidazole ribonucleotide biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 1.4.7.1 L-glutamate = 2-oxoglutarate + L-glutamine glutamate biosynthesis V L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 1.4.7.1 L-glutamate = 2-oxoglutarate + L-glutamine glutamine biosynthesis III L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 1.4.7.1 L-glutamate = 2-oxoglutarate + L-glutamine ammonia assimilation cycle II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.39 2-aminoadipate + 2-oxoglutarate = L-glutamate + 2-oxoadipate lysine degradation II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 1.5.1.12 (S)-1-pyrroline-5-carboxylate + NAD+ + H2O = H+ + L-glutamate + NADH proline degradation L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 1.5.1.12 (S)-1-pyrroline-5-carboxylate + NAD+ + H2O = H+ + L-glutamate + NADH arginine degradation I (arginase pathway) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 4.1.3.27 chorismate + L-glutamine = H+ + anthranilate + L-glutamate + pyruvate tryptophan biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.5 L-tyrosine + 2-oxoglutarate = L-glutamate + 4-hydroxyphenylpyruvate 4-hydroxyphenylpyruvate biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 L-glutamate + ATP = AMP + diphosphate L-glutamine biosynthesis II (tRNA-dependent) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP glutamine biosynthesis III L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP nitrate reduction II (assimilatory) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP ammonia assimilation cycle II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 3.5.1.2 L-glutamine + H2O = H+ + L-glutamate + ammonia glutamine degradation I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 3.5.1.2 L-glutamine + H2O = H+ + L-glutamate + ammonia citrulline biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.4 2-oxoglutarate + glycine = L-glutamate + glyoxylate photorespiration L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.80 nicotianamine + 2-oxoglutarate = L-glutamate + 3''-deamino-3''-oxonicotianamine 2'-deoxymugineic acid phytosiderophore biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.27 2-oxoglutarate + L-tryptophan = L-glutamate + indole-3-pyruvate IAA biosynthesis I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis II (acetyl cycle) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate uridine-5'-phosphate biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.3.1.1 L-glutamate + acetyl-CoA = H+ + N-acetyl-L-glutamate + coenzyme A arginine biosynthesis II (acetyl cycle) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.3.1.1 L-glutamate + acetyl-CoA = H+ + N-acetyl-L-glutamate + coenzyme A ornithine biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 1.5.1.9 L-saccharopine + H2O + NAD+ = L-glutamate + 2-aminoadipate-6-semialdehyde + NADH + H+ lysine degradation II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 4.1.1.15 H+ + L-glutamate = CO2 + 4-aminobutyrate glutamate degradation III (via 4-aminobutyrate) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 4.1.1.15 H+ + L-glutamate = CO2 + 4-aminobutyrate glutamate degradation IX (via 4-aminobutyrate) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 4.1.1.15 H+ + L-glutamate = CO2 + 4-aminobutyrate glutamate dependent acid resistance L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.22 2-oxoglutarate + (S)-3-amino-2-methylpropanoate = L-glutamate + (S)-methylmalonate-semialdehyde valine degradation I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.7.2.11 L-glutamate + ATP = L-glutamate-5-phosphate + ADP proline biosynthesis I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.7.2.11 L-glutamate + ATP = L-glutamate-5-phosphate + ADP citrulline biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 1.4.1.3 H2O + L-glutamate = ammonia + 2-oxoglutarate glutamate degradation X L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 1.4.1.3 H2O + L-glutamate = ammonia + 2-oxoglutarate glutamate biosynthesis II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.2 2-oxoglutarate + L-alanine = L-glutamate + pyruvate alanine biosynthesis II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.2 2-oxoglutarate + L-alanine = L-glutamate + pyruvate alanine degradation II (to D-lactate) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 1.4.1.2 H2O + NAD+ + L-glutamate = H+ + ammonia + NADH + 2-oxoglutarate glutamate degradation I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 1.4.1.2 H2O + NAD+ + L-glutamate = H+ + ammonia + NADH + 2-oxoglutarate alanine degradation II (to D-lactate) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.57 keto-phenylpyruvate + L-glutamate = L-phenylalanine + 2-oxoglutarate phenylalanine biosynthesis I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.52 3-phospho-L-serine + 2-oxoglutarate = L-glutamate + 3-phospho-hydroxypyruvate serine biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.2 L-cysteine + L-glutamate + ATP = H+ + L-γ-glutamylcysteine + ADP γ-glutamyl cycle (plant pathway) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.2 L-cysteine + L-glutamate + ATP = H+ + L-γ-glutamylcysteine + ADP glutathione biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate valine degradation I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate valine biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate pantothenate biosynthesis I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate valine degradation II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.79 prephenate + L-glutamate = L-arogenate + 2-oxoglutarate tyrosine biosynthesis II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.79 prephenate + L-glutamate = L-arogenate + 2-oxoglutarate phenylalanine biosynthesis II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.19 4-aminobutyrate + 2-oxoglutarate = succinate semialdehyde + L-glutamate glutamate degradation III (via 4-aminobutyrate) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.19 4-aminobutyrate + 2-oxoglutarate = succinate semialdehyde + L-glutamate 4-aminobutyrate degradation II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.19 4-aminobutyrate + 2-oxoglutarate = succinate semialdehyde + L-glutamate 4-aminobutyrate degradation I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.3.1.35 L-glutamate + N-acetyl-L-ornithine = N-acetyl-L-glutamate + L-ornithine arginine biosynthesis II (acetyl cycle) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.4.2 ATP + UTP + L-glutamine + H2O = H+ + ADP + CTP + L-glutamate pyrimidine ribonucleotides interconversion L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.83 L,L-diaminopimelate + 2-oxoglutarate = tetrahydrodipicolinate + L-glutamate + H2O + H+ lysine biosynthesis VI L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.11 N-acetyl-L-ornithine + 2-oxoglutarate = L-glutamate + N-acetyl-L-glutamate 5-semialdehyde arginine biosynthesis II (acetyl cycle) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.11 N-acetyl-L-ornithine + 2-oxoglutarate = L-glutamate + N-acetyl-L-glutamate 5-semialdehyde ornithine biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.1.1.17 L-glutamate + ATP = diphosphate + AMP tRNA charging pathway L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.1.1.17 L-glutamate + ATP = diphosphate + AMP tetrapyrrole biosynthesis I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.16 D-fructose-6-phosphate + L-glutamine = L-glutamate + D-glucosamine-6-phosphate UDP-N-acetyl-D-glucosamine biosynthesis II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde arginine degradation VI (arginase 2 pathway) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde arginine degradation I (arginase pathway) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde proline biosynthesis II (from arginine) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde citrulline biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.9 imidazole acetol-phosphate + L-glutamate = L-histidinol-phosphate + 2-oxoglutarate histidine biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-isoleucine + 2-oxoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine degradation I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-isoleucine + 2-oxoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine biosynthesis I (from threonine) L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.4.2.- phosphoribulosylformimino-AICAR-P + L-glutamine = H+ + L-glutamate + D-erythro-imidazole-glycerol-phosphate + aminoimidazole carboxamide ribonucleotide histidine biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = H+ + L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis II L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-leucine + 2-oxoglutarate = L-glutamate + 4-methyl-2-oxopentanoate leucine degradation III L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-leucine + 2-oxoglutarate = L-glutamate + 4-methyl-2-oxopentanoate leucine biosynthesis L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-leucine + 2-oxoglutarate = L-glutamate + 4-methyl-2-oxopentanoate leucine degradation I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = H+ + L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis I L-glutamate L-Glutamate*1-amino-propane-1,3-dicarboxylic acid*glutacid*glutaminic acid*L-glutamic acid*α-aminoglutaric acid*E*glt*glu*glut*glutamate*L-glu*2-aminopentanedioic acid 146.122 C5 H8 N1 O4 C([N+])(C(=O)[O-])CCC(=O)[O-] PUBCHEM:5460299:*PUBCHEM:5460299:*CHEBI:29985:*KNAPSACK:C00001358:*KNAPKSACK:C00001358*CAS:6893-26-1*LIGAND:C00217:*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.7 L-glutamine + ATP = L-glutamate + ADP L-glutamine biosynthesis II (tRNA-dependent) aminoimidazole carboxamide ribonucleotide 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide*AICAR*Z-nucleotide*aminoimidazole carboxamide ribonucleotide*AICA ribonucleotide*5'-phosphoribosyl-5-amino-4-imidazole carboxamide*5-amino-4-imidazolecarboxamide ribotide*5'-P-ribosyl-5-amino-4-imidazole carboxamide 336.197 C9 H13 N4 O8 P1 N1(C=NC(C(N)=O)=C(N)1)C2(OC(C(O)C(O)2)COP(=O)([O-])[O-]) CHEBI:289555:*PUBCHEM:25244110:*LIGAND-CPD:C04677:*CAS:3031-94-5 2.1.2.3 10-formyl-tetrahydrofolate + aminoimidazole carboxamide ribonucleotide = tetrahydrofolate + phosphoribosyl-formamido-carboxamide inosine-5'-phosphate biosynthesis II aminoimidazole carboxamide ribonucleotide 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide*AICAR*Z-nucleotide*aminoimidazole carboxamide ribonucleotide*AICA ribonucleotide*5'-phosphoribosyl-5-amino-4-imidazole carboxamide*5-amino-4-imidazolecarboxamide ribotide*5'-P-ribosyl-5-amino-4-imidazole carboxamide 336.197 C9 H13 N4 O8 P1 N1(C=NC(C(N)=O)=C(N)1)C2(OC(C(O)C(O)2)COP(=O)([O-])[O-]) CHEBI:289555:*PUBCHEM:25244110:*LIGAND-CPD:C04677:*CAS:3031-94-5 4.3.2.2 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole = fumarate + aminoimidazole carboxamide ribonucleotide inosine-5'-phosphate biosynthesis II aminoimidazole carboxamide ribonucleotide 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide*AICAR*Z-nucleotide*aminoimidazole carboxamide ribonucleotide*AICA ribonucleotide*5'-phosphoribosyl-5-amino-4-imidazole carboxamide*5-amino-4-imidazolecarboxamide ribotide*5'-P-ribosyl-5-amino-4-imidazole carboxamide 336.197 C9 H13 N4 O8 P1 N1(C=NC(C(N)=O)=C(N)1)C2(OC(C(O)C(O)2)COP(=O)([O-])[O-]) CHEBI:289555:*PUBCHEM:25244110:*LIGAND-CPD:C04677:*CAS:3031-94-5 2.4.2.- phosphoribulosylformimino-AICAR-P + L-glutamine = H+ + L-glutamate + D-erythro-imidazole-glycerol-phosphate + aminoimidazole carboxamide ribonucleotide histidine biosynthesis 1-pyrroline 70.114 C4 H8 N1 C1([N+]=CCC1) PUBCHEM:11966285:*CHEBI:36781:*LIGAND-CPD:C15668: 4-aminobutanal = 1-pyrroline + H2O putrescine degradation IV 1-pyrroline 70.114 C4 H8 N1 C1([N+]=CCC1) PUBCHEM:11966285:*CHEBI:36781:*LIGAND-CPD:C15668: 4-aminobutanal = 1-pyrroline + H2O spermine and spermidine degradation II 2-C-methyl-D-erythritol-4-phosphate MEP 214.111 C5 H11 O7 P1 [O-]P([O-])(=O)OCC(O)C(O)(C)CO PUBCHEM:21896402:*LIGAND-CPD:C11434: 1.1.1.267 2-C-methyl-D-erythritol-4-phosphate + NADP+ = 1-deoxy-D-xylulose 5-phosphate + NADPH + H+ methylerythritol phosphate pathway 2-C-methyl-D-erythritol-4-phosphate MEP 214.111 C5 H11 O7 P1 [O-]P([O-])(=O)OCC(O)C(O)(C)CO PUBCHEM:21896402:*LIGAND-CPD:C11434: 2.7.7.60 H+ + 2-C-methyl-D-erythritol-4-phosphate + CTP = 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + diphosphate methylerythritol phosphate pathway 6-hydroxymethyl-7,8-dihydropterin 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine*2-amino-4-hydroxy-6-hydroxymethyl dihydropteridin*dihydropterin-CH2OH 195.18 C7 H9 N5 O2 N2(C1(=C(C(=O)NC(N)=N1)N=C(CO)C2)) CHEBI:17083:*LIGAND-CPD:C01300:*PUBCHEM:218: 2.7.6.3 6-hydroxymethyl-7,8-dihydropterin + ATP = H+ + 6-hydroxymethyl-dihydropterin diphosphate + AMP 6-hydroxymethyl-dihydropterin diphosphate biosynthesis 6-hydroxymethyl-7,8-dihydropterin 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine*2-amino-4-hydroxy-6-hydroxymethyl dihydropteridin*dihydropterin-CH2OH 195.18 C7 H9 N5 O2 N2(C1(=C(C(=O)NC(N)=N1)N=C(CO)C2)) CHEBI:17083:*LIGAND-CPD:C01300:*PUBCHEM:218: 4.1.2.25 7,8-dihydro-D-neopterin = glycolaldehyde + 6-hydroxymethyl-7,8-dihydropterin 6-hydroxymethyl-dihydropterin diphosphate biosynthesis histidinol histidinol*histidol*L-histidinol 142.18 C6 H12 N3 O1 C1(=CNC=N1)CC(CO)[N+] KNAPSACK:C00007479:*PUBCHEM:25244116:*LIGAND-CPD:C00860:*CAS:501-28-0 1.1.1.23 histidinol + NAD+ = H+ + histidinal + NADH histidine biosynthesis histidinol histidinol*histidol*L-histidinol 142.18 C6 H12 N3 O1 C1(=CNC=N1)CC(CO)[N+] KNAPSACK:C00007479:*PUBCHEM:25244116:*LIGAND-CPD:C00860:*CAS:501-28-0 3.1.3.15 L-histidinol-phosphate + H2O = histidinol histidine biosynthesis dihydroconiferyl alcohol 182.219 C10 H14 O3 C1(C(=CC(=C(C=1)O)OC)CCCO) PUBCHEM:16822:*LIGAND-CPD:C10448: 2.4.1.- dihydroconiferyl alcohol = H+ + dihydroconiferyl alcohol glucoside + UDP monolignol glucosides biosynthesis urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(=O)(N)N PUBCHEM:1176:*CHEBI:16199:*LIGAND-CPD:C00086:*CAS:57-13-6 3.5.3.1 H2O + L-arginine = urea + L-ornithine urea cycle urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(=O)(N)N PUBCHEM:1176:*CHEBI:16199:*LIGAND-CPD:C00086:*CAS:57-13-6 3.5.3.1 H2O + L-arginine = urea + L-ornithine arginine degradation VI (arginase 2 pathway) urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(=O)(N)N PUBCHEM:1176:*CHEBI:16199:*LIGAND-CPD:C00086:*CAS:57-13-6 3.5.3.1 H2O + L-arginine = urea + L-ornithine putrescine biosynthesis IV urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(=O)(N)N PUBCHEM:1176:*CHEBI:16199:*LIGAND-CPD:C00086:*CAS:57-13-6 3.5.3.1 H2O + L-arginine = urea + L-ornithine arginine degradation I (arginase pathway) urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(=O)(N)N PUBCHEM:1176:*CHEBI:16199:*LIGAND-CPD:C00086:*CAS:57-13-6 3.5.3.1 H2O + L-arginine = urea + L-ornithine citrulline biosynthesis urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(=O)(N)N PUBCHEM:1176:*CHEBI:16199:*LIGAND-CPD:C00086:*CAS:57-13-6 3.5.1.5 urea + H2O = ammonia + CO2 urea degradation II urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(=O)(N)N PUBCHEM:1176:*CHEBI:16199:*LIGAND-CPD:C00086:*CAS:57-13-6 3.5.3.11 H2O + agmatine = urea + putrescine arginine degradation III (arginine decarboxylase/agmatinase pathway) urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(=O)(N)N PUBCHEM:1176:*CHEBI:16199:*LIGAND-CPD:C00086:*CAS:57-13-6 3.5.3.11 H2O + agmatine = urea + putrescine putrescine biosynthesis IV urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(=O)(N)N PUBCHEM:1176:*CHEBI:16199:*LIGAND-CPD:C00086:*CAS:57-13-6 3.5.3.7 H2O + 4-guanidinobutyrate = urea + 4-aminobutyrate arginine degradation X (arginine monooxygenase pathway) urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(=O)(N)N PUBCHEM:1176:*CHEBI:16199:*LIGAND-CPD:C00086:*CAS:57-13-6 3.5.3.4 H2O + allantoate = S-(-)-ureidoglycolate + urea allantoin degradation to ureidoglycolate I (urea producing) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.29 oxygen = H2O hypusine biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.- 7,8-dihydroneopterin phosphate + H2O = 7,8-dihydro-D-neopterin 6-hydroxymethyl-dihydropterin diphosphate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 N6-(Δ2-isopentenyl)-adenosine 5'-triphosphate + NADPH + H2O = H+ + trans-zeatin riboside triphosphate + NADP+ trans-zeatin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.- 18-oxo-oleate + NADP+ + H2O = H+ + octadecenedioate + NADPH suberin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.2.5 S-allantoin + H2O = H+ + allantoate allantoin degradation to ureidoglycolate I (urea producing) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.2.5 S-allantoin + H2O = H+ + allantoate allantoin degradation to ureidoglycolate II (ammonia producing) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.3 afzelechin + NADP+ + H2O = leucopelargonidin + NADPH + H+ 2,3-trans-flavanols biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.88 H+ + dihydrokaempferol + NADPH + oxygen = dihydromyricetin + NADP+ + H2O leucodelphinidin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.88 H+ + dihydrokaempferol + NADPH + oxygen = dihydromyricetin + NADP+ + H2O syringetin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.3.10 acetoacetyl-CoA + H2O + acetyl-CoA = H+ + coenzyme A + (S)-3-hydroxy-3-methylglutaryl-CoA mevalonate pathway I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.7 H2O + 4-guanidinobutyrate = urea + 4-aminobutyrate arginine degradation X (arginine monooxygenase pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (1,2,3,6) tetrakisphosphate + H2O = D-myo-inositol (1,2,3) trisphosphate phytate degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- 4α-formyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NADH + oxygen = 4α-carboxy-4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 9'-cis-neurosporene + oxygen = 7',9'-cis-lycopene + H2O trans-lycopene biosynthesis II (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- gibberellin A8 + 2-oxoglutarate + oxygen = H+ + GA8-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ adenosine nucleotides degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ adenosine nucleotides degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ guanosine nucleotides degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.33 H2O = β-D-glucose glycogen degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 (E)-cinnamoyl-CoA + H2O = 3-hydroxy-3-phenylpropionyl-CoA benzoate biosynthesis III (CoA-dependent, non-β-oxidative) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.1 H2O + L-arginine = urea + L-ornithine urea cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.1 H2O + L-arginine = urea + L-ornithine arginine degradation VI (arginase 2 pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.1 H2O + L-arginine = urea + L-ornithine putrescine biosynthesis IV H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.1 H2O + L-arginine = urea + L-ornithine arginine degradation I (arginase pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.1 H2O + L-arginine = urea + L-ornithine citrulline biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.11 H2O = methanol homogalacturonan degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.7.3.3 urate + oxygen + H2O = 5-hydroxyisourate + hydrogen peroxide urate degradation to allantoin H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.99.12 H+ + trans-zeatin riboside + H2O + FAD = adenosine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.1 starch degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- L-tryptophan + oxygen + NADPH = N-hydroxy-L-tryptophan + NADP+ + H2O IAA biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.3 3-phospho-L-serine + H2O = L-serine serine biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.1.48 H+ + 1-(o-carboxyphenylamino)-1'-deoxyribulose-5'-phosphate = (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + CO2 + H2O tryptophan biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.10 3-dehydroquinate = H2O + 3-dehydroshikimate chorismate biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 OPC6-3-hydroxyacyl-CoA = OPC6-trans-2-enoyl-CoA + H2O jasmonic acid biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.- fatty acid elongation -- saturated H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.- N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate + H2O = N6-dimethylallyladenine + D-ribose-5-phosphate trans-zeatin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.- H2O = H+ 3-phosphoinositide biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- GA29 + 2-oxoglutarate + oxygen = H+ + GA29-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.22 L-homocysteine + L-serine = H2O + L-cystathionine homocysteine and cysteine interconversion H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.8.7.1 hydrogen sulfide + H2O = sulfite sulfate reduction II (assimilatory) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.3.36 H+ + 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA = 1,4-dihydroxy-2-naphthoyl-CoA + H2O 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.11 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 4-coumarate suberin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.11 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 4-coumarate phenylpropanoid biosynthesis, initial reactions H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1-(3-aminopropyl)-4-aminobutanal = 1-(3-aminopropyl)-pyrrolinium + H2O spermine and spermidine degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate folate transformations I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate folate transformations II (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate formaldehyde oxidation V (tetrahydrofolate pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O glycine biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O folate transformations I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O folate transformations II (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O folate polyglutamylation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O photorespiration H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (2,3,4) trisphosphate + H2O = D-myo-inositol (2,4) bisphosphate phytate degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.4.46 H2O = sn-glycerol-3-phosphate + H+ glycerol degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.13.12.1 oxygen + L-arginine = 4-guanidinobutyramide + H2O + CO2 arginine degradation X (arginine monooxygenase pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.4.2 ATP + UTP + L-glutamine + H2O = H+ + ADP + CTP + L-glutamate pyrimidine ribonucleotides interconversion H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.31 6-phospho-D-glucono-1,5-lactone + H2O = H+ + 6-phospho-D-gluconate pentose phosphate pathway (oxidative branch) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.6.1.83 L,L-diaminopimelate + 2-oxoglutarate = tetrahydrodipicolinate + L-glutamate + H2O + H+ lysine biosynthesis VI H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.5 inosine-5'-phosphate + H2O = inosine adenosine nucleotides degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- 4α-formyl-ergosta-7,24(241)-dien-3β-ol + oxygen + NADH = 4α-carboxy-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.59 palmitate biosynthesis II (bacteria and plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.3.14 spermidine + oxygen + H2O = propane-1,3-diamine + 4-aminobutanal + hydrogen peroxide spermine and spermidine degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.3.- Cu2+ + H2O + ATP = Cu2+ + ADP copper transport I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.4 indole-3-acetamide + H2O = H+ + indole-3-acetate + ammonia IAA biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.- ADP ribose 1''-phosphate + H2O = ADP-ribose tRNA splicing H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.1 xanthosine + H2O = xanthine adenosine nucleotides degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.3.- H+ + 2-nonaprenyl-6-methoxyphenol + oxygen = 2-methoxy-6-all trans-nonaprenyl-2-methoxy-1,4-benzoquinol + H2O ubiquinol-9 biosynthesis (eukaryotic) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = H+ + L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.11.1.12 glutathione = glutathione disulfide + H2O glutathione redox reactions I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.19 1-(5-phospho-D-ribosyl)-AMP + H2O = 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide histidine biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.14 H2O = cis-vaccenate cis-vaccenate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.1.- H+ + 4-coumaroyl-CoA + H2O + malonyl-CoA = coenzyme A + CO2 + p-coumaroyltriacetate resveratrol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.25 H2O + 1D-myo-inositol (1)-monophosphate = myo-inositol phytate degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.5 H2O + cytidine = uridine + ammonia salvage pathways of pyrimidine ribonucleotides H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.5 H2O + cytidine = uridine + ammonia pyrimidine ribonucleosides degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.14 acyl-ACP thioesterase pathway H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.8.1.2 H2O + NADP+ + hydrogen sulfide = H+ + sulfite + NADPH sulfate reduction I (assimilatory) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3-(2-propenoic acid)-o-benzoquinone + H2O = H+ + 3-(2-propenoic acid)-4,6-hydroxy cyclohexa-2,5-dienone esculetin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ adenosine nucleotides degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ adenosine nucleotides degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.3.26 geranyl diphosphate + H2O = (3R)-linalool + diphosphate linalool biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.7.9.3 H2O + hydrogen selenide + ATP = selenophosphate + AMP selenocysteine biosynthesis II (archaea and eukaryotes) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- H+ + (3R,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.65 L-asparagine = H+ + H2O + 3-cyano-L-alanine cyanide detoxification H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 L-phenylalanine + oxygen + H2O = phenylacetaldehyde + ammonia + hydrogen peroxide + CO2 phenylethanol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- H+ + (22α)-hydroxy-campest-4-en-3-one + NADPH + oxygen = (22R,23R)-22,23-dihydroxy-campest-4-en-3-one + NADP+ + H2O brassinosteroid biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.3 cyanidin + NADPH = epicatechin + NADP+ + H2O 2,3-cis-flavanols biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- oleate + NADPH + oxygen = 18-hydroxyoleate + NADP+ + H2O suberin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.33 H2O = maltotetraose glycogen degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.3 3-dimethylsulfoniopropionaldehyde + H2O + NAD+ = dimethylsulfoniopropionate + NADH + H+ dimethylsulfoniopropionate biosynthesis II (Spartina) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.3 3-dimethylsulfoniopropionaldehyde + H2O + NAD+ = dimethylsulfoniopropionate + NADH + H+ dimethylsulfoniopropionate biosynthesis I (Wollastonia) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.3.1.1 S-adenosyl-L-homocysteine + H2O = L-homocysteine + adenosine methionine degradation I (to homocysteine) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.3.1.1 S-adenosyl-L-homocysteine + H2O = L-homocysteine + adenosine S-adenosyl-L-methionine cycle II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.23 H2O + lactose = β-D-galactose + β-D-glucose lactose degradation III H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.22 eriodictyol + 2-oxoglutarate + oxygen = luteolin + succinate + CO2 + H2O luteolin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (1,2,3,5,6) pentakisphosphate + H2O = D-myo-inositol (1,2,5,6) tetrakisphosphate phytate degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.2 thiamine-phosphate + H2O = thiamin thiamine biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.- nicotinate mononucleotide + H2O = H+ + nicotinate + D-ribose-5-phosphate pyridine nucleotide cycling (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol + oxygen + NADH = 4α-formyl-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.11.1.6 hydrogen peroxide = H2O + oxygen superoxide radicals degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.23 dihydromyricetin + 2-oxoglutarate + oxygen = myricetin + succinate + CO2 + H2O syringetin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.- indole + L-serine = L-tryptophan + H2O tryptophan biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.10.99.3 H+ + antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O antheraxanthin and violaxanthin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.10.99.3 H+ + antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.17 D-glucono-1,5-lactone + H2O = H+ + D-gluconate glucose and glucose-1-phosphate degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.- NADPH + H2O = NADH NAD/NADH phosphorylation and dephosphorylation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.19 leucocyanidin + 2-oxoglutarate + oxygen = succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.5.1.72 α-iminosuccinate + dihydroxyacetone phosphate = quinolinate + H2O NAD biosynthesis I (from aspartate) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.8 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + H2O = D-myo-inositol (1,2,4,5,6)-pentakisphosphate phytate degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.3 citrate = cis-aconitate + H2O glyoxylate cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.3 citrate = cis-aconitate + H2O TCA cycle variation III (eukaryotic) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.3 citrate = cis-aconitate + H2O glutamine biosynthesis III H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.1.8 L-saccharopine + H2O + NADP+ = L-lysine + 2-oxoglutarate + NADPH + H+ lysine degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 N6-dimethylallyladenine + H2O = trans-zeatin + H+ trans-zeatin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.51 H+ + prephenate = keto-phenylpyruvate + H2O + CO2 phenylalanine biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.- petroselinate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.116 3-hydroxypropanoyl-CoA = acrylyl-CoA + H2O β-alanine biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.16 N-acetyl-L-ornithine + H2O = L-ornithine + acetate ornithine biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 5-amino-6-(5-phospho-D-ribitylamino)uracil + H2O = 5-amino-6-(D-ribitylamino)uracil flavin biosynthesis I (bacteria and plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine methionine degradation I (to homocysteine) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine 2'-deoxymugineic acid phytosiderophore biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine ethylene biosynthesis from methionine H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine S-adenosyl-L-methionine cycle II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine S-adenosyl-L-methionine biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.14 nicotinamide mononucleotide + H2O = H+ + D-ribose-5-phosphate + nicotinamide pyridine nucleotide cycling (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.2.2 5,6-dihydrothymine + H2O = 3-ureido-isobutyrate + H+ thymine degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.11 2-phospho-D-glycerate = phosphoenolpyruvate + H2O gluconeogenesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.11 2-phospho-D-glycerate = phosphoenolpyruvate + H2O Rubisco shunt H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.11 2-phospho-D-glycerate = phosphoenolpyruvate + H2O glycolysis III H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.11 2-phospho-D-glycerate = phosphoenolpyruvate + H2O glycolysis IV (plant cytosol) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.11 2-phospho-D-glycerate = phosphoenolpyruvate + H2O glycolysis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- 4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol + NADH + oxygen = 4α-formyl-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.11 H2O + agmatine = urea + putrescine arginine degradation III (arginine decarboxylase/agmatinase pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.11 H2O + agmatine = urea + putrescine putrescine biosynthesis IV H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.12 H2O + agmatine = H+ + ammonia + N-carbamoylputrescine putrescine biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.12 H2O + agmatine = H+ + ammonia + N-carbamoylputrescine arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.15 L-histidinol-phosphate + H2O = histidinol histidine biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.4.11.1 seed germination protein turnover H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.4.11.1 wound-induced proteolysis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.3 acetaldehyde + H2O + NAD+ = acetate + NADH + H+ ethanol degradation II (cytosol) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.3 acetaldehyde + H2O + NAD+ = acetate + NADH + H+ ethanol degradation IV (peroxisomal) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ chlorogenic acid biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ chlorogenic acid biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ phenylpropanoid biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.88 H+ + eriodictyol + NADPH + oxygen = 3',4',5'-pentahydroxyflavanone + NADP+ + H2O leucodelphinidin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 5-hydroxy-2-oxopentanoate = 2-oxopentenoate + H2O hypoglycin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.26 H2O + 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one = 5-amino-6-(5-phospho-D-ribosylamino)uracil + ammonia flavin biosynthesis I (bacteria and plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.32 H2O = H+ phospholipases H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.113 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate = o-succinylbenzoate + H2O 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.4 (S)-3-hydroxy-isobutyryl-CoA + H2O = (S)-3-hydroxy-isobutyrate + H+ + coenzyme A valine degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 H+ + coumarinate = coumarin + H2O coumarin biosynthesis (via 2-coumarate) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.3 3-aminopropanal + H2O = β-alanine β-alanine biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (1,2,3,6) tetrakisphosphate + H2O = D-myo-inositol (1,2,6) trisphosphate phytate degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.37 H2O + D-sedoheptulose-1,7-bisphosphate = D-sedoheptulose-7-phosphate Calvin-Benson-Bassham cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine superpathway of 5-aminoimidazole ribonucleotide biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.3.3.3 coproporphyrinogen III + oxygen + H+ = protoporphyrinogen IX + CO2 + H2O chlorophyllide a biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.3.3.3 coproporphyrinogen III + oxygen + H+ = protoporphyrinogen IX + CO2 + H2O heme biosynthesis from uroporphyrinogen-III I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.76 UDP-L-rhamnose biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.92 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoate = H2O + 12,13(S)-epoxylinolenate jasmonic acid biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- N-hydroxy-L-tryptophan + oxygen + NADPH + H+ = N,N-dihydroxy-L-tryptophan + NADP+ + H2O IAA biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.3.49 (2E,6E)-farnesyl diphosphate + H2O = (3R,6E)-nerolidol + diphosphate (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 3-(4-hydroxyphenyl)-3-hydroxy-propionyl-CoA = 4-coumaroyl-CoA + H2O 4-hydroxybenzoate biosynthesis V H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.1.12 (S)-1-pyrroline-5-carboxylate + NAD+ + H2O = H+ + L-glutamate + NADH proline degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.1.12 (S)-1-pyrroline-5-carboxylate + NAD+ + H2O = H+ + L-glutamate + NADH arginine degradation I (arginase pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.- D-myo-inositol (1,3,4,5,6)-pentakisphosphate + H2O = D-myo-inositol (1,4,5,6)-tetrakisphosphate D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.3.1.- 24-epi-campesterol + NADPH + H+ + oxygen = brassicasterol + NADP+ + H2O plant sterol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (1,2) bisphosphate + H2O = 1D-myo-inositol (1)-monophosphate phytate degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.3.14 H+ + H2O + ATP = H+ + ADP adenosine nucleotides de novo biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.8.3.1 sulfite + oxygen + H2O = hydrogen peroxide + sulfate sulfite oxidation IV H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 p-coumaroyltriacetate = p-coumaroyltriacetic acid lactone + H2O resveratrol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.99.12 N6-dimethylallyladenine + H+ + FAD + H2O = 3-methyl-2-butenal + adenine + FADH2 cytokinins degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.2 L-glutamine + H2O = H+ + L-glutamate + ammonia glutamine degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.2 L-glutamine + H2O = H+ + L-glutamate + ammonia citrulline biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.15 homogalacturonan degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.7 H2O + adenosine = adenine adenine and adenosine salvage II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 H+ + eriodictyol + NADPH + oxygen = luteolin + NADP+ + H2O luteolin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.20 jasmonoyl-CoA + H2O = H+ + (+)-7-iso-jasmonate + coenzyme A jasmonic acid biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (1,2,3,4,5)-pentakisphosphate + H2O = D-myo-inositol (1,2,3,4) tetrakisphosphate phytate degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 H+ + naringenin + NADPH + oxygen = apigenin + NADP+ + H2O luteolin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (1,2,5,6) tetrakisphosphate + H2O = D-myo-inositol (1,2,6) trisphosphate phytate degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.27 (S)-methylmalonate-semialdehyde + coenzyme A + NAD+ + H2O = propanoyl-CoA + bicarbonate + NADH + H+ valine degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.1 starch degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.3 H2O + guanine = ammonia + xanthine guanosine nucleotides degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.70 NADPH + oxygen + obtusifoliol + H+ = H2O + NADP+ + formate + 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol plant sterol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.22 H2O + NAD+ = H+ + UDP-D-glucuronate + NADH UDP-D-xylose and UDP-D-glucuronate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.22 H2O + NAD+ = H+ + UDP-D-glucuronate + NADH colanic acid building blocks biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.22 H2O + NAD+ = H+ + UDP-D-glucuronate + NADH galactose degradation III H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.75 hydroxymethylbilane = uroporphyrinogen-III + H2O tetrapyrrole biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.- oxygen = H2O palmitoleate biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.2 (S)-malate = fumarate + H2O TCA cycle variation III (eukaryotic) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.2 (S)-malate = fumarate + H2O superpathway of glyoxylate cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 H+ + ferulate + NADPH + oxygen = 5-hydroxyferulate + H2O + NADP+ free phenylpropanoid acid biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.-.- H+ + sphinganine + oxygen + NADPH = 4-hydroxysphinganine + H2O + NADP+ sphingolipid biosynthesis (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.- 7,8-dihydroneopterin triphosphate + H2O = H+ + 7,8-dihydroneopterin phosphate + diphosphate 6-hydroxymethyl-dihydropterin diphosphate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.9.1.2 selenophosphate = H2O + diphosphate selenocysteine biosynthesis II (archaea and eukaryotes) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.2 isopentenyl diphosphate + H2O = 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H+ methylerythritol phosphate pathway H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.53 H+ + N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia putrescine biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.53 H+ + N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.4 H2O + allantoate = S-(-)-ureidoglycolate + urea allantoin degradation to ureidoglycolate I (urea producing) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.26 sucrose + H2O = α-D-glucose + β-D-fructofuranose sucrose degradation III H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.68 coniferaldehyde + H2O = ferulate + H+ ferulate and sinapate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.5 AMP + H2O = adenosine adenosine nucleotides degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.4.3 H2O = phosphoryl-choline phospholipases H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.4 H2O + adenosine = ammonia + inosine adenosine nucleotides degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 gluconeogenesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 glutamine biosynthesis III H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 CO2 fixation into oxaloacetate H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 C4 photosynthetic carbon assimilation cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.6 AMP + H2O = inosine-5'-phosphate + ammonia adenosine nucleotides degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.23 trans dihydroquercetin + 2-oxoglutarate + oxygen = quercetin + succinate + CO2 + H2O flavonol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.2.3 (S)-dihydroorotate + H2O = H+ + N-carbamoyl-L-aspartate uridine-5'-phosphate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.14 H2O = palmitate palmitate biosynthesis II (bacteria and plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 trans-zeatin riboside monophosphate + H2O = trans-zeatin + D-ribose-5-phosphate trans-zeatin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.20 maltotriose + H2O = maltose + α-D-glucose glycogen degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.56 H2O + D-myo-inositol (1,4,5)-trisphosphate = D-myo-inositol (1,4)-bisphosphate D-myo-inositol (1,4,5)-trisphosphate degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.82 pheophorbide a + H2O = pyropheophorbide a + methanol + CO2 chlorophyll a degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.- 6G,6-kestotetraose + H2O = 6G-kestotriose fructan degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.3.7 indole acetaldehyde + oxygen + H2O = H+ + indole-3-acetate + hydrogen peroxide IAA biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.2 inosine + H2O = hypoxanthine adenosine nucleotides degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.61 cis-vaccenate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.14 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 2-coumarate coumarin biosynthesis (via 2-coumarate) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.58 palmitate biosynthesis II (bacteria and plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.4 4-guanidinobutyramide + H2O = H+ + ammonia + 4-guanidinobutyrate arginine degradation X (arginine monooxygenase pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.4.14 H2O = 4'-phosphopantetheine acyl carrier protein metabolism H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.14 H2O = stearate stearate biosynthesis II (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.2.9 5-oxoproline + H2O + ATP = H+ + L-glutamate + ADP γ-glutamyl cycle (plant pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.2.9 5-oxoproline + H2O + ATP = H+ + L-glutamate + ADP γ-glutamyl cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- 4α-formyl-stigmasta-7,24(241)-dien-3β-ol + NADH + oxygen = 4α-carboxy-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.-.- 2-oxohexa-4,5-cyclopropyl-5-enoate + acetyl-CoA + H2O = H+ + 3-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate + coenzyme A hypoglycin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.23 histidinal + NAD+ + H2O = H+ + L-histidine + NADH histidine biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.17.4 H+ + L-ascorbate + 1-aminocyclopropane-1-carboxylate + oxygen = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.11.1.11 H+ + L-ascorbate + hydrogen peroxide = monodehydroascorbate + H2O ascorbate glutathione cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.4.1.8 L-cystathionine + H2O = H+ + ammonia + pyruvate + L-homocysteine methionine biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.4.1.8 L-cystathionine + H2O = H+ + ammonia + pyruvate + L-homocysteine homocysteine and cysteine interconversion H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.1 methyl indole-3-acetate + H2O = H+ + indole-3-acetate + methanol methyl indole-3-acetate interconversion H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.3.- Cu2+ + H2O + ATP = Cu2+ + ADP copper transport I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.99.12 H+ + trans-zeatin + H2O + FAD = adenine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.9.3.1 oxygen = H2O aerobic respiration -- electron donor II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.7.7.1 ammonia + H2O = nitrite + H+ nitrate reduction II (assimilatory) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.6 H2O + L-arginine = H+ + ammonia + L-citrulline proline biosynthesis II (from arginine) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- 2-decaprenyl-6-methoxyphenol + oxygen + NADPH + H+ = 2-methoxy-6-all trans-decaprenyl-2-methoxy-1,4-benzoquinol + H2O + NADP+ ubiquinol-10 biosynthesis (eukaryotic) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.19.6 oxygen = H2O linoleate biosynthesis I (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.2 H2O = coenzyme A + H+ acyl-CoA hydrolysis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.45 3-deoxy-D-manno-octulosonate 8-P + H2O = 3-deoxy-D-manno-octulosonate CMP-KDO biosynthesis II (from D-arabinose 5-phosphate) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.6 3-ureido-isobutyrate + H2O + H+ = (R)-3-amino-2-methylpropanoate + ammonia + CO2 thymine degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.3.25 geranyl diphosphate + H2O = (3S)-linalool + diphosphate linalool biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.59 palmitate biosynthesis II (bacteria and plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (2,4) bisphosphate + H2O = 1D-myo-inositol (2) monophosphate phytate degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- leucodelphinidin + oxygen + 2-oxoglutarate = H+ + delphinidin + H2O + CO2 + succinate anthocyanin biosynthesis (delphinidin 3-O-glucoside) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- H+ + GA44 (open lactone form) + 2-oxoglutarate + oxygen = GA38 + succinate + CO2 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.109 5-methylthioribulose-1-phosphate = 5-(methylthio)-2,3-dioxopentyl phosphate + H2O methionine salvage I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.9 S-adenosyl-L-homocysteine + H2O = S-ribosyl-L-homocysteine + adenine S-adenosyl-L-methionine cycle I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.4 cellulose biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 CTP = dCTP + H2O pyrimidine deoxyribonucleotides de novo biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.26 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + H2O = D-myo-inositol (1,2,3,5,6) pentakisphosphate phytate degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.5.1.54 phosphoenolpyruvate + D-erythrose-4-phosphate + H2O = 3-deoxy-D-arabino-heptulosonate-7-phosphate chorismate biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.5.1.54 phosphoenolpyruvate + D-erythrose-4-phosphate + H2O = 3-deoxy-D-arabino-heptulosonate-7-phosphate 3-dehydroquinate biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.33 (2S)-2-isopropylmalate = 2-isopropylmaleate + H2O leucine biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.90 antheraxanthin + H+ + oxygen = violaxanthin + H2O antheraxanthin and violaxanthin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.90 antheraxanthin + H+ + oxygen = violaxanthin + H2O xanthophyll cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.25 H2O + GTP = H+ + diphosphate + 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one + formate flavin biosynthesis I (bacteria and plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.21 DIMBOA-Glc + H2O = DIMBOA + β-D-glucose DIMBOA-glucoside degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.93 H+ + 2-cis-abscisic acid + NADPH + oxygen = 8'-hydroxyabscisate + NADP+ + H2O phaseic acid biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.28 1,4-dihydroxy-2-naphthoyl-CoA + H2O = H+ + 1,4-dihydroxy-2-naphthoate + coenzyme A 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.4.- dCDP + H2O = CDP pyrimidine deoxyribonucleotides de novo biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.22 stachyose + H2O = raffinose + α-D-galactose stachyose degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.11.1.9 hydrogen peroxide + glutathione = glutathione disulfide + H2O glutathione redox reactions I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.28 trehalose + H2O = β-D-glucose trehalose degradation II (trehalase) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.4.- ADP = dADP + H2O adenosine nucleotides de novo biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.3.9 acetyl-CoA + H2O + glyoxylate = H+ + (S)-malate + coenzyme A glyoxylate cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.3.9 acetyl-CoA + H2O + glyoxylate = H+ + (S)-malate + coenzyme A glycolate and glyoxylate degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.10.3.1 cis-caffeate + oxygen = 3-(2-propenoic acid)-o-benzoquinone + H2O esculetin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.4 triacylglycerol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.3 catechin + NADP+ + H2O = leucocyanidin + NADPH + H+ 2,3-trans-flavanols biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.3.14 spermine + oxygen + H2O = 1-(3-aminopropyl)-4-aminobutanal + propane-1,3-diamine + hydrogen peroxide spermine and spermidine degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- H+ + leucopelargonidin + 2-oxoglutarate + oxygen = pelargonidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- H+ + coniferaldehyde + NADPH + oxygen = 5-hydroxy-coniferaldehyde + NADP+ + H2O phenylpropanoid biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- H+ + coniferaldehyde + NADPH + oxygen = 5-hydroxy-coniferaldehyde + NADP+ + H2O ferulate and sinapate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.68 sinapaldehyde + NADP+ + H2O = H+ + sinapate + NADPH ferulate and sinapate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- GA34 + 2-oxoglutarate + oxygen = H+ + GA34-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.3.1 oxygen + H2O = hydrogen peroxide aldehyde oxidation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.21 H+ + apigenin + NADPH + oxygen = luteolin + NADP+ + H2O luteolin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.23 dUTP + H2O = H+ + dUMP + diphosphate pyrimidine deoxyribonucleotides de novo biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 5,10-methenyltetrahydrofolate + H2O = H+ + 5-formyl-tetrahydrofolate folate transformations II (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- 24-methylenelophenol + oxygen + NADH = 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- 24-ethylidenelophenol + NADH + oxygen = 4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- GA51 + 2-oxoglutarate + oxygen = H+ + GA51-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.8 betaine aldehyde + NAD+ + H2O = H+ + glycine betaine + NADH glycine betaine biosynthesis III (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.52 pyruvate + L-aspartate-semialdehyde = H+ + H2O + L-2,3-dihydrodipicolinate lysine biosynthesis VI H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- H+ + N,N-dihydroxy-L-tryptophan = (E)-indol-3-ylacetaldoxime + CO2 + H2O IAA biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.23 4-hydroxybenzoyl-CoA + H2O = H+ + coenzyme A 4-hydroxybenzoate biosynthesis V H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.5 urea + H2O = ammonia + CO2 urea degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.79 H+ + ent-kaurenoate + oxygen + NADPH = ent-7-α-hydroxykaurenoate + H2O + NADP+ GA12 biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.-.- H+ + 6-deoxocathasterone + oxygen = 6-deoxoteasterone + H2O brassinosteroid biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.9 H+ + allantoate + H2O = S-ureidoglycine + ammonia + CO2 allantoin degradation to ureidoglycolate II (ammonia producing) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (1,2,3) trisphosphate + H2O = D-myo-inositol (1,2) bisphosphate phytate degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (1,2,3) trisphosphate + H2O = D-myo-inositol (1,2) bisphosphate phytate degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate arginine degradation VI (arginase 2 pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate arginine degradation I (arginase pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate proline biosynthesis II (from arginine) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate proline biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate citrulline biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (1,2,6) trisphosphate + H2O = D-myo-inositol (1,2) bisphosphate phytate degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis II (acetyl cycle) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate uridine-5'-phosphate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.22 naringenin + 2-oxoglutarate + oxygen = apigenin + succinate + CO2 + H2O luteolin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.- 15-cis-phytoene + oxygen = 9,15,9'-tri-cis-ζ-carotene + H2O trans-lycopene biosynthesis II (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 N6-(Δ2-isopentenyl)-adenosine 5'-diphosphate + NADPH + H2O = H+ + trans-zeatin riboside diphosphate + NADP+ trans-zeatin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.2 NADP+ + H2O = NAD+ NAD/NADH phosphorylation and dephosphorylation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2,3-dihydroxybenzoate-VibB + norspermidine = norspermidine-2,3-dihydroxybenzoate + H2O vibriobactin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.4.1.3 H2O + L-glutamate = ammonia + 2-oxoglutarate glutamate degradation X H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.4.1.3 H2O + L-glutamate = ammonia + 2-oxoglutarate glutamate biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 formaldehyde + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H2O formaldehyde oxidation V (tetrahydrofolate pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.5.1 indole-3-acetonitrile + H2O = H+ + ammonia + indole-3-acetate IAA biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- laurate + oxygen + NADPH + H+ = ω-hydroxylaurate + NADP+ + H2O ω-hydroxylation of caprate and laurate H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.1.170 H+ + 4-coumaroyl-CoA + malonyl-CoA + NADPH = isoliquiritigenin + coenzyme A + CO2 + NADP+ + H2O flavonoid biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O leucopelargonidin and leucocyanidin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O leucodelphinidin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O flavonol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.5 nicotinamide mononucleotide + H2O = nicotinamide riboside pyridine nucleotide cycling (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 trans-cinnamate + H2O = 3-hydroxy-3-phenylpropionate benzoate biosynthesis II (CoA-independent, non-β-oxidative) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.11.1.7 betanidin + hydrogen peroxide = betanidin + betanidin quinone + H2O betanidin degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.4.1 dUDP + H2O = UDP pyrimidine deoxyribonucleotides de novo biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.11 fructose-1,6-bisphosphate + H2O = D-fructose-6-phosphate gluconeogenesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.11 fructose-1,6-bisphosphate + H2O = D-fructose-6-phosphate glycolysis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.11 fructose-1,6-bisphosphate + H2O = D-fructose-6-phosphate Calvin-Benson-Bassham cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 2-methyl-3-hydroxybutyryl-CoA = 2-methyl-crotonyl-CoA + H2O isoleucine degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.5.4 H2O + 3-cyano-L-alanine = ammonia + L-aspartate cyanide detoxification H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.23 dihydrokaempferol + 2-oxoglutarate + oxygen = kaempferol + succinate + CO2 + H2O flavonol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- 4α-hydroxymethyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NADH + oxygen = 4α-formyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.4.3.22 propane-1,3-diamine + H2O + oxygen = H+ + 3-aminopropanal + ammonia + hydrogen peroxide β-alanine biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.18 (S)-3-hydroxy-3-methylglutaryl-CoA = H2O + 3-methylglutaconyl-CoA leucine degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.11 5,10-methylenetetrahydropteroyl mono-L-glutamate + 2-oxoisovalerate + H2O = H+ + 2-dehydropantoate + tetrahydrofolate phosphopantothenate biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.11 5,10-methylenetetrahydropteroyl mono-L-glutamate + 2-oxoisovalerate + H2O = H+ + 2-dehydropantoate + tetrahydrofolate pantothenate biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.25 1D-myo-inositol (4)-monophosphate + H2O = myo-inositol D-myo-inositol (1,4,5)-trisphosphate degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.2 lauroyl-CoA + H2O = H+ + laurate + coenzyme A ω-hydroxylation of caprate and laurate H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.3.1.- sitosterol + NADPH + H+ + oxygen = stigmasterol + NADP+ + H2O plant sterol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.3.3.9 H+ + oxygen + NADPH + loganin = H2O + NADP+ + secologanin camptothecin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.59 palmitate biosynthesis II (bacteria and plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.- indole-3-acetyl-alanine + H2O = indole-3-acetate + L-alanine IAA biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.4.4 H2O = choline phospholipases H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.4.4 H2O = choline choline biosynthesis III H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.12 trehalose 6-phosphate + H2O = trehalose trehalose biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.84 indole-3-acetonitrile + H2O = indole-3-acetamide IAA biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.25 1D-myo-inositol (3)-monophosphate + H2O = myo-inositol myo-inositol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.3.3.2 tryptamine + secologanin = strictosidine + H2O camptothecin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.9 2,3-dihydroxy-isovalerate = 2-oxoisovalerate + H2O valine biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.4.11.2 cysteinylglycine + H2O = L-cysteine + glycine γ-glutamyl cycle (plant pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.4.11.2 cysteinylglycine + H2O = L-cysteine + glycine glutathione degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.4.11.2 cysteinylglycine + H2O = L-cysteine + glycine γ-glutamyl cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.2.2 glutathione + H2O = cysteinylglycine + L-glutamate glutathione degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.14 H2O = oleate oleate biosynthesis I (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.61 palmitate biosynthesis II (bacteria and plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.4.11 H2O = D-myo-inositol (1,4,5)-trisphosphate phospholipases H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.4.11 H2O = D-myo-inositol (1,4,5)-trisphosphate D-myo-inositol (1,4,5)-trisphosphate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.- β-cryptoxanthin + oxygen = zeaxanthin + H2O zeaxanthin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.14 H2O = petroselinate petroselinate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 betaine aldehyde hydrate = betaine aldehyde + H2O glycine betaine biosynthesis III (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.19 D-erythro-imidazole-glycerol-phosphate = imidazole acetol-phosphate + H2O histidine biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.12 GA44 (open lactone form) + 2-oxoglutarate + oxygen = GA19 + succinate + CO2 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.5 xanthosine-5-phosphate + H2O = xanthosine adenosine nucleotides degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.18.6.1 H+ + N2 + ATP + H2O = H2 + ammonia + ADP nitrogen fixation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.19 4-aminobutanal + NAD+ + H2O = 4-aminobutyrate + NADH + H+ putrescine degradation IV H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- 7-hydroxy-chlorophyllide a + oxygen + NADPH = chlorophyllide b + H2O + NADP+ chlorophyll cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.4.3.5 oxygen + H2O + pyridoxamine 5'-phosphate = H+ + ammonia + hydrogen peroxide + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.10 glucose and glucose-1-phosphate degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- leucocyanidin + 2-oxoglutarate + oxygen = H+ + cyanidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.24 sucrose-6-phosphate + H2O = sucrose sucrose biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- H+ + (22α)-hydroxy-campesterol + NADPH + oxygen = (22R,23R)-22,23-dihydroxycampesterol + NADP+ + H2O brassinosteroid biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- H+ + (5α)-campestan-3-one + oxygen + NADPH = (22S,24R)-22-hydroxy-5α-ergostan-3-one + H2O + NADP+ brassinosteroid biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.1 H2O + diphosphate = H+ UDP-glucose biosynthesis (from glucose 6-phosphate) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.19.2 oxygen = H2O oleate biosynthesis I (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.205 inosine-5'-phosphate + H2O + NAD+ = xanthosine-5-phosphate + NADH + H+ adenosine nucleotides degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.205 inosine-5'-phosphate + H2O + NAD+ = xanthosine-5-phosphate + NADH + H+ purine nucleotides de novo biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.21 H+ + naringenin + NADPH + oxygen = eriodictyol + NADP+ + H2O luteolin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.2 H2O = α-maltose starch degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 trans-zeatin riboside triphosphate + H2O = H+ + trans-zeatin riboside diphosphate trans-zeatin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.5 GMP + H2O = guanosine guanosine nucleotides degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.7.1 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H2O = 2-C-methyl-D-erythritol-2,4-cyclodiphosphate methylerythritol phosphate pathway H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.70 D-ribose-5-phosphate + uracil = H2O + pseudouridine 5'-phosphate pseudouridine degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- H+ + campestanol + oxygen + NADPH = 6-deoxocathasterone + H2O + NADP+ brassinosteroid biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.99.1.6 (Z)-indol-3-ylacetaldoxime = indole-3-acetonitrile + H2O IAA biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.- raffinose + H2O = α-D-galactose + sucrose stachyose degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.- β-carotene + oxygen = β-cryptoxanthin + H2O zeaxanthin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate + NADPH + H2O = H+ + trans-zeatin riboside monophosphate + NADP+ trans-zeatin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.19 nicotinamide + H2O = H+ + ammonia + nicotinate pyridine nucleotide cycling (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 9,9'-di-cis-ζ-carotene + oxygen = 7,9,9'-cis-neurosporene + H2O trans-lycopene biosynthesis II (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (1,2) bisphosphate + H2O = 1D-myo-inositol (2) monophosphate phytate degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (1,2) bisphosphate + H2O = 1D-myo-inositol (2) monophosphate phytate degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.2.17 5-hydroxyisourate + H2O = H+ + 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate urate degradation to allantoin H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 UTP = dUTP + H2O pyrimidine deoxyribonucleotides de novo biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 6.6.1.1 ATP + protoporphyrin IX + Mg2+ + H2O = H+ + Mg-protoporphyrin + ADP chlorophyllide a biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.81 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + oxygen + NADPH + H+ = divinyl protochlorophyllide a + NADP+ + H2O chlorophyllide a biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- 24-methylenecycloartanol + NADH + oxygen = 4α-hydroxymethyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.59 stearate biosynthesis II (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.119 fatty acid β-oxidation IV (unsaturated, even number) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.91 H+ + L-arogenate = CO2 + H2O + L-phenylalanine phenylalanine biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.4.3.10 oxygen + H2O + putrescine = H+ + ammonia + hydrogen peroxide + 4-aminobutanal putrescine degradation IV H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.6 3-ureidopropionate + H2O + H+ = β-alanine + ammonia + CO2 uracil degradation II (reductive) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 ATP = dATP + H2O adenosine nucleotides de novo biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.80 1-kestotriose + H2O = sucrose fructan degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2-hydroxy-3-keto-5-methylthio-1-phosphopentene + H2O = 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one methionine salvage I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = H+ + L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.3 triacylglycerol degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 fatty acid β-oxidation II (core pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 fatty acid β-oxidation IV (unsaturated, even number) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ pyridine nucleotide cycling (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.2.2 H2O + 5,6-dihydrouracil = H+ + 3-ureidopropionate uracil degradation II (reductive) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.5.1.55 D-arabinose 5-phosphate + H2O + phosphoenolpyruvate = 3-deoxy-D-manno-octulosonate 8-P CMP-KDO biosynthesis II (from D-arabinose 5-phosphate) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.2 phosphate utilization in cell wall regeneration H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.2 phosphate acquisition H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 trans-zeatin riboside diphosphate + H2O = H+ + trans-zeatin riboside monophosphate trans-zeatin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.79 GA12-aldehyde + NADPH + oxygen = gibberellin A12 + NADP+ + H2O GA12 biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.78 ent-kaurenol + NADPH + H+ + oxygen = ent-kaurenal + NADP+ + H2O GA12 biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.3.4 Cu2+ + H2O + ATP = Cu2+ + ADP copper transport II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.20 α-maltose + H2O = α-D-glucose starch degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O 5-aminoimidazole ribonucleotide biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O 5-aminoimidazole ribonucleotide biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O superpathway of 5-aminoimidazole ribonucleotide biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.15.7 choline + oxygen + H+ = betaine aldehyde hydrate + H2O glycine betaine biosynthesis III (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.21 H2O = laurate palmitate biosynthesis II (bacteria and plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.31 H+ + Δ1-piperideine-6-carboxylate + H2O = 2-aminoadipate-6-semialdehyde lysine degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.11.1.6 ethanol + hydrogen peroxide = H2O + acetaldehyde ethanol degradation IV (peroxisomal) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 dopamine + betalamic acid = H+ + miraxanthin V + H2O betaxanthin biosynthesis (via dopamine) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.3.14 abscisic aldehyde + H2O + oxygen = H+ + 2-cis-abscisic acid + hydrogen peroxide abscisic acid biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.3.14 abscisic aldehyde + H2O + oxygen = H+ + 2-cis-abscisic acid + hydrogen peroxide aldehyde oxidation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.99.12 H+ + isopentenyl adenosine + H2O + FAD = adenosine + 3-methyl-2-butenal + FADH2 cytokinins degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.4.- ADP ribose 1'',2''-cyclic phosphate + H2O = H+ + ADP ribose 1''-phosphate tRNA splicing H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 (S)-3-hydroxy-isobutyryl-CoA = methylacrylyl-CoA + H2O valine degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.-.- 6-methoxy-5-methyl-2-all-trans-decaprenyl-1,4-benzoquinol + oxygen = 3-demethylubiquinol-10 + H2O ubiquinol-10 biosynthesis (eukaryotic) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.5.1.61 H2O + porphobilinogen = H+ + ammonia + hydroxymethylbilane tetrapyrrole biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.2 dimethylallyl diphosphate + H2O = 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H+ methylerythritol phosphate pathway H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.59 palmitate biosynthesis II (bacteria and plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.79 succinate semialdehyde + NADP+ + H2O = succinate + NADPH + H+ 4-aminobutyrate degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.13 H2O + dCTP = ammonia + dUTP pyrimidine deoxyribonucleotides de novo biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.99.12 H+ + cis-zeatin + H2O + FAD = 3-methyl-4-cis-hydroxy-2-butenal + adenine + FADH2 cytokinins degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate = etheroleate + H2O divinyl ether biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.13.99.1 oxygen + myo-inositol = H+ + H2O UDP-D-glucuronate biosynthesis (from myo-inositol) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- nonaprenyl-4-hydroxybenzoate + oxygen + NADPH + H+ = 3,4-dihydroxy-5-all-trans-nonaprenylbenzoate + H2O + NADP+ ubiquinol-9 biosynthesis (eukaryotic) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.1 guanosine + H2O = guanine guanosine nucleotides degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.1 guanosine + H2O = guanine guanine and guanosine salvage II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.1.9 L-saccharopine + H2O + NAD+ = L-glutamate + 2-aminoadipate-6-semialdehyde + NADH + H+ lysine degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A glyoxylate cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A TCA cycle variation III (eukaryotic) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A glutamine biosynthesis III H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.3 cis-aconitate + H2O = D-threo-isocitrate glyoxylate cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.3 cis-aconitate + H2O = D-threo-isocitrate TCA cycle variation III (eukaryotic) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.3 cis-aconitate + H2O = D-threo-isocitrate glutamine biosynthesis III H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.4.1.1 L-cystathionine + H2O = H+ + ammonia + 2-oxobutanoate + L-cysteine homocysteine and cysteine interconversion H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.3 protoheme IX + oxygen = biliverdin-IX-α + Fe2+ + carbon monoxide + H2O heme degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.13.1.1 UDP-α-D-glucose + H+ + sulfite = UDP-α-D-sulfoquinovopyranose + H2O sulfolipid biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 tryptamine + oxygen + NADPH = N-hydroxyl-tryptamine + H2O + NADP+ IAA biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.16 GTP + H2O = H+ + formate + 7,8-dihydroneopterin triphosphate 6-hydroxymethyl-dihydropterin diphosphate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.18 H2O + 2-phosphoglycolate = glycolate photorespiration H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.14.8 anthranilate + oxygen + FADH2 = 3-hydroxyanthranilate + H2O + FAD + H+ anthranilate degradation IV (aerobic) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 H+ + gibberellin A12 + oxygen = GA53 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 H+ + 3,4,6-trihydroxy-cis-cinnamate = esculetin + H2O esculetin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.- H2O = 2-monoacylglycerol triacylglycerol degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.3 H2O = β-D-glucose glycogen degradation III H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.2 decanoyl-CoA + H2O = H+ + caprate + coenzyme A ω-hydroxylation of caprate and laurate H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.4.1.2 H2O + NAD+ + L-glutamate = H+ + ammonia + NADH + 2-oxoglutarate glutamate degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.4.1.2 H2O + NAD+ + L-glutamate = H+ + ammonia + NADH + 2-oxoglutarate alanine degradation II (to D-lactate) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4-aminobutanal = 1-pyrroline + H2O putrescine degradation IV H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4-aminobutanal = 1-pyrroline + H2O spermine and spermidine degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.33 (2R,3S)-3-isopropylmalate = 2-isopropylmaleate + H2O leucine biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.3.13 2-oxoisovalerate + acetyl-CoA + H2O = H+ + (2S)-2-isopropylmalate + coenzyme A leucine biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.4.1 dCDP + H2O = CDP pyrimidine deoxyribonucleotides de novo biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- H+ + campesterol + oxygen + NADPH = (22α)-hydroxy-campesterol + H2O + NADP+ brassinosteroid biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.1 H2O + cytosine = ammonia + uracil salvage pathways of pyrimidine ribonucleotides H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.9 2,3-dihydroxy-3-methylvalerate = 2-keto-3-methyl-valerate + H2O isoleucine biosynthesis I (from threonine) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.90 zeaxanthin + H+ + oxygen = antheraxanthin + H2O antheraxanthin and violaxanthin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.90 zeaxanthin + H+ + oxygen = antheraxanthin + H2O xanthophyll cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.112 (22S,24R)-22-hydroxy-5α-ergostan-3-one + oxygen + NADPH + H+ = 3-dehydro-6-deoxoteasterone + NADP+ + H2O brassinosteroid biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 sphingolipid biosynthesis (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 7-hydroxy-chlorophyll a + H2O + NADP+ = H+ + chlorophyll a + oxygen + NADPH chlorophyll cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.10 H2O + 10-formyl-tetrahydrofolate = H+ + tetrahydrofolate + formate folate transformations I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 DMSP-amine + oxygen + H2O = H+ + 3-dimethylsulfoniopropionaldehyde + ammonia + hydrogen peroxide dimethylsulfoniopropionate biosynthesis II (Spartina) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- H+ + 3-epi-6-deoxocathasterone + NADPH + oxygen = 6-deoxotyphasterol + NADP+ + H2O brassinosteroid biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.78 ent-kaurenal + NADPH + oxygen = ent-kaurenoate + NADP+ + H2O GA12 biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 all-trans-geranyl-geranyl diphosphate + H2O = ent-16-a-hydroxy-kaurene + diphosphate ent -kaurene biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.23 1-monoacylglycerol + H2O = glycerol triacylglycerol degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.4.16 ammonia + H2O + CO2 + ATP = H+ + carbamoyl-phosphate + ADP urea cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.7.1.160 NAD+ = ADP ribose 1'',2''-cyclic phosphate + nicotinamide + H2O tRNA splicing H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.4.1.11 L-methionine + H2O = H+ + methanethiol + ammonia + 2-oxobutanoate methionine degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 strictosidine = strictosamide + H2O + CO2 camptothecin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (1,2,3,4) tetrakisphosphate + H2O = D-myo-inositol (2,3,4) trisphosphate phytate degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.27 phosphatidylglycerol biosynthesis I (plastidic) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.27 phosphatidylglycerol biosynthesis II (non-plastidic) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.27 cardiolipin biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.79 ent-7-α-hydroxykaurenoate + NADPH + H+ + oxygen = GA12-aldehyde + NADP+ + H2O GA12 biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.7.1.1 nitrite + H2O + NAD+ = H+ + nitrate + NADH nitrate reduction II (assimilatory) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.3.9 benzaldehyde + oxygen + H2O = H+ + benzoate + hydrogen peroxide aldehyde oxidation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.26 sucrose-6-phosphate + H2O = β-D-glucose-6-phosphate + β-D-fructofuranose sucrose degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.16 S-methyl-5'-thioadenosine + H2O = S-methyl-5-thio-D-ribose + adenine methylthioadenosine degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.16 S-methyl-5'-thioadenosine + H2O = S-methyl-5-thio-D-ribose + adenine methionine salvage I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.3.- geranyl diphosphate + H2O = (-)-α-terpineol + diphosphate monoterpene biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.4 phospholipases H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (1,2,4,5,6)-pentakisphosphate + H2O = D-myo-inositol (1,2,5,6) tetrakisphosphate phytate degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.81 magnesium-protoporphyrin IX 13-monomethyl ester + oxygen + NADPH + H+ = 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 cis-zeatin riboside monophosphate + H2O = cis-zeatin riboside cis-zeatin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.7.9.2 H2O + pyruvate + ATP = H+ + phosphoenolpyruvate + AMP gluconeogenesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.7.9.2 H2O + pyruvate + ATP = H+ + phosphoenolpyruvate + AMP glycolysis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- H+ + chlorophyllide a + oxygen + NADPH = 7-hydroxy-chlorophyllide a + H2O + NADP+ chlorophyll cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.24 succinate semialdehyde + H2O + NAD+ = succinate + NADH + H+ glutamate degradation III (via 4-aminobutyrate) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.24 succinate semialdehyde + H2O + NAD+ = succinate + NADH + H+ 4-aminobutyrate degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.21 cis-coumarinic acid-β-D-glucoside + H2O = coumarinate + β-D-glucose coumarin biosynthesis (via 2-coumarate) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.10.3.- H+ + oxygen = H+ + H2O NADH to cytochrome bd oxidase electron transfer H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.10.3.- H+ + oxygen = H+ + H2O succinate to cytochrome bd oxidase electron transfer H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.3.2.1 H2O + isochorismate = pyruvate + 2,3-dihydro-2,3-dihydroxybenzoate 2,3-dihydroxybenzoate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.3.1 O-phospho-L-homoserine + H2O = L-threonine threonine biosynthesis from homoserine H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.126 H2O + coniferin = coniferyl alcohol + β-D-glucose coniferin metabolism H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.78 H+ + ent-kaurene + oxygen + NADPH = H2O + NADP+ + ent-kaurenol GA12 biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.22 H2O + melibiose = α-D-galactose + β-D-glucose melibiose degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.14 chlorophyll a + H2O = H+ + chlorophyllide a + phytol chlorophyll a degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 cis-zeatin riboside + H2O = cis-zeatin cis-zeatin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.- D-myo-inositol (1,3,4,5,6)-pentakisphosphate + H2O = D-myo-inositol (3,4,5,6)-tetrakisphosphate D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.- indole-3-acetyl-leucine + H2O = indole-3-acetate + L-leucine IAA biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- H+ + campest-4-en-3-one + oxygen + NADPH = (22α)-hydroxy-campest-4-en-3-one + H2O + NADP+ brassinosteroid biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.31 Δ1-piperideine-6-carboxylate + NAD+ + H2O = 2-aminoadipate + NADH + H+ lysine degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.- S-ureidoglycine + H2O = H+ + ammonia + S-(-)-ureidoglycolate allantoin degradation to ureidoglycolate II (ammonia producing) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.4.- UDP = dUDP + H2O pyrimidine deoxyribonucleotides de novo biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.14 H2O = palmitoleate palmitoleate biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.- nicotinamide riboside + H2O = nicotinamide pyridine nucleotide cycling (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.23 methylglyoxal + NAD+ + H2O = H+ + pyruvate + NADH methylglyoxal degradation VII H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.59 palmitate biosynthesis II (bacteria and plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1D-myo-inositol (2) monophosphate + H2O = myo-inositol phytate degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.28 benzaldehyde + H2O + NAD+ = benzoate + NADH + H+ benzoate biosynthesis III (CoA-dependent, non-β-oxidative) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.28 benzaldehyde + H2O + NAD+ = benzoate + NADH + H+ benzoate biosynthesis II (CoA-independent, non-β-oxidative) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.4.3.21 2-phenylethylamine + oxygen + H2O = H+ + phenylacetaldehyde + ammonia + hydrogen peroxide phenylethanol biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.7 squalene + oxygen = (S)-2,3-epoxysqualene + H2O epoxysqualene biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.9 D-glyceraldehyde-3-phosphate + NADP+ + H2O = H+ + 3-phospho-D-glycerate + NADPH glycolysis IV (plant cytosol) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.4 3-hydroxypropanoyl-CoA + H2O = H+ + 3-hydroxypropionate + coenzyme A β-alanine biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.22 H2O + NAD+ = H+ + nicotinamide mononucleotide + AMP pyridine nucleotide cycling (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.4.1 dADP + H2O = ADP adenosine nucleotides de novo biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.47 GDP-α-D-mannose = GDP-4-dehydro-6-deoxy-D-mannose + H2O GDP-L-fucose biosynthesis I (from GDP-D-mannose) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- H+ + (3S,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.1.39 D-ribulose-1,5-bisphosphate + CO2 + H2O = 3-phospho-D-glycerate + H+ Rubisco shunt H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.1.39 D-ribulose-1,5-bisphosphate + CO2 + H2O = 3-phospho-D-glycerate + H+ Calvin-Benson-Bassham cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 OPC8-3-hydroxyacyl-CoA = OPC8-trans-2-enoyl-CoA + H2O jasmonic acid biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.3.48 (2E,6E)-farnesyl diphosphate + H2O = (3S,6E)-nerolidol + diphosphate (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.26 H2O + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate = D-myo-inositol (1,2,3,4,5)-pentakisphosphate phytate degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 OPC4-3-hydroxyacyl-CoA = OPC4-trans-2-enoyl-CoA + H2O jasmonic acid biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (1,2,3,4) tetrakisphosphate + H2O = D-myo-inositol (1,2,3) trisphosphate phytate degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.20 H+ + L-citrulline + H2O = L-ornithine + CO2 + ammonia proline biosynthesis II (from arginine) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 7,9,9'-cis-neurosporene + oxygen = prolycopene + H2O trans-lycopene biosynthesis II (plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 H+ + 4-coumarate + NADPH + oxygen = trans-caffeate + H2O + NADP+ suberin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 H+ + 4-coumarate + NADPH + oxygen = trans-caffeate + H2O + NADP+ free phenylpropanoid acid biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 fatty acid β-oxidation IV (unsaturated, even number) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.10.3.- H2O = oxygen photosynthesis light reactions H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.- α-L-galactose-1-phosphate + H2O = L-galactose ascorbate biosynthesis I (L-galactose pathway) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.119 very long chain fatty acid biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.10 inosine-5'-phosphate + H2O = phosphoribosyl-formamido-carboxamide inosine-5'-phosphate biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- 3-decaprenyl-4-hydroxybenzoate + oxygen + NADPH + H+ = 3,4-dihydroxy-5-all-trans-decaprenylbenzoate + H2O + NADP+ ubiquinol-10 biosynthesis (eukaryotic) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.-.- 6-methoxy-5-methyl-2-all-trans-nonaprenyl-1,4-benzoquinol + oxygen = 3-demethylubiquinol-9 + H2O ubiquinol-9 biosynthesis (eukaryotic) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O chlorogenic acid biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O chlorogenic acid biosynthesis II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O simplecoumarins biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O phenylpropanoid biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.75 phosphoryl-choline + H2O = choline choline biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2,3-dihydroxybenzoate-VibB + L-threonine = dihydroxyphenyl-5-methyloxazoline-VibF + H2O vibriobactin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.1 L-asparagine + H2O = L-aspartate + ammonia + H+ asparagine degradation I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.31 phosphoribosyl-ATP + H2O = 1-(5-phospho-D-ribosyl)-AMP + diphosphate + H+ histidine biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.3 gallocatechin + NADP+ + H2O = leucodelphinidin + NADPH + H+ 2,3-trans-flavanols biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.1 bicarbonate + H+ = CO2 + H2O cyanate degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.57 D-myo-inositol (1,4)-bisphosphate + H2O = 1D-myo-inositol (4)-monophosphate D-myo-inositol (1,4,5)-trisphosphate degradation H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.3 uridine + H2O = uracil pyrimidine ribonucleosides degradation II H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.81 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + oxygen = 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.24 5-amino-levulinate = H+ + H2O + porphobilinogen tetrapyrrole biosynthesis I H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 2.5.1.78 5-amino-6-(D-ribitylamino)uracil + 1-deoxy-L-glycero-tetrulose 4-phosphate = H+ + 6,7-dimethyl-8-(1-D-ribityl)lumazine + H2O flavin biosynthesis I (bacteria and plants) H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.10.99.3 H+ + violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O antheraxanthin and violaxanthin biosynthesis H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 1.10.99.3 H+ + violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle H2O H2O*H20*hydrogen oxide*water 18.015 H2 O1 O CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*CHEBI:15377:*PUBCHEM:962:*LIGAND-CPD:C00001:*CAS:7732-18-5 D-myo-inositol (1,2,3,5,6) pentakisphosphate + H2O = D-myo-inositol (1,2,3,6) tetrakisphosphate phytate degradation I (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoate*13-HPOD*(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate*13(S)-hydroperoxyoctadeca-9,11-dienoate 311.44 C18 H31 O4 CCCCCC(C=CC=CCCCCCCCC(=O)[O-])OO PUBCHEM:25244708:*LIGAND-CPD:C04717: 1.13.11.12 linoleate + oxygen = (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate traumatin and (Z)-3-hexen-1-yl acetate biosynthesis (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoate*13-HPOD*(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate*13(S)-hydroperoxyoctadeca-9,11-dienoate 311.44 C18 H31 O4 CCCCCC(C=CC=CCCCCCCCC(=O)[O-])OO PUBCHEM:25244708:*LIGAND-CPD:C04717: 1.13.11.12 linoleate + oxygen = (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate divinyl ether biosynthesis II (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoate*13-HPOD*(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate*13(S)-hydroperoxyoctadeca-9,11-dienoate 311.44 C18 H31 O4 CCCCCC(C=CC=CCCCCCCCC(=O)[O-])OO PUBCHEM:25244708:*LIGAND-CPD:C04717: (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate = 12-oxo-cis-9-dodecenoate + hexanal traumatin and (Z)-3-hexen-1-yl acetate biosynthesis (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoate*13-HPOD*(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate*13(S)-hydroperoxyoctadeca-9,11-dienoate 311.44 C18 H31 O4 CCCCCC(C=CC=CCCCCCCCC(=O)[O-])OO PUBCHEM:25244708:*LIGAND-CPD:C04717: (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate = etheroleate + H2O divinyl ether biosynthesis II avenastenone stigmasta-7,24(28)-dien-3-one, (5α,24Z)-*5α-stigmasta-7,Z-24(28)-dien-3-one 410.682 C29 H46 O1 CC=C(CCC(C)C2(CCC1(C3(=CCC4(CC(=O)CCC(C)(C(CCC(C)12)3)4)))))C(C)C 1.1.1.- 4α-carboxy-stigmasta-7,24(241)-dien-3β-ol + NAD+ = avenastenone + NADH + CO2 plant sterol biosynthesis avenastenone stigmasta-7,24(28)-dien-3-one, (5α,24Z)-*5α-stigmasta-7,Z-24(28)-dien-3-one 410.682 C29 H46 O1 CC=C(CCC(C)C2(CCC1(C3(=CCC4(CC(=O)CCC(C)(C(CCC(C)12)3)4)))))C(C)C 1.1.1.- avenastenone + NADPH + H+ = avenasterol + NADP+ plant sterol biosynthesis 4-amino-4-deoxychorismate 224.193 C10 H10 N1 O5 C=C(OC1(C=C(C=CC([N+])1)C(=O)[O-]))C(=O)[O-] PUBCHEM:25244713:*LIGAND-CPD:C11355:*CAS:97279-79-3 2.6.1.85 chorismate + L-glutamine = 4-amino-4-deoxychorismate + L-glutamate p-aminobenzoate biosynthesis 4-amino-4-deoxychorismate 224.193 C10 H10 N1 O5 C=C(OC1(C=C(C=CC([N+])1)C(=O)[O-]))C(=O)[O-] PUBCHEM:25244713:*LIGAND-CPD:C11355:*CAS:97279-79-3 4.1.3.38 4-amino-4-deoxychorismate = H+ + p-aminobenzoate + pyruvate p-aminobenzoate biosynthesis β-cryptoxanthin β,β-carotene-3-ol 552.882 C40 H56 O1 C1(C(C(=C(CC1O)C)C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC2(=C(CCCC2(C)C)C))C)C)(C)C) PUBCHEM:5281235:*CHEBI:10362:*LIGAND-CPD:C08591: 1.14.99.- β-cryptoxanthin + oxygen = zeaxanthin + H2O zeaxanthin biosynthesis β-cryptoxanthin β,β-carotene-3-ol 552.882 C40 H56 O1 C1(C(C(=C(CC1O)C)C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC2(=C(CCCC2(C)C)C))C)C)(C)C) PUBCHEM:5281235:*CHEBI:10362:*LIGAND-CPD:C08591: 1.14.99.- β-carotene + oxygen = β-cryptoxanthin + H2O zeaxanthin biosynthesis cis-vaccenate cis-vaccenic acid*(Z)-octadec-13-enoate*(Z)-11-octadecenoic acid 281.457 C18 H33 O2 [O-]C(=O)CCCCCCCCCC=CCCCCCC PUBCHEM:5461069:*CHEBI:30827: 3.1.2.14 H2O = cis-vaccenate cis-vaccenate biosynthesis nitrate NO3-*NO3*nitrate 62.005 N1 O3 N(=O)(=O)[O-] PUBCHEM:943:*CHEBI:17632:*LIGAND-CPD:C00244:*CAS:14797-55-8 1.7.1.1 nitrite + H2O + NAD+ = H+ + nitrate + NADH nitrate reduction II (assimilatory) coumaryl-alcohol 150.177 C9 H10 O2 C(=CCO)C1(=CC=C(O)C=C1) PUBCHEM:5280535:*CHEBI:28386:*LIGAND-CPD:C02646: 1.1.1.195 H+ + coumaraldehyde + NADPH = coumaryl-alcohol + NADP+ phenylpropanoid biosynthesis coniferaldehyde glucoside coniferyl aldehyde-4-O-β-D-glucopyranoside 340.329 C16 H20 O8 C1(C(=CC(=C(C=1)OC2(C(C(C(C(O2)CO)O)O)O))OC)C=CC=O) PUBCHEM:25245998: 2.4.1.- coniferaldehyde = H+ + coniferaldehyde glucoside + UDP monolignol glucosides biosynthesis cyanidin 285.232 C15 H9 O6 C3(=C(C(C1(C=CC(=C(C=1)O)O))=[O+]C2(C=C(C=C(C=23)[O-])O))[O-]) PUBCHEM:25202542:*LIGAND-CPD:C05905: 1.17.1.3 cyanidin + NADPH = epicatechin + NADP+ + H2O 2,3-cis-flavanols biosynthesis cyanidin 285.232 C15 H9 O6 C3(=C(C(C1(C=CC(=C(C=1)O)O))=[O+]C2(C=C(C=C(C=23)[O-])O))[O-]) PUBCHEM:25202542:*LIGAND-CPD:C05905: 1.14.11.- leucocyanidin + 2-oxoglutarate + oxygen = H+ + cyanidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) cyanidin 285.232 C15 H9 O6 C3(=C(C(C1(C=CC(=C(C=1)O)O))=[O+]C2(C=C(C=C(C=23)[O-])O))[O-]) PUBCHEM:25202542:*LIGAND-CPD:C05905: 2.4.1.115 cyanidin = cyanidin-3-O-β-D-glucoside + UDP anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) dCDP 2'-deoxycytidine diphosphate*2'-deoxycytidine-5'-diphosphate*deoxycytidine-diphosphate 384.155 C9 H12 N3 O10 P2 NC2(=NC(N(C1(CC(C(O1)COP(OP(=O)([O-])[O-])([O-])=O)O))C=C2)=O) CHEBI:58593:*PUBCHEM:21122964:*LIGAND-CPD:C00705:*CAS:800-73-7 1.17.4.1 dCDP + H2O = CDP pyrimidine deoxyribonucleotides de novo biosynthesis I dCDP 2'-deoxycytidine diphosphate*2'-deoxycytidine-5'-diphosphate*deoxycytidine-diphosphate 384.155 C9 H12 N3 O10 P2 NC2(=NC(N(C1(CC(C(O1)COP(OP(=O)([O-])[O-])([O-])=O)O))C=C2)=O) CHEBI:58593:*PUBCHEM:21122964:*LIGAND-CPD:C00705:*CAS:800-73-7 1.17.4.- dCDP + H2O = CDP pyrimidine deoxyribonucleotides de novo biosynthesis I dCDP 2'-deoxycytidine diphosphate*2'-deoxycytidine-5'-diphosphate*deoxycytidine-diphosphate 384.155 C9 H12 N3 O10 P2 NC2(=NC(N(C1(CC(C(O1)COP(OP(=O)([O-])[O-])([O-])=O)O))C=C2)=O) CHEBI:58593:*PUBCHEM:21122964:*LIGAND-CPD:C00705:*CAS:800-73-7 2.7.4.6 dCDP + ATP = dCTP + ADP pyrimidine deoxyribonucleotides de novo biosynthesis I OH- hydroxyl*hydroxyl ion*OH*hydroxide*hydroxide ion 18.015 H1 O1 [O-] PUBCHEM:961:*CHEBI:16234:*LIGAND-CPD:C01328:*CHEBI:15377:*PUBCHEM:962:*CAS:14280-30-9 caprate + NADP+ + OH- = ω-hydroxycaprate + NADPH ω-hydroxylation of caprate and laurate D-myo-inositol (2,3,4) trisphosphate 1D-myo-inositol (2,3,4) trisphosphate*myo-inositol (2,3,4) trisphosphate*Ins(2,3,4)P3*I(2,3,4)P3 414.049 C6 H9 O15 P3 O=P([O-])([O-])OC1(C(O)C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:25200766:*PUBCHEM:25244128: D-myo-inositol (2,3,4) trisphosphate + H2O = D-myo-inositol (2,4) bisphosphate phytate degradation II D-myo-inositol (2,3,4) trisphosphate 1D-myo-inositol (2,3,4) trisphosphate*myo-inositol (2,3,4) trisphosphate*Ins(2,3,4)P3*I(2,3,4)P3 414.049 C6 H9 O15 P3 O=P([O-])([O-])OC1(C(O)C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:25200766:*PUBCHEM:25244128: D-myo-inositol (1,2,3,4) tetrakisphosphate + H2O = D-myo-inositol (2,3,4) trisphosphate phytate degradation II 1-deoxy-L-glycero-tetrulose 4-phosphate 3,4-dihydroxy-2-butanone-4-phosphate*tetrolose phosphate*3,4-dihydroxy-2-butanone-4-P*L-3,4-dihydroxybutan-2-one-4-phosphate 182.069 C4 H7 O6 P1 P(=O)([O-])([O-])OCC(O)C(=O)C PUBCHEM:21983291:*LIGAND-CPD:C15556: 2.5.1.78 5-amino-6-(D-ribitylamino)uracil + 1-deoxy-L-glycero-tetrulose 4-phosphate = H+ + 6,7-dimethyl-8-(1-D-ribityl)lumazine + H2O flavin biosynthesis I (bacteria and plants) 1-deoxy-L-glycero-tetrulose 4-phosphate 3,4-dihydroxy-2-butanone-4-phosphate*tetrolose phosphate*3,4-dihydroxy-2-butanone-4-P*L-3,4-dihydroxybutan-2-one-4-phosphate 182.069 C4 H7 O6 P1 P(=O)([O-])([O-])OCC(O)C(=O)C PUBCHEM:21983291:*LIGAND-CPD:C15556: 4.1.99.12 D-ribulose-5-phosphate = H+ + formate + 1-deoxy-L-glycero-tetrulose 4-phosphate flavin biosynthesis I (bacteria and plants) D-myo-inositol (1,2,3,4,5)-pentakisphosphate 1-myo-inositol (1,2,3,4,5)-pentakisphosphate*inositol (1,2,3,4,5)-pentakisphosphate*myo-inositol (1,2,3,4,5)-pentakisphosphate*1L-myo-inositol (1,2,3,4,5)-pentakisphosphate*1D-myo-inositol (1,2,3,4,5)-pentakisphosphate*I(1,2,3,4,5)P5*Ins(1,2,3,4,5)P5 569.977 C6 H7 O21 P5 C1(OP([O-])([O-])=O)(C(O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])(=O)[O-])C(OP([O-])([O-])=O)1) PUBCHEM:25203450:*PUBCHEM:25246002:*LIGAND-CPD:C04579: 3.1.3.26 H2O + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate = D-myo-inositol (1,2,3,4,5)-pentakisphosphate phytate degradation II D-myo-inositol (1,2,3,4,5)-pentakisphosphate 1-myo-inositol (1,2,3,4,5)-pentakisphosphate*inositol (1,2,3,4,5)-pentakisphosphate*myo-inositol (1,2,3,4,5)-pentakisphosphate*1L-myo-inositol (1,2,3,4,5)-pentakisphosphate*1D-myo-inositol (1,2,3,4,5)-pentakisphosphate*I(1,2,3,4,5)P5*Ins(1,2,3,4,5)P5 569.977 C6 H7 O21 P5 C1(OP([O-])([O-])=O)(C(O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])(=O)[O-])C(OP([O-])([O-])=O)1) PUBCHEM:25203450:*PUBCHEM:25246002:*LIGAND-CPD:C04579: D-myo-inositol (1,2,3,4,5)-pentakisphosphate + H2O = D-myo-inositol (1,2,3,4) tetrakisphosphate phytate degradation II D-myo-inositol (1,4,5,6)-tetrakisphosphate inositol (1,4,5,6)-tetrakisphosphate*1D-myo-inositol (1,4,5,6)-tetrakisphosphate*Ins(1,4,5,6)P4*I(1,4,5,6)P4 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(OP([O-])([O-])=O)C(O)C(O)C(OP(=O)([O-])[O-])1) CHEBI:57627:*PUBCHEM:25201642:*LIGAND-CPD:C11555: 2.7.1.151 D-myo-inositol (1,4,5)-trisphosphate + ATP = H+ + D-myo-inositol (1,4,5,6)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) D-myo-inositol (1,4,5,6)-tetrakisphosphate inositol (1,4,5,6)-tetrakisphosphate*1D-myo-inositol (1,4,5,6)-tetrakisphosphate*Ins(1,4,5,6)P4*I(1,4,5,6)P4 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(OP([O-])([O-])=O)C(O)C(O)C(OP(=O)([O-])[O-])1) CHEBI:57627:*PUBCHEM:25201642:*LIGAND-CPD:C11555: 2.7.1.151 D-myo-inositol (1,4,5)-trisphosphate + ATP = H+ + D-myo-inositol (1,4,5,6)-tetrakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) D-myo-inositol (1,4,5,6)-tetrakisphosphate inositol (1,4,5,6)-tetrakisphosphate*1D-myo-inositol (1,4,5,6)-tetrakisphosphate*Ins(1,4,5,6)P4*I(1,4,5,6)P4 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(OP([O-])([O-])=O)C(O)C(O)C(OP(=O)([O-])[O-])1) CHEBI:57627:*PUBCHEM:25201642:*LIGAND-CPD:C11555: 2.7.1.- D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,2,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) D-myo-inositol (1,4,5,6)-tetrakisphosphate inositol (1,4,5,6)-tetrakisphosphate*1D-myo-inositol (1,4,5,6)-tetrakisphosphate*Ins(1,4,5,6)P4*I(1,4,5,6)P4 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(OP([O-])([O-])=O)C(O)C(O)C(OP(=O)([O-])[O-])1) CHEBI:57627:*PUBCHEM:25201642:*LIGAND-CPD:C11555: 2.7.1.151 D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) D-myo-inositol (1,4,5,6)-tetrakisphosphate inositol (1,4,5,6)-tetrakisphosphate*1D-myo-inositol (1,4,5,6)-tetrakisphosphate*Ins(1,4,5,6)P4*I(1,4,5,6)P4 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(OP([O-])([O-])=O)C(O)C(O)C(OP(=O)([O-])[O-])1) CHEBI:57627:*PUBCHEM:25201642:*LIGAND-CPD:C11555: 2.7.1.151 D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) D-myo-inositol (1,4,5,6)-tetrakisphosphate inositol (1,4,5,6)-tetrakisphosphate*1D-myo-inositol (1,4,5,6)-tetrakisphosphate*Ins(1,4,5,6)P4*I(1,4,5,6)P4 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(OP([O-])([O-])=O)C(O)C(O)C(OP(=O)([O-])[O-])1) CHEBI:57627:*PUBCHEM:25201642:*LIGAND-CPD:C11555: 2.7.1.151 D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis D-myo-inositol (1,4,5,6)-tetrakisphosphate inositol (1,4,5,6)-tetrakisphosphate*1D-myo-inositol (1,4,5,6)-tetrakisphosphate*Ins(1,4,5,6)P4*I(1,4,5,6)P4 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(OP([O-])([O-])=O)C(O)C(O)C(OP(=O)([O-])[O-])1) CHEBI:57627:*PUBCHEM:25201642:*LIGAND-CPD:C11555: 3.1.3.- D-myo-inositol (1,3,4,5,6)-pentakisphosphate + H2O = D-myo-inositol (1,4,5,6)-tetrakisphosphate D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis CDP cytidine-diphosphate*cytidine-5'-diphosphate 400.155 C9 H12 N3 O11 P2 NC2(=NC(N(C1(C(C(C(O1)COP(OP([O-])([O-])=O)([O-])=O)O)O))C=C2)=O) PUBCHEM:20056867:*LIGAND-CPD:C00112:*CAS:63-38-7 2.7.4.6 CDP + ATP = CTP + ADP pyrimidine ribonucleotides interconversion CDP cytidine-diphosphate*cytidine-5'-diphosphate 400.155 C9 H12 N3 O11 P2 NC2(=NC(N(C1(C(C(C(O1)COP(OP([O-])([O-])=O)([O-])=O)O)O))C=C2)=O) PUBCHEM:20056867:*LIGAND-CPD:C00112:*CAS:63-38-7 2.7.4.6 CDP + ATP = CTP + ADP salvage pathways of pyrimidine ribonucleotides CDP cytidine-diphosphate*cytidine-5'-diphosphate 400.155 C9 H12 N3 O11 P2 NC2(=NC(N(C1(C(C(C(O1)COP(OP([O-])([O-])=O)([O-])=O)O)O))C=C2)=O) PUBCHEM:20056867:*LIGAND-CPD:C00112:*CAS:63-38-7 1.17.4.1 dCDP + H2O = CDP pyrimidine deoxyribonucleotides de novo biosynthesis I CDP cytidine-diphosphate*cytidine-5'-diphosphate 400.155 C9 H12 N3 O11 P2 NC2(=NC(N(C1(C(C(C(O1)COP(OP([O-])([O-])=O)([O-])=O)O)O))C=C2)=O) PUBCHEM:20056867:*LIGAND-CPD:C00112:*CAS:63-38-7 1.17.4.- dCDP + H2O = CDP pyrimidine deoxyribonucleotides de novo biosynthesis I CDP cytidine-diphosphate*cytidine-5'-diphosphate 400.155 C9 H12 N3 O11 P2 NC2(=NC(N(C1(C(C(C(O1)COP(OP([O-])([O-])=O)([O-])=O)O)O))C=C2)=O) PUBCHEM:20056867:*LIGAND-CPD:C00112:*CAS:63-38-7 2.7.4.25 ATP + CMP = ADP + CDP salvage pathways of pyrimidine ribonucleotides myricetin 317.231 C15 H9 O8 O=C1(C([O-])=C(OC2(C=C(O)C=C(O)C1=2))C3(=CC(O)=C(O)C(O)=C3)) PUBCHEM:25201643:*CHEBI:58395:*PUBCHEM:25201643:*LIGAND-CPD:C10107: 2.1.1.149 myricetin + S-adenosyl-L-methionine = H+ + laricitrin + S-adenosyl-L-homocysteine syringetin biosynthesis myricetin 317.231 C15 H9 O8 O=C1(C([O-])=C(OC2(C=C(O)C=C(O)C1=2))C3(=CC(O)=C(O)C(O)=C3)) PUBCHEM:25201643:*CHEBI:58395:*PUBCHEM:25201643:*LIGAND-CPD:C10107: 1.14.11.23 dihydromyricetin + 2-oxoglutarate + oxygen = myricetin + succinate + CO2 + H2O syringetin biosynthesis trimethyl sulfonium 77.164 C3 H9 S1 [S+](C)(C)C PUBCHEM:1147:*LIGAND-CPD:C01008:*CHEBI:17434:*CAS:2181-42-2 2.1.1.19 tetrahydrofolate + trimethyl sulfonium = H+ + dimethylsulfide + 5-methyl-tetrahydrofolate folate transformations I 5-formyl-tetrahydrofolate N5-formyl-THF*5-formyl-THF leucovorin*n5-formyltetrahydrofolate*n5-formyl-thf*5-formyltetrahydrofolate*5-formyl-H4F*5-formyl-THF*folinic acid*5-CHO-THF*folinate*formyl-H4F*citrovorum factor*N5-formyl-H4F 471.429 C20 H21 N7 O7 NC3(NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))N(C=O)C=2C(=O)N=3)) CHEBI:57457:*PUBCHEM:6560146:*LIGAND-CPD:C03479:*CAS:58-05-9 5,10-methenyltetrahydrofolate + H2O = H+ + 5-formyl-tetrahydrofolate folate transformations II (plants) 5-formyl-tetrahydrofolate N5-formyl-THF*5-formyl-THF leucovorin*n5-formyltetrahydrofolate*n5-formyl-thf*5-formyltetrahydrofolate*5-formyl-H4F*5-formyl-THF*folinic acid*5-CHO-THF*folinate*formyl-H4F*citrovorum factor*N5-formyl-H4F 471.429 C20 H21 N7 O7 NC3(NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))N(C=O)C=2C(=O)N=3)) CHEBI:57457:*PUBCHEM:6560146:*LIGAND-CPD:C03479:*CAS:58-05-9 6.3.3.2 5-formyl-tetrahydrofolate + ATP = 5,10-methenyltetrahydrofolate + ADP folate transformations I 5-formyl-tetrahydrofolate N5-formyl-THF*5-formyl-THF leucovorin*n5-formyltetrahydrofolate*n5-formyl-thf*5-formyltetrahydrofolate*5-formyl-H4F*5-formyl-THF*folinic acid*5-CHO-THF*folinate*formyl-H4F*citrovorum factor*N5-formyl-H4F 471.429 C20 H21 N7 O7 NC3(NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))N(C=O)C=2C(=O)N=3)) CHEBI:57457:*PUBCHEM:6560146:*LIGAND-CPD:C03479:*CAS:58-05-9 6.3.3.2 5-formyl-tetrahydrofolate + ATP = 5,10-methenyltetrahydrofolate + ADP folate transformations II (plants) 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate (E)-4-hydroxy-3-methylbut 2-en-1-yl diphosphate*HMBDP*(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate 259.069 C5 H9 O8 P2 P(OP([O-])(=O)[O-])(=O)([O-])OCC=C(C)CO CHEBI:128753:*PUBCHEM:21597501:*LIGAND-CPD:C11811: 1.17.1.2 dimethylallyl diphosphate + H2O = 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H+ methylerythritol phosphate pathway 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate (E)-4-hydroxy-3-methylbut 2-en-1-yl diphosphate*HMBDP*(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate 259.069 C5 H9 O8 P2 P(OP([O-])(=O)[O-])(=O)([O-])OCC=C(C)CO CHEBI:128753:*PUBCHEM:21597501:*LIGAND-CPD:C11811: 1.17.1.2 isopentenyl diphosphate + H2O = 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H+ methylerythritol phosphate pathway 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate (E)-4-hydroxy-3-methylbut 2-en-1-yl diphosphate*HMBDP*(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate 259.069 C5 H9 O8 P2 P(OP([O-])(=O)[O-])(=O)([O-])OCC=C(C)CO CHEBI:128753:*PUBCHEM:21597501:*LIGAND-CPD:C11811: 1.17.7.1 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H2O = 2-C-methyl-D-erythritol-2,4-cyclodiphosphate methylerythritol phosphate pathway etheroleate etheroleic acid*(9Z,11E,1'E)-12-(1'-hexenyloxy)-9,11-dodecadienoic acid 293.425 C18 H29 O3 C(CCC=COC=CC=CCCCCCCCC([O-])=O)C PUBCHEM:25246007: (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate = etheroleate + H2O divinyl ether biosynthesis II 3-methylglutaconyl-CoA 3-Methylglutaconyl-CoA*trans-3-methylglutaconyl-CoA*(E)-3-methylglutaconyl-1-CoA 888.606 C27 H37 N7 O19 P3 S1 C1(C(O)C(C(COP(=O)(OP([O-])(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)C=C(CC(=O)[O-])C)O)=O)[O-])O1)OP([O-])([O-])=O)(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25244136:*LIGAND-CPD:C03231: 6.4.1.4 ATP + 3-methylcrotonyl-CoA + bicarbonate = H+ + ADP + 3-methylglutaconyl-CoA leucine degradation I 3-methylglutaconyl-CoA 3-Methylglutaconyl-CoA*trans-3-methylglutaconyl-CoA*(E)-3-methylglutaconyl-1-CoA 888.606 C27 H37 N7 O19 P3 S1 C1(C(O)C(C(COP(=O)(OP([O-])(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)C=C(CC(=O)[O-])C)O)=O)[O-])O1)OP([O-])([O-])=O)(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25244136:*LIGAND-CPD:C03231: 4.2.1.18 (S)-3-hydroxy-3-methylglutaryl-CoA = H2O + 3-methylglutaconyl-CoA leucine degradation I D-myo-inositol (1,2,3,6) tetrakisphosphate 1D-myo-inositol (1,2,3,6) tetrakisphosphate*Ins(1,2,3,6)P4*I(1,2,3,6)P4 492.013 C6 H8 O18 P4 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:25201651: D-myo-inositol (1,2,3,6) tetrakisphosphate + H2O = D-myo-inositol (1,2,6) trisphosphate phytate degradation I D-myo-inositol (1,2,3,6) tetrakisphosphate 1D-myo-inositol (1,2,3,6) tetrakisphosphate*Ins(1,2,3,6)P4*I(1,2,3,6)P4 492.013 C6 H8 O18 P4 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:25201651: D-myo-inositol (1,2,3,5,6) pentakisphosphate + H2O = D-myo-inositol (1,2,3,6) tetrakisphosphate phytate degradation I D-myo-inositol (1,2,3,6) tetrakisphosphate 1D-myo-inositol (1,2,3,6) tetrakisphosphate*Ins(1,2,3,6)P4*I(1,2,3,6)P4 492.013 C6 H8 O18 P4 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:25201651: D-myo-inositol (1,2,3,6) tetrakisphosphate + H2O = D-myo-inositol (1,2,3) trisphosphate phytate degradation I indole-3-acetyl-leucine IAA-Leu*indole-3-acetyl-Leu*indole-3-acetyl-leucine 287.338 C16 H19 N2 O3 C2(C=C1(C(C(CC(=O)NC(CC(C)C)C(=O)[O-])=CN1)=CC=2)) PUBCHEM:25244137: 3.5.1.- indole-3-acetyl-leucine + H2O = indole-3-acetate + L-leucine IAA biosynthesis II phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.9.2 H2O + pyruvate + ATP = H+ + phosphoenolpyruvate + AMP gluconeogenesis I phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.9.2 H2O + pyruvate + ATP = H+ + phosphoenolpyruvate + AMP glycolysis I phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.5.1.55 D-arabinose 5-phosphate + H2O + phosphoenolpyruvate = 3-deoxy-D-manno-octulosonate 8-P CMP-KDO biosynthesis II (from D-arabinose 5-phosphate) phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.2.1.11 2-phospho-D-glycerate = phosphoenolpyruvate + H2O gluconeogenesis I phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.2.1.11 2-phospho-D-glycerate = phosphoenolpyruvate + H2O Rubisco shunt phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.2.1.11 2-phospho-D-glycerate = phosphoenolpyruvate + H2O glycolysis III phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.2.1.11 2-phospho-D-glycerate = phosphoenolpyruvate + H2O glycolysis IV (plant cytosol) phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.2.1.11 2-phospho-D-glycerate = phosphoenolpyruvate + H2O glycolysis I phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.9.1 pyruvate + ATP = H+ + phosphoenolpyruvate + AMP + diphosphate glutamine biosynthesis III phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.9.1 pyruvate + ATP = H+ + phosphoenolpyruvate + AMP + diphosphate C4 photosynthetic carbon assimilation cycle phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.1.1.49 oxaloacetate + ATP = CO2 + phosphoenolpyruvate + ADP gluconeogenesis I phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.1.1.49 oxaloacetate + ATP = CO2 + phosphoenolpyruvate + ADP superpathway of glyoxylate cycle phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 gluconeogenesis I phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 glutamine biosynthesis III phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 CO2 fixation into oxaloacetate phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 C4 photosynthetic carbon assimilation cycle phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.5.1.19 shikimate-3-phosphate + phosphoenolpyruvate = 5-enolpyruvyl-shikimate-3-phosphate chorismate biosynthesis I phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP Rubisco shunt phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP glycolysis III phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP glycolysis IV (plant cytosol) phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP glycolysis I phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.5.1.54 phosphoenolpyruvate + D-erythrose-4-phosphate + H2O = 3-deoxy-D-arabino-heptulosonate-7-phosphate chorismate biosynthesis I phosphoenolpyruvate P-enol-pyr*P-enol-pyruvate*P-enol-pyruvate*P-enol-pyr*PEP 165.019 C3 H2 O6 P1 O(P([O-])([O-])=O)C(=C)C([O-])=O CHEBI:58702:*LIGAND-CPD:c00074:*CAS:73-89-2*PUBCHEM:3674425:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.5.1.54 phosphoenolpyruvate + D-erythrose-4-phosphate + H2O = 3-deoxy-D-arabino-heptulosonate-7-phosphate 3-dehydroquinate biosynthesis I hydroxymethylpyrimidine 6-amino-5-hydroxymethyl-2-methylpyrimidine*4-amino-2-methyl-5-pyrimidinemethanol*pyramine*pyramin*Toxopyrimidine*HMP*4-amino-2-methyl-5-hydroxymethylpyrimidine*4-amino-5-hydroxymethyl-2-methylpyrimidine 139.157 C6 H9 N3 O1 C1(N=C(N=C(C=1CO)N)C) PUBCHEM:777:*CHEBI:16892:*LIGAND-CPD:C01279:*CAS:73-67-6: 2.7.1.49 ATP + hydroxymethylpyrimidine = H+ + ADP + hydroxymethylpyrimidine phosphate thiamine biosynthesis II β-L-arabinose 1-phosphate β-L-arabinose 1-P 228.095 C5 H9 O8 P1 C1(OC(C(C(C1O)O)O)OP([O-])([O-])=O) CHEBI:57521:*PUBCHEM:25244737:*LIGAND-CPD:C03906: 2.7.7.37 H+ + β-L-arabinose 1-phosphate + UTP = diphosphate UDP-L-arabinose biosynthesis II (from L-arabinose) β-L-arabinose 1-phosphate β-L-arabinose 1-P 228.095 C5 H9 O8 P1 C1(OC(C(C(C1O)O)O)OP([O-])([O-])=O) CHEBI:57521:*PUBCHEM:25244737:*LIGAND-CPD:C03906: 2.7.1.46 ATP = β-L-arabinose 1-phosphate + ADP UDP-L-arabinose biosynthesis II (from L-arabinose) myo-inositol cis-1,2,3,5-trans-4,6-Cyclohexanehexol*dambose*chiro-inositol*mesoinositol*meso-inositol*inositol 180.157 C6 H12 O6 OC1(C(C(C(C(C1O)O)O)O)O) CHEBI:17268:*KNAPSACK:C00001164:*CHEBI:17268:*LIGAND-CPD:C00137:*CHEBI:24848:*PUBCHEM:892:*CAS:6917-35-7:*CAS:87-89-8:*LIGAND-CPD:C00137: 3.1.3.25 1D-myo-inositol (3)-monophosphate + H2O = myo-inositol myo-inositol biosynthesis myo-inositol cis-1,2,3,5-trans-4,6-Cyclohexanehexol*dambose*chiro-inositol*mesoinositol*meso-inositol*inositol 180.157 C6 H12 O6 OC1(C(C(C(C(C1O)O)O)O)O) CHEBI:17268:*KNAPSACK:C00001164:*CHEBI:17268:*LIGAND-CPD:C00137:*CHEBI:24848:*PUBCHEM:892:*CAS:6917-35-7:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.3.1.72 myo-inositol + indole-3-acetyl-β-1-D-glucose = indol-3-yl-acetyl-myo-inositol + β-D-glucose IAA conjugate biosynthesis I myo-inositol cis-1,2,3,5-trans-4,6-Cyclohexanehexol*dambose*chiro-inositol*mesoinositol*meso-inositol*inositol 180.157 C6 H12 O6 OC1(C(C(C(C(C1O)O)O)O)O) CHEBI:17268:*KNAPSACK:C00001164:*CHEBI:17268:*LIGAND-CPD:C00137:*CHEBI:24848:*PUBCHEM:892:*CAS:6917-35-7:*CAS:87-89-8:*LIGAND-CPD:C00137: 1D-myo-inositol (2) monophosphate + H2O = myo-inositol phytate degradation I myo-inositol cis-1,2,3,5-trans-4,6-Cyclohexanehexol*dambose*chiro-inositol*mesoinositol*meso-inositol*inositol 180.157 C6 H12 O6 OC1(C(C(C(C(C1O)O)O)O)O) CHEBI:17268:*KNAPSACK:C00001164:*CHEBI:17268:*LIGAND-CPD:C00137:*CHEBI:24848:*PUBCHEM:892:*CAS:6917-35-7:*CAS:87-89-8:*LIGAND-CPD:C00137: 3.1.3.25 H2O + 1D-myo-inositol (1)-monophosphate = myo-inositol phytate degradation I myo-inositol cis-1,2,3,5-trans-4,6-Cyclohexanehexol*dambose*chiro-inositol*mesoinositol*meso-inositol*inositol 180.157 C6 H12 O6 OC1(C(C(C(C(C1O)O)O)O)O) CHEBI:17268:*KNAPSACK:C00001164:*CHEBI:17268:*LIGAND-CPD:C00137:*CHEBI:24848:*PUBCHEM:892:*CAS:6917-35-7:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.7.1.64 myo-inositol + ATP = H+ + 1D-myo-inositol (3)-monophosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) myo-inositol cis-1,2,3,5-trans-4,6-Cyclohexanehexol*dambose*chiro-inositol*mesoinositol*meso-inositol*inositol 180.157 C6 H12 O6 OC1(C(C(C(C(C1O)O)O)O)O) CHEBI:17268:*KNAPSACK:C00001164:*CHEBI:17268:*LIGAND-CPD:C00137:*CHEBI:24848:*PUBCHEM:892:*CAS:6917-35-7:*CAS:87-89-8:*LIGAND-CPD:C00137: 3.1.3.25 1D-myo-inositol (4)-monophosphate + H2O = myo-inositol D-myo-inositol (1,4,5)-trisphosphate degradation myo-inositol cis-1,2,3,5-trans-4,6-Cyclohexanehexol*dambose*chiro-inositol*mesoinositol*meso-inositol*inositol 180.157 C6 H12 O6 OC1(C(C(C(C(C1O)O)O)O)O) CHEBI:17268:*KNAPSACK:C00001164:*CHEBI:17268:*LIGAND-CPD:C00137:*CHEBI:24848:*PUBCHEM:892:*CAS:6917-35-7:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.4.1.123 myo-inositol + UDP-D-galactose = H+ + galactinol + UDP stachyose biosynthesis myo-inositol cis-1,2,3,5-trans-4,6-Cyclohexanehexol*dambose*chiro-inositol*mesoinositol*meso-inositol*inositol 180.157 C6 H12 O6 OC1(C(C(C(C(C1O)O)O)O)O) CHEBI:17268:*KNAPSACK:C00001164:*CHEBI:17268:*LIGAND-CPD:C00137:*CHEBI:24848:*PUBCHEM:892:*CAS:6917-35-7:*CAS:87-89-8:*LIGAND-CPD:C00137: 1.13.99.1 oxygen + myo-inositol = H+ + H2O UDP-D-glucuronate biosynthesis (from myo-inositol) myo-inositol cis-1,2,3,5-trans-4,6-Cyclohexanehexol*dambose*chiro-inositol*mesoinositol*meso-inositol*inositol 180.157 C6 H12 O6 OC1(C(C(C(C(C1O)O)O)O)O) CHEBI:17268:*KNAPSACK:C00001164:*CHEBI:17268:*LIGAND-CPD:C00137:*CHEBI:24848:*PUBCHEM:892:*CAS:6917-35-7:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.4.1.67 galactinol + raffinose = myo-inositol + stachyose stachyose biosynthesis myo-inositol cis-1,2,3,5-trans-4,6-Cyclohexanehexol*dambose*chiro-inositol*mesoinositol*meso-inositol*inositol 180.157 C6 H12 O6 OC1(C(C(C(C(C1O)O)O)O)O) CHEBI:17268:*KNAPSACK:C00001164:*CHEBI:17268:*LIGAND-CPD:C00137:*CHEBI:24848:*PUBCHEM:892:*CAS:6917-35-7:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.4.1.82 galactinol + sucrose = myo-inositol + raffinose stachyose biosynthesis myo-inositol cis-1,2,3,5-trans-4,6-Cyclohexanehexol*dambose*chiro-inositol*mesoinositol*meso-inositol*inositol 180.157 C6 H12 O6 OC1(C(C(C(C(C1O)O)O)O)O) CHEBI:17268:*KNAPSACK:C00001164:*CHEBI:17268:*LIGAND-CPD:C00137:*CHEBI:24848:*PUBCHEM:892:*CAS:6917-35-7:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.7.8.11 myo-inositol = CMP phospholipid biosynthesis II myo-inositol cis-1,2,3,5-trans-4,6-Cyclohexanehexol*dambose*chiro-inositol*mesoinositol*meso-inositol*inositol 180.157 C6 H12 O6 OC1(C(C(C(C(C1O)O)O)O)O) CHEBI:17268:*KNAPSACK:C00001164:*CHEBI:17268:*LIGAND-CPD:C00137:*CHEBI:24848:*PUBCHEM:892:*CAS:6917-35-7:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.7.8.11 myo-inositol = CMP 3-phosphoinositide biosynthesis myo-inositol cis-1,2,3,5-trans-4,6-Cyclohexanehexol*dambose*chiro-inositol*mesoinositol*meso-inositol*inositol 180.157 C6 H12 O6 OC1(C(C(C(C(C1O)O)O)O)O) CHEBI:17268:*KNAPSACK:C00001164:*CHEBI:17268:*LIGAND-CPD:C00137:*CHEBI:24848:*PUBCHEM:892:*CAS:6917-35-7:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.7.8.11 myo-inositol = CMP D-myo-inositol (1,4,5)-trisphosphate biosynthesis 3-dehydroquinate 3-dehydroquinic acid*5-dehydroquinic acid*5-dehydroquinate*5-de-H-quinate 189.144 C7 H9 O6 C1(O)(C([O-])=O)(CC(=O)C(O)C(O)C1) PUBCHEM:5460271:*CHEBI:32364:*LIGAND-CPD:C00944:*CAS:10534-44-8 4.2.1.10 3-dehydroquinate = H2O + 3-dehydroshikimate chorismate biosynthesis I 3-dehydroquinate 3-dehydroquinic acid*5-dehydroquinic acid*5-dehydroquinate*5-de-H-quinate 189.144 C7 H9 O6 C1(O)(C([O-])=O)(CC(=O)C(O)C(O)C1) PUBCHEM:5460271:*CHEBI:32364:*LIGAND-CPD:C00944:*CAS:10534-44-8 4.2.3.4 3-deoxy-D-arabino-heptulosonate-7-phosphate = 3-dehydroquinate chorismate biosynthesis I 3-dehydroquinate 3-dehydroquinic acid*5-dehydroquinic acid*5-dehydroquinate*5-de-H-quinate 189.144 C7 H9 O6 C1(O)(C([O-])=O)(CC(=O)C(O)C(O)C1) PUBCHEM:5460271:*CHEBI:32364:*LIGAND-CPD:C00944:*CAS:10534-44-8 4.2.3.4 3-deoxy-D-arabino-heptulosonate-7-phosphate = 3-dehydroquinate 3-dehydroquinate biosynthesis I decanoyl-CoA 917.754 C31 H50 N7 O17 P3 S1 O=C(CCCCCCCCC)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-] PUBCHEM:25244140:*LIGAND-CPD:C05274: 3.1.2.2 decanoyl-CoA + H2O = H+ + caprate + coenzyme A ω-hydroxylation of caprate and laurate indole-3-acetyl-β-1-D-glucose 1-O-indol-3-ylacetyl-β-D-glucose*IAA-Glc*indole-3-acetyl-glucose*Indole-3-acetyl-beta-1-D-glucoside*IAA-glucose 337.329 C16 H19 N1 O7 O=C(CC1(=CNC2(C=CC=CC1=2)))OC3(OC(CO)C(O)C(O)C(O)3) PUBCHEM:440255:*CHEBI:17990:*LIGAND-CPD:C04197: 2.4.1.121 indole-3-acetate = indole-3-acetyl-β-1-D-glucose + UDP IAA conjugate biosynthesis I indole-3-acetyl-β-1-D-glucose 1-O-indol-3-ylacetyl-β-D-glucose*IAA-Glc*indole-3-acetyl-glucose*Indole-3-acetyl-beta-1-D-glucoside*IAA-glucose 337.329 C16 H19 N1 O7 O=C(CC1(=CNC2(C=CC=CC1=2)))OC3(OC(CO)C(O)C(O)C(O)3) PUBCHEM:440255:*CHEBI:17990:*LIGAND-CPD:C04197: 2.3.1.72 myo-inositol + indole-3-acetyl-β-1-D-glucose = indol-3-yl-acetyl-myo-inositol + β-D-glucose IAA conjugate biosynthesis I umbelliferone 7-oxycoumarin*skimmetin*hydrangin*7-hydroxycoumarin 162.145 C9 H6 O3 OC2(C=C1(OC(=O)C=CC1=CC=2)) PUBCHEM:5281426:*PUBCHEM:5281426:*CHEBI:27510:*LIGAND-CPD:C09315: 2,4-dihydroxycinnamate = umbelliferone simplecoumarins biosynthesis umbelliferone 7-oxycoumarin*skimmetin*hydrangin*7-hydroxycoumarin 162.145 C9 H6 O3 OC2(C=C1(OC(=O)C=CC1=CC=2)) PUBCHEM:5281426:*PUBCHEM:5281426:*CHEBI:27510:*LIGAND-CPD:C09315: umbelliferone = esculetin simplecoumarins biosynthesis umbelliferone 7-oxycoumarin*skimmetin*hydrangin*7-hydroxycoumarin 162.145 C9 H6 O3 OC2(C=C1(OC(=O)C=CC1=CC=2)) PUBCHEM:5281426:*PUBCHEM:5281426:*CHEBI:27510:*LIGAND-CPD:C09315: umbelliferone = herniarin simplecoumarins biosynthesis 3,4-dihydroxy-5-all-trans-nonaprenylbenzoate 3-(3,7,11,15,19,23-nonamethyltetracosa-2,6,10,14,18,22-hexaenyl) -4,5-dihydroxy-benzoic acid*3-nonaprenyl-4,5-dihydroxybenzoate 766.178 C52 H77 O4 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(=C(C(=CC(C([O-])=O)=C1)O)O))C)C)C)C)C)CCC=C(CCC=C(C)CCC=C(C)C)C PUBCHEM:25245371: 2.1.1.114 3,4-dihydroxy-5-all-trans-nonaprenylbenzoate + S-adenosyl-L-methionine = H+ + 3-methoxy-4-hydroxy-5-all-trans-nonaprenylbenzoate + S-adenosyl-L-homocysteine ubiquinol-9 biosynthesis (eukaryotic) 3,4-dihydroxy-5-all-trans-nonaprenylbenzoate 3-(3,7,11,15,19,23-nonamethyltetracosa-2,6,10,14,18,22-hexaenyl) -4,5-dihydroxy-benzoic acid*3-nonaprenyl-4,5-dihydroxybenzoate 766.178 C52 H77 O4 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(=C(C(=CC(C([O-])=O)=C1)O)O))C)C)C)C)C)CCC=C(CCC=C(C)CCC=C(C)C)C PUBCHEM:25245371: 1.14.13.- nonaprenyl-4-hydroxybenzoate + oxygen + NADPH + H+ = 3,4-dihydroxy-5-all-trans-nonaprenylbenzoate + H2O + NADP+ ubiquinol-9 biosynthesis (eukaryotic) sabinene (-)-(1S)-sabinene 136.236 C10 H16 C1(CCC2(C(C)C)(C1C2))=C PUBCHEM:6429260:*LIGAND-CPD:C16777: 4.2.3.- geranyl diphosphate = sabinene + diphosphate monoterpene biosynthesis UDP-L-rhamnose UDP-rhamnose 548.29 C15 H22 N2 O16 P2 CC3(OC(OP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(=O)NC(=O)2)))C(O)C(O)C(O)3) PUBCHEM:25246011:*LIGAND-CPD:C02199: H+ + UDP-4-dehydro-6-deoxy-D-glucose + NADPH = UDP-L-rhamnose + NADP+ UDP-L-rhamnose biosynthesis 3-deoxy-D-manno-octulosonate 3-deoxy-D-manno-2-octulosonate*3-deoxy-D-manno-octulosonate*3-deoxyoctulosonate*3-Deoxy-D-mannooctulosonate*3-KDO*3-Deoxyoctulosonic acid*2-keto-3-deoxyoctonate*deoxy-manno-octulosonate*2-dehydro-3-deoxy-D-octonate*KDO*ketodeoxyoctonate 237.186 C8 H13 O8 OCC(O)C(O)C(O)C(O)CC(=O)C(=O)[O-] CHEBI:32817:*PUBCHEM:22706768:*CHEBI:16064:*PUBCHEM:5460395:*LIGAND-CPD:C01187: 2.7.7.38 3-deoxy-D-manno-octulosonate + CTP = CMP-3-deoxy-D-manno-octulosonate + diphosphate CMP-KDO biosynthesis II (from D-arabinose 5-phosphate) 3-deoxy-D-manno-octulosonate 3-deoxy-D-manno-2-octulosonate*3-deoxy-D-manno-octulosonate*3-deoxyoctulosonate*3-Deoxy-D-mannooctulosonate*3-KDO*3-Deoxyoctulosonic acid*2-keto-3-deoxyoctonate*deoxy-manno-octulosonate*2-dehydro-3-deoxy-D-octonate*KDO*ketodeoxyoctonate 237.186 C8 H13 O8 OCC(O)C(O)C(O)C(O)CC(=O)C(=O)[O-] CHEBI:32817:*PUBCHEM:22706768:*CHEBI:16064:*PUBCHEM:5460395:*LIGAND-CPD:C01187: 3.1.3.45 3-deoxy-D-manno-octulosonate 8-P + H2O = 3-deoxy-D-manno-octulosonate CMP-KDO biosynthesis II (from D-arabinose 5-phosphate) pyridoxal 5'-phosphate PLP*pyridoxal phosphate*pyridoxal-5P*pyridoxal 5-phosphate*pyridoxal-P*vitamin B6 245.128 C8 H8 N1 O6 P1 C1(C(=C(C(=C(N=1)C)O)C=O)COP(=O)([O-])[O-]) CHEBI:597326:*METACYC:PYRIDOXAL_PHOSPHATE:*PUBCHEM:644168:*PUBCHEM:644168:*LIGAND-CPD:C00018:*CAS:54-47-7 1.4.3.5 oxygen + H2O + pyridoxamine 5'-phosphate = H+ + ammonia + hydrogen peroxide + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway pyridoxal 5'-phosphate PLP*pyridoxal phosphate*pyridoxal-5P*pyridoxal 5-phosphate*pyridoxal-P*vitamin B6 245.128 C8 H8 N1 O6 P1 C1(C(=C(C(=C(N=1)C)O)C=O)COP(=O)([O-])[O-]) CHEBI:597326:*METACYC:PYRIDOXAL_PHOSPHATE:*PUBCHEM:644168:*PUBCHEM:644168:*LIGAND-CPD:C00018:*CAS:54-47-7 2.7.1.35 ATP + pyridoxal = H+ + ADP + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway pyridoxal 5'-phosphate PLP*pyridoxal phosphate*pyridoxal-5P*pyridoxal 5-phosphate*pyridoxal-P*vitamin B6 245.128 C8 H8 N1 O6 P1 C1(C(=C(C(=C(N=1)C)O)C=O)COP(=O)([O-])[O-]) CHEBI:597326:*METACYC:PYRIDOXAL_PHOSPHATE:*PUBCHEM:644168:*PUBCHEM:644168:*LIGAND-CPD:C00018:*CAS:54-47-7 1.4.3.5 oxygen + pyridoxine-5'-phosphate = hydrogen peroxide + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway dihydrozeatin-9-N-glucoside-O-glucoside 545.545 C22 H35 N5 O11 C1(C2(=C(N=CN=1)N(C=N2)C3(C(C(C(C(O3)CO)O)O)O)))NCCC(COC4(C(C(C(C(O4)CO)O)O)O))C PUBCHEM:25201670: 2.4.1.- dihydrozeatin-9-N-glucoside = H+ + dihydrozeatin-9-N-glucoside-O-glucoside + UDP cytokinins-O-glucoside biosynthesis dihydrogeranylgeranyl-chlorophyll a dihydrogeranylgeranyl-chl a*dihydroGG-chl a*dihydroGG-chlorophyll a 889.471 C55 H68 N4 O5 MG1 C24(C=C9(C(C)C(CCC(=O)OCC=C(C)CCCC(C)CCC=C(C)CCC=C(C)C)C5(=N([Mg]36(N1(=C(C(CC)=C(C)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) PUBCHEM:25245376: 1.3.1.- H+ + dihydrogeranylgeranyl-chlorophyll a + NADPH = tetrahydrogeranylgeranyl-chlorophyll a + NADP+ chlorophyll a biosynthesis II dihydrogeranylgeranyl-chlorophyll a dihydrogeranylgeranyl-chl a*dihydroGG-chl a*dihydroGG-chlorophyll a 889.471 C55 H68 N4 O5 MG1 C24(C=C9(C(C)C(CCC(=O)OCC=C(C)CCCC(C)CCC=C(C)CCC=C(C)C)C5(=N([Mg]36(N1(=C(C(CC)=C(C)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) PUBCHEM:25245376: 1.3.1.- H+ + geranylgeranyl-chlorophyll a + NADPH = dihydrogeranylgeranyl-chlorophyll a + NADP+ chlorophyll a biosynthesis II ent-kaurenoate ent-kaur-16-en-19-oate*ent-kaurenoic acid 301.448 C20 H29 O2 C1(CCC(C2(C1(C3(CCC4(CC(CC2)3CC4=C)))C))(C)C([O-])=O) PUBCHEM:25200785:*LIGAND-CPD:C11874: 1.14.13.79 H+ + ent-kaurenoate + oxygen + NADPH = ent-7-α-hydroxykaurenoate + H2O + NADP+ GA12 biosynthesis ent-kaurenoate ent-kaur-16-en-19-oate*ent-kaurenoic acid 301.448 C20 H29 O2 C1(CCC(C2(C1(C3(CCC4(CC(CC2)3CC4=C)))C))(C)C([O-])=O) PUBCHEM:25200785:*LIGAND-CPD:C11874: 1.14.13.78 ent-kaurenal + NADPH + oxygen = ent-kaurenoate + NADP+ + H2O GA12 biosynthesis laurate n-dodecanoic acid*tin II 2-ethylhexanoate*dodecanoic acid*dodecylcarboxylate*lauric acid*laurostearic acid*dodecoic acid*dodecylic acid*duodecylic acid*n-dodecanoic acid*1-undecanecarboxylic acid*dodecanoate (n-C12:0)*dodecanoate 199.312 C12 H23 O2 C(CCC([O-])=O)CCCCCCCC CHEBI:18262:*PUBCHEM:4149208:*CHEBI:30805:*LIGAND-CPD:C02679:*NCI:5026*CAS:143-07-7 3.1.2.2 lauroyl-CoA + H2O = H+ + laurate + coenzyme A ω-hydroxylation of caprate and laurate laurate n-dodecanoic acid*tin II 2-ethylhexanoate*dodecanoic acid*dodecylcarboxylate*lauric acid*laurostearic acid*dodecoic acid*dodecylic acid*duodecylic acid*n-dodecanoic acid*1-undecanecarboxylic acid*dodecanoate (n-C12:0)*dodecanoate 199.312 C12 H23 O2 C(CCC([O-])=O)CCCCCCCC CHEBI:18262:*PUBCHEM:4149208:*CHEBI:30805:*LIGAND-CPD:C02679:*NCI:5026*CAS:143-07-7 3.1.2.21 H2O = laurate palmitate biosynthesis II (bacteria and plants) laurate n-dodecanoic acid*tin II 2-ethylhexanoate*dodecanoic acid*dodecylcarboxylate*lauric acid*laurostearic acid*dodecoic acid*dodecylic acid*duodecylic acid*n-dodecanoic acid*1-undecanecarboxylic acid*dodecanoate (n-C12:0)*dodecanoate 199.312 C12 H23 O2 C(CCC([O-])=O)CCCCCCCC CHEBI:18262:*PUBCHEM:4149208:*CHEBI:30805:*LIGAND-CPD:C02679:*NCI:5026*CAS:143-07-7 1.14.13.- laurate + oxygen + NADPH + H+ = ω-hydroxylaurate + NADP+ + H2O ω-hydroxylation of caprate and laurate palmitate Hexadecanoate (n-C16:0)*palmitic acid*hexadecanoate 255.42 C16 H31 O2 C(CCCCCCCCC(=O)[O-])CCCCCC CHEBI:29889:*PUBCHEM:504166:*|Wikipedia|:Palmitic_acid:*LIGAND-CPD:C00249:*PUBCHEM:985:*CAS:57-10-3 3.1.2.14 H2O = palmitate palmitate biosynthesis II (bacteria and plants) 5'-phosphoribosyl-N-formylglycineamide N2-formyl-N1-(5-phospho-D-ribosyl)glycinamide*N2-Formyl-N1-(5-phospho-D-ribosyl)glycinamide*5'-P-ribosyl-N-formylglycineamide*5'-phosphoribosyl-N-formylglycinamide*5'-phosphoribosyl-N-formylglycineamide*FGAR*5-phosphoribosyl-N-formalglycineamide*5'-phosphoribosyl-formylglycinamide 312.172 C8 H13 N2 O9 P1 C(NC1(C(C(C(COP([O-])(=O)[O-])O1)O)O))(=O)CNC=O PUBCHEM:440313:*PUBCHEM:25245380:*LIGAND-CPD:C04376: 2.1.2.2 10-formyl-tetrahydrofolate + 5-phospho-ribosyl-glycineamide = H+ + tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate 5'-phosphoribosyl-N-formylglycineamide N2-formyl-N1-(5-phospho-D-ribosyl)glycinamide*N2-Formyl-N1-(5-phospho-D-ribosyl)glycinamide*5'-P-ribosyl-N-formylglycineamide*5'-phosphoribosyl-N-formylglycinamide*5'-phosphoribosyl-N-formylglycineamide*FGAR*5-phosphoribosyl-N-formalglycineamide*5'-phosphoribosyl-formylglycinamide 312.172 C8 H13 N2 O9 P1 C(NC1(C(C(C(COP([O-])(=O)[O-])O1)O)O))(=O)CNC=O PUBCHEM:440313:*PUBCHEM:25245380:*LIGAND-CPD:C04376: 2.1.2.2 10-formyl-tetrahydrofolate + 5-phospho-ribosyl-glycineamide = H+ + tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide 5-aminoimidazole ribonucleotide biosynthesis I 5'-phosphoribosyl-N-formylglycineamide N2-formyl-N1-(5-phospho-D-ribosyl)glycinamide*N2-Formyl-N1-(5-phospho-D-ribosyl)glycinamide*5'-P-ribosyl-N-formylglycineamide*5'-phosphoribosyl-N-formylglycinamide*5'-phosphoribosyl-N-formylglycineamide*FGAR*5-phosphoribosyl-N-formalglycineamide*5'-phosphoribosyl-formylglycinamide 312.172 C8 H13 N2 O9 P1 C(NC1(C(C(C(COP([O-])(=O)[O-])O1)O)O))(=O)CNC=O PUBCHEM:440313:*PUBCHEM:25245380:*LIGAND-CPD:C04376: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis II 5'-phosphoribosyl-N-formylglycineamide N2-formyl-N1-(5-phospho-D-ribosyl)glycinamide*N2-Formyl-N1-(5-phospho-D-ribosyl)glycinamide*5'-P-ribosyl-N-formylglycineamide*5'-phosphoribosyl-N-formylglycinamide*5'-phosphoribosyl-N-formylglycineamide*FGAR*5-phosphoribosyl-N-formalglycineamide*5'-phosphoribosyl-formylglycinamide 312.172 C8 H13 N2 O9 P1 C(NC1(C(C(C(COP([O-])(=O)[O-])O1)O)O))(=O)CNC=O PUBCHEM:440313:*PUBCHEM:25245380:*LIGAND-CPD:C04376: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis I 5'-phosphoribosyl-N-formylglycineamide N2-formyl-N1-(5-phospho-D-ribosyl)glycinamide*N2-Formyl-N1-(5-phospho-D-ribosyl)glycinamide*5'-P-ribosyl-N-formylglycineamide*5'-phosphoribosyl-N-formylglycinamide*5'-phosphoribosyl-N-formylglycineamide*FGAR*5-phosphoribosyl-N-formalglycineamide*5'-phosphoribosyl-formylglycinamide 312.172 C8 H13 N2 O9 P1 C(NC1(C(C(C(COP([O-])(=O)[O-])O1)O)O))(=O)CNC=O PUBCHEM:440313:*PUBCHEM:25245380:*LIGAND-CPD:C04376: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine superpathway of 5-aminoimidazole ribonucleotide biosynthesis 5'-phosphoribosyl-N-formylglycineamide N2-formyl-N1-(5-phospho-D-ribosyl)glycinamide*N2-Formyl-N1-(5-phospho-D-ribosyl)glycinamide*5'-P-ribosyl-N-formylglycineamide*5'-phosphoribosyl-N-formylglycinamide*5'-phosphoribosyl-N-formylglycineamide*FGAR*5-phosphoribosyl-N-formalglycineamide*5'-phosphoribosyl-formylglycinamide 312.172 C8 H13 N2 O9 P1 C(NC1(C(C(C(COP([O-])(=O)[O-])O1)O)O))(=O)CNC=O PUBCHEM:440313:*PUBCHEM:25245380:*LIGAND-CPD:C04376: 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = H+ + 5'-phosphoribosyl-N-formylglycineamide + ADP 5-aminoimidazole ribonucleotide biosynthesis II 5'-phosphoribosyl-N-formylglycineamide N2-formyl-N1-(5-phospho-D-ribosyl)glycinamide*N2-Formyl-N1-(5-phospho-D-ribosyl)glycinamide*5'-P-ribosyl-N-formylglycineamide*5'-phosphoribosyl-N-formylglycinamide*5'-phosphoribosyl-N-formylglycineamide*FGAR*5-phosphoribosyl-N-formalglycineamide*5'-phosphoribosyl-formylglycinamide 312.172 C8 H13 N2 O9 P1 C(NC1(C(C(C(COP([O-])(=O)[O-])O1)O)O))(=O)CNC=O PUBCHEM:440313:*PUBCHEM:25245380:*LIGAND-CPD:C04376: 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = H+ + 5'-phosphoribosyl-N-formylglycineamide + ADP superpathway of 5-aminoimidazole ribonucleotide biosynthesis 6-deoxotyphasterol deoxotyphasterol 434.701 C28 H50 O3 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(C(C(C(C(C)C)C)O)O)C)C(CC3)(C)4)))C))O) PUBCHEM:25203471:*LIGAND-CPD:C15801: H+ + 3-dehydro-6-deoxoteasterone = 6-deoxotyphasterol brassinosteroid biosynthesis II 6-deoxotyphasterol deoxotyphasterol 434.701 C28 H50 O3 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(C(C(C(C(C)C)C)O)O)C)C(CC3)(C)4)))C))O) PUBCHEM:25203471:*LIGAND-CPD:C15801: 1.14.13.- H+ + 3-epi-6-deoxocathasterone + NADPH + oxygen = 6-deoxotyphasterol + NADP+ + H2O brassinosteroid biosynthesis II α-D-ribose-1-phosphate ribose-1-phosphate*D-ribose-1-phosphate*α-D-ribose-1P*α-D-ribofuranose 1-phosphate*α-D-ribose-1-phosphate 228.095 C5 H9 O8 P1 C1(OP(=O)([O-])[O-])(OC(C(O)C(O)1)CO) PUBCHEM:44229232:*PUBCHEM:123732:*LIGAND-CPD:C00620:*CHEBI:16300:*CAS:58459-37-3:*LIGAND-CPD:C00442:*CAS:14075-00-4 2.4.2.3 uridine = α-D-ribose-1-phosphate + uracil salvage pathways of pyrimidine ribonucleotides α-D-ribose-1-phosphate ribose-1-phosphate*D-ribose-1-phosphate*α-D-ribose-1P*α-D-ribofuranose 1-phosphate*α-D-ribose-1-phosphate 228.095 C5 H9 O8 P1 C1(OP(=O)([O-])[O-])(OC(C(O)C(O)1)CO) PUBCHEM:44229232:*PUBCHEM:123732:*LIGAND-CPD:C00620:*CHEBI:16300:*CAS:58459-37-3:*LIGAND-CPD:C00442:*CAS:14075-00-4 2.4.2.1 inosine = hypoxanthine + α-D-ribose-1-phosphate adenosine nucleotides degradation II hydroxypyruvate β-hydroxypyruvate*OH-pyruvate*OH-pyr*3-hydroxypyruvate 103.054 C3 H3 O4 C(=O)(C([O-])=O)CO PUBCHEM:4186339:*CHEBI:17180:*LIGAND-CPD:C00168:*CAS:1113-60-6 1.1.1.29 D-glycerate + NAD+ = H+ + hydroxypyruvate + NADH photorespiration hydroxypyruvate β-hydroxypyruvate*OH-pyruvate*OH-pyr*3-hydroxypyruvate 103.054 C3 H3 O4 C(=O)(C([O-])=O)CO PUBCHEM:4186339:*CHEBI:17180:*LIGAND-CPD:C00168:*CAS:1113-60-6 2.6.1.45 glyoxylate + L-serine = hydroxypyruvate + glycine photorespiration 7,9,9'-cis-neurosporene proneurosporene*7,9,9'-tri-cis-neurosporene 538.898 C40 H58 CC(=CCCC(=CC=CC(C)=CC=CC(=CC=CC=C(C=CC=C(C)CCC=C(CCC=C(C)C)C)C)C)C)C PUBCHEM:25244751: 9,9'-di-cis-ζ-carotene + oxygen = 7,9,9'-cis-neurosporene + H2O trans-lycopene biosynthesis II (plants) 7,9,9'-cis-neurosporene proneurosporene*7,9,9'-tri-cis-neurosporene 538.898 C40 H58 CC(=CCCC(=CC=CC(C)=CC=CC(=CC=CC=C(C=CC=C(C)CCC=C(CCC=C(C)C)C)C)C)C)C PUBCHEM:25244751: 7,9,9'-cis-neurosporene + oxygen = prolycopene + H2O trans-lycopene biosynthesis II (plants) 7,9,9'-cis-neurosporene proneurosporene*7,9,9'-tri-cis-neurosporene 538.898 C40 H58 CC(=CCCC(=CC=CC(C)=CC=CC(=CC=CC=C(C=CC=C(C)CCC=C(CCC=C(C)C)C)C)C)C)C PUBCHEM:25244751: 5.2.1.- 7,9,9'-cis-neurosporene = 9'-cis-neurosporene trans-lycopene biosynthesis II (plants) D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.134 D-myo-inositol (3,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.134 D-myo-inositol (3,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 3.1.3.- D-myo-inositol (1,3,4,5,6)-pentakisphosphate + H2O = D-myo-inositol (3,4,5,6)-tetrakisphosphate D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.151 D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.151 D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.151 D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 3.1.3.- D-myo-inositol (1,3,4,5,6)-pentakisphosphate + H2O = D-myo-inositol (1,4,5,6)-tetrakisphosphate D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.151 D-myo-inositol (1,3,4,5)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.151 D-myo-inositol (1,3,4,5)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) D-myo-inositol (1,3,4,5,6)-pentakisphosphate Ins(1,3,4,5,6)P5*1D-myo-inositol (1,3,4,5,6)-pentakisphosphate*inositol (1,3,4,5,6)-pentakisphosphate*I(1,3,4,5,6)P5 569.977 C6 H7 O21 P5 C1(C(C(OP([O-])(=O)[O-])C(C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])1)OP([O-])([O-])=O)OP([O-])([O-])=O)O PUBCHEM:23615305:*LIGAND-CPD:C01284: 2.7.1.151 D-myo-inositol (1,3,4,5)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) thiamin thiamin*thiamine*vitamin B1 265.352 C12 H17 N4 O1 S1 OCCC1(=C([N+](=CS1)CC2(=C(N=C(C)N=C2)N))C) PUBCHEM:1130:*CHEBI:18385:*CAS:67-03-8:*LIGAND-CPD:C00378:*CAS:59-43-8 3.1.3.2 thiamine-phosphate + H2O = thiamin thiamine biosynthesis II thiamin thiamin*thiamine*vitamin B1 265.352 C12 H17 N4 O1 S1 OCCC1(=C([N+](=CS1)CC2(=C(N=C(C)N=C2)N))C) PUBCHEM:1130:*CHEBI:18385:*CAS:67-03-8:*LIGAND-CPD:C00378:*CAS:59-43-8 2.7.6.2 thiamin + ATP = H+ + thiamine diphosphate + AMP thiamine biosynthesis II UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 2.4.1.156 indol-3-yl-acetyl-myo-inositol + UDP-D-galactose = H+ + 5-O-(indol-3-ylacetyl-myo-inositol) D-galactoside + UDP IAA conjugate biosynthesis I UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 2.4.1.241 UDP-D-galactose = UDP glycolipid biosynthesis UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 5.1.3.2 galactose degradation I (Leloir pathway) UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 5.1.3.2 UDP-galactose biosynthesis UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 5.1.3.2 stachyose degradation UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 5.1.3.2 colanic acid building blocks biosynthesis UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 5.1.3.2 UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 5.1.3.2 galactose degradation III UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 2.7.7.10 H+ + α-D-galactose 1-phosphate + UTP = UDP-D-galactose + diphosphate stachyose degradation UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 2.7.7.10 H+ + α-D-galactose 1-phosphate + UTP = UDP-D-galactose + diphosphate galactose degradation III UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 UDP-D-galactose = UDP xyloglucan biosynthesis UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 2.4.1.46 UDP-D-galactose = UDP glycolipid biosynthesis UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 2.4.1.123 myo-inositol + UDP-D-galactose = H+ + galactinol + UDP stachyose biosynthesis UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 2.7.7.12 α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-D-galactose galactose degradation I (Leloir pathway) UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 2.7.7.12 α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-D-galactose stachyose degradation UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 2.7.7.12 α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-D-galactose colanic acid building blocks biosynthesis UDP-D-galactose UDP-galactose*UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:58439:*PUBCHEM:44229096:*LIGAND-CPD:C00052:*CAS:2956-16-3 2.7.7.12 α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-D-galactose UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) norspermidine 3,3'-Iminobispropylamine*bis(3-aminopropyl)amine*N-3-aminopropyl-1,3-diaminopropane*sym-norspermidine 134.244 C6 H20 N3 C([N+])CC[N+]CCC[N+] PUBCHEM:6991998:*CHEBI:16841:*LIGAND-CPD:C03375:*CAS:56-18-8 2,3-dihydroxybenzoate-VibB + norspermidine = norspermidine-2,3-dihydroxybenzoate + H2O vibriobactin biosynthesis L-valine V*val*valine 117.147 C5 H11 N1 O2 CC(C)C([N+])C([O-])=O PUBCHEM:6971018:*KNAPSACK:C00001398:*CHEBI:57762:*PUBCHEM:6971018:*LIGAND-CPD:C00183:*CAS:72-18-4 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate valine degradation I L-valine V*val*valine 117.147 C5 H11 N1 O2 CC(C)C([N+])C([O-])=O PUBCHEM:6971018:*KNAPSACK:C00001398:*CHEBI:57762:*PUBCHEM:6971018:*LIGAND-CPD:C00183:*CAS:72-18-4 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate valine biosynthesis L-valine V*val*valine 117.147 C5 H11 N1 O2 CC(C)C([N+])C([O-])=O PUBCHEM:6971018:*KNAPSACK:C00001398:*CHEBI:57762:*PUBCHEM:6971018:*LIGAND-CPD:C00183:*CAS:72-18-4 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate pantothenate biosynthesis I L-valine V*val*valine 117.147 C5 H11 N1 O2 CC(C)C([N+])C([O-])=O PUBCHEM:6971018:*KNAPSACK:C00001398:*CHEBI:57762:*PUBCHEM:6971018:*LIGAND-CPD:C00183:*CAS:72-18-4 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate valine degradation II L-valine V*val*valine 117.147 C5 H11 N1 O2 CC(C)C([N+])C([O-])=O PUBCHEM:6971018:*KNAPSACK:C00001398:*CHEBI:57762:*PUBCHEM:6971018:*LIGAND-CPD:C00183:*CAS:72-18-4 6.1.1.9 H+ + L-valine + ATP = diphosphate + AMP tRNA charging pathway cis-zeatin-O-glucoside O-β-D-glucosyl-cis-zeatin 381.388 C16 H23 N5 O6 C1(C2(=C(N=CN=1)N=CN2))NCC=C(COC3(C(C(C(C(O3)CO)O)O)O))C CHEBI:29043:*PUBCHEM:5461146: 2.4.1.215 cis-zeatin = cis-zeatin-O-glucoside + H+ + UDP cytokinins-O-glucoside biosynthesis crinosterol 398.671 C28 H46 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CC3)4C)C(C=CC(C)C(C)C)C)))C))O) PUBCHEM:25244148: 1.3.1.- campesterol + NADP+ = H+ + crinosterol + NADPH plant sterol biosynthesis 5-methylthioribulose-1-phosphate 5-methylthio-5-deoxy-D-ribulose-1-phosphate*1-phosphomethylthioribulose*methylthioribulose-1-phosphate*MTRu-1-P*1PMT-ribulose*1-phospho-5-S-methylthioribulose 258.182 C6 H11 O7 P1 S1 O(P([O-])(=O)[O-])CC(=O)C(O)C(O)CSC PUBCHEM:329:*CHEBI:58548:*PUBCHEM:23615271:*LIGAND-CPD:C04582: 5.3.1.23 5-methylthioribose-1-phosphate = 5-methylthioribulose-1-phosphate methionine salvage I 5-methylthioribulose-1-phosphate 5-methylthio-5-deoxy-D-ribulose-1-phosphate*1-phosphomethylthioribulose*methylthioribulose-1-phosphate*MTRu-1-P*1PMT-ribulose*1-phospho-5-S-methylthioribulose 258.182 C6 H11 O7 P1 S1 O(P([O-])(=O)[O-])CC(=O)C(O)C(O)CSC PUBCHEM:329:*CHEBI:58548:*PUBCHEM:23615271:*LIGAND-CPD:C04582: 4.2.1.109 5-methylthioribulose-1-phosphate = 5-(methylthio)-2,3-dioxopentyl phosphate + H2O methionine salvage I riboflavin vitamin B2*vitamin B2 375.36 C17 H19 N4 O6 C(CO)(C(C(CN3(C1(C(=CC(C)=C(C=1)C)N=C2(C(=O)[N-]C(=O)N=C23))))O)O)O PUBCHEM:6759:*PUBCHEM:6759:*PUBCHEM:122171:*PUBCHEM:122171:*LIGAND-CPD:C00255:*CAS:83-88-5 2.7.1.26 riboflavin + ATP = H+ + FMN + ADP flavin biosynthesis I (bacteria and plants) riboflavin vitamin B2*vitamin B2 375.36 C17 H19 N4 O6 C(CO)(C(C(CN3(C1(C(=CC(C)=C(C=1)C)N=C2(C(=O)[N-]C(=O)N=C23))))O)O)O PUBCHEM:6759:*PUBCHEM:6759:*PUBCHEM:122171:*PUBCHEM:122171:*LIGAND-CPD:C00255:*CAS:83-88-5 2.5.1.9 H+ + 6,7-dimethyl-8-(1-D-ribityl)lumazine = 5-amino-6-(D-ribitylamino)uracil + riboflavin flavin biosynthesis I (bacteria and plants) N-carbamoyl-L-aspartate carbamyul-L-aspartate*N-carbamoyl-L-aspartate*carbamyul-aspartate*carbamoyl-aspartate*carbamyl-aspartate*carbamyl-L-aspartate 174.113 C5 H6 N2 O5 C(CC(C(=O)[O-])NC(=O)N)(=O)[O-] PUBCHEM:21960964:*LIGAND-CPD:C00438:*CAS:16649-79-9 3.5.2.3 (S)-dihydroorotate + H2O = H+ + N-carbamoyl-L-aspartate uridine-5'-phosphate biosynthesis N-carbamoyl-L-aspartate carbamyul-L-aspartate*N-carbamoyl-L-aspartate*carbamyul-aspartate*carbamoyl-aspartate*carbamyl-aspartate*carbamyl-L-aspartate 174.113 C5 H6 N2 O5 C(CC(C(=O)[O-])NC(=O)N)(=O)[O-] PUBCHEM:21960964:*LIGAND-CPD:C00438:*CAS:16649-79-9 2.1.3.2 L-aspartate + carbamoyl-phosphate = H+ + N-carbamoyl-L-aspartate uridine-5'-phosphate biosynthesis 2-aceto-2-hydroxy-butanoate α-aceto-α-hydroxybutyrate*acetohydroxybutyrate*acetohydroxybutanoate*2-aceto-2-hydroxy-butyrate 145.135 C6 H9 O4 C(C(O)(C(=O)[O-])C(C)=O)C PUBCHEM:21:*PUBCHEM:13999771:*LIGAND-CPD:C06006:*CAS:3142-65-2 2.2.1.6 H+ + pyruvate + 2-oxobutanoate = 2-aceto-2-hydroxy-butanoate + CO2 isoleucine biosynthesis I (from threonine) 2-aceto-2-hydroxy-butanoate α-aceto-α-hydroxybutyrate*acetohydroxybutyrate*acetohydroxybutanoate*2-aceto-2-hydroxy-butyrate 145.135 C6 H9 O4 C(C(O)(C(=O)[O-])C(C)=O)C PUBCHEM:21:*PUBCHEM:13999771:*LIGAND-CPD:C06006:*CAS:3142-65-2 1.1.1.86 H+ + 2-aceto-2-hydroxy-butanoate + NADPH = 2,3-dihydroxy-3-methylvalerate + NADP+ isoleucine biosynthesis I (from threonine) 5-amino-6-(D-ribitylamino)uracil compound 6*4-(1-D-ribitylamino)-5-aminouracil*4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine*6-(1-D-ribitylamino)-5-amino-2,4-dihydroxypyrimidine*5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione*ARP*6-(1-D-ribitylamino)-5-aminouracil*5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione 276.249 C9 H16 N4 O6 N(CC(O)C(O)C(O)CO)C1(NC(=O)NC(=O)C(N)=1) PUBCHEM:14056325:*LIGAND-CPD:C04732: 2.5.1.78 5-amino-6-(D-ribitylamino)uracil + 1-deoxy-L-glycero-tetrulose 4-phosphate = H+ + 6,7-dimethyl-8-(1-D-ribityl)lumazine + H2O flavin biosynthesis I (bacteria and plants) 5-amino-6-(D-ribitylamino)uracil compound 6*4-(1-D-ribitylamino)-5-aminouracil*4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine*6-(1-D-ribitylamino)-5-amino-2,4-dihydroxypyrimidine*5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione*ARP*6-(1-D-ribitylamino)-5-aminouracil*5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione 276.249 C9 H16 N4 O6 N(CC(O)C(O)C(O)CO)C1(NC(=O)NC(=O)C(N)=1) PUBCHEM:14056325:*LIGAND-CPD:C04732: 2.5.1.9 H+ + 6,7-dimethyl-8-(1-D-ribityl)lumazine = 5-amino-6-(D-ribitylamino)uracil + riboflavin flavin biosynthesis I (bacteria and plants) 5-amino-6-(D-ribitylamino)uracil compound 6*4-(1-D-ribitylamino)-5-aminouracil*4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine*6-(1-D-ribitylamino)-5-amino-2,4-dihydroxypyrimidine*5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione*ARP*6-(1-D-ribitylamino)-5-aminouracil*5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione 276.249 C9 H16 N4 O6 N(CC(O)C(O)C(O)CO)C1(NC(=O)NC(=O)C(N)=1) PUBCHEM:14056325:*LIGAND-CPD:C04732: 5-amino-6-(5-phospho-D-ribitylamino)uracil + H2O = 5-amino-6-(D-ribitylamino)uracil flavin biosynthesis I (bacteria and plants) norspermidine-2,3-dihydroxybenzoate NS-DHB*N1-(2, 3-dihydroxybenzoyl)norspermidine*DHB-NSPD 267.327 C13 H21 N3 O3 C1(O)(=C(C(=CC=C1)C(=O)NCCCNCCCN)O) PUBCHEM:45479385: norspermidine-2,3-dihydroxybenzoate + dihydroxyphenyl-5-methyloxazoline-VibF = dihydroxyphenyl-5-methyloxazoline-norspermidine-2,3-dihydroxybenzoate vibriobactin biosynthesis norspermidine-2,3-dihydroxybenzoate NS-DHB*N1-(2, 3-dihydroxybenzoyl)norspermidine*DHB-NSPD 267.327 C13 H21 N3 O3 C1(O)(=C(C(=CC=C1)C(=O)NCCCNCCCN)O) PUBCHEM:45479385: 2,3-dihydroxybenzoate-VibB + norspermidine = norspermidine-2,3-dihydroxybenzoate + H2O vibriobactin biosynthesis cyanate cyanic acid*hydrogen cyanate 42.017 C1 N1 O1 C([O-])#N PUBCHEM:105034:*CHEBI:29195:*LIGAND-CPD:C01417:*CAS:420-05-3 4.2.1.104 cyanate + bicarbonate + H+ = carbamate + CO2 cyanate degradation methylglyoxal oxopropanal*acetylformaldehyde*pyruvic aldehyde*pyruvaldehyde*methyl-glyoxal*2-oxo-propanal 72.063 C3 H4 O2 O=C(C=O)C PUBCHEM:880:*CHEBI:17158:*LIGAND-CPD:C00546:*CAS:78-98-8 1.2.1.23 methylglyoxal + NAD+ + H2O = H+ + pyruvate + NADH methylglyoxal degradation VII GDP-α-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 603.329 C16 H23 N5 O16 P2 N2(C=NC1(C(=O)NC(N)=NC=12))(C4(C(O)C(C(COP(=O)([O-])OP(=O)([O-])OC3(OC(C(O)C(O)C(O)3)CO))O4)O)) PUBCHEM:25246025:*CAS:18441-12-8*CAS:3123-67-9*LIGAND-CPD:C00096: 4.2.1.47 GDP-α-D-mannose = GDP-4-dehydro-6-deoxy-D-mannose + H2O GDP-L-fucose biosynthesis I (from GDP-D-mannose) GDP-α-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 603.329 C16 H23 N5 O16 P2 N2(C=NC1(C(=O)NC(N)=NC=12))(C4(C(O)C(C(COP(=O)([O-])OP(=O)([O-])OC3(OC(C(O)C(O)C(O)3)CO))O4)O)) PUBCHEM:25246025:*CAS:18441-12-8*CAS:3123-67-9*LIGAND-CPD:C00096: 2.4.1.- GDP-α-D-mannose = H+ + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP-α-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 603.329 C16 H23 N5 O16 P2 N2(C=NC1(C(=O)NC(N)=NC=12))(C4(C(O)C(C(COP(=O)([O-])OP(=O)([O-])OC3(OC(C(O)C(O)C(O)3)CO))O4)O)) PUBCHEM:25246025:*CAS:18441-12-8*CAS:3123-67-9*LIGAND-CPD:C00096: 2.4.1.132 GDP-α-D-mannose = H+ + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP-α-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 603.329 C16 H23 N5 O16 P2 N2(C=NC1(C(=O)NC(N)=NC=12))(C4(C(O)C(C(COP(=O)([O-])OP(=O)([O-])OC3(OC(C(O)C(O)C(O)3)CO))O4)O)) PUBCHEM:25246025:*CAS:18441-12-8*CAS:3123-67-9*LIGAND-CPD:C00096: 2.4.1.131 GDP-α-D-mannose = GDP + H+ dolichyl-diphosphooligosaccharide biosynthesis GDP-α-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 603.329 C16 H23 N5 O16 P2 N2(C=NC1(C(=O)NC(N)=NC=12))(C4(C(O)C(C(COP(=O)([O-])OP(=O)([O-])OC3(OC(C(O)C(O)C(O)3)CO))O4)O)) PUBCHEM:25246025:*CAS:18441-12-8*CAS:3123-67-9*LIGAND-CPD:C00096: 2.4.1.83 GDP-α-D-mannose = GDP dolichyl-diphosphooligosaccharide biosynthesis GDP-α-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 603.329 C16 H23 N5 O16 P2 N2(C=NC1(C(=O)NC(N)=NC=12))(C4(C(O)C(C(COP(=O)([O-])OP(=O)([O-])OC3(OC(C(O)C(O)C(O)3)CO))O4)O)) PUBCHEM:25246025:*CAS:18441-12-8*CAS:3123-67-9*LIGAND-CPD:C00096: 5.1.3.18 GDP-α-D-mannose = GDP-L-galactose ascorbate biosynthesis I (L-galactose pathway) GDP-α-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 603.329 C16 H23 N5 O16 P2 N2(C=NC1(C(=O)NC(N)=NC=12))(C4(C(O)C(C(COP(=O)([O-])OP(=O)([O-])OC3(OC(C(O)C(O)C(O)3)CO))O4)O)) PUBCHEM:25246025:*CAS:18441-12-8*CAS:3123-67-9*LIGAND-CPD:C00096: 2.4.1.142 GDP-α-D-mannose = H+ + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP-α-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 603.329 C16 H23 N5 O16 P2 N2(C=NC1(C(=O)NC(N)=NC=12))(C4(C(O)C(C(COP(=O)([O-])OP(=O)([O-])OC3(OC(C(O)C(O)C(O)3)CO))O4)O)) PUBCHEM:25246025:*CAS:18441-12-8*CAS:3123-67-9*LIGAND-CPD:C00096: 2.7.7.13 H+ + α-D-mannose 1-phosphate + GTP = GDP-α-D-mannose + diphosphate ascorbate biosynthesis I (L-galactose pathway) GDP-α-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 603.329 C16 H23 N5 O16 P2 N2(C=NC1(C(=O)NC(N)=NC=12))(C4(C(O)C(C(COP(=O)([O-])OP(=O)([O-])OC3(OC(C(O)C(O)C(O)3)CO))O4)O)) PUBCHEM:25246025:*CAS:18441-12-8*CAS:3123-67-9*LIGAND-CPD:C00096: 2.7.7.13 H+ + α-D-mannose 1-phosphate + GTP = GDP-α-D-mannose + diphosphate GDP-mannose biosynthesis obtusifoliol 4α,14α-dimethyl-5α-ergosta-8,24(28)-dien-3β-ol*4α,14α-dimethyl-24-methylene-5α-cholesta-8-en-3β-ol 426.724 C30 H50 O1 C1(CC(C(C2(C1(C3(=C(CC2)C4(C)(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))C)O) PUBCHEM:25203494:*LIGAND-CPD:C01943: 1.14.13.70 NADPH + oxygen + obtusifoliol + H+ = H2O + NADP+ + formate + 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol plant sterol biosynthesis obtusifoliol 4α,14α-dimethyl-5α-ergosta-8,24(28)-dien-3β-ol*4α,14α-dimethyl-24-methylene-5α-cholesta-8-en-3β-ol 426.724 C30 H50 O1 C1(CC(C(C2(C1(C3(=C(CC2)C4(C)(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))C)O) PUBCHEM:25203494:*LIGAND-CPD:C01943: 5.5.1.9 cycloeucalenol = obtusifoliol plant sterol biosynthesis 3-cyano-L-alanine 3-cyanoalanine*L-3-Cyanoalanine 113.096 C4 H5 N2 O2 NC(C(=O)[O-])CC#N PUBCHEM:25203495:*LIGAND-CPD:C02512: 4.4.1.9 L-cysteine + hydrogen cyanide = hydrogen sulfide + 3-cyano-L-alanine + H+ cyanide detoxification 3-cyano-L-alanine 3-cyanoalanine*L-3-Cyanoalanine 113.096 C4 H5 N2 O2 NC(C(=O)[O-])CC#N PUBCHEM:25203495:*LIGAND-CPD:C02512: 4.4.1.9 L-cysteine + hydrogen cyanide = hydrogen sulfide + 3-cyano-L-alanine + H+ cyanide degradation 3-cyano-L-alanine 3-cyanoalanine*L-3-Cyanoalanine 113.096 C4 H5 N2 O2 NC(C(=O)[O-])CC#N PUBCHEM:25203495:*LIGAND-CPD:C02512: 3.5.5.4 H2O + 3-cyano-L-alanine = ammonia + L-aspartate cyanide detoxification 3-cyano-L-alanine 3-cyanoalanine*L-3-Cyanoalanine 113.096 C4 H5 N2 O2 NC(C(=O)[O-])CC#N PUBCHEM:25203495:*LIGAND-CPD:C02512: 4.2.1.65 L-asparagine = H+ + H2O + 3-cyano-L-alanine cyanide detoxification cycloeucalenone 9,19-cyclo-5α,9β-ergost-24(28)-en-3-one*3H,19H-cyclopropa[9,10]cyclopenta[a]phenanthrene*4α,14α-dimethyl-9β,19-cyclo-ergost-24(241)-en-3-one 424.709 C30 H48 O1 C1(CC(C(C2(C51(C3(C(CC2)C4(C)(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4))C5)))C)=O) CAS:1255-12-5: 1.1.1.- 4α-carboxy-4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ = cycloeucalenone + NADH + CO2 plant sterol biosynthesis cycloeucalenone 9,19-cyclo-5α,9β-ergost-24(28)-en-3-one*3H,19H-cyclopropa[9,10]cyclopenta[a]phenanthrene*4α,14α-dimethyl-9β,19-cyclo-ergost-24(241)-en-3-one 424.709 C30 H48 O1 C1(CC(C(C2(C51(C3(C(CC2)C4(C)(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4))C5)))C)=O) CAS:1255-12-5: 1.1.1.- cycloeucalenone + NADPH + H+ = cycloeucalenol + NADP+ plant sterol biosynthesis tryptamine 3-(2-aminoethyl)indole 161.226 C10 H13 N2 C(CC1(=CNC2(C=CC=CC1=2)))[N+] CHEBI:57887:*PUBCHEM:3985862:*LIGAND-CPD:C00398:*CAS:61-54-1 4.3.3.2 tryptamine + secologanin = strictosidine + H2O camptothecin biosynthesis tryptamine 3-(2-aminoethyl)indole 161.226 C10 H13 N2 C(CC1(=CNC2(C=CC=CC1=2)))[N+] CHEBI:57887:*PUBCHEM:3985862:*LIGAND-CPD:C00398:*CAS:61-54-1 4.1.1.28 H+ + L-tryptophan = CO2 + tryptamine IAA biosynthesis I tryptamine 3-(2-aminoethyl)indole 161.226 C10 H13 N2 C(CC1(=CNC2(C=CC=CC1=2)))[N+] CHEBI:57887:*PUBCHEM:3985862:*LIGAND-CPD:C00398:*CAS:61-54-1 4.1.1.28 H+ + L-tryptophan = CO2 + tryptamine camptothecin biosynthesis tryptamine 3-(2-aminoethyl)indole 161.226 C10 H13 N2 C(CC1(=CNC2(C=CC=CC1=2)))[N+] CHEBI:57887:*PUBCHEM:3985862:*LIGAND-CPD:C00398:*CAS:61-54-1 tryptamine + oxygen + NADPH = N-hydroxyl-tryptamine + H2O + NADP+ IAA biosynthesis I dTMP T*thymidylic acid*thymidine monophosphate*deoxythymidylate*TMP*thymidine-5'-monophosphate*thymidine-phosphate*thymidine-5'-phosphate*Deoxythymidine 5'-phosphate*5'-Thymidylic acid*Deoxythymidylic acid*Thymidylate 320.195 C10 H13 N2 O8 P1 CC1(=CN(C(=O)NC(=O)1)C2(CC(O)C(COP(=O)([O-])[O-])O2)) PUBCHEM:16755631:*CHEBI:26999:*LIGAND-CPD:C00364:*CAS:365-07-1 2.7.4.9 ATP + dTMP = ADP + dTDP pyrimidine deoxyribonucleotides de novo biosynthesis I dTMP T*thymidylic acid*thymidine monophosphate*deoxythymidylate*TMP*thymidine-5'-monophosphate*thymidine-phosphate*thymidine-5'-phosphate*Deoxythymidine 5'-phosphate*5'-Thymidylic acid*Deoxythymidylic acid*Thymidylate 320.195 C10 H13 N2 O8 P1 CC1(=CN(C(=O)NC(=O)1)C2(CC(O)C(COP(=O)([O-])[O-])O2)) PUBCHEM:16755631:*CHEBI:26999:*LIGAND-CPD:C00364:*CAS:365-07-1 2.1.1.45 5,10-methylenetetrahydropteroyl mono-L-glutamate + dUMP = dTMP + 7,8-dihydrofolate monoglutamate pyrimidine deoxyribonucleotides de novo biosynthesis I dTMP T*thymidylic acid*thymidine monophosphate*deoxythymidylate*TMP*thymidine-5'-monophosphate*thymidine-phosphate*thymidine-5'-phosphate*Deoxythymidine 5'-phosphate*5'-Thymidylic acid*Deoxythymidylic acid*Thymidylate 320.195 C10 H13 N2 O8 P1 CC1(=CN(C(=O)NC(=O)1)C2(CC(O)C(COP(=O)([O-])[O-])O2)) PUBCHEM:16755631:*CHEBI:26999:*LIGAND-CPD:C00364:*CAS:365-07-1 2.1.1.45 5,10-methylenetetrahydropteroyl mono-L-glutamate + dUMP = dTMP + 7,8-dihydrofolate monoglutamate folate transformations II (plants) D-mannitol D-mannitol*mannitol*mitobronitol 182.173 C6 H14 O6 C(C(CO)O)(C(C(CO)O)O)O CHEBI:16899:*PUBCHEM:6251:*LIGAND-CPD:C00392:*CAS:69-65-8 1.1.1.255 NAD+ + D-mannitol = H+ + NADH mannitol degradation II adenosine 5'-phosphosulfate Adenosine 5'-phosphosulfate*adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 425.266 C10 H12 N5 O10 P1 S1 NC3(=NC=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OS(=O)(=O)[O-])C(O)C(O)2))3)) PUBCHEM:25246029:*PUBCHEM:10238:*LIGAND-CPD:C00224:*CAS:485-84-7 2.7.1.25 adenosine 5'-phosphosulfate + ATP = H+ + phosphoadenosine-5'-phosphosulfate + ADP sulfate activation for sulfonation adenosine 5'-phosphosulfate Adenosine 5'-phosphosulfate*adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 425.266 C10 H12 N5 O10 P1 S1 NC3(=NC=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OS(=O)(=O)[O-])C(O)C(O)2))3)) PUBCHEM:25246029:*PUBCHEM:10238:*LIGAND-CPD:C00224:*CAS:485-84-7 1.8.4.9 H+ + sulfite + AMP + glutathione disulfide = adenosine 5'-phosphosulfate + glutathione sulfate reduction II (assimilatory) adenosine 5'-phosphosulfate Adenosine 5'-phosphosulfate*adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 425.266 C10 H12 N5 O10 P1 S1 NC3(=NC=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OS(=O)(=O)[O-])C(O)C(O)2))3)) PUBCHEM:25246029:*PUBCHEM:10238:*LIGAND-CPD:C00224:*CAS:485-84-7 2.7.7.4 H+ + sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate reduction II (assimilatory) adenosine 5'-phosphosulfate Adenosine 5'-phosphosulfate*adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 425.266 C10 H12 N5 O10 P1 S1 NC3(=NC=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OS(=O)(=O)[O-])C(O)C(O)2))3)) PUBCHEM:25246029:*PUBCHEM:10238:*LIGAND-CPD:C00224:*CAS:485-84-7 2.7.7.4 H+ + sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfite oxidation III adenosine 5'-phosphosulfate Adenosine 5'-phosphosulfate*adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 425.266 C10 H12 N5 O10 P1 S1 NC3(=NC=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OS(=O)(=O)[O-])C(O)C(O)2))3)) PUBCHEM:25246029:*PUBCHEM:10238:*LIGAND-CPD:C00224:*CAS:485-84-7 2.7.7.4 H+ + sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate activation for sulfonation adenosine 5'-phosphosulfate Adenosine 5'-phosphosulfate*adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 425.266 C10 H12 N5 O10 P1 S1 NC3(=NC=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OS(=O)(=O)[O-])C(O)C(O)2))3)) PUBCHEM:25246029:*PUBCHEM:10238:*LIGAND-CPD:C00224:*CAS:485-84-7 2.7.7.5 sulfate + H+ + ADP = adenosine 5'-phosphosulfate sulfite oxidation II adenosine 5'-phosphosulfate Adenosine 5'-phosphosulfate*adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 425.266 C10 H12 N5 O10 P1 S1 NC3(=NC=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OS(=O)(=O)[O-])C(O)C(O)2))3)) PUBCHEM:25246029:*PUBCHEM:10238:*LIGAND-CPD:C00224:*CAS:485-84-7 1.8.99.2 sulfite + AMP = adenosine 5'-phosphosulfate sulfite oxidation III adenosine 5'-phosphosulfate Adenosine 5'-phosphosulfate*adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 425.266 C10 H12 N5 O10 P1 S1 NC3(=NC=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OS(=O)(=O)[O-])C(O)C(O)2))3)) PUBCHEM:25246029:*PUBCHEM:10238:*LIGAND-CPD:C00224:*CAS:485-84-7 1.8.99.2 sulfite + AMP = adenosine 5'-phosphosulfate sulfite oxidation II 3-decaprenyl-4-hydroxybenzoate 818.297 C57 H85 O3 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(C=C(C=CC=1O)C(=O)[O-]))C)C)C)C)C)C)C)CCC=C(C)CCC=C(C)C PUBCHEM:25244159: 2.5.1.39 all-trans-decaprenyl diphosphate = 3-decaprenyl-4-hydroxybenzoate + diphosphate ubiquinol-10 biosynthesis (eukaryotic) 3-decaprenyl-4-hydroxybenzoate 818.297 C57 H85 O3 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(C=C(C=CC=1O)C(=O)[O-]))C)C)C)C)C)C)C)CCC=C(C)CCC=C(C)C PUBCHEM:25244159: 1.14.13.- 3-decaprenyl-4-hydroxybenzoate + oxygen + NADPH + H+ = 3,4-dihydroxy-5-all-trans-decaprenylbenzoate + H2O + NADP+ ubiquinol-10 biosynthesis (eukaryotic) geranylgeranyl-chlorophyll a geranylgeranyl-chl a*GG-chl a*GG-chlorophyll a 887.455 C55 H66 N4 O5 MG1 C24(C=C9(C(C)C(CCC(=O)OCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C5(=N([Mg]36(N1(=C(C(CC)=C(C)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) PUBCHEM:25244764: 1.3.1.- H+ + geranylgeranyl-chlorophyll a + NADPH = dihydrogeranylgeranyl-chlorophyll a + NADP+ chlorophyll a biosynthesis II geranylgeranyl-chlorophyll a geranylgeranyl-chl a*GG-chl a*GG-chlorophyll a 887.455 C55 H66 N4 O5 MG1 C24(C=C9(C(C)C(CCC(=O)OCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C5(=N([Mg]36(N1(=C(C(CC)=C(C)C1=CC(=C(C=C)C(C)=2)N34)C=C7(C(C)=C8(C(=O)C(C(OC)=O)C5=C(N67)8)))))9))) PUBCHEM:25244764: 2.5.1.- H+ + chlorophyllide a + all-trans-geranyl-geranyl diphosphate = geranylgeranyl-chlorophyll a + diphosphate chlorophyll a biosynthesis II 2-phenylethylamine Phenethylamine*β-phenylethylamine*phenylethylamine*2-phenylethylamine 122.189 C8 H12 N1 C1(C=CC(CC[N+])=CC=1) CHEBI:225237:*PUBCHEM:448751:*LIGAND-CPD:C05332:*CAS:64-04-0 4.1.1.53 H+ + L-phenylalanine = 2-phenylethylamine + CO2 phenylethanol biosynthesis 2-phenylethylamine Phenethylamine*β-phenylethylamine*phenylethylamine*2-phenylethylamine 122.189 C8 H12 N1 C1(C=CC(CC[N+])=CC=1) CHEBI:225237:*PUBCHEM:448751:*LIGAND-CPD:C05332:*CAS:64-04-0 1.4.3.21 2-phenylethylamine + oxygen + H2O = H+ + phenylacetaldehyde + ammonia + hydrogen peroxide phenylethanol biosynthesis trans-zeatin-O-glucoside O-β-D-Glucosylzeatin 381.388 C16 H23 N5 O6 C1(C2(=C(N=CN=1)NC=N2))NCC=C(COC3(C(C(C(C(O3)CO)O)O)O))C CHEBI:38266:*PUBCHEM:25244165:*LIGAND-CPD:C03423: 2.4.1.203 trans-zeatin = H+ + trans-zeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis 3-methylbutanol isoamyl alcohol*isopentanol 88.149 C5 H12 O1 C(C(C)C)CO PUBCHEM:31260:*LIGAND-CPD:C07328:*CHEBI:15837: 1.1.1.1 H+ + 3-methylbutanal + NADH = 3-methylbutanol + NAD+ leucine degradation III S-allantoin 158.116 C4 H6 N4 O3 NC(=O)NC1(NC(=O)NC(=O)1) PUBCHEM:439714:*CHEBI:15678:*LIGAND-CPD:C02350: H+ + 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate = S-allantoin + CO2 urate degradation to allantoin S-allantoin 158.116 C4 H6 N4 O3 NC(=O)NC1(NC(=O)NC(=O)1) PUBCHEM:439714:*CHEBI:15678:*LIGAND-CPD:C02350: 3.5.2.5 S-allantoin + H2O = H+ + allantoate allantoin degradation to ureidoglycolate I (urea producing) S-allantoin 158.116 C4 H6 N4 O3 NC(=O)NC1(NC(=O)NC(=O)1) PUBCHEM:439714:*CHEBI:15678:*LIGAND-CPD:C02350: 3.5.2.5 S-allantoin + H2O = H+ + allantoate allantoin degradation to ureidoglycolate II (ammonia producing) N6-dimethylallyladenine N(6)-dimethylallyladenine*isopentenyladenine*N6-Δ2-isopentenyladenine*iP 203.246 C10 H13 N5 C1(C2(=C(N=CN=1)NC=N2))NCC=C(C)C PUBCHEM:92180:*LIGAND-CPD:C04083:*CHEBI:17660:*NCI:106958:*CAS:2365-40-4: N6-dimethylallyladenine + H2O = trans-zeatin + H+ trans-zeatin biosynthesis N6-dimethylallyladenine N(6)-dimethylallyladenine*isopentenyladenine*N6-Δ2-isopentenyladenine*iP 203.246 C10 H13 N5 C1(C2(=C(N=CN=1)NC=N2))NCC=C(C)C PUBCHEM:92180:*LIGAND-CPD:C04083:*CHEBI:17660:*NCI:106958:*CAS:2365-40-4: 1.5.99.12 N6-dimethylallyladenine + H+ + FAD + H2O = 3-methyl-2-butenal + adenine + FADH2 cytokinins degradation N6-dimethylallyladenine N(6)-dimethylallyladenine*isopentenyladenine*N6-Δ2-isopentenyladenine*iP 203.246 C10 H13 N5 C1(C2(=C(N=CN=1)NC=N2))NCC=C(C)C PUBCHEM:92180:*LIGAND-CPD:C04083:*CHEBI:17660:*NCI:106958:*CAS:2365-40-4: 3.2.2.- N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate + H2O = N6-dimethylallyladenine + D-ribose-5-phosphate trans-zeatin biosynthesis 8'-hydroxyabscisate 8´-HOABA*8'-HOABA 279.312 C15 H19 O5 C1(C(C(C(=CC1=O)C)(C=CC(=CC([O-])=O)C)O)(C)CO) CHEBI:58490:*PUBCHEM:25245404:*LIGAND-CPD:C15514: 8'-hydroxyabscisate = phaseic acid phaseic acid biosynthesis 8'-hydroxyabscisate 8´-HOABA*8'-HOABA 279.312 C15 H19 O5 C1(C(C(C(=CC1=O)C)(C=CC(=CC([O-])=O)C)O)(C)CO) CHEBI:58490:*PUBCHEM:25245404:*LIGAND-CPD:C15514: 1.14.13.93 H+ + 2-cis-abscisic acid + NADPH + oxygen = 8'-hydroxyabscisate + NADP+ + H2O phaseic acid biosynthesis scoparone scoparon*6,7-dimethylesculetin*6,7-dimethoxycoumarin 206.198 C11 H10 O4 COC1(=C(C=C2(C(=C1)C=CC(=O)O2))OC) isoscopoletin = scoparone simplecoumarins biosynthesis scoparone scoparon*6,7-dimethylesculetin*6,7-dimethoxycoumarin 206.198 C11 H10 O4 COC1(=C(C=C2(C(=C1)C=CC(=O)O2))OC) scopoletin = scoparone simplecoumarins biosynthesis 3,7-di-O-methylquercetin 3',4',5-trihydroxy-3,7-dimethoxyflavone 330.293 C17 H14 O7 COC3(C(=O)C1(C(=CC(OC)=CC(O)=1)OC(C2(C=C(O)C(O)=CC=2))=3)) PUBCHEM:5280417:*CHEBI:18010:*LIGAND-CPD:C01265: 2.1.1.83 3,7-di-O-methylquercetin + S-adenosyl-L-methionine = H+ + 3,7,4'-tri-O-methylquercetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis 3,7-di-O-methylquercetin 3',4',5-trihydroxy-3,7-dimethoxyflavone 330.293 C17 H14 O7 COC3(C(=O)C1(C(=CC(OC)=CC(O)=1)OC(C2(C=C(O)C(O)=CC=2))=3)) PUBCHEM:5280417:*CHEBI:18010:*LIGAND-CPD:C01265: 2.1.1.82 3-O-methylquercetin + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + 3,7-di-O-methylquercetin methylquercetin biosynthesis dUDP 2'-deoxyuridine-5'-diphosphate*deoxyuridine-diphosphate 385.14 C9 H11 N2 O11 P2 O=C1(C=CN(C(=O)N1)C2(CC(O)C(COP(=O)([O-])OP(=O)([O-])[O-])O2)) PUBCHEM:25246037:*LIGAND-CPD:C01346: 2.7.4.6 dUDP + ATP = dUTP + ADP pyrimidine deoxyribonucleotides de novo biosynthesis I dUDP 2'-deoxyuridine-5'-diphosphate*deoxyuridine-diphosphate 385.14 C9 H11 N2 O11 P2 O=C1(C=CN(C(=O)N1)C2(CC(O)C(COP(=O)([O-])OP(=O)([O-])[O-])O2)) PUBCHEM:25246037:*LIGAND-CPD:C01346: 1.17.4.1 dUDP + H2O = UDP pyrimidine deoxyribonucleotides de novo biosynthesis I dUDP 2'-deoxyuridine-5'-diphosphate*deoxyuridine-diphosphate 385.14 C9 H11 N2 O11 P2 O=C1(C=CN(C(=O)N1)C2(CC(O)C(COP(=O)([O-])OP(=O)([O-])[O-])O2)) PUBCHEM:25246037:*LIGAND-CPD:C01346: 1.17.4.- UDP = dUDP + H2O pyrimidine deoxyribonucleotides de novo biosynthesis I 2-aminoadipate-6-semialdehyde allysine*L-2-aminoadipate 6-semialdehyde*2-aminoadipate 6-semialdehyde*α-aminoadipate 6-semialdehyde*2-aminoadipate semialdehyde*L-allysine*(S)-2-aminoadipate 6-semialdehyde 145.158 C6 H11 N1 O3 C(CCC=O)C([N+])C(=O)[O-] LIGAND-CPD:C01475:*PUBCHEM:45479557:*LIGAND-CPD:C04076:*CHEBI:17917:*CAS:1962-83-0 1.2.1.31 H+ + Δ1-piperideine-6-carboxylate + H2O = 2-aminoadipate-6-semialdehyde lysine degradation II 2-aminoadipate-6-semialdehyde allysine*L-2-aminoadipate 6-semialdehyde*2-aminoadipate 6-semialdehyde*α-aminoadipate 6-semialdehyde*2-aminoadipate semialdehyde*L-allysine*(S)-2-aminoadipate 6-semialdehyde 145.158 C6 H11 N1 O3 C(CCC=O)C([N+])C(=O)[O-] LIGAND-CPD:C01475:*PUBCHEM:45479557:*LIGAND-CPD:C04076:*CHEBI:17917:*CAS:1962-83-0 1.5.1.9 L-saccharopine + H2O + NAD+ = L-glutamate + 2-aminoadipate-6-semialdehyde + NADH + H+ lysine degradation II D-glucosamine-6-phosphate D-glucosamine phosphate*D-glucosamine 6-phosphate*D-glucosamine-6-P*glucosamine-6-P*glucosamine-6-phosphate 258.144 C6 H13 N1 O8 P1 [N+]C1(C(O)OC(COP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:25244770:*LIGAND-CPD:C00352:*CAS:3616-42-0 2.6.1.16 D-fructose-6-phosphate + L-glutamine = L-glutamate + D-glucosamine-6-phosphate UDP-N-acetyl-D-glucosamine biosynthesis II D-glucosamine-6-phosphate D-glucosamine phosphate*D-glucosamine 6-phosphate*D-glucosamine-6-P*glucosamine-6-P*glucosamine-6-phosphate 258.144 C6 H13 N1 O8 P1 [N+]C1(C(O)OC(COP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:25244770:*LIGAND-CPD:C00352:*CAS:3616-42-0 2.3.1.4 D-glucosamine-6-phosphate + acetyl-CoA = H+ + N-acetyl-D-glucosamine-6-phosphate + coenzyme A UDP-N-acetyl-D-glucosamine biosynthesis II octadecanal 268.482 C18 H36 O1 C(CCCCCCCC=O)CCCCCCCCC PUBCHEM:12533:*CHEBI:17034:*LIGAND-CPD:C01838:*CAS:638-66-4 4.1.99.5 octadecanal = heptadecane + carbon monoxide heptadecane biosynthesis octadecanal 268.482 C18 H36 O1 C(CCCCCCCC=O)CCCCCCCCC PUBCHEM:12533:*CHEBI:17034:*LIGAND-CPD:C01838:*CAS:638-66-4 1.2.1.80 octadecanal = H+ heptadecane biosynthesis L-lysine K*lysine*L-lys*lys*2,6-diaminohexanoic acid*lysine acid 147.197 C6 H15 N2 O2 C([N+])(C(=O)[O-])CCCC[N+] PUBCHEM:5242389:*CHEBI:32564:*PUBCHEM:5242389:*CHEBI:32564:*KNAPSACK:C00001378:*LIGAND-CPD:C00047:*CAS:56-87-1 4.1.1.20 H+ + meso-diaminopimelate = CO2 + L-lysine lysine biosynthesis VI L-lysine K*lysine*L-lys*lys*2,6-diaminohexanoic acid*lysine acid 147.197 C6 H15 N2 O2 C([N+])(C(=O)[O-])CCCC[N+] PUBCHEM:5242389:*CHEBI:32564:*PUBCHEM:5242389:*CHEBI:32564:*KNAPSACK:C00001378:*LIGAND-CPD:C00047:*CAS:56-87-1 4.1.1.18 H+ + L-lysine = CO2 + cadaverine lysine degradation I L-lysine K*lysine*L-lys*lys*2,6-diaminohexanoic acid*lysine acid 147.197 C6 H15 N2 O2 C([N+])(C(=O)[O-])CCCC[N+] PUBCHEM:5242389:*CHEBI:32564:*PUBCHEM:5242389:*CHEBI:32564:*KNAPSACK:C00001378:*LIGAND-CPD:C00047:*CAS:56-87-1 6.1.1.6 H+ + L-lysine + ATP = diphosphate + AMP tRNA charging pathway L-lysine K*lysine*L-lys*lys*2,6-diaminohexanoic acid*lysine acid 147.197 C6 H15 N2 O2 C([N+])(C(=O)[O-])CCCC[N+] PUBCHEM:5242389:*CHEBI:32564:*PUBCHEM:5242389:*CHEBI:32564:*KNAPSACK:C00001378:*LIGAND-CPD:C00047:*CAS:56-87-1 1.5.1.8 L-saccharopine + H2O + NADP+ = L-lysine + 2-oxoglutarate + NADPH + H+ lysine degradation II D-sedoheptulose-1,7-bisphosphate sedoheptulose 1,7-bisphosphate*D-sedoheptulose-1,7-diphosphate*D-sedoheptulose-1,7-P2*SBP 366.112 C7 H12 O13 P2 C(C(C(C(C(O)C(O)COP([O-])([O-])=O)O)O)=O)OP([O-])(=O)[O-] PUBCHEM:25244771:*LIGAND-CPD:C00447: 4.1.2.- dihydroxyacetone phosphate + D-erythrose-4-phosphate = D-sedoheptulose-1,7-bisphosphate Calvin-Benson-Bassham cycle D-sedoheptulose-1,7-bisphosphate sedoheptulose 1,7-bisphosphate*D-sedoheptulose-1,7-diphosphate*D-sedoheptulose-1,7-P2*SBP 366.112 C7 H12 O13 P2 C(C(C(C(C(O)C(O)COP([O-])([O-])=O)O)O)=O)OP([O-])(=O)[O-] PUBCHEM:25244771:*LIGAND-CPD:C00447: 3.1.3.37 H2O + D-sedoheptulose-1,7-bisphosphate = D-sedoheptulose-7-phosphate Calvin-Benson-Bassham cycle N,N-dihydroxy-L-tryptophan 235.219 C11 H11 N2 O4 C2(CC(N(O)O)C([O-])=O)(C1(C=CC=CC=1NC=2)) 1.14.13.- N-hydroxy-L-tryptophan + oxygen + NADPH + H+ = N,N-dihydroxy-L-tryptophan + NADP+ + H2O IAA biosynthesis I N,N-dihydroxy-L-tryptophan 235.219 C11 H11 N2 O4 C2(CC(N(O)O)C([O-])=O)(C1(C=CC=CC=1NC=2)) 1.14.13.- H+ + N,N-dihydroxy-L-tryptophan = (E)-indol-3-ylacetaldoxime + CO2 + H2O IAA biosynthesis I biotin vitamin H*coenzyme R*d-biotin 243.3 C10 H15 N2 O3 S1 O=C([O-])CCCCC1(SCC2(NC(=O)NC12)) CHEBI:57586:*PUBCHEM:6560210:*LIGAND-CPD:C00120:*CAS:58-85-5 6.3.4.15 biotin + ATP = diphosphate + AMP biotin-carboxyl carrier protein assembly biotin vitamin H*coenzyme R*d-biotin 243.3 C10 H15 N2 O3 S1 O=C([O-])CCCCC1(SCC2(NC(=O)NC12)) CHEBI:57586:*PUBCHEM:6560210:*LIGAND-CPD:C00120:*CAS:58-85-5 2.8.1.6 dethiobiotin + S-adenosyl-L-methionine = biotin + 5'-deoxyadenosine + L-methionine biotin biosynthesis from 7-keto-8-aminopelargonate phosphoryl-choline O-phosphocholine*choline-phosphate*choline phosphate*phosphocholine*N-Trimethyl-2-aminoethylphosphonate*O-Phosphocholine 182.136 C5 H13 N1 O4 P1 [N+](CCOP([O-])([O-])=O)(C)(C)C CHEBI:295975:*PUBCHEM:3330960:*LIGAND-CPD:C00588:*CAS:107-73-3 2.1.1.103 N-dimethylethanolamine phosphate + S-adenosyl-L-methionine = H+ + phosphoryl-choline + S-adenosyl-L-homocysteine choline biosynthesis I phosphoryl-choline O-phosphocholine*choline-phosphate*choline phosphate*phosphocholine*N-Trimethyl-2-aminoethylphosphonate*O-Phosphocholine 182.136 C5 H13 N1 O4 P1 [N+](CCOP([O-])([O-])=O)(C)(C)C CHEBI:295975:*PUBCHEM:3330960:*LIGAND-CPD:C00588:*CAS:107-73-3 2.1.1.103 N-dimethylethanolamine phosphate + S-adenosyl-L-methionine = H+ + phosphoryl-choline + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis II phosphoryl-choline O-phosphocholine*choline-phosphate*choline phosphate*phosphocholine*N-Trimethyl-2-aminoethylphosphonate*O-Phosphocholine 182.136 C5 H13 N1 O4 P1 [N+](CCOP([O-])([O-])=O)(C)(C)C CHEBI:295975:*PUBCHEM:3330960:*LIGAND-CPD:C00588:*CAS:107-73-3 3.1.3.75 phosphoryl-choline + H2O = choline choline biosynthesis I phosphoryl-choline O-phosphocholine*choline-phosphate*choline phosphate*phosphocholine*N-Trimethyl-2-aminoethylphosphonate*O-Phosphocholine 182.136 C5 H13 N1 O4 P1 [N+](CCOP([O-])([O-])=O)(C)(C)C CHEBI:295975:*PUBCHEM:3330960:*LIGAND-CPD:C00588:*CAS:107-73-3 3.1.4.3 H2O = phosphoryl-choline phospholipases phosphoryl-choline O-phosphocholine*choline-phosphate*choline phosphate*phosphocholine*N-Trimethyl-2-aminoethylphosphonate*O-Phosphocholine 182.136 C5 H13 N1 O4 P1 [N+](CCOP([O-])([O-])=O)(C)(C)C CHEBI:295975:*PUBCHEM:3330960:*LIGAND-CPD:C00588:*CAS:107-73-3 2.7.1.32 choline + ATP = H+ + phosphoryl-choline + ADP phosphatidylcholine biosynthesis I phosphoryl-choline O-phosphocholine*choline-phosphate*choline phosphate*phosphocholine*N-Trimethyl-2-aminoethylphosphonate*O-Phosphocholine 182.136 C5 H13 N1 O4 P1 [N+](CCOP([O-])([O-])=O)(C)(C)C CHEBI:295975:*PUBCHEM:3330960:*LIGAND-CPD:C00588:*CAS:107-73-3 2.7.7.15 H+ + phosphoryl-choline + CTP = CDP-choline + diphosphate phosphatidylcholine biosynthesis I phosphoryl-choline O-phosphocholine*choline-phosphate*choline phosphate*phosphocholine*N-Trimethyl-2-aminoethylphosphonate*O-Phosphocholine 182.136 C5 H13 N1 O4 P1 [N+](CCOP([O-])([O-])=O)(C)(C)C CHEBI:295975:*PUBCHEM:3330960:*LIGAND-CPD:C00588:*CAS:107-73-3 2.7.7.15 H+ + phosphoryl-choline + CTP = CDP-choline + diphosphate choline biosynthesis III phosphoryl-choline O-phosphocholine*choline-phosphate*choline phosphate*phosphocholine*N-Trimethyl-2-aminoethylphosphonate*O-Phosphocholine 182.136 C5 H13 N1 O4 P1 [N+](CCOP([O-])([O-])=O)(C)(C)C CHEBI:295975:*PUBCHEM:3330960:*LIGAND-CPD:C00588:*CAS:107-73-3 2.7.7.15 H+ + phosphoryl-choline + CTP = CDP-choline + diphosphate phosphatidylcholine biosynthesis II uridine 244.204 C9 H12 N2 O6 O=C1(C=CN(C(=O)N1)C2(OC(CO)C(O)C(O)2)) PUBCHEM:6029:*CHEBI:16704:*LIGAND-CPD:C00299:*CAS:58-96-8 3.2.2.3 uridine + H2O = uracil pyrimidine ribonucleosides degradation II uridine 244.204 C9 H12 N2 O6 O=C1(C=CN(C(=O)N1)C2(OC(CO)C(O)C(O)2)) PUBCHEM:6029:*CHEBI:16704:*LIGAND-CPD:C00299:*CAS:58-96-8 2.7.1.48 uridine + GTP = H+ + uridine-5'-phosphate + GDP salvage pathways of pyrimidine ribonucleotides uridine 244.204 C9 H12 N2 O6 O=C1(C=CN(C(=O)N1)C2(OC(CO)C(O)C(O)2)) PUBCHEM:6029:*CHEBI:16704:*LIGAND-CPD:C00299:*CAS:58-96-8 3.5.4.5 H2O + cytidine = uridine + ammonia salvage pathways of pyrimidine ribonucleotides uridine 244.204 C9 H12 N2 O6 O=C1(C=CN(C(=O)N1)C2(OC(CO)C(O)C(O)2)) PUBCHEM:6029:*CHEBI:16704:*LIGAND-CPD:C00299:*CAS:58-96-8 3.5.4.5 H2O + cytidine = uridine + ammonia pyrimidine ribonucleosides degradation II uridine 244.204 C9 H12 N2 O6 O=C1(C=CN(C(=O)N1)C2(OC(CO)C(O)C(O)2)) PUBCHEM:6029:*CHEBI:16704:*LIGAND-CPD:C00299:*CAS:58-96-8 2.4.2.3 uridine = α-D-ribose-1-phosphate + uracil salvage pathways of pyrimidine ribonucleotides 2,3-dihydroxybenzoyl-AMP 2,3-dihydroxybenzoyl adenylate*(2,3-dihydroxybenzoyl)adenylate 482.323 C17 H17 N5 O10 P1 NC4(=NC=NC1(=C(N=CN1C3(OC(COP(=O)([O-])OC(=O)C2(C=CC=C(O)C(O)=2))C(O)C(O)3))4)) CHEBI:57417:*PUBCHEM:636431:*LIGAND-CPD:C04030: 2,3-dihydroxybenzoyl-AMP = 2,3-dihydroxybenzoate-VibB + AMP vibriobactin biosynthesis 2,3-dihydroxybenzoyl-AMP 2,3-dihydroxybenzoyl adenylate*(2,3-dihydroxybenzoyl)adenylate 482.323 C17 H17 N5 O10 P1 NC4(=NC=NC1(=C(N=CN1C3(OC(COP(=O)([O-])OC(=O)C2(C=CC=C(O)C(O)=2))C(O)C(O)3))4)) CHEBI:57417:*PUBCHEM:636431:*LIGAND-CPD:C04030: 2.7.7.58 H+ + 2,3-dihydroxybenzoate + ATP = 2,3-dihydroxybenzoyl-AMP + diphosphate vibriobactin biosynthesis D-threo-isocitrate (1R, 2S)-1-hydroxypropane-1,2,3-tricarboxylate*D-threo-isocitric acid*isocitric acid*isocitrate*threo-Ds-isocitrate*I-CIT*D-isocitrate 189.101 C6 H5 O7 C(=O)(C(CC([O-])=O)C(O)C([O-])=O)[O-] CHEBI:15562:*PUBCHEM:5459771:*LIGAND-CPD:C00451:*KNAPSACK:C00001188:*CAS:30810-51-6:*LIGAND-CPD:C00311:*CAS:320-77-4 1.1.1.41 D-threo-isocitrate + NAD+ = 2-oxoglutarate + CO2 + NADH TCA cycle variation III (eukaryotic) D-threo-isocitrate (1R, 2S)-1-hydroxypropane-1,2,3-tricarboxylate*D-threo-isocitric acid*isocitric acid*isocitrate*threo-Ds-isocitrate*I-CIT*D-isocitrate 189.101 C6 H5 O7 C(=O)(C(CC([O-])=O)C(O)C([O-])=O)[O-] CHEBI:15562:*PUBCHEM:5459771:*LIGAND-CPD:C00451:*KNAPSACK:C00001188:*CAS:30810-51-6:*LIGAND-CPD:C00311:*CAS:320-77-4 1.1.1.41 D-threo-isocitrate + NAD+ = 2-oxoglutarate + CO2 + NADH glutamine biosynthesis III D-threo-isocitrate (1R, 2S)-1-hydroxypropane-1,2,3-tricarboxylate*D-threo-isocitric acid*isocitric acid*isocitrate*threo-Ds-isocitrate*I-CIT*D-isocitrate 189.101 C6 H5 O7 C(=O)(C(CC([O-])=O)C(O)C([O-])=O)[O-] CHEBI:15562:*PUBCHEM:5459771:*LIGAND-CPD:C00451:*KNAPSACK:C00001188:*CAS:30810-51-6:*LIGAND-CPD:C00311:*CAS:320-77-4 4.2.1.3 cis-aconitate + H2O = D-threo-isocitrate glyoxylate cycle D-threo-isocitrate (1R, 2S)-1-hydroxypropane-1,2,3-tricarboxylate*D-threo-isocitric acid*isocitric acid*isocitrate*threo-Ds-isocitrate*I-CIT*D-isocitrate 189.101 C6 H5 O7 C(=O)(C(CC([O-])=O)C(O)C([O-])=O)[O-] CHEBI:15562:*PUBCHEM:5459771:*LIGAND-CPD:C00451:*KNAPSACK:C00001188:*CAS:30810-51-6:*LIGAND-CPD:C00311:*CAS:320-77-4 4.2.1.3 cis-aconitate + H2O = D-threo-isocitrate TCA cycle variation III (eukaryotic) D-threo-isocitrate (1R, 2S)-1-hydroxypropane-1,2,3-tricarboxylate*D-threo-isocitric acid*isocitric acid*isocitrate*threo-Ds-isocitrate*I-CIT*D-isocitrate 189.101 C6 H5 O7 C(=O)(C(CC([O-])=O)C(O)C([O-])=O)[O-] CHEBI:15562:*PUBCHEM:5459771:*LIGAND-CPD:C00451:*KNAPSACK:C00001188:*CAS:30810-51-6:*LIGAND-CPD:C00311:*CAS:320-77-4 4.2.1.3 cis-aconitate + H2O = D-threo-isocitrate glutamine biosynthesis III D-threo-isocitrate (1R, 2S)-1-hydroxypropane-1,2,3-tricarboxylate*D-threo-isocitric acid*isocitric acid*isocitrate*threo-Ds-isocitrate*I-CIT*D-isocitrate 189.101 C6 H5 O7 C(=O)(C(CC([O-])=O)C(O)C([O-])=O)[O-] CHEBI:15562:*PUBCHEM:5459771:*LIGAND-CPD:C00451:*KNAPSACK:C00001188:*CAS:30810-51-6:*LIGAND-CPD:C00311:*CAS:320-77-4 4.1.3.1 D-threo-isocitrate = glyoxylate + succinate glyoxylate cycle D-threo-isocitrate (1R, 2S)-1-hydroxypropane-1,2,3-tricarboxylate*D-threo-isocitric acid*isocitric acid*isocitrate*threo-Ds-isocitrate*I-CIT*D-isocitrate 189.101 C6 H5 O7 C(=O)(C(CC([O-])=O)C(O)C([O-])=O)[O-] CHEBI:15562:*PUBCHEM:5459771:*LIGAND-CPD:C00451:*KNAPSACK:C00001188:*CAS:30810-51-6:*LIGAND-CPD:C00311:*CAS:320-77-4 1.1.1.42 D-threo-isocitrate + NADP+ = 2-oxoglutarate + CO2 + NADPH glutamine biosynthesis III L-leucine (2S)-α-2-amino-4-methylvaleric acid*L*leu*leucine*2-amino-4-methylvaleric acid*(2S)-α-leucine 131.174 C6 H13 N1 O2 C([N+])(C(=O)[O-])CC(C)C PUBCHEM:7045798:*CHEBI:57427:*PUBCHEM:5255803:*KNAPSACK:C00001377:*PUBCHEM:5255803:*CAS:7005-03-0*LIGAND-CPD:C00123:*NCI:46709*CAS:61-90-5 6.1.1.4 H+ + L-leucine + ATP = diphosphate + AMP tRNA charging pathway L-leucine (2S)-α-2-amino-4-methylvaleric acid*L*leu*leucine*2-amino-4-methylvaleric acid*(2S)-α-leucine 131.174 C6 H13 N1 O2 C([N+])(C(=O)[O-])CC(C)C PUBCHEM:7045798:*CHEBI:57427:*PUBCHEM:5255803:*KNAPSACK:C00001377:*PUBCHEM:5255803:*CAS:7005-03-0*LIGAND-CPD:C00123:*NCI:46709*CAS:61-90-5 3.5.1.- indole-3-acetyl-leucine + H2O = indole-3-acetate + L-leucine IAA biosynthesis II L-leucine (2S)-α-2-amino-4-methylvaleric acid*L*leu*leucine*2-amino-4-methylvaleric acid*(2S)-α-leucine 131.174 C6 H13 N1 O2 C([N+])(C(=O)[O-])CC(C)C PUBCHEM:7045798:*CHEBI:57427:*PUBCHEM:5255803:*KNAPSACK:C00001377:*PUBCHEM:5255803:*CAS:7005-03-0*LIGAND-CPD:C00123:*NCI:46709*CAS:61-90-5 2.6.1.42 L-leucine + 2-oxoglutarate = L-glutamate + 4-methyl-2-oxopentanoate leucine degradation III L-leucine (2S)-α-2-amino-4-methylvaleric acid*L*leu*leucine*2-amino-4-methylvaleric acid*(2S)-α-leucine 131.174 C6 H13 N1 O2 C([N+])(C(=O)[O-])CC(C)C PUBCHEM:7045798:*CHEBI:57427:*PUBCHEM:5255803:*KNAPSACK:C00001377:*PUBCHEM:5255803:*CAS:7005-03-0*LIGAND-CPD:C00123:*NCI:46709*CAS:61-90-5 2.6.1.42 L-leucine + 2-oxoglutarate = L-glutamate + 4-methyl-2-oxopentanoate leucine biosynthesis L-leucine (2S)-α-2-amino-4-methylvaleric acid*L*leu*leucine*2-amino-4-methylvaleric acid*(2S)-α-leucine 131.174 C6 H13 N1 O2 C([N+])(C(=O)[O-])CC(C)C PUBCHEM:7045798:*CHEBI:57427:*PUBCHEM:5255803:*KNAPSACK:C00001377:*PUBCHEM:5255803:*CAS:7005-03-0*LIGAND-CPD:C00123:*NCI:46709*CAS:61-90-5 2.6.1.42 L-leucine + 2-oxoglutarate = L-glutamate + 4-methyl-2-oxopentanoate leucine degradation I hypoglycin B hypoglycine B*L-gamma-Glutamyl-L-hypoglycin*γ-glutamyl-β-(methylenecyclopropyl)-alanine*y-L-glutamyl-a-amino-β-2-methylenecyclopropylpropionic acid*(2S)-2-amino-5-[[(2S)-1-hydroxy-3-[(1S)-2-methylidenecyclopropyl]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid 269.277 C12 H17 N2 O5 C=C1(C(CC(NC(CCC([N+])C([O-])=O)=O)C([O-])=O)C1) PUBCHEM:108105:*PUBCHEM:25246042:*|Wikipedia|:Hypoglycin_B:*LIGAND-CPD:C08280: 2.3.2.2 hypoglycin A + glutathione = hypoglycin B + cysteinylglycine hypoglycin biosynthesis 1-(o-carboxyphenylamino)-1'-deoxyribulose-5'-phosphate 1-(o-carboxyphenylamino)-1'-deoxyribulose-5'-P*1-(2-carboxyphenylamino)-1-deoxy-D-ribulose-5-phosphate*1-(2-carboxyphenylamino)-1-deoxy-D-ribulose-5-P 346.21 C12 H13 N1 O9 P1 C1(C=CC=CC(C(=O)[O-])=1)(NCC(=O)C(O)C(O)COP(=O)([O-])[O-]) PUBCHEM:25244176:*LIGAND-CPD:C01302: 4.1.1.48 H+ + 1-(o-carboxyphenylamino)-1'-deoxyribulose-5'-phosphate = (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + CO2 + H2O tryptophan biosynthesis 1-(o-carboxyphenylamino)-1'-deoxyribulose-5'-phosphate 1-(o-carboxyphenylamino)-1'-deoxyribulose-5'-P*1-(2-carboxyphenylamino)-1-deoxy-D-ribulose-5-phosphate*1-(2-carboxyphenylamino)-1-deoxy-D-ribulose-5-P 346.21 C12 H13 N1 O9 P1 C1(C=CC=CC(C(=O)[O-])=1)(NCC(=O)C(O)C(O)COP(=O)([O-])[O-]) PUBCHEM:25244176:*LIGAND-CPD:C01302: 5.3.1.24 N-(5'-phosphoribosyl)-anthranilate = 1-(o-carboxyphenylamino)-1'-deoxyribulose-5'-phosphate tryptophan biosynthesis 6-methoxy-5-methyl-2-all-trans-decaprenyl-1,4-benzoquinol 6-methoxy-5-methyl-2-decaprenyl-1,4-benzoquinol 835.347 C58 H90 O3 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(=C(C(OC)=CC(=C1C)O)O))C)C)C)C)C)C)C)CCC=C(CCC=C(C)C)C PUBCHEM:25244775: 1.14.-.- 6-methoxy-5-methyl-2-all-trans-decaprenyl-1,4-benzoquinol + oxygen = 3-demethylubiquinol-10 + H2O ubiquinol-10 biosynthesis (eukaryotic) 6-methoxy-5-methyl-2-all-trans-decaprenyl-1,4-benzoquinol 6-methoxy-5-methyl-2-decaprenyl-1,4-benzoquinol 835.347 C58 H90 O3 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(=C(C(OC)=CC(=C1C)O)O))C)C)C)C)C)C)C)CCC=C(CCC=C(C)C)C PUBCHEM:25244775: 2.1.1.- 2-methoxy-6-all trans-decaprenyl-2-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine = H+ + 6-methoxy-5-methyl-2-all-trans-decaprenyl-1,4-benzoquinol + S-adenosyl-L-homocysteine ubiquinol-10 biosynthesis (eukaryotic) (3E)-4,8-dimethylnona-1,3,7-triene (3E)-4,8-dimethyl-1,3,7-nonatriene*4,8-dimethyl-1,3(E),7-nonatriene*DMNT 150.263 C11 H18 C(CCC(=CC=C)C)=C(C)C CHEBI:60158:*PUBCHEM:6427110: 1.14.13.- H+ + (3S,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis (3E)-4,8-dimethylnona-1,3,7-triene (3E)-4,8-dimethyl-1,3,7-nonatriene*4,8-dimethyl-1,3(E),7-nonatriene*DMNT 150.263 C11 H18 C(CCC(=CC=C)C)=C(C)C CHEBI:60158:*PUBCHEM:6427110: 1.14.13.- H+ + (3R,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis GDP GDP*ppG*guanosine-5'-diphosphate*guanosine-diphosphate 440.179 C10 H12 N5 O11 P2 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) CHEBI:456089:*PUBCHEM:21604868:*LIGAND-CPD:C00035:*CAS:146-91-8 2.7.1.48 uridine + GTP = H+ + uridine-5'-phosphate + GDP salvage pathways of pyrimidine ribonucleotides GDP GDP*ppG*guanosine-5'-diphosphate*guanosine-diphosphate 440.179 C10 H12 N5 O11 P2 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) CHEBI:456089:*PUBCHEM:21604868:*LIGAND-CPD:C00035:*CAS:146-91-8 2.4.1.- GDP-α-D-mannose = H+ + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP GDP*ppG*guanosine-5'-diphosphate*guanosine-diphosphate 440.179 C10 H12 N5 O11 P2 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) CHEBI:456089:*PUBCHEM:21604868:*LIGAND-CPD:C00035:*CAS:146-91-8 2.4.1.131 GDP-α-D-mannose = GDP + H+ dolichyl-diphosphooligosaccharide biosynthesis GDP GDP*ppG*guanosine-5'-diphosphate*guanosine-diphosphate 440.179 C10 H12 N5 O11 P2 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) CHEBI:456089:*PUBCHEM:21604868:*LIGAND-CPD:C00035:*CAS:146-91-8 2.7.7.69 GDP-L-galactose = H+ + GDP + α-L-galactose-1-phosphate ascorbate biosynthesis I (L-galactose pathway) GDP GDP*ppG*guanosine-5'-diphosphate*guanosine-diphosphate 440.179 C10 H12 N5 O11 P2 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) CHEBI:456089:*PUBCHEM:21604868:*LIGAND-CPD:C00035:*CAS:146-91-8 GDP-L-fucose + GDP-L-galactose = GDP xyloglucan biosynthesis GDP GDP*ppG*guanosine-5'-diphosphate*guanosine-diphosphate 440.179 C10 H12 N5 O11 P2 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) CHEBI:456089:*PUBCHEM:21604868:*LIGAND-CPD:C00035:*CAS:146-91-8 2.4.1.132 GDP-α-D-mannose = H+ + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP GDP*ppG*guanosine-5'-diphosphate*guanosine-diphosphate 440.179 C10 H12 N5 O11 P2 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) CHEBI:456089:*PUBCHEM:21604868:*LIGAND-CPD:C00035:*CAS:146-91-8 2.7.1.- cytidine + GTP = H+ + CMP + GDP salvage pathways of pyrimidine ribonucleotides GDP GDP*ppG*guanosine-5'-diphosphate*guanosine-diphosphate 440.179 C10 H12 N5 O11 P2 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) CHEBI:456089:*PUBCHEM:21604868:*LIGAND-CPD:C00035:*CAS:146-91-8 2.4.1.83 GDP-α-D-mannose = GDP dolichyl-diphosphooligosaccharide biosynthesis GDP GDP*ppG*guanosine-5'-diphosphate*guanosine-diphosphate 440.179 C10 H12 N5 O11 P2 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) CHEBI:456089:*PUBCHEM:21604868:*LIGAND-CPD:C00035:*CAS:146-91-8 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = H+ + adenylo-succinate + GDP purine nucleotides de novo biosynthesis II GDP GDP*ppG*guanosine-5'-diphosphate*guanosine-diphosphate 440.179 C10 H12 N5 O11 P2 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) CHEBI:456089:*PUBCHEM:21604868:*LIGAND-CPD:C00035:*CAS:146-91-8 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = H+ + adenylo-succinate + GDP adenosine nucleotides de novo biosynthesis GDP GDP*ppG*guanosine-5'-diphosphate*guanosine-diphosphate 440.179 C10 H12 N5 O11 P2 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) CHEBI:456089:*PUBCHEM:21604868:*LIGAND-CPD:C00035:*CAS:146-91-8 2.4.1.142 GDP-α-D-mannose = H+ + GDP dolichyl-diphosphooligosaccharide biosynthesis sphinganine dihydrosphingosine*sphinganine*erythro-D-sphinganine*DHS 302.519 C18 H40 N1 O2 CCCCCCCCCCCCCCCC(O)C([N+])CO PUBCHEM:25202626:*LIGAND-CPD:C00836:*CAS:764-22-7 1.14.-.- H+ + sphinganine + oxygen + NADPH = 4-hydroxysphinganine + H2O + NADP+ sphingolipid biosynthesis (plants) sphinganine dihydrosphingosine*sphinganine*erythro-D-sphinganine*DHS 302.519 C18 H40 N1 O2 CCCCCCCCCCCCCCCC(O)C([N+])CO PUBCHEM:25202626:*LIGAND-CPD:C00836:*CAS:764-22-7 2.7.1.91 sphinganine + ATP = H+ + sphinganine 1-phosphate + ADP sphingolipid biosynthesis (plants) sphinganine dihydrosphingosine*sphinganine*erythro-D-sphinganine*DHS 302.519 C18 H40 N1 O2 CCCCCCCCCCCCCCCC(O)C([N+])CO PUBCHEM:25202626:*LIGAND-CPD:C00836:*CAS:764-22-7 2.3.1.- sphinganine = coenzyme A sphingolipid biosynthesis (plants) sphinganine dihydrosphingosine*sphinganine*erythro-D-sphinganine*DHS 302.519 C18 H40 N1 O2 CCCCCCCCCCCCCCCC(O)C([N+])CO PUBCHEM:25202626:*LIGAND-CPD:C00836:*CAS:764-22-7 1.1.1.102 NADP+ + sphinganine = H+ + NADPH + 3-dehydrosphinganine sphingolipid biosynthesis (plants) kaempferol-3-glucoside kaempferol-3-O-D-glucoside 447.374 C21 H19 O11 O=C2(C(OC1(OC(CO)C(O)C(O)C(O)1))=C(OC3(C=C([O-])C=C(O)C2=3))C4(=CC=C(O)C=C4)) PUBCHEM:25203515:*LIGAND-CPD:C12249: 2.4.1.91 kaempferol = kaempferol-3-glucoside + UDP + H+ flavonol glucosylation I L-dopa DOPA*3-hydroxytyrosine*3,4-dihydroxy-L-phenylalanine*dihydroxyphenylalanine*L-dihydroxy-phenylalanine*levodopa 197.19 C9 H11 N1 O4 C1(C(=C(C=CC=1CC(C(=O)[O-])[N+])O)O) CHEBI:57504:*PUBCHEM:6971033:*NCI:118381*CAS:59-92-7*LIGAND-CPD:C00355: 4.1.1.28 H+ + L-dopa = dopamine + CO2 betaxanthin biosynthesis (via dopamine) (S)-3-hydroxy-isobutyryl-CoA (S)-3-hydroxy-2-methylpropanoyl-CoA*(S)-3-hydroxy-isobutyryl-coenzyme A*(S)-3-Hydroxy-2-methylpropionyl-CoA*(S)-β-hydroxy-isobutyryl-CoA 849.593 C25 H38 N7 O18 P3 S1 O=C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(C)CO CHEBI:28259:*LIGAND-CPD:C06000:*PUBCHEM:46173170: 4.2.1.17 (S)-3-hydroxy-isobutyryl-CoA = methylacrylyl-CoA + H2O valine degradation I (S)-3-hydroxy-isobutyryl-CoA (S)-3-hydroxy-2-methylpropanoyl-CoA*(S)-3-hydroxy-isobutyryl-coenzyme A*(S)-3-Hydroxy-2-methylpropionyl-CoA*(S)-β-hydroxy-isobutyryl-CoA 849.593 C25 H38 N7 O18 P3 S1 O=C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(C)CO CHEBI:28259:*LIGAND-CPD:C06000:*PUBCHEM:46173170: 3.1.2.4 (S)-3-hydroxy-isobutyryl-CoA + H2O = (S)-3-hydroxy-isobutyrate + H+ + coenzyme A valine degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.86 H+ + 2-aceto-2-hydroxy-butanoate + NADPH = 2,3-dihydroxy-3-methylvalerate + NADP+ isoleucine biosynthesis I (from threonine) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.- 18-oxo-oleate + NADP+ + H2O = H+ + octadecenedioate + NADPH suberin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.3 afzelechin + NADP+ + H2O = leucopelargonidin + NADPH + H+ 2,3-trans-flavanols biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: isorhamnetin + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + isorhamnetin 3-sulphate quercetinsulphates biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.- H+ + 3-methoxy-4-hydroxy-5-all-trans-decaprenylbenzoate = 2-decaprenyl-6-methoxyphenol + CO2 ubiquinol-10 biosynthesis (eukaryotic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.88 H+ + dihydrokaempferol + NADPH + oxygen = dihydromyricetin + NADP+ + H2O leucodelphinidin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.88 H+ + dihydrokaempferol + NADPH + oxygen = dihydromyricetin + NADP+ + H2O syringetin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.3.10 acetoacetyl-CoA + H2O + acetyl-CoA = H+ + coenzyme A + (S)-3-hydroxy-3-methylglutaryl-CoA mevalonate pathway I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.3 NADP+ + tetrahydrofolate = H+ + NADPH + 7,8-dihydrofolate monoglutamate folate transformations II (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.3 NADP+ + tetrahydrofolate = H+ + NADPH + 7,8-dihydrofolate monoglutamate tetrahydrofolate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.- ATP + pyridoxine = H+ + ADP + pyridoxine-5'-phosphate pyridoxal 5'-phosphate salvage pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.17 H+ + L-ornithine = CO2 + putrescine putrescine biosynthesis IV H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.1.14 ammonia + ATP = H+ + ADP diphthamide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: (22R,23R)-22,23-dihydroxycampesterol = H+ + (22R,23R)-22,23-dihydroxy-campest-4-en-3-one brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: (22α)-hydroxy-campesterol = H+ + (22α)-hydroxy-campest-4-en-3-one brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.48 H+ + 1-(o-carboxyphenylamino)-1'-deoxyribulose-5'-phosphate = (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + CO2 + H2O tryptophan biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = H+ + N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis IV H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = H+ + N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine choline biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = H+ + N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.3.- H2O = H+ 3-phosphoinositide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.11.- GA29 + 2-oxoglutarate + oxygen = H+ + GA29-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.193 5-amino-6-(5-phospho-D-ribitylamino)uracil + NADP+ = 5-amino-6-(5-phospho-D-ribosylamino)uracil + NADPH + H+ flavin biosynthesis I (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.2.1.104 carbamate + H+ = ammonia + CO2 cyanate degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.4.2 ATP + UTP + L-glutamine + H2O = H+ + ADP + CTP + L-glutamate pyrimidine ribonucleotides interconversion H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.1.31 6-phospho-D-glucono-1,5-lactone + H2O = H+ + 6-phospho-D-gluconate pentose phosphate pathway (oxidative branch) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.219 H+ + dihydrokaempferol + NADPH = leucopelargonidin + NADP+ leucopelargonidin and leucocyanidin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.100 NADP+ = NADPH + H+ cis-vaccenate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.- dolichyl-diphosphooligosaccharide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.- H+ + chlorophyllide b + phytyl diphosphate = chlorophyll b + diphosphate chlorophyll cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.- H+ + 3-methoxy-4-hydroxy-5-all-trans-nonaprenylbenzoate = 2-nonaprenyl-6-methoxyphenol + CO2 ubiquinol-9 biosynthesis (eukaryotic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.1.4 indole-3-acetamide + H2O = H+ + indole-3-acetate + ammonia IAA biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.18 H+ + ATP + nicotinate mononucleotide = diphosphate + nicotinate adenine dinucleotide NAD biosynthesis I (from aspartate) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.18 H+ + ATP + nicotinate mononucleotide = diphosphate + nicotinate adenine dinucleotide pyridine nucleotide cycling (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.4.1.4 ATP + 3-methylcrotonyl-CoA + bicarbonate = H+ + ADP + 3-methylglutaconyl-CoA leucine degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.4.1.14 NAD+ + L-glutamate = H+ + NADH + 2-oxoglutarate + L-glutamine ammonia assimilation cycle II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.4.1.14 NAD+ + L-glutamate = H+ + NADH + 2-oxoglutarate + L-glutamine glutamate biosynthesis IV H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.169 (R)-pantoate + NADP+ = H+ + 2-dehydropantoate + NADPH phosphopantothenate biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.169 (R)-pantoate + NADP+ = H+ + 2-dehydropantoate + NADPH pantothenate biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.- dihydrozeatin = H+ + dihydrozeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.8.1.2 H2O + NADP+ + hydrogen sulfide = H+ + sulfite + NADPH sulfate reduction I (assimilatory) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3-(2-propenoic acid)-o-benzoquinone + H2O = H+ + 3-(2-propenoic acid)-4,6-hydroxy cyclohexa-2,5-dienone esculetin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.11.- GA19 + oxygen + 2-oxoglutarate = H+ + gibberellin A20 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- H+ + (3R,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.1.- H+ + 4-coumaroyl-CoA + malonyl-CoA = p-coumaroyltriacetic acid lactone + coenzyme A + CO2 aromatic polyketides biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.14 D-sorbitol + NAD+ = NADH + H+ sorbitol degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.98 2-(3-carboxy-3-aminopropyl)-L-histidine in eEF-2 + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine diphthamide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.127 D-myo-inositol (1,4,5)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + (22S,24R)-22-hydroxy-5α-ergostan-3-one = 6-deoxocathasterone brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.41 L-glutamate γ-semialdehyde + NADP+ = L-glutamate-5-phosphate + NADPH + H+ proline biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.41 L-glutamate γ-semialdehyde + NADP+ = L-glutamate-5-phosphate + NADPH + H+ citrulline biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.3 3-dimethylsulfoniopropionaldehyde + H2O + NAD+ = dimethylsulfoniopropionate + NADH + H+ dimethylsulfoniopropionate biosynthesis II (Spartina) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.3 3-dimethylsulfoniopropionaldehyde + H2O + NAD+ = dimethylsulfoniopropionate + NADH + H+ dimethylsulfoniopropionate biosynthesis I (Wollastonia) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.- D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,2,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.2.2.- nicotinate mononucleotide + H2O = H+ + nicotinate + D-ribose-5-phosphate pyridine nucleotide cycling (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: D-myo-inositol (3,4)-bisphosphate + ATP = H+ + D-myo-inositol (3,4,6)-trisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.- sinapaldehyde = H+ + sinapaldehyde glucoside + UDP monolignol glucosides biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.2.1.51 H+ + prephenate = keto-phenylpyruvate + H2O + CO2 phenylalanine biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.1.95 H+ + 4-coumaroyl-CoA + malonyl-CoA = resveratrol + coenzyme A + CO2 resveratrol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.8.2.26 quercetin 3-sulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin-3,3'-bissulfate quercetinsulphates biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.28 H+ + L-tryptophan = CO2 + tryptamine IAA biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.28 H+ + L-tryptophan = CO2 + tryptamine camptothecin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.215 cis-zeatin = cis-zeatin-O-glucoside + H+ + UDP cytokinins-O-glucoside biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.2.2 5,6-dihydrothymine + H2O = 3-ureido-isobutyrate + H+ thymine degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.3.12 H2O + agmatine = H+ + ammonia + N-carbamoylputrescine putrescine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.3.12 H2O + agmatine = H+ + ammonia + N-carbamoylputrescine arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.- H+ + N-dimethylethanolamine phosphate + CTP = CDP-N-dimethylethanolamine + diphosphate phosphatidylcholine biosynthesis IV H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.88 H+ + eriodictyol + NADPH + oxygen = 3',4',5'-pentahydroxyflavanone + NADP+ + H2O leucodelphinidin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.23 H+ + orotidine-5'-phosphate = CO2 + uridine-5'-phosphate uridine-5'-phosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.2.- phosphoribulosylformimino-AICAR-P + L-glutamine = H+ + L-glutamate + D-erythro-imidazole-glycerol-phosphate + aminoimidazole carboxamide ribonucleotide histidine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.2.4 (S)-3-hydroxy-isobutyryl-CoA + H2O = (S)-3-hydroxy-isobutyrate + H+ + coenzyme A valine degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.3.3 coproporphyrinogen III + oxygen + H+ = protoporphyrinogen IX + CO2 + H2O chlorophyllide a biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.3.3 coproporphyrinogen III + oxygen + H+ = protoporphyrinogen IX + CO2 + H2O heme biosynthesis from uroporphyrinogen-III I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + (22R,23R)-22,23-dihydroxy-campest-4-en-3-one = 3-dehydro-6-deoxoteasterone brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.123 myo-inositol + UDP-D-galactose = H+ + galactinol + UDP stachyose biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.- episterone + NADPH + H+ = episterol + NADP+ plant sterol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- N-hydroxy-L-tryptophan + oxygen + NADPH + H+ = N,N-dihydroxy-L-tryptophan + NADP+ + H2O IAA biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.83 geranylfarnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-hexaprenyl diphosphate + diphosphate hexaprenyl diphosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.83 geranylfarnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-hexaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.12 (S)-1-pyrroline-5-carboxylate + NAD+ + H2O = H+ + L-glutamate + NADH proline degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.12 (S)-1-pyrroline-5-carboxylate + NAD+ + H2O = H+ + L-glutamate + NADH arginine degradation I (arginase pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: dihydrosterculate = H+ + sterculate cyclopropane and cyclopropene fatty acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.- H+ + dimethylallyl diphosphate + ATP = N6-(Δ2-isopentenyl)-adenosine 5'-triphosphate + diphosphate trans-zeatin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.76 precorrin-2 + NAD+ = H+ + sirohydrochlorin + NADH siroheme biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.74 H+ + indole-3-pyruvate = CO2 + indole acetaldehyde IAA biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.64 3-demethylubiquinol-9 + S-adenosyl-L-methionine = H+ + ubiquinol-9 + S-adenosyl-L-homocysteine ubiquinol-9 biosynthesis (eukaryotic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.2.20 jasmonoyl-CoA + H2O = H+ + (+)-7-iso-jasmonate + coenzyme A jasmonic acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.20 adenosine + ATP = H+ + AMP + ADP adenine and adenosine salvage VI H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.22 H2O + NAD+ = H+ + UDP-D-glucuronate + NADH UDP-D-xylose and UDP-D-glucuronate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.22 H2O + NAD+ = H+ + UDP-D-glucuronate + NADH colanic acid building blocks biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.22 H2O + NAD+ = H+ + UDP-D-glucuronate + NADH galactose degradation III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + ferulate + NADPH + oxygen = 5-hydroxyferulate + H2O + NADP+ free phenylpropanoid acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.-.- H+ + sphinganine + oxygen + NADPH = 4-hydroxysphinganine + H2O + NADP+ sphingolipid biosynthesis (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.6.1.- 7,8-dihydroneopterin triphosphate + H2O = H+ + 7,8-dihydroneopterin phosphate + diphosphate 6-hydroxymethyl-dihydropterin diphosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.2 isopentenyl diphosphate + H2O = 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H+ methylerythritol phosphate pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.1.4 D-glucosamine-6-phosphate + acetyl-CoA = H+ + N-acetyl-D-glucosamine-6-phosphate + coenzyme A UDP-N-acetyl-D-glucosamine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.1 H+ + 4-methyl-2-oxopentanoate = 3-methylbutanal + CO2 leucine degradation III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.- H+ + L-serine = ethanolamine + CO2 choline biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 gluconeogenesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 glutamine biosynthesis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 CO2 fixation into oxaloacetate H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 C4 photosynthetic carbon assimilation cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.- dihydrozeatin-9-N-glucoside = H+ + dihydrozeatin-9-N-glucoside-O-glucoside + UDP cytokinins-O-glucoside biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.148 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + ATP = H+ + 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + ADP methylerythritol phosphate pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.8.4.9 H+ + sulfite + AMP + glutathione disulfide = adenosine 5'-phosphosulfate + glutathione sulfate reduction II (assimilatory) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.8.1.9 NADP+ = NADPH + H+ thioredoxin pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP galactose degradation I (Leloir pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP stachyose degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP colanic acid building blocks biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP galactose degradation III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.35 H+ + UDP-D-glucuronate = UDP-α-D-xylose + CO2 UDP-D-xylose and UDP-D-glucuronate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.1 α-D-glucose + ATP = H+ + α-D-glucose 6-phosphate + ADP sucrose degradation III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.1 α-D-glucose + ATP = H+ + α-D-glucose 6-phosphate + ADP starch degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.156 indol-3-yl-acetyl-myo-inositol + UDP-D-galactose = H+ + 5-O-(indol-3-ylacetyl-myo-inositol) D-galactoside + UDP IAA conjugate biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.132 GDP-α-D-mannose = H+ + GDP dolichyl-diphosphooligosaccharide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.1 H+ + isobutanal + NADH = isobutanol + NAD+ valine degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.14 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 2-coumarate coumarin biosynthesis (via 2-coumarate) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.1 H+ + 2-oxoisovalerate = isobutanal + CO2 valine degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.-.- 2-oxohexa-4,5-cyclopropyl-5-enoate + acetyl-CoA + H2O = H+ + 3-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate + coenzyme A hypoglycin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.23 histidinal + NAD+ + H2O = H+ + L-histidine + NADH histidine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.255 NAD+ + D-mannitol = H+ + NADH mannitol degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.7.7.1 ammonia + H2O = nitrite + H+ nitrate reduction II (assimilatory) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.1 H+ + pyruvate = acetaldehyde + CO2 acetaldehyde biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.1 H+ + pyruvate = acetaldehyde + CO2 acetaldehyde biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.1 H+ + pyruvate = acetaldehyde + CO2 pyruvate fermentation to ethanol II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.2 5,6-dihydrouracil + NADP+ = uracil + NADPH + H+ uracil degradation II (reductive) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.-.- H+ + 24-methyldesmosterol = 24-epi-campesterol plant sterol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ suberin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ phenylpropanoid biosynthesis, initial reactions H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ trans-cinnamoyl-CoA biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.3.1.24 L-phenylalanine = trans-cinnamate + ammonia + H+ benzoate biosynthesis II (CoA-independent, non-β-oxidative) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.1.6 3-ureido-isobutyrate + H2O + H+ = (R)-3-amino-2-methylpropanoate + ammonia + CO2 thymine degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1D-myo-inositol (3)-monophosphate + ATP = H+ + D-myo-inositol (3,4)-bisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.8.1.1 thiosulfate + hydrogen cyanide = H+ + sulfite + thiocyanate thiosulfate disproportionation III (rhodanese) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.1.- H+ + 4-coumaroyl-CoA + malonyl-CoA = bis-noryangonin + coenzyme A + CO2 resveratrol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.- coniferaldehyde = H+ + coniferaldehyde glucoside + UDP monolignol glucosides biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.- delphinidin 3-O-glucosyl-5-O-caffeoylglucoside = H+ + delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + UDP gentiodelphin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = H+ + dethiobiotin + ADP biotin biosynthesis from 7-keto-8-aminopelargonate H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.77 H+ + pelargonidin = epiafzelechin 2,3-cis-flavanols biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.93 H+ + 2-cis-abscisic acid + NADPH + oxygen = 8'-hydroxyabscisate + NADP+ + H2O phaseic acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.82 (S)-malate + NADP+ = H+ + NADPH + oxaloacetate C4 photosynthetic carbon assimilation cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.2.28 1,4-dihydroxy-2-naphthoyl-CoA + H2O = H+ + 1,4-dihydroxy-2-naphthoate + coenzyme A 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.21.3.3 oxygen + (S)-reticuline = H+ + hydrogen peroxide + S-scoulerine dehydroscoulerine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + 3-dehydro-6-deoxoteasterone = 6-deoxotyphasterol brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.18.1.2 NADP+ = NADPH + H+ photosynthesis light reactions H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate phosphatidylcholine biosynthesis IV H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate choline biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate phosphatidylcholine biosynthesis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate phosphatidylcholine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.47 O-acetyl-L-serine + hydrogen sulfide = H+ + L-cysteine + acetate cysteine biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.- dolichyl-diphosphooligosaccharide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.11.- H+ + leucopelargonidin + 2-oxoglutarate + oxygen = pelargonidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.25 shikimate + NADP+ = H+ + 3-dehydroshikimate + NADPH chorismate biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.2.2 ammonia + CO2 + ATP = H+ + carbamoyl-phosphate + ADP citrulline degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.2.2 ammonia + CO2 + ATP = H+ + carbamoyl-phosphate + ADP allantoin degradation IV (anaerobic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.- dolichyl-diphosphooligosaccharide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.267 2-C-methyl-D-erythritol-4-phosphate + NADP+ = 1-deoxy-D-xylulose 5-phosphate + NADPH + H+ methylerythritol phosphate pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.23 H+ + N-acetyl-α-D-glucosamine 1-phosphate + UTP = UDP-α-N-acetyl-D-glucosamine + diphosphate UDP-N-acetyl-D-glucosamine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.21 H+ + apigenin + NADPH + oxygen = luteolin + NADP+ + H2O luteolin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.6.1.23 dUTP + H2O = H+ + dUMP + diphosphate pyrimidine deoxyribonucleotides de novo biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.- D-ribulose-1,5-bisphosphate + oxygen = 2-phosphoglycolate + 3-phospho-D-glycerate + H+ photorespiration H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.64 3-demethylubiquinol-10 + S-adenosyl-L-methionine = H+ + ubiquinol-10 + S-adenosyl-L-homocysteine ubiquinol-10 biosynthesis (eukaryotic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.3.27 chorismate + L-glutamine = H+ + anthranilate + L-glutamate + pyruvate tryptophan biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.2.1.52 pyruvate + L-aspartate-semialdehyde = H+ + H2O + L-2,3-dihydrodipicolinate lysine biosynthesis VI H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.33 (R)-pantothenate + ATP = H+ + D-4'-phosphopantothenate + ADP phosphopantothenate biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.79 H+ + ent-kaurenoate + oxygen + NADPH = ent-7-α-hydroxykaurenoate + H2O + NADP+ GA12 biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.3.9 H+ + allantoate + H2O = S-ureidoglycine + ammonia + CO2 allantoin degradation to ureidoglycolate II (ammonia producing) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate arginine degradation VI (arginase 2 pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate arginine degradation I (arginase pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate proline biosynthesis II (from arginine) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate proline biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: L-glutamate γ-semialdehyde = H+ + H2O + (S)-1-pyrroline-5-carboxylate citrulline biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.79 oleate + S-adenosyl-L-methionine = H+ + dihydrosterculate + S-adenosyl-L-homocysteine cyclopropane and cyclopropene fatty acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.57 H+ + N-methylethanolamine phosphate + CTP = CDP-N-methylethanolamine + diphosphate phosphatidylcholine biosynthesis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.1 H+ + 3-methylbutanal + NADH = 3-methylbutanol + NAD+ leucine degradation III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = H+ + 5'-phosphoribosyl-N-formylglycineamide + ADP 5-aminoimidazole ribonucleotide biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = H+ + 5'-phosphoribosyl-N-formylglycineamide + ADP superpathway of 5-aminoimidazole ribonucleotide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.- cycloeucalenone + NADPH + H+ = cycloeucalenol + NADP+ plant sterol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.5.1 indole-3-acetonitrile + H2O = H+ + ammonia + indole-3-acetate IAA biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.36 NADP+ = NADPH + H+ very long chain fatty acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.84 all-trans-octaprenyl diphosphate + isopentenyl diphosphate = H+ + all-trans-nonaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O leucopelargonidin and leucocyanidin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O leucodelphinidin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O flavonol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.2.1.7 H+ + pyruvate + D-glyceraldehyde-3-phosphate = 1-deoxy-D-xylulose 5-phosphate + CO2 methylerythritol phosphate pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.114 3,4-dihydroxy-5-all-trans-decaprenylbenzoate + S-adenosyl-L-methionine = H+ + 3-methoxy-4-hydroxy-5-all-trans-decaprenylbenzoate + S-adenosyl-L-homocysteine ubiquinol-10 biosynthesis (eukaryotic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = H+ + N-acetylglutamyl-phosphate + NADPH arginine biosynthesis II (acetyl cycle) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = H+ + N-acetylglutamyl-phosphate + NADPH ornithine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: NADPH + H+ = NADP+ cis-vaccenate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.195 coniferyl alcohol + NADP+ = coniferaldehyde + NADPH + H+ phenylpropanoid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.11 H+ + L-serine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.8.2 CDP-choline = CMP + H+ phosphatidylcholine biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.8.2 CDP-choline = CMP + H+ choline biosynthesis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.8.2 CDP-choline = CMP + H+ phosphatidylcholine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.4.3.22 propane-1,3-diamine + H2O + oxygen = H+ + 3-aminopropanal + ammonia + hydrogen peroxide β-alanine biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.9 NAD+ = NADH + H+ fatty acid elongation -- saturated H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.14 H+ + phosphoryl-ethanolamine + CTP = CDP-ethanolamine + diphosphate phosphatidylethanolamine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP Rubisco shunt H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP glycolysis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP glycolysis IV (plant cytosol) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP glycolysis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.2.2 lauroyl-CoA + H2O = H+ + laurate + coenzyme A ω-hydroxylation of caprate and laurate H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.7 ATP = H+ + D-mannose 6-phosphate + ADP mannitol degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.8.2.25 quercetin + phosphoadenosine-5'-phosphosulfate = H+ + adenosine 3',5'-bisphosphate + quercetin 3-sulfate quercetinsulphates biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.142 GDP-α-D-mannose = H+ + GDP dolichyl-diphosphooligosaccharide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.6.5.4 monodehydroascorbate + NADPH = H+ + L-ascorbate + NADP+ ascorbate glutathione cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.271 NADP+ + GDP-L-fucose = H+ + NADPH + GDP-4-dehydro-6-deoxy-D-mannose GDP-L-fucose biosynthesis I (from GDP-D-mannose) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.91 kaempferol = kaempferol-3-glucoside + UDP + H+ flavonol glucosylation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.2.99.20 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate = H+ + (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + pyruvate 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.18 H+ + L-lysine = CO2 + cadaverine lysine degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.8.1.4 NAD+ = NADH + H+ glycine cleavage complex H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.6.2 thiamin + ATP = H+ + thiamine diphosphate + AMP thiamine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + Δ24-25-sitosterol + NADPH = sitosterol + NADP+ plant sterol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.10 S-methyl-L-methionine + L-homocysteine = H+ + L-methionine methionine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.10 S-methyl-L-methionine + L-homocysteine = H+ + L-methionine S-methylmethionine cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.80 H+ + primary fluorescent chlorophyll catabolite + NADP+ = red chlorophyll catabolite + NADPH chlorophyll a degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.77 H+ + delphinidin = epigallocatechin 2,3-cis-flavanols biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.37 uroporphyrinogen-III + H+ = coproporphyrinogen III + CO2 chlorophyllide a biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.37 uroporphyrinogen-III + H+ = coproporphyrinogen III + CO2 heme biosynthesis from uroporphyrinogen-III I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.95 δ-tocopherol + S-adenosyl-L-methionine = H+ + β-tocopherol + S-adenosyl-L-homocysteine vitamin E biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.36 H+ + R-4'-phosphopantothenoyl-L-cysteine = 4'-phosphopantetheine + CO2 coenzyme A biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + chlorophyllide a = pheophorbide a + Mg2+ chlorophyll a degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.19 4-aminobutanal + NAD+ + H2O = 4-aminobutyrate + NADH + H+ putrescine degradation IV H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.18.6.1 H+ + N2 + ATP + H2O = H2 + ammonia + ADP nitrogen fixation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.76 quercetin + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + 3-O-methylquercetin methylquercetin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.11.- leucocyanidin + 2-oxoglutarate + oxygen = H+ + cyanidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.68 trans-caffeate + S-adenosyl-L-methionine = H+ + ferulate + S-adenosyl-L-homocysteine suberin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.68 trans-caffeate + S-adenosyl-L-methionine = H+ + ferulate + S-adenosyl-L-homocysteine free phenylpropanoid acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.68 trans-caffeate + S-adenosyl-L-methionine = H+ + ferulate + S-adenosyl-L-homocysteine simplecoumarins biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- H+ + (22α)-hydroxy-campesterol + NADPH + oxygen = (22R,23R)-22,23-dihydroxycampesterol + NADP+ + H2O brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.11.- GA19 + oxygen + 2-oxoglutarate = H+ + GA17 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.2.1 β-alanine + (R)-pantoate + ATP = H+ + (R)-pantothenate + diphosphate + AMP phosphopantothenate biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.2.1 β-alanine + (R)-pantoate + ATP = H+ + (R)-pantothenate + diphosphate + AMP pantothenate biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.205 inosine-5'-phosphate + H2O + NAD+ = xanthosine-5-phosphate + NADH + H+ adenosine nucleotides degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.205 inosine-5'-phosphate + H2O + NAD+ = xanthosine-5-phosphate + NADH + H+ purine nucleotides de novo biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.8.5 sn-glycerol-3-phosphate = CMP + H+ phosphatidylglycerol biosynthesis I (plastidic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.8.5 sn-glycerol-3-phosphate = CMP + H+ phosphatidylglycerol biosynthesis II (non-plastidic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.8.5 sn-glycerol-3-phosphate = CMP + H+ cardiolipin biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.21 H+ + naringenin + NADPH + oxygen = eriodictyol + NADP+ + H2O luteolin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: trans-zeatin riboside triphosphate + H2O = H+ + trans-zeatin riboside diphosphate trans-zeatin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + (5α)-campestan-3-one = campestanol brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.59 3-hydroxypropionate + NAD+ = malonate semialdehyde + NADH + H+ β-alanine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.28 H+ + L-dopa = dopamine + CO2 betaxanthin biosynthesis (via dopamine) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.35 3-(4-hydroxyphenyl)-3-hydroxy-propionyl-CoA + NAD+ = 3-(4-hydroxyphenyl)-3-oxo-propionyl-CoA + NADH + H+ 4-hydroxybenzoate biosynthesis V H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- H+ + campestanol + oxygen + NADPH = 6-deoxocathasterone + H2O + NADP+ brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.2.2 10-formyl-tetrahydrofolate + 5-phospho-ribosyl-glycineamide = H+ + tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.2.2 10-formyl-tetrahydrofolate + 5-phospho-ribosyl-glycineamide = H+ + tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide 5-aminoimidazole ribonucleotide biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.83 pseudouridine + ATP = H+ + pseudouridine 5'-phosphate + ADP pseudouridine degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.9 NADH + H+ = NAD+ palmitate biosynthesis II (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.1.19 nicotinamide + H2O = H+ + ammonia + nicotinate pyridine nucleotide cycling (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.2.17 5-hydroxyisourate + H2O = H+ + 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate urate degradation to allantoin H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: quercetin 3, 7, 4'-trisulphate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin 3, 7, 3', 4'-tetrasulphate quercetinsulphates biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.6.1.1 ATP + protoporphyrin IX + Mg2+ + H2O = H+ + Mg-protoporphyrin + ADP chlorophyllide a biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.81 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + oxygen + NADPH + H+ = divinyl protochlorophyllide a + NADP+ + H2O chlorophyllide a biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6-deoxoteasterone = H+ + 3-dehydro-6-deoxoteasterone brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.44 H+ + feruloyl-CoA + NADPH = coniferaldehyde + NADP+ + coenzyme A phenylpropanoid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.1.6 3-ureidopropionate + H2O + H+ = β-alanine + ammonia + CO2 uracil degradation II (reductive) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ pyridine nucleotide cycling (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.2.- H+ + nicotinate + D-ribulose-1-phosphate = nicotinate riboside pyridine nucleotide cycling (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.2.2 H2O + 5,6-dihydrouracil = H+ + 3-ureidopropionate uracil degradation II (reductive) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.2.6 ATP + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-aspartate = H+ + ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole inosine-5'-phosphate biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: trans-zeatin riboside diphosphate + H2O = H+ + trans-zeatin riboside monophosphate trans-zeatin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.3.2 L-aspartate + carbamoyl-phosphate = H+ + N-carbamoyl-L-aspartate uridine-5'-phosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.27 (S)-lactate + NAD+ = pyruvate + NADH + H+ pyruvate fermentation to lactate H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.- dolichyl-diphosphooligosaccharide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.44 H+ + α-D-glucuronate 1-phosphate + UTP = UDP-D-glucuronate + diphosphate UDP-D-glucuronate biosynthesis (from myo-inositol) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.31 H+ + Δ1-piperideine-6-carboxylate + H2O = 2-aminoadipate-6-semialdehyde lysine degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: dopamine + betalamic acid = H+ + miraxanthin V + H2O betaxanthin biosynthesis (via dopamine) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.3.14 abscisic aldehyde + H2O + oxygen = H+ + 2-cis-abscisic acid + hydrogen peroxide abscisic acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.3.14 abscisic aldehyde + H2O + oxygen = H+ + 2-cis-abscisic acid + hydrogen peroxide aldehyde oxidation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.4.- ADP ribose 1'',2''-cyclic phosphate + H2O = H+ + ADP ribose 1''-phosphate tRNA splicing H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.16.1.7 Fe3+ + NADH = H+ + Fe2+ + NAD+ Fe(III)-reduction and Fe(II) transport H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.14 H+ + glycine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.30 all-trans-hexaprenyl diphosphate + isopentenyl diphosphate = H+ + all-trans-heptaprenyl diphosphate + diphosphate heptaprenyl diphosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.30 all-trans-hexaprenyl diphosphate + isopentenyl diphosphate = H+ + all-trans-heptaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.99.12 H+ + cis-zeatin + H2O + FAD = 3-methyl-4-cis-hydroxy-2-butenal + adenine + FADH2 cytokinins degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: monodehydroascorbate = H+ + L-ascorbate + L-dehydro-ascorbate ascorbate glutathione cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.49 ATP + hydroxymethylpyrimidine = H+ + ADP + hydroxymethylpyrimidine phosphate thiamine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- nonaprenyl-4-hydroxybenzoate + oxygen + NADPH + H+ = 3,4-dihydroxy-5-all-trans-nonaprenylbenzoate + H2O + NADP+ ubiquinol-9 biosynthesis (eukaryotic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.107 S-adenosyl-L-methionine + uroporphyrinogen-III = H+ + S-adenosyl-L-homocysteine + precorrin-1 siroheme biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.9 L-saccharopine + H2O + NAD+ = L-glutamate + 2-aminoadipate-6-semialdehyde + NADH + H+ lysine degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A glyoxylate cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A TCA cycle variation III (eukaryotic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A glutamine biosynthesis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.34 NADP+ + coenzyme A + (R)-mevalonate = H+ + NADPH + (S)-3-hydroxy-3-methylglutaryl-CoA mevalonate pathway I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.4.1.1 L-cystathionine + H2O = H+ + ammonia + 2-oxobutanoate + L-cysteine homocysteine and cysteine interconversion H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.4.3.16 L-aspartate + oxygen = H+ + α-iminosuccinate + hydrogen peroxide NAD biosynthesis I (from aspartate) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.30 glycerol + ATP = H+ + sn-glycerol-3-phosphate + ADP glycerol degradation IV H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.30 glycerol + ATP = H+ + sn-glycerol-3-phosphate + ADP glycerol degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.13.1.1 UDP-α-D-glucose + H+ + sulfite = UDP-α-D-sulfoquinovopyranose + H2O sulfolipid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.28 NAD+ + 2,3-dihydro-2,3-dihydroxybenzoate = H+ + NADH + 2,3-dihydroxybenzoate 2,3-dihydroxybenzoate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.14.8 anthranilate + oxygen + FADH2 = 3-hydroxyanthranilate + H2O + FAD + H+ anthranilate degradation IV (aerobic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.3.- episterol = H+ + 5-dehydro episterol plant sterol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + gibberellin A12 + oxygen = GA53 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + 3,4,6-trihydroxy-cis-cinnamate = esculetin + H2O esculetin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.2.2 decanoyl-CoA + H2O = H+ + caprate + coenzyme A ω-hydroxylation of caprate and laurate H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.1.50 H+ + L-serine + palmitoyl-CoA = CO2 + 3-dehydrosphinganine + coenzyme A sphingolipid biosynthesis (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.31 D-glycerate + ATP = H+ + 3-phospho-D-glycerate + ADP photorespiration H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- H+ + campesterol + oxygen + NADPH = (22α)-hydroxy-campesterol + H2O + NADP+ brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.103 N-dimethylethanolamine phosphate + S-adenosyl-L-methionine = H+ + phosphoryl-choline + S-adenosyl-L-homocysteine choline biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.103 N-dimethylethanolamine phosphate + S-adenosyl-L-methionine = H+ + phosphoryl-choline + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.85 (2R,3S)-3-isopropylmalate + NAD+ = (2S)-2-isopropyl-3-oxosuccinate + NADH + H+ leucine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 7-hydroxy-chlorophyll a + H2O + NADP+ = H+ + chlorophyll a + oxygen + NADPH chlorophyll cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- H+ + 3-epi-6-deoxocathasterone + NADPH + oxygen = 6-deoxotyphasterol + NADP+ + H2O brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.4.16 ammonia + H2O + CO2 + ATP = H+ + carbamoyl-phosphate + ADP urea cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = H+ + glutathione + ADP γ-glutamyl cycle (plant pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = H+ + glutathione + ADP glutathione biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3,7-di-methylquercetagetin + S-adenosyl-L-methionine = H+ + 3,7,3'-tri-methylquercetagetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.4.1.11 L-methionine + H2O = H+ + methanethiol + ammonia + 2-oxobutanoate methionine degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.99.- H+ + campest-4-en-3-one + NADPH = (5α)-campestan-3-one + NADP+ brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.3.38 4-amino-4-deoxychorismate = H+ + p-aminobenzoate + pyruvate p-aminobenzoate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.244 methanol + NAD+ = H+ + formaldehyde + NADH methanol oxidation to formaldehyde II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.81 isopentenyl diphosphate + all-trans-geranyl-geranyl diphosphate = H+ + geranylfarnesyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.1.- H+ + malonyl-CoA + (E)-cinnamoyl-CoA = pinocembrin chalcone + coenzyme A + CO2 pinobanksin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.3.9 benzaldehyde + oxygen + H2O = H+ + benzoate + hydrogen peroxide aldehyde oxidation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + (2S)-2-isopropyl-3-oxosuccinate = 4-methyl-2-oxopentanoate + CO2 leucine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- H+ + chlorophyllide a + oxygen + NADPH = 7-hydroxy-chlorophyllide a + H2O + NADP+ chlorophyll cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.8.1.4 NAD+ = NADH + H+ acetyl-CoA biosynthesis (from pyruvate) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.2 H+ + L-tryptophan + ATP = AMP + diphosphate tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.24 succinate semialdehyde + H2O + NAD+ = succinate + NADH + H+ glutamate degradation III (via 4-aminobutyrate) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.24 succinate semialdehyde + H2O + NAD+ = succinate + NADH + H+ 4-aminobutyrate degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.10.3.- H+ + oxygen = H+ + H2O NADH to cytochrome bd oxidase electron transfer H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.10.3.- H+ + oxygen = H+ + H2O succinate to cytochrome bd oxidase electron transfer H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.3 H+ + 4-methyl-5-(2-phosphonooxyethyl)thiazole + 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate = thiamine-phosphate + diphosphate thiamine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.11 H+ + L-serine + ATP = diphosphate + AMP selenocysteine biosynthesis II (archaea and eukaryotes) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 5.5.1.6 pinocembrin chalcone = H+ + (2S)-pinocembrin pinobanksin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.21 H+ + L-histidine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.-.- H+ + 24-methyldesmosterol + NADPH = campesterol + NADP+ plant sterol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.19 D-ribulose-5-phosphate + ATP = H+ + D-ribulose-1,5-bisphosphate + ADP Rubisco shunt H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.19 D-ribulose-5-phosphate + ATP = H+ + D-ribulose-1,5-bisphosphate + ADP Calvin-Benson-Bassham cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.149 myricetin + S-adenosyl-L-methionine = H+ + laricitrin + S-adenosyl-L-homocysteine syringetin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.36 (R)-mevalonate + ATP = H+ + mevalonate-5-phosphate + ADP mevalonate pathway I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.151 D-myo-inositol (1,3,4,5)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.151 D-myo-inositol (1,3,4,5)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.151 D-myo-inositol (1,3,4,5)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations II (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH photorespiration H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- H+ + (3S,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.41 S-adenosyl-L-methionine + cycloartenol = H+ + S-adenosyl-L-homocysteine + 24-methylenecycloartanol plant sterol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 5.5.1.6 naringenin chalcone = H+ + naringenin flavonoid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.42 NADP+ + 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate = H+ + NADPH + 12-oxo-cis-10,15-phytodienoate jasmonic acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.111 coniferyl alcohol = H+ + coniferin + UDP coniferin metabolism H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.195 H+ + sinapaldehyde + NADPH = sinapyl-alcohol + NADP+ phenylpropanoid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ flavonoid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ simplecoumarins biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ phenylpropanoid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ 4-hydroxybenzoate biosynthesis V H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.9 H+ + 6,7-dimethyl-8-(1-D-ribityl)lumazine = 5-amino-6-(D-ribitylamino)uracil + riboflavin flavin biosynthesis I (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + 4-coumarate + NADPH + oxygen = trans-caffeate + H2O + NADP+ suberin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + 4-coumarate + NADPH + oxygen = trans-caffeate + H2O + NADP+ free phenylpropanoid acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.-.-.- 2-oxopentenoate = H+ + 2-oxopenta-3,4-dienoate hypoglycin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.3.1.19 L-threonine = H+ + 2-oxobutanoate + ammonia isoleucine biosynthesis I (from threonine) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.3.1.19 L-threonine = H+ + 2-oxobutanoate + ammonia hypoglycin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.34 H+ + α-D-glucose 1-phosphate + GTP = GDP-α-D-glucose + diphosphate GDP-glucose biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.2.2 L-cysteine + L-glutamate + ATP = H+ + L-γ-glutamylcysteine + ADP γ-glutamyl cycle (plant pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.2.2 L-cysteine + L-glutamate + ATP = H+ + L-γ-glutamylcysteine + ADP glutathione biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.12.20 pheophorbide a + oxygen + NADPH = H+ + red chlorophyll catabolite + NADP+ chlorophyll a degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.21 H+ + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate = 5-aminoimidazole ribonucleotide + CO2 inosine-5'-phosphate biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- 3-decaprenyl-4-hydroxybenzoate + oxygen + NADPH + H+ = 3,4-dihydroxy-5-all-trans-decaprenylbenzoate + H2O + NADP+ ubiquinol-10 biosynthesis (eukaryotic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.99.1.4 H+ + sirohydrochlorin + Fe2+ = siroheme siroheme biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.151 D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.151 D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.151 D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.1.1 L-asparagine + H2O = L-aspartate + ammonia + H+ asparagine degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: quercetin 3,3',7-trissulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin 3, 7, 3', 4'-tetrasulphate quercetinsulphates biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.- quercetin + S-adenosyl-L-methionine = H+ + isorhamnetin + S-adenosyl-L-homocysteine quercetinsulphates biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.- quercetin + S-adenosyl-L-methionine = H+ + isorhamnetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.3 gallocatechin + NADP+ + H2O = leucodelphinidin + NADPH + H+ 2,3-trans-flavanols biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.2.1.1 bicarbonate + H+ = CO2 + H2O cyanate degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.95 3-phospho-D-glycerate + NAD+ = H+ + 3-phospho-hydroxypyruvate + NADH serine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.81 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + oxygen = 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.285 2'-deoxymugineic acid = 3''-deamino-3''-oxonicotianamine + H+ 2'-deoxymugineic acid phytosiderophore biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.26 riboflavin + ATP = H+ + FMN + ADP flavin biosynthesis I (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.10.99.3 H+ + violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O antheraxanthin and violaxanthin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.10.99.3 H+ + violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.38 NADP+ = NADPH + H+ very long chain fatty acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH gluconeogenesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH glycolysis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH glycolysis IV (plant cytosol) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH glycolysis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: N6-(Δ2-isopentenyl)-adenosine 5'-triphosphate + NADPH + H2O = H+ + trans-zeatin riboside triphosphate + NADP+ trans-zeatin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.2.12 L-glutamate + 7,8-dihydropteroate + ATP = H+ + 7,8-dihydrofolate monoglutamate + ADP tetrahydrofolate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.- H+ + chlorophyllide a + all-trans-geranyl-geranyl diphosphate = geranylgeranyl-chlorophyll a + diphosphate chlorophyll a biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.2.5 S-allantoin + H2O = H+ + allantoate allantoin degradation to ureidoglycolate I (urea producing) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.2.5 S-allantoin + H2O = H+ + allantoate allantoin degradation to ureidoglycolate II (ammonia producing) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.69 GDP-L-galactose = H+ + GDP + α-L-galactose-1-phosphate ascorbate biosynthesis I (L-galactose pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.3.- avenasterol = H+ + 5-dehydroavenasterol plant sterol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.29 (2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-geranyl-geranyl diphosphate + diphosphate geranylgeranyldiphosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.29 (2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-geranyl-geranyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.- 2-methoxy-6-all trans-decaprenyl-2-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine = H+ + 6-methoxy-5-methyl-2-all-trans-decaprenyl-1,4-benzoquinol + S-adenosyl-L-homocysteine ubiquinol-10 biosynthesis (eukaryotic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.60 H+ + 2-C-methyl-D-erythritol-4-phosphate + CTP = 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + diphosphate methylerythritol phosphate pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.71 shikimate + ATP = H+ + shikimate-3-phosphate + ADP chorismate biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.- nicotinate riboside + ATP = H+ + nicotinate mononucleotide + ADP pyridine nucleotide cycling (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + S-methyl-L-methionine = DMSP-amine + CO2 dimethylsulfoniopropionate biosynthesis II (Spartina) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.11.- gibberellin A8 + 2-oxoglutarate + oxygen = H+ + GA8-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.23 NAD+ + ATP = H+ + NADP+ + ADP NAD/NADH phosphorylation and dephosphorylation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ adenosine nucleotides degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ adenosine nucleotides degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ guanosine nucleotides degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.99.12 H+ + 2-methylbutanoyl-CoA + FAD = 2-methyl-crotonyl-CoA + FADH2 isoleucine degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.- H+ + tetrahydrogeranylgeranyl-chlorophyll a + NADPH = chlorophyll a + NADP+ chlorophyll a biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.99.12 H+ + trans-zeatin riboside + H2O + FAD = adenosine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.294 7-hydroxy-chlorophyll a = chlorophyll b + H+ chlorophyll cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.11 ATP + D-fructose-6-phosphate = H+ + ADP + fructose-1,6-bisphosphate glycolysis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.11 ATP + D-fructose-6-phosphate = H+ + ADP + fructose-1,6-bisphosphate glycolysis IV (plant cytosol) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.11 ATP + D-fructose-6-phosphate = H+ + ADP + fructose-1,6-bisphosphate glycolysis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.26 tetrahydrodipicolinate = L-2,3-dihydrodipicolinate + H+ lysine biosynthesis VI H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.141 UDP-α-N-acetyl-D-glucosamine = H+ + UDP dolichyl-diphosphooligosaccharide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.11 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 4-coumarate suberin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.11 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 4-coumarate phenylpropanoid biosynthesis, initial reactions H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.3.36 H+ + 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA = 1,4-dihydroxy-2-naphthoyl-CoA + H2O 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate folate transformations I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate folate transformations II (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate formaldehyde oxidation V (tetrahydrofolate pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.- dihydroconiferyl alcohol = H+ + dihydroconiferyl alcohol glucoside + UDP monolignol glucosides biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3,7,3'-tri-methylquercetagetin + S-adenosyl-L-methionine = H+ + 3,6,7,3'-tetra-methylquercetagetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.4.46 H2O = sn-glycerol-3-phosphate + H+ glycerol degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.6.1.83 L,L-diaminopimelate + 2-oxoglutarate = tetrahydrodipicolinate + L-glutamate + H2O + H+ lysine biosynthesis VI H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.7.1 5-methyl-tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H+ folate transformations I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.140 1D-myo-inositol (1,2,3,4,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.98 S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + H+ diphthamide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.62 H+ + chlorophyllide a + phytyl diphosphate = chlorophyll a + diphosphate chlorophyll cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.62 H+ + chlorophyllide a + phytyl diphosphate = chlorophyll a + diphosphate chlorophyll a biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.71 S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.64 myo-inositol + ATP = H+ + 1D-myo-inositol (3)-monophosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.39 L-homoserine + ATP = H+ + O-phospho-L-homoserine + ADP threonine biosynthesis from homoserine H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.39 L-homoserine + ATP = H+ + O-phospho-L-homoserine + ADP methionine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.145 campest-4-en-3β-ol = H+ + campest-4-en-3-one brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.149 laricitrin + S-adenosyl-L-methionine = H+ + syringetin + S-adenosyl-L-homocysteine syringetin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.2.1.6 H+ + pyruvate + 2-oxobutanoate = 2-aceto-2-hydroxy-butanoate + CO2 isoleucine biosynthesis I (from threonine) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.3.- H+ + 2-nonaprenyl-6-methoxyphenol + oxygen = 2-methoxy-6-all trans-nonaprenyl-2-methoxy-1,4-benzoquinol + H2O ubiquinol-9 biosynthesis (eukaryotic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.178 NAD+ + 2-methyl-3-hydroxybutyryl-CoA = H+ + NADH + 2-methylacetoacetyl-CoA isoleucine degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = H+ + L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.5 H+ + L-isoleucine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.1.- H+ + 4-coumaroyl-CoA + H2O + malonyl-CoA = coenzyme A + CO2 + p-coumaroyltriacetate resveratrol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.27 H+ + α-D-glucose 1-phosphate + ATP = ADP-α-D-glucose + diphosphate glycogen biosynthesis I (from ADP-D-Glucose) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.27 H+ + α-D-glucose 1-phosphate + ATP = ADP-α-D-glucose + diphosphate starch biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.90 all-trans-heptaprenyl diphosphate + isopentenyl diphosphate = H+ + diphosphate + all-trans-octaprenyl diphosphate nonaprenyl diphosphate biosynthesis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.15 α-D-glucose 6-phosphate = H+ + UDP + trehalose 6-phosphate trehalose biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.6 H+ + L-lysine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.41 CTP + H+ = diphosphate CDP-diacylglycerol biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.41 CTP + H+ = diphosphate CDP-diacylglycerol biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ adenosine nucleotides degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ adenosine nucleotides degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + UDP-4-dehydro-6-deoxy-D-glucose + NADPH = UDP-L-rhamnose + NADP+ UDP-L-rhamnose biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.32 choline + ATP = H+ + phosphoryl-choline + ADP phosphatidylcholine biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.2.1.65 L-asparagine = H+ + H2O + 3-cyano-L-alanine cyanide detoxification H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- H+ + (22α)-hydroxy-campest-4-en-3-one + NADPH + oxygen = (22R,23R)-22,23-dihydroxy-campest-4-en-3-one + NADP+ + H2O brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.22 spermidine + S-adenosyl-L-methioninamine = H+ + spermine + S-methyl-5'-thioadenosine spermine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.115 pelargonidin = H+ + UDP + pelargonidin-3-O-β-D-glucoside anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.114 2-coumarate = H+ + trans-β-D-Glucosyl-2-hydroxycinnamate + UDP coumarin biosynthesis (via 2-coumarate) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.134 D-myo-inositol (3,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.134 D-myo-inositol (3,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.18 H+ + L-glutamine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.80 octadecanal = H+ heptadecane biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.23 histidinol + NAD+ = H+ + histidinal + NADH histidine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.11 NADP+ + L-aspartate-semialdehyde = H+ + NADPH + L-aspartyl-4-phosphate lysine biosynthesis VI H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.11 NADP+ + L-aspartate-semialdehyde = H+ + NADPH + L-aspartyl-4-phosphate homoserine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.99.1.1 protoporphyrin IX + Fe2+ = protoheme IX + H+ heme biosynthesis from uroporphyrinogen-III I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.1.1 L-glutamate + acetyl-CoA = H+ + N-acetyl-L-glutamate + coenzyme A arginine biosynthesis II (acetyl cycle) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.1.1 L-glutamate + acetyl-CoA = H+ + N-acetyl-L-glutamate + coenzyme A ornithine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.14 D-fructose-6-phosphate = H+ + sucrose-6-phosphate + UDP sucrose biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.10.99.3 H+ + antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O antheraxanthin and violaxanthin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.10.99.3 H+ + antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.1.17 D-glucono-1,5-lactone + H2O = H+ + D-gluconate glucose and glucose-1-phosphate degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.151 D-myo-inositol (1,4,5)-trisphosphate + ATP = H+ + D-myo-inositol (1,4,5,6)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.151 D-myo-inositol (1,4,5)-trisphosphate + ATP = H+ + D-myo-inositol (1,4,5,6)-tetrakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.- GDP-α-D-mannose = H+ + GDP dolichyl-diphosphooligosaccharide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.44 4-coumaroyl-CoA + NADPH + H+ = coumaraldehyde + coenzyme A + NADP+ phenylpropanoid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.8 L-saccharopine + H2O + NADP+ = L-lysine + 2-oxoglutarate + NADPH + H+ lysine degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: N6-dimethylallyladenine + H2O = trans-zeatin + H+ trans-zeatin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.- dolichyl-diphosphooligosaccharide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.35 ATP + pyridoxamine = H+ + ADP + pyridoxamine 5'-phosphate pyridoxal 5'-phosphate salvage pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.143 24-methylenelophenol + S-adenosyl-L-methionine = H+ + 24-ethylidenelophenol + S-adenosyl-L-homocysteine plant sterol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.219 H+ + trans dihydroquercetin + NADPH = leucocyanidin + NADP+ leucopelargonidin and leucocyanidin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.2.2.14 nicotinamide mononucleotide + H2O = H+ + D-ribose-5-phosphate + nicotinamide pyridine nucleotide cycling (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.13.11.54 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one + oxygen = H+ + 2-oxo-4-methylthiobutanoate + formate methionine salvage I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: isorhamnetin 3-sulphate + phosphoadenosine-5'-phosphosulfate = H+ + adenosine 3',5'-bisphosphate + isorhamnetin 3, 4'-bisulphate quercetinsulphates biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.3 acetaldehyde + H2O + NAD+ = acetate + NADH + H+ ethanol degradation II (cytosol) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.3 acetaldehyde + H2O + NAD+ = acetate + NADH + H+ ethanol degradation IV (peroxisomal) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.2.4 γ-glutamyl cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.37 H+ + β-L-arabinose 1-phosphate + UTP = diphosphate UDP-L-arabinose biosynthesis II (from L-arabinose) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.2 5,6-dihydrothymine + NADP+ = thymine + NADPH + H+ thymine degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ chlorogenic acid biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ chlorogenic acid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ phenylpropanoid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.3.1.18 D-serine = H+ + pyruvate + ammonia serine racemization H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.1.32 H2O = H+ phospholipases H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.2.19 H+ + 5-phospho-α-D-ribose 1-diphosphate + quinolinate = CO2 + diphosphate + nicotinate mononucleotide NAD biosynthesis I (from aspartate) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.8 sn-glycerol-3-phosphate + NAD+ = dihydroxyacetone phosphate + NADH + H+ glycerol-3-phosphate shuttle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.15.1.1 superoxide + H+ = hydrogen peroxide + oxygen superoxide radicals degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + coumarinate = coumarin + H2O coumarin biosynthesis (via 2-coumarate) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.11.- H+ + GA44 + 2-oxoglutarate + oxygen = GA98 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.6.3 6-hydroxymethyl-7,8-dihydropterin + ATP = H+ + 6-hydroxymethyl-dihydropterin diphosphate + AMP 6-hydroxymethyl-dihydropterin diphosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine superpathway of 5-aminoimidazole ribonucleotide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.1 ethanol + NAD+ = acetaldehyde + NADH + H+ acetaldehyde biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.1 ethanol + NAD+ = acetaldehyde + NADH + H+ ethanol degradation II (cytosol) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.1 ethanol + NAD+ = acetaldehyde + NADH + H+ pyruvate fermentation to ethanol II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.1.110 feruloyl-CoA + tyramine = H+ + N-feruloyltyramine + coenzyme A suberin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.94 sn-glycerol-3-phosphate = dihydroxyacetone phosphate + H+ CDP-diacylglycerol biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.94 sn-glycerol-3-phosphate = dihydroxyacetone phosphate + H+ CDP-diacylglycerol biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.- 24-epi-campesterol + NADPH + H+ + oxygen = brassicasterol + NADP+ + H2O plant sterol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.6.3.14 H+ + H2O + ATP = H+ + ADP adenosine nucleotides de novo biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.1.2 L-glutamine + H2O = H+ + L-glutamate + ammonia glutamine degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.1.2 L-glutamine + H2O = H+ + L-glutamate + ammonia citrulline biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.99.12 N6-dimethylallyladenine + H+ + FAD + H2O = 3-methyl-2-butenal + adenine + FADH2 cytokinins degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.100 NADP+ = NADPH + H+ fatty acid elongation -- saturated H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.3 L-homoserine = L-aspartate-semialdehyde + H+ homoserine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.5 sulfate + H+ + ADP = adenosine 5'-phosphosulfate sulfite oxidation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + eriodictyol + NADPH + oxygen = luteolin + NADP+ + H2O luteolin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.19 tetrahydrofolate + trimethyl sulfonium = H+ + dimethylsulfide + 5-methyl-tetrahydrofolate folate transformations I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + naringenin + NADPH + oxygen = apigenin + NADP+ + H2O luteolin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.68 5-hydroxyferulate + S-adenosyl-L-methionine = H+ + sinapate + S-adenosyl-L-homocysteine free phenylpropanoid acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.27 (S)-methylmalonate-semialdehyde + coenzyme A + NAD+ + H2O = propanoyl-CoA + bicarbonate + NADH + H+ valine degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.70 NADPH + oxygen + obtusifoliol + H+ = H2O + NADP+ + formate + 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol plant sterol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.4.1.14 S-adenosyl-L-methionine = H+ + S-methyl-5'-thioadenosine + 1-aminocyclopropane-1-carboxylate ethylene biosynthesis from methionine H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.102 NADP+ + sphinganine = H+ + NADPH + 3-dehydrosphinganine sphingolipid biosynthesis (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.19 H+ + L-arginine = CO2 + agmatine arginine degradation III (arginine decarboxylase/agmatinase pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.19 H+ + L-arginine = CO2 + agmatine arginine dependent acid resistance H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.19 H+ + L-arginine = CO2 + agmatine putrescine biosynthesis IV H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.19 H+ + L-arginine = CO2 + agmatine putrescine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.19 H+ + L-arginine = CO2 + agmatine arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.- campesterol + NADP+ = H+ + crinosterol + NADPH plant sterol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.4.1.9 L-cysteine + hydrogen cyanide = hydrogen sulfide + 3-cyano-L-alanine + H+ cyanide detoxification H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.4.1.9 L-cysteine + hydrogen cyanide = hydrogen sulfide + 3-cyano-L-alanine + H+ cyanide degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.48 uridine + GTP = H+ + uridine-5'-phosphate + GDP salvage pathways of pyrimidine ribonucleotides H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.9.1 pyruvate + ATP = H+ + phosphoenolpyruvate + AMP + diphosphate glutamine biosynthesis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.9.1 pyruvate + ATP = H+ + phosphoenolpyruvate + AMP + diphosphate C4 photosynthetic carbon assimilation cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.90 D-fructose-6-phosphate + diphosphate = H+ + fructose-1,6-bisphosphate glycolysis IV (plant cytosol) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.68 5-hydroxy-coniferaldehyde + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + sinapaldehyde phenylpropanoid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.68 5-hydroxy-coniferaldehyde + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + sinapaldehyde ferulate and sinapate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.1.53 H+ + N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia putrescine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.1.53 H+ + N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide 5-aminoimidazole ribonucleotide biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide 5-aminoimidazole ribonucleotide biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide superpathway of 5-aminoimidazole ribonucleotide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.238 delphinidin-3,5-diglucoside = H+ + delphinidin 3,5,3'-triglucoside + UDP gentiodelphin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: (3Z)-hex-3-en-ol + NAD+ = cis-3-hexenal + NADH + H+ traumatin and (Z)-3-hexen-1-yl acetate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.- H+ + 2-oxo-3-carboxy-4,5-cyclopropylhex-5-enoate = beta-methylenecyclopropyl pyruvate + CO2 hypoglycin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.68 coniferaldehyde + H2O = ferulate + H+ ferulate and sinapate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP urea cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP arginine biosynthesis II (acetyl cycle) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP citrulline-nitric oxide cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP arginine biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.4 β-D-fructofuranose + ATP = H+ + D-fructose-6-phosphate + ADP sucrose degradation III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.4 β-D-fructofuranose + ATP = H+ + D-fructose-6-phosphate + ADP sucrose degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.1.74 H+ + 4-coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A flavonoid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.1.74 H+ + 4-coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A aromatic polyketides biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.2.3 (S)-dihydroorotate + H2O = H+ + N-carbamoyl-L-aspartate uridine-5'-phosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.19 H+ + L-arginine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.10 H+ + α-D-galactose 1-phosphate + UTP = UDP-D-galactose + diphosphate stachyose degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.10 H+ + α-D-galactose 1-phosphate + UTP = UDP-D-galactose + diphosphate galactose degradation III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.99.12 H+ + isobutyryl-CoA + FAD = methylacrylyl-CoA + FADH2 valine degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.3.7 indole acetaldehyde + oxygen + H2O = H+ + indole-3-acetate + hydrogen peroxide IAA biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.99.- 5-aminoimidazole ribonucleotide + S-adenosyl-L-methionine = hydroxymethylpyrimidine phosphate + 5'-deoxyadenosine + L-methionine + formate + carbon monoxide + H+ thiamine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.1.4 4-guanidinobutyramide + H2O = H+ + ammonia + 4-guanidinobutyrate arginine degradation X (arginine monooxygenase pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.2.9 5-oxoproline + H2O + ATP = H+ + L-glutamate + ADP γ-glutamyl cycle (plant pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.2.9 5-oxoproline + H2O + ATP = H+ + L-glutamate + ADP γ-glutamyl cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.35 NAD+ + OPC8-3-hydroxyacyl-CoA = NADH + H+ + OPC8-3-ketoacyl-CoA jasmonic acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.17.4 H+ + L-ascorbate + 1-aminocyclopropane-1-carboxylate + oxygen = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.1.1 methyl indole-3-acetate + H2O = H+ + indole-3-acetate + methanol methyl indole-3-acetate interconversion H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.4.1.8 L-cystathionine + H2O = H+ + ammonia + pyruvate + L-homocysteine methionine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.4.1.8 L-cystathionine + H2O = H+ + ammonia + pyruvate + L-homocysteine homocysteine and cysteine interconversion H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.11.1.11 H+ + L-ascorbate + hydrogen peroxide = monodehydroascorbate + H2O ascorbate glutathione cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: indole + acetate = H+ + indole-3-acetate IAA biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.2.1.104 cyanate + bicarbonate + H+ = carbamate + CO2 cyanate degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = H+ + ADP + 5-aminoimidazole ribonucleotide 5-aminoimidazole ribonucleotide biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = H+ + ADP + 5-aminoimidazole ribonucleotide 5-aminoimidazole ribonucleotide biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = H+ + ADP + 5-aminoimidazole ribonucleotide superpathway of 5-aminoimidazole ribonucleotide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.2.34 indol-3-yl-acetyl-myo-inositol = H+ + UDP + indole-3-yl-acetyl-myo-inositol L-arabinoside IAA conjugate biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.- 18-hydroxyoleate + NADP+ = H+ + 18-oxo-oleate + NADPH suberin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.99.12 H+ + trans-zeatin + H2O + FAD = adenine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.99.12 D-ribulose-5-phosphate = H+ + formate + 1-deoxy-L-glycero-tetrulose 4-phosphate flavin biosynthesis I (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.53 H+ + L-phenylalanine = 2-phenylethylamine + CO2 phenylethanol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.1 H+ + L-tyrosine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.8.5.1 L-dehydro-ascorbate + glutathione = H+ + glutathione disulfide + L-ascorbate ascorbate glutathione cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- 2-decaprenyl-6-methoxyphenol + oxygen + NADPH + H+ = 2-methoxy-6-all trans-decaprenyl-2-methoxy-1,4-benzoquinol + H2O + NADP+ ubiquinol-10 biosynthesis (eukaryotic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.25 adenosine 5'-phosphosulfate + ATP = H+ + phosphoadenosine-5'-phosphosulfate + ADP sulfate activation for sulfonation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.3.6 H2O + L-arginine = H+ + ammonia + L-citrulline proline biosynthesis II (from arginine) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.35 NAD+ + OPC4-3-hydroxyacyl-CoA = NADH + H+ + OPC4-3-ketoacyl-CoA jasmonic acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.114 3,4-dihydroxy-5-all-trans-nonaprenylbenzoate + S-adenosyl-L-methionine = H+ + 3-methoxy-4-hydroxy-5-all-trans-nonaprenylbenzoate + S-adenosyl-L-homocysteine ubiquinol-9 biosynthesis (eukaryotic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.2.2 H2O = coenzyme A + H+ acyl-CoA hydrolysis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.50 H+ + S-adenosyl-L-methionine = CO2 + S-adenosyl-L-methioninamine spermine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.50 H+ + S-adenosyl-L-methionine = CO2 + S-adenosyl-L-methioninamine spermidine biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline urea cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline arginine biosynthesis II (acetyl cycle) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline proline biosynthesis II (from arginine) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline citrulline degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline arginine biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline citrulline biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.100 NADP+ = NADPH + H+ stearate biosynthesis II (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.11.- H+ + GA44 (open lactone form) + 2-oxoglutarate + oxygen = GA38 + succinate + CO2 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.11.- leucodelphinidin + oxygen + 2-oxoglutarate = H+ + delphinidin + H2O + CO2 + succinate anthocyanin biosynthesis (delphinidin 3-O-glucoside) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.7 H+ + L-alanine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.4.1.2 ATP + acetyl-CoA + bicarbonate = H+ + malonyl-CoA + ADP fatty acid biosynthesis initiation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate = S-allantoin + CO2 urate degradation to allantoin H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.13 NADP+ + D-glyceraldehyde-3-phosphate = H+ + NADPH + 1,3-bisphospho-D-glycerate Calvin-Benson-Bassham cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.90 antheraxanthin + H+ + oxygen = violaxanthin + H2O antheraxanthin and violaxanthin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.90 antheraxanthin + H+ + oxygen = violaxanthin + H2O xanthophyll cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.35 NAD+ + OPC6-3-hydroxyacyl-CoA = NADH + H+ + OPC6-3-ketoacyl-CoA jasmonic acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.58 H+ + 2,3-dihydroxybenzoate + ATP = 2,3-dihydroxybenzoyl-AMP + diphosphate vibriobactin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.4.25 H2O + GTP = H+ + diphosphate + 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one + formate flavin biosynthesis I (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH superpathway of glyoxylate cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1-(3-aminopropyl)-pyrrolinium = H+ + 1,5-diazabicyclononane spermine and spermidine degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.3.9 acetyl-CoA + H2O + glyoxylate = H+ + (S)-malate + coenzyme A glyoxylate cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.3.9 acetyl-CoA + H2O + glyoxylate = H+ + (S)-malate + coenzyme A glycolate and glyoxylate degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.111 sinapyl-alcohol = H+ + syringin + UDP monolignol glucosides biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.2.1.9 H+ + isochorismate + 2-oxoglutarate = 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + CO2 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.83 3,7-di-O-methylquercetin + S-adenosyl-L-methionine = H+ + 3,7,4'-tri-O-methylquercetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.4 H+ + sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate reduction II (assimilatory) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.4 H+ + sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfite oxidation III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.4 H+ + sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate activation for sulfonation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.3 catechin + NADP+ + H2O = leucocyanidin + NADPH + H+ 2,3-trans-flavanols biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.2.1.6 H+ + pyruvate = (S)-2-acetolactate + CO2 valine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.86 2,3-dihydroxy-isovalerate + NADP+ = (S)-2-acetolactate + NADPH + H+ valine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.50 coenzyme A + NADP+ = NADPH + H+ cuticular wax biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- H+ + coniferaldehyde + NADPH + oxygen = 5-hydroxy-coniferaldehyde + NADP+ + H2O phenylpropanoid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- H+ + coniferaldehyde + NADPH + oxygen = 5-hydroxy-coniferaldehyde + NADP+ + H2O ferulate and sinapate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.- 2-methyl-6-phytyl-1,4-benzoquinol + S-adenosyl-L-methionine = H+ + 2,3-dimethyl-6-phytyl-1,4-benzoquinol + S-adenosyl-L-homocysteine vitamin E biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.68 sinapaldehyde + NADP+ + H2O = H+ + sinapate + NADPH ferulate and sinapate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.11.- GA34 + 2-oxoglutarate + oxygen = H+ + GA34-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 5,10-methenyltetrahydrofolate + H2O = H+ + 5-formyl-tetrahydrofolate folate transformations II (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.8 betaine aldehyde + NAD+ + H2O = H+ + glycine betaine + NADH glycine betaine biosynthesis III (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.11.- GA51 + 2-oxoglutarate + oxygen = H+ + GA51-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- H+ + N,N-dihydroxy-L-tryptophan = (E)-indol-3-ylacetaldoxime + CO2 + H2O IAA biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate = H+ + 2-oxo-3-carboxy-4,5-cyclopropylhex-5-enoate hypoglycin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.2.23 4-hydroxybenzoyl-CoA + H2O = H+ + coenzyme A 4-hydroxybenzoate biosynthesis V H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.-.- H+ + 6-deoxocathasterone + oxygen = 6-deoxoteasterone + H2O brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.15 H+ + L-proline + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.8.8 L-serine = CMP + H+ phospholipid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.8.8 L-serine = CMP + H+ phosphatidylethanolamine biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.2 L-proline = (S)-1-pyrroline-5-carboxylate + H+ arginine degradation VI (arginase 2 pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.2 L-proline = (S)-1-pyrroline-5-carboxylate + H+ proline biosynthesis II (from arginine) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.2 L-proline = (S)-1-pyrroline-5-carboxylate + H+ proline biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis II (acetyl cycle) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate uridine-5'-phosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: N6-(Δ2-isopentenyl)-adenosine 5'-diphosphate + NADPH + H2O = H+ + trans-zeatin riboside diphosphate + NADP+ trans-zeatin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: D-myo-inositol (3,4,6)-trisphosphate + ATP = H+ + D-myo-inositol (3,4,5,6)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.65 H+ = CO2 phosphatidylethanolamine biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.- L-galactose + NAD+ = H+ + L-galactono-1,4-lactone + NADH ascorbate biosynthesis I (L-galactose pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.2 H+ + FMN + ATP = FAD + diphosphate flavin biosynthesis I (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- laurate + oxygen + NADPH + H+ = ω-hydroxylaurate + NADP+ + H2O ω-hydroxylation of caprate and laurate H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.1.170 H+ + 4-coumaroyl-CoA + malonyl-CoA + NADPH = isoliquiritigenin + coenzyme A + CO2 + NADP+ + H2O flavonoid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.17 D-xylulose + ATP = H+ + D-xylulose-5-phosphate + ADP xylose degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.10 H+ + L-methionine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.16 H+ + L-cysteine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.98 S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + H+ diphthamide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.35 NAD+ = NADH + H+ fatty acid β-oxidation II (core pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.2.11 5,10-methylenetetrahydropteroyl mono-L-glutamate + 2-oxoisovalerate + H2O = H+ + 2-dehydropantoate + tetrahydrofolate phosphopantothenate biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.2.11 5,10-methylenetetrahydropteroyl mono-L-glutamate + 2-oxoisovalerate + H2O = H+ + 2-dehydropantoate + tetrahydrofolate pantothenate biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.1.- p-dihydrocoumaroyl-CoA + malonyl-CoA + H+ = phloretin + coenzyme A + CO2 phloridzin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.75 H+ + divinyl protochlorophyllide a + NADPH = monovinyl protochlorophyllide a + NADP+ chlorophyllide a biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.3.9 H+ + oxygen + NADPH + loganin = H2O + NADP+ + secologanin camptothecin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.- sitosterol + NADPH + H+ + oxygen = stigmasterol + NADP+ + H2O plant sterol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.9 H+ + L-valine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.13 H+ + α-D-mannose 1-phosphate + GTP = GDP-α-D-mannose + diphosphate ascorbate biosynthesis I (L-galactose pathway) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.13 H+ + α-D-mannose 1-phosphate + GTP = GDP-α-D-mannose + diphosphate GDP-mannose biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.49 β-D-glucose-6-phosphate + NADP+ = 6-phospho-D-glucono-1,5-lactone + NADPH + H+ pentose phosphate pathway (oxidative branch) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.24 dephospho-CoA + ATP = H+ + coenzyme A + ADP coenzyme A biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.9 NAD+ = NADH + H+ palmitate biosynthesis II (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.8.2.27 quercetin 3-sulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin-3,4'-bissulfate quercetinsulphates biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + (22S,24R)-22-hydroxy-5α-ergostan-3-one = 3-epi-6-deoxocathasterone brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.- dolichyl-diphosphooligosaccharide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.4.3.5 oxygen + H2O + pyridoxamine 5'-phosphate = H+ + ammonia + hydrogen peroxide + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.288 xanthoxin + NAD+ = abscisic aldehyde + NADH + H+ abscisic acid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.86 NADH + ATP = H+ + NADPH + ADP NAD/NADH phosphorylation and dephosphorylation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.20 H+ + meso-diaminopimelate = CO2 + L-lysine lysine biosynthesis VI H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.22 H+ + L-asparagine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.43 S-adenosyl-L-methionine = H+ + nicotianamine + S-methyl-5'-thioadenosine 2'-deoxymugineic acid phytosiderophore biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.43 S-adenosyl-L-methionine = H+ + nicotianamine + S-methyl-5'-thioadenosine nicotianamine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.282 shikimate = 3-dehydroshikimate + H+ chorismate biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- H+ + (5α)-campestan-3-one + oxygen + NADPH = (22S,24R)-22-hydroxy-5α-ergostan-3-one + H2O + NADP+ brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.219 H+ + dihydromyricetin + NADPH = leucodelphinidin + NADP+ leucodelphinidin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.6.1.1 H2O + diphosphate = H+ UDP-glucose biosynthesis (from glucose 6-phosphate) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.95 γ-tocopherol + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + α-tocopherol vitamin E biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.8.1.7 glutathione + NADP+ = glutathione disulfide + NADPH + H+ glutathione redox reactions I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.8.1.7 glutathione + NADP+ = glutathione disulfide + NADPH + H+ glutathione redox reactions II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.43 ATP = H+ + α-D-glucuronate 1-phosphate + ADP UDP-D-glucuronate biosynthesis (from myo-inositol) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH glyoxylate cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH gluconeogenesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH TCA cycle variation III (eukaryotic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH aspartate degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate + NADPH + H2O = H+ + trans-zeatin riboside monophosphate + NADP+ trans-zeatin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.- avenastenone + NADPH + H+ = avenasterol + NADP+ plant sterol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.35 ATP + pyridoxal = H+ + ADP + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.8.1.4 NAD+ = NADH + H+ 2-ketoglutarate dehydrogenase complex H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.2.1.91 H+ + L-arogenate = CO2 + H2O + L-phenylalanine phenylalanine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.4.3.10 oxygen + H2O + putrescine = H+ + ammonia + hydrogen peroxide + 4-aminobutanal putrescine degradation IV H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.3 H+ + L-threonine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = H+ + L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.4 H+ + L-leucine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: H+ + homogentisate + phytyl diphosphate = 2-methyl-6-phytyl-1,4-benzoquinol + CO2 + diphosphate vitamin E biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.78 ent-kaurenol + NADPH + H+ + oxygen = ent-kaurenal + NADP+ + H2O GA12 biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.15.7 choline + oxygen + H+ = betaine aldehyde hydrate + H2O glycine betaine biosynthesis III (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.100 NADPH + H+ = NADP+ palmitate biosynthesis II (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4-coumaroyl-CoA + NADPH + FADH2 = p-dihydrocoumaroyl-CoA + NADP+ + FAD + H+ phloridzin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.- NADPH + H+ = NADP+ + coenzyme A cuticular wax biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.16 putrescine + S-adenosyl-L-methioninamine = H+ + spermidine + S-methyl-5'-thioadenosine spermidine biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.99.12 H+ + isopentenyl adenosine + H2O + FAD = adenosine + 3-methyl-2-butenal + FADH2 cytokinins degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.61 H2O + porphobilinogen = H+ + ammonia + hydroxymethylbilane tetrapyrrole biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.2 dimethylallyl diphosphate + H2O = 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H+ methylerythritol phosphate pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.79 succinate semialdehyde + NADP+ + H2O = succinate + NADPH + H+ 4-aminobutyrate degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.30 H+ + β-L-fucose 1-phosphate + GTP = GDP-L-fucose + diphosphate GDP-L-fucose biosynthesis II (from L-fucose) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.13.99.1 oxygen + myo-inositol = H+ + H2O UDP-D-glucuronate biosynthesis (from myo-inositol) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.- 2-methoxy-6-all trans-nonaprenyl-2-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine = H+ + 6-methoxy-5-methyl-2-all-trans-nonaprenyl-1,4-benzoquinol + S-adenosyl-L-homocysteine ubiquinol-9 biosynthesis (eukaryotic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.154 S-(-)-ureidoglycolate = oxalurate + H+ allantoin degradation IV (anaerobic) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.6.5.3 H+ + NADH = NAD+ NADH to cytochrome bd oxidase electron transfer H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.6.5.3 H+ + NADH = NAD+ aerobic respiration -- electron donor II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.6.5.3 H+ + NADH = NAD+ NAD/NADH phosphorylation and dephosphorylation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.15 H+ + L-glutamate = CO2 + 4-aminobutyrate glutamate degradation III (via 4-aminobutyrate) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.15 H+ + L-glutamate = CO2 + 4-aminobutyrate glutamate degradation IX (via 4-aminobutyrate) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.15 H+ + L-glutamate = CO2 + 4-aminobutyrate glutamate dependent acid resistance H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.4.16 GTP + H2O = H+ + formate + 7,8-dihydroneopterin triphosphate 6-hydroxymethyl-dihydropterin diphosphate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.70 4α-methyl-5α-ergosta-8,14,24(28)-dien-3β-ol + NADP+ = 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol + NADPH + H+ plant sterol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.20 5-methyl-tetrahydrofolate + NAD+ = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H+ + NADH folate transformations I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.20 5-methyl-tetrahydrofolate + NAD+ = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H+ + NADH folate transformations II (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.10 L-homocysteine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + L-methionine methionine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.- H+ + geranylgeranyl-chlorophyll a + NADPH = dihydrogeranylgeranyl-chlorophyll a + NADP+ chlorophyll a biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.4.1.2 H2O + NAD+ + L-glutamate = H+ + ammonia + NADH + 2-oxoglutarate glutamate degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.4.1.2 H2O + NAD+ + L-glutamate = H+ + ammonia + NADH + 2-oxoglutarate alanine degradation II (to D-lactate) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.6.1 ATP + D-ribose-5-phosphate = H+ + 5-phospho-α-D-ribose 1-diphosphate + AMP PRPP biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP GDP-glucose biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP glycolysis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP trehalose degradation II (trehalase) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP glucose and glucose-1-phosphate degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP glycogen degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.3.3.13 2-oxoisovalerate + acetyl-CoA + H2O = H+ + (2S)-2-isopropylmalate + coenzyme A leucine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.- dolichyl-diphosphooligosaccharide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.20 H+ + L-phenylalanine + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.15 H+ + phosphoryl-choline + CTP = CDP-choline + diphosphate phosphatidylcholine biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.15 H+ + phosphoryl-choline + CTP = CDP-choline + diphosphate choline biosynthesis III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.15 H+ + phosphoryl-choline + CTP = CDP-choline + diphosphate phosphatidylcholine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.203 trans-zeatin = H+ + trans-zeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.112 (22S,24R)-22-hydroxy-5α-ergostan-3-one + oxygen + NADPH + H+ = 3-dehydro-6-deoxoteasterone + NADP+ + H2O brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.90 zeaxanthin + H+ + oxygen = antheraxanthin + H2O antheraxanthin and violaxanthin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.90 zeaxanthin + H+ + oxygen = antheraxanthin + H2O xanthophyll cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.91 sphinganine + ATP = H+ + sphinganine 1-phosphate + ADP sphingolipid biosynthesis (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.- D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + 1D-myo-inositol (1,2,3,4,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.1.10 H2O + 10-formyl-tetrahydrofolate = H+ + tetrahydrofolate + formate folate transformations I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: DMSP-amine + oxygen + H2O = H+ + 3-dimethylsulfoniopropionaldehyde + ammonia + hydrogen peroxide dimethylsulfoniopropionate biosynthesis II (Spartina) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: O-acetyl-L-homoserine + L-cysteine = H+ + L-cystathionine + acetate homocysteine and cysteine interconversion H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.82 ethanolamine + ATP = H+ + phosphoryl-ethanolamine + ADP phosphatidylethanolamine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.82 ethanolamine + ATP = H+ + phosphoryl-ethanolamine + ADP choline biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: diphosphate = UTP + H+ stachyose degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.131 GDP-α-D-mannose = GDP + H+ dolichyl-diphosphooligosaccharide biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: N-hydroxyl-tryptamine = H+ + (E)-indol-3-ylacetaldoxime IAA biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.79 ent-7-α-hydroxykaurenoate + NADPH + H+ + oxygen = GA12-aldehyde + NADP+ + H2O GA12 biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.7.1.1 nitrite + H2O + NAD+ = H+ + nitrate + NADH nitrate reduction II (assimilatory) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.31 (S)-3-hydroxy-isobutyrate + NAD+ = H+ + NADH + (S)-methylmalonate-semialdehyde valine degradation I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.81 magnesium-protoporphyrin IX 13-monomethyl ester + oxygen + NADPH + H+ = 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.195 H+ + coumaraldehyde + NADPH = coumaryl-alcohol + NADP+ phenylpropanoid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.9.2 H2O + pyruvate + ATP = H+ + phosphoenolpyruvate + AMP gluconeogenesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.9.2 H2O + pyruvate + ATP = H+ + phosphoenolpyruvate + AMP glycolysis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.29 D-glycerate + NAD+ = H+ + hydroxypyruvate + NADH photorespiration H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.78 H+ + ent-kaurene + oxygen + NADPH = H2O + NADP+ + ent-kaurenol GA12 biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.1 H+ + phenylacetaldehyde + NADH = 2-phenylethanol + NAD+ phenylethanol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate glycogen biosynthesis II (from UDP-D-Glucose) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate sucrose degradation III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate stachyose degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate UDP-glucose biosynthesis (from glucose 6-phosphate) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate colanic acid building blocks biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate galactose degradation III H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate sucrose biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.1.14 chlorophyll a + H2O = H+ + chlorophyllide a + phytol chlorophyll a degradation H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.31 Δ1-piperideine-6-carboxylate + NAD+ + H2O = 2-aminoadipate + NADH + H+ lysine degradation II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.- H+ + campest-4-en-3-one + oxygen + NADPH = (22α)-hydroxy-campest-4-en-3-one + H2O + NADP+ brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.3.- S-ureidoglycine + H2O = H+ + ammonia + S-(-)-ureidoglycolate allantoin degradation to ureidoglycolate II (ammonia producing) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = H+ + adenylo-succinate + GDP purine nucleotides de novo biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = H+ + adenylo-succinate + GDP adenosine nucleotides de novo biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.7.3 H+ + 4'-phosphopantetheine + ATP = dephospho-CoA + diphosphate coenzyme A biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.23 methylglyoxal + NAD+ + H2O = H+ + pyruvate + NADH methylglyoxal degradation VII H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.3.2.5 D-4'-phosphopantothenate + L-cysteine + CTP = H+ + R-4'-phosphopantothenoyl-L-cysteine + diphosphate + CMP coenzyme A biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.28 benzaldehyde + H2O + NAD+ = benzoate + NADH + H+ benzoate biosynthesis III (CoA-dependent, non-β-oxidative) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.28 benzaldehyde + H2O + NAD+ = benzoate + NADH + H+ benzoate biosynthesis II (CoA-independent, non-β-oxidative) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 6.1.1.12 H+ + L-aspartate + ATP = diphosphate + AMP tRNA charging pathway H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.4.3.21 2-phenylethylamine + oxygen + H2O = H+ + phenylacetaldehyde + ammonia + hydrogen peroxide phenylethanol biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.1.2.4 3-hydroxypropanoyl-CoA + H2O = H+ + 3-hydroxypropionate + coenzyme A β-alanine biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.9 D-glyceraldehyde-3-phosphate + NADP+ + H2O = H+ + 3-phospho-D-glycerate + NADPH glycolysis IV (plant cytosol) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.100 ATP + S-methyl-5-thio-D-ribose = H+ + ADP + 5-methylthioribose-1-phosphate methionine salvage I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.6.1.22 H2O + NAD+ = H+ + nicotinamide mononucleotide + AMP pyridine nucleotide cycling (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.39 D-ribulose-1,5-bisphosphate + CO2 + H2O = 3-phospho-D-glycerate + H+ Rubisco shunt H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.39 D-ribulose-1,5-bisphosphate + CO2 + H2O = 3-phospho-D-glycerate + H+ Calvin-Benson-Bassham cycle H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.7.1.- cytidine + GTP = H+ + CMP + GDP salvage pathways of pyrimidine ribonucleotides H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.1.20 H+ + L-citrulline + H2O = L-ornithine + CO2 + ammonia proline biosynthesis II (from arginine) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.100 NADP+ = NADPH + H+ petroselinate biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.9 NAD+ = NADH + H+ stearate biosynthesis II (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 5-(methylthio)-2,3-dioxopentyl phosphate = H+ + 2-hydroxy-3-keto-5-methylthio-1-phosphopentene methionine salvage I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 5.3.-.- H+ + 3-(2-propenoic acid)-4,6-hydroxy cyclohexa-2,5-dienone = 3,4,6-trihydroxy-cis-cinnamate esculetin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O chlorogenic acid biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O chlorogenic acid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O simplecoumarins biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O phenylpropanoid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.99.- H+ + (22α)-hydroxy-campest-4-en-3-one + NADPH = (22S,24R)-22-hydroxy-5α-ergostan-3-one + NADP+ brassinosteroid biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 3.6.1.31 phosphoribosyl-ATP + H2O = 1-(5-phospho-D-ribosyl)-AMP + diphosphate + H+ histidine biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.28 (R)-lactate + NAD+ = pyruvate + NADH + H+ alanine degradation II (to D-lactate) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.- H+ + dihydrogeranylgeranyl-chlorophyll a + NADPH = tetrahydrogeranylgeranyl-chlorophyll a + NADP+ chlorophyll a biosynthesis II H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.2.11 nicotinate mononucleotide + diphosphate = H+ + nicotinate + 5-phospho-α-D-ribose 1-diphosphate pyridine nucleotide cycling (plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.5.1.78 5-amino-6-(D-ribitylamino)uracil + 1-deoxy-L-glycero-tetrulose 4-phosphate = H+ + 6,7-dimethyl-8-(1-D-ribityl)lumazine + H2O flavin biosynthesis I (bacteria and plants) H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 4.2.1.24 5-amino-levulinate = H+ + H2O + porphobilinogen tetrapyrrole biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.4.1.- delphinidin-3-O-β-D-glucoside = H+ + delphinidin-3,5-diglucoside + UDP gentiodelphin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = H+ + feruloyl-CoA + S-adenosyl-L-homocysteine chlorogenic acid biosynthesis I H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = H+ + feruloyl-CoA + S-adenosyl-L-homocysteine suberin biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = H+ + feruloyl-CoA + S-adenosyl-L-homocysteine phenylpropanoid biosynthesis H+ hydrogen ion*proton*H H1 [H+] PUBCHEM:1038:*CHEBI:15378:*PUBCHEM:1038:*CHEBI:24636*LIGAND-CPD:C00080*PUBCHEM:1038*CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.33 chlorophyllide a + NADP+ = H+ + monovinyl protochlorophyllide a + NADPH chlorophyllide a biosynthesis I gibberellin A8 gibberellin A8*gibberellin A8*GA8*GA8*2β-hydroxygibberellin 1 363.386 C19 H23 O7 C1(C(C(C2(C4(C1(OC2=O)C5(CCC3(CC(CC3=C)(C4C([O-])=O)5)O)))(C))O)O) PUBCHEM:25203521:*LIGAND-CPD:C03579: 1.14.11.- gibberellin A8 + 2-oxoglutarate + oxygen = H+ + GA8-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) gibberellin A8 gibberellin A8*gibberellin A8*GA8*GA8*2β-hydroxygibberellin 1 363.386 C19 H23 O7 C1(C(C(C2(C4(C1(OC2=O)C5(CCC3(CC(CC3=C)(C4C([O-])=O)5)O)))(C))O)O) PUBCHEM:25203521:*LIGAND-CPD:C03579: 1.14.11.13 gibberellin A1 + 2-oxoglutarate + oxygen = gibberellin A8 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) OPC8-trans-2-enoyl-CoA 1037.905 C39 H58 N7 O18 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)=CCCCCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237209: 4.2.1.17 OPC8-3-hydroxyacyl-CoA = OPC8-trans-2-enoyl-CoA + H2O jasmonic acid biosynthesis OPC8-trans-2-enoyl-CoA 1037.905 C39 H58 N7 O18 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)=CCCCCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237209: 1.3.3.6 OPC8-CoA + oxygen = OPC8-trans-2-enoyl-CoA + hydrogen peroxide jasmonic acid biosynthesis OPC6-3-ketoacyl-CoA 1025.85 C37 H54 N7 O19 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)C(=O)CCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237277: 1.1.1.35 NAD+ + OPC6-3-hydroxyacyl-CoA = NADH + H+ + OPC6-3-ketoacyl-CoA jasmonic acid biosynthesis OPC6-3-ketoacyl-CoA 1025.85 C37 H54 N7 O19 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)C(=O)CCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237277: 2.3.1.16 OPC6-3-ketoacyl-CoA + coenzyme A = acetyl-CoA + OPC4-CoA jasmonic acid biosynthesis dihydroxyphaseic acid (-)-dihydroxyphaseic acid*DPA 281.328 C15 H21 O5 C1(C2(C(C(CC1O)(C)OC2)(C=CC(=CC([O-])=O)C)O)(C)) PUBCHEM:25245414:*LIGAND-CPD:C15971: 1.-.-.- phaseic acid = dihydroxyphaseic acid phaseic acid biosynthesis ubiquinol-8 ubiquinol(8) 729.137 C49 H76 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(=C(C)C(O)=C(OC)C(OC)=C(O)1) PUBCHEM:25074411: 1.1.5.3 sn-glycerol-3-phosphate + ubiquinone-8 = ubiquinol-8 + dihydroxyacetone phosphate glycerol degradation I 2-methyl-crotonyl-CoA 2-methylcrotonoyl-CoA*methylcrotonoyl-CoA*(E)-2-Methylcrotonoyl-CoA*trans-2-Methylbut-2-enoyl-CoA*2-Methylbut-2-enoyl-CoA*methylcrotonyl-CoA*trans-2-methylbut-2-enoyl-CoA*2-methylbut-2-enoyl-CoA*tigloyl-CoA*tiglyl-CoA*(E)-2-methylcrotonoyl-CoA 845.604 C26 H38 N7 O17 P3 S1 CC=C(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(OP(=O)([O-])[O-])1)N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25244790:*CAS:6247-62-7*LIGAND-CPD:C03345: 1.3.99.12 H+ + 2-methylbutanoyl-CoA + FAD = 2-methyl-crotonyl-CoA + FADH2 isoleucine degradation I 2-methyl-crotonyl-CoA 2-methylcrotonoyl-CoA*methylcrotonoyl-CoA*(E)-2-Methylcrotonoyl-CoA*trans-2-Methylbut-2-enoyl-CoA*2-Methylbut-2-enoyl-CoA*methylcrotonyl-CoA*trans-2-methylbut-2-enoyl-CoA*2-methylbut-2-enoyl-CoA*tigloyl-CoA*tiglyl-CoA*(E)-2-methylcrotonoyl-CoA 845.604 C26 H38 N7 O17 P3 S1 CC=C(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(OP(=O)([O-])[O-])1)N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25244790:*CAS:6247-62-7*LIGAND-CPD:C03345: 4.2.1.17 2-methyl-3-hydroxybutyryl-CoA = 2-methyl-crotonyl-CoA + H2O isoleucine degradation I D-myo-inositol (1,2,4,5,6)-pentakisphosphate 1D-myo-inositol 1,2,4,5,6-pentakisphosphate*myo-inositol 1,2,4,5,6-pentakisphosphate*inositol 1,2,4,5,6-pentakisphosphate*Ins(1,2,4,5,6)P5 569.977 C6 H7 O21 P5 C1(OP([O-])([O-])=O)(C(OP([O-])([O-])=O)C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:25202636:*CHEBI:57798:*PUBCHEM:25245416:*LIGAND-CPD:C04563:*CAS:20298-95-7 2.7.1.- D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,2,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) D-myo-inositol (1,2,4,5,6)-pentakisphosphate 1D-myo-inositol 1,2,4,5,6-pentakisphosphate*myo-inositol 1,2,4,5,6-pentakisphosphate*inositol 1,2,4,5,6-pentakisphosphate*Ins(1,2,4,5,6)P5 569.977 C6 H7 O21 P5 C1(OP([O-])([O-])=O)(C(OP([O-])([O-])=O)C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:25202636:*CHEBI:57798:*PUBCHEM:25245416:*LIGAND-CPD:C04563:*CAS:20298-95-7 3.1.3.8 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + H2O = D-myo-inositol (1,2,4,5,6)-pentakisphosphate phytate degradation I D-myo-inositol (1,2,4,5,6)-pentakisphosphate 1D-myo-inositol 1,2,4,5,6-pentakisphosphate*myo-inositol 1,2,4,5,6-pentakisphosphate*inositol 1,2,4,5,6-pentakisphosphate*Ins(1,2,4,5,6)P5 569.977 C6 H7 O21 P5 C1(OP([O-])([O-])=O)(C(OP([O-])([O-])=O)C(OP([O-])(=O)[O-])C(OP([O-])(=O)[O-])C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:25202636:*CHEBI:57798:*PUBCHEM:25245416:*LIGAND-CPD:C04563:*CAS:20298-95-7 D-myo-inositol (1,2,4,5,6)-pentakisphosphate + H2O = D-myo-inositol (1,2,5,6) tetrakisphosphate phytate degradation I 1,8-cineole cineole*1,8-epoxy-p-menthane*1,8-oxido-p-menthane*eucalyptol*cajeputol 154.252 C10 H18 O1 CC12(CCC(CC1)C(C)(C)O2) PUBCHEM:2758:*CHEBI:27961:*LIGAND-CPD:C09844: (-)-α-terpineol = 1,8-cineole monoterpene biosynthesis S-methyl-5-thio-D-ribose 5-methylthioribose*S5-methyl-5-thio-D-ribose*5-methylthio-D-ribose*MTR*S-methyl-5-thio-D-ribose 180.218 C6 H12 O4 S1 C1(C(OC(C1O)CSC)O)O PUBCHEM:494:*PUBCHEM:439904:*LIGAND-CPD:C03089: 3.2.2.16 S-methyl-5'-thioadenosine + H2O = S-methyl-5-thio-D-ribose + adenine methylthioadenosine degradation S-methyl-5-thio-D-ribose 5-methylthioribose*S5-methyl-5-thio-D-ribose*5-methylthio-D-ribose*MTR*S-methyl-5-thio-D-ribose 180.218 C6 H12 O4 S1 C1(C(OC(C1O)CSC)O)O PUBCHEM:494:*PUBCHEM:439904:*LIGAND-CPD:C03089: 3.2.2.16 S-methyl-5'-thioadenosine + H2O = S-methyl-5-thio-D-ribose + adenine methionine salvage I S-methyl-5-thio-D-ribose 5-methylthioribose*S5-methyl-5-thio-D-ribose*5-methylthio-D-ribose*MTR*S-methyl-5-thio-D-ribose 180.218 C6 H12 O4 S1 C1(C(OC(C1O)CSC)O)O PUBCHEM:494:*PUBCHEM:439904:*LIGAND-CPD:C03089: 2.7.1.100 ATP + S-methyl-5-thio-D-ribose = H+ + ADP + 5-methylthioribose-1-phosphate methionine salvage I GA29-catabolite gibberellin A29-catabolite*gibberellin A29-catabolite*GA29-catabolite 344.363 C19 H20 O6 C1(C(CC(C2(C(C34(CC(CCC(C=12)3)(C(C4)=C)O))C([O-])=O))(C)C([O-])=O)=O) PUBCHEM:25200854:*LIGAND-CPD:C11855: 1.14.11.- GA29 + 2-oxoglutarate + oxygen = H+ + GA29-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) D-myo-inositol (1,4)-bisphosphate Ins(1,4)P2*myo-inositol (1,4)-bisphosphate*inositol (1,4)-bisphosphate*I(1,4)P2 336.085 C6 H10 O12 P2 [O-]P([O-])(=O)OC1(C(O)C(O)C(OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:25203530:*LIGAND-CPD:C01220:*CAS:47055-78-7 3.1.3.56 H2O + D-myo-inositol (1,4,5)-trisphosphate = D-myo-inositol (1,4)-bisphosphate D-myo-inositol (1,4,5)-trisphosphate degradation D-myo-inositol (1,4)-bisphosphate Ins(1,4)P2*myo-inositol (1,4)-bisphosphate*inositol (1,4)-bisphosphate*I(1,4)P2 336.085 C6 H10 O12 P2 [O-]P([O-])(=O)OC1(C(O)C(O)C(OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:25203530:*LIGAND-CPD:C01220:*CAS:47055-78-7 3.1.3.57 D-myo-inositol (1,4)-bisphosphate + H2O = 1D-myo-inositol (4)-monophosphate D-myo-inositol (1,4,5)-trisphosphate degradation 12-oxo-cis-10,15-phytodienoate 12-oxo-cis-10,15-phytodienoic acid*oxophytodienoic acid*(15Z)-12-oxophyto-10,15-dienoate*12-oxo-phytodienoic acid*OPDA 291.409 C18 H27 O3 C1(C(CCCCCCCC([O-])=O)C(CC=CCC)C(=O)C=1) PUBCHEM:25246059:*PUBCHEM:25246059:*LIGAND-CPD:C01226: 5.3.99.6 12,13(S)-epoxylinolenate = 12-oxo-cis-10,15-phytodienoate jasmonic acid biosynthesis 12-oxo-cis-10,15-phytodienoate 12-oxo-cis-10,15-phytodienoic acid*oxophytodienoic acid*(15Z)-12-oxophyto-10,15-dienoate*12-oxo-phytodienoic acid*OPDA 291.409 C18 H27 O3 C1(C(CCCCCCCC([O-])=O)C(CC=CCC)C(=O)C=1) PUBCHEM:25246059:*PUBCHEM:25246059:*LIGAND-CPD:C01226: 1.3.1.42 NADP+ + 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate = H+ + NADPH + 12-oxo-cis-10,15-phytodienoate jasmonic acid biosynthesis 2-decaprenyl-6-methoxyphenol 805.321 C57 H88 O2 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(C=CC=C(OC)C=1O))C)C)C)C)C)C)C)CCC=C(C)CCC=C(C)C PUBCHEM:25010760:*CHEBI:50774: 1.14.13.- 2-decaprenyl-6-methoxyphenol + oxygen + NADPH + H+ = 2-methoxy-6-all trans-decaprenyl-2-methoxy-1,4-benzoquinol + H2O + NADP+ ubiquinol-10 biosynthesis (eukaryotic) 2-decaprenyl-6-methoxyphenol 805.321 C57 H88 O2 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(C=CC=C(OC)C=1O))C)C)C)C)C)C)C)CCC=C(C)CCC=C(C)C PUBCHEM:25010760:*CHEBI:50774: 4.1.1.- H+ + 3-methoxy-4-hydroxy-5-all-trans-decaprenylbenzoate = 2-decaprenyl-6-methoxyphenol + CO2 ubiquinol-10 biosynthesis (eukaryotic) 5-hydroxyferulate 5-hydroxy ferulate*5-hydroxy ferulic acid 209.178 C10 H9 O5 C1(C=CC([O-])=O)(=CC(OC)=C(O)C(O)=C1) PUBCHEM:25245419:*LIGAND-CPD:C05619: H+ + ferulate + NADPH + oxygen = 5-hydroxyferulate + H2O + NADP+ free phenylpropanoid acid biosynthesis 5-hydroxyferulate 5-hydroxy ferulate*5-hydroxy ferulic acid 209.178 C10 H9 O5 C1(C=CC([O-])=O)(=CC(OC)=C(O)C(O)=C1) PUBCHEM:25245419:*LIGAND-CPD:C05619: 2.1.1.68 5-hydroxyferulate + S-adenosyl-L-methionine = H+ + sinapate + S-adenosyl-L-homocysteine free phenylpropanoid acid biosynthesis 6-kestotriose 6-kestose*2,6-β-D-Fructan 504.441 C18 H32 O16 C2(OC1(OC(C(O)C(C1O)O)CO))(C(C(O)C(O2)COC3(OC(CO)C(O)C3O)(CO))O)(CO) PUBCHEM:9914062:*LIGAND-CPD:G02540: 2.4.1.10 sucrose + sucrose = 6-kestotriose + β-D-glucose fructan biosynthesis caprate n-decanoate*decanoic acid*decanoate*n-capric acid*caprinic acid*caprinate 171.259 C10 H19 O2 CCCCCCCCCC(=O)[O-] PUBCHEM:4678093:*CHEBI:27689:*CAS:334-48-5:*LIGAND-CPD:C01571: 3.1.2.2 decanoyl-CoA + H2O = H+ + caprate + coenzyme A ω-hydroxylation of caprate and laurate caprate n-decanoate*decanoic acid*decanoate*n-capric acid*caprinic acid*caprinate 171.259 C10 H19 O2 CCCCCCCCCC(=O)[O-] PUBCHEM:4678093:*CHEBI:27689:*CAS:334-48-5:*LIGAND-CPD:C01571: caprate + NADP+ + OH- = ω-hydroxycaprate + NADPH ω-hydroxylation of caprate and laurate C25-allenic-apo-aldehyde (3S,5R,6R)-3,5-dihydroxy-6,7-didehydro-5,6-dihydro-12'-apo-β-caroten-12'-al 382.542 C25 H34 O3 C(=C1(C(O)(C)CC(O)CC(C)(C)1))=CC(C)=CC=CC(C)=CC=CC=C(C)C=O PUBCHEM:25245424:*LIGAND-CPD:C14044: 1.13.11.51 9'-cis-neoxanthin + oxygen = xanthoxin + C25-allenic-apo-aldehyde abscisic acid biosynthesis urate 8-hydroxyxanthine*2,6,8-trihydroxypurine*trioxopurine*2,6,8-trioxypurine*purine-2,6,8-(1H,3H,9H)-trione*uric acid 168.112 C5 H4 N4 O3 O=C2(C1(=C(NC(=O)N1)[N-]C(O)[N-]2)) PUBCHEM:44229235:*PUBCHEM:1175:*CHEBI:17775:*LIGAND-CPD:C00366:*CAS:69-93-2 1.7.3.3 urate + oxygen + H2O = 5-hydroxyisourate + hydrogen peroxide urate degradation to allantoin urate 8-hydroxyxanthine*2,6,8-trihydroxypurine*trioxopurine*2,6,8-trioxypurine*purine-2,6,8-(1H,3H,9H)-trione*uric acid 168.112 C5 H4 N4 O3 O=C2(C1(=C(NC(=O)N1)[N-]C(O)[N-]2)) PUBCHEM:44229235:*PUBCHEM:1175:*CHEBI:17775:*LIGAND-CPD:C00366:*CAS:69-93-2 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ adenosine nucleotides degradation II urate 8-hydroxyxanthine*2,6,8-trihydroxypurine*trioxopurine*2,6,8-trioxypurine*purine-2,6,8-(1H,3H,9H)-trione*uric acid 168.112 C5 H4 N4 O3 O=C2(C1(=C(NC(=O)N1)[N-]C(O)[N-]2)) PUBCHEM:44229235:*PUBCHEM:1175:*CHEBI:17775:*LIGAND-CPD:C00366:*CAS:69-93-2 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ adenosine nucleotides degradation I urate 8-hydroxyxanthine*2,6,8-trihydroxypurine*trioxopurine*2,6,8-trioxypurine*purine-2,6,8-(1H,3H,9H)-trione*uric acid 168.112 C5 H4 N4 O3 O=C2(C1(=C(NC(=O)N1)[N-]C(O)[N-]2)) PUBCHEM:44229235:*PUBCHEM:1175:*CHEBI:17775:*LIGAND-CPD:C00366:*CAS:69-93-2 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ guanosine nucleotides degradation II oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 2.6.1.1 L-aspartate + 2-oxoglutarate = L-glutamate + oxaloacetate aspartate biosynthesis oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 2.6.1.1 L-aspartate + 2-oxoglutarate = L-glutamate + oxaloacetate aspartate degradation II oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 4.1.1.49 oxaloacetate + ATP = CO2 + phosphoenolpyruvate + ADP gluconeogenesis I oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 4.1.1.49 oxaloacetate + ATP = CO2 + phosphoenolpyruvate + ADP superpathway of glyoxylate cycle oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 2.3.3.8 oxaloacetate + acetyl-CoA + ADP = citrate + coenzyme A + ATP acetyl-CoA biosynthesis (from citrate) oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH superpathway of glyoxylate cycle oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A glyoxylate cycle oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A TCA cycle variation III (eukaryotic) oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A glutamine biosynthesis III oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 gluconeogenesis I oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 glutamine biosynthesis III oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 CO2 fixation into oxaloacetate oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 4.1.1.31 H+ + oxaloacetate = phosphoenolpyruvate + H2O + CO2 C4 photosynthetic carbon assimilation cycle oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH glyoxylate cycle oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH gluconeogenesis I oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH TCA cycle variation III (eukaryotic) oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 1.1.1.37 (S)-malate + NAD+ = H+ + oxaloacetate + NADH aspartate degradation II oxaloacetate oxaloacetate*keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxalacetate 130.057 C4 H2 O5 [O-]C(C(=O)CC([O-])=O)=O PUBCHEM:164550:*CHEBI:16452:*LIGAND-CPD:C00036:*CAS:328-42-7 1.1.1.82 (S)-malate + NADP+ = H+ + NADPH + oxaloacetate C4 photosynthetic carbon assimilation cycle uroporphyrinogen-III uroporphyrinogen III 828.742 C40 H36 N4 O16 C15(NC(=C(C=1CC(=O)[O-])CCC([O-])=O)CC2(=C(C(=C(N2)CC3(NC(=C(C=3CC(=O)[O-])CCC([O-])=O)CC4(=C(C(=C(N4)C5)CCC(=O)[O-])CC([O-])=O)))CC([O-])=O)CCC(=O)[O-])) CHEBI:57308:*PUBCHEM:25202645:*LIGAND-CPD:C01051:*CAS:1976-85-8 4.2.1.75 hydroxymethylbilane = uroporphyrinogen-III + H2O tetrapyrrole biosynthesis I uroporphyrinogen-III uroporphyrinogen III 828.742 C40 H36 N4 O16 C15(NC(=C(C=1CC(=O)[O-])CCC([O-])=O)CC2(=C(C(=C(N2)CC3(NC(=C(C=3CC(=O)[O-])CCC([O-])=O)CC4(=C(C(=C(N4)C5)CCC(=O)[O-])CC([O-])=O)))CC([O-])=O)CCC(=O)[O-])) CHEBI:57308:*PUBCHEM:25202645:*LIGAND-CPD:C01051:*CAS:1976-85-8 2.1.1.107 S-adenosyl-L-methionine + uroporphyrinogen-III = H+ + S-adenosyl-L-homocysteine + precorrin-1 siroheme biosynthesis uroporphyrinogen-III uroporphyrinogen III 828.742 C40 H36 N4 O16 C15(NC(=C(C=1CC(=O)[O-])CCC([O-])=O)CC2(=C(C(=C(N2)CC3(NC(=C(C=3CC(=O)[O-])CCC([O-])=O)CC4(=C(C(=C(N4)C5)CCC(=O)[O-])CC([O-])=O)))CC([O-])=O)CCC(=O)[O-])) CHEBI:57308:*PUBCHEM:25202645:*LIGAND-CPD:C01051:*CAS:1976-85-8 4.1.1.37 uroporphyrinogen-III + H+ = coproporphyrinogen III + CO2 chlorophyllide a biosynthesis I uroporphyrinogen-III uroporphyrinogen III 828.742 C40 H36 N4 O16 C15(NC(=C(C=1CC(=O)[O-])CCC([O-])=O)CC2(=C(C(=C(N2)CC3(NC(=C(C=3CC(=O)[O-])CCC([O-])=O)CC4(=C(C(=C(N4)C5)CCC(=O)[O-])CC([O-])=O)))CC([O-])=O)CCC(=O)[O-])) CHEBI:57308:*PUBCHEM:25202645:*LIGAND-CPD:C01051:*CAS:1976-85-8 4.1.1.37 uroporphyrinogen-III + H+ = coproporphyrinogen III + CO2 heme biosynthesis from uroporphyrinogen-III I D-gluconate gluconate*gluconic acid*D-gluconic acid*dextronic acid*aldonic acid*maltonic acid 195.149 C6 H11 O7 C(O)C(O)C(O)C(O)C(O)C(=O)[O-] PUBCHEM:10690:*CHEBI:18391:*PUBCHEM:6419706:*LIGAND-CPD:C00257:*CAS:526-95-4 3.1.1.17 D-glucono-1,5-lactone + H2O = H+ + D-gluconate glucose and glucose-1-phosphate degradation D-myo-inositol (1,2,3) trisphosphate 1D-myo-inositol (1,2,3) trisphosphate*Ins(1,2,3)P3*I(1,2,3)P3 414.049 C6 H9 O15 P3 [O-]P([O-])(=O)OC1(C(O)C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:25201761:*PUBCHEM:25244812: D-myo-inositol (1,2,3,4) tetrakisphosphate + H2O = D-myo-inositol (1,2,3) trisphosphate phytate degradation II D-myo-inositol (1,2,3) trisphosphate 1D-myo-inositol (1,2,3) trisphosphate*Ins(1,2,3)P3*I(1,2,3)P3 414.049 C6 H9 O15 P3 [O-]P([O-])(=O)OC1(C(O)C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:25201761:*PUBCHEM:25244812: D-myo-inositol (1,2,3) trisphosphate + H2O = D-myo-inositol (1,2) bisphosphate phytate degradation II D-myo-inositol (1,2,3) trisphosphate 1D-myo-inositol (1,2,3) trisphosphate*Ins(1,2,3)P3*I(1,2,3)P3 414.049 C6 H9 O15 P3 [O-]P([O-])(=O)OC1(C(O)C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:25201761:*PUBCHEM:25244812: D-myo-inositol (1,2,3) trisphosphate + H2O = D-myo-inositol (1,2) bisphosphate phytate degradation I D-myo-inositol (1,2,3) trisphosphate 1D-myo-inositol (1,2,3) trisphosphate*Ins(1,2,3)P3*I(1,2,3)P3 414.049 C6 H9 O15 P3 [O-]P([O-])(=O)OC1(C(O)C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:25201761:*PUBCHEM:25244812: D-myo-inositol (1,2,3,6) tetrakisphosphate + H2O = D-myo-inositol (1,2,3) trisphosphate phytate degradation I episterone ergosta-7,24(28)-dien-3-one, (5α)- 396.655 C28 H44 O1 C1(CC(CC2(C1(C3(C(=CC2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))=O) 1.1.1.- episterone + NADPH + H+ = episterol + NADP+ plant sterol biosynthesis episterone ergosta-7,24(28)-dien-3-one, (5α)- 396.655 C28 H44 O1 C1(CC(CC2(C1(C3(C(=CC2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))=O) 1.1.1.- 4α-carboxy-ergosta-7,24(241)-dien-3β-ol + NAD+ = episterone + NADH + CO2 plant sterol biosynthesis CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.5 sn-glycerol-3-phosphate = CMP + H+ phosphatidylglycerol biosynthesis I (plastidic) CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.5 sn-glycerol-3-phosphate = CMP + H+ phosphatidylglycerol biosynthesis II (non-plastidic) CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.5 sn-glycerol-3-phosphate = CMP + H+ cardiolipin biosynthesis II CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.2 CDP-choline = CMP + H+ phosphatidylcholine biosynthesis I CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.2 CDP-choline = CMP + H+ choline biosynthesis III CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.2 CDP-choline = CMP + H+ phosphatidylcholine biosynthesis II CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 6.3.2.5 D-4'-phosphopantothenate + L-cysteine + CTP = H+ + R-4'-phosphopantothenoyl-L-cysteine + diphosphate + CMP coenzyme A biosynthesis CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.- CDP-N-dimethylethanolamine = CMP phosphatidylcholine biosynthesis IV CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.8 L-serine = CMP + H+ phospholipid biosynthesis II CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.8 L-serine = CMP + H+ phosphatidylethanolamine biosynthesis I CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.1 CDP-ethanolamine = CMP phosphatidylethanolamine biosynthesis II CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.1.- cytidine + GTP = H+ + CMP + GDP salvage pathways of pyrimidine ribonucleotides CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.4.25 ATP + CMP = ADP + CDP salvage pathways of pyrimidine ribonucleotides CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 4.6.1.12 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol = 2-C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP methylerythritol phosphate pathway CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.- CDP-N-methylethanolamine = CMP phosphatidylcholine biosynthesis III CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: cardiolipin biosynthesis II CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.11 myo-inositol = CMP phospholipid biosynthesis II CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.11 myo-inositol = CMP 3-phosphoinositide biosynthesis CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 321.183 C9 H12 N3 O8 P1 NC2(=NC(N(C1(C(C(C(O1)COP([O-])([O-])=O)O)O))C=C2)=O) PUBCHEM:7058165:*CHEBI:60377:*CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.11 myo-inositol = CMP D-myo-inositol (1,4,5)-trisphosphate biosynthesis 2-hydroxyferulate 2-hydroxy ferulic acid 210.186 C10 H10 O5 COC1(=C(C=C(C(=C1)C=CC(=O)O)O)O) 2-hydroxyferulate = scopoletin simplecoumarins biosynthesis 2-hydroxyferulate 2-hydroxy ferulic acid 210.186 C10 H10 O5 COC1(=C(C=C(C(=C1)C=CC(=O)O)O)O) ferulate = 2-hydroxyferulate simplecoumarins biosynthesis 1-aminocyclopropane-1-carboxylate 1-Aminocyclopropane-1-carboxylic acid*1-aminocyclopropane-1-carboxylic acid*ACC*1-aminocyclopropanecarboxylic acid*1-aminocyclopropanecarboxylate 101.105 C4 H7 N1 O2 C1(CC1(C([O-])=O)[N+]) PUBCHEM:6971063:*CHEBI:30526:*LIGAND-CPD:C01234:*CAS:22059-21-8 1.14.17.4 H+ + L-ascorbate + 1-aminocyclopropane-1-carboxylate + oxygen = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine 1-aminocyclopropane-1-carboxylate 1-Aminocyclopropane-1-carboxylic acid*1-aminocyclopropane-1-carboxylic acid*ACC*1-aminocyclopropanecarboxylic acid*1-aminocyclopropanecarboxylate 101.105 C4 H7 N1 O2 C1(CC1(C([O-])=O)[N+]) PUBCHEM:6971063:*CHEBI:30526:*LIGAND-CPD:C01234:*CAS:22059-21-8 4.4.1.14 S-adenosyl-L-methionine = H+ + S-methyl-5'-thioadenosine + 1-aminocyclopropane-1-carboxylate ethylene biosynthesis from methionine 1D-myo-inositol (2) monophosphate 1D-myo-inositol (2) monophosphate*D-myo-inositol (2) monophosphate*Ins(2)P1*Ins(2)P*Ins2P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(C(O)C(O)C(O)C(O)C(O)1) PUBCHEM:25203550: D-myo-inositol (1,2) bisphosphate + H2O = 1D-myo-inositol (2) monophosphate phytate degradation II 1D-myo-inositol (2) monophosphate 1D-myo-inositol (2) monophosphate*D-myo-inositol (2) monophosphate*Ins(2)P1*Ins(2)P*Ins2P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(C(O)C(O)C(O)C(O)C(O)1) PUBCHEM:25203550: D-myo-inositol (1,2) bisphosphate + H2O = 1D-myo-inositol (2) monophosphate phytate degradation I 1D-myo-inositol (2) monophosphate 1D-myo-inositol (2) monophosphate*D-myo-inositol (2) monophosphate*Ins(2)P1*Ins(2)P*Ins2P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(C(O)C(O)C(O)C(O)C(O)1) PUBCHEM:25203550: D-myo-inositol (2,4) bisphosphate + H2O = 1D-myo-inositol (2) monophosphate phytate degradation II 1D-myo-inositol (2) monophosphate 1D-myo-inositol (2) monophosphate*D-myo-inositol (2) monophosphate*Ins(2)P1*Ins(2)P*Ins2P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(C(O)C(O)C(O)C(O)C(O)1) PUBCHEM:25203550: 1D-myo-inositol (2) monophosphate + H2O = myo-inositol phytate degradation I cis-aconitate 171.086 C6 H3 O6 O=C(C=C(C([O-])=O)CC(=O)[O-])[O-] KNAPSACK:C00001177:*PUBCHEM:5459816:*CHEBI:16383:*LIGAND-CPD:C00417:*CAS:585-84-2 4.2.1.3 cis-aconitate + H2O = D-threo-isocitrate glyoxylate cycle cis-aconitate 171.086 C6 H3 O6 O=C(C=C(C([O-])=O)CC(=O)[O-])[O-] KNAPSACK:C00001177:*PUBCHEM:5459816:*CHEBI:16383:*LIGAND-CPD:C00417:*CAS:585-84-2 4.2.1.3 cis-aconitate + H2O = D-threo-isocitrate TCA cycle variation III (eukaryotic) cis-aconitate 171.086 C6 H3 O6 O=C(C=C(C([O-])=O)CC(=O)[O-])[O-] KNAPSACK:C00001177:*PUBCHEM:5459816:*CHEBI:16383:*LIGAND-CPD:C00417:*CAS:585-84-2 4.2.1.3 cis-aconitate + H2O = D-threo-isocitrate glutamine biosynthesis III cis-aconitate 171.086 C6 H3 O6 O=C(C=C(C([O-])=O)CC(=O)[O-])[O-] KNAPSACK:C00001177:*PUBCHEM:5459816:*CHEBI:16383:*LIGAND-CPD:C00417:*CAS:585-84-2 4.2.1.3 citrate = cis-aconitate + H2O glyoxylate cycle cis-aconitate 171.086 C6 H3 O6 O=C(C=C(C([O-])=O)CC(=O)[O-])[O-] KNAPSACK:C00001177:*PUBCHEM:5459816:*CHEBI:16383:*LIGAND-CPD:C00417:*CAS:585-84-2 4.2.1.3 citrate = cis-aconitate + H2O TCA cycle variation III (eukaryotic) cis-aconitate 171.086 C6 H3 O6 O=C(C=C(C([O-])=O)CC(=O)[O-])[O-] KNAPSACK:C00001177:*PUBCHEM:5459816:*CHEBI:16383:*LIGAND-CPD:C00417:*CAS:585-84-2 4.2.1.3 citrate = cis-aconitate + H2O glutamine biosynthesis III protoporphyrinogen IX protoporphyrinogen IX*protoporphyrinogen 566.699 C34 H38 N4 O4 C15(NC(=C(C=1C)CCC([O-])=O)CC2(=C(C(=C(N2)CC3(NC(=C(C=3C)C=C)CC4(=C(C(=C(N4)C5)C=C)C)))C)CCC(=O)[O-])) CHEBI:57307:*PUBCHEM:20849104:*LIGAND-CPD:C01079:*CAS:7412-77-3 1.3.3.4 protoporphyrinogen IX + oxygen = protoporphyrin IX + hydrogen peroxide chlorophyllide a biosynthesis I protoporphyrinogen IX protoporphyrinogen IX*protoporphyrinogen 566.699 C34 H38 N4 O4 C15(NC(=C(C=1C)CCC([O-])=O)CC2(=C(C(=C(N2)CC3(NC(=C(C=3C)C=C)CC4(=C(C(=C(N4)C5)C=C)C)))C)CCC(=O)[O-])) CHEBI:57307:*PUBCHEM:20849104:*LIGAND-CPD:C01079:*CAS:7412-77-3 1.3.3.4 protoporphyrinogen IX + oxygen = protoporphyrin IX + hydrogen peroxide heme biosynthesis from uroporphyrinogen-III I protoporphyrinogen IX protoporphyrinogen IX*protoporphyrinogen 566.699 C34 H38 N4 O4 C15(NC(=C(C=1C)CCC([O-])=O)CC2(=C(C(=C(N2)CC3(NC(=C(C=3C)C=C)CC4(=C(C(=C(N4)C5)C=C)C)))C)CCC(=O)[O-])) CHEBI:57307:*PUBCHEM:20849104:*LIGAND-CPD:C01079:*CAS:7412-77-3 1.3.3.3 coproporphyrinogen III + oxygen + H+ = protoporphyrinogen IX + CO2 + H2O chlorophyllide a biosynthesis I protoporphyrinogen IX protoporphyrinogen IX*protoporphyrinogen 566.699 C34 H38 N4 O4 C15(NC(=C(C=1C)CCC([O-])=O)CC2(=C(C(=C(N2)CC3(NC(=C(C=3C)C=C)CC4(=C(C(=C(N4)C5)C=C)C)))C)CCC(=O)[O-])) CHEBI:57307:*PUBCHEM:20849104:*LIGAND-CPD:C01079:*CAS:7412-77-3 1.3.3.3 coproporphyrinogen III + oxygen + H+ = protoporphyrinogen IX + CO2 + H2O heme biosynthesis from uroporphyrinogen-III I adenylo-succinate N6-(1,2-dicarboxyethyl)-AMP*N6-(1,2-dicarboxyethyl)-AMP*N6-(1,2-dicarboxyethyl)-AMP*adenylo-succ 459.265 C14 H14 N5 O11 P1 O=C([O-])CC(NC3(=NC=NC1(=C(N=CN1C2(OC(COP(=O)([O-])[O-])C(O)C(O)2))3)))C(=O)[O-] PUBCHEM:25245432:*LIGAND-CPD:C03794:*CAS:19240-42-7 4.3.2.2 adenylo-succinate = fumarate + AMP purine nucleotides de novo biosynthesis II adenylo-succinate N6-(1,2-dicarboxyethyl)-AMP*N6-(1,2-dicarboxyethyl)-AMP*N6-(1,2-dicarboxyethyl)-AMP*adenylo-succ 459.265 C14 H14 N5 O11 P1 O=C([O-])CC(NC3(=NC=NC1(=C(N=CN1C2(OC(COP(=O)([O-])[O-])C(O)C(O)2))3)))C(=O)[O-] PUBCHEM:25245432:*LIGAND-CPD:C03794:*CAS:19240-42-7 4.3.2.2 adenylo-succinate = fumarate + AMP adenosine nucleotides de novo biosynthesis adenylo-succinate N6-(1,2-dicarboxyethyl)-AMP*N6-(1,2-dicarboxyethyl)-AMP*N6-(1,2-dicarboxyethyl)-AMP*adenylo-succ 459.265 C14 H14 N5 O11 P1 O=C([O-])CC(NC3(=NC=NC1(=C(N=CN1C2(OC(COP(=O)([O-])[O-])C(O)C(O)2))3)))C(=O)[O-] PUBCHEM:25245432:*LIGAND-CPD:C03794:*CAS:19240-42-7 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = H+ + adenylo-succinate + GDP purine nucleotides de novo biosynthesis II adenylo-succinate N6-(1,2-dicarboxyethyl)-AMP*N6-(1,2-dicarboxyethyl)-AMP*N6-(1,2-dicarboxyethyl)-AMP*adenylo-succ 459.265 C14 H14 N5 O11 P1 O=C([O-])CC(NC3(=NC=NC1(=C(N=CN1C2(OC(COP(=O)([O-])[O-])C(O)C(O)2))3)))C(=O)[O-] PUBCHEM:25245432:*LIGAND-CPD:C03794:*CAS:19240-42-7 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = H+ + adenylo-succinate + GDP adenosine nucleotides de novo biosynthesis resveratrol 3,4',5-trihydroxystilbene*3,5,4'-trihydroxystilbene 228.247 C14 H12 O3 C1(C(=CC(=CC=1C=CC2(C=CC(=CC=2)O))O)O) LIGAND-CPD:C03582:*CHEBI:27881:*PUBCHEM:445154:*KNAPSACK:C00002903:*CAS:501-36-0: 2.3.1.95 H+ + 4-coumaroyl-CoA + malonyl-CoA = resveratrol + coenzyme A + CO2 resveratrol biosynthesis nicotinamide riboside N-ribosyl-nicotinamide*nicotinamide ribonucleoside*nicotinamide ribose*nicotinamide-β-riboside*ribosylnicotinamide 255.25 C11 H15 N2 O5 C1(C(OC(C(O)1)CO)[N+]2(C=C(C=CC=2)C(=O)N))(O) CHEBI:15927:*LIGAND-CPD:C03150:*PUBCHEM:940:*CAS:1341-23-7 3.1.3.5 nicotinamide mononucleotide + H2O = nicotinamide riboside pyridine nucleotide cycling (plants) nicotinamide riboside N-ribosyl-nicotinamide*nicotinamide ribonucleoside*nicotinamide ribose*nicotinamide-β-riboside*ribosylnicotinamide 255.25 C11 H15 N2 O5 C1(C(OC(C(O)1)CO)[N+]2(C=C(C=CC=2)C(=O)N))(O) CHEBI:15927:*LIGAND-CPD:C03150:*PUBCHEM:940:*CAS:1341-23-7 3.2.2.- nicotinamide riboside + H2O = nicotinamide pyridine nucleotide cycling (plants) 3-hydroxypropanoyl-CoA 3-Hydroxypropanoyl coenzymeA*3-Hydroxypropanoyl-CoA*3-hydroxypropionyl-coenzyme A*3-hydroxypropionyl-CoA*3-hydroxypropanoyl coenzymeA 835.566 C24 H36 N7 O18 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(CCO)=O PUBCHEM:25245434:*CHEBI:58528:*PUBCHEM:44229175:*LIGAND-CPD:C05668: 4.2.1.116 3-hydroxypropanoyl-CoA = acrylyl-CoA + H2O β-alanine biosynthesis II 3-hydroxypropanoyl-CoA 3-Hydroxypropanoyl coenzymeA*3-Hydroxypropanoyl-CoA*3-hydroxypropionyl-coenzyme A*3-hydroxypropionyl-CoA*3-hydroxypropanoyl coenzymeA 835.566 C24 H36 N7 O18 P3 S1 S(CCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C(CCO)=O PUBCHEM:25245434:*CHEBI:58528:*PUBCHEM:44229175:*LIGAND-CPD:C05668: 3.1.2.4 3-hydroxypropanoyl-CoA + H2O = H+ + 3-hydroxypropionate + coenzyme A β-alanine biosynthesis II thymine 5-methyluracil*5-methyl-2,4(1H,3H)-pyrimidinedione 126.115 C5 H6 N2 O2 C1(NC=C(C(=O)N1)C)(=O) PUBCHEM:1135:*CHEBI:17821:*LIGAND-CPD:C00178:*CAS:65-71-4: 1.3.1.2 5,6-dihydrothymine + NADP+ = thymine + NADPH + H+ thymine degradation N-benzoylanthranilate N-bezoylanthranilate*2-benzamidobenzoate 240.238 C14 H10 N1 O3 C1(C(=C(C=CC=1)NC(=O)C2(C=CC=CC=2))C([O-])=O) CHEBI:17331:*PUBCHEM:5091716:*LIGAND-CPD:C03141:*CAS:579-93-1 2.3.1.144 anthranilate + benzoyl-CoA = N-benzoylanthranilate + coenzyme A benzoylanthranilate biosynthesis β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 5.3.1.9 β-D-glucose-6-phosphate = D-fructose-6-phosphate sucrose degradation III β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 5.3.1.9 β-D-glucose-6-phosphate = D-fructose-6-phosphate gluconeogenesis I β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 5.3.1.9 β-D-glucose-6-phosphate = D-fructose-6-phosphate GDP-mannose biosynthesis β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 5.3.1.9 β-D-glucose-6-phosphate = D-fructose-6-phosphate starch biosynthesis β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 5.3.1.9 β-D-glucose-6-phosphate = D-fructose-6-phosphate glycolysis III β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 5.3.1.9 β-D-glucose-6-phosphate = D-fructose-6-phosphate glycolysis I β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 3.2.1.26 sucrose-6-phosphate + H2O = β-D-glucose-6-phosphate + β-D-fructofuranose sucrose degradation I β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP GDP-glucose biosynthesis β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP glycolysis III β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP trehalose degradation II (trehalase) β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP glucose and glucose-1-phosphate degradation β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP glycogen degradation I β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 5.4.2.6 β-D-glucose 1-phosphate = β-D-glucose-6-phosphate galactose degradation I (Leloir pathway) β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 1.1.1.49 β-D-glucose-6-phosphate + NADP+ = 6-phospho-D-glucono-1,5-lactone + NADPH + H+ pentose phosphate pathway (oxidative branch) β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 5.1.3.15 α-D-glucose 6-phosphate = β-D-glucose-6-phosphate sucrose degradation III β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 5.1.3.15 α-D-glucose 6-phosphate = β-D-glucose-6-phosphate GDP-glucose biosynthesis β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 5.1.3.15 α-D-glucose 6-phosphate = β-D-glucose-6-phosphate starch biosynthesis β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 5.1.3.15 α-D-glucose 6-phosphate = β-D-glucose-6-phosphate starch degradation β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 5.1.3.15 α-D-glucose 6-phosphate = β-D-glucose-6-phosphate glucose and glucose-1-phosphate degradation β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 258.121 C6 H11 O9 P1 C1(OC(C(C(C1O)O)O)O)COP([O-])([O-])=O PUBCHEM:23421199:*CHEBI:17719:*LIGAND-CPD:C00092:*LIGAND:C00092:*CAS:56-73-5*LIGAND-CPD:C01172: 5.1.3.15 α-D-glucose 6-phosphate = β-D-glucose-6-phosphate sucrose biosynthesis betalamic acid betalamate 209.158 C9 H7 N1 O5 C1(C(C=C(NC1C([O-])=O)C(=O)[O-])=CC=O) PUBCHEM:25246067:*LIGAND-CPD:C08538: dopamine + betalamic acid = H+ + miraxanthin V + H2O betaxanthin biosynthesis (via dopamine) CDP-N-methylethanolamine 459.266 C12 H21 N4 O11 P2 C[N+]CCOP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(N)=NC(=O)2)) PUBCHEM:25244196:*LIGAND-CPD:C03486: 2.7.7.57 H+ + N-methylethanolamine phosphate + CTP = CDP-N-methylethanolamine + diphosphate phosphatidylcholine biosynthesis III CDP-N-methylethanolamine 459.266 C12 H21 N4 O11 P2 C[N+]CCOP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(N)=NC(=O)2)) PUBCHEM:25244196:*LIGAND-CPD:C03486: 2.7.8.- CDP-N-methylethanolamine = CMP phosphatidylcholine biosynthesis III phaseic acid 5-[(1R,5R,8S)-8-hydroxy-1,5-dimethyl-3-oxo-7-oxabicyclo[3.2.1]oct-8-yl]-3-methyl-penta-2,4-dienoic acid*(-)-phaseic acid*PA*phaseate 279.312 C15 H19 O5 C1(C2(C(C(CC1=O)(C)OC2)(C=CC(=CC([O-])=O)C)O)(C)) PUBCHEM:442386:*PUBCHEM:25244821:*LIGAND-CPD:C09707: 8'-hydroxyabscisate = phaseic acid phaseic acid biosynthesis phaseic acid 5-[(1R,5R,8S)-8-hydroxy-1,5-dimethyl-3-oxo-7-oxabicyclo[3.2.1]oct-8-yl]-3-methyl-penta-2,4-dienoic acid*(-)-phaseic acid*PA*phaseate 279.312 C15 H19 O5 C1(C2(C(C(CC1=O)(C)OC2)(C=CC(=CC([O-])=O)C)O)(C)) PUBCHEM:442386:*PUBCHEM:25244821:*LIGAND-CPD:C09707: 1.-.-.- phaseic acid = dihydroxyphaseic acid phaseic acid biosynthesis primary fluorescent chlorophyll catabolite (82R,12S,13S)-12-(2-carboxyethyl)-3-ethyl-1-formyl-82-(methoxycarbonyl)-2,7,13,17-tetramethyl-18-vinyl-12,13-dihydro-8,10-ethanobilene-b-81,19(16H)-dione*pFCC*primary fluorescent catabolite 626.708 C35 H38 N4 O7 C1(=C(C(=C(N1)CC2(NC5(=C(C=2C)C([C-](C(=C4(N=C(CC3(NC(C(=C3C)C=C)=O))C(C4CCC([O-])=O)C))5)C(OC)=O)=O)))CC)C)C=O CHEBI:58719:*PUBCHEM:25244823: 1.3.1.80 H+ + primary fluorescent chlorophyll catabolite + NADP+ = red chlorophyll catabolite + NADPH chlorophyll a degradation ω-hydroxycaprate ω-hydroxycapric acid*10-hydroxydecanoate 187.258 C10 H19 O3 C(CCCC([O-])=O)CCCCCO CHEBI:11305:*PUBCHEM:6991989:*LIGAND-CPD:C02774:*NCI:15139*CAS:1679-53-4 caprate + NADP+ + OH- = ω-hydroxycaprate + NADPH ω-hydroxylation of caprate and laurate 3-deoxy-D-arabino-heptulosonate-7-phosphate 3-deoxy-D-arabino-heptulosonate-7-P*3-deoxy-arabino-heptulosonate 7-phosphate*3-deoxy-arabino-heptulosonate-7-P*2-dehydro-3-deoxy-D-arabino-heptonate 7-phosphate*3-deoxy-D-arabino-hept-2-ulosonate-7-phosphate*3-deoxy-arabino-heptulonate 7-phosphate*DAHP 285.124 C7 H10 O10 P1 P([O-])(=O)([O-])OCC(O)C(O)C(O)CC(=O)C(=O)[O-] PUBCHEM:5460215:*LIGAND-CPD:C04691:*CAS:2627-73-8 4.2.3.4 3-deoxy-D-arabino-heptulosonate-7-phosphate = 3-dehydroquinate chorismate biosynthesis I 3-deoxy-D-arabino-heptulosonate-7-phosphate 3-deoxy-D-arabino-heptulosonate-7-P*3-deoxy-arabino-heptulosonate 7-phosphate*3-deoxy-arabino-heptulosonate-7-P*2-dehydro-3-deoxy-D-arabino-heptonate 7-phosphate*3-deoxy-D-arabino-hept-2-ulosonate-7-phosphate*3-deoxy-arabino-heptulonate 7-phosphate*DAHP 285.124 C7 H10 O10 P1 P([O-])(=O)([O-])OCC(O)C(O)C(O)CC(=O)C(=O)[O-] PUBCHEM:5460215:*LIGAND-CPD:C04691:*CAS:2627-73-8 4.2.3.4 3-deoxy-D-arabino-heptulosonate-7-phosphate = 3-dehydroquinate 3-dehydroquinate biosynthesis I 3-deoxy-D-arabino-heptulosonate-7-phosphate 3-deoxy-D-arabino-heptulosonate-7-P*3-deoxy-arabino-heptulosonate 7-phosphate*3-deoxy-arabino-heptulosonate-7-P*2-dehydro-3-deoxy-D-arabino-heptonate 7-phosphate*3-deoxy-D-arabino-hept-2-ulosonate-7-phosphate*3-deoxy-arabino-heptulonate 7-phosphate*DAHP 285.124 C7 H10 O10 P1 P([O-])(=O)([O-])OCC(O)C(O)C(O)CC(=O)C(=O)[O-] PUBCHEM:5460215:*LIGAND-CPD:C04691:*CAS:2627-73-8 2.5.1.54 phosphoenolpyruvate + D-erythrose-4-phosphate + H2O = 3-deoxy-D-arabino-heptulosonate-7-phosphate chorismate biosynthesis I 3-deoxy-D-arabino-heptulosonate-7-phosphate 3-deoxy-D-arabino-heptulosonate-7-P*3-deoxy-arabino-heptulosonate 7-phosphate*3-deoxy-arabino-heptulosonate-7-P*2-dehydro-3-deoxy-D-arabino-heptonate 7-phosphate*3-deoxy-D-arabino-hept-2-ulosonate-7-phosphate*3-deoxy-arabino-heptulonate 7-phosphate*DAHP 285.124 C7 H10 O10 P1 P([O-])(=O)([O-])OCC(O)C(O)C(O)CC(=O)C(=O)[O-] PUBCHEM:5460215:*LIGAND-CPD:C04691:*CAS:2627-73-8 2.5.1.54 phosphoenolpyruvate + D-erythrose-4-phosphate + H2O = 3-deoxy-D-arabino-heptulosonate-7-phosphate 3-dehydroquinate biosynthesis I 7,8-dihydroneopterin triphosphate H2NTP*6-(L-erythro-1,2-Dihydroxypropyl 3-triphosphate)-7,8-dihydropterin*6-[(1S,2R)-1,2-dihydroxy-3-triphosphooxypropyl]-7,8-dihydropterin*6-(D-erythro-1',2',3'-trihydroxypropyl)-7,8-dihydropterin-3'-triphosphate*7,8-dihydroneopterin 3'-triphosphate*2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphate*dihydroneopterin triphosphate*H2NTP 491.141 C9 H12 N5 O13 P3 NC2(=NC1(NCC(=NC=1C(=O)N2)C(O)C(O)COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])) PUBCHEM:44229135:*CHEBI:58462:*PUBCHEM:25201779:*LIGAND-CPD:C04895: 3.6.1.- 7,8-dihydroneopterin triphosphate + H2O = H+ + 7,8-dihydroneopterin phosphate + diphosphate 6-hydroxymethyl-dihydropterin diphosphate biosynthesis 7,8-dihydroneopterin triphosphate H2NTP*6-(L-erythro-1,2-Dihydroxypropyl 3-triphosphate)-7,8-dihydropterin*6-[(1S,2R)-1,2-dihydroxy-3-triphosphooxypropyl]-7,8-dihydropterin*6-(D-erythro-1',2',3'-trihydroxypropyl)-7,8-dihydropterin-3'-triphosphate*7,8-dihydroneopterin 3'-triphosphate*2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphate*dihydroneopterin triphosphate*H2NTP 491.141 C9 H12 N5 O13 P3 NC2(=NC1(NCC(=NC=1C(=O)N2)C(O)C(O)COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])) PUBCHEM:44229135:*CHEBI:58462:*PUBCHEM:25201779:*LIGAND-CPD:C04895: 3.5.4.16 GTP + H2O = H+ + formate + 7,8-dihydroneopterin triphosphate 6-hydroxymethyl-dihydropterin diphosphate biosynthesis (1,4-α-D-glucosyl)n-glucosyl glucogenin C18 H25 O11 |Protein|1 2.4.1.186 glycogen biosynthesis II (from UDP-D-Glucose) O-acetyl-L-serine O3-acetyl-L-serine*O3-acetyl-L-serine*acetylserine*O-acetylserine 147.13 C5 H9 N1 O4 O(C(=O)C)CC([N+])C(=O)[O-] PUBCHEM:25245438:*LIGAND-CPD:C00979:*CAS:66638-22-0 2.3.1.30 L-serine + acetyl-CoA = O-acetyl-L-serine + coenzyme A cysteine biosynthesis I O-acetyl-L-serine O3-acetyl-L-serine*O3-acetyl-L-serine*acetylserine*O-acetylserine 147.13 C5 H9 N1 O4 O(C(=O)C)CC([N+])C(=O)[O-] PUBCHEM:25245438:*LIGAND-CPD:C00979:*CAS:66638-22-0 2.5.1.47 O-acetyl-L-serine + hydrogen sulfide = H+ + L-cysteine + acetate cysteine biosynthesis I propanoyl-CoA propionyl-CoA*n-propionyl-CoA*propanoyl-CoA*propionyl-coenzyme A 819.566 C24 H36 N7 O17 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP([O-])(=O)OCC(C)(C)C(C(NCCC(=O)NCCSC(=O)CC)=O)O)O1)OP([O-])(=O)[O-])(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25245439:*LIGAND-CPD:C00100:*CAS:317-66-8 2.3.1.9 2-methylacetoacetyl-CoA + coenzyme A = propanoyl-CoA + acetyl-CoA isoleucine degradation I propanoyl-CoA propionyl-CoA*n-propionyl-CoA*propanoyl-CoA*propionyl-coenzyme A 819.566 C24 H36 N7 O17 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP([O-])(=O)OCC(C)(C)C(C(NCCC(=O)NCCSC(=O)CC)=O)O)O1)OP([O-])(=O)[O-])(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25245439:*LIGAND-CPD:C00100:*CAS:317-66-8 1.3.99.3 propanoyl-CoA = acrylyl-CoA β-alanine biosynthesis II propanoyl-CoA propionyl-CoA*n-propionyl-CoA*propanoyl-CoA*propionyl-coenzyme A 819.566 C24 H36 N7 O17 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP([O-])(=O)OCC(C)(C)C(C(NCCC(=O)NCCSC(=O)CC)=O)O)O1)OP([O-])(=O)[O-])(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25245439:*LIGAND-CPD:C00100:*CAS:317-66-8 6.2.1.17 coenzyme A + propionate + ATP = propanoyl-CoA + diphosphate + AMP β-alanine biosynthesis II propanoyl-CoA propionyl-CoA*n-propionyl-CoA*propanoyl-CoA*propionyl-coenzyme A 819.566 C24 H36 N7 O17 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP([O-])(=O)OCC(C)(C)C(C(NCCC(=O)NCCSC(=O)CC)=O)O)O1)OP([O-])(=O)[O-])(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25245439:*LIGAND-CPD:C00100:*CAS:317-66-8 1.2.1.27 (S)-methylmalonate-semialdehyde + coenzyme A + NAD+ + H2O = propanoyl-CoA + bicarbonate + NADH + H+ valine degradation I pyridoxine vitamin B6*2-methyl-3-hydroxy-4,5-bis(hydroxy-methyl) pyridine 169.18 C8 H11 N1 O3 C1(C(=NC=C(C=1CO)CO)C)O PUBCHEM:1054:*CHEBI:16709:*LIGAND-CPD:C00314:*CAS:65-23-6 2.7.1.- ATP + pyridoxine = H+ + ADP + pyridoxine-5'-phosphate pyridoxal 5'-phosphate salvage pathway UDP-α-D-glucose 564.289 C15 H22 N2 O17 P2 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CO)C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:52249: 3.13.1.1 UDP-α-D-glucose + H+ + sulfite = UDP-α-D-sulfoquinovopyranose + H2O sulfolipid biosynthesis p-coumaroyltriacetic acid lactone p-coumaroyltriacetate lactone 272.257 C15 H11 O5 C2(C=C(C=CC(=O)CC1(OC(=O)C=C([O-])C=1))C=CC(O)=2) LIGAND-CPD:C12087:*PUBCHEM:25246069: p-coumaroyltriacetate = p-coumaroyltriacetic acid lactone + H2O resveratrol biosynthesis p-coumaroyltriacetic acid lactone p-coumaroyltriacetate lactone 272.257 C15 H11 O5 C2(C=C(C=CC(=O)CC1(OC(=O)C=C([O-])C=1))C=CC(O)=2) LIGAND-CPD:C12087:*PUBCHEM:25246069: 2.3.1.- H+ + 4-coumaroyl-CoA + malonyl-CoA = p-coumaroyltriacetic acid lactone + coenzyme A + CO2 aromatic polyketides biosynthesis pelargonidin 3,5,7-Trihydroxy-2-(4-hydroxyphenil)-1-benzopyrylium chloride*3,4',5,7-tetrahydroxyflavylium chloride*3,5,7-trihydroxy-2-(4-hydroxyphenyl)benzopyrylium chloride*1-Benzopyrylium, 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-, chloride*Flavylium, 3,4',5,7-tetrahydroxy-, chloride*Pelargonidin chloride*Pelargonidol chloride 271.249 C15 H11 O5 C1(C(=CC(=C2(C=1O=C(C(=C2)O)C3(C=CC(=CC=3)O)))O)O) KNAPSACK:C00007232:*CHEBI:25863:*LIGAND-CPD:C05904:*PUBCHEM:440832:*CAS:134-04-3 2.4.1.115 pelargonidin = H+ + UDP + pelargonidin-3-O-β-D-glucoside anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) pelargonidin 3,5,7-Trihydroxy-2-(4-hydroxyphenil)-1-benzopyrylium chloride*3,4',5,7-tetrahydroxyflavylium chloride*3,5,7-trihydroxy-2-(4-hydroxyphenyl)benzopyrylium chloride*1-Benzopyrylium, 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-, chloride*Flavylium, 3,4',5,7-tetrahydroxy-, chloride*Pelargonidin chloride*Pelargonidol chloride 271.249 C15 H11 O5 C1(C(=CC(=C2(C=1O=C(C(=C2)O)C3(C=CC(=CC=3)O)))O)O) KNAPSACK:C00007232:*CHEBI:25863:*LIGAND-CPD:C05904:*PUBCHEM:440832:*CAS:134-04-3 1.3.1.77 H+ + pelargonidin = epiafzelechin 2,3-cis-flavanols biosynthesis pelargonidin 3,5,7-Trihydroxy-2-(4-hydroxyphenil)-1-benzopyrylium chloride*3,4',5,7-tetrahydroxyflavylium chloride*3,5,7-trihydroxy-2-(4-hydroxyphenyl)benzopyrylium chloride*1-Benzopyrylium, 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-, chloride*Flavylium, 3,4',5,7-tetrahydroxy-, chloride*Pelargonidin chloride*Pelargonidol chloride 271.249 C15 H11 O5 C1(C(=CC(=C2(C=1O=C(C(=C2)O)C3(C=CC(=CC=3)O)))O)O) KNAPSACK:C00007232:*CHEBI:25863:*LIGAND-CPD:C05904:*PUBCHEM:440832:*CAS:134-04-3 1.14.11.- H+ + leucopelargonidin + 2-oxoglutarate + oxygen = pelargonidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) pheophorbide a pheide a 594.709 C35 H38 N4 O5 C13(C(=C(C(N=1)=CC2(NC6(=C(C=2C)C(C(C(C5(N=C(C=C4(NC(C=3)C(=C4C)C=C))C(C5CCC(O)=O)C))=6)C(OC)=O)=O)))CC)C) LIGAND-CPD:C18021:*CHEBI:38257:*PUBCHEM:5323510: 3.1.1.82 pheophorbide a + H2O = pyropheophorbide a + methanol + CO2 chlorophyll a degradation pheophorbide a pheide a 594.709 C35 H38 N4 O5 C13(C(=C(C(N=1)=CC2(NC6(=C(C=2C)C(C(C(C5(N=C(C=C4(NC(C=3)C(=C4C)C=C))C(C5CCC(O)=O)C))=6)C(OC)=O)=O)))CC)C) LIGAND-CPD:C18021:*CHEBI:38257:*PUBCHEM:5323510: H+ + chlorophyllide a = pheophorbide a + Mg2+ chlorophyll a degradation pheophorbide a pheide a 594.709 C35 H38 N4 O5 C13(C(=C(C(N=1)=CC2(NC6(=C(C=2C)C(C(C(C5(N=C(C=C4(NC(C=3)C(=C4C)C=C))C(C5CCC(O)=O)C))=6)C(OC)=O)=O)))CC)C) LIGAND-CPD:C18021:*CHEBI:38257:*PUBCHEM:5323510: 1.14.12.20 pheophorbide a + oxygen + NADPH = H+ + red chlorophyll catabolite + NADP+ chlorophyll a degradation 3-methoxy-4-hydroxy-5-all-trans-nonaprenylbenzoate 3-methoxy-4-hydroxy-5-nonaprenylbenzoate*3-(3,7,11,15,19,23-nonamethyltetracosa-2,6,10,14,18,22-hexaenyl) -4-hydroxy-5-methoxy-benzoic acid*3-nonaprenyl-4-hydroxy-5-methoxybenzoate 780.205 C53 H79 O4 COC1(C(=C(CC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(C)C)C)C)C)C)C)C)C)C)C=C(C([O-])=O)C=1)O) PUBCHEM:25245444: 4.1.1.- H+ + 3-methoxy-4-hydroxy-5-all-trans-nonaprenylbenzoate = 2-nonaprenyl-6-methoxyphenol + CO2 ubiquinol-9 biosynthesis (eukaryotic) 3-methoxy-4-hydroxy-5-all-trans-nonaprenylbenzoate 3-methoxy-4-hydroxy-5-nonaprenylbenzoate*3-(3,7,11,15,19,23-nonamethyltetracosa-2,6,10,14,18,22-hexaenyl) -4-hydroxy-5-methoxy-benzoic acid*3-nonaprenyl-4-hydroxy-5-methoxybenzoate 780.205 C53 H79 O4 COC1(C(=C(CC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(C)C)C)C)C)C)C)C)C)C)C=C(C([O-])=O)C=1)O) PUBCHEM:25245444: 2.1.1.114 3,4-dihydroxy-5-all-trans-nonaprenylbenzoate + S-adenosyl-L-methionine = H+ + 3-methoxy-4-hydroxy-5-all-trans-nonaprenylbenzoate + S-adenosyl-L-homocysteine ubiquinol-9 biosynthesis (eukaryotic) 2-phospho-D-glycerate 2-phospho-D-glyceric acid*2-phospho-(R)-glycerate*2-phospho-(D)-glycerate*2-PGA*phosphoglycerate*2-phosphoglyceric acid*2-PG*2-P-glycerate*glycerate 2-phosphate*2-phospho-D-glycerate*2-P-D-glycerate*D-Glycerate 2-phosphate 183.034 C3 H4 O7 P1 OCC(OP(=O)([O-])[O-])C(=O)[O-] PUBCHEM:25245446:*PUBCHEM:40467846:*LIGAND-CPD:C00631:*CAS:2553-59-5 4.2.1.11 2-phospho-D-glycerate = phosphoenolpyruvate + H2O gluconeogenesis I 2-phospho-D-glycerate 2-phospho-D-glyceric acid*2-phospho-(R)-glycerate*2-phospho-(D)-glycerate*2-PGA*phosphoglycerate*2-phosphoglyceric acid*2-PG*2-P-glycerate*glycerate 2-phosphate*2-phospho-D-glycerate*2-P-D-glycerate*D-Glycerate 2-phosphate 183.034 C3 H4 O7 P1 OCC(OP(=O)([O-])[O-])C(=O)[O-] PUBCHEM:25245446:*PUBCHEM:40467846:*LIGAND-CPD:C00631:*CAS:2553-59-5 4.2.1.11 2-phospho-D-glycerate = phosphoenolpyruvate + H2O Rubisco shunt 2-phospho-D-glycerate 2-phospho-D-glyceric acid*2-phospho-(R)-glycerate*2-phospho-(D)-glycerate*2-PGA*phosphoglycerate*2-phosphoglyceric acid*2-PG*2-P-glycerate*glycerate 2-phosphate*2-phospho-D-glycerate*2-P-D-glycerate*D-Glycerate 2-phosphate 183.034 C3 H4 O7 P1 OCC(OP(=O)([O-])[O-])C(=O)[O-] PUBCHEM:25245446:*PUBCHEM:40467846:*LIGAND-CPD:C00631:*CAS:2553-59-5 4.2.1.11 2-phospho-D-glycerate = phosphoenolpyruvate + H2O glycolysis III 2-phospho-D-glycerate 2-phospho-D-glyceric acid*2-phospho-(R)-glycerate*2-phospho-(D)-glycerate*2-PGA*phosphoglycerate*2-phosphoglyceric acid*2-PG*2-P-glycerate*glycerate 2-phosphate*2-phospho-D-glycerate*2-P-D-glycerate*D-Glycerate 2-phosphate 183.034 C3 H4 O7 P1 OCC(OP(=O)([O-])[O-])C(=O)[O-] PUBCHEM:25245446:*PUBCHEM:40467846:*LIGAND-CPD:C00631:*CAS:2553-59-5 4.2.1.11 2-phospho-D-glycerate = phosphoenolpyruvate + H2O glycolysis IV (plant cytosol) 2-phospho-D-glycerate 2-phospho-D-glyceric acid*2-phospho-(R)-glycerate*2-phospho-(D)-glycerate*2-PGA*phosphoglycerate*2-phosphoglyceric acid*2-PG*2-P-glycerate*glycerate 2-phosphate*2-phospho-D-glycerate*2-P-D-glycerate*D-Glycerate 2-phosphate 183.034 C3 H4 O7 P1 OCC(OP(=O)([O-])[O-])C(=O)[O-] PUBCHEM:25245446:*PUBCHEM:40467846:*LIGAND-CPD:C00631:*CAS:2553-59-5 4.2.1.11 2-phospho-D-glycerate = phosphoenolpyruvate + H2O glycolysis I 2-phospho-D-glycerate 2-phospho-D-glyceric acid*2-phospho-(R)-glycerate*2-phospho-(D)-glycerate*2-PGA*phosphoglycerate*2-phosphoglyceric acid*2-PG*2-P-glycerate*glycerate 2-phosphate*2-phospho-D-glycerate*2-P-D-glycerate*D-Glycerate 2-phosphate 183.034 C3 H4 O7 P1 OCC(OP(=O)([O-])[O-])C(=O)[O-] PUBCHEM:25245446:*PUBCHEM:40467846:*LIGAND-CPD:C00631:*CAS:2553-59-5 5.4.2.1 3-phospho-D-glycerate = 2-phospho-D-glycerate gluconeogenesis I 2-phospho-D-glycerate 2-phospho-D-glyceric acid*2-phospho-(R)-glycerate*2-phospho-(D)-glycerate*2-PGA*phosphoglycerate*2-phosphoglyceric acid*2-PG*2-P-glycerate*glycerate 2-phosphate*2-phospho-D-glycerate*2-P-D-glycerate*D-Glycerate 2-phosphate 183.034 C3 H4 O7 P1 OCC(OP(=O)([O-])[O-])C(=O)[O-] PUBCHEM:25245446:*PUBCHEM:40467846:*LIGAND-CPD:C00631:*CAS:2553-59-5 5.4.2.1 3-phospho-D-glycerate = 2-phospho-D-glycerate Rubisco shunt 2-phospho-D-glycerate 2-phospho-D-glyceric acid*2-phospho-(R)-glycerate*2-phospho-(D)-glycerate*2-PGA*phosphoglycerate*2-phosphoglyceric acid*2-PG*2-P-glycerate*glycerate 2-phosphate*2-phospho-D-glycerate*2-P-D-glycerate*D-Glycerate 2-phosphate 183.034 C3 H4 O7 P1 OCC(OP(=O)([O-])[O-])C(=O)[O-] PUBCHEM:25245446:*PUBCHEM:40467846:*LIGAND-CPD:C00631:*CAS:2553-59-5 5.4.2.1 3-phospho-D-glycerate = 2-phospho-D-glycerate glycolysis III 2-phospho-D-glycerate 2-phospho-D-glyceric acid*2-phospho-(R)-glycerate*2-phospho-(D)-glycerate*2-PGA*phosphoglycerate*2-phosphoglyceric acid*2-PG*2-P-glycerate*glycerate 2-phosphate*2-phospho-D-glycerate*2-P-D-glycerate*D-Glycerate 2-phosphate 183.034 C3 H4 O7 P1 OCC(OP(=O)([O-])[O-])C(=O)[O-] PUBCHEM:25245446:*PUBCHEM:40467846:*LIGAND-CPD:C00631:*CAS:2553-59-5 5.4.2.1 3-phospho-D-glycerate = 2-phospho-D-glycerate glycolysis IV (plant cytosol) 2-phospho-D-glycerate 2-phospho-D-glyceric acid*2-phospho-(R)-glycerate*2-phospho-(D)-glycerate*2-PGA*phosphoglycerate*2-phosphoglyceric acid*2-PG*2-P-glycerate*glycerate 2-phosphate*2-phospho-D-glycerate*2-P-D-glycerate*D-Glycerate 2-phosphate 183.034 C3 H4 O7 P1 OCC(OP(=O)([O-])[O-])C(=O)[O-] PUBCHEM:25245446:*PUBCHEM:40467846:*LIGAND-CPD:C00631:*CAS:2553-59-5 5.4.2.1 3-phospho-D-glycerate = 2-phospho-D-glycerate glycolysis I leucopelargonidin cis 3,4-leucopelargonidin 290.272 C15 H14 O6 C1(C(=CC(=C2(C=1OC(C(C2O)O)C3(C=CC(=CC=3)O)))O)O) PUBCHEM:3286789:*LIGAND-CPD:C03648: 1.17.1.3 afzelechin + NADP+ + H2O = leucopelargonidin + NADPH + H+ 2,3-trans-flavanols biosynthesis leucopelargonidin cis 3,4-leucopelargonidin 290.272 C15 H14 O6 C1(C(=CC(=C2(C=1OC(C(C2O)O)C3(C=CC(=CC=3)O)))O)O) PUBCHEM:3286789:*LIGAND-CPD:C03648: 1.1.1.219 H+ + dihydrokaempferol + NADPH = leucopelargonidin + NADP+ leucopelargonidin and leucocyanidin biosynthesis leucopelargonidin cis 3,4-leucopelargonidin 290.272 C15 H14 O6 C1(C(=CC(=C2(C=1OC(C(C2O)O)C3(C=CC(=CC=3)O)))O)O) PUBCHEM:3286789:*LIGAND-CPD:C03648: 1.14.11.- H+ + leucopelargonidin + 2-oxoglutarate + oxygen = pelargonidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) 4α-formyl-stigmasta-7,24(241)-dien-3β-ol 440.708 C30 H48 O2 CC=C(CCC(C)C2(CCC1(C3(=CCC4(C(C=O)C(O)CCC(C)(C(CCC(C)12)3)4)))))C(C)C 1.14.13.- 4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol + NADH + oxygen = 4α-formyl-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis 4α-formyl-stigmasta-7,24(241)-dien-3β-ol 440.708 C30 H48 O2 CC=C(CCC(C)C2(CCC1(C3(=CCC4(C(C=O)C(O)CCC(C)(C(CCC(C)12)3)4)))))C(C)C 1.14.13.- 4α-formyl-stigmasta-7,24(241)-dien-3β-ol + NADH + oxygen = 4α-carboxy-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis β-D-glucose 1-phosphate 258.121 C6 H11 O9 P1 O(C1(OC(C(C(C1O)O)O)CO))P([O-])([O-])=O CHEBI:57684:*PUBCHEM:25244208:*LIGAND-CPD:C00663: α-D-glucose 1-phosphate = β-D-glucose 1-phosphate galactose degradation I (Leloir pathway) β-D-glucose 1-phosphate 258.121 C6 H11 O9 P1 O(C1(OC(C(C(C1O)O)O)CO))P([O-])([O-])=O CHEBI:57684:*PUBCHEM:25244208:*LIGAND-CPD:C00663: 5.4.2.6 β-D-glucose 1-phosphate = β-D-glucose-6-phosphate galactose degradation I (Leloir pathway) isopentenyl adenosine iPA 335.362 C15 H21 N5 O4 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(NCC=C(C)C)2)))OC(CO)3) CHEBI:554300:*PUBCHEM:24405:*LIGAND-CPD:C16427: 1.5.99.12 H+ + isopentenyl adenosine + H2O + FAD = adenosine + 3-methyl-2-butenal + FADH2 cytokinins degradation mevalonate-diphosphate mevalonate-diphosphate*mevalonate-5-PP*(R)-5-Diphosphomevalonate 304.087 C6 H10 O10 P2 C(C(C)(O)CCOP(OP([O-])([O-])=O)([O-])=O)C([O-])=O PUBCHEM:24916915:*LIGAND-CPD:C01143:*CAS:4872-34-8 4.1.1.33 mevalonate-diphosphate + ATP = isopentenyl diphosphate + CO2 + ADP mevalonate pathway I mevalonate-diphosphate mevalonate-diphosphate*mevalonate-5-PP*(R)-5-Diphosphomevalonate 304.087 C6 H10 O10 P2 C(C(C)(O)CCOP(OP([O-])([O-])=O)([O-])=O)C([O-])=O PUBCHEM:24916915:*LIGAND-CPD:C01143:*CAS:4872-34-8 2.7.4.2 mevalonate-5-phosphate + ATP = mevalonate-diphosphate + ADP mevalonate pathway I 2-oxo-3-carboxy-4,5-cyclopropylhex-5-enoate 2-(2-methylidenecyclopropyl)-3-oxobutanedioic acid*2-keto-3-carboxy-4,5-cyclopropylhex-5-enoate 182.132 C8 H6 O5 C1(C(C(C(=O)[O-])C(C([O-])=O)=O)C1)(=C) PUBCHEM:25201789: 4.1.1.- H+ + 2-oxo-3-carboxy-4,5-cyclopropylhex-5-enoate = beta-methylenecyclopropyl pyruvate + CO2 hypoglycin biosynthesis 2-oxo-3-carboxy-4,5-cyclopropylhex-5-enoate 2-(2-methylidenecyclopropyl)-3-oxobutanedioic acid*2-keto-3-carboxy-4,5-cyclopropylhex-5-enoate 182.132 C8 H6 O5 C1(C(C(C(=O)[O-])C(C([O-])=O)=O)C1)(=C) PUBCHEM:25201789: 2-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate = H+ + 2-oxo-3-carboxy-4,5-cyclopropylhex-5-enoate hypoglycin biosynthesis 24-ethylidenelophenol (Z)-24-ethylidenelophenol*citrostadienol 426.724 C30 H50 O1 CC=C(CCC(C)C2(CCC1(C3(=CCC4(C(C)C(O)CCC(C)(C(CCC(C)12)3)4)))))C(C)C PUBCHEM:25245448:*LIGAND-CPD:C11523: 1.14.13.- 24-ethylidenelophenol + NADH + oxygen = 4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis 24-ethylidenelophenol (Z)-24-ethylidenelophenol*citrostadienol 426.724 C30 H50 O1 CC=C(CCC(C)C2(CCC1(C3(=CCC4(C(C)C(O)CCC(C)(C(CCC(C)12)3)4)))))C(C)C PUBCHEM:25245448:*LIGAND-CPD:C11523: 2.1.1.143 24-methylenelophenol + S-adenosyl-L-methionine = H+ + 24-ethylidenelophenol + S-adenosyl-L-homocysteine plant sterol biosynthesis 5-methyl-tetrahydrofolate 5-methyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid*5-methyl-THF*n5-CH3-THF*CH3-THF*N5-methyltetrahydropteroyl mono-L-glutamate*5-methyl-tetrahydrofolate*5-methyl-5,6,7,8-tetrahydrofolate*n5-methyltetrahydrofolate*N5-methyl-THF*methyl-THF*methyl-tetrahydrofolate*methyl-H4F 457.445 C20 H23 N7 O6 CN1(C(CNC2(=C1C(N=C(N2)N)=O))CNC3(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C3)) PUBCHEM:444412:*CHEBI:15641:*LIGAND-CPD:C00440:*CAS:134-35-0 2.1.1.19 tetrahydrofolate + trimethyl sulfonium = H+ + dimethylsulfide + 5-methyl-tetrahydrofolate folate transformations I 5-methyl-tetrahydrofolate 5-methyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid*5-methyl-THF*n5-CH3-THF*CH3-THF*N5-methyltetrahydropteroyl mono-L-glutamate*5-methyl-tetrahydrofolate*5-methyl-5,6,7,8-tetrahydrofolate*n5-methyltetrahydrofolate*N5-methyl-THF*methyl-THF*methyl-tetrahydrofolate*methyl-H4F 457.445 C20 H23 N7 O6 CN1(C(CNC2(=C1C(N=C(N2)N)=O))CNC3(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C3)) PUBCHEM:444412:*CHEBI:15641:*LIGAND-CPD:C00440:*CAS:134-35-0 2.1.1.13 L-homocysteine + 5-methyl-tetrahydrofolate = L-methionine + tetrahydrofolate folate transformations I 5-methyl-tetrahydrofolate 5-methyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid*5-methyl-THF*n5-CH3-THF*CH3-THF*N5-methyltetrahydropteroyl mono-L-glutamate*5-methyl-tetrahydrofolate*5-methyl-5,6,7,8-tetrahydrofolate*n5-methyltetrahydrofolate*N5-methyl-THF*methyl-THF*methyl-tetrahydrofolate*methyl-H4F 457.445 C20 H23 N7 O6 CN1(C(CNC2(=C1C(N=C(N2)N)=O))CNC3(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C3)) PUBCHEM:444412:*CHEBI:15641:*LIGAND-CPD:C00440:*CAS:134-35-0 2.1.1.13 L-homocysteine + 5-methyl-tetrahydrofolate = L-methionine + tetrahydrofolate folate transformations II (plants) 5-methyl-tetrahydrofolate 5-methyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid*5-methyl-THF*n5-CH3-THF*CH3-THF*N5-methyltetrahydropteroyl mono-L-glutamate*5-methyl-tetrahydrofolate*5-methyl-5,6,7,8-tetrahydrofolate*n5-methyltetrahydrofolate*N5-methyl-THF*methyl-THF*methyl-tetrahydrofolate*methyl-H4F 457.445 C20 H23 N7 O6 CN1(C(CNC2(=C1C(N=C(N2)N)=O))CNC3(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C3)) PUBCHEM:444412:*CHEBI:15641:*LIGAND-CPD:C00440:*CAS:134-35-0 1.5.7.1 5-methyl-tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H+ folate transformations I 5-methyl-tetrahydrofolate 5-methyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid*5-methyl-THF*n5-CH3-THF*CH3-THF*N5-methyltetrahydropteroyl mono-L-glutamate*5-methyl-tetrahydrofolate*5-methyl-5,6,7,8-tetrahydrofolate*n5-methyltetrahydrofolate*N5-methyl-THF*methyl-THF*methyl-tetrahydrofolate*methyl-H4F 457.445 C20 H23 N7 O6 CN1(C(CNC2(=C1C(N=C(N2)N)=O))CNC3(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C3)) PUBCHEM:444412:*CHEBI:15641:*LIGAND-CPD:C00440:*CAS:134-35-0 1.5.1.20 5-methyl-tetrahydrofolate + NAD+ = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H+ + NADH folate transformations I 5-methyl-tetrahydrofolate 5-methyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid*5-methyl-THF*n5-CH3-THF*CH3-THF*N5-methyltetrahydropteroyl mono-L-glutamate*5-methyl-tetrahydrofolate*5-methyl-5,6,7,8-tetrahydrofolate*n5-methyltetrahydrofolate*N5-methyl-THF*methyl-THF*methyl-tetrahydrofolate*methyl-H4F 457.445 C20 H23 N7 O6 CN1(C(CNC2(=C1C(N=C(N2)N)=O))CNC3(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C3)) PUBCHEM:444412:*CHEBI:15641:*LIGAND-CPD:C00440:*CAS:134-35-0 1.5.1.20 5-methyl-tetrahydrofolate + NAD+ = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H+ + NADH folate transformations II (plants) 7,8-diaminopelargonate 7,8-diaminononanoate*7,8-diaminopelargonate*DAPA 189.277 C9 H21 N2 O2 C(C)(C(CCCCCC([O-])=O)[N+])[N+] CHEBI:58500:*PUBCHEM:25245451:*LIGAND-CPD:C01037: 2.6.1.62 S-adenosyl-L-methionine + 7-keto-8-aminopelargonate = S-adenosyl-4-methylthio-2-oxobutanoate + 7,8-diaminopelargonate biotin biosynthesis from 7-keto-8-aminopelargonate 7,8-diaminopelargonate 7,8-diaminononanoate*7,8-diaminopelargonate*DAPA 189.277 C9 H21 N2 O2 C(C)(C(CCCCCC([O-])=O)[N+])[N+] CHEBI:58500:*PUBCHEM:25245451:*LIGAND-CPD:C01037: 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = H+ + dethiobiotin + ADP biotin biosynthesis from 7-keto-8-aminopelargonate 3-methylcrotonyl-CoA β-methylcrotonoyl-CoA*3-methylbut-2-enoyl-CoA 845.604 C26 H38 N7 O17 P3 S1 C1(C(O)C(C(COP(=O)([O-])OP(=O)(OCC(C)(C)C(C(NCCC(NCCSC(C=C(C)C)=O)=O)=O)O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25244212:*LIGAND-CPD:C03069: 6.4.1.4 ATP + 3-methylcrotonyl-CoA + bicarbonate = H+ + ADP + 3-methylglutaconyl-CoA leucine degradation I 3-methylcrotonyl-CoA β-methylcrotonoyl-CoA*3-methylbut-2-enoyl-CoA 845.604 C26 H38 N7 O17 P3 S1 C1(C(O)C(C(COP(=O)([O-])OP(=O)(OCC(C)(C)C(C(NCCC(NCCSC(C=C(C)C)=O)=O)=O)O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25244212:*LIGAND-CPD:C03069: 1.3.99.10 isovaleryl-CoA = 3-methylcrotonyl-CoA leucine degradation I 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one*1,2-dihydroxy-3-keto-5-methylthiopentene anion*1,2-dihydroxy-3-keto-5-methylthiopentane*1,2-dihydroxy-3-keto-5-methylthiopentene 161.195 C6 H9 O3 S1 OC=C([O-])C(=O)CCSC CHEBI:58795:*PUBCHEM:44229177:*LIGAND-CPD:C15606: 2-hydroxy-3-keto-5-methylthio-1-phosphopentene + H2O = 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one methionine salvage I 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one*1,2-dihydroxy-3-keto-5-methylthiopentene anion*1,2-dihydroxy-3-keto-5-methylthiopentane*1,2-dihydroxy-3-keto-5-methylthiopentene 161.195 C6 H9 O3 S1 OC=C([O-])C(=O)CCSC CHEBI:58795:*PUBCHEM:44229177:*LIGAND-CPD:C15606: 1.13.11.54 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one + oxygen = H+ + 2-oxo-4-methylthiobutanoate + formate methionine salvage I trans-5-O-(4-coumaroyl)-D-quinate trans-5-O-(4-coumaroyl)quinate*4-coumaroylquinate*trans-(p-coumaroyl)-quinate*trans-5-O-(4-coumaroyl)quinate 337.305 C16 H17 O8 O=C(C=CC1(=CC=C(O)C=C1))OC2(CC(O)(CC(O)C(O)2)C(=O)[O-]) PUBCHEM:25244213:*LIGAND-CPD:C12208: 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ chlorogenic acid biosynthesis I trans-5-O-(4-coumaroyl)-D-quinate trans-5-O-(4-coumaroyl)quinate*4-coumaroylquinate*trans-(p-coumaroyl)-quinate*trans-5-O-(4-coumaroyl)quinate 337.305 C16 H17 O8 O=C(C=CC1(=CC=C(O)C=C1))OC2(CC(O)(CC(O)C(O)2)C(=O)[O-]) PUBCHEM:25244213:*LIGAND-CPD:C12208: 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ chlorogenic acid biosynthesis II trans-5-O-(4-coumaroyl)-D-quinate trans-5-O-(4-coumaroyl)quinate*4-coumaroylquinate*trans-(p-coumaroyl)-quinate*trans-5-O-(4-coumaroyl)quinate 337.305 C16 H17 O8 O=C(C=CC1(=CC=C(O)C=C1))OC2(CC(O)(CC(O)C(O)2)C(=O)[O-]) PUBCHEM:25244213:*LIGAND-CPD:C12208: 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ phenylpropanoid biosynthesis trans-5-O-(4-coumaroyl)-D-quinate trans-5-O-(4-coumaroyl)quinate*4-coumaroylquinate*trans-(p-coumaroyl)-quinate*trans-5-O-(4-coumaroyl)quinate 337.305 C16 H17 O8 O=C(C=CC1(=CC=C(O)C=C1))OC2(CC(O)(CC(O)C(O)2)C(=O)[O-]) PUBCHEM:25244213:*LIGAND-CPD:C12208: 2.3.1.133 4-coumaroyl-CoA + L-quinate = trans-5-O-(4-coumaroyl)-D-quinate + coenzyme A chlorogenic acid biosynthesis I trans-5-O-(4-coumaroyl)-D-quinate trans-5-O-(4-coumaroyl)quinate*4-coumaroylquinate*trans-(p-coumaroyl)-quinate*trans-5-O-(4-coumaroyl)quinate 337.305 C16 H17 O8 O=C(C=CC1(=CC=C(O)C=C1))OC2(CC(O)(CC(O)C(O)2)C(=O)[O-]) PUBCHEM:25244213:*LIGAND-CPD:C12208: 2.3.1.133 4-coumaroyl-CoA + L-quinate = trans-5-O-(4-coumaroyl)-D-quinate + coenzyme A chlorogenic acid biosynthesis II trans-5-O-(4-coumaroyl)-D-quinate trans-5-O-(4-coumaroyl)quinate*4-coumaroylquinate*trans-(p-coumaroyl)-quinate*trans-5-O-(4-coumaroyl)quinate 337.305 C16 H17 O8 O=C(C=CC1(=CC=C(O)C=C1))OC2(CC(O)(CC(O)C(O)2)C(=O)[O-]) PUBCHEM:25244213:*LIGAND-CPD:C12208: 2.3.1.133 4-coumaroyl-CoA + L-quinate = trans-5-O-(4-coumaroyl)-D-quinate + coenzyme A phenylpropanoid biosynthesis quercetin 3, 7, 4'-trisulphate quercetin 3, 7, 4-trisulphate 539.391 C15 H7 O16 S3 O=C1(C(OS(=O)(=O)[O-])=C(OC2(C=C(C=C(O)C1=2)OS(=O)(=O)[O-]))C3(=CC=C(OS(=O)(=O)[O-])C(O)=C3)) PUBCHEM:21676176: quercetin 3, 7, 4'-trisulphate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin 3, 7, 3', 4'-tetrasulphate quercetinsulphates biosynthesis quercetin 3, 7, 4'-trisulphate quercetin 3, 7, 4-trisulphate 539.391 C15 H7 O16 S3 O=C1(C(OS(=O)(=O)[O-])=C(OC2(C=C(C=C(O)C1=2)OS(=O)(=O)[O-]))C3(=CC=C(OS(=O)(=O)[O-])C(O)=C3)) PUBCHEM:21676176: quercetin-3,4'-bissulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + quercetin 3, 7, 4'-trisulphate quercetinsulphates biosynthesis D-ribulose-1,5-bisphosphate ribulose 1,5-bisphosphate*D-ribulose-1,5-diphosphate*D-ribulose-1,5-P2 306.059 C5 H8 O11 P2 P(=O)([O-])([O-])OCC(=O)C(O)C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007293*PUBCHEM:4337391:*LIGAND-CPD:C01182:*CAS:14689-84-0 2.7.1.19 D-ribulose-5-phosphate + ATP = H+ + D-ribulose-1,5-bisphosphate + ADP Rubisco shunt D-ribulose-1,5-bisphosphate ribulose 1,5-bisphosphate*D-ribulose-1,5-diphosphate*D-ribulose-1,5-P2 306.059 C5 H8 O11 P2 P(=O)([O-])([O-])OCC(=O)C(O)C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007293*PUBCHEM:4337391:*LIGAND-CPD:C01182:*CAS:14689-84-0 2.7.1.19 D-ribulose-5-phosphate + ATP = H+ + D-ribulose-1,5-bisphosphate + ADP Calvin-Benson-Bassham cycle D-ribulose-1,5-bisphosphate ribulose 1,5-bisphosphate*D-ribulose-1,5-diphosphate*D-ribulose-1,5-P2 306.059 C5 H8 O11 P2 P(=O)([O-])([O-])OCC(=O)C(O)C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007293*PUBCHEM:4337391:*LIGAND-CPD:C01182:*CAS:14689-84-0 4.1.1.- D-ribulose-1,5-bisphosphate + oxygen = 2-phosphoglycolate + 3-phospho-D-glycerate + H+ photorespiration D-ribulose-1,5-bisphosphate ribulose 1,5-bisphosphate*D-ribulose-1,5-diphosphate*D-ribulose-1,5-P2 306.059 C5 H8 O11 P2 P(=O)([O-])([O-])OCC(=O)C(O)C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007293*PUBCHEM:4337391:*LIGAND-CPD:C01182:*CAS:14689-84-0 4.1.1.39 D-ribulose-1,5-bisphosphate + CO2 + H2O = 3-phospho-D-glycerate + H+ Rubisco shunt D-ribulose-1,5-bisphosphate ribulose 1,5-bisphosphate*D-ribulose-1,5-diphosphate*D-ribulose-1,5-P2 306.059 C5 H8 O11 P2 P(=O)([O-])([O-])OCC(=O)C(O)C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007293*PUBCHEM:4337391:*LIGAND-CPD:C01182:*CAS:14689-84-0 4.1.1.39 D-ribulose-1,5-bisphosphate + CO2 + H2O = 3-phospho-D-glycerate + H+ Calvin-Benson-Bassham cycle phytyl diphosphate phytyl pyrophosphate*phytyl-PP 453.471 C20 H39 O7 P2 CC(CCCC(CCCC(CCCC(=CCOP([O-])(=O)OP([O-])(=O)[O-])C)C)C)C CHEBI:58404:*PUBCHEM:25244831:*LIGAND-CPD:C05427: H+ + homogentisate + phytyl diphosphate = 2-methyl-6-phytyl-1,4-benzoquinol + CO2 + diphosphate vitamin E biosynthesis phytyl diphosphate phytyl pyrophosphate*phytyl-PP 453.471 C20 H39 O7 P2 CC(CCCC(CCCC(CCCC(=CCOP([O-])(=O)OP([O-])(=O)[O-])C)C)C)C CHEBI:58404:*PUBCHEM:25244831:*LIGAND-CPD:C05427: 2.5.1.62 H+ + chlorophyllide a + phytyl diphosphate = chlorophyll a + diphosphate chlorophyll cycle phytyl diphosphate phytyl pyrophosphate*phytyl-PP 453.471 C20 H39 O7 P2 CC(CCCC(CCCC(CCCC(=CCOP([O-])(=O)OP([O-])(=O)[O-])C)C)C)C CHEBI:58404:*PUBCHEM:25244831:*LIGAND-CPD:C05427: 2.5.1.62 H+ + chlorophyllide a + phytyl diphosphate = chlorophyll a + diphosphate chlorophyll a biosynthesis I phytyl diphosphate phytyl pyrophosphate*phytyl-PP 453.471 C20 H39 O7 P2 CC(CCCC(CCCC(CCCC(=CCOP([O-])(=O)OP([O-])(=O)[O-])C)C)C)C CHEBI:58404:*PUBCHEM:25244831:*LIGAND-CPD:C05427: 2.5.1.- H+ + chlorophyllide b + phytyl diphosphate = chlorophyll b + diphosphate chlorophyll cycle Mg2+ magnesium*Mg+2*Mg++*magnesium ion 24.305 MG1 [Mg++] PUBCHEM:888:*CHEBI:18420:*LIGAND-CPD:C00305: H+ + chlorophyllide a = pheophorbide a + Mg2+ chlorophyll a degradation Mg2+ magnesium*Mg+2*Mg++*magnesium ion 24.305 MG1 [Mg++] PUBCHEM:888:*CHEBI:18420:*LIGAND-CPD:C00305: 6.6.1.1 ATP + protoporphyrin IX + Mg2+ + H2O = H+ + Mg-protoporphyrin + ADP chlorophyllide a biosynthesis I S-adenosyl-L-methioninamine S-adenosyl-(5')-3-methylthiopropylamine*dcSAM*decarboxylated AdoMet*(5-deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium salt*decarboxylated SAM*S-adenosylmethioninamine*decarboxylated S-adenosylmethionine*dAdoMet*S-methyl-S-adenosyl homocysteamine*3-amino-propyl-S-adenosine 356.442 C14 H24 N6 O3 S1 C3(C[S+](C)CCC[N+])(C(O)C(O)C(N1(C=NC2(=C1N=CN=C(N)2)))O3) CHEBI:57443:*PUBCHEM:25203490:*LIGAND-CPD:C01137: 2.5.1.22 spermidine + S-adenosyl-L-methioninamine = H+ + spermine + S-methyl-5'-thioadenosine spermine biosynthesis S-adenosyl-L-methioninamine S-adenosyl-(5')-3-methylthiopropylamine*dcSAM*decarboxylated AdoMet*(5-deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium salt*decarboxylated SAM*S-adenosylmethioninamine*decarboxylated S-adenosylmethionine*dAdoMet*S-methyl-S-adenosyl homocysteamine*3-amino-propyl-S-adenosine 356.442 C14 H24 N6 O3 S1 C3(C[S+](C)CCC[N+])(C(O)C(O)C(N1(C=NC2(=C1N=CN=C(N)2)))O3) CHEBI:57443:*PUBCHEM:25203490:*LIGAND-CPD:C01137: 4.1.1.50 H+ + S-adenosyl-L-methionine = CO2 + S-adenosyl-L-methioninamine spermine biosynthesis S-adenosyl-L-methioninamine S-adenosyl-(5')-3-methylthiopropylamine*dcSAM*decarboxylated AdoMet*(5-deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium salt*decarboxylated SAM*S-adenosylmethioninamine*decarboxylated S-adenosylmethionine*dAdoMet*S-methyl-S-adenosyl homocysteamine*3-amino-propyl-S-adenosine 356.442 C14 H24 N6 O3 S1 C3(C[S+](C)CCC[N+])(C(O)C(O)C(N1(C=NC2(=C1N=CN=C(N)2)))O3) CHEBI:57443:*PUBCHEM:25203490:*LIGAND-CPD:C01137: 4.1.1.50 H+ + S-adenosyl-L-methionine = CO2 + S-adenosyl-L-methioninamine spermidine biosynthesis I S-adenosyl-L-methioninamine S-adenosyl-(5')-3-methylthiopropylamine*dcSAM*decarboxylated AdoMet*(5-deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium salt*decarboxylated SAM*S-adenosylmethioninamine*decarboxylated S-adenosylmethionine*dAdoMet*S-methyl-S-adenosyl homocysteamine*3-amino-propyl-S-adenosine 356.442 C14 H24 N6 O3 S1 C3(C[S+](C)CCC[N+])(C(O)C(O)C(N1(C=NC2(=C1N=CN=C(N)2)))O3) CHEBI:57443:*PUBCHEM:25203490:*LIGAND-CPD:C01137: 2.5.1.16 putrescine + S-adenosyl-L-methioninamine = H+ + spermidine + S-methyl-5'-thioadenosine spermidine biosynthesis I L-γ-glutamylcysteine γ-glutamylcysteine*γ-L-glutamyl-L-cysteine 249.261 C8 H13 N2 O5 S1 C(CCC(=O)NC(C(=O)[O-])CS)(C([O-])=O)[N+] PUBCHEM:25244219:*LIGAND-CPD:C00669:*CAS:686-58-8 glutathione = L-γ-glutamylcysteine γ-glutamyl cycle (plant pathway) L-γ-glutamylcysteine γ-glutamylcysteine*γ-L-glutamyl-L-cysteine 249.261 C8 H13 N2 O5 S1 C(CCC(=O)NC(C(=O)[O-])CS)(C([O-])=O)[N+] PUBCHEM:25244219:*LIGAND-CPD:C00669:*CAS:686-58-8 6.3.2.2 L-cysteine + L-glutamate + ATP = H+ + L-γ-glutamylcysteine + ADP γ-glutamyl cycle (plant pathway) L-γ-glutamylcysteine γ-glutamylcysteine*γ-L-glutamyl-L-cysteine 249.261 C8 H13 N2 O5 S1 C(CCC(=O)NC(C(=O)[O-])CS)(C([O-])=O)[N+] PUBCHEM:25244219:*LIGAND-CPD:C00669:*CAS:686-58-8 6.3.2.2 L-cysteine + L-glutamate + ATP = H+ + L-γ-glutamylcysteine + ADP glutathione biosynthesis L-γ-glutamylcysteine γ-glutamylcysteine*γ-L-glutamyl-L-cysteine 249.261 C8 H13 N2 O5 S1 C(CCC(=O)NC(C(=O)[O-])CS)(C([O-])=O)[N+] PUBCHEM:25244219:*LIGAND-CPD:C00669:*CAS:686-58-8 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = H+ + glutathione + ADP γ-glutamyl cycle (plant pathway) L-γ-glutamylcysteine γ-glutamylcysteine*γ-L-glutamyl-L-cysteine 249.261 C8 H13 N2 O5 S1 C(CCC(=O)NC(C(=O)[O-])CS)(C([O-])=O)[N+] PUBCHEM:25244219:*LIGAND-CPD:C00669:*CAS:686-58-8 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = H+ + glutathione + ADP glutathione biosynthesis L-γ-glutamylcysteine γ-glutamylcysteine*γ-L-glutamyl-L-cysteine 249.261 C8 H13 N2 O5 S1 C(CCC(=O)NC(C(=O)[O-])CS)(C([O-])=O)[N+] PUBCHEM:25244219:*LIGAND-CPD:C00669:*CAS:686-58-8 L-γ-glutamylcysteine = 5-oxoproline γ-glutamyl cycle (plant pathway) gibberellin A20 GA20*gibberellin 20*GA20*gibberellin A20*gibberellin A20 331.388 C19 H23 O5 C1(CCC2(C4(C1(OC2=O)C5(CCC3(CC(CC3=C)(C4C([O-])=O)5)O)))(C)) PUBCHEM:25201798:*LIGAND-CPD:C02035: 1.14.11.- gibberellin A20 + 2-oxoglutarate + oxygen = GA29 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) gibberellin A20 GA20*gibberellin 20*GA20*gibberellin A20*gibberellin A20 331.388 C19 H23 O5 C1(CCC2(C4(C1(OC2=O)C5(CCC3(CC(CC3=C)(C4C([O-])=O)5)O)))(C)) PUBCHEM:25201798:*LIGAND-CPD:C02035: 1.14.11.- GA19 + oxygen + 2-oxoglutarate = H+ + gibberellin A20 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) gibberellin A20 GA20*gibberellin 20*GA20*gibberellin A20*gibberellin A20 331.388 C19 H23 O5 C1(CCC2(C4(C1(OC2=O)C5(CCC3(CC(CC3=C)(C4C([O-])=O)5)O)))(C)) PUBCHEM:25201798:*LIGAND-CPD:C02035: 1.14.11.15 gibberellin A20 + 2-oxoglutarate + oxygen = gibberellin A1 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) hypoxanthine 136.113 C5 H4 N4 O1 N2(C=NC1(NC=NC=1C(=O)2)) PUBCHEM:790:*CHEBI:17368:*LIGAND-CPD:C00262:*CAS:68-94-0 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ adenosine nucleotides degradation II hypoxanthine 136.113 C5 H4 N4 O1 N2(C=NC1(NC=NC=1C(=O)2)) PUBCHEM:790:*CHEBI:17368:*LIGAND-CPD:C00262:*CAS:68-94-0 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ adenosine nucleotides degradation I hypoxanthine 136.113 C5 H4 N4 O1 N2(C=NC1(NC=NC=1C(=O)2)) PUBCHEM:790:*CHEBI:17368:*LIGAND-CPD:C00262:*CAS:68-94-0 3.2.2.2 inosine + H2O = hypoxanthine adenosine nucleotides degradation I hypoxanthine 136.113 C5 H4 N4 O1 N2(C=NC1(NC=NC=1C(=O)2)) PUBCHEM:790:*CHEBI:17368:*LIGAND-CPD:C00262:*CAS:68-94-0 2.4.2.1 inosine = hypoxanthine + α-D-ribose-1-phosphate adenosine nucleotides degradation II 4α-formyl-ergosta-7,24(241)-dien-3β-ol 426.681 C29 H46 O2 C1(CC(C(C2(C1(C3(C(=CC2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))C=O)O) 1.14.13.- 4α-formyl-ergosta-7,24(241)-dien-3β-ol + oxygen + NADH = 4α-carboxy-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis 4α-formyl-ergosta-7,24(241)-dien-3β-ol 426.681 C29 H46 O2 C1(CC(C(C2(C1(C3(C(=CC2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))C=O)O) 1.14.13.- 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol + oxygen + NADH = 4α-formyl-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 2.7.1.1 α-D-glucose + ATP = H+ + α-D-glucose 6-phosphate + ADP sucrose degradation III α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 2.7.1.1 α-D-glucose + ATP = H+ + α-D-glucose 6-phosphate + ADP starch degradation α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate sucrose degradation III α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate GDP-glucose biosynthesis α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate glycogen degradation II α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate UDP-glucose biosynthesis (from glucose 6-phosphate) α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate starch degradation α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate glycogen degradation I α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate starch biosynthesis α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate glucose and glucose-1-phosphate degradation α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate sucrose biosynthesis α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 2.4.1.15 α-D-glucose 6-phosphate = H+ + UDP + trehalose 6-phosphate trehalose biosynthesis I α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 5.1.3.15 α-D-glucose 6-phosphate = β-D-glucose-6-phosphate sucrose degradation III α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 5.1.3.15 α-D-glucose 6-phosphate = β-D-glucose-6-phosphate GDP-glucose biosynthesis α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 5.1.3.15 α-D-glucose 6-phosphate = β-D-glucose-6-phosphate starch biosynthesis α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 5.1.3.15 α-D-glucose 6-phosphate = β-D-glucose-6-phosphate starch degradation α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 5.1.3.15 α-D-glucose 6-phosphate = β-D-glucose-6-phosphate glucose and glucose-1-phosphate degradation α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) PUBCHEM:21604864:*CHEBI:17665:*LIGAND:C00092:*CAS:56-73-5*CAS:56-73-5:*LIGAND-CPD:C00668: 5.1.3.15 α-D-glucose 6-phosphate = β-D-glucose-6-phosphate sucrose biosynthesis 2-monoacylglycerol 2-Monoacylglycerol*2-glyceride*2-acylglycerol C4 H7 O4 R1 O(C(CO)CO)C([R])=O LIGAND-CPD:C02112:*CHEBI:17389: 3.1.1.- H2O = 2-monoacylglycerol triacylglycerol degradation 2-monoacylglycerol 2-Monoacylglycerol*2-glyceride*2-acylglycerol C4 H7 O4 R1 O(C(CO)CO)C([R])=O LIGAND-CPD:C02112:*CHEBI:17389: 2-monoacylglycerol = 1-monoacylglycerol triacylglycerol degradation L-aspartyl-4-phosphate 4-phospho-L-aspartate*L-4-aspartyl phosphate*L-β-aspartyl-P*L-β-aspartyl-phosphate*L-aspartyl-4-P*L-aspartyl-β-phosphate 211.068 C4 H6 N1 O7 P1 O=C(CC([N+])C(=O)[O-])OP([O-])(=O)[O-] CHEBI:57535:*PUBCHEM:11948925:*LIGAND-CPD:C03082:*CAS:22138-53-0 2.7.2.4 L-aspartate + ATP = L-aspartyl-4-phosphate + ADP lysine biosynthesis VI L-aspartyl-4-phosphate 4-phospho-L-aspartate*L-4-aspartyl phosphate*L-β-aspartyl-P*L-β-aspartyl-phosphate*L-aspartyl-4-P*L-aspartyl-β-phosphate 211.068 C4 H6 N1 O7 P1 O=C(CC([N+])C(=O)[O-])OP([O-])(=O)[O-] CHEBI:57535:*PUBCHEM:11948925:*LIGAND-CPD:C03082:*CAS:22138-53-0 2.7.2.4 L-aspartate + ATP = L-aspartyl-4-phosphate + ADP homoserine biosynthesis L-aspartyl-4-phosphate 4-phospho-L-aspartate*L-4-aspartyl phosphate*L-β-aspartyl-P*L-β-aspartyl-phosphate*L-aspartyl-4-P*L-aspartyl-β-phosphate 211.068 C4 H6 N1 O7 P1 O=C(CC([N+])C(=O)[O-])OP([O-])(=O)[O-] CHEBI:57535:*PUBCHEM:11948925:*LIGAND-CPD:C03082:*CAS:22138-53-0 1.2.1.11 NADP+ + L-aspartate-semialdehyde = H+ + NADPH + L-aspartyl-4-phosphate lysine biosynthesis VI L-aspartyl-4-phosphate 4-phospho-L-aspartate*L-4-aspartyl phosphate*L-β-aspartyl-P*L-β-aspartyl-phosphate*L-aspartyl-4-P*L-aspartyl-β-phosphate 211.068 C4 H6 N1 O7 P1 O=C(CC([N+])C(=O)[O-])OP([O-])(=O)[O-] CHEBI:57535:*PUBCHEM:11948925:*LIGAND-CPD:C03082:*CAS:22138-53-0 1.2.1.11 NADP+ + L-aspartate-semialdehyde = H+ + NADPH + L-aspartyl-4-phosphate homoserine biosynthesis 3-demethylubiquinol-10 851.347 C58 H90 O4 C(C1(C(=C(C(OC)=C(O)C(O)=1)O)C))C=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C PUBCHEM:25244223: 1.14.-.- 6-methoxy-5-methyl-2-all-trans-decaprenyl-1,4-benzoquinol + oxygen = 3-demethylubiquinol-10 + H2O ubiquinol-10 biosynthesis (eukaryotic) 3-demethylubiquinol-10 851.347 C58 H90 O4 C(C1(C(=C(C(OC)=C(O)C(O)=1)O)C))C=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C PUBCHEM:25244223: 2.1.1.64 3-demethylubiquinol-10 + S-adenosyl-L-methionine = H+ + ubiquinol-10 + S-adenosyl-L-homocysteine ubiquinol-10 biosynthesis (eukaryotic) hydrogen sulfide hydrogen sulfide*sulfide*H2S 34.076 H2 S1 S CHEBI:16136:*CAS:7783-06-4:*PUBCHEM:402:*LIGAND-CPD:C00283:*LIGAND-CPD:C00283:*CAS:06/04/7783: 1.8.1.2 H2O + NADP+ + hydrogen sulfide = H+ + sulfite + NADPH sulfate reduction I (assimilatory) hydrogen sulfide hydrogen sulfide*sulfide*H2S 34.076 H2 S1 S CHEBI:16136:*CAS:7783-06-4:*PUBCHEM:402:*LIGAND-CPD:C00283:*LIGAND-CPD:C00283:*CAS:06/04/7783: 4.4.1.9 L-cysteine + hydrogen cyanide = hydrogen sulfide + 3-cyano-L-alanine + H+ cyanide detoxification hydrogen sulfide hydrogen sulfide*sulfide*H2S 34.076 H2 S1 S CHEBI:16136:*CAS:7783-06-4:*PUBCHEM:402:*LIGAND-CPD:C00283:*LIGAND-CPD:C00283:*CAS:06/04/7783: 4.4.1.9 L-cysteine + hydrogen cyanide = hydrogen sulfide + 3-cyano-L-alanine + H+ cyanide degradation hydrogen sulfide hydrogen sulfide*sulfide*H2S 34.076 H2 S1 S CHEBI:16136:*CAS:7783-06-4:*PUBCHEM:402:*LIGAND-CPD:C00283:*LIGAND-CPD:C00283:*CAS:06/04/7783: 2.5.1.47 O-acetyl-L-serine + hydrogen sulfide = H+ + L-cysteine + acetate cysteine biosynthesis I hydrogen sulfide hydrogen sulfide*sulfide*H2S 34.076 H2 S1 S CHEBI:16136:*CAS:7783-06-4:*PUBCHEM:402:*LIGAND-CPD:C00283:*LIGAND-CPD:C00283:*CAS:06/04/7783: 1.8.7.1 hydrogen sulfide + H2O = sulfite sulfate reduction II (assimilatory) 7,8-dihydropteroate dihydropterate*H2Pte*dihydropteroate 313.295 C14 H13 N6 O3 NC3(=NC(C1(=C(NCC(=N1)CNC2(=CC=C(C([O-])=O)C=C2))N3))=O) CHEBI:17839:*PUBCHEM:5459950:*LIGAND-CPD:C00921: 2.5.1.15 p-aminobenzoate + 6-hydroxymethyl-dihydropterin diphosphate = 7,8-dihydropteroate + diphosphate tetrahydrofolate biosynthesis 7,8-dihydropteroate dihydropterate*H2Pte*dihydropteroate 313.295 C14 H13 N6 O3 NC3(=NC(C1(=C(NCC(=N1)CNC2(=CC=C(C([O-])=O)C=C2))N3))=O) CHEBI:17839:*PUBCHEM:5459950:*LIGAND-CPD:C00921: 6.3.2.12 L-glutamate + 7,8-dihydropteroate + ATP = H+ + 7,8-dihydrofolate monoglutamate + ADP tetrahydrofolate biosynthesis cysteinylglycine Cys-Gly 178.206 C5 H10 N2 O3 S1 N(CC([O-])=O)C(C(CS)[N+])=O CHEBI:356322:*PUBCHEM:25244227:*LIGAND-CPD:C01419: glutathione = 5-oxoproline + cysteinylglycine γ-glutamyl cycle (plant pathway) cysteinylglycine Cys-Gly 178.206 C5 H10 N2 O3 S1 N(CC([O-])=O)C(C(CS)[N+])=O CHEBI:356322:*PUBCHEM:25244227:*LIGAND-CPD:C01419: 2.3.2.2 hypoglycin A + glutathione = hypoglycin B + cysteinylglycine hypoglycin biosynthesis cysteinylglycine Cys-Gly 178.206 C5 H10 N2 O3 S1 N(CC([O-])=O)C(C(CS)[N+])=O CHEBI:356322:*PUBCHEM:25244227:*LIGAND-CPD:C01419: 3.4.11.2 cysteinylglycine + H2O = L-cysteine + glycine γ-glutamyl cycle (plant pathway) cysteinylglycine Cys-Gly 178.206 C5 H10 N2 O3 S1 N(CC([O-])=O)C(C(CS)[N+])=O CHEBI:356322:*PUBCHEM:25244227:*LIGAND-CPD:C01419: 3.4.11.2 cysteinylglycine + H2O = L-cysteine + glycine glutathione degradation cysteinylglycine Cys-Gly 178.206 C5 H10 N2 O3 S1 N(CC([O-])=O)C(C(CS)[N+])=O CHEBI:356322:*PUBCHEM:25244227:*LIGAND-CPD:C01419: 3.4.11.2 cysteinylglycine + H2O = L-cysteine + glycine γ-glutamyl cycle cysteinylglycine Cys-Gly 178.206 C5 H10 N2 O3 S1 N(CC([O-])=O)C(C(CS)[N+])=O CHEBI:356322:*PUBCHEM:25244227:*LIGAND-CPD:C01419: 2.3.2.2 glutathione + H2O = cysteinylglycine + L-glutamate glutathione degradation cysteinylglycine Cys-Gly 178.206 C5 H10 N2 O3 S1 N(CC([O-])=O)C(C(CS)[N+])=O CHEBI:356322:*PUBCHEM:25244227:*LIGAND-CPD:C01419: 2.3.2.2 cysteinylglycine = glutathione γ-glutamyl cycle 2-oxohexa-4,5-cyclopropyl-5-enoate 2-keto-4,5-cyclopropylhex-5-enoate*2-(2-methylidenecyclopropyl)-2-oxoacetate 125.104 C6 H5 O3 C1(CC(C(C([O-])=O)=O)1)(=C) PUBCHEM:25200910: 2.3.-.- 2-oxohexa-4,5-cyclopropyl-5-enoate + acetyl-CoA + H2O = H+ + 3-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate + coenzyme A hypoglycin biosynthesis 2-oxohexa-4,5-cyclopropyl-5-enoate 2-keto-4,5-cyclopropylhex-5-enoate*2-(2-methylidenecyclopropyl)-2-oxoacetate 125.104 C6 H5 O3 C1(CC(C(C([O-])=O)=O)1)(=C) PUBCHEM:25200910: 2.6.1.- 2-oxohexa-4,5-cyclopropyl-5-enoate = L-α-(methylenecyclopropyl)-glycine hypoglycin biosynthesis 2-oxohexa-4,5-cyclopropyl-5-enoate 2-keto-4,5-cyclopropylhex-5-enoate*2-(2-methylidenecyclopropyl)-2-oxoacetate 125.104 C6 H5 O3 C1(CC(C(C([O-])=O)=O)1)(=C) PUBCHEM:25200910: 2-oxopenta-3,4-dienoate = 2-oxohexa-4,5-cyclopropyl-5-enoate hypoglycin biosynthesis 24-methylenelophenol cpd-4101*cdp-4101*4α-methyl-5α-ergosta-7,24-dien-3β-ol 412.698 C29 H48 O1 C1(CC(C(C2(C1(C3(C(=CC2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))C)O) PUBCHEM:25201809:*LIGAND-CPD:C11522: 1.14.13.- 24-methylenelophenol + oxygen + NADH = 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis 24-methylenelophenol cpd-4101*cdp-4101*4α-methyl-5α-ergosta-7,24-dien-3β-ol 412.698 C29 H48 O1 C1(CC(C(C2(C1(C3(C(=CC2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))C)O) PUBCHEM:25201809:*LIGAND-CPD:C11522: 5.3.3.5 4α-methyl-5α-ergosta-8,14,24(28)-dien-3β-ol = 24-methylenelophenol plant sterol biosynthesis 24-methylenelophenol cpd-4101*cdp-4101*4α-methyl-5α-ergosta-7,24-dien-3β-ol 412.698 C29 H48 O1 C1(CC(C(C2(C1(C3(C(=CC2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))C)O) PUBCHEM:25201809:*LIGAND-CPD:C11522: 2.1.1.143 24-methylenelophenol + S-adenosyl-L-methionine = H+ + 24-ethylidenelophenol + S-adenosyl-L-homocysteine plant sterol biosynthesis 4-hydroxysphinganine phytosphingosine*PHS 318.519 C18 H40 N1 O3 CCCCCCCCCCCCCCC(O)C(O)C([N+])CO PUBCHEM:25203595:*CHEBI:46961:*LIGAND-CPD:C12144: 1.14.-.- H+ + sphinganine + oxygen + NADPH = 4-hydroxysphinganine + H2O + NADP+ sphingolipid biosynthesis (plants) herniarin herniarine*ayapanin*7-methoxycoumarin*methylumbelliferone 176.171 C10 H8 O3 COC1(C=C2(C(=CC=1)C=CC(=O)O2)) herniarin = isoscopoletin simplecoumarins biosynthesis herniarin herniarine*ayapanin*7-methoxycoumarin*methylumbelliferone 176.171 C10 H8 O3 COC1(C=C2(C(=CC=1)C=CC(=O)O2)) umbelliferone = herniarin simplecoumarins biosynthesis sinapate 3,5-dimethoxy-4-hydroxycinnamate*sinapinate*sinapinic acid*sinapic acid*3,5-dimethoxy-4-hydroxycinnamic acid 223.205 C11 H11 O5 O(C1(C=C(C=C(OC)C(O)=1)C=CC([O-])=O))C PUBCHEM:5460292:*CHEBI:30023:*LIGAND-CPD:C00482:*NCI:59261*CAS:530-59-6 2.1.1.68 5-hydroxyferulate + S-adenosyl-L-methionine = H+ + sinapate + S-adenosyl-L-homocysteine free phenylpropanoid acid biosynthesis sinapate 3,5-dimethoxy-4-hydroxycinnamate*sinapinate*sinapinic acid*sinapic acid*3,5-dimethoxy-4-hydroxycinnamic acid 223.205 C11 H11 O5 O(C1(C=C(C=C(OC)C(O)=1)C=CC([O-])=O))C PUBCHEM:5460292:*CHEBI:30023:*LIGAND-CPD:C00482:*NCI:59261*CAS:530-59-6 1.2.1.68 sinapaldehyde + NADP+ + H2O = H+ + sinapate + NADPH ferulate and sinapate biosynthesis glycerol 1,2,3-trihydroxypropane*glycerin*1,2,3-trihydroxypropanol 92.094 C3 H8 O3 C(CO)(O)CO PUBCHEM:753:*CHEBI:17754:*LIGAND-CPD:C00116:*CAS:56-81-5 3.1.1.23 1-monoacylglycerol + H2O = glycerol triacylglycerol degradation glycerol 1,2,3-trihydroxypropane*glycerin*1,2,3-trihydroxypropanol 92.094 C3 H8 O3 C(CO)(O)CO PUBCHEM:753:*CHEBI:17754:*LIGAND-CPD:C00116:*CAS:56-81-5 2.7.1.30 glycerol + ATP = H+ + sn-glycerol-3-phosphate + ADP glycerol degradation IV glycerol 1,2,3-trihydroxypropane*glycerin*1,2,3-trihydroxypropanol 92.094 C3 H8 O3 C(CO)(O)CO PUBCHEM:753:*CHEBI:17754:*LIGAND-CPD:C00116:*CAS:56-81-5 2.7.1.30 glycerol + ATP = H+ + sn-glycerol-3-phosphate + ADP glycerol degradation I phosphoadenosine-5'-phosphosulfate PAPS*phosphoadenosine phosphosulfate*3'-phosphoadenosine-5'-phosphosulfate*3'-phosphoadenylyl-sulfate*3'-phospho-5'-adenylyl sulfate 503.23 C10 H11 N5 O13 P2 S1 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP(=O)([O-])[O-])COP(=O)(OS([O-])(=O)=O)[O-])))N) PUBCHEM:4428037:*KNAPSACK:C00007446:*LIGAND-CPD:C00053:*CAS:482-67-7 quercetin 3, 7, 4'-trisulphate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin 3, 7, 3', 4'-tetrasulphate quercetinsulphates biosynthesis phosphoadenosine-5'-phosphosulfate PAPS*phosphoadenosine phosphosulfate*3'-phosphoadenosine-5'-phosphosulfate*3'-phosphoadenylyl-sulfate*3'-phospho-5'-adenylyl sulfate 503.23 C10 H11 N5 O13 P2 S1 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP(=O)([O-])[O-])COP(=O)(OS([O-])(=O)=O)[O-])))N) PUBCHEM:4428037:*KNAPSACK:C00007446:*LIGAND-CPD:C00053:*CAS:482-67-7 isorhamnetin 3-sulphate + phosphoadenosine-5'-phosphosulfate = H+ + adenosine 3',5'-bisphosphate + isorhamnetin 3, 4'-bisulphate quercetinsulphates biosynthesis phosphoadenosine-5'-phosphosulfate PAPS*phosphoadenosine phosphosulfate*3'-phosphoadenosine-5'-phosphosulfate*3'-phosphoadenylyl-sulfate*3'-phospho-5'-adenylyl sulfate 503.23 C10 H11 N5 O13 P2 S1 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP(=O)([O-])[O-])COP(=O)(OS([O-])(=O)=O)[O-])))N) PUBCHEM:4428037:*KNAPSACK:C00007446:*LIGAND-CPD:C00053:*CAS:482-67-7 quercetin 3,3',7-trissulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin 3, 7, 3', 4'-tetrasulphate quercetinsulphates biosynthesis phosphoadenosine-5'-phosphosulfate PAPS*phosphoadenosine phosphosulfate*3'-phosphoadenosine-5'-phosphosulfate*3'-phosphoadenylyl-sulfate*3'-phospho-5'-adenylyl sulfate 503.23 C10 H11 N5 O13 P2 S1 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP(=O)([O-])[O-])COP(=O)(OS([O-])(=O)=O)[O-])))N) PUBCHEM:4428037:*KNAPSACK:C00007446:*LIGAND-CPD:C00053:*CAS:482-67-7 isorhamnetin + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + isorhamnetin 3-sulphate quercetinsulphates biosynthesis phosphoadenosine-5'-phosphosulfate PAPS*phosphoadenosine phosphosulfate*3'-phosphoadenosine-5'-phosphosulfate*3'-phosphoadenylyl-sulfate*3'-phospho-5'-adenylyl sulfate 503.23 C10 H11 N5 O13 P2 S1 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP(=O)([O-])[O-])COP(=O)(OS([O-])(=O)=O)[O-])))N) PUBCHEM:4428037:*KNAPSACK:C00007446:*LIGAND-CPD:C00053:*CAS:482-67-7 1.8.4.8 adenosine 3',5'-bisphosphate + sulfite = phosphoadenosine-5'-phosphosulfate sulfate reduction I (assimilatory) phosphoadenosine-5'-phosphosulfate PAPS*phosphoadenosine phosphosulfate*3'-phosphoadenosine-5'-phosphosulfate*3'-phosphoadenylyl-sulfate*3'-phospho-5'-adenylyl sulfate 503.23 C10 H11 N5 O13 P2 S1 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP(=O)([O-])[O-])COP(=O)(OS([O-])(=O)=O)[O-])))N) PUBCHEM:4428037:*KNAPSACK:C00007446:*LIGAND-CPD:C00053:*CAS:482-67-7 2.8.2.28 quercetin-3,3'-bissulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + quercetin 3,3',7-trissulfate quercetinsulphates biosynthesis phosphoadenosine-5'-phosphosulfate PAPS*phosphoadenosine phosphosulfate*3'-phosphoadenosine-5'-phosphosulfate*3'-phosphoadenylyl-sulfate*3'-phospho-5'-adenylyl sulfate 503.23 C10 H11 N5 O13 P2 S1 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP(=O)([O-])[O-])COP(=O)(OS([O-])(=O)=O)[O-])))N) PUBCHEM:4428037:*KNAPSACK:C00007446:*LIGAND-CPD:C00053:*CAS:482-67-7 2.7.1.25 adenosine 5'-phosphosulfate + ATP = H+ + phosphoadenosine-5'-phosphosulfate + ADP sulfate activation for sulfonation phosphoadenosine-5'-phosphosulfate PAPS*phosphoadenosine phosphosulfate*3'-phosphoadenosine-5'-phosphosulfate*3'-phosphoadenylyl-sulfate*3'-phospho-5'-adenylyl sulfate 503.23 C10 H11 N5 O13 P2 S1 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP(=O)([O-])[O-])COP(=O)(OS([O-])(=O)=O)[O-])))N) PUBCHEM:4428037:*KNAPSACK:C00007446:*LIGAND-CPD:C00053:*CAS:482-67-7 2.8.2.26 quercetin 3-sulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin-3,3'-bissulfate quercetinsulphates biosynthesis phosphoadenosine-5'-phosphosulfate PAPS*phosphoadenosine phosphosulfate*3'-phosphoadenosine-5'-phosphosulfate*3'-phosphoadenylyl-sulfate*3'-phospho-5'-adenylyl sulfate 503.23 C10 H11 N5 O13 P2 S1 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP(=O)([O-])[O-])COP(=O)(OS([O-])(=O)=O)[O-])))N) PUBCHEM:4428037:*KNAPSACK:C00007446:*LIGAND-CPD:C00053:*CAS:482-67-7 2.8.2.25 quercetin + phosphoadenosine-5'-phosphosulfate = H+ + adenosine 3',5'-bisphosphate + quercetin 3-sulfate quercetinsulphates biosynthesis phosphoadenosine-5'-phosphosulfate PAPS*phosphoadenosine phosphosulfate*3'-phosphoadenosine-5'-phosphosulfate*3'-phosphoadenylyl-sulfate*3'-phospho-5'-adenylyl sulfate 503.23 C10 H11 N5 O13 P2 S1 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP(=O)([O-])[O-])COP(=O)(OS([O-])(=O)=O)[O-])))N) PUBCHEM:4428037:*KNAPSACK:C00007446:*LIGAND-CPD:C00053:*CAS:482-67-7 2.8.2.27 quercetin 3-sulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin-3,4'-bissulfate quercetinsulphates biosynthesis phosphoadenosine-5'-phosphosulfate PAPS*phosphoadenosine phosphosulfate*3'-phosphoadenosine-5'-phosphosulfate*3'-phosphoadenylyl-sulfate*3'-phospho-5'-adenylyl sulfate 503.23 C10 H11 N5 O13 P2 S1 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP(=O)([O-])[O-])COP(=O)(OS([O-])(=O)=O)[O-])))N) PUBCHEM:4428037:*KNAPSACK:C00007446:*LIGAND-CPD:C00053:*CAS:482-67-7 quercetin-3,4'-bissulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + quercetin 3, 7, 4'-trisulphate quercetinsulphates biosynthesis trans-neoxanthin 600.88 C40 H56 O4 C1(C(C(C(CC1O)(C)O)=C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC23(C(CC(CC2(C)C)O)(C)O3))C)C)(C)C) PUBCHEM:25244234:*LIGAND-CPD:C08606: 5.3.99.9 violaxanthin = trans-neoxanthin abscisic acid biosynthesis trans-neoxanthin 600.88 C40 H56 O4 C1(C(C(C(CC1O)(C)O)=C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC23(C(CC(CC2(C)C)O)(C)O3))C)C)(C)C) PUBCHEM:25244234:*LIGAND-CPD:C08606: trans-neoxanthin = 9'-cis-neoxanthin abscisic acid biosynthesis α-humulene humulene*2,6,6,9-tetramethyl-1,4,8-cycloundecatriene*2,6,6,9-tetramethyl-cycloundeca-1,4,8-triene 204.355 C15 H24 C1(C(=CCC(C=CCC(=CC1)C)(C)C)C) PUBCHEM:5281520:*CHEBI:5768:*LIGAND-CPD:C09684: 4.2.3.- (2E,6E)-farnesyl diphosphate = α-humulene + diphosphate β-caryophyllene biosynthesis GA19 GA19*gibberellin A19*gibberellin A19 360.406 C20 H24 O6 C1(CCC(C2(C(C34(CC(CCC(C1(C=O)2)3)(C(C4)=C)O))C([O-])=O))(C)C([O-])=O) CHEBI:58587:*PUBCHEM:25200921:*LIGAND-CPD:C02034: 1.14.11.- GA19 + oxygen + 2-oxoglutarate = H+ + gibberellin A20 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) GA19 GA19*gibberellin A19*gibberellin A19 360.406 C20 H24 O6 C1(CCC(C2(C(C34(CC(CCC(C1(C=O)2)3)(C(C4)=C)O))C([O-])=O))(C)C([O-])=O) CHEBI:58587:*PUBCHEM:25200921:*LIGAND-CPD:C02034: 1.14.11.- GA19 + oxygen + 2-oxoglutarate = H+ + GA17 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) GA19 GA19*gibberellin A19*gibberellin A19 360.406 C20 H24 O6 C1(CCC(C2(C(C34(CC(CCC(C1(C=O)2)3)(C(C4)=C)O))C([O-])=O))(C)C([O-])=O) CHEBI:58587:*PUBCHEM:25200921:*LIGAND-CPD:C02034: 1.14.11.12 GA44 (open lactone form) + 2-oxoglutarate + oxygen = GA19 + succinate + CO2 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) hydroxymethylpyrimidine phosphate 4-amino-2-methyl-5-phosphomethylpyrimidine*4-amino-5-phosphomethyl-2-methylpyrimidine*HMP-P*4-amino-5-hydroxymethyl-2-methylpyrimidine-P*4-amino-5-hydroxymethyl-2-methylpyrimidine-phosphate 217.121 C6 H8 N3 O4 P1 N1(C(N)=C(COP(=O)([O-])[O-])C=NC(C)=1) PUBCHEM:25244846:*LIGAND-CPD:C04556: 4.1.99.- 5-aminoimidazole ribonucleotide + S-adenosyl-L-methionine = hydroxymethylpyrimidine phosphate + 5'-deoxyadenosine + L-methionine + formate + carbon monoxide + H+ thiamine biosynthesis II hydroxymethylpyrimidine phosphate 4-amino-2-methyl-5-phosphomethylpyrimidine*4-amino-5-phosphomethyl-2-methylpyrimidine*HMP-P*4-amino-5-hydroxymethyl-2-methylpyrimidine-P*4-amino-5-hydroxymethyl-2-methylpyrimidine-phosphate 217.121 C6 H8 N3 O4 P1 N1(C(N)=C(COP(=O)([O-])[O-])C=NC(C)=1) PUBCHEM:25244846:*LIGAND-CPD:C04556: 2.7.4.7 hydroxymethylpyrimidine phosphate + ATP = 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate + ADP thiamine biosynthesis II hydroxymethylpyrimidine phosphate 4-amino-2-methyl-5-phosphomethylpyrimidine*4-amino-5-phosphomethyl-2-methylpyrimidine*HMP-P*4-amino-5-hydroxymethyl-2-methylpyrimidine-P*4-amino-5-hydroxymethyl-2-methylpyrimidine-phosphate 217.121 C6 H8 N3 O4 P1 N1(C(N)=C(COP(=O)([O-])[O-])C=NC(C)=1) PUBCHEM:25244846:*LIGAND-CPD:C04556: 2.7.1.49 ATP + hydroxymethylpyrimidine = H+ + ADP + hydroxymethylpyrimidine phosphate thiamine biosynthesis II feruloyl-CoA trans-feruloyl-CoA 939.674 C31 H40 N7 O19 P3 S1 C4(C=CC(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)(C=C(OC)C(O)=CC=4) CHEBI:57276:*PUBCHEM:44229137:*PUBCHEM:25244845:*PUBCHEM:656487:*PUBCHEM:11966129:*PUBCHEM:5280347:*LIGAND-CPD:C00406: 6.2.1.34 ferulate + ATP + coenzyme A = feruloyl-CoA + AMP + diphosphate suberin biosynthesis feruloyl-CoA trans-feruloyl-CoA 939.674 C31 H40 N7 O19 P3 S1 C4(C=CC(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)(C=C(OC)C(O)=CC=4) CHEBI:57276:*PUBCHEM:44229137:*PUBCHEM:25244845:*PUBCHEM:656487:*PUBCHEM:11966129:*PUBCHEM:5280347:*LIGAND-CPD:C00406: 2.3.1.110 feruloyl-CoA + tyramine = H+ + N-feruloyltyramine + coenzyme A suberin biosynthesis feruloyl-CoA trans-feruloyl-CoA 939.674 C31 H40 N7 O19 P3 S1 C4(C=CC(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)(C=C(OC)C(O)=CC=4) CHEBI:57276:*PUBCHEM:44229137:*PUBCHEM:25244845:*PUBCHEM:656487:*PUBCHEM:11966129:*PUBCHEM:5280347:*LIGAND-CPD:C00406: 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = H+ + feruloyl-CoA + S-adenosyl-L-homocysteine chlorogenic acid biosynthesis I feruloyl-CoA trans-feruloyl-CoA 939.674 C31 H40 N7 O19 P3 S1 C4(C=CC(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)(C=C(OC)C(O)=CC=4) CHEBI:57276:*PUBCHEM:44229137:*PUBCHEM:25244845:*PUBCHEM:656487:*PUBCHEM:11966129:*PUBCHEM:5280347:*LIGAND-CPD:C00406: 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = H+ + feruloyl-CoA + S-adenosyl-L-homocysteine suberin biosynthesis feruloyl-CoA trans-feruloyl-CoA 939.674 C31 H40 N7 O19 P3 S1 C4(C=CC(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)(C=C(OC)C(O)=CC=4) CHEBI:57276:*PUBCHEM:44229137:*PUBCHEM:25244845:*PUBCHEM:656487:*PUBCHEM:11966129:*PUBCHEM:5280347:*LIGAND-CPD:C00406: 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = H+ + feruloyl-CoA + S-adenosyl-L-homocysteine phenylpropanoid biosynthesis feruloyl-CoA trans-feruloyl-CoA 939.674 C31 H40 N7 O19 P3 S1 C4(C=CC(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)(C=C(OC)C(O)=CC=4) CHEBI:57276:*PUBCHEM:44229137:*PUBCHEM:25244845:*PUBCHEM:656487:*PUBCHEM:11966129:*PUBCHEM:5280347:*LIGAND-CPD:C00406: 1.2.1.44 H+ + feruloyl-CoA + NADPH = coniferaldehyde + NADP+ + coenzyme A phenylpropanoid biosynthesis xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 N2(C1(=C(NC=N1)C(=O)NC2=O)) PUBCHEM:1188:*CHEBI:17712:*LIGAND-CPD:C00385:*CAS:69-89-6 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ adenosine nucleotides degradation II xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 N2(C1(=C(NC=N1)C(=O)NC2=O)) PUBCHEM:1188:*CHEBI:17712:*LIGAND-CPD:C00385:*CAS:69-89-6 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ adenosine nucleotides degradation I xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 N2(C1(=C(NC=N1)C(=O)NC2=O)) PUBCHEM:1188:*CHEBI:17712:*LIGAND-CPD:C00385:*CAS:69-89-6 3.2.2.1 xanthosine + H2O = xanthine adenosine nucleotides degradation I xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 N2(C1(=C(NC=N1)C(=O)NC2=O)) PUBCHEM:1188:*CHEBI:17712:*LIGAND-CPD:C00385:*CAS:69-89-6 3.5.4.3 H2O + guanine = ammonia + xanthine guanosine nucleotides degradation II xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 N2(C1(=C(NC=N1)C(=O)NC2=O)) PUBCHEM:1188:*CHEBI:17712:*LIGAND-CPD:C00385:*CAS:69-89-6 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ adenosine nucleotides degradation II xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 N2(C1(=C(NC=N1)C(=O)NC2=O)) PUBCHEM:1188:*CHEBI:17712:*LIGAND-CPD:C00385:*CAS:69-89-6 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ adenosine nucleotides degradation I xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 N2(C1(=C(NC=N1)C(=O)NC2=O)) PUBCHEM:1188:*CHEBI:17712:*LIGAND-CPD:C00385:*CAS:69-89-6 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ guanosine nucleotides degradation II acetoacetate 3-ketobutyrate*3-oxobutanate*oxobutyrate*acetoacetic acid*3-oxobutyric acid*3-oxobutanoic acid*diacetic acid*β-ketobutyric acid 101.082 C4 H5 O3 C(C([O-])=O)C(C)=O PUBCHEM:6971017:*PUBCHEM:6971017:*CHEBI:13705:*LIGAND-CPD:C00164:*CAS:541-50-4 4.1.3.4 (S)-3-hydroxy-3-methylglutaryl-CoA = acetoacetate + acetyl-CoA leucine degradation I esculetin 6, 7-dihydroxycoumarin*6,7-Dihydroxy-2-chromenone*Cichorigenin 178.144 C9 H6 O4 OC2(C(O)=CC1(=C(OC(=O)C=C1)C=2)) CHEBI:490095:*|Wikipedia|:Aesculetin:*PUBCHEM:5281416:*LIGAND-CPD:C09263: H+ + 3,4,6-trihydroxy-cis-cinnamate = esculetin + H2O esculetin biosynthesis esculetin 6, 7-dihydroxycoumarin*6,7-Dihydroxy-2-chromenone*Cichorigenin 178.144 C9 H6 O4 OC2(C(O)=CC1(=C(OC(=O)C=C1)C=2)) CHEBI:490095:*|Wikipedia|:Aesculetin:*PUBCHEM:5281416:*LIGAND-CPD:C09263: esculetin = scopoletin simplecoumarins biosynthesis esculetin 6, 7-dihydroxycoumarin*6,7-Dihydroxy-2-chromenone*Cichorigenin 178.144 C9 H6 O4 OC2(C(O)=CC1(=C(OC(=O)C=C1)C=2)) CHEBI:490095:*|Wikipedia|:Aesculetin:*PUBCHEM:5281416:*LIGAND-CPD:C09263: esculetin = isoscopoletin simplecoumarins biosynthesis esculetin 6, 7-dihydroxycoumarin*6,7-Dihydroxy-2-chromenone*Cichorigenin 178.144 C9 H6 O4 OC2(C(O)=CC1(=C(OC(=O)C=C1)C=2)) CHEBI:490095:*|Wikipedia|:Aesculetin:*PUBCHEM:5281416:*LIGAND-CPD:C09263: 2-hydroxycaffeate = esculetin simplecoumarins biosynthesis esculetin 6, 7-dihydroxycoumarin*6,7-Dihydroxy-2-chromenone*Cichorigenin 178.144 C9 H6 O4 OC2(C(O)=CC1(=C(OC(=O)C=C1)C=2)) CHEBI:490095:*|Wikipedia|:Aesculetin:*PUBCHEM:5281416:*LIGAND-CPD:C09263: umbelliferone = esculetin simplecoumarins biosynthesis (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate SHCHC*(1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate*2-(3-CARBOXYPROPIONYL)-6-HYDROXY-CYCLOHEXA-2,4-DIENE CARBOXYLIC ACID 238.196 C11 H10 O6 O=C([O-])CCC(=O)C1(=CC=CC(O)C(C(=O)[O-])1) CHEBI:58689:*PUBCHEM:25246102:*LIGAND-CPD:C05817: 4.2.99.20 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate = H+ + (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + pyruvate 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate SHCHC*(1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate*2-(3-CARBOXYPROPIONYL)-6-HYDROXY-CYCLOHEXA-2,4-DIENE CARBOXYLIC ACID 238.196 C11 H10 O6 O=C([O-])CCC(=O)C1(=CC=CC(O)C(C(=O)[O-])1) CHEBI:58689:*PUBCHEM:25246102:*LIGAND-CPD:C05817: 4.2.1.113 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate = o-succinylbenzoate + H2O 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) 24-methyldesmosterol 398.671 C28 H46 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CCC(=C(C)C)C)C)C(CC3)(C)4)))C))O) PUBCHEM:25203608: 1.3.-.- H+ + 24-methyldesmosterol = 24-epi-campesterol plant sterol biosynthesis 24-methyldesmosterol 398.671 C28 H46 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CCC(=C(C)C)C)C)C(CC3)(C)4)))C))O) PUBCHEM:25203608: 24-methylenecholesterol = 24-methyldesmosterol plant sterol biosynthesis 24-methyldesmosterol 398.671 C28 H46 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CCC(=C(C)C)C)C)C(CC3)(C)4)))C))O) PUBCHEM:25203608: 1.3.-.- H+ + 24-methyldesmosterol + NADPH = campesterol + NADP+ plant sterol biosynthesis (-)-α-terpineol (-)-(4S)-α-terpineol 154.252 C10 H18 O1 C1(CCC(CC=1)C(O)(C)C)C CHEBI:128:*PUBCHEM:443162:*LIGAND-CPD:C11393: (-)-α-terpineol = 1,8-cineole monoterpene biosynthesis (-)-α-terpineol (-)-(4S)-α-terpineol 154.252 C10 H18 O1 C1(CCC(CC=1)C(O)(C)C)C CHEBI:128:*PUBCHEM:443162:*LIGAND-CPD:C11393: 4.2.3.- geranyl diphosphate + H2O = (-)-α-terpineol + diphosphate monoterpene biosynthesis formate formic acid 45.018 C1 H1 O2 C([H])([O-])=O CHEBI:15740:*PUBCHEM:283:*LIGAND-CPD:C00058:*CAS:64-18-6 4.1.99.12 D-ribulose-5-phosphate = H+ + formate + 1-deoxy-L-glycero-tetrulose 4-phosphate flavin biosynthesis I (bacteria and plants) formate formic acid 45.018 C1 H1 O2 C([H])([O-])=O CHEBI:15740:*PUBCHEM:283:*LIGAND-CPD:C00058:*CAS:64-18-6 1.13.11.54 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one + oxygen = H+ + 2-oxo-4-methylthiobutanoate + formate methionine salvage I formate formic acid 45.018 C1 H1 O2 C([H])([O-])=O CHEBI:15740:*PUBCHEM:283:*LIGAND-CPD:C00058:*CAS:64-18-6 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate folate transformations I formate formic acid 45.018 C1 H1 O2 C([H])([O-])=O CHEBI:15740:*PUBCHEM:283:*LIGAND-CPD:C00058:*CAS:64-18-6 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate folate transformations II (plants) formate formic acid 45.018 C1 H1 O2 C([H])([O-])=O CHEBI:15740:*PUBCHEM:283:*LIGAND-CPD:C00058:*CAS:64-18-6 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate formaldehyde oxidation V (tetrahydrofolate pathway) formate formic acid 45.018 C1 H1 O2 C([H])([O-])=O CHEBI:15740:*PUBCHEM:283:*LIGAND-CPD:C00058:*CAS:64-18-6 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate folate polyglutamylation formate formic acid 45.018 C1 H1 O2 C([H])([O-])=O CHEBI:15740:*PUBCHEM:283:*LIGAND-CPD:C00058:*CAS:64-18-6 3.5.4.25 H2O + GTP = H+ + diphosphate + 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one + formate flavin biosynthesis I (bacteria and plants) formate formic acid 45.018 C1 H1 O2 C([H])([O-])=O CHEBI:15740:*PUBCHEM:283:*LIGAND-CPD:C00058:*CAS:64-18-6 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = H+ + 5'-phosphoribosyl-N-formylglycineamide + ADP 5-aminoimidazole ribonucleotide biosynthesis II formate formic acid 45.018 C1 H1 O2 C([H])([O-])=O CHEBI:15740:*PUBCHEM:283:*LIGAND-CPD:C00058:*CAS:64-18-6 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = H+ + 5'-phosphoribosyl-N-formylglycineamide + ADP superpathway of 5-aminoimidazole ribonucleotide biosynthesis formate formic acid 45.018 C1 H1 O2 C([H])([O-])=O CHEBI:15740:*PUBCHEM:283:*LIGAND-CPD:C00058:*CAS:64-18-6 1.14.13.70 NADPH + oxygen + obtusifoliol + H+ = H2O + NADP+ + formate + 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol plant sterol biosynthesis formate formic acid 45.018 C1 H1 O2 C([H])([O-])=O CHEBI:15740:*PUBCHEM:283:*LIGAND-CPD:C00058:*CAS:64-18-6 3.5.1.10 H2O + 10-formyl-tetrahydrofolate = H+ + tetrahydrofolate + formate folate transformations I formate formic acid 45.018 C1 H1 O2 C([H])([O-])=O CHEBI:15740:*PUBCHEM:283:*LIGAND-CPD:C00058:*CAS:64-18-6 4.1.99.- 5-aminoimidazole ribonucleotide + S-adenosyl-L-methionine = hydroxymethylpyrimidine phosphate + 5'-deoxyadenosine + L-methionine + formate + carbon monoxide + H+ thiamine biosynthesis II formate formic acid 45.018 C1 H1 O2 C([H])([O-])=O CHEBI:15740:*PUBCHEM:283:*LIGAND-CPD:C00058:*CAS:64-18-6 3.5.4.16 GTP + H2O = H+ + formate + 7,8-dihydroneopterin triphosphate 6-hydroxymethyl-dihydropterin diphosphate biosynthesis formate formic acid 45.018 C1 H1 O2 C([H])([O-])=O CHEBI:15740:*PUBCHEM:283:*LIGAND-CPD:C00058:*CAS:64-18-6 1.2.1.2 formate + NAD+ = CO2 + NADH formate oxidation to CO2 D-mannose 6-phosphate D-mannose-6-phosphate*mannose-6-phosphate*α-D-mannose-6-phosphate*α-D-mannose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) CHEBI:60332:*PUBCHEM:25244236:*LIGAND-CPD:C00275:*CAS:3672-15-9 5.3.1.8 D-mannose 6-phosphate = D-fructose-6-phosphate ascorbate biosynthesis I (L-galactose pathway) D-mannose 6-phosphate D-mannose-6-phosphate*mannose-6-phosphate*α-D-mannose-6-phosphate*α-D-mannose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) CHEBI:60332:*PUBCHEM:25244236:*LIGAND-CPD:C00275:*CAS:3672-15-9 5.3.1.8 D-mannose 6-phosphate = D-fructose-6-phosphate GDP-mannose biosynthesis D-mannose 6-phosphate D-mannose-6-phosphate*mannose-6-phosphate*α-D-mannose-6-phosphate*α-D-mannose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) CHEBI:60332:*PUBCHEM:25244236:*LIGAND-CPD:C00275:*CAS:3672-15-9 5.3.1.8 D-mannose 6-phosphate = D-fructose-6-phosphate mannitol degradation II D-mannose 6-phosphate D-mannose-6-phosphate*mannose-6-phosphate*α-D-mannose-6-phosphate*α-D-mannose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) CHEBI:60332:*PUBCHEM:25244236:*LIGAND-CPD:C00275:*CAS:3672-15-9 5.3.1.8 D-mannose 6-phosphate = D-fructose-6-phosphate D-mannose degradation D-mannose 6-phosphate D-mannose-6-phosphate*mannose-6-phosphate*α-D-mannose-6-phosphate*α-D-mannose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) CHEBI:60332:*PUBCHEM:25244236:*LIGAND-CPD:C00275:*CAS:3672-15-9 2.7.1.7 ATP = H+ + D-mannose 6-phosphate + ADP mannitol degradation II D-mannose 6-phosphate D-mannose-6-phosphate*mannose-6-phosphate*α-D-mannose-6-phosphate*α-D-mannose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) CHEBI:60332:*PUBCHEM:25244236:*LIGAND-CPD:C00275:*CAS:3672-15-9 5.4.2.8 α-D-mannose 1-phosphate = D-mannose 6-phosphate ascorbate biosynthesis I (L-galactose pathway) D-mannose 6-phosphate D-mannose-6-phosphate*mannose-6-phosphate*α-D-mannose-6-phosphate*α-D-mannose-6-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OCC1(OC(O)C(O)C(O)C(O)1) CHEBI:60332:*PUBCHEM:25244236:*LIGAND-CPD:C00275:*CAS:3672-15-9 5.4.2.8 α-D-mannose 1-phosphate = D-mannose 6-phosphate GDP-mannose biosynthesis trehalose 6-phosphate α,α-trehalose 6-phosphate*trehalose phosphate 420.263 C12 H21 O14 P1 C1(OC(C(C(C1O)O)O)OC2(C(C(C(C(O2)CO)O)O)O))COP([O-])([O-])=O CHEBI:58429:*PUBCHEM:25246105:*LIGAND-CPD:C00689:*CAS:4484-88-2 3.1.3.12 trehalose 6-phosphate + H2O = trehalose trehalose biosynthesis I trehalose 6-phosphate α,α-trehalose 6-phosphate*trehalose phosphate 420.263 C12 H21 O14 P1 C1(OC(C(C(C1O)O)O)OC2(C(C(C(C(O2)CO)O)O)O))COP([O-])([O-])=O CHEBI:58429:*PUBCHEM:25246105:*LIGAND-CPD:C00689:*CAS:4484-88-2 2.4.1.15 α-D-glucose 6-phosphate = H+ + UDP + trehalose 6-phosphate trehalose biosynthesis I OPC4-CoA 983.813 C35 H52 N7 O18 P3 S1 C(C4(C(=O)CCC(CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])4))C=CCC PUBCHEM:44237211: 1.3.3.6 OPC4-CoA + oxygen = OPC4-trans-2-enoyl-CoA + hydrogen peroxide jasmonic acid biosynthesis OPC4-CoA 983.813 C35 H52 N7 O18 P3 S1 C(C4(C(=O)CCC(CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])4))C=CCC PUBCHEM:44237211: 2.3.1.16 OPC6-3-ketoacyl-CoA + coenzyme A = acetyl-CoA + OPC4-CoA jasmonic acid biosynthesis dephospho-CoA 3-dephospho-CoA*dephosphocoenzyme A 685.538 C21 H33 N7 O13 P2 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N3(C=NC2(C(N)=NC=NC=23))))C(O)C(=O)NCCC(=O)NCCS KNAPSACK:C00007257:*PUBCHEM:25244237:*LIGAND-CPD:C00882:*CAS:3633-59-8 2.7.1.24 dephospho-CoA + ATP = H+ + coenzyme A + ADP coenzyme A biosynthesis dephospho-CoA 3-dephospho-CoA*dephosphocoenzyme A 685.538 C21 H33 N7 O13 P2 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N3(C=NC2(C(N)=NC=NC=23))))C(O)C(=O)NCCC(=O)NCCS KNAPSACK:C00007257:*PUBCHEM:25244237:*LIGAND-CPD:C00882:*CAS:3633-59-8 2.7.7.3 H+ + 4'-phosphopantetheine + ATP = dephospho-CoA + diphosphate coenzyme A biosynthesis UDP-α-D-sulfoquinovopyranose UDP-6-sulfoquinovose*UDP-sulfoquinovose*UDP-α-D-sulfoquinovose 627.34 C15 H21 N2 O19 P2 S1 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CS(=O)(=O)[O-])C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:60009:*PUBCHEM:25200933:*LIGAND-CPD:C11521: UDP-α-D-sulfoquinovopyranose = sulfoquinovosyldiacylglycerol + UDP sulfolipid biosynthesis UDP-α-D-sulfoquinovopyranose UDP-6-sulfoquinovose*UDP-sulfoquinovose*UDP-α-D-sulfoquinovose 627.34 C15 H21 N2 O19 P2 S1 C2(C(O)C(O)C(COP(=O)([O-])OP(=O)(OC1(OC(CS(=O)(=O)[O-])C(O)C(O)C(O)1))[O-])O2)N3(C=CC(=O)NC(=O)3) CHEBI:60009:*PUBCHEM:25200933:*LIGAND-CPD:C11521: 3.13.1.1 UDP-α-D-glucose + H+ + sulfite = UDP-α-D-sulfoquinovopyranose + H2O sulfolipid biosynthesis protoporphyrin IX protoporphyrin 560.651 C34 H32 N4 O4 CC1(C2(=CC5(C(C=C)=C(C)C(=CC4(=C(C=C)C(C)=C(C=C3(C(C)=C(CCC([O-])=O)C(C=C(C(CCC([O-])=O)=1)N2)=N3))N4))N=5))) KNAPSACK:C00007370:*CHEBI:57306:*PUBCHEM:3794562:*LIGAND-CPD:C02191:*CAS:553-12-8 1.3.3.4 protoporphyrinogen IX + oxygen = protoporphyrin IX + hydrogen peroxide chlorophyllide a biosynthesis I protoporphyrin IX protoporphyrin 560.651 C34 H32 N4 O4 CC1(C2(=CC5(C(C=C)=C(C)C(=CC4(=C(C=C)C(C)=C(C=C3(C(C)=C(CCC([O-])=O)C(C=C(C(CCC([O-])=O)=1)N2)=N3))N4))N=5))) KNAPSACK:C00007370:*CHEBI:57306:*PUBCHEM:3794562:*LIGAND-CPD:C02191:*CAS:553-12-8 1.3.3.4 protoporphyrinogen IX + oxygen = protoporphyrin IX + hydrogen peroxide heme biosynthesis from uroporphyrinogen-III I protoporphyrin IX protoporphyrin 560.651 C34 H32 N4 O4 CC1(C2(=CC5(C(C=C)=C(C)C(=CC4(=C(C=C)C(C)=C(C=C3(C(C)=C(CCC([O-])=O)C(C=C(C(CCC([O-])=O)=1)N2)=N3))N4))N=5))) KNAPSACK:C00007370:*CHEBI:57306:*PUBCHEM:3794562:*LIGAND-CPD:C02191:*CAS:553-12-8 4.99.1.1 protoporphyrin IX + Fe2+ = protoheme IX + H+ heme biosynthesis from uroporphyrinogen-III I protoporphyrin IX protoporphyrin 560.651 C34 H32 N4 O4 CC1(C2(=CC5(C(C=C)=C(C)C(=CC4(=C(C=C)C(C)=C(C=C3(C(C)=C(CCC([O-])=O)C(C=C(C(CCC([O-])=O)=1)N2)=N3))N4))N=5))) KNAPSACK:C00007370:*CHEBI:57306:*PUBCHEM:3794562:*LIGAND-CPD:C02191:*CAS:553-12-8 6.6.1.1 ATP + protoporphyrin IX + Mg2+ + H2O = H+ + Mg-protoporphyrin + ADP chlorophyllide a biosynthesis I pyridoxamine PM 169.203 C8 H13 N2 O2 C([N+])C1(=C(O)C(C)=NC=C(CO)1) CHEBI:57761:*PUBCHEM:25245492:*LIGAND-CPD:C00534:*CAS:85-87-0 2.7.1.35 ATP + pyridoxamine = H+ + ADP + pyridoxamine 5'-phosphate pyridoxal 5'-phosphate salvage pathway N-acetylglutamyl-phosphate N-Acetyl-L-glutamyl 5-phosphate*N-acetyl-L-glutamate-5-phosphate*N-acetyl-glutamyl-P*N-acetylglutamyl-P*N-acetyl-5-glutamyl phosphate 266.124 C7 H9 N1 O8 P1 O=P([O-])(OC(=O)CCC(NC(C)=O)C(=O)[O-])[O-] PUBCHEM:440236:*PUBCHEM:25244860:*LIGAND-CPD:C04133: 2.7.2.8 N-acetyl-L-glutamate + ATP = N-acetylglutamyl-phosphate + ADP arginine biosynthesis II (acetyl cycle) N-acetylglutamyl-phosphate N-Acetyl-L-glutamyl 5-phosphate*N-acetyl-L-glutamate-5-phosphate*N-acetyl-glutamyl-P*N-acetylglutamyl-P*N-acetyl-5-glutamyl phosphate 266.124 C7 H9 N1 O8 P1 O=P([O-])(OC(=O)CCC(NC(C)=O)C(=O)[O-])[O-] PUBCHEM:440236:*PUBCHEM:25244860:*LIGAND-CPD:C04133: 2.7.2.8 N-acetyl-L-glutamate + ATP = N-acetylglutamyl-phosphate + ADP ornithine biosynthesis N-acetylglutamyl-phosphate N-Acetyl-L-glutamyl 5-phosphate*N-acetyl-L-glutamate-5-phosphate*N-acetyl-glutamyl-P*N-acetylglutamyl-P*N-acetyl-5-glutamyl phosphate 266.124 C7 H9 N1 O8 P1 O=P([O-])(OC(=O)CCC(NC(C)=O)C(=O)[O-])[O-] PUBCHEM:440236:*PUBCHEM:25244860:*LIGAND-CPD:C04133: 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = H+ + N-acetylglutamyl-phosphate + NADPH arginine biosynthesis II (acetyl cycle) N-acetylglutamyl-phosphate N-Acetyl-L-glutamyl 5-phosphate*N-acetyl-L-glutamate-5-phosphate*N-acetyl-glutamyl-P*N-acetylglutamyl-P*N-acetyl-5-glutamyl phosphate 266.124 C7 H9 N1 O8 P1 O=P([O-])(OC(=O)CCC(NC(C)=O)C(=O)[O-])[O-] PUBCHEM:440236:*PUBCHEM:25244860:*LIGAND-CPD:C04133: 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = H+ + N-acetylglutamyl-phosphate + NADPH ornithine biosynthesis oxalurate oxaluric acid*monooxalylurea*oxalureate*ureido(oxo)acetic acid*carbamyl oxamate 131.068 C3 H3 N2 O4 O=C(NC(=O)N)C([O-])=O CHEBI:57824:*PUBCHEM:20151193:*LIGAND-CPD:C00802:*CAS:585-05-7 1.1.1.154 S-(-)-ureidoglycolate = oxalurate + H+ allantoin degradation IV (anaerobic) oxalurate oxaluric acid*monooxalylurea*oxalureate*ureido(oxo)acetic acid*carbamyl oxamate 131.068 C3 H3 N2 O4 O=C(NC(=O)N)C([O-])=O CHEBI:57824:*PUBCHEM:20151193:*LIGAND-CPD:C00802:*CAS:585-05-7 2.1.3.5 oxamate + carbamoyl-phosphate = oxalurate allantoin degradation IV (anaerobic) 4,5-dihydroxy-2,3-pentanedione (S)-4,5-dihydroxypentan-2,3-dione*DHPD*DPD 132.116 C5 H8 O4 CC(C(C(CO)O)=O)=O CHEBI:425228:*PUBCHEM:25200942:*LIGAND-CPD:C11838: 4.4.1.21 S-ribosyl-L-homocysteine = L-homocysteine + 4,5-dihydroxy-2,3-pentanedione S-adenosyl-L-methionine cycle I 9,9'-di-cis-ζ-carotene 540.914 C40 H60 CC(=CCCC(=CCCC(C)=CC=CC(=CC=CC=C(C=CC=C(C)CCC=C(CCC=C(C)C)C)C)C)C)C PUBCHEM:6440490:*CHEBI:48716:*LIGAND-CPD:C15857: 9,9'-di-cis-ζ-carotene + oxygen = 7,9,9'-cis-neurosporene + H2O trans-lycopene biosynthesis II (plants) 9,9'-di-cis-ζ-carotene 540.914 C40 H60 CC(=CCCC(=CCCC(C)=CC=CC(=CC=CC=C(C=CC=C(C)CCC=C(CCC=C(C)C)C)C)C)C)C PUBCHEM:6440490:*CHEBI:48716:*LIGAND-CPD:C15857: 9,15,9'-tri-cis-ζ-carotene = 9,9'-di-cis-ζ-carotene trans-lycopene biosynthesis II (plants) nicotianamine NA 303.314 C12 H21 N3 O6 C1([N+](CC1)CCC([N+]CCC(C([O-])=O)[N+])C([O-])=O)(C([O-])=O) PUBCHEM:25202735:*PUBCHEM:25202735:*LIGAND-CPD:C05324:*CAS:34441-14-0 2.5.1.43 S-adenosyl-L-methionine = H+ + nicotianamine + S-methyl-5'-thioadenosine 2'-deoxymugineic acid phytosiderophore biosynthesis nicotianamine NA 303.314 C12 H21 N3 O6 C1([N+](CC1)CCC([N+]CCC(C([O-])=O)[N+])C([O-])=O)(C([O-])=O) PUBCHEM:25202735:*PUBCHEM:25202735:*LIGAND-CPD:C05324:*CAS:34441-14-0 2.5.1.43 S-adenosyl-L-methionine = H+ + nicotianamine + S-methyl-5'-thioadenosine nicotianamine biosynthesis nicotianamine NA 303.314 C12 H21 N3 O6 C1([N+](CC1)CCC([N+]CCC(C([O-])=O)[N+])C([O-])=O)(C([O-])=O) PUBCHEM:25202735:*PUBCHEM:25202735:*LIGAND-CPD:C05324:*CAS:34441-14-0 2.6.1.80 nicotianamine + 2-oxoglutarate = L-glutamate + 3''-deamino-3''-oxonicotianamine 2'-deoxymugineic acid phytosiderophore biosynthesis (22α)-hydroxy-campest-4-en-3-one (22S)-22-hydroxy-campest-4-en-3-one*(22S,24R)-22-hydroxy-ergost-4-en-3-one 414.67 C28 H46 O2 C1(CC(C=C2(C1(C3(C(CC2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))=O) PUBCHEM:25201842:*LIGAND-CPD:C15796: 1.14.13.- H+ + (22α)-hydroxy-campest-4-en-3-one + NADPH + oxygen = (22R,23R)-22,23-dihydroxy-campest-4-en-3-one + NADP+ + H2O brassinosteroid biosynthesis II (22α)-hydroxy-campest-4-en-3-one (22S)-22-hydroxy-campest-4-en-3-one*(22S,24R)-22-hydroxy-ergost-4-en-3-one 414.67 C28 H46 O2 C1(CC(C=C2(C1(C3(C(CC2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))=O) PUBCHEM:25201842:*LIGAND-CPD:C15796: 1.3.99.- H+ + (22α)-hydroxy-campest-4-en-3-one + NADPH = (22S,24R)-22-hydroxy-5α-ergostan-3-one + NADP+ brassinosteroid biosynthesis II (22α)-hydroxy-campest-4-en-3-one (22S)-22-hydroxy-campest-4-en-3-one*(22S,24R)-22-hydroxy-ergost-4-en-3-one 414.67 C28 H46 O2 C1(CC(C=C2(C1(C3(C(CC2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))=O) PUBCHEM:25201842:*LIGAND-CPD:C15796: 1.14.13.- H+ + campest-4-en-3-one + oxygen + NADPH = (22α)-hydroxy-campest-4-en-3-one + H2O + NADP+ brassinosteroid biosynthesis II (22α)-hydroxy-campest-4-en-3-one (22S)-22-hydroxy-campest-4-en-3-one*(22S,24R)-22-hydroxy-ergost-4-en-3-one 414.67 C28 H46 O2 C1(CC(C=C2(C1(C3(C(CC2)C4(CCC(C(C(CC(C(C)C)C)O)C)C(CC3)(C)4)))C))=O) PUBCHEM:25201842:*LIGAND-CPD:C15796: (22α)-hydroxy-campesterol = H+ + (22α)-hydroxy-campest-4-en-3-one brassinosteroid biosynthesis II 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- gibberellin A4 + 2-oxoglutarate + oxygen = GA34 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- H+ + GA44 + 2-oxoglutarate + oxygen = GA98 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.1 L-aspartate + 2-oxoglutarate = L-glutamate + oxaloacetate aspartate biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.1 L-aspartate + 2-oxoglutarate = L-glutamate + oxaloacetate aspartate degradation II 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- gibberellin A12 + 2-oxoglutarate + oxygen = GA110 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.4.1.14 NAD+ + L-glutamate = H+ + NADH + 2-oxoglutarate + L-glutamine ammonia assimilation cycle II 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.4.1.14 NAD+ + L-glutamate = H+ + NADH + 2-oxoglutarate + L-glutamine glutamate biosynthesis IV 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA34 + 2-oxoglutarate + oxygen = H+ + GA34-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2-oxoglutarate + coenzyme A + NAD+ = succinyl-CoA + CO2 + NADH TCA cycle variation III (eukaryotic) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.4.7.1 L-glutamate = 2-oxoglutarate + L-glutamine glutamate biosynthesis V 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.4.7.1 L-glutamate = 2-oxoglutarate + L-glutamine glutamine biosynthesis III 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.4.7.1 L-glutamate = 2-oxoglutarate + L-glutamine ammonia assimilation cycle II 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.39 2-aminoadipate + 2-oxoglutarate = L-glutamate + 2-oxoadipate lysine degradation II 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA19 + oxygen + 2-oxoglutarate = H+ + gibberellin A20 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA51 + 2-oxoglutarate + oxygen = H+ + GA51-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.5 L-tyrosine + 2-oxoglutarate = L-glutamate + 4-hydroxyphenylpyruvate 4-hydroxyphenylpyruvate biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.12 GA44 (open lactone form) + 2-oxoglutarate + oxygen = GA19 + succinate + CO2 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.2.4.2 2-oxoglutarate = CO2 2-ketoglutarate dehydrogenase complex 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA53 + oxygen + 2-oxoglutarate = GA44 (open lactone form) + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- gibberellin A8 + 2-oxoglutarate + oxygen = H+ + GA8-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.4 2-oxoglutarate + glycine = L-glutamate + glyoxylate photorespiration 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.80 nicotianamine + 2-oxoglutarate = L-glutamate + 3''-deamino-3''-oxonicotianamine 2'-deoxymugineic acid phytosiderophore biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.27 2-oxoglutarate + L-tryptophan = L-glutamate + indole-3-pyruvate IAA biosynthesis I 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.1.1.42 D-threo-isocitrate + NADP+ = 2-oxoglutarate + CO2 + NADPH glutamine biosynthesis III 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- leucocyanidin + 2-oxoglutarate + oxygen = H+ + cyanidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- gibberellin A9 + 2-oxoglutarate + oxygen = GA51 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 3',4',5'-pentahydroxyflavanone + 2-oxoglutarate + oxygen = dihydromyricetin + succinate + CO2 leucodelphinidin biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- gibberellin A20 + 2-oxoglutarate + oxygen = GA29 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.22 naringenin + 2-oxoglutarate + oxygen = apigenin + succinate + CO2 + H2O luteolin biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.22 eriodictyol + 2-oxoglutarate + oxygen = luteolin + succinate + CO2 + H2O luteolin biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA19 + oxygen + 2-oxoglutarate = H+ + GA17 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA53 + 2-oxoglutarate + oxygen = GA97 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.22 2-oxoglutarate + (S)-3-amino-2-methylpropanoate = L-glutamate + (S)-methylmalonate-semialdehyde valine degradation I 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.9 naringenin + oxygen + 2-oxoglutarate = CO2 + succinate + dihydrokaempferol flavonoid biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.23 dihydromyricetin + 2-oxoglutarate + oxygen = myricetin + succinate + CO2 + H2O syringetin biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.9 (2S)-pinocembrin + oxygen + 2-oxoglutarate = (2R,3R)-pinobanksin + CO2 + succinate pinobanksin biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.4.1.3 H2O + L-glutamate = ammonia + 2-oxoglutarate glutamate degradation X 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.4.1.3 H2O + L-glutamate = ammonia + 2-oxoglutarate glutamate biosynthesis II 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.19 leucocyanidin + 2-oxoglutarate + oxygen = succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- leucodelphinidin + oxygen + 2-oxoglutarate = H+ + delphinidin + H2O + CO2 + succinate anthocyanin biosynthesis (delphinidin 3-O-glucoside) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- H+ + GA44 (open lactone form) + 2-oxoglutarate + oxygen = GA38 + succinate + CO2 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.2 2-oxoglutarate + L-alanine = L-glutamate + pyruvate alanine biosynthesis II 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.2 2-oxoglutarate + L-alanine = L-glutamate + pyruvate alanine degradation II (to D-lactate) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.4.1.2 H2O + NAD+ + L-glutamate = H+ + ammonia + NADH + 2-oxoglutarate glutamate degradation I 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.4.1.2 H2O + NAD+ + L-glutamate = H+ + ammonia + NADH + 2-oxoglutarate alanine degradation II (to D-lactate) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA29 + 2-oxoglutarate + oxygen = H+ + GA29-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.5.1.8 L-saccharopine + H2O + NADP+ = L-lysine + 2-oxoglutarate + NADPH + H+ lysine degradation II 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.57 keto-phenylpyruvate + L-glutamate = L-phenylalanine + 2-oxoglutarate phenylalanine biosynthesis I 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.1.1.41 D-threo-isocitrate + NAD+ = 2-oxoglutarate + CO2 + NADH TCA cycle variation III (eukaryotic) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.1.1.41 D-threo-isocitrate + NAD+ = 2-oxoglutarate + CO2 + NADH glutamine biosynthesis III 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.52 3-phospho-L-serine + 2-oxoglutarate = L-glutamate + 3-phospho-hydroxypyruvate serine biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate valine degradation I 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate valine biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate pantothenate biosynthesis I 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate valine degradation II 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.79 prephenate + L-glutamate = L-arogenate + 2-oxoglutarate tyrosine biosynthesis II 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.79 prephenate + L-glutamate = L-arogenate + 2-oxoglutarate phenylalanine biosynthesis II 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.19 4-aminobutyrate + 2-oxoglutarate = succinate semialdehyde + L-glutamate glutamate degradation III (via 4-aminobutyrate) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.19 4-aminobutyrate + 2-oxoglutarate = succinate semialdehyde + L-glutamate 4-aminobutyrate degradation II 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.19 4-aminobutyrate + 2-oxoglutarate = succinate semialdehyde + L-glutamate 4-aminobutyrate degradation I 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.83 L,L-diaminopimelate + 2-oxoglutarate = tetrahydrodipicolinate + L-glutamate + H2O + H+ lysine biosynthesis VI 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.13 gibberellin A1 + 2-oxoglutarate + oxygen = gibberellin A8 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.23 dihydrokaempferol + 2-oxoglutarate + oxygen = kaempferol + succinate + CO2 + H2O flavonol biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.11 N-acetyl-L-ornithine + 2-oxoglutarate = L-glutamate + N-acetyl-L-glutamate 5-semialdehyde arginine biosynthesis II (acetyl cycle) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.11 N-acetyl-L-ornithine + 2-oxoglutarate = L-glutamate + N-acetyl-L-glutamate 5-semialdehyde ornithine biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.23 trans dihydroquercetin + 2-oxoglutarate + oxygen = quercetin + succinate + CO2 + H2O flavonol biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde arginine degradation VI (arginase 2 pathway) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde arginine degradation I (arginase pathway) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde proline biosynthesis II (from arginine) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.13 L-ornithine + 2-oxoglutarate = L-glutamate + L-glutamate γ-semialdehyde citrulline biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.9 imidazole acetol-phosphate + L-glutamate = L-histidinol-phosphate + 2-oxoglutarate histidine biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.15 gibberellin A20 + 2-oxoglutarate + oxygen = gibberellin A1 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.9 eriodictyol + oxygen + 2-oxoglutarate = trans dihydroquercetin + CO2 + succinate leucopelargonidin and leucocyanidin biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.9 eriodictyol + oxygen + 2-oxoglutarate = trans dihydroquercetin + CO2 + succinate leucodelphinidin biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-isoleucine + 2-oxoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine degradation I 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-isoleucine + 2-oxoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine biosynthesis I (from threonine) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.2.1.9 H+ + isochorismate + 2-oxoglutarate = 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + CO2 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-leucine + 2-oxoglutarate = L-glutamate + 4-methyl-2-oxopentanoate leucine degradation III 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-leucine + 2-oxoglutarate = L-glutamate + 4-methyl-2-oxopentanoate leucine biosynthesis 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-leucine + 2-oxoglutarate = L-glutamate + 4-methyl-2-oxopentanoate leucine degradation I 2-oxoglutarate 2-oxoglutarate*ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 144.084 C5 H4 O5 C(CC(=O)C([O-])=O)C([O-])=O CHEBI:16810:*PUBCHEM:164533:*KNAPSACK:C00000769:*PUBCHEM:164533:*CHEBI:16810:*CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- H+ + leucopelargonidin + 2-oxoglutarate + oxygen = pelargonidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) GA53 gibberellin A53*gibberellin A53*GA53 346.422 C20 H26 O5 C1(CCC(C2(C(C34(CC(CCC(C1(C)2)3)(C(C4)=C)O))C([O-])=O))(C)C([O-])=O) PUBCHEM:25203620:*LIGAND-CPD:C06094: H+ + gibberellin A12 + oxygen = GA53 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) GA53 gibberellin A53*gibberellin A53*GA53 346.422 C20 H26 O5 C1(CCC(C2(C(C34(CC(CCC(C1(C)2)3)(C(C4)=C)O))C([O-])=O))(C)C([O-])=O) PUBCHEM:25203620:*LIGAND-CPD:C06094: 1.14.11.- GA53 + oxygen + 2-oxoglutarate = GA44 (open lactone form) + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) GA53 gibberellin A53*gibberellin A53*GA53 346.422 C20 H26 O5 C1(CCC(C2(C(C34(CC(CCC(C1(C)2)3)(C(C4)=C)O))C([O-])=O))(C)C([O-])=O) PUBCHEM:25203620:*LIGAND-CPD:C06094: 1.14.11.- GA53 + 2-oxoglutarate + oxygen = GA97 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) chorismate chorismic acid 224.17 C10 H8 O6 C1(C(O)C(OC(=C)C(=O)[O-])C=C(C([O-])=O)C=1) CHEBI:29748:*PUBCHEM:5460312:*CAS:617-12-9*CAS:55508-12-8:*LIGAND-CPD:C00251: 4.2.3.5 5-enolpyruvyl-shikimate-3-phosphate = chorismate chorismate biosynthesis I chorismate chorismic acid 224.17 C10 H8 O6 C1(C(O)C(OC(=C)C(=O)[O-])C=C(C([O-])=O)C=1) CHEBI:29748:*PUBCHEM:5460312:*CAS:617-12-9*CAS:55508-12-8:*LIGAND-CPD:C00251: 2.6.1.85 chorismate + L-glutamine = 4-amino-4-deoxychorismate + L-glutamate p-aminobenzoate biosynthesis chorismate chorismic acid 224.17 C10 H8 O6 C1(C(O)C(OC(=C)C(=O)[O-])C=C(C([O-])=O)C=1) CHEBI:29748:*PUBCHEM:5460312:*CAS:617-12-9*CAS:55508-12-8:*LIGAND-CPD:C00251: 5.4.4.2 chorismate = isochorismate 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) chorismate chorismic acid 224.17 C10 H8 O6 C1(C(O)C(OC(=C)C(=O)[O-])C=C(C([O-])=O)C=1) CHEBI:29748:*PUBCHEM:5460312:*CAS:617-12-9*CAS:55508-12-8:*LIGAND-CPD:C00251: 5.4.4.2 chorismate = isochorismate 2,3-dihydroxybenzoate biosynthesis chorismate chorismic acid 224.17 C10 H8 O6 C1(C(O)C(OC(=C)C(=O)[O-])C=C(C([O-])=O)C=1) CHEBI:29748:*PUBCHEM:5460312:*CAS:617-12-9*CAS:55508-12-8:*LIGAND-CPD:C00251: 5.4.99.5 chorismate = prephenate tyrosine biosynthesis II chorismate chorismic acid 224.17 C10 H8 O6 C1(C(O)C(OC(=C)C(=O)[O-])C=C(C([O-])=O)C=1) CHEBI:29748:*PUBCHEM:5460312:*CAS:617-12-9*CAS:55508-12-8:*LIGAND-CPD:C00251: 5.4.99.5 chorismate = prephenate phenylalanine biosynthesis II chorismate chorismic acid 224.17 C10 H8 O6 C1(C(O)C(OC(=C)C(=O)[O-])C=C(C([O-])=O)C=1) CHEBI:29748:*PUBCHEM:5460312:*CAS:617-12-9*CAS:55508-12-8:*LIGAND-CPD:C00251: 5.4.99.5 chorismate = prephenate phenylalanine biosynthesis I chorismate chorismic acid 224.17 C10 H8 O6 C1(C(O)C(OC(=C)C(=O)[O-])C=C(C([O-])=O)C=1) CHEBI:29748:*PUBCHEM:5460312:*CAS:617-12-9*CAS:55508-12-8:*LIGAND-CPD:C00251: 4.1.3.27 chorismate + L-glutamine = H+ + anthranilate + L-glutamate + pyruvate tryptophan biosynthesis selenophosphate SePO3 158.94 H1 O3 P1 SE1 [O-]P([O-])(O)=[Se] CHEBI:58618:*PUBCHEM:25244868:*CAS:16561-29-8:*LIGAND-CPD:C05172: 2.7.9.3 H2O + hydrogen selenide + ATP = selenophosphate + AMP selenocysteine biosynthesis II (archaea and eukaryotes) selenophosphate SePO3 158.94 H1 O3 P1 SE1 [O-]P([O-])(O)=[Se] CHEBI:58618:*PUBCHEM:25244868:*CAS:16561-29-8:*LIGAND-CPD:C05172: 2.9.1.2 selenophosphate = H2O + diphosphate selenocysteine biosynthesis II (archaea and eukaryotes) ent-kaurenal ent-kaur-16-en-19-al 286.456 C20 H30 O1 C=C3(CC24(CCC1(C(C)(C=O)CCCC(C)1C(CCC(C2)3)4))) PUBCHEM:443466:*LIGAND-CPD:C11873: 1.14.13.78 ent-kaurenol + NADPH + H+ + oxygen = ent-kaurenal + NADP+ + H2O GA12 biosynthesis ent-kaurenal ent-kaur-16-en-19-al 286.456 C20 H30 O1 C=C3(CC24(CCC1(C(C)(C=O)CCCC(C)1C(CCC(C2)3)4))) PUBCHEM:443466:*LIGAND-CPD:C11873: 1.14.13.78 ent-kaurenal + NADPH + oxygen = ent-kaurenoate + NADP+ + H2O GA12 biosynthesis 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester 611.959 C35 H31 N4 O5 MG1 C16(N8(C(=C(C=1C)C(CC(OC)=O)=O)C=C2(C(=C(C7(=N2[Mg]5(N3(C(C(=C(C3=CC4(C(=C(C(N=45)=C6)C=C)C))C=C)C)=C7))8))C)CCC(=O)[O-]))) CHEBI:60490:*PUBCHEM:44229101:*LIGAND-CPD:C11830: 1.14.13.81 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + oxygen = 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis I 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester 611.959 C35 H31 N4 O5 MG1 C16(N8(C(=C(C=1C)C(CC(OC)=O)=O)C=C2(C(=C(C7(=N2[Mg]5(N3(C(C(=C(C3=CC4(C(=C(C(N=45)=C6)C=C)C))C=C)C)=C7))8))C)CCC(=O)[O-]))) CHEBI:60490:*PUBCHEM:44229101:*LIGAND-CPD:C11830: 1.14.13.81 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + oxygen + NADPH + H+ = divinyl protochlorophyllide a + NADP+ + H2O chlorophyllide a biosynthesis I L-galactono-1,4-lactone L-galactono-γ-lactone 178.141 C6 H10 O6 C1(C(C(C(O1)=O)O)O)C(CO)O PUBCHEM:439405:*LIGAND-CPD:C01115:*CAS:1668-08-2 1.3.2.3 L-galactono-1,4-lactone = L-ascorbate ascorbate biosynthesis I (L-galactose pathway) L-galactono-1,4-lactone L-galactono-γ-lactone 178.141 C6 H10 O6 C1(C(C(C(O1)=O)O)O)C(CO)O PUBCHEM:439405:*LIGAND-CPD:C01115:*CAS:1668-08-2 1.1.1.- L-galactose + NAD+ = H+ + L-galactono-1,4-lactone + NADH ascorbate biosynthesis I (L-galactose pathway) D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 228.095 C5 H9 O8 P1 OCC(=O)C(O)C(O)COP([O-])(=O)[O-] PUBCHEM:439190:*CHEBI:57737:*PUBCHEM:5459820:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate pentose phosphate pathway (partial) D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 228.095 C5 H9 O8 P1 OCC(=O)C(O)C(O)COP([O-])(=O)[O-] PUBCHEM:439190:*CHEBI:57737:*PUBCHEM:5459820:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate Rubisco shunt D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 228.095 C5 H9 O8 P1 OCC(=O)C(O)C(O)COP([O-])(=O)[O-] PUBCHEM:439190:*CHEBI:57737:*PUBCHEM:5459820:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate pentose phosphate pathway (non-oxidative branch) D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 228.095 C5 H9 O8 P1 OCC(=O)C(O)C(O)COP([O-])(=O)[O-] PUBCHEM:439190:*CHEBI:57737:*PUBCHEM:5459820:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate Calvin-Benson-Bassham cycle D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 228.095 C5 H9 O8 P1 OCC(=O)C(O)C(O)COP([O-])(=O)[O-] PUBCHEM:439190:*CHEBI:57737:*PUBCHEM:5459820:*LIGAND-CPD:C00231:*CAS:60802-29-1 5.1.3.1 D-ribulose-5-phosphate = D-xylulose-5-phosphate pentose phosphate pathway (partial) D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 228.095 C5 H9 O8 P1 OCC(=O)C(O)C(O)COP([O-])(=O)[O-] PUBCHEM:439190:*CHEBI:57737:*PUBCHEM:5459820:*LIGAND-CPD:C00231:*CAS:60802-29-1 5.1.3.1 D-ribulose-5-phosphate = D-xylulose-5-phosphate Rubisco shunt D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 228.095 C5 H9 O8 P1 OCC(=O)C(O)C(O)COP([O-])(=O)[O-] PUBCHEM:439190:*CHEBI:57737:*PUBCHEM:5459820:*LIGAND-CPD:C00231:*CAS:60802-29-1 5.1.3.1 D-ribulose-5-phosphate = D-xylulose-5-phosphate pentose phosphate pathway (non-oxidative branch) D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 228.095 C5 H9 O8 P1 OCC(=O)C(O)C(O)COP([O-])(=O)[O-] PUBCHEM:439190:*CHEBI:57737:*PUBCHEM:5459820:*LIGAND-CPD:C00231:*CAS:60802-29-1 5.1.3.1 D-ribulose-5-phosphate = D-xylulose-5-phosphate Calvin-Benson-Bassham cycle D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 228.095 C5 H9 O8 P1 OCC(=O)C(O)C(O)COP([O-])(=O)[O-] PUBCHEM:439190:*CHEBI:57737:*PUBCHEM:5459820:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.7.1.17 D-xylulose + ATP = H+ + D-xylulose-5-phosphate + ADP xylose degradation I D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 228.095 C5 H9 O8 P1 OCC(=O)C(O)C(O)COP([O-])(=O)[O-] PUBCHEM:439190:*CHEBI:57737:*PUBCHEM:5459820:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate pentose phosphate pathway (partial) D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 228.095 C5 H9 O8 P1 OCC(=O)C(O)C(O)COP([O-])(=O)[O-] PUBCHEM:439190:*CHEBI:57737:*PUBCHEM:5459820:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate Rubisco shunt D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 228.095 C5 H9 O8 P1 OCC(=O)C(O)C(O)COP([O-])(=O)[O-] PUBCHEM:439190:*CHEBI:57737:*PUBCHEM:5459820:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate pentose phosphate pathway (non-oxidative branch) D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 228.095 C5 H9 O8 P1 OCC(=O)C(O)C(O)COP([O-])(=O)[O-] PUBCHEM:439190:*CHEBI:57737:*PUBCHEM:5459820:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate Calvin-Benson-Bassham cycle 3-(2-propenoic acid)-o-benzoquinone 177.136 C9 H5 O4 O=C1(C(=O)C=C(C=C1)C=CC([O-])=O) PUBCHEM:25245497: 3-(2-propenoic acid)-o-benzoquinone + H2O = H+ + 3-(2-propenoic acid)-4,6-hydroxy cyclohexa-2,5-dienone esculetin biosynthesis 3-(2-propenoic acid)-o-benzoquinone 177.136 C9 H5 O4 O=C1(C(=O)C=C(C=C1)C=CC([O-])=O) PUBCHEM:25245497: 1.10.3.1 cis-caffeate + oxygen = 3-(2-propenoic acid)-o-benzoquinone + H2O esculetin biosynthesis L-glutamate-5-phosphate L-γ-glutamyl-5-phosphate*L-γ-glutamyl-5-P*L-glutamyl-5-phosphate 225.094 C5 H8 N1 O7 P1 C(C(CCC(=O)OP(=O)([O-])[O-])[N+])(=O)[O-] PUBCHEM:25246118:*LIGAND-CPD:C03287: 1.2.1.41 L-glutamate γ-semialdehyde + NADP+ = L-glutamate-5-phosphate + NADPH + H+ proline biosynthesis I L-glutamate-5-phosphate L-γ-glutamyl-5-phosphate*L-γ-glutamyl-5-P*L-glutamyl-5-phosphate 225.094 C5 H8 N1 O7 P1 C(C(CCC(=O)OP(=O)([O-])[O-])[N+])(=O)[O-] PUBCHEM:25246118:*LIGAND-CPD:C03287: 1.2.1.41 L-glutamate γ-semialdehyde + NADP+ = L-glutamate-5-phosphate + NADPH + H+ citrulline biosynthesis L-glutamate-5-phosphate L-γ-glutamyl-5-phosphate*L-γ-glutamyl-5-P*L-glutamyl-5-phosphate 225.094 C5 H8 N1 O7 P1 C(C(CCC(=O)OP(=O)([O-])[O-])[N+])(=O)[O-] PUBCHEM:25246118:*LIGAND-CPD:C03287: 2.7.2.11 L-glutamate + ATP = L-glutamate-5-phosphate + ADP proline biosynthesis I L-glutamate-5-phosphate L-γ-glutamyl-5-phosphate*L-γ-glutamyl-5-P*L-glutamyl-5-phosphate 225.094 C5 H8 N1 O7 P1 C(C(CCC(=O)OP(=O)([O-])[O-])[N+])(=O)[O-] PUBCHEM:25246118:*LIGAND-CPD:C03287: 2.7.2.11 L-glutamate + ATP = L-glutamate-5-phosphate + ADP citrulline biosynthesis oxamate 88.043 C2 H2 N1 O3 C(C([O-])=O)(=O)N CHEBI:58363:*PUBCHEM:3017661:*LIGAND-CPD:C01444:*CAS:471-47-6 2.1.3.5 oxamate + carbamoyl-phosphate = oxalurate allantoin degradation IV (anaerobic) adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(N)2)))OC(CO)3) PUBCHEM:60961:*CHEBI:16335:*LIGAND-CPD:C00212:*CAS:58-61-7 3.1.3.5 AMP + H2O = adenosine adenosine nucleotides degradation II adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(N)2)))OC(CO)3) PUBCHEM:60961:*CHEBI:16335:*LIGAND-CPD:C00212:*CAS:58-61-7 2.7.1.20 adenosine + ATP = H+ + AMP + ADP adenine and adenosine salvage VI adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(N)2)))OC(CO)3) PUBCHEM:60961:*CHEBI:16335:*LIGAND-CPD:C00212:*CAS:58-61-7 3.5.4.4 H2O + adenosine = ammonia + inosine adenosine nucleotides degradation II adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(N)2)))OC(CO)3) PUBCHEM:60961:*CHEBI:16335:*LIGAND-CPD:C00212:*CAS:58-61-7 1.5.99.12 H+ + trans-zeatin riboside + H2O + FAD = adenosine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(N)2)))OC(CO)3) PUBCHEM:60961:*CHEBI:16335:*LIGAND-CPD:C00212:*CAS:58-61-7 3.2.2.7 H2O + adenosine = adenine adenine and adenosine salvage II adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(N)2)))OC(CO)3) PUBCHEM:60961:*CHEBI:16335:*LIGAND-CPD:C00212:*CAS:58-61-7 3.3.1.1 S-adenosyl-L-homocysteine + H2O = L-homocysteine + adenosine methionine degradation I (to homocysteine) adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(N)2)))OC(CO)3) PUBCHEM:60961:*CHEBI:16335:*LIGAND-CPD:C00212:*CAS:58-61-7 3.3.1.1 S-adenosyl-L-homocysteine + H2O = L-homocysteine + adenosine S-adenosyl-L-methionine cycle II adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C3(O)(C(O)C(N1(C=NC2(=C1N=CN=C(N)2)))OC(CO)3) PUBCHEM:60961:*CHEBI:16335:*LIGAND-CPD:C00212:*CAS:58-61-7 1.5.99.12 H+ + isopentenyl adenosine + H2O + FAD = adenosine + 3-methyl-2-butenal + FADH2 cytokinins degradation apigenin 4',5,7-Trihydroxyflavone 269.233 C15 H9 O5 C1(C=CC(O)=CC=1)C3(=CC(=O)C2(=C(C=C([O-])C=C(O)2)O3)) CHEBI:58470:*PUBCHEM:25200950:*LIGAND-CPD:C01477:*CAS:520-36-5 1.14.11.22 naringenin + 2-oxoglutarate + oxygen = apigenin + succinate + CO2 + H2O luteolin biosynthesis apigenin 4',5,7-Trihydroxyflavone 269.233 C15 H9 O5 C1(C=CC(O)=CC=1)C3(=CC(=O)C2(=C(C=C([O-])C=C(O)2)O3)) CHEBI:58470:*PUBCHEM:25200950:*LIGAND-CPD:C01477:*CAS:520-36-5 H+ + naringenin + NADPH + oxygen = apigenin + NADP+ + H2O luteolin biosynthesis apigenin 4',5,7-Trihydroxyflavone 269.233 C15 H9 O5 C1(C=CC(O)=CC=1)C3(=CC(=O)C2(=C(C=C([O-])C=C(O)2)O3)) CHEBI:58470:*PUBCHEM:25200950:*LIGAND-CPD:C01477:*CAS:520-36-5 1.14.13.21 H+ + apigenin + NADPH + oxygen = luteolin + NADP+ + H2O luteolin biosynthesis D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 198.069 C4 H7 O7 P1 C(OP([O-])([O-])=O)C(C(C=O)O)O PUBCHEM:25244251:*PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate pentose phosphate pathway (partial) D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 198.069 C4 H7 O7 P1 C(OP([O-])([O-])=O)C(C(C=O)O)O PUBCHEM:25244251:*PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate Rubisco shunt D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 198.069 C4 H7 O7 P1 C(OP([O-])([O-])=O)C(C(C=O)O)O PUBCHEM:25244251:*PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate pentose phosphate pathway (non-oxidative branch) D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 198.069 C4 H7 O7 P1 C(OP([O-])([O-])=O)C(C(C=O)O)O PUBCHEM:25244251:*PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate Calvin-Benson-Bassham cycle D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 198.069 C4 H7 O7 P1 C(OP([O-])([O-])=O)C(C(C=O)O)O PUBCHEM:25244251:*PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = D-fructose-6-phosphate + D-erythrose-4-phosphate Rubisco shunt D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 198.069 C4 H7 O7 P1 C(OP([O-])([O-])=O)C(C(C=O)O)O PUBCHEM:25244251:*PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = D-fructose-6-phosphate + D-erythrose-4-phosphate pentose phosphate pathway (non-oxidative branch) D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 198.069 C4 H7 O7 P1 C(OP([O-])([O-])=O)C(C(C=O)O)O PUBCHEM:25244251:*PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 4.1.2.- dihydroxyacetone phosphate + D-erythrose-4-phosphate = D-sedoheptulose-1,7-bisphosphate Calvin-Benson-Bassham cycle D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 198.069 C4 H7 O7 P1 C(OP([O-])([O-])=O)C(C(C=O)O)O PUBCHEM:25244251:*PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 2.5.1.54 phosphoenolpyruvate + D-erythrose-4-phosphate + H2O = 3-deoxy-D-arabino-heptulosonate-7-phosphate chorismate biosynthesis I D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 198.069 C4 H7 O7 P1 C(OP([O-])([O-])=O)C(C(C=O)O)O PUBCHEM:25244251:*PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 2.5.1.54 phosphoenolpyruvate + D-erythrose-4-phosphate + H2O = 3-deoxy-D-arabino-heptulosonate-7-phosphate 3-dehydroquinate biosynthesis I betanidin betanidin radical*2,6-Pyridinedicarboxylic acid 386.317 C18 H14 N2 O8 C1(C(C=C(NC1C([O-])=O)C(=O)[O-])=CC=[N+]2(C(CC3(C=C(C(=CC2=3)O)O))C([O-])=O)) PUBCHEM:6451365:*PUBCHEM:25245506:*CHEBI:3079: 1.11.1.7 betanidin + hydrogen peroxide = betanidin + betanidin quinone + H2O betanidin degradation (S)-3-hydroxy-isobutyrate (S)-3-hydroxy-2-methylpropanoate*(S)-3-Hydroxyisobutyric acid*(S)-3-OH-iso-but*(S)-3-OH-isobutyrate 103.097 C4 H7 O3 C([O-])(C(C)CO)=O LIGAND-CPD:C06001:*PUBCHEM:20848931: 1.1.1.31 (S)-3-hydroxy-isobutyrate + NAD+ = H+ + NADH + (S)-methylmalonate-semialdehyde valine degradation I (S)-3-hydroxy-isobutyrate (S)-3-hydroxy-2-methylpropanoate*(S)-3-Hydroxyisobutyric acid*(S)-3-OH-iso-but*(S)-3-OH-isobutyrate 103.097 C4 H7 O3 C([O-])(C(C)CO)=O LIGAND-CPD:C06001:*PUBCHEM:20848931: 3.1.2.4 (S)-3-hydroxy-isobutyryl-CoA + H2O = (S)-3-hydroxy-isobutyrate + H+ + coenzyme A valine degradation I 15-cis-phytoene 544.946 C40 H64 C(=C(CCC=C(CCC=C(CCC=C(C)C)C)C)C)C=CC=C(CCC=C(CCC=C(CCC=C(C)C)C)C)C CHEBI:27787:*LIGAND-CPD:C05421:*PUBCHEM:9963391: 1.14.99.- 15-cis-phytoene + oxygen = 9,15,9'-tri-cis-ζ-carotene + H2O trans-lycopene biosynthesis II (plants) 15-cis-phytoene 544.946 C40 H64 C(=C(CCC=C(CCC=C(CCC=C(C)C)C)C)C)C=CC=C(CCC=C(CCC=C(CCC=C(C)C)C)C)C CHEBI:27787:*LIGAND-CPD:C05421:*PUBCHEM:9963391: 2.5.1.32 prephytoene diphosphate = 15-cis-phytoene + diphosphate trans-lycopene biosynthesis II (plants) GA38 gibberellin A38*gibberellin A38*GA38 361.414 C20 H25 O6 C1(CC(C3(C(=O)OCC41(C5(CCC2(CC(CC2=C)(C(C34)C([O-])=O)5)O)))C)O) PUBCHEM:25203635: 1.14.11.- H+ + GA44 (open lactone form) + 2-oxoglutarate + oxygen = GA38 + succinate + CO2 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) 4-hydroxyphenylpyruvate p-hydroxyphenylpyruvate*p-hydroxyphenylpyruvic acid*3-(4-hydroxyphenyl)pyruvate*hydroxyphenylpyruvate*4-hydroxyphenylpyruvate 179.152 C9 H7 O4 O=C(C(CC1(=CC=C(C=C1)O))=O)[O-] PUBCHEM:6971070:*CHEBI:36242:*PUBCHEM:6971070:*CHEBI:36242:*CAS:156-39-8*PUBCHEM:979:*LIGAND-CPD:C01179: 1.13.11.27 4-hydroxyphenylpyruvate + oxygen = CO2 + homogentisate vitamin E biosynthesis 4-hydroxyphenylpyruvate p-hydroxyphenylpyruvate*p-hydroxyphenylpyruvic acid*3-(4-hydroxyphenyl)pyruvate*hydroxyphenylpyruvate*4-hydroxyphenylpyruvate 179.152 C9 H7 O4 O=C(C(CC1(=CC=C(C=C1)O))=O)[O-] PUBCHEM:6971070:*CHEBI:36242:*PUBCHEM:6971070:*CHEBI:36242:*CAS:156-39-8*PUBCHEM:979:*LIGAND-CPD:C01179: 2.6.1.5 L-tyrosine + 2-oxoglutarate = L-glutamate + 4-hydroxyphenylpyruvate 4-hydroxyphenylpyruvate biosynthesis 18-oxo-oleate 18-oxo-9Z-octadecenoate*18-oxo-octadec-9-enoic acid*18-oxooctadec-9-enoic acid 295.441 C18 H31 O3 C(C=CCCCCCCCC=O)CCCCCCC(=O)[O-] PUBCHEM:25245507: 1.1.1.- 18-hydroxyoleate + NADP+ = H+ + 18-oxo-oleate + NADPH suberin biosynthesis 18-oxo-oleate 18-oxo-9Z-octadecenoate*18-oxo-octadec-9-enoic acid*18-oxooctadec-9-enoic acid 295.441 C18 H31 O3 C(C=CCCCCCCCC=O)CCCCCCC(=O)[O-] PUBCHEM:25245507: 1.2.1.- 18-oxo-oleate + NADP+ + H2O = H+ + octadecenedioate + NADPH suberin biosynthesis lactose α-lactose 342.299 C12 H22 O11 C1(OC(C(C(C1O)O)O)OC2(C(CO)OC(C(C2O)O)O))CO CHEBI:36219:*PUBCHEM:84571:*LIGAND-CPD:C00243:*CAS:63-42-3 3.2.1.23 H2O + lactose = β-D-galactose + β-D-glucose lactose degradation III L-saccharopine N6-(L-1,3-dicarboxypropyl)-L-lysine*ε-N-(L-glutar-2-yl)-L-lysine*saccharopine 275.281 C11 H19 N2 O6 C([O-])(C(CCCC[N+]C(CCC([O-])=O)C([O-])=O)[N+])=O CAS:997-68-2*CHEBI:997-68-2:*LIGAND-CPD:C00449:*PUBCHEM:25244871: 1.5.1.9 L-saccharopine + H2O + NAD+ = L-glutamate + 2-aminoadipate-6-semialdehyde + NADH + H+ lysine degradation II L-saccharopine N6-(L-1,3-dicarboxypropyl)-L-lysine*ε-N-(L-glutar-2-yl)-L-lysine*saccharopine 275.281 C11 H19 N2 O6 C([O-])(C(CCCC[N+]C(CCC([O-])=O)C([O-])=O)[N+])=O CAS:997-68-2*CHEBI:997-68-2:*LIGAND-CPD:C00449:*PUBCHEM:25244871: 1.5.1.8 L-saccharopine + H2O + NADP+ = L-lysine + 2-oxoglutarate + NADPH + H+ lysine degradation II N-acetyl-L-glutamate 5-semialdehyde N-acetylglutamate γ-semialdehyde*N-acetyl-L-glutamate-5-semialdehyde*N-acetyl-L-glutamate semialdehyde*N-acetylglutamate semialdehyde*2-acetamido-5-oxopentanoate 172.16 C7 H10 N1 O4 N(C(CCC=O)C([O-])=O)C(C)=O PUBCHEM:6857435:*CHEBI:29123:*LIGAND-CPD:C01250: 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = H+ + N-acetylglutamyl-phosphate + NADPH arginine biosynthesis II (acetyl cycle) N-acetyl-L-glutamate 5-semialdehyde N-acetylglutamate γ-semialdehyde*N-acetyl-L-glutamate-5-semialdehyde*N-acetyl-L-glutamate semialdehyde*N-acetylglutamate semialdehyde*2-acetamido-5-oxopentanoate 172.16 C7 H10 N1 O4 N(C(CCC=O)C([O-])=O)C(C)=O PUBCHEM:6857435:*CHEBI:29123:*LIGAND-CPD:C01250: 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = H+ + N-acetylglutamyl-phosphate + NADPH ornithine biosynthesis N-acetyl-L-glutamate 5-semialdehyde N-acetylglutamate γ-semialdehyde*N-acetyl-L-glutamate-5-semialdehyde*N-acetyl-L-glutamate semialdehyde*N-acetylglutamate semialdehyde*2-acetamido-5-oxopentanoate 172.16 C7 H10 N1 O4 N(C(CCC=O)C([O-])=O)C(C)=O PUBCHEM:6857435:*CHEBI:29123:*LIGAND-CPD:C01250: 2.6.1.11 N-acetyl-L-ornithine + 2-oxoglutarate = L-glutamate + N-acetyl-L-glutamate 5-semialdehyde arginine biosynthesis II (acetyl cycle) N-acetyl-L-glutamate 5-semialdehyde N-acetylglutamate γ-semialdehyde*N-acetyl-L-glutamate-5-semialdehyde*N-acetyl-L-glutamate semialdehyde*N-acetylglutamate semialdehyde*2-acetamido-5-oxopentanoate 172.16 C7 H10 N1 O4 N(C(CCC=O)C([O-])=O)C(C)=O PUBCHEM:6857435:*CHEBI:29123:*LIGAND-CPD:C01250: 2.6.1.11 N-acetyl-L-ornithine + 2-oxoglutarate = L-glutamate + N-acetyl-L-glutamate 5-semialdehyde ornithine biosynthesis 2-oxoadipate 2-oxoadipate*2-ketoadipate*α-ketoadipate*2-keto-adipate*2-oxohexanedionic acid 158.11 C6 H6 O5 C(CC(=O)C(=O)[O-])CC(=O)[O-] CHEBI:57499:*PUBCHEM:23615192:*LIGAND-CPD:C00322:*CAS:3184-35-8 2.6.1.39 2-aminoadipate + 2-oxoglutarate = L-glutamate + 2-oxoadipate lysine degradation II 2-oxoadipate 2-oxoadipate*2-ketoadipate*α-ketoadipate*2-keto-adipate*2-oxohexanedionic acid 158.11 C6 H6 O5 C(CC(=O)C(=O)[O-])CC(=O)[O-] CHEBI:57499:*PUBCHEM:23615192:*LIGAND-CPD:C00322:*CAS:3184-35-8 2-oxoadipate + NAD+ + coenzyme A = CO2 + NADH + glutaryl-CoA lysine degradation II FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 785.556 C27 H33 N9 O15 P2 N6(C(C4(=C(N(CC(O)C(O)C(COP(=O)([O-])OP(=O)(OCC1(C(O)C(C(O1)N2(C3(N=CN=C(C(N=C2)=3)N)))O))[O-])O)C5(C=C(C)C(=CC(N4)=5)C))NC6=O))=O) PUBCHEM:25244872:*LIGAND-CPD:C01352:*CAS:1910-41-4 1.5.99.12 H+ + trans-zeatin + H2O + FAD = adenine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 785.556 C27 H33 N9 O15 P2 N6(C(C4(=C(N(CC(O)C(O)C(COP(=O)([O-])OP(=O)(OCC1(C(O)C(C(O1)N2(C3(N=CN=C(C(N=C2)=3)N)))O))[O-])O)C5(C=C(C)C(=CC(N4)=5)C))NC6=O))=O) PUBCHEM:25244872:*LIGAND-CPD:C01352:*CAS:1910-41-4 1.21.3.- S-scoulerine + FAD = dehydroscoulerine + FADH2 dehydroscoulerine biosynthesis FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 785.556 C27 H33 N9 O15 P2 N6(C(C4(=C(N(CC(O)C(O)C(COP(=O)([O-])OP(=O)(OCC1(C(O)C(C(O1)N2(C3(N=CN=C(C(N=C2)=3)N)))O))[O-])O)C5(C=C(C)C(=CC(N4)=5)C))NC6=O))=O) PUBCHEM:25244872:*LIGAND-CPD:C01352:*CAS:1910-41-4 1.5.99.12 N6-dimethylallyladenine + H+ + FAD + H2O = 3-methyl-2-butenal + adenine + FADH2 cytokinins degradation FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 785.556 C27 H33 N9 O15 P2 N6(C(C4(=C(N(CC(O)C(O)C(COP(=O)([O-])OP(=O)(OCC1(C(O)C(C(O1)N2(C3(N=CN=C(C(N=C2)=3)N)))O))[O-])O)C5(C=C(C)C(=CC(N4)=5)C))NC6=O))=O) PUBCHEM:25244872:*LIGAND-CPD:C01352:*CAS:1910-41-4 1.5.99.12 H+ + cis-zeatin + H2O + FAD = 3-methyl-4-cis-hydroxy-2-butenal + adenine + FADH2 cytokinins degradation FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 785.556 C27 H33 N9 O15 P2 N6(C(C4(=C(N(CC(O)C(O)C(COP(=O)([O-])OP(=O)(OCC1(C(O)C(C(O1)N2(C3(N=CN=C(C(N=C2)=3)N)))O))[O-])O)C5(C=C(C)C(=CC(N4)=5)C))NC6=O))=O) PUBCHEM:25244872:*LIGAND-CPD:C01352:*CAS:1910-41-4 1.3.99.12 H+ + isobutyryl-CoA + FAD = methylacrylyl-CoA + FADH2 valine degradation I FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 785.556 C27 H33 N9 O15 P2 N6(C(C4(=C(N(CC(O)C(O)C(COP(=O)([O-])OP(=O)(OCC1(C(O)C(C(O1)N2(C3(N=CN=C(C(N=C2)=3)N)))O))[O-])O)C5(C=C(C)C(=CC(N4)=5)C))NC6=O))=O) PUBCHEM:25244872:*LIGAND-CPD:C01352:*CAS:1910-41-4 4-coumaroyl-CoA + NADPH + FADH2 = p-dihydrocoumaroyl-CoA + NADP+ + FAD + H+ phloridzin biosynthesis FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 785.556 C27 H33 N9 O15 P2 N6(C(C4(=C(N(CC(O)C(O)C(COP(=O)([O-])OP(=O)(OCC1(C(O)C(C(O1)N2(C3(N=CN=C(C(N=C2)=3)N)))O))[O-])O)C5(C=C(C)C(=CC(N4)=5)C))NC6=O))=O) PUBCHEM:25244872:*LIGAND-CPD:C01352:*CAS:1910-41-4 1.3.99.12 H+ + 2-methylbutanoyl-CoA + FAD = 2-methyl-crotonyl-CoA + FADH2 isoleucine degradation I FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 785.556 C27 H33 N9 O15 P2 N6(C(C4(=C(N(CC(O)C(O)C(COP(=O)([O-])OP(=O)(OCC1(C(O)C(C(O1)N2(C3(N=CN=C(C(N=C2)=3)N)))O))[O-])O)C5(C=C(C)C(=CC(N4)=5)C))NC6=O))=O) PUBCHEM:25244872:*LIGAND-CPD:C01352:*CAS:1910-41-4 1.5.99.12 H+ + trans-zeatin riboside + H2O + FAD = adenosine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 785.556 C27 H33 N9 O15 P2 N6(C(C4(=C(N(CC(O)C(O)C(COP(=O)([O-])OP(=O)(OCC1(C(O)C(C(O1)N2(C3(N=CN=C(C(N=C2)=3)N)))O))[O-])O)C5(C=C(C)C(=CC(N4)=5)C))NC6=O))=O) PUBCHEM:25244872:*LIGAND-CPD:C01352:*CAS:1910-41-4 1.5.99.12 H+ + isopentenyl adenosine + H2O + FAD = adenosine + 3-methyl-2-butenal + FADH2 cytokinins degradation FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 785.556 C27 H33 N9 O15 P2 N6(C(C4(=C(N(CC(O)C(O)C(COP(=O)([O-])OP(=O)(OCC1(C(O)C(C(O1)N2(C3(N=CN=C(C(N=C2)=3)N)))O))[O-])O)C5(C=C(C)C(=CC(N4)=5)C))NC6=O))=O) PUBCHEM:25244872:*LIGAND-CPD:C01352:*CAS:1910-41-4 1.14.14.8 anthranilate + oxygen + FADH2 = 3-hydroxyanthranilate + H2O + FAD + H+ anthranilate degradation IV (aerobic) delphinidin 3,5,3'-triglucoside 788.666 C33 H40 O22 C6(C4(=C(C=C(OC1(C(O)C(O)C(O)C(CO)O1))C(C3(C=C(O)C(O)=C(OC2(C(O)C(O)C(O)C(CO)O2))C=3))=[O+]4)C(OC5(OC(CO)C(O)C(O)C(O)5))=CC([O-])=6)) PUBCHEM:25244259:*LIGAND-CPD:C16314: 2.3.1.- delphinidin 3,5,3'-triglucoside + caffeoyl-CoA = delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + coenzyme A gentiodelphin biosynthesis delphinidin 3,5,3'-triglucoside 788.666 C33 H40 O22 C6(C4(=C(C=C(OC1(C(O)C(O)C(O)C(CO)O1))C(C3(C=C(O)C(O)=C(OC2(C(O)C(O)C(O)C(CO)O2))C=3))=[O+]4)C(OC5(OC(CO)C(O)C(O)C(O)5))=CC([O-])=6)) PUBCHEM:25244259:*LIGAND-CPD:C16314: 2.4.1.238 delphinidin-3,5-diglucoside = H+ + delphinidin 3,5,3'-triglucoside + UDP gentiodelphin biosynthesis L-citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 [O-]C(=O)C([N+])CCCNC(N)=O PUBCHEM:25244873:*LIGAND-CPD:C00327:*CAS:372-75-8 3.5.3.6 H2O + L-arginine = H+ + ammonia + L-citrulline proline biosynthesis II (from arginine) L-citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 [O-]C(=O)C([N+])CCCNC(N)=O PUBCHEM:25244873:*LIGAND-CPD:C00327:*CAS:372-75-8 1.14.13.39 oxygen + NADPH + L-arginine = L-citrulline + NADP+ + nitric oxide citrulline-nitric oxide cycle L-citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 [O-]C(=O)C([N+])CCCNC(N)=O PUBCHEM:25244873:*LIGAND-CPD:C00327:*CAS:372-75-8 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP urea cycle L-citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 [O-]C(=O)C([N+])CCCNC(N)=O PUBCHEM:25244873:*LIGAND-CPD:C00327:*CAS:372-75-8 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP arginine biosynthesis II (acetyl cycle) L-citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 [O-]C(=O)C([N+])CCCNC(N)=O PUBCHEM:25244873:*LIGAND-CPD:C00327:*CAS:372-75-8 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP citrulline-nitric oxide cycle L-citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 [O-]C(=O)C([N+])CCCNC(N)=O PUBCHEM:25244873:*LIGAND-CPD:C00327:*CAS:372-75-8 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP arginine biosynthesis I L-citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 [O-]C(=O)C([N+])CCCNC(N)=O PUBCHEM:25244873:*LIGAND-CPD:C00327:*CAS:372-75-8 3.5.1.20 H+ + L-citrulline + H2O = L-ornithine + CO2 + ammonia proline biosynthesis II (from arginine) L-citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 [O-]C(=O)C([N+])CCCNC(N)=O PUBCHEM:25244873:*LIGAND-CPD:C00327:*CAS:372-75-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline urea cycle L-citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 [O-]C(=O)C([N+])CCCNC(N)=O PUBCHEM:25244873:*LIGAND-CPD:C00327:*CAS:372-75-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline arginine biosynthesis II (acetyl cycle) L-citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 [O-]C(=O)C([N+])CCCNC(N)=O PUBCHEM:25244873:*LIGAND-CPD:C00327:*CAS:372-75-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline proline biosynthesis II (from arginine) L-citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 [O-]C(=O)C([N+])CCCNC(N)=O PUBCHEM:25244873:*LIGAND-CPD:C00327:*CAS:372-75-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline citrulline degradation L-citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 [O-]C(=O)C([N+])CCCNC(N)=O PUBCHEM:25244873:*LIGAND-CPD:C00327:*CAS:372-75-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline arginine biosynthesis I L-citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 [O-]C(=O)C([N+])CCCNC(N)=O PUBCHEM:25244873:*LIGAND-CPD:C00327:*CAS:372-75-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = H+ + L-citrulline citrulline biosynthesis N6-(Δ2-isopentenyl)-adenosine 5'-triphosphate iPTP*isopentenyladenosine riboside-5'-triphosphate*iPRTP*isopentenyladenosine-5'-triphosphate 572.278 C15 H21 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])O)(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)NCC=C(C)C)N=C2)))O3)O)O))[O-] PUBCHEM:25203647:*LIGAND-CPD:C16424: 2.5.1.- H+ + dimethylallyl diphosphate + ATP = N6-(Δ2-isopentenyl)-adenosine 5'-triphosphate + diphosphate trans-zeatin biosynthesis N6-(Δ2-isopentenyl)-adenosine 5'-triphosphate iPTP*isopentenyladenosine riboside-5'-triphosphate*iPRTP*isopentenyladenosine-5'-triphosphate 572.278 C15 H21 N5 O13 P3 O=P(OP(=O)([O-])OP(=O)([O-])O)(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)NCC=C(C)C)N=C2)))O3)O)O))[O-] PUBCHEM:25203647:*LIGAND-CPD:C16424: N6-(Δ2-isopentenyl)-adenosine 5'-triphosphate + NADPH + H2O = H+ + trans-zeatin riboside triphosphate + NADP+ trans-zeatin biosynthesis 1,4-dihydroxy-2-naphthoyl-CoA 1,4-dihydroxy-2-naphthoate-CoA*DHNA-CoA 949.669 C32 H38 N7 O19 P3 S1 C3(C(O)C(C(COP([O-])(=O)OP([O-])(OCC(C)(C)C(C(NCCC(NCCSC(C2(C=C(O)C1(C=CC=CC=1C(O)=2)))=O)=O)=O)O)=O)O3)OP([O-])(=O)[O-])(N5(C=NC4(C(=NC=NC=45)N))) PUBCHEM:25244874:*LIGAND-CPD:C15547: 3.1.2.28 1,4-dihydroxy-2-naphthoyl-CoA + H2O = H+ + 1,4-dihydroxy-2-naphthoate + coenzyme A 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) 1,4-dihydroxy-2-naphthoyl-CoA 1,4-dihydroxy-2-naphthoate-CoA*DHNA-CoA 949.669 C32 H38 N7 O19 P3 S1 C3(C(O)C(C(COP([O-])(=O)OP([O-])(OCC(C)(C)C(C(NCCC(NCCSC(C2(C=C(O)C1(C=CC=CC=1C(O)=2)))=O)=O)=O)O)=O)O3)OP([O-])(=O)[O-])(N5(C=NC4(C(=NC=NC=45)N))) PUBCHEM:25244874:*LIGAND-CPD:C15547: 4.1.3.36 H+ + 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA = 1,4-dihydroxy-2-naphthoyl-CoA + H2O 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) ubiquinone-8 ubiquinone(8)*coenzyme-Q8 727.121 C49 H74 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(=C(C)C(=O)C(OC)=C(OC)C(=O)1) LIGAND-CPD:C00399:RELATED-TO:|keseler|:3440190164:*LIGAND-CPD:C17569:*PUBCHEM:5283546:*CAS:1339-63-5: 1.1.5.3 sn-glycerol-3-phosphate + ubiquinone-8 = ubiquinol-8 + dihydroxyacetone phosphate glycerol degradation I (2R,3R)-pinobanksin 271.249 C15 H11 O5 C1(C(=CC(=C2(C=1OC(C(C2=O)O)C3(C=CC=CC=3)))O)[O-]) PUBCHEM:25200970:*LIGAND-CPD:C09826: 1.14.11.9 (2S)-pinocembrin + oxygen + 2-oxoglutarate = (2R,3R)-pinobanksin + CO2 + succinate pinobanksin biosynthesis betaine aldehyde hydrate 120.171 C5 H14 N1 O2 C[N+](C)(CC(O)O)C PUBCHEM:6395359:*LIGAND-CPD:C07345: betaine aldehyde hydrate = betaine aldehyde + H2O glycine betaine biosynthesis III (plants) betaine aldehyde hydrate 120.171 C5 H14 N1 O2 C[N+](C)(CC(O)O)C PUBCHEM:6395359:*LIGAND-CPD:C07345: 1.14.15.7 choline + oxygen + H+ = betaine aldehyde hydrate + H2O glycine betaine biosynthesis III (plants) 5-hydroxy-2-oxopentanoate 131.108 C5 H7 O4 C(CC(=O)C(=O)[O-])CO PUBCHEM:23572080:*PUBCHEM:25200972: 2-oxobutanoate = 5-hydroxy-2-oxopentanoate hypoglycin biosynthesis 5-hydroxy-2-oxopentanoate 131.108 C5 H7 O4 C(CC(=O)C(=O)[O-])CO PUBCHEM:23572080:*PUBCHEM:25200972: 5-hydroxy-2-oxopentanoate = 2-oxopentenoate + H2O hypoglycin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.38 NADP+ = NADPH + H+ very long chain fatty acid biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.25 shikimate + NADP+ = H+ + 3-dehydroshikimate + NADPH chorismate biosynthesis I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.86 2,3-dihydroxy-isovalerate + NADP+ = (S)-2-acetolactate + NADPH + H+ valine biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.50 coenzyme A + NADP+ = NADPH + H+ cuticular wax biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- H+ + coniferaldehyde + NADPH + oxygen = 5-hydroxy-coniferaldehyde + NADP+ + H2O phenylpropanoid biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- H+ + coniferaldehyde + NADPH + oxygen = 5-hydroxy-coniferaldehyde + NADP+ + H2O ferulate and sinapate biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 N6-(Δ2-isopentenyl)-adenosine 5'-triphosphate + NADPH + H2O = H+ + trans-zeatin riboside triphosphate + NADP+ trans-zeatin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.267 2-C-methyl-D-erythritol-4-phosphate + NADP+ = 1-deoxy-D-xylulose 5-phosphate + NADPH + H+ methylerythritol phosphate pathway NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.68 sinapaldehyde + NADP+ + H2O = H+ + sinapate + NADPH ferulate and sinapate biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.86 H+ + 2-aceto-2-hydroxy-butanoate + NADPH = 2,3-dihydroxy-3-methylvalerate + NADP+ isoleucine biosynthesis I (from threonine) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.- 18-oxo-oleate + NADP+ + H2O = H+ + octadecenedioate + NADPH suberin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.21 H+ + apigenin + NADPH + oxygen = luteolin + NADP+ + H2O luteolin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.17.1.3 afzelechin + NADP+ + H2O = leucopelargonidin + NADPH + H+ 2,3-trans-flavanols biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.88 H+ + dihydrokaempferol + NADPH + oxygen = dihydromyricetin + NADP+ + H2O leucodelphinidin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.88 H+ + dihydrokaempferol + NADPH + oxygen = dihydromyricetin + NADP+ + H2O syringetin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.5.1.3 NADP+ + tetrahydrofolate = H+ + NADPH + 7,8-dihydrofolate monoglutamate folate transformations II (plants) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.5.1.3 NADP+ + tetrahydrofolate = H+ + NADPH + 7,8-dihydrofolate monoglutamate tetrahydrofolate biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.79 H+ + ent-kaurenoate + oxygen + NADPH = ent-7-α-hydroxykaurenoate + H2O + NADP+ GA12 biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 2.7.1.23 NAD+ + ATP = H+ + NADP+ + ADP NAD/NADH phosphorylation and dephosphorylation NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.42 D-threo-isocitrate + NADP+ = 2-oxoglutarate + CO2 + NADPH glutamine biosynthesis III NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 N6-(Δ2-isopentenyl)-adenosine 5'-diphosphate + NADPH + H2O = H+ + trans-zeatin riboside diphosphate + NADP+ trans-zeatin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- H+ + tetrahydrogeranylgeranyl-chlorophyll a + NADPH = chlorophyll a + NADP+ chlorophyll a biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.- cycloeucalenone + NADPH + H+ = cycloeucalenol + NADP+ plant sterol biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 3.1.3.2 NADP+ + H2O = NAD+ NAD/NADH phosphorylation and dephosphorylation NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- L-tryptophan + oxygen + NADPH = N-hydroxy-L-tryptophan + NADP+ + H2O IAA biosynthesis I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- laurate + oxygen + NADPH + H+ = ω-hydroxylaurate + NADP+ + H2O ω-hydroxylation of caprate and laurate NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.36 NADP+ = NADPH + H+ very long chain fatty acid biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.70 glutamate-1-semialdehyde + NADP+ = NADPH tetrapyrrole biosynthesis I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 2.3.1.170 H+ + 4-coumaroyl-CoA + malonyl-CoA + NADPH = isoliquiritigenin + coenzyme A + CO2 + NADP+ + H2O flavonoid biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O leucopelargonidin and leucocyanidin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O leucodelphinidin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O flavonol biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.11 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 4-coumarate suberin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.11 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 4-coumarate phenylpropanoid biosynthesis, initial reactions NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.21 5-dehydro episterol + NADPH = 24-methylenecholesterol + NADP+ plant sterol biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.193 5-amino-6-(5-phospho-D-ribitylamino)uracil + NADP+ = 5-amino-6-(5-phospho-D-ribosylamino)uracil + NADPH + H+ flavin biosynthesis I (bacteria and plants) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = H+ + N-acetylglutamyl-phosphate + NADPH arginine biosynthesis II (acetyl cycle) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = H+ + N-acetylglutamyl-phosphate + NADPH ornithine biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 NADPH + H+ = NADP+ cis-vaccenate biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.195 coniferyl alcohol + NADP+ = coniferaldehyde + NADPH + H+ phenylpropanoid biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.219 H+ + dihydrokaempferol + NADPH = leucopelargonidin + NADP+ leucopelargonidin and leucocyanidin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.100 NADP+ = NADPH + H+ cis-vaccenate biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.75 H+ + divinyl protochlorophyllide a + NADPH = monovinyl protochlorophyllide a + NADP+ chlorophyllide a biosynthesis I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- sitosterol + NADPH + H+ + oxygen = stigmasterol + NADP+ + H2O plant sterol biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.3.9 H+ + oxygen + NADPH + loganin = H2O + NADP+ + secologanin camptothecin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.6.5.4 monodehydroascorbate + NADPH = H+ + L-ascorbate + NADP+ ascorbate glutathione cycle NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.271 NADP+ + GDP-L-fucose = H+ + NADPH + GDP-4-dehydro-6-deoxy-D-mannose GDP-L-fucose biosynthesis I (from GDP-D-mannose) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.49 β-D-glucose-6-phosphate + NADP+ = 6-phospho-D-glucono-1,5-lactone + NADPH + H+ pentose phosphate pathway (oxidative branch) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.169 (R)-pantoate + NADP+ = H+ + 2-dehydropantoate + NADPH phosphopantothenate biosynthesis I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.169 (R)-pantoate + NADP+ = H+ + 2-dehydropantoate + NADPH pantothenate biosynthesis I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 H+ + Δ24-25-sitosterol + NADPH = sitosterol + NADP+ plant sterol biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.8.1.2 H2O + NADP+ + hydrogen sulfide = H+ + sulfite + NADPH sulfate reduction I (assimilatory) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 H+ + UDP-4-dehydro-6-deoxy-D-glucose + NADPH = UDP-L-rhamnose + NADP+ UDP-L-rhamnose biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.80 H+ + primary fluorescent chlorophyll catabolite + NADP+ = red chlorophyll catabolite + NADPH chlorophyll a degradation NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- H+ + (3R,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- H+ + (22α)-hydroxy-campest-4-en-3-one + NADPH + oxygen = (22R,23R)-22,23-dihydroxy-campest-4-en-3-one + NADP+ + H2O brassinosteroid biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.17.1.3 cyanidin + NADPH = epicatechin + NADP+ + H2O 2,3-cis-flavanols biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.41 L-glutamate γ-semialdehyde + NADP+ = L-glutamate-5-phosphate + NADPH + H+ proline biosynthesis I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.41 L-glutamate γ-semialdehyde + NADP+ = L-glutamate-5-phosphate + NADPH + H+ citrulline biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- 7-hydroxy-chlorophyllide a + oxygen + NADPH = chlorophyllide b + H2O + NADP+ chlorophyll cycle NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- oleate + NADPH + oxygen = 18-hydroxyoleate + NADP+ + H2O suberin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.11 NADP+ + L-aspartate-semialdehyde = H+ + NADPH + L-aspartyl-4-phosphate lysine biosynthesis VI NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.11 NADP+ + L-aspartate-semialdehyde = H+ + NADPH + L-aspartyl-4-phosphate homoserine biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- H+ + (22α)-hydroxy-campesterol + NADPH + oxygen = (22R,23R)-22,23-dihydroxycampesterol + NADP+ + H2O brassinosteroid biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- H+ + (5α)-campestan-3-one + oxygen + NADPH = (22S,24R)-22-hydroxy-5α-ergostan-3-one + H2O + NADP+ brassinosteroid biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.219 H+ + dihydromyricetin + NADPH = leucodelphinidin + NADP+ leucodelphinidin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.21 H+ + naringenin + NADPH + oxygen = eriodictyol + NADP+ + H2O luteolin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.44 4-coumaroyl-CoA + NADPH + H+ = coumaraldehyde + coenzyme A + NADP+ phenylpropanoid biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.8.1.7 glutathione + NADP+ = glutathione disulfide + NADPH + H+ glutathione redox reactions I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.8.1.7 glutathione + NADP+ = glutathione disulfide + NADPH + H+ glutathione redox reactions II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- H+ + campestanol + oxygen + NADPH = 6-deoxocathasterone + H2O + NADP+ brassinosteroid biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.5.1.8 L-saccharopine + H2O + NADP+ = L-lysine + 2-oxoglutarate + NADPH + H+ lysine degradation II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate + NADPH + H2O = H+ + trans-zeatin riboside monophosphate + NADP+ trans-zeatin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.219 H+ + trans dihydroquercetin + NADPH = leucocyanidin + NADP+ leucopelargonidin and leucocyanidin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.81 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + oxygen + NADPH + H+ = divinyl protochlorophyllide a + NADP+ + H2O chlorophyllide a biosynthesis I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.- avenastenone + NADPH + H+ = avenasterol + NADP+ plant sterol biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.6.1.1 NAD+ + NADPH = NADH + NADP+ NAD/NADH phosphorylation and dephosphorylation NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.44 H+ + feruloyl-CoA + NADPH = coniferaldehyde + NADP+ + coenzyme A phenylpropanoid biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.2 5,6-dihydrothymine + NADP+ = thymine + NADPH + H+ thymine degradation NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.39 oxygen + NADPH + L-arginine = L-citrulline + NADP+ + nitric oxide citrulline-nitric oxide cycle NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ chlorogenic acid biosynthesis I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ chlorogenic acid biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ phenylpropanoid biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.88 H+ + eriodictyol + NADPH + oxygen = 3',4',5'-pentahydroxyflavanone + NADP+ + H2O leucodelphinidin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.21 5-dehydroavenasterol + NADPH = isofucosterol + NADP+ plant sterol biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.79 GA12-aldehyde + NADPH + oxygen = gibberellin A12 + NADP+ + H2O GA12 biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.78 ent-kaurenol + NADPH + H+ + oxygen = ent-kaurenal + NADP+ + H2O GA12 biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.100 NADPH + H+ = NADP+ palmitate biosynthesis II (bacteria and plants) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 4-coumaroyl-CoA + NADPH + FADH2 = p-dihydrocoumaroyl-CoA + NADP+ + FAD + H+ phloridzin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.- episterone + NADPH + H+ = episterol + NADP+ plant sterol biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- N-hydroxy-L-tryptophan + oxygen + NADPH + H+ = N,N-dihydroxy-L-tryptophan + NADP+ + H2O IAA biosynthesis I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.- NADPH + H+ = NADP+ + coenzyme A cuticular wax biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- 24-epi-campesterol + NADPH + H+ + oxygen = brassicasterol + NADP+ + H2O plant sterol biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.79 succinate semialdehyde + NADP+ + H2O = succinate + NADPH + H+ 4-aminobutyrate degradation II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.100 NADP+ = NADPH + H+ fatty acid elongation -- saturated NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 caprate + NADP+ + OH- = ω-hydroxycaprate + NADPH ω-hydroxylation of caprate and laurate NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 H+ + eriodictyol + NADPH + oxygen = luteolin + NADP+ + H2O luteolin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- nonaprenyl-4-hydroxybenzoate + oxygen + NADPH + H+ = 3,4-dihydroxy-5-all-trans-nonaprenylbenzoate + H2O + NADP+ ubiquinol-9 biosynthesis (eukaryotic) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.34 NADP+ + coenzyme A + (R)-mevalonate = H+ + NADPH + (S)-3-hydroxy-3-methylglutaryl-CoA mevalonate pathway I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 H+ + naringenin + NADPH + oxygen = apigenin + NADP+ + H2O luteolin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.70 NADPH + oxygen + obtusifoliol + H+ = H2O + NADP+ + formate + 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol plant sterol biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 tryptamine + oxygen + NADPH = N-hydroxyl-tryptamine + H2O + NADP+ IAA biosynthesis I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.70 4α-methyl-5α-ergosta-8,14,24(28)-dien-3β-ol + NADP+ = 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol + NADPH + H+ plant sterol biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.102 NADP+ + sphinganine = H+ + NADPH + 3-dehydrosphinganine sphingolipid biosynthesis (plants) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- campesterol + NADP+ = H+ + crinosterol + NADPH plant sterol biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.-.- H+ + sphinganine + oxygen + NADPH = 4-hydroxysphinganine + H2O + NADP+ sphingolipid biosynthesis (plants) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 H+ + ferulate + NADPH + oxygen = 5-hydroxyferulate + H2O + NADP+ free phenylpropanoid acid biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- H+ + geranylgeranyl-chlorophyll a + NADPH = dihydrogeranylgeranyl-chlorophyll a + NADP+ chlorophyll a biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.40 (S)-malate + NADP+ = NADPH + CO2 + pyruvate gluconeogenesis I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.40 (S)-malate + NADP+ = NADPH + CO2 + pyruvate C4 photosynthetic carbon assimilation cycle NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- H+ + campesterol + oxygen + NADPH = (22α)-hydroxy-campesterol + H2O + NADP+ brassinosteroid biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.112 (22S,24R)-22-hydroxy-5α-ergostan-3-one + oxygen + NADPH + H+ = 3-dehydro-6-deoxoteasterone + NADP+ + H2O brassinosteroid biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 7-hydroxy-chlorophyll a + H2O + NADP+ = H+ + chlorophyll a + oxygen + NADPH chlorophyll cycle NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- H+ + 3-epi-6-deoxocathasterone + NADPH + oxygen = 6-deoxotyphasterol + NADP+ + H2O brassinosteroid biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.78 ent-kaurenal + NADPH + oxygen = ent-kaurenoate + NADP+ + H2O GA12 biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.8.1.9 NADP+ = NADPH + H+ thioredoxin pathway NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.34 NADPH = NADP+ fatty acid β-oxidation IV (unsaturated, even number) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.99.- H+ + campest-4-en-3-one + NADPH = (5α)-campestan-3-one + NADP+ brassinosteroid biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.79 ent-7-α-hydroxykaurenoate + NADPH + H+ + oxygen = GA12-aldehyde + NADP+ + H2O GA12 biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- NADP+ = NADPH petroselinate biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.81 magnesium-protoporphyrin IX 13-monomethyl ester + oxygen + NADPH + H+ = 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.195 H+ + coumaraldehyde + NADPH = coumaryl-alcohol + NADP+ phenylpropanoid biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.14 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 2-coumarate coumarin biosynthesis (via 2-coumarate) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- H+ + chlorophyllide a + oxygen + NADPH = 7-hydroxy-chlorophyllide a + H2O + NADP+ chlorophyll cycle NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.78 L-arogenate + NADP+ = L-tyrosine + CO2 + NADPH tyrosine biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.78 H+ + ent-kaurene + oxygen + NADPH = H2O + NADP+ + ent-kaurenol GA12 biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.-.- H+ + 24-methyldesmosterol + NADPH = campesterol + NADP+ plant sterol biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- H+ + campest-4-en-3-one + oxygen + NADPH = (22α)-hydroxy-campest-4-en-3-one + H2O + NADP+ brassinosteroid biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.- 18-hydroxyoleate + NADP+ = H+ + 18-oxo-oleate + NADPH suberin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.9 D-glyceraldehyde-3-phosphate + NADP+ + H2O = H+ + 3-phospho-D-glycerate + NADPH glycolysis IV (plant cytosol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.2 5,6-dihydrouracil + NADP+ = uracil + NADPH + H+ uracil degradation II (reductive) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- 2-decaprenyl-6-methoxyphenol + oxygen + NADPH + H+ = 2-methoxy-6-all trans-decaprenyl-2-methoxy-1,4-benzoquinol + H2O + NADP+ ubiquinol-10 biosynthesis (eukaryotic) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- H+ + (3S,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.42 NADP+ + 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate = H+ + NADPH + 12-oxo-cis-10,15-phytodienoate jasmonic acid biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.100 NADP+ = NADPH + H+ stearate biosynthesis II (plants) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.195 H+ + sinapaldehyde + NADPH = sinapyl-alcohol + NADP+ phenylpropanoid biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 H+ + 4-coumarate + NADPH + oxygen = trans-caffeate + H2O + NADP+ suberin biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 H+ + 4-coumarate + NADPH + oxygen = trans-caffeate + H2O + NADP+ free phenylpropanoid acid biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.13 NADP+ + D-glyceraldehyde-3-phosphate = H+ + NADPH + 1,3-bisphospho-D-glycerate Calvin-Benson-Bassham cycle NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.10 NADP+ = NADPH fatty acid elongation -- saturated NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.100 NADP+ = NADPH + H+ petroselinate biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.82 (S)-malate + NADP+ = H+ + NADPH + oxaloacetate C4 photosynthetic carbon assimilation cycle NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.93 H+ + 2-cis-abscisic acid + NADPH + oxygen = 8'-hydroxyabscisate + NADP+ + H2O phaseic acid biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.12.20 pheophorbide a + oxygen + NADPH = H+ + red chlorophyll catabolite + NADP+ chlorophyll a degradation NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- 3-decaprenyl-4-hydroxybenzoate + oxygen + NADPH + H+ = 3,4-dihydroxy-5-all-trans-decaprenylbenzoate + H2O + NADP+ ubiquinol-10 biosynthesis (eukaryotic) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O chlorogenic acid biosynthesis I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O chlorogenic acid biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O simplecoumarins biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O phenylpropanoid biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.99.- H+ + (22α)-hydroxy-campest-4-en-3-one + NADPH = (22S,24R)-22-hydroxy-5α-ergostan-3-one + NADP+ brassinosteroid biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.18.1.2 NADP+ = NADPH + H+ photosynthesis light reactions NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.17.1.3 gallocatechin + NADP+ + H2O = leucodelphinidin + NADPH + H+ 2,3-trans-flavanols biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- H+ + dihydrogeranylgeranyl-chlorophyll a + NADPH = tetrahydrogeranylgeranyl-chlorophyll a + NADP+ chlorophyll a biosynthesis II NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.81 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + oxygen = 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.5.1.5 5,10-methylenetetrahydropteroyl mono-L-glutamate + NADP+ = NADPH + 5,10-methenyltetrahydrofolate folate transformations I NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.5.1.5 5,10-methylenetetrahydropteroyl mono-L-glutamate + NADP+ = NADPH + 5,10-methenyltetrahydrofolate folate transformations II (plants) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.5.1.5 5,10-methylenetetrahydropteroyl mono-L-glutamate + NADP+ = NADPH + 5,10-methenyltetrahydrofolate formaldehyde oxidation V (tetrahydrofolate pathway) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.17.1.3 catechin + NADP+ + H2O = leucocyanidin + NADPH + H+ 2,3-trans-flavanols biosynthesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 740.386 C21 H25 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)[N+]2(=CC(=CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15938972:*PUBCHEM:15938972:*PUBCHEM:15938972:*CHEBI:18009*LIGAND-CPD:C00006*PUBCHEM:5886*LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.33 chlorophyllide a + NADP+ = H+ + monovinyl protochlorophyllide a + NADPH chlorophyllide a biosynthesis I 1-dodecanol n-dodecanol*dodecyl alcohol*dodecan-1-ol*lauric alcohol*lauryl alcohol*laurinic alcohol*lorol 186.337 C12 H26 O1 OCCCCCCCCCCCC PUBCHEM:8193:*CHEBI:28878:*LIGAND-CPD:C02277: 1-dodecanol = coenzyme A wax esters biosynthesis II epicatechin (-)-epicatechin*2,3-cis-epicatechin 290.272 C15 H14 O6 C1(C(=CC(=C2(C=1OC(C(C2)O)C3(C=CC(=C(C=3)O)O)))O)O) PUBCHEM:72276:*CHEBI:28466:*LIGAND-CPD:C09727: 1.17.1.3 cyanidin + NADPH = epicatechin + NADP+ + H2O 2,3-cis-flavanols biosynthesis D-xylulose xylulose*D-xylulose*D-threo-pentulose 150.131 C5 H10 O5 OCC(=O)C(O)C(O)CO CHEBI:17140:*PUBCHEM:5289590:*LIGAND-CPD:C00310:*CAS:551-84-8 5.3.1.5 α-D-xylose = D-xylulose xylose degradation I D-xylulose xylulose*D-xylulose*D-threo-pentulose 150.131 C5 H10 O5 OCC(=O)C(O)C(O)CO CHEBI:17140:*PUBCHEM:5289590:*LIGAND-CPD:C00310:*CAS:551-84-8 2.7.1.17 D-xylulose + ATP = H+ + D-xylulose-5-phosphate + ADP xylose degradation I delphinidin-3-O-β-D-glucoside delfinidin-3-O-glucoside 464.382 C21 H20 O12 C4(C3(=C(C=C(OC1(C(O)C(O)C(O)C(CO)O1))C(C2(C=C(O)C(O)=C(O)C=2))=[O+]3)C([O-])=CC(O)=4)) PUBCHEM:25244882:*LIGAND-CPD:C12138: 2.4.1.115 delphinidin = UDP + delphinidin-3-O-β-D-glucoside anthocyanin biosynthesis (delphinidin 3-O-glucoside) delphinidin-3-O-β-D-glucoside delfinidin-3-O-glucoside 464.382 C21 H20 O12 C4(C3(=C(C=C(OC1(C(O)C(O)C(O)C(CO)O1))C(C2(C=C(O)C(O)=C(O)C=2))=[O+]3)C([O-])=CC(O)=4)) PUBCHEM:25244882:*LIGAND-CPD:C12138: 2.4.1.- delphinidin-3-O-β-D-glucoside = H+ + delphinidin-3,5-diglucoside + UDP gentiodelphin biosynthesis (R)-3-amino-2-methylpropanoate D-3-amino-isobutanoate*2-methyl-β-alanine 103.121 C4 H9 N1 O2 C(C(C([O-])=O)C)[N+] CHEBI:57731:*PUBCHEM:6971064:*LIGAND-CPD:C01205: 3.5.1.6 3-ureido-isobutyrate + H2O + H+ = (R)-3-amino-2-methylpropanoate + ammonia + CO2 thymine degradation (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate C'-(3-Indolyl)-glycerol 3-phosphate*C1-(3-Indolyl)-glycerol 3-phosphate*indole-3-glycerol-P*1-(indol-3-yl)glycerol-3-P*1-(indol-3-yl)glycerol-3-phosphate*indoleglycerol phosphate*indole-3-glycerol-phosphate 285.193 C11 H12 N1 O6 P1 N1(C2(C=CC=CC(C(=C1)C(C(COP([O-])(=O)[O-])O)O)=2)) CHEBI:51793:*PUBCHEM:25246146:*LIGAND-CPD:C03506: 4.1.1.48 H+ + 1-(o-carboxyphenylamino)-1'-deoxyribulose-5'-phosphate = (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + CO2 + H2O tryptophan biosynthesis (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate C'-(3-Indolyl)-glycerol 3-phosphate*C1-(3-Indolyl)-glycerol 3-phosphate*indole-3-glycerol-P*1-(indol-3-yl)glycerol-3-P*1-(indol-3-yl)glycerol-3-phosphate*indoleglycerol phosphate*indole-3-glycerol-phosphate 285.193 C11 H12 N1 O6 P1 N1(C2(C=CC=CC(C(=C1)C(C(COP([O-])(=O)[O-])O)O)=2)) CHEBI:51793:*PUBCHEM:25246146:*LIGAND-CPD:C03506: 4.1.2.8 (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate = indole + D-glyceraldehyde-3-phosphate IAA biosynthesis I (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate C'-(3-Indolyl)-glycerol 3-phosphate*C1-(3-Indolyl)-glycerol 3-phosphate*indole-3-glycerol-P*1-(indol-3-yl)glycerol-3-P*1-(indol-3-yl)glycerol-3-phosphate*indoleglycerol phosphate*indole-3-glycerol-phosphate 285.193 C11 H12 N1 O6 P1 N1(C2(C=CC=CC(C(=C1)C(C(COP([O-])(=O)[O-])O)O)=2)) CHEBI:51793:*PUBCHEM:25246146:*LIGAND-CPD:C03506: 4.1.2.8 (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate = indole + D-glyceraldehyde-3-phosphate tryptophan biosynthesis quercetin-3,3'-bissulfate quercetin-3,3-bissulfate 459.332 C15 H7 O13 S2 OC1(=C(C=C(C=C1)C2(=C(C(=O)C3(C(O2)=CC(=CC(O)=3)[O-]))OS(=O)(=O)[O-]))OS(=O)([O-])=O) PUBCHEM:25201878:*LIGAND-CPD:C01155: 2.8.2.28 quercetin-3,3'-bissulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + quercetin 3,3',7-trissulfate quercetinsulphates biosynthesis quercetin-3,3'-bissulfate quercetin-3,3-bissulfate 459.332 C15 H7 O13 S2 OC1(=C(C=C(C=C1)C2(=C(C(=O)C3(C(O2)=CC(=CC(O)=3)[O-]))OS(=O)(=O)[O-]))OS(=O)([O-])=O) PUBCHEM:25201878:*LIGAND-CPD:C01155: 2.8.2.26 quercetin 3-sulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin-3,3'-bissulfate quercetinsulphates biosynthesis 3-dimethylsulfoniopropionaldehyde DMSP-aldehyde 119.201 C5 H11 O1 S1 [S+](C)(C)CCC=O PUBCHEM:19824238: 1.2.1.3 3-dimethylsulfoniopropionaldehyde + H2O + NAD+ = dimethylsulfoniopropionate + NADH + H+ dimethylsulfoniopropionate biosynthesis II (Spartina) 3-dimethylsulfoniopropionaldehyde DMSP-aldehyde 119.201 C5 H11 O1 S1 [S+](C)(C)CCC=O PUBCHEM:19824238: 1.2.1.3 3-dimethylsulfoniopropionaldehyde + H2O + NAD+ = dimethylsulfoniopropionate + NADH + H+ dimethylsulfoniopropionate biosynthesis I (Wollastonia) 3-dimethylsulfoniopropionaldehyde DMSP-aldehyde 119.201 C5 H11 O1 S1 [S+](C)(C)CCC=O PUBCHEM:19824238: DMSP-amine + oxygen + H2O = H+ + 3-dimethylsulfoniopropionaldehyde + ammonia + hydrogen peroxide dimethylsulfoniopropionate biosynthesis II (Spartina) 3-dimethylsulfoniopropionaldehyde DMSP-aldehyde 119.201 C5 H11 O1 S1 [S+](C)(C)CCC=O PUBCHEM:19824238: S-methyl-L-methionine = 3-dimethylsulfoniopropionaldehyde + CO2 dimethylsulfoniopropionate biosynthesis I (Wollastonia) thiamine diphosphate TDP*thiamine diphosphate*thiamine pyrophosphate*Thaimine pyrophosphate*TPP*thiamin-PPi*thiamin pyrophosphate*thiamin diphosphate*thiamine-PPi*ThPP 422.288 C12 H16 N4 O7 P2 S1 NC1(N=C(N=CC=1C[N+]2(C(=C(CCOP([O-])(=O)OP([O-])([O-])=O)SC=2)C))C) CHEBI:58937:*PUBCHEM:15938963:*CAS:154-87-0:*LIGAND-CPD:C00068: 2.7.6.2 thiamin + ATP = H+ + thiamine diphosphate + AMP thiamine biosynthesis II D-myo-inositol (3,4,6)-trisphosphate 1D-myo-inositol (3,4,6)-trisphosphate*Ins(3,4,6)P3*I(3,4,6)P3 414.049 C6 H9 O15 P3 O=P([O-])([O-])OC1(C(O)C(OP([O-])(=O)[O-])C(O)C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:25200986: D-myo-inositol (3,4,6)-trisphosphate + ATP = H+ + D-myo-inositol (3,4,5,6)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) D-myo-inositol (3,4,6)-trisphosphate 1D-myo-inositol (3,4,6)-trisphosphate*Ins(3,4,6)P3*I(3,4,6)P3 414.049 C6 H9 O15 P3 O=P([O-])([O-])OC1(C(O)C(OP([O-])(=O)[O-])C(O)C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:25200986: D-myo-inositol (3,4)-bisphosphate + ATP = H+ + D-myo-inositol (3,4,6)-trisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) cis-coumarinic acid-β-D-glucoside coumarinic acid glucoside*coumarinate glucoside 325.294 C15 H17 O8 C1(C=CC(=C(C=1)C=CC(=O)[O-])OC2(C(C(C(C(O2)CO)O)O)O)) PUBCHEM:25245525: 5.2.1.- trans-β-D-Glucosyl-2-hydroxycinnamate = cis-coumarinic acid-β-D-glucoside coumarin biosynthesis (via 2-coumarate) cis-coumarinic acid-β-D-glucoside coumarinic acid glucoside*coumarinate glucoside 325.294 C15 H17 O8 C1(C=CC(=C(C=1)C=CC(=O)[O-])OC2(C(C(C(C(O2)CO)O)O)O)) PUBCHEM:25245525: 3.2.1.21 cis-coumarinic acid-β-D-glucoside + H2O = coumarinate + β-D-glucose coumarin biosynthesis (via 2-coumarate) O-acetyl-L-homoserine acetylhomoserine*O-acetylhomoserine 161.157 C6 H11 N1 O4 C(OCCC(C([O-])=O)[N+])(C)=O CHEBI:57716:*PUBCHEM:25244888:*LIGAND-CPD:C01077: O-acetyl-L-homoserine + L-cysteine = H+ + L-cystathionine + acetate homocysteine and cysteine interconversion benzaldehyde benzanoaldehyde 106.124 C7 H6 O1 C1(C=CC(=CC=1)C=O) PUBCHEM:240:*CHEBI:17169:*LIGAND-CPD:C00261:*CAS:100-52-7 1.2.3.9 benzaldehyde + oxygen + H2O = H+ + benzoate + hydrogen peroxide aldehyde oxidation I benzaldehyde benzanoaldehyde 106.124 C7 H6 O1 C1(C=CC(=CC=1)C=O) PUBCHEM:240:*CHEBI:17169:*LIGAND-CPD:C00261:*CAS:100-52-7 3-hydroxy-3-phenylpropionate = benzaldehyde + acetate benzoate biosynthesis II (CoA-independent, non-β-oxidative) benzaldehyde benzanoaldehyde 106.124 C7 H6 O1 C1(C=CC(=CC=1)C=O) PUBCHEM:240:*CHEBI:17169:*LIGAND-CPD:C00261:*CAS:100-52-7 1.2.1.28 benzaldehyde + H2O + NAD+ = benzoate + NADH + H+ benzoate biosynthesis III (CoA-dependent, non-β-oxidative) benzaldehyde benzanoaldehyde 106.124 C7 H6 O1 C1(C=CC(=CC=1)C=O) PUBCHEM:240:*CHEBI:17169:*LIGAND-CPD:C00261:*CAS:100-52-7 1.2.1.28 benzaldehyde + H2O + NAD+ = benzoate + NADH + H+ benzoate biosynthesis II (CoA-independent, non-β-oxidative) benzaldehyde benzanoaldehyde 106.124 C7 H6 O1 C1(C=CC(=CC=1)C=O) PUBCHEM:240:*CHEBI:17169:*LIGAND-CPD:C00261:*CAS:100-52-7 3-hydroxy-3-phenylpropionyl-CoA = benzaldehyde + acetyl-CoA benzoate biosynthesis III (CoA-dependent, non-β-oxidative) indole-3-yl-acetyl-myo-inositol L-arabinoside indole-3-yl-acetyl-myo-inositol 3-L-arabinoside 469.444 C21 H27 N1 O11 O=C(CC1(=CNC2(C=CC=CC1=2)))OC4(C(O)C(O)C(OC3(OCC(O)C(O)C(O)3))C(O)C(O)4) PUBCHEM:440406:*CHEBI:28071:*LIGAND-CPD:C04611: 2.4.2.34 indol-3-yl-acetyl-myo-inositol = H+ + UDP + indole-3-yl-acetyl-myo-inositol L-arabinoside IAA conjugate biosynthesis I (3S,6E)-nerolidol (3S)-(E)-nerolidol 222.37 C15 H26 O1 C(CCC(=CCCC(C=C)(C)O)C)=C(C)C CHEBI:59958:*KNAPSACK:C00003166:*LIGAND-CPD:C09704: 1.14.13.- H+ + (3S,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis (3S,6E)-nerolidol (3S)-(E)-nerolidol 222.37 C15 H26 O1 C(CCC(=CCCC(C=C)(C)O)C)=C(C)C CHEBI:59958:*KNAPSACK:C00003166:*LIGAND-CPD:C09704: 4.2.3.48 (2E,6E)-farnesyl diphosphate + H2O = (3S,6E)-nerolidol + diphosphate (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis L-tryptophan trp*W*tryptacin*trofan*tryptophan*2-amino-3-indolylpropanic acid*a1*a2 204.228 C11 H12 N2 O2 C2(CC([N+])C([O-])=O)(C1(C=CC=CC=1NC=2)) PUBCHEM:6923516:*KNAPSACK:C00001396:*PUBCHEM:6305:*PUBCHEM:6923516:*CAS:6912-86-3*LIGAND-CPD:C00078:*CAS:73-22-3 6.1.1.2 H+ + L-tryptophan + ATP = AMP + diphosphate tRNA charging pathway L-tryptophan trp*W*tryptacin*trofan*tryptophan*2-amino-3-indolylpropanic acid*a1*a2 204.228 C11 H12 N2 O2 C2(CC([N+])C([O-])=O)(C1(C=CC=CC=1NC=2)) PUBCHEM:6923516:*KNAPSACK:C00001396:*PUBCHEM:6305:*PUBCHEM:6923516:*CAS:6912-86-3*LIGAND-CPD:C00078:*CAS:73-22-3 4.1.1.28 H+ + L-tryptophan = CO2 + tryptamine IAA biosynthesis I L-tryptophan trp*W*tryptacin*trofan*tryptophan*2-amino-3-indolylpropanic acid*a1*a2 204.228 C11 H12 N2 O2 C2(CC([N+])C([O-])=O)(C1(C=CC=CC=1NC=2)) PUBCHEM:6923516:*KNAPSACK:C00001396:*PUBCHEM:6305:*PUBCHEM:6923516:*CAS:6912-86-3*LIGAND-CPD:C00078:*CAS:73-22-3 4.1.1.28 H+ + L-tryptophan = CO2 + tryptamine camptothecin biosynthesis L-tryptophan trp*W*tryptacin*trofan*tryptophan*2-amino-3-indolylpropanic acid*a1*a2 204.228 C11 H12 N2 O2 C2(CC([N+])C([O-])=O)(C1(C=CC=CC=1NC=2)) PUBCHEM:6923516:*KNAPSACK:C00001396:*PUBCHEM:6305:*PUBCHEM:6923516:*CAS:6912-86-3*LIGAND-CPD:C00078:*CAS:73-22-3 2.6.1.27 2-oxoglutarate + L-tryptophan = L-glutamate + indole-3-pyruvate IAA biosynthesis I L-tryptophan trp*W*tryptacin*trofan*tryptophan*2-amino-3-indolylpropanic acid*a1*a2 204.228 C11 H12 N2 O2 C2(CC([N+])C([O-])=O)(C1(C=CC=CC=1NC=2)) PUBCHEM:6923516:*KNAPSACK:C00001396:*PUBCHEM:6305:*PUBCHEM:6923516:*CAS:6912-86-3*LIGAND-CPD:C00078:*CAS:73-22-3 2.6.1.- L-tryptophan + pyruvate = L-alanine + indole-3-pyruvate IAA biosynthesis I L-tryptophan trp*W*tryptacin*trofan*tryptophan*2-amino-3-indolylpropanic acid*a1*a2 204.228 C11 H12 N2 O2 C2(CC([N+])C([O-])=O)(C1(C=CC=CC=1NC=2)) PUBCHEM:6923516:*KNAPSACK:C00001396:*PUBCHEM:6305:*PUBCHEM:6923516:*CAS:6912-86-3*LIGAND-CPD:C00078:*CAS:73-22-3 4.2.1.- indole + L-serine = L-tryptophan + H2O tryptophan biosynthesis L-tryptophan trp*W*tryptacin*trofan*tryptophan*2-amino-3-indolylpropanic acid*a1*a2 204.228 C11 H12 N2 O2 C2(CC([N+])C([O-])=O)(C1(C=CC=CC=1NC=2)) PUBCHEM:6923516:*KNAPSACK:C00001396:*PUBCHEM:6305:*PUBCHEM:6923516:*CAS:6912-86-3*LIGAND-CPD:C00078:*CAS:73-22-3 1.14.13.- L-tryptophan + oxygen + NADPH = N-hydroxy-L-tryptophan + NADP+ + H2O IAA biosynthesis I trans dihydroquercetin dihydro quercetin*(+)-taxifolin*(+)-dihydroquercetin*taxifolin 303.248 C15 H11 O7 O=C2(C3(C(O)=CC([O-])=CC(OC(C1(=CC=C(O)C(O)=C1))C(O)2)=3)) PUBCHEM:25244891:*LIGAND-CPD:C01617:*CAS:480-18-2 1.14.11.23 trans dihydroquercetin + 2-oxoglutarate + oxygen = quercetin + succinate + CO2 + H2O flavonol biosynthesis trans dihydroquercetin dihydro quercetin*(+)-taxifolin*(+)-dihydroquercetin*taxifolin 303.248 C15 H11 O7 O=C2(C3(C(O)=CC([O-])=CC(OC(C1(=CC=C(O)C(O)=C1))C(O)2)=3)) PUBCHEM:25244891:*LIGAND-CPD:C01617:*CAS:480-18-2 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O leucopelargonidin and leucocyanidin biosynthesis trans dihydroquercetin dihydro quercetin*(+)-taxifolin*(+)-dihydroquercetin*taxifolin 303.248 C15 H11 O7 O=C2(C3(C(O)=CC([O-])=CC(OC(C1(=CC=C(O)C(O)=C1))C(O)2)=3)) PUBCHEM:25244891:*LIGAND-CPD:C01617:*CAS:480-18-2 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O leucodelphinidin biosynthesis trans dihydroquercetin dihydro quercetin*(+)-taxifolin*(+)-dihydroquercetin*taxifolin 303.248 C15 H11 O7 O=C2(C3(C(O)=CC([O-])=CC(OC(C1(=CC=C(O)C(O)=C1))C(O)2)=3)) PUBCHEM:25244891:*LIGAND-CPD:C01617:*CAS:480-18-2 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O flavonol biosynthesis trans dihydroquercetin dihydro quercetin*(+)-taxifolin*(+)-dihydroquercetin*taxifolin 303.248 C15 H11 O7 O=C2(C3(C(O)=CC([O-])=CC(OC(C1(=CC=C(O)C(O)=C1))C(O)2)=3)) PUBCHEM:25244891:*LIGAND-CPD:C01617:*CAS:480-18-2 1.1.1.219 H+ + trans dihydroquercetin + NADPH = leucocyanidin + NADP+ leucopelargonidin and leucocyanidin biosynthesis trans dihydroquercetin dihydro quercetin*(+)-taxifolin*(+)-dihydroquercetin*taxifolin 303.248 C15 H11 O7 O=C2(C3(C(O)=CC([O-])=CC(OC(C1(=CC=C(O)C(O)=C1))C(O)2)=3)) PUBCHEM:25244891:*LIGAND-CPD:C01617:*CAS:480-18-2 1.14.11.9 eriodictyol + oxygen + 2-oxoglutarate = trans dihydroquercetin + CO2 + succinate leucopelargonidin and leucocyanidin biosynthesis trans dihydroquercetin dihydro quercetin*(+)-taxifolin*(+)-dihydroquercetin*taxifolin 303.248 C15 H11 O7 O=C2(C3(C(O)=CC([O-])=CC(OC(C1(=CC=C(O)C(O)=C1))C(O)2)=3)) PUBCHEM:25244891:*LIGAND-CPD:C01617:*CAS:480-18-2 1.14.11.9 eriodictyol + oxygen + 2-oxoglutarate = trans dihydroquercetin + CO2 + succinate leucodelphinidin biosynthesis tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 formaldehyde + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + H2O formaldehyde oxidation V (tetrahydrofolate pathway) tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 1.5.1.3 NADP+ + tetrahydrofolate = H+ + NADPH + 7,8-dihydrofolate monoglutamate folate transformations II (plants) tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 1.5.1.3 NADP+ + tetrahydrofolate = H+ + NADPH + 7,8-dihydrofolate monoglutamate tetrahydrofolate biosynthesis tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.11 5,10-methylenetetrahydropteroyl mono-L-glutamate + 2-oxoisovalerate + H2O = H+ + 2-dehydropantoate + tetrahydrofolate phosphopantothenate biosynthesis I tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.11 5,10-methylenetetrahydropteroyl mono-L-glutamate + 2-oxoisovalerate + H2O = H+ + 2-dehydropantoate + tetrahydrofolate pantothenate biosynthesis I tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.10 tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia glycine cleavage complex tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations I tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH folate transformations II (plants) tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 NAD+ + glycine + tetrahydrofolate = H+ + 5,10-methylenetetrahydropteroyl mono-L-glutamate + ammonia + CO2 + NADH photorespiration tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.3 10-formyl-tetrahydrofolate + aminoimidazole carboxamide ribonucleotide = tetrahydrofolate + phosphoribosyl-formamido-carboxamide inosine-5'-phosphate biosynthesis II tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate folate transformations I tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate folate transformations II (plants) tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate formaldehyde oxidation V (tetrahydrofolate pathway) tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate folate polyglutamylation tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O glycine biosynthesis I tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O folate transformations I tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O folate transformations II (plants) tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O folate polyglutamylation tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.1 L-serine + tetrahydrofolate = 5,10-methylenetetrahydropteroyl mono-L-glutamate + glycine + H2O photorespiration tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.1.19 tetrahydrofolate + trimethyl sulfonium = H+ + dimethylsulfide + 5-methyl-tetrahydrofolate folate transformations I tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.2 10-formyl-tetrahydrofolate + 5-phospho-ribosyl-glycineamide = H+ + tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.2 10-formyl-tetrahydrofolate + 5-phospho-ribosyl-glycineamide = H+ + tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide 5-aminoimidazole ribonucleotide biosynthesis I tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 3.5.1.10 H2O + 10-formyl-tetrahydrofolate = H+ + tetrahydrofolate + formate folate transformations I tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.1.13 L-homocysteine + 5-methyl-tetrahydrofolate = L-methionine + tetrahydrofolate folate transformations I tetrahydrofolate H4PteGlu*5,6,7,8-tetrahydrofolic acid*tetrahydrofolic acid*(6S)-tetrahydrofolate*H4PteGlu1*tetrahydropteroyl mono-L-glutamate*tetrahydrafolate*5,6,7,8-tetrahydrofolate*THF*tetra-H-folate*th-folate*FH4*folate-H4*tetrahydropteroylglutamate*H4F*vitamin B9 443.418 C19 H21 N7 O6 NC3(=NC2(NCC(CNC1(=CC=C(C=C1)C(=O)NC(CCC(=O)[O-])C(=O)[O-]))NC=2C(=O)N3)) KNAPSACK:C00007249:*CHEBI:57453:*PUBCHEM:25790919:*CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.1.13 L-homocysteine + 5-methyl-tetrahydrofolate = L-methionine + tetrahydrofolate folate transformations II (plants) 5,10-methenyltetrahydrofolate 5,10-methenyltetrahydrofolate*n5-n10-CH-THF*n5-n10-methenyltetrahydrofolate*CH-THF*5,10-methenyl-THF*anhydroleucovorin*methenyl-tetrahydrofolate*methenyl-THF*methenyl-H4F 454.421 C20 H20 N7 O6 NC4(=NC(C3([N+]2(C(CN(C1(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C1))C=2)CNC=3N4)))=O) PUBCHEM:644351:*CHEBI:15638:*LIGAND-CPD:C00445:*CAS:7444-29-3 5,10-methenyltetrahydrofolate + H2O = H+ + 5-formyl-tetrahydrofolate folate transformations II (plants) 5,10-methenyltetrahydrofolate 5,10-methenyltetrahydrofolate*n5-n10-CH-THF*n5-n10-methenyltetrahydrofolate*CH-THF*5,10-methenyl-THF*anhydroleucovorin*methenyl-tetrahydrofolate*methenyl-THF*methenyl-H4F 454.421 C20 H20 N7 O6 NC4(=NC(C3([N+]2(C(CN(C1(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C1))C=2)CNC=3N4)))=O) PUBCHEM:644351:*CHEBI:15638:*LIGAND-CPD:C00445:*CAS:7444-29-3 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate folate transformations I 5,10-methenyltetrahydrofolate 5,10-methenyltetrahydrofolate*n5-n10-CH-THF*n5-n10-methenyltetrahydrofolate*CH-THF*5,10-methenyl-THF*anhydroleucovorin*methenyl-tetrahydrofolate*methenyl-THF*methenyl-H4F 454.421 C20 H20 N7 O6 NC4(=NC(C3([N+]2(C(CN(C1(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C1))C=2)CNC=3N4)))=O) PUBCHEM:644351:*CHEBI:15638:*LIGAND-CPD:C00445:*CAS:7444-29-3 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate 5,10-methenyltetrahydrofolate 5,10-methenyltetrahydrofolate*n5-n10-CH-THF*n5-n10-methenyltetrahydrofolate*CH-THF*5,10-methenyl-THF*anhydroleucovorin*methenyl-tetrahydrofolate*methenyl-THF*methenyl-H4F 454.421 C20 H20 N7 O6 NC4(=NC(C3([N+]2(C(CN(C1(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C1))C=2)CNC=3N4)))=O) PUBCHEM:644351:*CHEBI:15638:*LIGAND-CPD:C00445:*CAS:7444-29-3 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate folate transformations II (plants) 5,10-methenyltetrahydrofolate 5,10-methenyltetrahydrofolate*n5-n10-CH-THF*n5-n10-methenyltetrahydrofolate*CH-THF*5,10-methenyl-THF*anhydroleucovorin*methenyl-tetrahydrofolate*methenyl-THF*methenyl-H4F 454.421 C20 H20 N7 O6 NC4(=NC(C3([N+]2(C(CN(C1(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C1))C=2)CNC=3N4)))=O) PUBCHEM:644351:*CHEBI:15638:*LIGAND-CPD:C00445:*CAS:7444-29-3 3.5.4.9 H2O + 5,10-methenyltetrahydrofolate = H+ + 10-formyl-tetrahydrofolate formaldehyde oxidation V (tetrahydrofolate pathway) 5,10-methenyltetrahydrofolate 5,10-methenyltetrahydrofolate*n5-n10-CH-THF*n5-n10-methenyltetrahydrofolate*CH-THF*5,10-methenyl-THF*anhydroleucovorin*methenyl-tetrahydrofolate*methenyl-THF*methenyl-H4F 454.421 C20 H20 N7 O6 NC4(=NC(C3([N+]2(C(CN(C1(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C1))C=2)CNC=3N4)))=O) PUBCHEM:644351:*CHEBI:15638:*LIGAND-CPD:C00445:*CAS:7444-29-3 1.5.1.15 5,10-methylenetetrahydropteroyl mono-L-glutamate + NAD+ = 5,10-methenyltetrahydrofolate + NADH folate transformations I 5,10-methenyltetrahydrofolate 5,10-methenyltetrahydrofolate*n5-n10-CH-THF*n5-n10-methenyltetrahydrofolate*CH-THF*5,10-methenyl-THF*anhydroleucovorin*methenyl-tetrahydrofolate*methenyl-THF*methenyl-H4F 454.421 C20 H20 N7 O6 NC4(=NC(C3([N+]2(C(CN(C1(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C1))C=2)CNC=3N4)))=O) PUBCHEM:644351:*CHEBI:15638:*LIGAND-CPD:C00445:*CAS:7444-29-3 6.3.3.2 5-formyl-tetrahydrofolate + ATP = 5,10-methenyltetrahydrofolate + ADP folate transformations I 5,10-methenyltetrahydrofolate 5,10-methenyltetrahydrofolate*n5-n10-CH-THF*n5-n10-methenyltetrahydrofolate*CH-THF*5,10-methenyl-THF*anhydroleucovorin*methenyl-tetrahydrofolate*methenyl-THF*methenyl-H4F 454.421 C20 H20 N7 O6 NC4(=NC(C3([N+]2(C(CN(C1(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C1))C=2)CNC=3N4)))=O) PUBCHEM:644351:*CHEBI:15638:*LIGAND-CPD:C00445:*CAS:7444-29-3 6.3.3.2 5-formyl-tetrahydrofolate + ATP = 5,10-methenyltetrahydrofolate + ADP folate transformations II (plants) 5,10-methenyltetrahydrofolate 5,10-methenyltetrahydrofolate*n5-n10-CH-THF*n5-n10-methenyltetrahydrofolate*CH-THF*5,10-methenyl-THF*anhydroleucovorin*methenyl-tetrahydrofolate*methenyl-THF*methenyl-H4F 454.421 C20 H20 N7 O6 NC4(=NC(C3([N+]2(C(CN(C1(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C1))C=2)CNC=3N4)))=O) PUBCHEM:644351:*CHEBI:15638:*LIGAND-CPD:C00445:*CAS:7444-29-3 1.5.1.5 5,10-methylenetetrahydropteroyl mono-L-glutamate + NADP+ = NADPH + 5,10-methenyltetrahydrofolate folate transformations I 5,10-methenyltetrahydrofolate 5,10-methenyltetrahydrofolate*n5-n10-CH-THF*n5-n10-methenyltetrahydrofolate*CH-THF*5,10-methenyl-THF*anhydroleucovorin*methenyl-tetrahydrofolate*methenyl-THF*methenyl-H4F 454.421 C20 H20 N7 O6 NC4(=NC(C3([N+]2(C(CN(C1(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C1))C=2)CNC=3N4)))=O) PUBCHEM:644351:*CHEBI:15638:*LIGAND-CPD:C00445:*CAS:7444-29-3 1.5.1.5 5,10-methylenetetrahydropteroyl mono-L-glutamate + NADP+ = NADPH + 5,10-methenyltetrahydrofolate folate transformations II (plants) 5,10-methenyltetrahydrofolate 5,10-methenyltetrahydrofolate*n5-n10-CH-THF*n5-n10-methenyltetrahydrofolate*CH-THF*5,10-methenyl-THF*anhydroleucovorin*methenyl-tetrahydrofolate*methenyl-THF*methenyl-H4F 454.421 C20 H20 N7 O6 NC4(=NC(C3([N+]2(C(CN(C1(=CC=C(C(NC(C([O-])=O)CCC([O-])=O)=O)C=C1))C=2)CNC=3N4)))=O) PUBCHEM:644351:*CHEBI:15638:*LIGAND-CPD:C00445:*CAS:7444-29-3 1.5.1.5 5,10-methylenetetrahydropteroyl mono-L-glutamate + NADP+ = NADPH + 5,10-methenyltetrahydrofolate formaldehyde oxidation V (tetrahydrofolate pathway) campest-4-en-3β-ol methylcholestenol*(24R)-24-methyl-cholest-4-en-3β-ol 400.687 C28 H48 O1 C1(CC(C=C2(C1(C3(C(CC2)C4(CCC(C(CCC(C(C)C)C)C)C(CC3)(C)4)))C))O) PUBCHEM:25203683:*LIGAND-CPD:C15784: 1.1.1.145 campest-4-en-3β-ol = H+ + campest-4-en-3-one brassinosteroid biosynthesis II campest-4-en-3β-ol methylcholestenol*(24R)-24-methyl-cholest-4-en-3β-ol 400.687 C28 H48 O1 C1(CC(C=C2(C1(C3(C(CC2)C4(CCC(C(CCC(C(C)C)C)C)C(CC3)(C)4)))C))O) PUBCHEM:25203683:*LIGAND-CPD:C15784: 5.3.3.1 campesterol = campest-4-en-3β-ol brassinosteroid biosynthesis II glycine betaine oxyneurine*lycine*acidin-pepsin*betaine*trimethylammonioacetate*N,N,N-trimethylglycine 117.147 C5 H11 N1 O2 C[N+](C)(CC([O-])=O)C PUBCHEM:247:*CHEBI:17750:*LIGAND-CPD:C00719:*CAS:107-43-7 1.2.1.8 betaine aldehyde + NAD+ + H2O = H+ + glycine betaine + NADH glycine betaine biosynthesis III (plants) adenosine 3',5'-bisphosphate adenosine-3',5'-bisphosphate*adenosine 3',5'-bisphosphate*PAP*phosphoadenosine phosphate*3',5'-ADP 423.172 C10 H11 N5 O10 P2 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP([O-])([O-])=O)COP([O-])(=O)[O-])))N) PUBCHEM:23615194:*CAS:1053-73-2:*LIGAND-CPD:C00054: quercetin 3, 7, 4'-trisulphate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin 3, 7, 3', 4'-tetrasulphate quercetinsulphates biosynthesis adenosine 3',5'-bisphosphate adenosine-3',5'-bisphosphate*adenosine 3',5'-bisphosphate*PAP*phosphoadenosine phosphate*3',5'-ADP 423.172 C10 H11 N5 O10 P2 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP([O-])([O-])=O)COP([O-])(=O)[O-])))N) PUBCHEM:23615194:*CAS:1053-73-2:*LIGAND-CPD:C00054: isorhamnetin 3-sulphate + phosphoadenosine-5'-phosphosulfate = H+ + adenosine 3',5'-bisphosphate + isorhamnetin 3, 4'-bisulphate quercetinsulphates biosynthesis adenosine 3',5'-bisphosphate adenosine-3',5'-bisphosphate*adenosine 3',5'-bisphosphate*PAP*phosphoadenosine phosphate*3',5'-ADP 423.172 C10 H11 N5 O10 P2 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP([O-])([O-])=O)COP([O-])(=O)[O-])))N) PUBCHEM:23615194:*CAS:1053-73-2:*LIGAND-CPD:C00054: quercetin 3,3',7-trissulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin 3, 7, 3', 4'-tetrasulphate quercetinsulphates biosynthesis adenosine 3',5'-bisphosphate adenosine-3',5'-bisphosphate*adenosine 3',5'-bisphosphate*PAP*phosphoadenosine phosphate*3',5'-ADP 423.172 C10 H11 N5 O10 P2 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP([O-])([O-])=O)COP([O-])(=O)[O-])))N) PUBCHEM:23615194:*CAS:1053-73-2:*LIGAND-CPD:C00054: 2.7.8.7 coenzyme A = adenosine 3',5'-bisphosphate acyl carrier protein metabolism adenosine 3',5'-bisphosphate adenosine-3',5'-bisphosphate*adenosine 3',5'-bisphosphate*PAP*phosphoadenosine phosphate*3',5'-ADP 423.172 C10 H11 N5 O10 P2 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP([O-])([O-])=O)COP([O-])(=O)[O-])))N) PUBCHEM:23615194:*CAS:1053-73-2:*LIGAND-CPD:C00054: isorhamnetin + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + isorhamnetin 3-sulphate quercetinsulphates biosynthesis adenosine 3',5'-bisphosphate adenosine-3',5'-bisphosphate*adenosine 3',5'-bisphosphate*PAP*phosphoadenosine phosphate*3',5'-ADP 423.172 C10 H11 N5 O10 P2 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP([O-])([O-])=O)COP([O-])(=O)[O-])))N) PUBCHEM:23615194:*CAS:1053-73-2:*LIGAND-CPD:C00054: 1.8.4.8 adenosine 3',5'-bisphosphate + sulfite = phosphoadenosine-5'-phosphosulfate sulfate reduction I (assimilatory) adenosine 3',5'-bisphosphate adenosine-3',5'-bisphosphate*adenosine 3',5'-bisphosphate*PAP*phosphoadenosine phosphate*3',5'-ADP 423.172 C10 H11 N5 O10 P2 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP([O-])([O-])=O)COP([O-])(=O)[O-])))N) PUBCHEM:23615194:*CAS:1053-73-2:*LIGAND-CPD:C00054: 2.8.2.28 quercetin-3,3'-bissulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + quercetin 3,3',7-trissulfate quercetinsulphates biosynthesis adenosine 3',5'-bisphosphate adenosine-3',5'-bisphosphate*adenosine 3',5'-bisphosphate*PAP*phosphoadenosine phosphate*3',5'-ADP 423.172 C10 H11 N5 O10 P2 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP([O-])([O-])=O)COP([O-])(=O)[O-])))N) PUBCHEM:23615194:*CAS:1053-73-2:*LIGAND-CPD:C00054: 2.8.2.26 quercetin 3-sulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin-3,3'-bissulfate quercetinsulphates biosynthesis adenosine 3',5'-bisphosphate adenosine-3',5'-bisphosphate*adenosine 3',5'-bisphosphate*PAP*phosphoadenosine phosphate*3',5'-ADP 423.172 C10 H11 N5 O10 P2 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP([O-])([O-])=O)COP([O-])(=O)[O-])))N) PUBCHEM:23615194:*CAS:1053-73-2:*LIGAND-CPD:C00054: 2.8.2.25 quercetin + phosphoadenosine-5'-phosphosulfate = H+ + adenosine 3',5'-bisphosphate + quercetin 3-sulfate quercetinsulphates biosynthesis adenosine 3',5'-bisphosphate adenosine-3',5'-bisphosphate*adenosine 3',5'-bisphosphate*PAP*phosphoadenosine phosphate*3',5'-ADP 423.172 C10 H11 N5 O10 P2 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP([O-])([O-])=O)COP([O-])(=O)[O-])))N) PUBCHEM:23615194:*CAS:1053-73-2:*LIGAND-CPD:C00054: 2.8.2.27 quercetin 3-sulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin-3,4'-bissulfate quercetinsulphates biosynthesis adenosine 3',5'-bisphosphate adenosine-3',5'-bisphosphate*adenosine 3',5'-bisphosphate*PAP*phosphoadenosine phosphate*3',5'-ADP 423.172 C10 H11 N5 O10 P2 N1(C(=C2(C(=NC=1)N(C=N2)C3(OC(C(C3O)OP([O-])([O-])=O)COP([O-])(=O)[O-])))N) PUBCHEM:23615194:*CAS:1053-73-2:*LIGAND-CPD:C00054: quercetin-3,4'-bissulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + quercetin 3, 7, 4'-trisulphate quercetinsulphates biosynthesis delphinidin-3,5-diglucoside 626.524 C27 H30 O17 C5(C3(=C(C=C(OC1(C(O)C(O)C(O)C(CO)O1))C(C2(C=C(O)C(O)=C(O)C=2))=[O+]3)C(OC4(OC(CO)C(O)C(O)C(O)4))=CC([O-])=5)) PUBCHEM:25244903:*LIGAND-CPD:C16312: 2.3.1.153 delphinidin-3,5-diglucoside + caffeoyl-CoA = delphinidin 3-O-glucosyl-5-O-caffeoylglucoside + coenzyme A gentiodelphin biosynthesis delphinidin-3,5-diglucoside 626.524 C27 H30 O17 C5(C3(=C(C=C(OC1(C(O)C(O)C(O)C(CO)O1))C(C2(C=C(O)C(O)=C(O)C=2))=[O+]3)C(OC4(OC(CO)C(O)C(O)C(O)4))=CC([O-])=5)) PUBCHEM:25244903:*LIGAND-CPD:C16312: 2.4.1.- delphinidin-3-O-β-D-glucoside = H+ + delphinidin-3,5-diglucoside + UDP gentiodelphin biosynthesis delphinidin-3,5-diglucoside 626.524 C27 H30 O17 C5(C3(=C(C=C(OC1(C(O)C(O)C(O)C(CO)O1))C(C2(C=C(O)C(O)=C(O)C=2))=[O+]3)C(OC4(OC(CO)C(O)C(O)C(O)4))=CC([O-])=5)) PUBCHEM:25244903:*LIGAND-CPD:C16312: 2.4.1.238 delphinidin-3,5-diglucoside = H+ + delphinidin 3,5,3'-triglucoside + UDP gentiodelphin biosynthesis N-dimethylethanolamine phosphate N,N-dimethylethanolamine phosphate*dimethylethanolamine phosphate*P-DME 168.109 C4 H11 N1 O4 P1 P([O-])(=O)(OCC[N+](C)C)[O-] CHEBI:58641:*PUBCHEM:25201906:*LIGAND-CPD:C13482: 2.1.1.103 N-dimethylethanolamine phosphate + S-adenosyl-L-methionine = H+ + phosphoryl-choline + S-adenosyl-L-homocysteine choline biosynthesis I N-dimethylethanolamine phosphate N,N-dimethylethanolamine phosphate*dimethylethanolamine phosphate*P-DME 168.109 C4 H11 N1 O4 P1 P([O-])(=O)(OCC[N+](C)C)[O-] CHEBI:58641:*PUBCHEM:25201906:*LIGAND-CPD:C13482: 2.1.1.103 N-dimethylethanolamine phosphate + S-adenosyl-L-methionine = H+ + phosphoryl-choline + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis II N-dimethylethanolamine phosphate N,N-dimethylethanolamine phosphate*dimethylethanolamine phosphate*P-DME 168.109 C4 H11 N1 O4 P1 P([O-])(=O)(OCC[N+](C)C)[O-] CHEBI:58641:*PUBCHEM:25201906:*LIGAND-CPD:C13482: 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = H+ + N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis IV N-dimethylethanolamine phosphate N,N-dimethylethanolamine phosphate*dimethylethanolamine phosphate*P-DME 168.109 C4 H11 N1 O4 P1 P([O-])(=O)(OCC[N+](C)C)[O-] CHEBI:58641:*PUBCHEM:25201906:*LIGAND-CPD:C13482: 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = H+ + N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine choline biosynthesis I N-dimethylethanolamine phosphate N,N-dimethylethanolamine phosphate*dimethylethanolamine phosphate*P-DME 168.109 C4 H11 N1 O4 P1 P([O-])(=O)(OCC[N+](C)C)[O-] CHEBI:58641:*PUBCHEM:25201906:*LIGAND-CPD:C13482: 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = H+ + N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis II N-dimethylethanolamine phosphate N,N-dimethylethanolamine phosphate*dimethylethanolamine phosphate*P-DME 168.109 C4 H11 N1 O4 P1 P([O-])(=O)(OCC[N+](C)C)[O-] CHEBI:58641:*PUBCHEM:25201906:*LIGAND-CPD:C13482: 2.7.7.- H+ + N-dimethylethanolamine phosphate + CTP = CDP-N-dimethylethanolamine + diphosphate phosphatidylcholine biosynthesis IV 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline*OHCU 201.118 C5 H5 N4 O5 C1(N=C(C(O)(N1)C(=O)[O-])NC(=O)N)=O CHEBI:58639:*PUBCHEM:21145222:*LIGAND-CPD:C12248: H+ + 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate = S-allantoin + CO2 urate degradation to allantoin 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline*OHCU 201.118 C5 H5 N4 O5 C1(N=C(C(O)(N1)C(=O)[O-])NC(=O)N)=O CHEBI:58639:*PUBCHEM:21145222:*LIGAND-CPD:C12248: 3.5.2.17 5-hydroxyisourate + H2O = H+ + 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate urate degradation to allantoin indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 174.179 C10 H8 N1 O2 O=C([O-])CC1(=CNC2(C=CC=CC1=2)) PUBCHEM:801:*KNAPSACK:C00000100:*PUBCHEM:801:*CHEBI:30854:*LIGAND-CPD:C00954:*CAS:87-51-4 3.5.5.1 indole-3-acetonitrile + H2O = H+ + ammonia + indole-3-acetate IAA biosynthesis I indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 174.179 C10 H8 N1 O2 O=C([O-])CC1(=CNC2(C=CC=CC1=2)) PUBCHEM:801:*KNAPSACK:C00000100:*PUBCHEM:801:*CHEBI:30854:*LIGAND-CPD:C00954:*CAS:87-51-4 2.4.1.121 indole-3-acetate = indole-3-acetyl-β-1-D-glucose + UDP IAA conjugate biosynthesis I indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 174.179 C10 H8 N1 O2 O=C([O-])CC1(=CNC2(C=CC=CC1=2)) PUBCHEM:801:*KNAPSACK:C00000100:*PUBCHEM:801:*CHEBI:30854:*LIGAND-CPD:C00954:*CAS:87-51-4 2.1.1.- indole-3-acetate + S-adenosyl-L-methionine = methyl indole-3-acetate + S-adenosyl-L-homocysteine methyl indole-3-acetate interconversion indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 174.179 C10 H8 N1 O2 O=C([O-])CC1(=CNC2(C=CC=CC1=2)) PUBCHEM:801:*KNAPSACK:C00000100:*PUBCHEM:801:*CHEBI:30854:*LIGAND-CPD:C00954:*CAS:87-51-4 3.5.1.4 indole-3-acetamide + H2O = H+ + indole-3-acetate + ammonia IAA biosynthesis I indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 174.179 C10 H8 N1 O2 O=C([O-])CC1(=CNC2(C=CC=CC1=2)) PUBCHEM:801:*KNAPSACK:C00000100:*PUBCHEM:801:*CHEBI:30854:*LIGAND-CPD:C00954:*CAS:87-51-4 3.1.1.1 methyl indole-3-acetate + H2O = H+ + indole-3-acetate + methanol methyl indole-3-acetate interconversion indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 174.179 C10 H8 N1 O2 O=C([O-])CC1(=CNC2(C=CC=CC1=2)) PUBCHEM:801:*KNAPSACK:C00000100:*PUBCHEM:801:*CHEBI:30854:*LIGAND-CPD:C00954:*CAS:87-51-4 3.5.1.- indole-3-acetyl-alanine + H2O = indole-3-acetate + L-alanine IAA biosynthesis II indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 174.179 C10 H8 N1 O2 O=C([O-])CC1(=CNC2(C=CC=CC1=2)) PUBCHEM:801:*KNAPSACK:C00000100:*PUBCHEM:801:*CHEBI:30854:*LIGAND-CPD:C00954:*CAS:87-51-4 indole + acetate = H+ + indole-3-acetate IAA biosynthesis I indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 174.179 C10 H8 N1 O2 O=C([O-])CC1(=CNC2(C=CC=CC1=2)) PUBCHEM:801:*KNAPSACK:C00000100:*PUBCHEM:801:*CHEBI:30854:*LIGAND-CPD:C00954:*CAS:87-51-4 1.2.3.7 indole acetaldehyde + oxygen + H2O = H+ + indole-3-acetate + hydrogen peroxide IAA biosynthesis I indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 174.179 C10 H8 N1 O2 O=C([O-])CC1(=CNC2(C=CC=CC1=2)) PUBCHEM:801:*KNAPSACK:C00000100:*PUBCHEM:801:*CHEBI:30854:*LIGAND-CPD:C00954:*CAS:87-51-4 3.5.1.- indole-3-acetyl-leucine + H2O = indole-3-acetate + L-leucine IAA biosynthesis II shikimate-3-phosphate shikimate-5-phosphate*shikimate-5-P*3-phosphoshikimate*5-phosphoshikimate*shikimate-3-P 251.109 C7 H8 O8 P1 C1(OP(=O)([O-])[O-])(C=C(C(=O)[O-])CC(O)C(O)1) CHEBI:145989:*PUBCHEM:14506806:*LIGAND-CPD:C03175: 2.5.1.19 shikimate-3-phosphate + phosphoenolpyruvate = 5-enolpyruvyl-shikimate-3-phosphate chorismate biosynthesis I shikimate-3-phosphate shikimate-5-phosphate*shikimate-5-P*3-phosphoshikimate*5-phosphoshikimate*shikimate-3-P 251.109 C7 H8 O8 P1 C1(OP(=O)([O-])[O-])(C=C(C(=O)[O-])CC(O)C(O)1) CHEBI:145989:*PUBCHEM:14506806:*LIGAND-CPD:C03175: 2.7.1.71 shikimate + ATP = H+ + shikimate-3-phosphate + ADP chorismate biosynthesis I phloretin 274.273 C15 H14 O5 C(C1(C(=CC(O)=CC(O)=1)O))(=O)CCC2(C=CC(O)=CC=2) PUBCHEM:4788:*CHEBI:17276:*LIGAND-CPD:C00774:*NCI:407292 phloretin = phlorizin + UDP phloridzin biosynthesis phloretin 274.273 C15 H14 O5 C(C1(C(=CC(O)=CC(O)=1)O))(=O)CCC2(C=CC(O)=CC=2) PUBCHEM:4788:*CHEBI:17276:*LIGAND-CPD:C00774:*NCI:407292 2.3.1.- p-dihydrocoumaroyl-CoA + malonyl-CoA + H+ = phloretin + coenzyme A + CO2 phloridzin biosynthesis ADP-α-D-glucose adenosine diphosphate glucose*ADP-glucose*ADP-D-glucose 587.33 C16 H23 N5 O15 P2 OC1(C(C(C(OC1OP(OP(OCC2(OC(C(C2O)O)N3(C4(C(=NC=NC(N=C3)=4)N))))(=O)[O-])(=O)[O-])CO)O)O) PUBCHEM:25244286:*LIGAND-CPD:C00498:*CAS:2140-58-1 2.7.7.27 H+ + α-D-glucose 1-phosphate + ATP = ADP-α-D-glucose + diphosphate glycogen biosynthesis I (from ADP-D-Glucose) ADP-α-D-glucose adenosine diphosphate glucose*ADP-glucose*ADP-D-glucose 587.33 C16 H23 N5 O15 P2 OC1(C(C(C(OC1OP(OP(OCC2(OC(C(C2O)O)N3(C4(C(=NC=NC(N=C3)=4)N))))(=O)[O-])(=O)[O-])CO)O)O) PUBCHEM:25244286:*LIGAND-CPD:C00498:*CAS:2140-58-1 2.7.7.27 H+ + α-D-glucose 1-phosphate + ATP = ADP-α-D-glucose + diphosphate starch biosynthesis ADP-α-D-glucose adenosine diphosphate glucose*ADP-glucose*ADP-D-glucose 587.33 C16 H23 N5 O15 P2 OC1(C(C(C(OC1OP(OP(OCC2(OC(C(C2O)O)N3(C4(C(=NC=NC(N=C3)=4)N))))(=O)[O-])(=O)[O-])CO)O)O) PUBCHEM:25244286:*LIGAND-CPD:C00498:*CAS:2140-58-1 2.4.1.21 ADP-α-D-glucose = ADP glycogen biosynthesis I (from ADP-D-Glucose) ADP-α-D-glucose adenosine diphosphate glucose*ADP-glucose*ADP-D-glucose 587.33 C16 H23 N5 O15 P2 OC1(C(C(C(OC1OP(OP(OCC2(OC(C(C2O)O)N3(C4(C(=NC=NC(N=C3)=4)N))))(=O)[O-])(=O)[O-])CO)O)O) PUBCHEM:25244286:*LIGAND-CPD:C00498:*CAS:2140-58-1 2.4.1.21 ADP-α-D-glucose = ADP starch biosynthesis L-tyrosine Y*tyr*tyrosine 181.191 C9 H11 N1 O3 C(C([O-])=O)(CC1(C=CC(O)=CC=1))[N+] PUBCHEM:6942100:*PUBCHEM:4300518:*KNAPSACK:C00001397:*PUBCHEM:4300518:*LIGAND-CPD:C00082:*CAS:60-18-4 1.3.1.78 L-arogenate + NADP+ = L-tyrosine + CO2 + NADPH tyrosine biosynthesis II L-tyrosine Y*tyr*tyrosine 181.191 C9 H11 N1 O3 C(C([O-])=O)(CC1(C=CC(O)=CC=1))[N+] PUBCHEM:6942100:*PUBCHEM:4300518:*KNAPSACK:C00001397:*PUBCHEM:4300518:*LIGAND-CPD:C00082:*CAS:60-18-4 2.6.1.5 L-tyrosine + 2-oxoglutarate = L-glutamate + 4-hydroxyphenylpyruvate 4-hydroxyphenylpyruvate biosynthesis L-tyrosine Y*tyr*tyrosine 181.191 C9 H11 N1 O3 C(C([O-])=O)(CC1(C=CC(O)=CC=1))[N+] PUBCHEM:6942100:*PUBCHEM:4300518:*KNAPSACK:C00001397:*PUBCHEM:4300518:*LIGAND-CPD:C00082:*CAS:60-18-4 6.1.1.1 H+ + L-tyrosine + ATP = diphosphate + AMP tRNA charging pathway 4α-carboxy-stigmasta-7,24(241)-dien-3β-ol 455.699 C30 H47 O3 CC=C(CCC(C)C2(CCC1(C3(=CCC4(C(C([O-])=O)C(O)CCC(C)(C(CCC(C)12)3)4)))))C(C)C 1.1.1.- 4α-carboxy-stigmasta-7,24(241)-dien-3β-ol + NAD+ = avenastenone + NADH + CO2 plant sterol biosynthesis 4α-carboxy-stigmasta-7,24(241)-dien-3β-ol 455.699 C30 H47 O3 CC=C(CCC(C)C2(CCC1(C3(=CCC4(C(C([O-])=O)C(O)CCC(C)(C(CCC(C)12)3)4)))))C(C)C 1.14.13.- 4α-formyl-stigmasta-7,24(241)-dien-3β-ol + NADH + oxygen = 4α-carboxy-stigmasta-7,24(241)-dien-3β-ol + NAD+ + H2O plant sterol biosynthesis abscisic aldehyde ABA aldehyde*abscisic acid aldehyde 248.321 C15 H20 O3 C1(C(C(C(=CC1=O)C)(O)C=CC(=CC=O)C)(C)C) PUBCHEM:5282224:*CHEBI:31157:*LIGAND-CPD:C13455: 1.1.1.288 xanthoxin + NAD+ = abscisic aldehyde + NADH + H+ abscisic acid biosynthesis abscisic aldehyde ABA aldehyde*abscisic acid aldehyde 248.321 C15 H20 O3 C1(C(C(C(=CC1=O)C)(O)C=CC(=CC=O)C)(C)C) PUBCHEM:5282224:*CHEBI:31157:*LIGAND-CPD:C13455: 1.2.3.14 abscisic aldehyde + H2O + oxygen = H+ + 2-cis-abscisic acid + hydrogen peroxide abscisic acid biosynthesis abscisic aldehyde ABA aldehyde*abscisic acid aldehyde 248.321 C15 H20 O3 C1(C(C(C(=CC1=O)C)(O)C=CC(=CC=O)C)(C)C) PUBCHEM:5282224:*CHEBI:31157:*LIGAND-CPD:C13455: 1.2.3.14 abscisic aldehyde + H2O + oxygen = H+ + 2-cis-abscisic acid + hydrogen peroxide aldehyde oxidation I D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH gluconeogenesis I D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH glycolysis III D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH glycolysis IV (plant cytosol) D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH glycolysis I D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate pentose phosphate pathway (partial) D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate Rubisco shunt D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate pentose phosphate pathway (non-oxidative branch) D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = D-fructose-6-phosphate + D-glyceraldehyde-3-phosphate Calvin-Benson-Bassham cycle D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = D-fructose-6-phosphate + D-erythrose-4-phosphate Rubisco shunt D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = D-fructose-6-phosphate + D-erythrose-4-phosphate pentose phosphate pathway (non-oxidative branch) D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate pentose phosphate pathway (partial) D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate Rubisco shunt D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate pentose phosphate pathway (non-oxidative branch) D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate = D-ribose-5-phosphate + D-xylulose-5-phosphate Calvin-Benson-Bassham cycle D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.7 H+ + pyruvate + D-glyceraldehyde-3-phosphate = 1-deoxy-D-xylulose 5-phosphate + CO2 methylerythritol phosphate pathway D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.8 (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate = indole + D-glyceraldehyde-3-phosphate IAA biosynthesis I D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.8 (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate = indole + D-glyceraldehyde-3-phosphate tryptophan biosynthesis D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 1.2.1.9 D-glyceraldehyde-3-phosphate + NADP+ + H2O = H+ + 3-phospho-D-glycerate + NADPH glycolysis IV (plant cytosol) D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.13 fructose-1,6-bisphosphate = dihydroxyacetone phosphate + D-glyceraldehyde-3-phosphate gluconeogenesis I D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.13 fructose-1,6-bisphosphate = dihydroxyacetone phosphate + D-glyceraldehyde-3-phosphate glycolysis III D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.13 fructose-1,6-bisphosphate = dihydroxyacetone phosphate + D-glyceraldehyde-3-phosphate glycolysis IV (plant cytosol) D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.13 fructose-1,6-bisphosphate = dihydroxyacetone phosphate + D-glyceraldehyde-3-phosphate glycolysis I D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.13 fructose-1,6-bisphosphate = dihydroxyacetone phosphate + D-glyceraldehyde-3-phosphate Calvin-Benson-Bassham cycle D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxyacetone phosphate glycolysis III D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxyacetone phosphate glycolysis IV (plant cytosol) D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxyacetone phosphate glycolysis I D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxyacetone phosphate Calvin-Benson-Bassham cycle D-glyceraldehyde-3-phosphate D-glyceraldehdye-3-phosphate*3-phosphoglyceraldehyde*D-glyceraldehyde-3-P*glyceraldehyde-3-phosphate*gap*glyceraldehyde-phosphate*glyceraldehyde-P*glyceraldehyde-3-P*(2R)-2-hydroxy-3-(phosphonooxy)-propanal*triose phosphate 168.043 C3 H5 O6 P1 O=CC(O)COP(=O)([O-])[O-] PUBCHEM:24794350:*CHEBI:59776:*PUBCHEM:24794350:*KNAPKSACK:C00007564*LIGAND-CPD:C00661:*CAS:142-10-9 1.2.1.13 NADP+ + D-glyceraldehyde-3-phosphate = H+ + NADPH + 1,3-bisphospho-D-glycerate Calvin-Benson-Bassham cycle nicotinate adenine dinucleotide deamido-NAD*Deamino-NAD+*NaADN*deamido-NAD+*deamidonicotinamide adenine dinucleoetide*nicotinate adenine dinucleotide*NAAD 662.399 C21 H24 N6 O15 P2 C5(C=[N+](C1(C(C(O)C(O1)COP(=O)([O-])OP([O-])(OCC4(C(O)C(O)C(N2(C3(C(N=C2)=C(N=CN=3)N)))O4))=O)O))C=C(C([O-])=O)C=5) PUBCHEM:25246170:*LIGAND-CPD:C00857:*CAS:6450-77-7 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) nicotinate adenine dinucleotide deamido-NAD*Deamino-NAD+*NaADN*deamido-NAD+*deamidonicotinamide adenine dinucleoetide*nicotinate adenine dinucleotide*NAAD 662.399 C21 H24 N6 O15 P2 C5(C=[N+](C1(C(C(O)C(O1)COP(=O)([O-])OP([O-])(OCC4(C(O)C(O)C(N2(C3(C(N=C2)=C(N=CN=3)N)))O4))=O)O))C=C(C([O-])=O)C=5) PUBCHEM:25246170:*LIGAND-CPD:C00857:*CAS:6450-77-7 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ pyridine nucleotide cycling (plants) nicotinate adenine dinucleotide deamido-NAD*Deamino-NAD+*NaADN*deamido-NAD+*deamidonicotinamide adenine dinucleoetide*nicotinate adenine dinucleotide*NAAD 662.399 C21 H24 N6 O15 P2 C5(C=[N+](C1(C(C(O)C(O1)COP(=O)([O-])OP([O-])(OCC4(C(O)C(O)C(N2(C3(C(N=C2)=C(N=CN=3)N)))O4))=O)O))C=C(C([O-])=O)C=5) PUBCHEM:25246170:*LIGAND-CPD:C00857:*CAS:6450-77-7 2.7.7.18 H+ + ATP + nicotinate mononucleotide = diphosphate + nicotinate adenine dinucleotide NAD biosynthesis I (from aspartate) nicotinate adenine dinucleotide deamido-NAD*Deamino-NAD+*NaADN*deamido-NAD+*deamidonicotinamide adenine dinucleoetide*nicotinate adenine dinucleotide*NAAD 662.399 C21 H24 N6 O15 P2 C5(C=[N+](C1(C(C(O)C(O1)COP(=O)([O-])OP([O-])(OCC4(C(O)C(O)C(N2(C3(C(N=C2)=C(N=CN=3)N)))O4))=O)O))C=C(C([O-])=O)C=5) PUBCHEM:25246170:*LIGAND-CPD:C00857:*CAS:6450-77-7 2.7.7.18 H+ + ATP + nicotinate mononucleotide = diphosphate + nicotinate adenine dinucleotide pyridine nucleotide cycling (plants) nicotinate adenine dinucleotide deamido-NAD*Deamino-NAD+*NaADN*deamido-NAD+*deamidonicotinamide adenine dinucleoetide*nicotinate adenine dinucleotide*NAAD 662.399 C21 H24 N6 O15 P2 C5(C=[N+](C1(C(C(O)C(O1)COP(=O)([O-])OP([O-])(OCC4(C(O)C(O)C(N2(C3(C(N=C2)=C(N=CN=3)N)))O4))=O)O))C=C(C([O-])=O)C=5) PUBCHEM:25246170:*LIGAND-CPD:C00857:*CAS:6450-77-7 6.3.1.5 ammonia + ATP + nicotinate adenine dinucleotide = AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) homogentisate 2,5-dihydroxyphenylacetate 167.141 C8 H7 O4 C1(C=C(C(=CC=1)O)CC([O-])=O)O PUBCHEM:5460389:*CHEBI:16169:*LIGAND-CPD:C00544: 1.13.11.27 4-hydroxyphenylpyruvate + oxygen = CO2 + homogentisate vitamin E biosynthesis homogentisate 2,5-dihydroxyphenylacetate 167.141 C8 H7 O4 C1(C=C(C(=CC=1)O)CC([O-])=O)O PUBCHEM:5460389:*CHEBI:16169:*LIGAND-CPD:C00544: H+ + homogentisate + phytyl diphosphate = 2-methyl-6-phytyl-1,4-benzoquinol + CO2 + diphosphate vitamin E biosynthesis porphobilinogen 225.224 C10 H13 N2 O4 C1(C(=C(NC=1)C[N+])CC(=O)[O-])CCC(=O)[O-] PUBCHEM:6921588:*LIGAND-CPD:C00931:*CAS:487-90-1 4.2.1.24 5-amino-levulinate = H+ + H2O + porphobilinogen tetrapyrrole biosynthesis I porphobilinogen 225.224 C10 H13 N2 O4 C1(C(=C(NC=1)C[N+])CC(=O)[O-])CCC(=O)[O-] PUBCHEM:6921588:*LIGAND-CPD:C00931:*CAS:487-90-1 2.5.1.61 H2O + porphobilinogen = H+ + ammonia + hydroxymethylbilane tetrapyrrole biosynthesis I Δ1-piperideine-6-carboxylate (S)-2,3,4,5-tetrahydropiperidine-2-carboxylate*Δ6-piperideine-2-carboxylate*1,6-didehydropiperidine-2-carboxylate*2,3,4,5-tetrahydropyridine-2-carboxylate*1-piperideine-6-carboxylate 126.135 C6 H8 N1 O2 C1(CC(N=CC1)C([O-])=O) PUBCHEM:5460090:*CHEBI:16987:*LIGAND-CPD:C00450: 1.2.1.31 H+ + Δ1-piperideine-6-carboxylate + H2O = 2-aminoadipate-6-semialdehyde lysine degradation II Δ1-piperideine-6-carboxylate (S)-2,3,4,5-tetrahydropiperidine-2-carboxylate*Δ6-piperideine-2-carboxylate*1,6-didehydropiperidine-2-carboxylate*2,3,4,5-tetrahydropyridine-2-carboxylate*1-piperideine-6-carboxylate 126.135 C6 H8 N1 O2 C1(CC(N=CC1)C([O-])=O) PUBCHEM:5460090:*CHEBI:16987:*LIGAND-CPD:C00450: 1.2.1.31 Δ1-piperideine-6-carboxylate + NAD+ + H2O = 2-aminoadipate + NADH + H+ lysine degradation II L-aspartate-semialdehyde L-aspartic 4-semialdehyde*L-aspartate-4-semialdehyde*L-aspartate β-semialdehyde 117.104 C4 H7 N1 O3 [N+]C(CC=O)C(=O)[O-] CHEBI:537519:*PUBCHEM:5287708:*LIGAND-CPD:C00441:*CAS:15106-57-7 1.2.1.11 NADP+ + L-aspartate-semialdehyde = H+ + NADPH + L-aspartyl-4-phosphate lysine biosynthesis VI L-aspartate-semialdehyde L-aspartic 4-semialdehyde*L-aspartate-4-semialdehyde*L-aspartate β-semialdehyde 117.104 C4 H7 N1 O3 [N+]C(CC=O)C(=O)[O-] CHEBI:537519:*PUBCHEM:5287708:*LIGAND-CPD:C00441:*CAS:15106-57-7 1.2.1.11 NADP+ + L-aspartate-semialdehyde = H+ + NADPH + L-aspartyl-4-phosphate homoserine biosynthesis L-aspartate-semialdehyde L-aspartic 4-semialdehyde*L-aspartate-4-semialdehyde*L-aspartate β-semialdehyde 117.104 C4 H7 N1 O3 [N+]C(CC=O)C(=O)[O-] CHEBI:537519:*PUBCHEM:5287708:*LIGAND-CPD:C00441:*CAS:15106-57-7 1.1.1.3 L-homoserine = L-aspartate-semialdehyde + H+ homoserine biosynthesis L-aspartate-semialdehyde L-aspartic 4-semialdehyde*L-aspartate-4-semialdehyde*L-aspartate β-semialdehyde 117.104 C4 H7 N1 O3 [N+]C(CC=O)C(=O)[O-] CHEBI:537519:*PUBCHEM:5287708:*LIGAND-CPD:C00441:*CAS:15106-57-7 4.2.1.52 pyruvate + L-aspartate-semialdehyde = H+ + H2O + L-2,3-dihydrodipicolinate lysine biosynthesis VI 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP gluconeogenesis I 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP glycolysis III 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP glycolysis IV (plant cytosol) 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP glycolysis I 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP Calvin-Benson-Bassham cycle 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 1.1.1.95 3-phospho-D-glycerate + NAD+ = H+ + 3-phospho-hydroxypyruvate + NADH serine biosynthesis 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 2.7.1.31 D-glycerate + ATP = H+ + 3-phospho-D-glycerate + ADP photorespiration 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 4.1.1.- D-ribulose-1,5-bisphosphate + oxygen = 2-phosphoglycolate + 3-phospho-D-glycerate + H+ photorespiration 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 5.4.2.1 3-phospho-D-glycerate = 2-phospho-D-glycerate gluconeogenesis I 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 5.4.2.1 3-phospho-D-glycerate = 2-phospho-D-glycerate Rubisco shunt 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 5.4.2.1 3-phospho-D-glycerate = 2-phospho-D-glycerate glycolysis III 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 5.4.2.1 3-phospho-D-glycerate = 2-phospho-D-glycerate glycolysis IV (plant cytosol) 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 5.4.2.1 3-phospho-D-glycerate = 2-phospho-D-glycerate glycolysis I 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 4.1.1.39 D-ribulose-1,5-bisphosphate + CO2 + H2O = 3-phospho-D-glycerate + H+ Rubisco shunt 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 4.1.1.39 D-ribulose-1,5-bisphosphate + CO2 + H2O = 3-phospho-D-glycerate + H+ Calvin-Benson-Bassham cycle 3-phospho-D-glycerate 3-phosphoglycerate*D-glycerate 3-phosphate*D-glycerate-3-P*3-phospho-D-glyceric acid*3-phospho-(R)-glycerate*3-phospho-glyceric acid*G3P*3-PG*3-P-glycerate*glycerate 3-phosphate*3-phospho-D-glycerate*3-P-D-glycerate*glycerate-3-P*D-Glycerate 3-phosphate*phosphoglycerate*3-PGA 183.034 C3 H4 O7 P1 O=C([O-])C(O)COP(=O)([O-])[O-] KNAPKSACK:C00007286*CHEBI:242490:*PUBCHEM:25245548:*LIGAND-CPD:C00197:*CAS:820-11-1 1.2.1.9 D-glyceraldehyde-3-phosphate + NADP+ + H2O = H+ + 3-phospho-D-glycerate + NADPH glycolysis IV (plant cytosol) α-D-glucose D-glucose*glucose*α-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OC1(OC(C(C(C1O)O)O)CO) CHEBI:17925:*PUBCHEM:79025:*LIGAND-CPD:C00267: 2.7.1.1 α-D-glucose + ATP = H+ + α-D-glucose 6-phosphate + ADP sucrose degradation III α-D-glucose D-glucose*glucose*α-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OC1(OC(C(C(C1O)O)O)CO) CHEBI:17925:*PUBCHEM:79025:*LIGAND-CPD:C00267: 2.7.1.1 α-D-glucose + ATP = H+ + α-D-glucose 6-phosphate + ADP starch degradation α-D-glucose D-glucose*glucose*α-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OC1(OC(C(C(C1O)O)O)CO) CHEBI:17925:*PUBCHEM:79025:*LIGAND-CPD:C00267: 3.2.1.26 sucrose + H2O = α-D-glucose + β-D-fructofuranose sucrose degradation III α-D-glucose D-glucose*glucose*α-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OC1(OC(C(C(C1O)O)O)CO) CHEBI:17925:*PUBCHEM:79025:*LIGAND-CPD:C00267: 3.2.1.20 maltotriose + H2O = maltose + α-D-glucose glycogen degradation I α-D-glucose D-glucose*glucose*α-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OC1(OC(C(C(C1O)O)O)CO) CHEBI:17925:*PUBCHEM:79025:*LIGAND-CPD:C00267: 2.4.1.25 starch degradation α-D-glucose D-glucose*glucose*α-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 OC1(OC(C(C(C1O)O)O)CO) CHEBI:17925:*PUBCHEM:79025:*LIGAND-CPD:C00267: 3.2.1.20 α-maltose + H2O = α-D-glucose starch degradation L-α-(methylenecyclopropyl)-glycine 127.143 C6 H9 N1 O2 C1(C(C([N+])C(=O)[O-])C1)(=C) PUBCHEM:25203707:*LIGAND-CPD:C08292: 2.6.1.- 2-oxohexa-4,5-cyclopropyl-5-enoate = L-α-(methylenecyclopropyl)-glycine hypoglycin biosynthesis glutaryl-CoA glutaryl-coenzyme A 876.595 C26 H37 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(NCCC(=O)NCCSC(CCCC(=O)[O-])=O)=O)O)[O-])O1)OP(=O)([O-])[O-])(N3(C=NC2(C(=NC=NC=23)N))) PUBCHEM:25244295:*LIGAND-CPD:C00527: 2-oxoadipate + NAD+ + coenzyme A = CO2 + NADH + glutaryl-CoA lysine degradation II fumarate fum*fumaric acid 114.057 C4 H2 O4 [O-]C(C=CC(=O)[O-])=O KNAPSACK:C00001183:*PUBCHEM:5460307:*CHEBI:29806:*LIGAND-CPD:C00122:*CAS:110-17-8 4.2.1.2 (S)-malate = fumarate + H2O TCA cycle variation III (eukaryotic) fumarate fum*fumaric acid 114.057 C4 H2 O4 [O-]C(C=CC(=O)[O-])=O KNAPSACK:C00001183:*PUBCHEM:5460307:*CHEBI:29806:*LIGAND-CPD:C00122:*CAS:110-17-8 4.2.1.2 (S)-malate = fumarate + H2O superpathway of glyoxylate cycle fumarate fum*fumaric acid 114.057 C4 H2 O4 [O-]C(C=CC(=O)[O-])=O KNAPSACK:C00001183:*PUBCHEM:5460307:*CHEBI:29806:*LIGAND-CPD:C00122:*CAS:110-17-8 4.3.2.2 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole = fumarate + aminoimidazole carboxamide ribonucleotide inosine-5'-phosphate biosynthesis II fumarate fum*fumaric acid 114.057 C4 H2 O4 [O-]C(C=CC(=O)[O-])=O KNAPSACK:C00001183:*PUBCHEM:5460307:*CHEBI:29806:*LIGAND-CPD:C00122:*CAS:110-17-8 4.3.2.2 adenylo-succinate = fumarate + AMP purine nucleotides de novo biosynthesis II fumarate fum*fumaric acid 114.057 C4 H2 O4 [O-]C(C=CC(=O)[O-])=O KNAPSACK:C00001183:*PUBCHEM:5460307:*CHEBI:29806:*LIGAND-CPD:C00122:*CAS:110-17-8 4.3.2.2 adenylo-succinate = fumarate + AMP adenosine nucleotides de novo biosynthesis fumarate fum*fumaric acid 114.057 C4 H2 O4 [O-]C(C=CC(=O)[O-])=O KNAPSACK:C00001183:*PUBCHEM:5460307:*CHEBI:29806:*LIGAND-CPD:C00122:*CAS:110-17-8 4.3.2.1 L-arginino-succinate = L-arginine + fumarate urea cycle fumarate fum*fumaric acid 114.057 C4 H2 O4 [O-]C(C=CC(=O)[O-])=O KNAPSACK:C00001183:*PUBCHEM:5460307:*CHEBI:29806:*LIGAND-CPD:C00122:*CAS:110-17-8 4.3.2.1 L-arginino-succinate = L-arginine + fumarate arginine biosynthesis II (acetyl cycle) fumarate fum*fumaric acid 114.057 C4 H2 O4 [O-]C(C=CC(=O)[O-])=O KNAPSACK:C00001183:*PUBCHEM:5460307:*CHEBI:29806:*LIGAND-CPD:C00122:*CAS:110-17-8 4.3.2.1 L-arginino-succinate = L-arginine + fumarate citrulline-nitric oxide cycle fumarate fum*fumaric acid 114.057 C4 H2 O4 [O-]C(C=CC(=O)[O-])=O KNAPSACK:C00001183:*PUBCHEM:5460307:*CHEBI:29806:*LIGAND-CPD:C00122:*CAS:110-17-8 4.3.2.1 L-arginino-succinate = L-arginine + fumarate arginine biosynthesis I fumarate fum*fumaric acid 114.057 C4 H2 O4 [O-]C(C=CC(=O)[O-])=O KNAPSACK:C00001183:*PUBCHEM:5460307:*CHEBI:29806:*LIGAND-CPD:C00122:*CAS:110-17-8 1.3.5.1 succinate = fumarate TCA cycle variation III (eukaryotic) fumarate fum*fumaric acid 114.057 C4 H2 O4 [O-]C(C=CC(=O)[O-])=O KNAPSACK:C00001183:*PUBCHEM:5460307:*CHEBI:29806:*LIGAND-CPD:C00122:*CAS:110-17-8 1.3.5.1 succinate = fumarate aerobic respiration -- electron donor II fumarate fum*fumaric acid 114.057 C4 H2 O4 [O-]C(C=CC(=O)[O-])=O KNAPSACK:C00001183:*PUBCHEM:5460307:*CHEBI:29806:*LIGAND-CPD:C00122:*CAS:110-17-8 1.3.5.1 succinate = fumarate succinate to cytochrome bd oxidase electron transfer fumarate fum*fumaric acid 114.057 C4 H2 O4 [O-]C(C=CC(=O)[O-])=O KNAPSACK:C00001183:*PUBCHEM:5460307:*CHEBI:29806:*LIGAND-CPD:C00122:*CAS:110-17-8 1.3.5.1 succinate = fumarate superpathway of glyoxylate cycle catechin catechin*Cianidanol*cianidanol*2,3-trans-catechin*(2R,3S)-catechin 290.272 C15 H14 O6 C1(C(=CC(=C2(C=1OC(C(C2)O)C3(C=CC(=C(C=3)O)O)))O)O) CHEBI:15600:*PUBCHEM:9064:*LIGAND-CPD:C06562: 1.17.1.3 catechin + NADP+ + H2O = leucocyanidin + NADPH + H+ 2,3-trans-flavanols biosynthesis 6-phospho-D-glucono-1,5-lactone 6-phospho-D-glucono-1,5-lactone*6-phosphogluconolactone*D-6-phosphoglucono-δ-lactone*D-6-P-glucono-δ-lactone*D-glucono-1,5-lactone-6-phosphate*D-glucono-δ-lactone-6-phosphate*D-6-phospho-glucono-δ-lactone 256.105 C6 H9 O9 P1 C1(C(O)C(O)C(O)C(=O)O1)COP([O-])([O-])=O CHEBI:16938:*PUBCHEM:25246175:*LIGAND-CPD:C01236:*CAS:2641-81-8 3.1.1.31 6-phospho-D-glucono-1,5-lactone + H2O = H+ + 6-phospho-D-gluconate pentose phosphate pathway (oxidative branch) 6-phospho-D-glucono-1,5-lactone 6-phospho-D-glucono-1,5-lactone*6-phosphogluconolactone*D-6-phosphoglucono-δ-lactone*D-6-P-glucono-δ-lactone*D-glucono-1,5-lactone-6-phosphate*D-glucono-δ-lactone-6-phosphate*D-6-phospho-glucono-δ-lactone 256.105 C6 H9 O9 P1 C1(C(O)C(O)C(O)C(=O)O1)COP([O-])([O-])=O CHEBI:16938:*PUBCHEM:25246175:*LIGAND-CPD:C01236:*CAS:2641-81-8 1.1.1.49 β-D-glucose-6-phosphate + NADP+ = 6-phospho-D-glucono-1,5-lactone + NADPH + H+ pentose phosphate pathway (oxidative branch) 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate 1D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*phytic acid*phytate*myo-inositol hexakisphosphate*D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*myo-Inositol 1,2,3,4,5,6-hexakisphosphate*Inositol 1,2,3,4,5,6-hexakisphosphate*InsP6*1D-myo-Inositol hexakisphosphate 647.942 C6 H6 O24 P6 C1(OP([O-])([O-])=O)(C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)1) PUBCHEM:16752675:*CHEBI:58130:*PUBCHEM:21584050:*LIGAND-CPD:C01204: 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate 1D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*phytic acid*phytate*myo-inositol hexakisphosphate*D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*myo-Inositol 1,2,3,4,5,6-hexakisphosphate*Inositol 1,2,3,4,5,6-hexakisphosphate*InsP6*1D-myo-Inositol hexakisphosphate 647.942 C6 H6 O24 P6 C1(OP([O-])([O-])=O)(C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)1) PUBCHEM:16752675:*CHEBI:58130:*PUBCHEM:21584050:*LIGAND-CPD:C01204: 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate 1D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*phytic acid*phytate*myo-inositol hexakisphosphate*D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*myo-Inositol 1,2,3,4,5,6-hexakisphosphate*Inositol 1,2,3,4,5,6-hexakisphosphate*InsP6*1D-myo-Inositol hexakisphosphate 647.942 C6 H6 O24 P6 C1(OP([O-])([O-])=O)(C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)1) PUBCHEM:16752675:*CHEBI:58130:*PUBCHEM:21584050:*LIGAND-CPD:C01204: 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate 1D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*phytic acid*phytate*myo-inositol hexakisphosphate*D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*myo-Inositol 1,2,3,4,5,6-hexakisphosphate*Inositol 1,2,3,4,5,6-hexakisphosphate*InsP6*1D-myo-Inositol hexakisphosphate 647.942 C6 H6 O24 P6 C1(OP([O-])([O-])=O)(C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)1) PUBCHEM:16752675:*CHEBI:58130:*PUBCHEM:21584050:*LIGAND-CPD:C01204: 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate 1D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*phytic acid*phytate*myo-inositol hexakisphosphate*D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*myo-Inositol 1,2,3,4,5,6-hexakisphosphate*Inositol 1,2,3,4,5,6-hexakisphosphate*InsP6*1D-myo-Inositol hexakisphosphate 647.942 C6 H6 O24 P6 C1(OP([O-])([O-])=O)(C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)1) PUBCHEM:16752675:*CHEBI:58130:*PUBCHEM:21584050:*LIGAND-CPD:C01204: 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate 1D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*phytic acid*phytate*myo-inositol hexakisphosphate*D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*myo-Inositol 1,2,3,4,5,6-hexakisphosphate*Inositol 1,2,3,4,5,6-hexakisphosphate*InsP6*1D-myo-Inositol hexakisphosphate 647.942 C6 H6 O24 P6 C1(OP([O-])([O-])=O)(C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)1) PUBCHEM:16752675:*CHEBI:58130:*PUBCHEM:21584050:*LIGAND-CPD:C01204: 3.1.3.8 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + H2O = D-myo-inositol (1,2,4,5,6)-pentakisphosphate phytate degradation I 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate 1D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*phytic acid*phytate*myo-inositol hexakisphosphate*D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*myo-Inositol 1,2,3,4,5,6-hexakisphosphate*Inositol 1,2,3,4,5,6-hexakisphosphate*InsP6*1D-myo-Inositol hexakisphosphate 647.942 C6 H6 O24 P6 C1(OP([O-])([O-])=O)(C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)1) PUBCHEM:16752675:*CHEBI:58130:*PUBCHEM:21584050:*LIGAND-CPD:C01204: 3.1.3.26 H2O + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate = D-myo-inositol (1,2,3,4,5)-pentakisphosphate phytate degradation II 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate 1D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*phytic acid*phytate*myo-inositol hexakisphosphate*D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*myo-Inositol 1,2,3,4,5,6-hexakisphosphate*Inositol 1,2,3,4,5,6-hexakisphosphate*InsP6*1D-myo-Inositol hexakisphosphate 647.942 C6 H6 O24 P6 C1(OP([O-])([O-])=O)(C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)1) PUBCHEM:16752675:*CHEBI:58130:*PUBCHEM:21584050:*LIGAND-CPD:C01204: 3.1.3.26 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + H2O = D-myo-inositol (1,2,3,5,6) pentakisphosphate phytate degradation I 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate 1D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*phytic acid*phytate*myo-inositol hexakisphosphate*D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate*myo-Inositol 1,2,3,4,5,6-hexakisphosphate*Inositol 1,2,3,4,5,6-hexakisphosphate*InsP6*1D-myo-Inositol hexakisphosphate 647.942 C6 H6 O24 P6 C1(OP([O-])([O-])=O)(C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)1) PUBCHEM:16752675:*CHEBI:58130:*PUBCHEM:21584050:*LIGAND-CPD:C01204: 2.7.1.140 1D-myo-inositol (1,2,3,4,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) (E)-cinnamoyl-CoA trans-cinnamoyl-CoA 893.648 C30 H38 N7 O17 P3 S1 C4(C=C(C=CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C=CC=4) PUBCHEM:44229143:*CHEBI:10956:*LIGAND-CPD:C16256: 2.3.1.- H+ + malonyl-CoA + (E)-cinnamoyl-CoA = pinocembrin chalcone + coenzyme A + CO2 pinobanksin biosynthesis (E)-cinnamoyl-CoA trans-cinnamoyl-CoA 893.648 C30 H38 N7 O17 P3 S1 C4(C=C(C=CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C=CC=4) PUBCHEM:44229143:*CHEBI:10956:*LIGAND-CPD:C16256: 6.2.1.- trans-cinnamate + coenzyme A + ATP = (E)-cinnamoyl-CoA + AMP + diphosphate trans-cinnamoyl-CoA biosynthesis (E)-cinnamoyl-CoA trans-cinnamoyl-CoA 893.648 C30 H38 N7 O17 P3 S1 C4(C=C(C=CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])C=CC=4) PUBCHEM:44229143:*CHEBI:10956:*LIGAND-CPD:C16256: (E)-cinnamoyl-CoA + H2O = 3-hydroxy-3-phenylpropionyl-CoA benzoate biosynthesis III (CoA-dependent, non-β-oxidative) 5-methyltetrahydropteroyltri-L-glutamate 717.691 C30 H39 N9 O12 CN3(C1(=C(NC(N)=NC(=O)1)NCC(CNC2(=CC=C(C=C2)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(=O)O)C(=O)O)C(=O)O))3)) PUBCHEM:16722111:*CHEBI:17614:*LIGAND-CPD:C04489: 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyl tri-L-glutamate + L-methionine methionine biosynthesis II 5-methyltetrahydropteroyltri-L-glutamate 717.691 C30 H39 N9 O12 CN3(C1(=C(NC(N)=NC(=O)1)NCC(CNC2(=CC=C(C=C2)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(=O)O)C(=O)O)C(=O)O))3)) PUBCHEM:16722111:*CHEBI:17614:*LIGAND-CPD:C04489: 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyl tri-L-glutamate + L-methionine S-adenosyl-L-methionine cycle I 5-methyltetrahydropteroyltri-L-glutamate 717.691 C30 H39 N9 O12 CN3(C1(=C(NC(N)=NC(=O)1)NCC(CNC2(=CC=C(C=C2)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(=O)O)C(=O)O)C(=O)O))3)) PUBCHEM:16722111:*CHEBI:17614:*LIGAND-CPD:C04489: 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyl tri-L-glutamate + L-methionine S-adenosyl-L-methionine cycle II dethiobiotin Desthiobiotin*DTB 213.256 C10 H17 N2 O3 [O-]C(=O)CCCCCC1(C(C)NC(=O)N1) CHEBI:57861:*PUBCHEM:25244917:*LIGAND-CPD:C01909:*CAS:533-48-2 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = H+ + dethiobiotin + ADP biotin biosynthesis from 7-keto-8-aminopelargonate dethiobiotin Desthiobiotin*DTB 213.256 C10 H17 N2 O3 [O-]C(=O)CCCCCC1(C(C)NC(=O)N1) CHEBI:57861:*PUBCHEM:25244917:*LIGAND-CPD:C01909:*CAS:533-48-2 2.8.1.6 dethiobiotin + S-adenosyl-L-methionine = biotin + 5'-deoxyadenosine + L-methionine biotin biosynthesis from 7-keto-8-aminopelargonate Δ24-25-sitosterol 412.698 C29 H48 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CCC(=C(C)C)CC)C)C(CC3)(C)4)))C))O) PUBCHEM:25201027: isofucosterol = Δ24-25-sitosterol plant sterol biosynthesis Δ24-25-sitosterol 412.698 C29 H48 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CCC(=C(C)C)CC)C)C(CC3)(C)4)))C))O) PUBCHEM:25201027: H+ + Δ24-25-sitosterol + NADPH = sitosterol + NADP+ plant sterol biosynthesis dADP deoxyadenosine-diphosphate*2'-deoxyadenosine-5'-diphosphate 408.18 C10 H12 N5 O9 P2 O=P(OP([O-])([O-])=O)(OCC3(C(CC(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O))[O-] CHEBI:57667:*PUBCHEM:21125569:*LIGAND-CPD:C00206:*CAS:2793-06-8 1.17.4.1 dADP + H2O = ADP adenosine nucleotides de novo biosynthesis dADP deoxyadenosine-diphosphate*2'-deoxyadenosine-5'-diphosphate 408.18 C10 H12 N5 O9 P2 O=P(OP([O-])([O-])=O)(OCC3(C(CC(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O))[O-] CHEBI:57667:*PUBCHEM:21125569:*LIGAND-CPD:C00206:*CAS:2793-06-8 2.7.4.6 dADP + ATP = dATP + ADP adenosine nucleotides de novo biosynthesis dADP deoxyadenosine-diphosphate*2'-deoxyadenosine-5'-diphosphate 408.18 C10 H12 N5 O9 P2 O=P(OP([O-])([O-])=O)(OCC3(C(CC(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O))[O-] CHEBI:57667:*PUBCHEM:21125569:*LIGAND-CPD:C00206:*CAS:2793-06-8 1.17.4.- ADP = dADP + H2O adenosine nucleotides de novo biosynthesis epigallocatechin 2,3-cis-epigallocatechin 306.271 C15 H14 O7 C3(C1(C(=CC(O)=CC(O)=1)OC(C2(C=C(O)C(O)=C(O)C=2))C(O)3)) PUBCHEM:72277:*LIGAND-CPD:C12136:*CHEBI:42255: 1.3.1.77 H+ + delphinidin = epigallocatechin 2,3-cis-flavanols biosynthesis phosphoribosyl-formamido-carboxamide 5-Phosphoribosyl-5-formamido-4-imid-carboxamide*5'-p-Ribosyl-5-formamido-4-imidazole carboxamide*5'-p-Ribosyl-5-formamido-4-imidazolecarboxamide*5-Formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide*5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide*5'-p-ribosyl-5-formamido-4-imidazolecarboxamide*5'-phosphoribosyl-5-formamido-4-imidazole carboxamide*5'-p-ribosyl-5-formamido-4-imidazole carboxamide*5-phosphoribosyl-5-formamido-4-imid-carboxamide*5-formamido-1-(5-phosphoribosyl)-imidazole-4-carboxamide*FAICAR*5-formylamidoimidazole-4-carboxamide ribonucleotide 364.208 C10 H13 N4 O9 P1 C1(N(C=NC=1C(=O)N)C2(C(O)C(C(COP([O-])(=O)[O-])O2)O))NC=O PUBCHEM:25244918:*LIGAND-CPD:C04734: 2.1.2.3 10-formyl-tetrahydrofolate + aminoimidazole carboxamide ribonucleotide = tetrahydrofolate + phosphoribosyl-formamido-carboxamide inosine-5'-phosphate biosynthesis II phosphoribosyl-formamido-carboxamide 5-Phosphoribosyl-5-formamido-4-imid-carboxamide*5'-p-Ribosyl-5-formamido-4-imidazole carboxamide*5'-p-Ribosyl-5-formamido-4-imidazolecarboxamide*5-Formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide*5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide*5'-p-ribosyl-5-formamido-4-imidazolecarboxamide*5'-phosphoribosyl-5-formamido-4-imidazole carboxamide*5'-p-ribosyl-5-formamido-4-imidazole carboxamide*5-phosphoribosyl-5-formamido-4-imid-carboxamide*5-formamido-1-(5-phosphoribosyl)-imidazole-4-carboxamide*FAICAR*5-formylamidoimidazole-4-carboxamide ribonucleotide 364.208 C10 H13 N4 O9 P1 C1(N(C=NC=1C(=O)N)C2(C(O)C(C(COP([O-])(=O)[O-])O2)O))NC=O PUBCHEM:25244918:*LIGAND-CPD:C04734: 3.5.4.10 inosine-5'-phosphate + H2O = phosphoribosyl-formamido-carboxamide inosine-5'-phosphate biosynthesis II β-tocopherol 5,8-dimethyltocol 416.686 C28 H48 O2 CC2(C=C(C(C)=C1(CCC(C)(CCCC(C)CCCC(C)CCCC(C)C)OC1=2))O) CHEBI:47771:*PUBCHEM:6857447:*LIGAND-CPD:C14152: 2.1.1.95 δ-tocopherol + S-adenosyl-L-methionine = H+ + β-tocopherol + S-adenosyl-L-homocysteine vitamin E biosynthesis coniferyl alcohol coniferyl alcohol*4-hydroxy-3-methoxycinnamyl alcohol*3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-ol*4-(3-hydroxy-1-propenyl)-2-methoxyphenol*γ-hydroxyisoeugenol*coniferol*E-coniferyl alcohol 180.203 C10 H12 O3 C1(C=C(C(=CC(C=CCO)=1)OC)O) PUBCHEM:1549095:*CHEBI:17745:*LIGAND-CPD:C00590:*CAS:458-35-5 2.4.1.111 coniferyl alcohol = H+ + coniferin + UDP coniferin metabolism coniferyl alcohol coniferyl alcohol*4-hydroxy-3-methoxycinnamyl alcohol*3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-ol*4-(3-hydroxy-1-propenyl)-2-methoxyphenol*γ-hydroxyisoeugenol*coniferol*E-coniferyl alcohol 180.203 C10 H12 O3 C1(C=C(C(=CC(C=CCO)=1)OC)O) PUBCHEM:1549095:*CHEBI:17745:*LIGAND-CPD:C00590:*CAS:458-35-5 1.1.1.195 coniferyl alcohol + NADP+ = coniferaldehyde + NADPH + H+ phenylpropanoid biosynthesis coniferyl alcohol coniferyl alcohol*4-hydroxy-3-methoxycinnamyl alcohol*3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-ol*4-(3-hydroxy-1-propenyl)-2-methoxyphenol*γ-hydroxyisoeugenol*coniferol*E-coniferyl alcohol 180.203 C10 H12 O3 C1(C=C(C(=CC(C=CCO)=1)OC)O) PUBCHEM:1549095:*CHEBI:17745:*LIGAND-CPD:C00590:*CAS:458-35-5 3.2.1.126 H2O + coniferin = coniferyl alcohol + β-D-glucose coniferin metabolism dihydroconiferyl alcohol glucoside dihydroconiferyl alcohol-4-O-β-D-glucopyranoside 344.361 C16 H24 O8 C1(C(=CC(=C(C=1)OC2(C(C(C(C(O2)CO)O)O)O))OC)CCCO) PUBCHEM:25244310: 2.4.1.- dihydroconiferyl alcohol = H+ + dihydroconiferyl alcohol glucoside + UDP monolignol glucosides biosynthesis isorhamnetin 3-sulphate 3' methylquercetin 3-sulphate*isorhamnetin 3-sulfate 394.309 C16 H10 O10 S1 O=C1(C(OS(=O)(=O)[O-])=C(OC2(C=C([O-])C=C(O)C1=2))C3(=CC=C(O)C(=C3)OC)) PUBCHEM:44123491: isorhamnetin + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + isorhamnetin 3-sulphate quercetinsulphates biosynthesis isorhamnetin 3-sulphate 3' methylquercetin 3-sulphate*isorhamnetin 3-sulfate 394.309 C16 H10 O10 S1 O=C1(C(OS(=O)(=O)[O-])=C(OC2(C=C([O-])C=C(O)C1=2))C3(=CC=C(O)C(=C3)OC)) PUBCHEM:44123491: isorhamnetin 3-sulphate + phosphoadenosine-5'-phosphosulfate = H+ + adenosine 3',5'-bisphosphate + isorhamnetin 3, 4'-bisulphate quercetinsulphates biosynthesis 3-dehydro-6-deoxoteasterone dehydro-deoxoteasterone 432.685 C28 H48 O3 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(C(C(C(C(C)C)C)O)O)C)C(CC3)(C)4)))C))=O) PUBCHEM:25203725:*LIGAND-CPD:C15800: 1.14.13.112 (22S,24R)-22-hydroxy-5α-ergostan-3-one + oxygen + NADPH + H+ = 3-dehydro-6-deoxoteasterone + NADP+ + H2O brassinosteroid biosynthesis II 3-dehydro-6-deoxoteasterone dehydro-deoxoteasterone 432.685 C28 H48 O3 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(C(C(C(C(C)C)C)O)O)C)C(CC3)(C)4)))C))=O) PUBCHEM:25203725:*LIGAND-CPD:C15800: 6-deoxoteasterone = H+ + 3-dehydro-6-deoxoteasterone brassinosteroid biosynthesis II 3-dehydro-6-deoxoteasterone dehydro-deoxoteasterone 432.685 C28 H48 O3 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(C(C(C(C(C)C)C)O)O)C)C(CC3)(C)4)))C))=O) PUBCHEM:25203725:*LIGAND-CPD:C15800: H+ + 3-dehydro-6-deoxoteasterone = 6-deoxotyphasterol brassinosteroid biosynthesis II 3-dehydro-6-deoxoteasterone dehydro-deoxoteasterone 432.685 C28 H48 O3 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(C(C(C(C(C)C)C)O)O)C)C(CC3)(C)4)))C))=O) PUBCHEM:25203725:*LIGAND-CPD:C15800: H+ + (22R,23R)-22,23-dihydroxy-campest-4-en-3-one = 3-dehydro-6-deoxoteasterone brassinosteroid biosynthesis II trans-β-D-Glucosyl-2-hydroxycinnamate β-D-Glucosyl-2-coumarate 325.294 C15 H17 O8 C1(C=CC(=C(C=1)C=CC([O-])=O)OC2(C(C(C(C(O2)CO)O)O)O)) PUBCHEM:25245559:*LIGAND-CPD:C05158: 5.2.1.- trans-β-D-Glucosyl-2-hydroxycinnamate = cis-coumarinic acid-β-D-glucoside coumarin biosynthesis (via 2-coumarate) trans-β-D-Glucosyl-2-hydroxycinnamate β-D-Glucosyl-2-coumarate 325.294 C15 H17 O8 C1(C=CC(=C(C=1)C=CC([O-])=O)OC2(C(C(C(C(O2)CO)O)O)O)) PUBCHEM:25245559:*LIGAND-CPD:C05158: 2.4.1.114 2-coumarate = H+ + trans-β-D-Glucosyl-2-hydroxycinnamate + UDP coumarin biosynthesis (via 2-coumarate) 3-methyl-4-cis-hydroxy-2-butenal 100.117 C5 H8 O2 O=CC=C(CO)C PUBCHEM:12487266: 1.5.99.12 H+ + cis-zeatin + H2O + FAD = 3-methyl-4-cis-hydroxy-2-butenal + adenine + FADH2 cytokinins degradation β-myrcene myrcene 136.236 C10 H16 C(CCC=C(C)C)(C=C)=C PUBCHEM:31253:*CHEBI:17221:*LIGAND-CPD:C06074: 4.2.3.15 geranyl diphosphate = β-myrcene + diphosphate monoterpene biosynthesis citrate citr*cit*citric acid*2-hydroxy-1,2,3-propanetricarboxylic acid 189.101 C6 H5 O7 C(=O)([O-])CC(C(=O)[O-])(O)CC(=O)[O-] CHEBI:16947:*KNAPSACK:C00007619:*PUBCHEM:31348:*PUBCHEM:311:*LIGAND-CPD:C00158:*CAS:77-92-9 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A glyoxylate cycle citrate citr*cit*citric acid*2-hydroxy-1,2,3-propanetricarboxylic acid 189.101 C6 H5 O7 C(=O)([O-])CC(C(=O)[O-])(O)CC(=O)[O-] CHEBI:16947:*KNAPSACK:C00007619:*PUBCHEM:31348:*PUBCHEM:311:*LIGAND-CPD:C00158:*CAS:77-92-9 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A TCA cycle variation III (eukaryotic) citrate citr*cit*citric acid*2-hydroxy-1,2,3-propanetricarboxylic acid 189.101 C6 H5 O7 C(=O)([O-])CC(C(=O)[O-])(O)CC(=O)[O-] CHEBI:16947:*KNAPSACK:C00007619:*PUBCHEM:31348:*PUBCHEM:311:*LIGAND-CPD:C00158:*CAS:77-92-9 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A glutamine biosynthesis III citrate citr*cit*citric acid*2-hydroxy-1,2,3-propanetricarboxylic acid 189.101 C6 H5 O7 C(=O)([O-])CC(C(=O)[O-])(O)CC(=O)[O-] CHEBI:16947:*KNAPSACK:C00007619:*PUBCHEM:31348:*PUBCHEM:311:*LIGAND-CPD:C00158:*CAS:77-92-9 4.2.1.3 citrate = cis-aconitate + H2O glyoxylate cycle citrate citr*cit*citric acid*2-hydroxy-1,2,3-propanetricarboxylic acid 189.101 C6 H5 O7 C(=O)([O-])CC(C(=O)[O-])(O)CC(=O)[O-] CHEBI:16947:*KNAPSACK:C00007619:*PUBCHEM:31348:*PUBCHEM:311:*LIGAND-CPD:C00158:*CAS:77-92-9 4.2.1.3 citrate = cis-aconitate + H2O TCA cycle variation III (eukaryotic) citrate citr*cit*citric acid*2-hydroxy-1,2,3-propanetricarboxylic acid 189.101 C6 H5 O7 C(=O)([O-])CC(C(=O)[O-])(O)CC(=O)[O-] CHEBI:16947:*KNAPSACK:C00007619:*PUBCHEM:31348:*PUBCHEM:311:*LIGAND-CPD:C00158:*CAS:77-92-9 4.2.1.3 citrate = cis-aconitate + H2O glutamine biosynthesis III citrate citr*cit*citric acid*2-hydroxy-1,2,3-propanetricarboxylic acid 189.101 C6 H5 O7 C(=O)([O-])CC(C(=O)[O-])(O)CC(=O)[O-] CHEBI:16947:*KNAPSACK:C00007619:*PUBCHEM:31348:*PUBCHEM:311:*LIGAND-CPD:C00158:*CAS:77-92-9 2.3.3.8 oxaloacetate + acetyl-CoA + ADP = citrate + coenzyme A + ATP acetyl-CoA biosynthesis (from citrate) N6-(Δ2-isopentenyl)-adenosine 5'-diphosphate iPDP*isopentenyladenosine riboside-5'-diphosphate*iPRDP*isopentenyladenosine-5'-diphosphate 492.298 C15 H20 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)NCC=C(C)C)N=C2)))O3)O)O))[O-] PUBCHEM:25202829:*LIGAND-CPD:C16426: N6-(Δ2-isopentenyl)-adenosine 5'-diphosphate + NADPH + H2O = H+ + trans-zeatin riboside diphosphate + NADP+ trans-zeatin biosynthesis N6-(Δ2-isopentenyl)-adenosine 5'-diphosphate iPDP*isopentenyladenosine riboside-5'-diphosphate*iPRDP*isopentenyladenosine-5'-diphosphate 492.298 C15 H20 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)NCC=C(C)C)N=C2)))O3)O)O))[O-] PUBCHEM:25202829:*LIGAND-CPD:C16426: 2.5.1.- dimethylallyl diphosphate + ADP = N6-(Δ2-isopentenyl)-adenosine 5'-diphosphate + diphosphate trans-zeatin biosynthesis D-myo-inositol (1,2,3,5,6) pentakisphosphate 1D-myo-inositol (1,2,3,5,6) pentakisphosphate*Ins(1,2,3,5,6)P5*I(1,2,3,5,6)P5 569.977 C6 H7 O21 P5 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(OP([O-])([O-])=O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) PUBCHEM:25203733:*CHEBI:58747:*PUBCHEM:25246187: D-myo-inositol (1,2,3,5,6) pentakisphosphate + H2O = D-myo-inositol (1,2,5,6) tetrakisphosphate phytate degradation I D-myo-inositol (1,2,3,5,6) pentakisphosphate 1D-myo-inositol (1,2,3,5,6) pentakisphosphate*Ins(1,2,3,5,6)P5*I(1,2,3,5,6)P5 569.977 C6 H7 O21 P5 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(OP([O-])([O-])=O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) PUBCHEM:25203733:*CHEBI:58747:*PUBCHEM:25246187: D-myo-inositol (1,2,3,5,6) pentakisphosphate + H2O = D-myo-inositol (1,2,3,6) tetrakisphosphate phytate degradation I D-myo-inositol (1,2,3,5,6) pentakisphosphate 1D-myo-inositol (1,2,3,5,6) pentakisphosphate*Ins(1,2,3,5,6)P5*I(1,2,3,5,6)P5 569.977 C6 H7 O21 P5 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(OP([O-])([O-])=O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) PUBCHEM:25203733:*CHEBI:58747:*PUBCHEM:25246187: 3.1.3.26 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + H2O = D-myo-inositol (1,2,3,5,6) pentakisphosphate phytate degradation I agmatine 132.208 C5 H16 N4 N(C(=[N+])N)CCCC[N+] PUBCHEM:5257176:*LIGAND-CPD:C00179:*CAS:306-60-5 4.1.1.19 H+ + L-arginine = CO2 + agmatine arginine degradation III (arginine decarboxylase/agmatinase pathway) agmatine 132.208 C5 H16 N4 N(C(=[N+])N)CCCC[N+] PUBCHEM:5257176:*LIGAND-CPD:C00179:*CAS:306-60-5 4.1.1.19 H+ + L-arginine = CO2 + agmatine arginine dependent acid resistance agmatine 132.208 C5 H16 N4 N(C(=[N+])N)CCCC[N+] PUBCHEM:5257176:*LIGAND-CPD:C00179:*CAS:306-60-5 4.1.1.19 H+ + L-arginine = CO2 + agmatine putrescine biosynthesis IV agmatine 132.208 C5 H16 N4 N(C(=[N+])N)CCCC[N+] PUBCHEM:5257176:*LIGAND-CPD:C00179:*CAS:306-60-5 4.1.1.19 H+ + L-arginine = CO2 + agmatine putrescine biosynthesis II agmatine 132.208 C5 H16 N4 N(C(=[N+])N)CCCC[N+] PUBCHEM:5257176:*LIGAND-CPD:C00179:*CAS:306-60-5 4.1.1.19 H+ + L-arginine = CO2 + agmatine arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) agmatine 132.208 C5 H16 N4 N(C(=[N+])N)CCCC[N+] PUBCHEM:5257176:*LIGAND-CPD:C00179:*CAS:306-60-5 3.5.3.11 H2O + agmatine = urea + putrescine arginine degradation III (arginine decarboxylase/agmatinase pathway) agmatine 132.208 C5 H16 N4 N(C(=[N+])N)CCCC[N+] PUBCHEM:5257176:*LIGAND-CPD:C00179:*CAS:306-60-5 3.5.3.11 H2O + agmatine = urea + putrescine putrescine biosynthesis IV agmatine 132.208 C5 H16 N4 N(C(=[N+])N)CCCC[N+] PUBCHEM:5257176:*LIGAND-CPD:C00179:*CAS:306-60-5 3.5.3.12 H2O + agmatine = H+ + ammonia + N-carbamoylputrescine putrescine biosynthesis II agmatine 132.208 C5 H16 N4 N(C(=[N+])N)CCCC[N+] PUBCHEM:5257176:*LIGAND-CPD:C00179:*CAS:306-60-5 3.5.3.12 H2O + agmatine = H+ + ammonia + N-carbamoylputrescine arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) glycolate hydroxyacetic acid*glycolic acid*glycollate 75.044 C2 H3 O3 C(CO)(=O)[O-] PUBCHEM:5460308:*CHEBI:29805:*LIGAND-CPD:C00160:*CAS:79-14-1 1.1.3.15 glycolate + oxygen = glyoxylate + hydrogen peroxide photorespiration glycolate hydroxyacetic acid*glycolic acid*glycollate 75.044 C2 H3 O3 C(CO)(=O)[O-] PUBCHEM:5460308:*CHEBI:29805:*LIGAND-CPD:C00160:*CAS:79-14-1 1.1.99.14 glycolate = glyoxylate glycolate and glyoxylate degradation II glycolate hydroxyacetic acid*glycolic acid*glycollate 75.044 C2 H3 O3 C(CO)(=O)[O-] PUBCHEM:5460308:*CHEBI:29805:*LIGAND-CPD:C00160:*CAS:79-14-1 3.1.3.18 H2O + 2-phosphoglycolate = glycolate photorespiration 2-oxoisovalerate 2-oxoisovalerate*2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-keto-isovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 115.108 C5 H7 O3 [O-]C(C(C(C)C)=O)=O KNAPSACK:C00007623:*PUBCHEM:5204641:*CHEBI:11851:*LIGAND-CPD:C00141:*CAS:759-05-7 1.2.1.25 2-oxoisovalerate + coenzyme A + NAD+ = isobutyryl-CoA + CO2 + NADH valine degradation I 2-oxoisovalerate 2-oxoisovalerate*2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-keto-isovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 115.108 C5 H7 O3 [O-]C(C(C(C)C)=O)=O KNAPSACK:C00007623:*PUBCHEM:5204641:*CHEBI:11851:*LIGAND-CPD:C00141:*CAS:759-05-7 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate valine degradation I 2-oxoisovalerate 2-oxoisovalerate*2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-keto-isovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 115.108 C5 H7 O3 [O-]C(C(C(C)C)=O)=O KNAPSACK:C00007623:*PUBCHEM:5204641:*CHEBI:11851:*LIGAND-CPD:C00141:*CAS:759-05-7 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate valine biosynthesis 2-oxoisovalerate 2-oxoisovalerate*2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-keto-isovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 115.108 C5 H7 O3 [O-]C(C(C(C)C)=O)=O KNAPSACK:C00007623:*PUBCHEM:5204641:*CHEBI:11851:*LIGAND-CPD:C00141:*CAS:759-05-7 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate pantothenate biosynthesis I 2-oxoisovalerate 2-oxoisovalerate*2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-keto-isovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 115.108 C5 H7 O3 [O-]C(C(C(C)C)=O)=O KNAPSACK:C00007623:*PUBCHEM:5204641:*CHEBI:11851:*LIGAND-CPD:C00141:*CAS:759-05-7 2.6.1.42 L-valine + 2-oxoglutarate = L-glutamate + 2-oxoisovalerate valine degradation II 2-oxoisovalerate 2-oxoisovalerate*2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-keto-isovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 115.108 C5 H7 O3 [O-]C(C(C(C)C)=O)=O KNAPSACK:C00007623:*PUBCHEM:5204641:*CHEBI:11851:*LIGAND-CPD:C00141:*CAS:759-05-7 4.2.1.9 2,3-dihydroxy-isovalerate = 2-oxoisovalerate + H2O valine biosynthesis 2-oxoisovalerate 2-oxoisovalerate*2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-keto-isovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 115.108 C5 H7 O3 [O-]C(C(C(C)C)=O)=O KNAPSACK:C00007623:*PUBCHEM:5204641:*CHEBI:11851:*LIGAND-CPD:C00141:*CAS:759-05-7 4.1.1.1 H+ + 2-oxoisovalerate = isobutanal + CO2 valine degradation II 2-oxoisovalerate 2-oxoisovalerate*2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-keto-isovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 115.108 C5 H7 O3 [O-]C(C(C(C)C)=O)=O KNAPSACK:C00007623:*PUBCHEM:5204641:*CHEBI:11851:*LIGAND-CPD:C00141:*CAS:759-05-7 2.1.2.11 5,10-methylenetetrahydropteroyl mono-L-glutamate + 2-oxoisovalerate + H2O = H+ + 2-dehydropantoate + tetrahydrofolate phosphopantothenate biosynthesis I 2-oxoisovalerate 2-oxoisovalerate*2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-keto-isovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 115.108 C5 H7 O3 [O-]C(C(C(C)C)=O)=O KNAPSACK:C00007623:*PUBCHEM:5204641:*CHEBI:11851:*LIGAND-CPD:C00141:*CAS:759-05-7 2.1.2.11 5,10-methylenetetrahydropteroyl mono-L-glutamate + 2-oxoisovalerate + H2O = H+ + 2-dehydropantoate + tetrahydrofolate pantothenate biosynthesis I 2-oxoisovalerate 2-oxoisovalerate*2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-keto-isovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 115.108 C5 H7 O3 [O-]C(C(C(C)C)=O)=O KNAPSACK:C00007623:*PUBCHEM:5204641:*CHEBI:11851:*LIGAND-CPD:C00141:*CAS:759-05-7 2.3.3.13 2-oxoisovalerate + acetyl-CoA + H2O = H+ + (2S)-2-isopropylmalate + coenzyme A leucine biosynthesis 5-dehydro episterol 396.655 C28 H44 O1 C1(CC(CC2(C1(C3(C(=CC=2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))O) PUBCHEM:44229243:*LIGAND-CPD:C15780: 1.3.3.- episterol = H+ + 5-dehydro episterol plant sterol biosynthesis 5-dehydro episterol 396.655 C28 H44 O1 C1(CC(CC2(C1(C3(C(=CC=2)C4(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4)))C))O) PUBCHEM:44229243:*LIGAND-CPD:C15780: 1.3.1.21 5-dehydro episterol + NADPH = 24-methylenecholesterol + NADP+ plant sterol biosynthesis di-trans,octa-cis-undecaprenyl diphosphate UPP (ambiguous)*undecaprenyl pyrophosphate (ambiguous)*undecaprenyl-PP (ambiguous)*di-trans-poly-cis-undecaprenyl diphosphate*di-trans-poly-cis-undecaprenyl diphosphate*undecaprenyl-PP*bactoprenyl pyrophosphate*undecaprenyl pyrophosphate*UPP*di-trans,poly-cis-undecaprenyl diphosphate 924.251 C55 H89 O7 P2 [O-]P(OP(OCC=C(CCC=C(CCC=C(CCC=C(CCC=C(C)CCC=C(CCC=C(CCC=C(CCC=C(C)CCC=C(C)CCC=C(C)C)C)C)C)C)C)C)C)([O-])=O)([O-])=O LIGAND-CPD:C03543:*PUBCHEM:5280700:*CHEBI:58405:*PUBCHEM:25245563:*LIGAND-CPD:C04574: 2.5.1.31 (2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = di-trans,octa-cis-undecaprenyl diphosphate + diphosphate di-trans,poly-cis-undecaprenyl phosphate biosynthesis maltotetraose 666.583 C24 H42 O21 OCC4(OC(OC1(C(O)C(O)C(OC(CO)1)OC2(C(O)C(O)C(OC(CO)2)OC3(C(O)C(O)C(O)OC(CO)3))))C(O)C(O)C(O)4) PUBCHEM:446495:*LIGAND-CPD:C02052:*CAS:34612-38-9 2.4.1.25 maltotriose + maltose = maltotetraose + β-D-glucose glycogen degradation I maltotetraose 666.583 C24 H42 O21 OCC4(OC(OC1(C(O)C(O)C(OC(CO)1)OC2(C(O)C(O)C(OC(CO)2)OC3(C(O)C(O)C(O)OC(CO)3))))C(O)C(O)C(O)4) PUBCHEM:446495:*LIGAND-CPD:C02052:*CAS:34612-38-9 3.2.1.33 H2O = maltotetraose glycogen degradation I maltotetraose 666.583 C24 H42 O21 OCC4(OC(OC1(C(O)C(O)C(OC(CO)1)OC2(C(O)C(O)C(OC(CO)2)OC3(C(O)C(O)C(O)OC(CO)3))))C(O)C(O)C(O)4) PUBCHEM:446495:*LIGAND-CPD:C02052:*CAS:34612-38-9 2.4.1.1 maltotetraose = maltotriose + α-D-glucose 1-phosphate glycogen degradation I 2,3-dihydroxybenzoate 2,3-dihydroxybenzoic acid*3-hydroxysalicylate*catechol-3-carboxylate*2-pyrocatechuate 153.114 C7 H5 O4 C1(C(=C(C(=CC=1)O)O)C([O-])=O) PUBCHEM:6950143:*CHEBI:36654:*LIGAND-CPD:C00196:*CAS:303-38-8 2.7.7.58 H+ + 2,3-dihydroxybenzoate + ATP = 2,3-dihydroxybenzoyl-AMP + diphosphate vibriobactin biosynthesis 2,3-dihydroxybenzoate 2,3-dihydroxybenzoic acid*3-hydroxysalicylate*catechol-3-carboxylate*2-pyrocatechuate 153.114 C7 H5 O4 C1(C(=C(C(=CC=1)O)O)C([O-])=O) PUBCHEM:6950143:*CHEBI:36654:*LIGAND-CPD:C00196:*CAS:303-38-8 1.3.1.28 NAD+ + 2,3-dihydro-2,3-dihydroxybenzoate = H+ + NADH + 2,3-dihydroxybenzoate 2,3-dihydroxybenzoate biosynthesis D-ribulose-1-phosphate D-ribulose-1-P 228.095 C5 H9 O8 P1 OCC(O)C(O)C(=O)COP([O-])(=O)[O-] PUBCHEM:22027282: 2.4.2.- H+ + nicotinate + D-ribulose-1-phosphate = nicotinate riboside pyridine nucleotide cycling (plants) isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 2.5.1.31 (2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = di-trans,octa-cis-undecaprenyl diphosphate + diphosphate di-trans,poly-cis-undecaprenyl phosphate biosynthesis isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 2.5.1.85 all-trans-geranyl-geranyl diphosphate + isopentenyl diphosphate = all-trans-nonaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis II isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 2.5.1.10 geranyl diphosphate + isopentenyl diphosphate = (2E,6E)-farnesyl diphosphate + diphosphate linalool biosynthesis isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 2.5.1.10 geranyl diphosphate + isopentenyl diphosphate = (2E,6E)-farnesyl diphosphate + diphosphate trans, trans-farnesyl diphosphate biosynthesis isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 2.5.1.90 all-trans-heptaprenyl diphosphate + isopentenyl diphosphate = H+ + diphosphate + all-trans-octaprenyl diphosphate nonaprenyl diphosphate biosynthesis III isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 2.5.1.84 all-trans-octaprenyl diphosphate + isopentenyl diphosphate = H+ + all-trans-nonaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 2.5.1.30 all-trans-hexaprenyl diphosphate + isopentenyl diphosphate = H+ + all-trans-heptaprenyl diphosphate + diphosphate heptaprenyl diphosphate biosynthesis isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 2.5.1.30 all-trans-hexaprenyl diphosphate + isopentenyl diphosphate = H+ + all-trans-heptaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 1.17.1.2 isopentenyl diphosphate + H2O = 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H+ methylerythritol phosphate pathway isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 2.5.1.81 isopentenyl diphosphate + all-trans-geranyl-geranyl diphosphate = H+ + geranylfarnesyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 4.1.1.33 mevalonate-diphosphate + ATP = isopentenyl diphosphate + CO2 + ADP mevalonate pathway I isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 2.5.1.1 dimethylallyl diphosphate + isopentenyl diphosphate = geranyl diphosphate + diphosphate geranyl diphosphate biosynthesis isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 2.5.1.1 dimethylallyl diphosphate + isopentenyl diphosphate = geranyl diphosphate + diphosphate trans, trans-farnesyl diphosphate biosynthesis isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 2.5.1.29 (2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-geranyl-geranyl diphosphate + diphosphate geranylgeranyldiphosphate biosynthesis isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 2.5.1.29 (2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-geranyl-geranyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 2.5.1.83 geranylfarnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-hexaprenyl diphosphate + diphosphate hexaprenyl diphosphate biosynthesis isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 2.5.1.83 geranylfarnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-hexaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 5.3.3.2 isopentenyl diphosphate = dimethylallyl diphosphate mevalonate pathway I isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 5.3.3.2 isopentenyl diphosphate = dimethylallyl diphosphate trans, trans-farnesyl diphosphate biosynthesis isopentenyl diphosphate isopentenyl diphosphate*isopentenyl-pp*isopentenyl pyrophosphate*IPP*δ(3)-isopentenyl-PP*Δ3-isopentenyl-PP 243.069 C5 H9 O7 P2 [O-]P([O-])(=O)OP([O-])(=O)OCCC(=C)C KNAPSACK:C00000848:*CHEBI:128769:*PUBCHEM:15983957:*PUBCHEM:15983957:*LIGAND-CPD:C00129: 5.3.3.2 isopentenyl diphosphate = dimethylallyl diphosphate methylerythritol phosphate pathway terpinolene 136.236 C10 H16 C1(CCC(CC=1)=C(C)C)C PUBCHEM:11463:*CHEBI:9457:*LIGAND-CPD:C06075: 4.2.3.- geranyl diphosphate = terpinolene + diphosphate monoterpene biosynthesis antheraxanthin 584.881 C40 H56 O3 C1(C(C2(C(CC1O)(C)O2)(C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC3(=C(CC(CC3(C)C)O)C))C)C))(C)C) PUBCHEM:25244322:*LIGAND-CPD:C08579: 1.14.13.90 antheraxanthin + H+ + oxygen = violaxanthin + H2O antheraxanthin and violaxanthin biosynthesis antheraxanthin 584.881 C40 H56 O3 C1(C(C2(C(CC1O)(C)O2)(C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC3(=C(CC(CC3(C)C)O)C))C)C))(C)C) PUBCHEM:25244322:*LIGAND-CPD:C08579: 1.14.13.90 antheraxanthin + H+ + oxygen = violaxanthin + H2O xanthophyll cycle antheraxanthin 584.881 C40 H56 O3 C1(C(C2(C(CC1O)(C)O2)(C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC3(=C(CC(CC3(C)C)O)C))C)C))(C)C) PUBCHEM:25244322:*LIGAND-CPD:C08579: 1.10.99.3 H+ + violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O antheraxanthin and violaxanthin biosynthesis antheraxanthin 584.881 C40 H56 O3 C1(C(C2(C(CC1O)(C)O2)(C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC3(=C(CC(CC3(C)C)O)C))C)C))(C)C) PUBCHEM:25244322:*LIGAND-CPD:C08579: 1.10.99.3 H+ + violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle antheraxanthin 584.881 C40 H56 O3 C1(C(C2(C(CC1O)(C)O2)(C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC3(=C(CC(CC3(C)C)O)C))C)C))(C)C) PUBCHEM:25244322:*LIGAND-CPD:C08579: 1.14.13.90 zeaxanthin + H+ + oxygen = antheraxanthin + H2O antheraxanthin and violaxanthin biosynthesis antheraxanthin 584.881 C40 H56 O3 C1(C(C2(C(CC1O)(C)O2)(C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC3(=C(CC(CC3(C)C)O)C))C)C))(C)C) PUBCHEM:25244322:*LIGAND-CPD:C08579: 1.14.13.90 zeaxanthin + H+ + oxygen = antheraxanthin + H2O xanthophyll cycle antheraxanthin 584.881 C40 H56 O3 C1(C(C2(C(CC1O)(C)O2)(C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC3(=C(CC(CC3(C)C)O)C))C)C))(C)C) PUBCHEM:25244322:*LIGAND-CPD:C08579: 1.10.99.3 H+ + antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O antheraxanthin and violaxanthin biosynthesis antheraxanthin 584.881 C40 H56 O3 C1(C(C2(C(CC1O)(C)O2)(C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC3(=C(CC(CC3(C)C)O)C))C)C))(C)C) PUBCHEM:25244322:*LIGAND-CPD:C08579: 1.10.99.3 H+ + antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle fructose-1,6-bisphosphate β-D-fructose-1,6-diphosphate*fructose-1,6-biphosphate*fructose-1,6-diphosphate*α-D-fructose-1,6-diphosphate*D-fructose-1,6-diphosphate*D-fructose-1,6-bisphosphate*fructose 1,6-bisphosphate*FBP 336.085 C6 H10 O12 P2 O=P(OCC1(C(C(C(O1)(COP([O-])([O-])=O)O)O)O))([O-])[O-] KNAPSACK:C00007386:*CHEBI:32966:*PUBCHEM:5460765:*KNAPKSACK:C00007386*PUBCHEM:718:*|Wikipedia|:Fructose_1,6-bisphosphate:*LIGAND-CPD:C00354:*CAS:488-69-7 2.7.1.11 ATP + D-fructose-6-phosphate = H+ + ADP + fructose-1,6-bisphosphate glycolysis III fructose-1,6-bisphosphate β-D-fructose-1,6-diphosphate*fructose-1,6-biphosphate*fructose-1,6-diphosphate*α-D-fructose-1,6-diphosphate*D-fructose-1,6-diphosphate*D-fructose-1,6-bisphosphate*fructose 1,6-bisphosphate*FBP 336.085 C6 H10 O12 P2 O=P(OCC1(C(C(C(O1)(COP([O-])([O-])=O)O)O)O))([O-])[O-] KNAPSACK:C00007386:*CHEBI:32966:*PUBCHEM:5460765:*KNAPKSACK:C00007386*PUBCHEM:718:*|Wikipedia|:Fructose_1,6-bisphosphate:*LIGAND-CPD:C00354:*CAS:488-69-7 2.7.1.11 ATP + D-fructose-6-phosphate = H+ + ADP + fructose-1,6-bisphosphate glycolysis IV (plant cytosol) fructose-1,6-bisphosphate β-D-fructose-1,6-diphosphate*fructose-1,6-biphosphate*fructose-1,6-diphosphate*α-D-fructose-1,6-diphosphate*D-fructose-1,6-diphosphate*D-fructose-1,6-bisphosphate*fructose 1,6-bisphosphate*FBP 336.085 C6 H10 O12 P2 O=P(OCC1(C(C(C(O1)(COP([O-])([O-])=O)O)O)O))([O-])[O-] KNAPSACK:C00007386:*CHEBI:32966:*PUBCHEM:5460765:*KNAPKSACK:C00007386*PUBCHEM:718:*|Wikipedia|:Fructose_1,6-bisphosphate:*LIGAND-CPD:C00354:*CAS:488-69-7 2.7.1.11 ATP + D-fructose-6-phosphate = H+ + ADP + fructose-1,6-bisphosphate glycolysis I fructose-1,6-bisphosphate β-D-fructose-1,6-diphosphate*fructose-1,6-biphosphate*fructose-1,6-diphosphate*α-D-fructose-1,6-diphosphate*D-fructose-1,6-diphosphate*D-fructose-1,6-bisphosphate*fructose 1,6-bisphosphate*FBP 336.085 C6 H10 O12 P2 O=P(OCC1(C(C(C(O1)(COP([O-])([O-])=O)O)O)O))([O-])[O-] KNAPSACK:C00007386:*CHEBI:32966:*PUBCHEM:5460765:*KNAPKSACK:C00007386*PUBCHEM:718:*|Wikipedia|:Fructose_1,6-bisphosphate:*LIGAND-CPD:C00354:*CAS:488-69-7 3.1.3.11 fructose-1,6-bisphosphate + H2O = D-fructose-6-phosphate gluconeogenesis I fructose-1,6-bisphosphate β-D-fructose-1,6-diphosphate*fructose-1,6-biphosphate*fructose-1,6-diphosphate*α-D-fructose-1,6-diphosphate*D-fructose-1,6-diphosphate*D-fructose-1,6-bisphosphate*fructose 1,6-bisphosphate*FBP 336.085 C6 H10 O12 P2 O=P(OCC1(C(C(C(O1)(COP([O-])([O-])=O)O)O)O))([O-])[O-] KNAPSACK:C00007386:*CHEBI:32966:*PUBCHEM:5460765:*KNAPKSACK:C00007386*PUBCHEM:718:*|Wikipedia|:Fructose_1,6-bisphosphate:*LIGAND-CPD:C00354:*CAS:488-69-7 3.1.3.11 fructose-1,6-bisphosphate + H2O = D-fructose-6-phosphate glycolysis I fructose-1,6-bisphosphate β-D-fructose-1,6-diphosphate*fructose-1,6-biphosphate*fructose-1,6-diphosphate*α-D-fructose-1,6-diphosphate*D-fructose-1,6-diphosphate*D-fructose-1,6-bisphosphate*fructose 1,6-bisphosphate*FBP 336.085 C6 H10 O12 P2 O=P(OCC1(C(C(C(O1)(COP([O-])([O-])=O)O)O)O))([O-])[O-] KNAPSACK:C00007386:*CHEBI:32966:*PUBCHEM:5460765:*KNAPKSACK:C00007386*PUBCHEM:718:*|Wikipedia|:Fructose_1,6-bisphosphate:*LIGAND-CPD:C00354:*CAS:488-69-7 3.1.3.11 fructose-1,6-bisphosphate + H2O = D-fructose-6-phosphate Calvin-Benson-Bassham cycle fructose-1,6-bisphosphate β-D-fructose-1,6-diphosphate*fructose-1,6-biphosphate*fructose-1,6-diphosphate*α-D-fructose-1,6-diphosphate*D-fructose-1,6-diphosphate*D-fructose-1,6-bisphosphate*fructose 1,6-bisphosphate*FBP 336.085 C6 H10 O12 P2 O=P(OCC1(C(C(C(O1)(COP([O-])([O-])=O)O)O)O))([O-])[O-] KNAPSACK:C00007386:*CHEBI:32966:*PUBCHEM:5460765:*KNAPKSACK:C00007386*PUBCHEM:718:*|Wikipedia|:Fructose_1,6-bisphosphate:*LIGAND-CPD:C00354:*CAS:488-69-7 2.7.1.90 D-fructose-6-phosphate + diphosphate = H+ + fructose-1,6-bisphosphate glycolysis IV (plant cytosol) fructose-1,6-bisphosphate β-D-fructose-1,6-diphosphate*fructose-1,6-biphosphate*fructose-1,6-diphosphate*α-D-fructose-1,6-diphosphate*D-fructose-1,6-diphosphate*D-fructose-1,6-bisphosphate*fructose 1,6-bisphosphate*FBP 336.085 C6 H10 O12 P2 O=P(OCC1(C(C(C(O1)(COP([O-])([O-])=O)O)O)O))([O-])[O-] KNAPSACK:C00007386:*CHEBI:32966:*PUBCHEM:5460765:*KNAPKSACK:C00007386*PUBCHEM:718:*|Wikipedia|:Fructose_1,6-bisphosphate:*LIGAND-CPD:C00354:*CAS:488-69-7 4.1.2.13 fructose-1,6-bisphosphate = dihydroxyacetone phosphate + D-glyceraldehyde-3-phosphate gluconeogenesis I fructose-1,6-bisphosphate β-D-fructose-1,6-diphosphate*fructose-1,6-biphosphate*fructose-1,6-diphosphate*α-D-fructose-1,6-diphosphate*D-fructose-1,6-diphosphate*D-fructose-1,6-bisphosphate*fructose 1,6-bisphosphate*FBP 336.085 C6 H10 O12 P2 O=P(OCC1(C(C(C(O1)(COP([O-])([O-])=O)O)O)O))([O-])[O-] KNAPSACK:C00007386:*CHEBI:32966:*PUBCHEM:5460765:*KNAPKSACK:C00007386*PUBCHEM:718:*|Wikipedia|:Fructose_1,6-bisphosphate:*LIGAND-CPD:C00354:*CAS:488-69-7 4.1.2.13 fructose-1,6-bisphosphate = dihydroxyacetone phosphate + D-glyceraldehyde-3-phosphate glycolysis III fructose-1,6-bisphosphate β-D-fructose-1,6-diphosphate*fructose-1,6-biphosphate*fructose-1,6-diphosphate*α-D-fructose-1,6-diphosphate*D-fructose-1,6-diphosphate*D-fructose-1,6-bisphosphate*fructose 1,6-bisphosphate*FBP 336.085 C6 H10 O12 P2 O=P(OCC1(C(C(C(O1)(COP([O-])([O-])=O)O)O)O))([O-])[O-] KNAPSACK:C00007386:*CHEBI:32966:*PUBCHEM:5460765:*KNAPKSACK:C00007386*PUBCHEM:718:*|Wikipedia|:Fructose_1,6-bisphosphate:*LIGAND-CPD:C00354:*CAS:488-69-7 4.1.2.13 fructose-1,6-bisphosphate = dihydroxyacetone phosphate + D-glyceraldehyde-3-phosphate glycolysis IV (plant cytosol) fructose-1,6-bisphosphate β-D-fructose-1,6-diphosphate*fructose-1,6-biphosphate*fructose-1,6-diphosphate*α-D-fructose-1,6-diphosphate*D-fructose-1,6-diphosphate*D-fructose-1,6-bisphosphate*fructose 1,6-bisphosphate*FBP 336.085 C6 H10 O12 P2 O=P(OCC1(C(C(C(O1)(COP([O-])([O-])=O)O)O)O))([O-])[O-] KNAPSACK:C00007386:*CHEBI:32966:*PUBCHEM:5460765:*KNAPKSACK:C00007386*PUBCHEM:718:*|Wikipedia|:Fructose_1,6-bisphosphate:*LIGAND-CPD:C00354:*CAS:488-69-7 4.1.2.13 fructose-1,6-bisphosphate = dihydroxyacetone phosphate + D-glyceraldehyde-3-phosphate glycolysis I fructose-1,6-bisphosphate β-D-fructose-1,6-diphosphate*fructose-1,6-biphosphate*fructose-1,6-diphosphate*α-D-fructose-1,6-diphosphate*D-fructose-1,6-diphosphate*D-fructose-1,6-bisphosphate*fructose 1,6-bisphosphate*FBP 336.085 C6 H10 O12 P2 O=P(OCC1(C(C(C(O1)(COP([O-])([O-])=O)O)O)O))([O-])[O-] KNAPSACK:C00007386:*CHEBI:32966:*PUBCHEM:5460765:*KNAPKSACK:C00007386*PUBCHEM:718:*|Wikipedia|:Fructose_1,6-bisphosphate:*LIGAND-CPD:C00354:*CAS:488-69-7 4.1.2.13 fructose-1,6-bisphosphate = dihydroxyacetone phosphate + D-glyceraldehyde-3-phosphate Calvin-Benson-Bassham cycle isobutanal isobutyraldehyde*isobutylaldehyde 72.107 C4 H8 O1 CC(C)C=O PUBCHEM:6561:*CHEBI:48943: 1.1.1.1 H+ + isobutanal + NADH = isobutanol + NAD+ valine degradation II isobutanal isobutyraldehyde*isobutylaldehyde 72.107 C4 H8 O1 CC(C)C=O PUBCHEM:6561:*CHEBI:48943: 4.1.1.1 H+ + 2-oxoisovalerate = isobutanal + CO2 valine degradation II 2-hydroxy-3-keto-5-methylthio-1-phosphopentene 1-phosphoryloxyl-2-hydroxy-3-keto-5-methylthiopentene 239.159 C6 H8 O6 P1 S1 O(P([O-])(=O)[O-])C=C([O-])C(=O)CCSC PUBCHEM:44229144:*LIGAND-CPD:C15651: 5-(methylthio)-2,3-dioxopentyl phosphate = H+ + 2-hydroxy-3-keto-5-methylthio-1-phosphopentene methionine salvage I 2-hydroxy-3-keto-5-methylthio-1-phosphopentene 1-phosphoryloxyl-2-hydroxy-3-keto-5-methylthiopentene 239.159 C6 H8 O6 P1 S1 O(P([O-])(=O)[O-])C=C([O-])C(=O)CCSC PUBCHEM:44229144:*LIGAND-CPD:C15651: 2-hydroxy-3-keto-5-methylthio-1-phosphopentene + H2O = 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one methionine salvage I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.6 ATP + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-aspartate = H+ + ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole inosine-5'-phosphate biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.14 ATP + uridine-5'-phosphate = ADP + UDP pyrimidine ribonucleotides interconversion ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.2 ammonia + CO2 + ATP = H+ + carbamoyl-phosphate + ADP citrulline degradation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.2 ammonia + CO2 + ATP = H+ + carbamoyl-phosphate + ADP allantoin degradation IV (anaerobic) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 5-aminoimidazole ribonucleotide biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = H+ + L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine superpathway of 5-aminoimidazole ribonucleotide biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 3.6.3.4 Cu2+ + H2O + ATP = Cu2+ + ADP copper transport II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.12 L-glutamate + 7,8-dihydropteroate + ATP = H+ + 7,8-dihydrofolate monoglutamate + ADP tetrahydrofolate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.3 AMP + ATP = ADP adenosine nucleotides de novo biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.6 dADP + ATP = dATP + ADP adenosine nucleotides de novo biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.71 shikimate + ATP = H+ + shikimate-3-phosphate + ADP chorismate biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.33 (R)-pantothenate + ATP = H+ + D-4'-phosphopantothenate + ADP phosphopantothenate biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 3.6.3.14 H+ + H2O + ATP = H+ + ADP adenosine nucleotides de novo biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.- nicotinate riboside + ATP = H+ + nicotinate mononucleotide + ADP pyridine nucleotide cycling (plants) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.68 ATP = ADP 3-phosphoinositide biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.68 ATP = ADP D-myo-inositol (1,4,5)-trisphosphate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP glutamine biosynthesis III ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP nitrate reduction II (assimilatory) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP ammonia assimilation cycle II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.153 ATP = ADP 3-phosphoinositide biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.- ATP + pyridoxine = H+ + ADP + pyridoxine-5'-phosphate pyridoxal 5'-phosphate salvage pathway ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.23 NAD+ + ATP = H+ + NADP+ + ADP NAD/NADH phosphorylation and dephosphorylation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.7.5 sulfate + H+ + ADP = adenosine 5'-phosphosulfate sulfite oxidation II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.3.3.8 oxaloacetate + acetyl-CoA + ADP = citrate + coenzyme A + ATP acetyl-CoA biosynthesis (from citrate) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.49 ATP + hydroxymethylpyrimidine = H+ + ADP + hydroxymethylpyrimidine phosphate thiamine biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.1.14 ammonia + ATP = H+ + ADP diphthamide biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis II (acetyl cycle) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate uridine-5'-phosphate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.5.5 ATP + L-glutamine + bicarbonate + H2O = H+ + L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.20 adenosine + ATP = H+ + AMP + ADP adenine and adenosine salvage VI ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.52 ATP = β-L-fucose 1-phosphate + ADP GDP-L-fucose biosynthesis II (from L-fucose) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.30 glycerol + ATP = H+ + sn-glycerol-3-phosphate + ADP glycerol degradation IV ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.30 glycerol + ATP = H+ + sn-glycerol-3-phosphate + ADP glycerol degradation I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = H+ + 5'-phosphoribosyl-N-formylglycineamide + ADP 5-aminoimidazole ribonucleotide biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = H+ + 5'-phosphoribosyl-N-formylglycineamide + ADP superpathway of 5-aminoimidazole ribonucleotide biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 D-myo-inositol (3,4,6)-trisphosphate + ATP = H+ + D-myo-inositol (3,4,5,6)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.11 L-glutamate + ATP = L-glutamate-5-phosphate + ADP proline biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.11 L-glutamate + ATP = L-glutamate-5-phosphate + ADP citrulline biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.150 ATP = ADP 3-phosphoinositide biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.11 ATP + D-fructose-6-phosphate = H+ + ADP + fructose-1,6-bisphosphate glycolysis III ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.11 ATP + D-fructose-6-phosphate = H+ + ADP + fructose-1,6-bisphosphate glycolysis IV (plant cytosol) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.11 ATP + D-fructose-6-phosphate = H+ + ADP + fructose-1,6-bisphosphate glycolysis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.2.1.5 succinate + coenzyme A + ATP = succinyl-CoA + ADP TCA cycle variation III (eukaryotic) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP GDP-glucose biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP glycolysis III ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP trehalose degradation II (trehalase) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP glucose and glucose-1-phosphate degradation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.2 β-D-glucose + ATP = H+ + β-D-glucose-6-phosphate + ADP glycogen degradation I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.67 ATP = ADP 3-phosphoinositide biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.67 ATP = ADP D-myo-inositol (1,4,5)-trisphosphate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.2.1.26 ATP + o-succinylbenzoate + coenzyme A = 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA + ADP 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide 5-aminoimidazole ribonucleotide biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide 5-aminoimidazole ribonucleotide biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = H+ + ADP + 5-phospho-ribosyl-glycineamide superpathway of 5-aminoimidazole ribonucleotide biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.6 dCDP + ATP = dCTP + ADP pyrimidine deoxyribonucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.6 CDP + ATP = CTP + ADP pyrimidine ribonucleotides interconversion ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.6 CDP + ATP = CTP + ADP salvage pathways of pyrimidine ribonucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.31 D-glycerate + ATP = H+ + 3-phospho-D-glycerate + ADP photorespiration ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.4 β-D-fructofuranose + ATP = H+ + D-fructose-6-phosphate + ADP sucrose degradation III ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.4 β-D-fructofuranose + ATP = H+ + D-fructose-6-phosphate + ADP sucrose degradation I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.3.2 5-formyl-tetrahydrofolate + ATP = 5,10-methenyltetrahydrofolate + ADP folate transformations I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.3.2 5-formyl-tetrahydrofolate + ATP = 5,10-methenyltetrahydrofolate + ADP folate transformations II (plants) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.2 ATP + UTP + L-glutamine + H2O = H+ + ADP + CTP + L-glutamate pyrimidine ribonucleotides interconversion ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.91 sphinganine + ATP = H+ + sphinganine 1-phosphate + ADP sphingolipid biosynthesis (plants) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.- D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + 1D-myo-inositol (1,2,3,4,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.17 D-xylulose + ATP = H+ + D-xylulose-5-phosphate + ADP xylose degradation I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.140 1D-myo-inositol (1,2,3,4,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.82 ethanolamine + ATP = H+ + phosphoryl-ethanolamine + ADP phosphatidylethanolamine biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.82 ethanolamine + ATP = H+ + phosphoryl-ethanolamine + ADP choline biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.16 ammonia + H2O + CO2 + ATP = H+ + carbamoyl-phosphate + ADP urea cycle ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = H+ + glutathione + ADP γ-glutamyl cycle (plant pathway) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = H+ + glutathione + ADP glutathione biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.148 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + ATP = H+ + 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + ADP methylerythritol phosphate pathway ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.138 ATP = ADP sphingolipid biosynthesis (plants) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 3.6.3.- Cu2+ + H2O + ATP = Cu2+ + ADP copper transport I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP galactose degradation I (Leloir pathway) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP stachyose degradation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP colanic acid building blocks biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP galactose degradation III ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP Rubisco shunt ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP glycolysis III ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP glycolysis IV (plant cytosol) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.40 pyruvate + ATP = H+ + phosphoenolpyruvate + ADP glycolysis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.6 dTDP + ATP = dTTP + ADP pyrimidine deoxyribonucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.64 myo-inositol + ATP = H+ + 1D-myo-inositol (3)-monophosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.39 L-homoserine + ATP = H+ + O-phospho-L-homoserine + ADP threonine biosynthesis from homoserine ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.39 L-homoserine + ATP = H+ + O-phospho-L-homoserine + ADP methionine biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.1 α-D-glucose + ATP = H+ + α-D-glucose 6-phosphate + ADP sucrose degradation III ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.1 α-D-glucose + ATP = H+ + α-D-glucose 6-phosphate + ADP starch degradation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.46 ATP = β-L-arabinose 1-phosphate + ADP UDP-L-arabinose biosynthesis II (from L-arabinose) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.7 ATP = H+ + D-mannose 6-phosphate + ADP mannitol degradation II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.22 ATP + uridine-5'-phosphate = ADP + UDP pyrimidine ribonucleotides interconversion ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.5.7 L-glutamine + ATP = L-glutamate + ADP L-glutamine biosynthesis II (tRNA-dependent) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.4.1.4 ATP + 3-methylcrotonyl-CoA + bicarbonate = H+ + ADP + 3-methylglutaconyl-CoA leucine degradation I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.24 dephospho-CoA + ATP = H+ + coenzyme A + ADP coenzyme A biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 3.5.2.9 5-oxoproline + H2O + ATP = H+ + L-glutamate + ADP γ-glutamyl cycle (plant pathway) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 3.5.2.9 5-oxoproline + H2O + ATP = H+ + L-glutamate + ADP γ-glutamyl cycle ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.4 L-aspartate + ATP = L-aspartyl-4-phosphate + ADP lysine biosynthesis VI ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.4 L-aspartate + ATP = L-aspartyl-4-phosphate + ADP homoserine biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate folate transformations I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate folate transformations II (plants) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate formaldehyde oxidation V (tetrahydrofolate pathway) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + 10-formyl-tetrahydrofolate folate polyglutamylation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.6 dUDP + ATP = dUTP + ADP pyrimidine deoxyribonucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 3.6.3.- Cu2+ + H2O + ATP = Cu2+ + ADP copper transport I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.32 choline + ATP = H+ + phosphoryl-choline + ADP phosphatidylcholine biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = H+ + ADP + 5-aminoimidazole ribonucleotide 5-aminoimidazole ribonucleotide biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = H+ + ADP + 5-aminoimidazole ribonucleotide 5-aminoimidazole ribonucleotide biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = H+ + ADP + 5-aminoimidazole ribonucleotide superpathway of 5-aminoimidazole ribonucleotide biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.19 D-ribulose-5-phosphate + ATP = H+ + D-ribulose-1,5-bisphosphate + ADP Rubisco shunt ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.19 D-ribulose-5-phosphate + ATP = H+ + D-ribulose-1,5-bisphosphate + ADP Calvin-Benson-Bassham cycle ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 1.18.6.1 H+ + N2 + ATP + H2O = H2 + ammonia + ADP nitrogen fixation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.127 D-myo-inositol (1,4,5)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.36 (R)-mevalonate + ATP = H+ + mevalonate-5-phosphate + ADP mevalonate pathway I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.134 D-myo-inositol (3,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.134 D-myo-inositol (3,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.86 NADH + ATP = H+ + NADPH + ADP NAD/NADH phosphorylation and dephosphorylation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.4.1.21 ADP-α-D-glucose = ADP glycogen biosynthesis I (from ADP-D-Glucose) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.4.1.21 ADP-α-D-glucose = ADP starch biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.151 D-myo-inositol (1,3,4,5)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.151 D-myo-inositol (1,3,4,5)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.151 D-myo-inositol (1,3,4,5)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.100 ATP + S-methyl-5-thio-D-ribose = H+ + ADP + 5-methylthioribose-1-phosphate methionine salvage I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.- D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,2,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.8 N-acetyl-L-glutamate + ATP = N-acetylglutamyl-phosphate + ADP arginine biosynthesis II (acetyl cycle) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.8 N-acetyl-L-glutamate + ATP = N-acetylglutamyl-phosphate + ADP ornithine biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 1.17.4.1 dADP + H2O = ADP adenosine nucleotides de novo biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.25 adenosine 5'-phosphosulfate + ATP = H+ + phosphoadenosine-5'-phosphosulfate + ADP sulfate activation for sulfonation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.149 ATP = ADP D-myo-inositol (1,4,5)-trisphosphate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.164 ATP = ADP selenocysteine biosynthesis II (archaea and eukaryotes) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.151 D-myo-inositol (1,4,5)-trisphosphate + ATP = H+ + D-myo-inositol (1,4,5,6)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.151 D-myo-inositol (1,4,5)-trisphosphate + ATP = H+ + D-myo-inositol (1,4,5,6)-tetrakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 1D-myo-inositol (3)-monophosphate + ATP = H+ + D-myo-inositol (3,4)-bisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.158 D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = H+ + 1D-myo-inositol 1,2,3,4,5,6-hexakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.4.1.2 ATP + acetyl-CoA + bicarbonate = H+ + malonyl-CoA + ADP fatty acid biosynthesis initiation I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 D-myo-inositol (3,4)-bisphosphate + ATP = H+ + D-myo-inositol (3,4,6)-trisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.43 ATP = H+ + α-D-glucuronate 1-phosphate + ADP UDP-D-glucuronate biosynthesis (from myo-inositol) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.140 D-myo-inositol (1,3,4,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.2 L-cysteine + L-glutamate + ATP = H+ + L-γ-glutamylcysteine + ADP γ-glutamyl cycle (plant pathway) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.2 L-cysteine + L-glutamate + ATP = H+ + L-γ-glutamylcysteine + ADP glutathione biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = H+ + dethiobiotin + ADP biotin biosynthesis from 7-keto-8-aminopelargonate ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.9 ATP + dTMP = ADP + dTDP pyrimidine deoxyribonucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.7 hydroxymethylpyrimidine phosphate + ATP = 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate + ADP thiamine biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.2 mevalonate-5-phosphate + ATP = mevalonate-diphosphate + ADP mevalonate pathway I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.14 bicarbonate + ATP = ADP biotin-carboxyl carrier protein assembly ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.25 ATP + CMP = ADP + CDP salvage pathways of pyrimidine ribonucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.35 ATP + pyridoxamine = H+ + ADP + pyridoxamine 5'-phosphate pyridoxal 5'-phosphate salvage pathway ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.83 pseudouridine + ATP = H+ + pseudouridine 5'-phosphate + ADP pseudouridine degradation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP gluconeogenesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP glycolysis III ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP glycolysis IV (plant cytosol) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP glycolysis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP Calvin-Benson-Bassham cycle ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 4.1.1.49 oxaloacetate + ATP = CO2 + phosphoenolpyruvate + ADP gluconeogenesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 4.1.1.49 oxaloacetate + ATP = CO2 + phosphoenolpyruvate + ADP superpathway of glyoxylate cycle ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.6.1.1 ATP + protoporphyrin IX + Mg2+ + H2O = H+ + Mg-protoporphyrin + ADP chlorophyllide a biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.35 ATP + pyridoxal = H+ + ADP + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.151 D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.151 D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-dependent phytate biosynthesis I (via Ins(1,4,5)P3) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.151 D-myo-inositol (1,4,5,6)-tetrakisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 1.17.4.- ADP = dADP + H2O adenosine nucleotides de novo biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.154 ATP = ADP 3-phosphoinositide biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 4.1.1.33 mevalonate-diphosphate + ATP = isopentenyl diphosphate + CO2 + ADP mevalonate pathway I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.26 riboflavin + ATP = H+ + FMN + ADP flavin biosynthesis I (bacteria and plants) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.5.1.- dimethylallyl diphosphate + ADP = N6-(Δ2-isopentenyl)-adenosine 5'-diphosphate + diphosphate trans-zeatin biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.137 ATP = ADP 3-phosphoinositide biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 424.18 C10 H12 N5 O10 P2 O=P(OP(=O)([O-])[O-])(OCC3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))[O-] PUBCHEM:7058055:*PUBCHEM:6022:*PUBCHEM:7058055:*CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.6 UDP + ATP = UTP + ADP pyrimidine ribonucleotides interconversion N-feruloyltyramine feruloyltyramine*N-feruloyltyramine 313.352 C18 H19 N1 O4 C2(C=C(C=CC(CCNC(=O)C=CC1(C=CC(=C(C=1)OC)O))=2)O) PUBCHEM:5280537:*CHEBI:17818:*LIGAND-CPD:C02717: 2.3.1.110 feruloyl-CoA + tyramine = H+ + N-feruloyltyramine + coenzyme A suberin biosynthesis D-myo-inositol (1,2,5,6) tetrakisphosphate 1D-myo-inositol (1,2,5,6) tetrakisphosphate*Ins(1,2,5,6)P4*I(1,2,5,6)P4 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(OP([O-])([O-])=O)C(OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:25201947:*PUBCHEM:25244938: D-myo-inositol (1,2,3,5,6) pentakisphosphate + H2O = D-myo-inositol (1,2,5,6) tetrakisphosphate phytate degradation I D-myo-inositol (1,2,5,6) tetrakisphosphate 1D-myo-inositol (1,2,5,6) tetrakisphosphate*Ins(1,2,5,6)P4*I(1,2,5,6)P4 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(OP([O-])([O-])=O)C(OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:25201947:*PUBCHEM:25244938: D-myo-inositol (1,2,5,6) tetrakisphosphate + H2O = D-myo-inositol (1,2,6) trisphosphate phytate degradation I D-myo-inositol (1,2,5,6) tetrakisphosphate 1D-myo-inositol (1,2,5,6) tetrakisphosphate*Ins(1,2,5,6)P4*I(1,2,5,6)P4 492.013 C6 H8 O18 P4 O=P([O-])([O-])OC1(C(OP([O-])(=O)[O-])C(OP([O-])([O-])=O)C(OP(=O)([O-])[O-])C(O)C(O)1) PUBCHEM:25201947:*PUBCHEM:25244938: D-myo-inositol (1,2,4,5,6)-pentakisphosphate + H2O = D-myo-inositol (1,2,5,6) tetrakisphosphate phytate degradation I S-methyl-L-methionine S-methylmethionine 164.242 C6 H14 N1 O2 S1 [N+]C(C(=O)[O-])CC[S+](C)C CAS:4727-40-6*CAS:4289-98-9:*CHEBI:17728:*PUBCHEM:7098638:*LIGAND-CPD:C03172: 2.1.1.10 S-methyl-L-methionine + L-homocysteine = H+ + L-methionine methionine biosynthesis II S-methyl-L-methionine S-methylmethionine 164.242 C6 H14 N1 O2 S1 [N+]C(C(=O)[O-])CC[S+](C)C CAS:4727-40-6*CAS:4289-98-9:*CHEBI:17728:*PUBCHEM:7098638:*LIGAND-CPD:C03172: 2.1.1.10 S-methyl-L-methionine + L-homocysteine = H+ + L-methionine S-methylmethionine cycle S-methyl-L-methionine S-methylmethionine 164.242 C6 H14 N1 O2 S1 [N+]C(C(=O)[O-])CC[S+](C)C CAS:4727-40-6*CAS:4289-98-9:*CHEBI:17728:*PUBCHEM:7098638:*LIGAND-CPD:C03172: H+ + S-methyl-L-methionine = DMSP-amine + CO2 dimethylsulfoniopropionate biosynthesis II (Spartina) S-methyl-L-methionine S-methylmethionine 164.242 C6 H14 N1 O2 S1 [N+]C(C(=O)[O-])CC[S+](C)C CAS:4727-40-6*CAS:4289-98-9:*CHEBI:17728:*PUBCHEM:7098638:*LIGAND-CPD:C03172: S-methyl-L-methionine = 3-dimethylsulfoniopropionaldehyde + CO2 dimethylsulfoniopropionate biosynthesis I (Wollastonia) S-methyl-L-methionine S-methylmethionine 164.242 C6 H14 N1 O2 S1 [N+]C(C(=O)[O-])CC[S+](C)C CAS:4727-40-6*CAS:4289-98-9:*CHEBI:17728:*PUBCHEM:7098638:*LIGAND-CPD:C03172: 2.1.1.12 L-methionine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine dimethylsulfoniopropionate biosynthesis II (Spartina) S-methyl-L-methionine S-methylmethionine 164.242 C6 H14 N1 O2 S1 [N+]C(C(=O)[O-])CC[S+](C)C CAS:4727-40-6*CAS:4289-98-9:*CHEBI:17728:*PUBCHEM:7098638:*LIGAND-CPD:C03172: 2.1.1.12 L-methionine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine dimethylsulfoniopropionate biosynthesis I (Wollastonia) S-methyl-L-methionine S-methylmethionine 164.242 C6 H14 N1 O2 S1 [N+]C(C(=O)[O-])CC[S+](C)C CAS:4727-40-6*CAS:4289-98-9:*CHEBI:17728:*PUBCHEM:7098638:*LIGAND-CPD:C03172: 2.1.1.12 L-methionine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine S-methylmethionine cycle 3-(4-hydroxyphenyl)-3-oxo-propionyl-CoA 3-(4-hydroxyphenyl)-3-keto-propionyl-CoA*3-(4-hydroxyphenyl)-3-keto-propanoyl-CoA*3-(4-hydroxyphenyl)-3-oxo-propanoyl-CoA 925.647 C30 H38 N7 O19 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)CC(=O)C4(=CC=C(O)C=C4) PUBCHEM:46173252: 2.3.1.16 3-(4-hydroxyphenyl)-3-oxo-propionyl-CoA + coenzyme A = acetyl-CoA + 4-hydroxybenzoyl-CoA 4-hydroxybenzoate biosynthesis V 3-(4-hydroxyphenyl)-3-oxo-propionyl-CoA 3-(4-hydroxyphenyl)-3-keto-propionyl-CoA*3-(4-hydroxyphenyl)-3-keto-propanoyl-CoA*3-(4-hydroxyphenyl)-3-oxo-propanoyl-CoA 925.647 C30 H38 N7 O19 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)CC(=O)C4(=CC=C(O)C=C4) PUBCHEM:46173252: 1.1.1.35 3-(4-hydroxyphenyl)-3-hydroxy-propionyl-CoA + NAD+ = 3-(4-hydroxyphenyl)-3-oxo-propionyl-CoA + NADH + H+ 4-hydroxybenzoate biosynthesis V 2-dehydropantoate ketopantoate*2-keto-pantoate 145.135 C6 H9 O4 C(=O)(C([O-])=O)C(CO)(C)C KNAPSACK:C00007477:*PUBCHEM:16755619:*CHEBI:11561:*LIGAND-CPD:C00966: 2.1.2.11 5,10-methylenetetrahydropteroyl mono-L-glutamate + 2-oxoisovalerate + H2O = H+ + 2-dehydropantoate + tetrahydrofolate phosphopantothenate biosynthesis I 2-dehydropantoate ketopantoate*2-keto-pantoate 145.135 C6 H9 O4 C(=O)(C([O-])=O)C(CO)(C)C KNAPSACK:C00007477:*PUBCHEM:16755619:*CHEBI:11561:*LIGAND-CPD:C00966: 2.1.2.11 5,10-methylenetetrahydropteroyl mono-L-glutamate + 2-oxoisovalerate + H2O = H+ + 2-dehydropantoate + tetrahydrofolate pantothenate biosynthesis I 2-dehydropantoate ketopantoate*2-keto-pantoate 145.135 C6 H9 O4 C(=O)(C([O-])=O)C(CO)(C)C KNAPSACK:C00007477:*PUBCHEM:16755619:*CHEBI:11561:*LIGAND-CPD:C00966: 1.1.1.169 (R)-pantoate + NADP+ = H+ + 2-dehydropantoate + NADPH phosphopantothenate biosynthesis I 2-dehydropantoate ketopantoate*2-keto-pantoate 145.135 C6 H9 O4 C(=O)(C([O-])=O)C(CO)(C)C KNAPSACK:C00007477:*PUBCHEM:16755619:*CHEBI:11561:*LIGAND-CPD:C00966: 1.1.1.169 (R)-pantoate + NADP+ = H+ + 2-dehydropantoate + NADPH pantothenate biosynthesis I OPC4-3-ketoacyl-CoA 997.797 C35 H50 N7 O19 P3 S1 C(C4(C(=O)CCC(CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])4))C=CCC PUBCHEM:44237346: 1.1.1.35 NAD+ + OPC4-3-hydroxyacyl-CoA = NADH + H+ + OPC4-3-ketoacyl-CoA jasmonic acid biosynthesis OPC4-3-ketoacyl-CoA 997.797 C35 H50 N7 O19 P3 S1 C(C4(C(=O)CCC(CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])4))C=CCC PUBCHEM:44237346: 2.3.1.16 OPC4-3-ketoacyl-CoA + coenzyme A = acetyl-CoA + jasmonoyl-CoA jasmonic acid biosynthesis (S)-2,3-epoxysqualene squalene 2,3-epoxide*squalene 2,3-oxide*(S)-squalene-2,3-epoxide*2,3-EDSQ*2,3-epoxisqualene*oxidosqualene*2,3-oxidosqualene 426.724 C30 H50 O1 C(CC(=CCCC(=CCCC=C(CCC=C(CCC=C(C)C)C)C)C)C)C1(C(C)(O1)C) PUBCHEM:5280395:*LIGAND-CPD:C01054:*CAS:9029-62-3 5.4.99.8 (S)-2,3-epoxysqualene = cycloartenol plant sterol biosynthesis (S)-2,3-epoxysqualene squalene 2,3-epoxide*squalene 2,3-oxide*(S)-squalene-2,3-epoxide*2,3-EDSQ*2,3-epoxisqualene*oxidosqualene*2,3-oxidosqualene 426.724 C30 H50 O1 C(CC(=CCCC(=CCCC=C(CCC=C(CCC=C(C)C)C)C)C)C)C1(C(C)(O1)C) PUBCHEM:5280395:*LIGAND-CPD:C01054:*CAS:9029-62-3 1.14.99.7 squalene + oxygen = (S)-2,3-epoxysqualene + H2O epoxysqualene biosynthesis sucrose Glc(α1->2β)Fru*sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C2(OC1(OC(C(O)C(C1O)O)CO))(OC(CO)C(C2O)O)CO LIGAND:C00089:*CHEBI:17992:*PUBCHEM:5988:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.99 sucrose + sucrose = 1-kestotriose + β-D-glucose fructan biosynthesis sucrose Glc(α1->2β)Fru*sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C2(OC1(OC(C(O)C(C1O)O)CO))(OC(CO)C(C2O)O)CO LIGAND:C00089:*CHEBI:17992:*PUBCHEM:5988:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.10 sucrose + sucrose = 6-kestotriose + β-D-glucose fructan biosynthesis sucrose Glc(α1->2β)Fru*sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C2(OC1(OC(C(O)C(C1O)O)CO))(OC(CO)C(C2O)O)CO LIGAND:C00089:*CHEBI:17992:*PUBCHEM:5988:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.- 1-kestotriose + sucrose = 6G-kestotriose + sucrose fructan biosynthesis sucrose Glc(α1->2β)Fru*sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C2(OC1(OC(C(O)C(C1O)O)CO))(OC(CO)C(C2O)O)CO LIGAND:C00089:*CHEBI:17992:*PUBCHEM:5988:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.13 β-D-fructofuranose = sucrose + UDP sucrose degradation III sucrose Glc(α1->2β)Fru*sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C2(OC1(OC(C(O)C(C1O)O)CO))(OC(CO)C(C2O)O)CO LIGAND:C00089:*CHEBI:17992:*PUBCHEM:5988:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.13 β-D-fructofuranose = sucrose + UDP galactose degradation III sucrose Glc(α1->2β)Fru*sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C2(OC1(OC(C(O)C(C1O)O)CO))(OC(CO)C(C2O)O)CO LIGAND:C00089:*CHEBI:17992:*PUBCHEM:5988:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.13 β-D-fructofuranose = sucrose + UDP sucrose biosynthesis sucrose Glc(α1->2β)Fru*sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C2(OC1(OC(C(O)C(C1O)O)CO))(OC(CO)C(C2O)O)CO LIGAND:C00089:*CHEBI:17992:*PUBCHEM:5988:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 3.1.3.24 sucrose-6-phosphate + H2O = sucrose sucrose biosynthesis sucrose Glc(α1->2β)Fru*sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C2(OC1(OC(C(O)C(C1O)O)CO))(OC(CO)C(C2O)O)CO LIGAND:C00089:*CHEBI:17992:*PUBCHEM:5988:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.10 1-kestotriose + sucrose = 1,6-kestotetraose + β-D-glucose fructan biosynthesis sucrose Glc(α1->2β)Fru*sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C2(OC1(OC(C(O)C(C1O)O)CO))(OC(CO)C(C2O)O)CO LIGAND:C00089:*CHEBI:17992:*PUBCHEM:5988:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 3.2.1.26 sucrose + H2O = α-D-glucose + β-D-fructofuranose sucrose degradation III sucrose Glc(α1->2β)Fru*sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C2(OC1(OC(C(O)C(C1O)O)CO))(OC(CO)C(C2O)O)CO LIGAND:C00089:*CHEBI:17992:*PUBCHEM:5988:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 3.2.1.- raffinose + H2O = α-D-galactose + sucrose stachyose degradation sucrose Glc(α1->2β)Fru*sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C2(OC1(OC(C(O)C(C1O)O)CO))(OC(CO)C(C2O)O)CO LIGAND:C00089:*CHEBI:17992:*PUBCHEM:5988:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.82 galactinol + sucrose = myo-inositol + raffinose stachyose biosynthesis sucrose Glc(α1->2β)Fru*sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C2(OC1(OC(C(O)C(C1O)O)CO))(OC(CO)C(C2O)O)CO LIGAND:C00089:*CHEBI:17992:*PUBCHEM:5988:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 3.2.1.80 1-kestotriose + H2O = sucrose fructan degradation sucrose Glc(α1->2β)Fru*sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C2(OC1(OC(C(O)C(C1O)O)CO))(OC(CO)C(C2O)O)CO LIGAND:C00089:*CHEBI:17992:*PUBCHEM:5988:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.100 1-kestotriose + 1-kestotriose = 1,1-kestotetraose + sucrose fructan biosynthesis D-myo-inositol (1,3,4)-trisphosphate Ins(1,3,4)P3*1-D-myo-inositol (1,3,4)-trisphosphate*inositol 1,3,4-trisphosphate 414.049 C6 H9 O15 P3 [O-]P([O-])(=O)OC1(C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) CHEBI:58414:*PUBCHEM:25201948:*LIGAND-CPD:C01243: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) D-myo-inositol (1,3,4)-trisphosphate Ins(1,3,4)P3*1-D-myo-inositol (1,3,4)-trisphosphate*inositol 1,3,4-trisphosphate 414.049 C6 H9 O15 P3 [O-]P([O-])(=O)OC1(C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) CHEBI:58414:*PUBCHEM:25201948:*LIGAND-CPD:C01243: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) D-myo-inositol (1,3,4)-trisphosphate Ins(1,3,4)P3*1-D-myo-inositol (1,3,4)-trisphosphate*inositol 1,3,4-trisphosphate 414.049 C6 H9 O15 P3 [O-]P([O-])(=O)OC1(C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) CHEBI:58414:*PUBCHEM:25201948:*LIGAND-CPD:C01243: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis V (from Ins(1,3,4)P3) D-myo-inositol (1,3,4)-trisphosphate Ins(1,3,4)P3*1-D-myo-inositol (1,3,4)-trisphosphate*inositol 1,3,4-trisphosphate 414.049 C6 H9 O15 P3 [O-]P([O-])(=O)OC1(C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) CHEBI:58414:*PUBCHEM:25201948:*LIGAND-CPD:C01243: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP D-myo-inositol (3,4,5,6)-tetrakisphosphate biosynthesis D-myo-inositol (1,3,4)-trisphosphate Ins(1,3,4)P3*1-D-myo-inositol (1,3,4)-trisphosphate*inositol 1,3,4-trisphosphate 414.049 C6 H9 O15 P3 [O-]P([O-])(=O)OC1(C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) CHEBI:58414:*PUBCHEM:25201948:*LIGAND-CPD:C01243: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP lipid-dependent phytate biosynthesis II (via Ins(1,3,4)P3) D-myo-inositol (1,3,4)-trisphosphate Ins(1,3,4)P3*1-D-myo-inositol (1,3,4)-trisphosphate*inositol 1,3,4-trisphosphate 414.049 C6 H9 O15 P3 [O-]P([O-])(=O)OC1(C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1) CHEBI:58414:*PUBCHEM:25201948:*LIGAND-CPD:C01243: 2.7.1.159 D-myo-inositol (1,3,4)-trisphosphate + ATP = H+ + D-myo-inositol (1,3,4,6)-tetrakisphosphate + ADP D-myo-inositol (1,4,5,6)-tetrakisphosphate biosynthesis benzoate benzoic acid*benzenecarboxylic acid*phenylformic acid 121.115 C7 H5 O2 C1(C(=CC=CC=1)C([O-])=O) PUBCHEM:242:*LIGAND-CPD:C00180:*CHEBI:16150:*CAS:65-85-0 1.2.3.9 benzaldehyde + oxygen + H2O = H+ + benzoate + hydrogen peroxide aldehyde oxidation I benzoate benzoic acid*benzenecarboxylic acid*phenylformic acid 121.115 C7 H5 O2 C1(C(=CC=CC=1)C([O-])=O) PUBCHEM:242:*LIGAND-CPD:C00180:*CHEBI:16150:*CAS:65-85-0 1.2.1.28 benzaldehyde + H2O + NAD+ = benzoate + NADH + H+ benzoate biosynthesis III (CoA-dependent, non-β-oxidative) benzoate benzoic acid*benzenecarboxylic acid*phenylformic acid 121.115 C7 H5 O2 C1(C(=CC=CC=1)C([O-])=O) PUBCHEM:242:*LIGAND-CPD:C00180:*CHEBI:16150:*CAS:65-85-0 1.2.1.28 benzaldehyde + H2O + NAD+ = benzoate + NADH + H+ benzoate biosynthesis II (CoA-independent, non-β-oxidative) all-trans-decaprenyl diphosphate 856.133 C50 H81 O7 P2 CC(CCC=C(C)C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] LIGAND-CPD:C17432:*PUBCHEM:25245574: 2.5.1.39 all-trans-decaprenyl diphosphate = 3-decaprenyl-4-hydroxybenzoate + diphosphate ubiquinol-10 biosynthesis (eukaryotic) hexanal hexaldehyde 100.16 C6 H12 O1 C(CCCC=O)C CHEBI:121338:*PUBCHEM:6184:*CAS:66-25-1 (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate = 12-oxo-cis-9-dodecenoate + hexanal traumatin and (Z)-3-hexen-1-yl acetate biosynthesis (R)-mevalonate mevalonate*mevalonic acid 147.15 C6 H11 O4 OCCC(C)(O)CC(=O)[O-] CAS:150-97-0*PUBCHEM:5288798:*CHEBI:36464:*LIGAND-CPD:C00418: 1.1.1.34 NADP+ + coenzyme A + (R)-mevalonate = H+ + NADPH + (S)-3-hydroxy-3-methylglutaryl-CoA mevalonate pathway I (R)-mevalonate mevalonate*mevalonic acid 147.15 C6 H11 O4 OCCC(C)(O)CC(=O)[O-] CAS:150-97-0*PUBCHEM:5288798:*CHEBI:36464:*LIGAND-CPD:C00418: 2.7.1.36 (R)-mevalonate + ATP = H+ + mevalonate-5-phosphate + ADP mevalonate pathway I indole-3-pyruvate indole-pyr*indolepyruvic acid*(indol-3-yl)pyruvate*indolepyruvate*3-(indol-3-yl)pyruvate*3-indole-2-oxopropanoate*IPA 202.189 C11 H8 N1 O3 O=C(C([O-])=O)CC1(C2(=C(NC=1)C=CC=C2)) PUBCHEM:5460337:*CHEBI:17640:*LIGAND-CPD:C00331:*CAS:35656-49-6 4.1.1.74 H+ + indole-3-pyruvate = CO2 + indole acetaldehyde IAA biosynthesis I indole-3-pyruvate indole-pyr*indolepyruvic acid*(indol-3-yl)pyruvate*indolepyruvate*3-(indol-3-yl)pyruvate*3-indole-2-oxopropanoate*IPA 202.189 C11 H8 N1 O3 O=C(C([O-])=O)CC1(C2(=C(NC=1)C=CC=C2)) PUBCHEM:5460337:*CHEBI:17640:*LIGAND-CPD:C00331:*CAS:35656-49-6 2.6.1.27 2-oxoglutarate + L-tryptophan = L-glutamate + indole-3-pyruvate IAA biosynthesis I indole-3-pyruvate indole-pyr*indolepyruvic acid*(indol-3-yl)pyruvate*indolepyruvate*3-(indol-3-yl)pyruvate*3-indole-2-oxopropanoate*IPA 202.189 C11 H8 N1 O3 O=C(C([O-])=O)CC1(C2(=C(NC=1)C=CC=C2)) PUBCHEM:5460337:*CHEBI:17640:*LIGAND-CPD:C00331:*CAS:35656-49-6 2.6.1.- L-tryptophan + pyruvate = L-alanine + indole-3-pyruvate IAA biosynthesis I 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one 2,5-diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine*DARP*2,5-diamino-6-(1-D-ribosylamino)pyrimidin-4(3H)-one 5'-phosphate*2,5-diamino-6-(ribosylamino)-4-(3H)-pyrimidinone 5'-phosphate*2,5-diamino-6-(D-ribosylamino)pyrimidin-4(3H)-one 5'-phosphate 351.212 C9 H14 N5 O8 P1 C2(COP(=O)([O-])[O-])(C(O)C(O)C(NC1(=C(N)C(=O)NC(=N1)N))O2) PUBCHEM:25244331:*LIGAND-CPD:C01304: 3.5.4.25 H2O + GTP = H+ + diphosphate + 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one + formate flavin biosynthesis I (bacteria and plants) 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one 2,5-diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine*DARP*2,5-diamino-6-(1-D-ribosylamino)pyrimidin-4(3H)-one 5'-phosphate*2,5-diamino-6-(ribosylamino)-4-(3H)-pyrimidinone 5'-phosphate*2,5-diamino-6-(D-ribosylamino)pyrimidin-4(3H)-one 5'-phosphate 351.212 C9 H14 N5 O8 P1 C2(COP(=O)([O-])[O-])(C(O)C(O)C(NC1(=C(N)C(=O)NC(=N1)N))O2) PUBCHEM:25244331:*LIGAND-CPD:C01304: 3.5.4.26 H2O + 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one = 5-amino-6-(5-phospho-D-ribosylamino)uracil + ammonia flavin biosynthesis I (bacteria and plants) α-D-galactose 1-phosphate α-D-galactopyranose 1-phosphate*α-D-Gal-1-P*galactose-1P*galactose-1-P*D-galactose-1-phosphate*galactose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) PUBCHEM:7098639:*LIGAND-CPD:C00446:*CAS:2255-14-3 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP galactose degradation I (Leloir pathway) α-D-galactose 1-phosphate α-D-galactopyranose 1-phosphate*α-D-Gal-1-P*galactose-1P*galactose-1-P*D-galactose-1-phosphate*galactose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) PUBCHEM:7098639:*LIGAND-CPD:C00446:*CAS:2255-14-3 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP stachyose degradation α-D-galactose 1-phosphate α-D-galactopyranose 1-phosphate*α-D-Gal-1-P*galactose-1P*galactose-1-P*D-galactose-1-phosphate*galactose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) PUBCHEM:7098639:*LIGAND-CPD:C00446:*CAS:2255-14-3 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP colanic acid building blocks biosynthesis α-D-galactose 1-phosphate α-D-galactopyranose 1-phosphate*α-D-Gal-1-P*galactose-1P*galactose-1-P*D-galactose-1-phosphate*galactose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) PUBCHEM:7098639:*LIGAND-CPD:C00446:*CAS:2255-14-3 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) α-D-galactose 1-phosphate α-D-galactopyranose 1-phosphate*α-D-Gal-1-P*galactose-1P*galactose-1-P*D-galactose-1-phosphate*galactose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) PUBCHEM:7098639:*LIGAND-CPD:C00446:*CAS:2255-14-3 2.7.1.6 α-D-galactose + ATP = H+ + α-D-galactose 1-phosphate + ADP galactose degradation III α-D-galactose 1-phosphate α-D-galactopyranose 1-phosphate*α-D-Gal-1-P*galactose-1P*galactose-1-P*D-galactose-1-phosphate*galactose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) PUBCHEM:7098639:*LIGAND-CPD:C00446:*CAS:2255-14-3 2.7.7.10 H+ + α-D-galactose 1-phosphate + UTP = UDP-D-galactose + diphosphate stachyose degradation α-D-galactose 1-phosphate α-D-galactopyranose 1-phosphate*α-D-Gal-1-P*galactose-1P*galactose-1-P*D-galactose-1-phosphate*galactose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) PUBCHEM:7098639:*LIGAND-CPD:C00446:*CAS:2255-14-3 2.7.7.10 H+ + α-D-galactose 1-phosphate + UTP = UDP-D-galactose + diphosphate galactose degradation III α-D-galactose 1-phosphate α-D-galactopyranose 1-phosphate*α-D-Gal-1-P*galactose-1P*galactose-1-P*D-galactose-1-phosphate*galactose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) PUBCHEM:7098639:*LIGAND-CPD:C00446:*CAS:2255-14-3 2.7.7.12 α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-D-galactose galactose degradation I (Leloir pathway) α-D-galactose 1-phosphate α-D-galactopyranose 1-phosphate*α-D-Gal-1-P*galactose-1P*galactose-1-P*D-galactose-1-phosphate*galactose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) PUBCHEM:7098639:*LIGAND-CPD:C00446:*CAS:2255-14-3 2.7.7.12 α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-D-galactose stachyose degradation α-D-galactose 1-phosphate α-D-galactopyranose 1-phosphate*α-D-Gal-1-P*galactose-1P*galactose-1-P*D-galactose-1-phosphate*galactose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) PUBCHEM:7098639:*LIGAND-CPD:C00446:*CAS:2255-14-3 2.7.7.12 α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-D-galactose colanic acid building blocks biosynthesis α-D-galactose 1-phosphate α-D-galactopyranose 1-phosphate*α-D-Gal-1-P*galactose-1P*galactose-1-P*D-galactose-1-phosphate*galactose-1-phosphate 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) PUBCHEM:7098639:*LIGAND-CPD:C00446:*CAS:2255-14-3 2.7.7.12 α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-D-galactose UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) indole-3-acetonitrile IAN*indole-3-ylacetonitrile*3-indoleacetonitrile*(indole-3-yl)acetonitrile 156.187 C10 H8 N2 C1(=C(C2(=CC=CC=C(N1)2))CC#N) PUBCHEM:351795:*KNAPSACK:C00000107:*CHEBI:17566:*LIGAND-CPD:C02938: 3.5.5.1 indole-3-acetonitrile + H2O = H+ + ammonia + indole-3-acetate IAA biosynthesis I indole-3-acetonitrile IAN*indole-3-ylacetonitrile*3-indoleacetonitrile*(indole-3-yl)acetonitrile 156.187 C10 H8 N2 C1(=C(C2(=CC=CC=C(N1)2))CC#N) PUBCHEM:351795:*KNAPSACK:C00000107:*CHEBI:17566:*LIGAND-CPD:C02938: 4.2.1.84 indole-3-acetonitrile + H2O = indole-3-acetamide IAA biosynthesis I indole-3-acetonitrile IAN*indole-3-ylacetonitrile*3-indoleacetonitrile*(indole-3-yl)acetonitrile 156.187 C10 H8 N2 C1(=C(C2(=CC=CC=C(N1)2))CC#N) PUBCHEM:351795:*KNAPSACK:C00000107:*CHEBI:17566:*LIGAND-CPD:C02938: 4.99.1.6 (Z)-indol-3-ylacetaldoxime = indole-3-acetonitrile + H2O IAA biosynthesis I (S)-2-acetolactate (S)-2-hydroxy-2-methyl-3-oxobutanoate*α-acetolactate*(2S)-2-hydroxy-2-methyl-3-oxobutanoate 131.108 C5 H7 O4 CC(=O)C(C)(O)C(=O)[O-] PUBCHEM:440878:*CHEBI:58476:*PUBCHEM:13999770:*LIGAND-CPD:C06010: 1.1.1.86 2,3-dihydroxy-isovalerate + NADP+ = (S)-2-acetolactate + NADPH + H+ valine biosynthesis (S)-2-acetolactate (S)-2-hydroxy-2-methyl-3-oxobutanoate*α-acetolactate*(2S)-2-hydroxy-2-methyl-3-oxobutanoate 131.108 C5 H7 O4 CC(=O)C(C)(O)C(=O)[O-] PUBCHEM:440878:*CHEBI:58476:*PUBCHEM:13999770:*LIGAND-CPD:C06010: 2.2.1.6 H+ + pyruvate = (S)-2-acetolactate + CO2 valine biosynthesis CDP-ethanolamine cytidine diphosphate ethanolamine 445.239 C11 H19 N4 O11 P2 NC2(=NC(N(C1(C(C(C(O1)COP(OP(OCC[N+])([O-])=O)([O-])=O)O)O))C=C2)=O) CHEBI:57876:*PUBCHEM:25202847:*LIGAND-CPD:C00570:*CAS:3036-18-8 2.7.7.14 H+ + phosphoryl-ethanolamine + CTP = CDP-ethanolamine + diphosphate phosphatidylethanolamine biosynthesis II CDP-ethanolamine cytidine diphosphate ethanolamine 445.239 C11 H19 N4 O11 P2 NC2(=NC(N(C1(C(C(C(O1)COP(OP(OCC[N+])([O-])=O)([O-])=O)O)O))C=C2)=O) CHEBI:57876:*PUBCHEM:25202847:*LIGAND-CPD:C00570:*CAS:3036-18-8 2.7.8.1 CDP-ethanolamine = CMP phosphatidylethanolamine biosynthesis II acetoacetyl-CoA 3-acetoacetyl-CoA*acetoacetyl-S-CoA 847.577 C25 H36 N7 O18 P3 S1 CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3) KNAPSACK:C00007269:*CHEBI:15345:*PUBCHEM:25245580:*LIGAND-CPD:C00332:*CAS:1420-36-6 2.3.1.9 acetyl-CoA = acetoacetyl-CoA + coenzyme A mevalonate pathway I acetoacetyl-CoA 3-acetoacetyl-CoA*acetoacetyl-S-CoA 847.577 C25 H36 N7 O18 P3 S1 CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3) KNAPSACK:C00007269:*CHEBI:15345:*PUBCHEM:25245580:*LIGAND-CPD:C00332:*CAS:1420-36-6 2.3.3.10 acetoacetyl-CoA + H2O + acetyl-CoA = H+ + coenzyme A + (S)-3-hydroxy-3-methylglutaryl-CoA mevalonate pathway I 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate 4-amino-2-methyl-5-diphosphomethylpyrimidine*2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate*HMP-PP*4-amino-5-hydroxymethyl-2-methylpyrimidine-PP 296.093 C6 H8 N3 O7 P2 C1(N=C(N=C(C=1COP(OP([O-])([O-])=O)([O-])=O)N)C) CHEBI:57841:*PUBCHEM:25245586:*CAS:745-65-3:*LIGAND-CPD:C04752:*CAS:841-01-0 2.5.1.3 H+ + 4-methyl-5-(2-phosphonooxyethyl)thiazole + 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate = thiamine-phosphate + diphosphate thiamine biosynthesis II 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate 4-amino-2-methyl-5-diphosphomethylpyrimidine*2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate*HMP-PP*4-amino-5-hydroxymethyl-2-methylpyrimidine-PP 296.093 C6 H8 N3 O7 P2 C1(N=C(N=C(C=1COP(OP([O-])([O-])=O)([O-])=O)N)C) CHEBI:57841:*PUBCHEM:25245586:*CAS:745-65-3:*LIGAND-CPD:C04752:*CAS:841-01-0 2.7.4.7 hydroxymethylpyrimidine phosphate + ATP = 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate + ADP thiamine biosynthesis II xanthoxin 2-cis,4-trans-xanthoxin 250.337 C15 H22 O3 C1(C(C2(C(CC1O)(C)O2)C=CC(=CC=O)C)(C)C) PUBCHEM:5282222:*CHEBI:32304:*LIGAND-CPD:C13453: 1.13.11.51 9'-cis-neoxanthin + oxygen = xanthoxin + C25-allenic-apo-aldehyde abscisic acid biosynthesis xanthoxin 2-cis,4-trans-xanthoxin 250.337 C15 H22 O3 C1(C(C2(C(CC1O)(C)O2)C=CC(=CC=O)C)(C)C) PUBCHEM:5282222:*CHEBI:32304:*LIGAND-CPD:C13453: 1.1.1.288 xanthoxin + NAD+ = abscisic aldehyde + NADH + H+ abscisic acid biosynthesis 3,4-dihydroxy-5-all-trans-decaprenylbenzoate 3-(3,7,11,15,19,23-decamethyltetracosa-2,6,10,14,18,22-hexaenyl) -4,5-dihydroxy-benzoic acid*3-decaprenyl-4,5-dihydroxybenzoate 834.296 C57 H85 O4 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(=C(C(=CC(C([O-])=O)=C1)O)O))C)C)C)C)C)CCC=C(CCC=C(C)CCC=C(CCC=C(C)C)C)C PUBCHEM:25245588: 2.1.1.114 3,4-dihydroxy-5-all-trans-decaprenylbenzoate + S-adenosyl-L-methionine = H+ + 3-methoxy-4-hydroxy-5-all-trans-decaprenylbenzoate + S-adenosyl-L-homocysteine ubiquinol-10 biosynthesis (eukaryotic) 3,4-dihydroxy-5-all-trans-decaprenylbenzoate 3-(3,7,11,15,19,23-decamethyltetracosa-2,6,10,14,18,22-hexaenyl) -4,5-dihydroxy-benzoic acid*3-decaprenyl-4,5-dihydroxybenzoate 834.296 C57 H85 O4 CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCC1(=C(C(=CC(C([O-])=O)=C1)O)O))C)C)C)C)C)CCC=C(CCC=C(C)CCC=C(CCC=C(C)C)C)C PUBCHEM:25245588: 1.14.13.- 3-decaprenyl-4-hydroxybenzoate + oxygen + NADPH + H+ = 3,4-dihydroxy-5-all-trans-decaprenylbenzoate + H2O + NADP+ ubiquinol-10 biosynthesis (eukaryotic) cycloartenol 9β,19-cyclo-24-lanosten-3β-ol 426.724 C30 H50 O1 C1(CC(C(C2(C51(C3(C(CC2)C4(C)(CCC(C(CCC=C(C)C)C)C(CC3)(C)4))C5)))(C)C)O) PUBCHEM:25244945:*LIGAND-CPD:C01902:*CAS:469-38-5 5.4.99.8 (S)-2,3-epoxysqualene = cycloartenol plant sterol biosynthesis cycloartenol 9β,19-cyclo-24-lanosten-3β-ol 426.724 C30 H50 O1 C1(CC(C(C2(C51(C3(C(CC2)C4(C)(CCC(C(CCC=C(C)C)C)C(CC3)(C)4))C5)))(C)C)O) PUBCHEM:25244945:*LIGAND-CPD:C01902:*CAS:469-38-5 2.1.1.41 S-adenosyl-L-methionine + cycloartenol = H+ + S-adenosyl-L-homocysteine + 24-methylenecycloartanol plant sterol biosynthesis 2-oxopenta-3,4-dienoate 111.077 C5 H3 O3 C(=CC(=O)C(=O)[O-])=C PUBCHEM:25203760: 2-oxopenta-3,4-dienoate = 2-oxohexa-4,5-cyclopropyl-5-enoate hypoglycin biosynthesis 2-oxopenta-3,4-dienoate 111.077 C5 H3 O3 C(=CC(=O)C(=O)[O-])=C PUBCHEM:25203760: 1.-.-.- 2-oxopentenoate = H+ + 2-oxopenta-3,4-dienoate hypoglycin biosynthesis inosine hypoxanthine-ribose*iso-prinosine*riboxine 268.229 C10 H12 N4 O5 O=C1(C2(N=CN(C(N=CN1)=2)C3(OC(CO)C(O)C(O)3))) CHEBI:17596:*PUBCHEM:6021:*LIGAND-CPD:C00294:*CAS:58-63-9 3.2.2.2 inosine + H2O = hypoxanthine adenosine nucleotides degradation I inosine hypoxanthine-ribose*iso-prinosine*riboxine 268.229 C10 H12 N4 O5 O=C1(C2(N=CN(C(N=CN1)=2)C3(OC(CO)C(O)C(O)3))) CHEBI:17596:*PUBCHEM:6021:*LIGAND-CPD:C00294:*CAS:58-63-9 3.5.4.4 H2O + adenosine = ammonia + inosine adenosine nucleotides degradation II inosine hypoxanthine-ribose*iso-prinosine*riboxine 268.229 C10 H12 N4 O5 O=C1(C2(N=CN(C(N=CN1)=2)C3(OC(CO)C(O)C(O)3))) CHEBI:17596:*PUBCHEM:6021:*LIGAND-CPD:C00294:*CAS:58-63-9 2.4.2.1 inosine = hypoxanthine + α-D-ribose-1-phosphate adenosine nucleotides degradation II inosine hypoxanthine-ribose*iso-prinosine*riboxine 268.229 C10 H12 N4 O5 O=C1(C2(N=CN(C(N=CN1)=2)C3(OC(CO)C(O)C(O)3))) CHEBI:17596:*PUBCHEM:6021:*LIGAND-CPD:C00294:*CAS:58-63-9 3.1.3.5 inosine-5'-phosphate + H2O = inosine adenosine nucleotides degradation I D-myo-inositol (1,2,3,4) tetrakisphosphate 1D-myo-inositol (1,2,3,4) tetrakisphosphate*myo-inositol (1,2,3,4) tetrakisphosphate*Ins(1,2,3,4)P4*I(1,2,3,4)P4 492.013 C6 H8 O18 P4 [O-]P([O-])(=O)OC1(C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:25201091:*PUBCHEM:25244337: D-myo-inositol (1,2,3,4) tetrakisphosphate + H2O = D-myo-inositol (1,2,3) trisphosphate phytate degradation II D-myo-inositol (1,2,3,4) tetrakisphosphate 1D-myo-inositol (1,2,3,4) tetrakisphosphate*myo-inositol (1,2,3,4) tetrakisphosphate*Ins(1,2,3,4)P4*I(1,2,3,4)P4 492.013 C6 H8 O18 P4 [O-]P([O-])(=O)OC1(C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:25201091:*PUBCHEM:25244337: D-myo-inositol (1,2,3,4) tetrakisphosphate + H2O = D-myo-inositol (2,3,4) trisphosphate phytate degradation II D-myo-inositol (1,2,3,4) tetrakisphosphate 1D-myo-inositol (1,2,3,4) tetrakisphosphate*myo-inositol (1,2,3,4) tetrakisphosphate*Ins(1,2,3,4)P4*I(1,2,3,4)P4 492.013 C6 H8 O18 P4 [O-]P([O-])(=O)OC1(C(O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])1) PUBCHEM:25201091:*PUBCHEM:25244337: D-myo-inositol (1,2,3,4,5)-pentakisphosphate + H2O = D-myo-inositol (1,2,3,4) tetrakisphosphate phytate degradation II thiosulfate S2O3*S2O32-*S2O3-2 113.126 H1 O3 S2 S(=O)([O-])(S)=O PUBCHEM:439208:*CHEBI:33539:*LIGAND-CPD:C00320: 2.8.1.1 thiosulfate + hydrogen cyanide = H+ + sulfite + thiocyanate thiosulfate disproportionation III (rhodanese) 1,4-dihydroxy-2-naphthoate DHNA 203.174 C11 H7 O4 C12(C(O)=C(C([O-])=O)C=C(O)C(C=CC=C1)=2) CHEBI:11173:*PUBCHEM:6951699:*LIGAND-CPD:C03657: 3.1.2.28 1,4-dihydroxy-2-naphthoyl-CoA + H2O = H+ + 1,4-dihydroxy-2-naphthoate + coenzyme A 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) indole 117.15 C8 H7 N1 C2(C1(=C(NC=C1)C=CC=2)) PUBCHEM:798:*CHEBI:16881:*LIGAND-CPD:C00463:*CAS:120-72-9 indole + acetate = H+ + indole-3-acetate IAA biosynthesis I indole 117.15 C8 H7 N1 C2(C1(=C(NC=C1)C=CC=2)) PUBCHEM:798:*CHEBI:16881:*LIGAND-CPD:C00463:*CAS:120-72-9 4.1.2.8 (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate = indole + D-glyceraldehyde-3-phosphate IAA biosynthesis I indole 117.15 C8 H7 N1 C2(C1(=C(NC=C1)C=CC=2)) PUBCHEM:798:*CHEBI:16881:*LIGAND-CPD:C00463:*CAS:120-72-9 4.1.2.8 (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate = indole + D-glyceraldehyde-3-phosphate tryptophan biosynthesis indole 117.15 C8 H7 N1 C2(C1(=C(NC=C1)C=CC=2)) PUBCHEM:798:*CHEBI:16881:*LIGAND-CPD:C00463:*CAS:120-72-9 4.2.1.- indole + L-serine = L-tryptophan + H2O tryptophan biosynthesis gibberellin A9 GA9*GA9*gibberellin A9*gibberellin A9 315.388 C19 H23 O4 C1(CCC2(C4([H])(C1(OC2=O)C5([H])(CCC3(CC(CC3=C)(C4C([O-])=O)5))))(C)) PUBCHEM:44229188:*CHEBI:29605:*LIGAND-CPD:C11863: 1.14.11.- gibberellin A9 + 2-oxoglutarate + oxygen = GA51 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) S-adenosyl-4-methylthio-2-oxobutanoate 397.405 C15 H19 N5 O6 S1 C(CC(C([O-])=O)=O)[S+](C)CC1(OC(C(C1O)O)N3(C2(=NC=NC(=C2N=C3)N))) CHEBI:16490:*PUBCHEM:5459852:*LIGAND-CPD:C04425: 2.6.1.62 S-adenosyl-L-methionine + 7-keto-8-aminopelargonate = S-adenosyl-4-methylthio-2-oxobutanoate + 7,8-diaminopelargonate biotin biosynthesis from 7-keto-8-aminopelargonate all-trans-hexaprenyl diphosphate hexaprenyl-diphosphate 583.66 C30 H49 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:58179:*PUBCHEM:25246217:*LIGAND-CPD:C01230: 2.5.1.83 geranylfarnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-hexaprenyl diphosphate + diphosphate hexaprenyl diphosphate biosynthesis all-trans-hexaprenyl diphosphate hexaprenyl-diphosphate 583.66 C30 H49 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:58179:*PUBCHEM:25246217:*LIGAND-CPD:C01230: 2.5.1.83 geranylfarnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-hexaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III all-trans-hexaprenyl diphosphate hexaprenyl-diphosphate 583.66 C30 H49 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:58179:*PUBCHEM:25246217:*LIGAND-CPD:C01230: 2.5.1.30 all-trans-hexaprenyl diphosphate + isopentenyl diphosphate = H+ + all-trans-heptaprenyl diphosphate + diphosphate heptaprenyl diphosphate biosynthesis all-trans-hexaprenyl diphosphate hexaprenyl-diphosphate 583.66 C30 H49 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-] CHEBI:58179:*PUBCHEM:25246217:*LIGAND-CPD:C01230: 2.5.1.30 all-trans-hexaprenyl diphosphate + isopentenyl diphosphate = H+ + all-trans-heptaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III luteolin 3',4',5,7-tetrahydroxyflavone*5,7,3',4'-tetrahydroxyflavone 285.232 C15 H9 O6 C1(C=CC(O)=C(O)C=1)C2(OC3(C=C([O-])C=C(O)C(C(=O)C=2)=3)) PUBCHEM:25201972:*LIGAND-CPD:C01514:*CAS:491-70-3 1.14.11.22 eriodictyol + 2-oxoglutarate + oxygen = luteolin + succinate + CO2 + H2O luteolin biosynthesis luteolin 3',4',5,7-tetrahydroxyflavone*5,7,3',4'-tetrahydroxyflavone 285.232 C15 H9 O6 C1(C=CC(O)=C(O)C=1)C2(OC3(C=C([O-])C=C(O)C(C(=O)C=2)=3)) PUBCHEM:25201972:*LIGAND-CPD:C01514:*CAS:491-70-3 H+ + eriodictyol + NADPH + oxygen = luteolin + NADP+ + H2O luteolin biosynthesis luteolin 3',4',5,7-tetrahydroxyflavone*5,7,3',4'-tetrahydroxyflavone 285.232 C15 H9 O6 C1(C=CC(O)=C(O)C=1)C2(OC3(C=C([O-])C=C(O)C(C(=O)C=2)=3)) PUBCHEM:25201972:*LIGAND-CPD:C01514:*CAS:491-70-3 1.14.13.21 H+ + apigenin + NADPH + oxygen = luteolin + NADP+ + H2O luteolin biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- S-adenosyl-L-methionine = S-adenosyl-L-homocysteine homogalacturonan biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- 2-methyl-6-phytyl-1,4-benzoquinol + S-adenosyl-L-methionine = H+ + 2,3-dimethyl-6-phytyl-1,4-benzoquinol + S-adenosyl-L-homocysteine vitamin E biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.11 Mg-protoporphyrin + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + magnesium-protoporphyrin IX 13-monomethyl ester chlorophyllide a biosynthesis I S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- 2-methoxy-6-all trans-decaprenyl-2-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine = H+ + 6-methoxy-5-methyl-2-all-trans-decaprenyl-1,4-benzoquinol + S-adenosyl-L-homocysteine ubiquinol-10 biosynthesis (eukaryotic) S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.64 3-demethylubiquinol-10 + S-adenosyl-L-methionine = H+ + ubiquinol-10 + S-adenosyl-L-homocysteine ubiquinol-10 biosynthesis (eukaryotic) S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.95 δ-tocopherol + S-adenosyl-L-methionine = H+ + β-tocopherol + S-adenosyl-L-homocysteine vitamin E biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.98 2-(3-carboxy-3-aminopropyl)-L-histidine in eEF-2 + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine diphthamide biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.149 myricetin + S-adenosyl-L-methionine = H+ + laricitrin + S-adenosyl-L-homocysteine syringetin biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.76 quercetin + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + 3-O-methylquercetin methylquercetin biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.64 3-demethylubiquinol-9 + S-adenosyl-L-methionine = H+ + ubiquinol-9 + S-adenosyl-L-homocysteine ubiquinol-9 biosynthesis (eukaryotic) S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 3.3.1.1 S-adenosyl-L-homocysteine + H2O = L-homocysteine + adenosine methionine degradation I (to homocysteine) S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 3.3.1.1 S-adenosyl-L-homocysteine + H2O = L-homocysteine + adenosine S-adenosyl-L-methionine cycle II S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.79 S-adenosyl-L-methionine = S-adenosyl-L-homocysteine cyclopropane fatty acid (CFA) biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.79 oleate + S-adenosyl-L-methionine = H+ + dihydrosterculate + S-adenosyl-L-homocysteine cyclopropane and cyclopropene fatty acid biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- 2-methoxy-6-all trans-nonaprenyl-2-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine = H+ + 6-methoxy-5-methyl-2-all-trans-nonaprenyl-1,4-benzoquinol + S-adenosyl-L-homocysteine ubiquinol-9 biosynthesis (eukaryotic) S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.68 trans-caffeate + S-adenosyl-L-methionine = H+ + ferulate + S-adenosyl-L-homocysteine suberin biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.68 trans-caffeate + S-adenosyl-L-methionine = H+ + ferulate + S-adenosyl-L-homocysteine free phenylpropanoid acid biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.68 trans-caffeate + S-adenosyl-L-methionine = H+ + ferulate + S-adenosyl-L-homocysteine simplecoumarins biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.107 S-adenosyl-L-methionine + uroporphyrinogen-III = H+ + S-adenosyl-L-homocysteine + precorrin-1 siroheme biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.68 5-hydroxyferulate + S-adenosyl-L-methionine = H+ + sinapate + S-adenosyl-L-homocysteine free phenylpropanoid acid biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.114 3,4-dihydroxy-5-all-trans-nonaprenylbenzoate + S-adenosyl-L-methionine = H+ + 3-methoxy-4-hydroxy-5-all-trans-nonaprenylbenzoate + S-adenosyl-L-homocysteine ubiquinol-9 biosynthesis (eukaryotic) S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.41 S-adenosyl-L-methionine + cycloartenol = H+ + S-adenosyl-L-homocysteine + 24-methylenecycloartanol plant sterol biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.107 S-adenosyl-L-methionine + precorrin-1 = S-adenosyl-L-homocysteine + precorrin-2 siroheme biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.95 γ-tocopherol + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + α-tocopherol vitamin E biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 (2S)-pinocembrin + S-adenosyl-L-methionine = pinostrobin + S-adenosyl-L-homocysteine pinobanksin biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.10 L-homocysteine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + L-methionine methionine biosynthesis II S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = H+ + N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis IV S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = H+ + N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine choline biosynthesis I S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = H+ + N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis II S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.68 5-hydroxy-coniferaldehyde + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + sinapaldehyde phenylpropanoid biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.68 5-hydroxy-coniferaldehyde + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + sinapaldehyde ferulate and sinapate biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.82 3-O-methylquercetin + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + 3,7-di-O-methylquercetin methylquercetin biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 3.2.2.9 S-adenosyl-L-homocysteine + H2O = S-ribosyl-L-homocysteine + adenine S-adenosyl-L-methionine cycle I S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.114 3,4-dihydroxy-5-all-trans-decaprenylbenzoate + S-adenosyl-L-methionine = H+ + 3-methoxy-4-hydroxy-5-all-trans-decaprenylbenzoate + S-adenosyl-L-homocysteine ubiquinol-10 biosynthesis (eukaryotic) S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.103 N-dimethylethanolamine phosphate + S-adenosyl-L-methionine = H+ + phosphoryl-choline + S-adenosyl-L-homocysteine choline biosynthesis I S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.103 N-dimethylethanolamine phosphate + S-adenosyl-L-methionine = H+ + phosphoryl-choline + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis II S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 3,7,3'-tri-methylquercetagetin + S-adenosyl-L-methionine = H+ + 3,6,7,3'-tetra-methylquercetagetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.12 L-methionine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine dimethylsulfoniopropionate biosynthesis II (Spartina) S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.12 L-methionine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine dimethylsulfoniopropionate biosynthesis I (Wollastonia) S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.12 L-methionine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine S-methylmethionine cycle S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.143 24-methylenelophenol + S-adenosyl-L-methionine = H+ + 24-ethylidenelophenol + S-adenosyl-L-homocysteine plant sterol biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.98 S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + H+ diphthamide biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- indole-3-acetate + S-adenosyl-L-methionine = methyl indole-3-acetate + S-adenosyl-L-homocysteine methyl indole-3-acetate interconversion S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.98 S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + H+ diphthamide biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 3,7-di-methylquercetagetin + S-adenosyl-L-methionine = H+ + 3,7,3'-tri-methylquercetagetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.71 S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis III S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- quercetin + S-adenosyl-L-methionine = H+ + isorhamnetin + S-adenosyl-L-homocysteine quercetinsulphates biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- quercetin + S-adenosyl-L-methionine = H+ + isorhamnetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.71 S-adenosyl-L-methionine = S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis IV S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.71 S-adenosyl-L-methionine = S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis III S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate phosphatidylcholine biosynthesis IV S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate choline biosynthesis I S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate phosphatidylcholine biosynthesis III S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate phosphatidylcholine biosynthesis II S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.149 laricitrin + S-adenosyl-L-methionine = H+ + syringetin + S-adenosyl-L-homocysteine syringetin biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.83 3,7-di-O-methylquercetin + S-adenosyl-L-methionine = H+ + 3,7,4'-tri-O-methylquercetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = H+ + feruloyl-CoA + S-adenosyl-L-homocysteine chlorogenic acid biosynthesis I S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = H+ + feruloyl-CoA + S-adenosyl-L-homocysteine suberin biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = H+ + feruloyl-CoA + S-adenosyl-L-homocysteine phenylpropanoid biosynthesis S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- S-adenosyl-L-methionine = S-adenosyl-L-homocysteine S-adenosyl-L-methionine cycle I S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- S-adenosyl-L-methionine = S-adenosyl-L-homocysteine methionine degradation I (to homocysteine) S-adenosyl-L-homocysteine S-adenosylhomocysteine*S-adenosyl-L-homocysteine*2-S-adenosyl-L-homocysteine*AdoHcy*2-S-adenosyl-L-homocysteine*S-adenosyl-homocysteine*S-adenosylhomocysteine*adenosyl-homo-cys*adenosylhomocysteine*adenosylhomo-cys*SAH 384.409 C14 H20 N6 O5 S1 C2(N=C(N)C3(N=CN(C1(OC(CSCCC(C([O-])=O)[N+])C(O)C(O)1))C(N=2)=3)) CHEBI:57856:*PUBCHEM:25246222:*KNAPSACK:C00007230:*PUBCHEM:25246222:*PUBCHEM:25203782:*LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- S-adenosyl-L-methionine = S-adenosyl-L-homocysteine S-adenosyl-L-methionine cycle II bilirubin 582.655 C33 H34 N4 O6 C1(=C(C(NC1=CC2(=C(C(=C(N2)CC3(NC(=C(C=3CCC(=O)[O-])C)C=C4(NC(C(=C4C)C=C)=O)))CCC(=O)[O-])C))=O)C)C=C PUBCHEM:7067843:*LIGAND-CPD:C00486: 1.3.1.24 bilirubin = biliverdin-IX-α heme degradation quercetin-3,4'-bissulfate quercetin-3,4-bissulfate 459.332 C15 H7 O13 S2 O=C1(C(OS(=O)(=O)[O-])=C(OC2(C=C([O-])C=C(O)C1=2))C3(=CC=C(OS(=O)(=O)[O-])C(O)=C3)) PUBCHEM:25202871:*LIGAND-CPD:C01156: 2.8.2.27 quercetin 3-sulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin-3,4'-bissulfate quercetinsulphates biosynthesis quercetin-3,4'-bissulfate quercetin-3,4-bissulfate 459.332 C15 H7 O13 S2 O=C1(C(OS(=O)(=O)[O-])=C(OC2(C=C([O-])C=C(O)C1=2))C3(=CC=C(OS(=O)(=O)[O-])C(O)=C3)) PUBCHEM:25202871:*LIGAND-CPD:C01156: quercetin-3,4'-bissulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + quercetin 3, 7, 4'-trisulphate quercetinsulphates biosynthesis methanethiol methanethiol*methylsulfanium*methylsulfide anion*methyl-mercaptan*methylmercaptan*mercaptomethane*thiomethane*methyl sulfhydrate*thiomethyl alcohol 48.103 C1 H4 S1 CS PUBCHEM:878:*PUBCHEM:878:*CHEBI:16007:*LIGAND-CPD:C00409: 4.4.1.11 L-methionine + H2O = H+ + methanethiol + ammonia + 2-oxobutanoate methionine degradation II D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 228.095 C5 H9 O8 P1 C(O)C(C(C(COP([O-])([O-])=O)O)O)=O PUBCHEM:21144996:*CHEBI:58121:*PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 2.7.1.19 D-ribulose-5-phosphate + ATP = H+ + D-ribulose-1,5-bisphosphate + ADP Rubisco shunt D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 228.095 C5 H9 O8 P1 C(O)C(C(C(COP([O-])([O-])=O)O)O)=O PUBCHEM:21144996:*CHEBI:58121:*PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 2.7.1.19 D-ribulose-5-phosphate + ATP = H+ + D-ribulose-1,5-bisphosphate + ADP Calvin-Benson-Bassham cycle D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 228.095 C5 H9 O8 P1 C(O)C(C(C(COP([O-])([O-])=O)O)O)=O PUBCHEM:21144996:*CHEBI:58121:*PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 4.1.99.12 D-ribulose-5-phosphate = H+ + formate + 1-deoxy-L-glycero-tetrulose 4-phosphate flavin biosynthesis I (bacteria and plants) D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 228.095 C5 H9 O8 P1 C(O)C(C(C(COP([O-])([O-])=O)O)O)=O PUBCHEM:21144996:*CHEBI:58121:*PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 5.1.3.1 D-ribulose-5-phosphate = D-xylulose-5-phosphate pentose phosphate pathway (partial) D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 228.095 C5 H9 O8 P1 C(O)C(C(C(COP([O-])([O-])=O)O)O)=O PUBCHEM:21144996:*CHEBI:58121:*PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 5.1.3.1 D-ribulose-5-phosphate = D-xylulose-5-phosphate Rubisco shunt D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 228.095 C5 H9 O8 P1 C(O)C(C(C(COP([O-])([O-])=O)O)O)=O PUBCHEM:21144996:*CHEBI:58121:*PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 5.1.3.1 D-ribulose-5-phosphate = D-xylulose-5-phosphate pentose phosphate pathway (non-oxidative branch) D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 228.095 C5 H9 O8 P1 C(O)C(C(C(COP([O-])([O-])=O)O)O)=O PUBCHEM:21144996:*CHEBI:58121:*PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 5.1.3.1 D-ribulose-5-phosphate = D-xylulose-5-phosphate Calvin-Benson-Bassham cycle D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 228.095 C5 H9 O8 P1 C(O)C(C(C(COP([O-])([O-])=O)O)O)=O PUBCHEM:21144996:*CHEBI:58121:*PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 5.3.1.6 D-ribose-5-phosphate = D-ribulose-5-phosphate Rubisco shunt D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 228.095 C5 H9 O8 P1 C(O)C(C(C(COP([O-])([O-])=O)O)O)=O PUBCHEM:21144996:*CHEBI:58121:*PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 5.3.1.6 D-ribose-5-phosphate = D-ribulose-5-phosphate pentose phosphate pathway (non-oxidative branch) D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 228.095 C5 H9 O8 P1 C(O)C(C(C(COP([O-])([O-])=O)O)O)=O PUBCHEM:21144996:*CHEBI:58121:*PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 5.3.1.6 D-ribose-5-phosphate = D-ribulose-5-phosphate Calvin-Benson-Bassham cycle D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 228.095 C5 H9 O8 P1 C(O)C(C(C(COP([O-])([O-])=O)O)O)=O PUBCHEM:21144996:*CHEBI:58121:*PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 1.1.1.44 6-phospho-D-gluconate = D-ribulose-5-phosphate + CO2 pentose phosphate pathway (oxidative branch) CTP cytidine-triphosphate*cytidine-5'-triphosphate 479.127 C9 H12 N3 O14 P3 NC1(C=CN(C(=O)N=1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058166:*CHEBI:37563:*LIGAND-CPD:C00063:*CAS:65-47-4 6.3.2.5 D-4'-phosphopantothenate + L-cysteine + CTP = H+ + R-4'-phosphopantothenoyl-L-cysteine + diphosphate + CMP coenzyme A biosynthesis CTP cytidine-triphosphate*cytidine-5'-triphosphate 479.127 C9 H12 N3 O14 P3 NC1(C=CN(C(=O)N=1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058166:*CHEBI:37563:*LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.14 H+ + phosphoryl-ethanolamine + CTP = CDP-ethanolamine + diphosphate phosphatidylethanolamine biosynthesis II CTP cytidine-triphosphate*cytidine-5'-triphosphate 479.127 C9 H12 N3 O14 P3 NC1(C=CN(C(=O)N=1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058166:*CHEBI:37563:*LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.15 H+ + phosphoryl-choline + CTP = CDP-choline + diphosphate phosphatidylcholine biosynthesis I CTP cytidine-triphosphate*cytidine-5'-triphosphate 479.127 C9 H12 N3 O14 P3 NC1(C=CN(C(=O)N=1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058166:*CHEBI:37563:*LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.15 H+ + phosphoryl-choline + CTP = CDP-choline + diphosphate choline biosynthesis III CTP cytidine-triphosphate*cytidine-5'-triphosphate 479.127 C9 H12 N3 O14 P3 NC1(C=CN(C(=O)N=1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058166:*CHEBI:37563:*LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.15 H+ + phosphoryl-choline + CTP = CDP-choline + diphosphate phosphatidylcholine biosynthesis II CTP cytidine-triphosphate*cytidine-5'-triphosphate 479.127 C9 H12 N3 O14 P3 NC1(C=CN(C(=O)N=1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058166:*CHEBI:37563:*LIGAND-CPD:C00063:*CAS:65-47-4 CTP = dCTP + H2O pyrimidine deoxyribonucleotides de novo biosynthesis I CTP cytidine-triphosphate*cytidine-5'-triphosphate 479.127 C9 H12 N3 O14 P3 NC1(C=CN(C(=O)N=1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058166:*CHEBI:37563:*LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.- H+ + N-dimethylethanolamine phosphate + CTP = CDP-N-dimethylethanolamine + diphosphate phosphatidylcholine biosynthesis IV CTP cytidine-triphosphate*cytidine-5'-triphosphate 479.127 C9 H12 N3 O14 P3 NC1(C=CN(C(=O)N=1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058166:*CHEBI:37563:*LIGAND-CPD:C00063:*CAS:65-47-4 2.7.4.6 CDP + ATP = CTP + ADP pyrimidine ribonucleotides interconversion CTP cytidine-triphosphate*cytidine-5'-triphosphate 479.127 C9 H12 N3 O14 P3 NC1(C=CN(C(=O)N=1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058166:*CHEBI:37563:*LIGAND-CPD:C00063:*CAS:65-47-4 2.7.4.6 CDP + ATP = CTP + ADP salvage pathways of pyrimidine ribonucleotides CTP cytidine-triphosphate*cytidine-5'-triphosphate 479.127 C9 H12 N3 O14 P3 NC1(C=CN(C(=O)N=1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058166:*CHEBI:37563:*LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.41 CTP + H+ = diphosphate CDP-diacylglycerol biosynthesis II CTP cytidine-triphosphate*cytidine-5'-triphosphate 479.127 C9 H12 N3 O14 P3 NC1(C=CN(C(=O)N=1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058166:*CHEBI:37563:*LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.41 CTP + H+ = diphosphate CDP-diacylglycerol biosynthesis I CTP cytidine-triphosphate*cytidine-5'-triphosphate 479.127 C9 H12 N3 O14 P3 NC1(C=CN(C(=O)N=1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058166:*CHEBI:37563:*LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.38 3-deoxy-D-manno-octulosonate + CTP = CMP-3-deoxy-D-manno-octulosonate + diphosphate CMP-KDO biosynthesis II (from D-arabinose 5-phosphate) CTP cytidine-triphosphate*cytidine-5'-triphosphate 479.127 C9 H12 N3 O14 P3 NC1(C=CN(C(=O)N=1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058166:*CHEBI:37563:*LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.57 H+ + N-methylethanolamine phosphate + CTP = CDP-N-methylethanolamine + diphosphate phosphatidylcholine biosynthesis III CTP cytidine-triphosphate*cytidine-5'-triphosphate 479.127 C9 H12 N3 O14 P3 NC1(C=CN(C(=O)N=1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058166:*CHEBI:37563:*LIGAND-CPD:C00063:*CAS:65-47-4 6.3.4.2 ATP + UTP + L-glutamine + H2O = H+ + ADP + CTP + L-glutamate pyrimidine ribonucleotides interconversion CTP cytidine-triphosphate*cytidine-5'-triphosphate 479.127 C9 H12 N3 O14 P3 NC1(C=CN(C(=O)N=1)C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2)) PUBCHEM:7058166:*CHEBI:37563:*LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.60 H+ + 2-C-methyl-D-erythritol-4-phosphate + CTP = 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + diphosphate methylerythritol phosphate pathway ent-16-a-hydroxy-kaurene phyllocladan-16α-ol 290.488 C20 H34 O1 CC4(C3(C(C1(C2(CC(O)(C)C(CC1)C2)CC3))(CCC4)C))C PUBCHEM:44237348: all-trans-geranyl-geranyl diphosphate + H2O = ent-16-a-hydroxy-kaurene + diphosphate ent -kaurene biosynthesis II Fe2+ Fe(II)*Fe+2*Fe++*ferrous iron*Fe+2*Fe2+*ferrous ion*fe(ii) 55.847 FE1 [Fe++] LIGAND-CPD:C14818:*PUBCHEM:27284:*CHEBI:29033:*LIGAND-CPD:C14818:*PUBCHEM:27284:*LIGAND-CPD:C00023: 1.16.1.7 Fe3+ + NADH = H+ + Fe2+ + NAD+ Fe(III)-reduction and Fe(II) transport Fe2+ Fe(II)*Fe+2*Fe++*ferrous iron*Fe+2*Fe2+*ferrous ion*fe(ii) 55.847 FE1 [Fe++] LIGAND-CPD:C14818:*PUBCHEM:27284:*CHEBI:29033:*LIGAND-CPD:C14818:*PUBCHEM:27284:*LIGAND-CPD:C00023: 4.99.1.1 protoporphyrin IX + Fe2+ = protoheme IX + H+ heme biosynthesis from uroporphyrinogen-III I Fe2+ Fe(II)*Fe+2*Fe++*ferrous iron*Fe+2*Fe2+*ferrous ion*fe(ii) 55.847 FE1 [Fe++] LIGAND-CPD:C14818:*PUBCHEM:27284:*CHEBI:29033:*LIGAND-CPD:C14818:*PUBCHEM:27284:*LIGAND-CPD:C00023: Fe2+ = Fe2+ Fe(III)-reduction and Fe(II) transport Fe2+ Fe(II)*Fe+2*Fe++*ferrous iron*Fe+2*Fe2+*ferrous ion*fe(ii) 55.847 FE1 [Fe++] LIGAND-CPD:C14818:*PUBCHEM:27284:*CHEBI:29033:*LIGAND-CPD:C14818:*PUBCHEM:27284:*LIGAND-CPD:C00023: 1.14.99.3 protoheme IX + oxygen = biliverdin-IX-α + Fe2+ + carbon monoxide + H2O heme degradation Fe2+ Fe(II)*Fe+2*Fe++*ferrous iron*Fe+2*Fe2+*ferrous ion*fe(ii) 55.847 FE1 [Fe++] LIGAND-CPD:C14818:*PUBCHEM:27284:*CHEBI:29033:*LIGAND-CPD:C14818:*PUBCHEM:27284:*LIGAND-CPD:C00023: 4.99.1.4 H+ + sirohydrochlorin + Fe2+ = siroheme siroheme biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.38 NADP+ = NADPH + H+ very long chain fatty acid biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.25 shikimate + NADP+ = H+ + 3-dehydroshikimate + NADPH chorismate biosynthesis I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.86 2,3-dihydroxy-isovalerate + NADP+ = (S)-2-acetolactate + NADPH + H+ valine biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.50 coenzyme A + NADP+ = NADPH + H+ cuticular wax biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- H+ + coniferaldehyde + NADPH + oxygen = 5-hydroxy-coniferaldehyde + NADP+ + H2O phenylpropanoid biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- H+ + coniferaldehyde + NADPH + oxygen = 5-hydroxy-coniferaldehyde + NADP+ + H2O ferulate and sinapate biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: N6-(Δ2-isopentenyl)-adenosine 5'-triphosphate + NADPH + H2O = H+ + trans-zeatin riboside triphosphate + NADP+ trans-zeatin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.267 2-C-methyl-D-erythritol-4-phosphate + NADP+ = 1-deoxy-D-xylulose 5-phosphate + NADPH + H+ methylerythritol phosphate pathway NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.68 sinapaldehyde + NADP+ + H2O = H+ + sinapate + NADPH ferulate and sinapate biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.86 H+ + 2-aceto-2-hydroxy-butanoate + NADPH = 2,3-dihydroxy-3-methylvalerate + NADP+ isoleucine biosynthesis I (from threonine) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.- 18-oxo-oleate + NADP+ + H2O = H+ + octadecenedioate + NADPH suberin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.21 H+ + apigenin + NADPH + oxygen = luteolin + NADP+ + H2O luteolin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.17.1.3 afzelechin + NADP+ + H2O = leucopelargonidin + NADPH + H+ 2,3-trans-flavanols biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.88 H+ + dihydrokaempferol + NADPH + oxygen = dihydromyricetin + NADP+ + H2O leucodelphinidin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.88 H+ + dihydrokaempferol + NADPH + oxygen = dihydromyricetin + NADP+ + H2O syringetin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.5.1.3 NADP+ + tetrahydrofolate = H+ + NADPH + 7,8-dihydrofolate monoglutamate folate transformations II (plants) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.5.1.3 NADP+ + tetrahydrofolate = H+ + NADPH + 7,8-dihydrofolate monoglutamate tetrahydrofolate biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.79 H+ + ent-kaurenoate + oxygen + NADPH = ent-7-α-hydroxykaurenoate + H2O + NADP+ GA12 biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.42 D-threo-isocitrate + NADP+ = 2-oxoglutarate + CO2 + NADPH glutamine biosynthesis III NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: N6-(Δ2-isopentenyl)-adenosine 5'-diphosphate + NADPH + H2O = H+ + trans-zeatin riboside diphosphate + NADP+ trans-zeatin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- H+ + tetrahydrogeranylgeranyl-chlorophyll a + NADPH = chlorophyll a + NADP+ chlorophyll a biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.- cycloeucalenone + NADPH + H+ = cycloeucalenol + NADP+ plant sterol biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- L-tryptophan + oxygen + NADPH = N-hydroxy-L-tryptophan + NADP+ + H2O IAA biosynthesis I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- laurate + oxygen + NADPH + H+ = ω-hydroxylaurate + NADP+ + H2O ω-hydroxylation of caprate and laurate NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.36 NADP+ = NADPH + H+ very long chain fatty acid biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.70 glutamate-1-semialdehyde + NADP+ = NADPH tetrapyrrole biosynthesis I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 2.3.1.170 H+ + 4-coumaroyl-CoA + malonyl-CoA + NADPH = isoliquiritigenin + coenzyme A + CO2 + NADP+ + H2O flavonoid biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O leucopelargonidin and leucocyanidin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O leucodelphinidin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O flavonol biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.11 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 4-coumarate suberin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.11 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 4-coumarate phenylpropanoid biosynthesis, initial reactions NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.21 5-dehydro episterol + NADPH = 24-methylenecholesterol + NADP+ plant sterol biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.193 5-amino-6-(5-phospho-D-ribitylamino)uracil + NADP+ = 5-amino-6-(5-phospho-D-ribosylamino)uracil + NADPH + H+ flavin biosynthesis I (bacteria and plants) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = H+ + N-acetylglutamyl-phosphate + NADPH arginine biosynthesis II (acetyl cycle) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = H+ + N-acetylglutamyl-phosphate + NADPH ornithine biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: NADPH + H+ = NADP+ cis-vaccenate biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.195 coniferyl alcohol + NADP+ = coniferaldehyde + NADPH + H+ phenylpropanoid biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.219 H+ + dihydrokaempferol + NADPH = leucopelargonidin + NADP+ leucopelargonidin and leucocyanidin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.100 NADP+ = NADPH + H+ cis-vaccenate biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.75 H+ + divinyl protochlorophyllide a + NADPH = monovinyl protochlorophyllide a + NADP+ chlorophyllide a biosynthesis I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- sitosterol + NADPH + H+ + oxygen = stigmasterol + NADP+ + H2O plant sterol biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.3.9 H+ + oxygen + NADPH + loganin = H2O + NADP+ + secologanin camptothecin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.6.5.4 monodehydroascorbate + NADPH = H+ + L-ascorbate + NADP+ ascorbate glutathione cycle NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.271 NADP+ + GDP-L-fucose = H+ + NADPH + GDP-4-dehydro-6-deoxy-D-mannose GDP-L-fucose biosynthesis I (from GDP-D-mannose) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.49 β-D-glucose-6-phosphate + NADP+ = 6-phospho-D-glucono-1,5-lactone + NADPH + H+ pentose phosphate pathway (oxidative branch) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.169 (R)-pantoate + NADP+ = H+ + 2-dehydropantoate + NADPH phosphopantothenate biosynthesis I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.169 (R)-pantoate + NADP+ = H+ + 2-dehydropantoate + NADPH pantothenate biosynthesis I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: H+ + Δ24-25-sitosterol + NADPH = sitosterol + NADP+ plant sterol biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.8.1.2 H2O + NADP+ + hydrogen sulfide = H+ + sulfite + NADPH sulfate reduction I (assimilatory) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: H+ + UDP-4-dehydro-6-deoxy-D-glucose + NADPH = UDP-L-rhamnose + NADP+ UDP-L-rhamnose biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.80 H+ + primary fluorescent chlorophyll catabolite + NADP+ = red chlorophyll catabolite + NADPH chlorophyll a degradation NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- H+ + (3R,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- H+ + (22α)-hydroxy-campest-4-en-3-one + NADPH + oxygen = (22R,23R)-22,23-dihydroxy-campest-4-en-3-one + NADP+ + H2O brassinosteroid biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.17.1.3 cyanidin + NADPH = epicatechin + NADP+ + H2O 2,3-cis-flavanols biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.41 L-glutamate γ-semialdehyde + NADP+ = L-glutamate-5-phosphate + NADPH + H+ proline biosynthesis I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.41 L-glutamate γ-semialdehyde + NADP+ = L-glutamate-5-phosphate + NADPH + H+ citrulline biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- 7-hydroxy-chlorophyllide a + oxygen + NADPH = chlorophyllide b + H2O + NADP+ chlorophyll cycle NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- oleate + NADPH + oxygen = 18-hydroxyoleate + NADP+ + H2O suberin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 2.7.1.86 NADH + ATP = H+ + NADPH + ADP NAD/NADH phosphorylation and dephosphorylation NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.11 NADP+ + L-aspartate-semialdehyde = H+ + NADPH + L-aspartyl-4-phosphate lysine biosynthesis VI NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.11 NADP+ + L-aspartate-semialdehyde = H+ + NADPH + L-aspartyl-4-phosphate homoserine biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- H+ + (22α)-hydroxy-campesterol + NADPH + oxygen = (22R,23R)-22,23-dihydroxycampesterol + NADP+ + H2O brassinosteroid biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- H+ + (5α)-campestan-3-one + oxygen + NADPH = (22S,24R)-22-hydroxy-5α-ergostan-3-one + H2O + NADP+ brassinosteroid biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.219 H+ + dihydromyricetin + NADPH = leucodelphinidin + NADP+ leucodelphinidin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 3.1.3.- NADPH + H2O = NADH NAD/NADH phosphorylation and dephosphorylation NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.21 H+ + naringenin + NADPH + oxygen = eriodictyol + NADP+ + H2O luteolin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.44 4-coumaroyl-CoA + NADPH + H+ = coumaraldehyde + coenzyme A + NADP+ phenylpropanoid biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.8.1.7 glutathione + NADP+ = glutathione disulfide + NADPH + H+ glutathione redox reactions I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.8.1.7 glutathione + NADP+ = glutathione disulfide + NADPH + H+ glutathione redox reactions II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- H+ + campestanol + oxygen + NADPH = 6-deoxocathasterone + H2O + NADP+ brassinosteroid biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.5.1.8 L-saccharopine + H2O + NADP+ = L-lysine + 2-oxoglutarate + NADPH + H+ lysine degradation II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate + NADPH + H2O = H+ + trans-zeatin riboside monophosphate + NADP+ trans-zeatin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.219 H+ + trans dihydroquercetin + NADPH = leucocyanidin + NADP+ leucopelargonidin and leucocyanidin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.81 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + oxygen + NADPH + H+ = divinyl protochlorophyllide a + NADP+ + H2O chlorophyllide a biosynthesis I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.- avenastenone + NADPH + H+ = avenasterol + NADP+ plant sterol biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.6.1.1 NAD+ + NADPH = NADH + NADP+ NAD/NADH phosphorylation and dephosphorylation NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.44 H+ + feruloyl-CoA + NADPH = coniferaldehyde + NADP+ + coenzyme A phenylpropanoid biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.2 5,6-dihydrothymine + NADP+ = thymine + NADPH + H+ thymine degradation NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.39 oxygen + NADPH + L-arginine = L-citrulline + NADP+ + nitric oxide citrulline-nitric oxide cycle NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ chlorogenic acid biosynthesis I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ chlorogenic acid biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.36 H+ + trans-5-O-(4-coumaroyl)-D-quinate + oxygen + NADPH = trans-5-O-caffeoyl-D-quinate + H2O + NADP+ phenylpropanoid biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.88 H+ + eriodictyol + NADPH + oxygen = 3',4',5'-pentahydroxyflavanone + NADP+ + H2O leucodelphinidin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.21 5-dehydroavenasterol + NADPH = isofucosterol + NADP+ plant sterol biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.79 GA12-aldehyde + NADPH + oxygen = gibberellin A12 + NADP+ + H2O GA12 biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.78 ent-kaurenol + NADPH + H+ + oxygen = ent-kaurenal + NADP+ + H2O GA12 biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.100 NADPH + H+ = NADP+ palmitate biosynthesis II (bacteria and plants) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 4-coumaroyl-CoA + NADPH + FADH2 = p-dihydrocoumaroyl-CoA + NADP+ + FAD + H+ phloridzin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.- episterone + NADPH + H+ = episterol + NADP+ plant sterol biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- N-hydroxy-L-tryptophan + oxygen + NADPH + H+ = N,N-dihydroxy-L-tryptophan + NADP+ + H2O IAA biosynthesis I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.- NADPH + H+ = NADP+ + coenzyme A cuticular wax biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- 24-epi-campesterol + NADPH + H+ + oxygen = brassicasterol + NADP+ + H2O plant sterol biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.79 succinate semialdehyde + NADP+ + H2O = succinate + NADPH + H+ 4-aminobutyrate degradation II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.100 NADP+ = NADPH + H+ fatty acid elongation -- saturated NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: caprate + NADP+ + OH- = ω-hydroxycaprate + NADPH ω-hydroxylation of caprate and laurate NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: H+ + eriodictyol + NADPH + oxygen = luteolin + NADP+ + H2O luteolin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- nonaprenyl-4-hydroxybenzoate + oxygen + NADPH + H+ = 3,4-dihydroxy-5-all-trans-nonaprenylbenzoate + H2O + NADP+ ubiquinol-9 biosynthesis (eukaryotic) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.34 NADP+ + coenzyme A + (R)-mevalonate = H+ + NADPH + (S)-3-hydroxy-3-methylglutaryl-CoA mevalonate pathway I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: H+ + naringenin + NADPH + oxygen = apigenin + NADP+ + H2O luteolin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.70 NADPH + oxygen + obtusifoliol + H+ = H2O + NADP+ + formate + 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol plant sterol biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: tryptamine + oxygen + NADPH = N-hydroxyl-tryptamine + H2O + NADP+ IAA biosynthesis I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.70 4α-methyl-5α-ergosta-8,14,24(28)-dien-3β-ol + NADP+ = 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol + NADPH + H+ plant sterol biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.102 NADP+ + sphinganine = H+ + NADPH + 3-dehydrosphinganine sphingolipid biosynthesis (plants) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- campesterol + NADP+ = H+ + crinosterol + NADPH plant sterol biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.-.- H+ + sphinganine + oxygen + NADPH = 4-hydroxysphinganine + H2O + NADP+ sphingolipid biosynthesis (plants) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: H+ + ferulate + NADPH + oxygen = 5-hydroxyferulate + H2O + NADP+ free phenylpropanoid acid biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- H+ + geranylgeranyl-chlorophyll a + NADPH = dihydrogeranylgeranyl-chlorophyll a + NADP+ chlorophyll a biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.40 (S)-malate + NADP+ = NADPH + CO2 + pyruvate gluconeogenesis I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.40 (S)-malate + NADP+ = NADPH + CO2 + pyruvate C4 photosynthetic carbon assimilation cycle NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- H+ + campesterol + oxygen + NADPH = (22α)-hydroxy-campesterol + H2O + NADP+ brassinosteroid biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.112 (22S,24R)-22-hydroxy-5α-ergostan-3-one + oxygen + NADPH + H+ = 3-dehydro-6-deoxoteasterone + NADP+ + H2O brassinosteroid biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 7-hydroxy-chlorophyll a + H2O + NADP+ = H+ + chlorophyll a + oxygen + NADPH chlorophyll cycle NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- H+ + 3-epi-6-deoxocathasterone + NADPH + oxygen = 6-deoxotyphasterol + NADP+ + H2O brassinosteroid biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.78 ent-kaurenal + NADPH + oxygen = ent-kaurenoate + NADP+ + H2O GA12 biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.8.1.9 NADP+ = NADPH + H+ thioredoxin pathway NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.34 NADPH = NADP+ fatty acid β-oxidation IV (unsaturated, even number) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.99.- H+ + campest-4-en-3-one + NADPH = (5α)-campestan-3-one + NADP+ brassinosteroid biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.79 ent-7-α-hydroxykaurenoate + NADPH + H+ + oxygen = GA12-aldehyde + NADP+ + H2O GA12 biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- NADP+ = NADPH petroselinate biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.81 magnesium-protoporphyrin IX 13-monomethyl ester + oxygen + NADPH + H+ = 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.195 H+ + coumaraldehyde + NADPH = coumaryl-alcohol + NADP+ phenylpropanoid biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.14 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 2-coumarate coumarin biosynthesis (via 2-coumarate) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- H+ + chlorophyllide a + oxygen + NADPH = 7-hydroxy-chlorophyllide a + H2O + NADP+ chlorophyll cycle NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.78 L-arogenate + NADP+ = L-tyrosine + CO2 + NADPH tyrosine biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.78 H+ + ent-kaurene + oxygen + NADPH = H2O + NADP+ + ent-kaurenol GA12 biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.-.- H+ + 24-methyldesmosterol + NADPH = campesterol + NADP+ plant sterol biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- H+ + campest-4-en-3-one + oxygen + NADPH = (22α)-hydroxy-campest-4-en-3-one + H2O + NADP+ brassinosteroid biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.- 18-hydroxyoleate + NADP+ = H+ + 18-oxo-oleate + NADPH suberin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.9 D-glyceraldehyde-3-phosphate + NADP+ + H2O = H+ + 3-phospho-D-glycerate + NADPH glycolysis IV (plant cytosol) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.2 5,6-dihydrouracil + NADP+ = uracil + NADPH + H+ uracil degradation II (reductive) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- 2-decaprenyl-6-methoxyphenol + oxygen + NADPH + H+ = 2-methoxy-6-all trans-decaprenyl-2-methoxy-1,4-benzoquinol + H2O + NADP+ ubiquinol-10 biosynthesis (eukaryotic) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- H+ + (3S,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.100 NADP+ = NADPH + H+ palmitate biosynthesis II (bacteria and plants) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.42 NADP+ + 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate = H+ + NADPH + 12-oxo-cis-10,15-phytodienoate jasmonic acid biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.100 NADP+ = NADPH + H+ stearate biosynthesis II (plants) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.195 H+ + sinapaldehyde + NADPH = sinapyl-alcohol + NADP+ phenylpropanoid biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: H+ + 4-coumarate + NADPH + oxygen = trans-caffeate + H2O + NADP+ suberin biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: H+ + 4-coumarate + NADPH + oxygen = trans-caffeate + H2O + NADP+ free phenylpropanoid acid biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.13 NADP+ + D-glyceraldehyde-3-phosphate = H+ + NADPH + 1,3-bisphospho-D-glycerate Calvin-Benson-Bassham cycle NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.10 NADP+ = NADPH fatty acid elongation -- saturated NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.100 NADP+ = NADPH + H+ petroselinate biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.82 (S)-malate + NADP+ = H+ + NADPH + oxaloacetate C4 photosynthetic carbon assimilation cycle NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.93 H+ + 2-cis-abscisic acid + NADPH + oxygen = 8'-hydroxyabscisate + NADP+ + H2O phaseic acid biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.12.20 pheophorbide a + oxygen + NADPH = H+ + red chlorophyll catabolite + NADP+ chlorophyll a degradation NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- 3-decaprenyl-4-hydroxybenzoate + oxygen + NADPH + H+ = 3,4-dihydroxy-5-all-trans-decaprenylbenzoate + H2O + NADP+ ubiquinol-10 biosynthesis (eukaryotic) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O chlorogenic acid biosynthesis I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O chlorogenic acid biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O simplecoumarins biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.36 4-coumaroylshikimate + NADPH + oxygen + H+ = caffeoylshikimate + NADP+ + H2O phenylpropanoid biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.99.- H+ + (22α)-hydroxy-campest-4-en-3-one + NADPH = (22S,24R)-22-hydroxy-5α-ergostan-3-one + NADP+ brassinosteroid biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.18.1.2 NADP+ = NADPH + H+ photosynthesis light reactions NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.17.1.3 gallocatechin + NADP+ + H2O = leucodelphinidin + NADPH + H+ 2,3-trans-flavanols biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- H+ + dihydrogeranylgeranyl-chlorophyll a + NADPH = tetrahydrogeranylgeranyl-chlorophyll a + NADP+ chlorophyll a biosynthesis II NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.81 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + oxygen = 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.5.1.5 5,10-methylenetetrahydropteroyl mono-L-glutamate + NADP+ = NADPH + 5,10-methenyltetrahydrofolate folate transformations I NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.5.1.5 5,10-methylenetetrahydropteroyl mono-L-glutamate + NADP+ = NADPH + 5,10-methenyltetrahydrofolate folate transformations II (plants) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.5.1.5 5,10-methylenetetrahydropteroyl mono-L-glutamate + NADP+ = NADPH + 5,10-methenyltetrahydrofolate formaldehyde oxidation V (tetrahydrofolate pathway) NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.17.1.3 catechin + NADP+ + H2O = leucocyanidin + NADPH + H+ 2,3-trans-flavanols biosynthesis NADPH Nicotinamide adenine dinucleotide phosphate - reduced*NADPH+H+*NADPH2*NADPH2*dihydrotriphosphopyridine nucleotide*dihydrotriphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide phosphate*dihydronicotinamide adenine dinucleotide phosphate reduced*NADP-reduced*NADP-red*NADPH+H+*TPNH*dihydronicotinamide adenine dinucleotide-P*NADP(H) 741.394 C21 H26 N7 O17 P3 O=P(OP(=O)([O-])OCC1(C(C(C(O1)N2(C=C(CC=C2)C(=O)N))O)O))(OCC5(C(C(C(N4(C3(=C(C(=NC=N3)N)N=C4)))O5)OP([O-])([O-])=O)O))[O-] PUBCHEM:15983949:*CHEBI:57783:*PUBCHEM:15983949:*PUBCHEM:15983949:*CHEBI:16474*LIGAND-CPD:C00005*PUBCHEM:5884*CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.33 chlorophyllide a + NADP+ = H+ + monovinyl protochlorophyllide a + NADPH chlorophyllide a biosynthesis I traumatin traumatin*12-oxo-t-10-dodecenoate*12-oxo-trans-10-dodecenoate*Delta(10)-ODA*12-oxo-10E-dodecenoic acid 211.28 C12 H19 O3 C(CCCC(=O)[O-])CCCCC=CC=O PUBCHEM:5312889:*PUBCHEM:15388629:*CHEBI:19144:*LIGAND-CPD:C16309: 12-oxo-cis-9-dodecenoate = traumatin traumatin and (Z)-3-hexen-1-yl acetate biosynthesis γ-carotene β,ψ-carotene 536.882 C40 H56 C1(C(C(=C(CC1)C)C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC=C(CCC=C(C)C)C)C)C)(C)C) PUBCHEM:5280791:*CHEBI:27740:*LIGAND-CPD:C05435: 5.5.1.- all-trans-lycopene = γ-carotene β-carotene biosynthesis γ-carotene β,ψ-carotene 536.882 C40 H56 C1(C(C(=C(CC1)C)C=CC(C)=CC=CC(C)=CC=CC=C(C=CC=C(C=CC=C(CCC=C(C)C)C)C)C)(C)C) PUBCHEM:5280791:*CHEBI:27740:*LIGAND-CPD:C05435: 5.5.1.- γ-carotene = β-carotene β-carotene biosynthesis isofucosterol 412.698 C29 H48 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CCC(C(C)C)=CC)C)C(CC3)(C)4)))C))O) PUBCHEM:25244964:*LIGAND-CPD:C08821: isofucosterol = Δ24-25-sitosterol plant sterol biosynthesis isofucosterol 412.698 C29 H48 O1 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(CCC(C(C)C)=CC)C)C(CC3)(C)4)))C))O) PUBCHEM:25244964:*LIGAND-CPD:C08821: 1.3.1.21 5-dehydroavenasterol + NADPH = isofucosterol + NADP+ plant sterol biosynthesis 2,3-dihydro-2,3-dihydroxybenzoate 2,3-Dihydroxy-2,3-dihydrobenzoate 155.13 C7 H7 O4 C1(=C(C(C(C=C1)O)O)C([O-])=O) CHEBI:57576:*PUBCHEM:23615184:*LIGAND-CPD:C04171: 3.3.2.1 H2O + isochorismate = pyruvate + 2,3-dihydro-2,3-dihydroxybenzoate 2,3-dihydroxybenzoate biosynthesis 2,3-dihydro-2,3-dihydroxybenzoate 2,3-Dihydroxy-2,3-dihydrobenzoate 155.13 C7 H7 O4 C1(=C(C(C(C=C1)O)O)C([O-])=O) CHEBI:57576:*PUBCHEM:23615184:*LIGAND-CPD:C04171: 1.3.1.28 NAD+ + 2,3-dihydro-2,3-dihydroxybenzoate = H+ + NADH + 2,3-dihydroxybenzoate 2,3-dihydroxybenzoate biosynthesis D-erythro-imidazole-glycerol-phosphate D-erythro-1-(imidazol-4-yl)-glycerol-3-phosphate*D-erythro-imidazole-glycerol-P*erythro-imidazole-glycerol-P*erythro-imidazole-glycerol-phosphate*imidazole glycerol phosphate*IGP 236.121 C6 H9 N2 O6 P1 C1(N=CNC=1)C(C(O)COP(=O)([O-])[O-])O PUBCHEM:25246234:*LIGAND-CPD:C04666: 2.4.2.- phosphoribulosylformimino-AICAR-P + L-glutamine = H+ + L-glutamate + D-erythro-imidazole-glycerol-phosphate + aminoimidazole carboxamide ribonucleotide histidine biosynthesis D-erythro-imidazole-glycerol-phosphate D-erythro-1-(imidazol-4-yl)-glycerol-3-phosphate*D-erythro-imidazole-glycerol-P*erythro-imidazole-glycerol-P*erythro-imidazole-glycerol-phosphate*imidazole glycerol phosphate*IGP 236.121 C6 H9 N2 O6 P1 C1(N=CNC=1)C(C(O)COP(=O)([O-])[O-])O PUBCHEM:25246234:*LIGAND-CPD:C04666: 4.2.1.19 D-erythro-imidazole-glycerol-phosphate = imidazole acetol-phosphate + H2O histidine biosynthesis GMP GMP*guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 361.207 C10 H12 N5 O8 P1 NC3(=NC1(=C(N=CN1C2(OC(COP([O-])(=O)[O-])C(O)C(O)2))C(=O)N3)) PUBCHEM:1807035:*LIGAND-CPD:C00144:*CAS:85-32-5 2.4.2.8 GMP + diphosphate = guanine + 5-phospho-α-D-ribose 1-diphosphate guanine and guanosine salvage II GMP GMP*guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 361.207 C10 H12 N5 O8 P1 NC3(=NC1(=C(N=CN1C2(OC(COP([O-])(=O)[O-])C(O)C(O)2))C(=O)N3)) PUBCHEM:1807035:*LIGAND-CPD:C00144:*CAS:85-32-5 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = H+ + L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis II GMP GMP*guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 361.207 C10 H12 N5 O8 P1 NC3(=NC1(=C(N=CN1C2(OC(COP([O-])(=O)[O-])C(O)C(O)2))C(=O)N3)) PUBCHEM:1807035:*LIGAND-CPD:C00144:*CAS:85-32-5 3.1.3.5 GMP + H2O = guanosine guanosine nucleotides degradation II dihydrokaempferol aromadendrin*(+)-aromadendrin*(+)-Dihydrokaempferol 287.248 C15 H11 O6 C1(C(=CC=C(C=1)C2(OC3(C(C(C2O)=O)=C(O)C=C([O-])C=3)))O) PUBCHEM:25244967:*CHEBI:57294:*PUBCHEM:25244967:*LIGAND-CPD:C00974:*CAS:480-20-6 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O leucopelargonidin and leucocyanidin biosynthesis dihydrokaempferol aromadendrin*(+)-aromadendrin*(+)-Dihydrokaempferol 287.248 C15 H11 O6 C1(C(=CC=C(C=1)C2(OC3(C(C(C2O)=O)=C(O)C=C([O-])C=3)))O) PUBCHEM:25244967:*CHEBI:57294:*PUBCHEM:25244967:*LIGAND-CPD:C00974:*CAS:480-20-6 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O leucodelphinidin biosynthesis dihydrokaempferol aromadendrin*(+)-aromadendrin*(+)-Dihydrokaempferol 287.248 C15 H11 O6 C1(C(=CC=C(C=1)C2(OC3(C(C(C2O)=O)=C(O)C=C([O-])C=3)))O) PUBCHEM:25244967:*CHEBI:57294:*PUBCHEM:25244967:*LIGAND-CPD:C00974:*CAS:480-20-6 1.14.13.21 H+ + dihydrokaempferol + NADPH + oxygen = trans dihydroquercetin + NADP+ + H2O flavonol biosynthesis dihydrokaempferol aromadendrin*(+)-aromadendrin*(+)-Dihydrokaempferol 287.248 C15 H11 O6 C1(C(=CC=C(C=1)C2(OC3(C(C(C2O)=O)=C(O)C=C([O-])C=3)))O) PUBCHEM:25244967:*CHEBI:57294:*PUBCHEM:25244967:*LIGAND-CPD:C00974:*CAS:480-20-6 1.14.13.88 H+ + dihydrokaempferol + NADPH + oxygen = dihydromyricetin + NADP+ + H2O leucodelphinidin biosynthesis dihydrokaempferol aromadendrin*(+)-aromadendrin*(+)-Dihydrokaempferol 287.248 C15 H11 O6 C1(C(=CC=C(C=1)C2(OC3(C(C(C2O)=O)=C(O)C=C([O-])C=3)))O) PUBCHEM:25244967:*CHEBI:57294:*PUBCHEM:25244967:*LIGAND-CPD:C00974:*CAS:480-20-6 1.14.13.88 H+ + dihydrokaempferol + NADPH + oxygen = dihydromyricetin + NADP+ + H2O syringetin biosynthesis dihydrokaempferol aromadendrin*(+)-aromadendrin*(+)-Dihydrokaempferol 287.248 C15 H11 O6 C1(C(=CC=C(C=1)C2(OC3(C(C(C2O)=O)=C(O)C=C([O-])C=3)))O) PUBCHEM:25244967:*CHEBI:57294:*PUBCHEM:25244967:*LIGAND-CPD:C00974:*CAS:480-20-6 1.14.11.9 naringenin + oxygen + 2-oxoglutarate = CO2 + succinate + dihydrokaempferol flavonoid biosynthesis dihydrokaempferol aromadendrin*(+)-aromadendrin*(+)-Dihydrokaempferol 287.248 C15 H11 O6 C1(C(=CC=C(C=1)C2(OC3(C(C(C2O)=O)=C(O)C=C([O-])C=3)))O) PUBCHEM:25244967:*CHEBI:57294:*PUBCHEM:25244967:*LIGAND-CPD:C00974:*CAS:480-20-6 1.14.11.23 dihydrokaempferol + 2-oxoglutarate + oxygen = kaempferol + succinate + CO2 + H2O flavonol biosynthesis dihydrokaempferol aromadendrin*(+)-aromadendrin*(+)-Dihydrokaempferol 287.248 C15 H11 O6 C1(C(=CC=C(C=1)C2(OC3(C(C(C2O)=O)=C(O)C=C([O-])C=3)))O) PUBCHEM:25244967:*CHEBI:57294:*PUBCHEM:25244967:*LIGAND-CPD:C00974:*CAS:480-20-6 1.1.1.219 H+ + dihydrokaempferol + NADPH = leucopelargonidin + NADP+ leucopelargonidin and leucocyanidin biosynthesis uracil 112.088 C4 H4 N2 O2 C1(=CNC(=O)NC(=O)1) PUBCHEM:1174:*CHEBI:17568:*LIGAND-CPD:C00106:*CAS:66-22-8 2.4.2.9 diphosphate + uridine-5'-phosphate = 5-phospho-α-D-ribose 1-diphosphate + uracil salvage pathways of pyrimidine ribonucleotides uracil 112.088 C4 H4 N2 O2 C1(=CNC(=O)NC(=O)1) PUBCHEM:1174:*CHEBI:17568:*LIGAND-CPD:C00106:*CAS:66-22-8 3.2.2.3 uridine + H2O = uracil pyrimidine ribonucleosides degradation II uracil 112.088 C4 H4 N2 O2 C1(=CNC(=O)NC(=O)1) PUBCHEM:1174:*CHEBI:17568:*LIGAND-CPD:C00106:*CAS:66-22-8 1.3.1.2 5,6-dihydrouracil + NADP+ = uracil + NADPH + H+ uracil degradation II (reductive) uracil 112.088 C4 H4 N2 O2 C1(=CNC(=O)NC(=O)1) PUBCHEM:1174:*CHEBI:17568:*LIGAND-CPD:C00106:*CAS:66-22-8 3.5.4.1 H2O + cytosine = ammonia + uracil salvage pathways of pyrimidine ribonucleotides uracil 112.088 C4 H4 N2 O2 C1(=CNC(=O)NC(=O)1) PUBCHEM:1174:*CHEBI:17568:*LIGAND-CPD:C00106:*CAS:66-22-8 2.4.2.3 uridine = α-D-ribose-1-phosphate + uracil salvage pathways of pyrimidine ribonucleotides uracil 112.088 C4 H4 N2 O2 C1(=CNC(=O)NC(=O)1) PUBCHEM:1174:*CHEBI:17568:*LIGAND-CPD:C00106:*CAS:66-22-8 4.2.1.70 D-ribose-5-phosphate + uracil = H2O + pseudouridine 5'-phosphate pseudouridine degradation α-D-mannose 1-phosphate D-mannose-1-phosphate*mannose-1-phosphate*α-D-mannose 1-phosphate*mannose-1-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) LIGAND-CPD:C03812:*CHEBI:58409:*PUBCHEM:25245607:*LIGAND-CPD:C00636:*CAS:27251-84-9 5.4.2.8 α-D-mannose 1-phosphate = D-mannose 6-phosphate ascorbate biosynthesis I (L-galactose pathway) α-D-mannose 1-phosphate D-mannose-1-phosphate*mannose-1-phosphate*α-D-mannose 1-phosphate*mannose-1-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) LIGAND-CPD:C03812:*CHEBI:58409:*PUBCHEM:25245607:*LIGAND-CPD:C00636:*CAS:27251-84-9 5.4.2.8 α-D-mannose 1-phosphate = D-mannose 6-phosphate GDP-mannose biosynthesis α-D-mannose 1-phosphate D-mannose-1-phosphate*mannose-1-phosphate*α-D-mannose 1-phosphate*mannose-1-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) LIGAND-CPD:C03812:*CHEBI:58409:*PUBCHEM:25245607:*LIGAND-CPD:C00636:*CAS:27251-84-9 2.7.7.13 H+ + α-D-mannose 1-phosphate + GTP = GDP-α-D-mannose + diphosphate ascorbate biosynthesis I (L-galactose pathway) α-D-mannose 1-phosphate D-mannose-1-phosphate*mannose-1-phosphate*α-D-mannose 1-phosphate*mannose-1-P 258.121 C6 H11 O9 P1 O=P([O-])([O-])OC1(OC(CO)C(O)C(O)C(O)1) LIGAND-CPD:C03812:*CHEBI:58409:*PUBCHEM:25245607:*LIGAND-CPD:C00636:*CAS:27251-84-9 2.7.7.13 H+ + α-D-mannose 1-phosphate + GTP = GDP-α-D-mannose + diphosphate GDP-mannose biosynthesis dehydroscoulerine 324.355 C19 H18 N1 O4 C4(=C3(C(C2(=CC1(C=CC(O)=C(OC)C=1C=[N+]2CC3)))=CC(O)=C(OC)4)) CHEBI:521121:*PUBCHEM:10358881: 1.21.3.- S-scoulerine + FAD = dehydroscoulerine + FADH2 dehydroscoulerine biosynthesis R-4'-phosphopantothenoyl-L-cysteine (R)-4'-phospho-N-pantothenoyl-L-cysteine*4-P-N-pantothenoylcysteine*4'-P-N-pantothenoylcysteine*N-((R)-4-phosphopantothenoyl)-L-cysteine*4'-phosphopantothenoylcysteine*4'-phospho-N-pantothenoylcysteine*(R)-4'-phosphopantothenoyl-L-cysteine*N-[(R)-4'-phosphopantothenoyl]-L-cysteine*PPC 399.332 C12 H20 N2 O9 P1 S1 CC(C)(COP(=O)([O-])[O-])C(O)C(=O)NCCC(=O)NC(CS)C(=O)[O-] CHEBI:59458:*PUBCHEM:25245609:*LIGAND-CPD:C04352: 4.1.1.36 H+ + R-4'-phosphopantothenoyl-L-cysteine = 4'-phosphopantetheine + CO2 coenzyme A biosynthesis R-4'-phosphopantothenoyl-L-cysteine (R)-4'-phospho-N-pantothenoyl-L-cysteine*4-P-N-pantothenoylcysteine*4'-P-N-pantothenoylcysteine*N-((R)-4-phosphopantothenoyl)-L-cysteine*4'-phosphopantothenoylcysteine*4'-phospho-N-pantothenoylcysteine*(R)-4'-phosphopantothenoyl-L-cysteine*N-[(R)-4'-phosphopantothenoyl]-L-cysteine*PPC 399.332 C12 H20 N2 O9 P1 S1 CC(C)(COP(=O)([O-])[O-])C(O)C(=O)NCCC(=O)NC(CS)C(=O)[O-] CHEBI:59458:*PUBCHEM:25245609:*LIGAND-CPD:C04352: 6.3.2.5 D-4'-phosphopantothenate + L-cysteine + CTP = H+ + R-4'-phosphopantothenoyl-L-cysteine + diphosphate + CMP coenzyme A biosynthesis carbon monoxide CO*carbon monoxide*carbon monooxide 29.018 C1 O1 [O+]#[C-] PUBCHEM:281:*CHEBI:17245:*PUBCHEM:6432172:*LIGAND-CPD:C00237:*CAS:630-08-0 4.1.99.5 octadecanal = heptadecane + carbon monoxide heptadecane biosynthesis carbon monoxide CO*carbon monoxide*carbon monooxide 29.018 C1 O1 [O+]#[C-] PUBCHEM:281:*CHEBI:17245:*PUBCHEM:6432172:*LIGAND-CPD:C00237:*CAS:630-08-0 1.14.99.3 protoheme IX + oxygen = biliverdin-IX-α + Fe2+ + carbon monoxide + H2O heme degradation carbon monoxide CO*carbon monoxide*carbon monooxide 29.018 C1 O1 [O+]#[C-] PUBCHEM:281:*CHEBI:17245:*PUBCHEM:6432172:*LIGAND-CPD:C00237:*CAS:630-08-0 4.1.99.5 cuticular wax biosynthesis carbon monoxide CO*carbon monoxide*carbon monooxide 29.018 C1 O1 [O+]#[C-] PUBCHEM:281:*CHEBI:17245:*PUBCHEM:6432172:*LIGAND-CPD:C00237:*CAS:630-08-0 4.1.99.- 5-aminoimidazole ribonucleotide + S-adenosyl-L-methionine = hydroxymethylpyrimidine phosphate + 5'-deoxyadenosine + L-methionine + formate + carbon monoxide + H+ thiamine biosynthesis II (22R,23R)-22,23-dihydroxycampesterol 432.685 C28 H48 O3 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(C(C(O)C(C(C)C)C)O)C)C(CC3)(C)4)))C))O) 1.14.13.- H+ + (22α)-hydroxy-campesterol + NADPH + oxygen = (22R,23R)-22,23-dihydroxycampesterol + NADP+ + H2O brassinosteroid biosynthesis II (22R,23R)-22,23-dihydroxycampesterol 432.685 C28 H48 O3 C1(CC(CC2(C1(C3(C(CC=2)C4(CCC(C(C(C(O)C(C(C)C)C)O)C)C(CC3)(C)4)))C))O) (22R,23R)-22,23-dihydroxycampesterol = H+ + (22R,23R)-22,23-dihydroxy-campest-4-en-3-one brassinosteroid biosynthesis II dihydrozeatin-9-N-glucoside 383.403 C16 H25 N5 O6 C1(C2(=C(N=CN=1)N(C=N2)C3(C(C(C(C(O3)CO)O)O)O)))NCCC(CO)C PUBCHEM:25201996: 2.4.1.- dihydrozeatin-9-N-glucoside = H+ + dihydrozeatin-9-N-glucoside-O-glucoside + UDP cytokinins-O-glucoside biosynthesis α-tocopherol vitamin E*(2R,4'R,8'R)-α-tocopherol*(R,R,R)-α-tocopherol*5,7,8-trimethyltocol 430.713 C29 H50 O2 CC2(C(=C(C(C)=C1(CCC(C)(CCCC(C)CCCC(C)CCCC(C)C)OC1=2))O)C) CHEBI:18145:*PUBCHEM:14985:*LIGAND-CPD:C02477:*NCI:82623*CAS:2074-53-5 2.1.1.95 γ-tocopherol + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + α-tocopherol vitamin E biosynthesis N-methylethanolamine phosphate P-MME 154.082 C3 H9 N1 O4 P1 [O-]P(OCC[N+]C)(=O)[O-] CHEBI:57781:*PUBCHEM:25201132:*LIGAND-CPD:C01210: 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate phosphatidylcholine biosynthesis IV N-methylethanolamine phosphate P-MME 154.082 C3 H9 N1 O4 P1 [O-]P(OCC[N+]C)(=O)[O-] CHEBI:57781:*PUBCHEM:25201132:*LIGAND-CPD:C01210: 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate choline biosynthesis I N-methylethanolamine phosphate P-MME 154.082 C3 H9 N1 O4 P1 [O-]P(OCC[N+]C)(=O)[O-] CHEBI:57781:*PUBCHEM:25201132:*LIGAND-CPD:C01210: 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate phosphatidylcholine biosynthesis III N-methylethanolamine phosphate P-MME 154.082 C3 H9 N1 O4 P1 [O-]P(OCC[N+]C)(=O)[O-] CHEBI:57781:*PUBCHEM:25201132:*LIGAND-CPD:C01210: 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + N-methylethanolamine phosphate phosphatidylcholine biosynthesis II N-methylethanolamine phosphate P-MME 154.082 C3 H9 N1 O4 P1 [O-]P(OCC[N+]C)(=O)[O-] CHEBI:57781:*PUBCHEM:25201132:*LIGAND-CPD:C01210: 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = H+ + N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis IV N-methylethanolamine phosphate P-MME 154.082 C3 H9 N1 O4 P1 [O-]P(OCC[N+]C)(=O)[O-] CHEBI:57781:*PUBCHEM:25201132:*LIGAND-CPD:C01210: 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = H+ + N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine choline biosynthesis I N-methylethanolamine phosphate P-MME 154.082 C3 H9 N1 O4 P1 [O-]P(OCC[N+]C)(=O)[O-] CHEBI:57781:*PUBCHEM:25201132:*LIGAND-CPD:C01210: 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = H+ + N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine phosphatidylcholine biosynthesis II N-methylethanolamine phosphate P-MME 154.082 C3 H9 N1 O4 P1 [O-]P(OCC[N+]C)(=O)[O-] CHEBI:57781:*PUBCHEM:25201132:*LIGAND-CPD:C01210: 2.7.7.57 H+ + N-methylethanolamine phosphate + CTP = CDP-N-methylethanolamine + diphosphate phosphatidylcholine biosynthesis III quercetin 3, 7, 3', 4'-tetrasulphate quercetin 3, 7, 3', 4'-tetrasulfate*quercetin 3, 7, 3, 4-tetrasulphate 618.441 C15 H6 O19 S4 O=C1(C(OS(=O)(=O)[O-])=C(OC2(C=C(C=C(O)C1=2)OS(=O)(=O)[O-]))C3(=CC=C(OS(=O)(=O)[O-])C(OS(=O)(=O)[O-])=C3)) PUBCHEM:44123499: quercetin 3, 7, 4'-trisulphate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin 3, 7, 3', 4'-tetrasulphate quercetinsulphates biosynthesis quercetin 3, 7, 3', 4'-tetrasulphate quercetin 3, 7, 3', 4'-tetrasulfate*quercetin 3, 7, 3, 4-tetrasulphate 618.441 C15 H6 O19 S4 O=C1(C(OS(=O)(=O)[O-])=C(OC2(C=C(C=C(O)C1=2)OS(=O)(=O)[O-]))C3(=CC=C(OS(=O)(=O)[O-])C(OS(=O)(=O)[O-])=C3)) PUBCHEM:44123499: quercetin 3,3',7-trissulfate + phosphoadenosine-5'-phosphosulfate = adenosine 3',5'-bisphosphate + H+ + quercetin 3, 7, 3', 4'-tetrasulphate quercetinsulphates biosynthesis 4α-hydroxymethyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol 9,19-cyclolanostane-3,28-diol, 24-methylene-, (3β,4α)- 456.751 C31 H52 O2 C1(CC(C(C2(C51(C3(C(CC2)C4(C)(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4))C5)))(C)CO)O) CAS:149252-86-8: 1.14.13.- 24-methylenecycloartanol + NADH + oxygen = 4α-hydroxymethyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis 4α-hydroxymethyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol 9,19-cyclolanostane-3,28-diol, 24-methylene-, (3β,4α)- 456.751 C31 H52 O2 C1(CC(C(C2(C51(C3(C(CC2)C4(C)(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4))C5)))(C)CO)O) CAS:149252-86-8: 1.14.13.- 4α-hydroxymethyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NADH + oxygen = 4α-formyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis indole acetaldehyde indole-3-acetaldehyde*2-(indol-3-yl)acetaldehyde*(indol-3-yl)acetaldehyde 159.187 C10 H9 N1 O1 O=CCC1(C2(=C(NC=1)C=CC=C2)) PUBCHEM:800:*CHEBI:18086:*LIGAND-CPD:C00637:*CAS:2591-98-2 1.2.3.7 indole acetaldehyde + oxygen + H2O = H+ + indole-3-acetate + hydrogen peroxide IAA biosynthesis I indole acetaldehyde indole-3-acetaldehyde*2-(indol-3-yl)acetaldehyde*(indol-3-yl)acetaldehyde 159.187 C10 H9 N1 O1 O=CCC1(C2(=C(NC=1)C=CC=C2)) PUBCHEM:800:*CHEBI:18086:*LIGAND-CPD:C00637:*CAS:2591-98-2 4.1.1.74 H+ + indole-3-pyruvate = CO2 + indole acetaldehyde IAA biosynthesis I N-acetyl-L-glutamate acetyl-L-glutamate*acetyl-L-glu*N-acetyl-L-glutamic acid*N-acetylglutamic acid*acetyl-glu*N-acetyl-glutamate*acetyl-glutamate*N-acetyl L-glutamic acid*NAG 187.152 C7 H9 N1 O5 [O-]C(=O)CCC(NC(=O)C)C(=O)[O-] CHEBI:44337:*PUBCHEM:1549099:*LIGAND-CPD:C00624:*CAS:1188-37-0 2.7.2.8 N-acetyl-L-glutamate + ATP = N-acetylglutamyl-phosphate + ADP arginine biosynthesis II (acetyl cycle) N-acetyl-L-glutamate acetyl-L-glutamate*acetyl-L-glu*N-acetyl-L-glutamic acid*N-acetylglutamic acid*acetyl-glu*N-acetyl-glutamate*acetyl-glutamate*N-acetyl L-glutamic acid*NAG 187.152 C7 H9 N1 O5 [O-]C(=O)CCC(NC(=O)C)C(=O)[O-] CHEBI:44337:*PUBCHEM:1549099:*LIGAND-CPD:C00624:*CAS:1188-37-0 2.7.2.8 N-acetyl-L-glutamate + ATP = N-acetylglutamyl-phosphate + ADP ornithine biosynthesis N-acetyl-L-glutamate acetyl-L-glutamate*acetyl-L-glu*N-acetyl-L-glutamic acid*N-acetylglutamic acid*acetyl-glu*N-acetyl-glutamate*acetyl-glutamate*N-acetyl L-glutamic acid*NAG 187.152 C7 H9 N1 O5 [O-]C(=O)CCC(NC(=O)C)C(=O)[O-] CHEBI:44337:*PUBCHEM:1549099:*LIGAND-CPD:C00624:*CAS:1188-37-0 2.3.1.1 L-glutamate + acetyl-CoA = H+ + N-acetyl-L-glutamate + coenzyme A arginine biosynthesis II (acetyl cycle) N-acetyl-L-glutamate acetyl-L-glutamate*acetyl-L-glu*N-acetyl-L-glutamic acid*N-acetylglutamic acid*acetyl-glu*N-acetyl-glutamate*acetyl-glutamate*N-acetyl L-glutamic acid*NAG 187.152 C7 H9 N1 O5 [O-]C(=O)CCC(NC(=O)C)C(=O)[O-] CHEBI:44337:*PUBCHEM:1549099:*LIGAND-CPD:C00624:*CAS:1188-37-0 2.3.1.1 L-glutamate + acetyl-CoA = H+ + N-acetyl-L-glutamate + coenzyme A ornithine biosynthesis N-acetyl-L-glutamate acetyl-L-glutamate*acetyl-L-glu*N-acetyl-L-glutamic acid*N-acetylglutamic acid*acetyl-glu*N-acetyl-glutamate*acetyl-glutamate*N-acetyl L-glutamic acid*NAG 187.152 C7 H9 N1 O5 [O-]C(=O)CCC(NC(=O)C)C(=O)[O-] CHEBI:44337:*PUBCHEM:1549099:*LIGAND-CPD:C00624:*CAS:1188-37-0 2.3.1.35 L-glutamate + N-acetyl-L-ornithine = N-acetyl-L-glutamate + L-ornithine arginine biosynthesis II (acetyl cycle) sulfate H2SO4*sulfuric acid*sulfate*sulphate*SO4-2*SO42-*SO4-- 96.058 O4 S1 O=S(=O)([O-])[O-] PUBCHEM:1117:*CHEBI:16189:*LIGAND-CPD:C00059:*CAS:7664-93-9:*CAS:14808-79-8 1.8.3.1 sulfite + oxygen + H2O = hydrogen peroxide + sulfate sulfite oxidation IV sulfate H2SO4*sulfuric acid*sulfate*sulphate*SO4-2*SO42-*SO4-- 96.058 O4 S1 O=S(=O)([O-])[O-] PUBCHEM:1117:*CHEBI:16189:*LIGAND-CPD:C00059:*CAS:7664-93-9:*CAS:14808-79-8 2.7.7.4 H+ + sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate reduction II (assimilatory) sulfate H2SO4*sulfuric acid*sulfate*sulphate*SO4-2*SO42-*SO4-- 96.058 O4 S1 O=S(=O)([O-])[O-] PUBCHEM:1117:*CHEBI:16189:*LIGAND-CPD:C00059:*CAS:7664-93-9:*CAS:14808-79-8 2.7.7.4 H+ + sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfite oxidation III sulfate H2SO4*sulfuric acid*sulfate*sulphate*SO4-2*SO42-*SO4-- 96.058 O4 S1 O=S(=O)([O-])[O-] PUBCHEM:1117:*CHEBI:16189:*LIGAND-CPD:C00059:*CAS:7664-93-9:*CAS:14808-79-8 2.7.7.4 H+ + sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate activation for sulfonation sulfate H2SO4*sulfuric acid*sulfate*sulphate*SO4-2*SO42-*SO4-- 96.058 O4 S1 O=S(=O)([O-])[O-] PUBCHEM:1117:*CHEBI:16189:*LIGAND-CPD:C00059:*CAS:7664-93-9:*CAS:14808-79-8 2.7.7.5 sulfate + H+ + ADP = adenosine 5'-phosphosulfate sulfite oxidation II syringin sinapyl alcohol-4-O-β-D-glucopyranoside 372.371 C17 H24 O9 C1(C(=CC(=C(C=1OC)OC2(C(C(C(C(O2)CO)O)O)O))OC)C=CCO) PUBCHEM:12443176:*LIGAND-CPD:C01533: 2.4.1.111 sinapyl-alcohol = H+ + syringin + UDP monolignol glucosides biosynthesis hydroxymethylbilane 846.757 C40 H38 N4 O17 C1(NC(=C(C=1CC(=O)[O-])CCC([O-])=O)CC2(=C(C(=CN2)CC([O-])=O)CCC(=O)[O-]))CC3(=C(C(=C(N3)CC4(NC(=C(C=4CCC([O-])=O)CC(=O)[O-])CO))CC([O-])=O)CCC(=O)[O-]) PUBCHEM:25202903:*LIGAND-CPD:C01024:*CAS:73023-76-4 4.2.1.75 hydroxymethylbilane = uroporphyrinogen-III + H2O tetrapyrrole biosynthesis I hydroxymethylbilane 846.757 C40 H38 N4 O17 C1(NC(=C(C=1CC(=O)[O-])CCC([O-])=O)CC2(=C(C(=CN2)CC([O-])=O)CCC(=O)[O-]))CC3(=C(C(=C(N3)CC4(NC(=C(C=4CCC([O-])=O)CC(=O)[O-])CO))CC([O-])=O)CCC(=O)[O-]) PUBCHEM:25202903:*LIGAND-CPD:C01024:*CAS:73023-76-4 2.5.1.61 H2O + porphobilinogen = H+ + ammonia + hydroxymethylbilane tetrapyrrole biosynthesis I S-(-)-ureidoglycolate (-)-ureidoglycolate*ureidoglycolate*S-ureidoglycolate 133.083 C3 H5 N2 O4 C(=O)(N)NC(O)C([O-])=O CHEBI:57296:*PUBCHEM:23615273:*LIGAND-CPD:C00603:*CAS:2017665 1.1.1.154 S-(-)-ureidoglycolate = oxalurate + H+ allantoin degradation IV (anaerobic) S-(-)-ureidoglycolate (-)-ureidoglycolate*ureidoglycolate*S-ureidoglycolate 133.083 C3 H5 N2 O4 C(=O)(N)NC(O)C([O-])=O CHEBI:57296:*PUBCHEM:23615273:*LIGAND-CPD:C00603:*CAS:2017665 3.5.3.- S-ureidoglycine + H2O = H+ + ammonia + S-(-)-ureidoglycolate allantoin degradation to ureidoglycolate II (ammonia producing) S-(-)-ureidoglycolate (-)-ureidoglycolate*ureidoglycolate*S-ureidoglycolate 133.083 C3 H5 N2 O4 C(=O)(N)NC(O)C([O-])=O CHEBI:57296:*PUBCHEM:23615273:*LIGAND-CPD:C00603:*CAS:2017665 3.5.3.4 H2O + allantoate = S-(-)-ureidoglycolate + urea allantoin degradation to ureidoglycolate I (urea producing) choline 104.172 C5 H14 N1 O1 C[N+](C)(CCO)C PUBCHEM:305:*KNAPSACK:C00007298:*PUBCHEM:305:*CHEBI:15354:*CAS:62-49-7*CAS:123-41-1:*LIGAND-CPD:C00114: 3.1.3.75 phosphoryl-choline + H2O = choline choline biosynthesis I choline 104.172 C5 H14 N1 O1 C[N+](C)(CCO)C PUBCHEM:305:*KNAPSACK:C00007298:*PUBCHEM:305:*CHEBI:15354:*CAS:62-49-7*CAS:123-41-1:*LIGAND-CPD:C00114: 3.1.4.4 H2O = choline phospholipases choline 104.172 C5 H14 N1 O1 C[N+](C)(CCO)C PUBCHEM:305:*KNAPSACK:C00007298:*PUBCHEM:305:*CHEBI:15354:*CAS:62-49-7*CAS:123-41-1:*LIGAND-CPD:C00114: 3.1.4.4 H2O = choline choline biosynthesis III choline 104.172 C5 H14 N1 O1 C[N+](C)(CCO)C PUBCHEM:305:*KNAPSACK:C00007298:*PUBCHEM:305:*CHEBI:15354:*CAS:62-49-7*CAS:123-41-1:*LIGAND-CPD:C00114: 2.7.1.32 choline + ATP = H+ + phosphoryl-choline + ADP phosphatidylcholine biosynthesis I choline 104.172 C5 H14 N1 O1 C[N+](C)(CCO)C PUBCHEM:305:*KNAPSACK:C00007298:*PUBCHEM:305:*CHEBI:15354:*CAS:62-49-7*CAS:123-41-1:*LIGAND-CPD:C00114: 1.14.15.7 choline + oxygen + H+ = betaine aldehyde hydrate + H2O glycine betaine biosynthesis III (plants) 4-methyl-5-(2-phosphonooxyethyl)thiazole 4-methyl-5-(β-hydroxyethyl)thiazole phosphate*HET-P*4-4-methyl-5-(2-phosphonooxyethyl)-thiazole*4-methyl-5-(2-phosphoethyl)-thiazole*THZ-P*4-Methyl-5-(2-phosphono-oxyethyl)-thiazole 221.167 C6 H8 N1 O4 P1 S1 C1(=C(C)N=CS1)CCOP([O-])([O-])=O PUBCHEM:25245616:*LIGAND-CPD:C04327: 2.5.1.3 H+ + 4-methyl-5-(2-phosphonooxyethyl)thiazole + 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate = thiamine-phosphate + diphosphate thiamine biosynthesis II 4-methyl-5-(2-phosphonooxyethyl)thiazole 4-methyl-5-(β-hydroxyethyl)thiazole phosphate*HET-P*4-4-methyl-5-(2-phosphonooxyethyl)-thiazole*4-methyl-5-(2-phosphoethyl)-thiazole*THZ-P*4-Methyl-5-(2-phosphono-oxyethyl)-thiazole 221.167 C6 H8 N1 O4 P1 S1 C1(=C(C)N=CS1)CCOP([O-])([O-])=O PUBCHEM:25245616:*LIGAND-CPD:C04327: 2-carboxylate-4-methyl-5-beta-(ethyl adenosine 5-diphosphate) thiazole = AMP + 4-methyl-5-(2-phosphonooxyethyl)thiazole thiamine biosynthesis II L-dehydro-ascorbate dehydroascorbate 174.11 C6 H6 O6 O1(C([H])(C(O)CO)C(C(C(=O)1)=O)=O) CHEBI:58539:*CHEBI:27956:*LIGAND-CPD:C05422:*PUBCHEM:44123501:*PUBCHEM:440667:*LIGAND-CPD:C00425: 1.8.5.1 L-dehydro-ascorbate + glutathione = H+ + glutathione disulfide + L-ascorbate ascorbate glutathione cycle L-dehydro-ascorbate dehydroascorbate 174.11 C6 H6 O6 O1(C([H])(C(O)CO)C(C(C(=O)1)=O)=O) CHEBI:58539:*CHEBI:27956:*LIGAND-CPD:C05422:*PUBCHEM:44123501:*PUBCHEM:440667:*LIGAND-CPD:C00425: 1.14.17.4 H+ + L-ascorbate + 1-aminocyclopropane-1-carboxylate + oxygen = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine L-dehydro-ascorbate dehydroascorbate 174.11 C6 H6 O6 O1(C([H])(C(O)CO)C(C(C(=O)1)=O)=O) CHEBI:58539:*CHEBI:27956:*LIGAND-CPD:C05422:*PUBCHEM:44123501:*PUBCHEM:440667:*LIGAND-CPD:C00425: 1.10.99.3 H+ + violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O antheraxanthin and violaxanthin biosynthesis L-dehydro-ascorbate dehydroascorbate 174.11 C6 H6 O6 O1(C([H])(C(O)CO)C(C(C(=O)1)=O)=O) CHEBI:58539:*CHEBI:27956:*LIGAND-CPD:C05422:*PUBCHEM:44123501:*PUBCHEM:440667:*LIGAND-CPD:C00425: 1.10.99.3 H+ + violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle L-dehydro-ascorbate dehydroascorbate 174.11 C6 H6 O6 O1(C([H])(C(O)CO)C(C(C(=O)1)=O)=O) CHEBI:58539:*CHEBI:27956:*LIGAND-CPD:C05422:*PUBCHEM:44123501:*PUBCHEM:440667:*LIGAND-CPD:C00425: 1.10.99.3 H+ + antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O antheraxanthin and violaxanthin biosynthesis L-dehydro-ascorbate dehydroascorbate 174.11 C6 H6 O6 O1(C([H])(C(O)CO)C(C(C(=O)1)=O)=O) CHEBI:58539:*CHEBI:27956:*LIGAND-CPD:C05422:*PUBCHEM:44123501:*PUBCHEM:440667:*LIGAND-CPD:C00425: 1.10.99.3 H+ + antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle L-dehydro-ascorbate dehydroascorbate 174.11 C6 H6 O6 O1(C([H])(C(O)CO)C(C(C(=O)1)=O)=O) CHEBI:58539:*CHEBI:27956:*LIGAND-CPD:C05422:*PUBCHEM:44123501:*PUBCHEM:440667:*LIGAND-CPD:C00425: monodehydroascorbate = H+ + L-ascorbate + L-dehydro-ascorbate ascorbate glutathione cycle GA34-catabolite gibberellin A34-catabolite*gibberellin A34-catabolite*GA34-catabolite 344.363 C19 H20 O6 C1(C(C(C(C2(C(C34(CC(CCC(C=12)3)C(C4)=C))C([O-])=O))(C)C([O-])=O)O)=O) PUBCHEM:25201142:*LIGAND-CPD:C11869: 1.14.11.- GA34 + 2-oxoglutarate + oxygen = H+ + GA34-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) α-D-glucuronate 1-phosphate glucuronate-1-P*glucuronate-1-phosphate*D-glucuronate-1-P*D-glucuronate-1-phosphate*1-phospho-α-D-glucuronate 271.097 C6 H8 O10 P1 C1(OC(C(C(C1O)O)O)OP([O-])([O-])=O)C([O-])=O PUBCHEM:25244365:*CAS:583-08-4:*LIGAND-CPD:C05385: 2.7.7.44 H+ + α-D-glucuronate 1-phosphate + UTP = UDP-D-glucuronate + diphosphate UDP-D-glucuronate biosynthesis (from myo-inositol) α-D-glucuronate 1-phosphate glucuronate-1-P*glucuronate-1-phosphate*D-glucuronate-1-P*D-glucuronate-1-phosphate*1-phospho-α-D-glucuronate 271.097 C6 H8 O10 P1 C1(OC(C(C(C1O)O)O)OP([O-])([O-])=O)C([O-])=O PUBCHEM:25244365:*CAS:583-08-4:*LIGAND-CPD:C05385: 2.7.1.43 ATP = H+ + α-D-glucuronate 1-phosphate + ADP UDP-D-glucuronate biosynthesis (from myo-inositol) dTDP TDP*thymidine 5'-(trihydrogen diphosphate) (9CI)*deoxy-TDP*thymidine-5'-diphosphate*thymidine-diphosphate 399.167 C10 H13 N2 O11 P2 CC1(=CN(C(=O)NC(=O)1)C2(CC(O)C(COP(=O)([O-])OP(=O)([O-])[O-])O2)) PUBCHEM:21124327:*LIGAND-CPD:C00363:*CAS:491-97-4 2.7.4.9 ATP + dTMP = ADP + dTDP pyrimidine deoxyribonucleotides de novo biosynthesis I dTDP TDP*thymidine 5'-(trihydrogen diphosphate) (9CI)*deoxy-TDP*thymidine-5'-diphosphate*thymidine-diphosphate 399.167 C10 H13 N2 O11 P2 CC1(=CN(C(=O)NC(=O)1)C2(CC(O)C(COP(=O)([O-])OP(=O)([O-])[O-])O2)) PUBCHEM:21124327:*LIGAND-CPD:C00363:*CAS:491-97-4 2.7.4.6 dTDP + ATP = dTTP + ADP pyrimidine deoxyribonucleotides de novo biosynthesis I glycolaldehyde glycoaldehyde*2-OH-acetaldehyde*glycolaldehyde*hydroxyacetaldehyde*2-hydroxyethanal 60.052 C2 H4 O2 O=C(CO)[H] PUBCHEM:756:*CHEBI:17071:*LIGAND-CPD:C00266:*CAS:141-46-8 4.1.2.25 7,8-dihydro-D-neopterin = glycolaldehyde + 6-hydroxymethyl-7,8-dihydropterin 6-hydroxymethyl-dihydropterin diphosphate biosynthesis L-asparagine asparagine*α-aminosuccinamic acid*(-)-asparagine*(S)-2,4-diamino-4-oxobutanoic acid*(S)-asparagine*2,4-diamino-4-oxobutanoic acid, (S)-*2-aminosuccinamic acid, L-*agedoite*altheine*asparagine acid*aspartic acid β-amide*butanoic acid, 2,4-diamino-4-oxo-, (S)-*L-2,4-diamino-4-oxobutanoic acid*L-asparatamine*L-β-asparagine*asn 132.119 C4 H8 N2 O3 C([N+])(C(=O)[O-])CC(=O)N CAS:7006-34-0*KNAPSACK:C00001341:*CHEBI:17196:*PUBCHEM:5247114:*LIGAND-CPD:C00152:*CAS:70-47-3 6.1.1.22 H+ + L-asparagine + ATP = diphosphate + AMP tRNA charging pathway L-asparagine asparagine*α-aminosuccinamic acid*(-)-asparagine*(S)-2,4-diamino-4-oxobutanoic acid*(S)-asparagine*2,4-diamino-4-oxobutanoic acid, (S)-*2-aminosuccinamic acid, L-*agedoite*altheine*asparagine acid*aspartic acid β-amide*butanoic acid, 2,4-diamino-4-oxo-, (S)-*L-2,4-diamino-4-oxobutanoic acid*L-asparatamine*L-β-asparagine*asn 132.119 C4 H8 N2 O3 C([N+])(C(=O)[O-])CC(=O)N CAS:7006-34-0*KNAPSACK:C00001341:*CHEBI:17196:*PUBCHEM:5247114:*LIGAND-CPD:C00152:*CAS:70-47-3 3.5.1.1 L-asparagine + H2O = L-aspartate + ammonia + H+ asparagine degradation I L-asparagine asparagine*α-aminosuccinamic acid*(-)-asparagine*(S)-2,4-diamino-4-oxobutanoic acid*(S)-asparagine*2,4-diamino-4-oxobutanoic acid, (S)-*2-aminosuccinamic acid, L-*agedoite*altheine*asparagine acid*aspartic acid β-amide*butanoic acid, 2,4-diamino-4-oxo-, (S)-*L-2,4-diamino-4-oxobutanoic acid*L-asparatamine*L-β-asparagine*asn 132.119 C4 H8 N2 O3 C([N+])(C(=O)[O-])CC(=O)N CAS:7006-34-0*KNAPSACK:C00001341:*CHEBI:17196:*PUBCHEM:5247114:*LIGAND-CPD:C00152:*CAS:70-47-3 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = H+ + L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis I L-asparagine asparagine*α-aminosuccinamic acid*(-)-asparagine*(S)-2,4-diamino-4-oxobutanoic acid*(S)-asparagine*2,4-diamino-4-oxobutanoic acid, (S)-*2-aminosuccinamic acid, L-*agedoite*altheine*asparagine acid*aspartic acid β-amide*butanoic acid, 2,4-diamino-4-oxo-, (S)-*L-2,4-diamino-4-oxobutanoic acid*L-asparatamine*L-β-asparagine*asn 132.119 C4 H8 N2 O3 C([N+])(C(=O)[O-])CC(=O)N CAS:7006-34-0*KNAPSACK:C00001341:*CHEBI:17196:*PUBCHEM:5247114:*LIGAND-CPD:C00152:*CAS:70-47-3 4.2.1.65 L-asparagine = H+ + H2O + 3-cyano-L-alanine cyanide detoxification L-asparagine asparagine*α-aminosuccinamic acid*(-)-asparagine*(S)-2,4-diamino-4-oxobutanoic acid*(S)-asparagine*2,4-diamino-4-oxobutanoic acid, (S)-*2-aminosuccinamic acid, L-*agedoite*altheine*asparagine acid*aspartic acid β-amide*butanoic acid, 2,4-diamino-4-oxo-, (S)-*L-2,4-diamino-4-oxobutanoic acid*L-asparatamine*L-β-asparagine*asn 132.119 C4 H8 N2 O3 C([N+])(C(=O)[O-])CC(=O)N CAS:7006-34-0*KNAPSACK:C00001341:*CHEBI:17196:*PUBCHEM:5247114:*LIGAND-CPD:C00152:*CAS:70-47-3 6.3.1.1 ammonia + L-aspartate + ATP = L-asparagine + diphosphate + AMP asparagine biosynthesis II octadecenedioate octadecenedioic acid*octadec-9-ene-1,18-dioic-acid*1,18-9Z-octadecenedioic acid*α,ω-9Z-octadecenedioic acid 310.433 C18 H30 O4 C(C=CCCCCCCCC(=O)[O-])CCCCCCC(=O)[O-] PUBCHEM:20482290:*PUBCHEM:9543674: 1.2.1.- 18-oxo-oleate + NADP+ + H2O = H+ + octadecenedioate + NADPH suberin biosynthesis melibiose 6-O-(α-D-galactopyranosyl)-D-glucopyranose*D-Gal-α(1->6)-D-glucose*D-melibiose*melibiose*6-O-α-D-Galactopyranosyl-D-glucose*6-(α-D-galactosido)-D-glucose*α-D-Galp-(1->6)-D-Glc 342.299 C12 H22 O11 C1(OC(C(C(C1O)O)O)OCC2(OC(C(C(C2O)O)O)O))CO PUBCHEM:11458:*CAS:585-99-9:*LIGAND-CPD:C05402: 3.2.1.22 H2O + melibiose = α-D-galactose + β-D-glucose melibiose degradation uridine-5'-phosphate UMP*uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 322.168 C9 H11 N2 O9 P1 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])[O-])C(O)C(O)2)) CHEBI:57865:*PUBCHEM:1778309:*LIGAND-CPD:C00105:*CAS:58-97-9 2.4.2.9 diphosphate + uridine-5'-phosphate = 5-phospho-α-D-ribose 1-diphosphate + uracil salvage pathways of pyrimidine ribonucleotides uridine-5'-phosphate UMP*uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 322.168 C9 H11 N2 O9 P1 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])[O-])C(O)C(O)2)) CHEBI:57865:*PUBCHEM:1778309:*LIGAND-CPD:C00105:*CAS:58-97-9 2.7.1.48 uridine + GTP = H+ + uridine-5'-phosphate + GDP salvage pathways of pyrimidine ribonucleotides uridine-5'-phosphate UMP*uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 322.168 C9 H11 N2 O9 P1 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])[O-])C(O)C(O)2)) CHEBI:57865:*PUBCHEM:1778309:*LIGAND-CPD:C00105:*CAS:58-97-9 4.1.1.23 H+ + orotidine-5'-phosphate = CO2 + uridine-5'-phosphate uridine-5'-phosphate biosynthesis uridine-5'-phosphate UMP*uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 322.168 C9 H11 N2 O9 P1 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])[O-])C(O)C(O)2)) CHEBI:57865:*PUBCHEM:1778309:*LIGAND-CPD:C00105:*CAS:58-97-9 2.7.4.14 ATP + uridine-5'-phosphate = ADP + UDP pyrimidine ribonucleotides interconversion uridine-5'-phosphate UMP*uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 322.168 C9 H11 N2 O9 P1 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])[O-])C(O)C(O)2)) CHEBI:57865:*PUBCHEM:1778309:*LIGAND-CPD:C00105:*CAS:58-97-9 2.7.8.15 UDP-α-N-acetyl-D-glucosamine = uridine-5'-phosphate dolichyl-diphosphooligosaccharide biosynthesis uridine-5'-phosphate UMP*uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 322.168 C9 H11 N2 O9 P1 O=C1(C=CN(C(=O)N1)C2(OC(COP(=O)([O-])[O-])C(O)C(O)2)) CHEBI:57865:*PUBCHEM:1778309:*LIGAND-CPD:C00105:*CAS:58-97-9 2.7.4.22 ATP + uridine-5'-phosphate = ADP + UDP pyrimidine ribonucleotides interconversion 1-(5-phospho-D-ribosyl)-AMP 1-(5-Phosphoribosyl)-AMP*1-(5-phosphoribosyl)-AMP*phosphoribosyl-AMP*5-phosphoribosyl-AMP*N-(5-phospho-D-ribosyl)-AMP*N-(5'-phospho-D-ribosyl)-AMP*N1-(5-phospho-D-ribosyl)-AMP 555.288 C15 H19 N5 O14 P2 O=P([O-])(OCC4(C(C(C(N3(C1(=C(C(N(C=N1)C2(OC(C(C2O)O)COP([O-])([O-])=O))=N)N=C3)))O4)O)O))[O-] PUBCHEM:25244977:*LIGAND-CPD:C02741: 3.5.4.19 1-(5-phospho-D-ribosyl)-AMP + H2O = 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide histidine biosynthesis 1-(5-phospho-D-ribosyl)-AMP 1-(5-Phosphoribosyl)-AMP*1-(5-phosphoribosyl)-AMP*phosphoribosyl-AMP*5-phosphoribosyl-AMP*N-(5-phospho-D-ribosyl)-AMP*N-(5'-phospho-D-ribosyl)-AMP*N1-(5-phospho-D-ribosyl)-AMP 555.288 C15 H19 N5 O14 P2 O=P([O-])(OCC4(C(C(C(N3(C1(=C(C(N(C=N1)C2(OC(C(C2O)O)COP([O-])([O-])=O))=N)N=C3)))O4)O)O))[O-] PUBCHEM:25244977:*LIGAND-CPD:C02741: 3.6.1.31 phosphoribosyl-ATP + H2O = 1-(5-phospho-D-ribosyl)-AMP + diphosphate + H+ histidine biosynthesis coniferin coniferyl alcohol-4-O-β-D-glucopyranoside 342.345 C16 H22 O8 COC2(=CC(C=CCO)=CC=C(OC1(OC(CO)C(O)C(O)C(O)1))2) PUBCHEM:5280372:*CHEBI:16220:*LIGAND-CPD:C00761: 2.4.1.111 coniferyl alcohol = H+ + coniferin + UDP coniferin metabolism coniferin coniferyl alcohol-4-O-β-D-glucopyranoside 342.345 C16 H22 O8 COC2(=CC(C=CCO)=CC=C(OC1(OC(CO)C(O)C(O)C(O)1))2) PUBCHEM:5280372:*CHEBI:16220:*LIGAND-CPD:C00761: 3.2.1.126 H2O + coniferin = coniferyl alcohol + β-D-glucose coniferin metabolism isobutanol butanol 74.122 C4 H10 O1 CC(C)CO PUBCHEM:6560:*CHEBI:46645:*LIGAND-CPD:C14710: 1.1.1.1 H+ + isobutanal + NADH = isobutanol + NAD+ valine degradation II 1-(3-aminopropyl)-pyrrolinium 128.217 C7 H16 N2 C([N+])CC[N+]1(=CCCC1) PUBCHEM:25202014: 1-(3-aminopropyl)-4-aminobutanal = 1-(3-aminopropyl)-pyrrolinium + H2O spermine and spermidine degradation II 1-(3-aminopropyl)-pyrrolinium 128.217 C7 H16 N2 C([N+])CC[N+]1(=CCCC1) PUBCHEM:25202014: 1-(3-aminopropyl)-pyrrolinium = H+ + 1,5-diazabicyclononane spermine and spermidine degradation II 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate*1-(5-phosphoribosyl)-4-carboxy-5-aminoimidazole*5'-P-ribosyl-4-carboxy-5-aminoimidazole*5'-phosphoribosyl-4-carboxy-5-aminoimidazole*5-phosphoribosyl-4-carboxy-5-aminoimidazole*1-(5'-phosphoribosyl)-5-amino-4-imidazole carboxylate*1-(5'-phosphoribosyl)-4-carboxy-5-aminoimidazole*CAIR*4-carboxyaminoimidazole ribonucleotide*phosphoribosyl-carboxy-aminoimidazole 336.174 C9 H11 N3 O9 P1 O2(C(N1(C=NC(C([O-])=O)=C(N)1))C(O)C(O)C(COP([O-])([O-])=O)2) CHEBI:58564:*PUBCHEM:24916886:*LIGAND-CPD:C04751: 6.3.2.6 ATP + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-aspartate = H+ + ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole inosine-5'-phosphate biosynthesis II 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate*1-(5-phosphoribosyl)-4-carboxy-5-aminoimidazole*5'-P-ribosyl-4-carboxy-5-aminoimidazole*5'-phosphoribosyl-4-carboxy-5-aminoimidazole*5-phosphoribosyl-4-carboxy-5-aminoimidazole*1-(5'-phosphoribosyl)-5-amino-4-imidazole carboxylate*1-(5'-phosphoribosyl)-4-carboxy-5-aminoimidazole*CAIR*4-carboxyaminoimidazole ribonucleotide*phosphoribosyl-carboxy-aminoimidazole 336.174 C9 H11 N3 O9 P1 O2(C(N1(C=NC(C([O-])=O)=C(N)1))C(O)C(O)C(COP([O-])([O-])=O)2) CHEBI:58564:*PUBCHEM:24916886:*LIGAND-CPD:C04751: 4.1.1.21 H+ + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate = 5-aminoimidazole ribonucleotide + CO2 inosine-5'-phosphate biosynthesis II dihydromyricetin ampelopsin 319.247 C15 H11 O8 C1(C(=CC(=C2(C=1OC(C(C2=O)O)C3(C=C(C(=C(C=3)O)O)O)))O)[O-]) PUBCHEM:25244375:*LIGAND-CPD:C02906: 3',4',5'-pentahydroxyflavanone + 2-oxoglutarate + oxygen = dihydromyricetin + succinate + CO2 leucodelphinidin biosynthesis dihydromyricetin ampelopsin 319.247 C15 H11 O8 C1(C(=CC(=C2(C=1OC(C(C2=O)O)C3(C=C(C(=C(C=3)O)O)O)))O)[O-]) PUBCHEM:25244375:*LIGAND-CPD:C02906: 1.14.13.88 H+ + dihydrokaempferol + NADPH + oxygen = dihydromyricetin + NADP+ + H2O leucodelphinidin biosynthesis dihydromyricetin ampelopsin 319.247 C15 H11 O8 C1(C(=CC(=C2(C=1OC(C(C2=O)O)C3(C=C(C(=C(C=3)O)O)O)))O)[O-]) PUBCHEM:25244375:*LIGAND-CPD:C02906: 1.14.13.88 H+ + dihydrokaempferol + NADPH + oxygen = dihydromyricetin + NADP+ + H2O syringetin biosynthesis dihydromyricetin ampelopsin 319.247 C15 H11 O8 C1(C(=CC(=C2(C=1OC(C(C2=O)O)C3(C=C(C(=C(C=3)O)O)O)))O)[O-]) PUBCHEM:25244375:*LIGAND-CPD:C02906: 1.14.11.23 dihydromyricetin + 2-oxoglutarate + oxygen = myricetin + succinate + CO2 + H2O syringetin biosynthesis dihydromyricetin ampelopsin 319.247 C15 H11 O8 C1(C(=CC(=C2(C=1OC(C(C2=O)O)C3(C=C(C(=C(C=3)O)O)O)))O)[O-]) PUBCHEM:25244375:*LIGAND-CPD:C02906: 1.1.1.219 H+ + dihydromyricetin + NADPH = leucodelphinidin + NADP+ leucodelphinidin biosynthesis 6G,6-kestotetraose kestotetraose 666.583 C24 H42 O21 C1(C(C(C(O1)CO)O)O)(CO)(OC2(OC(C(O)C(O)C(O)2)COC3(C(C(O)C(O3)COC4(OC(CO)C(C(O)4)O)CO)O)(CO))) PUBCHEM:25202930: 3.2.1.- 6G,6-kestotetraose + H2O = 6G-kestotriose fructan degradation 5,6-dihydrothymine dihydrothymine 128.13 C5 H8 N2 O2 N1(C(=O)C(C)CNC(=O)1) PUBCHEM:93556:*CHEBI:27468:*LIGAND-CPD:C00906: 3.5.2.2 5,6-dihydrothymine + H2O = 3-ureido-isobutyrate + H+ thymine degradation 5,6-dihydrothymine dihydrothymine 128.13 C5 H8 N2 O2 N1(C(=O)C(C)CNC(=O)1) PUBCHEM:93556:*CHEBI:27468:*LIGAND-CPD:C00906: 1.3.1.2 5,6-dihydrothymine + NADP+ = thymine + NADPH + H+ thymine degradation 1,3-bisphospho-D-glycerate glycerate 1,3-diphosphate*3-phospho-D-glyceroyl-phosphate*3-phosphoglyceroyl-P*P-glyceroyl-P*phosphoglyceroyl-P*3-phosphoglyceroyl-phosphate*3-P-glyceroyl-P*DPG*13-DPG*glycerate 1,3-bisphosphate*1,3-biphosphoglycerate 262.006 C3 H4 O10 P2 C(O)(COP(=O)([O-])[O-])C(OP(=O)([O-])[O-])=O PUBCHEM:23405621:*LIGAND-CPD:C00236:*CAS:1981-49-3 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP gluconeogenesis I 1,3-bisphospho-D-glycerate glycerate 1,3-diphosphate*3-phospho-D-glyceroyl-phosphate*3-phosphoglyceroyl-P*P-glyceroyl-P*phosphoglyceroyl-P*3-phosphoglyceroyl-phosphate*3-P-glyceroyl-P*DPG*13-DPG*glycerate 1,3-bisphosphate*1,3-biphosphoglycerate 262.006 C3 H4 O10 P2 C(O)(COP(=O)([O-])[O-])C(OP(=O)([O-])[O-])=O PUBCHEM:23405621:*LIGAND-CPD:C00236:*CAS:1981-49-3 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP glycolysis III 1,3-bisphospho-D-glycerate glycerate 1,3-diphosphate*3-phospho-D-glyceroyl-phosphate*3-phosphoglyceroyl-P*P-glyceroyl-P*phosphoglyceroyl-P*3-phosphoglyceroyl-phosphate*3-P-glyceroyl-P*DPG*13-DPG*glycerate 1,3-bisphosphate*1,3-biphosphoglycerate 262.006 C3 H4 O10 P2 C(O)(COP(=O)([O-])[O-])C(OP(=O)([O-])[O-])=O PUBCHEM:23405621:*LIGAND-CPD:C00236:*CAS:1981-49-3 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP glycolysis IV (plant cytosol) 1,3-bisphospho-D-glycerate glycerate 1,3-diphosphate*3-phospho-D-glyceroyl-phosphate*3-phosphoglyceroyl-P*P-glyceroyl-P*phosphoglyceroyl-P*3-phosphoglyceroyl-phosphate*3-P-glyceroyl-P*DPG*13-DPG*glycerate 1,3-bisphosphate*1,3-biphosphoglycerate 262.006 C3 H4 O10 P2 C(O)(COP(=O)([O-])[O-])C(OP(=O)([O-])[O-])=O PUBCHEM:23405621:*LIGAND-CPD:C00236:*CAS:1981-49-3 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP glycolysis I 1,3-bisphospho-D-glycerate glycerate 1,3-diphosphate*3-phospho-D-glyceroyl-phosphate*3-phosphoglyceroyl-P*P-glyceroyl-P*phosphoglyceroyl-P*3-phosphoglyceroyl-phosphate*3-P-glyceroyl-P*DPG*13-DPG*glycerate 1,3-bisphosphate*1,3-biphosphoglycerate 262.006 C3 H4 O10 P2 C(O)(COP(=O)([O-])[O-])C(OP(=O)([O-])[O-])=O PUBCHEM:23405621:*LIGAND-CPD:C00236:*CAS:1981-49-3 2.7.2.3 3-phospho-D-glycerate + ATP = 1,3-bisphospho-D-glycerate + ADP Calvin-Benson-Bassham cycle 1,3-bisphospho-D-glycerate glycerate 1,3-diphosphate*3-phospho-D-glyceroyl-phosphate*3-phosphoglyceroyl-P*P-glyceroyl-P*phosphoglyceroyl-P*3-phosphoglyceroyl-phosphate*3-P-glyceroyl-P*DPG*13-DPG*glycerate 1,3-bisphosphate*1,3-biphosphoglycerate 262.006 C3 H4 O10 P2 C(O)(COP(=O)([O-])[O-])C(OP(=O)([O-])[O-])=O PUBCHEM:23405621:*LIGAND-CPD:C00236:*CAS:1981-49-3 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH gluconeogenesis I 1,3-bisphospho-D-glycerate glycerate 1,3-diphosphate*3-phospho-D-glyceroyl-phosphate*3-phosphoglyceroyl-P*P-glyceroyl-P*phosphoglyceroyl-P*3-phosphoglyceroyl-phosphate*3-P-glyceroyl-P*DPG*13-DPG*glycerate 1,3-bisphosphate*1,3-biphosphoglycerate 262.006 C3 H4 O10 P2 C(O)(COP(=O)([O-])[O-])C(OP(=O)([O-])[O-])=O PUBCHEM:23405621:*LIGAND-CPD:C00236:*CAS:1981-49-3 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH glycolysis III 1,3-bisphospho-D-glycerate glycerate 1,3-diphosphate*3-phospho-D-glyceroyl-phosphate*3-phosphoglyceroyl-P*P-glyceroyl-P*phosphoglyceroyl-P*3-phosphoglyceroyl-phosphate*3-P-glyceroyl-P*DPG*13-DPG*glycerate 1,3-bisphosphate*1,3-biphosphoglycerate 262.006 C3 H4 O10 P2 C(O)(COP(=O)([O-])[O-])C(OP(=O)([O-])[O-])=O PUBCHEM:23405621:*LIGAND-CPD:C00236:*CAS:1981-49-3 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH glycolysis IV (plant cytosol) 1,3-bisphospho-D-glycerate glycerate 1,3-diphosphate*3-phospho-D-glyceroyl-phosphate*3-phosphoglyceroyl-P*P-glyceroyl-P*phosphoglyceroyl-P*3-phosphoglyceroyl-phosphate*3-P-glyceroyl-P*DPG*13-DPG*glycerate 1,3-bisphosphate*1,3-biphosphoglycerate 262.006 C3 H4 O10 P2 C(O)(COP(=O)([O-])[O-])C(OP(=O)([O-])[O-])=O PUBCHEM:23405621:*LIGAND-CPD:C00236:*CAS:1981-49-3 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = H+ + 1,3-bisphospho-D-glycerate + NADH glycolysis I 1,3-bisphospho-D-glycerate glycerate 1,3-diphosphate*3-phospho-D-glyceroyl-phosphate*3-phosphoglyceroyl-P*P-glyceroyl-P*phosphoglyceroyl-P*3-phosphoglyceroyl-phosphate*3-P-glyceroyl-P*DPG*13-DPG*glycerate 1,3-bisphosphate*1,3-biphosphoglycerate 262.006 C3 H4 O10 P2 C(O)(COP(=O)([O-])[O-])C(OP(=O)([O-])[O-])=O PUBCHEM:23405621:*LIGAND-CPD:C00236:*CAS:1981-49-3 1.2.1.13 NADP+ + D-glyceraldehyde-3-phosphate = H+ + NADPH + 1,3-bisphospho-D-glycerate Calvin-Benson-Bassham cycle α-D-xylose α-D-xylose*xylose*D-xylose*wood sugar 150.131 C5 H10 O5 OC1(COC(O)C(O)C(O)1) LIGAND-CPD:C00181:*PUBCHEM:6027:*LIGAND-CPD:C01394:*CHEBI:28518:*PUBCHEM:6027:*CAS:58-86-6 5.3.1.5 α-D-xylose = D-xylulose xylose degradation I isoliquiritigenin 42'4'-trihydroxychalcone 256.257 C15 H12 O4 OC1(=CC=C(C(=C1)O)C(C=CC2(=CC=C(C=C2)O))=O) PUBCHEM:638278:*CHEBI:310312:*PUBCHEM:638278:*LIGAND-CPD:C08650: 2.3.1.170 H+ + 4-coumaroyl-CoA + malonyl-CoA + NADPH = isoliquiritigenin + coenzyme A + CO2 + NADP+ + H2O flavonoid biosynthesis prephenate 224.17 C10 H8 O6 C1(=CC(C(=O)[O-])(CC(=O)C([O-])=O)C=CC(O)1) PUBCHEM:5460303:*CHEBI:29934:*LIGAND-CPD:C00254:*CAS:126-49-8 4.2.1.51 H+ + prephenate = keto-phenylpyruvate + H2O + CO2 phenylalanine biosynthesis I prephenate 224.17 C10 H8 O6 C1(=CC(C(=O)[O-])(CC(=O)C([O-])=O)C=CC(O)1) PUBCHEM:5460303:*CHEBI:29934:*LIGAND-CPD:C00254:*CAS:126-49-8 2.6.1.79 prephenate + L-glutamate = L-arogenate + 2-oxoglutarate tyrosine biosynthesis II prephenate 224.17 C10 H8 O6 C1(=CC(C(=O)[O-])(CC(=O)C([O-])=O)C=CC(O)1) PUBCHEM:5460303:*CHEBI:29934:*LIGAND-CPD:C00254:*CAS:126-49-8 2.6.1.79 prephenate + L-glutamate = L-arogenate + 2-oxoglutarate phenylalanine biosynthesis II prephenate 224.17 C10 H8 O6 C1(=CC(C(=O)[O-])(CC(=O)C([O-])=O)C=CC(O)1) PUBCHEM:5460303:*CHEBI:29934:*LIGAND-CPD:C00254:*CAS:126-49-8 5.4.99.5 chorismate = prephenate tyrosine biosynthesis II prephenate 224.17 C10 H8 O6 C1(=CC(C(=O)[O-])(CC(=O)C([O-])=O)C=CC(O)1) PUBCHEM:5460303:*CHEBI:29934:*LIGAND-CPD:C00254:*CAS:126-49-8 5.4.99.5 chorismate = prephenate phenylalanine biosynthesis II prephenate 224.17 C10 H8 O6 C1(=CC(C(=O)[O-])(CC(=O)C([O-])=O)C=CC(O)1) PUBCHEM:5460303:*CHEBI:29934:*LIGAND-CPD:C00254:*CAS:126-49-8 5.4.99.5 chorismate = prephenate phenylalanine biosynthesis I guanine 151.127 C5 H5 N5 O1 C2(=NC1(=C(N=C(NC(=O)1)N)N2)) CHEBI:16235:*PUBCHEM:764:*LIGAND-CPD:C00242:*CAS:73-40-5 3.2.2.1 guanosine + H2O = guanine guanosine nucleotides degradation II guanine 151.127 C5 H5 N5 O1 C2(=NC1(=C(N=C(NC(=O)1)N)N2)) CHEBI:16235:*PUBCHEM:764:*LIGAND-CPD:C00242:*CAS:73-40-5 3.2.2.1 guanosine + H2O = guanine guanine and guanosine salvage II guanine 151.127 C5 H5 N5 O1 C2(=NC1(=C(N=C(NC(=O)1)N)N2)) CHEBI:16235:*PUBCHEM:764:*LIGAND-CPD:C00242:*CAS:73-40-5 2.4.2.8 GMP + diphosphate = guanine + 5-phospho-α-D-ribose 1-diphosphate guanine and guanosine salvage II guanine 151.127 C5 H5 N5 O1 C2(=NC1(=C(N=C(NC(=O)1)N)N2)) CHEBI:16235:*PUBCHEM:764:*LIGAND-CPD:C00242:*CAS:73-40-5 3.5.4.3 H2O + guanine = ammonia + xanthine guanosine nucleotides degradation II 5-(methylthio)-2,3-dioxopentyl phosphate 1-phosphoryloxy-2,3-diketo-5-methylthiopentane*1-phospho-2,3-diketo-5-methylthiopentane*DKM-1-P*2,3-diketo-5-methylthio-1-phosphopentane*2,3-diketo-5-methylthiopentyl-1-phosphate*5-(methylsulfanyl)-2,3-dioxopentyl phosphate*5-methylthio-1-(phosphonooxy)pentane-2,3-dione 240.167 C6 H9 O6 P1 S1 O(P([O-])(=O)[O-])CC(=O)C(=O)CCSC CHEBI:50604:*CHEBI:58828:*PUBCHEM:25244990:*LIGAND-CPD:C15650: 5-(methylthio)-2,3-dioxopentyl phosphate = H+ + 2-hydroxy-3-keto-5-methylthio-1-phosphopentene methionine salvage I 5-(methylthio)-2,3-dioxopentyl phosphate 1-phosphoryloxy-2,3-diketo-5-methylthiopentane*1-phospho-2,3-diketo-5-methylthiopentane*DKM-1-P*2,3-diketo-5-methylthio-1-phosphopentane*2,3-diketo-5-methylthiopentyl-1-phosphate*5-(methylsulfanyl)-2,3-dioxopentyl phosphate*5-methylthio-1-(phosphonooxy)pentane-2,3-dione 240.167 C6 H9 O6 P1 S1 O(P([O-])(=O)[O-])CC(=O)C(=O)CCSC CHEBI:50604:*CHEBI:58828:*PUBCHEM:25244990:*LIGAND-CPD:C15650: 4.2.1.109 5-methylthioribulose-1-phosphate = 5-(methylthio)-2,3-dioxopentyl phosphate + H2O methionine salvage I (-)-α-pinene (-)-(1S,5S)-α-pinene 136.236 C10 H16 C1(=CCC2(CC1C2(C)C))C PUBCHEM:440968:*CHEBI:28660:*LIGAND-CPD:C06308: 4.2.3.14 geranyl diphosphate = (-)-α-pinene + diphosphate monoterpene biosynthesis coumarinate coumarinic acid 163.152 C9 H7 O3 C1(C=CC(=C(C=1)C=CC(=O)[O-])O) PUBCHEM:21158468:*CHEBI:47921:*LIGAND-CPD:C05838: H+ + coumarinate = coumarin + H2O coumarin biosynthesis (via 2-coumarate) coumarinate coumarinic acid 163.152 C9 H7 O3 C1(C=CC(=C(C=1)C=CC(=O)[O-])O) PUBCHEM:21158468:*CHEBI:47921:*LIGAND-CPD:C05838: 3.2.1.21 cis-coumarinic acid-β-D-glucoside + H2O = coumarinate + β-D-glucose coumarin biosynthesis (via 2-coumarate) vibriobactin 705.72 C35 H39 N5 O11 CC5(C(C(NCCCN(CCCNC(C1(=CC=CC(=C1O)O))=O)C(C3(C(C)OC(C2(=CC=CC(=C2O)O))=N3))=O)=O)N=C(C4(=CC=CC(=C4O)O))O5) PUBCHEM:5462333:*LIGAND-CPD:C06769: dihydroxyphenyl-5-methyloxazoline-norspermidine-2,3-dihydroxybenzoate + dihydroxyphenyl-5-methyloxazoline-VibF = vibriobactin vibriobactin biosynthesis all-trans-lycopene ψ,ψ-carotene 536.882 C40 H56 CC(=CCCC(=CC=CC(=CC=CC(=CC=CC=C(C=CC=C(C=CC=C(CCC=C(C)C)C)C)C)C)C)C)C KNAPSACK:C00000911:*CHEBI:15948:*PUBCHEM:446925:*LIGAND-CPD:C05432: 5.5.1.- all-trans-lycopene = γ-carotene β-carotene biosynthesis all-trans-lycopene ψ,ψ-carotene 536.882 C40 H56 CC(=CCCC(=CC=CC(=CC=CC(=CC=CC=C(C=CC=C(C=CC=C(CCC=C(C)C)C)C)C)C)C)C)C KNAPSACK:C00000911:*CHEBI:15948:*PUBCHEM:446925:*LIGAND-CPD:C05432: 5.2.1.- 7',9'-cis-lycopene = all-trans-lycopene trans-lycopene biosynthesis II (plants) all-trans-lycopene ψ,ψ-carotene 536.882 C40 H56 CC(=CCCC(=CC=CC(=CC=CC(=CC=CC=C(C=CC=C(C=CC=C(CCC=C(C)C)C)C)C)C)C)C)C KNAPSACK:C00000911:*CHEBI:15948:*PUBCHEM:446925:*LIGAND-CPD:C05432: 5.2.1.- prolycopene = all-trans-lycopene trans-lycopene biosynthesis II (plants) 5-hydroxy-coniferaldehyde 194.187 C10 H10 O4 O(C)C1(C(=C(O)C=C(C=1)C=CC=O)O) PUBCHEM:5282094:*LIGAND-CPD:C12204: 1.14.13.- H+ + coniferaldehyde + NADPH + oxygen = 5-hydroxy-coniferaldehyde + NADP+ + H2O phenylpropanoid biosynthesis 5-hydroxy-coniferaldehyde 194.187 C10 H10 O4 O(C)C1(C(=C(O)C=C(C=1)C=CC=O)O) PUBCHEM:5282094:*LIGAND-CPD:C12204: 1.14.13.- H+ + coniferaldehyde + NADPH + oxygen = 5-hydroxy-coniferaldehyde + NADP+ + H2O ferulate and sinapate biosynthesis 5-hydroxy-coniferaldehyde 194.187 C10 H10 O4 O(C)C1(C(=C(O)C=C(C=1)C=CC=O)O) PUBCHEM:5282094:*LIGAND-CPD:C12204: 2.1.1.68 5-hydroxy-coniferaldehyde + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + sinapaldehyde phenylpropanoid biosynthesis 5-hydroxy-coniferaldehyde 194.187 C10 H10 O4 O(C)C1(C(=C(O)C=C(C=1)C=CC=O)O) PUBCHEM:5282094:*LIGAND-CPD:C12204: 2.1.1.68 5-hydroxy-coniferaldehyde + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + sinapaldehyde ferulate and sinapate biosynthesis coumaraldehyde 148.161 C9 H8 O2 OC1(=CC=C(C=CC=O)C=C1) CHEBI:278852:*PUBCHEM:641301:*LIGAND-CPD:C05608: 1.1.1.195 H+ + coumaraldehyde + NADPH = coumaryl-alcohol + NADP+ phenylpropanoid biosynthesis coumaraldehyde 148.161 C9 H8 O2 OC1(=CC=C(C=CC=O)C=C1) CHEBI:278852:*PUBCHEM:641301:*LIGAND-CPD:C05608: 1.2.1.44 4-coumaroyl-CoA + NADPH + H+ = coumaraldehyde + coenzyme A + NADP+ phenylpropanoid biosynthesis oleoyl-CoA cis-octadec-9-enoyl-CoA*(9Z)-octadec-9-enoyl-CoA*18:1 cis-9*18:1(n-9)*oleoyl-CoA (cis) 1027.953 C39 H64 N7 O17 P3 S1 CCCCCCCCC=CCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(OP(=O)([O-])[O-])1)N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25244993:*LIGAND-CPD:C00510: oleoyl-CoA = coenzyme A linoleate biosynthesis I (plants) oleoyl-CoA cis-octadec-9-enoyl-CoA*(9Z)-octadec-9-enoyl-CoA*18:1 cis-9*18:1(n-9)*oleoyl-CoA (cis) 1027.953 C39 H64 N7 O17 P3 S1 CCCCCCCCC=CCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(OP(=O)([O-])[O-])1)N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25244993:*LIGAND-CPD:C00510: 6.2.1.3 oleate + coenzyme A + ATP = oleoyl-CoA + AMP + diphosphate linoleate biosynthesis I (plants) 5-aminoimidazole ribonucleotide 5-amino-1-(5-phospho-D-ribosyl)imidazole*5-aminoimidazole ribotide*AIR*1-(5'-phosphoribosyl)-5-aminoimidazole*5'-phosphoribosyl-5-aminoimidazole*phosphoribosylaminoimidazole 294.18 C8 H13 N3 O7 P1 C2(=[N+]C=C(N)N(C1(OC(COP([O-])(=O)[O-])C(O)C(O)1))2) PUBCHEM:44229244:*CAS:25635-88-5:*LIGAND-CPD:C03373: 4.1.99.- 5-aminoimidazole ribonucleotide + S-adenosyl-L-methionine = hydroxymethylpyrimidine phosphate + 5'-deoxyadenosine + L-methionine + formate + carbon monoxide + H+ thiamine biosynthesis II 5-aminoimidazole ribonucleotide 5-amino-1-(5-phospho-D-ribosyl)imidazole*5-aminoimidazole ribotide*AIR*1-(5'-phosphoribosyl)-5-aminoimidazole*5'-phosphoribosyl-5-aminoimidazole*phosphoribosylaminoimidazole 294.18 C8 H13 N3 O7 P1 C2(=[N+]C=C(N)N(C1(OC(COP([O-])(=O)[O-])C(O)C(O)1))2) PUBCHEM:44229244:*CAS:25635-88-5:*LIGAND-CPD:C03373: 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = H+ + ADP + 5-aminoimidazole ribonucleotide 5-aminoimidazole ribonucleotide biosynthesis II 5-aminoimidazole ribonucleotide 5-amino-1-(5-phospho-D-ribosyl)imidazole*5-aminoimidazole ribotide*AIR*1-(5'-phosphoribosyl)-5-aminoimidazole*5'-phosphoribosyl-5-aminoimidazole*phosphoribosylaminoimidazole 294.18 C8 H13 N3 O7 P1 C2(=[N+]C=C(N)N(C1(OC(COP([O-])(=O)[O-])C(O)C(O)1))2) PUBCHEM:44229244:*CAS:25635-88-5:*LIGAND-CPD:C03373: 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = H+ + ADP + 5-aminoimidazole ribonucleotide 5-aminoimidazole ribonucleotide biosynthesis I 5-aminoimidazole ribonucleotide 5-amino-1-(5-phospho-D-ribosyl)imidazole*5-aminoimidazole ribotide*AIR*1-(5'-phosphoribosyl)-5-aminoimidazole*5'-phosphoribosyl-5-aminoimidazole*phosphoribosylaminoimidazole 294.18 C8 H13 N3 O7 P1 C2(=[N+]C=C(N)N(C1(OC(COP([O-])(=O)[O-])C(O)C(O)1))2) PUBCHEM:44229244:*CAS:25635-88-5:*LIGAND-CPD:C03373: 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = H+ + ADP + 5-aminoimidazole ribonucleotide superpathway of 5-aminoimidazole ribonucleotide biosynthesis 5-aminoimidazole ribonucleotide 5-amino-1-(5-phospho-D-ribosyl)imidazole*5-aminoimidazole ribotide*AIR*1-(5'-phosphoribosyl)-5-aminoimidazole*5'-phosphoribosyl-5-aminoimidazole*phosphoribosylaminoimidazole 294.18 C8 H13 N3 O7 P1 C2(=[N+]C=C(N)N(C1(OC(COP([O-])(=O)[O-])C(O)C(O)1))2) PUBCHEM:44229244:*CAS:25635-88-5:*LIGAND-CPD:C03373: 4.1.1.21 H+ + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate = 5-aminoimidazole ribonucleotide + CO2 inosine-5'-phosphate biosynthesis II 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester 131-hydroxy-Mg-protoporphyrin IX 13-monomethyl ester 613.974 C35 H33 N4 O5 MG1 C16(N8(C(=C(C=1C)C(CC(OC)=O)O)C=C2(C(=C(C7(=N2[Mg]5(N3(C(C(=C(C3=CC4(C(=C(C(N=45)=C6)C=C)C))C=C)C)=C7))8))C)CCC(=O)[O-]))) CHEBI:60489:*PUBCHEM:44229246:*LIGAND-CPD:C11829: 1.14.13.81 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + oxygen = 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis I 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester 131-hydroxy-Mg-protoporphyrin IX 13-monomethyl ester 613.974 C35 H33 N4 O5 MG1 C16(N8(C(=C(C=1C)C(CC(OC)=O)O)C=C2(C(=C(C7(=N2[Mg]5(N3(C(C(=C(C3=CC4(C(=C(C(N=45)=C6)C=C)C))C=C)C)=C7))8))C)CCC(=O)[O-]))) CHEBI:60489:*PUBCHEM:44229246:*LIGAND-CPD:C11829: 1.14.13.81 magnesium-protoporphyrin IX 13-monomethyl ester + oxygen + NADPH + H+ = 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis I 2'-deoxymugineic acid 1-azetidinebutanoic acid 303.291 C12 H19 N2 O7 O=C([O-])C1([N+](CC1)CCC([N+]CCC(C([O-])=O)O)C([O-])=O) PUBCHEM:189811:*PUBCHEM:25244997:*LIGAND-CPD:C15485: 1.1.1.285 2'-deoxymugineic acid = 3''-deamino-3''-oxonicotianamine + H+ 2'-deoxymugineic acid phytosiderophore biosynthesis thiamine-phosphate TMP*thiamin monophosphate*thiamin phosphate*thiamin-P*thiamine-Pi*ThP*thiamine monophosphate 343.317 C12 H16 N4 O4 P1 S1 N2(C(=C(C[N+]1(C(C)=C(CCOP([O-])(=O)[O-])SC=1))C=NC(C)=2)N) PUBCHEM:15942892:*CHEBI:37575:*CAS:532-40-1:*LIGAND-CPD:C01081: 3.1.3.2 thiamine-phosphate + H2O = thiamin thiamine biosynthesis II thiamine-phosphate TMP*thiamin monophosphate*thiamin phosphate*thiamin-P*thiamine-Pi*ThP*thiamine monophosphate 343.317 C12 H16 N4 O4 P1 S1 N2(C(=C(C[N+]1(C(C)=C(CCOP([O-])(=O)[O-])SC=1))C=NC(C)=2)N) PUBCHEM:15942892:*CHEBI:37575:*CAS:532-40-1:*LIGAND-CPD:C01081: 2.5.1.3 H+ + 4-methyl-5-(2-phosphonooxyethyl)thiazole + 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate = thiamine-phosphate + diphosphate thiamine biosynthesis II N-carbamoylputrescine 132.185 C5 H14 N3 O1 C(CCCNC(N)=O)[N+] PUBCHEM:25244388:*LIGAND-CPD:C00436:*CAS:6851-51-0 3.5.3.12 H2O + agmatine = H+ + ammonia + N-carbamoylputrescine putrescine biosynthesis II N-carbamoylputrescine 132.185 C5 H14 N3 O1 C(CCCNC(N)=O)[N+] PUBCHEM:25244388:*LIGAND-CPD:C00436:*CAS:6851-51-0 3.5.3.12 H2O + agmatine = H+ + ammonia + N-carbamoylputrescine arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) N-carbamoylputrescine 132.185 C5 H14 N3 O1 C(CCCNC(N)=O)[N+] PUBCHEM:25244388:*LIGAND-CPD:C00436:*CAS:6851-51-0 3.5.1.53 H+ + N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia putrescine biosynthesis II N-carbamoylputrescine 132.185 C5 H14 N3 O1 C(CCCNC(N)=O)[N+] PUBCHEM:25244388:*LIGAND-CPD:C00436:*CAS:6851-51-0 3.5.1.53 H+ + N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) 5'-deoxyadenosine 5'-deoxyadenosine*CH3Ado 251.244 C10 H13 N5 O3 C2(N=C(N)C3(N=CN(C1(OC(C)C(O)C(O)1))C(N=2)=3)) PUBCHEM:439182:*CHEBI:17319:*LIGAND-CPD:C05198: 4.1.99.- 5-aminoimidazole ribonucleotide + S-adenosyl-L-methionine = hydroxymethylpyrimidine phosphate + 5'-deoxyadenosine + L-methionine + formate + carbon monoxide + H+ thiamine biosynthesis II 5'-deoxyadenosine 5'-deoxyadenosine*CH3Ado 251.244 C10 H13 N5 O3 C2(N=C(N)C3(N=CN(C1(OC(C)C(O)C(O)1))C(N=2)=3)) PUBCHEM:439182:*CHEBI:17319:*LIGAND-CPD:C05198: 2.8.1.8 S-adenosyl-L-methionine + S2- = 5'-deoxyadenosine + L-methionine lipoate biosynthesis and incorporation I 5'-deoxyadenosine 5'-deoxyadenosine*CH3Ado 251.244 C10 H13 N5 O3 C2(N=C(N)C3(N=CN(C1(OC(C)C(O)C(O)1))C(N=2)=3)) PUBCHEM:439182:*CHEBI:17319:*LIGAND-CPD:C05198: 2.8.1.6 dethiobiotin + S-adenosyl-L-methionine = biotin + 5'-deoxyadenosine + L-methionine biotin biosynthesis from 7-keto-8-aminopelargonate nicotinate 3-pyridinecarboxylic acid*nicotinic acid*wampocap*nicolar*nicocap*nicobid*nico-400-*nicamin*niacin*niacine*vitamin B3*3-pyridinecarboxylate 122.103 C6 H4 N1 O2 C1(C=CC(C([O-])=O)=CN=1) PUBCHEM:937:*CHEBI:32544:*LIGAND-CPD:C00253:*CAS:59-67-6 2.4.2.- H+ + nicotinate + D-ribulose-1-phosphate = nicotinate riboside pyridine nucleotide cycling (plants) nicotinate 3-pyridinecarboxylic acid*nicotinic acid*wampocap*nicolar*nicocap*nicobid*nico-400-*nicamin*niacin*niacine*vitamin B3*3-pyridinecarboxylate 122.103 C6 H4 N1 O2 C1(C=CC(C([O-])=O)=CN=1) PUBCHEM:937:*CHEBI:32544:*LIGAND-CPD:C00253:*CAS:59-67-6 2.4.2.11 nicotinate mononucleotide + diphosphate = H+ + nicotinate + 5-phospho-α-D-ribose 1-diphosphate pyridine nucleotide cycling (plants) nicotinate 3-pyridinecarboxylic acid*nicotinic acid*wampocap*nicolar*nicocap*nicobid*nico-400-*nicamin*niacin*niacine*vitamin B3*3-pyridinecarboxylate 122.103 C6 H4 N1 O2 C1(C=CC(C([O-])=O)=CN=1) PUBCHEM:937:*CHEBI:32544:*LIGAND-CPD:C00253:*CAS:59-67-6 3.2.2.- nicotinate mononucleotide + H2O = H+ + nicotinate + D-ribose-5-phosphate pyridine nucleotide cycling (plants) nicotinate 3-pyridinecarboxylic acid*nicotinic acid*wampocap*nicolar*nicocap*nicobid*nico-400-*nicamin*niacin*niacine*vitamin B3*3-pyridinecarboxylate 122.103 C6 H4 N1 O2 C1(C=CC(C([O-])=O)=CN=1) PUBCHEM:937:*CHEBI:32544:*LIGAND-CPD:C00253:*CAS:59-67-6 3.5.1.19 nicotinamide + H2O = H+ + ammonia + nicotinate pyridine nucleotide cycling (plants) chlorophyllide b 627.958 C35 H31 N4 O6 MG1 C24(=CC9(C(C)C(CCC(=O)[O-])C5(N([Mg]36(N1(C(C(CC)=C(C=O)C=1C=C(C(C=C)=C(C)2)N34)=CC7(=C(C)C8(C(=O)C(C(OC)=O)C=5C(N67)=8)))))=9))) PUBCHEM:25245000:*LIGAND-CPD:C16541: 1.14.13.- 7-hydroxy-chlorophyllide a + oxygen + NADPH = chlorophyllide b + H2O + NADP+ chlorophyll cycle chlorophyllide b 627.958 C35 H31 N4 O6 MG1 C24(=CC9(C(C)C(CCC(=O)[O-])C5(N([Mg]36(N1(C(C(CC)=C(C=O)C=1C=C(C(C=C)=C(C)2)N34)=CC7(=C(C)C8(C(=O)C(C(OC)=O)C=5C(N67)=8)))))=9))) PUBCHEM:25245000:*LIGAND-CPD:C16541: 2.5.1.- H+ + chlorophyllide b + phytyl diphosphate = chlorophyll b + diphosphate chlorophyll cycle campestanol 5α-campestanol 402.702 C28 H50 O1 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(CCC(C(C)C)C)C)C(CC3)(C)4)))C))O) PUBCHEM:25202034:*LIGAND-CPD:C15787: H+ + (5α)-campestan-3-one = campestanol brassinosteroid biosynthesis II campestanol 5α-campestanol 402.702 C28 H50 O1 C1(CC(CC2(C1(C3(C(CC2)C4(CCC(C(CCC(C(C)C)C)C)C(CC3)(C)4)))C))O) PUBCHEM:25202034:*LIGAND-CPD:C15787: 1.14.13.- H+ + campestanol + oxygen + NADPH = 6-deoxocathasterone + H2O + NADP+ brassinosteroid biosynthesis II α-iminosuccinate α-iminosuccinate 129.072 C4 H3 N1 O4 C(=O)([O-])CC(=N)C(=O)[O-] CHEBI:58831:*PUBCHEM:23615393:*LIGAND-CPD:C05840: 2.5.1.72 α-iminosuccinate + dihydroxyacetone phosphate = quinolinate + H2O NAD biosynthesis I (from aspartate) α-iminosuccinate α-iminosuccinate 129.072 C4 H3 N1 O4 C(=O)([O-])CC(=N)C(=O)[O-] CHEBI:58831:*PUBCHEM:23615393:*LIGAND-CPD:C05840: 1.4.3.16 L-aspartate + oxygen = H+ + α-iminosuccinate + hydrogen peroxide NAD biosynthesis I (from aspartate) UDP-4-dehydro-6-deoxy-D-glucose UDP-4-keto-6-deoxyglucose*UDP-4-keto-6-deoxy-D-glucose*UDP-4-oxo-6-deoxy-D-glucose 546.274 C15 H20 N2 O16 P2 CC3(OC(OP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(=O)NC(=O)2)))C(O)C(O)C(=O)3) PUBCHEM:44237375:*PUBCHEM:25246268:*LIGAND-CPD:C04089: H+ + UDP-4-dehydro-6-deoxy-D-glucose + NADPH = UDP-L-rhamnose + NADP+ UDP-L-rhamnose biosynthesis UDP-4-dehydro-6-deoxy-D-glucose UDP-4-keto-6-deoxyglucose*UDP-4-keto-6-deoxy-D-glucose*UDP-4-oxo-6-deoxy-D-glucose 546.274 C15 H20 N2 O16 P2 CC3(OC(OP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(=O)NC(=O)2)))C(O)C(O)C(=O)3) PUBCHEM:44237375:*PUBCHEM:25246268:*LIGAND-CPD:C04089: 4.2.1.76 UDP-L-rhamnose biosynthesis xanthosine 9 β-D-ribofuranosylxanthine 284.228 C10 H12 N4 O6 OCC3(OC(N2(C1(=C(C(NC(=O)N1)=O)N=C2)))C(O)C(O)3) PUBCHEM:1189:*LIGAND-CPD:C01762:*CAS:146-80-5 3.1.3.5 xanthosine-5-phosphate + H2O = xanthosine adenosine nucleotides degradation I xanthosine 9 β-D-ribofuranosylxanthine 284.228 C10 H12 N4 O6 OCC3(OC(N2(C1(=C(C(NC(=O)N1)=O)N=C2)))C(O)C(O)3) PUBCHEM:1189:*LIGAND-CPD:C01762:*CAS:146-80-5 3.2.2.1 xanthosine + H2O = xanthine adenosine nucleotides degradation I pinocembrin chalcone 256.257 C15 H12 O4 C1(C(=CC(=C(C=1O)C(C=CC2(C=CC=CC=2))=O)O)O) CHEBI:310313:*PUBCHEM:6474295:*LIGAND-CPD:C16404: 2.3.1.- H+ + malonyl-CoA + (E)-cinnamoyl-CoA = pinocembrin chalcone + coenzyme A + CO2 pinobanksin biosynthesis pinocembrin chalcone 256.257 C15 H12 O4 C1(C(=CC(=C(C=1O)C(C=CC2(C=CC=CC=2))=O)O)O) CHEBI:310313:*PUBCHEM:6474295:*LIGAND-CPD:C16404: 5.5.1.6 pinocembrin chalcone = H+ + (2S)-pinocembrin pinobanksin biosynthesis 1-monoacylglycerol Monoacylglycerol*Glyceride*monoglyceride*1-acylglycerol C4 H7 O4 R1 OC(CO)COC([R])=O CHEBI:35759: 3.1.1.23 1-monoacylglycerol + H2O = glycerol triacylglycerol degradation 1-monoacylglycerol Monoacylglycerol*Glyceride*monoglyceride*1-acylglycerol C4 H7 O4 R1 OC(CO)COC([R])=O CHEBI:35759: 2-monoacylglycerol = 1-monoacylglycerol triacylglycerol degradation o-succinylbenzoate o-succinyl-benzoate*2-succinyl-benzoate*2-succinylbenzoate*succinylbenzoate 220.181 C11 H8 O5 O=C([O-])CCC(=O)C1(C=CC=CC(C(=O)[O-])=1) PUBCHEM:5459922:*CHEBI:18325:*LIGAND-CPD:C02730: 6.2.1.26 ATP + o-succinylbenzoate + coenzyme A = 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA + ADP 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) o-succinylbenzoate o-succinyl-benzoate*2-succinyl-benzoate*2-succinylbenzoate*succinylbenzoate 220.181 C11 H8 O5 O=C([O-])CCC(=O)C1(C=CC=CC(C(=O)[O-])=1) PUBCHEM:5459922:*CHEBI:18325:*LIGAND-CPD:C02730: 4.2.1.113 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate = o-succinylbenzoate + H2O 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) pyridoxamine 5'-phosphate pyridoxamine phosphate*PMP 247.167 C8 H12 N2 O5 P1 C1(C(=C(N=CC(COP([O-])([O-])=O)=1)C)O)C[N+] CHEBI:58451:*PUBCHEM:25246271:*CAS:529-96-4:*LIGAND-CPD:C00647: 1.4.3.5 oxygen + H2O + pyridoxamine 5'-phosphate = H+ + ammonia + hydrogen peroxide + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway pyridoxamine 5'-phosphate pyridoxamine phosphate*PMP 247.167 C8 H12 N2 O5 P1 C1(C(=C(N=CC(COP([O-])([O-])=O)=1)C)O)C[N+] CHEBI:58451:*PUBCHEM:25246271:*CAS:529-96-4:*LIGAND-CPD:C00647: 2.7.1.35 ATP + pyridoxamine = H+ + ADP + pyridoxamine 5'-phosphate pyridoxal 5'-phosphate salvage pathway 2,4-dihydroxycinnamate 2,4-dihydroxycinnamicacid 180.16 C9 H8 O4 C1(C=C(C=C(C=1C=CC(=O)O)O)O) 4-coumarate = 2,4-dihydroxycinnamate simplecoumarins biosynthesis 2,4-dihydroxycinnamate 2,4-dihydroxycinnamicacid 180.16 C9 H8 O4 C1(C=C(C=C(C=1C=CC(=O)O)O)O) 2,4-dihydroxycinnamate = umbelliferone simplecoumarins biosynthesis D-serine 105.093 C3 H7 N1 O3 C(C([O-])=O)(CO)[N+] PUBCHEM:6857549:*CHEBI:35247:*LIGAND-CPD:C00740:*CAS:312-84-5 4.3.1.18 D-serine = H+ + pyruvate + ammonia serine racemization D-serine 105.093 C3 H7 N1 O3 C(C([O-])=O)(CO)[N+] PUBCHEM:6857549:*CHEBI:35247:*LIGAND-CPD:C00740:*CAS:312-84-5 5.1.1.18 L-serine = D-serine serine racemization spermidine 148.271 C7 H22 N3 [N+]CCCC[N+]CCC[N+] PUBCHEM:6992097:*CHEBI:57834:*PUBCHEM:6992097:*LIGAND-CPD:C00315:*CAS:124-20-9 2.5.1.46 spermidine = propane-1,3-diamine hypusine biosynthesis spermidine 148.271 C7 H22 N3 [N+]CCCC[N+]CCC[N+] PUBCHEM:6992097:*CHEBI:57834:*PUBCHEM:6992097:*LIGAND-CPD:C00315:*CAS:124-20-9 2.5.1.22 spermidine + S-adenosyl-L-methioninamine = H+ + spermine + S-methyl-5'-thioadenosine spermine biosynthesis spermidine 148.271 C7 H22 N3 [N+]CCCC[N+]CCC[N+] PUBCHEM:6992097:*CHEBI:57834:*PUBCHEM:6992097:*LIGAND-CPD:C00315:*CAS:124-20-9 1.5.3.14 spermidine + oxygen + H2O = propane-1,3-diamine + 4-aminobutanal + hydrogen peroxide spermine and spermidine degradation II spermidine 148.271 C7 H22 N3 [N+]CCCC[N+]CCC[N+] PUBCHEM:6992097:*CHEBI:57834:*PUBCHEM:6992097:*LIGAND-CPD:C00315:*CAS:124-20-9 2.5.1.16 putrescine + S-adenosyl-L-methioninamine = H+ + spermidine + S-methyl-5'-thioadenosine spermidine biosynthesis I lauroyl-CoA Dodecanoyl-CoA (n-C12:0CoA)*lauroyl coenzyme A*dodecanoyl-CoA 945.808 C33 H54 N7 O17 P3 S1 O=C(CCCCCCCCCCC)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-] CHEBI:57375:*PUBCHEM:25113193:*LIGAND-CPD:C01832:*CAS:6244-92-4 3.1.2.2 lauroyl-CoA + H2O = H+ + laurate + coenzyme A ω-hydroxylation of caprate and laurate D-myo-inositol (1,2,6) trisphosphate 1D-myo-inositol (1,2,6) trisphosphate*Ins(1,2,6)P3*I(1,2,6)P3 414.049 C6 H9 O15 P3 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(O)C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:25201188:*PUBCHEM:25244400: D-myo-inositol (1,2,6) trisphosphate + H2O = D-myo-inositol (1,2) bisphosphate phytate degradation I D-myo-inositol (1,2,6) trisphosphate 1D-myo-inositol (1,2,6) trisphosphate*Ins(1,2,6)P3*I(1,2,6)P3 414.049 C6 H9 O15 P3 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(O)C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:25201188:*PUBCHEM:25244400: D-myo-inositol (1,2,5,6) tetrakisphosphate + H2O = D-myo-inositol (1,2,6) trisphosphate phytate degradation I D-myo-inositol (1,2,6) trisphosphate 1D-myo-inositol (1,2,6) trisphosphate*Ins(1,2,6)P3*I(1,2,6)P3 414.049 C6 H9 O15 P3 [O-]P([O-])(=O)OC1(C(OP([O-])(=O)[O-])C(O)C(O)C(O)C(OP(=O)([O-])[O-])1) PUBCHEM:25201188:*PUBCHEM:25244400: D-myo-inositol (1,2,3,6) tetrakisphosphate + H2O = D-myo-inositol (1,2,6) trisphosphate phytate degradation I 2-oxobutanoate 2-oxobutyrate*2-ketobutyrate*2-oxobutyric acid*α-oxobutyric acid*α-ketobutyrate*α-ketobutyric acid*2-oxo-butyrate*2-keto-butyrate*2-ketobutyric acid 101.082 C4 H5 O3 O=C(CC)C([O-])=O CHEBI:16763:*PUBCHEM:3593277:*LIGAND-CPD:C00109:*CAS:600-18-0 2-oxobutanoate = 5-hydroxy-2-oxopentanoate hypoglycin biosynthesis 2-oxobutanoate 2-oxobutyrate*2-ketobutyrate*2-oxobutyric acid*α-oxobutyric acid*α-ketobutyrate*α-ketobutyric acid*2-oxo-butyrate*2-keto-butyrate*2-ketobutyric acid 101.082 C4 H5 O3 O=C(CC)C([O-])=O CHEBI:16763:*PUBCHEM:3593277:*LIGAND-CPD:C00109:*CAS:600-18-0 4.3.1.19 L-threonine = H+ + 2-oxobutanoate + ammonia isoleucine biosynthesis I (from threonine) 2-oxobutanoate 2-oxobutyrate*2-ketobutyrate*2-oxobutyric acid*α-oxobutyric acid*α-ketobutyrate*α-ketobutyric acid*2-oxo-butyrate*2-keto-butyrate*2-ketobutyric acid 101.082 C4 H5 O3 O=C(CC)C([O-])=O CHEBI:16763:*PUBCHEM:3593277:*LIGAND-CPD:C00109:*CAS:600-18-0 4.3.1.19 L-threonine = H+ + 2-oxobutanoate + ammonia hypoglycin biosynthesis 2-oxobutanoate 2-oxobutyrate*2-ketobutyrate*2-oxobutyric acid*α-oxobutyric acid*α-ketobutyrate*α-ketobutyric acid*2-oxo-butyrate*2-keto-butyrate*2-ketobutyric acid 101.082 C4 H5 O3 O=C(CC)C([O-])=O CHEBI:16763:*PUBCHEM:3593277:*LIGAND-CPD:C00109:*CAS:600-18-0 4.4.1.1 L-cystathionine + H2O = H+ + ammonia + 2-oxobutanoate + L-cysteine homocysteine and cysteine interconversion 2-oxobutanoate 2-oxobutyrate*2-ketobutyrate*2-oxobutyric acid*α-oxobutyric acid*α-ketobutyrate*α-ketobutyric acid*2-oxo-butyrate*2-keto-butyrate*2-ketobutyric acid 101.082 C4 H5 O3 O=C(CC)C([O-])=O CHEBI:16763:*PUBCHEM:3593277:*LIGAND-CPD:C00109:*CAS:600-18-0 4.4.1.11 L-methionine + H2O = H+ + methanethiol + ammonia + 2-oxobutanoate methionine degradation II 2-oxobutanoate 2-oxobutyrate*2-ketobutyrate*2-oxobutyric acid*α-oxobutyric acid*α-ketobutyrate*α-ketobutyric acid*2-oxo-butyrate*2-keto-butyrate*2-ketobutyric acid 101.082 C4 H5 O3 O=C(CC)C([O-])=O CHEBI:16763:*PUBCHEM:3593277:*LIGAND-CPD:C00109:*CAS:600-18-0 2.2.1.6 H+ + pyruvate + 2-oxobutanoate = 2-aceto-2-hydroxy-butanoate + CO2 isoleucine biosynthesis I (from threonine) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 1.2.1.50 coenzyme A + NADP+ = NADPH + H+ cuticular wax biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid activation coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.- trans-cinnamate + coenzyme A + ATP = (E)-cinnamoyl-CoA + AMP + diphosphate trans-cinnamoyl-CoA biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.16 3-(4-hydroxyphenyl)-3-oxo-propionyl-CoA + coenzyme A = acetyl-CoA + 4-hydroxybenzoyl-CoA 4-hydroxybenzoate biosynthesis V coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.- sphinganine = coenzyme A sphingolipid biosynthesis (plants) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.20 wax esters biosynthesis II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.20 triacylglycerol biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2-oxoglutarate + coenzyme A + NAD+ = succinyl-CoA + CO2 + NADH TCA cycle variation III (eukaryotic) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 1.2.1.- NADPH + H+ = NADP+ + coenzyme A cuticular wax biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.110 feruloyl-CoA + tyramine = H+ + N-feruloyltyramine + coenzyme A suberin biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2-oxoadipate + NAD+ + coenzyme A = CO2 + NADH + glutaryl-CoA lysine degradation II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.10 acetoacetyl-CoA + H2O + acetyl-CoA = H+ + coenzyme A + (S)-3-hydroxy-3-methylglutaryl-CoA mevalonate pathway I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.12 acetyl-CoA = coenzyme A acetyl-CoA biosynthesis (from pyruvate) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.3 oleate + coenzyme A + ATP = oleoyl-CoA + AMP + diphosphate linoleate biosynthesis I (plants) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.23 4-hydroxybenzoyl-CoA + H2O = H+ + coenzyme A 4-hydroxybenzoate biosynthesis V coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: p-dihydrocoumaroyl-CoA + malonyl-CoA = naringenin + coenzyme A + CO2 phloridzin biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 4-methyl-2-oxopentanoate + coenzyme A + NAD+ = isovaleryl-CoA + CO2 + NADH leucine degradation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 1-dodecanol = coenzyme A wax esters biosynthesis II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.8 oxaloacetate + acetyl-CoA + ADP = citrate + coenzyme A + ATP acetyl-CoA biosynthesis (from citrate) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.20 jasmonoyl-CoA + H2O = H+ + (+)-7-iso-jasmonate + coenzyme A jasmonic acid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A glyoxylate cycle coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A TCA cycle variation III (eukaryotic) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = H+ + citrate + coenzyme A glutamine biosynthesis III coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2-keto-3-methyl-valerate + NAD+ + coenzyme A = 2-methylbutanoyl-CoA + NADH + CO2 isoleucine degradation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 1.1.1.34 NADP+ + coenzyme A + (R)-mevalonate = H+ + NADPH + (S)-3-hydroxy-3-methylglutaryl-CoA mevalonate pathway I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 1.2.1.27 (S)-methylmalonate-semialdehyde + coenzyme A + NAD+ + H2O = propanoyl-CoA + bicarbonate + NADH + H+ valine degradation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.9 acetyl-CoA = acetoacetyl-CoA + coenzyme A mevalonate pathway I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.16 OPC6-3-ketoacyl-CoA + coenzyme A = acetyl-CoA + OPC4-CoA jasmonic acid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.5 succinate + coenzyme A + ATP = succinyl-CoA + ADP TCA cycle variation III (eukaryotic) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.9 2-methylacetoacetyl-CoA + coenzyme A = propanoyl-CoA + acetyl-CoA isoleucine degradation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.170 H+ + 4-coumaroyl-CoA + malonyl-CoA + NADPH = isoliquiritigenin + coenzyme A + CO2 + NADP+ + H2O flavonoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.2 decanoyl-CoA + H2O = H+ + caprate + coenzyme A ω-hydroxylation of caprate and laurate coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.50 H+ + L-serine + palmitoyl-CoA = CO2 + 3-dehydrosphinganine + coenzyme A sphingolipid biosynthesis (plants) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.16 acetyl-CoA = coenzyme A fatty acid β-oxidation II (core pathway) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.4 D-glucosamine-6-phosphate + acetyl-CoA = H+ + N-acetyl-D-glucosamine-6-phosphate + coenzyme A UDP-N-acetyl-D-glucosamine biosynthesis II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.26 ATP + o-succinylbenzoate + coenzyme A = 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA + ADP 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.13 2-oxoisovalerate + acetyl-CoA + H2O = H+ + (2S)-2-isopropylmalate + coenzyme A leucine biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.75 cuticular wax biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.- 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate + coenzyme A + ATP = OPC8-CoA + AMP + diphosphate jasmonic acid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 1.2.1.25 2-oxoisovalerate + coenzyme A + NAD+ = isobutyryl-CoA + CO2 + NADH valine degradation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.74 H+ + 4-coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A flavonoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.74 H+ + 4-coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A aromatic polyketides biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.- malonyl-CoA = CO2 + coenzyme A very long chain fatty acid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.39 malonyl-CoA = coenzyme A fatty acid biosynthesis initiation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.41 malonyl-CoA = CO2 + coenzyme A stearate biosynthesis II (plants) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.- p-dihydrocoumaroyl-CoA + malonyl-CoA + H+ = phloretin + coenzyme A + CO2 phloridzin biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.- H+ + malonyl-CoA + (E)-cinnamoyl-CoA = pinocembrin chalcone + coenzyme A + CO2 pinobanksin biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.2 lauroyl-CoA + H2O = H+ + laurate + coenzyme A ω-hydroxylation of caprate and laurate coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: oleoyl-CoA = coenzyme A linoleate biosynthesis I (plants) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid β-oxidation II (core pathway) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.- H+ + 4-coumaroyl-CoA + H2O + malonyl-CoA = coenzyme A + CO2 + p-coumaroyltriacetate resveratrol biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.180 acetyl-CoA = coenzyme A + CO2 fatty acid biosynthesis initiation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP acetate conversion to acetyl-CoA coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP ethanol degradation II (cytosol) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP ethanol degradation IV (peroxisomal) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.153 delphinidin-3,5-diglucoside + caffeoyl-CoA = delphinidin 3-O-glucosyl-5-O-caffeoylglucoside + coenzyme A gentiodelphin biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.51 CDP-diacylglycerol biosynthesis I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.51 triacylglycerol biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.7.1.24 dephospho-CoA + ATP = H+ + coenzyme A + ADP coenzyme A biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.133 4-coumaroyl-CoA + L-quinate = trans-5-O-(4-coumaroyl)-D-quinate + coenzyme A chlorogenic acid biosynthesis I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.133 4-coumaroyl-CoA + L-quinate = trans-5-O-(4-coumaroyl)-D-quinate + coenzyme A chlorogenic acid biosynthesis II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.133 4-coumaroyl-CoA + L-quinate = trans-5-O-(4-coumaroyl)-D-quinate + coenzyme A phenylpropanoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.-.- 2-oxohexa-4,5-cyclopropyl-5-enoate + acetyl-CoA + H2O = H+ + 3-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate + coenzyme A hypoglycin biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.7.8.7 coenzyme A = adenosine 3',5'-bisphosphate acyl carrier protein metabolism coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.144 anthranilate + benzoyl-CoA = N-benzoylanthranilate + coenzyme A benzoylanthranilate biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.61 succinyl-CoA = coenzyme A 2-ketoglutarate dehydrogenase complex coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.- H+ + 4-coumaroyl-CoA + malonyl-CoA = p-coumaroyltriacetic acid lactone + coenzyme A + CO2 aromatic polyketides biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.17 coenzyme A + propionate + ATP = propanoyl-CoA + diphosphate + AMP β-alanine biosynthesis II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.12 trans-caffeate + coenzyme A + ATP = caffeoyl-CoA + AMP + diphosphate suberin biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.- acetyl-CoA + (3Z)-hex-3-en-ol = (3Z)-hex-3-en-1-yl acetate + coenzyme A traumatin and (Z)-3-hexen-1-yl acetate biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.4 3-hydroxypropanoyl-CoA + H2O = H+ + 3-hydroxypropionate + coenzyme A β-alanine biosynthesis II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A chlorogenic acid biosynthesis I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A chlorogenic acid biosynthesis II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A simplecoumarins biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.133 4-coumaroyl-CoA + shikimate = 4-coumaroylshikimate + coenzyme A phenylpropanoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.- caffeoylshikimate + coenzyme A = caffeoyl-CoA + shikimate chlorogenic acid biosynthesis I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.- caffeoylshikimate + coenzyme A = caffeoyl-CoA + shikimate phenylpropanoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.1 L-glutamate + acetyl-CoA = H+ + N-acetyl-L-glutamate + coenzyme A arginine biosynthesis II (acetyl cycle) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.1 L-glutamate + acetyl-CoA = H+ + N-acetyl-L-glutamate + coenzyme A ornithine biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.2 H2O = coenzyme A + H+ acyl-CoA hydrolysis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.- delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + caffeoyl-CoA = gentiodelphin + coenzyme A gentiodelphin biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.- delphinidin 3,5,3'-triglucoside + caffeoyl-CoA = delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + coenzyme A gentiodelphin biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.15 sn-glycerol-3-phosphate = coenzyme A CDP-diacylglycerol biosynthesis I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.15 sn-glycerol-3-phosphate = coenzyme A triacylglycerol biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 1.2.1.44 4-coumaroyl-CoA + NADPH + H+ = coumaraldehyde + coenzyme A + NADP+ phenylpropanoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ flavonoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ simplecoumarins biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ phenylpropanoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ 4-hydroxybenzoate biosynthesis V coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.- H+ + 4-coumaroyl-CoA + malonyl-CoA = bis-noryangonin + coenzyme A + CO2 resveratrol biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.- trans-5-O-caffeoyl-D-quinate + coenzyme A = caffeoyl-CoA + L-quinate chlorogenic acid biosynthesis I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.- trans-5-O-caffeoyl-D-quinate + coenzyme A = caffeoyl-CoA + L-quinate phenylpropanoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.95 H+ + 4-coumaroyl-CoA + malonyl-CoA = resveratrol + coenzyme A + CO2 resveratrol biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.28 1,4-dihydroxy-2-naphthoyl-CoA + H2O = H+ + 1,4-dihydroxy-2-naphthoate + coenzyme A 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.34 ferulate + ATP + coenzyme A = feruloyl-CoA + AMP + diphosphate suberin biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 1.2.1.44 H+ + feruloyl-CoA + NADPH = coniferaldehyde + NADP+ + coenzyme A phenylpropanoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.16 OPC4-3-ketoacyl-CoA + coenzyme A = acetyl-CoA + jasmonoyl-CoA jasmonic acid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.16 OPC8-3-ketoacyl-CoA + coenzyme A = acetyl-CoA + OPC6-CoA jasmonic acid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.9 acetyl-CoA + H2O + glyoxylate = H+ + (S)-malate + coenzyme A glyoxylate cycle coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.9 acetyl-CoA + H2O + glyoxylate = H+ + (S)-malate + coenzyme A glycolate and glyoxylate degradation II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.30 L-serine + acetyl-CoA = O-acetyl-L-serine + coenzyme A cysteine biosynthesis I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 763.502 C21 H32 N7 O16 P3 S1 C1(OC(COP(=O)(OP(=O)(OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)[O-])[O-])C(OP([O-])(=O)[O-])C(O)1)N3(C2(=C(C(N)=NC=N2)N=C3)) CHEBI:57287:*PUBCHEM:25113190:*PUBCHEM:25113190:*KNAPSACK:C00007258:*CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.4 (S)-3-hydroxy-isobutyryl-CoA + H2O = (S)-3-hydroxy-isobutyrate + H+ + coenzyme A valine degradation I 3,7,3'-tri-methylquercetagetin 3, 7, 3’-O-trimethylquercetagetin*3, 7, 3'-O-trimethylquercetagetin 360.32 C18 H16 O8 COC3(C(=O)C1(C(=CC(OC)=C(O)C(O)=1)OC(C2(C=C(OC)C(O)=CC=2))=3)) PUBCHEM:189065:*CHEBI:584570:*PUBCHEM:189065:*LIGAND-CPD:C10031: 3,7-di-methylquercetagetin + S-adenosyl-L-methionine = H+ + 3,7,3'-tri-methylquercetagetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis 3,7,3'-tri-methylquercetagetin 3, 7, 3’-O-trimethylquercetagetin*3, 7, 3'-O-trimethylquercetagetin 360.32 C18 H16 O8 COC3(C(=O)C1(C(=CC(OC)=C(O)C(O)=1)OC(C2(C=C(OC)C(O)=CC=2))=3)) PUBCHEM:189065:*CHEBI:584570:*PUBCHEM:189065:*LIGAND-CPD:C10031: 3,7,3'-tri-methylquercetagetin + S-adenosyl-L-methionine = H+ + 3,6,7,3'-tetra-methylquercetagetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis L-proline 2-pyrrolidinecarboxylic acid*P*proline*prol*pro 115.132 C5 H9 N1 O2 [N+]1(C(C(=O)[O-])CCC1) KNAPSACK:C00001388:*PUBCHEM:25246272:*CHEBI:60039:*PUBCHEM:6971047:*LIGAND-CPD:C00148:*CAS:147-85-3 1.5.1.2 L-proline = (S)-1-pyrroline-5-carboxylate + H+ arginine degradation VI (arginase 2 pathway) L-proline 2-pyrrolidinecarboxylic acid*P*proline*prol*pro 115.132 C5 H9 N1 O2 [N+]1(C(C(=O)[O-])CCC1) KNAPSACK:C00001388:*PUBCHEM:25246272:*CHEBI:60039:*PUBCHEM:6971047:*LIGAND-CPD:C00148:*CAS:147-85-3 1.5.1.2 L-proline = (S)-1-pyrroline-5-carboxylate + H+ proline biosynthesis II (from arginine) L-proline 2-pyrrolidinecarboxylic acid*P*proline*prol*pro 115.132 C5 H9 N1 O2 [N+]1(C(C(=O)[O-])CCC1) KNAPSACK:C00001388:*PUBCHEM:25246272:*CHEBI:60039:*PUBCHEM:6971047:*LIGAND-CPD:C00148:*CAS:147-85-3 1.5.1.2 L-proline = (S)-1-pyrroline-5-carboxylate + H+ proline biosynthesis I L-proline 2-pyrrolidinecarboxylic acid*P*proline*prol*pro 115.132 C5 H9 N1 O2 [N+]1(C(C(=O)[O-])CCC1) KNAPSACK:C00001388:*PUBCHEM:25246272:*CHEBI:60039:*PUBCHEM:6971047:*LIGAND-CPD:C00148:*CAS:147-85-3 6.1.1.15 H+ + L-proline + ATP = diphosphate + AMP tRNA charging pathway L-proline 2-pyrrolidinecarboxylic acid*P*proline*prol*pro 115.132 C5 H9 N1 O2 [N+]1(C(C(=O)[O-])CCC1) KNAPSACK:C00001388:*PUBCHEM:25246272:*CHEBI:60039:*PUBCHEM:6971047:*LIGAND-CPD:C00148:*CAS:147-85-3 1.5.99.8 L-proline = (S)-1-pyrroline-5-carboxylate proline degradation L-proline 2-pyrrolidinecarboxylic acid*P*proline*prol*pro 115.132 C5 H9 N1 O2 [N+]1(C(C(=O)[O-])CCC1) KNAPSACK:C00001388:*PUBCHEM:25246272:*CHEBI:60039:*PUBCHEM:6971047:*LIGAND-CPD:C00148:*CAS:147-85-3 1.5.99.8 L-proline = (S)-1-pyrroline-5-carboxylate citrulline biosynthesis 3,6,7,3'-tetra-methylquercetagetin 374.346 C19 H18 O8 COC3(C(=O)C1(C(=CC(OC)=C(OC)C(O)=1)OC(C2(C=C(OC)C(O)=CC=2))=3)) PUBCHEM:5281608:*CHEBI:150139:*PUBCHEM:5281608:*LIGAND-CPD:C10030: 3,7,3'-tri-methylquercetagetin + S-adenosyl-L-methionine = H+ + 3,6,7,3'-tetra-methylquercetagetin + S-adenosyl-L-homocysteine methylquercetin biosynthesis dUTP deoxy-UTP*2'-deoxyuridine-5'-triphosphate*deoxyuridine-triphosphate 464.112 C9 H11 N2 O14 P3 O=C1(C=CN(C(=O)N1)C2(CC(O)C(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])O2)) PUBCHEM:25244408:*LIGAND-CPD:C00460:*CAS:1173-82-6 2.7.4.6 dUDP + ATP = dUTP + ADP pyrimidine deoxyribonucleotides de novo biosynthesis I dUTP deoxy-UTP*2'-deoxyuridine-5'-triphosphate*deoxyuridine-triphosphate 464.112 C9 H11 N2 O14 P3 O=C1(C=CN(C(=O)N1)C2(CC(O)C(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])O2)) PUBCHEM:25244408:*LIGAND-CPD:C00460:*CAS:1173-82-6 UTP = dUTP + H2O pyrimidine deoxyribonucleotides de novo biosynthesis I dUTP deoxy-UTP*2'-deoxyuridine-5'-triphosphate*deoxyuridine-triphosphate 464.112 C9 H11 N2 O14 P3 O=C1(C=CN(C(=O)N1)C2(CC(O)C(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])O2)) PUBCHEM:25244408:*LIGAND-CPD:C00460:*CAS:1173-82-6 3.5.4.13 H2O + dCTP = ammonia + dUTP pyrimidine deoxyribonucleotides de novo biosynthesis I dUTP deoxy-UTP*2'-deoxyuridine-5'-triphosphate*deoxyuridine-triphosphate 464.112 C9 H11 N2 O14 P3 O=C1(C=CN(C(=O)N1)C2(CC(O)C(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])O2)) PUBCHEM:25244408:*LIGAND-CPD:C00460:*CAS:1173-82-6 3.6.1.23 dUTP + H2O = H+ + dUMP + diphosphate pyrimidine deoxyribonucleotides de novo biosynthesis I 1D-myo-inositol (3)-monophosphate 1D-myo-inositol 3-monophosphate*1-L-myo-inositol-1-p*L-myo-inositol 1-phosphate*inositol 1-phosphate*myo-inositol 1-phosphate*1D-myo-inositol 3-phosphate*Ins(3)P1*D-myo-inositol (3)-monophosphate*myo-inositol 1-monophosphate*Ins3P*1L-myo-inositol 1-phosphate*myo-inositol phosphate 258.121 C6 H11 O9 P1 O=P([O-])(OC1(C(O)C(O)C(O)C(O)C(O)1))[O-] PUBCHEM:5288700:*CHEBI:58401:*PUBCHEM:5288700:*LIGAND-CPD:C04006: 1D-myo-inositol (3)-monophosphate + ATP = H+ + D-myo-inositol (3,4)-bisphosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) 1D-myo-inositol (3)-monophosphate 1D-myo-inositol 3-monophosphate*1-L-myo-inositol-1-p*L-myo-inositol 1-phosphate*inositol 1-phosphate*myo-inositol 1-phosphate*1D-myo-inositol 3-phosphate*Ins(3)P1*D-myo-inositol (3)-monophosphate*myo-inositol 1-monophosphate*Ins3P*1L-myo-inositol 1-phosphate*myo-inositol phosphate 258.121 C6 H11 O9 P1 O=P([O-])(OC1(C(O)C(O)C(O)C(O)C(O)1))[O-] PUBCHEM:5288700:*CHEBI:58401:*PUBCHEM:5288700:*LIGAND-CPD:C04006: 3.1.3.25 1D-myo-inositol (3)-monophosphate + H2O = myo-inositol myo-inositol biosynthesis 1D-myo-inositol (3)-monophosphate 1D-myo-inositol 3-monophosphate*1-L-myo-inositol-1-p*L-myo-inositol 1-phosphate*inositol 1-phosphate*myo-inositol 1-phosphate*1D-myo-inositol 3-phosphate*Ins(3)P1*D-myo-inositol (3)-monophosphate*myo-inositol 1-monophosphate*Ins3P*1L-myo-inositol 1-phosphate*myo-inositol phosphate 258.121 C6 H11 O9 P1 O=P([O-])(OC1(C(O)C(O)C(O)C(O)C(O)1))[O-] PUBCHEM:5288700:*CHEBI:58401:*PUBCHEM:5288700:*LIGAND-CPD:C04006: 5.5.1.4 myo-inositol biosynthesis 1D-myo-inositol (3)-monophosphate 1D-myo-inositol 3-monophosphate*1-L-myo-inositol-1-p*L-myo-inositol 1-phosphate*inositol 1-phosphate*myo-inositol 1-phosphate*1D-myo-inositol 3-phosphate*Ins(3)P1*D-myo-inositol (3)-monophosphate*myo-inositol 1-monophosphate*Ins3P*1L-myo-inositol 1-phosphate*myo-inositol phosphate 258.121 C6 H11 O9 P1 O=P([O-])(OC1(C(O)C(O)C(O)C(O)C(O)1))[O-] PUBCHEM:5288700:*CHEBI:58401:*PUBCHEM:5288700:*LIGAND-CPD:C04006: 5.5.1.4 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) 1D-myo-inositol (3)-monophosphate 1D-myo-inositol 3-monophosphate*1-L-myo-inositol-1-p*L-myo-inositol 1-phosphate*inositol 1-phosphate*myo-inositol 1-phosphate*1D-myo-inositol 3-phosphate*Ins(3)P1*D-myo-inositol (3)-monophosphate*myo-inositol 1-monophosphate*Ins3P*1L-myo-inositol 1-phosphate*myo-inositol phosphate 258.121 C6 H11 O9 P1 O=P([O-])(OC1(C(O)C(O)C(O)C(O)C(O)1))[O-] PUBCHEM:5288700:*CHEBI:58401:*PUBCHEM:5288700:*LIGAND-CPD:C04006: 2.7.1.64 myo-inositol + ATP = H+ + 1D-myo-inositol (3)-monophosphate + ADP 1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) pelargonidin-3-O-β-D-glucoside C21H21CLO5*callistephin*3-(β-D-glucopyranosyloxy)-55,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chloride 433.391 C21 H21 O10 C1(C(=CC(=C2(C=1O=C(C(=C2)OC3(OC(C(C(C3O)O)O)CO))C4(C=CC(=CC=4)O)))O)O) LIGAND-CPD:C12137:*CHEBI:31967: 2.4.1.115 pelargonidin = H+ + UDP + pelargonidin-3-O-β-D-glucoside anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) (3Z)-hex-3-en-ol cis-3-hexenol 100.16 C6 H12 O1 CCC=CCCO PUBCHEM:5284503:*LIGAND-CPD:C08492:*NCI:74451*CAS:928-96-1 2.3.1.- acetyl-CoA + (3Z)-hex-3-en-ol = (3Z)-hex-3-en-1-yl acetate + coenzyme A traumatin and (Z)-3-hexen-1-yl acetate biosynthesis (3Z)-hex-3-en-ol cis-3-hexenol 100.16 C6 H12 O1 CCC=CCCO PUBCHEM:5284503:*LIGAND-CPD:C08492:*NCI:74451*CAS:928-96-1 (3Z)-hex-3-en-ol + NAD+ = cis-3-hexenal + NADH + H+ traumatin and (Z)-3-hexen-1-yl acetate biosynthesis leucocyanidin a flavan-3,4-diol*2,3-trans-3,4-cis-leucocyanidin 306.271 C15 H14 O7 C1(C(=CC(=C2(C=1OC(C(C2O)O)C3(C=CC(=C(C=3)O)O)))O)O) PUBCHEM:440833:*CHEBI:11412:*LIGAND-CPD:C05906: 1.14.11.19 leucocyanidin + 2-oxoglutarate + oxygen = succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) leucocyanidin a flavan-3,4-diol*2,3-trans-3,4-cis-leucocyanidin 306.271 C15 H14 O7 C1(C(=CC(=C2(C=1OC(C(C2O)O)C3(C=CC(=C(C=3)O)O)))O)O) PUBCHEM:440833:*CHEBI:11412:*LIGAND-CPD:C05906: 1.17.1.3 catechin + NADP+ + H2O = leucocyanidin + NADPH + H+ 2,3-trans-flavanols biosynthesis leucocyanidin a flavan-3,4-diol*2,3-trans-3,4-cis-leucocyanidin 306.271 C15 H14 O7 C1(C(=CC(=C2(C=1OC(C(C2O)O)C3(C=CC(=C(C=3)O)O)))O)O) PUBCHEM:440833:*CHEBI:11412:*LIGAND-CPD:C05906: 1.14.11.- leucocyanidin + 2-oxoglutarate + oxygen = H+ + cyanidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) leucocyanidin a flavan-3,4-diol*2,3-trans-3,4-cis-leucocyanidin 306.271 C15 H14 O7 C1(C(=CC(=C2(C=1OC(C(C2O)O)C3(C=CC(=C(C=3)O)O)))O)O) PUBCHEM:440833:*CHEBI:11412:*LIGAND-CPD:C05906: 1.1.1.219 H+ + trans dihydroquercetin + NADPH = leucocyanidin + NADP+ leucopelargonidin and leucocyanidin biosynthesis dihydrosterculate dihydrosterculic acid 295.484 C19 H35 O2 CCCCCCCCC1(CC(CCCCCCCC(=O)[O-])1) PUBCHEM:25246275: 2.1.1.79 oleate + S-adenosyl-L-methionine = H+ + dihydrosterculate + S-adenosyl-L-homocysteine cyclopropane and cyclopropene fatty acid biosynthesis dihydrosterculate dihydrosterculic acid 295.484 C19 H35 O2 CCCCCCCCC1(CC(CCCCCCCC(=O)[O-])1) PUBCHEM:25246275: dihydrosterculate = H+ + sterculate cyclopropane and cyclopropene fatty acid biosynthesis gentiodelphin delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-caffeoylglucoside 1112.955 C51 H52 O28 C8(C5(=C(C=C(OC1(OC(CO)C(O)C(O)C(O)1))C(C4(C=C(O)C(O)=C(OC3(C(O)C(O)C(O)C(COC(=O)C=CC2(C=CC(O)=C(O)C=2))O3))C=4))=[O+]5)C(OC7(C(O)C(O)C(O)C(COC(=O)C=CC6(C=CC(O)=C(O)C=6))O7))=CC([O-])=8)) PUBCHEM:25244415:*LIGAND-CPD:C08641: 2.3.1.- delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + caffeoyl-CoA = gentiodelphin + coenzyme A gentiodelphin biosynthesis but-1-en-3-one methyl vinyl ketone*3-buten-2-one*1-buten-3-one*but-3-en-2-one*3-oxo-1-butene 70.091 C4 H6 O1 C(C=C)(C)=O PUBCHEM:6570:*CHEBI:48058: 1.14.13.- H+ + (3S,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis but-1-en-3-one methyl vinyl ketone*3-buten-2-one*1-buten-3-one*but-3-en-2-one*3-oxo-1-butene 70.091 C4 H6 O1 C(C=C)(C)=O PUBCHEM:6570:*CHEBI:48058: 1.14.13.- H+ + (3R,6E)-nerolidol + NADPH + oxygen = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis OPC6-trans-2-enoyl-CoA 1009.851 C37 H54 N7 O18 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)=CCCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237321: 4.2.1.17 OPC6-3-hydroxyacyl-CoA = OPC6-trans-2-enoyl-CoA + H2O jasmonic acid biosynthesis OPC6-trans-2-enoyl-CoA 1009.851 C37 H54 N7 O18 P3 S1 C(C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-])=O)=CCCCC4(CCC(=O)C(CC=CCC)4) PUBCHEM:44237321: 1.3.3.6 OPC6-CoA + oxygen = OPC6-trans-2-enoyl-CoA + hydrogen peroxide jasmonic acid biosynthesis GA12-aldehyde gibberellin A12-aldehyde*gibberellin A12-aldehyde*GA12-aldehyde 315.431 C20 H27 O3 C1(CCC(C2(C(C34(CC(CCC(C1(C)2)3)C(C4)=C))C=O))(C)C([O-])=O) CHEBI:57432:*PUBCHEM:25244417:*LIGAND-CPD:C06093: 1.14.13.79 GA12-aldehyde + NADPH + oxygen = gibberellin A12 + NADP+ + H2O GA12 biosynthesis GA12-aldehyde gibberellin A12-aldehyde*gibberellin A12-aldehyde*GA12-aldehyde 315.431 C20 H27 O3 C1(CCC(C2(C(C34(CC(CCC(C1(C)2)3)C(C4)=C))C=O))(C)C([O-])=O) CHEBI:57432:*PUBCHEM:25244417:*LIGAND-CPD:C06093: 1.14.13.79 ent-7-α-hydroxykaurenoate + NADPH + H+ + oxygen = GA12-aldehyde + NADP+ + H2O GA12 biosynthesis γ-tocopherol 7,8-dimethyltocol 416.686 C28 H48 O2 CC2(C(=C(C=C1(CCC(C)(CCCC(C)CCCC(C)CCCC(C)C)OC1=2))O)C) CHEBI:18185:*PUBCHEM:92729:*LIGAND-CPD:C02483: 2,3-dimethyl-6-phytyl-1,4-benzoquinol = γ-tocopherol vitamin E biosynthesis γ-tocopherol 7,8-dimethyltocol 416.686 C28 H48 O2 CC2(C(=C(C=C1(CCC(C)(CCCC(C)CCCC(C)CCCC(C)C)OC1=2))O)C) CHEBI:18185:*PUBCHEM:92729:*LIGAND-CPD:C02483: 2.1.1.95 γ-tocopherol + S-adenosyl-L-methionine = H+ + S-adenosyl-L-homocysteine + α-tocopherol vitamin E biosynthesis 3-methoxy-4-hydroxy-5-all-trans-decaprenylbenzoate 3-methoxy-4-hydroxy-5-decaprenylbenzoate*3-(3,7,11,15,19,23-decamethyltetracosa-2,6,10,14,18,22-hexaenyl) -4-hydroxy-5-methoxy-benzoic acid*3-decaprenyl-4-hydroxy-5-methoxybenzoate 848.323 C58 H87 O4 COC1(C(=C(CC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(C)C)C)C)C)C)C)C)C)C)C)C=C(C([O-])=O)C=1)O) PUBCHEM:25246278: 4.1.1.- H+ + 3-methoxy-4-hydroxy-5-all-trans-decaprenylbenzoate = 2-decaprenyl-6-methoxyphenol + CO2 ubiquinol-10 biosynthesis (eukaryotic) 3-methoxy-4-hydroxy-5-all-trans-decaprenylbenzoate 3-methoxy-4-hydroxy-5-decaprenylbenzoate*3-(3,7,11,15,19,23-decamethyltetracosa-2,6,10,14,18,22-hexaenyl) -4-hydroxy-5-methoxy-benzoic acid*3-decaprenyl-4-hydroxy-5-methoxybenzoate 848.323 C58 H87 O4 COC1(C(=C(CC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(C)C)C)C)C)C)C)C)C)C)C)C=C(C([O-])=O)C=1)O) PUBCHEM:25246278: 2.1.1.114 3,4-dihydroxy-5-all-trans-decaprenylbenzoate + S-adenosyl-L-methionine = H+ + 3-methoxy-4-hydroxy-5-all-trans-decaprenylbenzoate + S-adenosyl-L-homocysteine ubiquinol-10 biosynthesis (eukaryotic) indol-3-yl-acetyl-myo-inositol indole-3-acetyl-myo-inositol*Indole-3-ylacetyl-myo-inositol*indol-3-ylacetyl-1D-myo-inositol 337.329 C16 H19 N1 O7 O=C(CC1(=CNC2(C=CC=CC1=2)))OC3(C(O)C(O)C(O)C(O)C(O)3) PUBCHEM:440152:*CHEBI:15711:*LIGAND-CPD:C03868: 2.4.1.156 indol-3-yl-acetyl-myo-inositol + UDP-D-galactose = H+ + 5-O-(indol-3-ylacetyl-myo-inositol) D-galactoside + UDP IAA conjugate biosynthesis I indol-3-yl-acetyl-myo-inositol indole-3-acetyl-myo-inositol*Indole-3-ylacetyl-myo-inositol*indol-3-ylacetyl-1D-myo-inositol 337.329 C16 H19 N1 O7 O=C(CC1(=CNC2(C=CC=CC1=2)))OC3(C(O)C(O)C(O)C(O)C(O)3) PUBCHEM:440152:*CHEBI:15711:*LIGAND-CPD:C03868: 2.4.2.34 indol-3-yl-acetyl-myo-inositol = H+ + UDP + indole-3-yl-acetyl-myo-inositol L-arabinoside IAA conjugate biosynthesis I indol-3-yl-acetyl-myo-inositol indole-3-acetyl-myo-inositol*Indole-3-ylacetyl-myo-inositol*indol-3-ylacetyl-1D-myo-inositol 337.329 C16 H19 N1 O7 O=C(CC1(=CNC2(C=CC=CC1=2)))OC3(C(O)C(O)C(O)C(O)C(O)3) PUBCHEM:440152:*CHEBI:15711:*LIGAND-CPD:C03868: 2.3.1.72 myo-inositol + indole-3-acetyl-β-1-D-glucose = indol-3-yl-acetyl-myo-inositol + β-D-glucose IAA conjugate biosynthesis I malonyl-CoA malonylCoenzyme A 848.541 C24 H33 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-])O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25246281:*LIGAND-CPD:C00083:*CAS:524-14-1 6.4.1.2 acetyl-CoA = malonyl-CoA biotin-carboxyl carrier protein assembly malonyl-CoA malonylCoenzyme A 848.541 C24 H33 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-])O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25246281:*LIGAND-CPD:C00083:*CAS:524-14-1 p-dihydrocoumaroyl-CoA + malonyl-CoA = naringenin + coenzyme A + CO2 phloridzin biosynthesis malonyl-CoA malonylCoenzyme A 848.541 C24 H33 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-])O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25246281:*LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.- malonyl-CoA = CO2 + coenzyme A very long chain fatty acid biosynthesis malonyl-CoA malonylCoenzyme A 848.541 C24 H33 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-])O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25246281:*LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.170 H+ + 4-coumaroyl-CoA + malonyl-CoA + NADPH = isoliquiritigenin + coenzyme A + CO2 + NADP+ + H2O flavonoid biosynthesis malonyl-CoA malonylCoenzyme A 848.541 C24 H33 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-])O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25246281:*LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.39 malonyl-CoA = coenzyme A fatty acid biosynthesis initiation I malonyl-CoA malonylCoenzyme A 848.541 C24 H33 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-])O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25246281:*LIGAND-CPD:C00083:*CAS:524-14-1 6.4.1.2 ATP + acetyl-CoA + bicarbonate = H+ + malonyl-CoA + ADP fatty acid biosynthesis initiation I malonyl-CoA malonylCoenzyme A 848.541 C24 H33 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-])O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25246281:*LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.41 malonyl-CoA = CO2 + coenzyme A stearate biosynthesis II (plants) malonyl-CoA malonylCoenzyme A 848.541 C24 H33 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-])O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25246281:*LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.- p-dihydrocoumaroyl-CoA + malonyl-CoA + H+ = phloretin + coenzyme A + CO2 phloridzin biosynthesis malonyl-CoA malonylCoenzyme A 848.541 C24 H33 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-])O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25246281:*LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.- H+ + 4-coumaroyl-CoA + malonyl-CoA = bis-noryangonin + coenzyme A + CO2 resveratrol biosynthesis malonyl-CoA malonylCoenzyme A 848.541 C24 H33 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-])O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25246281:*LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.- H+ + malonyl-CoA + (E)-cinnamoyl-CoA = pinocembrin chalcone + coenzyme A + CO2 pinobanksin biosynthesis malonyl-CoA malonylCoenzyme A 848.541 C24 H33 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-])O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25246281:*LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.95 H+ + 4-coumaroyl-CoA + malonyl-CoA = resveratrol + coenzyme A + CO2 resveratrol biosynthesis malonyl-CoA malonylCoenzyme A 848.541 C24 H33 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-])O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25246281:*LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.74 H+ + 4-coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A flavonoid biosynthesis malonyl-CoA malonylCoenzyme A 848.541 C24 H33 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-])O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25246281:*LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.74 H+ + 4-coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A aromatic polyketides biosynthesis malonyl-CoA malonylCoenzyme A 848.541 C24 H33 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-])O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25246281:*LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.- H+ + 4-coumaroyl-CoA + malonyl-CoA = p-coumaroyltriacetic acid lactone + coenzyme A + CO2 aromatic polyketides biosynthesis malonyl-CoA malonylCoenzyme A 848.541 C24 H33 N7 O19 P3 S1 C1(C(O)C(C(COP([O-])(=O)OP(=O)(OCC(C)(C)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-])O)[O-])O1)OP([O-])(=O)[O-])(N3(C=NC2(C(N)=NC=NC=23))) PUBCHEM:25246281:*LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.- H+ + 4-coumaroyl-CoA + H2O + malonyl-CoA = coenzyme A + CO2 + p-coumaroyltriacetate resveratrol biosynthesis anthranilate anthranilic acid*2-aminobenzoic acid*vitamin L1*o-aminobenzoic acid*2-aminobenzoate 136.13 C7 H6 N1 O2 C1(C(=C(C=CC=1)N)C(=O)[O-]) CHEBI:16567:*PUBCHEM:5459842:*PUBCHEM:227:*LIGAND-CPD:C00108:*CAS:118-92-3 2.3.1.144 anthranilate + benzoyl-CoA = N-benzoylanthranilate + coenzyme A benzoylanthranilate biosynthesis anthranilate anthranilic acid*2-aminobenzoic acid*vitamin L1*o-aminobenzoic acid*2-aminobenzoate 136.13 C7 H6 N1 O2 C1(C(=C(C=CC=1)N)C(=O)[O-]) CHEBI:16567:*PUBCHEM:5459842:*PUBCHEM:227:*LIGAND-CPD:C00108:*CAS:118-92-3 2.4.2.18 N-(5'-phosphoribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-α-D-ribose 1-diphosphate tryptophan biosynthesis anthranilate anthranilic acid*2-aminobenzoic acid*vitamin L1*o-aminobenzoic acid*2-aminobenzoate 136.13 C7 H6 N1 O2 C1(C(=C(C=CC=1)N)C(=O)[O-]) CHEBI:16567:*PUBCHEM:5459842:*PUBCHEM:227:*LIGAND-CPD:C00108:*CAS:118-92-3 4.1.3.27 chorismate + L-glutamine = H+ + anthranilate + L-glutamate + pyruvate tryptophan biosynthesis anthranilate anthranilic acid*2-aminobenzoic acid*vitamin L1*o-aminobenzoic acid*2-aminobenzoate 136.13 C7 H6 N1 O2 C1(C(=C(C=CC=1)N)C(=O)[O-]) CHEBI:16567:*PUBCHEM:5459842:*PUBCHEM:227:*LIGAND-CPD:C00108:*CAS:118-92-3 1.14.14.8 anthranilate + oxygen + FADH2 = 3-hydroxyanthranilate + H2O + FAD + H+ anthranilate degradation IV (aerobic) L-ascorbate L-ascorbic acid*L-ascorbate (vitamin C)*ascorbate*vitamin C*ascorbic acid 175.118 C6 H7 O6 O1(C([H])(C(O)CO)C(=C(C(=O)1)O)[O-]) CHEBI:38290:*PUBCHEM:44229109:*PUBCHEM:25200374:*KNAPSACK:C00001179:*LIGAND-CPD:C00072:*CAS:50-81-7 1.8.5.1 L-dehydro-ascorbate + glutathione = H+ + glutathione disulfide + L-ascorbate ascorbate glutathione cycle L-ascorbate L-ascorbic acid*L-ascorbate (vitamin C)*ascorbate*vitamin C*ascorbic acid 175.118 C6 H7 O6 O1(C([H])(C(O)CO)C(=C(C(=O)1)O)[O-]) CHEBI:38290:*PUBCHEM:44229109:*PUBCHEM:25200374:*KNAPSACK:C00001179:*LIGAND-CPD:C00072:*CAS:50-81-7 1.6.5.4 monodehydroascorbate + NADPH = H+ + L-ascorbate + NADP+ ascorbate glutathione cycle L-ascorbate L-ascorbic acid*L-ascorbate (vitamin C)*ascorbate*vitamin C*ascorbic acid 175.118 C6 H7 O6 O1(C([H])(C(O)CO)C(=C(C(=O)1)O)[O-]) CHEBI:38290:*PUBCHEM:44229109:*PUBCHEM:25200374:*KNAPSACK:C00001179:*LIGAND-CPD:C00072:*CAS:50-81-7 1.14.17.4 H+ + L-ascorbate + 1-aminocyclopropane-1-carboxylate + oxygen = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine L-ascorbate L-ascorbic acid*L-ascorbate (vitamin C)*ascorbate*vitamin C*ascorbic acid 175.118 C6 H7 O6 O1(C([H])(C(O)CO)C(=C(C(=O)1)O)[O-]) CHEBI:38290:*PUBCHEM:44229109:*PUBCHEM:25200374:*KNAPSACK:C00001179:*LIGAND-CPD:C00072:*CAS:50-81-7 1.11.1.11 H+ + L-ascorbate + hydrogen peroxide = monodehydroascorbate + H2O ascorbate glutathione cycle L-ascorbate L-ascorbic acid*L-ascorbate (vitamin C)*ascorbate*vitamin C*ascorbic acid 175.118 C6 H7 O6 O1(C([H])(C(O)CO)C(=C(C(=O)1)O)[O-]) CHEBI:38290:*PUBCHEM:44229109:*PUBCHEM:25200374:*KNAPSACK:C00001179:*LIGAND-CPD:C00072:*CAS:50-81-7 1.10.99.3 H+ + violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O antheraxanthin and violaxanthin biosynthesis L-ascorbate L-ascorbic acid*L-ascorbate (vitamin C)*ascorbate*vitamin C*ascorbic acid 175.118 C6 H7 O6 O1(C([H])(C(O)CO)C(=C(C(=O)1)O)[O-]) CHEBI:38290:*PUBCHEM:44229109:*PUBCHEM:25200374:*KNAPSACK:C00001179:*LIGAND-CPD:C00072:*CAS:50-81-7 1.10.99.3 H+ + violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle L-ascorbate L-ascorbic acid*L-ascorbate (vitamin C)*ascorbate*vitamin C*ascorbic acid 175.118 C6 H7 O6 O1(C([H])(C(O)CO)C(=C(C(=O)1)O)[O-]) CHEBI:38290:*PUBCHEM:44229109:*PUBCHEM:25200374:*KNAPSACK:C00001179:*LIGAND-CPD:C00072:*CAS:50-81-7 1.3.2.3 L-galactono-1,4-lactone = L-ascorbate ascorbate biosynthesis I (L-galactose pathway) L-ascorbate L-ascorbic acid*L-ascorbate (vitamin C)*ascorbate*vitamin C*ascorbic acid 175.118 C6 H7 O6 O1(C([H])(C(O)CO)C(=C(C(=O)1)O)[O-]) CHEBI:38290:*PUBCHEM:44229109:*PUBCHEM:25200374:*KNAPSACK:C00001179:*LIGAND-CPD:C00072:*CAS:50-81-7 1.10.99.3 H+ + antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O antheraxanthin and violaxanthin biosynthesis L-ascorbate L-ascorbic acid*L-ascorbate (vitamin C)*ascorbate*vitamin C*ascorbic acid 175.118 C6 H7 O6 O1(C([H])(C(O)CO)C(=C(C(=O)1)O)[O-]) CHEBI:38290:*PUBCHEM:44229109:*PUBCHEM:25200374:*KNAPSACK:C00001179:*LIGAND-CPD:C00072:*CAS:50-81-7 1.10.99.3 H+ + antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle L-ascorbate L-ascorbic acid*L-ascorbate (vitamin C)*ascorbate*vitamin C*ascorbic acid 175.118 C6 H7 O6 O1(C([H])(C(O)CO)C(=C(C(=O)1)O)[O-]) CHEBI:38290:*PUBCHEM:44229109:*PUBCHEM:25200374:*KNAPSACK:C00001179:*LIGAND-CPD:C00072:*CAS:50-81-7 monodehydroascorbate = H+ + L-ascorbate + L-dehydro-ascorbate ascorbate glutathione cycle L-histidinol-phosphate L-histidinol-phosphate*histidinol-P*L-histidinol-p*histidinol-phosphate 220.144 C6 H11 N3 O4 P1 C1(=C(CC([N+])COP(=O)([O-])[O-])N=CN1) KNAPSACK:C00007480:*PUBCHEM:25245017:*LIGAND-CPD:C01100:*CAS:25679-93-0 2.6.1.9 imidazole acetol-phosphate + L-glutamate = L-histidinol-phosphate + 2-oxoglutarate histidine biosynthesis L-histidinol-phosphate L-histidinol-phosphate*histidinol-P*L-histidinol-p*histidinol-phosphate 220.144 C6 H11 N3 O4 P1 C1(=C(CC([N+])COP(=O)([O-])[O-])N=CN1) KNAPSACK:C00007480:*PUBCHEM:25245017:*LIGAND-CPD:C01100:*CAS:25679-93-0 3.1.3.15 L-histidinol-phosphate + H2O = histidinol histidine biosynthesis kaempferol 285.232 C15 H9 O6 C3(O)(C=CC(C1(=C([O-])C(=O)C2(C(O)=CC(O)=CC(O1)=2)))=CC=3) PUBCHEM:25202062:*CHEBI:58573:*PUBCHEM:25202062:*LIGAND-CPD:C05903: 2.4.1.91 kaempferol = kaempferol-3-glucoside + UDP + H+ flavonol glucosylation I kaempferol 285.232 C15 H9 O6 C3(O)(C=CC(C1(=C([O-])C(=O)C2(C(O)=CC(O)=CC(O1)=2)))=CC=3) PUBCHEM:25202062:*CHEBI:58573:*PUBCHEM:25202062:*LIGAND-CPD:C05903: 1.14.11.23 dihydrokaempferol + 2-oxoglutarate + oxygen = kaempferol + succinate + CO2 + H2O flavonol biosynthesis cadaverine diaminopentane*1,5-Diaminopentane*1,5-pentanediamine*pentamethylenediamine*BioDex 1-*cadaverine 104.195 C5 H16 N2 [N+]CCCCC[N+] PUBCHEM:273:*CHEBI:58384:*PUBCHEM:3718401:*LIGAND-CPD:C01672:*CAS:462-94-2 4.1.1.18 H+ + L-lysine = CO2 + cadaverine lysine degradation I delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside 950.81 C42 H46 O25 C7(C4(=C(C=C(OC1(OC(CO)C(O)C(O)C(O)1))C(C3(C=C(O)C(O)=C(OC2(C(O)C(O)C(O)C(CO)O2))C=3))=[O+]4)C(OC6(C(O)C(O)C(O)C(COC(=O)C=CC5(C=CC(O)=C(O)C=5))O6))=CC([O-])=7)) PUBCHEM:25245657: 2.4.1.- delphinidin 3-O-glucosyl-5-O-caffeoylglucoside = H+ + delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + UDP gentiodelphin biosynthesis delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside 950.81 C42 H46 O25 C7(C4(=C(C=C(OC1(OC(CO)C(O)C(O)C(O)1))C(C3(C=C(O)C(O)=C(OC2(C(O)C(O)C(O)C(CO)O2))C=3))=[O+]4)C(OC6(C(O)C(O)C(O)C(COC(=O)C=CC5(C=CC(O)=C(O)C=5))O6))=CC([O-])=7)) PUBCHEM:25245657: 2.3.1.- delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + caffeoyl-CoA = gentiodelphin + coenzyme A gentiodelphin biosynthesis delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside 950.81 C42 H46 O25 C7(C4(=C(C=C(OC1(OC(CO)C(O)C(O)C(O)1))C(C3(C=C(O)C(O)=C(OC2(C(O)C(O)C(O)C(CO)O2))C=3))=[O+]4)C(OC6(C(O)C(O)C(O)C(COC(=O)C=CC5(C=CC(O)=C(O)C=5))O6))=CC([O-])=7)) PUBCHEM:25245657: 2.3.1.- delphinidin 3,5,3'-triglucoside + caffeoyl-CoA = delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + coenzyme A gentiodelphin biosynthesis gallocatechin gallocatechol 306.271 C15 H14 O7 C3(C1(C(=CC(O)=CC(O)=1)OC(C2(C=C(O)C(O)=C(O)C=2))C(O)3)) PUBCHEM:12309543:*LIGAND-CPD:C12127: 1.17.1.3 gallocatechin + NADP+ + H2O = leucodelphinidin + NADPH + H+ 2,3-trans-flavanols biosynthesis cis-zeatin riboside cZR 351.361 C15 H21 N5 O5 C1(C(OC(C1O)N3(C2(N=CN=C(C=2N=C3)NCC=C(C)CO)))CO)O PUBCHEM:5354008:*LIGAND-CPD:C16449: cis-zeatin riboside monophosphate + H2O = cis-zeatin riboside cis-zeatin biosynthesis cis-zeatin riboside cZR 351.361 C15 H21 N5 O5 C1(C(OC(C1O)N3(C2(N=CN=C(C=2N=C3)NCC=C(C)CO)))CO)O PUBCHEM:5354008:*LIGAND-CPD:C16449: cis-zeatin riboside + H2O = cis-zeatin cis-zeatin biosynthesis L-alanine alanine*L-α-alanine*ala 89.094 C3 H7 N1 O2 C([N+])(C)C(=O)[O-] PUBCHEM:7311724:*KNAPSACK:C00001332:*PUBCHEM:5950:*PUBCHEM:7311724:*CAS:6898-94-8*LIGAND-CPD:C00041:*CAS:56-41-7 2.6.1.2 2-oxoglutarate + L-alanine = L-glutamate + pyruvate alanine biosynthesis II L-alanine alanine*L-α-alanine*ala 89.094 C3 H7 N1 O2 C([N+])(C)C(=O)[O-] PUBCHEM:7311724:*KNAPSACK:C00001332:*PUBCHEM:5950:*PUBCHEM:7311724:*CAS:6898-94-8*LIGAND-CPD:C00041:*CAS:56-41-7 2.6.1.2 2-oxoglutarate + L-alanine = L-glutamate + pyruvate alanine degradation II (to D-lactate) L-alanine alanine*L-α-alanine*ala 89.094 C3 H7 N1 O2 C([N+])(C)C(=O)[O-] PUBCHEM:7311724:*KNAPSACK:C00001332:*PUBCHEM:5950:*PUBCHEM:7311724:*CAS:6898-94-8*LIGAND-CPD:C00041:*CAS:56-41-7 2.6.1.- beta-methylenecyclopropyl pyruvate + L-alanine = hypoglycin A + pyruvate hypoglycin biosynthesis L-alanine alanine*L-α-alanine*ala 89.094 C3 H7 N1 O2 C([N+])(C)C(=O)[O-] PUBCHEM:7311724:*KNAPSACK:C00001332:*PUBCHEM:5950:*PUBCHEM:7311724:*CAS:6898-94-8*LIGAND-CPD:C00041:*CAS:56-41-7 2.8.1.7 L-cysteine = L-alanine alanine biosynthesis III L-alanine alanine*L-α-alanine*ala 89.094 C3 H7 N1 O2 C([N+])(C)C(=O)[O-] PUBCHEM:7311724:*KNAPSACK:C00001332:*PUBCHEM:5950:*PUBCHEM:7311724:*CAS:6898-94-8*LIGAND-CPD:C00041:*CAS:56-41-7 3.5.1.- indole-3-acetyl-alanine + H2O = indole-3-acetate + L-alanine IAA biosynthesis II L-alanine alanine*L-α-alanine*ala 89.094 C3 H7 N1 O2 C([N+])(C)C(=O)[O-] PUBCHEM:7311724:*KNAPSACK:C00001332:*PUBCHEM:5950:*PUBCHEM:7311724:*CAS:6898-94-8*LIGAND-CPD:C00041:*CAS:56-41-7 6.1.1.7 H+ + L-alanine + ATP = diphosphate + AMP tRNA charging pathway L-alanine alanine*L-α-alanine*ala 89.094 C3 H7 N1 O2 C([N+])(C)C(=O)[O-] PUBCHEM:7311724:*KNAPSACK:C00001332:*PUBCHEM:5950:*PUBCHEM:7311724:*CAS:6898-94-8*LIGAND-CPD:C00041:*CAS:56-41-7 2.6.1.- L-tryptophan + pyruvate = L-alanine + indole-3-pyruvate IAA biosynthesis I L-alanine alanine*L-α-alanine*ala 89.094 C3 H7 N1 O2 C([N+])(C)C(=O)[O-] PUBCHEM:7311724:*KNAPSACK:C00001332:*PUBCHEM:5950:*PUBCHEM:7311724:*CAS:6898-94-8*LIGAND-CPD:C00041:*CAS:56-41-7 2.6.1.18 malonate semialdehyde + L-alanine = β-alanine + pyruvate β-alanine biosynthesis II FMN flavin mononucleotide*riboflavin-5'-phosphate 453.324 C17 H18 N4 O9 P1 C13(C(N=C2(C(=O)[N-]C(=O)N=C(N(CC(O)C(O)C(O)COP([O-])(=O)[O-])1)2))=CC(C)=C(C)C=3) CHEBI:58210:*PUBCHEM:44229199:*|Wikipedia|:Flavin_mononucleotide:*PUBCHEM:25245661:*PUBCHEM:710:*PUBCHEM:710:*LIGAND-CPD:C00061:*CAS:146-17-8 2.7.1.26 riboflavin + ATP = H+ + FMN + ADP flavin biosynthesis I (bacteria and plants) FMN flavin mononucleotide*riboflavin-5'-phosphate 453.324 C17 H18 N4 O9 P1 C13(C(N=C2(C(=O)[N-]C(=O)N=C(N(CC(O)C(O)C(O)COP([O-])(=O)[O-])1)2))=CC(C)=C(C)C=3) CHEBI:58210:*PUBCHEM:44229199:*|Wikipedia|:Flavin_mononucleotide:*PUBCHEM:25245661:*PUBCHEM:710:*PUBCHEM:710:*LIGAND-CPD:C00061:*CAS:146-17-8 2.7.7.2 H+ + FMN + ATP = FAD + diphosphate flavin biosynthesis I (bacteria and plants) 5-methylthioribose-1-phosphate 5-methylthio-5-deoxy-D-ribose-1-phosphate*S5-methyl-5-thio-D-ribose-1-phosphate*5-methylthio-D-ribose-1-phosphate*5-MTR-1-P*1-phosphomethylthioribose*1-phospho-5-S-methylthioribose*1-PMTR*1-phospho-5-S-methylthio-α-D-ribofuranoside*S-methyl-5-thio-α-D-ribose 1-phosphate*S-methyl-5-thio-D-ribose 1-phosphate 258.182 C6 H11 O7 P1 S1 C1(C(OC(C1O)CSC)OP([O-])([O-])=O)O PUBCHEM:440251:*PUBCHEM:25245660:*LIGAND-CPD:C04188: 5.3.1.23 5-methylthioribose-1-phosphate = 5-methylthioribulose-1-phosphate methionine salvage I 5-methylthioribose-1-phosphate 5-methylthio-5-deoxy-D-ribose-1-phosphate*S5-methyl-5-thio-D-ribose-1-phosphate*5-methylthio-D-ribose-1-phosphate*5-MTR-1-P*1-phosphomethylthioribose*1-phospho-5-S-methylthioribose*1-PMTR*1-phospho-5-S-methylthio-α-D-ribofuranoside*S-methyl-5-thio-α-D-ribose 1-phosphate*S-methyl-5-thio-D-ribose 1-phosphate 258.182 C6 H11 O7 P1 S1 C1(C(OC(C1O)CSC)OP([O-])([O-])=O)O PUBCHEM:440251:*PUBCHEM:25245660:*LIGAND-CPD:C04188: 2.7.1.100 ATP + S-methyl-5-thio-D-ribose = H+ + ADP + 5-methylthioribose-1-phosphate methionine salvage I methyl indole-3-acetate IAA methyl ester*methyl IAA*MeIAA*Indole-3-acetic acid, methyl ester*methyl 2-(1H-indol-3-yl)acetate 189.213 C11 H11 N1 O2 COC(CC2(C1(=C(C=CC=C1)NC=2)))=O PUBCHEM:74706:*KNAPSACK:C00000101: 2.1.1.- indole-3-acetate + S-adenosyl-L-methionine = methyl indole-3-acetate + S-adenosyl-L-homocysteine methyl indole-3-acetate interconversion methyl indole-3-acetate IAA methyl ester*methyl IAA*MeIAA*Indole-3-acetic acid, methyl ester*methyl 2-(1H-indol-3-yl)acetate 189.213 C11 H11 N1 O2 COC(CC2(C1(=C(C=CC=C1)NC=2)))=O PUBCHEM:74706:*KNAPSACK:C00000101: 3.1.1.1 methyl indole-3-acetate + H2O = H+ + indole-3-acetate + methanol methyl indole-3-acetate interconversion magnesium-protoporphyrin IX 13-monomethyl ester magnesium-protoporphyrin IX 13-monomethyl ester*Mg-protoporphyrin monomethyl ester*magnesium protoporphyrin monomethyl ester*MgPMME*magnesium-protoporphyrin IX 13-methyl ester*MgP monomethyl ester 597.975 C35 H33 N4 O4 MG1 C16(N8(C(=C(C=1C)CCC(OC)=O)C=C2(C(=C(C7(=N2[Mg]5(N3(C(C(=C(C3=CC4(C(=C(C(N=45)=C6)C=C)C))C=C)C)=C7))8))C)CCC(=O)[O-]))) CHEBI:60491:*PUBCHEM:44229200:*LIGAND-CPD:C04536: 2.1.1.11 Mg-protoporphyrin + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + magnesium-protoporphyrin IX 13-monomethyl ester chlorophyllide a biosynthesis I magnesium-protoporphyrin IX 13-monomethyl ester magnesium-protoporphyrin IX 13-monomethyl ester*Mg-protoporphyrin monomethyl ester*magnesium protoporphyrin monomethyl ester*MgPMME*magnesium-protoporphyrin IX 13-methyl ester*MgP monomethyl ester 597.975 C35 H33 N4 O4 MG1 C16(N8(C(=C(C=1C)CCC(OC)=O)C=C2(C(=C(C7(=N2[Mg]5(N3(C(C(=C(C3=CC4(C(=C(C(N=45)=C6)C=C)C))C=C)C)=C7))8))C)CCC(=O)[O-]))) CHEBI:60491:*PUBCHEM:44229200:*LIGAND-CPD:C04536: 1.14.13.81 magnesium-protoporphyrin IX 13-monomethyl ester + oxygen + NADPH + H+ = 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis I hypoglycin A hypoglycine*hypoglycine A*hypoglycin*L-β-(methylenecyclopropyl)-alanine*2-amino-3-(2-methylidenecyclopropyl)propanoic acid 141.169 C7 H11 N1 O2 C=C1(C(CC([N+])C([O-])=O)C1) PUBCHEM:9081:*PUBCHEM:25244430:*LIGAND-CPD:C08287:*|Wikipedia|:Hypoglycin: 2.3.2.2 hypoglycin A + glutathione = hypoglycin B + cysteinylglycine hypoglycin biosynthesis hypoglycin A hypoglycine*hypoglycine A*hypoglycin*L-β-(methylenecyclopropyl)-alanine*2-amino-3-(2-methylidenecyclopropyl)propanoic acid 141.169 C7 H11 N1 O2 C=C1(C(CC([N+])C([O-])=O)C1) PUBCHEM:9081:*PUBCHEM:25244430:*LIGAND-CPD:C08287:*|Wikipedia|:Hypoglycin: 2.6.1.- beta-methylenecyclopropyl pyruvate + L-alanine = hypoglycin A + pyruvate hypoglycin biosynthesis GA51 gibberellin A51*gibberellin A51*GA51 331.388 C19 H23 O5 C1(C(CC2(C4(C1(OC2=O)C5(CCC3(CC(CC3=C)(C4C([O-])=O)5))))(C))O) PUBCHEM:25245666:*LIGAND-CPD:C11865: 1.14.11.- gibberellin A9 + 2-oxoglutarate + oxygen = GA51 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) GA51 gibberellin A51*gibberellin A51*GA51 331.388 C19 H23 O5 C1(C(CC2(C4(C1(OC2=O)C5(CCC3(CC(CC3=C)(C4C([O-])=O)5))))(C))O) PUBCHEM:25245666:*LIGAND-CPD:C11865: 1.14.11.- GA51 + 2-oxoglutarate + oxygen = H+ + GA51-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) prephytoene diphosphate 719.897 C40 H65 O7 P2 C(C1(C(C1COP(OP(=O)([O-])[O-])([O-])=O)C=C(C)CCC=C(CCC=C(C)CCC=C(C)C)C)C)CC=C(CCC=C(CCC=C(C)C)C)C PUBCHEM:25245670:*LIGAND-CPD:C03427: 2.5.1.32 all-trans-geranyl-geranyl diphosphate = prephytoene diphosphate + diphosphate trans-lycopene biosynthesis II (plants) prephytoene diphosphate 719.897 C40 H65 O7 P2 C(C1(C(C1COP(OP(=O)([O-])[O-])([O-])=O)C=C(C)CCC=C(CCC=C(C)CCC=C(C)C)C)C)CC=C(CCC=C(CCC=C(C)C)C)C PUBCHEM:25245670:*LIGAND-CPD:C03427: 2.5.1.32 prephytoene diphosphate = 15-cis-phytoene + diphosphate trans-lycopene biosynthesis II (plants) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.- trans-cinnamate + coenzyme A + ATP = (E)-cinnamoyl-CoA + AMP + diphosphate trans-cinnamoyl-CoA biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.23 H+ + N-acetyl-α-D-glucosamine 1-phosphate + UTP = UDP-α-N-acetyl-D-glucosamine + diphosphate UDP-N-acetyl-D-glucosamine biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.15 p-aminobenzoate + 6-hydroxymethyl-dihydropterin diphosphate = 7,8-dihydropteroate + diphosphate tetrahydrofolate biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.- H+ + chlorophyllide a + all-trans-geranyl-geranyl diphosphate = geranylgeranyl-chlorophyll a + diphosphate chlorophyll a biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 3.6.1.23 dUTP + H2O = H+ + dUMP + diphosphate pyrimidine deoxyribonucleotides de novo biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.29 (2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-geranyl-geranyl diphosphate + diphosphate geranylgeranyldiphosphate biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.29 (2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-geranyl-geranyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.39 all-trans-decaprenyl diphosphate = 3-decaprenyl-4-hydroxybenzoate + diphosphate ubiquinol-10 biosynthesis (eukaryotic) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.60 H+ + 2-C-methyl-D-erythritol-4-phosphate + CTP = 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + diphosphate methylerythritol phosphate pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- geranyl diphosphate = terpinolene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.1.1 ammonia + L-aspartate + ATP = L-asparagine + diphosphate + AMP asparagine biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 L-glutamate + ATP = AMP + diphosphate L-glutamine biosynthesis II (tRNA-dependent) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.15 H+ + L-proline + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 all-trans-geranyl-geranyl diphosphate = ent-kaurene + diphosphate ent -kaurene biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.14 geranyl diphosphate = (-)-β-pinene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.4.15 biotin + ATP = diphosphate + AMP biotin-carboxyl carrier protein assembly diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.57 H+ + N-methylethanolamine phosphate + CTP = CDP-N-methylethanolamine + diphosphate phosphatidylcholine biosynthesis III diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.2 H+ + FMN + ATP = FAD + diphosphate flavin biosynthesis I (bacteria and plants) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.5.1.- ATP = diphosphate + AMP tRNA splicing diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.85 all-trans-geranyl-geranyl diphosphate + isopentenyl diphosphate = all-trans-nonaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.84 all-trans-octaprenyl diphosphate + isopentenyl diphosphate = H+ + all-trans-nonaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- geranyl diphosphate = (Z)-β-ocimene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.- 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate + coenzyme A + ATP = OPC8-CoA + AMP + diphosphate jasmonic acid biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.15 geranyl diphosphate = β-myrcene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.10 H+ + L-methionine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.16 H+ + L-cysteine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.11 H+ + L-serine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.16 geranyl diphosphate = (-)-(4S)-limonene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.14 H+ + phosphoryl-ethanolamine + CTP = CDP-ethanolamine + diphosphate phosphatidylethanolamine biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.62 H+ + chlorophyllide a + phytyl diphosphate = chlorophyll a + diphosphate chlorophyll cycle diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.62 H+ + chlorophyllide a + phytyl diphosphate = chlorophyll a + diphosphate chlorophyll a biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.- H+ + chlorophyllide b + phytyl diphosphate = chlorophyll b + diphosphate chlorophyll cycle diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.10 orotidine-5'-phosphate + diphosphate = 5-phospho-α-D-ribose 1-diphosphate + orotate uridine-5'-phosphate biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.9 H+ + L-valine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.17 phosphoribosyl-ATP + diphosphate = ATP + 5-phospho-α-D-ribose 1-diphosphate histidine biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = H+ + L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.13 H+ + α-D-mannose 1-phosphate + GTP = GDP-α-D-mannose + diphosphate ascorbate biosynthesis I (L-galactose pathway) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.13 H+ + α-D-mannose 1-phosphate + GTP = GDP-α-D-mannose + diphosphate GDP-mannose biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.5 H+ + L-isoleucine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP acetate conversion to acetyl-CoA diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP ethanol degradation II (cytosol) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP ethanol degradation IV (peroxisomal) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.27 H+ + α-D-glucose 1-phosphate + ATP = ADP-α-D-glucose + diphosphate glycogen biosynthesis I (from ADP-D-Glucose) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.27 H+ + α-D-glucose 1-phosphate + ATP = ADP-α-D-glucose + diphosphate starch biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.18 H+ + ATP + nicotinate mononucleotide = diphosphate + nicotinate adenine dinucleotide NAD biosynthesis I (from aspartate) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.18 H+ + ATP + nicotinate mononucleotide = diphosphate + nicotinate adenine dinucleotide pyridine nucleotide cycling (plants) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.90 all-trans-heptaprenyl diphosphate + isopentenyl diphosphate = H+ + diphosphate + all-trans-octaprenyl diphosphate nonaprenyl diphosphate biosynthesis III diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.39 all-trans-nonaprenyl diphosphate = nonaprenyl-4-hydroxybenzoate + diphosphate ubiquinol-9 biosynthesis (eukaryotic) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.6 H+ + L-lysine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.21 (2E,6E)-farnesyl diphosphate = presqualene diphosphate + diphosphate epoxysqualene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.41 CTP + H+ = diphosphate CDP-diacylglycerol biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.41 CTP + H+ = diphosphate CDP-diacylglycerol biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.18 N-(5'-phosphoribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-α-D-ribose 1-diphosphate tryptophan biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.26 geranyl diphosphate + H2O = (3R)-linalool + diphosphate linalool biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.17 coenzyme A + propionate + ATP = propanoyl-CoA + diphosphate + AMP β-alanine biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.64 UTP = diphosphate stachyose degradation diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.12 trans-caffeate + coenzyme A + ATP = caffeoyl-CoA + AMP + diphosphate suberin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.18 H+ + L-glutamine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.22 H+ + L-asparagine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.2.1 β-alanine + (R)-pantoate + ATP = H+ + (R)-pantothenate + diphosphate + AMP phosphopantothenate biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.2.1 β-alanine + (R)-pantoate + ATP = H+ + (R)-pantothenate + diphosphate + AMP pantothenate biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.21 presqualene diphosphate = squalene + diphosphate epoxysqualene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 3.6.1.1 H2O + diphosphate = H+ UDP-glucose biosynthesis (from glucose 6-phosphate) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.1.5 ammonia + ATP + nicotinate adenine dinucleotide = AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine methionine degradation I (to homocysteine) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine 2'-deoxymugineic acid phytosiderophore biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine ethylene biosynthesis from methionine diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine S-adenosyl-L-methionine cycle II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine S-adenosyl-L-methionine biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- geranyl diphosphate = (E)-β-ocimene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.- H+ + N-dimethylethanolamine phosphate + CTP = CDP-N-dimethylethanolamine + diphosphate phosphatidylcholine biosynthesis IV diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.9 diphosphate + uridine-5'-phosphate = 5-phospho-α-D-ribose 1-diphosphate + uracil salvage pathways of pyrimidine ribonucleotides diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.37 H+ + β-L-arabinose 1-phosphate + UTP = diphosphate UDP-L-arabinose biosynthesis II (from L-arabinose) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.19 ent-copalyl diphosphate = diphosphate + ent-kaurene ent-kaurene biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.3 H+ + L-threonine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = H+ + L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.19 H+ + 5-phospho-α-D-ribose 1-diphosphate + quinolinate = CO2 + diphosphate + nicotinate mononucleotide NAD biosynthesis I (from aspartate) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.4 H+ + L-leucine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.5.1 ATP + nicotinate adenine dinucleotide + L-glutamine + H2O = H+ + L-glutamate + AMP + diphosphate + NAD+ pyridine nucleotide cycling (plants) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid activation diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 H+ + homogentisate + phytyl diphosphate = 2-methyl-6-phytyl-1,4-benzoquinol + CO2 + diphosphate vitamin E biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.27 dimethylallyl diphosphate + AMP = N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate + diphosphate trans-zeatin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O 5-aminoimidazole ribonucleotide biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O 5-aminoimidazole ribonucleotide biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O superpathway of 5-aminoimidazole ribonucleotide biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.44 H+ + α-D-glucuronate 1-phosphate + UTP = UDP-D-glucuronate + diphosphate UDP-D-glucuronate biosynthesis (from myo-inositol) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.49 (2E,6E)-farnesyl diphosphate + H2O = (3R,6E)-nerolidol + diphosphate (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.83 geranylfarnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-hexaprenyl diphosphate + diphosphate hexaprenyl diphosphate biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.83 geranylfarnesyl diphosphate + isopentenyl diphosphate = H+ + all-trans-hexaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.3 oleate + coenzyme A + ATP = oleoyl-CoA + AMP + diphosphate linoleate biosynthesis I (plants) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.- H+ + dimethylallyl diphosphate + ATP = N6-(Δ2-isopentenyl)-adenosine 5'-triphosphate + diphosphate trans-zeatin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.14 H+ + glycine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.30 all-trans-hexaprenyl diphosphate + isopentenyl diphosphate = H+ + all-trans-heptaprenyl diphosphate + diphosphate heptaprenyl diphosphate biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.30 all-trans-hexaprenyl diphosphate + isopentenyl diphosphate = H+ + all-trans-heptaprenyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.30 H+ + β-L-fucose 1-phosphate + GTP = GDP-L-fucose + diphosphate GDP-L-fucose biosynthesis II (from L-fucose) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.14 geranyl diphosphate = (-)-α-pinene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.75 dimethylallyl diphosphate = diphosphate cis-zeatin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.9.1.2 selenophosphate = H2O + diphosphate selenocysteine biosynthesis II (archaea and eukaryotes) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 3.6.1.- 7,8-dihydroneopterin triphosphate + H2O = H+ + 7,8-dihydroneopterin phosphate + diphosphate 6-hydroxymethyl-dihydropterin diphosphate biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.9.1 pyruvate + ATP = H+ + phosphoenolpyruvate + AMP + diphosphate glutamine biosynthesis III diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.9.1 pyruvate + ATP = H+ + phosphoenolpyruvate + AMP + diphosphate C4 photosynthetic carbon assimilation cycle diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.1.90 D-fructose-6-phosphate + diphosphate = H+ + fructose-1,6-bisphosphate glycolysis IV (plant cytosol) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.15 H+ + phosphoryl-choline + CTP = CDP-choline + diphosphate phosphatidylcholine biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.15 H+ + phosphoryl-choline + CTP = CDP-choline + diphosphate choline biosynthesis III diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.15 H+ + phosphoryl-choline + CTP = CDP-choline + diphosphate phosphatidylcholine biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.20 H+ + L-phenylalanine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- (2E,6E)-farnesyl diphosphate = α-humulene + diphosphate β-caryophyllene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- geranyl diphosphate = sabinene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP urea cycle diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP arginine biosynthesis II (acetyl cycle) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP citrulline-nitric oxide cycle diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.4.5 L-aspartate + L-citrulline + ATP = H+ + L-arginino-succinate + diphosphate + AMP arginine biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 all-trans-geranyl-geranyl diphosphate + H2O = ent-16-a-hydroxy-kaurene + diphosphate ent -kaurene biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 diphosphate = UTP + H+ stachyose degradation diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.19 H+ + L-arginine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.10 H+ + α-D-galactose 1-phosphate + UTP = UDP-D-galactose + diphosphate stachyose degradation diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.10 H+ + α-D-galactose 1-phosphate + UTP = UDP-D-galactose + diphosphate galactose degradation III diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.32 prephytoene diphosphate = 15-cis-phytoene + diphosphate trans-lycopene biosynthesis II (plants) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.81 isopentenyl diphosphate + all-trans-geranyl-geranyl diphosphate = H+ + geranylfarnesyl diphosphate + diphosphate nonaprenyl diphosphate biosynthesis III diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.1 dimethylallyl diphosphate + isopentenyl diphosphate = geranyl diphosphate + diphosphate geranyl diphosphate biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.1 dimethylallyl diphosphate + isopentenyl diphosphate = geranyl diphosphate + diphosphate trans, trans-farnesyl diphosphate biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid β-oxidation II (core pathway) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- geranyl diphosphate + H2O = (-)-α-terpineol + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.2 H+ + L-tryptophan + ATP = AMP + diphosphate tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.10 geranyl diphosphate + isopentenyl diphosphate = (2E,6E)-farnesyl diphosphate + diphosphate linalool biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.10 geranyl diphosphate + isopentenyl diphosphate = (2E,6E)-farnesyl diphosphate + diphosphate trans, trans-farnesyl diphosphate biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.3 H+ + 4-methyl-5-(2-phosphonooxyethyl)thiazole + 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate = thiamine-phosphate + diphosphate thiamine biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.32 all-trans-geranyl-geranyl diphosphate = prephytoene diphosphate + diphosphate trans-lycopene biosynthesis II (plants) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.11 H+ + L-serine + ATP = diphosphate + AMP selenocysteine biosynthesis II (archaea and eukaryotes) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate glycogen biosynthesis II (from UDP-D-Glucose) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate sucrose degradation III diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate stachyose degradation diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate UDP-glucose biosynthesis (from glucose 6-phosphate) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate colanic acid building blocks biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate galactose degradation III diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.9 H+ + α-D-glucose 1-phosphate + UTP = diphosphate sucrose biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.21 H+ + L-histidine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.7 AMP + diphosphate = adenine + 5-phospho-α-D-ribose 1-diphosphate adenine and adenosine salvage II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.3 H+ + 4'-phosphopantetheine + ATP = dephospho-CoA + diphosphate coenzyme A biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.31 (2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = di-trans,octa-cis-undecaprenyl diphosphate + diphosphate di-trans,poly-cis-undecaprenyl phosphate biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.2.5 D-4'-phosphopantothenate + L-cysteine + CTP = H+ + R-4'-phosphopantothenoyl-L-cysteine + diphosphate + CMP coenzyme A biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- (2E,6E)-farnesyl diphosphate = β-elemene + diphosphate β-caryophyllene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.12 H+ + L-aspartate + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.1 H+ + L-tyrosine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.48 (2E,6E)-farnesyl diphosphate + H2O = (3S,6E)-nerolidol + diphosphate (3E)-4,8-dimethylnona-1,3,7-triene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.25 geranyl diphosphate + H2O = (3S)-linalool + diphosphate linalool biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ flavonoid biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ simplecoumarins biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ phenylpropanoid biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.12 4-coumarate + coenzyme A + ATP = 4-coumaroyl-CoA + AMP + diphosphate + H+ 4-hydroxybenzoate biosynthesis V diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.7 H+ + L-alanine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 3.5.4.25 H2O + GTP = H+ + diphosphate + 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one + formate flavin biosynthesis I (bacteria and plants) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.58 H+ + 2,3-dihydroxybenzoate + ATP = 2,3-dihydroxybenzoyl-AMP + diphosphate vibriobactin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.34 H+ + α-D-glucose 1-phosphate + GTP = GDP-α-D-glucose + diphosphate GDP-glucose biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.38 3-deoxy-D-manno-octulosonate + CTP = CMP-3-deoxy-D-manno-octulosonate + diphosphate CMP-KDO biosynthesis II (from D-arabinose 5-phosphate) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- (2E,6E)-farnesyl diphosphate = (E)-β-caryophyllene + diphosphate β-caryophyllene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.17 L-glutamate + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.17 L-glutamate + ATP = diphosphate + AMP tetrapyrrole biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.34 ferulate + ATP + coenzyme A = feruloyl-CoA + AMP + diphosphate suberin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.8 GMP + diphosphate = guanine + 5-phospho-α-D-ribose 1-diphosphate guanine and guanosine salvage II diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 3.6.1.31 phosphoribosyl-ATP + H2O = 1-(5-phospho-D-ribosyl)-AMP + diphosphate + H+ histidine biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.11 nicotinate mononucleotide + diphosphate = H+ + nicotinate + 5-phospho-α-D-ribose 1-diphosphate pyridine nucleotide cycling (plants) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.4 H+ + sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate reduction II (assimilatory) diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.4 H+ + sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfite oxidation III diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.4 H+ + sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate activation for sulfonation diphosphate diphosphate*PPi*PP*pyrophosphate 174.951 H1 O7 P2 O(P([O-])([O-])=O)P(=O)(O)[O-] CAS:09/03/2466:*PUBCHEM:1023:*CHEBI:33019:*PUBCHEM:4097574:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.- dimethylallyl diphosphate + ADP = N6-(Δ2-isopentenyl)-adenosine 5'-diphosphate + diphosphate trans-zeatin biosynthesis 3-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate 2-hydroxy-2-(2-methylidenecyclopropyl)butanedioic acid 184.148 C8 H8 O5 C1(C(C(O)(C(=O)[O-])CC([O-])=O)C1)(=C) PUBCHEM:25201226: 2.3.-.- 2-oxohexa-4,5-cyclopropyl-5-enoate + acetyl-CoA + H2O = H+ + 3-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate + coenzyme A hypoglycin biosynthesis 3-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate 2-hydroxy-2-(2-methylidenecyclopropyl)butanedioic acid 184.148 C8 H8 O5 C1(C(C(O)(C(=O)[O-])CC([O-])=O)C1)(=C) PUBCHEM:25201226: 5.-.-.- 3-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate = 2-hydroxy-3-carboxy-4,5-cyclopropylhex-5-enoate hypoglycin biosynthesis 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide 1-(5-Phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide*phosphoribosylformiminoAICAR-phosphate*phosphoribosyl-formimino-aicar-P*phosphoribosylformiminoAICAR-P*5-(5-phospho-D-ribosyl-aminoformimino)-1-(5-phosphoribosyl)-imidazole4-carboxamide*5-(5'-phospho-D-ribosyl-aminoformimino)-1-(5-phosphoribosyl)-imidazole-4-carboxamide*N-5-phosphoribosyl-formimino-5-amino-imidazole-4-carboxamide ribonucleotide*N-(5'-phospho-D-ribosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolecarboxamide 573.303 C15 H21 N5 O15 P2 N3(C(C(N)=O)=C(N=CNC1(OC(COP(=O)([O-])[O-])C(O)C(O)1))N(C2(OC(COP(=O)([O-])[O-])C(O)C(O)2))C=3) PUBCHEM:440534:*PUBCHEM:25245036:*LIGAND-CPD:C04896: 5.3.1.16 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide = phosphoribulosylformimino-AICAR-P histidine biosynthesis 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide 1-(5-Phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide*phosphoribosylformiminoAICAR-phosphate*phosphoribosyl-formimino-aicar-P*phosphoribosylformiminoAICAR-P*5-(5-phospho-D-ribosyl-aminoformimino)-1-(5-phosphoribosyl)-imidazole4-carboxamide*5-(5'-phospho-D-ribosyl-aminoformimino)-1-(5-phosphoribosyl)-imidazole-4-carboxamide*N-5-phosphoribosyl-formimino-5-amino-imidazole-4-carboxamide ribonucleotide*N-(5'-phospho-D-ribosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolecarboxamide 573.303 C15 H21 N5 O15 P2 N3(C(C(N)=O)=C(N=CNC1(OC(COP(=O)([O-])[O-])C(O)C(O)1))N(C2(OC(COP(=O)([O-])[O-])C(O)C(O)2))C=3) PUBCHEM:440534:*PUBCHEM:25245036:*LIGAND-CPD:C04896: 3.5.4.19 1-(5-phospho-D-ribosyl)-AMP + H2O = 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide histidine biosynthesis (R)-pantothenate (R)-pantothenic acid*(R)-pantothenate*vitamin B5*pantothenic acid*D-pantothenic acid 218.229 C9 H16 N1 O5 O=C([O-])CCNC(=O)C(O)C(C)(C)CO KNAPSACK:C00001550:*|Wikipedia|:Vitamin_B5:*PUBCHEM:167945:*CHEBI:29032:*LIGAND-CPD:C00864:*CAS:79-83-4 6.3.2.1 β-alanine + (R)-pantoate + ATP = H+ + (R)-pantothenate + diphosphate + AMP phosphopantothenate biosynthesis I (R)-pantothenate (R)-pantothenic acid*(R)-pantothenate*vitamin B5*pantothenic acid*D-pantothenic acid 218.229 C9 H16 N1 O5 O=C([O-])CCNC(=O)C(O)C(C)(C)CO KNAPSACK:C00001550:*|Wikipedia|:Vitamin_B5:*PUBCHEM:167945:*CHEBI:29032:*LIGAND-CPD:C00864:*CAS:79-83-4 6.3.2.1 β-alanine + (R)-pantoate + ATP = H+ + (R)-pantothenate + diphosphate + AMP pantothenate biosynthesis I (R)-pantothenate (R)-pantothenic acid*(R)-pantothenate*vitamin B5*pantothenic acid*D-pantothenic acid 218.229 C9 H16 N1 O5 O=C([O-])CCNC(=O)C(O)C(C)(C)CO KNAPSACK:C00001550:*|Wikipedia|:Vitamin_B5:*PUBCHEM:167945:*CHEBI:29032:*LIGAND-CPD:C00864:*CAS:79-83-4 2.7.1.33 (R)-pantothenate + ATP = H+ + D-4'-phosphopantothenate + ADP phosphopantothenate biosynthesis I 5-O-(indol-3-ylacetyl-myo-inositol) D-galactoside 499.471 C22 H29 N1 O12 O=C(CC1(=CNC2(C=CC=CC1=2)))OC4(C(O)C(O)C(O)C(OC3(OC(CO)C(O)C(O)C(O)3))C(O)4) PUBCHEM:440445:*LIGAND-CPD:C04695: 2.4.1.156 indol-3-yl-acetyl-myo-inositol + UDP-D-galactose = H+ + 5-O-(indol-3-ylacetyl-myo-inositol) D-galactoside + UDP IAA conjugate biosynthesis I 5-oxoproline pyrrolidone-COO*pyrrolidone-carboxylate*L-5-pyrrolidone-2-carboxylic acid*L-pyroglutamic acid*5-oxo-L-proline*pyroglutamic acid*pyroglutamate*5-pyrrolidone-2-carboxylic acid 128.107 C5 H6 N1 O3 N1(C(CCC1=O)C(=O)[O-]) LIGAND-CPD:C02238:*CHEBI:58402:*PUBCHEM:5289118:*LIGAND-CPD:C01879:*CAS:98-79-3 glutathione = 5-oxoproline + cysteinylglycine γ-glutamyl cycle (plant pathway) 5-oxoproline pyrrolidone-COO*pyrrolidone-carboxylate*L-5-pyrrolidone-2-carboxylic acid*L-pyroglutamic acid*5-oxo-L-proline*pyroglutamic acid*pyroglutamate*5-pyrrolidone-2-carboxylic acid 128.107 C5 H6 N1 O3 N1(C(CCC1=O)C(=O)[O-]) LIGAND-CPD:C02238:*CHEBI:58402:*PUBCHEM:5289118:*LIGAND-CPD:C01879:*CAS:98-79-3 L-γ-glutamylcysteine = 5-oxoproline γ-glutamyl cycle (plant pathway) 5-oxoproline pyrrolidone-COO*pyrrolidone-carboxylate*L-5-pyrrolidone-2-carboxylic acid*L-pyroglutamic acid*5-oxo-L-proline*pyroglutamic acid*pyroglutamate*5-pyrrolidone-2-carboxylic acid 128.107 C5 H6 N1 O3 N1(C(CCC1=O)C(=O)[O-]) LIGAND-CPD:C02238:*CHEBI:58402:*PUBCHEM:5289118:*LIGAND-CPD:C01879:*CAS:98-79-3 3.5.2.9 5-oxoproline + H2O + ATP = H+ + L-glutamate + ADP γ-glutamyl cycle (plant pathway) 5-oxoproline pyrrolidone-COO*pyrrolidone-carboxylate*L-5-pyrrolidone-2-carboxylic acid*L-pyroglutamic acid*5-oxo-L-proline*pyroglutamic acid*pyroglutamate*5-pyrrolidone-2-carboxylic acid 128.107 C5 H6 N1 O3 N1(C(CCC1=O)C(=O)[O-]) LIGAND-CPD:C02238:*CHEBI:58402:*PUBCHEM:5289118:*LIGAND-CPD:C01879:*CAS:98-79-3 3.5.2.9 5-oxoproline + H2O + ATP = H+ + L-glutamate + ADP γ-glutamyl cycle 5-oxoproline pyrrolidone-COO*pyrrolidone-carboxylate*L-5-pyrrolidone-2-carboxylic acid*L-pyroglutamic acid*5-oxo-L-proline*pyroglutamic acid*pyroglutamate*5-pyrrolidone-2-carboxylic acid 128.107 C5 H6 N1 O3 N1(C(CCC1=O)C(=O)[O-]) LIGAND-CPD:C02238:*CHEBI:58402:*PUBCHEM:5289118:*LIGAND-CPD:C01879:*CAS:98-79-3 2.3.2.4 γ-glutamyl cycle nitric oxide NO*nitrogen monoxide*nitrogen protoxide 31.014 H1 N1 O1 N=O PUBCHEM:945:*LIGAND-CPD:C00533:*CAS:10102-43-9 1.14.13.39 oxygen + NADPH + L-arginine = L-citrulline + NADP+ + nitric oxide citrulline-nitric oxide cycle indole-3-acetamide 1H-indole-3-acetamide*indoleacetamide*(indol-3-yl)acetamide 174.202 C10 H10 N2 O1 C(C(=O)N)C1(C2(=CC=CC=C(NC=1)2)) PUBCHEM:397:*CHEBI:16031:*LIGAND-CPD:C02693:*CAS:879-37-8 3.5.1.4 indole-3-acetamide + H2O = H+ + indole-3-acetate + ammonia IAA biosynthesis I indole-3-acetamide 1H-indole-3-acetamide*indoleacetamide*(indol-3-yl)acetamide 174.202 C10 H10 N2 O1 C(C(=O)N)C1(C2(=CC=CC=C(NC=1)2)) PUBCHEM:397:*CHEBI:16031:*LIGAND-CPD:C02693:*CAS:879-37-8 4.2.1.84 indole-3-acetonitrile + H2O = indole-3-acetamide IAA biosynthesis I betanidin quinone 384.301 C18 H12 N2 O8 C1(C(C=C(NC1C([O-])=O)C(=O)[O-])=CC=[N+]2(C(CC3(=CC(C(C=C23)=O)=O))C([O-])=O)) PUBCHEM:25246300: 1.11.1.7 betanidin + hydrogen peroxide = betanidin + betanidin quinone + H2O betanidin degradation S-methyl-5'-thioadenosine S-methyl-adenosine*5'-S-methyl-5'-thioadenosine*5'-Deoxy-5'-(methylthio)adenosine*S-methyl-5'-thioadenosine*methylthioadenosine*5'-methylthioadenosine*5'-S-methyl-5'-thioadenosine*MTA*S-methyl-adenosine 297.331 C11 H15 N5 O3 S1 OC1(C(C(OC1N2(C=NC3(=C2N=CN=C3N)))CSC)O) PUBCHEM:439176:*CHEBI:17509:*LIGAND-CPD:C00170:*CAS:2457-80-9 S-adenosyl-L-methionine = 2-(3-carboxy-3-aminopropyl)-L-histidine in eEF-2 + S-methyl-5'-thioadenosine diphthamide biosynthesis S-methyl-5'-thioadenosine S-methyl-adenosine*5'-S-methyl-5'-thioadenosine*5'-Deoxy-5'-(methylthio)adenosine*S-methyl-5'-thioadenosine*methylthioadenosine*5'-methylthioadenosine*5'-S-methyl-5'-thioadenosine*MTA*S-methyl-adenosine 297.331 C11 H15 N5 O3 S1 OC1(C(C(OC1N2(C=NC3(=C2N=CN=C3N)))CSC)O) PUBCHEM:439176:*CHEBI:17509:*LIGAND-CPD:C00170:*CAS:2457-80-9 2.5.1.22 spermidine + S-adenosyl-L-methioninamine = H+ + spermine + S-methyl-5'-thioadenosine spermine biosynthesis S-methyl-5'-thioadenosine S-methyl-adenosine*5'-S-methyl-5'-thioadenosine*5'-Deoxy-5'-(methylthio)adenosine*S-methyl-5'-thioadenosine*methylthioadenosine*5'-methylthioadenosine*5'-S-methyl-5'-thioadenosine*MTA*S-methyl-adenosine 297.331 C11 H15 N5 O3 S1 OC1(C(C(OC1N2(C=NC3(=C2N=CN=C3N)))CSC)O) PUBCHEM:439176:*CHEBI:17509:*LIGAND-CPD:C00170:*CAS:2457-80-9 3.2.2.16 S-methyl-5'-thioadenosine + H2O = S-methyl-5-thio-D-ribose + adenine methylthioadenosine degradation S-methyl-5'-thioadenosine S-methyl-adenosine*5'-S-methyl-5'-thioadenosine*5'-Deoxy-5'-(methylthio)adenosine*S-methyl-5'-thioadenosine*methylthioadenosine*5'-methylthioadenosine*5'-S-methyl-5'-thioadenosine*MTA*S-methyl-adenosine 297.331 C11 H15 N5 O3 S1 OC1(C(C(OC1N2(C=NC3(=C2N=CN=C3N)))CSC)O) PUBCHEM:439176:*CHEBI:17509:*LIGAND-CPD:C00170:*CAS:2457-80-9 3.2.2.16 S-methyl-5'-thioadenosine + H2O = S-methyl-5-thio-D-ribose + adenine methionine salvage I S-methyl-5'-thioadenosine S-methyl-adenosine*5'-S-methyl-5'-thioadenosine*5'-Deoxy-5'-(methylthio)adenosine*S-methyl-5'-thioadenosine*methylthioadenosine*5'-methylthioadenosine*5'-S-methyl-5'-thioadenosine*MTA*S-methyl-adenosine 297.331 C11 H15 N5 O3 S1 OC1(C(C(OC1N2(C=NC3(=C2N=CN=C3N)))CSC)O) PUBCHEM:439176:*CHEBI:17509:*LIGAND-CPD:C00170:*CAS:2457-80-9 2.5.1.43 S-adenosyl-L-methionine = H+ + nicotianamine + S-methyl-5'-thioadenosine 2'-deoxymugineic acid phytosiderophore biosynthesis S-methyl-5'-thioadenosine S-methyl-adenosine*5'-S-methyl-5'-thioadenosine*5'-Deoxy-5'-(methylthio)adenosine*S-methyl-5'-thioadenosine*methylthioadenosine*5'-methylthioadenosine*5'-S-methyl-5'-thioadenosine*MTA*S-methyl-adenosine 297.331 C11 H15 N5 O3 S1 OC1(C(C(OC1N2(C=NC3(=C2N=CN=C3N)))CSC)O) PUBCHEM:439176:*CHEBI:17509:*LIGAND-CPD:C00170:*CAS:2457-80-9 2.5.1.43 S-adenosyl-L-methionine = H+ + nicotianamine + S-methyl-5'-thioadenosine nicotianamine biosynthesis S-methyl-5'-thioadenosine S-methyl-adenosine*5'-S-methyl-5'-thioadenosine*5'-Deoxy-5'-(methylthio)adenosine*S-methyl-5'-thioadenosine*methylthioadenosine*5'-methylthioadenosine*5'-S-methyl-5'-thioadenosine*MTA*S-methyl-adenosine 297.331 C11 H15 N5 O3 S1 OC1(C(C(OC1N2(C=NC3(=C2N=CN=C3N)))CSC)O) PUBCHEM:439176:*CHEBI:17509:*LIGAND-CPD:C00170:*CAS:2457-80-9 2.5.1.16 putrescine + S-adenosyl-L-methioninamine = H+ + spermidine + S-methyl-5'-thioadenosine spermidine biosynthesis I S-methyl-5'-thioadenosine S-methyl-adenosine*5'-S-methyl-5'-thioadenosine*5'-Deoxy-5'-(methylthio)adenosine*S-methyl-5'-thioadenosine*methylthioadenosine*5'-methylthioadenosine*5'-S-methyl-5'-thioadenosine*MTA*S-methyl-adenosine 297.331 C11 H15 N5 O3 S1 OC1(C(C(OC1N2(C=NC3(=C2N=CN=C3N)))CSC)O) PUBCHEM:439176:*CHEBI:17509:*LIGAND-CPD:C00170:*CAS:2457-80-9 4.4.1.14 S-adenosyl-L-methionine = H+ + S-methyl-5'-thioadenosine + 1-aminocyclopropane-1-carboxylate ethylene biosynthesis from methionine D-glucono-1,5-lactone D-glucono-1,5-lactone*D-aldonolactone*3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-one*gluconolactone*glucono-1,5-lactone*1,5-gluconolactone*D-gluconolactone*glucono-δ-lactone*δ-gluconolactone*D-glucono-δ-lactone*gluconic lactone*gluconic acid lactone 178.141 C6 H10 O6 C1(C(C(OC(C1O)=O)CO)O)O CHEBI:16217:*PUBCHEM:7027:*LIGAND-CPD:C00198:*CAS:90-80-2 3.1.1.17 D-glucono-1,5-lactone + H2O = H+ + D-gluconate glucose and glucose-1-phosphate degradation D-glucono-1,5-lactone D-glucono-1,5-lactone*D-aldonolactone*3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-one*gluconolactone*glucono-1,5-lactone*1,5-gluconolactone*D-gluconolactone*glucono-δ-lactone*δ-gluconolactone*D-glucono-δ-lactone*gluconic lactone*gluconic acid lactone 178.141 C6 H10 O6 C1(C(C(OC(C1O)=O)CO)O)O CHEBI:16217:*PUBCHEM:7027:*LIGAND-CPD:C00198:*CAS:90-80-2 1.1.5.2 β-D-glucose = D-glucono-1,5-lactone glucose and glucose-1-phosphate degradation 1,6-kestotetraose bifurcose 666.583 C24 H42 O21 C1(OC(C(O)C(O)1)COC2(OC(C(C2O)O)CO)CO)(COC3(OC(C(C3O)O)CO)CO)OC4(C(O)C(C(O)C(CO)O4)O) PUBCHEM:25202989: 2.4.1.10 1-kestotriose + sucrose = 1,6-kestotetraose + β-D-glucose fructan biosynthesis 3-(4-hydroxyphenyl)-3-hydroxy-propionyl-CoA 3-(4-hydroxyphenyl)-3-hydroxy-propanoyl-CoA 927.663 C30 H40 N7 O19 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)C4(=CC=C(O)C=C4) PUBCHEM:46173446: 4.2.1.17 3-(4-hydroxyphenyl)-3-hydroxy-propionyl-CoA = 4-coumaroyl-CoA + H2O 4-hydroxybenzoate biosynthesis V 3-(4-hydroxyphenyl)-3-hydroxy-propionyl-CoA 3-(4-hydroxyphenyl)-3-hydroxy-propanoyl-CoA 927.663 C30 H40 N7 O19 P3 S1 CC(C)(COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3))C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)C4(=CC=C(O)C=C4) PUBCHEM:46173446: 1.1.1.35 3-(4-hydroxyphenyl)-3-hydroxy-propionyl-CoA + NAD+ = 3-(4-hydroxyphenyl)-3-oxo-propionyl-CoA + NADH + H+ 4-hydroxybenzoate biosynthesis V 3-deoxy-D-manno-octulosonate 8-P 3-deoxy-D-manno-octulosonate 8-phosphate*2-dehydro-3-deoxy-D-octonate 8-P*2-dehydro-3-deoxy-D-octonate 8-phosphate*KDO-8P 315.15 C8 H12 O11 P1 C(C(CC(C(C(C(COP([O-])([O-])=O)O)O)O)O)=O)([O-])=O PUBCHEM:25244441:*PUBCHEM:46173377:*LIGAND-CPD:C04478: 2.5.1.55 D-arabinose 5-phosphate + H2O + phosphoenolpyruvate = 3-deoxy-D-manno-octulosonate 8-P CMP-KDO biosynthesis II (from D-arabinose 5-phosphate) 3-deoxy-D-manno-octulosonate 8-P 3-deoxy-D-manno-octulosonate 8-phosphate*2-dehydro-3-deoxy-D-octonate 8-P*2-dehydro-3-deoxy-D-octonate 8-phosphate*KDO-8P 315.15 C8 H12 O11 P1 C(C(CC(C(C(C(COP([O-])([O-])=O)O)O)O)O)=O)([O-])=O PUBCHEM:25244441:*PUBCHEM:46173377:*LIGAND-CPD:C04478: 3.1.3.45 3-deoxy-D-manno-octulosonate 8-P + H2O = 3-deoxy-D-manno-octulosonate CMP-KDO biosynthesis II (from D-arabinose 5-phosphate) 2-coumarate 2-hydroxycinnamate*o-coumarate*trans-2-hydroxycinnamate*2-Hydroxycinnamate*trans-2-hydroxycinnamate*o-coumarate 163.152 C9 H7 O3 C1(C=CC(=C(C=1)C=CC([O-])=O)O) CHEBI:11594:*PUBCHEM:6201201:*LIGAND-CPD:C03549: 1.14.13.14 H+ + trans-cinnamate + oxygen + NADPH = H2O + NADP+ + 2-coumarate coumarin biosynthesis (via 2-coumarate) 2-coumarate 2-hydroxycinnamate*o-coumarate*trans-2-hydroxycinnamate*2-Hydroxycinnamate*trans-2-hydroxycinnamate*o-coumarate 163.152 C9 H7 O3 C1(C=CC(=C(C=1)C=CC([O-])=O)O) CHEBI:11594:*PUBCHEM:6201201:*LIGAND-CPD:C03549: 2.4.1.114 2-coumarate = H+ + trans-β-D-Glucosyl-2-hydroxycinnamate + UDP coumarin biosynthesis (via 2-coumarate) N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate iPMP*isopentenyladenosine riboside-5'-monophosphate*iPRMP*N6-(dimethylallyl)adenosine 5'-phosphate*isopentenyladenosine-5'-monophosphate 413.326 C15 H20 N5 O7 P1 C1(C(OC(C1O)N3(C2(N=CN=C(C=2N=C3)NCC=C(C)C)))COP([O-])([O-])=O)O CHEBI:57526:*PUBCHEM:25245046:*LIGAND-CPD:C04713: 3.2.2.- N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate + H2O = N6-dimethylallyladenine + D-ribose-5-phosphate trans-zeatin biosynthesis N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate iPMP*isopentenyladenosine riboside-5'-monophosphate*iPRMP*N6-(dimethylallyl)adenosine 5'-phosphate*isopentenyladenosine-5'-monophosphate 413.326 C15 H20 N5 O7 P1 C1(C(OC(C1O)N3(C2(N=CN=C(C=2N=C3)NCC=C(C)C)))COP([O-])([O-])=O)O CHEBI:57526:*PUBCHEM:25245046:*LIGAND-CPD:C04713: N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate + NADPH + H2O = H+ + trans-zeatin riboside monophosphate + NADP+ trans-zeatin biosynthesis N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate iPMP*isopentenyladenosine riboside-5'-monophosphate*iPRMP*N6-(dimethylallyl)adenosine 5'-phosphate*isopentenyladenosine-5'-monophosphate 413.326 C15 H20 N5 O7 P1 C1(C(OC(C1O)N3(C2(N=CN=C(C=2N=C3)NCC=C(C)C)))COP([O-])([O-])=O)O CHEBI:57526:*PUBCHEM:25245046:*LIGAND-CPD:C04713: 2.5.1.27 dimethylallyl diphosphate + AMP = N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate + diphosphate trans-zeatin biosynthesis (S)-dihydroorotate (S)-4-pyrimidinecarboxylic acid*4,5-dihydro-L-orotate*(S)-di-H-orotate*(S)-hydroorotic acid*(S)-4,5-dihydroorotic acid*(S)-4,5-dihydroorotate*4,5-dihydroorotate*4,5-dihydroorotic acid*hydroorotic acid*(S)-dihydroorotate*di-H-orotate*L-dihydroorotate*5,6-dihydroorotate*L-4,5-dihydroorotate*4-pyrimidinecarboxylic acid*hexahydro-2,6-dioxo- 157.105 C5 H5 N2 O4 O=C1(NC(=O)CC(C(=O)[O-])N1) PUBCHEM:5460289:*CHEBI:30864:*CAS:5988-19-2:*LIGAND-CPD:C00337:*CAS:155-54-4 3.5.2.3 (S)-dihydroorotate + H2O = H+ + N-carbamoyl-L-aspartate uridine-5'-phosphate biosynthesis (S)-dihydroorotate (S)-4-pyrimidinecarboxylic acid*4,5-dihydro-L-orotate*(S)-di-H-orotate*(S)-hydroorotic acid*(S)-4,5-dihydroorotic acid*(S)-4,5-dihydroorotate*4,5-dihydroorotate*4,5-dihydroorotic acid*hydroorotic acid*(S)-dihydroorotate*di-H-orotate*L-dihydroorotate*5,6-dihydroorotate*L-4,5-dihydroorotate*4-pyrimidinecarboxylic acid*hexahydro-2,6-dioxo- 157.105 C5 H5 N2 O4 O=C1(NC(=O)CC(C(=O)[O-])N1) PUBCHEM:5460289:*CHEBI:30864:*CAS:5988-19-2:*LIGAND-CPD:C00337:*CAS:155-54-4 1.3.5.2 (S)-dihydroorotate = orotate uridine-5'-phosphate biosynthesis chlorophyllide a chlorophyllide*chlorophyllide a*chlorophyllide a 613.974 C35 H33 N4 O5 MG1 C17(N9(C2(=C(C=1C)C(=O)C(C(OC)=O)([H])C2=C3(C([H])(C([H])(C8(=N3[Mg]6(N4(C(C(=C(C4=CC5(C(=C(C(N=56)=C7)CC)C))C=C)C)=C8))9))C)CCC(=O)[O-])))) PUBCHEM:44229203:*CAS:14897-06-4*LIGAND-CPD:C02139: 1.14.13.- H+ + chlorophyllide a + oxygen + NADPH = 7-hydroxy-chlorophyllide a + H2O + NADP+ chlorophyll cycle chlorophyllide a chlorophyllide*chlorophyllide a*chlorophyllide a 613.974 C35 H33 N4 O5 MG1 C17(N9(C2(=C(C=1C)C(=O)C(C(OC)=O)([H])C2=C3(C([H])(C([H])(C8(=N3[Mg]6(N4(C(C(=C(C4=CC5(C(=C(C(N=56)=C7)CC)C))C=C)C)=C8))9))C)CCC(=O)[O-])))) PUBCHEM:44229203:*CAS:14897-06-4*LIGAND-CPD:C02139: H+ + chlorophyllide a = pheophorbide a + Mg2+ chlorophyll a degradation chlorophyllide a chlorophyllide*chlorophyllide a*chlorophyllide a 613.974 C35 H33 N4 O5 MG1 C17(N9(C2(=C(C=1C)C(=O)C(C(OC)=O)([H])C2=C3(C([H])(C([H])(C8(=N3[Mg]6(N4(C(C(=C(C4=CC5(C(=C(C(N=56)=C7)CC)C))C=C)C)=C8))9))C)CCC(=O)[O-])))) PUBCHEM:44229203:*CAS:14897-06-4*LIGAND-CPD:C02139: 3.1.1.14 chlorophyll a + H2O = H+ + chlorophyllide a + phytol chlorophyll a degradation chlorophyllide a chlorophyllide*chlorophyllide a*chlorophyllide a 613.974 C35 H33 N4 O5 MG1 C17(N9(C2(=C(C=1C)C(=O)C(C(OC)=O)([H])C2=C3(C([H])(C([H])(C8(=N3[Mg]6(N4(C(C(=C(C4=CC5(C(=C(C(N=56)=C7)CC)C))C=C)C)=C8))9))C)CCC(=O)[O-])))) PUBCHEM:44229203:*CAS:14897-06-4*LIGAND-CPD:C02139: 2.5.1.62 H+ + chlorophyllide a + phytyl diphosphate = chlorophyll a + diphosphate chlorophyll cycle chlorophyllide a chlorophyllide*chlorophyllide a*chlorophyllide a 613.974 C35 H33 N4 O5 MG1 C17(N9(C2(=C(C=1C)C(=O)C(C(OC)=O)([H])C2=C3(C([H])(C([H])(C8(=N3[Mg]6(N4(C(C(=C(C4=CC5(C(=C(C(N=56)=C7)CC)C))C=C)C)=C8))9))C)CCC(=O)[O-])))) PUBCHEM:44229203:*CAS:14897-06-4*LIGAND-CPD:C02139: 2.5.1.62 H+ + chlorophyllide a + phytyl diphosphate = chlorophyll a + diphosphate chlorophyll a biosynthesis I chlorophyllide a chlorophyllide*chlorophyllide a*chlorophyllide a 613.974 C35 H33 N4 O5 MG1 C17(N9(C2(=C(C=1C)C(=O)C(C(OC)=O)([H])C2=C3(C([H])(C([H])(C8(=N3[Mg]6(N4(C(C(=C(C4=CC5(C(=C(C(N=56)=C7)CC)C))C=C)C)=C8))9))C)CCC(=O)[O-])))) PUBCHEM:44229203:*CAS:14897-06-4*LIGAND-CPD:C02139: 2.5.1.- H+ + chlorophyllide a + all-trans-geranyl-geranyl diphosphate = geranylgeranyl-chlorophyll a + diphosphate chlorophyll a biosynthesis II chlorophyllide a chlorophyllide*chlorophyllide a*chlorophyllide a 613.974 C35 H33 N4 O5 MG1 C17(N9(C2(=C(C=1C)C(=O)C(C(OC)=O)([H])C2=C3(C([H])(C([H])(C8(=N3[Mg]6(N4(C(C(=C(C4=CC5(C(=C(C(N=56)=C7)CC)C))C=C)C)=C8))9))C)CCC(=O)[O-])))) PUBCHEM:44229203:*CAS:14897-06-4*LIGAND-CPD:C02139: 1.3.1.33 chlorophyllide a + NADP+ = H+ + monovinyl protochlorophyllide a + NADPH chlorophyllide a biosynthesis I GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 519.151 C10 H12 N5 O14 P3 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) PUBCHEM:7058167:*KNAPSACK:C00007223:*PUBCHEM:7058167:*CHEBI:37565:*LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 2.7.1.48 uridine + GTP = H+ + uridine-5'-phosphate + GDP salvage pathways of pyrimidine ribonucleotides GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 519.151 C10 H12 N5 O14 P3 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) PUBCHEM:7058167:*KNAPSACK:C00007223:*PUBCHEM:7058167:*CHEBI:37565:*LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 2.7.7.30 H+ + β-L-fucose 1-phosphate + GTP = GDP-L-fucose + diphosphate GDP-L-fucose biosynthesis II (from L-fucose) GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 519.151 C10 H12 N5 O14 P3 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) PUBCHEM:7058167:*KNAPSACK:C00007223:*PUBCHEM:7058167:*CHEBI:37565:*LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 3.5.4.25 H2O + GTP = H+ + diphosphate + 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one + formate flavin biosynthesis I (bacteria and plants) GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 519.151 C10 H12 N5 O14 P3 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) PUBCHEM:7058167:*KNAPSACK:C00007223:*PUBCHEM:7058167:*CHEBI:37565:*LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 2.7.7.34 H+ + α-D-glucose 1-phosphate + GTP = GDP-α-D-glucose + diphosphate GDP-glucose biosynthesis GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 519.151 C10 H12 N5 O14 P3 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) PUBCHEM:7058167:*KNAPSACK:C00007223:*PUBCHEM:7058167:*CHEBI:37565:*LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = H+ + adenylo-succinate + GDP purine nucleotides de novo biosynthesis II GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 519.151 C10 H12 N5 O14 P3 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) PUBCHEM:7058167:*KNAPSACK:C00007223:*PUBCHEM:7058167:*CHEBI:37565:*LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = H+ + adenylo-succinate + GDP adenosine nucleotides de novo biosynthesis GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 519.151 C10 H12 N5 O14 P3 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) PUBCHEM:7058167:*KNAPSACK:C00007223:*PUBCHEM:7058167:*CHEBI:37565:*LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 2.7.1.- cytidine + GTP = H+ + CMP + GDP salvage pathways of pyrimidine ribonucleotides GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 519.151 C10 H12 N5 O14 P3 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) PUBCHEM:7058167:*KNAPSACK:C00007223:*PUBCHEM:7058167:*CHEBI:37565:*LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 3.5.4.16 GTP + H2O = H+ + formate + 7,8-dihydroneopterin triphosphate 6-hydroxymethyl-dihydropterin diphosphate biosynthesis GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 519.151 C10 H12 N5 O14 P3 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) PUBCHEM:7058167:*KNAPSACK:C00007223:*PUBCHEM:7058167:*CHEBI:37565:*LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 2.7.7.13 H+ + α-D-mannose 1-phosphate + GTP = GDP-α-D-mannose + diphosphate ascorbate biosynthesis I (L-galactose pathway) GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 519.151 C10 H12 N5 O14 P3 NC3(=NC1(=C(N=CN1C2(OC(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C(O)C(O)2))C(=O)N3)) PUBCHEM:7058167:*KNAPSACK:C00007223:*PUBCHEM:7058167:*CHEBI:37565:*LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 2.7.7.13 H+ + α-D-mannose 1-phosphate + GTP = GDP-α-D-mannose + diphosphate GDP-mannose biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- gibberellin A4 + 2-oxoglutarate + oxygen = GA34 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- H+ + GA44 + 2-oxoglutarate + oxygen = GA98 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.2.1.24 succinate semialdehyde + H2O + NAD+ = succinate + NADH + H+ glutamate degradation III (via 4-aminobutyrate) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.2.1.24 succinate semialdehyde + H2O + NAD+ = succinate + NADH + H+ 4-aminobutyrate degradation I succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- gibberellin A12 + 2-oxoglutarate + oxygen = GA110 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA34 + 2-oxoglutarate + oxygen = H+ + GA34-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.3.5.1 succinate = fumarate TCA cycle variation III (eukaryotic) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.3.5.1 succinate = fumarate aerobic respiration -- electron donor II succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.3.5.1 succinate = fumarate succinate to cytochrome bd oxidase electron transfer succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.3.5.1 succinate = fumarate superpathway of glyoxylate cycle succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA19 + oxygen + 2-oxoglutarate = H+ + gibberellin A20 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA51 + 2-oxoglutarate + oxygen = H+ + GA51-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.12 GA44 (open lactone form) + 2-oxoglutarate + oxygen = GA19 + succinate + CO2 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA53 + oxygen + 2-oxoglutarate = GA44 (open lactone form) + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- gibberellin A8 + 2-oxoglutarate + oxygen = H+ + GA8-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.2.1.79 succinate semialdehyde + NADP+ + H2O = succinate + NADPH + H+ 4-aminobutyrate degradation II succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- leucocyanidin + 2-oxoglutarate + oxygen = H+ + cyanidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- gibberellin A9 + 2-oxoglutarate + oxygen = GA51 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 3',4',5'-pentahydroxyflavanone + 2-oxoglutarate + oxygen = dihydromyricetin + succinate + CO2 leucodelphinidin biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- gibberellin A20 + 2-oxoglutarate + oxygen = GA29 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.22 naringenin + 2-oxoglutarate + oxygen = apigenin + succinate + CO2 + H2O luteolin biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.22 eriodictyol + 2-oxoglutarate + oxygen = luteolin + succinate + CO2 + H2O luteolin biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA19 + oxygen + 2-oxoglutarate = H+ + GA17 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA53 + 2-oxoglutarate + oxygen = GA97 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.9 naringenin + oxygen + 2-oxoglutarate = CO2 + succinate + dihydrokaempferol flavonoid biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.23 dihydromyricetin + 2-oxoglutarate + oxygen = myricetin + succinate + CO2 + H2O syringetin biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.9 (2S)-pinocembrin + oxygen + 2-oxoglutarate = (2R,3R)-pinobanksin + CO2 + succinate pinobanksin biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.19 leucocyanidin + 2-oxoglutarate + oxygen = succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- H+ + GA44 (open lactone form) + 2-oxoglutarate + oxygen = GA38 + succinate + CO2 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- leucodelphinidin + oxygen + 2-oxoglutarate = H+ + delphinidin + H2O + CO2 + succinate anthocyanin biosynthesis (delphinidin 3-O-glucoside) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 6.2.1.5 succinate + coenzyme A + ATP = succinyl-CoA + ADP TCA cycle variation III (eukaryotic) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA29 + 2-oxoglutarate + oxygen = H+ + GA29-catabolite + succinate + CO2 + H2O gibberellin inactivation I (2β-hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.23 dihydrokaempferol + 2-oxoglutarate + oxygen = kaempferol + succinate + CO2 + H2O flavonol biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.13 gibberellin A1 + 2-oxoglutarate + oxygen = gibberellin A8 + succinate + CO2 gibberellin inactivation I (2β-hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.23 trans dihydroquercetin + 2-oxoglutarate + oxygen = quercetin + succinate + CO2 + H2O flavonol biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.15 gibberellin A20 + 2-oxoglutarate + oxygen = gibberellin A1 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.9 eriodictyol + oxygen + 2-oxoglutarate = trans dihydroquercetin + CO2 + succinate leucopelargonidin and leucocyanidin biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.9 eriodictyol + oxygen + 2-oxoglutarate = trans dihydroquercetin + CO2 + succinate leucodelphinidin biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 4.1.3.1 D-threo-isocitrate = glyoxylate + succinate glyoxylate cycle succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 116.073 C4 H4 O4 O=C(CCC([O-])=O)[O-] CHEBI:30031:*PUBCHEM:160419:*KNAPSACK:C00001205:*PUBCHEM:160419:*CHEBI:30031:*CHEBI:15741*LIGAND-CPD:C00042*PUBCHEM:1110*CAS:110-15-6:*LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- H+ + leucopelargonidin + 2-oxoglutarate + oxygen = pelargonidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) Cu2+ Cu+2*Cu++*cupric ion*cupric copper*Ci(II) 63.546 CU1 [Cu++] PUBCHEM:27099:*CHEBI:29036: 3.6.3.- Cu2+ + H2O + ATP = Cu2+ + ADP copper transport I Cu2+ Cu+2*Cu++*cupric ion*cupric copper*Ci(II) 63.546 CU1 [Cu++] PUBCHEM:27099:*CHEBI:29036: 3.6.3.- Cu2+ + H2O + ATP = Cu2+ + ADP copper transport I Cu2+ Cu+2*Cu++*cupric ion*cupric copper*Ci(II) 63.546 CU1 [Cu++] PUBCHEM:27099:*CHEBI:29036: 3.6.3.4 Cu2+ + H2O + ATP = Cu2+ + ADP copper transport II 4α-carboxy-4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol 9,19-cyclolanostan-28-oic acid, 3-hydroxy-24-methylene-, (3β,4α)- 469.726 C31 H49 O3 C1(CC(C(C2(C51(C3(C(CC2)C4(C)(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4))C5)))(C)C([O-])=O)O) CAS:149252-87-9: 1.14.13.- 4α-formyl,4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NADH + oxygen = 4α-carboxy-4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ + H2O plant sterol biosynthesis 4α-carboxy-4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol 9,19-cyclolanostan-28-oic acid, 3-hydroxy-24-methylene-, (3β,4α)- 469.726 C31 H49 O3 C1(CC(C(C2(C51(C3(C(CC2)C4(C)(CCC(C(CCC(C(C)C)=C)C)C(CC3)(C)4))C5)))(C)C([O-])=O)O) CAS:149252-87-9: 1.1.1.- 4α-carboxy-4β,14α-dimethyl-9β,19-cyclo-5α-ergost-24(241)-en-3β-ol + NAD+ = cycloeucalenone + NADH + CO2 plant sterol biosynthesis scopoletin 192.171 C10 H8 O4 O(C)C2(C=C1(C(OC(=O)C=C1)=CC=2O)) PUBCHEM:5280460:*CHEBI:17488:*LIGAND-CPD:C01752:*NCI:405647 esculetin = scopoletin simplecoumarins biosynthesis scopoletin 192.171 C10 H8 O4 O(C)C2(C=C1(C(OC(=O)C=C1)=CC=2O)) PUBCHEM:5280460:*CHEBI:17488:*LIGAND-CPD:C01752:*NCI:405647 scopoletin = ayapin simplecoumarins biosynthesis scopoletin 192.171 C10 H8 O4 O(C)C2(C=C1(C(OC(=O)C=C1)=CC=2O)) PUBCHEM:5280460:*CHEBI:17488:*LIGAND-CPD:C01752:*NCI:405647 2-hydroxyferulate = scopoletin simplecoumarins biosynthesis scopoletin 192.171 C10 H8 O4 O(C)C2(C=C1(C(OC(=O)C=C1)=CC=2O)) PUBCHEM:5280460:*CHEBI:17488:*LIGAND-CPD:C01752:*NCI:405647 scopoletin = scoparone simplecoumarins biosynthesis laricitrin 331.258 C16 H11 O8 C1(C(=CC(=C2(C=1OC(=C(C2=O)[O-])C3(C=C(C(=C(C=3)O)O)OC)))O)O) PUBCHEM:25203006:*CHEBI:60006:*PUBCHEM:25203006:*LIGAND-CPD:C12633: 2.1.1.149 laricitrin + S-adenosyl-L-methionine = H+ + syringetin + S-adenosyl-L-homocysteine syringetin biosynthesis laricitrin 331.258 C16 H11 O8 C1(C(=CC(=C2(C=1OC(=C(C2=O)[O-])C3(C=C(C(=C(C=3)O)O)OC)))O)O) PUBCHEM:25203006:*CHEBI:60006:*PUBCHEM:25203006:*LIGAND-CPD:C12633: 2.1.1.149 myricetin + S-adenosyl-L-methionine = H+ + laricitrin + S-adenosyl-L-homocysteine syringetin biosynthesis nicotinate riboside nicotinic acid riboside*ribosylnicotinate*nicotinic acid ribose 255.227 C11 H13 N1 O6 C2(C(O)C(CO)OC([N+]1(C=CC=C(C([O-])=O)C=1))2)(O) PUBCHEM:25203005:*LIGAND-CPD:C05841: 2.4.2.- H+ + nicotinate + D-ribulose-1-phosphate = nicotinate riboside pyridine nucleotide cycling (plants) nicotinate riboside nicotinic acid riboside*ribosylnicotinate*nicotinic acid ribose 255.227 C11 H13 N1 O6 C2(C(O)C(CO)OC([N+]1(C=CC=C(C([O-])=O)C=1))2)(O) PUBCHEM:25203005:*LIGAND-CPD:C05841: 2.7.1.- nicotinate riboside + ATP = H+ + nicotinate mononucleotide + ADP pyridine nucleotide cycling (plants) ethanol absolute alcohol*alcohol*EtOH*eth*ethyl alcohol*grain alcohol 46.069 C2 H6 O1 OCC PUBCHEM:702:*CHEBI:16236:*LIGAND-CPD:C00469:*CAS:64-17-5 1.11.1.6 ethanol + hydrogen peroxide = H2O + acetaldehyde ethanol degradation IV (peroxisomal) ethanol absolute alcohol*alcohol*EtOH*eth*ethyl alcohol*grain alcohol 46.069 C2 H6 O1 OCC PUBCHEM:702:*CHEBI:16236:*LIGAND-CPD:C00469:*CAS:64-17-5 1.1.1.1 ethanol + NAD+ = acetaldehyde + NADH + H+ acetaldehyde biosynthesis I ethanol absolute alcohol*alcohol*EtOH*eth*ethyl alcohol*grain alcohol 46.069 C2 H6 O1 OCC PUBCHEM:702:*CHEBI:16236:*LIGAND-CPD:C00469:*CAS:64-17-5 1.1.1.1 ethanol + NAD+ = acetaldehyde + NADH + H+ ethanol degradation II (cytosol) ethanol absolute alcohol*alcohol*EtOH*eth*ethyl alcohol*grain alcohol 46.069 C2 H6 O1 OCC PUBCHEM:702:*CHEBI:16236:*LIGAND-CPD:C00469:*CAS:64-17-5 1.1.1.1 ethanol + NAD+ = acetaldehyde + NADH + H+ pyruvate fermentation to ethanol II phytol 296.535 C20 H40 O1 C(CO)=C(CCCC(CCCC(CCCC(C)C)C)C)C PUBCHEM:5280435:*CHEBI:17327:*LIGAND-CPD:C01389: 3.1.1.14 chlorophyll a + H2O = H+ + chlorophyllide a + phytol chlorophyll a degradation phosphoribulosylformimino-AICAR-P 5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide*N-(5'-phospho-D-1'-ribulosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolecarboxamide*phosphoribulosylformiminoAICAR-phosphate*phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribotide phosphate*phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribonucleotide phosphate*PRFAR*N-(5'phospho-D-1'-ribulosylformimino)-5-amino-1-(5-phosphoribosyl)-4-imidazolecarboxamide 573.303 C15 H21 N5 O15 P2 N1(C=NC(C(=O)N)=C(NC=NCC(=O)C(O)C(O)COP(=O)([O-])[O-])1)C2(C(O)C(C(COP(=O)([O-])[O-])O2)O) PUBCHEM:193735:*PUBCHEM:25246314:*LIGAND-CPD:C04916: 5.3.1.16 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide = phosphoribulosylformimino-AICAR-P histidine biosynthesis phosphoribulosylformimino-AICAR-P 5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide*N-(5'-phospho-D-1'-ribulosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolecarboxamide*phosphoribulosylformiminoAICAR-phosphate*phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribotide phosphate*phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribonucleotide phosphate*PRFAR*N-(5'phospho-D-1'-ribulosylformimino)-5-amino-1-(5-phosphoribosyl)-4-imidazolecarboxamide 573.303 C15 H21 N5 O15 P2 N1(C=NC(C(=O)N)=C(NC=NCC(=O)C(O)C(O)COP(=O)([O-])[O-])1)C2(C(O)C(C(COP(=O)([O-])[O-])O2)O) PUBCHEM:193735:*PUBCHEM:25246314:*LIGAND-CPD:C04916: 2.4.2.- phosphoribulosylformimino-AICAR-P + L-glutamine = H+ + L-glutamate + D-erythro-imidazole-glycerol-phosphate + aminoimidazole carboxamide ribonucleotide histidine biosynthesis 3',4',5'-pentahydroxyflavanone dihydrotricetin*5,7,3',4',5'-pentahydroxyflavanone 303.248 C15 H11 O7 C1(C(=CC(=C2(C=1OC(CC2=O)C3(C=C(C(=C(C=3)O)O)O)))O)[O-]) CHEBI:48026:*LIGAND-CPD:C05911:*PUBCHEM:25202110: 3',4',5'-pentahydroxyflavanone + 2-oxoglutarate + oxygen = dihydromyricetin + succinate + CO2 leucodelphinidin biosynthesis 3',4',5'-pentahydroxyflavanone dihydrotricetin*5,7,3',4',5'-pentahydroxyflavanone 303.248 C15 H11 O7 C1(C(=CC(=C2(C=1OC(CC2=O)C3(C=C(C(=C(C=3)O)O)O)))O)[O-]) CHEBI:48026:*LIGAND-CPD:C05911:*PUBCHEM:25202110: 1.14.13.88 H+ + eriodictyol + NADPH + oxygen = 3',4',5'-pentahydroxyflavanone + NADP+ + H2O leucodelphinidin biosynthesis