!Compound_common_name Compound_synonyms Molecular_weight Chemical_formula Smiles Links EC Reaction_equation Pathway 5-phosphoribosyl-N-formylglycineamidine 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine*5'-phosphoribosyl-N-formyl glycineamidine*FGAM*5-phosphoribosyl-N-formylglycineamidine*5'-phosphoribosylformylglycinamidine 313.203 C8 H16 N3 O8 P1 C(=N)(CNC=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(=O)(O)O) PUBCHEM:440417:*LIGAND-CPD:C04640: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine purine nucleotides de novo 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 313.203 C8 H16 N3 O8 P1 C(=N)(CNC=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(=O)(O)O) PUBCHEM:440417:*LIGAND-CPD:C04640: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine purine nucleotides de novo 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 313.203 C8 H16 N3 O8 P1 C(=N)(CNC=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(=O)(O)O) PUBCHEM:440417:*LIGAND-CPD:C04640: 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = ADP + 5-aminoimidazole ribonucleotide purine nucleotides de novo 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 313.203 C8 H16 N3 O8 P1 C(=N)(CNC=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(=O)(O)O) PUBCHEM:440417:*LIGAND-CPD:C04640: 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = ADP + 5-aminoimidazole ribonucleotide purine nucleotides de novo biosynthesis I UDP-D-xylose udp-xylose*UDP-α-D-xylose 536.279 C14 H22 N2 O16 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)CO3))) CAS:3616-06-6 5.1.3.5 UDP-L-arabinose = UDP-D-xylose UDP-L-arabinose biosynthesis I (from UDP-xylose) UDP-D-xylose udp-xylose*UDP-α-D-xylose 536.279 C14 H22 N2 O16 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)CO3))) CAS:3616-06-6 4.1.1.35 UDP-D-glucuronate = UDP-D-xylose + CO2 UDP-D-xylose biosynthesis L-isoleucine I*ile*iso-leucine 131.174 C6 H13 N1 O2 C(=O)(O)C(N)C(C)CC CAS:73-32-5:*LIGAND-CPD:C00407: 2.6.1.42 L-isoleucine + α-ketoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine degradation I L-isoleucine I*ile*iso-leucine 131.174 C6 H13 N1 O2 C(=O)(O)C(N)C(C)CC CAS:73-32-5:*LIGAND-CPD:C00407: 2.6.1.42 L-isoleucine + α-ketoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine biosynthesis from threonine L-isoleucine I*ile*iso-leucine 131.174 C6 H13 N1 O2 C(=O)(O)C(N)C(C)CC CAS:73-32-5:*LIGAND-CPD:C00407: 2.6.1.42 L-isoleucine + α-ketoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine degradation II L-isoleucine I*ile*iso-leucine 131.174 C6 H13 N1 O2 C(=O)(O)C(N)C(C)CC CAS:73-32-5:*LIGAND-CPD:C00407: 6.1.1.5 L-isoleucine + ATP = diphosphate + AMP tRNA charging pathway crotonyl-CoA crotonyl-S-CoA*crotonyl-coenzyme A*crotonoyl-CoA*2-butenoyl-CoA*trans-but-2-enoyl-CoA*but-2-enoyl-CoA*trans-butyr-2-enoyl-CoA 835.609 C25 H40 N7 O17 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC)(n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00877:*UM-BBD-CPD:c0032:*CAS:102680-35-3 1.3.99.2 butyryl-CoA = crotonyl-CoA gallate degradation III (anaerobic) crotonyl-CoA crotonyl-S-CoA*crotonyl-coenzyme A*crotonoyl-CoA*2-butenoyl-CoA*trans-but-2-enoyl-CoA*but-2-enoyl-CoA*trans-butyr-2-enoyl-CoA 835.609 C25 H40 N7 O17 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC)(n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00877:*UM-BBD-CPD:c0032:*CAS:102680-35-3 1.3.1.- crotonyl-CoA + NADH = butyryl-CoA + NAD+ ethanol fermentation to acetate crotonyl-CoA crotonyl-S-CoA*crotonyl-coenzyme A*crotonoyl-CoA*2-butenoyl-CoA*trans-but-2-enoyl-CoA*but-2-enoyl-CoA*trans-butyr-2-enoyl-CoA 835.609 C25 H40 N7 O17 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC)(n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00877:*UM-BBD-CPD:c0032:*CAS:102680-35-3 4.1.1.70 glutaconyl-CoA = CO2 + crotonyl-CoA glutaryl-CoA degradation crotonyl-CoA crotonyl-S-CoA*crotonyl-coenzyme A*crotonoyl-CoA*2-butenoyl-CoA*trans-but-2-enoyl-CoA*but-2-enoyl-CoA*trans-butyr-2-enoyl-CoA 835.609 C25 H40 N7 O17 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC)(n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00877:*UM-BBD-CPD:c0032:*CAS:102680-35-3 4.2.1.17 3-hydroxybutyryl-CoA = crotonyl-CoA + H2O gallate degradation III (anaerobic) crotonyl-CoA crotonyl-S-CoA*crotonyl-coenzyme A*crotonoyl-CoA*2-butenoyl-CoA*trans-but-2-enoyl-CoA*but-2-enoyl-CoA*trans-butyr-2-enoyl-CoA 835.609 C25 H40 N7 O17 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC)(n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00877:*UM-BBD-CPD:c0032:*CAS:102680-35-3 1.3.99.2 butyryl-CoA = crotonyl-CoA acetyl CoA fermentation to butyrate crotonyl-CoA crotonyl-S-CoA*crotonyl-coenzyme A*crotonoyl-CoA*2-butenoyl-CoA*trans-but-2-enoyl-CoA*but-2-enoyl-CoA*trans-butyr-2-enoyl-CoA 835.609 C25 H40 N7 O17 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC)(n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00877:*UM-BBD-CPD:c0032:*CAS:102680-35-3 4.2.1.55 3-hydroxybutyryl-CoA = H2O + crotonyl-CoA acetyl CoA fermentation to butyrate crotonyl-CoA crotonyl-S-CoA*crotonyl-coenzyme A*crotonoyl-CoA*2-butenoyl-CoA*trans-but-2-enoyl-CoA*but-2-enoyl-CoA*trans-butyr-2-enoyl-CoA 835.609 C25 H40 N7 O17 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC)(n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00877:*UM-BBD-CPD:c0032:*CAS:102680-35-3 4.2.1.55 3-hydroxybutyryl-CoA = H2O + crotonyl-CoA glutaryl-CoA degradation crotonyl-CoA crotonyl-S-CoA*crotonyl-coenzyme A*crotonoyl-CoA*2-butenoyl-CoA*trans-but-2-enoyl-CoA*but-2-enoyl-CoA*trans-butyr-2-enoyl-CoA 835.609 C25 H40 N7 O17 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC)(n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00877:*UM-BBD-CPD:c0032:*CAS:102680-35-3 4.2.1.55 3-hydroxybutyryl-CoA = H2O + crotonyl-CoA ethanol fermentation to acetate mannose mannopyranoside*mannopyranose*D-mannose 180.157 C6 H12 O6 C(=O)C(O)C(O)C(O)C(O)CO LIGAND-CPD:C00159:*CAS:3458-28-4 GDP-D-mannose + H2O = GDP + mannose GDP-mannose metabolism mannose mannopyranoside*mannopyranose*D-mannose 180.157 C6 H12 O6 C(=O)C(O)C(O)C(O)C(O)CO LIGAND-CPD:C00159:*CAS:3458-28-4 2.7.1.7 mannose + ATP = mannose-6-phosphate + ADP GDP-mannose metabolism mannose mannopyranoside*mannopyranose*D-mannose 180.157 C6 H12 O6 C(=O)C(O)C(O)C(O)C(O)CO LIGAND-CPD:C00159:*CAS:3458-28-4 2.7.1.7 mannose + ATP = mannose-6-phosphate + ADP mannose degradation (2S)-2-amino-3-oxo-4-phosphonooxybutanoate 2-amino-3-oxo-4-phosphonooxybutyrate*L-2-amino-3-oxo-4-phosphonooxybutyrate 213.083 C4 H8 N1 O7 P1 C(OP(O)(O)=O)C(=O)C(N)C(O)=O PUBCHEM:441260: 1.1.1.262 4-(phosphonooxy)-threonine + NAD+ = NADH + (2S)-2-amino-3-oxo-4-phosphonooxybutanoate pyridoxal 5'-phosphate biosynthesis (2S)-2-amino-3-oxo-4-phosphonooxybutanoate 2-amino-3-oxo-4-phosphonooxybutyrate*L-2-amino-3-oxo-4-phosphonooxybutyrate 213.083 C4 H8 N1 O7 P1 C(OP(O)(O)=O)C(=O)C(N)C(O)=O PUBCHEM:441260: (2S)-2-amino-3-oxo-4-phosphonooxybutanoate + H+ = 1-amino-propan-2-one-3-phosphate + CO2 pyridoxal 5'-phosphate biosynthesis UDP-N-acetylmuramoyl-L-alanyl-D-glutamate 879.615 C28 H43 N5 O23 P2 CC(=O)NC1(C(OC(CO)C(O)C1OC(C)C(=O)NC(C)C(=O)NC(C(O)=O)CCC(O)=O)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c(=O)[nH]c(=O)cc3))) LIGAND-CPD:C00692: 6.3.2.13 UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + meso-diaminopimelate + ATP = UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + ADP peptidoglycan biosynthesis I UDP-N-acetylmuramoyl-L-alanyl-D-glutamate 879.615 C28 H43 N5 O23 P2 CC(=O)NC1(C(OC(CO)C(O)C1OC(C)C(=O)NC(C)C(=O)NC(C(O)=O)CCC(O)=O)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c(=O)[nH]c(=O)cc3))) LIGAND-CPD:C00692: 6.3.2.9 UDP-N-acetylmuramoyl-L-alanine + D-glutamate + ATP = UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + ADP peptidoglycan biosynthesis I 5-epi-aristolochene 5-epiaristolochene 204.355 C15 H24 CC12(C(=CCC(C1)C(=C)C)CCCC(C)2) 5-epi-aristolochene + O2 + NADPH = 1-deoxy-capsidiol + H2O + NADP+ capsidiol biosynthesis 5-epi-aristolochene 5-epiaristolochene 204.355 C15 H24 CC12(C(=CCC(C1)C(=C)C)CCCC(C)2) 5-epi-aristolochene + O2 + NADPH = 3-deoxy-capsidiol + H2O + NADP+ capsidiol biosynthesis 5-epi-aristolochene 5-epiaristolochene 204.355 C15 H24 CC12(C(=CCC(C1)C(=C)C)CCCC(C)2) 4.2.3.9 trans, trans-farnesyl diphosphate = 5-epi-aristolochene + diphosphate capsidiol biosynthesis D-glutamate D-glutamic acid 147.13 C5 H9 N1 O4 C(O)(=O)C(N)CCC(=O)O LIGAND-CPD:C00217:*PUBCHEM:23327:*CAS:6893-26-1 6.3.2.9 UDP-N-acetylmuramoyl-L-alanine + D-glutamate + ATP = UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + ADP peptidoglycan biosynthesis I D-glutamate D-glutamic acid 147.13 C5 H9 N1 O4 C(O)(=O)C(N)CCC(=O)O LIGAND-CPD:C00217:*PUBCHEM:23327:*CAS:6893-26-1 5.1.1.3 L-glutamate = D-glutamate peptidoglycan biosynthesis I 5-formyl-tetrahydromethanopterin N5-formyl-5,6,7,8-tetrahydromethanopterin*5-formyl-5,6,7,8-tetrahydromethanopterin*5-formyl-H4MPT*formyl-H4MPT*5-formyl-THMPT 803.692 C31 H44 N6 O17 P1 C[CH]([CH]1(N(C=O)c2(c([NH][CH]1C)nc(N)[nH]c2=O)))Nc3(ccc(cc3)CC(O)C(O)C(O)COC4(OC(C(O)C4O)COP(=O)([O-])OC(C(O)=O)CCC(O)=O)) 3.5.4.27 5,10-methenyltetrahydromethanopterin + H2O = 5-formyl-tetrahydromethanopterin methanogenesis from CO2 5-formyl-tetrahydromethanopterin N5-formyl-5,6,7,8-tetrahydromethanopterin*5-formyl-5,6,7,8-tetrahydromethanopterin*5-formyl-H4MPT*formyl-H4MPT*5-formyl-THMPT 803.692 C31 H44 N6 O17 P1 C[CH]([CH]1(N(C=O)c2(c([NH][CH]1C)nc(N)[nH]c2=O)))Nc3(ccc(cc3)CC(O)C(O)C(O)COC4(OC(C(O)C4O)COP(=O)([O-])OC(C(O)=O)CCC(O)=O)) 2.3.1.101 tetrahydromethanopterin = 5-formyl-tetrahydromethanopterin methanogenesis from CO2 pyridoxine-5'-phosphate pyridoxine-phosphate*pyridoxine-5P*pyridoxine-P 249.16 C8 H12 N1 O6 P1 c1(c(c(CO)c(O)c(C)n1)COP(=O)(O)O) CAS:447-05-2:*LIGAND-CPD:C00627: 2.6.99.2 1-deoxy-D-xylulose 5-phosphate + 1-amino-propan-2-one-3-phosphate = pyridoxine-5'-phosphate + H2O pyridoxal 5'-phosphate biosynthesis pyridoxine-5'-phosphate pyridoxine-phosphate*pyridoxine-5P*pyridoxine-P 249.16 C8 H12 N1 O6 P1 c1(c(c(CO)c(O)c(C)n1)COP(=O)(O)O) CAS:447-05-2:*LIGAND-CPD:C00627: 2.7.1.- ATP + pyridoxine = ADP + pyridoxine-5'-phosphate pyridoxal 5'-phosphate salvage pathway pyridoxine-5'-phosphate pyridoxine-phosphate*pyridoxine-5P*pyridoxine-P 249.16 C8 H12 N1 O6 P1 c1(c(c(CO)c(O)c(C)n1)COP(=O)(O)O) CAS:447-05-2:*LIGAND-CPD:C00627: 1.4.3.5 O2 + pyridoxine-5'-phosphate = H2O2 + pyridoxal 5'-phosphate pyridoxal 5'-phosphate biosynthesis pyridoxine-5'-phosphate pyridoxine-phosphate*pyridoxine-5P*pyridoxine-P 249.16 C8 H12 N1 O6 P1 c1(c(c(CO)c(O)c(C)n1)COP(=O)(O)O) CAS:447-05-2:*LIGAND-CPD:C00627: 1.4.3.5 O2 + pyridoxine-5'-phosphate = H2O2 + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway 16:0-18:2-DGDG 1-16:0-2-18:2-digalactosyldiacylglycerol*1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-3-O-[alpha-D-galactosyl-(1>6)-O-beta-D-galactosyl]-sn-glycerol 917.225 C49 H88 O15 C(OC1(OC(C(O)C(O)C1O)COC2(C(O)C(O)C(O)C(O2)CO)))C(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 16:0-18:2-DGDG = 16:0-18:3-DGDG glycolipid desaturation RCC red chlorophyll catabolite*red bilin 626.708 C35 H36 N4 O7 CCc1(c(nc([CH]=O)c(C)1)Cc2(c(C)c3(c(n2)C(C(C(=O)3)C(=O)OC)=C4(N=C(C(C)C4CCC(=O)O)C=C5(C(C)=C(C=C)C(=O)N5))))) 1.-.-.- RCC + H+ = pFCC chlorophyll a degradation RCC red chlorophyll catabolite*red bilin 626.708 C35 H36 N4 O7 CCc1(c(nc([CH]=O)c(C)1)Cc2(c(C)c3(c(n2)C(C(C(=O)3)C(=O)OC)=C4(N=C(C(C)C4CCC(=O)O)C=C5(C(C)=C(C=C)C(=O)N5))))) 1.-.-.- pheophorbide a + O2 = RCC + H2O chlorophyll a degradation 7-hydroxy-chlorophyll a 7-OH-chlorophyll a 909.502 C55 H72 N4 O6 MG1 CC(CCCC(C)CCCC(C)CCCC(C)C)=CCOC(=O)CCC7(C6(C1(C(C(=O)OC)C(=O)c2(c(C)c3(n(c=12)[Mg]59(N4(C(C(CO)=C(CC)C(C=3)=4)=Cc8(n(c(C=C(N5=6)C(C)7)c(C)c8C=C)9)))))))) chlorophyll b + H2O + NADP+ = 7-hydroxy-chlorophyll a + O2 + NADPH chlorophyll cycle 7-hydroxy-chlorophyll a 7-OH-chlorophyll a 909.502 C55 H72 N4 O6 MG1 CC(CCCC(C)CCCC(C)CCCC(C)C)=CCOC(=O)CCC7(C6(C1(C(C(=O)OC)C(=O)c2(c(C)c3(n(c=12)[Mg]59(N4(C(C(CO)=C(CC)C(C=3)=4)=Cc8(n(c(C=C(N5=6)C(C)7)c(C)c8C=C)9)))))))) 7-hydroxy-chlorophyll a + H2O + NADP+ = chlorophyll a + O2 + NADPH chlorophyll cycle 7-dehydrodesmosterol 5α-cholesta-5,7,24-trien-3β-ol 382.628 C27 H42 O1 CC(C)=CCCC(C)C1(C2(C(CC1)C3(C(CC2)C4(C(=CC=3)CC(O)CC4)(C)))(C)) PUBCHEM:440558: 1.3.1.21 7-dehydrodesmosterol + NADPH = desmosterol + NADP+ cholesterol biosynthesis III (via desmosterol) 7-dehydrodesmosterol 5α-cholesta-5,7,24-trien-3β-ol 382.628 C27 H42 O1 CC(C)=CCCC(C)C1(C2(C(CC1)C3(C(CC2)C4(C(=CC=3)CC(O)CC4)(C)))(C)) PUBCHEM:440558: 1.14.21.6 5α-cholesta-7,24-dien-3β-ol + O2 = 7-dehydrodesmosterol + H2O cholesterol biosynthesis III (via desmosterol) 3-dehydrosphinganine 3-dehydro-D-sphinganine*3-dehydrosphinganine*KDHS 299.496 C18 H37 N1 O2 CCCCCCCCCCCCCCCC(=O)C(N)CO 2.3.1.50 L-serine + palmitoyl CoA = CO2 + 3-dehydrosphinganine + coenzyme A sphingolipid metabolism 3-dehydrosphinganine 3-dehydro-D-sphinganine*3-dehydrosphinganine*KDHS 299.496 C18 H37 N1 O2 CCCCCCCCCCCCCCCC(=O)C(N)CO 1.1.1.102 NADP+ + sphinganine = NADPH + 3-dehydrosphinganine sphingolipid metabolism 7,8-dihydrofolate H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 443.418 C19 H21 N7 O6 C(C1(=Nc2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00415:*CAS:4033-27-6 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate formylTHF biosynthesis II 7,8-dihydrofolate H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 443.418 C19 H21 N7 O6 C(C1(=Nc2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00415:*CAS:4033-27-6 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate tetrahydrofolate biosynthesis I 7,8-dihydrofolate H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 443.418 C19 H21 N7 O6 C(C1(=Nc2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00415:*CAS:4033-27-6 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate formylTHF biosynthesis I 7,8-dihydrofolate H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 443.418 C19 H21 N7 O6 C(C1(=Nc2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00415:*CAS:4033-27-6 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate tetrahydrofolate biosynthesis II 7,8-dihydrofolate H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 443.418 C19 H21 N7 O6 C(C1(=Nc2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00415:*CAS:4033-27-6 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP formylTHF biosynthesis II 7,8-dihydrofolate H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 443.418 C19 H21 N7 O6 C(C1(=Nc2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00415:*CAS:4033-27-6 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP tetrahydrofolate biosynthesis I 7,8-dihydrofolate H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 443.418 C19 H21 N7 O6 C(C1(=Nc2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00415:*CAS:4033-27-6 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP formylTHF biosynthesis I 7,8-dihydrofolate H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 443.418 C19 H21 N7 O6 C(C1(=Nc2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00415:*CAS:4033-27-6 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP tetrahydrofolate biosynthesis II 7,8-dihydrofolate H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 443.418 C19 H21 N7 O6 C(C1(=Nc2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00415:*CAS:4033-27-6 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate salvage pathways of purine and pyrimidine nucleotides 7,8-dihydrofolate H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 443.418 C19 H21 N7 O6 C(C1(=Nc2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00415:*CAS:4033-27-6 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate de novo biosynthesis of pyrimidine deoxyribonucleotides 7,8-dihydrofolate H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 443.418 C19 H21 N7 O6 C(C1(=Nc2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00415:*CAS:4033-27-6 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate formylTHF biosynthesis II 7,8-dihydrofolate H2PteGlu*FH2*H2PteGlu1*dihydrofolate*DHF*7,8-dihydropteroylglutamate 443.418 C19 H21 N7 O6 C(C1(=Nc2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00415:*CAS:4033-27-6 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate formylTHF biosynthesis I sinapyl-alcohol 210.229 C11 H14 O4 C(O)C=Cc1(cc(OC)c(O)c(c1)OC) 1.1.1.195 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:*CAS:124-38-9 2.7.2.2 ammonia + CO2 + ATP = carbamoyl-phosphate + ADP citrulline degradation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.2.2.2 pyruvate + ubiquinone-8 + H2O = ubiquinol-8 + acetate + CO2 mixed acid fermentation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA34 + α-ketoglutarate + O2 = GA34-catabolite + succinate + CO2 + H2O gibberellin inactivation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 (2S)-2-amino-3-oxo-4-phosphonooxybutanoate + H+ = 1-amino-propan-2-one-3-phosphate + CO2 pyridoxal 5'-phosphate biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 α-ketoglutarate + coenzyme A + NAD+ = succinyl-CoA + CO2 + NADH TCA cycle CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.2.1.27 NAD+ + coenzyme A + methylmalonate-semialdehyde = NADH + CO2 + propionyl-CoA valine degradation I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.1.1.170 4α-carboxy-5α-cholesta-8-en-3β-ol = 5α-cholesta-8-en-3-one + CO2 cholesterol biosynthesis II (via 24,25-dihydrolanosterol) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.47 glyoxylate = CO2 + tartronate semialdehyde glycolate and glyoxylate degradation I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.47 glyoxylate = CO2 + tartronate semialdehyde allantoin degradation I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 α-ketoadipate + 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:*CAS:124-38-9 α-ketoadipate + NAD+ + coenzyme A = CO2 + NADH + glutaryl-CoA tryptophan degradation III (eukaryotic) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA51 + α-ketoglutarate + O2 = GA51-catabolite + succinate + CO2 + H2O gibberellin inactivation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 3.5.1.5 H2O + urea = ammonia + CO2 canavanine degradation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 3.5.1.5 H2O + urea = ammonia + CO2 arginine degradation VII (arginase 3 pathway) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.1.1.38 NAD+ + malate = NADH + CO2 + pyruvate gluconeogenesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA8 + α-ketoglutarate + O2 = GA8-catabolite + succinate + CO2 + H2O gibberellin inactivation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2-ketoisocaproate + 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:*CAS:124-38-9 1.1.1.42 NADP+ = NADPH + α-ketoglutarate + CO2 TCA cycle variation I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.1.1.42 NADP+ = NADPH + α-ketoglutarate + CO2 respiration (anaerobic) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.1.1.42 NADP+ = NADPH + α-ketoglutarate + CO2 TCA cycle CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.17 L-ornithine = CO2 + putrescine putrescine biosynthesis III CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.1.1.87 homoisocitrate + NAD+ = α-ketoadipate + CO2 + NADH + H+ lysine biosynthesis IV CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate de novo biosynthesis of pyrimidine ribonucleotides CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis II (acetyl cycle) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.65 phospholipid biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.65 phospholipid biosynthesis II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.2.99.5 H2O = CO2 methanogenesis from CO2 CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA53 + α-ketoglutarate + O2 = GA97 + succinate + CO2 gibberellin inactivation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.2.7.1 pyruvate + coenzyme A = acetyl-CoA + CO2 reductive TCA cycle I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.2.7.1 pyruvate + coenzyme A = acetyl-CoA + CO2 D-lactate fermentation to propionate and acetate CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.2.7.1 pyruvate + coenzyme A = acetyl-CoA + CO2 glutamate degradation VII (to butyrate) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.48 1-(o-carboxyphenylamino)-1'-deoxyribulose-5'-phosphate = indole-3-glycerol-phosphate + CO2 + H2O tryptophan biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.70 glutaconyl-CoA = CO2 + crotonyl-CoA glutaryl-CoA degradation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.3.1.170 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:*CAS:124-38-9 1.1.1.170 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol = 4α-methyl-5α-cholesta-8,24-dien-3-one + CO2 cholesterol biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.1.1.170 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol = 4α-methyl-5α-cholesta-8,24-dien-3-one + CO2 cholesterol biosynthesis III (via desmosterol) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.45 2-amino-3-carboxymuconate semialdehyde = CO2 + 2-aminomuconate semialdehyde tryptophan degradation III (eukaryotic) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.2.1.7 pyruvate + D-glyceraldehyde-3-phosphate = 1-deoxy-D-xylulose 5-phosphate + CO2 pyridoxal 5'-phosphate biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.2.1.7 pyruvate + D-glyceraldehyde-3-phosphate = 1-deoxy-D-xylulose 5-phosphate + CO2 thiamine biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.2.1.7 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:*CAS:124-38-9 1.14.11.- GA29 + α-ketoglutarate + O2 = GA29-catabolite + succinate + CO2 + H2O gibberellin inactivation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 3.5.3.- N2-succinyl-L-arginine + H2O = ammonia + N2-succinyl-L-ornithine + CO2 arginine degradation II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.7.3.3 urate + O2 = allantoin + CO2 + H2O2 purine degradation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.13.12.1 O2 + 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:*CAS:124-38-9 1.14.11.23 dihydrokaempferol + α-ketoglutarate + O2 = kaempferol + succinate + CO2 + H2O flavonol biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA12 + O2 + α-ketoglutarate = GA15 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA24 + α-ketoglutarate + O2 = GA36 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2-oxo-4-methylthiobutanoate = 3-methylthiopropanal + CO2 methionine degradation III CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.2.1.6 pyruvate + 2-oxobutanoate = 2-aceto-2-hydroxy-butyrate + CO2 isoleucine biosynthesis from threonine CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.3.1.- H2O + coumaroyl-CoA + 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:*CAS:124-38-9 1.14.11.- GA4 + α-ketoglutarate + O2 = GA34 + succinate + CO2 gibberellin inactivation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.3.1.- acetyl-CoA = coenzyme A + CO2 fatty acid biosynthesis - initial steps CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.1.1.170 4α-carboxy-4β-methyl-5α-cholesta-8-en-3β-ol = 4α-methyl-5α-cholesta-8-en-3-one + CO2 cholesterol biosynthesis II (via 24,25-dihydrolanosterol) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA9 + α-ketoglutarate + O2 = GA4 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.18 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:*CAS:124-38-9 4.1.1.59 gallate = CO2 + pyrogallol gallate degradation III (anaerobic) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA36 + O2 + α-ketoglutarate = GA4 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA15 + α-ketoglutarate + O2 = GA24 + succinate + CO2 + H2O gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA19 + O2 + α-ketoglutarate = GA20 + 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:*CAS:124-38-9 4.1.1.37 uroporphyrinogen-III = CO2 + coproporphyrinogen III heme biosynthesis II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.37 uroporphyrinogen-III = CO2 + coproporphyrinogen III chlorophyllide a biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 fatty acid elongation -- unsaturated II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.12 GA44 + α-ketoglutarate + O2 = GA19 + 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:*CAS:124-38-9 4.1.1.36 R-4'-phosphopantothenoyl-L-cysteine = pantetheine 4'-phosphate + CO2 coenzyme A biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.2.4.2 α-ketoglutarate = CO2 2-keto glutarate dehydrogenase complex CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.71 α-ketoglutarate = succinate semialdehyde + CO2 TCA cycle variation I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- leucocyanidin + α-ketoglutarate + O2 = 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:*CAS:124-38-9 4.1.1.71 α-ketoglutarate + thiamine diphosphate = succinate-semialdehyde-thiamine PPi + CO2 menaquinone biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.20 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:*CAS:124-38-9 4.1.1.20 meso-diaminopimelate = CO2 + L-lysine lysine biosynthesis II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.20 meso-diaminopimelate = CO2 + L-lysine lysine biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.32 oxaloacetate + GTP = CO2 + phosphoenolpyruvate + GDP asparagine degradation I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.3.1.156 malonyl-CoA + isobutyryl-CoA = phlorisobutyrophenone + CO2 + coenzyme A cohumulone biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA20 + α-ketoglutarate + O2 = GA29 + succinate + CO2 gibberellin inactivation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA19 + O2 + α-ketoglutarate = 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:*CAS:124-38-9 1.2.7.3 α-ketoglutarate + coenzyme A = succinyl-CoA + CO2 reductive TCA cycle I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.9 (2S)-pinocembrin + O2 + α-ketoglutarate = (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:*CAS:124-38-9 1.2.1.- pyruvate + coenzyme A + NAD+ = acetyl-CoA + CO2 + NADH respiration (anaerobic) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA12 + α-ketoglutarate + O2 = GA14 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.2.1.51 prephenate = phenylpyruvate + H2O + CO2 phenylalanine biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.3.1.95 malonyl-CoA + coumaroyl-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:*CAS:124-38-9 4.1.1.28 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:*CAS:124-38-9 4.1.1.28 L-tryptophan = CO2 + tryptamine secologanin and strictosidine biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.3.1.41 fatty acid biosynthesis - initial steps CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O 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:*CAS:124-38-9 4.1.1.49 oxaloacetate + ATP = CO2 + phosphoenolpyruvate + ADP gluconeogenesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.15 GA20 + α-ketoglutarate + O2 = GA1 + 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:*CAS:124-38-9 3.5.1.6 H2O + 3-ureidopropionate = ammonia + CO2 + β-alanine β-alanine biosynthesis III CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.3.1.47 pimeloyl-CoA + L-alanine = CO2 + coenzyme A + 7-keto-8-aminopelargonate biotin biosynthesis II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.3.1.47 pimeloyl-CoA + L-alanine = CO2 + coenzyme A + 7-keto-8-aminopelargonate biotin biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.33 mevalonate-5-PP + ATP = CO2 + ADP mevalonate pathway CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.23 orotidine-5'-phosphate = CO2 + UMP de novo biosynthesis of pyrimidine ribonucleotides CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA25 + α-ketoglutarate + O2 = GA13 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.2.1.2 formate + menaquinone-8 = CO2 + menaquinol respiration (anaerobic)-- electron donors reaction list CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.2.1.2 formate + menaquinone-8 = CO2 + menaquinol formate oxidation to CO2 CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.4.2.19 CO2 + diphosphate + nicotinate nucleotide = 5-phosphoribosyl 1-pyrophosphate + quinolinate NAD biosynthesis I (from aspartate) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA44 + α-ketoglutarate + O2 = GA98 + succinate + CO2 gibberellin inactivation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 homogentisate + phytyl-PP = 2-methyl-6-phytyl-1,4-benzoquinone + CO2 + diphosphate vitamin E biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA12 + α-ketoglutarate + O2 = GA110 + succinate + CO2 gibberellin inactivation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.43 phenylpyruvate = CO2 + phenylacetaldehyde phenylalanine degradation III CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.3.3.3 coproporphyrinogen III + O2 + H+ = protoporphyrinogen IX + CO2 + H2O heme biosynthesis II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.3.3.3 coproporphyrinogen III + O2 + H+ = protoporphyrinogen IX + CO2 + H2O chlorophyllide a biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 homogentisate + solanyl pyrophosphate = 2-methyl-6-solanyl-1,4-benzoquinone + CO2 + diphosphate plastoquinone biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.72 2-keto-3-methyl-valerate = 2-methylbutanal + CO2 isoleucine degradation II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.3.1.41 fatty acid biosynthesis - initial steps CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.2.1.1 H2CO3 = H2O + CO2 cyanate degradation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.74 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:*CAS:124-38-9 1.14.11.- GA9 + α-ketoglutarate + O2 = GA51 + succinate + CO2 gibberellin inactivation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 3',4',5'-pentahydroxyflavanone + α-ketoglutarate + O2 = dihydromyricetin + succinate + CO2 leucodelphinidin biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2-keto-3-methyl-valerate + NAD+ + coenzyme A = S-2-methyl-butyryl-CoA + NADH + CO2 isoleucine degradation I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.1.1.- 3-(2'-methylthio)ethylmalic-acid = 2-oxo-5-methylthiopentanoic-acid + CO2 homomethionine biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.15 L-glutamate = CO2 + 4-aminobutyrate glutamate degradation III CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.3.99.1 HCO3- + cyanate = carbamate + CO2 cyanate degradation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.19 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:*CAS:124-38-9 4.1.1.19 L-arginine = CO2 + agmatine putrescine biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.19 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:*CAS:124-38-9 4.1.1.19 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:*CAS:124-38-9 4.1.1.4 acetoacetate + H+ = acetone + CO2 acetone degradation (to methylglyoxal) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.1.1.40 NADP+ + malate = NADPH + CO2 + pyruvate gluconeogenesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.3.1.50 L-serine + palmitoyl CoA = CO2 + 3-dehydrosphinganine + coenzyme A sphingolipid metabolism CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate = demethylmenaquinone-8 + diphosphate + CO2 menaquinone biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 3.5.1.53 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:*CAS:124-38-9 3.5.1.53 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:*CAS:124-38-9 1.2.4.4 2-keto-isovalerate = CO2 branched-chain α-keto acid dehydrogenase complex CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.13.11.27 p-hydroxyphenylpyruvate + O2 = CO2 + homogentisate vitamin E biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.13.11.27 p-hydroxyphenylpyruvate + O2 = CO2 + homogentisate tyrosine degradation I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.13.11.27 p-hydroxyphenylpyruvate + O2 = CO2 + homogentisate plastoquinone biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.1 2-ketoisocaproate = 3-methylbutanal + CO2 leucine degradation III CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.2.1.25 NAD+ + coenzyme A + 2-keto-isovalerate = NADH + CO2 + isobutyryl-CoA valine degradation I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.- 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:*CAS:124-38-9 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 mixed acid fermentation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 reductive TCA cycle I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 gluconeogenesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 respiration (anaerobic) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.3.1.74 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:*CAS:124-38-9 1.14.11.13 GA1 + α-ketoglutarate + O2 = GA8 + succinate + CO2 gibberellin inactivation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.23 dihydroquercetin + α-ketoglutarate + O2 = quercetin + succinate + CO2 + H2O flavonol biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 6.3.4.16 ammonia + H2O + CO2 + ATP = carbamoyl-phosphate + ADP urea cycle CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O 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:*CAS:124-38-9 3.5.3.19 H2O + (S)-ureidoglycolate = ammonia + CO2 + glyoxylate allantoin degradation I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.35 UDP-D-glucuronate = UDP-D-xylose + CO2 UDP-D-xylose biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.9 eriodictyol + O2 + α-ketoglutarate = 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:*CAS:124-38-9 1.14.11.9 eriodictyol + O2 + α-ketoglutarate = dihydroquercetin + CO2 + succinate leucodelphinidin biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.3.1.- 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:*CAS:124-38-9 2-isopropyl-3-oxosuccinate = 2-ketoisocaproate + CO2 leucine biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.1 2-keto-isovalerate = isobutanal + CO2 valine degradation II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.17.4 L-ascorbate + 1-aminocyclopropane-1-carboxylate + O2 = 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:*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:*CAS:124-38-9 1.14.11.- GA53 + O2 + α-ketoglutarate = GA44 + 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:*CAS:124-38-9 4.1.1.1 pyruvate = acetaldehyde + CO2 sucrose degradation to ethanol and lactate (anaerobic) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA37 + α-ketoglutarate + O2 = GA36 + succinate + CO2 + H2O gibberellin biosynthesis II (early C-3 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH folate transformations CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH formylTHF biosynthesis II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH formylTHF biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH photorespiration CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 malonyl-CoA = CO2 epicuticular wax biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1,4-dihydroxy-2-naphthoate + phytyl-PP = demethylphylloquinone + CO2 + diphosphate phylloquinone biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.39 CO2 + H2O = 3-phosphoglycerate + H+ Calvin cycle CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA24 + O2 + α-ketoglutarate = GA9 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.50 S-adenosyl-L-methionine = CO2 + S-adenosyl-L-methioninamine spermidine biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.50 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:*CAS:124-38-9 1.14.11.9 naringenin + O2 + α-ketoglutarate = CO2 + succinate + dihydrokaempferol flavonoid biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA15 + α-ketoglutarate + O2 = GA37 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 formate = CO2 + H2 mixed acid fermentation CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 formate = CO2 + H2 respiration (anaerobic) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- leucodelphinidin + O2 + α-ketoglutarate = 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:*CAS:124-38-9 1.14.11.- GA44 + α-ketoglutarate + O2 = GA38 + 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:*CAS:124-38-9 3.5.1.20 citrulline + H2O = L-ornithine + CO2 + ammonia proline biosynthesis V (from arginine) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.3.1.- 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:*CAS:124-38-9 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate = allantoin + CO2 ureide biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.13.99.3 L-tryptophan + O2 = indole acetaldehyde + ammonia + CO2 tryptophan degradation V (side chain pathway) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.1.1.170 4α-carboxy-5α-cholesta-8,24-dien-3β-ol = 5α-cholesta-8,24-dien-3-one + CO2 cholesterol biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.1.1.170 4α-carboxy-5α-cholesta-8,24-dien-3β-ol = 5α-cholesta-8,24-dien-3-one + CO2 cholesterol biosynthesis III (via desmosterol) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = dethiobiotin + ADP biotin biosynthesis II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = dethiobiotin + ADP biotin biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 reductive TCA cycle I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 6.3.4.14 CO2 + ATP = ADP biotin-carboxyl carrier protein CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.3.1.156 malonyl-CoA + isovaleryl-CoA = phlorisovalerophenone + CO2 + coenzyme A humulone biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 4.1.1.21 4-carboxyaminoimidazole ribonucleotide = 5-aminoimidazole ribonucleotide + CO2 purine nucleotides de novo biosynthesis II CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2-amino-3-oxobutanoate = aminoacetone + CO2 threonine degradation III (to methylglyoxal) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2-amino-3-oxobutanoate = aminoacetone + CO2 aminopropanol biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.2.4.1 pyruvate = CO2 pyruvate dehydrogenase complex CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA24 + O2 + α-ketoglutarate = GA25 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- GA14 + O2 + α-ketoglutarate = GA37 + CO2 + succinate gibberellin biosynthesis II (early C-3 hydroxylation) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.13.12.3 O2 + L-tryptophan = indole-3-acetamide + H2O + CO2 IAA biosynthesis VI (via indole-3-acetamide) CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O 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:*CAS:124-38-9 1.14.13.- L-tryptophan + NADPH + O2 = indole-3-acetaldoxime + CO2 + NADP+ + H2O IAA biosynthesis I CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 2.2.1.6 pyruvate = 2-acetolactate + CO2 valine biosynthesis CO2 carbonic anhydride*carbonic acid gas*carbon dioxide 44.01 C1 O2 C(=O)=O LIGAND-CPD:C00011:*CAS:124-38-9 1.14.11.- leucopelargonidin + α-ketoglutarate + O2 = pelargonidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) 3-cyanopyridine 104.111 C6 H4 N2 C(#N)C1(=CC=CN=C1) NCI:17558*CAS:100-54-9 4.2.1.- E-pyridine-3-aldoxime = 3-cyanopyridine + H2O aldoxime degradation 3-cyanopyridine 104.111 C6 H4 N2 C(#N)C1(=CC=CN=C1) NCI:17558*CAS:100-54-9 4.2.1.84 3-cyanopyridine + H2O = nicotinamide aldoxime degradation strictosidine 3-α(S)-strictosidine 530.574 C27 H33 N2 O9 C1(N[CH](c2(c(C1)c3(c(n2)cccc3)))C[CH]4([CH](C=C)C(OC=C4C(=O)OC)OC5(C(O)C(O)C(O)C(O5)CO))) CAS:20824-29-7 4.3.3.2 tryptamine + secologanin = strictosidine + H2O secologanin and strictosidine biosynthesis β-alanine betaine N,N,N-trimethyl-β-alanine 131.174 C6 H13 N1 O2 C([N+](C)(C)C)CC(=O)[O-] 2.1.1.- N,N-dimethyl-β-alanine + S-adenosyl-L-methionine = β-alanine betaine + S-adenosyl-L-homocysteine β-alanine betaine biosynthesis GA4 gibberellin A4*gibberellin A4*GA4 332.396 C19 H24 O5 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(C(O)CC3)(C)[CH]4C5C(=O)O)))) 1.14.11.- GA4 + α-ketoglutarate + O2 = GA34 + succinate + CO2 gibberellin inactivation GA4 gibberellin A4*gibberellin A4*GA4 332.396 C19 H24 O5 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(C(O)CC3)(C)[CH]4C5C(=O)O)))) 1.14.11.- GA9 + α-ketoglutarate + O2 = GA4 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) GA4 gibberellin A4*gibberellin A4*GA4 332.396 C19 H24 O5 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(C(O)CC3)(C)[CH]4C5C(=O)O)))) 1.14.11.- GA36 + O2 + α-ketoglutarate = GA4 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) 3-pyridylacetate 3-pyridylacetic acid*3-pyridineacetic acid*2-(3-pyridyl)acetic acid*coletin*lessterol*lioxone*minedil*piridil*pyridine-3-acetic acid*toneon 137.138 C7 H7 N1 O2 c1(ncc(cc1)CC(O)=O) 4-(3-pyridyl)-butanoate = 3-pyridylacetate nicotine degradation II 3-pyridylacetate 3-pyridylacetic acid*3-pyridineacetic acid*2-(3-pyridyl)acetic acid*coletin*lessterol*lioxone*minedil*piridil*pyridine-3-acetic acid*toneon 137.138 C7 H7 N1 O2 c1(ncc(cc1)CC(O)=O) 4-(3-pyridyl)-butanoate = 3-pyridylacetate nicotine degradation III N10-formyl-THF 10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 473.444 C20 H23 N7 O7 C2(C(Nc1(c(=O)[nH]c(N)nc1N2))CN(C=O)c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) LIGAND-CPD:C00234:*CAS:2800-34-2 2.1.2.3 N10-formyl-THF + AICAR = tetrahydrofolate + phosphoribosyl-formamido-carboxamide purine nucleotides de novo biosynthesis II N10-formyl-THF 10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 473.444 C20 H23 N7 O7 C2(C(Nc1(c(=O)[nH]c(N)nc1N2))CN(C=O)c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) LIGAND-CPD:C00234:*CAS:2800-34-2 2.1.2.3 N10-formyl-THF + AICAR = tetrahydrofolate + phosphoribosyl-formamido-carboxamide purine nucleotides de novo biosynthesis I N10-formyl-THF 10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 473.444 C20 H23 N7 O7 C2(C(Nc1(c(=O)[nH]c(N)nc1N2))CN(C=O)c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) LIGAND-CPD:C00234:*CAS:2800-34-2 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF folate polyglutamylation I N10-formyl-THF 10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 473.444 C20 H23 N7 O7 C2(C(Nc1(c(=O)[nH]c(N)nc1N2))CN(C=O)c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) LIGAND-CPD:C00234:*CAS:2800-34-2 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF folate transformations N10-formyl-THF 10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 473.444 C20 H23 N7 O7 C2(C(Nc1(c(=O)[nH]c(N)nc1N2))CN(C=O)c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) LIGAND-CPD:C00234:*CAS:2800-34-2 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF formylTHF biosynthesis II N10-formyl-THF 10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 473.444 C20 H23 N7 O7 C2(C(Nc1(c(=O)[nH]c(N)nc1N2))CN(C=O)c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) LIGAND-CPD:C00234:*CAS:2800-34-2 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF formylTHF biosynthesis I N10-formyl-THF 10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 473.444 C20 H23 N7 O7 C2(C(Nc1(c(=O)[nH]c(N)nc1N2))CN(C=O)c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) LIGAND-CPD:C00234:*CAS:2800-34-2 3.5.4.9 H2O = N10-formyl-THF folate transformations N10-formyl-THF 10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 473.444 C20 H23 N7 O7 C2(C(Nc1(c(=O)[nH]c(N)nc1N2))CN(C=O)c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) LIGAND-CPD:C00234:*CAS:2800-34-2 3.5.4.9 H2O = N10-formyl-THF formylTHF biosynthesis II N10-formyl-THF 10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 473.444 C20 H23 N7 O7 C2(C(Nc1(c(=O)[nH]c(N)nc1N2))CN(C=O)c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) LIGAND-CPD:C00234:*CAS:2800-34-2 3.5.4.9 H2O = N10-formyl-THF tetrahydrofolate biosynthesis I N10-formyl-THF 10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 473.444 C20 H23 N7 O7 C2(C(Nc1(c(=O)[nH]c(N)nc1N2))CN(C=O)c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) LIGAND-CPD:C00234:*CAS:2800-34-2 3.5.4.9 H2O = N10-formyl-THF formylTHF biosynthesis I N10-formyl-THF 10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 473.444 C20 H23 N7 O7 C2(C(Nc1(c(=O)[nH]c(N)nc1N2))CN(C=O)c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) LIGAND-CPD:C00234:*CAS:2800-34-2 2.1.2.2 N10-formyl-THF + 5-phospho-ribosyl-glycineamide = tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide purine nucleotides de novo biosynthesis II N10-formyl-THF 10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 473.444 C20 H23 N7 O7 C2(C(Nc1(c(=O)[nH]c(N)nc1N2))CN(C=O)c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) LIGAND-CPD:C00234:*CAS:2800-34-2 2.1.2.2 N10-formyl-THF + 5-phospho-ribosyl-glycineamide = tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide tetrahydrofolate biosynthesis I N10-formyl-THF 10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 473.444 C20 H23 N7 O7 C2(C(Nc1(c(=O)[nH]c(N)nc1N2))CN(C=O)c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) LIGAND-CPD:C00234:*CAS:2800-34-2 2.1.2.2 N10-formyl-THF + 5-phospho-ribosyl-glycineamide = tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide purine nucleotides de novo biosynthesis I N10-formyl-THF 10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 473.444 C20 H23 N7 O7 C2(C(Nc1(c(=O)[nH]c(N)nc1N2))CN(C=O)c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) LIGAND-CPD:C00234:*CAS:2800-34-2 3.5.1.10 H2O + N10-formyl-THF = tetrahydrofolate + formate folate transformations N10-formyl-THF 10-formyl-tetrahydrofolate*n10-formyltetrahydrofolate*N10-formyl-H4F*10-formyl-THF*10-formyl-H4PteGlu1 473.444 C20 H23 N7 O7 C2(C(Nc1(c(=O)[nH]c(N)nc1N2))CN(C=O)c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) LIGAND-CPD:C00234:*CAS:2800-34-2 3.5.1.10 H2O + N10-formyl-THF = tetrahydrofolate + formate formylTHF biosynthesis I (-)-menthone l-menthone*p-menthan-3-one 154.252 C10 H18 O1 CC(C)C1(C(=O)CC(C)CC1) NCI:113134*CAS:14073-97-3*CAS:10458-14-7 (+)-pulegone + NADPH = (-)-menthone + NADP+ menthol biosynthesis 3-methylbutanal 3-methylbutanal*isoamylaldehyde*isopentaldehyde 86.133 C5 H10 O1 CC(C)C[CH]=O PUBCHEM:11552: 4.1.1.1 2-ketoisocaproate = 3-methylbutanal + CO2 leucine degradation III 3-methylbutanal 3-methylbutanal*isoamylaldehyde*isopentaldehyde 86.133 C5 H10 O1 CC(C)C[CH]=O PUBCHEM:11552: 1.1.1.1 3-methylbutanal + NADH = isoamyl alcohol + NAD+ leucine degradation III coumarin coumarin*cumarin*1,2-Benzopyrone 146.145 C9 H6 O2 c1(ccc2(c(o1)cccc2))(=O) PUBCHEM:323: coumarinate = coumarin + H2O coumarin biosynthesis (via 2-coumarate) N-acetylglucosaminyl-diphosphodolichol N-acetyl-D-glucosaminyldiphosphodolichol 1473.076 C88 H147 N1 O12 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(O)C(O1)CO) 2.4.1.141 N-acetylglucosaminyl-diphosphodolichol + UDP-N-acetyl-D-glucosamine = (N-acetylglucosaminyl)2-diphosphodolichol + UDP dolichyl-diphosphooligosaccharide biosynthesis N-acetylglucosaminyl-diphosphodolichol N-acetyl-D-glucosaminyldiphosphodolichol 1473.076 C88 H147 N1 O12 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(O)C(O1)CO) 2.7.8.15 dolichyl-phosphate + UDP-N-acetyl-D-glucosamine = N-acetylglucosaminyl-diphosphodolichol + UMP dolichyl-diphosphooligosaccharide biosynthesis ent-cassa-12,15-diene-2,3α-ol-11-keto ent-cassa-12,15-diene-2,3alpha-ol-11-keto*ent-cassadiene-2,3α-ol-11-keto*ent-cassadiene-2,3alpha-ol-11-keto 318.455 C20 H30 O3 CC1([CH]2(C(CC(O)C(O)1)(C)C3([CH](CC2)C(C)C(C=C)=CC3=O)))(C) ent-cassa-12,15-diene-2,3α-ol-11-keto = phytocassane A phytocassane biosynthesis ent-cassa-12,15-diene-2,3α-ol-11-keto ent-cassa-12,15-diene-2,3alpha-ol-11-keto*ent-cassadiene-2,3α-ol-11-keto*ent-cassadiene-2,3alpha-ol-11-keto 318.455 C20 H30 O3 CC1([CH]2(C(CC(O)C(O)1)(C)C3([CH](CC2)C(C)C(C=C)=CC3=O)))(C) ent-cassa-12,15-diene-3α-ol-11-keto = ent-cassa-12,15-diene-2,3α-ol-11-keto phytocassane biosynthesis ent-cassa-12,15-diene-2,3α-ol-11-keto ent-cassa-12,15-diene-2,3alpha-ol-11-keto*ent-cassadiene-2,3α-ol-11-keto*ent-cassadiene-2,3alpha-ol-11-keto 318.455 C20 H30 O3 CC1([CH]2(C(CC(O)C(O)1)(C)C3([CH](CC2)C(C)C(C=C)=CC3=O)))(C) ent-cassa-12,15-diene-2,3α-ol-11-keto = phytocassane D phytocassane biosynthesis ent-cassa-12,15-diene-2,3α-ol-11-keto ent-cassa-12,15-diene-2,3alpha-ol-11-keto*ent-cassadiene-2,3α-ol-11-keto*ent-cassadiene-2,3alpha-ol-11-keto 318.455 C20 H30 O3 CC1([CH]2(C(CC(O)C(O)1)(C)C3([CH](CC2)C(C)C(C=C)=CC3=O)))(C) ent-cassa-12,15-diene-2,3α-ol-11-keto = phytocassane B phytocassane biosynthesis ε-carotene ε,ε-carotene 536.882 C40 H56 CC(C=CC1(C(C)(C)CCC=C1C))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)=CCCC(C)2C) 5.5.1.- δ-carotene = ε-carotene lactucaxanthin biosynthesis ε-carotene ε,ε-carotene 536.882 C40 H56 CC(C=CC1(C(C)(C)CCC=C1C))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)=CCCC(C)2C) 1.14.99.- ε-carotene + O2 = ε,ε-carotene-3-diol + H2O lactucaxanthin biosynthesis ent-7-α-hydroxykaurenoate ent-7α-hydroxykaur-16-en-19-oate*ent-7-α-hydroxykaurenoic acid*7-hydroxy-kaurenoic acid 318.455 C20 H30 O3 CC1([CH]2(C(CCC1)(C)[CH]4(C3(C(O)C2)(CC(C(=C)C3)CC4))))(C(=O)O) 1.14.13.79 ent-kaurenoate + O2 + 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 318.455 C20 H30 O3 CC1([CH]2(C(CCC1)(C)[CH]4(C3(C(O)C2)(CC(C(=C)C3)CC4))))(C(=O)O) 1.14.13.79 ent-7-α-hydroxykaurenoate + NADPH + H+ + O2 = GA12-aldehyde + NADP+ + H2O GA12 biosynthesis m-chlorohippurate m-chlorohippuric acid 213.62 C9 H8 N1 O3 CL1 C(C(O)=O)NC(=O)c1(cc(Cl)ccc1) m-chlorobenzoate + glycine = m-chlorohippurate + H2O bupropion degradation orotate orotic acid 156.098 C5 H4 N2 O4 C(O)(=O)c1([nH]c(=O)[nH]c(c1)=O) LIGAND-CPD:C00295:*CAS:65-86-1 1.3.3.1 O2 + dihydroorotate = H2O2 + orotate de novo biosynthesis of pyrimidine ribonucleotides orotate orotic acid 156.098 C5 H4 N2 O4 C(O)(=O)c1([nH]c(=O)[nH]c(c1)=O) LIGAND-CPD:C00295:*CAS:65-86-1 2.4.2.10 orotidine-5'-phosphate + diphosphate = 5-phosphoribosyl 1-pyrophosphate + orotate de novo biosynthesis of pyrimidine ribonucleotides 18:3-16:0-PG 1-18:3-2-16:0-phosphatidylglycerol*1-(9Z,12Z,15Z-octadecatrienoyl)-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) 744.984 C40 H73 O10 P1 C(OP(=O)(O)OCC(O)CO)C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:2-16:0-PG = 18:3-16:0-PG phospholipid desaturation 18:3-16:0-PG 1-18:3-2-16:0-phosphatidylglycerol*1-(9Z,12Z,15Z-octadecatrienoyl)-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) 744.984 C40 H73 O10 P1 C(OP(=O)(O)OCC(O)CO)C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:3-16:0-PG = 18:3-t16:1-PG phospholipid desaturation GA34 gibberellin A34*gibberellin A34*GA34 348.395 C19 H24 O6 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(C(O)C(O)C3)(C)[CH]4C5C(=O)O)))) 1.14.11.- GA4 + α-ketoglutarate + O2 = GA34 + succinate + CO2 gibberellin inactivation GA34 gibberellin A34*gibberellin A34*GA34 348.395 C19 H24 O6 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(C(O)C(O)C3)(C)[CH]4C5C(=O)O)))) 1.14.11.- GA34 + α-ketoglutarate + O2 = GA34-catabolite + succinate + CO2 + H2O gibberellin inactivation malonate semialdehyde 3-oxopropanoate*malonate-S-ald 88.063 C3 H4 O3 C(O)(=O)C[CH]=O CAS:926-61-4 1.1.1.59 NAD+ + 3-hydroxy-propionate = NADH + malonate semialdehyde β-alanine biosynthesis II malonate semialdehyde 3-oxopropanoate*malonate-S-ald 88.063 C3 H4 O3 C(O)(=O)C[CH]=O CAS:926-61-4 2.6.1.18 malonate semialdehyde + L-alanine = β-alanine + pyruvate β-alanine biosynthesis II 1-(3-aminopropyl)-4-aminobutanal 144.216 C7 H16 N2 O1 C(N)CCNCCCC=O 1-(3-aminopropyl)-4-aminobutanal = 1-(3-aminopropyl)-pyrrolinium + H2O β-alanine biosynthesis I 1-(3-aminopropyl)-4-aminobutanal 144.216 C7 H16 N2 O1 C(N)CCNCCCC=O 1.5.3.11 spermine + O2 + H2O = 1-(3-aminopropyl)-4-aminobutanal + 1,3-diaminopropane + H2O2 β-alanine biosynthesis I sucrose-6-phosphate sucrose 6F-phosphate*sucrose-6-P 422.279 C12 H23 O14 P1 C(O)C1(OC(C(O)C(O)C1O)OC2(CO)(OC(C(O)C2O)COP(O)(O)=O)) PUBCHEM:439762:*LIGAND-CPD:C02591: 3.2.1.26 H2O + sucrose-6-phosphate = β-D-glucose-6-phosphate + fructose sucrose degradation I sucrose-6-phosphate sucrose 6F-phosphate*sucrose-6-P 422.279 C12 H23 O14 P1 C(O)C1(OC(C(O)C(O)C1O)OC2(CO)(OC(C(O)C2O)COP(O)(O)=O)) PUBCHEM:439762:*LIGAND-CPD:C02591: 2.7.1.69 sucrose = sucrose-6-phosphate sucrose degradation I sucrose-6-phosphate sucrose 6F-phosphate*sucrose-6-P 422.279 C12 H23 O14 P1 C(O)C1(OC(C(O)C(O)C1O)OC2(CO)(OC(C(O)C2O)COP(O)(O)=O)) PUBCHEM:439762:*LIGAND-CPD:C02591: 2.4.1.14 fructose-6-phosphate + UDP-D-glucose = sucrose-6-phosphate + UDP sucrose biosynthesis sucrose-6-phosphate sucrose 6F-phosphate*sucrose-6-P 422.279 C12 H23 O14 P1 C(O)C1(OC(C(O)C(O)C1O)OC2(CO)(OC(C(O)C2O)COP(O)(O)=O)) PUBCHEM:439762:*LIGAND-CPD:C02591: 3.1.3.24 sucrose-6-phosphate + H2O = sucrose sucrose biosynthesis O-ureidohomoserine 177.16 C5 H11 N3 O4 C(ONC(=O)N)CC(N)C(O)=O 6.3.4.5 O-ureidohomoserine + L-aspartate + ATP = canavaninosuccinate + AMP + diphosphate canavanine biosynthesis O-ureidohomoserine 177.16 C5 H11 N3 O4 C(ONC(=O)N)CC(N)C(O)=O 2.1.3.3 L-canaline + carbamoyl-phosphate = O-ureidohomoserine canavanine biosynthesis 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 867.651 C26 H44 N7 O18 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)C(O)C) 4.2.1.17 tiglyl-CoA + H2O = 2-methyl-3-hydroxybutyryl-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 867.651 C26 H44 N7 O18 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)C(O)C) 1.1.1.178 NAD+ + 2-methyl-3-hydroxybutyryl-CoA = NADH + 2-methylacetoacetyl-CoA isoleucine degradation I trans-2-hexenol 100.16 C6 H12 O1 CCCC=CCO trans-2-hexenal = trans-2-hexenol 13-LOX and 13-HPL pathway daidzein 7,4'-dihydroxyisoflavone 254.242 C15 H10 O4 C2(=C(c1(ccc(O)cc1))C(=O)c3(c(O2)cc(O)cc3)) 4.2.1.105 2-hydroxyisoflavanone = daidzein + H2O pterocarpan biosynthesis daidzein 7,4'-dihydroxyisoflavone 254.242 C15 H10 O4 C2(=C(c1(ccc(O)cc1))C(=O)c3(c(O2)cc(O)cc3)) 2.1.1.46 daidzein + S-adenosyl-L-methionine = formononetin + S-adenosyl-L-homocysteine pterocarpan biosynthesis campesterol 400.687 C28 H48 O1 CC(C)C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) 1.3.1.- campesterol + NADP+ = crinosterol + NADPH sterol biosynthesis campesterol 400.687 C28 H48 O1 CC(C)C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) 1.14.13.- campesterol + O2 + NADPH = (22α)-hydroxy-campesterol + H2O + NADP+ brassinosteroid biosynthesis II campesterol 400.687 C28 H48 O1 CC(C)C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) 1.3.-.- 24-methyldesmosterol = campesterol sterol biosynthesis campesterol 400.687 C28 H48 O1 CC(C)C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) 5.3.3.1 campesterol = campest-4-en-3β-ol brassinosteroid biosynthesis II chlorophyll b chlorophyll b 907.486 C55 H70 N4 O6 MG1 CC(CCCC(C)CCCC(C)CCCC(C)C)=CCOC(=O)CCC7(C6(C1(C(C(=O)OC)C(=O)c2(c(C)c3(n(c=12)[Mg]59(N4(C(C(C=O)=C(CC)C(C=3)=4)=Cc8(n(c(C=C(N5=6)C(C)7)c(C)c8C=C)9)))))))) chlorophyll b + H2O + NADP+ = 7-hydroxy-chlorophyll a + O2 + NADPH chlorophyll cycle chlorophyll b chlorophyll b 907.486 C55 H70 N4 O6 MG1 CC(CCCC(C)CCCC(C)CCCC(C)C)=CCOC(=O)CCC7(C6(C1(C(C(=O)OC)C(=O)c2(c(C)c3(n(c=12)[Mg]59(N4(C(C(C=O)=C(CC)C(C=3)=4)=Cc8(n(c(C=C(N5=6)C(C)7)c(C)c8C=C)9)))))))) 2.5.1.- chlorophyllide b + phytyl-PP = chlorophyll b + diphosphate chlorophyll cycle benzoyl-CoA 871.642 C28 H40 N7 O17 P3 S1 C(NCCC(=O)NCCSC(=O)c1(ccccc1))(=O)C(O)C(C)(C)COP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C2OP(=O)(O)O)n3(c4(c(nc3)c(N)ncn4))) CAS:102185-37-5 oxocinnamoyl-CoA + coenzyme A = benzoyl-CoA + acetyl-CoA salicylate biosynthesis benzoyl-CoA 871.642 C28 H40 N7 O17 P3 S1 C(NCCC(=O)NCCSC(=O)c1(ccccc1))(=O)C(O)C(C)(C)COP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C2OP(=O)(O)O)n3(c4(c(nc3)c(N)ncn4))) CAS:102185-37-5 benzoyl-CoA + H2O = benzoate + coenzyme A salicylate biosynthesis benzoyl-CoA 871.642 C28 H40 N7 O17 P3 S1 C(NCCC(=O)NCCSC(=O)c1(ccccc1))(=O)C(O)C(C)(C)COP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C2OP(=O)(O)O)n3(c4(c(nc3)c(N)ncn4))) CAS:102185-37-5 benzoyl-CoA = salicyloyl-CoA salicylate biosynthesis L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine S-adenosylmethionine biosynthesis L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine methionine salvage pathway L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC 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(=O)(O)C(N)CCSC 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(=O)(O)C(N)CCSC 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(=O)(O)C(N)CCSC 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 L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.10 L-homocysteine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + L-methionine methionine biosynthesis II L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 4.4.1.11 L-methionine + H2O = methanethiol + ammonia + 2-oxobutanoate methionine degradation II L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 L-methionine + phenylpyruvate = 2-oxo-4-methylthiobutanoate + L-phenylalanine methionine degradation III L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.6.1.- L-methionine = 2-oxo-4-methylthiobutanoate homomethionine biosynthesis L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.5 L-homocysteine + glycine betaine = L-methionine + dimethylglycine glycine betaine degradation L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.10 S-methyl-L-methionine + L-homocysteine = L-methionine methionine biosynthesis II L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.10 S-methyl-L-methionine + L-homocysteine = L-methionine S-methylmethionine cycle L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine S-adenosylmethionine biosynthesis L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine methionine biosynthesis II L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine methionine biosynthesis I L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine S-adenosyl-L-methionine cycle L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.6.1.5 2-oxo-4-methylthiobutanoate = L-methionine methionine salvage pathway L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 6.1.1.10 L-methionine + ATP = diphosphate + AMP tRNA charging pathway L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.8.1.6 dethiobiotin + S-adenosyl-L-methionine + sulfur donor = biotin + 5'-deoxyadenosine + L-methionine biotin biosynthesis I L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate S-adenosylmethionine biosynthesis L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate methionine biosynthesis I L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate folate transformations L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate formylTHF biosynthesis II L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC LIGAND-CPD:C00073:*CAS:63-68-3 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate formylTHF biosynthesis I L-methionine M*met*methionine 149.207 C5 H11 N1 O2 S1 C(=O)(O)C(N)CCSC 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 deoxyribose-5-phosphate 2-deoxy-D-ribose-5-phosphate*deoxyribose-5-P*2-deoxyribose-5-P*2-deoxyribose-5-phosphate*2-deoxy-α-D-ribose 5-phosphate 214.111 C5 H11 O7 P1 C(OP(=O)(O)O)[CH]1([CH](O)[CH2][CH](O)O1) LIGAND-CPD:C00673:*CAS:102916-66-5 5.4.2.7 deoxyribose-1-phosphate = deoxyribose-5-phosphate (deoxy)ribose phosphate degradation deoxyribose-5-phosphate 2-deoxy-D-ribose-5-phosphate*deoxyribose-5-P*2-deoxyribose-5-P*2-deoxyribose-5-phosphate*2-deoxy-α-D-ribose 5-phosphate 214.111 C5 H11 O7 P1 C(OP(=O)(O)O)[CH]1([CH](O)[CH2][CH](O)O1) LIGAND-CPD:C00673:*CAS:102916-66-5 4.1.2.4 deoxyribose-5-phosphate = acetaldehyde + D-glyceraldehyde-3-phosphate (deoxy)ribose phosphate degradation L-histidine L-histidine*glyoxaline-5-alanine*α-amino-4-imidazoleproprionic acid*(S)-α-amino-1H-imidazole-4-propanoic acid*H*histidine*his 154.148 C6 H8 N3 O2 c1(c(ncn1)CC(N)C(O)=O) LIGAND-CPD:C00135:*CAS:71-00-1 1.1.1.23 histidinal + NAD+ + H2O = L-histidine + NADH histidine biosynthesis I L-histidine L-histidine*glyoxaline-5-alanine*α-amino-4-imidazoleproprionic acid*(S)-α-amino-1H-imidazole-4-propanoic acid*H*histidine*his 154.148 C6 H8 N3 O2 c1(c(ncn1)CC(N)C(O)=O) LIGAND-CPD:C00135:*CAS:71-00-1 6.1.1.21 L-histidine + ATP = diphosphate + AMP tRNA charging pathway L-pantoate pantoate*(R)-pantoate 148.158 C6 H12 O4 C(O)C(C)(C)C(O)C(=O)O CAS:470-29-1:*LIGAND-CPD:C00522: 6.3.2.1 β-alanine + L-pantoate + ATP = pantothenate + diphosphate + AMP pantothenate biosynthesis I L-pantoate pantoate*(R)-pantoate 148.158 C6 H12 O4 C(O)C(C)(C)C(O)C(=O)O CAS:470-29-1:*LIGAND-CPD:C00522: 6.3.2.1 β-alanine + L-pantoate + ATP = pantothenate + diphosphate + AMP pantothenate biosynthesis II L-pantoate pantoate*(R)-pantoate 148.158 C6 H12 O4 C(O)C(C)(C)C(O)C(=O)O CAS:470-29-1:*LIGAND-CPD:C00522: 1.1.1.169 L-pantoate + NADP+ = 2-dehydropantoate + NADPH pantothenate biosynthesis I L-pantoate pantoate*(R)-pantoate 148.158 C6 H12 O4 C(O)C(C)(C)C(O)C(=O)O CAS:470-29-1:*LIGAND-CPD:C00522: 1.1.1.169 L-pantoate + NADP+ = 2-dehydropantoate + NADPH pantothenate biosynthesis II monovinyl protochlorophyllide a protochlorophyllide*monovinyl protochlrophyllide a 612.967 C35 H32 N4 O5 MG1 CCC8(C3(=N7([Mg]59(n2(c1(=C(C(C(=O)OC)C(=O)c1c(C)c2=C3)C4(=N(C(C(C)=C4CCC(=O)O)=Cc6(n5c(c(C=C)c(C)6)C=C7C(C)=8))9))))))) LIGAND-CPD:C02880:*CAS:14751-08-7 1.3.1.75 divinyl protochlorophyllide a + NADPH + H+ + H+ = monovinyl protochlorophyllide a + NADP+ chlorophyllide a biosynthesis monovinyl protochlorophyllide a protochlorophyllide*monovinyl protochlrophyllide a 612.967 C35 H32 N4 O5 MG1 CCC8(C3(=N7([Mg]59(n2(c1(=C(C(C(=O)OC)C(=O)c1c(C)c2=C3)C4(=N(C(C(C)=C4CCC(=O)O)=Cc6(n5c(c(C=C)c(C)6)C=C7C(C)=8))9))))))) LIGAND-CPD:C02880:*CAS:14751-08-7 monovinyl protochlorophyllide a + NADPH = NADP+ + chlorophyllide a chlorophyllide a biosynthesis 4α-methyl-5α-cholesta-8,24-dien-3-one 396.655 C28 H44 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)C(=O)CC4)))) 1.1.1.170 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol = 4α-methyl-5α-cholesta-8,24-dien-3-one + CO2 cholesterol biosynthesis I 4α-methyl-5α-cholesta-8,24-dien-3-one 396.655 C28 H44 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)C(=O)CC4)))) 1.1.1.170 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol = 4α-methyl-5α-cholesta-8,24-dien-3-one + CO2 cholesterol biosynthesis III (via desmosterol) 4α-methyl-5α-cholesta-8,24-dien-3-one 396.655 C28 H44 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)C(=O)CC4)))) 1.1.1.270 4α-methyl-5α-cholesta-8,24-dien-3-one + NADPH = 4-α-methyl zymosterol + NADP+ cholesterol biosynthesis I 4α-methyl-5α-cholesta-8,24-dien-3-one 396.655 C28 H44 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)C(=O)CC4)))) 1.1.1.270 4α-methyl-5α-cholesta-8,24-dien-3-one + NADPH = 4-α-methyl zymosterol + NADP+ cholesterol biosynthesis III (via desmosterol) momilactone A 314.424 C20 H26 O3 CC1(C=C)(CC4([CH](CC1)C2(C)([CH]3(C(C(=O)CC2)(C)C(=O)O[CH]3C=4)))) 3β-Hydroxy-9β-pimara-7,15-diene-19,6β-olide = momilactone A momilactone biosynthesis momilactone A 314.424 C20 H26 O3 CC1(C=C)(CC4([CH](CC1)C2(C)([CH]3(C(C(=O)CC2)(C)C(=O)O[CH]3C=4)))) momilactone A = momilactone B momilactone biosynthesis monodehydroascorbate 175.118 C6 H7 O6 C(O)C(O)c1(c(O)c(O)c([O-])o1) 1.6.5.4 monodehydroascorbate + NADPH = L-ascorbate + NADP+ ascorbate glutathione cycle monodehydroascorbate 175.118 C6 H7 O6 C(O)C(O)c1(c(O)c(O)c([O-])o1) 1.11.1.11 L-ascorbate + H2O2 = monodehydroascorbate + H2O ascorbate glutathione cycle monodehydroascorbate 175.118 C6 H7 O6 C(O)C(O)c1(c(O)c(O)c([O-])o1) 1.10.3.3 L-ascorbate + O2 = monodehydroascorbate + H2O ascorbate glutathione cycle monodehydroascorbate 175.118 C6 H7 O6 C(O)C(O)c1(c(O)c(O)c([O-])o1) monodehydroascorbate = L-ascorbate + L-dehydro-ascorbate ascorbate glutathione cycle brassicasterol 398.671 C28 H46 O1 CC(C(C)C)C=CC(C)C1(C2(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))(C)) 1.3.1.- 24-epi-campesterol + NADP+ = brassicasterol + NADPH sterol biosynthesis H2 hydrogen*hydrogen molecule 2.016 H2 [HH] LIGAND-CPD:C00282:*CAS:1333-74-0: 1.12.99.6 H2 = H+ respiration (anaerobic)-- electron donors reaction list H2 hydrogen*hydrogen molecule 2.016 H2 [HH] LIGAND-CPD:C00282:*CAS:1333-74-0: formate = CO2 + H2 mixed acid fermentation H2 hydrogen*hydrogen molecule 2.016 H2 [HH] LIGAND-CPD:C00282:*CAS:1333-74-0: formate = CO2 + H2 respiration (anaerobic) H2 hydrogen*hydrogen molecule 2.016 H2 [HH] LIGAND-CPD:C00282:*CAS:1333-74-0: 1.12.98.2 5,10-methenyltetrahydromethanopterin + H2 = 5,10-methylene-tetrahydromethanopterin + H+ methanogenesis from CO2 H2 hydrogen*hydrogen molecule 2.016 H2 [HH] LIGAND-CPD:C00282:*CAS:1333-74-0: 1.12.7.2 H2 = H+ glutamate degradation VII (to butyrate) 1-kestotriose 1-kestose 504.441 C18 H32 O16 C(O)C1(OC(C(O)C(O)C(O)1)OC2(OC(CO)C(O)C(O)2)COC3(C(O)C(O)C(O3)CO)(CO)) 2.4.1.99 sucrose + sucrose = 1-kestotriose + β-D-glucose fructan biosynthesis 1-kestotriose 1-kestose 504.441 C18 H32 O16 C(O)C1(OC(C(O)C(O)C(O)1)OC2(OC(CO)C(O)C(O)2)COC3(C(O)C(O)C(O3)CO)(CO)) 2.4.1.- 1-kestotriose + sucrose = 6G-kestotriose + sucrose fructan biosynthesis 1-kestotriose 1-kestose 504.441 C18 H32 O16 C(O)C1(OC(C(O)C(O)C(O)1)OC2(OC(CO)C(O)C(O)2)COC3(C(O)C(O)C(O3)CO)(CO)) 3.2.1.80 1-kestotriose + H2O = fructose + sucrose fructan degradation 1-kestotriose 1-kestose 504.441 C18 H32 O16 C(O)C1(OC(C(O)C(O)C(O)1)OC2(OC(CO)C(O)C(O)2)COC3(C(O)C(O)C(O3)CO)(CO)) 2.4.1.100 1-kestotriose + 1-kestotriose = 1,1-kestotetraose + sucrose fructan biosynthesis 1-kestotriose 1-kestose 504.441 C18 H32 O16 C(O)C1(OC(C(O)C(O)C(O)1)OC2(OC(CO)C(O)C(O)2)COC3(C(O)C(O)C(O3)CO)(CO)) 2.4.1.10 1-kestotriose + sucrose = 1,6-kestotetraose + β-D-glucose fructan biosynthesis 2-dehydro-3-deoxy-D-gluconate 2-keto-3-deoxy-D-gluconate*3-deoxy-2-oxo-D-gluconate*2-keto-3-deoxygluconate 178.141 C6 H10 O6 C(=O)(O)C(=O)[CH2][CH](O)[CH](O)CO LIGAND-CPD:C00204:*CAS:17510-99-5 2.7.1.45 2-dehydro-3-deoxy-D-gluconate + ATP = 2-keto-3-deoxy-6-phospho-gluconate + ADP β-D-glucuronide degradation 2-dehydro-3-deoxy-D-gluconate 2-keto-3-deoxy-D-gluconate*3-deoxy-2-oxo-D-gluconate*2-keto-3-deoxygluconate 178.141 C6 H10 O6 C(=O)(O)C(=O)[CH2][CH](O)[CH](O)CO LIGAND-CPD:C00204:*CAS:17510-99-5 4.2.1.8 D-mannonate = H2O + 2-dehydro-3-deoxy-D-gluconate β-D-glucuronide degradation N2 nitrogen molecule*nitrogen 28.013 N2 N#N CAS:7727-37-9 1.7.99.6 N2 + H2O = nitrous oxide nitrate reduction I dihydrophloroglucinol 128.127 C6 H8 O3 C1(=O)(CC(O)CC(O)=C1) UM-BBD-CPD:c0027:*LIGAND-CPD:c06719: 1.3.1.57 dihydrophloroglucinol + NADP+ = phloroglucinol + NADPH gallate degradation III (anaerobic) dihydrophloroglucinol 128.127 C6 H8 O3 C1(=O)(CC(O)CC(O)=C1) UM-BBD-CPD:c0027:*LIGAND-CPD:c06719: 3.7.1.- dihydrophloroglucinol + OH- = 3-hydroxy-5-oxohexanoate gallate degradation III (anaerobic) phytocassane A 316.439 C20 H28 O3 CC2(C(C=C)=CC(=O)[CH]1(C3([CH](CC[CH]12)C(C)(C)C(=O)C(C3)O)(C))) ent-cassa-12,15-diene-2,3α-ol-11-keto = phytocassane A phytocassane biosynthesis 18:2-16:2-MGDG 1-18:2-2-16:2-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(7Z,10Z-hexadecadienoyl)-3-O-beta-D-galactosyl-sn-glycerol 751.052 C43 H74 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:1-16:2-MGDG = 18:2-16:2-MGDG glycolipid desaturation 18:2-16:2-MGDG 1-18:2-2-16:2-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(7Z,10Z-hexadecadienoyl)-3-O-beta-D-galactosyl-sn-glycerol 751.052 C43 H74 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-16:2-MGDG = 18:2-16:3-MGDG glycolipid desaturation 18:2-16:2-MGDG 1-18:2-2-16:2-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(7Z,10Z-hexadecadienoyl)-3-O-beta-D-galactosyl-sn-glycerol 751.052 C43 H74 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-16:1-MGDG = 18:2-16:2-MGDG glycolipid desaturation 18:2-16:2-MGDG 1-18:2-2-16:2-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(7Z,10Z-hexadecadienoyl)-3-O-beta-D-galactosyl-sn-glycerol 751.052 C43 H74 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-16:2-MGDG = 18:3-16:2-MGDG glycolipid desaturation lutein 568.881 C40 H56 O2 CC1(C(=C(C)CC(O)C1)C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)(C)CC(O)C=C(C)2))(C) 1.14.99.- zeinoxanthin + NADPH + O2 = lutein + NADP+ + H2O carotenoid biosynthesis L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O LIGAND-CPD:C00062:*CAS:74-79-3 4.1.1.19 L-arginine = CO2 + agmatine arginine degradation III (arginine decarboxylase/agmatinase pathway) L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O LIGAND-CPD:C00062:*CAS:74-79-3 4.1.1.19 L-arginine = CO2 + agmatine putrescine biosynthesis I L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O LIGAND-CPD:C00062:*CAS:74-79-3 4.1.1.19 L-arginine = CO2 + agmatine putrescine biosynthesis II L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O LIGAND-CPD:C00062:*CAS:74-79-3 4.1.1.19 L-arginine = CO2 + agmatine arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O 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 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O 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 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O LIGAND-CPD:C00062:*CAS:74-79-3 3.5.3.1 H2O + L-arginine = urea + L-ornithine arginine degradation VII (arginase 3 pathway) L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O 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 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O 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 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O LIGAND-CPD:C00062:*CAS:74-79-3 3.5.3.6 H2O + L-arginine = ammonia + citrulline proline biosynthesis V (from arginine) L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O LIGAND-CPD:C00062:*CAS:74-79-3 2.3.1.109 L-arginine + succinyl-CoA = N2-succinyl-L-arginine + coenzyme A arginine degradation II L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O LIGAND-CPD:C00062:*CAS:74-79-3 1.14.13.39 O2 + NADPH + L-arginine = citrulline + NADP+ + nitric oxide citrulline-nitric oxide cycle L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O LIGAND-CPD:C00062:*CAS:74-79-3 1.13.12.1 O2 + L-arginine = 4-guanidinobutyramide + H2O + CO2 arginine degradation X (arginine monooxygenase pathway) L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O LIGAND-CPD:C00062:*CAS:74-79-3 6.1.1.19 L-arginine + ATP = diphosphate + AMP tRNA charging pathway L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O 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 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O 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 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O 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 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O LIGAND-CPD:C00062:*CAS:74-79-3 4.3.2.1 L-arginino-succinate = L-arginine + fumarate arginine biosynthesis IV L-arginine 2-amino-5-guanidinovaleric acid*R*arginine*arg 174.202 C6 H14 N4 O2 C(NC(N)=N)CCC(N)C(O)=O LIGAND-CPD:C00062:*CAS:74-79-3 4.3.2.1 L-arginino-succinate = L-arginine + fumarate arginine biosynthesis I 18:2-18:2-PC 1-18:2-2-18:2-sn-glycerol-3-phosphocholine*1,2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine 783.1 C44 H81 N1 O8 P1 C(OP(O)(=O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC PUBCHEM:5313522: 1.14.99.- 18:1-18:2-PC = 18:2-18:2-PC phospholipid desaturation 18:2-18:2-PC 1-18:2-2-18:2-sn-glycerol-3-phosphocholine*1,2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine 783.1 C44 H81 N1 O8 P1 C(OP(O)(=O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC PUBCHEM:5313522: 1.14.99.- 18:2-18:1-PC = 18:2-18:2-PC phospholipid desaturation 18:2-18:2-PC 1-18:2-2-18:2-sn-glycerol-3-phosphocholine*1,2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine 783.1 C44 H81 N1 O8 P1 C(OP(O)(=O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC PUBCHEM:5313522: 1.14.99.- 18:2-18:2-PC = 18:3-18:2-PC phospholipid desaturation 18:2-18:2-PC 1-18:2-2-18:2-sn-glycerol-3-phosphocholine*1,2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine 783.1 C44 H81 N1 O8 P1 C(OP(O)(=O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC PUBCHEM:5313522: 1.14.99.- 18:2-18:2-PC = 18:2-18:3-PC phospholipid desaturation 2'-hydroxygenistein 5,7,2',4'-tetrahydroxyisoflavone 286.24 C15 H10 O6 C2(=C(c1(c(O)cc(O)cc1))C(=O)c3(c(O2)cc(O)cc3O)) 2.5.1.1 2'-hydroxygenistein + dimethylallyl-PP = phaseoluteone + diphosphate wighteone and luteone biosynthesis 2'-hydroxygenistein 5,7,2',4'-tetrahydroxyisoflavone 286.24 C15 H10 O6 C2(=C(c1(c(O)cc(O)cc1))C(=O)c3(c(O2)cc(O)cc3O)) 2.5.1.1 2'-hydroxygenistein + dimethylallyl-PP = 2,3-dehydrokievitone + diphosphate kievitone biosynthesis 2'-hydroxygenistein 5,7,2',4'-tetrahydroxyisoflavone 286.24 C15 H10 O6 C2(=C(c1(c(O)cc(O)cc1))C(=O)c3(c(O2)cc(O)cc3O)) 2.5.1.1 2'-hydroxygenistein + dimethylallyl-PP = luteone + diphosphate wighteone and luteone biosynthesis 2'-hydroxygenistein 5,7,2',4'-tetrahydroxyisoflavone 286.24 C15 H10 O6 C2(=C(c1(c(O)cc(O)cc1))C(=O)c3(c(O2)cc(O)cc3O)) 1.3.1.51 dalbergioidin + NADP+ = 2'-hydroxygenistein + NADPH + H+ kievitone biosynthesis 2'-hydroxygenistein 5,7,2',4'-tetrahydroxyisoflavone 286.24 C15 H10 O6 C2(=C(c1(c(O)cc(O)cc1))C(=O)c3(c(O2)cc(O)cc3O)) 1.14.13.89 genistein + NADPH + O2 = 2'-hydroxygenistein + NADP+ + H2O wighteone and luteone biosynthesis episterol 398.671 C28 H46 O1 CC(C)C(=C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC=3)CC(O)CC4)(C)))) 1.3.3.- episterol = 5-dehydro episterol sterol biosynthesis episterol 398.671 C28 H46 O1 CC(C)C(=C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC=3)CC(O)CC4)(C)))) 2.1.1.- 24-methylenelophenol = episterol sterol 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 589.345 C16 H25 N5 O15 P2 C(OP(O)(=O)OP(O)(=O)OC1(C(O)C(O)C(O)C(C)O1))C2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4))) LIGAND-CPD:C00325:*CAS:15839-70-0 1.1.1.271 NADP+ + GDP-L-fucose = NADPH + GDP-4-dehydro-6-deoxy-D-mannose GDP-L-fucose biosynthesis I (from GDP-D-mannose) carbamate 60.032 C1 H2 N1 O2 C([O-])(N)=O 4.3.99.1 HCO3- + cyanate = carbamate + CO2 cyanate degradation 18:1-18:3-PC 1-18:1-2-18:3-phosphatidylcholine*1-(9Z-octadecenoyl)-2-(9Z,12Z,15Z-octadecatrienoyl)-sn-glycero-3-phosphocholine 783.1 C44 H81 N1 O8 P1 C(OC(=O)CCCCCCCC=CCCCCCCCC)C(COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCC=CCC PUBCHEM:5313483: 1.14.99.- 18:1-18:2-PC = 18:1-18:3-PC phospholipid desaturation 18:1-18:3-PC 1-18:1-2-18:3-phosphatidylcholine*1-(9Z-octadecenoyl)-2-(9Z,12Z,15Z-octadecatrienoyl)-sn-glycero-3-phosphocholine 783.1 C44 H81 N1 O8 P1 C(OC(=O)CCCCCCCC=CCCCCCCCC)C(COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCC=CCC PUBCHEM:5313483: 1.14.99.- 18:1-18:3-PC = 18:2-18:3-PC phospholipid desaturation (Z)-β-ocimene cis-β-ocimene 136.236 C10 H16 C=CC(C)=CCC=C(C)C 4.2.3.- geranyl-PP = (Z)-β-ocimene + diphosphate monoterpene biosynthesis trans-cinnamate β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 148.161 C9 H8 O2 C(O)(=O)C=Cc1(ccccc1) LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 1.14.13.14 trans-cinnamate + O2 + NADPH = H2O + NADP+ + 2-coumarate coumarin biosynthesis (via 2-coumarate) trans-cinnamate β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 148.161 C9 H8 O2 C(O)(=O)C=Cc1(ccccc1) LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 4.3.1.5 L-phenylalanine = ammonia + trans-cinnamate suberin biosynthesis trans-cinnamate β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 148.161 C9 H8 O2 C(O)(=O)C=Cc1(ccccc1) LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 4.3.1.5 L-phenylalanine = ammonia + trans-cinnamate phenylpropanoid biosynthesis, initial reactions trans-cinnamate β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 148.161 C9 H8 O2 C(O)(=O)C=Cc1(ccccc1) LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 4.3.1.5 L-phenylalanine = ammonia + trans-cinnamate salicylate biosynthesis trans-cinnamate β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 148.161 C9 H8 O2 C(O)(=O)C=Cc1(ccccc1) LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 6.2.1.- trans-cinnamate + coenzyme A = (E)-cinnamoyl-CoA + H2O salicylate biosynthesis trans-cinnamate β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 148.161 C9 H8 O2 C(O)(=O)C=Cc1(ccccc1) LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 1.14.13.11 trans-cinnamate + O2 + NADPH = H2O + NADP+ + 4-coumarate suberin biosynthesis trans-cinnamate β-phenylacrylic acid*3-phenyl-2-propenoic acid*cinnamic acid*cinnamate*trans-cinnamic acid*(E)-cinnamate 148.161 C9 H8 O2 C(O)(=O)C=Cc1(ccccc1) LIGAND-CPD:C00423:*PUBCHEM:444539:*CAS:140-10-3 1.14.13.11 trans-cinnamate + O2 + NADPH = H2O + NADP+ + 4-coumarate phenylpropanoid biosynthesis, initial reactions 9,10-epoxy-18-hydroxystearate 314.464 C18 H34 O4 C(O)CCCCCCCC1(C(O1)CCCCCCCC(O)=O) 9,10-epoxy-18-hydroxystearate + H2O = 9,10,18-trihydroxystearate cutin biosynthesis 9,10-epoxy-18-hydroxystearate 314.464 C18 H34 O4 C(O)CCCCCCCC1(C(O1)CCCCCCCC(O)=O) 18-hydroxyoleate + NADPH + O2 = 9,10-epoxy-18-hydroxystearate + NADP+ + H2O cutin biosynthesis cytidine 243.219 C9 H13 N3 O5 [CH]1(O[CH](CO)[CH](O)[CH](O)1)n2(c(=O)nc(N)cc2) LIGAND-CPD:C00475:*CAS:65-46-3 3.5.4.5 H2O + cytidine = ammonia + uridine salvage pathways of purine and pyrimidine nucleotides cytidine 243.219 C9 H13 N3 O5 [CH]1(O[CH](CO)[CH](O)[CH](O)1)n2(c(=O)nc(N)cc2) LIGAND-CPD:C00475:*CAS:65-46-3 3.5.4.5 H2O + cytidine = ammonia + uridine (deoxy)ribose phosphate degradation cytidine 243.219 C9 H13 N3 O5 [CH]1(O[CH](CO)[CH](O)[CH](O)1)n2(c(=O)nc(N)cc2) LIGAND-CPD:C00475:*CAS:65-46-3 3.5.4.5 H2O + cytidine = ammonia + uridine salvage pathways of pyrimidine ribonucleotides cytidine 243.219 C9 H13 N3 O5 [CH]1(O[CH](CO)[CH](O)[CH](O)1)n2(c(=O)nc(N)cc2) LIGAND-CPD:C00475:*CAS:65-46-3 2.7.1.- cytidine + ATP = CMP + ADP salvage pathways of purine and pyrimidine nucleotides cytidine 243.219 C9 H13 N3 O5 [CH]1(O[CH](CO)[CH](O)[CH](O)1)n2(c(=O)nc(N)cc2) LIGAND-CPD:C00475:*CAS:65-46-3 2.7.1.- cytidine + GTP = CMP + GDP salvage pathways of pyrimidine ribonucleotides 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol 444.74 C30 H52 O2 CC(C)CCCC(C)C1(C2(C(CC1)(CO)C3(=C(CC2)C4(C(CC3)C(C)(C)C(O)CC4)(C)))(C)) 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol + O2 + NADPH = 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol 444.74 C30 H52 O2 CC(C)CCCC(C)C1(C2(C(CC1)(CO)C3(=C(CC2)C4(C(CC3)C(C)(C)C(O)CC4)(C)))(C)) 1.14.13.70 24,25-dihydrolanosterol + O2 + NADPH = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA 971.716 C32 H44 N7 O20 P3 S1 C(=O)(O)c1(c(cccc1)C(=O)CCC(=O)SCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC2(OC(C)(C(O)C2OP(O)(=O)O)n3(c4(c(nc3)c(N)ncn4)))) 4.1.3.36 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA = coenzyme A + 1,4-dihydroxy-2-naphthoate phylloquinone biosynthesis 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA 971.716 C32 H44 N7 O20 P3 S1 C(=O)(O)c1(c(cccc1)C(=O)CCC(=O)SCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC2(OC(C)(C(O)C2OP(O)(=O)O)n3(c4(c(nc3)c(N)ncn4)))) 6.2.1.26 ATP + O-succinylbenzoate + coenzyme A = 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA + AMP + diphosphate phylloquinone biosynthesis 6-deoxoteasterone deoxoteasterone 434.701 C28 H50 O3 CC(C)C(C)C(O)C(O)C(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC3)CC(O)CC4)(C)))) 1.14.-.- 6-deoxocathasterone + O2 = 6-deoxoteasterone + H2O brassinosteroid biosynthesis II 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 338.101 C6 H12 O12 P2 C1(C(OP(O)([O-])=O)C(O)C(O)C(O)C(O)1)(OP(O)([O-])=O) D-myo-inositol (3)-monophosphate + ATP = D-myo-inositol (3,4)-bisphosphate + ADP lipid-independent phytate biosynthesis 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 338.101 C6 H12 O12 P2 C1(C(OP(O)([O-])=O)C(O)C(O)C(O)C(O)1)(OP(O)([O-])=O) D-myo-inositol (3,4)-bisphosphate + ATP = D-myo-inositol (3,4,6)-trisphosphate + ADP lipid-independent phytate 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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.27 α-D-glucose 1-phosphate + ATP = ADP-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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) 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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) 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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) CAS:59-56-3*LIGAND-CPD:C00103: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate sucrose degradation to ethanol and lactate (anaerobic) 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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) 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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) 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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) CAS:59-56-3*LIGAND-CPD:C00103: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate UDP-glucose conversion 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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) 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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + 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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate sucrose degradation to ethanol and lactate (anaerobic) 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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate galactose 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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate UDP-glucose conversion 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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + 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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + 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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.12 UDP-D-glucose + α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-galactose 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 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) CAS:59-56-3*LIGAND-CPD:C00103: 2.7.7.24 α-D-glucose 1-phosphate + dTTP = dTDP-D-glucose + diphosphate dTDP-L-rhamnose biosynthesis I phlorisobutyrophenone 196.202 C10 H12 O4 CC(C)C(=O)c1(c(O)cc(O)cc(O)1) 2.5.1.- phlorisobutyrophenone + dimethylallyl-PP = 4-prenylphlorisobutyrophenone + diphosphate cohumulone biosynthesis phlorisobutyrophenone 196.202 C10 H12 O4 CC(C)C(=O)c1(c(O)cc(O)cc(O)1) 2.3.1.156 malonyl-CoA + isobutyryl-CoA = phlorisobutyrophenone + CO2 + coenzyme A cohumulone biosynthesis trehalose α,α-trehalose 342.299 C12 H22 O11 C1(OC(CO)C(O)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND-CPD:C01083:*CAS:99-20-7 3.2.1.141 maltooligosyl-trehalose = maltodextrin + trehalose trehalose biosynthesis V trehalose α,α-trehalose 342.299 C12 H22 O11 C1(OC(CO)C(O)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND-CPD:C01083:*CAS:99-20-7 3.2.1.28 trehalose + H2O = β-D-glucose trehalose degradation II (high osmolarity) trehalose α,α-trehalose 342.299 C12 H22 O11 C1(OC(CO)C(O)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND-CPD:C01083:*CAS:99-20-7 3.1.3.12 trehalose 6-phosphate + H2O = trehalose trehalose biosynthesis I glucuronate D-glucuronate*glucuronic acid*D-glucuronic acid 194.141 C6 H10 O7 C(=O)(O)C1(C(O)C(O)C(O)C(O1)O) CAS:12/03/6556:*LIGAND-CPD:C00191:*CAS:576-37-4 3.2.1.31 H2O = glucuronate β-D-glucuronide degradation glucuronate D-glucuronate*glucuronic acid*D-glucuronic acid 194.141 C6 H10 O7 C(=O)(O)C1(C(O)C(O)C(O)C(O1)O) CAS:12/03/6556:*LIGAND-CPD:C00191:*CAS:576-37-4 5.3.1.12 glucuronate = fructuronate β-D-glucuronide degradation glucuronate D-glucuronate*glucuronic acid*D-glucuronic acid 194.141 C6 H10 O7 C(=O)(O)C1(C(O)C(O)C(O)C(O1)O) CAS:12/03/6556:*LIGAND-CPD:C00191:*CAS:576-37-4 2.7.1.43 glucuronate + ATP = α-D-glucuronate 1-phosphate + ADP UDP-D-glucuronate biosynthesis (from myo-inositol) glucuronate D-glucuronate*glucuronic acid*D-glucuronic acid 194.141 C6 H10 O7 C(=O)(O)C1(C(O)C(O)C(O)C(O1)O) CAS:12/03/6556:*LIGAND-CPD:C00191:*CAS:576-37-4 1.13.99.1 O2 + myo-inositol = H2O + glucuronate UDP-D-glucuronate biosynthesis (from myo-inositol) lathosterol 5α-Cholest-8-en-3β-ol*lathosterol*5α-cholest-7-en-3β-ol*α-cholest-7-en-3β-ol*cholesta-7-enol*Δ7-cholesten-3-β-ol*γ-cholesterol 386.66 C27 H46 O1 CC(C)CCCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(CC=3)CC(O)CC4)(C)))) CAS:80-99-9*PUBCHEM:65728: 5.3.3.5 zymostenol = lathosterol cholesterol biosynthesis II (via 24,25-dihydrolanosterol) lathosterol 5α-Cholest-8-en-3β-ol*lathosterol*5α-cholest-7-en-3β-ol*α-cholest-7-en-3β-ol*cholesta-7-enol*Δ7-cholesten-3-β-ol*γ-cholesterol 386.66 C27 H46 O1 CC(C)CCCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(CC=3)CC(O)CC4)(C)))) CAS:80-99-9*PUBCHEM:65728: 1.3.1.72 5α-cholesta-7,24-dien-3β-ol + NADPH = lathosterol + NADP+ cholesterol biosynthesis I lathosterol 5α-Cholest-8-en-3β-ol*lathosterol*5α-cholest-7-en-3β-ol*α-cholest-7-en-3β-ol*cholesta-7-enol*Δ7-cholesten-3-β-ol*γ-cholesterol 386.66 C27 H46 O1 CC(C)CCCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(CC=3)CC(O)CC4)(C)))) CAS:80-99-9*PUBCHEM:65728: 1.14.21.6 lathosterol + O2 = 7-dehydro-cholesterol + H2O cholesterol biosynthesis I lathosterol 5α-Cholest-8-en-3β-ol*lathosterol*5α-cholest-7-en-3β-ol*α-cholest-7-en-3β-ol*cholesta-7-enol*Δ7-cholesten-3-β-ol*γ-cholesterol 386.66 C27 H46 O1 CC(C)CCCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(CC=3)CC(O)CC4)(C)))) CAS:80-99-9*PUBCHEM:65728: 1.14.21.6 lathosterol + O2 = 7-dehydro-cholesterol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) canavanine L-canavanine*2-amino-4-(guanidinooxy)butyrate*2-amino-4-(guanidinooxy)butyric acid 176.175 C5 H12 N4 O3 C(ONC(N)=N)CC(N)C(O)=O CAS:543-38-4 3.5.3.1 canavanine + H2O = L-canaline + urea canavanine degradation canavanine L-canavanine*2-amino-4-(guanidinooxy)butyrate*2-amino-4-(guanidinooxy)butyric acid 176.175 C5 H12 N4 O3 C(ONC(N)=N)CC(N)C(O)=O CAS:543-38-4 4.3.2.1 canavaninosuccinate = canavanine + fumarate canavanine biosynthesis 18:1-18:2-PC 1-18:1-2-18:2-phosphatidylcholine*1-(9Z-octadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine 785.115 C44 H83 N1 O8 P1 C(OP(=O)(O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PUBCHEM:5313480: 1.14.99.- 18:1-18:1-PC = 18:1-18:2-PC phospholipid desaturation 18:1-18:2-PC 1-18:1-2-18:2-phosphatidylcholine*1-(9Z-octadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine 785.115 C44 H83 N1 O8 P1 C(OP(=O)(O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PUBCHEM:5313480: 1.14.99.- 18:1-18:2-PC = 18:2-18:2-PC phospholipid desaturation 18:1-18:2-PC 1-18:1-2-18:2-phosphatidylcholine*1-(9Z-octadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine 785.115 C44 H83 N1 O8 P1 C(OP(=O)(O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PUBCHEM:5313480: 1.14.99.- 18:1-18:2-PC = 18:1-18:3-PC phospholipid desaturation NH(4)OH ammonium hydroxide 34.038 H4 N1 O1 [NH3+]O 2-amino-muconate + H2O + NADH = NH(4)OH + α-ketoadipate + NAD+ tryptophan degradation III (eukaryotic) methylmalonate-semialdehyde 2-methyl-3-oxopropanoate*CH3-malonate-S-ald*ch3-malonate-semialdehyde 102.09 C4 H6 O3 C(=O)(O)C(C)C=O CAS:6236-08-4 1.2.1.27 NAD+ + coenzyme A + methylmalonate-semialdehyde = NADH + CO2 + propionyl-CoA valine degradation I methylmalonate-semialdehyde 2-methyl-3-oxopropanoate*CH3-malonate-S-ald*ch3-malonate-semialdehyde 102.09 C4 H6 O3 C(=O)(O)C(C)C=O CAS:6236-08-4 1.1.1.31 NAD+ + 3-hydroxy-isobutyrate = NADH + methylmalonate-semialdehyde valine degradation I L-erythro-4-hydroxy-glutamate 4-Hydroxy-L-glutamate*erythro-4-hydroxyglutamate*4-Hydroxy-L-glutamic acid 163.13 C5 H9 N1 O5 C(O)(=O)C(N)CC(O)C(=O)O 1.5.1.12 pyrroline-hydroxy-carboxylate + NAD+ + H2O = L-erythro-4-hydroxy-glutamate + NADH 4-hydroxyproline degradation I L-erythro-4-hydroxy-glutamate 4-Hydroxy-L-glutamate*erythro-4-hydroxyglutamate*4-Hydroxy-L-glutamic acid 163.13 C5 H9 N1 O5 C(O)(=O)C(N)CC(O)C(=O)O 2.6.1.23 α-ketoglutarate + L-erythro-4-hydroxy-glutamate = L-glutamate + D-4-hydroxy-2-keto-glutarate 4-hydroxyproline degradation I dihydro-neo-pterin 2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine*dihydro-neo-pterin*2-amino-4-hydroxy-6-(D-erythro)-trihydroxypropyldihydropteridin 255.233 C9 H13 N5 O4 C(O)C(O)C(O)C1(=Nc2(c(NC1)nc(N)[nH]c2=O)) LIGAND-CPD:C04874: 3.6.1.- dihydroneopterin phosphate + H2O = dihydro-neo-pterin tetrahydrofolate biosynthesis I dihydro-neo-pterin 2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine*dihydro-neo-pterin*2-amino-4-hydroxy-6-(D-erythro)-trihydroxypropyldihydropteridin 255.233 C9 H13 N5 O4 C(O)C(O)C(O)C1(=Nc2(c(NC1)nc(N)[nH]c2=O)) LIGAND-CPD:C04874: 3.6.1.- dihydroneopterin phosphate + H2O = dihydro-neo-pterin tetrahydrofolate biosynthesis II dihydro-neo-pterin 2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine*dihydro-neo-pterin*2-amino-4-hydroxy-6-(D-erythro)-trihydroxypropyldihydropteridin 255.233 C9 H13 N5 O4 C(O)C(O)C(O)C1(=Nc2(c(NC1)nc(N)[nH]c2=O)) LIGAND-CPD:C04874: 4.1.2.25 dihydro-neo-pterin = glycolaldehyde + 6-hydroxymethyl-dihydropterin tetrahydrofolate biosynthesis I dihydro-neo-pterin 2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine*dihydro-neo-pterin*2-amino-4-hydroxy-6-(D-erythro)-trihydroxypropyldihydropteridin 255.233 C9 H13 N5 O4 C(O)C(O)C(O)C1(=Nc2(c(NC1)nc(N)[nH]c2=O)) LIGAND-CPD:C04874: 4.1.2.25 dihydro-neo-pterin = glycolaldehyde + 6-hydroxymethyl-dihydropterin tetrahydrofolate biosynthesis II 3-hydroxybutyryl-CoA 3-OH-butyryl-CoA*OH-butyryl-CoA*β-hydroxybutyryl-S-CoA*D-3-hydroxybutyryl-CoA*hydroxy-butyryl-CoA*β-hydroxybutyryl-CoA*(R)-3-Hydroxybutanoyl-CoA*(3R)-3-Hydroxybutanoyl-CoA*3-hydroxybutanoyl-CoA 853.624 C25 H42 N7 O18 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)C)(n2(c3(c(nc2)c(N)ncn3))) UM-BBD-CPD:c0030: 1.1.1.35 acetoacetyl-CoA + NADH = 3-hydroxybutyryl-CoA + NAD+ acetyl CoA fermentation to butyrate 3-hydroxybutyryl-CoA 3-OH-butyryl-CoA*OH-butyryl-CoA*β-hydroxybutyryl-S-CoA*D-3-hydroxybutyryl-CoA*hydroxy-butyryl-CoA*β-hydroxybutyryl-CoA*(R)-3-Hydroxybutanoyl-CoA*(3R)-3-Hydroxybutanoyl-CoA*3-hydroxybutanoyl-CoA 853.624 C25 H42 N7 O18 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)C)(n2(c3(c(nc2)c(N)ncn3))) UM-BBD-CPD:c0030: 1.1.1.35 acetoacetyl-CoA + NADH = 3-hydroxybutyryl-CoA + NAD+ glutaryl-CoA degradation 3-hydroxybutyryl-CoA 3-OH-butyryl-CoA*OH-butyryl-CoA*β-hydroxybutyryl-S-CoA*D-3-hydroxybutyryl-CoA*hydroxy-butyryl-CoA*β-hydroxybutyryl-CoA*(R)-3-Hydroxybutanoyl-CoA*(3R)-3-Hydroxybutanoyl-CoA*3-hydroxybutanoyl-CoA 853.624 C25 H42 N7 O18 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)C)(n2(c3(c(nc2)c(N)ncn3))) UM-BBD-CPD:c0030: 4.2.1.17 3-hydroxybutyryl-CoA = crotonyl-CoA + H2O gallate degradation III (anaerobic) 3-hydroxybutyryl-CoA 3-OH-butyryl-CoA*OH-butyryl-CoA*β-hydroxybutyryl-S-CoA*D-3-hydroxybutyryl-CoA*hydroxy-butyryl-CoA*β-hydroxybutyryl-CoA*(R)-3-Hydroxybutanoyl-CoA*(3R)-3-Hydroxybutanoyl-CoA*3-hydroxybutanoyl-CoA 853.624 C25 H42 N7 O18 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)C)(n2(c3(c(nc2)c(N)ncn3))) UM-BBD-CPD:c0030: 1.1.1.36 acetoacetyl-CoA + NADPH = 3-hydroxybutyryl-CoA + NADP+ ethanol fermentation to acetate 3-hydroxybutyryl-CoA 3-OH-butyryl-CoA*OH-butyryl-CoA*β-hydroxybutyryl-S-CoA*D-3-hydroxybutyryl-CoA*hydroxy-butyryl-CoA*β-hydroxybutyryl-CoA*(R)-3-Hydroxybutanoyl-CoA*(3R)-3-Hydroxybutanoyl-CoA*3-hydroxybutanoyl-CoA 853.624 C25 H42 N7 O18 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)C)(n2(c3(c(nc2)c(N)ncn3))) UM-BBD-CPD:c0030: 4.2.1.55 3-hydroxybutyryl-CoA = H2O + crotonyl-CoA acetyl CoA fermentation to butyrate 3-hydroxybutyryl-CoA 3-OH-butyryl-CoA*OH-butyryl-CoA*β-hydroxybutyryl-S-CoA*D-3-hydroxybutyryl-CoA*hydroxy-butyryl-CoA*β-hydroxybutyryl-CoA*(R)-3-Hydroxybutanoyl-CoA*(3R)-3-Hydroxybutanoyl-CoA*3-hydroxybutanoyl-CoA 853.624 C25 H42 N7 O18 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)C)(n2(c3(c(nc2)c(N)ncn3))) UM-BBD-CPD:c0030: 4.2.1.55 3-hydroxybutyryl-CoA = H2O + crotonyl-CoA glutaryl-CoA degradation 3-hydroxybutyryl-CoA 3-OH-butyryl-CoA*OH-butyryl-CoA*β-hydroxybutyryl-S-CoA*D-3-hydroxybutyryl-CoA*hydroxy-butyryl-CoA*β-hydroxybutyryl-CoA*(R)-3-Hydroxybutanoyl-CoA*(3R)-3-Hydroxybutanoyl-CoA*3-hydroxybutanoyl-CoA 853.624 C25 H42 N7 O18 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)C)(n2(c3(c(nc2)c(N)ncn3))) UM-BBD-CPD:c0030: 4.2.1.55 3-hydroxybutyryl-CoA = H2O + crotonyl-CoA ethanol fermentation to acetate 3-hydroxybutyryl-CoA 3-OH-butyryl-CoA*OH-butyryl-CoA*β-hydroxybutyryl-S-CoA*D-3-hydroxybutyryl-CoA*hydroxy-butyryl-CoA*β-hydroxybutyryl-CoA*(R)-3-Hydroxybutanoyl-CoA*(3R)-3-Hydroxybutanoyl-CoA*3-hydroxybutanoyl-CoA 853.624 C25 H42 N7 O18 P3 S1 C1(OC(C(C(O)1)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)C)(n2(c3(c(nc2)c(N)ncn3))) UM-BBD-CPD:c0030: 2.3.1.- 3-hydroxy-5- oxohexanoyl-CoA + coenzyme A = 3-hydroxybutyryl-CoA + acetyl-CoA gallate degradation III (anaerobic) trans-3'-hydroxycotinine 192.217 C10 H12 N2 O2 c1(ncc(cc1)[CH]2(N(C)C(=O)[CH](C2)O)) 1.14.14.1 cotinine + NADPH + O2 = trans-3'-hydroxycotinine + NADP+ + H2O nicotine degradation III trans-3'-hydroxycotinine 192.217 C10 H12 N2 O2 c1(ncc(cc1)[CH]2(N(C)C(=O)[CH](C2)O)) 2.4.1.17 trans-3'-hydroxycotinine + UDP-D-glucuronate = trans-3-hydroxycotinine-glucuronide + UDP nicotine degradation III hygrine 141.213 C8 H15 N1 O1 C1(N(C)C(CC1)CC(=O)C) N-methyl-Δ1-pyrrolinium cation = hygrine calystegine biosynthesis hygrine 141.213 C8 H15 N1 O1 C1(N(C)C(CC1)CC(=O)C) hygrine = unknown calystegine biosynthesis (mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->3)-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 2000.555 C108 H180 N2 O27 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC3(C(O)C(C(O)C(O3)CO)OC4(OC(CO)C(O)C(O)C(O)4)))) (mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)3-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis (mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->3)-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 2000.555 C108 H180 N2 O27 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC3(C(O)C(C(O)C(O3)CO)OC4(OC(CO)C(O)C(O)C(O)4)))) 2.4.1.132 mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis GA29 gibberellin A29*gibberellin A29*GA29 348.395 C19 H24 O6 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(CC(O)C3)(C)[CH]4C5C(=O)O)))(O)) 1.14.11.- GA20 + α-ketoglutarate + O2 = GA29 + succinate + CO2 gibberellin inactivation GA29 gibberellin A29*gibberellin A29*GA29 348.395 C19 H24 O6 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(CC(O)C3)(C)[CH]4C5C(=O)O)))(O)) 1.14.11.- GA29 + α-ketoglutarate + O2 = GA29-catabolite + succinate + CO2 + H2O gibberellin inactivation 2-oxopantoyl lactone 2-dehydropantolactone*2-dehydropantoyl lactone 128.127 C6 H8 O3 C1(C(C)(C)C(=O)C(=O)O1) 1.1.1.168 NADP+ + pantoyl lactone = NADPH + 2-oxopantoyl lactone pantothenate biosynthesis III β-D-glucose beta-glucose*beta-D-glucopyranose*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 C(O)C1(C(O)C(O)C(O)C(O1)O) 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 beta-glucose*beta-D-glucopyranose*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 C(O)C1(C(O)C(O)C(O)C(O1)O) 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 beta-glucose*beta-D-glucopyranose*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 C(O)C1(C(O)C(O)C(O)C(O1)O) PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 3.2.1.21 coumarinic acid-β-D-glucoside + H2O = coumarinate + β-D-glucose coumarin biosynthesis (via 2-coumarate) β-D-glucose beta-glucose*beta-D-glucopyranose*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 C(O)C1(C(O)C(O)C(O)C(O1)O) 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 beta-glucose*beta-D-glucopyranose*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 C(O)C1(C(O)C(O)C(O)C(O1)O) PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 2.7.1.2 β-D-glucose + ATP = β-D-glucose-6-phosphate + ADP trehalose degradation II (high osmolarity) β-D-glucose beta-glucose*beta-D-glucopyranose*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 C(O)C1(C(O)C(O)C(O)C(O1)O) PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 3.2.1.28 trehalose + H2O = β-D-glucose trehalose degradation II (high osmolarity) β-D-glucose beta-glucose*beta-D-glucopyranose*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 C(O)C1(C(O)C(O)C(O)C(O1)O) 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 beta-glucose*beta-D-glucopyranose*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 C(O)C1(C(O)C(O)C(O)C(O1)O) PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 3.2.1.21 DIMBOA-Glc + H2O = DIMBOA + β-D-glucose DIMBOA-glucoside degradation β-D-glucose beta-glucose*beta-D-glucopyranose*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 C(O)C1(C(O)C(O)C(O)C(O1)O) PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 2.7.1.1 β-D-glucose + ATP = β-D-glucose-6-phosphate + ADP glucose fermentation to lactate II β-D-glucose beta-glucose*beta-D-glucopyranose*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 C(O)C1(C(O)C(O)C(O)C(O1)O) PUBCHEM:64689:*LIGAND-CPD:C00031:*CAS:50-99-7 3.2.1.21 linamarin + H2O = acetone cyanohydrin + β-D-glucose linamarin degradation trans-zeatin riboside ZR*zeatin riboside 351.361 C15 H21 N5 O5 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(ncn3)NCC=C(C)CO)) trans-zeatin riboside monophosphate + H2O = trans-zeatin riboside trans-zeatin biosynthesis trans-zeatin riboside ZR*zeatin riboside 351.361 C15 H21 N5 O5 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(ncn3)NCC=C(C)CO)) 1.5.99.12 trans-zeatin riboside + H2O + FAD = adenosine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation trans-zeatin riboside ZR*zeatin riboside 351.361 C15 H21 N5 O5 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(ncn3)NCC=C(C)CO)) isopentenyl adenosine + H2O = trans-zeatin riboside + H+ trans-zeatin biosynthesis trans-zeatin riboside ZR*zeatin riboside 351.361 C15 H21 N5 O5 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(ncn3)NCC=C(C)CO)) trans-zeatin riboside + H2O = trans-zeatin + D-ribose trans-zeatin biosynthesis 2-methylbutanol active amyl alcohol*2-methyl-n-butanol*2-methylbutyl alcohol*sec-butylcarbinol 88.149 C5 H12 O1 CCC(C)CO 1.1.1.1 2-methylbutanal + NADH = 2-methylbutanol + NAD+ isoleucine degradation II 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 364.208 C10 H13 N4 O9 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c([nH]3)=O))) CAS:523-98-8:*LIGAND-CPD:C00655: 6.3.4.1 ammonia + xanthosine-5-phosphate + ATP = AMP + diphosphate + GMP salvage pathways of purine nucleosides II (plant) 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 364.208 C10 H13 N4 O9 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c([nH]3)=O))) CAS:523-98-8:*LIGAND-CPD:C00655: 6.3.4.1 ammonia + xanthosine-5-phosphate + ATP = AMP + diphosphate + GMP purine nucleotides de novo biosynthesis I 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 364.208 C10 H13 N4 O9 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c([nH]3)=O))) CAS:523-98-8:*LIGAND-CPD:C00655: 3.1.3.5 xanthosine-5-phosphate + H2O = xanthosine purine degradation 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 364.208 C10 H13 N4 O9 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c([nH]3)=O))) CAS:523-98-8:*LIGAND-CPD:C00655: 3.1.3.5 xanthosine-5-phosphate + H2O = xanthosine ureide biosynthesis 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 364.208 C10 H13 N4 O9 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c([nH]3)=O))) CAS:523-98-8:*LIGAND-CPD:C00655: 3.1.3.5 xanthosine-5-phosphate + H2O = xanthosine salvage pathways of purine nucleosides II (plant) 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 364.208 C10 H13 N4 O9 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c([nH]3)=O))) CAS:523-98-8:*LIGAND-CPD:C00655: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH purine degradation 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 364.208 C10 H13 N4 O9 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c([nH]3)=O))) CAS:523-98-8:*LIGAND-CPD:C00655: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH salvage pathways of purine nucleosides 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 364.208 C10 H13 N4 O9 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c([nH]3)=O))) CAS:523-98-8:*LIGAND-CPD:C00655: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH ureide biosynthesis 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 364.208 C10 H13 N4 O9 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c([nH]3)=O))) CAS:523-98-8:*LIGAND-CPD:C00655: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH salvage pathways of purine nucleosides II (plant) 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 364.208 C10 H13 N4 O9 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c([nH]3)=O))) CAS:523-98-8:*LIGAND-CPD:C00655: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH purine nucleotides de novo biosynthesis II 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 364.208 C10 H13 N4 O9 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c([nH]3)=O))) CAS:523-98-8:*LIGAND-CPD:C00655: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH purine nucleotides de novo biosynthesis I 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 364.208 C10 H13 N4 O9 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c([nH]3)=O))) CAS:523-98-8:*LIGAND-CPD:C00655: 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis II 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 364.208 C10 H13 N4 O9 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c([nH]3)=O))) CAS:523-98-8:*LIGAND-CPD:C00655: 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis I 5-hydroxyisourate 183.103 C5 H3 N4 O4 C12(=NC(=O)[NH]C(=O)C([NH]C(=N1)[O-])(O)2) 3.5.2.17 5-hydroxyisourate + H2O = 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate ureide biosynthesis 5-hydroxyisourate 183.103 C5 H3 N4 O4 C12(=NC(=O)[NH]C(=O)C([NH]C(=N1)[O-])(O)2) 1.7.3.3 urate + O2 + H2O = 5-hydroxyisourate + H2O2 ureide biosynthesis marmesin (+)-Marmesin 246.262 C14 H14 O4 CC(O)(C)C1(Cc2(c(O1)cc3(c(c2)ccc(=O)o3))) PUBCHEM:334704: demethylsuberosin + O2 + NADPH = marmesin + NADP+ + H2O linear furanocoumarin biosynthesis marmesin (+)-Marmesin 246.262 C14 H14 O4 CC(O)(C)C1(Cc2(c(O1)cc3(c(c2)ccc(=O)o3))) PUBCHEM:334704: marmesin + NADPH + O2 = psoralen + NADP+ + acetone + H2O linear furanocoumarin biosynthesis dihydrogeranylgeranyl-PP dihydroGGPP*dihydrogeranylgeranyl diphosphate*dihydrogeranylgeranyl pyrophosphate 452.463 C20 H38 O7 P2 CC(C)=CCCC(C)=CCCC(C)CCCC(C)=CCOP(O)(=O)OP(=O)(O)O 1.3.1.- dihydrogeranylgeranyl-PP + NADPH = tetrahydrogeranylgeranyl-PP + NADP+ phytyl-PP biosynthesis dihydrogeranylgeranyl-PP dihydroGGPP*dihydrogeranylgeranyl diphosphate*dihydrogeranylgeranyl pyrophosphate 452.463 C20 H38 O7 P2 CC(C)=CCCC(C)=CCCC(C)CCCC(C)=CCOP(O)(=O)OP(=O)(O)O 1.3.1.- geranylgeranyl diphosphate + NADPH = dihydrogeranylgeranyl-PP + NADP+ phytyl-PP biosynthesis 5,10-methylene-tetrahydromethanopterin N5,N10-methylene-5,6,7,8-tetrahydromethanopterin*5,10-methylene-5,6,7,8-tetrahydromethanopterin*methylene-H4MPT*5,10-methylene-H4MPT*N5,N10-methylenetetrahydromethanopterin 787.693 C31 H44 N6 O16 P1 C[CH]2([CH]1([CH](C)N(CN1c3(c(=O)[nH]c(N)nc([NH]2)3))c4(ccc(cc4)CC(O)C(O)C(O)COC5(OC(C(O)C5O)COP(=O)([O-])OC(C(O)=O)CCC(O)=O)))) 1.12.98.2 5,10-methenyltetrahydromethanopterin + H2 = 5,10-methylene-tetrahydromethanopterin + H+ methanogenesis from CO2 5,10-methylene-tetrahydromethanopterin N5,N10-methylene-5,6,7,8-tetrahydromethanopterin*5,10-methylene-5,6,7,8-tetrahydromethanopterin*methylene-H4MPT*5,10-methylene-H4MPT*N5,N10-methylenetetrahydromethanopterin 787.693 C31 H44 N6 O16 P1 C[CH]2([CH]1([CH](C)N(CN1c3(c(=O)[nH]c(N)nc([NH]2)3))c4(ccc(cc4)CC(O)C(O)C(O)COC5(OC(C(O)C5O)COP(=O)([O-])OC(C(O)=O)CCC(O)=O)))) 1.5.99.9 5,10-methylene-tetrahydromethanopterin = 5,10-methenyltetrahydromethanopterin methanogenesis from CO2 5,10-methylene-tetrahydromethanopterin N5,N10-methylene-5,6,7,8-tetrahydromethanopterin*5,10-methylene-5,6,7,8-tetrahydromethanopterin*methylene-H4MPT*5,10-methylene-H4MPT*N5,N10-methylenetetrahydromethanopterin 787.693 C31 H44 N6 O16 P1 C[CH]2([CH]1([CH](C)N(CN1c3(c(=O)[nH]c(N)nc([NH]2)3))c4(ccc(cc4)CC(O)C(O)C(O)COC5(OC(C(O)C5O)COP(=O)([O-])OC(C(O)=O)CCC(O)=O)))) 1.5.99.11 5-methyl-tetrahydromethanopterin = 5,10-methylene-tetrahydromethanopterin methanogenesis from CO2 (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->2)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1,6)]-α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 2973.407 C144 H240 N2 O57 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC7(OC(COC3(C(O)C(C(O)C(O3)COC4(OC(CO)C(O)C(O)C(O)4))OC5(C(C(O)C(O)C(O5)CO)OC6(OC(CO)C(O)C(O)C(O)6))))C(O)C(C(O)7)OC8(C(C(O)C(O)C(O8)CO)OC9(C(C(O)C(O)C(O9)CO)OC10(OC(CO)C(O)C(O)C(O)10)))))) (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->2)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1,6)]-α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 2973.407 C144 H240 N2 O57 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC7(OC(COC3(C(O)C(C(O)C(O3)COC4(OC(CO)C(O)C(O)C(O)4))OC5(C(C(O)C(O)C(O5)CO)OC6(OC(CO)C(O)C(O)C(O)6))))C(O)C(C(O)7)OC8(C(C(O)C(O)C(O8)CO)OC9(C(C(O)C(O)C(O9)CO)OC10(OC(CO)C(O)C(O)C(O)10)))))) (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis neurosporene 538.898 C40 H58 CC(C)=CCCC(C)=CC=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)CCC=C(C)CCC=C(C)C PUBCHEM:164636: 1.14.99.30 O2 + neurosporene = H2O + trans-lycopene carotenoid biosynthesis neurosporene 538.898 C40 H58 CC(C)=CCCC(C)=CC=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)CCC=C(C)CCC=C(C)C PUBCHEM:164636: 1.14.99.30 ζ-carotene + O2 = neurosporene + H2O carotenoid biosynthesis sphinganine 1-phosphate Dihydrosphingosine 1-phosphate*Sphinganine 1-phosphate*DHS-1-P 381.491 C18 H40 N1 O5 P1 C(OP(O)(=O)O)C(N)C(O)CCCCCCCCCCCCCCC 2.7.1.91 sphinganine + ATP = sphinganine 1-phosphate + ADP sphingolipid metabolism sphinganine 1-phosphate Dihydrosphingosine 1-phosphate*Sphinganine 1-phosphate*DHS-1-P 381.491 C18 H40 N1 O5 P1 C(OP(O)(=O)O)C(N)C(O)CCCCCCCCCCCCCCC 2.7.1.91 sphinganine + ATP = sphinganine 1-phosphate + ADP sphingolipid metabolism sphinganine 1-phosphate Dihydrosphingosine 1-phosphate*Sphinganine 1-phosphate*DHS-1-P 381.491 C18 H40 N1 O5 P1 C(OP(O)(=O)O)C(N)C(O)CCCCCCCCCCCCCCC 4.1.2.27 sphinganine 1-phosphate = palmitaldehyde + phosphoryl-ethanolamine sphingolipid metabolism nicotine isomethonium ion N-methylnicotinium ion 177.269 C11 H17 N2 c1([n+](C)cc(cc1)[CH]2(N(C)CCC2)) 2.1.1.49 nicotine + S-adenosyl-L-methionine = nicotine isomethonium ion + S-adenosyl-L-homocysteine nicotine degradation II eriodictyol 288.256 C15 H12 O6 c3(c2(OC(c1(ccc(O)c(O)c1))CC(=O)c2c(O)cc(O)3)) 1.14.13.- eriodictyol + NADPH + O2 = 3',4',5'-pentahydroxyflavanone + NADP+ + H2O leucodelphinidin biosynthesis eriodictyol 288.256 C15 H12 O6 c3(c2(OC(c1(ccc(O)c(O)c1))CC(=O)c2c(O)cc(O)3)) 1.14.11.9 eriodictyol + O2 + α-ketoglutarate = dihydroquercetin + CO2 + succinate leucopelargonidin and leucocyanidin biosynthesis eriodictyol 288.256 C15 H12 O6 c3(c2(OC(c1(ccc(O)c(O)c1))CC(=O)c2c(O)cc(O)3)) 1.14.11.9 eriodictyol + O2 + α-ketoglutarate = dihydroquercetin + CO2 + succinate leucodelphinidin biosynthesis (-)-jasmonate (-)-jasmonic acid*jasmonic acid*(3R,7R)-(-)-jasmonate 210.272 C12 H18 O3 C(=O)(O)CC1(C(C(=O)CC1)CC=CCC) 2.1.1.141 (-)-jasmonate + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + (-)-jasmonic acid methyl ester jasmonic acid biosynthesis (-)-jasmonate (-)-jasmonic acid*jasmonic acid*(3R,7R)-(-)-jasmonate 210.272 C12 H18 O3 C(=O)(O)CC1(C(C(=O)CC1)CC=CCC) (+)-7-isojasmonate = (-)-jasmonate jasmonic acid biosynthesis trans-zeatin-9-N-glucoside 381.388 C16 H23 N5 O6 c1(c2(c(ncn1)N(C=N2)C3(OC(CO)C(O)C(O)C(O)3)))(NCC=C(C)CO) 2.4.1.- trans-zeatin + UDP-D-glucose = trans-zeatin-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis (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 CC(C)C(C)CC(O)C(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC3)CC(=O)CC4)(C)))) 1.3.99.- (22α)-hydroxy-campest-4-en-3-one + NADPH = (22α)-hydroxy-5α-campestan-3-one + NADP+ brassinosteroid biosynthesis II (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 CC(C)C(C)CC(O)C(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC3)CC(=O)CC4)(C)))) (22α)-hydroxy-5α-campestan-3-one = 6-deoxocathasterone brassinosteroid biosynthesis II (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 CC(C)C(C)CC(O)C(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC3)CC(=O)CC4)(C)))) 1.14.13.- (5α)-campestan-3-one + O2 + NADPH = (22α)-hydroxy-5α-campestan-3-one + H2O + NADP+ brassinosteroid biosynthesis II xanthoxin 248.321 C15 H20 O3 CC2(C1(C(C)(O1)CC(=O)C2)C=CC(C)=CC=O)(C) 1.13.11.51 9'-cis-neoxanthin + O2 = xanthoxin + C25-allenic-apo-aldehyde abscisic acid biosynthesis xanthoxin 248.321 C15 H20 O3 CC2(C1(C(C)(O1)CC(=O)C2)C=CC(C)=CC=O)(C) 1.1.1.288 xanthoxin + NAD+ = abscisic aldehyde + NADH + H+ abscisic acid 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(O)(=O)C(N)CCCC(N)C(=O)O LIGAND-CPD:C00680:*CAS:922-54-3 6.3.2.13 UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + meso-diaminopimelate + ATP = UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + ADP peptidoglycan biosynthesis I 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(O)(=O)C(N)CCCC(N)C(=O)O LIGAND-CPD:C00680:*CAS:922-54-3 4.1.1.20 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(O)(=O)C(N)CCCC(N)C(=O)O LIGAND-CPD:C00680:*CAS:922-54-3 4.1.1.20 meso-diaminopimelate = CO2 + L-lysine lysine biosynthesis II 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(O)(=O)C(N)CCCC(N)C(=O)O LIGAND-CPD:C00680:*CAS:922-54-3 4.1.1.20 meso-diaminopimelate = CO2 + L-lysine lysine biosynthesis I 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(O)(=O)C(N)CCCC(N)C(=O)O LIGAND-CPD:C00680:*CAS:922-54-3 5.1.1.7 L,L-diaminopimelate = meso-diaminopimelate 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(O)(=O)C(N)CCCC(N)C(=O)O LIGAND-CPD:C00680:*CAS:922-54-3 5.1.1.7 L,L-diaminopimelate = meso-diaminopimelate lysine biosynthesis II 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(O)(=O)C(N)CCCC(N)C(=O)O LIGAND-CPD:C00680:*CAS:922-54-3 5.1.1.7 L,L-diaminopimelate = meso-diaminopimelate lysine biosynthesis I 4-coumaroylshikimate trans-5-O-(4-Coumaroyl)shikimate*trans-(p-coumaroyl)-shikimate 320.298 C16 H16 O7 C(=O)(O)C1(CC(C(O)C(C=1)O)OC(=O)C=CC2(=CC=C(O)C=C2)) 1.14.13.36 4-coumaroylshikimate + NADPH + O2 = caffeoylshikimate + NADP+ + H2O phenylpropanoid biosynthesis 4-coumaroylshikimate trans-5-O-(4-Coumaroyl)shikimate*trans-(p-coumaroyl)-shikimate 320.298 C16 H16 O7 C(=O)(O)C1(CC(C(O)C(C=1)O)OC(=O)C=CC2(=CC=C(O)C=C2)) 2.3.1.133 shikimate + coumaroyl-CoA = 4-coumaroylshikimate + coenzyme A phenylpropanoid biosynthesis delphinidin 3-O-glucosyl-5-O-caffeoylglucoside 789.676 C36 H37 O20 C1(OC(C(O)C(O)C(O)1)COC(=O)C=Cc2(ccc(O)c(O)c2))Oc4(c3(C=C(C(=Oc3cc(O)c4)c5(cc(O)c(O)c(O)c5))OC6(OC(CO)C(O)C(O)C(O)6))) 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 789.676 C36 H37 O20 C1(OC(C(O)C(O)C(O)1)COC(=O)C=Cc2(ccc(O)c(O)c2))Oc4(c3(C=C(C(=Oc3cc(O)c4)c5(cc(O)c(O)c(O)c5))OC6(OC(CO)C(O)C(O)C(O)6))) 2.4.1.- delphinidin 3-O-glucosyl-5-O-caffeoylglucoside + UDP-D-glucose = delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + UDP gentiodelphin biosynthesis 3''-deamino-3''-oxonicotianamine 302.283 C12 H18 N2 O7 C(N1(C(C(=O)O)CC1))CC(C(=O)O)NCCC(=O)C(=O)O LIGAND-CPD:C15486: 1.1.1.285 3''-deamino-3''-oxonicotianamine = 2'-deoxymugineic acid 2'-deoxymugineic acid phytosiderophore biosynthesis 3''-deamino-3''-oxonicotianamine 302.283 C12 H18 N2 O7 C(N1(C(C(=O)O)CC1))CC(C(=O)O)NCCC(=O)C(=O)O LIGAND-CPD:C15486: 2.6.1.80 nicotianamine + α-ketoglutarate = L-glutamate + 3''-deamino-3''-oxonicotianamine 2'-deoxymugineic acid phytosiderophore biosynthesis cholesterol 386.66 C27 H46 O1 CC(C)CCCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C)(C(=CC3)CC(O)CC4)))) CAS:57-88-5 1.3.1.72 desmosterol + NADPH = cholesterol + NADP+ cholesterol biosynthesis III (via desmosterol) cholesterol 386.66 C27 H46 O1 CC(C)CCCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C)(C(=CC3)CC(O)CC4)))) CAS:57-88-5 1.3.1.21 7-dehydro-cholesterol + NADPH = cholesterol + NADP+ cholesterol biosynthesis I cholesterol 386.66 C27 H46 O1 CC(C)CCCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C)(C(=CC3)CC(O)CC4)))) CAS:57-88-5 1.3.1.21 7-dehydro-cholesterol + NADPH = cholesterol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 7,2'-dihydroxy-4'-methoxy-isoflavanol DMI 288.299 C16 H16 O5 C2([CH](c1(c(O)cc(OC)cc1))[CH](O)c3(c(O2)cc(O)cc3)) 1.1.1.246 (-)-vestitone + NADPH + H+ = 7,2'-dihydroxy-4'-methoxy-isoflavanol + NADP+ medicarpin biosynthesis 7,2'-dihydroxy-4'-methoxy-isoflavanol DMI 288.299 C16 H16 O5 C2([CH](c1(c(O)cc(OC)cc1))[CH](O)c3(c(O2)cc(O)cc3)) 7,2'-dihydroxy-4'-methoxy-isoflavanol = 7,2'-dihydroxy-4'-methoxy-isoflavanol-quinonemethide-intermediate-1 medicarpin biosynthesis 7,2'-dihydroxy-4'-methoxy-isoflavanol DMI 288.299 C16 H16 O5 C2([CH](c1(c(O)cc(OC)cc1))[CH](O)c3(c(O2)cc(O)cc3)) 7,2'-dihydroxy-4'-methoxy-isoflavanol = 7,2'-dihydroxy-4'-methoxy-isoflavanol carbocation intermediate 1 medicarpin biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.1 2'-hydroxygenistein + dimethylallyl-PP = phaseoluteone + diphosphate wighteone and luteone biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.1 2'-hydroxygenistein + dimethylallyl-PP = 2,3-dehydrokievitone + diphosphate kievitone biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.1 genistein + dimethylallyl-PP = wighteone + diphosphate wighteone and luteone biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.8 dimethylallyl-PP = diphosphate cis-zeatin biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.27 dimethylallyl-PP + AMP = isopentenyladenosine-5'-monophosphate + diphosphate trans-zeatin biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.- umbelliferone + dimethylallyl-PP = demethylsuberosin + diphosphate linear furanocoumarin biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.- 4-prenylphlorisovalerophenone + dimethylallyl-PP = diprenylphlorisovalerophenone + diphosphate humulone biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.- 4-prenylphlorisobutyrophenone + dimethylallyl-PP = diprenylphlorisobutyrophenone + diphosphate cohumulone biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.- dimethylallyl-PP + ATP = isopentenyladenosine-5'-triphosphate + diphosphate trans-zeatin biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.- phlorisobutyrophenone + dimethylallyl-PP = 4-prenylphlorisobutyrophenone + diphosphate cohumulone biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 1.17.1.2 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H+ = dimethylallyl-PP + H2O methylerythritol phosphate pathway dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.1 2'-hydroxygenistein + dimethylallyl-PP = luteone + diphosphate wighteone and luteone biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.- phlorisovalerophenone + dimethylallyl-PP = 4-prenylphlorisovalerophenone + diphosphate humulone biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.1 genistein + dimethylallyl-PP = isowighteone + diphosphate wighteone and luteone biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.1 dimethylallyl-PP = diphosphate + geranyl-PP geranylgeranyldiphosphate biosynthesis II (plastidic) dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.1 dimethylallyl-PP = diphosphate + geranyl-PP polyisoprenoid biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.1 dimethylallyl-PP = diphosphate + geranyl-PP geranyldiphosphate biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.1 dimethylallyl-PP = diphosphate + geranyl-PP trans,trans-farnesyl diphosphate biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: dalbergioidin + dimethylallyl-PP = kievitone + diphosphate kievitone biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.1 genistein + dimethylallyl-PP = lupiwighteone + diphosphate wighteone and luteone biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 2.5.1.- dimethylallyl-PP + ADP = isopentenyladenosine-5'-diphosphate + diphosphate trans-zeatin biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 5.3.3.2 mevalonate pathway dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 5.3.3.2 polyisoprenoid biosynthesis dimethylallyl-PP delta2-isopentenyl-diphosphate*delta-prenyl diphosphate*prenyl-diphosphate*δ-prenyl diphosphate*δ2-isopentenyl-diphosphate*2-isopentenyl diphosphate*prenyl diphosphate*DMAPP*DPP*dimethylallyl-diphosphate*di-CH3-allyl-PPi*dimethylallyl-PP*dimethylallyl-PPi*DMPP 246.093 C5 H12 O7 P2 C(C=C(C)C)OP(O)(=O)OP(O)(=O)O LIGAND-CPD:C02742:*CAS:358-71-4:*CAS:358-72-5*LIGAND-CPD:C00235:*CAS:358-71-4: 5.3.3.2 methylerythritol phosphate pathway 24-methylenecycloartenol 24(28)-methylenecycloartenol 440.751 C31 H52 O1 CC(C)C(=C)CCC(C)C1(C5(C)(C(C)(CC1)C2(C4(C3([CH](CC2)C(C)(C)C(O)CC3)(C4))(CC5)))) 2.1.1.- 24-methylenecycloartenol = cycloeucalenol sterol biosynthesis 24-methylenecycloartenol 24(28)-methylenecycloartenol 440.751 C31 H52 O1 CC(C)C(=C)CCC(C)C1(C5(C)(C(C)(CC1)C2(C4(C3([CH](CC2)C(C)(C)C(O)CC3)(C4))(CC5)))) 2.1.1.41 S-adenosyl-L-methionine + cycloartenol = S-adenosyl-L-homocysteine + 24-methylenecycloartenol sterol biosynthesis galactopinitol B O-α-D-galactopyranosyl-(1->2)-3-O-methyl-chiro-inositol 356.326 C13 H24 O11 C1(OC(CO)C(O)C(O)C(O)1)OC2(C(OC)C(O)C(O)C(O)C(O)2) 2.4.1.- D-pinitol + galactinol = galactopinitol B + myo-inositol galactosylcyclitol biosynthesis β-alanine β-alanine*3-aminopropanoate 89.094 C3 H7 N1 O2 C(O)(=O)CCN LIGAND-CPD:C00099:*CAS:107-95-9 3.5.1.6 H2O + 3-ureidopropionate = ammonia + CO2 + β-alanine β-alanine biosynthesis III β-alanine β-alanine*3-aminopropanoate 89.094 C3 H7 N1 O2 C(O)(=O)CCN LIGAND-CPD:C00099:*CAS:107-95-9 1.2.1.3 3-aminopropionaldehyde + H2O = β-alanine β-alanine biosynthesis I β-alanine β-alanine*3-aminopropanoate 89.094 C3 H7 N1 O2 C(O)(=O)CCN LIGAND-CPD:C00099:*CAS:107-95-9 6.3.2.1 pantoyl lactone + β-alanine = pantothenate pantothenate biosynthesis III β-alanine β-alanine*3-aminopropanoate 89.094 C3 H7 N1 O2 C(O)(=O)CCN LIGAND-CPD:C00099:*CAS:107-95-9 6.3.2.1 β-alanine + L-pantoate + ATP = pantothenate + diphosphate + AMP pantothenate biosynthesis I β-alanine β-alanine*3-aminopropanoate 89.094 C3 H7 N1 O2 C(O)(=O)CCN LIGAND-CPD:C00099:*CAS:107-95-9 6.3.2.1 β-alanine + L-pantoate + ATP = pantothenate + diphosphate + AMP pantothenate biosynthesis II β-alanine β-alanine*3-aminopropanoate 89.094 C3 H7 N1 O2 C(O)(=O)CCN LIGAND-CPD:C00099:*CAS:107-95-9 2.6.1.18 malonate semialdehyde + L-alanine = β-alanine + pyruvate β-alanine biosynthesis II β-alanine β-alanine*3-aminopropanoate 89.094 C3 H7 N1 O2 C(O)(=O)CCN LIGAND-CPD:C00099:*CAS:107-95-9 2.1.1.49 β-alanine + S-adenosyl-L-methionine = N-methyl-β-alanine + S-adenosyl-L-homocysteine β-alanine betaine biosynthesis (+)-menthofuran menthofuran 150.22 C10 H14 O1 CC1(Cc2(c(CC1)c(C)co2)) (+)-pulegone + NADPH + O2 = (+)-menthofuran + NADP+ + H2O menthol biosynthesis GA36 gibberellin A36*gibberellin A36*GA36 362.422 C20 H26 O6 CC1([CH]4(C(CCC(O)1)(C=O)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA36 + O2 + α-ketoglutarate = GA4 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) GA36 gibberellin A36*gibberellin A36*GA36 362.422 C20 H26 O6 CC1([CH]4(C(CCC(O)1)(C=O)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA37 + α-ketoglutarate + O2 = GA36 + succinate + CO2 + H2O gibberellin biosynthesis II (early C-3 hydroxylation) GA36 gibberellin A36*gibberellin A36*GA36 362.422 C20 H26 O6 CC1([CH]4(C(CCC(O)1)(C=O)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA24 + α-ketoglutarate + O2 = GA36 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) quinate L-quinate*quinic acid 192.168 C7 H12 O6 C(=O)(O)C1([CH2][CH](O)[CH](O)[CH](O)[CH2]1)(O) LIGAND-CPD:C00296:*CAS:77-95-2 3.1.2.- caffeoylquinate + coenzyme A = caffeoyl-CoA + quinate phenylpropanoid biosynthesis quinate L-quinate*quinic acid 192.168 C7 H12 O6 C(=O)(O)C1([CH2][CH](O)[CH](O)[CH](O)[CH2]1)(O) LIGAND-CPD:C00296:*CAS:77-95-2 1.1.99.25 quinate + pyrroloquinoline quinone = 3-dehydroquinate + reduced pyrroloquinoline-quinone quinate degradation quinate L-quinate*quinic acid 192.168 C7 H12 O6 C(=O)(O)C1([CH2][CH](O)[CH](O)[CH](O)[CH2]1)(O) LIGAND-CPD:C00296:*CAS:77-95-2 2.3.1.133 quinate + coumaroyl-CoA = 4-coumaroylquinate + coenzyme A phenylpropanoid biosynthesis dihydrouracil 5,6-dihydrouracil*DI-H-uracil*4,5-dihydrouracil 114.104 C4 H6 N2 O2 C1(NC(=O)NC(=O)C1) CAS:504-07-4 1.3.1.2 NADP+ + dihydrouracil = NADPH + uracil β-alanine biosynthesis III dihydrouracil 5,6-dihydrouracil*DI-H-uracil*4,5-dihydrouracil 114.104 C4 H6 N2 O2 C1(NC(=O)NC(=O)C1) CAS:504-07-4 3.5.2.2 H2O + dihydrouracil = 3-ureidopropionate β-alanine biosynthesis III 18-hydroxyoleate 18-hydroxyoctadec-9-enoic acid 298.465 C18 H34 O3 C(O)CCCCCCCC=CCCCCCCCC(=O)O 1.1.1.- 18-hydroxyoleate + NADP+ = 18-oxooleate + NADPH suberin biosynthesis 18-hydroxyoleate 18-hydroxyoctadec-9-enoic acid 298.465 C18 H34 O3 C(O)CCCCCCCC=CCCCCCCCC(=O)O 1.14.13.- oleate + NADPH + O2 = 18-hydroxyoleate + NADP+ + H2O cutin biosynthesis 18-hydroxyoleate 18-hydroxyoctadec-9-enoic acid 298.465 C18 H34 O3 C(O)CCCCCCCC=CCCCCCCCC(=O)O 1.14.13.- oleate + NADPH + O2 = 18-hydroxyoleate + NADP+ + H2O suberin biosynthesis 18-hydroxyoleate 18-hydroxyoctadec-9-enoic acid 298.465 C18 H34 O3 C(O)CCCCCCCC=CCCCCCCCC(=O)O 18-hydroxyoleate + NADPH + O2 = 9,10-epoxy-18-hydroxystearate + NADP+ + H2O cutin biosynthesis 4-guanidinobutyrate γ-guanidinobutyrate*4-guanidinobutanoate 145.161 C5 H11 N3 O2 C(NC(N)=N)CCC(=O)O 3.5.1.4 4-guanidinobutyramide + H2O = ammonia + 4-guanidinobutyrate arginine degradation X (arginine monooxygenase pathway) 4-guanidinobutyrate γ-guanidinobutyrate*4-guanidinobutanoate 145.161 C5 H11 N3 O2 C(NC(N)=N)CCC(=O)O 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 c2(c1(c(NC=N1)ncn2))NCCC(C)COC3(OC(CO)C(O)C(O)C(O)3) 2.4.1.- dihydrozeatin + UDP-D-glucose = dihydrozeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol 4,4-dimethyl-8,24-cholestadienol*4,4-dimethylzymosterol*14-demethyllanosterol*17-(1,5-dimethylhex-4-enyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7, 10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a] phenanthren-3-ol*4,4-dimethyl-5α-cholesta-8,24-dien-3β-ol 412.698 C29 H48 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.3.1.70 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADPH = 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + NADP+ cholesterol biosynthesis I 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol 4,4-dimethyl-8,24-cholestadienol*4,4-dimethylzymosterol*14-demethyllanosterol*17-(1,5-dimethylhex-4-enyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7, 10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a] phenanthren-3-ol*4,4-dimethyl-5α-cholesta-8,24-dien-3β-ol 412.698 C29 H48 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.3.1.70 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADPH = 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + NADP+ cholesterol biosynthesis III (via desmosterol) 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol 4,4-dimethyl-8,24-cholestadienol*4,4-dimethylzymosterol*14-demethyllanosterol*17-(1,5-dimethylhex-4-enyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7, 10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a] phenanthren-3-ol*4,4-dimethyl-5α-cholesta-8,24-dien-3β-ol 412.698 C29 H48 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.14.13.72 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + O2 = 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol 4,4-dimethyl-8,24-cholestadienol*4,4-dimethylzymosterol*14-demethyllanosterol*17-(1,5-dimethylhex-4-enyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7, 10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a] phenanthren-3-ol*4,4-dimethyl-5α-cholesta-8,24-dien-3β-ol 412.698 C29 H48 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.14.13.72 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + O2 = 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) dUMP U*deoxyurdine-phosphate*2'-deoxyuridine-5-monophosphate*deoxyuridine-phosphate*2'-deoxyuridine-5'-phosphate*2'-deoxyuridylic acid*2'-deoxy-5'-uridylic acid 308.184 C9 H13 N2 O8 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)COP(O)(O)=O)) LIGAND-CPD:C00365:*CAS:964-26-1 2.7.1.21 deoxyuridine + ATP = dUMP + ADP salvage pathways of pyrimidine deoxyribonucleotides dUMP U*deoxyurdine-phosphate*2'-deoxyuridine-5-monophosphate*deoxyuridine-phosphate*2'-deoxyuridine-5'-phosphate*2'-deoxyuridylic acid*2'-deoxy-5'-uridylic acid 308.184 C9 H13 N2 O8 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)COP(O)(O)=O)) LIGAND-CPD:C00365:*CAS:964-26-1 3.6.1.23 H2O + dUTP = diphosphate + dUMP de novo biosynthesis of pyrimidine deoxyribonucleotides dUMP U*deoxyurdine-phosphate*2'-deoxyuridine-5-monophosphate*deoxyuridine-phosphate*2'-deoxyuridine-5'-phosphate*2'-deoxyuridylic acid*2'-deoxy-5'-uridylic acid 308.184 C9 H13 N2 O8 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)COP(O)(O)=O)) LIGAND-CPD:C00365:*CAS:964-26-1 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate salvage pathways of purine and pyrimidine nucleotides dUMP U*deoxyurdine-phosphate*2'-deoxyuridine-5-monophosphate*deoxyuridine-phosphate*2'-deoxyuridine-5'-phosphate*2'-deoxyuridylic acid*2'-deoxy-5'-uridylic acid 308.184 C9 H13 N2 O8 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)COP(O)(O)=O)) LIGAND-CPD:C00365:*CAS:964-26-1 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate de novo biosynthesis of pyrimidine deoxyribonucleotides dUMP U*deoxyurdine-phosphate*2'-deoxyuridine-5-monophosphate*deoxyuridine-phosphate*2'-deoxyuridine-5'-phosphate*2'-deoxyuridylic acid*2'-deoxy-5'-uridylic acid 308.184 C9 H13 N2 O8 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)COP(O)(O)=O)) LIGAND-CPD:C00365:*CAS:964-26-1 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate formylTHF biosynthesis II dUMP U*deoxyurdine-phosphate*2'-deoxyuridine-5-monophosphate*deoxyuridine-phosphate*2'-deoxyuridine-5'-phosphate*2'-deoxyuridylic acid*2'-deoxy-5'-uridylic acid 308.184 C9 H13 N2 O8 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)COP(O)(O)=O)) LIGAND-CPD:C00365:*CAS:964-26-1 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate formylTHF biosynthesis I phytosphingosine-1-P 2.7.1.91 4-hydroxysphinganine + ATP = phytosphingosine-1-P + ADP sphingolipid metabolism phytosphingosine-1-P 2.7.1.91 phytosphingosine-1-P + ADP = ATP + 4-hydroxysphinganine sphingolipid metabolism 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole (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 454.286 C13 H19 N4 O12 P1 [CH]1([CH](O)[CH](O)[CH](O1)COP(=O)(O)O)n2(c(N)c(nc2)C(=O)NC(C(O)=O)CC(O)=O) LIGAND-CPD:C04823: 6.3.2.6 ATP + 4-carboxyaminoimidazole ribonucleotide + L-aspartate = ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole purine nucleotides de novo biosynthesis II 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole (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 454.286 C13 H19 N4 O12 P1 [CH]1([CH](O)[CH](O)[CH](O1)COP(=O)(O)O)n2(c(N)c(nc2)C(=O)NC(C(O)=O)CC(O)=O) LIGAND-CPD:C04823: 6.3.2.6 ATP + 4-carboxyaminoimidazole ribonucleotide + L-aspartate = ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole purine nucleotides de novo biosynthesis I 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole (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 454.286 C13 H19 N4 O12 P1 [CH]1([CH](O)[CH](O)[CH](O1)COP(=O)(O)O)n2(c(N)c(nc2)C(=O)NC(C(O)=O)CC(O)=O) LIGAND-CPD:C04823: 4.3.2.2 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole = fumarate + AICAR purine nucleotides de novo biosynthesis II 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole (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 454.286 C13 H19 N4 O12 P1 [CH]1([CH](O)[CH](O)[CH](O1)COP(=O)(O)O)n2(c(N)c(nc2)C(=O)NC(C(O)=O)CC(O)=O) LIGAND-CPD:C04823: 4.3.2.2 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole = fumarate + AICAR purine nucleotides de novo biosynthesis I L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 6.3.2.6 ATP + 4-carboxyaminoimidazole ribonucleotide + L-aspartate = ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole purine nucleotides de novo biosynthesis II L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 6.3.2.6 ATP + 4-carboxyaminoimidazole ribonucleotide + L-aspartate = ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole purine nucleotides de novo biosynthesis I L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate glutamine degradation III L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate asparagine degradation I L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate aspartate biosynthesis I L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate aspartate degradation II L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate asparagine biosynthesis I L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 4.3.1.1 L-aspartate = ammonia + fumarate glutamine degradation III L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 6.1.1.12 L-aspartate + ATP = diphosphate + AMP tRNA charging pathway L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 3.5.1.1 L-asparagine + H2O = ammonia + L-aspartate asparagine degradation I L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 3.5.1.1 L-asparagine + H2O = ammonia + L-aspartate asparagine degradation II L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 2.1.3.2 L-aspartate + carbamoyl-phosphate = N-carbamoyl-L-aspartate de novo biosynthesis of pyrimidine ribonucleotides L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O 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 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 2.7.2.4 L-aspartate + ATP = L-aspartyl-4-phosphate + ADP lysine biosynthesis II L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 2.7.2.4 L-aspartate + ATP = L-aspartyl-4-phosphate + ADP lysine biosynthesis I L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O 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 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 6.3.4.5 O-ureidohomoserine + L-aspartate + ATP = canavaninosuccinate + AMP + diphosphate canavanine biosynthesis L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 indole-3-acetate + L-aspartate = indole-3-acetyl-asp + H2O IAA conjugate biosynthesis II L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP urea cycle L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis II (acetyl cycle) L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP citrulline-nitric oxide cycle L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis IV L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis I L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 1.4.3.- O2 + L-aspartate = H2O2 + iminoaspartate NAD biosynthesis I (from aspartate) L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = adenylo-succinate + GDP salvage pathways of purine nucleosides L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = adenylo-succinate + GDP purine nucleotides de novo biosynthesis II L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = adenylo-succinate + GDP purine nucleotides de novo biosynthesis I L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis III L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis I L-aspartate L-aspartic acid*aspartic acid*D*aspartate*asp 133.104 C4 H7 N1 O4 C(=O)(O)C(N)CC(O)=O LIGAND-CPD:C00049:*CAS:56-84-8 6.3.1.1 ammonia + L-aspartate + ATP = L-asparagine + diphosphate + AMP asparagine biosynthesis III indole-3-acetyl-ala indole-3-acetyl-alanine 246.265 C13 H14 N2 O3 C(O)(=O)C(C)NC(=O)Cc2(c[nH]c1(ccccc12)) indole-3-acetate + L-alanine = indole-3-acetyl-ala + H2O IAA conjugate biosynthesis II indole-3-acetyl-ala indole-3-acetyl-alanine 246.265 C13 H14 N2 O3 C(O)(=O)C(C)NC(=O)Cc2(c[nH]c1(ccccc12)) 3.5.1.- indole-3-acetyl-ala + H2O = indole-3-acetate + L-alanine IAA biosynthesis II arachidonate 5,8,11,14-icosatetraenoate*arachidonic acid*arachidonate 304.472 C20 H32 O2 C(O)(=O)CCCC=CCC=CCC=CCC=CCCCCC CAS:506-32-1 3.5.1.4 anandamide + H2O = arachidonate + ethanolamine anandamide degradation 5-amino-6-(5'-phosphoribitylamino)uracil 5-amino-6-(5'-phosphoribitylamino)uracil*5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione 5'-phosphate 356.228 C9 H17 N4 O9 P1 C(C(O)C(O)C(O)COP(O)(O)=O)Nc1(c(N)c(=O)[nH]c([nH]1)=O) LIGAND-CPD:C04454: 1.1.1.193 5-amino-6-(5'-phosphoribitylamino)uracil + NADP+ = 5-amino-6-(5'-phosphoribosylamino)uracil + NADPH + H+ flavin biosynthesis 5-amino-6-(5'-phosphoribitylamino)uracil 5-amino-6-(5'-phosphoribitylamino)uracil*5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione 5'-phosphate 356.228 C9 H17 N4 O9 P1 C(C(O)C(O)C(O)COP(O)(O)=O)Nc1(c(N)c(=O)[nH]c([nH]1)=O) LIGAND-CPD:C04454: 5-amino-6-(5'-phosphoribitylamino)uracil + H2O = 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione flavin biosynthesis 24-epi-campesterol 400.687 C28 H48 O1 CC(C(C)C)CCC(C)C1(C2(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))(C)) 1.3.-.- 24-methyldesmosterol = 24-epi-campesterol sterol biosynthesis 24-epi-campesterol 400.687 C28 H48 O1 CC(C(C)C)CCC(C)C1(C2(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))(C)) 1.3.1.- 24-epi-campesterol + NADP+ = brassicasterol + NADPH sterol 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 500.077 C6 H16 O18 P4 C1(C(OP(O)(=O)O)C(OP(O)(=O)O)C(OP(O)(=O)O)C(C(O)1)OP(O)(=O)O)(O) 2.7.1.134 D-myo-inositol (3,4,5,6)-tetrakisphosphate + ATP = D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-independent phytate 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 500.077 C6 H16 O18 P4 C1(C(OP(O)(=O)O)C(OP(O)(=O)O)C(OP(O)(=O)O)C(C(O)1)OP(O)(=O)O)(O) D-myo-inositol (3,4,6)-trisphosphate + ATP = D-myo-inositol (3,4,5,6)-tetrakisphosphate + ADP lipid-independent phytate biosynthesis phenylacetaldehyde 120.151 C8 H8 O1 C(=O)Cc1(ccccc1) CAS:122-78-1:*LIGAND-CPD:C00601: 1.1.1.1 phenylacetaldehyde + NADH = 2-phenylethanol + NAD+ phenylalanine degradation III phenylacetaldehyde 120.151 C8 H8 O1 C(=O)Cc1(ccccc1) CAS:122-78-1:*LIGAND-CPD:C00601: 4.1.1.43 phenylpyruvate = CO2 + phenylacetaldehyde phenylalanine degradation III (2S)-pinocembrin 256.257 C15 H12 O4 c3(c2(OC(c1(ccccc1))CC(=O)c2c(O)cc(O)3)) (2S)-pinocembrin + S-adenosyl-L-methionine = pinostrobin + S-adenosyl-L-homocysteine pinobanksin biosynthesis (2S)-pinocembrin 256.257 C15 H12 O4 c3(c2(OC(c1(ccccc1))CC(=O)c2c(O)cc(O)3)) 5.5.1.6 pinocembrin chalcone = (2S)-pinocembrin pinobanksin biosynthesis (2S)-pinocembrin 256.257 C15 H12 O4 c3(c2(OC(c1(ccccc1))CC(=O)c2c(O)cc(O)3)) 1.14.11.9 (2S)-pinocembrin + O2 + α-ketoglutarate = (2R,3R)-pinobanksin + CO2 + succinate pinobanksin biosynthesis p-aminobenzoate para-aminobenzoic acid*p-aminobenzoic acid*para-aminobenzoate*4-aminobenzoate*4-aminobenzoic acid 137.138 C7 H7 N1 O2 C(=O)(O)c1(ccc(N)cc1) CAS:150-13-0:*LIGAND-CPD:C00568: p-aminobenzoate + UDP-D-glucose = p-aminobenzoate-β-D-glucopyranosyl ester + UDP tetrahydrofolate biosynthesis II p-aminobenzoate para-aminobenzoic acid*p-aminobenzoic acid*para-aminobenzoate*4-aminobenzoate*4-aminobenzoic acid 137.138 C7 H7 N1 O2 C(=O)(O)c1(ccc(N)cc1) CAS:150-13-0:*LIGAND-CPD:C00568: 4.1.3.38 4-amino-4-deoxychorismate = p-aminobenzoate + pyruvate tetrahydrofolate biosynthesis I p-aminobenzoate para-aminobenzoic acid*p-aminobenzoic acid*para-aminobenzoate*4-aminobenzoate*4-aminobenzoic acid 137.138 C7 H7 N1 O2 C(=O)(O)c1(ccc(N)cc1) CAS:150-13-0:*LIGAND-CPD:C00568: 4.1.3.38 4-amino-4-deoxychorismate = p-aminobenzoate + pyruvate tetrahydrofolate biosynthesis II p-aminobenzoate para-aminobenzoic acid*p-aminobenzoic acid*para-aminobenzoate*4-aminobenzoate*4-aminobenzoic acid 137.138 C7 H7 N1 O2 C(=O)(O)c1(ccc(N)cc1) CAS:150-13-0:*LIGAND-CPD:C00568: 2.5.1.15 p-aminobenzoate + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate = diphosphate tetrahydrofolate biosynthesis I p-aminobenzoate para-aminobenzoic acid*p-aminobenzoic acid*para-aminobenzoate*4-aminobenzoate*4-aminobenzoic acid 137.138 C7 H7 N1 O2 C(=O)(O)c1(ccc(N)cc1) CAS:150-13-0:*LIGAND-CPD:C00568: 2.5.1.15 p-aminobenzoate + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate = diphosphate tetrahydrofolate biosynthesis II 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol 442.724 C30 H50 O2 CC(C)=CCCC(C)C1(C2(C)(C(CO)(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis I 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol 442.724 C30 H50 O2 CC(C)=CCCC(C)C1(C2(C)(C(CO)(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol 442.724 C30 H50 O2 CC(C)=CCCC(C)C1(C2(C)(C(CO)(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.14.13.70 lanosterol + NADPH + O2 = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis I 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol 442.724 C30 H50 O2 CC(C)=CCCC(C)C1(C2(C)(C(CO)(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.14.13.70 lanosterol + NADPH + O2 = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) (E)-α-bisabolene trans-α-bisabolene 204.355 C15 H24 CC1(CCC(CC=1)C(C)=CCC=C(C)C) 4.2.3.- trans, trans-farnesyl diphosphate = (E)-α-bisabolene + diphosphate oleoresin sesquiterpene volatiles biosynthesis trans-zeatin-7-N-glucoside 381.388 C16 H23 N5 O6 c2(c1(N(C=Nc1ncn2)C3(OC(CO)C(O)C(O)C(O)3)))(NCC=C(C)CO) 2.4.1.- trans-zeatin + UDP-D-glucose = trans-zeatin-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis cycloeucalenol 426.724 C30 H50 O1 CC(C)C(=C)CCC(C)C1(C5(C)(C(C)(CC1)C2(C4(C3([CH](CC2)C(C)C(O)CC3)(C4))(CC5)))) LIGAND-CPD:C02141:*CAS:469-39-6 2.1.1.- 24-methylenecycloartenol = cycloeucalenol sterol biosynthesis cycloeucalenol 426.724 C30 H50 O1 CC(C)C(=C)CCC(C)C1(C5(C)(C(C)(CC1)C2(C4(C3([CH](CC2)C(C)C(O)CC3)(C4))(CC5)))) LIGAND-CPD:C02141:*CAS:469-39-6 5.5.1.9 cycloeucalenol = obtusifoliol sterol biosynthesis geranylgeranyl diphosphate all-trans-geranyl-geranyl-pp*geranylgeranyl-PP*GGPP 450.448 C20 H36 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(O)(O)=O 5.5.1.13 geranylgeranyl diphosphate = ent-copalyl diphosphate ent-kaurene biosynthesis geranylgeranyl diphosphate all-trans-geranyl-geranyl-pp*geranylgeranyl-PP*GGPP 450.448 C20 H36 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(O)(O)=O 2.5.1.29 trans, trans-farnesyl diphosphate = geranylgeranyl diphosphate + diphosphate geranylgeranyldiphosphate biosynthesis II (plastidic) geranylgeranyl diphosphate all-trans-geranyl-geranyl-pp*geranylgeranyl-PP*GGPP 450.448 C20 H36 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(O)(O)=O 2.5.1.32 geranylgeranyl diphosphate = prephytoene diphosphate + diphosphate carotenoid biosynthesis geranylgeranyl diphosphate all-trans-geranyl-geranyl-pp*geranylgeranyl-PP*GGPP 450.448 C20 H36 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(O)(O)=O geranylgeranyl diphosphate = syn-copalyl diphosphate momilactone biosynthesis geranylgeranyl diphosphate all-trans-geranyl-geranyl-pp*geranylgeranyl-PP*GGPP 450.448 C20 H36 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(O)(O)=O 2.5.1.- chlorophyllide a + geranylgeranyl diphosphate = geranylgeranyl-chlorophyll a + diphosphate chlorophyll a biosynthesis II geranylgeranyl diphosphate all-trans-geranyl-geranyl-pp*geranylgeranyl-PP*GGPP 450.448 C20 H36 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(O)(O)=O 1.3.1.- geranylgeranyl diphosphate + NADPH = dihydrogeranylgeranyl-PP + NADP+ phytyl-PP biosynthesis dipicolinate dipicolinic acid*DPA 167.121 C7 H5 N1 O4 C(=O)(O)c1(nc(C(O)=O)ccc1) NAD+ = dipicolinate + NADH + H+ lysine biosynthesis II methanol MetOH*carbinol*MeOH*methyl alcohol*wood alcohol 32.042 C1 H4 O1 CO CAS:67-56-1 3.1.1.11 H2O = methanol homogalacturonan degradation spermine gerontine*musculamine*neuridine*diaminopropyl-tetramethylenediamine 202.342 C10 H26 N4 C(CCN)NCCCCNCCCN CAS:71-44-3 2.5.1.22 spermidine + S-adenosyl-L-methioninamine = spermine + 5'-methylthioadenosine spermine biosynthesis spermine gerontine*musculamine*neuridine*diaminopropyl-tetramethylenediamine 202.342 C10 H26 N4 C(CCN)NCCCCNCCCN CAS:71-44-3 1.5.3.11 spermine + O2 + H2O = 1-(3-aminopropyl)-4-aminobutanal + 1,3-diaminopropane + H2O2 β-alanine biosynthesis I 12-oxo-cis-9-dodecenoate 12-oxo-c-9-dodecenoate 212.288 C12 H20 O3 C(=O)CC=CCCCCCCCC(O)=O PUBCHEM:543432: 12-oxo-cis-9-dodecenoate = 12-oxo-trans-10-dodecenoate 13-LOX and 13-HPL pathway 12-oxo-cis-9-dodecenoate 12-oxo-c-9-dodecenoate 212.288 C12 H20 O3 C(=O)CC=CCCCCCCCC(O)=O PUBCHEM:543432: 13-HPOT = 12-oxo-cis-9-dodecenoate + cis-3-hexenal 13-LOX and 13-HPL pathway 12-oxo-cis-9-dodecenoate 12-oxo-c-9-dodecenoate 212.288 C12 H20 O3 C(=O)CC=CCCCCCCCC(O)=O PUBCHEM:543432: 13-HPOD = 12-oxo-cis-9-dodecenoate + hexanal 13-LOX and 13-HPL pathway mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol α-D-mannosylchitobiosyldiphosphodolichol*{β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol*β-1,4-D-mannosylchitobiosyldiphosphodolichol 1838.413 C102 H170 N2 O22 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC3(OC(CO)C(O)C(O)C(O)3))) 2.4.1.132 mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol α-D-mannosylchitobiosyldiphosphodolichol*{β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol*β-1,4-D-mannosylchitobiosyldiphosphodolichol 1838.413 C102 H170 N2 O22 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC3(OC(CO)C(O)C(O)C(O)3))) 2.4.1.142 (N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis butyryl-CoA butanoyl-CoA*butyryl-coenzyme A 837.625 C25 H42 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(O)=O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC) LIGAND-CPD:C00136:*LIGAND-CPD:c00136:*UM-BBD-CPD:c0023:*CAS:2140-48-9 1.3.99.2 butyryl-CoA = crotonyl-CoA gallate degradation III (anaerobic) butyryl-CoA butanoyl-CoA*butyryl-coenzyme A 837.625 C25 H42 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(O)=O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC) LIGAND-CPD:C00136:*LIGAND-CPD:c00136:*UM-BBD-CPD:c0023:*CAS:2140-48-9 1.3.1.- crotonyl-CoA + NADH = butyryl-CoA + NAD+ ethanol fermentation to acetate butyryl-CoA butanoyl-CoA*butyryl-coenzyme A 837.625 C25 H42 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(O)=O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC) LIGAND-CPD:C00136:*LIGAND-CPD:c00136:*UM-BBD-CPD:c0023:*CAS:2140-48-9 2.8.3.8 butyryl-CoA + acetate = butyrate + acetyl-CoA ethanol fermentation to acetate butyryl-CoA butanoyl-CoA*butyryl-coenzyme A 837.625 C25 H42 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(O)=O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC) LIGAND-CPD:C00136:*LIGAND-CPD:c00136:*UM-BBD-CPD:c0023:*CAS:2140-48-9 2.8.3.8 butyryl-CoA + acetate = butyrate + acetyl-CoA gallate degradation III (anaerobic) butyryl-CoA butanoyl-CoA*butyryl-coenzyme A 837.625 C25 H42 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(O)=O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC) LIGAND-CPD:C00136:*LIGAND-CPD:c00136:*UM-BBD-CPD:c0023:*CAS:2140-48-9 2.3.1.19 butyryl-CoA = butyryl phosphate + coenzyme A acetyl CoA fermentation to butyrate butyryl-CoA butanoyl-CoA*butyryl-coenzyme A 837.625 C25 H42 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(O)=O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC) LIGAND-CPD:C00136:*LIGAND-CPD:c00136:*UM-BBD-CPD:c0023:*CAS:2140-48-9 1.3.99.2 butyryl-CoA = crotonyl-CoA acetyl CoA fermentation to butyrate shikimate shikimic acid 174.153 C7 H10 O5 C(=O)(O)C1(=[CH][CH](O)[CH](O)[CH](O)[CH2]1) LIGAND-CPD:C00493:*CAS:138-59-0 1.1.1.25 NADP+ + shikimate = NADPH + 3-dehydro-shikimate chorismate biosynthesis shikimate shikimic acid 174.153 C7 H10 O5 C(=O)(O)C1(=[CH][CH](O)[CH](O)[CH](O)[CH2]1) LIGAND-CPD:C00493:*CAS:138-59-0 1.1.1.282 shikimate = 3-dehydro-shikimate + H+ chorismate biosynthesis shikimate shikimic acid 174.153 C7 H10 O5 C(=O)(O)C1(=[CH][CH](O)[CH](O)[CH](O)[CH2]1) LIGAND-CPD:C00493:*CAS:138-59-0 2.7.1.71 shikimate + ATP = shikimate-3-phosphate + ADP chorismate biosynthesis shikimate shikimic acid 174.153 C7 H10 O5 C(=O)(O)C1(=[CH][CH](O)[CH](O)[CH](O)[CH2]1) LIGAND-CPD:C00493:*CAS:138-59-0 2.3.1.133 shikimate + coumaroyl-CoA = 4-coumaroylshikimate + coenzyme A phenylpropanoid biosynthesis shikimate shikimic acid 174.153 C7 H10 O5 C(=O)(O)C1(=[CH][CH](O)[CH](O)[CH](O)[CH2]1) LIGAND-CPD:C00493:*CAS:138-59-0 3.1.2.- caffeoylshikimate + coenzyme A = caffeoyl-CoA + shikimate phenylpropanoid biosynthesis 4-prenylphlorisobutyrophenone compound co-X*PPIBP 264.321 C15 H20 O4 CC(C)=CCc1(c(O)c(C(=O)C(C)C)c(O)cc(O)1) 2.5.1.- phlorisobutyrophenone + dimethylallyl-PP = 4-prenylphlorisobutyrophenone + diphosphate cohumulone biosynthesis 4-prenylphlorisobutyrophenone compound co-X*PPIBP 264.321 C15 H20 O4 CC(C)=CCc1(c(O)c(C(=O)C(C)C)c(O)cc(O)1) 2.5.1.- 4-prenylphlorisobutyrophenone + dimethylallyl-PP = diprenylphlorisobutyrophenone + diphosphate cohumulone biosynthesis divinyl protochlorophyllide a divinylprotochlorophyllide*divinyl protochlrophyllide a 610.951 C35 H30 N4 O5 MG1 C=CC8(C3(=N7([Mg]59(n2(c1(=C(C(C(=O)OC)C(=O)c1c(C)c2=C3)C4(=N(C(C(C)=C4CCC(=O)O)=Cc6(n5c(c(C=C)c(C)6)C=C7C(C)=8))9))))))) 1.14.13.81 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = divinyl protochlorophyllide a + NADP+ + H2O chlorophyllide a biosynthesis divinyl protochlorophyllide a divinylprotochlorophyllide*divinyl protochlrophyllide a 610.951 C35 H30 N4 O5 MG1 C=CC8(C3(=N7([Mg]59(n2(c1(=C(C(C(=O)OC)C(=O)c1c(C)c2=C3)C4(=N(C(C(C)=C4CCC(=O)O)=Cc6(n5c(c(C=C)c(C)6)C=C7C(C)=8))9))))))) 1.3.1.75 divinyl protochlorophyllide a + NADPH + H+ + H+ = monovinyl protochlorophyllide a + NADP+ chlorophyllide a biosynthesis 4-fumaryl-acetoacetate 200.148 C8 H8 O6 C(=O)(O)C=CC(=O)CC(=O)CC(O)=O 5.2.1.2 4-maleyl-acetoacetate = 4-fumaryl-acetoacetate tyrosine degradation I 4-fumaryl-acetoacetate 200.148 C8 H8 O6 C(=O)(O)C=CC(=O)CC(=O)CC(O)=O 3.7.1.2 H2O + 4-fumaryl-acetoacetate = fumarate + acetoacetate tyrosine degradation I pyridoxal 167.164 C8 H9 N1 O3 C(=O)c1(c(CO)cnc(C)c(O)1) LIGAND-CPD:C00250:*CAS:66-72-8 2.6.1.30 pyruvate + pyridoxamine = L-alanine + pyridoxal pyridoxamine anabolism pyridoxal 167.164 C8 H9 N1 O3 C(=O)c1(c(CO)cnc(C)c(O)1) LIGAND-CPD:C00250:*CAS:66-72-8 2.7.1.35 ATP + pyridoxal = ADP + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway pyridoxal 167.164 C8 H9 N1 O3 C(=O)c1(c(CO)cnc(C)c(O)1) LIGAND-CPD:C00250:*CAS:66-72-8 2.7.1.35 ATP + pyridoxal = ADP + pyridoxal 5'-phosphate pyridoxamine anabolism 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(C(O)=O)CCCN 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(C(O)=O)CCCN LIGAND-CPD:C00437:*CAS:2185-16-2 2.6.1.11 N-acetyl-L-ornithine + α-ketoglutarate = 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(C(O)=O)CCCN LIGAND-CPD:C00437:*CAS:2185-16-2 2.6.1.11 N-acetyl-L-ornithine + α-ketoglutarate = 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(C(O)=O)CCCN 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 144.176 C5 H12 N4 O1 C(NC(=N)N)CCC(N)=O 3.5.1.4 4-guanidinobutyramide + H2O = ammonia + 4-guanidinobutyrate arginine degradation X (arginine monooxygenase pathway) 4-guanidinobutyramide 4-guanidinobutanamide*4-guanidobutanamide*4-guanido-butyramide*γ-guanidinobutyramide 144.176 C5 H12 N4 O1 C(NC(=N)N)CCC(N)=O 1.13.12.1 O2 + L-arginine = 4-guanidinobutyramide + H2O + CO2 arginine degradation X (arginine monooxygenase pathway) imidazole acetol-phosphate imidazole acetol-P*3-(imidazol-4-yl)-2-oxopropyl phosphate 220.121 C6 H9 N2 O5 P1 c1(c(nc[nH]1)CC(=O)COP(=O)(O)O) LIGAND-CPD:C01267:*CAS:99979-59-6 2.6.1.9 imidazole acetol-phosphate + L-glutamate = L-histidinol-phosphate + α-ketoglutarate histidine biosynthesis I imidazole acetol-phosphate imidazole acetol-P*3-(imidazol-4-yl)-2-oxopropyl phosphate 220.121 C6 H9 N2 O5 P1 c1(c(nc[nH]1)CC(=O)COP(=O)(O)O) LIGAND-CPD:C01267:*CAS:99979-59-6 4.2.1.19 D-erythro-imidazole-glycerol-phosphate = imidazole acetol-phosphate + H2O histidine biosynthesis I N-acetyl-glucosamine-1-phosphate N-acetyl-D-glucosamine 1-phosphate*N-acetyl-α-D-glucosamine 1-phosphate 301.189 C8 H16 N1 O9 P1 CC(=O)NC1(C(OP(O)(O)=O)OC(CO)C(O)C1O) LIGAND-CPD:C04256: 5.4.2.3 N-acetyl-glucosamine-1-phosphate = N-acetyl-D-glucosamine-6-phosphate UDP-N-acetylgalactosamine biosynthesis N-acetyl-glucosamine-1-phosphate N-acetyl-D-glucosamine 1-phosphate*N-acetyl-α-D-glucosamine 1-phosphate 301.189 C8 H16 N1 O9 P1 CC(=O)NC1(C(OP(O)(O)=O)OC(CO)C(O)C1O) LIGAND-CPD:C04256: 2.7.7.23 N-acetyl-glucosamine-1-phosphate + UTP = UDP-N-acetyl-D-glucosamine + diphosphate UDP-N-acetylgalactosamine biosynthesis indole-3-glyoxal 3-indoleglyoxal 173.171 C10 H7 N1 O2 C(=O)C(=O)c1(c2(c([nH]c1)cccc2)) 1.2.1.5 indole-3-glyoxal + H2O + an oxidized acceptor = indole-3-glyoxylate tryptophan degradation V (side chain pathway) indole-3-glyoxal 3-indoleglyoxal 173.171 C10 H7 N1 O2 C(=O)C(=O)c1(c2(c([nH]c1)cccc2)) indole-3-glycol aldehyde = indole-3-glyoxal tryptophan degradation V (side chain pathway) indole-3-glyoxal 3-indoleglyoxal 173.171 C10 H7 N1 O2 C(=O)C(=O)c1(c2(c([nH]c1)cccc2)) 1.1.99.8 indole-3-glyoxal + NADH + H+ = indole-3-ketol + NAD+ tryptophan degradation V (side chain pathway) 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 867.608 C25 H40 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(=O)O)COP(=O)(O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O) LIGAND-CPD:C00091:*CAS:604-98-8 α-ketoglutarate + coenzyme A + NAD+ = succinyl-CoA + CO2 + NADH TCA cycle 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 867.608 C25 H40 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(=O)O)COP(=O)(O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O) LIGAND-CPD:C00091:*CAS:604-98-8 6.2.1.5 succinate + coenzyme A + ATP = succinyl-CoA + ADP reductive TCA cycle I 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 867.608 C25 H40 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(=O)O)COP(=O)(O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O) LIGAND-CPD:C00091:*CAS:604-98-8 6.2.1.5 succinate + coenzyme A + ATP = succinyl-CoA + ADP TCA cycle 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 867.608 C25 H40 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(=O)O)COP(=O)(O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O) LIGAND-CPD:C00091:*CAS:604-98-8 2.3.1.109 L-arginine + succinyl-CoA = N2-succinyl-L-arginine + coenzyme A arginine degradation II 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 867.608 C25 H40 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(=O)O)COP(=O)(O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O) LIGAND-CPD:C00091:*CAS:604-98-8 2.3.1.61 succinyl-CoA = coenzyme A 2-keto glutarate dehydrogenase complex 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 867.608 C25 H40 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(=O)O)COP(=O)(O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O) LIGAND-CPD:C00091:*CAS:604-98-8 2.3.1.46 homoserine + succinyl-CoA = O-succinyl-L-homoserine + coenzyme A methionine biosynthesis I 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 867.608 C25 H40 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(=O)O)COP(=O)(O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O) LIGAND-CPD:C00091:*CAS:604-98-8 1.2.7.3 α-ketoglutarate + coenzyme A = succinyl-CoA + CO2 reductive TCA cycle I 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 867.608 C25 H40 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(=O)O)COP(=O)(O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O) LIGAND-CPD:C00091:*CAS:604-98-8 2.3.1.117 H2O + tetrahydrodipicolinate + succinyl-CoA = N-succinyl-2-amino-6-ketopimelate + coenzyme A lysine biosynthesis I 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 194.187 C10 H10 O4 C(O)(=O)C=Cc1(cc(OC)c(O)cc1) CAS:1135-24-6*LIGAND-CPD:C01494: 2.1.1.68 caffeate + S-adenosyl-L-methionine = 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 194.187 C10 H10 O4 C(O)(=O)C=Cc1(cc(OC)c(O)cc1) CAS:1135-24-6*LIGAND-CPD:C01494: 2.1.1.68 caffeate + S-adenosyl-L-methionine = 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 194.187 C10 H10 O4 C(O)(=O)C=Cc1(cc(OC)c(O)cc1) CAS:1135-24-6*LIGAND-CPD:C01494: ferulate + NADPH + O2 = 5-hydroxy-ferulic-acid + 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 194.187 C10 H10 O4 C(O)(=O)C=Cc1(cc(OC)c(O)cc1) CAS:1135-24-6*LIGAND-CPD:C01494: 6.2.1.12 ferulate + coenzyme A + ATP = feruloyl-CoA + AMP + diphosphate suberin biosynthesis crocetin 328.407 C20 H24 O4 CC(C(O)=O)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C(O)=O 1.2.99.3 crocetin dialdehyde + H2O = crocetin crocetin biosynthesis hydroxy-β-cyclocitral 168.235 C10 H16 O2 CC1(C)(C(C=O)=C(C)CC(C1)O) 1.14.99.- zeaxanthin + O2 = crocetin dialdehyde + hydroxy-β-cyclocitral crocetin biosynthesis hydroxy-β-cyclocitral 168.235 C10 H16 O2 CC1(C)(C(C=O)=C(C)CC(C1)O) 2.4.1.- hydroxy-β-cyclocitral + UDP-D-glucose = picrocrocin + UDP crocetin biosynthesis 5-ketogluconate 5-k-gluconate*5-keto-D-gluconate*5-dehydro-D-gluconate*5-dehydrogluconate 194.141 C6 H10 O7 C(O)C(=O)C(O)C(O)C(O)C(O)=O LIGAND-CPD:C01062: 1.1.1.69 gluconate = 5-ketogluconate L-idonate degradation 5-ketogluconate 5-k-gluconate*5-keto-D-gluconate*5-dehydro-D-gluconate*5-dehydrogluconate 194.141 C6 H10 O7 C(O)C(=O)C(O)C(O)C(O)C(O)=O LIGAND-CPD:C01062: 1.1.1.264 L-idonate = 5-ketogluconate L-idonate degradation 3-methyl-4-trans-hydroxy-2-butenal 100.117 C5 H8 O2 C(=O)C=C(C)CO 1.5.99.12 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 C(=O)C=C(C)CO 1.5.99.12 trans-zeatin riboside + H2O + FAD = adenosine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation cohumulone 348.438 C20 H28 O5 CC(C)=CCC1(=C(O)C(O)(CC=C(C)C)C(=O)C(=C(O)1)C(=O)C(C)C) diprenylphlorisobutyrophenone + O2 = cohumulone + H2O cohumulone biosynthesis H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.15.1.1 O2- + H+ = H2O2 + O2 removal of superoxide radicals H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.1.3.15 glycolate + O2 = glyoxylate + H2O2 photorespiration H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.5.3.1 O2 + H2O + sarcosine = H2O2 + formaldehyde + glycine glycine betaine degradation H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.2.3.1 nicotine-Δ1'5'-iminium ion + O2 + H2O = cotinine + H2O2 nicotine degradation II H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.2.3.1 nicotine-Δ1'5'-iminium ion + O2 + H2O = cotinine + H2O2 nicotine degradation III H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.4.3.6 tryptamine + H2O + O2 = ammonia + indole acetaldehyde + H2O2 IAA biosynthesis I H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.11.1.7 betanidin + H2O2 = betanidin + betanidin quinone + H2O betanidin degradation H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.11.1.11 L-ascorbate + H2O2 = monodehydroascorbate + H2O ascorbate glutathione cycle H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.11.1.6 ethanol + H2O2 = H2O + acetaldehyde oxidative ethanol degradation III H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.7.3.3 urate + O2 = allantoin + CO2 + H2O2 purine degradation H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.2.3.14 abscisic aldehyde + H2O + O2 = (+)-abscisate + H2O2 abscisic acid biosynthesis H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.4.3.6 aminoacetone + H2O + O2 = ammonia + methylglyoxal + H2O2 threonine degradation III (to methylglyoxal) H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.4.3.6 1,3-diaminopropane + H2O + O2 = 3-aminopropionaldehyde + ammonia + H2O2 β-alanine biosynthesis I H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.11.1.9 H2O2 + glutathione = glutathione disulfide + H2O glutathione redox reactions I H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.4.3.5 O2 + H2O + pyridoxamine 5'-phosphate = ammonia + H2O2 + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.4.3.5 O2 + pyridoxine-5'-phosphate = H2O2 + pyridoxal 5'-phosphate pyridoxal 5'-phosphate biosynthesis H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.4.3.5 O2 + pyridoxine-5'-phosphate = H2O2 + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.3.3.1 O2 + dihydroorotate = H2O2 + orotate de novo biosynthesis of pyrimidine ribonucleotides H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.7.3.3 urate + O2 + H2O = 5-hydroxyisourate + H2O2 ureide biosynthesis H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.2.3.7 indole acetaldehyde + O2 + H2O = indole-3-acetate + H2O2 IAA biosynthesis I H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.4.3.- O2 + L-aspartate = H2O2 + iminoaspartate NAD biosynthesis I (from aspartate) H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.5.3.11 spermine + O2 + H2O = 1-(3-aminopropyl)-4-aminobutanal + 1,3-diaminopropane + H2O2 β-alanine biosynthesis I H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.11.1.6 H2O2 = H2O + O2 removal of superoxide radicals H2O2 hydroperoxide*perhydrol*hydrogen peroxide 34.015 H2 O2 OO LIGAND-CPD:C00027:*CAS:7722-84-1 1.3.3.6 O2 = H2O2 fatty acid β-oxidation II (plant, saturated) fructuronate D-fructuronate 194.141 C6 H10 O7 C(O)C1(O)(C(O)C(O)C(O1)C(O)=O) CAS:669-90-9:*LIGAND-CPD:C00905: 1.1.1.57 NAD+ + D-mannonate = NADH + fructuronate β-D-glucuronide degradation fructuronate D-fructuronate 194.141 C6 H10 O7 C(O)C1(O)(C(O)C(O)C(O1)C(O)=O) CAS:669-90-9:*LIGAND-CPD:C00905: 5.3.1.12 glucuronate = fructuronate β-D-glucuronide degradation bergapten 5-methoxypsoralen*O-methylbergaptol*5-methoxyfuranocoumarin 216.193 C12 H8 O4 c1(oc2(c(cc1)c(OC)c3(c(c2)occ3)))(=O) PUBCHEM:2355:*NCI:95437*CAS:484-20-8 2.1.1.69 bergaptol + S-adenosyl-L-methionine = bergapten + S-adenosyl-L-homocysteine linear furanocoumarin biosynthesis 3-methyl-2-butenal 3-methylbut-2-enal*3,3-dimethyl-acrylaldehyde*prenal 84.118 C5 H8 O1 C(=O)C=C(C)C LIGAND-CPD:C07330: 1.5.99.12 isopentenyladenine + FAD + H2O = 3-methyl-2-butenal + adenine + FADH2 cytokinins degradation 3-methyl-2-butenal 3-methylbut-2-enal*3,3-dimethyl-acrylaldehyde*prenal 84.118 C5 H8 O1 C(=O)C=C(C)C LIGAND-CPD:C07330: 1.5.99.12 isopentenyl adenosine + H2O + FAD = adenosine + 3-methyl-2-butenal + FADH2 cytokinins degradation kievitone 356.374 C20 H20 O6 C2(C(c1(c(O)cc(O)cc1))C(=O)c3(c(O2)c(CC=C(C)C)c(O)cc(O)3)) CAS:62682-11-5 dalbergioidin + dimethylallyl-PP = kievitone + diphosphate kievitone biosynthesis kievitone 356.374 C20 H20 O6 C2(C(c1(c(O)cc(O)cc1))C(=O)c3(c(O2)c(CC=C(C)C)c(O)cc(O)3)) CAS:62682-11-5 2,3-dehydrokievitone + NADPH = kievitone + NADP+ kievitone biosynthesis nicotinamide mononucleotide β-nicotinamide D-ribonucleotide*nicotinamide ribonucleotide*nicotinamide nucleotide*NMN*nicotinamide D-ribonucleotide 335.23 C11 H16 N2 O8 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH](O)1)[n+]2(cc(C(N)=O)ccc2)) LIGAND-CPD:C00455:*CAS:1094-61-7 3.2.2.14 nicotinamide mononucleotide + H2O = D-ribose-5-phosphate + nicotinamide NAD salvage pathway I nicotinamide mononucleotide β-nicotinamide D-ribonucleotide*nicotinamide ribonucleotide*nicotinamide nucleotide*NMN*nicotinamide D-ribonucleotide 335.23 C11 H16 N2 O8 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH](O)1)[n+]2(cc(C(N)=O)ccc2)) LIGAND-CPD:C00455:*CAS:1094-61-7 3.2.2.14 nicotinamide mononucleotide + H2O = D-ribose-5-phosphate + nicotinamide pyridine nucleotide cycling (plants) nicotinamide mononucleotide β-nicotinamide D-ribonucleotide*nicotinamide ribonucleotide*nicotinamide nucleotide*NMN*nicotinamide D-ribonucleotide 335.23 C11 H16 N2 O8 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH](O)1)[n+]2(cc(C(N)=O)ccc2)) LIGAND-CPD:C00455:*CAS:1094-61-7 2.7.1.22 nicotinamide riboside + ATP = nicotinamide mononucleotide + ADP NAD salvage pathway II nicotinamide mononucleotide β-nicotinamide D-ribonucleotide*nicotinamide ribonucleotide*nicotinamide nucleotide*NMN*nicotinamide D-ribonucleotide 335.23 C11 H16 N2 O8 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH](O)1)[n+]2(cc(C(N)=O)ccc2)) LIGAND-CPD:C00455:*CAS:1094-61-7 3.5.1.42 nicotinamide mononucleotide + H2O = ammonia + nicotinate nucleotide NAD salvage pathway I nicotinamide mononucleotide β-nicotinamide D-ribonucleotide*nicotinamide ribonucleotide*nicotinamide nucleotide*NMN*nicotinamide D-ribonucleotide 335.23 C11 H16 N2 O8 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH](O)1)[n+]2(cc(C(N)=O)ccc2)) LIGAND-CPD:C00455:*CAS:1094-61-7 3.1.3.5 nicotinamide mononucleotide + H2O = nicotinamide riboside NAD salvage pathway II nicotinamide mononucleotide β-nicotinamide D-ribonucleotide*nicotinamide ribonucleotide*nicotinamide nucleotide*NMN*nicotinamide D-ribonucleotide 335.23 C11 H16 N2 O8 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH](O)1)[n+]2(cc(C(N)=O)ccc2)) 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 335.23 C11 H16 N2 O8 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH](O)1)[n+]2(cc(C(N)=O)ccc2)) LIGAND-CPD:C00455:*CAS:1094-61-7 2.7.7.1 nicotinamide mononucleotide + ATP = NAD+ + diphosphate NAD salvage pathway II nicotinamide mononucleotide β-nicotinamide D-ribonucleotide*nicotinamide ribonucleotide*nicotinamide nucleotide*NMN*nicotinamide D-ribonucleotide 335.23 C11 H16 N2 O8 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH](O)1)[n+]2(cc(C(N)=O)ccc2)) LIGAND-CPD:C00455:*CAS:1094-61-7 3.6.1.22 H2O + NAD+ = nicotinamide mononucleotide + AMP NAD salvage pathway II nicotinamide mononucleotide β-nicotinamide D-ribonucleotide*nicotinamide ribonucleotide*nicotinamide nucleotide*NMN*nicotinamide D-ribonucleotide 335.23 C11 H16 N2 O8 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH](O)1)[n+]2(cc(C(N)=O)ccc2)) LIGAND-CPD:C00455:*CAS:1094-61-7 3.6.1.22 H2O + NAD+ = nicotinamide mononucleotide + AMP NAD salvage pathway I nicotinamide mononucleotide β-nicotinamide D-ribonucleotide*nicotinamide ribonucleotide*nicotinamide nucleotide*NMN*nicotinamide D-ribonucleotide 335.23 C11 H16 N2 O8 P1 C(OP(O)(O)=O)[CH]1(O[CH]([CH](O)[CH](O)1)[n+]2(cc(C(N)=O)ccc2)) LIGAND-CPD:C00455:*CAS:1094-61-7 3.6.1.22 H2O + NAD+ = nicotinamide mononucleotide + AMP pyridine nucleotide cycling (plants) 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 1.5.1.15 5,10-methylene-THF + NAD+ = NADH folate transformations 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 2.1.2.10 tetrahydrofolate = 5,10-methylene-THF + ammonia glycine cleavage complex 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 2.1.2.11 5,10-methylene-THF + 2-keto-isovalerate + H2O = tetrahydrofolate + 2-dehydropantoate pantothenate biosynthesis I 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 2.1.2.11 5,10-methylene-THF + 2-keto-isovalerate + H2O = tetrahydrofolate + 2-dehydropantoate pantothenate biosynthesis II 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH folate transformations 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH formylTHF biosynthesis II 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH formylTHF biosynthesis I 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH photorespiration 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate glycine biosynthesis I 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate folate polyglutamylation I 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate folate transformations 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate glycine betaine degradation 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate formylTHF biosynthesis II 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate formylTHF biosynthesis I 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate photorespiration 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 1.5.1.5 5,10-methylene-THF + NADP+ = NADPH folate transformations 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 1.5.1.5 5,10-methylene-THF + NADP+ = NADPH formylTHF biosynthesis II 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 1.5.1.5 5,10-methylene-THF + NADP+ = NADPH formylTHF biosynthesis I 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 1.5.7.1 5-methyl-THF = 5,10-methylene-THF folate transformations 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 1.5.1.20 5-methyl-THF = 5,10-methylene-THF + H+ folate transformations 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 1.5.1.20 5-methyl-THF = 5,10-methylene-THF + H+ formylTHF biosynthesis II 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 1.5.1.20 5-methyl-THF = 5,10-methylene-THF + H+ formylTHF biosynthesis I 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate salvage pathways of purine and pyrimidine nucleotides 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate de novo biosynthesis of pyrimidine deoxyribonucleotides 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate formylTHF biosynthesis II 5,10-methylene-THF 5,10-methylenetetrahydrofolate*N5,N10-methylenetetrahydrofolate 457.445 C20 H23 N7 O6 C(=O)(NC(C(O)=O)CCC(=O)O)c1(ccc(cc1)N2(CN4([CH](C2)[CH2]Nc3(nc(N)[nH]c(c34)=O)))) LIGAND-CPD:C00143: 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate formylTHF biosynthesis I 7,2'-dihydroxy-4'-methoxy-isoflavanol-quinonemethide-intermediate-2 289.307 C16 H17 O5 C2([CH](c1(c([OH])cc(OC)cc1))[CH]=C3(C(O2)=CC(=[OH])C=C3)) 7,2'-dihydroxy-4'-methoxy-isoflavanol-quinonemethide-intermediate-1 = 7,2'-dihydroxy-4'-methoxy-isoflavanol-quinonemethide-intermediate-2 medicarpin biosynthesis 7,2'-dihydroxy-4'-methoxy-isoflavanol-quinonemethide-intermediate-2 289.307 C16 H17 O5 C2([CH](c1(c([OH])cc(OC)cc1))[CH]=C3(C(O2)=CC(=[OH])C=C3)) 7,2'-dihydroxy-4'-methoxy-isoflavanol-quinonemethide-intermediate-2 = (-)-medicarpin + H2O medicarpin biosynthesis palmitoyl CoA Palmitoyl-CoA (n-C16:0CoA)*hexadecanoyl CoA*palmityl-CoA*palmitoyl coenzyme A*palmitoyl-CoA 1005.946 C37 H66 N7 O17 P3 S1 c1(c2(c(ncn1)n(cn2)C3(OC(C(C(O)3)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCCCC)))(N) LIGAND-CPD:C00154:*CAS:1763-10-6 2.3.1.50 L-serine + palmitoyl CoA = CO2 + 3-dehydrosphinganine + coenzyme A sphingolipid metabolism phenylpyruvate phenylpyruvate*phenylpyruvic acid*α-ketohydrocinnamic acid*3-phenyl-2-oxopropanoate*keto-phenylpyruvate 164.16 C9 H8 O3 C(=O)(O)C(=O)Cc1(ccccc1) LIGAND-CPD:C00166:*CAS:156-06-9 2.6.1.57 phenylpyruvate + L-glutamate = L-phenylalanine + α-ketoglutarate phenylalanine degradation III phenylpyruvate phenylpyruvate*phenylpyruvic acid*α-ketohydrocinnamic acid*3-phenyl-2-oxopropanoate*keto-phenylpyruvate 164.16 C9 H8 O3 C(=O)(O)C(=O)Cc1(ccccc1) LIGAND-CPD:C00166:*CAS:156-06-9 2.6.1.57 phenylpyruvate + L-glutamate = L-phenylalanine + α-ketoglutarate phenylalanine biosynthesis I phenylpyruvate phenylpyruvate*phenylpyruvic acid*α-ketohydrocinnamic acid*3-phenyl-2-oxopropanoate*keto-phenylpyruvate 164.16 C9 H8 O3 C(=O)(O)C(=O)Cc1(ccccc1) LIGAND-CPD:C00166:*CAS:156-06-9 4.2.1.51 prephenate = phenylpyruvate + H2O + CO2 phenylalanine biosynthesis I phenylpyruvate phenylpyruvate*phenylpyruvic acid*α-ketohydrocinnamic acid*3-phenyl-2-oxopropanoate*keto-phenylpyruvate 164.16 C9 H8 O3 C(=O)(O)C(=O)Cc1(ccccc1) LIGAND-CPD:C00166:*CAS:156-06-9 L-methionine + phenylpyruvate = 2-oxo-4-methylthiobutanoate + L-phenylalanine methionine degradation III phenylpyruvate phenylpyruvate*phenylpyruvic acid*α-ketohydrocinnamic acid*3-phenyl-2-oxopropanoate*keto-phenylpyruvate 164.16 C9 H8 O3 C(=O)(O)C(=O)Cc1(ccccc1) LIGAND-CPD:C00166:*CAS:156-06-9 4.1.1.43 phenylpyruvate = CO2 + phenylacetaldehyde phenylalanine degradation III phenylpyruvate phenylpyruvate*phenylpyruvic acid*α-ketohydrocinnamic acid*3-phenyl-2-oxopropanoate*keto-phenylpyruvate 164.16 C9 H8 O3 C(=O)(O)C(=O)Cc1(ccccc1) LIGAND-CPD:C00166:*CAS:156-06-9 2.6.1.58 pyruvate + L-phenylalanine = phenylpyruvate + L-alanine phenylalanine degradation III (-)-trans-Isopiperitenol 152.236 C10 H16 O1 C=C(C)C1(C(O)C=C(C)CC1) LIGAND-CPD:C01123: 1.1.1.223 NAD+ + (-)-trans-Isopiperitenol = NADH + (-)-isopiperitenone menthol biosynthesis 2-methyl-6-phytyl-1,4-benzoquinone 402.659 C27 H46 O2 CC(CCCC(C)CCCC(C)C)CCCC(C)=CCc1(c(O)c(C)cc(O)c1) 2-methyl-6-phytyl-1,4-benzoquinone = δ-tocopherol vitamin E biosynthesis 2-methyl-6-phytyl-1,4-benzoquinone 402.659 C27 H46 O2 CC(CCCC(C)CCCC(C)C)CCCC(C)=CCc1(c(O)c(C)cc(O)c1) 2.1.1.- 2-methyl-6-phytyl-1,4-benzoquinone + S-adenosyl-L-methionine = 2,3-dimethyl-6-phytyl-1,4-benzoquinone + S-adenosyl-L-homocysteine vitamin E biosynthesis 2-methyl-6-phytyl-1,4-benzoquinone 402.659 C27 H46 O2 CC(CCCC(C)CCCC(C)C)CCCC(C)=CCc1(c(O)c(C)cc(O)c1) homogentisate + phytyl-PP = 2-methyl-6-phytyl-1,4-benzoquinone + CO2 + diphosphate vitamin E biosynthesis caffeoyl-CoA 929.679 C30 H42 N7 O19 P3 S1 C(CC(=O)NCCSC(=O)C=Cc1(cc(O)c(O)cc1))NC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(=O)(O)O)n3(c4(c(nc3)c(N)ncn4))) 3.1.2.- caffeoylquinate + coenzyme A = caffeoyl-CoA + quinate phenylpropanoid biosynthesis caffeoyl-CoA 929.679 C30 H42 N7 O19 P3 S1 C(CC(=O)NCCSC(=O)C=Cc1(cc(O)c(O)cc1))NC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(=O)(O)O)n3(c4(c(nc3)c(N)ncn4))) 2.3.1.153 delphinidin-3,5-diglucoside + caffeoyl-CoA = delphinidin 3-O-glucosyl-5-O-caffeoylglucoside + coenzyme A gentiodelphin biosynthesis caffeoyl-CoA 929.679 C30 H42 N7 O19 P3 S1 C(CC(=O)NCCSC(=O)C=Cc1(cc(O)c(O)cc1))NC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(=O)(O)O)n3(c4(c(nc3)c(N)ncn4))) 6.2.1.12 caffeate + coenzyme A + ATP = caffeoyl-CoA + AMP + diphosphate suberin biosynthesis caffeoyl-CoA 929.679 C30 H42 N7 O19 P3 S1 C(CC(=O)NCCSC(=O)C=Cc1(cc(O)c(O)cc1))NC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(=O)(O)O)n3(c4(c(nc3)c(N)ncn4))) 2.3.1.- delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + caffeoyl-CoA = gentiodelphin + coenzyme A gentiodelphin biosynthesis caffeoyl-CoA 929.679 C30 H42 N7 O19 P3 S1 C(CC(=O)NCCSC(=O)C=Cc1(cc(O)c(O)cc1))NC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(=O)(O)O)n3(c4(c(nc3)c(N)ncn4))) 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 929.679 C30 H42 N7 O19 P3 S1 C(CC(=O)NCCSC(=O)C=Cc1(cc(O)c(O)cc1))NC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(=O)(O)O)n3(c4(c(nc3)c(N)ncn4))) 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + feruloyl-CoA suberin biosynthesis caffeoyl-CoA 929.679 C30 H42 N7 O19 P3 S1 C(CC(=O)NCCSC(=O)C=Cc1(cc(O)c(O)cc1))NC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(=O)(O)O)n3(c4(c(nc3)c(N)ncn4))) 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + feruloyl-CoA phenylpropanoid biosynthesis caffeoyl-CoA 929.679 C30 H42 N7 O19 P3 S1 C(CC(=O)NCCSC(=O)C=Cc1(cc(O)c(O)cc1))NC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(=O)(O)O)n3(c4(c(nc3)c(N)ncn4))) 3.1.2.- caffeoylshikimate + coenzyme A = caffeoyl-CoA + shikimate phenylpropanoid biosynthesis lactucaxanthin ε,ε-carotene-3,3'-diol 568.881 C40 H56 O2 CC(C=CC1(C(C)(C)CC(O)C=C1C))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)=CC(O)CC(C)2C) 1.14.99.- ε,ε-carotene-3-diol + O2 = lactucaxanthin + H2O lactucaxanthin biosynthesis AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ NAD salvage pathway I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ pyridine nucleotide cycling (plants) AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP oxidative ethanol degradation III AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP glutamate degradation VII (to butyrate) AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP oxidative ethanol degradation I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.4 L-leucine + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.9.2 H2O + pyruvate + ATP = phosphoenolpyruvate + AMP reductive TCA cycle I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.9.2 H2O + pyruvate + ATP = phosphoenolpyruvate + AMP gluconeogenesis AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.9.2 H2O + pyruvate + ATP = phosphoenolpyruvate + AMP glycolysis I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.2 ATP + L-tryptophan = AMP + diphosphate tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.6.3 6-hydroxymethyl-dihydropterin + ATP = 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + AMP tetrahydrofolate biosynthesis I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.6.3 6-hydroxymethyl-dihydropterin + ATP = 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + AMP tetrahydrofolate biosynthesis II AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.3 coenzyme A + ATP = diphosphate + AMP acyl-CoA synthetase pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.26 ATP + O-succinylbenzoate + coenzyme A = AMP + diphosphate + O-succinylbenzoyl-CoA menaquinone biosynthesis AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.6 L-lysine + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 ATP + L-serine + 2,3-dihydroxybenzoate = enterobactin + diphosphate + AMP enterobactin biosynthesis AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.5.1.27 dimethylallyl-PP + AMP = isopentenyladenosine-5'-monophosphate + diphosphate trans-zeatin biosynthesis AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 1.8.99.2 sulfite + AMP = adenosine 5'-phosphosulfate sulfite oxidation III AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.4.3 AMP + ATP = ADP salvage pathways of purine and pyrimidine nucleotides AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.4.3 AMP + ATP = ADP purine nucleotides de novo biosynthesis I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.11 L-serine + ATP = diphosphate + AMP selenocysteine biosynthesis AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 3.2.2.4 AMP + H2O = D-ribose-5-phosphate + adenine salvage pathways of adenine, hypoxanthine, and their nucleosides AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.21 L-histidine + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.9.3 H2O + selenide + ATP = selenophosphate + AMP selenocysteine biosynthesis AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.6.5 ATP + GDP = AMP + guanosine 5'-diphosphate,3'-diphosphate ppGpp biosynthesis AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.1.1 ammonia + L-aspartate + ATP = L-asparagine + diphosphate + AMP asparagine biosynthesis III AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of adenine, hypoxanthine, and their nucleosides AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of purine nucleosides AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of purine and pyrimidine nucleotides AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of purine nucleosides II (plant) AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.4.1 ammonia + xanthosine-5-phosphate + ATP = AMP + diphosphate + GMP salvage pathways of purine nucleosides II (plant) AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.4.1 ammonia + xanthosine-5-phosphate + ATP = AMP + diphosphate + GMP purine nucleotides de novo biosynthesis I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.15 L-proline + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.14 glycine + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.17 coenzyme A + propionate + ATP = propionyl-CoA + diphosphate + AMP β-alanine biosynthesis II AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.12 caffeate + coenzyme A + ATP = caffeoyl-CoA + AMP + diphosphate suberin biosynthesis AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.18 L-glutamine + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.12 L-aspartate + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.6.5 GTP + ATP = guanosine 3'-diphosphate 5'-triphosphate + AMP ppGpp biosynthesis AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.1 L-tyrosine + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 3.6.1.22 H2O + NAD+ = nicotinamide mononucleotide + AMP NAD salvage pathway II AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 3.6.1.22 H2O + NAD+ = nicotinamide mononucleotide + AMP NAD salvage pathway I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 3.6.1.22 H2O + NAD+ = nicotinamide mononucleotide + AMP pyridine nucleotide cycling (plants) AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.4.15 biotin + ATP = diphosphate + AMP biotin-carboxyl carrier protein AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.22 L-asparagine + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.1.20 adenosine + ATP = AMP + ADP salvage pathways of purine nucleosides II (plant) AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.2.1 β-alanine + L-pantoate + ATP = pantothenate + diphosphate + AMP pantothenate biosynthesis I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.2.1 β-alanine + L-pantoate + ATP = pantothenate + diphosphate + AMP pantothenate biosynthesis II AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.6.1 ATP + D-ribose-5-phosphate = 5-phosphoribosyl 1-pyrophosphate + AMP salvage pathways of purine and pyrimidine nucleotides AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 2.7.6.1 ATP + D-ribose-5-phosphate = 5-phosphoribosyl 1-pyrophosphate + AMP PRPP biosynthesis I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.12 coenzyme A + 4-coumarate + ATP = coumaroyl-CoA + diphosphate + AMP flavonoid biosynthesis AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.12 coenzyme A + 4-coumarate + ATP = coumaroyl-CoA + diphosphate + AMP phenylpropanoid biosynthesis AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.7 L-alanine + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.1.5 ammonia + ATP + deamido-NAD = AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.26 ATP + O-succinylbenzoate + coenzyme A = 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA + AMP + diphosphate phylloquinone biosynthesis AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.20 L-phenylalanine + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.4.5 O-ureidohomoserine + L-aspartate + ATP = canavaninosuccinate + AMP + diphosphate canavanine biosynthesis AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP urea cycle AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis II (acetyl cycle) AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP citrulline-nitric oxide cycle AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis IV AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 3.1.3.5 AMP + H2O = adenosine salvage pathways of purine nucleosides II (plant) AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.12 ferulate + coenzyme A + ATP = feruloyl-CoA + AMP + diphosphate suberin biosynthesis AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.10 L-methionine + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 3.5.4.6 AMP + H2O = inosine-5'-phosphate + ammonia purine degradation AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 3.5.4.6 AMP + H2O = inosine-5'-phosphate + ammonia salvage pathways of purine nucleosides II (plant) AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.16 L-cysteine + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.17 L-glutamate + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.17 L-glutamate + ATP = diphosphate + AMP tetrapyrrole biosynthesis I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.11 L-serine + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 1.8.4.9 sulfite + AMP + glutathione disulfide = adenosine 5'-phosphosulfate + glutathione sulfate reduction II (assimilatory) AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 4.3.2.2 adenylo-succinate = fumarate + AMP salvage pathways of purine nucleosides AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 4.3.2.2 adenylo-succinate = fumarate + AMP purine nucleotides de novo biosynthesis II AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 4.3.2.2 adenylo-succinate = fumarate + AMP purine nucleotides de novo biosynthesis I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.19 L-arginine + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid β-oxidation I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid β-oxidation II (plant, saturated) AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.9 L-valine + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.3 L-threonine + ATP = diphosphate + AMP tRNA charging pathway AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis II AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis III AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis I AMP A*adenosine-5'-phosphate*adenosine-phosphate*5'-AMP*adenosine-monophosphate*adenylic acid*AMP*adenosine 5'-monophosphate*adenylate*5'-adenylic acid*5'-adenosine monophosphate*adenosine 5'-phosphate 347.224 C10 H14 N5 O7 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00020:*CAS:61-19-8*NCI:20264 6.1.1.5 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 CC(C)C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC3)CC(=O)CC4)(C)))) (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 CC(C)C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC3)CC(=O)CC4)(C)))) 1.3.99.- 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 CC(C)C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC3)CC(=O)CC4)(C)))) 1.14.13.- (5α)-campestan-3-one + O2 + NADPH = (22α)-hydroxy-5α-campestan-3-one + H2O + NADP+ brassinosteroid biosynthesis II ADP-ribose ADP-D-ribose*adenosine diphosphate ribose 559.319 C15 H23 N5 O14 P2 C(OP(O)(=O)OP(=O)(O)OC1(OC(CO)C(O)C(O)1))C2(OC(C(O)C(O)2)n3(c4(c(nc3)c(N)ncn4))) LIGAND-CPD:C00301:*CAS:20762-30-5 3.2.2.5 H2O + NAD+ = ADP-ribose + nicotinamide NAD salvage pathway I α-aminoadipate 2-aminoadipic acid*hexanedioic acid, 2-amino-*2-aminoadipate*L-α-aminoadipate*L-α-aminoadipic acid*L-2-aminoadipic acid*L-2-aminoadipate 161.157 C6 H11 N1 O4 C(O)(=O)C(N)CCCC(=O)O CAS:542-32-5 2.6.1.39 α-ketoglutarate + α-aminoadipate = L-glutamate + α-ketoadipate lysine biosynthesis IV α-aminoadipate 2-aminoadipic acid*hexanedioic acid, 2-amino-*2-aminoadipate*L-α-aminoadipate*L-α-aminoadipic acid*L-2-aminoadipic acid*L-2-aminoadipate 161.157 C6 H11 N1 O4 C(O)(=O)C(N)CCCC(=O)O CAS:542-32-5 2.6.1.39 α-ketoglutarate + α-aminoadipate = L-glutamate + α-ketoadipate lysine degradation II α-aminoadipate 2-aminoadipic acid*hexanedioic acid, 2-amino-*2-aminoadipate*L-α-aminoadipate*L-α-aminoadipic acid*L-2-aminoadipic acid*L-2-aminoadipate 161.157 C6 H11 N1 O4 C(O)(=O)C(N)CCCC(=O)O CAS:542-32-5 1.2.1.31 2-aminoadipate-6-semialdehyde + H2O = α-aminoadipate + H+ lysine biosynthesis IV α-aminoadipate 2-aminoadipic acid*hexanedioic acid, 2-amino-*2-aminoadipate*L-α-aminoadipate*L-α-aminoadipic acid*L-2-aminoadipic acid*L-2-aminoadipate 161.157 C6 H11 N1 O4 C(O)(=O)C(N)CCCC(=O)O CAS:542-32-5 1.2.1.31 2-aminoadipate-6-semialdehyde + H2O + NAD+ = α-aminoadipate + NADH lysine degradation II cardiolipin diphosphatidylglycerol C13 H20 O17 R4 P2 LIGAND-CPD:C05980: 2.7.8.- phospholipid biosynthesis I cardiolipin diphosphatidylglycerol C13 H20 O17 R4 P2 LIGAND-CPD:C05980: cardiolipin biosynthesis 2-phosphoglycolate 2-P-glycolate*phosphoglycolate*Phosphoglycolic acid 156.032 C2 H5 O6 P1 C(C(=O)O)OP(=O)(O)O LIGAND-CPD:C00988: 4.1.1.- O2 = 2-phosphoglycolate + 3-phosphoglycerate + H+ photorespiration 2-phosphoglycolate 2-P-glycolate*phosphoglycolate*Phosphoglycolic acid 156.032 C2 H5 O6 P1 C(C(=O)O)OP(=O)(O)O LIGAND-CPD:C00988: 3.1.3.18 H2O + 2-phosphoglycolate = glycolate photorespiration S-lactoyl-glutathione S-D-lactoylglutathione*D-lactoylglutathione*(R)-S-lactoylglutathione 379.384 C13 H21 N3 O8 S1 C(O)(=O)C(N)CCC(=O)NC(CSC(=O)C(C)O)C(=O)NCC(=O)O CAS:59-85-8:*LIGAND-CPD:C03451:*CAS:25138-66-3 4.4.1.5 S-lactoyl-glutathione = methylglyoxal + glutathione methylglyoxal degradation I S-lactoyl-glutathione S-D-lactoylglutathione*D-lactoylglutathione*(R)-S-lactoylglutathione 379.384 C13 H21 N3 O8 S1 C(O)(=O)C(N)CCC(=O)NC(CSC(=O)C(C)O)C(=O)NCC(=O)O CAS:59-85-8:*LIGAND-CPD:C03451:*CAS:25138-66-3 3.1.2.6 S-lactoyl-glutathione + H2O = glutathione + D-lactate methylglyoxal degradation I UDP-D-glucuronate udp-glcua*UDP-glucuronate*uridine diphosphate glucuronate*uridine diphosphate glucuronic acid 580.289 C15 H22 N2 O18 P2 C1(C(O)C(O)C(O)C(O1)C(=O)O)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00167:*CAS:2616-64-0 2.7.7.44 α-D-glucuronate 1-phosphate + UTP = UDP-D-glucuronate + diphosphate UDP-D-glucuronate biosynthesis (from myo-inositol) UDP-D-glucuronate udp-glcua*UDP-glucuronate*uridine diphosphate glucuronate*uridine diphosphate glucuronic acid 580.289 C15 H22 N2 O18 P2 C1(C(O)C(O)C(O)C(O1)C(=O)O)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00167:*CAS:2616-64-0 2.4.1.17 nicotine + UDP-D-glucuronate = nicotine-Glucuronide + UDP nicotine degradation II UDP-D-glucuronate udp-glcua*UDP-glucuronate*uridine diphosphate glucuronate*uridine diphosphate glucuronic acid 580.289 C15 H22 N2 O18 P2 C1(C(O)C(O)C(O)C(O1)C(=O)O)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00167:*CAS:2616-64-0 2.4.1.17 cotinine + UDP-D-glucuronate = cotinine-glucuronide + UDP nicotine degradation III UDP-D-glucuronate udp-glcua*UDP-glucuronate*uridine diphosphate glucuronate*uridine diphosphate glucuronic acid 580.289 C15 H22 N2 O18 P2 C1(C(O)C(O)C(O)C(O1)C(=O)O)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) 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-glcua*UDP-glucuronate*uridine diphosphate glucuronate*uridine diphosphate glucuronic acid 580.289 C15 H22 N2 O18 P2 C1(C(O)C(O)C(O)C(O1)C(=O)O)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00167:*CAS:2616-64-0 1.1.1.22 UDP-D-glucose + H2O + NAD+ = UDP-D-glucuronate + NADH UDP-D-xylose biosynthesis UDP-D-glucuronate udp-glcua*UDP-glucuronate*uridine diphosphate glucuronate*uridine diphosphate glucuronic acid 580.289 C15 H22 N2 O18 P2 C1(C(O)C(O)C(O)C(O1)C(=O)O)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00167:*CAS:2616-64-0 1.1.1.22 UDP-D-glucose + H2O + NAD+ = UDP-D-glucuronate + NADH galactose degradation II UDP-D-glucuronate udp-glcua*UDP-glucuronate*uridine diphosphate glucuronate*uridine diphosphate glucuronic acid 580.289 C15 H22 N2 O18 P2 C1(C(O)C(O)C(O)C(O1)C(=O)O)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00167:*CAS:2616-64-0 4.1.1.35 UDP-D-glucuronate = UDP-D-xylose + CO2 UDP-D-xylose biosynthesis UDP-D-glucuronate udp-glcua*UDP-glucuronate*uridine diphosphate glucuronate*uridine diphosphate glucuronic acid 580.289 C15 H22 N2 O18 P2 C1(C(O)C(O)C(O)C(O1)C(=O)O)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00167:*CAS:2616-64-0 2.4.1.17 trans-3'-hydroxycotinine + UDP-D-glucuronate = trans-3-hydroxycotinine-glucuronide + UDP nicotine degradation III 1,1-kestotetraose nystose 666.583 C24 H42 O21 C(O)C1(OC(C(O)C(O)C(O)1)OC2(OC(CO)C(O)C(O)2)COC3(OC(CO)C(O)C(O)3)COC4(CO)(OC(CO)C(O)C(O)4)) 2.4.1.100 1-kestotriose + 1-kestotriose = 1,1-kestotetraose + sucrose fructan biosynthesis 18:2-18:2-DGDG 1-18:2-2-18:2-digalactosyldiacylglycerol*1,2-(9Z,12Z-octadecadienoyl)-3-O-[alpha-D-galactosyl-(1>6)-O-beta-D-galactosyl]-sn-glycerol 941.247 C51 H88 O15 C(OC1(OC(C(O)C(O)C1O)COC2(C(O)C(O)C(O)C(O2)CO)))C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-18:2-DGDG = 18:3-18:2-DGDG glycolipid desaturation 18:2-18:2-DGDG 1-18:2-2-18:2-digalactosyldiacylglycerol*1,2-(9Z,12Z-octadecadienoyl)-3-O-[alpha-D-galactosyl-(1>6)-O-beta-D-galactosyl]-sn-glycerol 941.247 C51 H88 O15 C(OC1(OC(C(O)C(O)C1O)COC2(C(O)C(O)C(O)C(O2)CO)))C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-18:2-DGDG = 18:2-18:3-DGDG glycolipid desaturation L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 6.1.1.11 L-serine + ATP = diphosphate + AMP tRNA charging pathway L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.3.1.50 L-serine + palmitoyl CoA = CO2 + 3-dehydrosphinganine + coenzyme A sphingolipid metabolism L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.7.8.8 L-serine = CMP phospholipid biosynthesis I L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.7.8.8 L-serine = CMP phospholipid biosynthesis II L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 L-serine + α-ketoglutarate = L-glutamate + hydroxypyruvate photorespiration L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 ATP + L-serine + 2,3-dihydroxybenzoate = enterobactin + diphosphate + AMP enterobactin biosynthesis L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 4.2.1.22 L-homocysteine + L-serine = H2O + cystathionine homocysteine degradation L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 4.2.1.22 L-homocysteine + L-serine = H2O + cystathionine homocysteine and cysteine interconversion L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.7.8.- L-serine = ethanolamine phospholipid biosynthesis II L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate glycine biosynthesis I L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate folate polyglutamylation I L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate folate transformations L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate glycine betaine degradation L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate formylTHF biosynthesis II L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate formylTHF biosynthesis I L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate photorespiration L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO 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(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 6.1.1.11 L-serine + ATP = diphosphate + AMP selenocysteine biosynthesis L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 4.1.1.- L-serine = ethanolamine + CO2 choline biosynthesis I L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 4.2.1.20 indole + L-serine = L-tryptophan + H2O tryptophan biosynthesis L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 4.3.1.17 L-serine = pyruvate + ammonia glycine betaine degradation L-serine S*serine*ser*L-ser 105.093 C3 H7 N1 O3 C(=O)(O)C(N)CO LIGAND:C00065:*LIGAND-CPD:C00065:*CAS:56-45-1 3.1.3.3 3-phospho-serine + H2O = L-serine serine biosynthesis 3-sulfinyl-pyruvate 3-sulphinyl-pyruvate*β-sulfinylpyruvate 152.122 C3 H4 O5 S1 C(S(=O)O)C(=O)C(O)=O 3-sulfinyl-pyruvate + H2O = sulfite + pyruvate L-cysteine degradation I 3-sulfinyl-pyruvate 3-sulphinyl-pyruvate*β-sulfinylpyruvate 152.122 C3 H4 O5 S1 C(S(=O)O)C(=O)C(O)=O 2.6.1.1 3-sulfinoalanine + α-ketoglutarate = L-glutamate + 3-sulfinyl-pyruvate L-cysteine degradation I 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 301.189 C8 H16 N1 O9 P1 CC(=O)NC1(C(O)C(O)C(OC1O)COP(O)(O)=O) LIGAND-CPD:C00357:*CAS:102029-88-9 5.4.2.3 N-acetyl-glucosamine-1-phosphate = N-acetyl-D-glucosamine-6-phosphate UDP-N-acetylgalactosamine 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 301.189 C8 H16 N1 O9 P1 CC(=O)NC1(C(O)C(O)C(OC1O)COP(O)(O)=O) LIGAND-CPD:C00357:*CAS:102029-88-9 2.3.1.4 D-glucosamine-6-phosphate + acetyl-CoA = N-acetyl-D-glucosamine-6-phosphate + coenzyme A UDP-N-acetylgalactosamine biosynthesis nicotine-Δ1'5'-iminium ion nicotine imine*(S)-1-(methylene-11C)-2-(3-pyridinyl)pyrrolidinium*11C-nicotine imine*nicotine iminium*pyrrolidium, 1-(methylene-11C)-2-(3-pyridinyl)-, (S)- 161.226 C10 H13 N2 C1(=[N+](C)[CH](CC1)c2(cnccc2)) 1.14.14.1 nicotine + NADPH = nicotine-Δ1'5'-iminium ion + NADP+ nicotine degradation II nicotine-Δ1'5'-iminium ion nicotine imine*(S)-1-(methylene-11C)-2-(3-pyridinyl)pyrrolidinium*11C-nicotine imine*nicotine iminium*pyrrolidium, 1-(methylene-11C)-2-(3-pyridinyl)-, (S)- 161.226 C10 H13 N2 C1(=[N+](C)[CH](CC1)c2(cnccc2)) 1.14.14.1 nicotine + NADPH = nicotine-Δ1'5'-iminium ion + NADP+ nicotine degradation III nicotine-Δ1'5'-iminium ion nicotine imine*(S)-1-(methylene-11C)-2-(3-pyridinyl)pyrrolidinium*11C-nicotine imine*nicotine iminium*pyrrolidium, 1-(methylene-11C)-2-(3-pyridinyl)-, (S)- 161.226 C10 H13 N2 C1(=[N+](C)[CH](CC1)c2(cnccc2)) 1.2.3.1 nicotine-Δ1'5'-iminium ion + O2 + H2O = cotinine + H2O2 nicotine degradation II nicotine-Δ1'5'-iminium ion nicotine imine*(S)-1-(methylene-11C)-2-(3-pyridinyl)pyrrolidinium*11C-nicotine imine*nicotine iminium*pyrrolidium, 1-(methylene-11C)-2-(3-pyridinyl)-, (S)- 161.226 C10 H13 N2 C1(=[N+](C)[CH](CC1)c2(cnccc2)) 1.2.3.1 nicotine-Δ1'5'-iminium ion + O2 + H2O = cotinine + H2O2 nicotine degradation III caffeoylshikimate 336.298 C16 H16 O8 C(=O)(O)C1(CC(C(O)C(C=1)O)OC(=O)C=CC2(C=C(O)C(O)=CC=2)) 1.14.13.36 4-coumaroylshikimate + NADPH + O2 = caffeoylshikimate + NADP+ + H2O phenylpropanoid biosynthesis caffeoylshikimate 336.298 C16 H16 O8 C(=O)(O)C1(CC(C(O)C(C=1)O)OC(=O)C=CC2(C=C(O)C(O)=CC=2)) 3.1.2.- caffeoylshikimate + coenzyme A = caffeoyl-CoA + shikimate phenylpropanoid biosynthesis isopentenyladenine-9-N-glucoside 365.388 C16 H23 N5 O5 c1(c2(c(ncn1)N(C=N2)C3(OC(CO)C(O)C(O)C(O)3)))(NCC=C(C)C) 2.4.1.- isopentenyladenine + UDP-D-glucose = isopentenyladenine-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis 4,4-dimethyl-5-α-cholesta-8,14-dien-3-β-ol 412.698 C29 H48 O1 CC(C)CCCC(C)C1(C2(C(=CC1)C3(=C(CC2)C4(C(CC3)C(C)(C)C(O)CC4)(C)))(C)) 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol + O2 + NADPH = 4,4-dimethyl-5-α-cholesta-8,14-dien-3-β-ol + formate + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 4,4-dimethyl-5-α-cholesta-8,14-dien-3-β-ol 412.698 C29 H48 O1 CC(C)CCCC(C)C1(C2(C(=CC1)C3(=C(CC2)C4(C(CC3)C(C)(C)C(O)CC4)(C)))(C)) 1.3.1.70 4,4-dimethyl-5-α-cholesta-8,14-dien-3-β-ol + NADPH = 4,4-dimethyl-5α-cholesta-8-en-3-β-ol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 3.2.2.14 nicotinamide mononucleotide + H2O = D-ribose-5-phosphate + nicotinamide NAD salvage pathway I 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 3.2.2.14 nicotinamide mononucleotide + H2O = D-ribose-5-phosphate + nicotinamide pyridine nucleotide cycling (plants) 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 2.7.1.15 D-ribose + ATP = D-ribose-5-phosphate + ADP ribose degradation 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 2.7.6.1 ATP + D-ribose-5-phosphate = 5-phosphoribosyl 1-pyrophosphate + AMP salvage pathways of purine and pyrimidine nucleotides 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 2.7.6.1 ATP + D-ribose-5-phosphate = 5-phosphoribosyl 1-pyrophosphate + AMP PRPP biosynthesis I 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: trans-zeatin riboside monophosphate = trans-zeatin + D-ribose-5-phosphate trans-zeatin biosynthesis 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 5.4.2.7 ribose-1-phosphate = D-ribose-5-phosphate (deoxy)ribose phosphate degradation 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate pentose phosphate pathway (partial) 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate Calvin cycle 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate pentose phosphate pathway (non-oxidative branch) 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate (deoxy)ribose phosphate degradation 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate glucose fermentation to lactate II 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: isopentenyladenosine-5'-monophosphate + H2O = isopentenyladenine + D-ribose-5-phosphate trans-zeatin biosynthesis 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 3.2.2.4 AMP + H2O = D-ribose-5-phosphate + adenine salvage pathways of adenine, hypoxanthine, and their nucleosides 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 3.2.2.- nicotinate nucleotide + H2O = nicotinate + D-ribose-5-phosphate pyridine nucleotide cycling (plants) 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 5.3.1.6 D-ribose-5-phosphate = D-ribulose-5-phosphate Calvin cycle 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 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*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-phosphoric acid*ribose-5-phosphoric acid*ribose-5P*D-ribose-5-P*ribose-5-P*ribose-5-phosphate*α-D-ribose-5-phosphate 230.111 C5 H11 O8 P1 C(OP(=O)(O)O)C(O)C(O)C(O)C=O CAS:3615-55-2*PUBCHEM:77982:*PUBCHEM:439167:*LIGAND-CPD:C00117:*CAS:4300-28-1: 5.3.1.6 D-ribose-5-phosphate = D-ribulose-5-phosphate glucose fermentation to lactate II dihydroneopterin phosphate Dihydroneopterin monophosphate*dihydroneopterin-p*2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphate 335.213 C9 H14 N5 O7 P1 C2(C(C(O)C(O)COP(O)(O)=O)=Nc1(c(=O)[nH]c(N)nc1N2)) LIGAND-CPD:C05925: 3.6.1.- dihydroneopterin phosphate + H2O = dihydro-neo-pterin tetrahydrofolate biosynthesis I dihydroneopterin phosphate Dihydroneopterin monophosphate*dihydroneopterin-p*2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphate 335.213 C9 H14 N5 O7 P1 C2(C(C(O)C(O)COP(O)(O)=O)=Nc1(c(=O)[nH]c(N)nc1N2)) LIGAND-CPD:C05925: 3.6.1.- dihydroneopterin phosphate + H2O = dihydro-neo-pterin tetrahydrofolate biosynthesis II dihydroneopterin phosphate Dihydroneopterin monophosphate*dihydroneopterin-p*2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphate 335.213 C9 H14 N5 O7 P1 C2(C(C(O)C(O)COP(O)(O)=O)=Nc1(c(=O)[nH]c(N)nc1N2)) LIGAND-CPD:C05925: 3.6.1.- 7,8-dihydroneopterin 3'-triphosphate + H2O = dihydroneopterin phosphate + diphosphate tetrahydrofolate biosynthesis I dihydroneopterin phosphate Dihydroneopterin monophosphate*dihydroneopterin-p*2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphate 335.213 C9 H14 N5 O7 P1 C2(C(C(O)C(O)COP(O)(O)=O)=Nc1(c(=O)[nH]c(N)nc1N2)) LIGAND-CPD:C05925: 3.6.1.- 7,8-dihydroneopterin 3'-triphosphate + H2O = dihydroneopterin phosphate + diphosphate tetrahydrofolate biosynthesis II 2-methylacetoacetyl-CoA 2-methyl-3-acetoacetyl-CoA*2-methylacetoacetyl coenzyme A 865.635 C26 H42 N7 O18 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)C(C)=O) CAS:6712-01-2 2.3.1.9 2-methylacetoacetyl-CoA + coenzyme A = propionyl-CoA + acetyl-CoA isoleucine degradation I 2-methylacetoacetyl-CoA 2-methyl-3-acetoacetyl-CoA*2-methylacetoacetyl coenzyme A 865.635 C26 H42 N7 O18 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)C(C)=O) CAS:6712-01-2 1.1.1.178 NAD+ + 2-methyl-3-hydroxybutyryl-CoA = NADH + 2-methylacetoacetyl-CoA isoleucine degradation I L-fucose fucose*6-deoxy-L-galactose*L-galactomethylose 164.158 C6 H12 O5 C1(C(O)C(O)C(O)C(C)O1)(O) CAS:2438-80-4:*LIGAND-CPD:C01019: 5.3.1.25 L-fucose = L-fuculose fucose degradation ent-sandaracopimaradiene-3α-ol hydroxy-sandaracopimaradiene*ent-sandaracopimaradiene-3alpha-ol 288.472 C20 H32 O1 C=CC2(C)(CCC3(C1(C)([CH](C(C)(C)C(O)CC1)CCC(=C2)3))) ent-sandaracopimaradiene-3α-ol = oryzalexin E oryzalexin A-F biosynthesis ent-sandaracopimaradiene-3α-ol hydroxy-sandaracopimaradiene*ent-sandaracopimaradiene-3alpha-ol 288.472 C20 H32 O1 C=CC2(C)(CCC3(C1(C)([CH](C(C)(C)C(O)CC1)CCC(=C2)3))) ent-sandaracopimaradiene = ent-sandaracopimaradiene-3α-ol oryzalexin A-F biosynthesis ent-sandaracopimaradiene-3α-ol hydroxy-sandaracopimaradiene*ent-sandaracopimaradiene-3alpha-ol 288.472 C20 H32 O1 C=CC2(C)(CCC3(C1(C)([CH](C(C)(C)C(O)CC1)CCC(=C2)3))) ent-sandaracopimaradiene-3α-ol = oryzalexin D oryzalexin A-F biosynthesis ent-sandaracopimaradiene-3α-ol hydroxy-sandaracopimaradiene*ent-sandaracopimaradiene-3alpha-ol 288.472 C20 H32 O1 C=CC2(C)(CCC3(C1(C)([CH](C(C)(C)C(O)CC1)CCC(=C2)3))) ent-sandaracopimaradiene-3α-ol = oryzalexin F oryzalexin A-F biosynthesis thiocyanate thiocyanic acid*thiocyanate*hydrogen thiocyanate 59.086 C1 H1 N1 S1 C([SH])#N CAS:463-56-9:*LIGAND-CPD:C01755: 2.8.1.2 hydrogen cyanide + 3-mercaptopyruvate = pyruvate + thiocyanate L-cysteine degradation III thiocyanate thiocyanic acid*thiocyanate*hydrogen thiocyanate 59.086 C1 H1 N1 S1 C([SH])#N CAS:463-56-9:*LIGAND-CPD:C01755: 2.8.1.1 thiosulfate + hydrogen cyanide = sulfite + thiocyanate thiosulfate disproportionation III (rhodanese) 18:1-t16:1-PG 1-18:1-2-trans-16:1-phosphatidylglycerol*1-(9Z-octadecenoyl)-2-(3E-hexadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) 747. C40 H75 O10 P1 C(OP(=O)(O)OCC(O)CO)C(OC(=O)CC=CCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC 1.14.99.- 18:1-16:0-PG = 18:1-t16:1-PG phospholipid desaturation 18:1-t16:1-PG 1-18:1-2-trans-16:1-phosphatidylglycerol*1-(9Z-octadecenoyl)-2-(3E-hexadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) 747. C40 H75 O10 P1 C(OP(=O)(O)OCC(O)CO)C(OC(=O)CC=CCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC 1.14.99.- 18:1-t16:1-PG = 18:2-t16:1-PG phospholipid desaturation 5-phospho-β-D-ribosyl-amine 5-phospho-β-D-ribosyl-amine*5-P-β-D-ribosyl-amine*PRA*5-phosphoribosylamine 229.126 C5 H12 N1 O7 P1 C(OP(O)(=O)O)[CH]1([CH](O)[CH](O)[CH](O1)N) LIGAND-CPD:C03090: 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = ADP + 5-phospho-ribosyl-glycineamide purine nucleotides de novo biosynthesis II 5-phospho-β-D-ribosyl-amine 5-phospho-β-D-ribosyl-amine*5-P-β-D-ribosyl-amine*PRA*5-phosphoribosylamine 229.126 C5 H12 N1 O7 P1 C(OP(O)(=O)O)[CH]1([CH](O)[CH](O)[CH](O1)N) LIGAND-CPD:C03090: 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = ADP + 5-phospho-ribosyl-glycineamide purine nucleotides de novo biosynthesis I 5-phospho-β-D-ribosyl-amine 5-phospho-β-D-ribosyl-amine*5-P-β-D-ribosyl-amine*PRA*5-phosphoribosylamine 229.126 C5 H12 N1 O7 P1 C(OP(O)(=O)O)[CH]1([CH](O)[CH](O)[CH](O1)N) LIGAND-CPD:C03090: 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phosphoribosyl 1-pyrophosphate + L-glutamine + H2O purine nucleotides de novo biosynthesis II 5-phospho-β-D-ribosyl-amine 5-phospho-β-D-ribosyl-amine*5-P-β-D-ribosyl-amine*PRA*5-phosphoribosylamine 229.126 C5 H12 N1 O7 P1 C(OP(O)(=O)O)[CH]1([CH](O)[CH](O)[CH](O1)N) LIGAND-CPD:C03090: 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phosphoribosyl 1-pyrophosphate + L-glutamine + H2O purine nucleotides de novo biosynthesis I stachyose (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 C(O)C1(OC(CO)(C(O)C1O)OC2(OC(C(O)C(O)C2O)COC3(OC(C(O)C(O)C3O)COC4(C(O)C(O)C(O)C(O4)CO)))) CAS:10094-58-3 2.4.1.67 galactinol + raffinose = myo-inositol + stachyose stachyose biosynthesis 18:1-16:0-MGDG 1-18:1-2-16:0-monogalactosyldiacylglycerol*1-(9Z-octadecenoyl)-2-hexadecanoyl-3-O-beta-D-galactosyl-sn-glycerol 757.099 C43 H80 O10 C1(OC(CO)C(O)C(O)C(O)1)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC 1.14.99.- 18:1-16:0-MGDG = 18:2-16:0-MGDG glycolipid desaturation 18:1-16:0-MGDG 1-18:1-2-16:0-monogalactosyldiacylglycerol*1-(9Z-octadecenoyl)-2-hexadecanoyl-3-O-beta-D-galactosyl-sn-glycerol 757.099 C43 H80 O10 C1(OC(CO)C(O)C(O)C(O)1)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC 1.14.99.- 18:1-16:0-MGDG = 18:1-16:1-MGDG glycolipid desaturation oryzalexin C 3,7-Dioxo-sandaracopimaradien*3,7-Dioxo-sandaracopimaradiene 300.44 C20 H28 O2 C=CC2(C)(CCC3(C1(C)(C(C(C)(C)C(=O)CC1)CC(=O)C(=C2)3))) oryzalexin B = oryzalexin C oryzalexin A-F biosynthesis oryzalexin C 3,7-Dioxo-sandaracopimaradien*3,7-Dioxo-sandaracopimaradiene 300.44 C20 H28 O2 C=CC2(C)(CCC3(C1(C)(C(C(C)(C)C(=O)CC1)CC(=O)C(=C2)3))) oryzalexin A = oryzalexin C oryzalexin A-F biosynthesis 7,2'-dihydroxy-4'-methoxy-isoflavanol carbocation intermediate 2 291.323 C16 H19 O5 C2([CH](c1(c([OH])cc(OC)cc1))[CH+]c3(c(O2)cc(O)cc3)) 7,2'-dihydroxy-4'-methoxy-isoflavanol carbocation intermediate 2 = (-)-medicarpin + H2O medicarpin biosynthesis 7,2'-dihydroxy-4'-methoxy-isoflavanol carbocation intermediate 2 291.323 C16 H19 O5 C2([CH](c1(c([OH])cc(OC)cc1))[CH+]c3(c(O2)cc(O)cc3)) 7,2'-dihydroxy-4'-methoxy-isoflavanol carbocation intermediate 1 = 7,2'-dihydroxy-4'-methoxy-isoflavanol carbocation intermediate 2 medicarpin biosynthesis 18:2-16:0-DGDG 1-18:2-2-16:0-digalactosyldiacylglycerol 917.225 C49 H88 O15 C(OC1(OC(C(O)C(O)C1O)COC2(C(O)C(O)C(O)C(O2)CO)))C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:1-16:0-DGDG = 18:2-16:0-DGDG glycolipid desaturation 18:2-16:0-DGDG 1-18:2-2-16:0-digalactosyldiacylglycerol 917.225 C49 H88 O15 C(OC1(OC(C(O)C(O)C1O)COC2(C(O)C(O)C(O)C(O2)CO)))C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-16:0-DGDG = 18:3-16:0-DGDG glycolipid desaturation GA110 gibberellin A110*gibberellin A110*GA110 348.438 C20 H28 O5 CC1([CH]4(C(CC(O)C1)(C)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA12 + α-ketoglutarate + O2 = GA110 + succinate + CO2 gibberellin inactivation 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 5-phosphoribosyl 1-pyrophosphate + hypoxanthine = inosine-5'-phosphate + diphosphate salvage pathways of adenine, hypoxanthine, and their nucleosides 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH purine degradation 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH salvage pathways of purine nucleosides 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH ureide biosynthesis 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH salvage pathways of purine nucleosides II (plant) 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH purine nucleotides de novo biosynthesis II 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH purine nucleotides de novo biosynthesis I 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 2.4.2.8 diphosphate + inosine-5'-phosphate = 5-phosphoribosyl 1-pyrophosphate + hypoxanthine salvage pathways of purine nucleosides 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 2.4.2.8 diphosphate + inosine-5'-phosphate = 5-phosphoribosyl 1-pyrophosphate + hypoxanthine salvage pathways of purine nucleosides II (plant) 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 2.7.1.73 inosine + ATP = inosine-5'-phosphate + ADP salvage pathways of adenine, hypoxanthine, and their nucleosides 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 2.7.1.73 inosine + ATP = inosine-5'-phosphate + ADP salvage pathways of purine nucleosides 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 2.7.1.73 inosine + ATP = inosine-5'-phosphate + ADP salvage pathways of purine nucleosides II (plant) 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 3.5.4.10 inosine-5'-phosphate + H2O = phosphoribosyl-formamido-carboxamide purine nucleotides de novo biosynthesis II 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 3.5.4.10 inosine-5'-phosphate + H2O = phosphoribosyl-formamido-carboxamide purine nucleotides de novo biosynthesis I 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = adenylo-succinate + GDP salvage pathways of purine nucleosides 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = adenylo-succinate + GDP purine nucleotides de novo biosynthesis II 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = adenylo-succinate + GDP purine nucleotides de novo biosynthesis I 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 3.1.3.5 inosine-5'-phosphate + H2O = inosine purine degradation 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 3.1.3.5 inosine-5'-phosphate + H2O = inosine salvage pathways of purine nucleosides II (plant) 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 3.5.4.6 AMP + H2O = inosine-5'-phosphate + ammonia purine degradation 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 348.208 C10 H13 N4 O8 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) CAS:131-99-7*LIGAND-CPD:C00130: 3.5.4.6 AMP + H2O = inosine-5'-phosphate + ammonia salvage pathways of purine nucleosides II (plant) 4-α-methyl zymosterol 4-methyl-8,24-cholestadienol*4-α-methyl-5α-cholesta-8,24-dien-3β-ol 398.671 C28 H46 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)C(O)CC4)))) 1.14.13.72 4-α-methyl zymosterol + O2 = 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I 4-α-methyl zymosterol 4-methyl-8,24-cholestadienol*4-α-methyl-5α-cholesta-8,24-dien-3β-ol 398.671 C28 H46 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)C(O)CC4)))) 1.14.13.72 4-α-methyl zymosterol + O2 = 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) 4-α-methyl zymosterol 4-methyl-8,24-cholestadienol*4-α-methyl-5α-cholesta-8,24-dien-3β-ol 398.671 C28 H46 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)C(O)CC4)))) 1.1.1.270 4α-methyl-5α-cholesta-8,24-dien-3-one + NADPH = 4-α-methyl zymosterol + NADP+ cholesterol biosynthesis I 4-α-methyl zymosterol 4-methyl-8,24-cholestadienol*4-α-methyl-5α-cholesta-8,24-dien-3β-ol 398.671 C28 H46 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)C(O)CC4)))) 1.1.1.270 4α-methyl-5α-cholesta-8,24-dien-3-one + NADPH = 4-α-methyl zymosterol + NADP+ cholesterol biosynthesis III (via desmosterol) bis-noryangonin BNY 230.22 C13 H10 O4 C1(=O)(OC(=CC(O)=C1)C=Cc2(ccc(O)cc2)) 2.3.1.- coumaroyl-CoA + malonyl-CoA = bis-noryangonin + coenzyme A + CO2 resveratrol biosynthesis phylloquinone 2-methyl-3-phytyl-1,4-naphthoquinone*phytonadione*phytomenadione*3-phytylmenadione*vitamin K1 450.703 C31 H46 O2 CC1(=C(C(=O)C2(=C(C(=O)1)C=CC=C2))CC=C(C)CCCC(C)CCCC(C)CCCC(C)C) NCI:270681*CAS:84-80-0 demethylphylloquinone + S-adenosyl-L-methionine = phylloquinone + S-adenosyl-L-homocysteine phylloquinone biosynthesis ethylene glycol monoethylene glycol*2-hydroxyethanol*ethanediol*1,2-ethanediol*glycol 62.068 C2 H6 O2 C(O)CO CAS:107-21-1 NAD+ + ethylene glycol = glycolaldehyde + NADH ethylene glycol degradation (-)-maackiain 284.268 C16 H12 O5 C1([CH]3([CH](c2(c(O1)cc(O)cc2))Oc4(c3cc5(c(c4)OCO5)))) 1.1.1.246 (-)-sophorol + NADPH = (-)-maackiain + NADP+ + H2O maackiain biosynthesis 2-keto-3-deoxy-6-phospho-gluconate 2-dehydro-3-deoxy-D-gluconate-6-phosphate*2-dehydro-3-deoxy-6-phospho-D-gluconate*6-phospho-2-dehydro-3-deoxy-D-gluconate*2-keto-3-deoxy-6-phosphogluconate*2-keto-3-deoxy-6-P-gluconate*6-p-2-k-3-deo-gluconate*6-phospho-2-keto-3-deoxygluconate*6-phospho-2-dehydro-3-deoxygluconate*2-keto-3-deoxygluconate-6-P 258.121 C6 H11 O9 P1 C(OP(O)(O)=O)[CH](O)[CH](O)[CH2]C(=O)C(=O)O LIGAND-CPD:C04442:*CAS:27244-54-8 2.7.1.45 2-dehydro-3-deoxy-D-gluconate + ATP = 2-keto-3-deoxy-6-phospho-gluconate + ADP β-D-glucuronide degradation L-lactaldehyde lactaldehyde*(S)-lactaldehyde*L-lactaldehyde*lactald 74.079 C3 H6 O2 C(=O)C(O)C LIGAND-CPD:C00424:*CAS:598-35-6 1.2.1.22 H2O + NAD+ + L-lactaldehyde = NADH + L-lactate fucose degradation L-lactaldehyde lactaldehyde*(S)-lactaldehyde*L-lactaldehyde*lactald 74.079 C3 H6 O2 C(=O)C(O)C LIGAND-CPD:C00424:*CAS:598-35-6 1.1.1.77 NADH + L-lactaldehyde = NAD+ fucose degradation L-lactaldehyde lactaldehyde*(S)-lactaldehyde*L-lactaldehyde*lactald 74.079 C3 H6 O2 C(=O)C(O)C LIGAND-CPD:C00424:*CAS:598-35-6 4.1.2.17 fuculose-1-phosphate = L-lactaldehyde + dihydroxy-acetone-phosphate fucose degradation 2,3-dihydroxy-isovalerate 2,3-dihydroxy-3-methylbutanoate*(R)-2,3-dihydroxy-3-methylbutanoate*α,β-dihydroxy-isovalerate 134.132 C5 H10 O4 CC(C)(O)C(O)C(O)=O LIGAND-CPD:C04272: 1.1.1.86 2,3-dihydroxy-isovalerate + NADP+ = 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 134.132 C5 H10 O4 CC(C)(O)C(O)C(O)=O LIGAND-CPD:C04272: 4.2.1.9 2,3-dihydroxy-isovalerate = 2-keto-isovalerate + H2O valine biosynthesis 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 228.138 C6 H13 O7 P1 CC(O)(CC(O)=O)CCOP(O)(O)=O CAS:73566-35-5 2.7.1.36 (R)-mevalonate + ATP = mevalonate-5P + ADP mevalonate pathway 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 228.138 C6 H13 O7 P1 CC(O)(CC(O)=O)CCOP(O)(O)=O CAS:73566-35-5 2.7.4.2 mevalonate-5P + ATP = mevalonate-5-PP + ADP mevalonate pathway unknown unknown = 7-deoxyloganin secologanin and strictosidine biosynthesis unknown unknown = calystegine A3 calystegine biosynthesis unknown unknown = tropinone calystegine biosynthesis unknown hygrine = unknown calystegine biosynthesis unknown pseudotropine = unknown calystegine biosynthesis unknown 10-hydroxygeraniol = unknown secologanin and strictosidine biosynthesis stemar-13-ene endo-stemarene*endo-stemarene 272.473 C20 H32 CC1(C)([CH]4(C(CCC1)(C)C23(CC(CC2)C(C)=C[CH]3CC4))) stemar-13-ene = oryzalexin S Oryzalexin S biosynthesis stemar-13-ene endo-stemarene*endo-stemarene 272.473 C20 H32 CC1(C)([CH]4(C(CCC1)(C)C23(CC(CC2)C(C)=C[CH]3CC4))) syn-copalyl diphosphate = stemar-13-ene Oryzalexin S biosynthesis ent-kaur-16-ene ent-kaurene 272.473 C20 H32 CC1([CH]2(C(CCC1)(C)[CH]4(C3(CC2)(CC(C(=C)C3)CC4))))(C) 4.2.3.19 ent-copalyl diphosphate = diphosphate + ent-kaur-16-ene ent-kaurene biosynthesis ent-kaur-16-ene ent-kaurene 272.473 C20 H32 CC1([CH]2(C(CCC1)(C)[CH]4(C3(CC2)(CC(C(=C)C3)CC4))))(C) 1.14.13.78 ent-kaur-16-ene + O2 + NADPH = H2O + NADP+ + ent-kaur-16-en-19-ol GA12 biosynthesis carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 141.02 C1 H4 N1 O5 P1 C(N)(=O)OP(=O)(O)O LIGAND-CPD:C00169:*CAS:590-55-6 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate de novo biosynthesis of pyrimidine ribonucleotides carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 141.02 C1 H4 N1 O5 P1 C(N)(=O)OP(=O)(O)O LIGAND-CPD:C00169:*CAS:590-55-6 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis II (acetyl cycle) carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 141.02 C1 H4 N1 O5 P1 C(N)(=O)OP(=O)(O)O LIGAND-CPD:C00169:*CAS:590-55-6 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis I carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 141.02 C1 H4 N1 O5 P1 C(N)(=O)OP(=O)(O)O LIGAND-CPD:C00169:*CAS:590-55-6 6.3.4.16 ammonia + H2O + CO2 + ATP = carbamoyl-phosphate + ADP urea cycle carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 141.02 C1 H4 N1 O5 P1 C(N)(=O)OP(=O)(O)O LIGAND-CPD:C00169:*CAS:590-55-6 2.7.2.2 ammonia + CO2 + ATP = carbamoyl-phosphate + ADP citrulline degradation carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 141.02 C1 H4 N1 O5 P1 C(N)(=O)OP(=O)(O)O LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.3 L-canaline + carbamoyl-phosphate = O-ureidohomoserine canavanine biosynthesis carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 141.02 C1 H4 N1 O5 P1 C(N)(=O)OP(=O)(O)O LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.2 L-aspartate + carbamoyl-phosphate = N-carbamoyl-L-aspartate de novo biosynthesis of pyrimidine ribonucleotides carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 141.02 C1 H4 N1 O5 P1 C(N)(=O)OP(=O)(O)O LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline urea cycle carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 141.02 C1 H4 N1 O5 P1 C(N)(=O)OP(=O)(O)O LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline proline biosynthesis V (from arginine) carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 141.02 C1 H4 N1 O5 P1 C(N)(=O)OP(=O)(O)O LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline arginine biosynthesis II (acetyl cycle) carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 141.02 C1 H4 N1 O5 P1 C(N)(=O)OP(=O)(O)O LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline arginine biosynthesis IV carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 141.02 C1 H4 N1 O5 P1 C(N)(=O)OP(=O)(O)O LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline citrulline degradation carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 141.02 C1 H4 N1 O5 P1 C(N)(=O)OP(=O)(O)O LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline arginine biosynthesis I carbamoyl-phosphate carbamoyl-P*carbamyl-phosphate 141.02 C1 H4 N1 O5 P1 C(N)(=O)OP(=O)(O)O LIGAND-CPD:C00169:*CAS:590-55-6 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline citrulline biosynthesis linoleate cis,cis-9,12-octadecadienoate*9-cis,12-cis-octadecadienoate*linoleic acid*linoleate*9,12-linoleic acid*(9Z,12Z)-octadeca-9,12-dienoate 280.45 C18 H32 O2 CCCCCC=CCC=CCCCCCCCC(=O)O NCI:281243*CAS:60-33-3 1.13.11.12 linoleate + O2 = 13-HPOD 13-LOX and 13-HPL pathway linoleate cis,cis-9,12-octadecadienoate*9-cis,12-cis-octadecadienoate*linoleic acid*linoleate*9,12-linoleic acid*(9Z,12Z)-octadeca-9,12-dienoate 280.45 C18 H32 O2 CCCCCC=CCC=CCCCCCCCC(=O)O NCI:281243*CAS:60-33-3 1.13.11.12 linoleate + O2 = 13-HPOD divinyl ether biosynthesis II (13-LOX) linoleate cis,cis-9,12-octadecadienoate*9-cis,12-cis-octadecadienoate*linoleic acid*linoleate*9,12-linoleic acid*(9Z,12Z)-octadeca-9,12-dienoate 280.45 C18 H32 O2 CCCCCC=CCC=CCCCCCCCC(=O)O NCI:281243*CAS:60-33-3 1.13.11.- linoleate + O2 = 9-HPOD 9-LOX and 9-HPL pathway 2-C-methyl-D-erythritol-2,4-cyclodiphosphate ME-2,4cPP 278.092 C5 H12 O9 P2 CC1(CO)(C(O)COP(=O)(O)OP(O)(O1)=O) LIGAND-CPD:C11453: 1.17.4.3 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 278.092 C5 H12 O9 P2 CC1(CO)(C(O)COP(=O)(O)OP(O)(O1)=O) 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 N2-succinyl-L-ornithine N2-succinylornithine 232.236 C9 H16 N2 O5 C(N)CCC(C(=O)O)NC(=O)CCC(=O)O CAS:80102-04-1:*LIGAND-CPD:C03415: 3.5.3.- N2-succinyl-L-arginine + H2O = ammonia + N2-succinyl-L-ornithine + CO2 arginine degradation II N2-succinyl-L-ornithine N2-succinylornithine 232.236 C9 H16 N2 O5 C(N)CCC(C(=O)O)NC(=O)CCC(=O)O CAS:80102-04-1:*LIGAND-CPD:C03415: 2.6.1.11 N2-succinyl-L-ornithine + α-ketoglutarate = L-glutamate + N2-succinyl-L-glutamate 5-semialdehyde arginine degradation II guanosine 5'-diphosphate,3'-diphosphate guanosine tetraphosphate*ppGpp*guanosine 3',5'-bispyrophosphate*guanosine 3',5'-bis(diphosphate)*Guanosine 3'-diphosphate 5'-diphosphate 603.163 C10 H17 N5 O17 P4 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1OP(=O)(O)OP(O)(O)=O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C01228: 2.7.6.5 ATP + GDP = AMP + guanosine 5'-diphosphate,3'-diphosphate ppGpp biosynthesis guanosine 5'-diphosphate,3'-diphosphate guanosine tetraphosphate*ppGpp*guanosine 3',5'-bispyrophosphate*guanosine 3',5'-bis(diphosphate)*Guanosine 3'-diphosphate 5'-diphosphate 603.163 C10 H17 N5 O17 P4 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1OP(=O)(O)OP(O)(O)=O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C01228: 3.1.7.2 guanosine 5'-diphosphate,3'-diphosphate + H2O = diphosphate + GDP ppGpp biosynthesis guanosine 5'-diphosphate,3'-diphosphate guanosine tetraphosphate*ppGpp*guanosine 3',5'-bispyrophosphate*guanosine 3',5'-bis(diphosphate)*Guanosine 3'-diphosphate 5'-diphosphate 603.163 C10 H17 N5 O17 P4 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1OP(=O)(O)OP(O)(O)=O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C01228: 3.6.1.40 H2O + guanosine 3'-diphosphate 5'-triphosphate = guanosine 5'-diphosphate,3'-diphosphate ppGpp biosynthesis (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->2)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->3)-α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 2649.123 C132 H220 N2 O47 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC3(C(O)C(C(O)C(O3)COC4(C(O)C(C(O)C(O4)CO)OC5(OC(CO)C(O)C(O)C(O)5)))OC6(C(C(O)C(O)C(O6)CO)OC7(C(C(O)C(O)C(O7)CO)OC8(OC(CO)C(O)C(O)C(O)8)))))) (mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->2)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->3)-α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 2649.123 C132 H220 N2 O47 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC3(C(O)C(C(O)C(O3)COC4(C(O)C(C(O)C(O4)CO)OC5(OC(CO)C(O)C(O)C(O)5)))OC6(C(C(O)C(O)C(O6)CO)OC7(C(C(O)C(O)C(O7)CO)OC8(OC(CO)C(O)C(O)C(O)8)))))) (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis N,N-dimethyl-β-alanine 117.147 C5 H11 N1 O2 C(N(C)C)CC(=O)O 2.1.1.- N-methyl-β-alanine + S-adenosyl-L-methionine = N,N-dimethyl-β-alanine + S-adenosyl-L-homocysteine β-alanine betaine biosynthesis N,N-dimethyl-β-alanine 117.147 C5 H11 N1 O2 C(N(C)C)CC(=O)O 2.1.1.- N,N-dimethyl-β-alanine + S-adenosyl-L-methionine = β-alanine betaine + S-adenosyl-L-homocysteine β-alanine betaine biosynthesis salicylate salicylic acid*o-hydroxybenzoic acid 138.123 C7 H6 O3 C(O)(=O)c1(c(O)cccc1) CAS:69-72-7 salicyloyl-CoA + H2O = salicylate + coenzyme A salicylate biosynthesis salicylate salicylic acid*o-hydroxybenzoic acid 138.123 C7 H6 O3 C(O)(=O)c1(c(O)cccc1) CAS:69-72-7 1.14.13.- benzoate + NADPH + O2 = salicylate + NADP+ + H2O salicylate biosynthesis salicylate salicylic acid*o-hydroxybenzoic acid 138.123 C7 H6 O3 C(O)(=O)c1(c(O)cccc1) CAS:69-72-7 isochorismate = salicylate + pyruvate salicylate biosynthesis L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = 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(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ NAD salvage pathway I L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = 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(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.8 L-glutamine + chorismate = L-glutamate + 4-amino-4-deoxychorismate tetrahydrofolate biosynthesis I L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.8 L-glutamine + chorismate = L-glutamate + 4-amino-4-deoxychorismate tetrahydrofolate biosynthesis II L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 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(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine purine nucleotides de novo biosynthesis I L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 1.4.1.13 L-glutamate + NADP+ = L-glutamine + α-ketoglutarate + NADPH glutamine degradation III L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 1.4.1.13 L-glutamate + NADP+ = L-glutamine + α-ketoglutarate + NADPH glutamate biosynthesis I L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phosphoribosyl 1-pyrophosphate + L-glutamine + H2O 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(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phosphoribosyl 1-pyrophosphate + L-glutamine + H2O purine nucleotides de novo biosynthesis I L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.4.2 ATP + UTP + L-glutamine + H2O = ADP + CTP + L-glutamate de novo biosynthesis of pyrimidine ribonucleotides L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 4.1.3.27 chorismate + L-glutamine = L-glutamate + anthranilate + 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(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP glutamine biosynthesis I L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O 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(=O)(O)C(N)CCC(N)=O 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(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: indole-3-acetate + L-glutamine = indole-3-acetyl-gln + H2O IAA conjugate biosynthesis II L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 2.6.1.16 fructose-6-phosphate + L-glutamine = L-glutamate + D-glucosamine-6-phosphate UDP-N-acetylgalactosamine biosynthesis L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 3.5.1.2 L-glutamine + H2O = 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(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.1.1.18 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(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate de novo biosynthesis of pyrimidine ribonucleotides L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.5 ATP + L-glutamine + CO2 + H2O = 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(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.5 ATP + L-glutamine + CO2 + H2O = 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(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 2.4.2.- phosphoribulosylformimino-AICAR-P + L-glutamine = L-glutamate + D-erythro-imidazole-glycerol-phosphate + AICAR histidine biosynthesis I L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = 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(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis I L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis III L-glutamine Q*proglumide*glum*gln*glutamine*glumin*2-aminoglutaramic acid*glutamic acid 5-amide 146.146 C5 H10 N2 O3 C(=O)(O)C(N)CCC(N)=O LIGAND-CPD:C00064:*CAS:56-85-9: 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis I 2-cis,6-trans,10-trans-geranylgeranyl diphosphate 450.448 C20 H36 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(O)(O)=O 2.5.1.31 trans, trans-farnesyl diphosphate = 2-cis,6-trans,10-trans-geranylgeranyl diphosphate + diphosphate polyisoprenoid biosynthesis D-sedoheptulose-7-phosphate D-Sedoheptulose-7-P*sedoheptulose-7-phosphate*heptulose-7-phosphate*sedoheptulose-7-P 290.163 C7 H15 O10 P1 C(O)C(=O)C(O)C(O)C(O)C(O)COP(=O)(O)O PUBCHEM:165007:*LIGAND-CPD:C00281:*CAS:2646-35-7 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = 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 290.163 C7 H15 O10 P1 C(O)C(=O)C(O)C(O)C(O)C(O)COP(=O)(O)O PUBCHEM:165007:*LIGAND-CPD:C00281:*CAS:2646-35-7 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = fructose-6-phosphate + D-erythrose-4-phosphate glucose fermentation to lactate II D-sedoheptulose-7-phosphate D-Sedoheptulose-7-P*sedoheptulose-7-phosphate*heptulose-7-phosphate*sedoheptulose-7-P 290.163 C7 H15 O10 P1 C(O)C(=O)C(O)C(O)C(O)C(O)COP(=O)(O)O PUBCHEM:165007:*LIGAND-CPD:C00281:*CAS:2646-35-7 3.1.3.37 H2O = D-sedoheptulose-7-phosphate Calvin cycle D-sedoheptulose-7-phosphate D-Sedoheptulose-7-P*sedoheptulose-7-phosphate*heptulose-7-phosphate*sedoheptulose-7-P 290.163 C7 H15 O10 P1 C(O)C(=O)C(O)C(O)C(O)C(O)COP(=O)(O)O PUBCHEM:165007:*LIGAND-CPD:C00281:*CAS:2646-35-7 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate pentose phosphate pathway (partial) D-sedoheptulose-7-phosphate D-Sedoheptulose-7-P*sedoheptulose-7-phosphate*heptulose-7-phosphate*sedoheptulose-7-P 290.163 C7 H15 O10 P1 C(O)C(=O)C(O)C(O)C(O)C(O)COP(=O)(O)O PUBCHEM:165007:*LIGAND-CPD:C00281:*CAS:2646-35-7 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate Calvin cycle D-sedoheptulose-7-phosphate D-Sedoheptulose-7-P*sedoheptulose-7-phosphate*heptulose-7-phosphate*sedoheptulose-7-P 290.163 C7 H15 O10 P1 C(O)C(=O)C(O)C(O)C(O)C(O)COP(=O)(O)O PUBCHEM:165007:*LIGAND-CPD:C00281:*CAS:2646-35-7 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate pentose phosphate pathway (non-oxidative branch) D-sedoheptulose-7-phosphate D-Sedoheptulose-7-P*sedoheptulose-7-phosphate*heptulose-7-phosphate*sedoheptulose-7-P 290.163 C7 H15 O10 P1 C(O)C(=O)C(O)C(O)C(O)C(O)COP(=O)(O)O PUBCHEM:165007:*LIGAND-CPD:C00281:*CAS:2646-35-7 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate (deoxy)ribose phosphate degradation D-sedoheptulose-7-phosphate D-Sedoheptulose-7-P*sedoheptulose-7-phosphate*heptulose-7-phosphate*sedoheptulose-7-P 290.163 C7 H15 O10 P1 C(O)C(=O)C(O)C(O)C(O)C(O)COP(=O)(O)O PUBCHEM:165007:*LIGAND-CPD:C00281:*CAS:2646-35-7 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate glucose fermentation to lactate II malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 2.3.3.9 acetyl-CoA + H2O + glyoxylate = malate + coenzyme A TCA cycle variation I malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 4.2.1.2 malate = fumarate + H2O mixed acid fermentation malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 4.2.1.2 malate = fumarate + H2O TCA cycle variation I malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 4.2.1.2 malate = fumarate + H2O reductive TCA cycle I malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 4.2.1.2 malate = fumarate + H2O respiration (anaerobic) malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 4.2.1.2 malate = fumarate + H2O TCA cycle malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.38 NAD+ + malate = NADH + CO2 + pyruvate gluconeogenesis malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.40 NADP+ + malate = NADPH + CO2 + pyruvate gluconeogenesis malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.37 malate + NAD+ = oxaloacetate + NADH mixed acid fermentation malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.37 malate + NAD+ = oxaloacetate + NADH TCA cycle variation I malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.37 malate + NAD+ = oxaloacetate + NADH reductive TCA cycle I malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.37 malate + NAD+ = oxaloacetate + NADH gluconeogenesis malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.37 malate + NAD+ = oxaloacetate + NADH respiration (anaerobic) malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.37 malate + NAD+ = oxaloacetate + NADH aspartate degradation II malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.1.1.37 malate + NAD+ = oxaloacetate + NADH TCA cycle malate hydroxysuccinic acid*hydroxybutanedioic acid*malic acid*L-mal*mal*L-malate*(S)-malate*DL-malic acid 134.088 C4 H6 O5 C(O)(=O)CC(O)C(O)=O CAS:97-67-6:*LIGAND-CPD:C00149:*LIGAND-CPD:C00497:*CAS:6915-15-7 1.2.1.5 D,L-malic semialdehyde + H2O = malate + H+ carnitine degradation III cis-zeatin-9-N-glucoside 381.388 C16 H23 N5 O6 c1(c2(c(ncn1)N(C=N2)C3(OC(CO)C(O)C(O)C(O)3)))(NCC=C(C)CO) 2.4.1.- cis-zeatin + UDP-D-glucose = cis-zeatin-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 4.2.3.- trans, trans-farnesyl diphosphate = α-longipinene + diphosphate oleoresin sesquiterpene volatiles biosynthesis trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 2.5.1.10 geranyl-PP = diphosphate + trans, trans-farnesyl diphosphate geranylgeranyldiphosphate biosynthesis II (plastidic) trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 2.5.1.10 geranyl-PP = diphosphate + trans, trans-farnesyl diphosphate polyisoprenoid biosynthesis trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 2.5.1.10 geranyl-PP = diphosphate + trans, trans-farnesyl diphosphate trans,trans-farnesyl diphosphate biosynthesis trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 4.2.3.9 trans, trans-farnesyl diphosphate = 5-epi-aristolochene + diphosphate capsidiol biosynthesis trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 4.2.3.- trans, trans-farnesyl diphosphate = γ-humulene + diphosphate oleoresin sesquiterpene volatiles biosynthesis trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 4.2.3.- trans, trans-farnesyl diphosphate = δ-selinene + diphosphate oleoresin sesquiterpene volatiles biosynthesis trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 2.5.1.21 trans, trans-farnesyl diphosphate = presqualene diphosphate + diphosphate cholesterol biosynthesis I trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 2.5.1.21 trans, trans-farnesyl diphosphate = presqualene diphosphate + diphosphate cholesterol biosynthesis III (via desmosterol) trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 2.5.1.21 trans, trans-farnesyl diphosphate = presqualene diphosphate + diphosphate cholesterol biosynthesis II (via 24,25-dihydrolanosterol) trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 2.5.1.21 trans, trans-farnesyl diphosphate = presqualene diphosphate + diphosphate sterol biosynthesis trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 2.5.1.29 trans, trans-farnesyl diphosphate = geranylgeranyl diphosphate + diphosphate geranylgeranyldiphosphate biosynthesis II (plastidic) trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 4.2.3.- trans, trans-farnesyl diphosphate = (E)-α-bisabolene + diphosphate oleoresin sesquiterpene volatiles biosynthesis trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 4.2.3.- trans, trans-farnesyl diphosphate = (E)-β-caryophyllene + diphosphate oleoresin sesquiterpene volatiles biosynthesis trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 2.5.1.31 trans, trans-farnesyl diphosphate = 2-cis,6-trans,10-trans-geranylgeranyl diphosphate + diphosphate polyisoprenoid biosynthesis trans, trans-farnesyl diphosphate FPP*farnesyl pyrophosphate*farnesyl-PP*farnesyl diphosphate*2-trans,6-trans-farnesyl diphosphate*(E,E)-farnesyl diphosphate 382.33 C15 H28 O7 P2 CC(C)=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C00448:*CAS:13058-04-3 4.2.3.- trans, trans-farnesyl diphosphate = longifolene + diphosphate oleoresin sesquiterpene volatiles biosynthesis pseudotropine 141.213 C8 H15 N1 O1 CN1(C2(CC(O)CC1CC2)) NCI:43871*CAS:135-97-7 1.1.1.236 NADP+ + pseudotropine = NADPH + tropinone calystegine biosynthesis pseudotropine 141.213 C8 H15 N1 O1 CN1(C2(CC(O)CC1CC2)) NCI:43871*CAS:135-97-7 pseudotropine = unknown calystegine biosynthesis tyramine tyrosamine*4-(2-Aminoethyl)phenol*p-Hydroxyphenethylamine*2-(p-Hydroxyphenyl)ethylamine 137.181 C8 H11 N1 O1 C(N)Cc1(ccc(O)cc1) CAS:51-67-2:*LIGAND-CPD:C00483:*PUBCHEM:5610: 2.3.1.110 feruloyl-CoA + tyramine = N-feruloyltyramine + coenzyme A suberin biosynthesis cis-3-hexenal 98.144 C6 H10 O1 C(=O)CC=CCC CAS:6789-80-6 13-HPOT = 12-oxo-cis-9-dodecenoate + cis-3-hexenal 13-LOX and 13-HPL pathway cis-3-hexenal 98.144 C6 H10 O1 C(=O)CC=CCC CAS:6789-80-6 cis-3-hexenal = cis-3-hexenol 13-LOX and 13-HPL pathway cis-3-hexenal 98.144 C6 H10 O1 C(=O)CC=CCC CAS:6789-80-6 cis-3-hexenal = trans-2-hexenal 13-LOX and 13-HPL pathway 5-amino-6-(5'-phosphoribosylamino)uracil 5-amino-6-(ribosylamino)-2,4-(1H,3H)-pyrimidinedione 5'-phosphate 354.213 C9 H15 N4 O9 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)Nc2(c(N)c(=O)[nH]c([nH]2)=O)) LIGAND-CPD:C01268: 1.1.1.193 5-amino-6-(5'-phosphoribitylamino)uracil + NADP+ = 5-amino-6-(5'-phosphoribosylamino)uracil + NADPH + H+ flavin biosynthesis 5-amino-6-(5'-phosphoribosylamino)uracil 5-amino-6-(ribosylamino)-2,4-(1H,3H)-pyrimidinedione 5'-phosphate 354.213 C9 H15 N4 O9 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)Nc2(c(N)c(=O)[nH]c([nH]2)=O)) LIGAND-CPD:C01268: 3.5.4.26 H2O + 2,5-diamino-6-(ribosylamino)-4-(3H)-pyrimidinone 5'-phosphate = 5-amino-6-(5'-phosphoribosylamino)uracil + ammonia flavin biosynthesis dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 2.7.1.29 dihydroxy-acetone + ATP = dihydroxy-acetone-phosphate + ADP xylulose-monophosphate cycle dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 iminoaspartate + dihydroxy-acetone-phosphate = quinolinate + H2O NAD biosynthesis I (from aspartate) dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 4.1.2.- Calvin cycle dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 1.1.99.5 sn-glycerol-3-phosphate + ubiquinone-8 = dihydroxy-acetone-phosphate + ubiquinol-8 aerobic respiration -- electron donors reaction list dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 1.1.99.5 sn-glycerol-3-phosphate + ubiquinone-8 = dihydroxy-acetone-phosphate + ubiquinol-8 respiration (anaerobic)-- electron donors reaction list dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 1.1.99.5 sn-glycerol-3-phosphate + ubiquinone-8 = dihydroxy-acetone-phosphate + ubiquinol-8 glycerol degradation I dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxy-acetone-phosphate Calvin cycle dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxy-acetone-phosphate sucrose degradation to ethanol and lactate (anaerobic) dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxy-acetone-phosphate glycolysis IV (plant cytosol) dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxy-acetone-phosphate fructose degradation to pyruvate and lactate (anaerobic) dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxy-acetone-phosphate glycolysis I dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate xylulose-monophosphate cycle dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate Calvin cycle dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate gluconeogenesis dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate sucrose degradation to ethanol and lactate (anaerobic) dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate glycolysis IV (plant cytosol) dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate fructose degradation to pyruvate and lactate (anaerobic) dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate glycolysis I dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 1.1.99.5 sn-glycerol-3-phosphate + FAD = dihydroxy-acetone-phosphate + FADH2 glycerol degradation IV dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 4.1.2.17 fuculose-1-phosphate = L-lactaldehyde + dihydroxy-acetone-phosphate fucose degradation dihydroxy-acetone-phosphate DHAP*glycerone-phosphate*dihydroxyacetone 3-phosphate*dihydroxyacetone-P*di-OH-acetone-P*dihydroxyacetone-phosphate 170.058 C3 H7 O6 P1 C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C00111:*CAS:57-04-5 1.1.1.94 sn-glycerol-3-phosphate = dihydroxy-acetone-phosphate + H+ phospholipid biosynthesis I (22α)-hydroxy-campesterol (22S)-22-hydroxy-campesterol 416.686 C28 H48 O2 CC(C)C(C)CC(O)C(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) 1.14.13.- campesterol + O2 + NADPH = (22α)-hydroxy-campesterol + H2O + NADP+ brassinosteroid biosynthesis II (22α)-hydroxy-campesterol (22S)-22-hydroxy-campesterol 416.686 C28 H48 O2 CC(C)C(C)CC(O)C(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) (22α)-hydroxy-campesterol = (22α)-hydroxy-campest-4-en-3-one brassinosteroid biosynthesis II 4-aminobutanal 4-amino-butyraldehyde*γ-aminobutyraldehyde*4-aminobutyraldehyde 87.121 C4 H9 N1 O1 C(=O)CCCN LIGAND-CPD:C00555:*CAS:4390-05-0 1.5.99.6 H2O + spermidine = 4-aminobutanal + 1,3-diaminopropane β-alanine biosynthesis I 4-aminobutanal 4-amino-butyraldehyde*γ-aminobutyraldehyde*4-aminobutyraldehyde 87.121 C4 H9 N1 O1 C(=O)CCCN LIGAND-CPD:C00555:*CAS:4390-05-0 4-aminobutanal = 1-pyrroline + H2O β-alanine biosynthesis I acetone dimethylketone*2-propanone*propanone 58.08 C3 H6 O1 CC(C)=O LIGAND-CPD:C00207:*CAS:67-64-1 4.1.1.4 acetoacetate + H+ = acetone + CO2 acetone degradation (to methylglyoxal) acetone dimethylketone*2-propanone*propanone 58.08 C3 H6 O1 CC(C)=O LIGAND-CPD:C00207:*CAS:67-64-1 4.1.2.37 acetone cyanohydrin = acetone + hydrogen cyanide linamarin degradation acetone dimethylketone*2-propanone*propanone 58.08 C3 H6 O1 CC(C)=O LIGAND-CPD:C00207:*CAS:67-64-1 marmesin + NADPH + O2 = psoralen + NADP+ + acetone + H2O linear furanocoumarin biosynthesis acetone dimethylketone*2-propanone*propanone 58.08 C3 H6 O1 CC(C)=O LIGAND-CPD:C00207:*CAS:67-64-1 1.14.14.1 acetone + NADPH + O2 = acetol + NADP+ + H2O acetone degradation (to methylglyoxal) succinate semialdehyde succinyl semialdehyde*succ-S-ald*succinic semialdehyde 102.09 C4 H6 O3 C(=O)(O)CC[CH]=O CAS:692-29-5:*LIGAND-CPD:C00232: 1.2.1.24 H2O + NAD+ + succinate semialdehyde = NADH + succinate glutamate degradation III succinate semialdehyde succinyl semialdehyde*succ-S-ald*succinic semialdehyde 102.09 C4 H6 O3 C(=O)(O)CC[CH]=O CAS:692-29-5:*LIGAND-CPD:C00232: 4.1.1.71 α-ketoglutarate = succinate semialdehyde + CO2 TCA cycle variation I succinate semialdehyde succinyl semialdehyde*succ-S-ald*succinic semialdehyde 102.09 C4 H6 O3 C(=O)(O)CC[CH]=O CAS:692-29-5:*LIGAND-CPD:C00232: 1.2.1.16 succinate semialdehyde + NADP+ + H2O = NADPH + succinate TCA cycle variation I succinate semialdehyde succinyl semialdehyde*succ-S-ald*succinic semialdehyde 102.09 C4 H6 O3 C(=O)(O)CC[CH]=O CAS:692-29-5:*LIGAND-CPD:C00232: 2.6.1.19 α-ketoglutarate + 4-aminobutyrate = L-glutamate + succinate semialdehyde glutamate degradation III 4-(3-pyridyl)-3-butenoate 4-(3-pyridyl)-3-butenoic acid 163.176 C9 H9 N1 O2 c1(ncc(cc1)C=CCC(O)=O) 4-hydroxy-4-(3-pyridyl)-butanoate = 4-(3-pyridyl)-3-butenoate nicotine degradation II 4-(3-pyridyl)-3-butenoate 4-(3-pyridyl)-3-butenoic acid 163.176 C9 H9 N1 O2 c1(ncc(cc1)C=CCC(O)=O) 4-hydroxy-4-(3-pyridyl)-butanoate = 4-(3-pyridyl)-3-butenoate nicotine degradation III 4-(3-pyridyl)-3-butenoate 4-(3-pyridyl)-3-butenoic acid 163.176 C9 H9 N1 O2 c1(ncc(cc1)C=CCC(O)=O) 4-(3-pyridyl)-3-butenoate = 4-(3-pyridyl)-butanoate nicotine degradation II 4-(3-pyridyl)-3-butenoate 4-(3-pyridyl)-3-butenoic acid 163.176 C9 H9 N1 O2 c1(ncc(cc1)C=CCC(O)=O) 4-(3-pyridyl)-3-butenoate = 4-(3-pyridyl)-butanoate nicotine degradation III (mannosyl)4-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 2324.839 C120 H200 N2 O37 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC3(C(O)C(C(O)C(O3)COC4(OC(CO)C(O)C(O)C(O)4))OC5(C(C(O)C(O)C(O5)CO)OC6(OC(CO)C(O)C(O)C(O)6))))) (mannosyl)3-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)4-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis (mannosyl)4-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 2324.839 C120 H200 N2 O37 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC3(C(O)C(C(O)C(O3)COC4(OC(CO)C(O)C(O)C(O)4))OC5(C(C(O)C(O)C(O5)CO)OC6(OC(CO)C(O)C(O)C(O)6))))) (mannosyl)4-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis 4-aminobutyrate 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)CCCN LIGAND-CPD:C00334:*CAS:56-12-2 2.6.1.19 α-ketoglutarate + 4-aminobutyrate = L-glutamate + succinate semialdehyde glutamate degradation III 4-aminobutyrate 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)CCCN LIGAND-CPD:C00334:*CAS:56-12-2 4.1.1.15 L-glutamate = CO2 + 4-aminobutyrate glutamate degradation III 4-aminobutyrate 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)CCCN LIGAND-CPD:C00334:*CAS:56-12-2 3.5.3.7 H2O + 4-guanidinobutyrate = urea + 4-aminobutyrate arginine degradation X (arginine monooxygenase pathway) solanyl pyrophosphate 791.039 C45 H76 O7 P2 CC(=CCCC(C)=CCCC(C)=CCOP(=O)(O)OP(O)(=O)O)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C homogentisate + solanyl pyrophosphate = 2-methyl-6-solanyl-1,4-benzoquinone + CO2 + diphosphate plastoquinone biosynthesis 18:1-16:3-MGDG 1-18:1-2-16:3-monogalactosyldiacylglycerol*1-(9Z-octadecenoyl)-2-(7Z,10Z,13Z-hexadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerol 751.052 C43 H74 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCC=CCC)COC(=O)CCCCCCCC=CCCCCCCCC 1.14.99.- 18:1-16:3-MGDG = 18:2-16:3-MGDG glycolipid desaturation 18:1-16:3-MGDG 1-18:1-2-16:3-monogalactosyldiacylglycerol*1-(9Z-octadecenoyl)-2-(7Z,10Z,13Z-hexadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerol 751.052 C43 H74 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCC=CCC)COC(=O)CCCCCCCC=CCCCCCCCC 1.14.99.- 18:1-16:2-MGDG = 18:1-16:3-MGDG glycolipid desaturation delphinidin delfinidin 303.248 C15 H11 O7 c3(c2(O=C(c1(cc(O)c(O)c(O)c1))C(O)=Cc2c(O)cc(O)3)) 2.4.1.115 UDP-D-glucose + delphinidin = UDP + delphinidin-3-O-β-D-glucoside anthocyanin biosynthesis (delphinidin 3-O-glucoside) delphinidin delfinidin 303.248 C15 H11 O7 c3(c2(O=C(c1(cc(O)c(O)c(O)c1))C(O)=Cc2c(O)cc(O)3)) 1.14.11.- leucodelphinidin + O2 + α-ketoglutarate = delphinidin + H2O + CO2 + succinate anthocyanin biosynthesis (delphinidin 3-O-glucoside) dihydroxy-acetone glycerone*1,3-dihydroxyacetone 90.079 C3 H6 O3 C(O)C(=O)CO LIGAND-CPD:C00184:*NCI:24343:*CAS:96-26-4 2.7.1.29 dihydroxy-acetone + ATP = dihydroxy-acetone-phosphate + ADP xylulose-monophosphate cycle dihydroxy-acetone glycerone*1,3-dihydroxyacetone 90.079 C3 H6 O3 C(O)C(=O)CO LIGAND-CPD:C00184:*NCI:24343:*CAS:96-26-4 2.2.1.3 formaldehyde + D-xylulose-5-phosphate = dihydroxy-acetone + D-glyceraldehyde-3-phosphate xylulose-monophosphate cycle ent-copalyl diphosphate ent-CPP*ent-CDP*(-)-CPP*(-)-CDP*(-)-copalyl diphosphate 450.448 C20 H36 O7 P2 CC(=CCOP(O)(=O)OP(O)(=O)O)CCC1(C(=C)CC[CH]2(C1(C)CCCC(C)(C)2)) 4.2.3.19 ent-copalyl diphosphate = diphosphate + ent-kaur-16-ene ent-kaurene biosynthesis ent-copalyl diphosphate ent-CPP*ent-CDP*(-)-CPP*(-)-CDP*(-)-copalyl diphosphate 450.448 C20 H36 O7 P2 CC(=CCOP(O)(=O)OP(O)(=O)O)CCC1(C(=C)CC[CH]2(C1(C)CCCC(C)(C)2)) 5.5.1.13 geranylgeranyl diphosphate = ent-copalyl diphosphate ent-kaurene biosynthesis ent-copalyl diphosphate ent-CPP*ent-CDP*(-)-CPP*(-)-CDP*(-)-copalyl diphosphate 450.448 C20 H36 O7 P2 CC(=CCOP(O)(=O)OP(O)(=O)O)CCC1(C(=C)CC[CH]2(C1(C)CCCC(C)(C)2)) ent-copalyl diphosphate = ent-cassa-12,15-diene + diphosphate phytocassane biosynthesis ent-copalyl diphosphate ent-CPP*ent-CDP*(-)-CPP*(-)-CDP*(-)-copalyl diphosphate 450.448 C20 H36 O7 P2 CC(=CCOP(O)(=O)OP(O)(=O)O)CCC1(C(=C)CC[CH]2(C1(C)CCCC(C)(C)2)) ent-copalyl diphosphate = ent-sandaracopimaradiene + diphosphate oryzalexin A-F biosynthesis acrylate 72.063 C3 H4 O2 C(O)(=O)C=C 3.5.1.4 acrylamide + H2O = ammonia + acrylate + H+ acrylonitrile degradation acrylate 72.063 C3 H4 O2 C(O)(=O)C=C 3.5.5.7 acrylonitrile + H2O = acrylate + ammonia acrylonitrile degradation orotidine-5'-phosphate 368.193 C10 H13 N2 O11 P1 c1(=O)([nH]c(=O)n(c(c1)C(O)=O)[CH]2(O[CH]([CH](O)[CH]2O)COP(O)(=O)O)) LIGAND-CPD:C01103:*CAS:2149-82-8 4.1.1.23 orotidine-5'-phosphate = CO2 + UMP de novo biosynthesis of pyrimidine ribonucleotides orotidine-5'-phosphate 368.193 C10 H13 N2 O11 P1 c1(=O)([nH]c(=O)n(c(c1)C(O)=O)[CH]2(O[CH]([CH](O)[CH]2O)COP(O)(=O)O)) LIGAND-CPD:C01103:*CAS:2149-82-8 2.4.2.10 orotidine-5'-phosphate + diphosphate = 5-phosphoribosyl 1-pyrophosphate + orotate de novo biosynthesis of pyrimidine ribonucleotides dihydrozeatin-7-N-dihydrozeatin 383.403 C16 H25 N5 O6 c2(c1(N(C=Nc1ncn2)C3(OC(CO)C(O)C(O)C(O)3)))(NCCC(C)CO) 2.4.1.- dihydrozeatin + UDP-D-glucose = dihydrozeatin-7-N-dihydrozeatin + UDP cytokinins 7-N-glucoside biosynthesis thymidine deoxythymidine 242.231 C10 H14 N2 O5 C(O)C1(OC(CC(O)1)n2(c(=O)[nH]c(=O)c(C)c2)) LIGAND-CPD:C00214:*CAS:50-89-5 2.7.1.21 thymidine + ATP = dTMP + ADP salvage pathways of purine and pyrimidine nucleotides thymidine deoxythymidine 242.231 C10 H14 N2 O5 C(O)C1(OC(CC(O)1)n2(c(=O)[nH]c(=O)c(C)c2)) LIGAND-CPD:C00214:*CAS:50-89-5 2.7.1.21 thymidine + ATP = dTMP + ADP salvage pathways of pyrimidine deoxyribonucleotides thymidine deoxythymidine 242.231 C10 H14 N2 O5 C(O)C1(OC(CC(O)1)n2(c(=O)[nH]c(=O)c(C)c2)) LIGAND-CPD:C00214:*CAS:50-89-5 2.4.2.4 thymidine = deoxyribose-1-phosphate + thymine salvage pathways of purine and pyrimidine nucleotides thymidine deoxythymidine 242.231 C10 H14 N2 O5 C(O)C1(OC(CC(O)1)n2(c(=O)[nH]c(=O)c(C)c2)) LIGAND-CPD:C00214:*CAS:50-89-5 2.4.2.4 thymidine = deoxyribose-1-phosphate + thymine (deoxy)ribose phosphate degradation thymidine deoxythymidine 242.231 C10 H14 N2 O5 C(O)C1(OC(CC(O)1)n2(c(=O)[nH]c(=O)c(C)c2)) LIGAND-CPD:C00214:*CAS:50-89-5 2.4.2.4 thymidine = deoxyribose-1-phosphate + thymine salvage pathways of pyrimidine deoxyribonucleotides 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 185.073 C3 H8 N1 O6 P1 C(C(N)C(O)=O)OP(O)(=O)O CAS:407-41-0:*LIGAND-CPD:C01005:*CAS:17885-08-4: 2.6.1.52 3-phospho-serine + α-ketoglutarate = L-glutamate + 3-phospho-hydroxypyruvate serine biosynthesis 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 185.073 C3 H8 N1 O6 P1 C(C(N)C(O)=O)OP(O)(=O)O CAS:407-41-0:*LIGAND-CPD:C01005:*CAS:17885-08-4: 3.1.3.3 3-phospho-serine + H2O = L-serine serine biosynthesis GA12 gibberellin A12*gibberellin A12*GA12 332.439 C20 H28 O4 CC1([CH]4(C(CCC1)(C)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) GA12 + O2 = GA53 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) GA12 gibberellin A12*gibberellin A12*GA12 332.439 C20 H28 O4 CC1([CH]4(C(CCC1)(C)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA12 + O2 + α-ketoglutarate = GA15 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) GA12 gibberellin A12*gibberellin A12*GA12 332.439 C20 H28 O4 CC1([CH]4(C(CCC1)(C)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.13.79 GA12-aldehyde + NADPH + O2 = GA12 + NADP+ + H2O GA12 biosynthesis GA12 gibberellin A12*gibberellin A12*GA12 332.439 C20 H28 O4 CC1([CH]4(C(CCC1)(C)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA12 + α-ketoglutarate + O2 = GA110 + succinate + CO2 gibberellin inactivation GA12 gibberellin A12*gibberellin A12*GA12 332.439 C20 H28 O4 CC1([CH]4(C(CCC1)(C)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA12 + α-ketoglutarate + O2 = GA14 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) 1,3-diaminopropane Trimethylenediamine*1,3-Propanediamine*Propane-1,3-diamine*1,3-DAP 74.125 C3 H10 N2 C(N)CCN CAS:109-76-2 1.5.99.6 H2O + spermidine = 4-aminobutanal + 1,3-diaminopropane β-alanine biosynthesis I 1,3-diaminopropane Trimethylenediamine*1,3-Propanediamine*Propane-1,3-diamine*1,3-DAP 74.125 C3 H10 N2 C(N)CCN CAS:109-76-2 1.4.3.6 1,3-diaminopropane + H2O + O2 = 3-aminopropionaldehyde + ammonia + H2O2 β-alanine biosynthesis I 1,3-diaminopropane Trimethylenediamine*1,3-Propanediamine*Propane-1,3-diamine*1,3-DAP 74.125 C3 H10 N2 C(N)CCN CAS:109-76-2 1.5.3.11 spermine + O2 + H2O = 1-(3-aminopropyl)-4-aminobutanal + 1,3-diaminopropane + H2O2 β-alanine biosynthesis I UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.17 nicotine + UDP-D-glucuronate = nicotine-Glucuronide + UDP nicotine degradation II UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 p-aminobenzoate + UDP-D-glucose = p-aminobenzoate-β-D-glucopyranosyl ester + UDP tetrahydrofolate biosynthesis II UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.117 dolichyl-phosphate + UDP-D-glucose = dolichyl β-D-glucosyl phosphate + UDP dolichyl-diphosphooligosaccharide biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.15 UDP-D-glucose + α-D-glucose 6-phosphate = UDP + trehalose 6-phosphate trehalose biosynthesis I UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- isopentenyladenine + UDP-D-glucose = isopentenyladenine-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- trans-zeatin + UDP-D-glucose = trans-zeatin-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.123 myo-inositol + UDP-galactose = galactinol + UDP stachyose biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- dihydrozeatin + UDP-D-glucose = dihydrozeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- trans-zeatin-O-glucoside + UDP-D-glucose = trans-zeatin-O-glucoside-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 1.17.4.- UDP = dUDP + H2O de novo biosynthesis of pyrimidine deoxyribonucleotides UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.2.34 UDP-L-arabinose + indol-3-yl-acetyl-myo-inositol = UDP + indole-3-yl-acetyl-myo-inositol L-arabinoside IAA conjugate biosynthesis I UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.182 2,3-bis(3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate + UDP-2,3-bis(3-hydroxymyristoyl)glucosamine = lipid A disaccharide + UDP lipid-A-precursor biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP sucrose degradation III UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP sucrose degradation to ethanol and lactate (anaerobic) UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP galactose degradation II UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP sucrose biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- cis-zeatin + UDP-D-glucose = cis-zeatin-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.114 2-coumarate + UDP-D-glucose = trans-β-D-Glucosyl-2-hydroxycinnamate + UDP coumarin biosynthesis (via 2-coumarate) UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.115 UDP-D-glucose + pelargonidin = UDP + pelargonidin-3-O-β-D-glucoside anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- kinetin + UDP-D-glucose = kinetin-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- trans-zeatin + UDP-D-glucose = trans-zeatin-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.14 fructose-6-phosphate + UDP-D-glucose = sucrose-6-phosphate + UDP sucrose biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.115 UDP-D-glucose + delphinidin = UDP + delphinidin-3-O-β-D-glucoside anthocyanin biosynthesis (delphinidin 3-O-glucoside) UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- dihydrozeatin + UDP-D-glucose = dihydrozeatin-7-N-dihydrozeatin + UDP cytokinins 7-N-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- benzyladenine + UDP-D-glucose = benzyladenine-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.141 N-acetylglucosaminyl-diphosphodolichol + UDP-N-acetyl-D-glucosamine = (N-acetylglucosaminyl)2-diphosphodolichol + UDP dolichyl-diphosphooligosaccharide biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.238 delphinidin-3,5-diglucoside + UDP-D-glucose = delphinidin 3,5,3'-triglucoside + UDP gentiodelphin biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 UDP-sulfoquinovose = sulfoquinovosyldiacylglycerol + UDP glycolipid biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- delphinidin 3-O-glucosyl-5-O-caffeoylglucoside + UDP-D-glucose = delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + UDP gentiodelphin biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 1.17.4.1 dUDP + H2O = UDP de novo biosynthesis of pyrimidine deoxyribonucleotides UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.241 UDP-galactose = UDP glycolipid biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.203 trans-zeatin + UDP-D-glucose = trans-zeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- hydroxy-β-cyclocitral + UDP-D-glucose = picrocrocin + UDP crocetin biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- dihydrozeatin + UDP-D-glucose = dihydrozeatin-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.215 cis-zeatin + UDP-D-glucose = cis-zeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.17 trans-3'-hydroxycotinine + UDP-D-glucuronate = trans-3-hydroxycotinine-glucuronide + UDP nicotine degradation III UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- dihydrozeatin-9-N-glucoside + UDP-D-glucose = dihydrozeatin-9-N-glucoside-O-glucoside + UDP cytokinins-O-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.121 indole-3-acetate + UDP-D-glucose = indole-3-acetyl-β-1-D-glucose + UDP IAA conjugate biosynthesis II UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.121 indole-3-acetate + UDP-D-glucose = indole-3-acetyl-β-1-D-glucose + UDP IAA conjugate biosynthesis I UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.17 cotinine + UDP-D-glucuronate = cotinine-glucuronide + UDP nicotine degradation III UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- kinetin + UDP-D-glucose = kinetin-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- cis-zeatin + UDP-D-glucose = cis-zeatin-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.115 UDP-D-glucose + cyanidin = UDP + cyanidin-3-O-β-D-glucoside anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- isopentenyladenine + UDP-D-glucose = isopentenyladenine-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.156 indol-3-yl-acetyl-myo-inositol + UDP-galactose = 5-O-(indol-3-ylacetyl-myo-inositol) D-galactoside + UDP IAA conjugate biosynthesis I UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.7.4.- ATP + UMP = ADP + UDP de novo biosynthesis of pyrimidine ribonucleotides UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.7.4.- ATP + UMP = ADP + UDP salvage pathways of purine and pyrimidine nucleotides UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- benzyladenine + UDP-D-glucose = benzyladenine-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.- delphinidin-3-O-β-D-glucoside + UDP-D-glucose = delphinidin-3,5-diglucoside + UDP gentiodelphin biosynthesis UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.227 UDP-N-acetyl-D-glucosamine = UDP peptidoglycan biosynthesis I UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.7.4.6 UDP + ATP = UTP + ADP de novo biosynthesis of pyrimidine ribonucleotides UDP uridine-diphosphate*uridine-5'-diphosphate 404.163 C9 H14 N2 O12 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00015:*CAS:58-98-0 2.4.1.46 UDP-galactose = UDP glycolipid biosynthesis 5,10-methenyltetrahydromethanopterin methenyl-H4MPT*N5,N10-methenyltetrahydromethanopterin*5,10-methenyl-H4MPT*N5,N10-methenyl-5,6,7,8-tetrahydromethanopterin*5,10-methenyl-5,6,7,8-tetrahydromethanopterin*5,10-methenyl-tetrahydromethanopterin 786.685 C31 H43 N6 O16 P1 C[CH]2([CH]1([CH](C)[N+](=CN1c3(c(=O)[nH]c(N)nc([NH]2)3))c4(ccc(cc4)CC(O)C(O)C(O)COC5(OC(C(O)C5O)COP(=O)([O-])OC(C(O)=O)CCC(O)=O)))) LIGAND-CPD:C04330: 1.12.98.2 5,10-methenyltetrahydromethanopterin + H2 = 5,10-methylene-tetrahydromethanopterin + H+ methanogenesis from CO2 5,10-methenyltetrahydromethanopterin methenyl-H4MPT*N5,N10-methenyltetrahydromethanopterin*5,10-methenyl-H4MPT*N5,N10-methenyl-5,6,7,8-tetrahydromethanopterin*5,10-methenyl-5,6,7,8-tetrahydromethanopterin*5,10-methenyl-tetrahydromethanopterin 786.685 C31 H43 N6 O16 P1 C[CH]2([CH]1([CH](C)[N+](=CN1c3(c(=O)[nH]c(N)nc([NH]2)3))c4(ccc(cc4)CC(O)C(O)C(O)COC5(OC(C(O)C5O)COP(=O)([O-])OC(C(O)=O)CCC(O)=O)))) LIGAND-CPD:C04330: 3.5.4.27 5,10-methenyltetrahydromethanopterin + H2O = 5-formyl-tetrahydromethanopterin methanogenesis from CO2 5,10-methenyltetrahydromethanopterin methenyl-H4MPT*N5,N10-methenyltetrahydromethanopterin*5,10-methenyl-H4MPT*N5,N10-methenyl-5,6,7,8-tetrahydromethanopterin*5,10-methenyl-5,6,7,8-tetrahydromethanopterin*5,10-methenyl-tetrahydromethanopterin 786.685 C31 H43 N6 O16 P1 C[CH]2([CH]1([CH](C)[N+](=CN1c3(c(=O)[nH]c(N)nc([NH]2)3))c4(ccc(cc4)CC(O)C(O)C(O)COC5(OC(C(O)C5O)COP(=O)([O-])OC(C(O)=O)CCC(O)=O)))) LIGAND-CPD:C04330: 1.5.99.9 5,10-methylene-tetrahydromethanopterin = 5,10-methenyltetrahydromethanopterin methanogenesis from CO2 L-threonine T*thr*thre*L-thr*threonine*2-amino-3-hydroxybutyric acid 119.12 C4 H9 N1 O3 C(=O)(O)C(N)C(C)O LIGAND-CPD:C00188:*CAS:72-19-5 4.3.1.19 L-threonine = 2-oxobutanoate + ammonia isoleucine biosynthesis from threonine L-threonine T*thr*thre*L-thr*threonine*2-amino-3-hydroxybutyric acid 119.12 C4 H9 N1 O3 C(=O)(O)C(N)C(C)O LIGAND-CPD:C00188:*CAS:72-19-5 6.1.1.3 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 C(=O)(O)C(N)C(C)O 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 C(=O)(O)C(N)C(C)O LIGAND-CPD:C00188:*CAS:72-19-5 1.1.1.103 L-threonine + NAD+ = 2-amino-3-oxobutanoate + NADH threonine degradation II L-threonine T*thr*thre*L-thr*threonine*2-amino-3-hydroxybutyric acid 119.12 C4 H9 N1 O3 C(=O)(O)C(N)C(C)O LIGAND-CPD:C00188:*CAS:72-19-5 1.1.1.103 L-threonine + NAD+ = 2-amino-3-oxobutanoate + NADH threonine degradation III (to methylglyoxal) L-threonine T*thr*thre*L-thr*threonine*2-amino-3-hydroxybutyric acid 119.12 C4 H9 N1 O3 C(=O)(O)C(N)C(C)O LIGAND-CPD:C00188:*CAS:72-19-5 1.1.1.103 L-threonine + NAD+ = 2-amino-3-oxobutanoate + NADH aminopropanol biosynthesis salicyloyl-CoA 887.641 C28 H40 N7 O18 P3 S1 C(NCCC(=O)NCCSC(=O)c1(c(O)cccc1))(=O)C(O)C(C)(C)COP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C2OP(=O)(O)O)n3(c4(c(nc3)c(N)ncn4))) salicyloyl-CoA + H2O = salicylate + coenzyme A salicylate biosynthesis salicyloyl-CoA 887.641 C28 H40 N7 O18 P3 S1 C(NCCC(=O)NCCSC(=O)c1(c(O)cccc1))(=O)C(O)C(C)(C)COP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C2OP(=O)(O)O)n3(c4(c(nc3)c(N)ncn4))) benzoyl-CoA = salicyloyl-CoA salicylate biosynthesis (+)-abscisate abscisic acid*ABA*abscisate*(+)-ABA*(+)-S-ABA*abscisin II*2-cis-ABA 264.321 C15 H20 O4 CC1(C(C(C)=CC(=O)C1)(O)C=CC(C)=CC(=O)O)(C) 1.2.3.14 abscisic aldehyde + H2O + O2 = (+)-abscisate + H2O2 abscisic acid biosynthesis (+)-abscisate abscisic acid*ABA*abscisate*(+)-ABA*(+)-S-ABA*abscisin II*2-cis-ABA 264.321 C15 H20 O4 CC1(C(C(C)=CC(=O)C1)(O)C=CC(C)=CC(=O)O)(C) 1.14.13.93 (+)-abscisate + NADPH + O2 = 8'-hydroxyabscisate + NADP+ + H2O phaseic acid biosynthesis L-2-acetamido-6-oxoheptanedioate N-acetyl-L-2-amino-6-oxo-pimelate*N-acetyl-2-amino-6-ketopimelate 231.205 C9 H13 N1 O6 CC(=O)NC(C(O)=O)CCCC(=O)C(O)=O L-2-acetamido-6-oxoheptanedioate + L-glutamate = N-acetyl-L,L-2,6-diaminopimelate + α-ketoglutarate lysine biosynthesis II L-2-acetamido-6-oxoheptanedioate N-acetyl-L-2-amino-6-oxo-pimelate*N-acetyl-2-amino-6-ketopimelate 231.205 C9 H13 N1 O6 CC(=O)NC(C(O)=O)CCCC(=O)C(O)=O 2.3.1.89 acetyl-CoA + tetrahydrodipicolinate + H2O = coenzyme A + L-2-acetamido-6-oxoheptanedioate lysine biosynthesis II (-)-camphene (-)-(1S,4R)-camphene 136.236 C10 H16 C=C1(C(C)(C)C2(CC1CC2)) 4.2.3.- geranyl-PP = (-)-camphene + diphosphate oleoresin monoterpene volatiles biosynthesis dimethylsulfide reduced dimethyl sulfoxide*dimethyl sulphide*dimethylsulphide*DMS*dimethyl sulfide 62.129 C2 H6 S1 CSC PUBCHEM:1068:*LIGAND-CPD:C00580:*CAS:75-18-3 2.1.1.19 tetrahydrofolate + trimethyl sulfonium = dimethylsulfide + 5-methyl-THF folate transformations O-succinylbenzoyl-CoA 2-Succinylbenzoyl-CoA*Succinylbenzoyl-CoA*2-(3'-carboxypropionyl)benzoyl-CoA 971.716 C32 H44 N7 O20 P3 S1 c1(c2(c(ncn1)n(cn2)C3(OC(C(C(O)3)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)c4(c(cccc4)C(=O)CCC(=O)O))))(N) LIGAND-CPD:C03160: 6.2.1.26 ATP + O-succinylbenzoate + coenzyme A = AMP + diphosphate + O-succinylbenzoyl-CoA menaquinone biosynthesis O-succinylbenzoyl-CoA 2-Succinylbenzoyl-CoA*Succinylbenzoyl-CoA*2-(3'-carboxypropionyl)benzoyl-CoA 971.716 C32 H44 N7 O20 P3 S1 c1(c2(c(ncn1)n(cn2)C3(OC(C(C(O)3)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)c4(c(cccc4)C(=O)CCC(=O)O))))(N) LIGAND-CPD:C03160: 4.1.3.36 O-succinylbenzoyl-CoA = coenzyme A + 1,4-dihydroxy-2-naphthoate menaquinone biosynthesis enterobactin Enterochelin 669.554 C30 H27 N3 O15 C(=O)(c1(c(O)c(O)ccc1))NC3(C(=O)OCC(NC(=O)c2(c(O)c(O)ccc2))C(=O)OCC(C(=O)OC3)NC(=O)c4(c(O)c(O)ccc4)) ATP + L-serine + 2,3-dihydroxybenzoate = enterobactin + diphosphate + AMP enterobactin biosynthesis betaine aldehyde glycine betaine aldehyde 102.156 C5 H12 N1 O1 C(=O)CN(C)(C)C 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 C(=O)CN(C)(C)C LIGAND-CPD:C00576:*CAS:7418-61-3 1.2.1.8 betaine aldehyde + NAD+ + H2O = glycine betaine + NADH glycine betaine biosynthesis III (plants) 9'-cis-neoxanthin 9cNeox*9c-neoxanthin*9'-cis-neoxanthin 600.88 C40 H56 O4 CC(C=C=C1(C(C)(C)CC(O)CC(C)1O))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC23(C(O2)(C)CC(O)CC(C)(C)3) 1.13.11.51 9'-cis-neoxanthin + O2 = xanthoxin + C25-allenic-apo-aldehyde abscisic acid biosynthesis 9'-cis-neoxanthin 9cNeox*9c-neoxanthin*9'-cis-neoxanthin 600.88 C40 H56 O4 CC(C=C=C1(C(C)(C)CC(O)CC(C)1O))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC23(C(O2)(C)CC(O)CC(C)(C)3) trans-neoxanthin = 9'-cis-neoxanthin abscisic acid biosynthesis O-phospho-L-homoserine o-phosphohomoserine 199.1 C4 H10 N1 O6 P1 C(O)(=O)C(N)CCOP(O)(=O)O LIGAND-CPD:C01102: 2.7.1.39 homoserine + ATP = O-phospho-L-homoserine + ADP threonine biosynthesis from homoserine O-phospho-L-homoserine o-phosphohomoserine 199.1 C4 H10 N1 O6 P1 C(O)(=O)C(N)CCOP(O)(=O)O LIGAND-CPD:C01102: 2.7.1.39 homoserine + ATP = O-phospho-L-homoserine + ADP methionine biosynthesis II O-phospho-L-homoserine o-phosphohomoserine 199.1 C4 H10 N1 O6 P1 C(O)(=O)C(N)CCOP(O)(=O)O LIGAND-CPD:C01102: 4.2.3.1 O-phospho-L-homoserine + H2O = L-threonine threonine biosynthesis from homoserine O-phospho-L-homoserine o-phosphohomoserine 199.1 C4 H10 N1 O6 P1 C(O)(=O)C(N)CCOP(O)(=O)O LIGAND-CPD:C01102: 2.5.1.- L-cysteine + O-phospho-L-homoserine = 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 587.33 C16 H23 N5 O15 P2 CC1(OC(C(O)C(O)C1=O)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c4(c(nc3)c(=O)[nH]c(n4)N)))) LIGAND-CPD:C01222: 4.2.1.47 GDP-D-mannose = H2O + GDP-4-dehydro-6-deoxy-D-mannose GDP-D-rhamnose biosynthesis 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 587.33 C16 H23 N5 O15 P2 CC1(OC(C(O)C(O)C1=O)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c4(c(nc3)c(=O)[nH]c(n4)N)))) LIGAND-CPD:C01222: 4.2.1.47 GDP-D-mannose = H2O + GDP-4-dehydro-6-deoxy-D-mannose 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 587.33 C16 H23 N5 O15 P2 CC1(OC(C(O)C(O)C1=O)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c4(c(nc3)c(=O)[nH]c(n4)N)))) LIGAND-CPD:C01222: 1.1.1.271 NADP+ + GDP-L-fucose = NADPH + GDP-4-dehydro-6-deoxy-D-mannose 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 587.33 C16 H23 N5 O15 P2 CC1(OC(C(O)C(O)C1=O)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c4(c(nc3)c(=O)[nH]c(n4)N)))) LIGAND-CPD:C01222: 1.1.1.187 GDP-D-rhamnose = GDP-4-dehydro-6-deoxy-D-mannose + H+ GDP-D-rhamnose biosynthesis (-)-carvone 150.22 C10 H14 O1 C=C(C)C1(CC=C(C)C(=O)C1) CAS:6485-40-1 1.1.1.243 (-)-trans-carveol + NADP+ = (-)-carvone + NADPH + H+ menthol biosynthesis tetrahydropteroyltri-L-glutamate 687.665 C29 H37 N9 O11 C(C1(CNc2(c([NH]1)c(=O)[nH]c(N)n2)))Nc3(ccc(cc3)C(=O)NC(C(=O)O)CCC(=O)NC(C(=O)O)CCC(=O)NC(C(=O)O)CCC=O) LIGAND-CPD:C04144: 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine S-adenosylmethionine biosynthesis tetrahydropteroyltri-L-glutamate 687.665 C29 H37 N9 O11 C(C1(CNc2(c([NH]1)c(=O)[nH]c(N)n2)))Nc3(ccc(cc3)C(=O)NC(C(=O)O)CCC(=O)NC(C(=O)O)CCC(=O)NC(C(=O)O)CCC=O) LIGAND-CPD:C04144: 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine methionine biosynthesis II tetrahydropteroyltri-L-glutamate 687.665 C29 H37 N9 O11 C(C1(CNc2(c([NH]1)c(=O)[nH]c(N)n2)))Nc3(ccc(cc3)C(=O)NC(C(=O)O)CCC(=O)NC(C(=O)O)CCC(=O)NC(C(=O)O)CCC=O) LIGAND-CPD:C04144: 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine methionine biosynthesis I tetrahydropteroyltri-L-glutamate 687.665 C29 H37 N9 O11 C(C1(CNc2(c([NH]1)c(=O)[nH]c(N)n2)))Nc3(ccc(cc3)C(=O)NC(C(=O)O)CCC(=O)NC(C(=O)O)CCC(=O)NC(C(=O)O)CCC=O) LIGAND-CPD:C04144: 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine S-adenosyl-L-methionine cycle hydrogen cyanide cyanide*hydrocyanic acid 27.026 C1 H1 N1 [CH]#N CAS:57-12-5:*LIGAND-CPD:C01326: 1.14.17.4 L-ascorbate + 1-aminocyclopropane-1-carboxylate + O2 = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine hydrogen cyanide cyanide*hydrocyanic acid 27.026 C1 H1 N1 [CH]#N CAS:57-12-5:*LIGAND-CPD:C01326: 4.1.2.37 acetone cyanohydrin = acetone + hydrogen cyanide linamarin degradation hydrogen cyanide cyanide*hydrocyanic acid 27.026 C1 H1 N1 [CH]#N CAS:57-12-5:*LIGAND-CPD:C01326: 2.8.1.2 hydrogen cyanide + 3-mercaptopyruvate = pyruvate + thiocyanate L-cysteine degradation III hydrogen cyanide cyanide*hydrocyanic acid 27.026 C1 H1 N1 [CH]#N CAS:57-12-5:*LIGAND-CPD:C01326: 2.8.1.1 thiosulfate + hydrogen cyanide = 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 286.178 C7 H15 N2 O8 P1 C(CN)(=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(O)(=O)O) LIGAND-CPD:C03838: 2.1.2.2 N10-formyl-THF + 5-phospho-ribosyl-glycineamide = tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide purine nucleotides de novo biosynthesis II 5-phospho-ribosyl-glycineamide N1-(5-Phospho-D-ribosyl)glycinamide*5'-phosphoribosylglycinamide*5'-phosphoribosylglycineamide*5'-p-ribosylglycinamide*5'-p-ribosylglycineamide*GAR 286.178 C7 H15 N2 O8 P1 C(CN)(=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(O)(=O)O) LIGAND-CPD:C03838: 2.1.2.2 N10-formyl-THF + 5-phospho-ribosyl-glycineamide = tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide tetrahydrofolate biosynthesis I 5-phospho-ribosyl-glycineamide N1-(5-Phospho-D-ribosyl)glycinamide*5'-phosphoribosylglycinamide*5'-phosphoribosylglycineamide*5'-p-ribosylglycinamide*5'-p-ribosylglycineamide*GAR 286.178 C7 H15 N2 O8 P1 C(CN)(=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(O)(=O)O) LIGAND-CPD:C03838: 2.1.2.2 N10-formyl-THF + 5-phospho-ribosyl-glycineamide = tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide purine nucleotides de novo biosynthesis I 5-phospho-ribosyl-glycineamide N1-(5-Phospho-D-ribosyl)glycinamide*5'-phosphoribosylglycinamide*5'-phosphoribosylglycineamide*5'-p-ribosylglycinamide*5'-p-ribosylglycineamide*GAR 286.178 C7 H15 N2 O8 P1 C(CN)(=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(O)(=O)O) LIGAND-CPD:C03838: 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = 5'-phosphoribosyl-N-formylglycineamide + ADP purine nucleotides de novo biosynthesis I 5-phospho-ribosyl-glycineamide N1-(5-Phospho-D-ribosyl)glycinamide*5'-phosphoribosylglycinamide*5'-phosphoribosylglycineamide*5'-p-ribosylglycinamide*5'-p-ribosylglycineamide*GAR 286.178 C7 H15 N2 O8 P1 C(CN)(=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(O)(=O)O) LIGAND-CPD:C03838: 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = ADP + 5-phospho-ribosyl-glycineamide purine nucleotides de novo biosynthesis II 5-phospho-ribosyl-glycineamide N1-(5-Phospho-D-ribosyl)glycinamide*5'-phosphoribosylglycinamide*5'-phosphoribosylglycineamide*5'-p-ribosylglycinamide*5'-p-ribosylglycineamide*GAR 286.178 C7 H15 N2 O8 P1 C(CN)(=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(O)(=O)O) LIGAND-CPD:C03838: 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = ADP + 5-phospho-ribosyl-glycineamide purine nucleotides de novo biosynthesis I 2-ketoisocaproate 2-keto-4-methyl-pentanoate*2-oxoisocaproate*4-methyl-2-oxopentanoate*2-oxo-4-methylpentanoate*α-ketoisocaproate*α-oxoisocaproate 130.143 C6 H10 O3 CC(C)CC(=O)C(=O)O LIGAND-CPD:C00233:*CAS:816-66-0 4.1.1.1 2-ketoisocaproate = 3-methylbutanal + CO2 leucine degradation III 2-ketoisocaproate 2-keto-4-methyl-pentanoate*2-oxoisocaproate*4-methyl-2-oxopentanoate*2-oxo-4-methylpentanoate*α-ketoisocaproate*α-oxoisocaproate 130.143 C6 H10 O3 CC(C)CC(=O)C(=O)O LIGAND-CPD:C00233:*CAS:816-66-0 2.6.1.42 L-leucine + α-ketoglutarate = L-glutamate + 2-ketoisocaproate leucine degradation III 2-ketoisocaproate 2-keto-4-methyl-pentanoate*2-oxoisocaproate*4-methyl-2-oxopentanoate*2-oxo-4-methylpentanoate*α-ketoisocaproate*α-oxoisocaproate 130.143 C6 H10 O3 CC(C)CC(=O)C(=O)O LIGAND-CPD:C00233:*CAS:816-66-0 2.6.1.42 L-leucine + α-ketoglutarate = L-glutamate + 2-ketoisocaproate leucine biosynthesis 2-ketoisocaproate 2-keto-4-methyl-pentanoate*2-oxoisocaproate*4-methyl-2-oxopentanoate*2-oxo-4-methylpentanoate*α-ketoisocaproate*α-oxoisocaproate 130.143 C6 H10 O3 CC(C)CC(=O)C(=O)O LIGAND-CPD:C00233:*CAS:816-66-0 2.6.1.42 L-leucine + α-ketoglutarate = L-glutamate + 2-ketoisocaproate leucine degradation I 2-ketoisocaproate 2-keto-4-methyl-pentanoate*2-oxoisocaproate*4-methyl-2-oxopentanoate*2-oxo-4-methylpentanoate*α-ketoisocaproate*α-oxoisocaproate 130.143 C6 H10 O3 CC(C)CC(=O)C(=O)O LIGAND-CPD:C00233:*CAS:816-66-0 2-isopropyl-3-oxosuccinate = 2-ketoisocaproate + CO2 leucine biosynthesis 2-ketoisocaproate 2-keto-4-methyl-pentanoate*2-oxoisocaproate*4-methyl-2-oxopentanoate*2-oxo-4-methylpentanoate*α-ketoisocaproate*α-oxoisocaproate 130.143 C6 H10 O3 CC(C)CC(=O)C(=O)O LIGAND-CPD:C00233:*CAS:816-66-0 2-ketoisocaproate + coenzyme A + NAD+ = isovaleryl-CoA + CO2 + NADH leucine degradation I quercetin 3,5,7,3',4'-Pentahydroxyflavone 302.24 C15 H10 O7 c1(c(ccc(O)c1O)C2(=C(O)C(=O)c3(c(O)cc(O)cc(O2)3))) 1.14.11.23 dihydroquercetin + α-ketoglutarate + O2 = quercetin + succinate + CO2 + H2O flavonol biosynthesis quercetin 3,5,7,3',4'-Pentahydroxyflavone 302.24 C15 H10 O7 c1(c(ccc(O)c1O)C2(=C(O)C(=O)c3(c(O)cc(O)cc(O2)3))) 2.1.1.- quercetin + S-adenosyl-L-methionine = isorhamnetin + S-adenosyl-L-homocysteine flavonol biosynthesis 4α-methylfecosterol 4α-methyl-5α-ergosta-8,24-dien-3β-ol 412.698 C29 H48 O1 CC(C)C(=C)CCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4([CH](CC3)C(C)C(O)CC4)(C)))) 5.3.3.5 4α-methylfecosterol = 24-methylenelophenol sterol biosynthesis 4α-methylfecosterol 4α-methyl-5α-ergosta-8,24-dien-3β-ol 412.698 C29 H48 O1 CC(C)C(=C)CCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4([CH](CC3)C(C)C(O)CC4)(C)))) 1.3.1.70 (4α)-methyl-(5α)-ergosta-8,14,24(28)-trien-3β-ol + NADPH = 4α-methylfecosterol + NADP+ sterol biosynthesis sitosterol 414.713 C29 H50 O1 CC(C)C(CC)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) 1.3.1.- sitosterol + NADP+ = stigmasterol + NADPH sterol biosynthesis sitosterol 414.713 C29 H50 O1 CC(C)C(CC)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) Δ24-25-sitosterol = sitosterol sterol biosynthesis butyryl phosphate butyryl-P*butanoyl phosphate*phosphobutyrate 168.086 C4 H9 O5 P1 C(OP(O)(=O)O)(=O)CCC 2.3.1.19 butyryl-CoA = butyryl phosphate + coenzyme A acetyl CoA fermentation to butyrate butyryl phosphate butyryl-P*butanoyl phosphate*phosphobutyrate 168.086 C4 H9 O5 P1 C(OP(O)(=O)O)(=O)CCC 2.7.2.7 butyrate + ATP = butyryl phosphate + ADP acetyl CoA fermentation to butyrate 3-hydroxy-propionate 3-Hydroxypropanoate*β-hydroxypropionate*3-Hydroxypropanoic acid*3-Hydropropionic acid*Hydracrylic acid 90.079 C3 H6 O3 C(O)(=O)CCO CAS:96-26-4*CAS:503-66-2 1.1.1.59 NAD+ + 3-hydroxy-propionate = NADH + malonate semialdehyde β-alanine biosynthesis II 3-hydroxy-propionate 3-Hydroxypropanoate*β-hydroxypropionate*3-Hydroxypropanoic acid*3-Hydropropionic acid*Hydracrylic acid 90.079 C3 H6 O3 C(O)(=O)CCO CAS:96-26-4*CAS:503-66-2 3.1.2.4 3-hydroxypropionyl-CoA + H2O = 3-hydroxy-propionate + 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.9.2 H2O + pyruvate + ATP = phosphoenolpyruvate + AMP reductive TCA cycle I pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.9.2 H2O + pyruvate + ATP = phosphoenolpyruvate + AMP gluconeogenesis pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.9.2 H2O + pyruvate + ATP = 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C 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 enterobactin biosynthesis pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.6.1.30 pyruvate + pyridoxamine = L-alanine + pyridoxal pyridoxamine anabolism pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.1.2.4 D-lactate = pyruvate aerobic respiration -- electron donors reaction list pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.1.2.4 D-lactate = pyruvate methylglyoxal degradation I pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.2.2.2 pyruvate + ubiquinone-8 + H2O = ubiquinol-8 + acetate + CO2 mixed acid fermentation pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.1.1.27 NAD+ + L-lactate = NADH + pyruvate sucrose degradation to ethanol and lactate (anaerobic) pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.1.1.27 NAD+ + L-lactate = NADH + pyruvate fructose degradation to pyruvate and lactate (anaerobic) pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.1.1.27 NAD+ + L-lactate = NADH + pyruvate glucose fermentation to lactate II pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.4.1.1 H2O = pyruvate + ammonia glutathione-mediated detoxification pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.4.1.8 cystathionine + H2O = 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.4.1.8 cystathionine + H2O = ammonia + pyruvate + L-homocysteine methionine 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.4.1.8 cystathionine + H2O = 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: L-lactate = pyruvate fucose degradation pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: L-lactate = pyruvate aerobic respiration -- electron donors reaction list pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: L-lactate = pyruvate respiration (anaerobic)-- electron donors reaction list pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.1.3.27 chorismate + L-glutamine = L-glutamate + anthranilate + 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.6.1.58 pyruvate + L-phenylalanine = phenylpyruvate + L-alanine phenylalanine degradation III pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.2.1.52 pyruvate + L-aspartate-semialdehyde = H2O 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.2.1.52 pyruvate + L-aspartate-semialdehyde = H2O lysine 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.2.1.52 pyruvate + L-aspartate-semialdehyde = H2O lysine 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.1.1.38 NAD+ + malate = NADH + CO2 + pyruvate gluconeogenesis pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.3.1.54 formate + acetyl-CoA = pyruvate + coenzyme A mixed acid fermentation pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.3.1.54 formate + acetyl-CoA = pyruvate + coenzyme A respiration (anaerobic) pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.1.1.1 pyruvate = acetaldehyde + CO2 sucrose degradation to ethanol and lactate (anaerobic) pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: isochorismate = salicylate + pyruvate salicylate biosynthesis pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 3-sulfinyl-pyruvate + H2O = sulfite + pyruvate L-cysteine degradation I pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.2.7.1 pyruvate + coenzyme A = acetyl-CoA + CO2 reductive TCA cycle I pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.2.7.1 pyruvate + coenzyme A = acetyl-CoA + CO2 D-lactate fermentation to propionate and acetate pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.2.7.1 pyruvate + coenzyme A = acetyl-CoA + CO2 glutamate degradation VII (to butyrate) pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.3.1.17 L-serine = pyruvate + ammonia glycine betaine degradation pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.6.1.2 α-ketoglutarate + 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.6.1.2 α-ketoglutarate + L-alanine = L-glutamate + pyruvate alanine degradation III pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.1.1.40 NADP+ + malate = NADPH + CO2 + pyruvate gluconeogenesis pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.2.1.7 pyruvate + D-glyceraldehyde-3-phosphate = 1-deoxy-D-xylulose 5-phosphate + CO2 pyridoxal 5'-phosphate biosynthesis pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.2.1.7 pyruvate + D-glyceraldehyde-3-phosphate = 1-deoxy-D-xylulose 5-phosphate + CO2 thiamine biosynthesis pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.2.1.7 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.1.3.16 D-4-hydroxy-2-keto-glutarate = glyoxylate + pyruvate 4-hydroxyproline degradation I pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.2.1.- pyruvate + coenzyme A + NAD+ = acetyl-CoA + CO2 + NADH respiration (anaerobic) pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.8.1.2 hydrogen cyanide + 3-mercaptopyruvate = pyruvate + thiocyanate L-cysteine degradation III pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: succinate-semialdehyde-thiamine PPi + isochorismate = 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate + thiamine diphosphate + pyruvate menaquinone biosynthesis pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: succinate-semialdehyde-thiamine PPi + isochorismate = 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate + thiamine diphosphate + pyruvate phylloquinone biosynthesis pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.2.4.1 pyruvate = CO2 pyruvate dehydrogenase complex pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.1.3.38 4-amino-4-deoxychorismate = p-aminobenzoate + pyruvate tetrahydrofolate 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 4.1.3.38 4-amino-4-deoxychorismate = p-aminobenzoate + pyruvate tetrahydrofolate 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.1.1.28 NAD+ + D-lactate = NADH + pyruvate mixed acid fermentation pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 1.1.1.28 NAD+ + D-lactate = NADH + pyruvate D-lactate fermentation to propionate and acetate pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate mixed acid fermentation pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate sucrose degradation to ethanol and lactate (anaerobic) pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate respiration (anaerobic) pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate fructose degradation to pyruvate and lactate (anaerobic) pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate glucose fermentation to lactate II pyruvate alpha-ketopropionic acid*BTS*α-ketopropionic acid*acetylformic acid*pyroracemic acid*2-oxopropanoic acid*pyruvic acid*2-oxopropanoate*2-oxo-propionic acid 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.2.1.6 pyruvate + 2-oxobutanoate = 2-aceto-2-hydroxy-butyrate + CO2 isoleucine biosynthesis 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 88.063 C3 H4 O3 C(=O)(O)C(=O)C LIGAND-CPD:C00022:*CAS:127-17-3*LIGAND-CPD:c00022:*UM-BBD-CPD:c0159: 2.2.1.6 pyruvate = 2-acetolactate + CO2 valine biosynthesis 5α-cholesta-7,24-dien-3β-ol 5α-cholesta-7,24-dien-3-β-ol*(24R)-cholest-5-ene 3-β,7-α,24-triol 384.644 C27 H44 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C)(C(CC=3)CC(O)CC4)))) 1.3.1.72 5α-cholesta-7,24-dien-3β-ol + NADPH = lathosterol + NADP+ cholesterol biosynthesis I 5α-cholesta-7,24-dien-3β-ol 5α-cholesta-7,24-dien-3-β-ol*(24R)-cholest-5-ene 3-β,7-α,24-triol 384.644 C27 H44 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C)(C(CC=3)CC(O)CC4)))) 5.3.3.5 zymosterol = 5α-cholesta-7,24-dien-3β-ol cholesterol biosynthesis I 5α-cholesta-7,24-dien-3β-ol 5α-cholesta-7,24-dien-3-β-ol*(24R)-cholest-5-ene 3-β,7-α,24-triol 384.644 C27 H44 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C)(C(CC=3)CC(O)CC4)))) 5.3.3.5 zymosterol = 5α-cholesta-7,24-dien-3β-ol cholesterol biosynthesis III (via desmosterol) 5α-cholesta-7,24-dien-3β-ol 5α-cholesta-7,24-dien-3-β-ol*(24R)-cholest-5-ene 3-β,7-α,24-triol 384.644 C27 H44 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C)(C(CC=3)CC(O)CC4)))) 1.14.21.6 5α-cholesta-7,24-dien-3β-ol + O2 = 7-dehydrodesmosterol + H2O cholesterol biosynthesis III (via desmosterol) formaldehyde formalin*methanal*formol 30.026 C1 H2 O1 [CH2]=O LIGAND-CPD:C00067:*CAS:50-00-0 2.2.1.3 formaldehyde + D-xylulose-5-phosphate = dihydroxy-acetone + D-glyceraldehyde-3-phosphate xylulose-monophosphate cycle formaldehyde formalin*methanal*formol 30.026 C1 H2 O1 [CH2]=O LIGAND-CPD:C00067:*CAS:50-00-0 1.5.99.2 dimethylglycine + H2O = formaldehyde + sarcosine glycine betaine degradation formaldehyde formalin*methanal*formol 30.026 C1 H2 O1 [CH2]=O LIGAND-CPD:C00067:*CAS:50-00-0 nicotine + H2O = nornicotine + formaldehyde nicotine degradation II formaldehyde formalin*methanal*formol 30.026 C1 H2 O1 [CH2]=O LIGAND-CPD:C00067:*CAS:50-00-0 4.4.1.22 S-hydroxymethylglutathione = formaldehyde + glutathione formaldehyde oxidation II (glutathione-dependent) formaldehyde formalin*methanal*formol 30.026 C1 H2 O1 [CH2]=O LIGAND-CPD:C00067:*CAS:50-00-0 1.5.3.1 O2 + H2O + sarcosine = H2O2 + formaldehyde + glycine glycine betaine degradation GDP-L-galactose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C(O)1)OP(O)(=O)OP(O)(=O)OCC2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4)))) 5.1.3.- GDP-L-gulose = GDP-L-galactose ascorbate biosynthesis GDP-L-galactose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C(O)1)OP(O)(=O)OP(O)(=O)OCC2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4)))) GDP-L-galactose + H2O = L-galactose + GMP ascorbate biosynthesis 2-isopropylmalate 3-hydroxy-4-methyl-3-carboxypentanoate*3-carboxy-3-hydroxy-4-methylpentanoate*3-carboxy-3-hydroxy-isocaproate*α-isopropylmalate*(2S)-2-isopropylmalate 176.169 C7 H12 O5 C(=O)(O)CC(O)(C(=O)O)C(C)C LIGAND-CPD:C02504: 2.3.3.13 2-keto-isovalerate + acetyl-CoA + H2O = 2-isopropylmalate + coenzyme A leucine biosynthesis 2-isopropylmalate 3-hydroxy-4-methyl-3-carboxypentanoate*3-carboxy-3-hydroxy-4-methylpentanoate*3-carboxy-3-hydroxy-isocaproate*α-isopropylmalate*(2S)-2-isopropylmalate 176.169 C7 H12 O5 C(=O)(O)CC(O)(C(=O)O)C(C)C LIGAND-CPD:C02504: 4.2.1.33 2-isopropylmalate = 3-isopropylmalate leucine biosynthesis 4-coumarate p-coumarate*trans-4-hydroxycinnamate*p-coumaric acid*4-Hydroxycinnamic acid*4-Hydroxycinnamate*coumarate 164.16 C9 H8 O3 C(O)(=O)C=Cc1(ccc(O)cc1) CAS:7400-08-0 6.2.1.12 coenzyme A + 4-coumarate + ATP = coumaroyl-CoA + diphosphate + AMP flavonoid biosynthesis 4-coumarate p-coumarate*trans-4-hydroxycinnamate*p-coumaric acid*4-Hydroxycinnamic acid*4-Hydroxycinnamate*coumarate 164.16 C9 H8 O3 C(O)(=O)C=Cc1(ccc(O)cc1) CAS:7400-08-0 6.2.1.12 coenzyme A + 4-coumarate + ATP = coumaroyl-CoA + diphosphate + AMP phenylpropanoid biosynthesis 4-coumarate p-coumarate*trans-4-hydroxycinnamate*p-coumaric acid*4-Hydroxycinnamic acid*4-Hydroxycinnamate*coumarate 164.16 C9 H8 O3 C(O)(=O)C=Cc1(ccc(O)cc1) CAS:7400-08-0 4-coumarate + NADPH + O2 = H2O + caffeate + NADP+ suberin biosynthesis 4-coumarate p-coumarate*trans-4-hydroxycinnamate*p-coumaric acid*4-Hydroxycinnamic acid*4-Hydroxycinnamate*coumarate 164.16 C9 H8 O3 C(O)(=O)C=Cc1(ccc(O)cc1) CAS:7400-08-0 4-coumarate + NADPH + O2 = H2O + caffeate + NADP+ free phenylpropanoid acid biosynthesis 4-coumarate p-coumarate*trans-4-hydroxycinnamate*p-coumaric acid*4-Hydroxycinnamic acid*4-Hydroxycinnamate*coumarate 164.16 C9 H8 O3 C(O)(=O)C=Cc1(ccc(O)cc1) CAS:7400-08-0 1.14.13.11 trans-cinnamate + O2 + NADPH = H2O + NADP+ + 4-coumarate suberin biosynthesis 4-coumarate p-coumarate*trans-4-hydroxycinnamate*p-coumaric acid*4-Hydroxycinnamic acid*4-Hydroxycinnamate*coumarate 164.16 C9 H8 O3 C(O)(=O)C=Cc1(ccc(O)cc1) CAS:7400-08-0 1.14.13.11 trans-cinnamate + O2 + NADPH = H2O + NADP+ + 4-coumarate phenylpropanoid biosynthesis, initial reactions UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate UDP-N-acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelate*UDP-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelate*UDP-MurNAc-L-Ala-D-Glu-mesoA2pm 1050.79 C35 H55 N7 O26 P2 CC(=O)NC1(C(OC(C)C(=O)NC(C)C(=O)NC(C(O)=O)CCC(=O)NC(C(O)=O)CCCC(N)C(O)=O)C(O)C(CO)OC1OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c(=O)[nH]c(=O)cc3))) LIGAND-CPD:C04877: 6.3.2.13 UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + meso-diaminopimelate + ATP = UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + ADP peptidoglycan biosynthesis I UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate UDP-N-acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelate*UDP-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelate*UDP-MurNAc-L-Ala-D-Glu-mesoA2pm 1050.79 C35 H55 N7 O26 P2 CC(=O)NC1(C(OC(C)C(=O)NC(C)C(=O)NC(C(O)=O)CCC(=O)NC(C(O)=O)CCCC(N)C(O)=O)C(O)C(CO)OC1OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c(=O)[nH]c(=O)cc3))) LIGAND-CPD:C04877: 6.3.2.10 UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + D-alanyl-D-alanine + ATP = ADP peptidoglycan biosynthesis I e- e*electron 1.000d-3 H2O = H+ + e- + O2 photosynthesis, light reaction e- e*electron 1.000d-3 photosynthesis, light reaction e- e*electron 1.000d-3 thioredoxin pathway oryzalexin S 304.472 C20 H32 O2 C(O)C1([CH]2(C(C)(CC(C1)O)C34(C(CC2)C=C(C)C(C3)CC4)))(C) stemar-13-ene = oryzalexin S Oryzalexin S biosynthesis avenasterol 412.698 C29 H48 O1 CC(C)C(=CC)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC=3)CC(O)CC4)(C)))) 1.3.3.- avenasterol = 5-dehydroavenasterol sterol biosynthesis avenasterol 412.698 C29 H48 O1 CC(C)C(=CC)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC=3)CC(O)CC4)(C)))) 2.1.1.- 24-ethylidenelophenol = avenasterol sterol biosynthesis trans-zeatin riboside monophosphate ZMP*tZRMP 431.341 C15 H22 N5 O8 P1 C1(C(O)C(O)C(O1)COP(O)(O)=O)n2(c3(c(nc2)c(ncn3)NCC=C(C)CO)) trans-zeatin riboside monophosphate + H2O = trans-zeatin riboside trans-zeatin biosynthesis trans-zeatin riboside monophosphate ZMP*tZRMP 431.341 C15 H22 N5 O8 P1 C1(C(O)C(O)C(O1)COP(O)(O)=O)n2(c3(c(nc2)c(ncn3)NCC=C(C)CO)) trans-zeatin riboside monophosphate = trans-zeatin + D-ribose-5-phosphate trans-zeatin biosynthesis trans-zeatin riboside monophosphate ZMP*tZRMP 431.341 C15 H22 N5 O8 P1 C1(C(O)C(O)C(O1)COP(O)(O)=O)n2(c3(c(nc2)c(ncn3)NCC=C(C)CO)) trans-zeatin riboside diphosphate + H2O = trans-zeatin riboside monophosphate trans-zeatin biosynthesis trans-zeatin riboside monophosphate ZMP*tZRMP 431.341 C15 H22 N5 O8 P1 C1(C(O)C(O)C(O1)COP(O)(O)=O)n2(c3(c(nc2)c(ncn3)NCC=C(C)CO)) isopentenyladenosine-5'-monophosphate + NADPH + H2O = trans-zeatin riboside monophosphate + NADP+ trans-zeatin biosynthesis 6G-kestotriose kestotriose 504.441 C18 H32 O16 C(O)C1(OC(C(O)C(O)1)(CO)OC2(OC(C(O)C(O)C2O)COC3(CO)(OC(CO)C(O)C(O)3))) 3.2.1.- 6G,6-kestotetraose + H2O = 6G-kestotriose + fructose fructan degradation 6G-kestotriose kestotriose 504.441 C18 H32 O16 C(O)C1(OC(C(O)C(O)1)(CO)OC2(OC(C(O)C(O)C2O)COC3(CO)(OC(CO)C(O)C(O)3))) 2.4.1.- 1-kestotriose + sucrose = 6G-kestotriose + sucrose fructan biosynthesis FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 785.556 C27 H33 N9 O15 P2 Cc3(cc2(n(c1(c(C(=O)[NH]C(=O)N=1)nc2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH](O)4)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C00016:*CAS:146-14-5 1.5.99.12 trans-zeatin + H2O + FAD = adenine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 785.556 C27 H33 N9 O15 P2 Cc3(cc2(n(c1(c(C(=O)[NH]C(=O)N=1)nc2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH](O)4)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C00016:*CAS:146-14-5 1.5.99.12 isopentenyladenine + FAD + H2O = 3-methyl-2-butenal + adenine + FADH2 cytokinins degradation FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 785.556 C27 H33 N9 O15 P2 Cc3(cc2(n(c1(c(C(=O)[NH]C(=O)N=1)nc2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH](O)4)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C00016:*CAS:146-14-5 1.5.99.12 cis-zeatin + H2O + FAD = 3-methyl-4-cis-hydroxy-2-butenal + adenine + FADH2 cytokinins degradation FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 785.556 C27 H33 N9 O15 P2 Cc3(cc2(n(c1(c(C(=O)[NH]C(=O)N=1)nc2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH](O)4)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C00016:*CAS:146-14-5 1.1.99.5 sn-glycerol-3-phosphate + FAD = dihydroxy-acetone-phosphate + FADH2 glycerol degradation IV FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 785.556 C27 H33 N9 O15 P2 Cc3(cc2(n(c1(c(C(=O)[NH]C(=O)N=1)nc2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH](O)4)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C00016:*CAS:146-14-5 1.3.99.10 isovaleryl-CoA + FAD = 3-methylcrotonyl-CoA + FADH2 leucine degradation I FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 785.556 C27 H33 N9 O15 P2 Cc3(cc2(n(c1(c(C(=O)[NH]C(=O)N=1)nc2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH](O)4)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C00016:*CAS:146-14-5 1.3.99.12 isobutyryl-CoA + FAD = methylacrylyl-CoA + FADH2 valine degradation I FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 785.556 C27 H33 N9 O15 P2 Cc3(cc2(n(c1(c(C(=O)[NH]C(=O)N=1)nc2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH](O)4)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C00016:*CAS:146-14-5 1.3.99.12 S-2-methyl-butyryl-CoA + FAD = tiglyl-CoA + FADH2 isoleucine degradation I FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 785.556 C27 H33 N9 O15 P2 Cc3(cc2(n(c1(c(C(=O)[NH]C(=O)N=1)nc2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH](O)4)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C00016:*CAS:146-14-5 1.5.99.8 L-proline + FAD = FADH2 proline degradation I FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 785.556 C27 H33 N9 O15 P2 Cc3(cc2(n(c1(c(C(=O)[NH]C(=O)N=1)nc2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH](O)4)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C00016:*CAS:146-14-5 1.5.99.8 L-proline + FAD = FADH2 citrulline biosynthesis FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 785.556 C27 H33 N9 O15 P2 Cc3(cc2(n(c1(c(C(=O)[NH]C(=O)N=1)nc2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH](O)4)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C00016:*CAS:146-14-5 1.3.99.3 FADH2 + acrylyl-CoA = FAD + propionyl-CoA β-alanine biosynthesis II FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 785.556 C27 H33 N9 O15 P2 Cc3(cc2(n(c1(c(C(=O)[NH]C(=O)N=1)nc2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH](O)4)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C00016:*CAS:146-14-5 1.3.99.3 FAD = FADH2 fatty acid β-oxidation I FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 785.556 C27 H33 N9 O15 P2 Cc3(cc2(n(c1(c(C(=O)[NH]C(=O)N=1)nc2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH](O)4)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C00016:*CAS:146-14-5 1.5.99.12 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 785.556 C27 H33 N9 O15 P2 Cc3(cc2(n(c1(c(C(=O)[NH]C(=O)N=1)nc2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH](O)4)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C00016:*CAS:146-14-5 2.7.7.2 FMN + ATP = FAD + diphosphate flavin biosynthesis FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 785.556 C27 H33 N9 O15 P2 Cc3(cc2(n(c1(c(C(=O)[NH]C(=O)N=1)nc2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH](O)4)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C00016:*CAS:146-14-5 1.5.99.12 isopentenyl adenosine + H2O + FAD = adenosine + 3-methyl-2-butenal + FADH2 cytokinins degradation FAD flavin adenine dinucleotide oxidized*flavin adenine dinucleotide*flavitan 785.556 C27 H33 N9 O15 P2 Cc3(cc2(n(c1(c(C(=O)[NH]C(=O)N=1)nc2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH](O)4)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C00016:*CAS:146-14-5 glutaryl-CoA + FAD = glutaconyl-CoA + FADH2 glutaryl-CoA degradation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- coniferyl aldehyde + NADPH + O2 = 5-hydroxy-coniferaldehyde + NADP+ + H2O phenylpropanoid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA34 + α-ketoglutarate + O2 = GA34-catabolite + succinate + CO2 + H2O gibberellin inactivation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.2.3.1 nicotine-Δ1'5'-iminium ion + O2 + H2O = cotinine + H2O2 nicotine degradation II O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.2.3.1 nicotine-Δ1'5'-iminium ion + O2 + H2O = cotinine + H2O2 nicotine degradation III O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.4.3.6 tryptamine + H2O + O2 = ammonia + indole acetaldehyde + H2O2 IAA biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 liquiritigenin + NADPH + O2 = 6,7,4'-trihydroxyflavanone + NADP+ + H2O 6,7,4'-trihydroxyisoflavone biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- dihydrokaempferol + NADPH + O2 = dihydromyricetin + NADP+ + H2O leucodelphinidin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 4.1.1.- O2 = 2-phosphoglycolate + 3-phosphoglycerate + H+ photorespiration O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 calycosin + NADPH + O2 = pseudobaptigenin + NADP+ + H2O maackiain biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA51 + α-ketoglutarate + O2 = GA51-catabolite + succinate + CO2 + H2O gibberellin inactivation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.79 ent-kaurenoate + O2 + NADPH = ent-7-α-hydroxykaurenoate + H2O + NADP+ GA12 biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.-.- 6-deoxocathasterone + O2 = 6-deoxoteasterone + H2O brassinosteroid biosynthesis II O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol + O2 = 4α-formyl-4β-methyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA8 + α-ketoglutarate + O2 = GA8-catabolite + succinate + CO2 + H2O gibberellin inactivation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.4.3.5 O2 + pyridoxine-5'-phosphate = H2O2 + pyridoxal 5'-phosphate pyridoxal 5'-phosphate biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.4.3.5 O2 + pyridoxine-5'-phosphate = H2O2 + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4α-formyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4α-formyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.1 O2 + dihydroorotate = H2O2 + orotate de novo biosynthesis of pyrimidine ribonucleotides O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.7.3.3 urate + O2 + H2O = 5-hydroxyisourate + H2O2 ureide biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.12 O2 + linolenate = 13-HPOT 13-LOX and 13-HPL pathway O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.12 O2 + linolenate = 13-HPOT jasmonic acid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA53 + α-ketoglutarate + O2 = GA97 + succinate + CO2 gibberellin inactivation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 chlorophyll b + H2O + NADP+ = 7-hydroxy-chlorophyll a + O2 + NADPH chlorophyll cycle O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 O2 + H+ = trimethylamine + D,L-malic semialdehyde + H2O carnitine degradation III O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.21 dihydrokaempferol + NADPH + O2 = dihydroquercetin + NADP+ + H2O leucopelargonidin and leucocyanidin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.21 dihydrokaempferol + NADPH + O2 = dihydroquercetin + NADP+ + H2O leucodelphinidin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.21 dihydrokaempferol + NADPH + O2 = dihydroquercetin + NADP+ + H2O flavonol biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA29 + α-ketoglutarate + O2 = GA29-catabolite + succinate + CO2 + H2O gibberellin inactivation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.11 trans-cinnamate + O2 + NADPH = H2O + NADP+ + 4-coumarate suberin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.11 trans-cinnamate + O2 + NADPH = H2O + NADP+ + 4-coumarate phenylpropanoid biosynthesis, initial reactions O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.- α-carotene + NADPH + O2 = zeinoxanthin + NADP+ + H2O carotenoid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.7.3.3 urate + O2 = allantoin + CO2 + H2O2 purine degradation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.12.1 O2 + L-arginine = 4-guanidinobutyramide + H2O + CO2 arginine degradation X (arginine monooxygenase pathway) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.23 dihydrokaempferol + α-ketoglutarate + O2 = kaempferol + succinate + CO2 + H2O flavonol biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA12 + O2 + α-ketoglutarate = GA15 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.4.3.6 1,3-diaminopropane + H2O + O2 = 3-aminopropionaldehyde + ammonia + H2O2 β-alanine biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA24 + α-ketoglutarate + O2 = GA36 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.9 O2 + NADPH + loganin = H2O + NADP+ + secologanin secologanin and strictosidine biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.14.1 cotinine + NADPH + O2 = N'-hydroxymethyl-norcotinine + NADP+ + H2O nicotine degradation III O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA4 + α-ketoglutarate + O2 = GA34 + succinate + CO2 gibberellin inactivation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA9 + α-ketoglutarate + O2 = GA4 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4α-methyl-cholesta-8-enol + O2 = 4α-hydroxymethyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA36 + O2 + α-ketoglutarate = GA4 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA15 + α-ketoglutarate + O2 = GA24 + succinate + CO2 + H2O gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.- β-cryptoxanthin + O2 = zeaxanthin + H2O carotenoid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA19 + O2 + α-ketoglutarate = GA20 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADP+ + H2O + formate cholesterol biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADP+ + H2O + formate cholesterol biosynthesis III (via desmosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol + O2 + NADPH = 4,4-dimethyl-5-α-cholesta-8,14-dien-3-β-ol + formate + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate + O2 = (+)-7-isojasmonate + acetate jasmonic acid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.12 GA44 + α-ketoglutarate + O2 = GA19 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.30 O2 + neurosporene = H2O + trans-lycopene carotenoid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.4.3.5 O2 + H2O + pyridoxamine 5'-phosphate = ammonia + H2O2 + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 7-hydroxy-chlorophyllide a + O2 + NADPH = chlorophyllide b + H2O + NADP+ chlorophyll cycle O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- oleate + NADPH + O2 = 18-hydroxyoleate + NADP+ + H2O cutin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- oleate + NADPH + O2 = 18-hydroxyoleate + NADP+ + H2O suberin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- leucocyanidin + α-ketoglutarate + O2 = cyanidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol + O2 + NADPH = 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA20 + α-ketoglutarate + O2 = GA29 + succinate + CO2 gibberellin inactivation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA19 + O2 + α-ketoglutarate = GA17 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.10.3.3 L-ascorbate + O2 = monodehydroascorbate + H2O ascorbate glutathione cycle O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- (5α)-campestan-3-one + O2 + NADPH = (22α)-hydroxy-5α-campestan-3-one + H2O + NADP+ brassinosteroid biosynthesis II O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.11.1.6 H2O2 = H2O + O2 removal of superoxide radicals O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.9 (2S)-pinocembrin + O2 + α-ketoglutarate = (2R,3R)-pinobanksin + CO2 + succinate pinobanksin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.9 O2 + NADPH + kynurenine = H2O + NADP+ + 3-hydroxy-L-kynurenine tryptophan degradation III (eukaryotic) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.1.3.15 glycolate + O2 = glyoxylate + H2O2 photorespiration O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.19.2 O2 = H2O stearoyl-ACP desaturation pathway O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.88 dihydroquercetin + NADPH + O2 = dihydromyricetin + NADP+ + H2O leucodelphinidin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- palmitate + NADPH + O2 = 16-hydroxypalmitate + NADP+ + H2O cutin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.14.1 N'-hydroxymethyl-norcotinine + NADPH + O2 = norcotinine + NADP+ + H2O nicotine degradation III O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- campestanol + O2 + NADPH = 6-deoxocathasterone + H2O + NADP+ brassinosteroid biosynthesis II O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.5.3.1 O2 + H2O + sarcosine = H2O2 + formaldehyde + glycine glycine betaine degradation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA12 + α-ketoglutarate + O2 = GA14 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.- β-carotene + O2 = β-cryptoxanthin + H2O carotenoid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 3-deoxy-capsidiol + O2 + NADPH = capsidiol + H2O + NADP+ capsidiol biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.4.3.6 aminoacetone + H2O + O2 = ammonia + methylglyoxal + H2O2 threonine degradation III (to methylglyoxal) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.- phytoene + O2 = phytofluene + H2O carotenoid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.- linolenate + O2 = 9-HPOT 9-LOX and 9-HPL pathway O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 marmesin + NADPH + O2 = psoralen + NADP+ + acetone + H2O linear furanocoumarin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.81 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = divinyl protochlorophyllide a + NADP+ + H2O chlorophyllide a biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 L-4-hydroxy-proline + O2 = pyrroline-hydroxy-carboxylate + H2O 4-hydroxyproline degradation I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.54 1,2-dihydroxy-3-keto-5-methylthiopentene + O2 = 2-oxo-4-methylthiobutanoate + formate methionine salvage pathway O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.15 GA20 + α-ketoglutarate + O2 = GA1 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- eriodictyol + NADPH + O2 = 3',4',5'-pentahydroxyflavanone + NADP+ + H2O leucodelphinidin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.39 O2 + NADPH + L-arginine = citrulline + NADP+ + nitric oxide citrulline-nitric oxide cycle O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA25 + α-ketoglutarate + O2 = GA13 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.21.6 lathosterol + O2 = 7-dehydro-cholesterol + H2O cholesterol biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.21.6 lathosterol + O2 = 7-dehydro-cholesterol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 5-epi-aristolochene + O2 + NADPH = 3-deoxy-capsidiol + H2O + NADP+ capsidiol biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.15.1.1 O2- + H+ = H2O2 + O2 removal of superoxide radicals O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.14.1 cotinine + NADPH + O2 = trans-3'-hydroxycotinine + NADP+ + H2O nicotine degradation III O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA44 + α-ketoglutarate + O2 = GA98 + succinate + CO2 gibberellin inactivation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA12 + α-ketoglutarate + O2 = GA110 + succinate + CO2 gibberellin inactivation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.79 GA12-aldehyde + NADPH + O2 = GA12 + NADP+ + H2O GA12 biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.3 coproporphyrinogen III + O2 + H+ = protoporphyrinogen IX + CO2 + H2O heme biosynthesis II O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.3 coproporphyrinogen III + O2 + H+ = protoporphyrinogen IX + CO2 + H2O chlorophyllide a biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.78 ent-kaur-16-en-19-ol + NADPH + H+ + O2 = ent-kaur-16-en-19-al + NADP+ + H2O GA12 biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.14.1 bupropion + NADPH + O2 = hydroxybupropion + NADP+ + H2O bupropion degradation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.15.7 choline + O2 + H+ = betaine aldehyde hydrate + H2O glycine betaine biosynthesis III (plants) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.14.1 acetone + NADPH + O2 = acetol + NADP+ + H2O acetone degradation (to methylglyoxal) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.- zeinoxanthin + NADPH + O2 = lutein + NADP+ + H2O carotenoid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.20 O2 + L-cysteine = 3-sulfinoalanine L-cysteine degradation I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- 6,7,4'-trihydroxyflavanone + NADPH + O2 = 2,6,7,4'-tetrahydroxyisoflavanone + NADP+ + H2O 6,7,4'-trihydroxyisoflavone biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.14.1 cotinine + NADPH + O2 = 5'-hydroxycotinine + NADP+ + H2O nicotine degradation III O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + O2 = 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + O2 = 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.70 24,25-dihydrolanosterol + O2 + NADPH = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.2.3.14 abscisic aldehyde + H2O + O2 = (+)-abscisate + H2O2 abscisic acid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4α-formyl-5α-cholesta-8-en-3β-ol + O2 = 4α-carboxy-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4,4-dimethyl-5α-cholesta-8-en-3-β-ol + O2 = 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.4 protoporphyrinogen IX + O2 = protoporphyrin IX + H2O heme biosynthesis II O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.4 protoporphyrinogen IX + O2 = protoporphyrin IX + H2O chlorophyllide a biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.-.-.- O2 = H2O aerobic respiration -- electron donor III O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.52 formononetin + NADPH + O2 = calycosin + NADP+ + H2O maackiain biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 diprenylphlorisovalerophenone + O2 = humulone + H2O humulone biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.99.1 O2 + myo-inositol = H2O + glucuronate UDP-D-glucuronate biosynthesis (from myo-inositol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA9 + α-ketoglutarate + O2 = GA51 + succinate + CO2 gibberellin inactivation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 3',4',5'-pentahydroxyflavanone + α-ketoglutarate + O2 = dihydromyricetin + succinate + CO2 leucodelphinidin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.99.3 indole-3-ethanol + O2 = indole-3-glycol tryptophan degradation V (side chain pathway) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.4.3.- O2 + L-aspartate = H2O2 + iminoaspartate NAD biosynthesis I (from aspartate) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.70 NADPH + O2 + obtusifoliol + H+ = H2O + NADP+ + formate + (4α)-methyl-(5α)-ergosta-8,14,24(28)-trien-3β-ol sterol biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 tryptamine + O2 + NADPH = N-hydroxyl-tryptamine + H2O + NADP+ IAA biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 GA12 + O2 = GA53 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 ferulate + NADPH + O2 = 5-hydroxy-ferulic-acid + H2O + NADP+ free phenylpropanoid acid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.-.- sphinganine + O2 + NADPH = 4-hydroxysphinganine + H2O + NADP+ sphingolipid metabolism O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 demethylsuberosin + O2 + NADPH = marmesin + NADP+ + H2O linear furanocoumarin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.99.3 indole-3-acetate + O2 = indole-3-glycolate tryptophan degradation V (side chain pathway) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.27 p-hydroxyphenylpyruvate + O2 = CO2 + homogentisate vitamin E biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.27 p-hydroxyphenylpyruvate + O2 = CO2 + homogentisate tyrosine degradation I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.27 p-hydroxyphenylpyruvate + O2 = CO2 + homogentisate plastoquinone biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- campesterol + O2 + NADPH = (22α)-hydroxy-campesterol + H2O + NADP+ brassinosteroid biosynthesis II O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.90 zeaxanthin + H+ + O2 = antheraxanthin + H2O carotenoid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.90 zeaxanthin + H+ + O2 = antheraxanthin + H2O xanthophyll cycle O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 7-hydroxy-chlorophyll a + H2O + NADP+ = chlorophyll a + O2 + NADPH chlorophyll cycle O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.13 GA1 + α-ketoglutarate + O2 = GA8 + succinate + CO2 gibberellin inactivation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.78 ent-kaur-16-en-19-al + NADPH + H+ + O2 = ent-kaurenoate + NADP+ + H2O GA12 biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.- linoleate + O2 = 9-HPOD 9-LOX and 9-HPL pathway O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.89 genistein + NADPH + O2 = 2'-hydroxygenistein + NADP+ + H2O wighteone and luteone biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.23 dihydroquercetin + α-ketoglutarate + O2 = quercetin + succinate + CO2 + H2O flavonol biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.9 eriodictyol + O2 + α-ketoglutarate = dihydroquercetin + CO2 + succinate leucopelargonidin and leucocyanidin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.9 eriodictyol + O2 + α-ketoglutarate = dihydroquercetin + CO2 + succinate leucodelphinidin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.79 ent-7-α-hydroxykaurenoate + NADPH + H+ + O2 = GA12-aldehyde + NADP+ + H2O GA12 biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.2.3.7 indole acetaldehyde + O2 + H2O = indole-3-acetate + H2O2 IAA biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- benzoate + NADPH + O2 = salicylate + NADP+ + H2O salicylate biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 18-hydroxyoleate + NADPH + O2 = 9,10-epoxy-18-hydroxystearate + NADP+ + H2O cutin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.70 lanosterol + NADPH + O2 = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.70 lanosterol + NADPH + O2 = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.81 Mg-protoporphyrin monomethyl ester + NADPH + H+ + O2 = 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.14 trans-cinnamate + O2 + NADPH = H2O + NADP+ + 2-coumarate coumarin biosynthesis (via 2-coumarate) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 chlorophyllide a + O2 + NADPH = 7-hydroxy-chlorophyllide a + H2O + NADP+ chlorophyll cycle O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.12 linoleate + O2 = 13-HPOD 13-LOX and 13-HPL pathway O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.12 linoleate + O2 = 13-HPOD divinyl ether biosynthesis II (13-LOX) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.21.6 5α-cholesta-7,24-dien-3β-ol + O2 = 7-dehydrodesmosterol + H2O cholesterol biosynthesis III (via desmosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.78 ent-kaur-16-ene + O2 + NADPH = H2O + NADP+ + ent-kaur-16-en-19-ol GA12 biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4α-formyl-4β-methyl-5α-cholesta-8-en-3β-ol + O2 = 4α-carboxy-4β-methyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.51 9'-cis-neoxanthin + O2 = xanthoxin + C25-allenic-apo-aldehyde abscisic acid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.17.4 L-ascorbate + 1-aminocyclopropane-1-carboxylate + O2 = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.14.1 nicotine + NADPH + O2 = 2'-hydroxynicotine + NADP+ + H2O nicotine degradation II O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 16-hydroxypalmitate + NADPH + O2 = 10,16-dihydroxypalmitate + NADP+ + H2O cutin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.99.3 indole acetaldehyde + O2 = indole-3-glycol aldehyde tryptophan degradation V (side chain pathway) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- campest-4-en-3-one + O2 + NADPH = (22α)-hydroxy-campest-4-en-3-one + H2O + NADP+ brassinosteroid biosynthesis II O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.53 pseudobaptigenin + NADPH + O2 = 2'-hydroxypseudobaptigenin + NADP+ + H2O maackiain biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA53 + O2 + α-ketoglutarate = GA44 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.9.3.1 O2 = H2O aerobic respiration -- electron donor II O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.7 O2 + squalene = (S)-2,3-Epoxysqualene + H2O sterol biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA37 + α-ketoglutarate + O2 = GA36 + succinate + CO2 + H2O gibberellin biosynthesis II (early C-3 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.- ε-carotene + O2 = ε,ε-carotene-3-diol + H2O lactucaxanthin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 diprenylphlorisobutyrophenone + O2 = cohumulone + H2O cohumulone biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.- zeaxanthin + O2 = crocetin dialdehyde + hydroxy-β-cyclocitral crocetin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA24 + O2 + α-ketoglutarate = GA9 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.- ε,ε-carotene-3-diol + O2 = lactucaxanthin + H2O lactucaxanthin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.9 naringenin + O2 + α-ketoglutarate = CO2 + succinate + dihydrokaempferol flavonoid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.11.6 O2 + 3-hydroxy-anthranilate = 2-amino-3-carboxymuconate semialdehyde tryptophan degradation III (eukaryotic) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA15 + α-ketoglutarate + O2 = GA37 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 5-epi-aristolochene + O2 + NADPH = 1-deoxy-capsidiol + H2O + NADP+ capsidiol biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.74 O2 + NADPH + 7-deoxyloganin = H2O + NADP+ + loganin secologanin and strictosidine biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA44 + α-ketoglutarate + O2 = GA38 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 (+)-pulegone + NADPH + O2 = (+)-menthofuran + NADP+ + H2O menthol biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- leucodelphinidin + O2 + α-ketoglutarate = delphinidin + H2O + CO2 + succinate anthocyanin biosynthesis (delphinidin 3-O-glucoside) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 4-coumarate + NADPH + O2 = H2O + caffeate + NADP+ suberin biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 4-coumarate + NADPH + O2 = H2O + caffeate + NADP+ free phenylpropanoid acid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.- phytofluene + O2 = ζ-carotene + H2O carotenoid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.90 antheraxanthin + H+ + O2 = violaxanthin + H2O carotenoid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.90 antheraxanthin + H+ + O2 = violaxanthin + H2O xanthophyll cycle O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.99.3 L-tryptophan + O2 = indole acetaldehyde + ammonia + CO2 tryptophan degradation V (side chain pathway) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 H2O = H+ + e- + O2 photosynthesis, light reaction O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.36 4-coumaroylquinate + NADPH + O2 = caffeoylquinate + NADP+ + H2O phenylpropanoid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.93 (+)-abscisate + NADPH + O2 = 8'-hydroxyabscisate + NADP+ + H2O phaseic acid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.-.-.- pheophorbide a + O2 = RCC + H2O chlorophyll a degradation O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.36 4-coumaroylshikimate + NADPH + O2 = caffeoylshikimate + NADP+ + H2O phenylpropanoid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4α-hydroxymethyl-5α-cholesta-8-en-3β-ol + O2 = 4α-formyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA24 + O2 + α-ketoglutarate = GA25 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- GA14 + O2 + α-ketoglutarate = GA37 + CO2 + succinate gibberellin biosynthesis II (early C-3 hydroxylation) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.13.12.3 O2 + L-tryptophan = indole-3-acetamide + H2O + CO2 IAA biosynthesis VI (via indole-3-acetamide) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.81 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.- L-tryptophan + NADPH + O2 = indole-3-acetaldoxime + CO2 + NADP+ + H2O IAA biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1-deoxy-capsidiol + O2 + NADPH = capsidiol + H2O + NADP+ capsidiol biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.5.3.11 spermine + O2 + H2O = 1-(3-aminopropyl)-4-aminobutanal + 1,3-diaminopropane + H2O2 β-alanine biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.8 nicotine + NADPH + O2 = nicotine-1'-N-oxide + NADP+ + H2O nicotine degradation II O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4-α-methyl zymosterol + O2 = 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.13.72 4-α-methyl zymosterol + O2 = 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.3.3.6 O2 = H2O2 fatty acid β-oxidation II (plant, saturated) O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.99.30 ζ-carotene + O2 = neurosporene + H2O carotenoid biosynthesis O2 oxygen*oxygen molecule 31.999 O2 O=O LIGAND-CPD:C00007:*CAS:7782-44-7 1.14.11.- leucopelargonidin + α-ketoglutarate + O2 = pelargonidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) trans-zeatin riboside triphosphate ZTP*zeatin triphosphate*tZRTP 591.301 C15 H24 N5 O14 P3 C1(C(O)C(O)C(O1)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)n2(c3(c(nc2)c(ncn3)NCC=C(C)CO)) trans-zeatin riboside triphosphate + H2O = trans-zeatin riboside diphosphate trans-zeatin biosynthesis trans-zeatin riboside triphosphate ZTP*zeatin triphosphate*tZRTP 591.301 C15 H24 N5 O14 P3 C1(C(O)C(O)C(O1)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)n2(c3(c(nc2)c(ncn3)NCC=C(C)CO)) isopentenyladenosine-5'-triphosphate + NADPH + H2O = trans-zeatin riboside triphosphate + NADP+ trans-zeatin biosynthesis 6-phospho-D-gluconate 6-p-gluconate*6-phospho-gluconate*6-phosphogluconic acid 276.136 C6 H13 O10 P1 C(OP(O)(=O)O)C(O)C(O)C(O)C(O)C(=O)O PUBCHEM:5459869:*LIGAND-CPD:C00345: 2.7.1.12 ATP + gluconate = 6-phospho-D-gluconate + ADP L-idonate degradation 6-phospho-D-gluconate 6-p-gluconate*6-phospho-gluconate*6-phosphogluconic acid 276.136 C6 H13 O10 P1 C(OP(O)(=O)O)C(O)C(O)C(O)C(O)C(=O)O PUBCHEM:5459869:*LIGAND-CPD:C00345: 3.1.1.31 D-glucono-δ-lactone-6-phosphate + H2O = 6-phospho-D-gluconate pentose phosphate pathway (oxidative branch) 6-phospho-D-gluconate 6-p-gluconate*6-phospho-gluconate*6-phosphogluconic acid 276.136 C6 H13 O10 P1 C(OP(O)(=O)O)C(O)C(O)C(O)C(O)C(=O)O PUBCHEM:5459869:*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 449.39 C21 H21 O11 C1(OC(CO)C(O)C(O)C(O)1)OC3(C(c2(ccc(O)c(O)c2))=Oc4(c(C=3)c(O)cc(O)c4)) 2.4.1.115 UDP-D-glucose + cyanidin = UDP + cyanidin-3-O-β-D-glucoside anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) L-galactose 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O1)CO)(O) GDP-L-galactose + H2O = L-galactose + GMP ascorbate biosynthesis L-galactose 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O1)CO)(O) 1.1.1.- L-galactose + NAD+ = L-galactono-1,4-lactone + NADH ascorbate biosynthesis HCO3- HCO3*bicarbonate*CO32-*CO3-2*carbonate 61.017 C1 H1 O3 C(=O)(O)[O-] CAS:71-52-3:*LIGAND-CPD:C00288:*CAS:144-55-8 6.3.4.18 5-aminoimidazole ribonucleotide + ATP + HCO3- = N5-carboxyaminoimidazole ribonucleotide + ADP purine nucleotides de novo biosynthesis I HCO3- HCO3*bicarbonate*CO32-*CO3-2*carbonate 61.017 C1 H1 O3 C(=O)(O)[O-] CAS:71-52-3:*LIGAND-CPD:C00288:*CAS:144-55-8 6.4.1.4 ATP + 3-methylcrotonyl-CoA + HCO3- = ADP + 3-methylglutaconyl-CoA leucine degradation I HCO3- HCO3*bicarbonate*CO32-*CO3-2*carbonate 61.017 C1 H1 O3 C(=O)(O)[O-] CAS:71-52-3:*LIGAND-CPD:C00288:*CAS:144-55-8 6.4.1.2 ATP + acetyl-CoA + HCO3- + H+ = ADP + malonyl-CoA fatty acid biosynthesis - initial steps HCO3- HCO3*bicarbonate*CO32-*CO3-2*carbonate 61.017 C1 H1 O3 C(=O)(O)[O-] CAS:71-52-3:*LIGAND-CPD:C00288:*CAS:144-55-8 4.3.99.1 HCO3- + cyanate = carbamate + CO2 cyanate degradation indole-3-ethanol Tryptophol 161.203 C10 H11 N1 O1 c1(c(CCO)c2(c([nH]1)cccc2)) CAS:526-55-6 1.13.99.3 indole-3-ethanol + O2 = indole-3-glycol tryptophan degradation V (side chain pathway) indole-3-ethanol Tryptophol 161.203 C10 H11 N1 O1 c1(c(CCO)c2(c([nH]1)cccc2)) CAS:526-55-6 1.1.99.8 indole-3-ethanol = indole acetaldehyde tryptophan degradation V (side chain pathway) dimethylglycine N,N-dimethylglycine 103.121 C4 H9 N1 O2 C(C(=O)O)N(C)C CAS:1118-68-9 2.1.1.5 L-homocysteine + glycine betaine = L-methionine + dimethylglycine glycine betaine degradation dimethylglycine N,N-dimethylglycine 103.121 C4 H9 N1 O2 C(C(=O)O)N(C)C CAS:1118-68-9 1.5.99.2 dimethylglycine + H2O = formaldehyde + sarcosine glycine betaine degradation GA17 gibberellin A17*gibberellin A17*GA17 378.421 C20 H26 O7 CC1([CH]4(C(CCC1)(C(=O)O)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA19 + O2 + α-ketoglutarate = GA17 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) kinetin 215.214 C10 H9 N5 O1 c2(ncnc1(c(NC=N1)2))(NCc3(occc3)) 2.4.1.- kinetin + UDP-D-glucose = kinetin-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis kinetin 215.214 C10 H9 N5 O1 c2(ncnc1(c(NC=N1)2))(NCc3(occc3)) 2.4.1.- kinetin + UDP-D-glucose = kinetin-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis 2-hydroxyformononetin 284.268 C16 H12 O5 C2(=C(c1(c(O)cc(cc1)OC))C(=O)c3(c(O2)cc(O)cc3)) CAS:1890-99-9 1.3.1.45 2-hydroxyformononetin + NADPH = (-)-vestitone + NADP+ medicarpin biosynthesis acrylyl-CoA acryloyl-CoA*acryloyl-coenzyme A*acrylyl-CoA 821.582 C24 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=C) CAS:5776-58-9 1.3.99.3 FADH2 + acrylyl-CoA = FAD + propionyl-CoA β-alanine biosynthesis II acrylyl-CoA acryloyl-CoA*acryloyl-coenzyme A*acrylyl-CoA 821.582 C24 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=C) CAS:5776-58-9 1.3.99.3 NADH + acrylyl-CoA = NAD+ + propionyl-CoA D-lactate fermentation to propionate and acetate acrylyl-CoA acryloyl-CoA*acryloyl-coenzyme A*acrylyl-CoA 821.582 C24 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=C) CAS:5776-58-9 4.2.1.54 D-lactoyl-CoA = H2O + acrylyl-CoA D-lactate fermentation to propionate and acetate acrylyl-CoA acryloyl-CoA*acryloyl-coenzyme A*acrylyl-CoA 821.582 C24 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=C) CAS:5776-58-9 4.2.1.17 acrylyl-CoA + H2O = 3-hydroxypropionyl-CoA β-alanine biosynthesis II isobutyryl-CoA 2-methylpropanoyl-CoA*isobutyryl-coenzyme A*2-methylpropionyl-CoA*S-(2-methylpropanoyl)-CoA 837.625 C25 H42 N7 O17 P3 S1 c1(c2(c(ncn1)n(cn2)C3(OC(C(C(O)3)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)C)))(N) CAS:15621-60-0 1.3.99.12 isobutyryl-CoA + FAD = methylacrylyl-CoA + FADH2 valine degradation I isobutyryl-CoA 2-methylpropanoyl-CoA*isobutyryl-coenzyme A*2-methylpropionyl-CoA*S-(2-methylpropanoyl)-CoA 837.625 C25 H42 N7 O17 P3 S1 c1(c2(c(ncn1)n(cn2)C3(OC(C(C(O)3)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)C)))(N) CAS:15621-60-0 2.3.1.156 malonyl-CoA + isobutyryl-CoA = phlorisobutyrophenone + CO2 + coenzyme A cohumulone biosynthesis isobutyryl-CoA 2-methylpropanoyl-CoA*isobutyryl-coenzyme A*2-methylpropionyl-CoA*S-(2-methylpropanoyl)-CoA 837.625 C25 H42 N7 O17 P3 S1 c1(c2(c(ncn1)n(cn2)C3(OC(C(C(O)3)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)C)))(N) CAS:15621-60-0 1.2.1.25 NAD+ + coenzyme A + 2-keto-isovalerate = NADH + CO2 + isobutyryl-CoA valine degradation I isobutyryl-CoA 2-methylpropanoyl-CoA*isobutyryl-coenzyme A*2-methylpropionyl-CoA*S-(2-methylpropanoyl)-CoA 837.625 C25 H42 N7 O17 P3 S1 c1(c2(c(ncn1)n(cn2)C3(OC(C(C(O)3)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)C)))(N) CAS:15621-60-0 2.3.1.168 coenzyme A = isobutyryl-CoA branched-chain α-keto acid dehydrogenase complex D-lactate (R)-2-hydroxypropanate*(R)-lactate*lactate 90.079 C3 H6 O3 C(=O)(O)C(O)C LIGAND-CPD:C00256:*CAS:10326-41-7 1.1.2.4 D-lactate = pyruvate aerobic respiration -- electron donors reaction list D-lactate (R)-2-hydroxypropanate*(R)-lactate*lactate 90.079 C3 H6 O3 C(=O)(O)C(O)C LIGAND-CPD:C00256:*CAS:10326-41-7 1.1.2.4 D-lactate = pyruvate methylglyoxal degradation I D-lactate (R)-2-hydroxypropanate*(R)-lactate*lactate 90.079 C3 H6 O3 C(=O)(O)C(O)C LIGAND-CPD:C00256:*CAS:10326-41-7 3.1.2.6 S-lactoyl-glutathione + H2O = glutathione + D-lactate methylglyoxal degradation I D-lactate (R)-2-hydroxypropanate*(R)-lactate*lactate 90.079 C3 H6 O3 C(=O)(O)C(O)C LIGAND-CPD:C00256:*CAS:10326-41-7 1.1.1.28 NAD+ + D-lactate = NADH + pyruvate mixed acid fermentation D-lactate (R)-2-hydroxypropanate*(R)-lactate*lactate 90.079 C3 H6 O3 C(=O)(O)C(O)C LIGAND-CPD:C00256:*CAS:10326-41-7 1.1.1.28 NAD+ + D-lactate = NADH + pyruvate D-lactate fermentation to propionate and acetate D-lactate (R)-2-hydroxypropanate*(R)-lactate*lactate 90.079 C3 H6 O3 C(=O)(O)C(O)C LIGAND-CPD:C00256:*CAS:10326-41-7 2.8.3.- D-lactate + propionyl-CoA = D-lactoyl-CoA + propionate D-lactate fermentation to propionate and acetate naringenin pelargidanon*salipurpol*naringetol*4;,5',7-trihydroxyflavanone*4',5,7-Trihydroxyflavanone*flavanone naringenin 272.257 C15 H12 O5 c1(cc(ccc1O)[CH]2(Oc3(c(C(C2)=O)c(O)cc(c3)O))) CAS:480-41-1 5.5.1.6 naringenin chalcone = naringenin flavonoid biosynthesis naringenin pelargidanon*salipurpol*naringetol*4;,5',7-trihydroxyflavanone*4',5,7-Trihydroxyflavanone*flavanone naringenin 272.257 C15 H12 O5 c1(cc(ccc1O)[CH]2(Oc3(c(C(C2)=O)c(O)cc(c3)O))) CAS:480-41-1 1.14.11.9 naringenin + O2 + α-ketoglutarate = CO2 + succinate + dihydrokaempferol flavonoid biosynthesis homoserine homo-ser*L-homoserine 119.12 C4 H9 N1 O3 C(O)(=O)[CH](N)CCO CAS:672-15-1:*LIGAND-CPD:C00263: 2.7.1.39 homoserine + ATP = O-phospho-L-homoserine + ADP threonine biosynthesis from homoserine homoserine homo-ser*L-homoserine 119.12 C4 H9 N1 O3 C(O)(=O)[CH](N)CCO CAS:672-15-1:*LIGAND-CPD:C00263: 2.7.1.39 homoserine + ATP = O-phospho-L-homoserine + ADP methionine biosynthesis II homoserine homo-ser*L-homoserine 119.12 C4 H9 N1 O3 C(O)(=O)[CH](N)CCO CAS:672-15-1:*LIGAND-CPD:C00263: 1.6.6.- L-canaline + NADPH = homoserine + ammonia + NADP+ canavanine degradation homoserine homo-ser*L-homoserine 119.12 C4 H9 N1 O3 C(O)(=O)[CH](N)CCO CAS:672-15-1:*LIGAND-CPD:C00263: 2.3.1.46 homoserine + succinyl-CoA = O-succinyl-L-homoserine + coenzyme A methionine biosynthesis I homoserine homo-ser*L-homoserine 119.12 C4 H9 N1 O3 C(O)(=O)[CH](N)CCO CAS:672-15-1:*LIGAND-CPD:C00263: 2.3.1.31 homoserine + acetyl-CoA = O-acetyl-L-homoserine + coenzyme A homocysteine biosynthesis homoserine homo-ser*L-homoserine 119.12 C4 H9 N1 O3 C(O)(=O)[CH](N)CCO CAS:672-15-1:*LIGAND-CPD:C00263: 1.1.1.3 homoserine = L-aspartate-semialdehyde + H+ homoserine biosynthesis homoserine homo-ser*L-homoserine 119.12 C4 H9 N1 O3 C(O)(=O)[CH](N)CCO CAS:672-15-1:*LIGAND-CPD:C00263: homoserine + ammonia = L-canaline canavanine biosynthesis 2,6,7,4'-tetrahydroxyisoflavanone 288.256 C15 H12 O6 C2(C(c1(ccc(O)cc1))C(=O)c3(c(O2)cc(O)c(O)c3))(O) 1.14.13.- 6,7,4'-trihydroxyflavanone + NADPH + O2 = 2,6,7,4'-tetrahydroxyisoflavanone + NADP+ + H2O 6,7,4'-trihydroxyisoflavone biosynthesis 2,6,7,4'-tetrahydroxyisoflavanone 288.256 C15 H12 O6 C2(C(c1(ccc(O)cc1))C(=O)c3(c(O2)cc(O)c(O)c3))(O) 4.2.1.- 2,6,7,4'-tetrahydroxyisoflavanone = 6,7,4'-trihydroxyisoflavone + H2O 6,7,4'-trihydroxyisoflavone biosynthesis cystathionine DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(CC(N)C(O)=O)SCC(N)C(=O)O LIGAND-CPD:C00542:*CAS:56-88-2 4.4.1.8 cystathionine + H2O = ammonia + pyruvate + L-homocysteine methionine biosynthesis II cystathionine DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(CC(N)C(O)=O)SCC(N)C(=O)O LIGAND-CPD:C00542:*CAS:56-88-2 4.4.1.8 cystathionine + H2O = ammonia + pyruvate + L-homocysteine methionine biosynthesis I cystathionine DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(CC(N)C(O)=O)SCC(N)C(=O)O LIGAND-CPD:C00542:*CAS:56-88-2 4.4.1.8 cystathionine + H2O = ammonia + pyruvate + L-homocysteine homocysteine and cysteine interconversion cystathionine DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(CC(N)C(O)=O)SCC(N)C(=O)O LIGAND-CPD:C00542:*CAS:56-88-2 4.4.1.1 cystathionine + H2O = ammonia + 2-oxobutanoate + L-cysteine homocysteine degradation cystathionine DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(CC(N)C(O)=O)SCC(N)C(=O)O LIGAND-CPD:C00542:*CAS:56-88-2 4.4.1.1 cystathionine + H2O = ammonia + 2-oxobutanoate + L-cysteine homocysteine and cysteine interconversion cystathionine DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(CC(N)C(O)=O)SCC(N)C(=O)O LIGAND-CPD:C00542:*CAS:56-88-2 2.5.1.- L-cysteine + O-phospho-L-homoserine = cystathionine methionine biosynthesis II cystathionine DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(CC(N)C(O)=O)SCC(N)C(=O)O LIGAND-CPD:C00542:*CAS:56-88-2 4.2.1.22 L-homocysteine + L-serine = H2O + cystathionine homocysteine degradation cystathionine DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(CC(N)C(O)=O)SCC(N)C(=O)O LIGAND-CPD:C00542:*CAS:56-88-2 4.2.1.22 L-homocysteine + L-serine = H2O + cystathionine homocysteine and cysteine interconversion cystathionine DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(CC(N)C(O)=O)SCC(N)C(=O)O LIGAND-CPD:C00542:*CAS:56-88-2 O-acetyl-L-homoserine + L-cysteine = cystathionine + acetate homocysteine and cysteine interconversion cystathionine DL-cystathionine*L-cystathionine 222.259 C7 H14 N2 O4 S1 C(CC(N)C(O)=O)SCC(N)C(=O)O LIGAND-CPD:C00542:*CAS:56-88-2 2.5.1.48 L-cysteine + O-succinyl-L-homoserine = succinate + cystathionine methionine biosynthesis I adenosine-3',5'-bisphosphate PAP*phosphoadenosine phosphate*adenosine 3',5'-bisphosphate 427.203 C10 H15 N5 O10 P2 C(OP(=O)(O)O)[CH]1(O[CH](C(O)C1OP(=O)(O)O)n2(c3(c(nc2)c(N)ncn3))) CAS:1053-73-2:*LIGAND-CPD:C00054: 1.8.4.8 sulfite + adenosine-3',5'-bisphosphate = phosphoadenosine-5'-phosphosulfate sulfate reduction I (assimilatory) D-ononitol 1D-4-O-methyl-myo-inositol*4-methyl-myo-inositol 194.184 C7 H14 O6 C1(C(OC)C(O)C(O)C(O)C(O)1)(O) 2.4.1.- D-ononitol + galactinol = D-galactosylononitol + myo-inositol galactosylcyclitol biosynthesis D-4'-phosphopantothenate 4'-phosphopantothenate*4'-P-Pantothenate*(R)-4'-phosphopantothenate 299.217 C9 H18 N1 O8 P1 C(OP(O)(=O)O)C(C)(C)C(O)C(=O)NCCC(O)=O LIGAND-CPD:C03492: 6.3.2.5 D-4'-phosphopantothenate + L-cysteine + CTP = R-4'-phosphopantothenoyl-L-cysteine + diphosphate + CMP coenzyme A biosynthesis D-4'-phosphopantothenate 4'-phosphopantothenate*4'-P-Pantothenate*(R)-4'-phosphopantothenate 299.217 C9 H18 N1 O8 P1 C(OP(O)(=O)O)C(C)(C)C(O)C(=O)NCCC(O)=O LIGAND-CPD:C03492: 2.7.1.33 pantothenate + ATP = D-4'-phosphopantothenate + ADP coenzyme A biosynthesis acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 6.4.1.2 acetyl-CoA = malonyl-CoA biotin-carboxyl carrier protein acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP oxidative ethanol degradation III acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP glutamate degradation VII (to butyrate) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP oxidative ethanol degradation I acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.- acetyl-CoA = coenzyme A + CO2 fatty acid biosynthesis - initial steps acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.10 acetoacetyl-CoA + H2O + acetyl-CoA = coenzyme A + 3-hydroxy-3-methyl-glutaryl-CoA mevalonate pathway acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.89 acetyl-CoA + tetrahydrodipicolinate + H2O = coenzyme A + L-2-acetamido-6-oxoheptanedioate lysine biosynthesis II acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.12 acetyl-CoA = coenzyme A pyruvate dehydrogenase complex acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 1.2.1.10 NAD+ + coenzyme A + acetaldehyde = NADH + acetyl-CoA mixed acid fermentation acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 1.2.1.10 NAD+ + coenzyme A + acetaldehyde = NADH + acetyl-CoA ethanol fermentation to acetate acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.8 acetyl-CoA = acetylphosphate + coenzyme A mixed acid fermentation acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.8 acetyl-CoA = acetylphosphate + coenzyme A D-lactate fermentation to propionate and acetate acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.8 acetyl-CoA = acetylphosphate + coenzyme A ethanol fermentation to acetate acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.8 acetyl-CoA = acetylphosphate + coenzyme A gallate degradation III (anaerobic) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.54 formate + acetyl-CoA = pyruvate + coenzyme A mixed acid fermentation acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.54 formate + acetyl-CoA = pyruvate + coenzyme A respiration (anaerobic) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 4.1.3.4 3-hydroxy-3-methyl-glutaryl-CoA = acetoacetate + acetyl-CoA mevalonate degradation acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 4.1.3.4 3-hydroxy-3-methyl-glutaryl-CoA = acetoacetate + acetyl-CoA leucine degradation I acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.- 3-hydroxy-5- oxohexanoyl-CoA + coenzyme A = 3-hydroxybutyryl-CoA + acetyl-CoA gallate degradation III (anaerobic) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.80 acetyl-CoA = coenzyme A glutathione-mediated detoxification acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.8.3.8 butyryl-CoA + acetate = butyrate + acetyl-CoA ethanol fermentation to acetate acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.8.3.8 butyryl-CoA + acetate = butyrate + acetyl-CoA gallate degradation III (anaerobic) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.14 α-ketoglutarate + H2O + acetyl-CoA = homocitrate + coenzyme A lysine biosynthesis IV acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.1 L-glutamate + acetyl-CoA = 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 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.1 L-glutamate + acetyl-CoA = N-acetyl-L-glutamate + coenzyme A ornithine biosynthesis acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = citrate + coenzyme A TCA cycle variation I acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = citrate + coenzyme A respiration (anaerobic) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = citrate + coenzyme A TCA cycle acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.9 acetyl-CoA = acetoacetyl-CoA + coenzyme A acetyl CoA fermentation to butyrate acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.9 acetyl-CoA = acetoacetyl-CoA + coenzyme A mevalonate pathway acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.9 acetyl-CoA = acetoacetyl-CoA + coenzyme A glutaryl-CoA degradation acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.9 acetyl-CoA = acetoacetyl-CoA + coenzyme A ethanol fermentation to acetate acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.31 homoserine + acetyl-CoA = O-acetyl-L-homoserine + coenzyme A homocysteine biosynthesis acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 1.2.7.1 pyruvate + coenzyme A = acetyl-CoA + CO2 reductive TCA cycle I acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 1.2.7.1 pyruvate + coenzyme A = acetyl-CoA + CO2 D-lactate fermentation to propionate and acetate acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 1.2.7.1 pyruvate + coenzyme A = acetyl-CoA + CO2 glutamate degradation VII (to butyrate) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.9 2-methylacetoacetyl-CoA + coenzyme A = propionyl-CoA + acetyl-CoA isoleucine degradation I acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.4 D-glucosamine-6-phosphate + acetyl-CoA = N-acetyl-D-glucosamine-6-phosphate + coenzyme A UDP-N-acetylgalactosamine biosynthesis acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.16 acetyl-CoA = coenzyme A fatty acid β-oxidation IV (plant, unsaturated, even number) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.16 acetyl-CoA = coenzyme A fatty acid β-oxidation I acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.16 acetyl-CoA = coenzyme A fatty acid β-oxidation II (plant, saturated) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 6.4.1.2 ATP + acetyl-CoA + HCO3- + H+ = ADP + malonyl-CoA fatty acid biosynthesis - initial steps acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.13 2-keto-isovalerate + acetyl-CoA + H2O = 2-isopropylmalate + coenzyme A leucine biosynthesis acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 1.2.1.- pyruvate + coenzyme A + NAD+ = acetyl-CoA + CO2 + NADH respiration (anaerobic) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.8.3.1 propionate + acetyl-CoA = propionyl-CoA + acetate D-lactate fermentation to propionate and acetate acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.38 acetyl-CoA = coenzyme A fatty acid biosynthesis - initial steps acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: oxocinnamoyl-CoA + coenzyme A = benzoyl-CoA + acetyl-CoA salicylate biosynthesis acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.9 acetyl-CoA + H2O + glyoxylate = malate + coenzyme A TCA cycle variation I acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) 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 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.3.- 2-oxo-4-methylthiobutanoate + acetyl-CoA + H2O = 2-(2'-methylthio)ethylmalic-acid + coenzyme A homomethionine biosynthesis acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.8.3.- 3-hydroxy-5-oxohexanoate + acetyl-CoA = 3-hydroxy-5- oxohexanoyl-CoA + acetate gallate degradation III (anaerobic) acetyl-CoA acetyl coenzyme-A*ac-CoA*acetylcoenzyme-A*acetyl-S-CoA*ac-S-CoA 809.571 C23 H38 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(C)=O) CAS:72-89-9*UM-BBD-CPD:c0031:*LIGAND-CPD:C00024: 2.3.1.29 glycine + acetyl-CoA = 2-amino-3-oxobutanoate + coenzyme A threonine degradation II N-hydroxyl-tryptamine 176.218 C10 H12 N2 O1 c1(c(CCNO)c2(c([nH]1)cccc2)) tryptamine + O2 + NADPH = N-hydroxyl-tryptamine + H2O + NADP+ IAA biosynthesis I N-hydroxyl-tryptamine 176.218 C10 H12 N2 O1 c1(c(CCNO)c2(c([nH]1)cccc2)) N-hydroxyl-tryptamine = indole-3-acetaldoxime IAA biosynthesis I 3-phospho-hydroxypyruvate 3-phosphonooxypyruvate*3-P-hydroxypyruvate*3-p-OH-pyr*3-phosphohydroxypyruvate*3-p-OH-pyruvate*3-p-hydroxy-pyr*3-phosphohydroxy-pyr*phosphohydroxypyruate 184.042 C3 H5 O7 P1 C(C(=O)C(O)=O)OP(=O)(O)O LIGAND-CPD:C03232:*CAS:3913-50-6 1.1.1.95 3-phosphoglycerate + NAD+ = 3-phospho-hydroxypyruvate + NADH serine biosynthesis 3-phospho-hydroxypyruvate 3-phosphonooxypyruvate*3-P-hydroxypyruvate*3-p-OH-pyr*3-phosphohydroxypyruvate*3-p-OH-pyruvate*3-p-hydroxy-pyr*3-phosphohydroxy-pyr*phosphohydroxypyruate 184.042 C3 H5 O7 P1 C(C(=O)C(O)=O)OP(=O)(O)O LIGAND-CPD:C03232:*CAS:3913-50-6 2.6.1.52 3-phospho-serine + α-ketoglutarate = L-glutamate + 3-phospho-hydroxypyruvate serine biosynthesis UDP-D-galacturonate UDP-galacturonate 580.289 C15 H22 N2 O18 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)C(O3)C(O)=O))) 5.1.3.6 UDP-D-glucuronate = UDP-D-galacturonate UDP-D-galacturonate biosynthesis I (from UDP-D-glucuronate) kynurenine L-kynurenine 208.216 C10 H12 N2 O3 C(=O)(O)C(N)CC(=O)c1(c(N)cccc1) CAS:343-65-7 1.14.13.9 O2 + NADPH + kynurenine = H2O + NADP+ + 3-hydroxy-L-kynurenine tryptophan degradation III (eukaryotic) kynurenine L-kynurenine 208.216 C10 H12 N2 O3 C(=O)(O)C(N)CC(=O)c1(c(N)cccc1) CAS:343-65-7 3.5.1.9 N-formylkynurenine + H2O = kynurenine + formate tryptophan degradation III (eukaryotic) tetrahydrogeranylgeranyl-chlorophyll a tetrahydroGG-chlorophyll a*tetrahydroGG-chl a*tetrahydrogeranylgeranyl-chl a 891.487 C55 H70 N4 O5 MG1 CC(CCCC(C)CCCC(C)CCC=C(C)C)=CCOC(=O)CCC6(C4(C1(C(C(=O)OC)C(=O)c2(c(C)c7(n(c=12)[Mg]58(n3(c(c(C=C)c(C)c3C=C(N=45)C(C)6)C=C9(C(C)=C(CC)C(C=7)=N89)))))))) 1.3.1.- 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 CC(CCCC(C)CCCC(C)CCC=C(C)C)=CCOC(=O)CCC6(C4(C1(C(C(=O)OC)C(=O)c2(c(C)c7(n(c=12)[Mg]58(n3(c(c(C=C)c(C)c3C=C(N=45)C(C)6)C=C9(C(C)=C(CC)C(C=7)=N89)))))))) 1.3.1.- tetrahydrogeranylgeranyl-chlorophyll a + NADPH = chlorophyll a + NADP+ chlorophyll a biosynthesis II selenide Hydrogen selenide 80.976 H2 SE1 [SeH2] CAS:531-44-2:*LIGAND-CPD:C01528: 2.7.9.3 H2O + selenide + ATP = selenophosphate + AMP selenocysteine biosynthesis violaxanthin 5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-β,β-carotene-3,3'-diol 600.88 C40 H56 O4 CC(C=CC12(C(C)(C)CC(O)CC(C)(O1)2))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC34(C(C)(O3)CC(O)CC(C)(C)4) 1.14.13.90 antheraxanthin + H+ + O2 = violaxanthin + H2O carotenoid biosynthesis violaxanthin 5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-β,β-carotene-3,3'-diol 600.88 C40 H56 O4 CC(C=CC12(C(C)(C)CC(O)CC(C)(O1)2))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC34(C(C)(O3)CC(O)CC(C)(C)4) 1.14.13.90 antheraxanthin + H+ + O2 = 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 CC(C=CC12(C(C)(C)CC(O)CC(C)(O1)2))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC34(C(C)(O3)CC(O)CC(C)(C)4) 1.10.99.3 violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O carotenoid biosynthesis violaxanthin 5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-β,β-carotene-3,3'-diol 600.88 C40 H56 O4 CC(C=CC12(C(C)(C)CC(O)CC(C)(O1)2))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC34(C(C)(O3)CC(O)CC(C)(C)4) 1.10.99.3 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 CC(C=CC12(C(C)(C)CC(O)CC(C)(O1)2))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC34(C(C)(O3)CC(O)CC(C)(C)4) 5.3.99.9 violaxanthin = trans-neoxanthin carotenoid biosynthesis (-)-jasmonic acid methyl ester jasmonic acid methyl ester*methyl jasmonate 224.299 C13 H20 O3 CCC=CC[CH]1([CH](CC(=O)OC)CCC(=O)1) 2.1.1.141 (-)-jasmonate + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + (-)-jasmonic acid methyl ester jasmonic 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 CC2(=CCCC(=C)C1(C(C(C)(C)C1)CC2)) 4.2.3.- trans, trans-farnesyl diphosphate = (E)-β-caryophyllene + diphosphate oleoresin sesquiterpene volatiles 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 130.143 C6 H10 O3 CCC(C)C(=O)C(=O)O LIGAND-CPD:C00671:*CAS:1460-34-0 2.6.1.42 L-isoleucine + α-ketoglutarate = 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 130.143 C6 H10 O3 CCC(C)C(=O)C(=O)O LIGAND-CPD:C00671:*CAS:1460-34-0 2.6.1.42 L-isoleucine + α-ketoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine biosynthesis 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 130.143 C6 H10 O3 CCC(C)C(=O)C(=O)O LIGAND-CPD:C00671:*CAS:1460-34-0 2.6.1.42 L-isoleucine + α-ketoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine degradation II 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 130.143 C6 H10 O3 CCC(C)C(=O)C(=O)O LIGAND-CPD:C00671:*CAS:1460-34-0 4.1.1.72 2-keto-3-methyl-valerate = 2-methylbutanal + CO2 isoleucine degradation II 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 130.143 C6 H10 O3 CCC(C)C(=O)C(=O)O LIGAND-CPD:C00671:*CAS:1460-34-0 4.2.1.9 2,3-dihydroxy-3-methylvalerate = 2-keto-3-methyl-valerate + H2O isoleucine biosynthesis 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 130.143 C6 H10 O3 CCC(C)C(=O)C(=O)O LIGAND-CPD:C00671:*CAS:1460-34-0 2-keto-3-methyl-valerate + NAD+ + coenzyme A = S-2-methyl-butyryl-CoA + NADH + CO2 isoleucine degradation I (+)-isomenthol 156.267 C10 H20 O1 CC(C)C1(C(O)CC(C)CC1) (+)-isomenthone + NADPH = (+)-isomenthol + NADP+ menthol biosynthesis nicotinamide 6-aminonicotinamide*vitamin PP*niacinamide 122.126 C6 H6 N2 O1 c1(ccc(cn1)C(N)=O) LIGAND-CPD:C00153:*CAS:98-92-0 3.2.2.14 nicotinamide mononucleotide + H2O = D-ribose-5-phosphate + nicotinamide NAD salvage pathway I nicotinamide 6-aminonicotinamide*vitamin PP*niacinamide 122.126 C6 H6 N2 O1 c1(ccc(cn1)C(N)=O) LIGAND-CPD:C00153:*CAS:98-92-0 3.2.2.14 nicotinamide mononucleotide + H2O = D-ribose-5-phosphate + nicotinamide pyridine nucleotide cycling (plants) nicotinamide 6-aminonicotinamide*vitamin PP*niacinamide 122.126 C6 H6 N2 O1 c1(ccc(cn1)C(N)=O) LIGAND-CPD:C00153:*CAS:98-92-0 4.2.1.84 3-cyanopyridine + H2O = nicotinamide aldoxime degradation nicotinamide 6-aminonicotinamide*vitamin PP*niacinamide 122.126 C6 H6 N2 O1 c1(ccc(cn1)C(N)=O) LIGAND-CPD:C00153:*CAS:98-92-0 3.5.1.4 nicotinamide + H2O = ammonia + nicotinate aldoxime degradation nicotinamide 6-aminonicotinamide*vitamin PP*niacinamide 122.126 C6 H6 N2 O1 c1(ccc(cn1)C(N)=O) LIGAND-CPD:C00153:*CAS:98-92-0 3.2.2.5 H2O + NAD+ = ADP-ribose + nicotinamide NAD salvage pathway I nicotinamide 6-aminonicotinamide*vitamin PP*niacinamide 122.126 C6 H6 N2 O1 c1(ccc(cn1)C(N)=O) LIGAND-CPD:C00153:*CAS:98-92-0 3.5.1.19 nicotinamide + H2O = ammonia + nicotinate NAD salvage pathway I nicotinamide 6-aminonicotinamide*vitamin PP*niacinamide 122.126 C6 H6 N2 O1 c1(ccc(cn1)C(N)=O) LIGAND-CPD:C00153:*CAS:98-92-0 3.5.1.19 nicotinamide + H2O = ammonia + nicotinate pyridine nucleotide cycling (plants) nicotinamide 6-aminonicotinamide*vitamin PP*niacinamide 122.126 C6 H6 N2 O1 c1(ccc(cn1)C(N)=O) LIGAND-CPD:C00153:*CAS:98-92-0 3.2.2.1 nicotinamide riboside + H2O = nicotinamide + D-ribose pyridine nucleotide cycling (plants) (+)-7-isojasmonate (+)-7-isojasmonic acid*isojasmonic acid*(3R,7S)-(+)-7-isojasmonate 210.272 C12 H18 O3 CCC=CCC1(C(CC(=O)O)CCC1=O) 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate + O2 = (+)-7-isojasmonate + acetate jasmonic acid biosynthesis (+)-7-isojasmonate (+)-7-isojasmonic acid*isojasmonic acid*(3R,7S)-(+)-7-isojasmonate 210.272 C12 H18 O3 CCC=CCC1(C(CC(=O)O)CCC1=O) (+)-7-isojasmonate = (-)-jasmonate 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 292.417 C18 H28 O3 CCC=CCC1(C(O1)=CC=CCCCCCCCC(O)=O) 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 292.417 C18 H28 O3 CCC=CCC1(C(O1)=CC=CCCCCCCCC(O)=O) 4.2.1.92 13-HPOT = H2O + 12,13(S)-epoxylinolenate jasmonic acid biosynthesis glycerate (R)-glycerate*D-glycerate 106.078 C3 H6 O4 C(O)C(O)C(O)=O CAS:473-81-4:*LIGAND-CPD:C00258:*CAS:6000-40-4 2.7.1.31 glycerate + ATP = 3-phosphoglycerate + ADP glycolate and glyoxylate degradation I glycerate (R)-glycerate*D-glycerate 106.078 C3 H6 O4 C(O)C(O)C(O)=O CAS:473-81-4:*LIGAND-CPD:C00258:*CAS:6000-40-4 2.7.1.31 glycerate + ATP = 3-phosphoglycerate + ADP allantoin degradation I glycerate (R)-glycerate*D-glycerate 106.078 C3 H6 O4 C(O)C(O)C(O)=O CAS:473-81-4:*LIGAND-CPD:C00258:*CAS:6000-40-4 2.7.1.31 glycerate + ATP = 3-phosphoglycerate + ADP photorespiration glycerate (R)-glycerate*D-glycerate 106.078 C3 H6 O4 C(O)C(O)C(O)=O CAS:473-81-4:*LIGAND-CPD:C00258:*CAS:6000-40-4 1.1.1.60 glycerate = tartronate semialdehyde + H+ glycolate and glyoxylate degradation I glycerate (R)-glycerate*D-glycerate 106.078 C3 H6 O4 C(O)C(O)C(O)=O CAS:473-81-4:*LIGAND-CPD:C00258:*CAS:6000-40-4 1.1.1.60 glycerate = tartronate semialdehyde + H+ allantoin degradation I glycerate (R)-glycerate*D-glycerate 106.078 C3 H6 O4 C(O)C(O)C(O)=O CAS:473-81-4:*LIGAND-CPD:C00258:*CAS:6000-40-4 1.1.1.29 glycerate + NAD+ = hydroxypyruvate + NADH photorespiration CMP-3-deoxy-D-manno-octulosonate CMP-2-dehydro-3-deoxy-D-octonate*CMP-KDO 543.377 C17 H26 N3 O15 P1 C(O)(=O)C(=O)CC(O)C(O)C(O)C(O)COP(=O)(O)OCC1(OC(C(O)C(O)1)n2(c(=O)nc(N)cc2)) 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) methylacrylyl-CoA methacrylyl-CoA*2-methylprop-2-enoyl-CoA*methacrylyl-coenzyme A 835.609 C25 H40 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(O)=O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)=C) CAS:6008-91-9 4.2.1.17 methylacrylyl-CoA + H2O = 3-hydroxy-isobutyryl-CoA valine degradation I methylacrylyl-CoA methacrylyl-CoA*2-methylprop-2-enoyl-CoA*methacrylyl-coenzyme A 835.609 C25 H40 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(O)=O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)=C) CAS:6008-91-9 1.3.99.12 isobutyryl-CoA + FAD = methylacrylyl-CoA + FADH2 valine degradation I 3-hydroxy-isobutyryl-CoA 3-Hydroxy-2-methylpropanoyl-CoA*3-hydroxy-isobutyryl-coenzyme A*3-Hydroxy-2-methylpropionyl-CoA 853.624 C25 H42 N7 O18 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)CO) 4.2.1.17 methylacrylyl-CoA + H2O = 3-hydroxy-isobutyryl-CoA valine degradation I 3-hydroxy-isobutyryl-CoA 3-Hydroxy-2-methylpropanoyl-CoA*3-hydroxy-isobutyryl-coenzyme A*3-Hydroxy-2-methylpropionyl-CoA 853.624 C25 H42 N7 O18 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)CO) 3.1.2.4 H2O + 3-hydroxy-isobutyryl-CoA = 3-hydroxy-isobutyrate + coenzyme A valine degradation I quinolinate 2,3-pyridinedicarboxylic acid*2,3-pyridinedicarboxylate*quinolinic acid*pyridine-2,3-dicarboxylic acid*pyridine-2,3-dicarboxylate 167.121 C7 H5 N1 O4 C(O)(=O)c1(c(C(=O)O)cccn1) LIGAND-CPD:C03722:*CAS:89-00-9 iminoaspartate + dihydroxy-acetone-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 167.121 C7 H5 N1 O4 C(O)(=O)c1(c(C(=O)O)cccn1) LIGAND-CPD:C03722:*CAS:89-00-9 2.4.2.19 CO2 + diphosphate + nicotinate nucleotide = 5-phosphoribosyl 1-pyrophosphate + quinolinate NAD biosynthesis I (from aspartate) 16:0-18:1-PC 1-16:0-2-18:1-phosphatidylcholine*1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine 761.093 C42 H83 N1 O8 P1 C(OP(=O)(O)OCC[N+](C)(C)C)C(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCC=CCCCCCCCC PUBCHEM:5282288: 1.14.99.- 16:0-18:1-PC = 16:0-18:2-PC phospholipid desaturation sulfoquinovosyldiacylglycerol SQDG C11 H16 O12 R11 R21 S1 C1(OC(CS(=O)(=O)O)C(O)C(O)C(O)1)OCC(OC([R2])=O)COC([R1])=O PUBCHEM:448048: UDP-sulfoquinovose = sulfoquinovosyldiacylglycerol + UDP glycolipid biosynthesis (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-glucosyl-(1->3)-α-D-glucosyl-(1->3)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1,6)]-α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 3459.833 C162 H270 N2 O72 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC3(C(O)C(C(O)C(O3)COC6(OC(COC4(C(C(O)C(O)C(O4)CO)OC5(OC(CO)C(O)C(O)C(O)5)))C(O)C(C(O)6)OC7(C(C(O)C(O)C(O7)CO)OC8(OC(CO)C(O)C(O)C(O)8))))OC9(C(C(O)C(O)C(O9)CO)OC10(C(C(O)C(O)C(O10)CO)OC11(C(O)C(C(O)C(O11)CO)OC12(C(O)C(C(O)C(O12)CO)OC13(OC(CO)C(O)C(O)C(O)13)))))))) glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-glucosyl phosphate = (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-glucosyl-(1->3)-α-D-glucosyl-(1->3)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1,6)]-α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 3459.833 C162 H270 N2 O72 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC3(C(O)C(C(O)C(O3)COC6(OC(COC4(C(C(O)C(O)C(O4)CO)OC5(OC(CO)C(O)C(O)C(O)5)))C(O)C(C(O)6)OC7(C(C(O)C(O)C(O7)CO)OC8(OC(CO)C(O)C(O)C(O)8))))OC9(C(C(O)C(O)C(O9)CO)OC10(C(C(O)C(O)C(O10)CO)OC11(C(O)C(C(O)C(O11)CO)OC12(C(O)C(C(O)C(O12)CO)OC13(OC(CO)C(O)C(O)C(O)13)))))))) (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-glucosyl phosphate = oligosaccharide-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis 3-hydroxy-3-methyl-glutaryl-CoA (S)-3-hydroxy-3-methylglutaryl-CoA*HMG-CoA*hydroxymethylglutaryl-CoA*3-hydroxy-3-methylglutaryl-coenzyme A*3-Hydroxy-3-methylglutaryl-CoA 911.661 C27 H44 N7 O20 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(=O)(O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(C)(O)CC(O)=O) CAS:1553-55-5 1.1.1.34 NADP+ + coenzyme A + (R)-mevalonate = NADPH + 3-hydroxy-3-methyl-glutaryl-CoA mevalonate pathway 3-hydroxy-3-methyl-glutaryl-CoA (S)-3-hydroxy-3-methylglutaryl-CoA*HMG-CoA*hydroxymethylglutaryl-CoA*3-hydroxy-3-methylglutaryl-coenzyme A*3-Hydroxy-3-methylglutaryl-CoA 911.661 C27 H44 N7 O20 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(=O)(O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(C)(O)CC(O)=O) CAS:1553-55-5 4.2.1.18 3-hydroxy-3-methyl-glutaryl-CoA = H2O + 3-methylglutaconyl-CoA leucine degradation I 3-hydroxy-3-methyl-glutaryl-CoA (S)-3-hydroxy-3-methylglutaryl-CoA*HMG-CoA*hydroxymethylglutaryl-CoA*3-hydroxy-3-methylglutaryl-coenzyme A*3-Hydroxy-3-methylglutaryl-CoA 911.661 C27 H44 N7 O20 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(=O)(O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(C)(O)CC(O)=O) CAS:1553-55-5 2.3.3.10 acetoacetyl-CoA + H2O + acetyl-CoA = coenzyme A + 3-hydroxy-3-methyl-glutaryl-CoA mevalonate pathway 3-hydroxy-3-methyl-glutaryl-CoA (S)-3-hydroxy-3-methylglutaryl-CoA*HMG-CoA*hydroxymethylglutaryl-CoA*3-hydroxy-3-methylglutaryl-coenzyme A*3-Hydroxy-3-methylglutaryl-CoA 911.661 C27 H44 N7 O20 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(=O)(O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(C)(O)CC(O)=O) CAS:1553-55-5 4.1.3.4 3-hydroxy-3-methyl-glutaryl-CoA = acetoacetate + acetyl-CoA mevalonate degradation 3-hydroxy-3-methyl-glutaryl-CoA (S)-3-hydroxy-3-methylglutaryl-CoA*HMG-CoA*hydroxymethylglutaryl-CoA*3-hydroxy-3-methylglutaryl-coenzyme A*3-Hydroxy-3-methylglutaryl-CoA 911.661 C27 H44 N7 O20 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(=O)(O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(C)(O)CC(O)=O) CAS:1553-55-5 4.1.3.4 3-hydroxy-3-methyl-glutaryl-CoA = acetoacetate + acetyl-CoA leucine degradation I 3-hydroxy-3-methyl-glutaryl-CoA (S)-3-hydroxy-3-methylglutaryl-CoA*HMG-CoA*hydroxymethylglutaryl-CoA*3-hydroxy-3-methylglutaryl-coenzyme A*3-Hydroxy-3-methylglutaryl-CoA 911.661 C27 H44 N7 O20 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(=O)(O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(C)(O)CC(O)=O) CAS:1553-55-5 1.1.1.88 (R)-mevalonate + NAD+ + coenzyme A = 3-hydroxy-3-methyl-glutaryl-CoA + NADH + H+ mevalonate degradation leucodelphinidin leucoefdin*leucodelfinidin 322.271 C15 H14 O8 c3(c2(OC(c1(cc(O)c(O)c(O)c1))C(O)C(O)c2c(O)cc(O)3)) 1.14.11.- leucodelphinidin + O2 + α-ketoglutarate = delphinidin + H2O + CO2 + succinate anthocyanin biosynthesis (delphinidin 3-O-glucoside) leucodelphinidin leucoefdin*leucodelfinidin 322.271 C15 H14 O8 c3(c2(OC(c1(cc(O)c(O)c(O)c1))C(O)C(O)c2c(O)cc(O)3)) 1.1.1.219 dihydromyricetin + NADPH = leucodelphinidin + NADP+ leucodelphinidin biosynthesis S-hydroxymethylglutathione glycine, N-(N-L-γ-S-(hydroxymethyl)-L-cysteinyl)-*HMGSH*HM-GSH*GS-CH2-OH*hydroxymethylglutathione 337.347 C11 H19 N3 O7 S1 C(C(O)=O)NC(=O)C(CSCO)NC(=O)CCC(N)C(O)=O 1.1.1.284 S-hydroxymethylglutathione = S-formylglutathione + H+ formaldehyde oxidation II (glutathione-dependent) S-hydroxymethylglutathione glycine, N-(N-L-γ-S-(hydroxymethyl)-L-cysteinyl)-*HMGSH*HM-GSH*GS-CH2-OH*hydroxymethylglutathione 337.347 C11 H19 N3 O7 S1 C(C(O)=O)NC(=O)C(CSCO)NC(=O)CCC(N)C(O)=O 4.4.1.22 S-hydroxymethylglutathione = formaldehyde + glutathione formaldehyde oxidation II (glutathione-dependent) 2,3-dimethyl-6-phytyl-1,4-benzoquinone 416.686 C28 H48 O2 CC(CCCC(C)C)CCCC(C)CCCC(C)=CCc1(c(O)c(C)c(C)c(c1)O) 2.1.1.- 2-methyl-6-phytyl-1,4-benzoquinone + S-adenosyl-L-methionine = 2,3-dimethyl-6-phytyl-1,4-benzoquinone + S-adenosyl-L-homocysteine vitamin E biosynthesis 2,3-dimethyl-6-phytyl-1,4-benzoquinone 416.686 C28 H48 O2 CC(CCCC(C)C)CCCC(C)CCCC(C)=CCc1(c(O)c(C)c(C)c(c1)O) 2,3-dimethyl-6-phytyl-1,4-benzoquinone = γ-tocopherol vitamin E biosynthesis (3Z)-nonenal 140.225 C9 H16 O1 CCCCCC=CCC=O 9-HPOD = (3Z)-nonenal + 9-oxo-nonanoate 9-LOX and 9-HPL pathway GA97 gibberellin A97*gibberellin A97*GA97 364.438 C20 H28 O6 CC1([CH]4(C(CC(O)C1)(C)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA53 + α-ketoglutarate + O2 = GA97 + succinate + CO2 gibberellin inactivation Fe3+ ferric iron*Fe3+*Fe+++*Fe+3 55.847 FE1 [Fe+++] 1.16.1.7 Fe2+ + NAD+ = Fe3+ + NADH Fe(III)-reduction and Fe(II) transport (mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->2)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 2486.981 C126 H210 N2 O42 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC3(C(O)C(C(O)C(O3)COC4(OC(CO)C(O)C(O)C(O)4))OC5(C(C(O)C(O)C(O5)CO)OC6(C(C(O)C(O)C(O6)CO)OC7(OC(CO)C(O)C(O)C(O)7)))))) (mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis (mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->2)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 2486.981 C126 H210 N2 O42 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC3(C(O)C(C(O)C(O3)COC4(OC(CO)C(O)C(O)C(O)4))OC5(C(C(O)C(O)C(O5)CO)OC6(C(C(O)C(O)C(O6)CO)OC7(OC(CO)C(O)C(O)C(O)7)))))) (mannosyl)4-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis 5-dehydroavenasterol 410.682 C29 H46 O1 CC(C)C(=CC)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC=3)CC(O)CC4)(C)))) 1.3.3.- avenasterol = 5-dehydroavenasterol sterol biosynthesis 5-dehydroavenasterol 410.682 C29 H46 O1 CC(C)C(=CC)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC=3)CC(O)CC4)(C)))) 1.3.1.21 5-dehydroavenasterol + NADPH = isofucosterol + NADP+ sterol biosynthesis cotinine 176.218 C10 H12 N2 O1 c1(ncc(cc1)[CH]2(N(C)C(=O)CC2)) 1.14.14.1 cotinine + NADPH + O2 = trans-3'-hydroxycotinine + NADP+ + H2O nicotine degradation III cotinine 176.218 C10 H12 N2 O1 c1(ncc(cc1)[CH]2(N(C)C(=O)CC2)) 2.4.1.17 cotinine + UDP-D-glucuronate = cotinine-glucuronide + UDP nicotine degradation III cotinine 176.218 C10 H12 N2 O1 c1(ncc(cc1)[CH]2(N(C)C(=O)CC2)) 1.14.14.1 cotinine + NADPH + O2 = 5'-hydroxycotinine + NADP+ + H2O nicotine degradation III cotinine 176.218 C10 H12 N2 O1 c1(ncc(cc1)[CH]2(N(C)C(=O)CC2)) 1.14.14.1 cotinine + NADPH + O2 = N'-hydroxymethyl-norcotinine + NADP+ + H2O nicotine degradation III cotinine 176.218 C10 H12 N2 O1 c1(ncc(cc1)[CH]2(N(C)C(=O)CC2)) cotinine = cotinine N-oxide nicotine degradation III cotinine 176.218 C10 H12 N2 O1 c1(ncc(cc1)[CH]2(N(C)C(=O)CC2)) 1.2.3.1 nicotine-Δ1'5'-iminium ion + O2 + H2O = cotinine + H2O2 nicotine degradation II cotinine 176.218 C10 H12 N2 O1 c1(ncc(cc1)[CH]2(N(C)C(=O)CC2)) 1.2.3.1 nicotine-Δ1'5'-iminium ion + O2 + H2O = cotinine + H2O2 nicotine degradation III cotinine 176.218 C10 H12 N2 O1 c1(ncc(cc1)[CH]2(N(C)C(=O)CC2)) cotinine = cotinine methonium ion nicotine degradation III propionate propionic acid*ethylformic acid*methylacetic acid*propanoate 74.079 C3 H6 O2 C(=O)(O)CC LIGAND-CPD:C00163:*CAS:79-09-4: 2.8.3.1 propionate + acetyl-CoA = propionyl-CoA + acetate D-lactate fermentation to propionate and acetate propionate propionic acid*ethylformic acid*methylacetic acid*propanoate 74.079 C3 H6 O2 C(=O)(O)CC LIGAND-CPD:C00163:*CAS:79-09-4: 6.2.1.17 coenzyme A + propionate + ATP = propionyl-CoA + diphosphate + AMP β-alanine biosynthesis II propionate propionic acid*ethylformic acid*methylacetic acid*propanoate 74.079 C3 H6 O2 C(=O)(O)CC LIGAND-CPD:C00163:*CAS:79-09-4: 2.8.3.- D-lactate + propionyl-CoA = D-lactoyl-CoA + propionate D-lactate fermentation to propionate and acetate fructose laevosan*levugen*laevoral*fructosteril*levulose*fru*fru-ring*D-fructose-ring*D-fructose 180.157 C6 H12 O6 C(O)C1(C(O)C(O)C(O)(O1)CO) CAS:57-48-7:*LIGAND-CPD:C00095:*CAS:30237-26-4 3.2.1.26 sucrose + H2O = α-D-glucose + fructose sucrose degradation III fructose laevosan*levugen*laevoral*fructosteril*levulose*fru*fru-ring*D-fructose-ring*D-fructose 180.157 C6 H12 O6 C(O)C1(C(O)C(O)C(O)(O1)CO) CAS:57-48-7:*LIGAND-CPD:C00095:*CAS:30237-26-4 3.2.1.- 6G,6-kestotetraose + H2O = 6G-kestotriose + fructose fructan degradation fructose laevosan*levugen*laevoral*fructosteril*levulose*fru*fru-ring*D-fructose-ring*D-fructose 180.157 C6 H12 O6 C(O)C1(C(O)C(O)C(O)(O1)CO) CAS:57-48-7:*LIGAND-CPD:C00095:*CAS:30237-26-4 3.2.1.26 H2O + sucrose-6-phosphate = β-D-glucose-6-phosphate + fructose sucrose degradation I fructose laevosan*levugen*laevoral*fructosteril*levulose*fru*fru-ring*D-fructose-ring*D-fructose 180.157 C6 H12 O6 C(O)C1(C(O)C(O)C(O)(O1)CO) CAS:57-48-7:*LIGAND-CPD:C00095:*CAS:30237-26-4 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP sucrose degradation III fructose laevosan*levugen*laevoral*fructosteril*levulose*fru*fru-ring*D-fructose-ring*D-fructose 180.157 C6 H12 O6 C(O)C1(C(O)C(O)C(O)(O1)CO) CAS:57-48-7:*LIGAND-CPD:C00095:*CAS:30237-26-4 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP sucrose degradation I fructose laevosan*levugen*laevoral*fructosteril*levulose*fru*fru-ring*D-fructose-ring*D-fructose 180.157 C6 H12 O6 C(O)C1(C(O)C(O)C(O)(O1)CO) CAS:57-48-7:*LIGAND-CPD:C00095:*CAS:30237-26-4 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP sucrose degradation to ethanol and lactate (anaerobic) fructose laevosan*levugen*laevoral*fructosteril*levulose*fru*fru-ring*D-fructose-ring*D-fructose 180.157 C6 H12 O6 C(O)C1(C(O)C(O)C(O)(O1)CO) CAS:57-48-7:*LIGAND-CPD:C00095:*CAS:30237-26-4 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP fructose degradation to pyruvate and lactate (anaerobic) fructose laevosan*levugen*laevoral*fructosteril*levulose*fru*fru-ring*D-fructose-ring*D-fructose 180.157 C6 H12 O6 C(O)C1(C(O)C(O)C(O)(O1)CO) CAS:57-48-7:*LIGAND-CPD:C00095:*CAS:30237-26-4 3.2.1.80 1-kestotriose + H2O = fructose + sucrose fructan degradation fructose laevosan*levugen*laevoral*fructosteril*levulose*fru*fru-ring*D-fructose-ring*D-fructose 180.157 C6 H12 O6 C(O)C1(C(O)C(O)C(O)(O1)CO) CAS:57-48-7:*LIGAND-CPD:C00095:*CAS:30237-26-4 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP sucrose degradation III fructose laevosan*levugen*laevoral*fructosteril*levulose*fru*fru-ring*D-fructose-ring*D-fructose 180.157 C6 H12 O6 C(O)C1(C(O)C(O)C(O)(O1)CO) CAS:57-48-7:*LIGAND-CPD:C00095:*CAS:30237-26-4 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP sucrose degradation to ethanol and lactate (anaerobic) fructose laevosan*levugen*laevoral*fructosteril*levulose*fru*fru-ring*D-fructose-ring*D-fructose 180.157 C6 H12 O6 C(O)C1(C(O)C(O)C(O)(O1)CO) CAS:57-48-7:*LIGAND-CPD:C00095:*CAS:30237-26-4 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP galactose degradation II fructose laevosan*levugen*laevoral*fructosteril*levulose*fru*fru-ring*D-fructose-ring*D-fructose 180.157 C6 H12 O6 C(O)C1(C(O)C(O)C(O)(O1)CO) CAS:57-48-7:*LIGAND-CPD:C00095:*CAS:30237-26-4 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP sucrose biosynthesis fructose laevosan*levugen*laevoral*fructosteril*levulose*fru*fru-ring*D-fructose-ring*D-fructose 180.157 C6 H12 O6 C(O)C1(C(O)C(O)C(O)(O1)CO) CAS:57-48-7:*LIGAND-CPD:C00095:*CAS:30237-26-4 2.7.1.69 fructose = fructose-6-phosphate fructose degradation to pyruvate and lactate (anaerobic) N'-hydroxymethyl-norcotinine 192.217 C10 H12 N2 O2 c1(ncc(cc1)[CH]2(N(CO)C(=O)CC2)) 1.14.14.1 cotinine + NADPH + O2 = N'-hydroxymethyl-norcotinine + NADP+ + H2O nicotine degradation III N'-hydroxymethyl-norcotinine 192.217 C10 H12 N2 O2 c1(ncc(cc1)[CH]2(N(CO)C(=O)CC2)) 1.14.14.1 N'-hydroxymethyl-norcotinine + NADPH + O2 = norcotinine + NADP+ + H2O nicotine degradation III 9,10,18-trihydroxystearate 332.479 C18 H36 O5 C(O)(=O)CCCCCCCC(O)C(O)CCCCCCCCO 9,10-epoxy-18-hydroxystearate + H2O = 9,10,18-trihydroxystearate cutin biosynthesis nornicotine 148.207 C9 H12 N2 c1(ncc(cc1)[CH]2([NH]CCC2)) nornicotine + H2O = norcotinine nicotine degradation II nornicotine 148.207 C9 H12 N2 c1(ncc(cc1)[CH]2([NH]CCC2)) nicotine + H2O = nornicotine + formaldehyde nicotine degradation II S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- 2-methyl-6-phytyl-1,4-benzoquinone + S-adenosyl-L-methionine = 2,3-dimethyl-6-phytyl-1,4-benzoquinone + S-adenosyl-L-homocysteine vitamin E biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.11 Mg-protoporphyrin + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + Mg-protoporphyrin monomethyl ester chlorophyllide a biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- N-methyl-β-alanine + S-adenosyl-L-methionine = N,N-dimethyl-β-alanine + S-adenosyl-L-homocysteine β-alanine betaine biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- N,N-dimethyl-β-alanine + S-adenosyl-L-methionine = β-alanine betaine + S-adenosyl-L-homocysteine β-alanine betaine biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- 2-methyl-6-solanyl-1,4-benzoquinone + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine plastoquinone biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 demethylphylloquinone + S-adenosyl-L-methionine = phylloquinone + S-adenosyl-L-homocysteine phylloquinone biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.49 nicotine + S-adenosyl-L-methionine = nicotine isomethonium ion + S-adenosyl-L-homocysteine nicotine degradation II S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.46 daidzein + S-adenosyl-L-methionine = formononetin + S-adenosyl-L-homocysteine pterocarpan biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.95 δ-tocopherol + S-adenosyl-L-methionine = β-tocopherol + S-adenosyl-L-homocysteine vitamin E biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 demethylmenaquinone-8 + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + menaquinone-8 menaquinone biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.79 oleate + S-adenosyl-L-methionine = dihydrosterculate + S-adenosyl-L-homocysteine cyclopropane and cyclopropene fatty acid biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) 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 S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.68 caffeate + S-adenosyl-L-methionine = ferulate + S-adenosyl-L-homocysteine suberin biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.68 caffeate + S-adenosyl-L-methionine = ferulate + S-adenosyl-L-homocysteine free phenylpropanoid acid biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.5.1.43 S-adenosyl-L-methionine = nicotianamine + 5'-methylthioadenosine 2'-deoxymugineic acid phytosiderophore biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.141 (-)-jasmonate + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + (-)-jasmonic acid methyl ester jasmonic acid biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.68 5-hydroxy-ferulic-acid + S-adenosyl-L-methionine = sinapate + S-adenosyl-L-homocysteine free phenylpropanoid acid biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 4.4.1.14 S-adenosyl-L-methionine = 5'-methylthioadenosine + 1-aminocyclopropane-1-carboxylate methionine salvage pathway S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 4.4.1.14 S-adenosyl-L-methionine = 5'-methylthioadenosine + 1-aminocyclopropane-1-carboxylate ethylene biosynthesis from methionine S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 4.1.1.50 S-adenosyl-L-methionine = CO2 + S-adenosyl-L-methioninamine spermidine biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 4.1.1.50 S-adenosyl-L-methionine = CO2 + S-adenosyl-L-methioninamine spermine biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.41 S-adenosyl-L-methionine + cycloartenol = S-adenosyl-L-homocysteine + 24-methylenecycloartenol sterol biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.95 γ-tocopherol + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + α-tocopherol vitamin E biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 (2S)-pinocembrin + S-adenosyl-L-methionine = pinostrobin + S-adenosyl-L-homocysteine pinobanksin biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.10 L-homocysteine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + L-methionine methionine biosynthesis II S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine choline biosynthesis I S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.68 5-hydroxy-coniferaldehyde + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + sinapaldehyde phenylpropanoid biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.103 N-dimethylethanolamine phosphate + S-adenosyl-L-methionine = phosphoryl-choline + S-adenosyl-L-homocysteine choline biosynthesis I S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.143 24-methylenelophenol + S-adenosyl-L-methionine = 24-ethylidenelophenol + S-adenosyl-L-homocysteine sterol biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) 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 S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine S-adenosylmethionine biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine methionine salvage pathway S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) 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 S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) 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 S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) 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 S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) 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 S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) 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 II S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) 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 I S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.69 bergaptol + S-adenosyl-L-methionine = bergapten + S-adenosyl-L-homocysteine linear furanocoumarin biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.49 β-alanine + S-adenosyl-L-methionine = N-methyl-β-alanine + S-adenosyl-L-homocysteine β-alanine betaine biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- quercetin + S-adenosyl-L-methionine = isorhamnetin + S-adenosyl-L-homocysteine flavonol biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + N-methylethanolamine phosphate choline biosynthesis I S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2-hydroxyisoflavanone + S-adenosyl-L-methionine = 2,7-dihydroxy-4'-methoxyisoflavanone + S-adenosyl-L-homocysteine pterocarpan biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + feruloyl-CoA suberin biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + feruloyl-CoA phenylpropanoid biosynthesis S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.8.1.6 dethiobiotin + S-adenosyl-L-methionine + sulfur donor = biotin + 5'-deoxyadenosine + L-methionine biotin biosynthesis I S-adenosyl-L-methionine S-adenosylmethionine*S-adenosyl-methionine*2-S-adenosyl-L-methionine*AdoMet*SAM*2-S-adenosyl-L-methionine*S-adenosyl-methionine*adenosylmethionine*S-adenosylmethionine 399.444 C15 H23 N6 O5 S1 C(CC(N)C(O)=O)[S+](C)CC1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00019:*CAS:29908-03-0 2.1.1.- S-adenosyl-L-methionine = S-adenosyl-L-homocysteine S-adenosyl-L-methionine cycle phosphoribosyl-ATP 1-(5-Phosphoribosyl)-ATP*N1-(5-phospho-D-ribosyl)-ATP*5-phosphoribosyl-ATP*1-(5-phospho-D-ribosyl)-ATP 719.279 C15 H25 N5 O20 P4 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n3(c2(ncn(c(=N)c2nc3)C4(OC(C(O)C(O)4)COP(O)(=O)O)))) LIGAND-CPD:C02739: 2.4.2.17 phosphoribosyl-ATP + diphosphate = ATP + 5-phosphoribosyl 1-pyrophosphate histidine biosynthesis I phosphoribosyl-ATP 1-(5-Phosphoribosyl)-ATP*N1-(5-phospho-D-ribosyl)-ATP*5-phosphoribosyl-ATP*1-(5-phospho-D-ribosyl)-ATP 719.279 C15 H25 N5 O20 P4 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n3(c2(ncn(c(=N)c2nc3)C4(OC(C(O)C(O)4)COP(O)(=O)O)))) LIGAND-CPD:C02739: 3.6.1.31 phosphoribosyl-ATP + H2O = phosphoribosyl-AMP + diphosphate histidine biosynthesis I sterculate sterculic acid 294.476 C19 H34 O2 CCCCCCCCC1(=C(C1)CCCCCCCC(O)=O) dihydrosterculate = sterculate cyclopropane and cyclopropene fatty acid biosynthesis 4-maleyl-acetoacetate 200.148 C8 H8 O6 C(=O)(O)C=CC(=O)CC(=O)CC(O)=O 5.2.1.2 4-maleyl-acetoacetate = 4-fumaryl-acetoacetate tyrosine degradation I (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->2)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 2811.265 C138 H230 N2 O52 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC6(OC(COC3(C(O)C(C(O)C(O3)CO)OC4(C(C(O)C(O)C(O4)CO)OC5(OC(CO)C(O)C(O)C(O)5))))C(O)C(C(O)6)OC7(C(C(O)C(O)C(O7)CO)OC8(C(C(O)C(O)C(O8)CO)OC9(OC(CO)C(O)C(O)C(O)9)))))) (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->2)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 2811.265 C138 H230 N2 O52 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC6(OC(COC3(C(O)C(C(O)C(O3)CO)OC4(C(C(O)C(O)C(O4)CO)OC5(OC(CO)C(O)C(O)C(O)5))))C(O)C(C(O)6)OC7(C(C(O)C(O)C(O7)CO)OC8(C(C(O)C(O)C(O8)CO)OC9(OC(CO)C(O)C(O)C(O)9)))))) (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis oligosaccharide-diphosphodolichol (glucosyl)3-(mannosyl)9-(N-acetylglucosaminyl)2-PP-Dol*{α-D-glucosyl-(1->2)-α-D-glucosyl-(1->3)-α-D-glucosyl-(1->3)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1,6)]-α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol*dolichyl diphosphooligosaccharide*(glucosyl)3-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol 3621.975 C168 H280 N2 O77 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC3(C(O)C(C(O)C(O3)COC6(OC(COC4(C(C(O)C(O)C(O4)CO)OC5(OC(CO)C(O)C(O)C(O)5)))C(O)C(C(O)6)OC7(C(C(O)C(O)C(O7)CO)OC8(OC(CO)C(O)C(O)C(O)8))))OC9(C(C(O)C(O)C(O9)CO)OC10(C(C(O)C(O)C(O10)CO)OC11(C(O)C(C(O)C(O11)CO)OC12(C(O)C(C(O)C(O12)CO)OC13(C(C(O)C(O)C(O13)CO)OC14(OC(CO)C(O)C(O)C(O)14))))))))) LIGAND-CPD:C04213: (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-glucosyl phosphate = oligosaccharide-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 [CH](C)=O LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 4.1.2.4 deoxyribose-5-phosphate = acetaldehyde + D-glyceraldehyde-3-phosphate (deoxy)ribose phosphate degradation acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 [CH](C)=O LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 1.2.1.10 NAD+ + coenzyme A + acetaldehyde = NADH + acetyl-CoA mixed acid fermentation acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 [CH](C)=O LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 1.2.1.10 NAD+ + coenzyme A + acetaldehyde = NADH + acetyl-CoA ethanol fermentation to acetate acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 [CH](C)=O LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 1.11.1.6 ethanol + H2O2 = H2O + acetaldehyde oxidative ethanol degradation III acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 [CH](C)=O LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ mixed acid fermentation acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 [CH](C)=O LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ sucrose degradation to ethanol and lactate (anaerobic) acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 [CH](C)=O LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ ethanol fermentation to acetate acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 [CH](C)=O LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ oxidative ethanol degradation I acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 [CH](C)=O LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 4.1.1.1 pyruvate = acetaldehyde + CO2 sucrose degradation to ethanol and lactate (anaerobic) acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 [CH](C)=O LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 1.2.1.3 acetaldehyde + NAD+ + H2O = NADH + acetate oxidative ethanol degradation III acetaldehyde acetic aldehyde*ethanal*aldehyde*ethyl aldehyde 44.053 C2 H4 O1 [CH](C)=O LIGAND-CPD:C00084:*UM-BBD-CPD:c0160:*LIGAND-CPD:c00084:*CAS:75-07-0 1.2.1.3 acetaldehyde + NAD+ + H2O = NADH + acetate oxidative ethanol degradation I 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol 428.697 C29 H48 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(CO)C(O)CC4)))) 1.14.13.72 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol 428.697 C29 H48 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(CO)C(O)CC4)))) 1.14.13.72 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol 428.697 C29 H48 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(CO)C(O)CC4)))) 1.14.13.72 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + O2 = 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol 428.697 C29 H48 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(CO)C(O)CC4)))) 1.14.13.72 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + O2 = 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) 2-isopropyl-3-oxosuccinate (2S)-2-isopropyl-3-oxosuccinate 174.153 C7 H10 O5 C(=O)(O)C(C(C)C)C(=O)C(O)=O 1.1.1.85 3-isopropylmalate + NAD+ = 2-isopropyl-3-oxosuccinate + NADH + H+ leucine biosynthesis 2-isopropyl-3-oxosuccinate (2S)-2-isopropyl-3-oxosuccinate 174.153 C7 H10 O5 C(=O)(O)C(C(C)C)C(=O)C(O)=O 2-isopropyl-3-oxosuccinate = 2-ketoisocaproate + CO2 leucine biosynthesis syn-copalyl diphosphate syn-copalyl diphosphate*syn-CDP 450.448 C20 H36 O7 P2 CC(=CCOP(=O)(O)OP(O)(=O)O)CCC2(C1(C)([CH](C(C)(C)CCC1)CCC2=C)) syn-copalyl diphosphate = 9β-pimara-7,15-diene momilactone biosynthesis syn-copalyl diphosphate syn-copalyl diphosphate*syn-CDP 450.448 C20 H36 O7 P2 CC(=CCOP(=O)(O)OP(O)(=O)O)CCC2(C1(C)([CH](C(C)(C)CCC1)CCC2=C)) syn-copalyl diphosphate = stemar-13-ene Oryzalexin S biosynthesis syn-copalyl diphosphate syn-copalyl diphosphate*syn-CDP 450.448 C20 H36 O7 P2 CC(=CCOP(=O)(O)OP(O)(=O)O)CCC2(C1(C)([CH](C(C)(C)CCC1)CCC2=C)) geranylgeranyl diphosphate = syn-copalyl diphosphate momilactone biosynthesis 10-hydroxygeraniol 8-hydroxygeraniol 170.251 C10 H18 O2 CC(=CCO)CCC=C(C)CO geraniol = 10-hydroxygeraniol secologanin and strictosidine biosynthesis 10-hydroxygeraniol 8-hydroxygeraniol 170.251 C10 H18 O2 CC(=CCO)CCC=C(C)CO 10-hydroxygeraniol = unknown secologanin and strictosidine biosynthesis 6,7,4'-trihydroxyflavanone 272.257 C15 H12 O5 c3(c2(OC(c1(ccc(O)cc1))CC(=O)c2cc(O)c(O)3)) liquiritigenin + NADPH + O2 = 6,7,4'-trihydroxyflavanone + NADP+ + H2O 6,7,4'-trihydroxyisoflavone biosynthesis 6,7,4'-trihydroxyflavanone 272.257 C15 H12 O5 c3(c2(OC(c1(ccc(O)cc1))CC(=O)c2cc(O)c(O)3)) 1.14.13.- 6,7,4'-trihydroxyflavanone + NADPH + O2 = 2,6,7,4'-tetrahydroxyisoflavanone + NADP+ + H2O 6,7,4'-trihydroxyisoflavone biosynthesis D-alanyl-D-alanine 160.172 C6 H12 N2 O3 CC(N)C(=O)NC(C)C(O)=O LIGAND-CPD:C00993:*CAS:923-16-0 6.3.2.10 UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + D-alanyl-D-alanine + ATP = ADP peptidoglycan biosynthesis I D-alanyl-D-alanine 160.172 C6 H12 N2 O3 CC(N)C(=O)NC(C)C(O)=O LIGAND-CPD:C00993:*CAS:923-16-0 6.3.2.4 D-alanine + ATP = D-alanyl-D-alanine + ADP peptidoglycan biosynthesis I cis-zeatin (Z)-2-methyl-4-(1H-purin-6-ylamino)but-2-en-1-ol*cZ 219.246 C10 H13 N5 O1 CC(CO)=CCNc1(ncnc2(c1nc[nH]2)) 2.4.1.- cis-zeatin + UDP-D-glucose = cis-zeatin-9-N-glucoside + UDP cytokinins 9-N-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)=CCNc1(ncnc2(c1nc[nH]2)) cis-zeatin riboside + H2O = cis-zeatin + D-ribose 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)=CCNc1(ncnc2(c1nc[nH]2)) 2.4.1.- cis-zeatin + UDP-D-glucose = cis-zeatin-7-N-glucoside + UDP cytokinins 7-N-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)=CCNc1(ncnc2(c1nc[nH]2)) 2.4.1.215 cis-zeatin + UDP-D-glucose = cis-zeatin-O-glucoside + 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)=CCNc1(ncnc2(c1nc[nH]2)) 1.5.99.12 cis-zeatin + H2O + FAD = 3-methyl-4-cis-hydroxy-2-butenal + adenine + FADH2 cytokinins degradation 5'-hydroxycotinine allohydroxycotinine 192.217 C10 H12 N2 O2 c1(ncc(cc1)C2(O)(N(C)C(=O)CC2)) 5'-hydroxycotinine = 4-oxo-4-(3-pyridyl)-N-methylbutanamide nicotine degradation III 5'-hydroxycotinine allohydroxycotinine 192.217 C10 H12 N2 O2 c1(ncc(cc1)C2(O)(N(C)C(=O)CC2)) 1.14.14.1 cotinine + NADPH + O2 = 5'-hydroxycotinine + NADP+ + H2O nicotine degradation III 18:2-t16:1-PG 1-18:2-2-trans-16:1-phosphatidylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(3E-hexadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) 744.984 C40 H73 O10 P1 C(OP(=O)(O)OCC(O)CO)C(OC(=O)CC=CCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-t16:1-PG = 18:3-t16:1-PG phospholipid desaturation 18:2-t16:1-PG 1-18:2-2-trans-16:1-phosphatidylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(3E-hexadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) 744.984 C40 H73 O10 P1 C(OP(=O)(O)OCC(O)CO)C(OC(=O)CC=CCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:1-t16:1-PG = 18:2-t16:1-PG phospholipid desaturation 18:2-t16:1-PG 1-18:2-2-trans-16:1-phosphatidylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(3E-hexadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) 744.984 C40 H73 O10 P1 C(OP(=O)(O)OCC(O)CO)C(OC(=O)CC=CCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-16:0-PG = 18:2-t16:1-PG phospholipid desaturation norcotinine demethylcotinine 162.191 C9 H10 N2 O1 c1(ncc(cc1)[CH]2([NH]C(=O)CC2)) norcotinine = 4-oxo-4-(3-pyridyl)-butanamide nicotine degradation II norcotinine demethylcotinine 162.191 C9 H10 N2 O1 c1(ncc(cc1)[CH]2([NH]C(=O)CC2)) norcotinine = 4-oxo-4-(3-pyridyl)-butanamide nicotine degradation III norcotinine demethylcotinine 162.191 C9 H10 N2 O1 c1(ncc(cc1)[CH]2([NH]C(=O)CC2)) nornicotine + H2O = norcotinine nicotine degradation II norcotinine demethylcotinine 162.191 C9 H10 N2 O1 c1(ncc(cc1)[CH]2([NH]C(=O)CC2)) 1.14.14.1 N'-hydroxymethyl-norcotinine + NADPH + O2 = norcotinine + NADP+ + H2O nicotine degradation III 7-keto-8-aminopelargonate 8-amino-7-oxononanoate*KAPA*7-KAP 187.238 C9 H17 N1 O3 CC(N)C(=O)CCCCCC(=O)O LIGAND-CPD:C01092: 2.3.1.47 pimeloyl-CoA + L-alanine = CO2 + coenzyme A + 7-keto-8-aminopelargonate biotin biosynthesis II 7-keto-8-aminopelargonate 8-amino-7-oxononanoate*KAPA*7-KAP 187.238 C9 H17 N1 O3 CC(N)C(=O)CCCCCC(=O)O LIGAND-CPD:C01092: 2.3.1.47 pimeloyl-CoA + L-alanine = CO2 + coenzyme A + 7-keto-8-aminopelargonate biotin biosynthesis I 7-keto-8-aminopelargonate 8-amino-7-oxononanoate*KAPA*7-KAP 187.238 C9 H17 N1 O3 CC(N)C(=O)CCCCCC(=O)O 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 II 7-keto-8-aminopelargonate 8-amino-7-oxononanoate*KAPA*7-KAP 187.238 C9 H17 N1 O3 CC(N)C(=O)CCCCCC(=O)O 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 I zeaxanthin β,β-carotene-3,3'-diol 568.881 C40 H56 O2 CC(C=CC1(=C(C)CC(O)CC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)(C)CC(O)CC(C)=2) 1.14.99.- zeaxanthin + O2 = crocetin dialdehyde + hydroxy-β-cyclocitral crocetin biosynthesis zeaxanthin β,β-carotene-3,3'-diol 568.881 C40 H56 O2 CC(C=CC1(=C(C)CC(O)CC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)(C)CC(O)CC(C)=2) 1.14.99.- β-cryptoxanthin + O2 = zeaxanthin + H2O carotenoid biosynthesis zeaxanthin β,β-carotene-3,3'-diol 568.881 C40 H56 O2 CC(C=CC1(=C(C)CC(O)CC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)(C)CC(O)CC(C)=2) 1.14.13.90 zeaxanthin + H+ + O2 = antheraxanthin + H2O carotenoid biosynthesis zeaxanthin β,β-carotene-3,3'-diol 568.881 C40 H56 O2 CC(C=CC1(=C(C)CC(O)CC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)(C)CC(O)CC(C)=2) 1.14.13.90 zeaxanthin + H+ + O2 = antheraxanthin + H2O xanthophyll cycle zeaxanthin β,β-carotene-3,3'-diol 568.881 C40 H56 O2 CC(C=CC1(=C(C)CC(O)CC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)(C)CC(O)CC(C)=2) 1.10.99.3 antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O carotenoid biosynthesis zeaxanthin β,β-carotene-3,3'-diol 568.881 C40 H56 O2 CC(C=CC1(=C(C)CC(O)CC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)(C)CC(O)CC(C)=2) 1.10.99.3 antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle isochorismate Isochorismic acid 226.185 C10 H10 O6 C(O)(=O)C1(C(O)C(C=CC=1)OC(=C)C(=O)O) LIGAND-CPD:C00885:*CAS:22642-82-6 5.4.4.2 chorismate = isochorismate menaquinone biosynthesis isochorismate Isochorismic acid 226.185 C10 H10 O6 C(O)(=O)C1(C(O)C(C=CC=1)OC(=C)C(=O)O) LIGAND-CPD:C00885:*CAS:22642-82-6 5.4.4.2 chorismate = isochorismate phylloquinone biosynthesis isochorismate Isochorismic acid 226.185 C10 H10 O6 C(O)(=O)C1(C(O)C(C=CC=1)OC(=C)C(=O)O) LIGAND-CPD:C00885:*CAS:22642-82-6 5.4.4.2 chorismate = isochorismate enterobactin biosynthesis isochorismate Isochorismic acid 226.185 C10 H10 O6 C(O)(=O)C1(C(O)C(C=CC=1)OC(=C)C(=O)O) LIGAND-CPD:C00885:*CAS:22642-82-6 5.4.4.2 chorismate = isochorismate salicylate biosynthesis isochorismate Isochorismic acid 226.185 C10 H10 O6 C(O)(=O)C1(C(O)C(C=CC=1)OC(=C)C(=O)O) LIGAND-CPD:C00885:*CAS:22642-82-6 3.3.2.1 H2O + isochorismate = pyruvate + 2,3-dihydro-2,3-dihydroxybenzoate enterobactin biosynthesis isochorismate Isochorismic acid 226.185 C10 H10 O6 C(O)(=O)C1(C(O)C(C=CC=1)OC(=C)C(=O)O) LIGAND-CPD:C00885:*CAS:22642-82-6 succinate-semialdehyde-thiamine PPi + isochorismate = 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate + thiamine diphosphate + pyruvate menaquinone biosynthesis isochorismate Isochorismic acid 226.185 C10 H10 O6 C(O)(=O)C1(C(O)C(C=CC=1)OC(=C)C(=O)O) LIGAND-CPD:C00885:*CAS:22642-82-6 succinate-semialdehyde-thiamine PPi + isochorismate = 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate + thiamine diphosphate + pyruvate phylloquinone biosynthesis isochorismate Isochorismic acid 226.185 C10 H10 O6 C(O)(=O)C1(C(O)C(C=CC=1)OC(=C)C(=O)O) LIGAND-CPD:C00885:*CAS:22642-82-6 isochorismate = salicylate + pyruvate salicylate biosynthesis S-2-methyl-butyryl-CoA 2-methylbutyryl-CoA*α-methylbutyryl-CoA*α-methylbutanoyl-CoA*2-methylbutanoyl-CoA 851.652 C26 H44 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)CC) 1.3.99.12 S-2-methyl-butyryl-CoA + FAD = tiglyl-CoA + FADH2 isoleucine degradation I S-2-methyl-butyryl-CoA 2-methylbutyryl-CoA*α-methylbutyryl-CoA*α-methylbutanoyl-CoA*2-methylbutanoyl-CoA 851.652 C26 H44 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)CC) 2-keto-3-methyl-valerate + NAD+ + coenzyme A = S-2-methyl-butyryl-CoA + NADH + CO2 isoleucine degradation I 4-prenylphlorisovalerophenone PPIVP*compound-X 278.347 C16 H22 O4 CC(C)=CCc1(c(O)c(C(=O)CC(C)C)c(O)cc(O)1) 2.5.1.- 4-prenylphlorisovalerophenone + dimethylallyl-PP = diprenylphlorisovalerophenone + diphosphate humulone biosynthesis 4-prenylphlorisovalerophenone PPIVP*compound-X 278.347 C16 H22 O4 CC(C)=CCc1(c(O)c(C(=O)CC(C)C)c(O)cc(O)1) 2.5.1.- phlorisovalerophenone + dimethylallyl-PP = 4-prenylphlorisovalerophenone + diphosphate humulone biosynthesis L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(=O)(O)C(N)CCC=O LIGAND-CPD:C01165: L-glutamate γ-semialdehyde = H2O proline biosynthesis V (from arginine) L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(=O)(O)C(N)CCC=O LIGAND-CPD:C01165: L-glutamate γ-semialdehyde = H2O proline biosynthesis II L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(=O)(O)C(N)CCC=O LIGAND-CPD:C01165: L-glutamate γ-semialdehyde = H2O 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(=O)(O)C(N)CCC=O LIGAND-CPD:C01165: L-glutamate γ-semialdehyde = H2O 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(=O)(O)C(N)CCC=O LIGAND-CPD:C01165: L-glutamate γ-semialdehyde = H2O proline biosynthesis I L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(=O)(O)C(N)CCC=O LIGAND-CPD:C01165: L-glutamate γ-semialdehyde = H2O citrulline biosynthesis L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(=O)(O)C(N)CCC=O LIGAND-CPD:C01165: L-glutamate + ATP + NADPH = ADP + L-glutamate γ-semialdehyde + NADP+ arginine biosynthesis IV L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(=O)(O)C(N)CCC=O LIGAND-CPD:C01165: 1.2.1.41 L-glutamate γ-semialdehyde + NADP+ = L-glutamate-5-phosphate + NADPH + H+ proline biosynthesis II L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(=O)(O)C(N)CCC=O 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(=O)(O)C(N)CCC=O 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(=O)(O)C(N)CCC=O LIGAND-CPD:C01165: 2.6.1.13 L-ornithine + α-ketoglutarate = L-glutamate + L-glutamate γ-semialdehyde proline biosynthesis V (from arginine) L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(=O)(O)C(N)CCC=O LIGAND-CPD:C01165: 2.6.1.13 L-ornithine + α-ketoglutarate = 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(=O)(O)C(N)CCC=O LIGAND-CPD:C01165: 2.6.1.13 L-ornithine + α-ketoglutarate = L-glutamate + L-glutamate γ-semialdehyde arginine biosynthesis IV L-glutamate γ-semialdehyde glutamic γ-semialdehyde*L-glutamate-5-semialdehyde*glutamate-semialdehyde 131.131 C5 H9 N1 O3 C(=O)(O)C(N)CCC=O LIGAND-CPD:C01165: 2.6.1.13 L-ornithine + α-ketoglutarate = 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(=O)(O)C(N)CCC=O LIGAND-CPD:C01165: 2.6.1.13 L-ornithine + α-ketoglutarate = L-glutamate + L-glutamate γ-semialdehyde citrulline biosynthesis formononetin 7-hydroxy-4'-methoxyisoflavone*4'-O-methyldaidzein 268.268 C16 H12 O4 C2(=C(c1(ccc(cc1)OC))C(=O)c3(c(O2)cc(O)cc3)) CAS:485-72-3:*NCI:93360: 1.14.13.52 formononetin + NADPH + O2 = calycosin + NADP+ + H2O maackiain biosynthesis formononetin 7-hydroxy-4'-methoxyisoflavone*4'-O-methyldaidzein 268.268 C16 H12 O4 C2(=C(c1(ccc(cc1)OC))C(=O)c3(c(O2)cc(O)cc3)) CAS:485-72-3:*NCI:93360: 2.1.1.46 daidzein + S-adenosyl-L-methionine = formononetin + S-adenosyl-L-homocysteine pterocarpan biosynthesis formononetin 7-hydroxy-4'-methoxyisoflavone*4'-O-methyldaidzein 268.268 C16 H12 O4 C2(=C(c1(ccc(cc1)OC))C(=O)c3(c(O2)cc(O)cc3)) CAS:485-72-3:*NCI:93360: 2,7-dihydroxy-4'-methoxyisoflavanone = formononetin + H2O pterocarpan biosynthesis L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 C(S)C(N)C(=O)O LIGAND-CPD:C00097:*CAS:52-90-4 6.1.1.16 L-cysteine + ATP = diphosphate + AMP tRNA charging pathway L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 C(S)C(N)C(=O)O LIGAND-CPD:C00097:*CAS:52-90-4 2.6.1.3 α-ketoglutarate + L-cysteine = L-glutamate + 3-mercaptopyruvate L-cysteine degradation III L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 C(S)C(N)C(=O)O LIGAND-CPD:C00097:*CAS:52-90-4 6.3.2.5 D-4'-phosphopantothenate + L-cysteine + CTP = R-4'-phosphopantothenoyl-L-cysteine + diphosphate + CMP coenzyme A biosynthesis L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 C(S)C(N)C(=O)O LIGAND-CPD:C00097:*CAS:52-90-4 3.4.11.2 Cys-Gly + H2O = L-cysteine + glycine γ-glutamyl cycle L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 C(S)C(N)C(=O)O LIGAND-CPD:C00097:*CAS:52-90-4 2.8.1.7 L-cysteine = L-alanine + protein-S-sulfanylcysteine alanine biosynthesis III L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 C(S)C(N)C(=O)O LIGAND-CPD:C00097:*CAS:52-90-4 2.5.1.- L-cysteine + O-phospho-L-homoserine = cystathionine methionine biosynthesis II L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 C(S)C(N)C(=O)O LIGAND-CPD:C00097:*CAS:52-90-4 6.3.2.2 L-cysteine + L-glutamate + ATP = L-γ-glutamylcysteine + ADP glutathione biosynthesis L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 C(S)C(N)C(=O)O LIGAND-CPD:C00097:*CAS:52-90-4 2.5.1.47 O-acetyl-L-serine + hydrogen sulfide = L-cysteine + acetate cysteine biosynthesis I L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 C(S)C(N)C(=O)O LIGAND-CPD:C00097:*CAS:52-90-4 4.4.1.1 cystathionine + H2O = ammonia + 2-oxobutanoate + L-cysteine homocysteine degradation L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 C(S)C(N)C(=O)O LIGAND-CPD:C00097:*CAS:52-90-4 4.4.1.1 cystathionine + H2O = ammonia + 2-oxobutanoate + L-cysteine homocysteine and cysteine interconversion L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 C(S)C(N)C(=O)O LIGAND-CPD:C00097:*CAS:52-90-4 1.13.11.20 O2 + L-cysteine = 3-sulfinoalanine L-cysteine degradation I L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 C(S)C(N)C(=O)O LIGAND-CPD:C00097:*CAS:52-90-4 O-acetyl-L-homoserine + L-cysteine = cystathionine + acetate homocysteine and cysteine interconversion L-cysteine C*carbocysteine*cysteine*Cys 121.154 C3 H7 N1 O2 S1 C(S)C(N)C(=O)O LIGAND-CPD:C00097:*CAS:52-90-4 2.5.1.48 L-cysteine + O-succinyl-L-homoserine = succinate + cystathionine methionine biosynthesis I campest-4-en-3-one methylcholestenone*(24R)-24-methyl-cholest-4-en-3-one*3-dehydro-Δ4-5-campesterol 398.671 C28 H46 O1 CC(C)C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(CC3)=CC(=O)CC4)(C)))) 1.1.1.145 campest-4-en-3β-ol = 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 CC(C)C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(CC3)=CC(=O)CC4)(C)))) 1.14.13.- campest-4-en-3-one + O2 + 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 CC(C)C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(CC3)=CC(=O)CC4)(C)))) 1.3.99.- campest-4-en-3-one + NADPH = (5α)-campestan-3-one + NADP+ brassinosteroid biosynthesis II maltodextrin 4-{(1,4)-α-D-glucosyl}(n-1)-D-glucose*maltodextrins*maltodextrin(n)*maltodextrin(n-2)*n+2 maltodextrin*linear maltodextrin 504.441 C18 H32 O16 C(O)C2(C(OC1(OC(CO)C(O)C(O)C1O))C(O)C(O)C(O2)OC3(C(CO)OC(O)C(O)C3O)) LIGAND-CPD:C01935: 5.4.99.15 maltodextrin = maltooligosyl-trehalose trehalose biosynthesis V maltodextrin 4-{(1,4)-α-D-glucosyl}(n-1)-D-glucose*maltodextrins*maltodextrin(n)*maltodextrin(n-2)*n+2 maltodextrin*linear maltodextrin 504.441 C18 H32 O16 C(O)C2(C(OC1(OC(CO)C(O)C(O)C1O))C(O)C(O)C(O2)OC3(C(CO)OC(O)C(O)C3O)) LIGAND-CPD:C01935: 3.2.1.141 maltooligosyl-trehalose = maltodextrin + trehalose trehalose biosynthesis V maltodextrin 4-{(1,4)-α-D-glucosyl}(n-1)-D-glucose*maltodextrins*maltodextrin(n)*maltodextrin(n-2)*n+2 maltodextrin*linear maltodextrin 504.441 C18 H32 O16 C(O)C2(C(OC1(OC(CO)C(O)C(O)C1O))C(O)C(O)C(O2)OC3(C(CO)OC(O)C(O)C3O)) LIGAND-CPD:C01935: 3.2.1.68 trehalose biosynthesis V isorhamnetin 3'-methoxyquercetin*3-methylquercetin 316.267 C16 H12 O7 c3(c2(oc(c1(cc(OC)c(O)cc1))c(O)c(=O)c2c(O)cc(O)3)) PUBCHEM:5281654: 2.1.1.- quercetin + S-adenosyl-L-methionine = isorhamnetin + S-adenosyl-L-homocysteine flavonol biosynthesis picrocrocin 330.377 C16 H26 O7 CC1(C)(CC(CC(C)=C1C=O)OC2(OC(CO)C(O)C(O)C(O)2)) 2.4.1.- hydroxy-β-cyclocitral + UDP-D-glucose = picrocrocin + UDP crocetin biosynthesis δ-tocopherol 402.659 C27 H46 O2 CC(C)CCCC(C)CCCC(C)CCCC1(C)(OC2(C(CC1)=CC(O)=CC=2C)) 2-methyl-6-phytyl-1,4-benzoquinone = δ-tocopherol vitamin E biosynthesis δ-tocopherol 402.659 C27 H46 O2 CC(C)CCCC(C)CCCC(C)CCCC1(C)(OC2(C(CC1)=CC(O)=CC=2C)) 2.1.1.95 δ-tocopherol + S-adenosyl-L-methionine = β-tocopherol + S-adenosyl-L-homocysteine vitamin E biosynthesis 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 336.215 C11 H15 N1 O9 P1 [CH]2([n+]1(cc(C(=O)O)ccc1))(O[CH]([CH](O)[CH](O)2)COP(O)(=O)O) LIGAND-CPD:C01185:*CAS:321-02-8 2.7.1.- nicotinate riboside + ATP = nicotinate nucleotide + ADP pyridine nucleotide cycling (plants) 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 336.215 C11 H15 N1 O9 P1 [CH]2([n+]1(cc(C(=O)O)ccc1))(O[CH]([CH](O)[CH](O)2)COP(O)(=O)O) LIGAND-CPD:C01185:*CAS:321-02-8 2.4.2.11 nicotinate nucleotide + diphosphate = nicotinate + 5-phosphoribosyl 1-pyrophosphate NAD salvage pathway I 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 336.215 C11 H15 N1 O9 P1 [CH]2([n+]1(cc(C(=O)O)ccc1))(O[CH]([CH](O)[CH](O)2)COP(O)(=O)O) LIGAND-CPD:C01185:*CAS:321-02-8 2.4.2.11 nicotinate nucleotide + diphosphate = nicotinate + 5-phosphoribosyl 1-pyrophosphate pyridine nucleotide cycling (plants) 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 336.215 C11 H15 N1 O9 P1 [CH]2([n+]1(cc(C(=O)O)ccc1))(O[CH]([CH](O)[CH](O)2)COP(O)(=O)O) LIGAND-CPD:C01185:*CAS:321-02-8 3.5.1.42 nicotinamide mononucleotide + H2O = ammonia + nicotinate nucleotide NAD salvage pathway I 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 336.215 C11 H15 N1 O9 P1 [CH]2([n+]1(cc(C(=O)O)ccc1))(O[CH]([CH](O)[CH](O)2)COP(O)(=O)O) LIGAND-CPD:C01185:*CAS:321-02-8 2.7.7.18 ATP + nicotinate nucleotide = diphosphate + deamido-NAD NAD biosynthesis I (from aspartate) 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 336.215 C11 H15 N1 O9 P1 [CH]2([n+]1(cc(C(=O)O)ccc1))(O[CH]([CH](O)[CH](O)2)COP(O)(=O)O) LIGAND-CPD:C01185:*CAS:321-02-8 2.7.7.18 ATP + nicotinate nucleotide = diphosphate + deamido-NAD NAD salvage pathway I 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 336.215 C11 H15 N1 O9 P1 [CH]2([n+]1(cc(C(=O)O)ccc1))(O[CH]([CH](O)[CH](O)2)COP(O)(=O)O) LIGAND-CPD:C01185:*CAS:321-02-8 2.7.7.18 ATP + nicotinate nucleotide = diphosphate + deamido-NAD pyridine nucleotide cycling (plants) 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 336.215 C11 H15 N1 O9 P1 [CH]2([n+]1(cc(C(=O)O)ccc1))(O[CH]([CH](O)[CH](O)2)COP(O)(=O)O) LIGAND-CPD:C01185:*CAS:321-02-8 3.2.2.- nicotinate nucleotide + H2O = nicotinate + D-ribose-5-phosphate pyridine nucleotide cycling (plants) 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 336.215 C11 H15 N1 O9 P1 [CH]2([n+]1(cc(C(=O)O)ccc1))(O[CH]([CH](O)[CH](O)2)COP(O)(=O)O) LIGAND-CPD:C01185:*CAS:321-02-8 2.4.2.19 CO2 + diphosphate + nicotinate nucleotide = 5-phosphoribosyl 1-pyrophosphate + quinolinate NAD biosynthesis I (from aspartate) (E)-β-ocimene trans-β-ocimene 136.236 C10 H16 CC(C=C)=CCC=C(C)C 4.2.3.- geranyl-PP = (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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ NAD salvage pathway 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH gluconeogenesis 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH sucrose degradation to ethanol and lactate (anaerobic) 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH fructose degradation to pyruvate and lactate (anaerobic) 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH glucose fermentation to lactate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.77 NADH + L-lactaldehyde = NAD+ fucose 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ mixed acid fermentation 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ sucrose degradation to ethanol and lactate (anaerobic) 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ ethanol fermentation to acetate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ oxidative ethanol 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.27 NAD+ + L-lactate = NADH + pyruvate sucrose degradation to ethanol and lactate (anaerobic) 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.27 NAD+ + L-lactate = NADH + pyruvate fructose degradation to pyruvate and lactate (anaerobic) 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.27 NAD+ + L-lactate = NADH + pyruvate glucose fermentation to lactate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 α-ketoglutarate + coenzyme A + NAD+ = succinyl-CoA + CO2 + NADH TCA 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.27 NAD+ + coenzyme A + methylmalonate-semialdehyde = NADH + CO2 + propionyl-CoA 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.5.1.12 NAD+ + H2O = L-glutamate + NADH proline 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.5.1.12 NAD+ + H2O = 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.3.99.3 NADH + acrylyl-CoA = NAD+ + propionyl-CoA D-lactate fermentation to propionate and acetate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 α-ketoadipate + 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 α-ketoadipate + NAD+ + coenzyme A = CO2 + NADH + glutaryl-CoA tryptophan degradation 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 3.2.2.5 H2O + NAD+ = ADP-ribose + nicotinamide NAD salvage pathway 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.8 betaine aldehyde + NAD+ + H2O = 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.32 H2O + NAD+ + 2-aminomuconate semialdehyde = NADH + 2-amino-muconate tryptophan degradation 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.103 L-threonine + NAD+ = 2-amino-3-oxobutanoate + NADH threonine 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.103 L-threonine + NAD+ = 2-amino-3-oxobutanoate + NADH threonine degradation III (to methylglyoxal) 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.103 L-threonine + NAD+ = 2-amino-3-oxobutanoate + NADH aminopropanol 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.5.1.15 5,10-methylene-THF + NAD+ = NADH folate transformations 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.16.1.7 Fe2+ + NAD+ = Fe3+ + NADH 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.38 NAD+ + malate = NADH + CO2 + pyruvate gluconeogenesis 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 2.7.1.23 NAD+ + ATP = 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 2-ketoisocaproate + 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ purine 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ salvage pathways of adenine, hypoxanthine, and their nucleosides 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ ureide 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.87 homoisocitrate + NAD+ = α-ketoadipate + CO2 + NADH + H+ lysine 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.8.1.4 NAD+ = NADH + H+ branched-chain α-keto acid 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.5.1.9 H2O + NAD+ + saccharopine = L-glutamate + NADH + 2-aminoadipate-6-semialdehyde 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.6.5.3 ubiquinone-8 + NADH = ubiquinol-8 + NAD+ aerobic respiration -- electron donors reaction list 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.6.5.3 ubiquinone-8 + NADH = ubiquinol-8 + NAD+ respiration (anaerobic)-- electron donors reaction list 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.6.5.3 ubiquinone-8 + NADH = ubiquinol-8 + 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 2-keto-3-methyl-valerate + NAD+ + coenzyme A = S-2-methyl-butyryl-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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.99.8 indole-3-glyoxal + NADH + H+ = indole-3-ketol + NAD+ tryptophan degradation V (side chain 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.22 UDP-D-glucose + H2O + NAD+ = UDP-D-glucuronate + NADH UDP-D-xylose 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.22 UDP-D-glucose + H2O + NAD+ = UDP-D-glucuronate + NADH galactose 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.1 3-methylbutanal + NADH = isoamyl alcohol + 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 3.1.3.2 NADP+ + H2O = NAD+ NAD salvage pathway 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.3.1.28 NAD+ + 2,3-dihydro-2,3-dihydroxybenzoate = NADH + 2,3-dihydroxybenzoate enterobactin 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.- L-galactose + NAD+ = L-galactono-1,4-lactone + NADH ascorbate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 2-amino-muconate + H2O + NADH = NH(4)OH + α-ketoadipate + NAD+ tryptophan degradation 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.88 (R)-mevalonate + NAD+ + coenzyme A = 3-hydroxy-3-methyl-glutaryl-CoA + NADH + H+ mevalonate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.5.1.7 H2O + NAD+ + saccharopine = NADH + α-ketoglutarate + L-lysine lysine 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.1 3-methylthiopropanal + NADH + H+ = methionol + NAD+ methionine 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.262 4-(phosphonooxy)-threonine + NAD+ = NADH + (2S)-2-amino-3-oxo-4-phosphonooxybutanoate pyridoxal 5'-phosphate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.3.1.- crotonyl-CoA + NADH = butyryl-CoA + NAD+ ethanol fermentation to acetate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.22 H2O + NAD+ + L-lactaldehyde = NADH + L-lactate fucose 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.25 NAD+ + coenzyme A + 2-keto-isovalerate = NADH + CO2 + isobutyryl-CoA 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.85 3-isopropylmalate + NAD+ = 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.99.8 indole-3-glycol aldehyde + NADH + H+ = indole-3-glycol + NAD+ tryptophan degradation V (side chain 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.223 NAD+ + (-)-trans-Isopiperitenol = NADH + (-)-isopiperitenone menthol 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.35 NAD+ = NADH fatty acid β-oxidation IV (plant, unsaturated, even number) 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.35 NAD+ = NADH fatty acid β-oxidation 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.35 NAD+ = NADH fatty acid β-oxidation II (plant, 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.3.1.9 NAD+ = NADH 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.72 D-erythrose-4-phosphate + NAD+ + H2O = erythronate-4-phosphate + NADH + H+ pyridoxal 5'-phosphate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.- N2-succinyl-L-glutamate 5-semialdehyde + NAD+ + H2O = N2-succinylglutamate + NADH arginine 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.178 NAD+ + 2-methyl-3-hydroxybutyryl-CoA = 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.31 NAD+ + 3-hydroxy-isobutyrate = NADH + 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.1 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.8.1.4 NAD+ = NADH + H+ pyruvate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 4.3.1.12 L-ornithine + NAD+ = L-proline + ammonia + NADH + H+ arginine degradation VII (arginase 3 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.24 H2O + NAD+ + succinate semialdehyde = NADH + succinate glutamate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.29 glycerate + NAD+ = 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.23 histidinal + NAD+ + H2O = L-histidine + NADH histidine 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.1 phenylacetaldehyde + NADH = 2-phenylethanol + NAD+ phenylalanine 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.6.5.3 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.6.5.3 NADH = NAD+ aerobic respiration -- electron donor 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ purine 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ salvage pathways of purine nucleosides II (plant) 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.10 NAD+ + coenzyme A + acetaldehyde = NADH + acetyl-CoA mixed acid fermentation 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.10 NAD+ + coenzyme A + acetaldehyde = NADH + acetyl-CoA ethanol fermentation to acetate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH folate transformations 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH formylTHF 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH formylTHF 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 3.6.1.22 H2O + NAD+ = nicotinamide mononucleotide + AMP NAD salvage pathway 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 3.6.1.22 H2O + NAD+ = nicotinamide mononucleotide + AMP NAD salvage pathway 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 3.6.1.22 H2O + NAD+ = 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.23 histidinol + NAD+ = histidinal + NADH histidine 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.57 NAD+ + D-mannonate = NADH + fructuronate β-D-glucuronide 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.21 H2O + NAD+ + glycolaldehyde = NADH + glycolate ethylene glycol 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 NAD+ = dipicolinate + NADH + H+ lysine 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH purine 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH salvage pathways of purine nucleosides 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH ureide 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH salvage pathways of purine nucleosides II (plant) 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH purine nucleotides de novo 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.35 acetoacetyl-CoA + NADH = 3-hydroxybutyryl-CoA + NAD+ acetyl CoA fermentation to butyrate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.35 acetoacetyl-CoA + NADH = 3-hydroxybutyryl-CoA + NAD+ glutaryl-CoA 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.59 NAD+ + 3-hydroxy-propionate = NADH + malonate semialdehyde 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 6.3.1.5 ammonia + ATP + deamido-NAD = 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.- pyruvate + coenzyme A + NAD+ = acetyl-CoA + CO2 + NADH respiration (anaerobic) 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 NAD+ + ethylene glycol = glycolaldehyde + NADH ethylene glycol 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.37 malate + NAD+ = oxaloacetate + NADH mixed acid fermentation 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.37 malate + NAD+ = oxaloacetate + NADH TCA cycle variation 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.37 malate + NAD+ = oxaloacetate + NADH reductive TCA cycle 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.37 malate + NAD+ = oxaloacetate + NADH gluconeogenesis 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.37 malate + NAD+ = oxaloacetate + NADH respiration (anaerobic) 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.37 malate + NAD+ = 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.37 malate + NAD+ = oxaloacetate + NADH TCA 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 3.1.3.- H2O + NADP+ = 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.290 erythronate-4-phosphate + NAD+ = 2-oxo-3-hydroxy-4-phosphobutanoate + NADH + H+ pyridoxal 5'-phosphate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.31 2-aminoadipate-6-semialdehyde + H2O + NAD+ = α-aminoadipate + NADH 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.1 2-methylbutanal + NADH = 2-methylbutanol + NAD+ isoleucine 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.8.1.4 NAD+ = NADH + H+ 2-keto glutarate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.28 NAD+ + D-lactate = NADH + pyruvate mixed acid fermentation 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.28 NAD+ + D-lactate = NADH + pyruvate D-lactate fermentation to propionate and acetate 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.75 1-amino-propan-2-ol + NAD+ = aminoacetone + NADH aminopropanol 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.3 acetaldehyde + NAD+ + H2O = NADH + acetate oxidative ethanol 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.2.1.3 acetaldehyde + NAD+ + H2O = NADH + acetate oxidative ethanol 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.1.1.95 3-phosphoglycerate + NAD+ = 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 1.5.1.12 pyrroline-hydroxy-carboxylate + NAD+ + H2O = L-erythro-4-hydroxy-glutamate + NADH 4-hydroxyproline 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 664.438 C21 H28 N7 O14 P2 c1([n+](cc(C(=O)N)cc1)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OCC3(OC(C(O)C3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00003:*CAS:53-84-9 2.7.7.1 nicotinamide mononucleotide + ATP = NAD+ + diphosphate NAD salvage pathway II pantetheine 4'-phosphate phosphopantotheine*pantotheine-4'-phosphate*4'-phosphopantetheine*phosphopantetheine 358.346 C11 H23 N2 O7 P1 S1 CC(C)(COP(O)(=O)O)C(O)C(=O)NCCC(=O)NCCS LIGAND-CPD:C01134: 4.1.1.36 R-4'-phosphopantothenoyl-L-cysteine = pantetheine 4'-phosphate + CO2 coenzyme A biosynthesis pantetheine 4'-phosphate phosphopantotheine*pantotheine-4'-phosphate*4'-phosphopantetheine*phosphopantetheine 358.346 C11 H23 N2 O7 P1 S1 CC(C)(COP(O)(=O)O)C(O)C(=O)NCCC(=O)NCCS LIGAND-CPD:C01134: 2.7.7.3 pantetheine 4'-phosphate + ATP = dephospho-CoA + diphosphate coenzyme A biosynthesis 16:0-18:3-PC 1-16:0-2-18:3-phosphatidylcholine*1-hexadecanoyl-2-(9Z,12Z,15Z-octadecatrienoyl)-sn-glycero-3-phosphocholine 757.062 C42 H79 N1 O8 P1 C(OP(=O)(O)OCC[N+](C)(C)C)C(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCC=CCC=CCC=CCC PUBCHEM:5313197: 16:0-18:2-PC = 16:0-18:3-PC phospholipid desaturation (-)-isopiperitenone 150.22 C10 H14 O1 C=C(C)C1(C(=O)C=C(C)CC1) CAS:529-01-1 1.1.1.223 NAD+ + (-)-trans-Isopiperitenol = NADH + (-)-isopiperitenone menthol biosynthesis (-)-isopiperitenone 150.22 C10 H14 O1 C=C(C)C1(C(=O)C=C(C)CC1) CAS:529-01-1 (-)-isopiperitenone + NADP+ = (+)-cis-isopulegone + NADPH menthol biosynthesis caffeoylquinate chlorogenate*chlorogenic acid 354.313 C16 H18 O9 C(=O)(OC1(C(O)C(O)CC(O)(C1)C(O)=O))C=Cc2(cc(O)c(O)cc2) 3.1.2.- caffeoylquinate + coenzyme A = caffeoyl-CoA + quinate phenylpropanoid biosynthesis caffeoylquinate chlorogenate*chlorogenic acid 354.313 C16 H18 O9 C(=O)(OC1(C(O)C(O)CC(O)(C1)C(O)=O))C=Cc2(cc(O)c(O)cc2) 1.14.13.36 4-coumaroylquinate + NADPH + O2 = caffeoylquinate + NADP+ + H2O phenylpropanoid biosynthesis 24-methylenecholesterol 398.671 C28 H46 O1 CC(C)C(=C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) 24-methylenecholesterol = 24-methyldesmosterol sterol biosynthesis 24-methylenecholesterol 398.671 C28 H46 O1 CC(C)C(=C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) 1.3.1.21 5-dehydro episterol + NADPH = 24-methylenecholesterol + NADP+ sterol biosynthesis UTP uridine-triphosphate*uridine-5'-triphosphate 484.143 C9 H15 N2 O15 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00075:*CAS:63-39-8 UTP = dUTP + H2O de novo biosynthesis of pyrimidine deoxyribonucleotides UTP uridine-triphosphate*uridine-5'-triphosphate 484.143 C9 H15 N2 O15 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.23 N-acetyl-glucosamine-1-phosphate + UTP = UDP-N-acetyl-D-glucosamine + diphosphate UDP-N-acetylgalactosamine biosynthesis UTP uridine-triphosphate*uridine-5'-triphosphate 484.143 C9 H15 N2 O15 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.10 α-D-galactose 1-phosphate + UTP = UDP-galactose + diphosphate galactose degradation II UTP uridine-triphosphate*uridine-5'-triphosphate 484.143 C9 H15 N2 O15 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.44 α-D-glucuronate 1-phosphate + UTP = UDP-D-glucuronate + diphosphate UDP-D-glucuronate biosynthesis (from myo-inositol) UTP uridine-triphosphate*uridine-5'-triphosphate 484.143 C9 H15 N2 O15 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.37 β-L-arabinose 1-phosphate + UTP = UDP-L-arabinose + diphosphate UDP-L-arabinose biosynthesis II (from L-arabinose) UTP uridine-triphosphate*uridine-5'-triphosphate 484.143 C9 H15 N2 O15 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate sucrose degradation III UTP uridine-triphosphate*uridine-5'-triphosphate 484.143 C9 H15 N2 O15 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate sucrose degradation to ethanol and lactate (anaerobic) UTP uridine-triphosphate*uridine-5'-triphosphate 484.143 C9 H15 N2 O15 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate galactose degradation II UTP uridine-triphosphate*uridine-5'-triphosphate 484.143 C9 H15 N2 O15 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate UDP-glucose conversion UTP uridine-triphosphate*uridine-5'-triphosphate 484.143 C9 H15 N2 O15 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) UTP uridine-triphosphate*uridine-5'-triphosphate 484.143 C9 H15 N2 O15 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00075:*CAS:63-39-8 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate sucrose biosynthesis UTP uridine-triphosphate*uridine-5'-triphosphate 484.143 C9 H15 N2 O15 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00075:*CAS:63-39-8 6.3.4.2 ATP + UTP + L-glutamine + H2O = ADP + CTP + L-glutamate de novo biosynthesis of pyrimidine ribonucleotides UTP uridine-triphosphate*uridine-5'-triphosphate 484.143 C9 H15 N2 O15 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00075:*CAS:63-39-8 2.7.4.6 UDP + ATP = UTP + ADP de novo biosynthesis of pyrimidine ribonucleotides guanosine nucleoside Q 283.243 C10 H13 N5 O5 C(O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00387:*CAS:118-00-3 3.2.2.1 guanosine + H2O = guanine + D-ribose purine degradation guanosine nucleoside Q 283.243 C10 H13 N5 O5 C(O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00387:*CAS:118-00-3 3.2.2.1 guanosine + H2O = guanine + D-ribose salvage pathways of purine nucleosides II (plant) guanosine nucleoside Q 283.243 C10 H13 N5 O5 C(O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00387:*CAS:118-00-3 2.4.2.15 guanosine = ribose-1-phosphate + guanine salvage pathways of purine nucleosides guanosine nucleoside Q 283.243 C10 H13 N5 O5 C(O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00387:*CAS:118-00-3 2.4.2.15 guanosine = ribose-1-phosphate + guanine salvage pathways of purine and pyrimidine nucleotides guanosine nucleoside Q 283.243 C10 H13 N5 O5 C(O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00387:*CAS:118-00-3 3.5.4.15 H2O + guanosine = ammonia + xanthosine purine degradation guanosine nucleoside Q 283.243 C10 H13 N5 O5 C(O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00387:*CAS:118-00-3 3.5.4.15 H2O + guanosine = ammonia + xanthosine salvage pathways of purine nucleosides II (plant) guanosine nucleoside Q 283.243 C10 H13 N5 O5 C(O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00387:*CAS:118-00-3 3.1.3.5 GMP + H2O = guanosine purine degradation guanosine nucleoside Q 283.243 C10 H13 N5 O5 C(O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00387:*CAS:118-00-3 3.1.3.5 GMP + H2O = guanosine salvage pathways of purine nucleosides II (plant) guanosine nucleoside Q 283.243 C10 H13 N5 O5 C(O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00387:*CAS:118-00-3 2.7.1.73 guanosine + ATP = GMP + ADP salvage pathways of purine nucleosides guanosine nucleoside Q 283.243 C10 H13 N5 O5 C(O)[CH]1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00387:*CAS:118-00-3 2.7.1.73 guanosine + ATP = GMP + ADP salvage pathways of purine nucleosides II (plant) 7-hydroxy-chlorophyllide a 7-OH-chlorophyllide a 630.982 C35 H34 N4 O6 MG1 CCC9(C1(=N8([Mg]46(N5(=C(C2(C(C(=O)OC)C(=O)c3(c(C)c(=C1)n(c=23)4)))C(CCC(=O)O)C(C)C5=Cc7(n6c(c(C=C)c(C)7)C=C8C=9CO)))))) chlorophyllide a + O2 + NADPH = 7-hydroxy-chlorophyllide a + H2O + NADP+ chlorophyll cycle 7-hydroxy-chlorophyllide a 7-OH-chlorophyllide a 630.982 C35 H34 N4 O6 MG1 CCC9(C1(=N8([Mg]46(N5(=C(C2(C(C(=O)OC)C(=O)c3(c(C)c(=C1)n(c=23)4)))C(CCC(=O)O)C(C)C5=Cc7(n6c(c(C=C)c(C)7)C=C8C=9CO)))))) 7-hydroxy-chlorophyllide a + O2 + NADPH = chlorophyllide b + H2O + NADP+ chlorophyll cycle Mg-protoporphyrin Mg-protoporphyrin IX*Mg-protoporphyrin*magnesium protoporphyrin*MgP 584.956 C34 H32 N4 O4 MG1 Cc7(c6(=CC3(=N2([Mg]58(n1(c(c(C)c(C=C)c1C=C2C(C)=C3C=C)C=C4(N(=C(C(=C(C)4)CCC(O)=O)C=c(n56)c7CCC(=O)O)8))))))) 6.6.1.1 ATP + protoporphyrin IX + Mg2+ + H2O = Mg-protoporphyrin + ADP + H+ chlorophyllide a biosynthesis Mg-protoporphyrin Mg-protoporphyrin IX*Mg-protoporphyrin*magnesium protoporphyrin*MgP 584.956 C34 H32 N4 O4 MG1 Cc7(c6(=CC3(=N2([Mg]58(n1(c(c(C)c(C=C)c1C=C2C(C)=C3C=C)C=C4(N(=C(C(=C(C)4)CCC(O)=O)C=c(n56)c7CCC(=O)O)8))))))) 2.1.1.11 Mg-protoporphyrin + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + Mg-protoporphyrin monomethyl ester chlorophyllide a biosynthesis adenine 6-aminopurine 135.128 C5 H5 N5 c1(ncnc2(c1N=CN2))(N) LIGAND-CPD:C00147:*CAS:73-24-5 1.5.99.12 trans-zeatin + H2O + FAD = adenine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation adenine 6-aminopurine 135.128 C5 H5 N5 c1(ncnc2(c1N=CN2))(N) LIGAND-CPD:C00147:*CAS:73-24-5 2.4.2.- adenosine = ribose-1-phosphate + adenine salvage pathways of adenine, hypoxanthine, and their nucleosides adenine 6-aminopurine 135.128 C5 H5 N5 c1(ncnc2(c1N=CN2))(N) LIGAND-CPD:C00147:*CAS:73-24-5 2.4.2.- adenosine = ribose-1-phosphate + adenine salvage pathways of purine nucleosides adenine 6-aminopurine 135.128 C5 H5 N5 c1(ncnc2(c1N=CN2))(N) LIGAND-CPD:C00147:*CAS:73-24-5 2.4.2.- adenosine = ribose-1-phosphate + adenine salvage pathways of purine and pyrimidine nucleotides adenine 6-aminopurine 135.128 C5 H5 N5 c1(ncnc2(c1N=CN2))(N) LIGAND-CPD:C00147:*CAS:73-24-5 1.5.99.12 isopentenyladenine + FAD + H2O = 3-methyl-2-butenal + adenine + FADH2 cytokinins degradation adenine 6-aminopurine 135.128 C5 H5 N5 c1(ncnc2(c1N=CN2))(N) LIGAND-CPD:C00147:*CAS:73-24-5 1.5.99.12 cis-zeatin + H2O + FAD = 3-methyl-4-cis-hydroxy-2-butenal + adenine + FADH2 cytokinins degradation adenine 6-aminopurine 135.128 C5 H5 N5 c1(ncnc2(c1N=CN2))(N) LIGAND-CPD:C00147:*CAS:73-24-5 3.2.2.7 H2O + adenosine = D-ribose + adenine salvage pathways of purine nucleosides II (plant) adenine 6-aminopurine 135.128 C5 H5 N5 c1(ncnc2(c1N=CN2))(N) LIGAND-CPD:C00147:*CAS:73-24-5 3.2.2.4 AMP + H2O = D-ribose-5-phosphate + adenine salvage pathways of adenine, hypoxanthine, and their nucleosides adenine 6-aminopurine 135.128 C5 H5 N5 c1(ncnc2(c1N=CN2))(N) LIGAND-CPD:C00147:*CAS:73-24-5 3.2.2.16 5'-methylthioadenosine + H2O = 5-methylthioribose + adenine methionine salvage pathway adenine 6-aminopurine 135.128 C5 H5 N5 c1(ncnc2(c1N=CN2))(N) LIGAND-CPD:C00147:*CAS:73-24-5 adenine + deoxyribose-1-phosphate = deoxyadenosine salvage pathways of adenine, hypoxanthine, and their nucleosides adenine 6-aminopurine 135.128 C5 H5 N5 c1(ncnc2(c1N=CN2))(N) LIGAND-CPD:C00147:*CAS:73-24-5 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of adenine, hypoxanthine, and their nucleosides adenine 6-aminopurine 135.128 C5 H5 N5 c1(ncnc2(c1N=CN2))(N) LIGAND-CPD:C00147:*CAS:73-24-5 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of purine nucleosides adenine 6-aminopurine 135.128 C5 H5 N5 c1(ncnc2(c1N=CN2))(N) LIGAND-CPD:C00147:*CAS:73-24-5 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of purine and pyrimidine nucleotides adenine 6-aminopurine 135.128 C5 H5 N5 c1(ncnc2(c1N=CN2))(N) LIGAND-CPD:C00147:*CAS:73-24-5 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of purine nucleosides II (plant) 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 521.311 C14 H25 N3 O14 P2 CC(O)(CO)C(O)COP(=O)(O)OP(=O)(O)OCC1(OC(C(O)C1O)n2(c(=O)nc(N)cc2)) LIGAND-CPD:C11435: 2.7.1.148 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + ATP = 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 521.311 C14 H25 N3 O14 P2 CC(O)(CO)C(O)COP(=O)(O)OP(=O)(O)OCC1(OC(C(O)C1O)n2(c(=O)nc(N)cc2)) LIGAND-CPD:C11435: 2.7.7.60 2-C-methyl-D-erythritol-4-phosphate + CTP = 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + diphosphate methylerythritol phosphate pathway 10,16-dihydroxypalmitate 288.426 C16 H32 O4 C(O)CCCCCC(O)CCCCCCCCC(O)=O 16-hydroxypalmitate + NADPH + O2 = 10,16-dihydroxypalmitate + NADP+ + H2O cutin biosynthesis D-pinitol 6-methoxycyclohexane-1,2,3,4,5-pentaol*inzitol*3-O-methyl-D-chiro-inositol 194.184 C7 H14 O6 C1(C(O)C(O)C(OC)C(O)C(O)1)(O) PUBCHEM:439990: 2.4.1.- D-pinitol + galactinol = galactopinitol A + myo-inositol galactosylcyclitol biosynthesis D-pinitol 6-methoxycyclohexane-1,2,3,4,5-pentaol*inzitol*3-O-methyl-D-chiro-inositol 194.184 C7 H14 O6 C1(C(O)C(O)C(OC)C(O)C(O)1)(O) PUBCHEM:439990: 2.4.1.- D-pinitol + galactinol = galactopinitol B + myo-inositol galactosylcyclitol biosynthesis α-maltose 342.299 C12 H22 O11 C1(OC(CO)C(O)C(O)C(O)1)OC2(C(CO)OC(O)C(O)C(O)2) 3.2.1.2 H2O = α-maltose starch degradation α-maltose 342.299 C12 H22 O11 C1(OC(CO)C(O)C(O)C(O)1)OC2(C(CO)OC(O)C(O)C(O)2) 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 230.111 C5 H11 O8 P1 C(OP(O)(=O)O)C(O)C(O)C(O)C=O 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 HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])(=O)[O-] CAS:7782-99-2:*LIGAND-CPD:C00094: 1.8.4.8 sulfite + adenosine-3',5'-bisphosphate = phosphoadenosine-5'-phosphosulfate sulfate reduction I (assimilatory) sulfite HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])(=O)[O-] CAS:7782-99-2:*LIGAND-CPD:C00094: 1.8.1.2 H2O + NADP+ + hydrogen sulfide = sulfite + NADPH sulfate reduction I (assimilatory) sulfite HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])(=O)[O-] CAS:7782-99-2:*LIGAND-CPD:C00094: 1.8.4.9 sulfite + AMP + glutathione disulfide = adenosine 5'-phosphosulfate + glutathione sulfate reduction II (assimilatory) sulfite HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])(=O)[O-] CAS:7782-99-2:*LIGAND-CPD:C00094: 3.13.1.1 sulfite + UDP-D-glucose = UDP-sulfoquinovose + H2O glycolipid biosynthesis sulfite HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])(=O)[O-] CAS:7782-99-2:*LIGAND-CPD:C00094: 2.8.1.1 thiosulfate + hydrogen cyanide = sulfite + thiocyanate thiosulfate disproportionation III (rhodanese) sulfite HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])(=O)[O-] CAS:7782-99-2:*LIGAND-CPD:C00094: 1.8.99.2 sulfite + AMP = adenosine 5'-phosphosulfate sulfite oxidation III sulfite HSO3-*HSO3*bisulfite*SO3*SO3-2 80.058 O3 S1 S([O-])(=O)[O-] CAS:7782-99-2:*LIGAND-CPD:C00094: 3-sulfinyl-pyruvate + H2O = sulfite + pyruvate L-cysteine degradation I humulone (6R)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)cyclo 362.465 C21 H30 O5 CC(C)=CCC1(=C(O)C(O)(CC=C(C)C)C(=O)C(=C(O)1)C(=O)CC(C)C) diprenylphlorisovalerophenone + O2 = humulone + H2O humulone biosynthesis GA14 gibberellin A14*gibberellin A14*GA14 348.438 C20 H28 O5 CC1([CH]4(C(CCC(O)1)(C)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA14 + O2 + α-ketoglutarate = GA37 + CO2 + succinate gibberellin biosynthesis II (early C-3 hydroxylation) GA14 gibberellin A14*gibberellin A14*GA14 348.438 C20 H28 O5 CC1([CH]4(C(CCC(O)1)(C)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA12 + α-ketoglutarate + O2 = GA14 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) (+)-neoisomenthol 156.267 C10 H20 O1 CC(C)C1(C(O)CC(C)CC1) (+)-isomenthone + NADPH = (+)-neoisomenthol + NADP+ menthol biosynthesis acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP oxidative ethanol degradation III acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP glutamate degradation VII (to butyrate) acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP oxidative ethanol degradation I acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 1.2.2.2 pyruvate + ubiquinone-8 + H2O = ubiquinol-8 + acetate + CO2 mixed acid fermentation acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 UDP-3-O-(3-hydroxymyristoyl)-N-acetylglucosamine + H2O = UDP-3-O-(3-hydroxymyristoyl)glucosamine + acetate lipid-A-precursor biosynthesis acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 2.7.2.1 ATP + acetate = ADP + acetylphosphate mixed acid fermentation acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 2.7.2.1 ATP + acetate = ADP + acetylphosphate D-lactate fermentation to propionate and acetate acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 2.7.2.1 ATP + acetate = ADP + acetylphosphate ethanol fermentation to acetate acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 2.7.2.1 ATP + acetate = ADP + acetylphosphate glucose fermentation to lactate II acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 2.7.2.1 ATP + acetate = ADP + acetylphosphate gallate degradation III (anaerobic) acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 1.2.1.3 acetaldehyde + NAD+ + H2O = NADH + acetate oxidative ethanol degradation III acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 1.2.1.3 acetaldehyde + NAD+ + H2O = NADH + acetate oxidative ethanol degradation I acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 2.5.1.49 O-acetyl-L-homoserine + hydrogen sulfide = L-homocysteine + acetate homocysteine biosynthesis acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 2.8.3.8 butyryl-CoA + acetate = butyrate + acetyl-CoA ethanol fermentation to acetate acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 2.8.3.8 butyryl-CoA + acetate = butyrate + acetyl-CoA gallate degradation III (anaerobic) acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 2.8.3.1 propionate + acetyl-CoA = propionyl-CoA + acetate D-lactate fermentation to propionate and acetate acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 2.5.1.47 O-acetyl-L-serine + hydrogen sulfide = L-cysteine + acetate cysteine biosynthesis I acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 3.5.1.47 H2O + N-acetyl-L,L-2,6-diaminopimelate = L,L-diaminopimelate + acetate lysine biosynthesis II acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 indole + acetate = indole-3-acetate IAA biosynthesis I acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate + O2 = (+)-7-isojasmonate + acetate jasmonic acid biosynthesis acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 2.8.3.- 3-hydroxy-5-oxohexanoate + acetyl-CoA = 3-hydroxy-5- oxohexanoyl-CoA + acetate gallate degradation III (anaerobic) acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*LIGAND-CPD:c00033:*CAS:71-50-1 O-acetyl-L-homoserine + L-cysteine = cystathionine + acetate homocysteine and cysteine interconversion acetate acet*acetic acid*ethanoic acid 59.044 C2 H3 O2 C([O-])(=O)C CAS:64-19-7:*LIGAND-CPD:C00033:*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 324.18 C10 H13 O10 P1 C(=O)(O)C1([CH2][CH](OC(=C)C(=O)O)[CH](O)[CH]([CH]=1)OP(O)(O)=O) LIGAND-CPD:C01269: 4.2.3.5 5-enolpyruvyl-shikimate-3-phosphate = chorismate chorismate biosynthesis 5-enolpyruvyl-shikimate-3-phosphate EPSP*3-enolpyruvyl-shikimate-5-phosphate*3-enolpyruvyl-shikimate-5-P*5-O-(1-carboxyvinyl)-3-phosphoshikimate 324.18 C10 H13 O10 P1 C(=O)(O)C1([CH2][CH](OC(=C)C(=O)O)[CH](O)[CH]([CH]=1)OP(O)(O)=O) LIGAND-CPD:C01269: 2.5.1.19 shikimate-3-phosphate + phosphoenolpyruvate = 5-enolpyruvyl-shikimate-3-phosphate chorismate biosynthesis p-coumaroyltriacetate p-coumaroyltriacetic acid 290.272 C15 H14 O6 C(O)(=O)CC(=O)CC(=O)CC(=O)C=Cc1(ccc(O)cc1) p-coumaroyltriacetate = p-coumaroyltriacetic acid lactone + H2O resveratrol biosynthesis p-coumaroyltriacetate p-coumaroyltriacetic acid 290.272 C15 H14 O6 C(O)(=O)CC(=O)CC(=O)CC(=O)C=Cc1(ccc(O)cc1) 2.3.1.- H2O + coumaroyl-CoA + malonyl-CoA = coenzyme A + CO2 + p-coumaroyltriacetate resveratrol biosynthesis presqualene diphosphate 586.684 C30 H52 O7 P2 CC(C)=CCCC(C)=CCCC(C)=C[CH]1(C([CH]1COP(O)(=O)OP(O)(=O)O)(C)CCC=C(C)CCC=C(C)C) 2.5.1.21 presqualene diphosphate = squalene + diphosphate cholesterol biosynthesis I presqualene diphosphate 586.684 C30 H52 O7 P2 CC(C)=CCCC(C)=CCCC(C)=C[CH]1(C([CH]1COP(O)(=O)OP(O)(=O)O)(C)CCC=C(C)CCC=C(C)C) 2.5.1.21 presqualene diphosphate = squalene + diphosphate cholesterol biosynthesis III (via desmosterol) presqualene diphosphate 586.684 C30 H52 O7 P2 CC(C)=CCCC(C)=CCCC(C)=C[CH]1(C([CH]1COP(O)(=O)OP(O)(=O)O)(C)CCC=C(C)CCC=C(C)C) 2.5.1.21 presqualene diphosphate = squalene + diphosphate cholesterol biosynthesis II (via 24,25-dihydrolanosterol) presqualene diphosphate 586.684 C30 H52 O7 P2 CC(C)=CCCC(C)=CCCC(C)=C[CH]1(C([CH]1COP(O)(=O)OP(O)(=O)O)(C)CCC=C(C)CCC=C(C)C) 2.5.1.21 presqualene diphosphate = squalene + diphosphate sterol biosynthesis presqualene diphosphate 586.684 C30 H52 O7 P2 CC(C)=CCCC(C)=CCCC(C)=C[CH]1(C([CH]1COP(O)(=O)OP(O)(=O)O)(C)CCC=C(C)CCC=C(C)C) 2.5.1.21 trans, trans-farnesyl diphosphate = presqualene diphosphate + diphosphate cholesterol biosynthesis I presqualene diphosphate 586.684 C30 H52 O7 P2 CC(C)=CCCC(C)=CCCC(C)=C[CH]1(C([CH]1COP(O)(=O)OP(O)(=O)O)(C)CCC=C(C)CCC=C(C)C) 2.5.1.21 trans, trans-farnesyl diphosphate = presqualene diphosphate + diphosphate cholesterol biosynthesis III (via desmosterol) presqualene diphosphate 586.684 C30 H52 O7 P2 CC(C)=CCCC(C)=CCCC(C)=C[CH]1(C([CH]1COP(O)(=O)OP(O)(=O)O)(C)CCC=C(C)CCC=C(C)C) 2.5.1.21 trans, trans-farnesyl diphosphate = presqualene diphosphate + diphosphate cholesterol biosynthesis II (via 24,25-dihydrolanosterol) presqualene diphosphate 586.684 C30 H52 O7 P2 CC(C)=CCCC(C)=CCCC(C)=C[CH]1(C([CH]1COP(O)(=O)OP(O)(=O)O)(C)CCC=C(C)CCC=C(C)C) 2.5.1.21 trans, trans-farnesyl diphosphate = presqualene diphosphate + diphosphate sterol biosynthesis sn-glycerol-3-phosphate 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 172.074 C3 H9 O6 P1 C(O)C(O)COP(O)(O)=O LIGAND-CPD:C00093:*CAS:57-03-4 2.7.8.5 sn-glycerol-3-phosphate = CMP phospholipid biosynthesis I sn-glycerol-3-phosphate 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 172.074 C3 H9 O6 P1 C(O)C(O)COP(O)(O)=O LIGAND-CPD:C00093:*CAS:57-03-4 2.7.8.5 sn-glycerol-3-phosphate = CMP phospholipid biosynthesis II sn-glycerol-3-phosphate 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 172.074 C3 H9 O6 P1 C(O)C(O)COP(O)(O)=O LIGAND-CPD:C00093:*CAS:57-03-4 2.7.8.5 sn-glycerol-3-phosphate = CMP cardiolipin biosynthesis sn-glycerol-3-phosphate 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 172.074 C3 H9 O6 P1 C(O)C(O)COP(O)(O)=O LIGAND-CPD:C00093:*CAS:57-03-4 2.3.1.15 sn-glycerol-3-phosphate = coenzyme A phospholipid biosynthesis II sn-glycerol-3-phosphate 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 172.074 C3 H9 O6 P1 C(O)C(O)COP(O)(O)=O LIGAND-CPD:C00093:*CAS:57-03-4 2.3.1.15 sn-glycerol-3-phosphate = coenzyme A triacylglycerol biosynthesis sn-glycerol-3-phosphate 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 172.074 C3 H9 O6 P1 C(O)C(O)COP(O)(O)=O LIGAND-CPD:C00093:*CAS:57-03-4 indole-3-glycerol-phosphate = indole + sn-glycerol-3-phosphate IAA biosynthesis I sn-glycerol-3-phosphate 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 172.074 C3 H9 O6 P1 C(O)C(O)COP(O)(O)=O LIGAND-CPD:C00093:*CAS:57-03-4 1.1.99.5 sn-glycerol-3-phosphate + ubiquinone-8 = dihydroxy-acetone-phosphate + ubiquinol-8 aerobic respiration -- electron donors reaction list sn-glycerol-3-phosphate 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 172.074 C3 H9 O6 P1 C(O)C(O)COP(O)(O)=O LIGAND-CPD:C00093:*CAS:57-03-4 1.1.99.5 sn-glycerol-3-phosphate + ubiquinone-8 = dihydroxy-acetone-phosphate + ubiquinol-8 respiration (anaerobic)-- electron donors reaction list sn-glycerol-3-phosphate 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 172.074 C3 H9 O6 P1 C(O)C(O)COP(O)(O)=O LIGAND-CPD:C00093:*CAS:57-03-4 1.1.99.5 sn-glycerol-3-phosphate + ubiquinone-8 = dihydroxy-acetone-phosphate + ubiquinol-8 glycerol degradation I sn-glycerol-3-phosphate 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 172.074 C3 H9 O6 P1 C(O)C(O)COP(O)(O)=O LIGAND-CPD:C00093:*CAS:57-03-4 1.1.99.5 sn-glycerol-3-phosphate + FAD = dihydroxy-acetone-phosphate + FADH2 glycerol degradation IV sn-glycerol-3-phosphate 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 172.074 C3 H9 O6 P1 C(O)C(O)COP(O)(O)=O LIGAND-CPD:C00093:*CAS:57-03-4 2.7.1.30 glycerol + ATP = sn-glycerol-3-phosphate + ADP glycerol degradation IV sn-glycerol-3-phosphate 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 172.074 C3 H9 O6 P1 C(O)C(O)COP(O)(O)=O LIGAND-CPD:C00093:*CAS:57-03-4 2.7.1.30 glycerol + ATP = sn-glycerol-3-phosphate + ADP glycerol degradation I sn-glycerol-3-phosphate 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 172.074 C3 H9 O6 P1 C(O)C(O)COP(O)(O)=O LIGAND-CPD:C00093:*CAS:57-03-4 3.1.4.46 H2O = sn-glycerol-3-phosphate glycerol degradation I sn-glycerol-3-phosphate 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 172.074 C3 H9 O6 P1 C(O)C(O)COP(O)(O)=O LIGAND-CPD:C00093:*CAS:57-03-4 1.1.1.94 sn-glycerol-3-phosphate = dihydroxy-acetone-phosphate + H+ phospholipid biosynthesis I sn-glycerol-3-phosphate 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 172.074 C3 H9 O6 P1 C(O)C(O)COP(O)(O)=O LIGAND-CPD:C00093:*CAS:57-03-4 2.3.1.15 phospholipid biosynthesis I L-arginino-succinate N-(L-arginino)-succinate*arginino-succinate 290.275 C10 H18 N4 O6 C(=O)(O)C(N)CCCNC(=N)NC(C(O)=O)CC(O)=O PUBCHEM:828:*LIGAND-CPD:C03406: 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP urea cycle L-arginino-succinate N-(L-arginino)-succinate*arginino-succinate 290.275 C10 H18 N4 O6 C(=O)(O)C(N)CCCNC(=N)NC(C(O)=O)CC(O)=O PUBCHEM:828:*LIGAND-CPD:C03406: 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis II (acetyl cycle) L-arginino-succinate N-(L-arginino)-succinate*arginino-succinate 290.275 C10 H18 N4 O6 C(=O)(O)C(N)CCCNC(=N)NC(C(O)=O)CC(O)=O PUBCHEM:828:*LIGAND-CPD:C03406: 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP citrulline-nitric oxide cycle L-arginino-succinate N-(L-arginino)-succinate*arginino-succinate 290.275 C10 H18 N4 O6 C(=O)(O)C(N)CCCNC(=N)NC(C(O)=O)CC(O)=O PUBCHEM:828:*LIGAND-CPD:C03406: 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis IV L-arginino-succinate N-(L-arginino)-succinate*arginino-succinate 290.275 C10 H18 N4 O6 C(=O)(O)C(N)CCCNC(=N)NC(C(O)=O)CC(O)=O PUBCHEM:828:*LIGAND-CPD:C03406: 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis I L-arginino-succinate N-(L-arginino)-succinate*arginino-succinate 290.275 C10 H18 N4 O6 C(=O)(O)C(N)CCCNC(=N)NC(C(O)=O)CC(O)=O 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 290.275 C10 H18 N4 O6 C(=O)(O)C(N)CCCNC(=N)NC(C(O)=O)CC(O)=O 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 290.275 C10 H18 N4 O6 C(=O)(O)C(N)CCCNC(=N)NC(C(O)=O)CC(O)=O 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 290.275 C10 H18 N4 O6 C(=O)(O)C(N)CCCNC(=N)NC(C(O)=O)CC(O)=O PUBCHEM:828:*LIGAND-CPD:C03406: 4.3.2.1 L-arginino-succinate = L-arginine + fumarate arginine biosynthesis IV L-arginino-succinate N-(L-arginino)-succinate*arginino-succinate 290.275 C10 H18 N4 O6 C(=O)(O)C(N)CCCNC(=N)NC(C(O)=O)CC(O)=O PUBCHEM:828:*LIGAND-CPD:C03406: 4.3.2.1 L-arginino-succinate = L-arginine + fumarate arginine biosynthesis I loganin 390.386 C17 H26 O10 CC2([CH]1(C(OC=C(C(=O)OC)[CH]1CC2O)OC3(C(O)C(O)C(O)C(O3)CO))) NCI:606403*CAS:18524-94-2 1.14.13.74 O2 + NADPH + 7-deoxyloganin = H2O + NADP+ + loganin secologanin and strictosidine biosynthesis loganin 390.386 C17 H26 O10 CC2([CH]1(C(OC=C(C(=O)OC)[CH]1CC2O)OC3(C(O)C(O)C(O)C(O3)CO))) NCI:606403*CAS:18524-94-2 1.3.3.9 O2 + NADPH + loganin = H2O + NADP+ + secologanin secologanin and strictosidine biosynthesis afzelechin 274.273 C15 H14 O5 c1(ccc(O)cc1)C2(C(O)Cc3(c(O)cc(O)cc(O2)3)) 1.17.1.3 leucopelargonidin + NADPH = afzelechin + NADP+ + H2O proanthocyanidin biosynthesis from flavanols afzelechin 274.273 C15 H14 O5 c1(ccc(O)cc1)C2(C(O)Cc3(c(O)cc(O)cc(O2)3)) afzelechin + 2,3-trans-catechin = 2,3-cis-proanthocyanidin proanthocyanidin biosynthesis from flavanols UDP-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 607.358 C17 H27 N3 O17 P2 C(C1(OC(C(O)C(O)1)n2(c(=O)[nH]c(=O)cc2)))OP(O)(=O)OP(O)(=O)OC3(C(NC(=O)C)C(O)C(O)C(O3)CO) LIGAND-CPD:C00043:*CAS:528-04-1 2.3.1.129 UDP-N-acetyl-D-glucosamine = UDP-3-O-(3-hydroxymyristoyl)-N-acetylglucosamine lipid-A-precursor biosynthesis UDP-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 607.358 C17 H27 N3 O17 P2 C(C1(OC(C(O)C(O)1)n2(c(=O)[nH]c(=O)cc2)))OP(O)(=O)OP(O)(=O)OC3(C(NC(=O)C)C(O)C(O)C(O3)CO) LIGAND-CPD:C00043:*CAS:528-04-1 2.4.1.141 N-acetylglucosaminyl-diphosphodolichol + UDP-N-acetyl-D-glucosamine = (N-acetylglucosaminyl)2-diphosphodolichol + UDP dolichyl-diphosphooligosaccharide biosynthesis UDP-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 607.358 C17 H27 N3 O17 P2 C(C1(OC(C(O)C(O)1)n2(c(=O)[nH]c(=O)cc2)))OP(O)(=O)OP(O)(=O)OC3(C(NC(=O)C)C(O)C(O)C(O3)CO) LIGAND-CPD:C00043:*CAS:528-04-1 2.5.1.7 UDP-N-acetyl-D-glucosamine + phosphoenolpyruvate = UDP-GlcNAc-enolpyruvate peptidoglycan biosynthesis I UDP-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 607.358 C17 H27 N3 O17 P2 C(C1(OC(C(O)C(O)1)n2(c(=O)[nH]c(=O)cc2)))OP(O)(=O)OP(O)(=O)OC3(C(NC(=O)C)C(O)C(O)C(O3)CO) LIGAND-CPD:C00043:*CAS:528-04-1 5.1.3.7 UDP-N-acetyl-D-glucosamine = UDP-N-acetyl-D-galactosamine UDP-N-acetylgalactosamine biosynthesis UDP-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 607.358 C17 H27 N3 O17 P2 C(C1(OC(C(O)C(O)1)n2(c(=O)[nH]c(=O)cc2)))OP(O)(=O)OP(O)(=O)OC3(C(NC(=O)C)C(O)C(O)C(O3)CO) LIGAND-CPD:C00043:*CAS:528-04-1 2.7.8.15 dolichyl-phosphate + UDP-N-acetyl-D-glucosamine = N-acetylglucosaminyl-diphosphodolichol + UMP dolichyl-diphosphooligosaccharide biosynthesis UDP-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 607.358 C17 H27 N3 O17 P2 C(C1(OC(C(O)C(O)1)n2(c(=O)[nH]c(=O)cc2)))OP(O)(=O)OP(O)(=O)OC3(C(NC(=O)C)C(O)C(O)C(O3)CO) LIGAND-CPD:C00043:*CAS:528-04-1 2.7.7.23 N-acetyl-glucosamine-1-phosphate + UTP = UDP-N-acetyl-D-glucosamine + diphosphate UDP-N-acetylgalactosamine biosynthesis UDP-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 607.358 C17 H27 N3 O17 P2 C(C1(OC(C(O)C(O)1)n2(c(=O)[nH]c(=O)cc2)))OP(O)(=O)OP(O)(=O)OC3(C(NC(=O)C)C(O)C(O)C(O3)CO) LIGAND-CPD:C00043:*CAS:528-04-1 2.4.1.227 UDP-N-acetyl-D-glucosamine = UDP peptidoglycan biosynthesis I 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 C1(OC(CO)C(O)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O)C(O)2) 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 C1(OC(CO)C(O)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O)C(O)2) 2.4.1.- D-pinitol + galactinol = galactopinitol A + myo-inositol galactosylcyclitol 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 C1(OC(CO)C(O)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O)C(O)2) 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 C1(OC(CO)C(O)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O)C(O)2) 2.4.1.- galactopinitol A + galactinol = ciceritol + myo-inositol galactosylcyclitol 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 C1(OC(CO)C(O)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O)C(O)2) 2.4.1.- D-ononitol + galactinol = D-galactosylononitol + myo-inositol galactosylcyclitol 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 C1(OC(CO)C(O)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O)C(O)2) 2.4.1.- D-pinitol + galactinol = galactopinitol B + myo-inositol galactosylcyclitol 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 C1(OC(CO)C(O)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O)C(O)2) 2.4.1.123 myo-inositol + UDP-galactose = galactinol + UDP stachyose biosynthesis N2-succinyl-L-glutamate 5-semialdehyde N2-succinylglutamic-semialdehyde*N2-succinylglutamate semialdehyde*N2-succinylglutamic semialdehyde 231.205 C9 H13 N1 O6 C(=O)(O)CCC(=O)NC(C(O)=O)CCC=O PUBCHEM:440848:*LIGAND-CPD:C05932: 1.2.1.- N2-succinyl-L-glutamate 5-semialdehyde + NAD+ + H2O = N2-succinylglutamate + NADH arginine degradation II N2-succinyl-L-glutamate 5-semialdehyde N2-succinylglutamic-semialdehyde*N2-succinylglutamate semialdehyde*N2-succinylglutamic semialdehyde 231.205 C9 H13 N1 O6 C(=O)(O)CCC(=O)NC(C(O)=O)CCC=O PUBCHEM:440848:*LIGAND-CPD:C05932: 2.6.1.11 N2-succinyl-L-ornithine + α-ketoglutarate = L-glutamate + N2-succinyl-L-glutamate 5-semialdehyde arginine degradation II wighteone 6-isopentenylgenistein*6-prenyl-5,7,4'-trihydroxyisoflavone 338.359 C20 H18 O5 CC(C)=CCc2(c(O)cc1(OC=C(C(=O)c1c2O)c3(ccc(O)cc3))) 2.5.1.1 genistein + dimethylallyl-PP = wighteone + diphosphate wighteone and luteone biosynthesis L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O 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 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O 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 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 3.5.3.1 H2O + L-arginine = urea + L-ornithine arginine degradation VII (arginase 3 pathway) L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O 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 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O 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 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 4.3.1.12 L-ornithine + NAD+ = L-proline + ammonia + NADH + H+ arginine degradation VII (arginase 3 pathway) L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 2.6.1.13 L-ornithine + α-ketoglutarate = L-glutamate + L-glutamate γ-semialdehyde proline biosynthesis V (from arginine) L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 2.6.1.13 L-ornithine + α-ketoglutarate = 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 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 2.6.1.13 L-ornithine + α-ketoglutarate = L-glutamate + L-glutamate γ-semialdehyde arginine biosynthesis IV L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 2.6.1.13 L-ornithine + α-ketoglutarate = 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 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 2.6.1.13 L-ornithine + α-ketoglutarate = 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 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O 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 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 3.5.1.20 citrulline + H2O = L-ornithine + CO2 + ammonia proline biosynthesis V (from arginine) L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 4.1.1.17 L-ornithine = CO2 + putrescine putrescine biosynthesis III L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline urea cycle L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline proline biosynthesis V (from arginine) L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline arginine biosynthesis II (acetyl cycle) L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline arginine biosynthesis IV L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline citrulline degradation L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline arginine biosynthesis I L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline citrulline biosynthesis L-ornithine Ornithine*2, 5-diaminovaleric acid*2, 5-diaminopentanoic acid*2, 5-diaminopentanoate*α,δ-diaminovaleric acid 132.162 C5 H12 N2 O2 C(N)CCC(N)C(O)=O LIGAND-CPD:C01602:*CAS:70-26-8 3.5.1.16 N-acetyl-L-ornithine + H2O = L-ornithine + acetate ornithine biosynthesis 4-(methylamino)-1-(3-pyridyl)-1-butanone pseudooxynicotine*1-butanone, 4-(methylamino)-1-(3-pyridinyl)- 178.233 C10 H14 N2 O1 c1(ncc(cc1)C(=O)CCCNC) 4-(methylamino)-1-(3-pyridyl)-1-butanone = 4-oxo-4-(3-pyridyl)-butanoate nicotine degradation II 4-(methylamino)-1-(3-pyridyl)-1-butanone pseudooxynicotine*1-butanone, 4-(methylamino)-1-(3-pyridinyl)- 178.233 C10 H14 N2 O1 c1(ncc(cc1)C(=O)CCCNC) 2'-hydroxynicotine = 4-(methylamino)-1-(3-pyridyl)-1-butanone nicotine degradation II ent-kaur-16-en-19-ol 288.472 C20 H32 O1 C=C1(C2(CC3(C1)(C(CC2)C4(C)(C(CC3)C(C)(CO)CCC4)))) 1.14.13.78 ent-kaur-16-en-19-ol + NADPH + H+ + O2 = ent-kaur-16-en-19-al + NADP+ + H2O GA12 biosynthesis ent-kaur-16-en-19-ol 288.472 C20 H32 O1 C=C1(C2(CC3(C1)(C(CC2)C4(C)(C(CC3)C(C)(CO)CCC4)))) 1.14.13.78 ent-kaur-16-ene + O2 + NADPH = H2O + NADP+ + ent-kaur-16-en-19-ol GA12 biosynthesis 2-amino-3-carboxymuconate semialdehyde 2-amino-3-carboxymuconate-6-semialdehyde*ACS 185.136 C7 H7 N1 O5 [CH](=O)C=CC(C(=O)O)=C(N)C(O)=O 4.1.1.45 2-amino-3-carboxymuconate semialdehyde = CO2 + 2-aminomuconate semialdehyde tryptophan degradation III (eukaryotic) 2-amino-3-carboxymuconate semialdehyde 2-amino-3-carboxymuconate-6-semialdehyde*ACS 185.136 C7 H7 N1 O5 [CH](=O)C=CC(C(=O)O)=C(N)C(O)=O 1.13.11.6 O2 + 3-hydroxy-anthranilate = 2-amino-3-carboxymuconate semialdehyde tryptophan degradation III (eukaryotic) 3-ureidopropionate 3-Ureidopropanoate*β-Ureidopropionic acid*N-Carbamoyl-β-alanine 132.119 C4 H8 N2 O3 C(CC(=O)O)NC(N)=O 3.5.1.6 H2O + 3-ureidopropionate = ammonia + CO2 + β-alanine β-alanine biosynthesis III 3-ureidopropionate 3-Ureidopropanoate*β-Ureidopropionic acid*N-Carbamoyl-β-alanine 132.119 C4 H8 N2 O3 C(CC(=O)O)NC(N)=O 3.5.2.2 H2O + dihydrouracil = 3-ureidopropionate β-alanine biosynthesis III 1-amino-propan-2-ol (R)-1-aminopropan-2-ol*D-1-amino-2-propanol*D-1-aminopropan-2-ol*aminopropanol 75.11 C3 H9 N1 O1 C(N)C(C)O CAS:78-96-6 1.1.1.75 1-amino-propan-2-ol + NAD+ = aminoacetone + NADH aminopropanol biosynthesis chlorophyll a chlorophyll a 893.503 C55 H72 N4 O5 MG1 CC(CCCC(C)CCCC(C)CCCC(C)C)=CCOC(=O)CCC6(C4(C1(C(C(=O)OC)C(=O)c2(c(C)c7(n(c=12)[Mg]58(n3(c(c(C=C)c(C)c3C=C(N=45)C(C)6)C=C9(C(C)=C(CC)C(C=7)=N89)))))))) 3.1.1.14 chlorophyll a + H2O = chlorophyllide a + phytol chlorophyll a degradation chlorophyll a chlorophyll a 893.503 C55 H72 N4 O5 MG1 CC(CCCC(C)CCCC(C)CCCC(C)C)=CCOC(=O)CCC6(C4(C1(C(C(=O)OC)C(=O)c2(c(C)c7(n(c=12)[Mg]58(n3(c(c(C=C)c(C)c3C=C(N=45)C(C)6)C=C9(C(C)=C(CC)C(C=7)=N89)))))))) 1.3.1.- tetrahydrogeranylgeranyl-chlorophyll a + NADPH = chlorophyll a + NADP+ chlorophyll a biosynthesis II chlorophyll a chlorophyll a 893.503 C55 H72 N4 O5 MG1 CC(CCCC(C)CCCC(C)CCCC(C)C)=CCOC(=O)CCC6(C4(C1(C(C(=O)OC)C(=O)c2(c(C)c7(n(c=12)[Mg]58(n3(c(c(C=C)c(C)c3C=C(N=45)C(C)6)C=C9(C(C)=C(CC)C(C=7)=N89)))))))) 7-hydroxy-chlorophyll a + H2O + NADP+ = chlorophyll a + O2 + NADPH chlorophyll cycle chlorophyll a chlorophyll a 893.503 C55 H72 N4 O5 MG1 CC(CCCC(C)CCCC(C)CCCC(C)C)=CCOC(=O)CCC6(C4(C1(C(C(=O)OC)C(=O)c2(c(C)c7(n(c=12)[Mg]58(n3(c(c(C=C)c(C)c3C=C(N=45)C(C)6)C=C9(C(C)=C(CC)C(C=7)=N89)))))))) 2.5.1.62 chlorophyllide a + phytyl-PP = chlorophyll a + diphosphate chlorophyll cycle chlorophyll a chlorophyll a 893.503 C55 H72 N4 O5 MG1 CC(CCCC(C)CCCC(C)CCCC(C)C)=CCOC(=O)CCC6(C4(C1(C(C(=O)OC)C(=O)c2(c(C)c7(n(c=12)[Mg]58(n3(c(c(C=C)c(C)c3C=C(N=45)C(C)6)C=C9(C(C)=C(CC)C(C=7)=N89)))))))) 2.5.1.62 chlorophyllide a + phytyl-PP = chlorophyll a + diphosphate chlorophyll a biosynthesis I 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(O)(=O)C(N)CCCC(N)C(=O)O 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(O)(=O)C(N)CCCC(N)C(=O)O CAS:583-93-7:*LIGAND-CPD:C00666:*CAS:14289-34-0 5.1.1.7 L,L-diaminopimelate = meso-diaminopimelate lysine biosynthesis II 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(O)(=O)C(N)CCCC(N)C(=O)O CAS:583-93-7:*LIGAND-CPD:C00666:*CAS:14289-34-0 5.1.1.7 L,L-diaminopimelate = meso-diaminopimelate lysine biosynthesis I 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(O)(=O)C(N)CCCC(N)C(=O)O CAS:583-93-7:*LIGAND-CPD:C00666:*CAS:14289-34-0 3.5.1.47 H2O + N-acetyl-L,L-2,6-diaminopimelate = L,L-diaminopimelate + acetate lysine biosynthesis II 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(O)(=O)C(N)CCCC(N)C(=O)O CAS:583-93-7:*LIGAND-CPD:C00666:*CAS:14289-34-0 2.6.1.- tetrahydrodipicolinate + L-glutamate + H2O = L,L-diaminopimelate + α-ketoglutarate 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(O)(=O)C(N)CCCC(N)C(=O)O CAS:583-93-7:*LIGAND-CPD:C00666:*CAS:14289-34-0 3.5.1.18 H2O = L,L-diaminopimelate + succinate lysine biosynthesis I hydroxybupropion 255.744 C13 H18 N1 O2 CL1 CC(NC(C)(C)CO)C(=O)c1(cc(Cl)ccc1) 1.14.14.1 bupropion + NADPH + O2 = hydroxybupropion + NADP+ + H2O bupropion degradation pinostrobin (S)-2,3-Dihydro-5-hydroxy-7-methoxy-2-phenyl-4-benzopyrone 270.284 C16 H14 O4 c1(c2(c(c(O)cc1OC)C(=O)CC(O2)c3(ccccc3))) (2S)-pinocembrin + S-adenosyl-L-methionine = pinostrobin + S-adenosyl-L-homocysteine pinobanksin biosynthesis 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol 442.724 C30 H50 O2 CC(C)CCCC(C)C1(C2(C(CC1)(C=O)C3(=C(CC2)C4(C(CC3)C(C)(C)C(O)CC4)(C)))(C)) 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol + O2 + NADPH = 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol 442.724 C30 H50 O2 CC(C)CCCC(C)C1(C2(C(CC1)(C=O)C3(=C(CC2)C4(C(CC3)C(C)(C)C(O)CC4)(C)))(C)) 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol + O2 + NADPH = 4,4-dimethyl-5-α-cholesta-8,14-dien-3-β-ol + formate + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) butyrate Butyrate (n-C4:0)*2-butanoate*butyric acid*butanoic acid*ethylacetic acid*butanoate*1-propanecarboxylic acid*propylformic acid 88.106 C4 H8 O2 C(=O)(O)CCC LIGAND-CPD:C00246:*UM-BBD-CPD:c0035:*CAS:107-92-6 2.8.3.8 butyryl-CoA + acetate = butyrate + acetyl-CoA ethanol fermentation to acetate butyrate Butyrate (n-C4:0)*2-butanoate*butyric acid*butanoic acid*ethylacetic acid*butanoate*1-propanecarboxylic acid*propylformic acid 88.106 C4 H8 O2 C(=O)(O)CCC LIGAND-CPD:C00246:*UM-BBD-CPD:c0035:*CAS:107-92-6 2.8.3.8 butyryl-CoA + acetate = butyrate + acetyl-CoA gallate degradation III (anaerobic) butyrate Butyrate (n-C4:0)*2-butanoate*butyric acid*butanoic acid*ethylacetic acid*butanoate*1-propanecarboxylic acid*propylformic acid 88.106 C4 H8 O2 C(=O)(O)CCC LIGAND-CPD:C00246:*UM-BBD-CPD:c0035:*CAS:107-92-6 2.7.2.7 butyrate + ATP = butyryl phosphate + ADP acetyl CoA fermentation to butyrate L-lactate lactic acid*L(+)-lactate*(S)-lactate*L-lactate*lactasol*lac*2-hydroxypropanoic acid*2-hydroxypropionic acid 90.079 C3 H6 O3 CC(O)C(=O)O CAS:79-33-4:*LIGAND-CPD:C00186: 1.2.1.22 H2O + NAD+ + L-lactaldehyde = NADH + L-lactate fucose degradation L-lactate lactic acid*L(+)-lactate*(S)-lactate*L-lactate*lactasol*lac*2-hydroxypropanoic acid*2-hydroxypropionic acid 90.079 C3 H6 O3 CC(O)C(=O)O CAS:79-33-4:*LIGAND-CPD:C00186: L-lactate = pyruvate fucose degradation L-lactate lactic acid*L(+)-lactate*(S)-lactate*L-lactate*lactasol*lac*2-hydroxypropanoic acid*2-hydroxypropionic acid 90.079 C3 H6 O3 CC(O)C(=O)O CAS:79-33-4:*LIGAND-CPD:C00186: L-lactate = pyruvate aerobic respiration -- electron donors reaction list L-lactate lactic acid*L(+)-lactate*(S)-lactate*L-lactate*lactasol*lac*2-hydroxypropanoic acid*2-hydroxypropionic acid 90.079 C3 H6 O3 CC(O)C(=O)O CAS:79-33-4:*LIGAND-CPD:C00186: L-lactate = pyruvate respiration (anaerobic)-- electron donors reaction list L-lactate lactic acid*L(+)-lactate*(S)-lactate*L-lactate*lactasol*lac*2-hydroxypropanoic acid*2-hydroxypropionic acid 90.079 C3 H6 O3 CC(O)C(=O)O CAS:79-33-4:*LIGAND-CPD:C00186: 1.1.1.27 NAD+ + L-lactate = NADH + pyruvate sucrose degradation to ethanol and lactate (anaerobic) L-lactate lactic acid*L(+)-lactate*(S)-lactate*L-lactate*lactasol*lac*2-hydroxypropanoic acid*2-hydroxypropionic acid 90.079 C3 H6 O3 CC(O)C(=O)O CAS:79-33-4:*LIGAND-CPD:C00186: 1.1.1.27 NAD+ + L-lactate = NADH + pyruvate fructose degradation to pyruvate and lactate (anaerobic) L-lactate lactic acid*L(+)-lactate*(S)-lactate*L-lactate*lactasol*lac*2-hydroxypropanoic acid*2-hydroxypropionic acid 90.079 C3 H6 O3 CC(O)C(=O)O CAS:79-33-4:*LIGAND-CPD:C00186: 1.1.1.27 NAD+ + L-lactate = NADH + pyruvate glucose fermentation to lactate II 13-HPOT 13(S)-hydroperoxylinolenic acid*hydroperoxylinolenic acid*13S-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid*13(S)-hydroperoxylinolenate 310.433 C18 H30 O4 CCC=CCC(OO)C=CC=CCCCCCCCC(=O)O 1.13.11.12 O2 + linolenate = 13-HPOT 13-LOX and 13-HPL pathway 13-HPOT 13(S)-hydroperoxylinolenic acid*hydroperoxylinolenic acid*13S-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid*13(S)-hydroperoxylinolenate 310.433 C18 H30 O4 CCC=CCC(OO)C=CC=CCCCCCCCC(=O)O 1.13.11.12 O2 + linolenate = 13-HPOT jasmonic acid biosynthesis 13-HPOT 13(S)-hydroperoxylinolenic acid*hydroperoxylinolenic acid*13S-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid*13(S)-hydroperoxylinolenate 310.433 C18 H30 O4 CCC=CCC(OO)C=CC=CCCCCCCCC(=O)O 13-HPOT = 12-oxo-cis-9-dodecenoate + cis-3-hexenal 13-LOX and 13-HPL pathway 13-HPOT 13(S)-hydroperoxylinolenic acid*hydroperoxylinolenic acid*13S-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid*13(S)-hydroperoxylinolenate 310.433 C18 H30 O4 CCC=CCC(OO)C=CC=CCCCCCCCC(=O)O 4.2.1.92 13-HPOT = H2O + 12,13(S)-epoxylinolenate jasmonic acid biosynthesis 3-aminopropionaldehyde 3-APA 73.094 C3 H7 N1 O1 C(N)CC=O 1.2.1.3 3-aminopropionaldehyde + H2O = β-alanine β-alanine biosynthesis I 3-aminopropionaldehyde 3-APA 73.094 C3 H7 N1 O1 C(N)CC=O 1.4.3.6 1,3-diaminopropane + H2O + O2 = 3-aminopropionaldehyde + ammonia + H2O2 β-alanine biosynthesis I ethylene olefiant gas*elayl*ethene 28.054 C2 H4 C=C 1.14.17.4 L-ascorbate + 1-aminocyclopropane-1-carboxylate + O2 = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine ent-sandaracopimaradiene 272.473 C20 H32 CC1([CH]2(C(CCC1)(C)C3(C(CC2)=CC(C)(C=C)CC3)))(C) ent-sandaracopimaradiene = ent-sandaracopimaradiene-3α-ol oryzalexin A-F biosynthesis ent-sandaracopimaradiene 272.473 C20 H32 CC1([CH]2(C(CCC1)(C)C3(C(CC2)=CC(C)(C=C)CC3)))(C) ent-copalyl diphosphate = ent-sandaracopimaradiene + diphosphate oryzalexin A-F biosynthesis 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 5-phosphoribosyl 1-pyrophosphate + hypoxanthine = inosine-5'-phosphate + diphosphate salvage pathways of adenine, hypoxanthine, and their nucleosides 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.7.6.1 ATP + D-ribose-5-phosphate = 5-phosphoribosyl 1-pyrophosphate + AMP salvage pathways of purine and pyrimidine nucleotides 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.7.6.1 ATP + D-ribose-5-phosphate = 5-phosphoribosyl 1-pyrophosphate + AMP PRPP biosynthesis I 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.8 5-phosphoribosyl 1-pyrophosphate + guanine = diphosphate + GMP salvage pathways of purine nucleosides 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.8 5-phosphoribosyl 1-pyrophosphate + guanine = diphosphate + GMP salvage pathways of purine and pyrimidine nucleotides 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.8 5-phosphoribosyl 1-pyrophosphate + guanine = diphosphate + GMP salvage pathways of purine nucleosides II (plant) 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phosphoribosyl 1-pyrophosphate + L-glutamine + H2O purine nucleotides de novo biosynthesis II 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phosphoribosyl 1-pyrophosphate + L-glutamine + H2O purine nucleotides de novo biosynthesis I 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.9 diphosphate + UMP = 5-phosphoribosyl 1-pyrophosphate + uracil salvage pathways of purine and pyrimidine nucleotides 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.9 diphosphate + UMP = 5-phosphoribosyl 1-pyrophosphate + uracil salvage pathways of pyrimidine ribonucleotides 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.11 nicotinate nucleotide + diphosphate = nicotinate + 5-phosphoribosyl 1-pyrophosphate NAD salvage pathway I 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.11 nicotinate nucleotide + diphosphate = nicotinate + 5-phosphoribosyl 1-pyrophosphate pyridine nucleotide cycling (plants) 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.18 diphosphate = anthranilate + 5-phosphoribosyl 1-pyrophosphate tryptophan biosynthesis 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.8 diphosphate + inosine-5'-phosphate = 5-phosphoribosyl 1-pyrophosphate + hypoxanthine salvage pathways of purine nucleosides 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.8 diphosphate + inosine-5'-phosphate = 5-phosphoribosyl 1-pyrophosphate + hypoxanthine salvage pathways of purine nucleosides II (plant) 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.10 orotidine-5'-phosphate + diphosphate = 5-phosphoribosyl 1-pyrophosphate + orotate de novo biosynthesis of pyrimidine ribonucleotides 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.17 phosphoribosyl-ATP + diphosphate = ATP + 5-phosphoribosyl 1-pyrophosphate histidine biosynthesis I 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.19 CO2 + diphosphate + nicotinate nucleotide = 5-phosphoribosyl 1-pyrophosphate + quinolinate NAD biosynthesis I (from aspartate) 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of adenine, hypoxanthine, and their nucleosides 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of purine nucleosides 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of purine and pyrimidine nucleotides 5-phosphoribosyl 1-pyrophosphate PRPP*5-phospho-α-D-ribose 1-diphosphate*5-phosphoribosyl diphosphate*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 390.071 C5 H13 O14 P3 C(OP(O)(O)=O)C1(OC(C(O)C1O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C00119:*CAS:13270-65-0 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of purine nucleosides II (plant) (-)-limonene (-)-(4S)-limonene*(-)-(S)-limonene 136.236 C10 H16 CC1(=CCC(C(=C)C)CC1) 4.2.3.16 geranyl-PP = (-)-limonene + diphosphate oleoresin monoterpene volatiles biosynthesis (-)-limonene (-)-(4S)-limonene*(-)-(S)-limonene 136.236 C10 H16 CC1(=CCC(C(=C)C)CC1) 4.2.3.16 geranyl-PP = (-)-limonene + diphosphate monoterpene biosynthesis (-)-limonene (-)-(4S)-limonene*(-)-(S)-limonene 136.236 C10 H16 CC1(=CCC(C(=C)C)CC1) 4.2.3.16 geranyl-PP = (-)-limonene + diphosphate menthol biosynthesis phytoene 7,7',8,8',11,11',12,12'-octahydro-ψ,ψ-caro 544.946 C40 H64 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CC=CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C CAS:540-04-5 1.14.99.- phytoene + O2 = phytofluene + H2O carotenoid biosynthesis phytoene 7,7',8,8',11,11',12,12'-octahydro-ψ,ψ-caro 544.946 C40 H64 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CC=CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C CAS:540-04-5 2.5.1.32 prephytoene diphosphate = phytoene + diphosphate carotenoid biosynthesis naringenin chalcone 2'44'6'-tetrahydroxychalcone 271.249 C15 H11 O5 c1(c(o)c(c(O)cc(O)1)C(=O)C=Cc2(ccc(O)cc2)) CAS:520-36-5 2.3.1.74 coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A flavonoid biosynthesis naringenin chalcone 2'44'6'-tetrahydroxychalcone 271.249 C15 H11 O5 c1(c(o)c(c(O)cc(O)1)C(=O)C=Cc2(ccc(O)cc2)) CAS:520-36-5 5.5.1.6 naringenin chalcone = naringenin flavonoid biosynthesis stigmasterol 412.698 C29 H48 O1 CC(C)C(CC)C=CC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) 1.3.1.- sitosterol + NADP+ = stigmasterol + NADPH sterol biosynthesis 3-dehydro-shikimate 3-dehydroshikimic acid*5-dehydroshikimic acid*5-dehydroshikimate 172.137 C7 H8 O5 C(=O)(O)C1(=[CH]C(=O)[CH](O)[CH]([CH2]1)O) CAS:10457-99-5:*LIGAND-CPD:C02637:*CAS:2922-42-1 4.2.1.10 3-dehydroquinate = H2O + 3-dehydro-shikimate quinate degradation 3-dehydro-shikimate 3-dehydroshikimic acid*5-dehydroshikimic acid*5-dehydroshikimate 172.137 C7 H8 O5 C(=O)(O)C1(=[CH]C(=O)[CH](O)[CH]([CH2]1)O) CAS:10457-99-5:*LIGAND-CPD:C02637:*CAS:2922-42-1 4.2.1.10 3-dehydroquinate = H2O + 3-dehydro-shikimate chorismate biosynthesis 3-dehydro-shikimate 3-dehydroshikimic acid*5-dehydroshikimic acid*5-dehydroshikimate 172.137 C7 H8 O5 C(=O)(O)C1(=[CH]C(=O)[CH](O)[CH]([CH2]1)O) CAS:10457-99-5:*LIGAND-CPD:C02637:*CAS:2922-42-1 1.1.1.25 NADP+ + shikimate = NADPH + 3-dehydro-shikimate chorismate biosynthesis 3-dehydro-shikimate 3-dehydroshikimic acid*5-dehydroshikimic acid*5-dehydroshikimate 172.137 C7 H8 O5 C(=O)(O)C1(=[CH]C(=O)[CH](O)[CH]([CH2]1)O) CAS:10457-99-5:*LIGAND-CPD:C02637:*CAS:2922-42-1 1.1.1.282 shikimate = 3-dehydro-shikimate + H+ chorismate biosynthesis 3-dehydro-shikimate 3-dehydroshikimic acid*5-dehydroshikimic acid*5-dehydroshikimate 172.137 C7 H8 O5 C(=O)(O)C1(=[CH]C(=O)[CH](O)[CH]([CH2]1)O) CAS:10457-99-5:*LIGAND-CPD:C02637:*CAS:2922-42-1 3-dehydro-shikimate = H2O quinate degradation phosphoryl-ethanolamine phosphoethanolamine*ethanolamine phosphate*O-Phosphorylethanolamine*O-Phosphoethanolamine 141.063 C2 H8 N1 O4 P1 C(N)COP(O)(=O)O CAS:1071-23-4:*CAS:1071-23-4 2.7.1.82 ethanolamine + ATP = phosphoryl-ethanolamine + ADP choline biosynthesis I phosphoryl-ethanolamine phosphoethanolamine*ethanolamine phosphate*O-Phosphorylethanolamine*O-Phosphoethanolamine 141.063 C2 H8 N1 O4 P1 C(N)COP(O)(=O)O CAS:1071-23-4:*CAS:1071-23-4 2.7.1.82 ethanolamine + ATP = phosphoryl-ethanolamine + ADP phospholipid biosynthesis II phosphoryl-ethanolamine phosphoethanolamine*ethanolamine phosphate*O-Phosphorylethanolamine*O-Phosphoethanolamine 141.063 C2 H8 N1 O4 P1 C(N)COP(O)(=O)O CAS:1071-23-4:*CAS:1071-23-4 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + N-methylethanolamine phosphate choline biosynthesis I phosphoryl-ethanolamine phosphoethanolamine*ethanolamine phosphate*O-Phosphorylethanolamine*O-Phosphoethanolamine 141.063 C2 H8 N1 O4 P1 C(N)COP(O)(=O)O CAS:1071-23-4:*CAS:1071-23-4 2.7.7.14 phosphoryl-ethanolamine + CTP = CDP-ethanolamine + diphosphate phospholipid biosynthesis II phosphoryl-ethanolamine phosphoethanolamine*ethanolamine phosphate*O-Phosphorylethanolamine*O-Phosphoethanolamine 141.063 C2 H8 N1 O4 P1 C(N)COP(O)(=O)O CAS:1071-23-4:*CAS:1071-23-4 4.1.2.27 sphinganine 1-phosphate = palmitaldehyde + phosphoryl-ethanolamine sphingolipid metabolism (-)-vestitone (3R)-vestitone 286.284 C16 H14 O5 C2([CH](c1(c(O)cc(OC)cc1))C(=O)c3(c(O2)cc(O)cc3)) 1.3.1.45 2-hydroxyformononetin + NADPH = (-)-vestitone + NADP+ medicarpin biosynthesis (-)-vestitone (3R)-vestitone 286.284 C16 H14 O5 C2([CH](c1(c(O)cc(OC)cc1))C(=O)c3(c(O2)cc(O)cc3)) 1.1.1.246 (-)-vestitone + NADPH + H+ = 7,2'-dihydroxy-4'-methoxy-isoflavanol + NADP+ medicarpin biosynthesis p-aminobenzoate-β-D-glucopyranosyl ester p-PAPA-Glc 299.28 C13 H17 N1 O7 C(=O)(c1(ccc(N)cc1))OC2(OC(CO)C(O)C(O)C2O) p-aminobenzoate + UDP-D-glucose = p-aminobenzoate-β-D-glucopyranosyl ester + UDP tetrahydrofolate biosynthesis II allantoate 176.132 C4 H8 N4 O4 C(C(O)=O)(NC(N)=O)NC(N)=O LIGAND-CPD:C00499:*CAS:99-16-1 3.5.3.4 H2O + allantoate = (S)-ureidoglycolate + urea allantoin degradation I allantoate 176.132 C4 H8 N4 O4 C(C(O)=O)(NC(N)=O)NC(N)=O LIGAND-CPD:C00499:*CAS:99-16-1 3.5.2.5 H2O + allantoin = allantoate ureide biosynthesis allantoate 176.132 C4 H8 N4 O4 C(C(O)=O)(NC(N)=O)NC(N)=O LIGAND-CPD:C00499:*CAS:99-16-1 3.5.2.5 H2O + allantoin = allantoate allantoin degradation I (-)-β-pinene (-)-(1S,5S)-β-pinene 136.236 C10 H16 CC1(C2(CC1C(=C)CC2))(C) 4.2.3.14 geranyl-PP = (-)-β-pinene + diphosphate oleoresin monoterpene volatiles biosynthesis (-)-β-pinene (-)-(1S,5S)-β-pinene 136.236 C10 H16 CC1(C2(CC1C(=C)CC2))(C) 4.2.3.14 geranyl-PP = (-)-β-pinene + diphosphate monoterpene biosynthesis 2-(2'-methylthio)ethylmalic-acid 208.229 C7 H12 O5 S1 C(SC)CC(O)(C(O)=O)CC(=O)O 5.4.4.- 2-(2'-methylthio)ethylmalic-acid = 3-(2'-methylthio)ethylmalic-acid homomethionine biosynthesis 2-(2'-methylthio)ethylmalic-acid 208.229 C7 H12 O5 S1 C(SC)CC(O)(C(O)=O)CC(=O)O 2.3.3.- 2-oxo-4-methylthiobutanoate + acetyl-CoA + H2O = 2-(2'-methylthio)ethylmalic-acid + coenzyme A homomethionine biosynthesis coniferyl aldehyde 4-hydroxy-3-methoxycinnamaldehyde*4-hydroxy-3-methoxycinnamic aldehyde*coniferaldehyde 178.187 C10 H10 O3 C(=O)C=Cc1(cc(OC)c(O)cc1) CAS:458-36-6 1.14.13.- coniferyl aldehyde + NADPH + O2 = 5-hydroxy-coniferaldehyde + NADP+ + H2O phenylpropanoid biosynthesis coniferyl aldehyde 4-hydroxy-3-methoxycinnamaldehyde*4-hydroxy-3-methoxycinnamic aldehyde*coniferaldehyde 178.187 C10 H10 O3 C(=O)C=Cc1(cc(OC)c(O)cc1) CAS:458-36-6 1.1.1.195 coniferyl aldehyde + NADPH = coniferyl alcohol + NADP+ phenylpropanoid biosynthesis coniferyl aldehyde 4-hydroxy-3-methoxycinnamaldehyde*4-hydroxy-3-methoxycinnamic aldehyde*coniferaldehyde 178.187 C10 H10 O3 C(=O)C=Cc1(cc(OC)c(O)cc1) CAS:458-36-6 1.2.1.44 feruloyl-CoA + NADPH = coniferyl aldehyde + NADP+ + coenzyme A phenylpropanoid biosynthesis N-methyl-β-alanine 103.121 C4 H9 N1 O2 C(NC)CC(=O)O 2.1.1.- N-methyl-β-alanine + S-adenosyl-L-methionine = N,N-dimethyl-β-alanine + S-adenosyl-L-homocysteine β-alanine betaine biosynthesis N-methyl-β-alanine 103.121 C4 H9 N1 O2 C(NC)CC(=O)O 2.1.1.49 β-alanine + S-adenosyl-L-methionine = N-methyl-β-alanine + S-adenosyl-L-homocysteine β-alanine betaine biosynthesis GA15 gibberellin A15*gibberellin A15*GA15 (open lactone form)*gibberellin A15 (open lactone form) 348.438 C20 H28 O5 CC1([CH]4(C(CCC1)(CO)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA15 + α-ketoglutarate + O2 = GA24 + succinate + CO2 + H2O gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) GA15 gibberellin A15*gibberellin A15*GA15 (open lactone form)*gibberellin A15 (open lactone form) 348.438 C20 H28 O5 CC1([CH]4(C(CCC1)(CO)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA12 + O2 + α-ketoglutarate = GA15 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) GA15 gibberellin A15*gibberellin A15*GA15 (open lactone form)*gibberellin A15 (open lactone form) 348.438 C20 H28 O5 CC1([CH]4(C(CCC1)(CO)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA15 + α-ketoglutarate + O2 = GA37 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) cytosine 4-amino-2-oxo-1,2-dihydropyrimidine 111.103 C4 H5 N3 O1 c1(N)(cc[nH]c(n1)=O) 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 C[CH](CO)CCNc2(c1(c([nH]cn1)ncn2)) CAS:23599-75-9 2.4.1.- dihydrozeatin + UDP-D-glucose = dihydrozeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis dihydrozeatin 2-Methyl-4-(1H-purin-6-ylamino)butan-1-ol*N6-(4-Hydroxyisopentanyl)adenine 221.261 C10 H15 N5 O1 C[CH](CO)CCNc2(c1(c([nH]cn1)ncn2)) CAS:23599-75-9 2.4.1.- dihydrozeatin + UDP-D-glucose = dihydrozeatin-7-N-dihydrozeatin + UDP cytokinins 7-N-glucoside biosynthesis dihydrozeatin 2-Methyl-4-(1H-purin-6-ylamino)butan-1-ol*N6-(4-Hydroxyisopentanyl)adenine 221.261 C10 H15 N5 O1 C[CH](CO)CCNc2(c1(c([nH]cn1)ncn2)) CAS:23599-75-9 2.4.1.- dihydrozeatin + UDP-D-glucose = dihydrozeatin-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis aminoacetone 73.094 C3 H7 N1 O1 C(N)C(C)=O LIGAND-CPD:C01888:*CAS:298-08-8 2-amino-3-oxobutanoate = aminoacetone + CO2 threonine degradation III (to methylglyoxal) aminoacetone 73.094 C3 H7 N1 O1 C(N)C(C)=O LIGAND-CPD:C01888:*CAS:298-08-8 2-amino-3-oxobutanoate = aminoacetone + CO2 aminopropanol biosynthesis aminoacetone 73.094 C3 H7 N1 O1 C(N)C(C)=O LIGAND-CPD:C01888:*CAS:298-08-8 1.4.3.6 aminoacetone + H2O + O2 = ammonia + methylglyoxal + H2O2 threonine degradation III (to methylglyoxal) aminoacetone 73.094 C3 H7 N1 O1 C(N)C(C)=O LIGAND-CPD:C01888:*CAS:298-08-8 1.1.1.75 1-amino-propan-2-ol + NAD+ = aminoacetone + NADH aminopropanol biosynthesis GA51-catabolite gibberellin A51-catabolite*gibberellin A51-catabolite*GA51-catabolite 330.38 C19 H22 O5 CC1([CH]4(C(=CC(=O)C1)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA51 + α-ketoglutarate + O2 = GA51-catabolite + succinate + CO2 + H2O gibberellin inactivation GA98 gibberellin A98*gibberellin A98*GA98 380.437 C20 H28 O7 CC1([CH]4(C(CC(O)C1)(CO)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA44 + α-ketoglutarate + O2 = GA98 + succinate + CO2 gibberellin inactivation 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 C(N)C(=O)CCC(=O)O CAS:5451-09-2:*PUBCHEM:137:*LIGAND-CPD:C00430:*CAS:106-60-5 4.2.1.24 5-amino-levulinate = 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 C(N)C(=O)CCC(=O)O CAS:5451-09-2:*PUBCHEM:137:*LIGAND-CPD:C00430:*CAS:106-60-5 5.4.3.8 glutamate-1-semialdehyde = 5-amino-levulinate tetrapyrrole biosynthesis I 4α-formyl-5α-cholesta-8,24-dien-3β-ol 412.654 C28 H44 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C=O)C(O)CC4)))) 1.14.13.72 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I 4α-formyl-5α-cholesta-8,24-dien-3β-ol 412.654 C28 H44 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C=O)C(O)CC4)))) 1.14.13.72 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) 4α-formyl-5α-cholesta-8,24-dien-3β-ol 412.654 C28 H44 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C=O)C(O)CC4)))) 1.14.13.72 4α-formyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I 4α-formyl-5α-cholesta-8,24-dien-3β-ol 412.654 C28 H44 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C=O)C(O)CC4)))) 1.14.13.72 4α-formyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) cis-zeatin riboside monophosphate cZRMP 431.341 C15 H22 N5 O8 P1 C1(O[CH](C(O)C(O)1)COP(O)(=O)O)N2(c3(c(N=C2)c(ncn3)NCC=C(C)CO)) cis-zeatin riboside monophosphate + H2O = cis-zeatin riboside cis-zeatin biosynthesis cis-zeatin riboside monophosphate cZRMP 431.341 C15 H22 N5 O8 P1 C1(O[CH](C(O)C(O)1)COP(O)(=O)O)N2(c3(c(N=C2)c(ncn3)NCC=C(C)CO)) cis-zeatin biosynthesis histidinal L-histidinal 139.157 C6 H9 N3 O1 c1(c(nc[nH]1)C[CH](N)C=O) 1.1.1.23 histidinol + NAD+ = histidinal + NADH histidine biosynthesis I histidinal L-histidinal 139.157 C6 H9 N3 O1 c1(c(nc[nH]1)C[CH](N)C=O) 1.1.1.23 histidinal + NAD+ + H2O = L-histidine + NADH histidine biosynthesis I sinapaldehyde 208.213 C11 H12 O4 C(=O)C=Cc1(cc(OC)c(O)c(c1)OC) 2.1.1.68 5-hydroxy-coniferaldehyde + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + sinapaldehyde phenylpropanoid biosynthesis sinapaldehyde 208.213 C11 H12 O4 C(=O)C=Cc1(cc(OC)c(O)c(c1)OC) 1.1.1.195 sinapaldehyde + NADPH = sinapyl-alcohol + NADP+ phenylpropanoid biosynthesis GA8-catabolite gibberellin A8-catabolite*gibberellin A8-catabolite*GA8-catabolite 362.379 C19 H22 O7 CC1([CH]4(C(=CC(=O)C(O)1)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA8 + α-ketoglutarate + O2 = GA8-catabolite + succinate + CO2 + H2O gibberellin inactivation longifolene 204.355 C15 H24 CC1(CCCC3(C(=C)C2(C1C(CC2)3))(C))(C) 4.2.3.- trans, trans-farnesyl diphosphate = longifolene + diphosphate oleoresin sesquiterpene volatiles biosynthesis a lipid hydroperoxide H1 O2 R1 1.11.1.12 glutathione + a lipid hydroperoxide = glutathione disulfide + lipid + H2O glutathione redox reactions I ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.4 4-guanidinobutyramide + H2O = ammonia + 4-guanidinobutyrate arginine degradation X (arginine monooxygenase pathway) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 4.3.1.12 L-ornithine + NAD+ = L-proline + ammonia + NADH + H+ arginine degradation VII (arginase 3 pathway) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.5 H2O + cytidine = ammonia + uridine salvage pathways of purine and pyrimidine nucleotides ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.5 H2O + cytidine = ammonia + uridine (deoxy)ribose phosphate degradation ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.5 H2O + cytidine = ammonia + uridine salvage pathways of pyrimidine ribonucleotides ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 2.7.2.2 ammonia + CO2 + ATP = carbamoyl-phosphate + ADP citrulline degradation ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 1.4.3.6 tryptamine + H2O + O2 = ammonia + indole acetaldehyde + H2O2 IAA biosynthesis I ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 4.4.1.1 H2O = pyruvate + ammonia glutathione-mediated detoxification ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 4.4.1.8 cystathionine + H2O = ammonia + pyruvate + L-homocysteine methionine biosynthesis II ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 4.4.1.8 cystathionine + H2O = ammonia + pyruvate + L-homocysteine methionine biosynthesis I ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 4.4.1.8 cystathionine + H2O = ammonia + pyruvate + L-homocysteine homocysteine and cysteine interconversion ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 6.3.1.1 ammonia + L-aspartate + ATP = L-asparagine + diphosphate + AMP asparagine biosynthesis III ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 6.3.4.1 ammonia + xanthosine-5-phosphate + ATP = AMP + diphosphate + GMP salvage pathways of purine nucleosides II (plant) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 6.3.4.1 ammonia + xanthosine-5-phosphate + ATP = AMP + diphosphate + GMP purine nucleotides de novo biosynthesis I ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.5 H2O + urea = ammonia + CO2 canavanine degradation ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.5 H2O + urea = ammonia + CO2 arginine degradation VII (arginase 3 pathway) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP glutamine biosynthesis I ammonia NH3 17.03 H3 N1 [NH3] 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 [NH3] 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 [NH3] CAS:7664-41-7 3.5.1.4 acrylamide + H2O = ammonia + acrylate + H+ acrylonitrile degradation ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 2.5.1.61 H2O + porphobilinogen = ammonia + hydroxymethylbilane tetrapyrrole biosynthesis I ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.13 H2O + dCTP = ammonia + dUTP de novo biosynthesis of pyrimidine deoxyribonucleotides ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.2 L-glutamine + H2O = L-glutamate + ammonia citrulline biosynthesis ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 H2O + deoxyadenosine = ammonia + deoxyinosine salvage pathways of adenine, hypoxanthine, and their nucleosides ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 1.4.3.5 O2 + H2O + pyridoxamine 5'-phosphate = ammonia + H2O2 + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.4 nicotinamide + H2O = ammonia + nicotinate aldoxime degradation ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH folate transformations ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH formylTHF biosynthesis II ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH formylTHF biosynthesis I ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH photorespiration ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.3.6 H2O + L-arginine = ammonia + citrulline proline biosynthesis V (from arginine) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 4.3.1.5 L-phenylalanine = ammonia + trans-cinnamate suberin biosynthesis ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 4.3.1.5 L-phenylalanine = ammonia + trans-cinnamate phenylpropanoid biosynthesis, initial reactions ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 4.3.1.5 L-phenylalanine = ammonia + trans-cinnamate salicylate biosynthesis ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 1.6.6.- L-canaline + NADPH = homoserine + ammonia + NADP+ canavanine degradation ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 4.4.1.1 cystathionine + H2O = ammonia + 2-oxobutanoate + L-cysteine homocysteine degradation ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 4.4.1.1 cystathionine + H2O = ammonia + 2-oxobutanoate + L-cysteine homocysteine and cysteine interconversion ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.3 H2O + guanine = ammonia + xanthine purine degradation ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.3 H2O + guanine = ammonia + xanthine salvage pathways of purine nucleosides ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.3 H2O + guanine = ammonia + xanthine salvage pathways of purine nucleosides II (plant) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 4.3.1.17 L-serine = pyruvate + ammonia glycine betaine degradation ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.5.1 indole-3-acetonitrile + H2O = ammonia + indole-3-acetate IAA biosynthesis I ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 4.3.1.1 L-aspartate = ammonia + fumarate glutamine degradation III ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 6.3.1.5 ammonia + ATP + deamido-NAD = AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.5.7 acrylonitrile + H2O = acrylate + ammonia acrylonitrile degradation ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 2.1.2.10 tetrahydrofolate = 5,10-methylene-THF + ammonia glycine cleavage complex ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.20 citrulline + H2O = L-ornithine + CO2 + ammonia proline biosynthesis V (from arginine) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.53 N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia putrescine biosynthesis II ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.53 N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 homoserine + ammonia = L-canaline canavanine biosynthesis ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 4.3.1.19 L-threonine = 2-oxobutanoate + ammonia isoleucine biosynthesis from threonine ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.1 H2O + cytosine = ammonia + uracil salvage pathways of pyrimidine ribonucleotides ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 1.13.99.3 L-tryptophan + O2 = indole acetaldehyde + ammonia + CO2 tryptophan degradation V (side chain pathway) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.3.- N2-succinyl-L-arginine + H2O = ammonia + N2-succinyl-L-ornithine + CO2 arginine degradation II ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.4 H2O + adenosine = ammonia + inosine salvage pathways of adenine, hypoxanthine, and their nucleosides ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.4 H2O + adenosine = ammonia + inosine salvage pathways of purine nucleosides ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.19 nicotinamide + H2O = ammonia + nicotinate NAD salvage pathway I ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.19 nicotinamide + H2O = ammonia + nicotinate pyridine nucleotide cycling (plants) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.6 AMP + H2O = inosine-5'-phosphate + ammonia purine degradation ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.6 AMP + H2O = inosine-5'-phosphate + ammonia salvage pathways of purine nucleosides II (plant) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 6.3.4.16 ammonia + H2O + CO2 + ATP = carbamoyl-phosphate + ADP urea cycle ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 1.4.3.6 aminoacetone + H2O + O2 = ammonia + methylglyoxal + H2O2 threonine degradation III (to methylglyoxal) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.42 nicotinamide mononucleotide + H2O = ammonia + nicotinate nucleotide NAD salvage pathway I ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 4.4.1.11 L-methionine + H2O = methanethiol + ammonia + 2-oxobutanoate methionine degradation II ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.5 H2O + deoxycytidine = ammonia + deoxyuridine (deoxy)ribose phosphate degradation ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.5 H2O + deoxycytidine = ammonia + deoxyuridine salvage pathways of pyrimidine deoxyribonucleotides ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 1.4.3.6 1,3-diaminopropane + H2O + O2 = 3-aminopropionaldehyde + ammonia + H2O2 β-alanine biosynthesis I ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.3.19 H2O + (S)-ureidoglycolate = ammonia + CO2 + glyoxylate allantoin degradation I ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.3.12 H2O + agmatine = ammonia + N-carbamoylputrescine putrescine biosynthesis II ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.3.12 H2O + agmatine = ammonia + N-carbamoylputrescine arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.1 L-asparagine + H2O = ammonia + L-aspartate asparagine degradation I ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.1 L-asparagine + H2O = ammonia + L-aspartate asparagine degradation II ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.6 H2O + 3-ureidopropionate = ammonia + CO2 + β-alanine β-alanine biosynthesis III ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.4 indole-3-acetamide + H2O = indole-3-acetate + ammonia IAA biosynthesis VI (via indole-3-acetamide) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.1.4 indole-3-acetamide + H2O = indole-3-acetate + ammonia IAA biosynthesis IV ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.26 H2O + 2,5-diamino-6-(ribosylamino)-4-(3H)-pyrimidinone 5'-phosphate = 5-amino-6-(5'-phosphoribosylamino)uracil + ammonia flavin biosynthesis ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.15 H2O + guanosine = ammonia + xanthosine purine degradation ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 3.5.4.15 H2O + guanosine = ammonia + xanthosine salvage pathways of purine nucleosides II (plant) ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 1.4.1.4 L-glutamate + H2O + NADP+ = ammonia + α-ketoglutarate + NADPH proline biosynthesis I ammonia NH3 17.03 H3 N1 [NH3] CAS:7664-41-7 1.7.7.- nitrite = ammonia + H2O nitrate reduction II (assimilatory) 2'-hydroxypseudobaptigenin 2',7-dihydroxy-3',4'-methylenedioxyisoflavone*DMI 298.251 C16 H10 O6 C1(=C(C(=O)c2(c(O1)cc(O)cc2))c3(c(O)cc4(c(c3)OCO4))) 1.14.13.53 pseudobaptigenin + NADPH + O2 = 2'-hydroxypseudobaptigenin + NADP+ + H2O maackiain biosynthesis 2'-hydroxypseudobaptigenin 2',7-dihydroxy-3',4'-methylenedioxyisoflavone*DMI 298.251 C16 H10 O6 C1(=C(C(=O)c2(c(O1)cc(O)cc2))c3(c(O)cc4(c(c3)OCO4))) 1.3.1.45 2'-hydroxypseudobaptigenin + NADPH = (-)-sophorol + NADP+ maackiain biosynthesis 3-hydroxy-anthranilate 3-hydroxyanthranilate 153.137 C7 H7 N1 O3 C(O)(=O)c1(c(N)c(O)ccc1) CAS:548-93-6 3.7.1.3 3-hydroxy-L-kynurenine + H2O = 3-hydroxy-anthranilate + L-alanine tryptophan degradation III (eukaryotic) 3-hydroxy-anthranilate 3-hydroxyanthranilate 153.137 C7 H7 N1 O3 C(O)(=O)c1(c(N)c(O)ccc1) CAS:548-93-6 1.13.11.6 O2 + 3-hydroxy-anthranilate = 2-amino-3-carboxymuconate semialdehyde tryptophan degradation III (eukaryotic) dolichyl β-D-glucosyl phosphate 1352.044 C86 H143 O9 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(O)(=O)OC1(OC(CO)C(O)C(O)C(O)1) 2.4.1.117 dolichyl-phosphate + UDP-D-glucose = dolichyl β-D-glucosyl phosphate + UDP dolichyl-diphosphooligosaccharide biosynthesis dolichyl β-D-glucosyl phosphate 1352.044 C86 H143 O9 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(O)(=O)OC1(OC(CO)C(O)C(O)C(O)1) glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-glucosyl phosphate = (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis dolichyl β-D-glucosyl phosphate 1352.044 C86 H143 O9 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(O)(=O)OC1(OC(CO)C(O)C(O)C(O)1) (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-glucosyl phosphate = oligosaccharide-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis dolichyl β-D-glucosyl phosphate 1352.044 C86 H143 O9 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(O)(=O)OC1(OC(CO)C(O)C(O)C(O)1) (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-glucosyl phosphate = glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis putrescine 1,4-diaminobutane*1,4-butanediamine*tetramethylenediamine*putrescine 88.152 C4 H12 N2 C(N)CCCN LIGAND-CPD:C00134:*CAS:110-60-1 3.5.3.11 H2O + agmatine = urea + putrescine arginine degradation III (arginine decarboxylase/agmatinase pathway) putrescine 1,4-diaminobutane*1,4-butanediamine*tetramethylenediamine*putrescine 88.152 C4 H12 N2 C(N)CCCN LIGAND-CPD:C00134:*CAS:110-60-1 3.5.3.11 H2O + agmatine = urea + putrescine putrescine biosynthesis I putrescine 1,4-diaminobutane*1,4-butanediamine*tetramethylenediamine*putrescine 88.152 C4 H12 N2 C(N)CCCN LIGAND-CPD:C00134:*CAS:110-60-1 3.5.1.53 N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia putrescine biosynthesis II putrescine 1,4-diaminobutane*1,4-butanediamine*tetramethylenediamine*putrescine 88.152 C4 H12 N2 C(N)CCCN LIGAND-CPD:C00134:*CAS:110-60-1 3.5.1.53 N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) putrescine 1,4-diaminobutane*1,4-butanediamine*tetramethylenediamine*putrescine 88.152 C4 H12 N2 C(N)CCCN LIGAND-CPD:C00134:*CAS:110-60-1 2.5.1.16 putrescine + S-adenosyl-L-methioninamine = spermidine + 5'-methylthioadenosine spermidine biosynthesis putrescine 1,4-diaminobutane*1,4-butanediamine*tetramethylenediamine*putrescine 88.152 C4 H12 N2 C(N)CCCN LIGAND-CPD:C00134:*CAS:110-60-1 4.1.1.17 L-ornithine = CO2 + putrescine putrescine biosynthesis III 2,7-dihydroxy-4'-methoxyisoflavanone 286.284 C16 H14 O5 C2(C(c1(ccc(OC)cc1))C(=O)c3(c(O2)cc(O)cc3))(O) 2-hydroxyisoflavanone + S-adenosyl-L-methionine = 2,7-dihydroxy-4'-methoxyisoflavanone + S-adenosyl-L-homocysteine pterocarpan biosynthesis 2,7-dihydroxy-4'-methoxyisoflavanone 286.284 C16 H14 O5 C2(C(c1(ccc(OC)cc1))C(=O)c3(c(O2)cc(O)cc3))(O) 2,7-dihydroxy-4'-methoxyisoflavanone = formononetin + H2O pterocarpan biosynthesis 18:2-18:3-MGDG 1-18:2-2-18:3-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(9Z,12Z,15Z-octadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerol 793.089 C45 H76 O11 C(OC1(C(O)C(O)C(OO)C(O1)CO))C(OC(=O)CCCCCCCC=CCC=CCC=CCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-18:2-MGDG = 18:2-18:3-MGDG glycolipid desaturation 18:2-18:3-MGDG 1-18:2-2-18:3-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(9Z,12Z,15Z-octadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerol 793.089 C45 H76 O11 C(OC1(C(O)C(O)C(OO)C(O1)CO))C(OC(=O)CCCCCCCC=CCC=CCC=CCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-18:3-MGDG = 18:3-18:3-MGDG glycolipid desaturation 2,3-dihydroxy-3-methylvalerate (R)-2,3-Dihydroxy-3-methylpentanoate*(R)-2,3-Dihydroxy-3-methylvalerate*2,3-dihydroxy-3-methylpentanoate 148.158 C6 H12 O4 CC(CC)(O)C(O)C(=O)O LIGAND-CPD:C06007: 4.2.1.9 2,3-dihydroxy-3-methylvalerate = 2-keto-3-methyl-valerate + H2O isoleucine biosynthesis from threonine 2,3-dihydroxy-3-methylvalerate (R)-2,3-Dihydroxy-3-methylpentanoate*(R)-2,3-Dihydroxy-3-methylvalerate*2,3-dihydroxy-3-methylpentanoate 148.158 C6 H12 O4 CC(CC)(O)C(O)C(=O)O LIGAND-CPD:C06007: 1.1.1.86 2-aceto-2-hydroxy-butyrate + NADPH = 2,3-dihydroxy-3-methylvalerate + NADP+ isoleucine biosynthesis from threonine trans-zeatin zeatin*cytokinin*(2E)-2-methyl-4-(1H-purin-6-ylamino)-2-buten-1-ol*t-zeatin 218.238 C10 H12 N5 O1 c2(ncnc1(c(ncn1)2))(NCC=C(C)CO) 1.5.99.12 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 218.238 C10 H12 N5 O1 c2(ncnc1(c(ncn1)2))(NCC=C(C)CO) isopentenyladenine + 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 218.238 C10 H12 N5 O1 c2(ncnc1(c(ncn1)2))(NCC=C(C)CO) 2.4.1.203 trans-zeatin + UDP-D-glucose = trans-zeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis trans-zeatin zeatin*cytokinin*(2E)-2-methyl-4-(1H-purin-6-ylamino)-2-buten-1-ol*t-zeatin 218.238 C10 H12 N5 O1 c2(ncnc1(c(ncn1)2))(NCC=C(C)CO) trans-zeatin riboside monophosphate = 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 218.238 C10 H12 N5 O1 c2(ncnc1(c(ncn1)2))(NCC=C(C)CO) 2.4.1.- trans-zeatin + UDP-D-glucose = trans-zeatin-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis trans-zeatin zeatin*cytokinin*(2E)-2-methyl-4-(1H-purin-6-ylamino)-2-buten-1-ol*t-zeatin 218.238 C10 H12 N5 O1 c2(ncnc1(c(ncn1)2))(NCC=C(C)CO) 2.4.1.- trans-zeatin + UDP-D-glucose = trans-zeatin-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis trans-zeatin zeatin*cytokinin*(2E)-2-methyl-4-(1H-purin-6-ylamino)-2-buten-1-ol*t-zeatin 218.238 C10 H12 N5 O1 c2(ncnc1(c(ncn1)2))(NCC=C(C)CO) trans-zeatin riboside + H2O = trans-zeatin + D-ribose trans-zeatin biosynthesis dolichol 1109.922 C80 H132 O1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCO 2.7.1.108 dolichol + CTP = dolichyl-phosphate + CDP dolichyl-diphosphooligosaccharide biosynthesis 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate 6-hydroxymethyl-dihydropterin pyrophosphate*2-amino-7,8-dihydro-4-hydroxy-6-(diphosphooxymethyl)-pteridine*dihydropterin-CH2OH-diphosphate*dihydropterin-CH2OH-pp 355.14 C7 H11 N5 O8 P2 C2(C(COP(O)(=O)OP(O)(=O)O)=Nc1(c(O)nc(N)nc1N2)) 2.7.6.3 6-hydroxymethyl-dihydropterin + ATP = 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + AMP tetrahydrofolate biosynthesis I 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate 6-hydroxymethyl-dihydropterin pyrophosphate*2-amino-7,8-dihydro-4-hydroxy-6-(diphosphooxymethyl)-pteridine*dihydropterin-CH2OH-diphosphate*dihydropterin-CH2OH-pp 355.14 C7 H11 N5 O8 P2 C2(C(COP(O)(=O)OP(O)(=O)O)=Nc1(c(O)nc(N)nc1N2)) 2.7.6.3 6-hydroxymethyl-dihydropterin + ATP = 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + AMP tetrahydrofolate biosynthesis II 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate 6-hydroxymethyl-dihydropterin pyrophosphate*2-amino-7,8-dihydro-4-hydroxy-6-(diphosphooxymethyl)-pteridine*dihydropterin-CH2OH-diphosphate*dihydropterin-CH2OH-pp 355.14 C7 H11 N5 O8 P2 C2(C(COP(O)(=O)OP(O)(=O)O)=Nc1(c(O)nc(N)nc1N2)) 2.5.1.15 p-aminobenzoate + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate = diphosphate tetrahydrofolate biosynthesis I 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate 6-hydroxymethyl-dihydropterin pyrophosphate*2-amino-7,8-dihydro-4-hydroxy-6-(diphosphooxymethyl)-pteridine*dihydropterin-CH2OH-diphosphate*dihydropterin-CH2OH-pp 355.14 C7 H11 N5 O8 P2 C2(C(COP(O)(=O)OP(O)(=O)O)=Nc1(c(O)nc(N)nc1N2)) 2.5.1.15 p-aminobenzoate + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate = diphosphate tetrahydrofolate biosynthesis II L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.10 L-homocysteine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + L-methionine methionine biosynthesis II L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 4.2.1.22 L-homocysteine + L-serine = H2O + cystathionine homocysteine degradation L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 4.2.1.22 L-homocysteine + L-serine = H2O + cystathionine homocysteine and cysteine interconversion L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O 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 homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O 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 L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.5 L-homocysteine + glycine betaine = L-methionine + dimethylglycine glycine betaine degradation L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.5.1.49 O-acetyl-L-homoserine + hydrogen sulfide = L-homocysteine + acetate homocysteine biosynthesis L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.10 S-methyl-L-methionine + L-homocysteine = L-methionine methionine biosynthesis II L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.10 S-methyl-L-methionine + L-homocysteine = L-methionine S-methylmethionine cycle L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 4.4.1.8 cystathionine + H2O = ammonia + pyruvate + L-homocysteine methionine biosynthesis II L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 4.4.1.8 cystathionine + H2O = ammonia + pyruvate + L-homocysteine methionine biosynthesis I L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 4.4.1.8 cystathionine + H2O = ammonia + pyruvate + L-homocysteine homocysteine and cysteine interconversion L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine S-adenosylmethionine biosynthesis L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine methionine biosynthesis II L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine methionine biosynthesis I L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine S-adenosyl-L-methionine cycle L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate S-adenosylmethionine biosynthesis L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate methionine biosynthesis I L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate folate transformations L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate formylTHF biosynthesis II L-homocysteine homo-cys*homocysteine 135.181 C4 H9 N1 O2 S1 C(S)CC(N)C(O)=O CAS:6027-13-0:*LIGAND-CPD:C00155:*CAS:454-28-4 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate formylTHF biosynthesis I fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = fructose-6-phosphate + D-glyceraldehyde-3-phosphate pentose phosphate pathway (partial) fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = fructose-6-phosphate + D-glyceraldehyde-3-phosphate xylulose-monophosphate cycle fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = fructose-6-phosphate + D-glyceraldehyde-3-phosphate Calvin cycle fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = fructose-6-phosphate + D-glyceraldehyde-3-phosphate pentose phosphate pathway (non-oxidative branch) fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate sucrose degradation to ethanol and lactate (anaerobic) fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate glycolysis IV (plant cytosol) fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate fructose degradation to pyruvate and lactate (anaerobic) fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate glycolysis I fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = fructose-6-phosphate + D-erythrose-4-phosphate pentose phosphate pathway (non-oxidative branch) fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = fructose-6-phosphate + D-erythrose-4-phosphate glucose fermentation to lactate II fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.6.1.16 fructose-6-phosphate + L-glutamine = L-glutamate + D-glucosamine-6-phosphate UDP-N-acetylgalactosamine biosynthesis fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.8 mannose-6-phosphate = fructose-6-phosphate ascorbate biosynthesis fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.8 mannose-6-phosphate = fructose-6-phosphate GDP-mannose metabolism fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.8 mannose-6-phosphate = fructose-6-phosphate mannose degradation fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 4.1.2.22 fructose-6-phosphate = H2O + D-erythrose-4-phosphate + acetylphosphate glucose fermentation to lactate II fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.90 fructose-6-phosphate + diphosphate = fructose-1,6-bisphosphate glycolysis IV (plant cytosol) fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.9 β-D-glucose-6-phosphate = fructose-6-phosphate ascorbate biosynthesis fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.9 β-D-glucose-6-phosphate = fructose-6-phosphate sucrose degradation III fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.9 β-D-glucose-6-phosphate = fructose-6-phosphate gluconeogenesis fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.9 β-D-glucose-6-phosphate = fructose-6-phosphate starch biosynthesis fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.9 β-D-glucose-6-phosphate = fructose-6-phosphate glucose fermentation to lactate II fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.9 β-D-glucose-6-phosphate = fructose-6-phosphate glycolysis I fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.4.1.14 fructose-6-phosphate + UDP-D-glucose = sucrose-6-phosphate + UDP sucrose biosynthesis fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP sucrose degradation III fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP sucrose degradation I fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP sucrose degradation to ethanol and lactate (anaerobic) fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP fructose degradation to pyruvate and lactate (anaerobic) fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 3.1.3.11 fructose-1,6-bisphosphate + H2O = fructose-6-phosphate xylulose-monophosphate cycle fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 3.1.3.11 fructose-1,6-bisphosphate + H2O = fructose-6-phosphate Calvin cycle fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 3.1.3.11 fructose-1,6-bisphosphate + H2O = fructose-6-phosphate gluconeogenesis fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 3.1.3.11 fructose-1,6-bisphosphate + H2O = fructose-6-phosphate glycolysis I fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 2.7.1.69 fructose = fructose-6-phosphate fructose degradation to pyruvate and lactate (anaerobic) fructose-6-phosphate fructose-6-phosphate*F6P*fructose-6P*fructose-6-P*fruc6p*fru-6-P*D-fructose-6-phosphate*A-D-fructose-6-P*D-fructose-6-P 260.137 C6 H13 O9 P1 C(O)C1(O)(OC(C(O)C1O)COP(O)(O)=O) LIGAND-CPD:C00085:*CAS:643-13-0 5.3.1.9 α-D-glucose 6-phosphate = fructose-6-phosphate sucrose degradation to ethanol and lactate (anaerobic) 5α-cholesta-8-en-3-one 384.644 C27 H44 O1 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)CC(=O)CC4)(C)))(C)) 1.1.1.170 4α-carboxy-5α-cholesta-8-en-3β-ol = 5α-cholesta-8-en-3-one + CO2 cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 5α-cholesta-8-en-3-one 384.644 C27 H44 O1 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)CC(=O)CC4)(C)))(C)) 1.1.1.270 5α-cholesta-8-en-3-one + NADPH = zymostenol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) β-carotene 536.882 C40 H56 CC(C=CC1(=C(C)CCCC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)(C)CCCC(C)=2) CAS:7235-40-7 5.5.1.- γ-carotene = β-carotene carotenoid biosynthesis β-carotene 536.882 C40 H56 CC(C=CC1(=C(C)CCCC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)(C)CCCC(C)=2) CAS:7235-40-7 1.14.99.- β-carotene + O2 = β-cryptoxanthin + H2O carotenoid biosynthesis D-mannonate mannonate 196.157 C6 H12 O7 C(=O)(O)[CH](O)[CH](O)[CH](O)[CH](O)CO LIGAND-CPD:C00514: 1.1.1.57 NAD+ + D-mannonate = NADH + fructuronate β-D-glucuronide degradation D-mannonate mannonate 196.157 C6 H12 O7 C(=O)(O)[CH](O)[CH](O)[CH](O)[CH](O)CO LIGAND-CPD:C00514: 4.2.1.8 D-mannonate = H2O + 2-dehydro-3-deoxy-D-gluconate β-D-glucuronide degradation dCTP 2'-deoxycytidine-5'-triphosphate*deoxycytidine-triphosphate*deoxy-CTP 467.159 C9 H16 N3 O13 P3 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C2)COP(O)(=O)OP(O)(=O)OP(O)(=O)O)) LIGAND-CPD:C00458:*CAS:2056-98-6 3.5.4.13 H2O + dCTP = ammonia + dUTP de novo biosynthesis of pyrimidine deoxyribonucleotides dCTP 2'-deoxycytidine-5'-triphosphate*deoxycytidine-triphosphate*deoxy-CTP 467.159 C9 H16 N3 O13 P3 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C2)COP(O)(=O)OP(O)(=O)OP(O)(=O)O)) LIGAND-CPD:C00458:*CAS:2056-98-6 CTP = dCTP + H2O de novo biosynthesis of pyrimidine deoxyribonucleotides dCTP 2'-deoxycytidine-5'-triphosphate*deoxycytidine-triphosphate*deoxy-CTP 467.159 C9 H16 N3 O13 P3 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C2)COP(O)(=O)OP(O)(=O)OP(O)(=O)O)) LIGAND-CPD:C00458:*CAS:2056-98-6 2.7.4.6 dCDP + ATP = dCTP + ADP de novo biosynthesis of pyrimidine deoxyribonucleotides trans-zeatin riboside diphosphate ZDP*zeatin diphosphate*tZRDP 511.321 C15 H23 N5 O11 P2 C1(C(O)C(O)C(O1)COP(=O)(O)OP(O)(O)=O)n2(c3(c(nc2)c(ncn3)NCC=C(C)CO)) trans-zeatin riboside triphosphate + H2O = trans-zeatin riboside diphosphate trans-zeatin biosynthesis trans-zeatin riboside diphosphate ZDP*zeatin diphosphate*tZRDP 511.321 C15 H23 N5 O11 P2 C1(C(O)C(O)C(O1)COP(=O)(O)OP(O)(O)=O)n2(c3(c(nc2)c(ncn3)NCC=C(C)CO)) isopentenyladenosine-5'-diphosphate + NADPH + H2O = trans-zeatin riboside diphosphate + NADP+ trans-zeatin biosynthesis trans-zeatin riboside diphosphate ZDP*zeatin diphosphate*tZRDP 511.321 C15 H23 N5 O11 P2 C1(C(O)C(O)C(O1)COP(=O)(O)OP(O)(O)=O)n2(c3(c(nc2)c(ncn3)NCC=C(C)CO)) trans-zeatin riboside diphosphate + H2O = trans-zeatin riboside monophosphate trans-zeatin biosynthesis 1,5-diazabicyclononane 1,5-diazabicyclo[4.3.0]nonane 126.201 C7 H14 N2 C1(CCC2(N1CCCN2)) 1-(3-aminopropyl)-pyrrolinium = 1,5-diazabicyclononane β-alanine biosynthesis I (+)-pulegone 152.236 C10 H16 O1 CC(C)=C1(C(=O)CC(C)CC1) (+)-pulegone + NADPH = (+)-isomenthone + NADP+ menthol biosynthesis (+)-pulegone 152.236 C10 H16 O1 CC(C)=C1(C(=O)CC(C)CC1) (+)-pulegone + NADPH + O2 = (+)-menthofuran + NADP+ + H2O menthol biosynthesis (+)-pulegone 152.236 C10 H16 O1 CC(C)=C1(C(=O)CC(C)CC1) (+)-pulegone + NADPH = (-)-menthone + NADP+ menthol biosynthesis (+)-pulegone 152.236 C10 H16 O1 CC(C)=C1(C(=O)CC(C)CC1) (+)-cis-isopulegone + NADP+ = (+)-pulegone + NADPH menthol biosynthesis demethylphylloquinone 3-phytyl-1,4-naphtoquinone 436.676 C30 H44 O2 CC(CCCC(C)CCCC(C)C)CCCC(C)=CCC1(C(=O)C2(=C(C(=O)C=1)C=CC=C2)) 1,4-dihydroxy-2-naphthoate + phytyl-PP = demethylphylloquinone + CO2 + diphosphate phylloquinone biosynthesis demethylphylloquinone 3-phytyl-1,4-naphtoquinone 436.676 C30 H44 O2 CC(CCCC(C)CCCC(C)C)CCCC(C)=CCC1(C(=O)C2(=C(C(=O)C=1)C=CC=C2)) demethylphylloquinone + S-adenosyl-L-methionine = phylloquinone + S-adenosyl-L-homocysteine phylloquinone biosynthesis liquiritigenin 7,4'-dihydroxyflavanone 256.257 C15 H12 O4 c3(c2(OC(c1(ccc(O)cc1))CC(=O)c2ccc(O)3)) liquiritigenin + NADPH + O2 = 6,7,4'-trihydroxyflavanone + NADP+ + H2O 6,7,4'-trihydroxyisoflavone 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 294.433 C18 H30 O3 CCC=CCC1(C(CCC1=O)CCCCCCCC(=O)O) 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate + O2 = (+)-7-isojasmonate + acetate 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 294.433 C18 H30 O3 CCC=CCC1(C(CCC1=O)CCCCCCCC(=O)O) 1.3.1.42 NADP+ + 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate = NADPH + 12-oxo-cis-10,15-phytodienoate jasmonic acid biosynthesis raffinose 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 C(O)C1(OC(CO)(C(O)C1O)OC2(OC(C(O)C(O)C2O)COC3(OC(CO)C(O)C(O)C3O))) CAS:512-69-6 2.4.1.67 galactinol + raffinose = myo-inositol + stachyose stachyose biosynthesis raffinose 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 C(O)C1(OC(CO)(C(O)C1O)OC2(OC(C(O)C(O)C2O)COC3(OC(CO)C(O)C(O)C3O))) CAS:512-69-6 2.4.1.82 galactinol + sucrose = myo-inositol + raffinose stachyose biosynthesis oleate octadecenoate (n-C18:1)*oleic acid*9-octadecenoic acid 282.465 C18 H34 O2 CCCCCCCCC=CCCCCCCCC(=O)O PUBCHEM:445639:*LIGAND-CPD:C00712:*CAS:112-80-1 2.1.1.79 oleate + S-adenosyl-L-methionine = dihydrosterculate + S-adenosyl-L-homocysteine cyclopropane and cyclopropene fatty acid biosynthesis oleate octadecenoate (n-C18:1)*oleic acid*9-octadecenoic acid 282.465 C18 H34 O2 CCCCCCCCC=CCCCCCCCC(=O)O PUBCHEM:445639:*LIGAND-CPD:C00712:*CAS:112-80-1 1.14.13.- oleate + NADPH + O2 = 18-hydroxyoleate + NADP+ + H2O cutin biosynthesis oleate octadecenoate (n-C18:1)*oleic acid*9-octadecenoic acid 282.465 C18 H34 O2 CCCCCCCCC=CCCCCCCCC(=O)O PUBCHEM:445639:*LIGAND-CPD:C00712:*CAS:112-80-1 1.14.13.- oleate + NADPH + O2 = 18-hydroxyoleate + NADP+ + H2O suberin biosynthesis DIMBOA-Glc DIMBOA-glucoside*2-(2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one)-β-D-glucopyranose 373.316 C15 H19 N1 O10 C2(C(OC1(OC(CO)C(O)C(O)C(O)1))Oc3(c(N(O)2)ccc(c3)OC))(=O) PUBCHEM:441563: 3.2.1.21 DIMBOA-Glc + H2O = DIMBOA + β-D-glucose DIMBOA-glucoside degradation 18:1-16:0-DGDG 1-18:1-2-16:0-digalactosyldiacylglycerol 919.241 C49 H90 O15 C(OC1(OC(C(O)C(O)C1O)COC2(C(O)C(O)C(O)C(O2)CO)))C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC 1.14.99.- 18:1-16:0-DGDG = 18:2-16:0-DGDG glycolipid desaturation tropinone 139.197 C8 H13 N1 O1 CN1(C2(CC(=O)CC1CC2)) NCI:118012*CAS:532-24-1 1.1.1.236 NADP+ + pseudotropine = NADPH + tropinone calystegine biosynthesis tropinone 139.197 C8 H13 N1 O1 CN1(C2(CC(=O)CC1CC2)) NCI:118012*CAS:532-24-1 unknown = tropinone calystegine biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.- geranyl-PP = (E)-β-ocimene + diphosphate monoterpene biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.- geranyl-PP = (-)-β-phellandrene + diphosphate oleoresin monoterpene volatiles biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.- geranyl-PP = tricyclene + diphosphate oleoresin monoterpene volatiles biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.16 geranyl-PP = (-)-limonene + diphosphate oleoresin monoterpene volatiles biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.16 geranyl-PP = (-)-limonene + diphosphate monoterpene biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.16 geranyl-PP = (-)-limonene + diphosphate menthol biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 2.5.1.10 geranyl-PP = diphosphate + trans, trans-farnesyl diphosphate geranylgeranyldiphosphate biosynthesis II (plastidic) geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 2.5.1.10 geranyl-PP = diphosphate + trans, trans-farnesyl diphosphate polyisoprenoid biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 2.5.1.10 geranyl-PP = diphosphate + trans, trans-farnesyl diphosphate trans,trans-farnesyl diphosphate biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.- geranyl-PP + H2O = geraniol + diphosphate secologanin and strictosidine biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.- geranyl-PP = (+)-3-carene + diphosphate oleoresin monoterpene volatiles biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.14 geranyl-PP = (-)-β-pinene + diphosphate oleoresin monoterpene volatiles biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.14 geranyl-PP = (-)-β-pinene + diphosphate monoterpene biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.- geranyl-PP = (Z)-β-ocimene + diphosphate monoterpene biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.- geranyl-PP = sabinene + diphosphate monoterpene biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 2.5.1.1 dimethylallyl-PP = diphosphate + geranyl-PP geranylgeranyldiphosphate biosynthesis II (plastidic) geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 2.5.1.1 dimethylallyl-PP = diphosphate + geranyl-PP polyisoprenoid biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 2.5.1.1 dimethylallyl-PP = diphosphate + geranyl-PP geranyldiphosphate biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 2.5.1.1 dimethylallyl-PP = diphosphate + geranyl-PP trans,trans-farnesyl diphosphate biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.14 geranyl-PP = (-)-α-pinene + diphosphate oleoresin monoterpene volatiles biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.14 geranyl-PP = (-)-α-pinene + diphosphate monoterpene biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.15 geranyl-PP = β-myrcene + diphosphate oleoresin monoterpene volatiles biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.15 geranyl-PP = β-myrcene + diphosphate monoterpene biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.- geranyl-PP + H2O = (-)-α-terpineol + diphosphate monoterpene biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.- geranyl-PP = terpinolene + diphosphate monoterpene biosynthesis geranyl-PP GPP*geranyl-diphosphate*geranyl-pyrophosphate 314.211 C10 H20 O7 P2 C(OP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)C LIGAND-CPD:C00341: 4.2.3.- geranyl-PP = (-)-camphene + diphosphate oleoresin monoterpene volatiles biosynthesis 18:3-16:0-MGDG 1-18:3-2-16:0-monogalactosyldiacylglycerol*1-(9Z,12Z,15Z-octadecatrienoyl)-2-hexadecanoyl-3-O-beta-D-galactosyl-sn-glycerol 753.067 C43 H76 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:2-16:0-MGDG = 18:3-16:0-MGDG glycolipid desaturation 18:3-16:0-MGDG 1-18:3-2-16:0-monogalactosyldiacylglycerol*1-(9Z,12Z,15Z-octadecatrienoyl)-2-hexadecanoyl-3-O-beta-D-galactosyl-sn-glycerol 753.067 C43 H76 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:3-16:0-MGDG = 18:3-16:1-MGDG glycolipid desaturation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.17 L-glutamate + ATP = ADP formylTHF biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.17 L-glutamate + ATP = ADP formylTHF biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 L-glutamate + ATP + NADPH = ADP + L-glutamate γ-semialdehyde + NADP+ arginine biosynthesis IV ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.2 ammonia + CO2 + ATP = carbamoyl-phosphate + ADP citrulline degradation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP formylTHF biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP tetrahydrofolate biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP formylTHF biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP tetrahydrofolate biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.3 AMP + ATP = ADP salvage pathways of purine and pyrimidine nucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.3 AMP + ATP = ADP purine nucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.6 dADP + ATP = dATP + ADP purine nucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.1.1 ammonia + L-aspartate + ATP = L-asparagine + diphosphate + AMP asparagine biosynthesis III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.71 shikimate + ATP = shikimate-3-phosphate + ADP chorismate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.33 pantothenate + ATP = D-4'-phosphopantothenate + ADP coenzyme A biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.- nicotinate riboside + ATP = nicotinate nucleotide + ADP pyridine nucleotide cycling (plants) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.15 L-proline + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.- ATP + pyridoxine = ADP + pyridoxine-5'-phosphate pyridoxal 5'-phosphate salvage pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.23 NAD+ + ATP = NADP+ + ADP NAD/NADH phosphorylation and dephosphorylation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate de novo biosynthesis of pyrimidine ribonucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis II (acetyl cycle) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.15 biotin + ATP = diphosphate + AMP biotin-carboxyl carrier protein ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.17 ATP + L-glutamate = ADP folate polyglutamylation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.17 ATP + L-glutamate = ADP formylTHF biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.17 ATP + L-glutamate = ADP tetrahydrofolate biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = 5'-phosphoribosyl-N-formylglycineamide + ADP purine nucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 D-myo-inositol (3,4,6)-trisphosphate + ATP = D-myo-inositol (3,4,5,6)-tetrakisphosphate + ADP lipid-independent phytate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.2 FMN + ATP = FAD + diphosphate flavin biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.11 L-glutamate + ATP = L-glutamate-5-phosphate + ADP proline biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate sucrose degradation to ethanol and lactate (anaerobic) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate glycolysis IV (plant cytosol) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate fructose degradation to pyruvate and lactate (anaerobic) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate glycolysis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.26 ATP + O-succinylbenzoate + coenzyme A = 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA + AMP + diphosphate phylloquinone biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.6 dCDP + ATP = dCTP + ADP de novo biosynthesis of pyrimidine deoxyribonucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.22 nicotinamide riboside + ATP = nicotinamide mononucleotide + ADP NAD salvage pathway II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.2 ATP + UTP + L-glutamine + H2O = ADP + CTP + L-glutamate de novo biosynthesis of pyrimidine ribonucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.3.2 N5-formyl-THF + ATP = ADP folate transformations ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.3.2 N5-formyl-THF + ATP = ADP formylTHF biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.10 L-methionine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.17 D-xylulose + ATP = D-xylulose-5-phosphate + ADP xylose degradation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.16 L-cysteine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.11 L-serine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate mixed acid fermentation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate sucrose degradation to ethanol and lactate (anaerobic) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate respiration (anaerobic) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate glycolysis IV (plant cytosol) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate fructose degradation to pyruvate and lactate (anaerobic) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate glucose fermentation to lactate II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate glycolysis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.64 myo-inositol + ATP = D-myo-inositol (3)-monophosphate + ADP lipid-independent phytate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.39 homoserine + ATP = O-phospho-L-homoserine + ADP threonine biosynthesis from homoserine ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.39 homoserine + ATP = O-phospho-L-homoserine + ADP methionine biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.9 L-valine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.- ATP + UMP = ADP + UDP de novo biosynthesis of pyrimidine ribonucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.- ATP + UMP = ADP + UDP salvage pathways of purine and pyrimidine nucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.3 ADP = ATP + formate tetrahydrofolate biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.4.2.17 phosphoribosyl-ATP + diphosphate = ATP + 5-phosphoribosyl 1-pyrophosphate histidine biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.7 mannose + ATP = mannose-6-phosphate + ADP GDP-mannose metabolism ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.7 mannose + ATP = mannose-6-phosphate + ADP mannose degradation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.5 L-isoleucine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP oxidative ethanol degradation III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP glutamate degradation VII (to butyrate) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP oxidative ethanol degradation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.27 α-D-glucose 1-phosphate + ATP = ADP-D-glucose + diphosphate starch biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.18 ATP + nicotinate nucleotide = diphosphate + deamido-NAD NAD biosynthesis I (from aspartate) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.18 ATP + nicotinate nucleotide = diphosphate + deamido-NAD NAD salvage pathway I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.18 ATP + nicotinate nucleotide = diphosphate + deamido-NAD pyridine nucleotide cycling (plants) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.4.1.4 ATP + 3-methylcrotonyl-CoA + HCO3- = ADP + 3-methylglutaconyl-CoA leucine degradation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.6 L-lysine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.24 dephospho-CoA + ATP = coenzyme A + ADP coenzyme A biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.4 L-aspartate + ATP = L-aspartyl-4-phosphate + ADP lysine biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.4 L-aspartate + ATP = L-aspartyl-4-phosphate + ADP lysine biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF folate polyglutamylation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF folate transformations ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF formylTHF biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF formylTHF biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.6 dUDP + ATP = dUTP + ADP de novo biosynthesis of pyrimidine deoxyribonucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.9.3 H2O + selenide + ATP = selenophosphate + AMP selenocysteine biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.32 choline + ATP = phosphoryl-choline + ADP phospholipid biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.1 ammonia + xanthosine-5-phosphate + ATP = AMP + diphosphate + GMP salvage pathways of purine nucleosides II (plant) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.1 ammonia + xanthosine-5-phosphate + ATP = AMP + diphosphate + GMP purine nucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.48 uridine + ATP = UMP + ADP salvage pathways of purine and pyrimidine nucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.17 coenzyme A + propionate + ATP = propionyl-CoA + diphosphate + AMP β-alanine biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.12 caffeate + coenzyme A + ATP = caffeoyl-CoA + AMP + diphosphate suberin biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.18 L-glutamine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.134 D-myo-inositol (3,4,5,6)-tetrakisphosphate + ATP = D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-independent phytate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.86 NADH + ATP = NADPH + ADP NAD/NADH phosphorylation and dephosphorylation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.10 UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + D-alanyl-D-alanine + ATP = ADP peptidoglycan biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.22 L-asparagine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.1 β-alanine + L-pantoate + ATP = pantothenate + diphosphate + AMP pantothenate biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.1 β-alanine + L-pantoate + ATP = pantothenate + diphosphate + AMP pantothenate biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.1 β-D-glucose + ATP = β-D-glucose-6-phosphate + ADP glucose fermentation to lactate II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.- D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = phytate + ADP lipid-independent phytate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.1.5 ammonia + ATP + deamido-NAD = AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 D-myo-inositol (3,4)-bisphosphate + ATP = D-myo-inositol (3,4,6)-trisphosphate + ADP lipid-independent phytate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.43 glucuronate + ATP = α-D-glucuronate 1-phosphate + ADP UDP-D-glucuronate biosynthesis (from myo-inositol) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.13 UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + meso-diaminopimelate + ATP = UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + ADP peptidoglycan biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.2 mevalonate-5P + ATP = mevalonate-5-PP + ADP mevalonate pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.9 ATP + dTMP = ADP + dTDP salvage pathways of purine and pyrimidine nucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.9 ATP + dTMP = ADP + dTDP de novo biosynthesis of pyrimidine deoxyribonucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.35 ATP + pyridoxamine = ADP + pyridoxamine 5'-phosphate pyridoxal 5'-phosphate salvage pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP Calvin cycle ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP gluconeogenesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP sucrose degradation to ethanol and lactate (anaerobic) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP glycolysis IV (plant cytosol) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP fructose degradation to pyruvate and lactate (anaerobic) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP glucose fermentation to lactate II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP glycolysis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.29 dihydroxy-acetone + ATP = dihydroxy-acetone-phosphate + ADP xylulose-monophosphate cycle ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine S-adenosylmethionine biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine methionine salvage pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.9 UDP-N-acetylmuramoyl-L-alanine + D-glutamate + ATP = UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + ADP peptidoglycan biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 4.1.1.49 oxaloacetate + ATP = CO2 + phosphoenolpyruvate + ADP gluconeogenesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.6.1.1 ATP + protoporphyrin IX + Mg2+ + H2O = Mg-protoporphyrin + ADP + H+ chlorophyllide a biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.35 ATP + pyridoxal = ADP + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.35 ATP + pyridoxal = ADP + pyridoxal 5'-phosphate pyridoxamine anabolism ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 4.1.1.33 mevalonate-5-PP + ATP = CO2 + ADP mevalonate pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 ATP = dATP + H2O purine nucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.3 L-threonine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.73 inosine + ATP = inosine-5'-phosphate + ADP salvage pathways of adenine, hypoxanthine, and their nucleosides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.73 inosine + ATP = inosine-5'-phosphate + ADP salvage pathways of purine nucleosides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.73 inosine + ATP = inosine-5'-phosphate + ADP salvage pathways of purine nucleosides II (plant) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.1 nicotinamide mononucleotide + ATP = NAD+ + diphosphate NAD salvage pathway II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ NAD salvage pathway I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ pyridine nucleotide cycling (plants) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.4 L-leucine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.6.3 6-hydroxymethyl-dihydropterin + ATP = 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + AMP tetrahydrofolate biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.6.3 6-hydroxymethyl-dihydropterin + ATP = 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + AMP tetrahydrofolate biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.6 ATP + 4-carboxyaminoimidazole ribonucleotide + L-aspartate = ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole purine nucleotides de novo biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.6 ATP + 4-carboxyaminoimidazole ribonucleotide + L-aspartate = ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole purine nucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.3 coenzyme A + ATP = diphosphate + AMP acyl-CoA synthetase pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine purine nucleotides de novo biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine purine nucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.26 ATP + O-succinylbenzoate + coenzyme A = AMP + diphosphate + O-succinylbenzoyl-CoA menaquinone biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.1 ATP + acetate = ADP + acetylphosphate mixed acid fermentation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.1 ATP + acetate = ADP + acetylphosphate D-lactate fermentation to propionate and acetate ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.1 ATP + acetate = ADP + acetylphosphate ethanol fermentation to acetate ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.1 ATP + acetate = ADP + acetylphosphate glucose fermentation to lactate II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.1 ATP + acetate = ADP + acetylphosphate gallate degradation III (anaerobic) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.6.5 ATP + GDP = AMP + guanosine 5'-diphosphate,3'-diphosphate ppGpp biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.5.1.- dimethylallyl-PP + ATP = isopentenyladenosine-5'-triphosphate + diphosphate trans-zeatin biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP glutamine biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.45 2-dehydro-3-deoxy-D-gluconate + ATP = 2-keto-3-deoxy-6-phospho-gluconate + ADP β-D-glucuronide degradation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.15 D-ribose + ATP = D-ribose-5-phosphate + ADP ribose degradation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.14 glycine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.6.5 GTP + ATP = guanosine 3'-diphosphate 5'-triphosphate + AMP ppGpp biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.49 ATP + hydroxymethylpyrimidine = ADP + hydroxymethylpyrimidine phosphate thiamine biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.91 4-hydroxysphinganine + ATP = phytosphingosine-1-P + ADP sphingolipid metabolism ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.20 adenosine + ATP = AMP + ADP salvage pathways of purine nucleosides II (plant) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.30 glycerol + ATP = sn-glycerol-3-phosphate + ADP glycerol degradation IV ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.30 glycerol + ATP = sn-glycerol-3-phosphate + ADP glycerol degradation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.50 ATP + 4-methyl-5-(β-hydroxyethyl)thiazole = ADP + 4-methyl-5-(β-hydroxyethyl)thiazole phosphate thiamine biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.5 succinate + coenzyme A + ATP = succinyl-CoA + ADP reductive TCA cycle I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.5 succinate + coenzyme A + ATP = succinyl-CoA + ADP TCA cycle ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.2 β-D-glucose + ATP = β-D-glucose-6-phosphate + ADP trehalose degradation II (high osmolarity) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.6 dGDP + ATP = dGTP + ADP purine nucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.6.1 ATP + D-ribose-5-phosphate = 5-phosphoribosyl 1-pyrophosphate + AMP salvage pathways of purine and pyrimidine nucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.6.1 ATP + D-ribose-5-phosphate = 5-phosphoribosyl 1-pyrophosphate + AMP PRPP biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = ADP + 5-phospho-ribosyl-glycineamide purine nucleotides de novo biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = ADP + 5-phospho-ribosyl-glycineamide purine nucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.20 L-phenylalanine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.12 ATP + gluconate = 6-phospho-D-gluconate + ADP L-idonate degradation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.130 lipid A disaccharide + ATP = lipid IVA + ADP lipid-A-precursor biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.6 CDP + ATP = CTP + ADP de novo biosynthesis of pyrimidine ribonucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.5 O-ureidohomoserine + L-aspartate + ATP = canavaninosuccinate + AMP + diphosphate canavanine biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.31 glycerate + ATP = 3-phosphoglycerate + ADP glycolate and glyoxylate degradation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.31 glycerate + ATP = 3-phosphoglycerate + ADP allantoin degradation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.31 glycerate + ATP = 3-phosphoglycerate + ADP photorespiration ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP urea cycle ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis II (acetyl cycle) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP citrulline-nitric oxide cycle ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis IV ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP sucrose degradation III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP sucrose degradation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP sucrose degradation to ethanol and lactate (anaerobic) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP fructose degradation to pyruvate and lactate (anaerobic) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.- cytidine + ATP = CMP + ADP salvage pathways of purine and pyrimidine nucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.91 sphinganine + ATP = sphinganine 1-phosphate + ADP sphingolipid metabolism ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.82 ethanolamine + ATP = phosphoryl-ethanolamine + ADP choline biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.82 ethanolamine + ATP = phosphoryl-ethanolamine + ADP phospholipid biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.16 ammonia + H2O + CO2 + ATP = carbamoyl-phosphate + ADP urea cycle ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = glutathione + ADP glutathione biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.148 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + ATP = 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + ADP methylerythritol phosphate pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.6 ATP = α-D-galactose 1-phosphate + ADP galactose degradation II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.6 ATP = α-D-galactose 1-phosphate + ADP UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.19 L-arginine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.4 D-alanine + ATP = D-alanyl-D-alanine + ADP peptidoglycan biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.2.7 butyrate + ATP = butyryl phosphate + ADP acetyl CoA fermentation to butyrate ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.6 dTDP + ATP = dTTP + ADP de novo biosynthesis of pyrimidine deoxyribonucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.1 α-D-glucose + ATP = α-D-glucose 6-phosphate + ADP sucrose degradation III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.1 α-D-glucose + ATP = α-D-glucose 6-phosphate + ADP starch degradation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid β-oxidation I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid β-oxidation II (plant, saturated) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.8 GMP + ATP = GDP + ADP salvage pathways of purine and pyrimidine nucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.8 GMP + ATP = GDP + ADP purine nucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.9.2 H2O + pyruvate + ATP = phosphoenolpyruvate + AMP reductive TCA cycle I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.9.2 H2O + pyruvate + ATP = phosphoenolpyruvate + AMP gluconeogenesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.9.2 H2O + pyruvate + ATP = phosphoenolpyruvate + AMP glycolysis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.2 ATP + L-tryptophan = AMP + diphosphate tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.21 thymidine + ATP = dTMP + ADP salvage pathways of purine and pyrimidine nucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.21 thymidine + ATP = dTMP + ADP salvage pathways of pyrimidine deoxyribonucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.17 tetrahydrofolate + L-glutamate + ATP = THF-L-glutamate + ADP tetrahydrofolate biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.21 deoxyuridine + ATP = dUMP + ADP salvage pathways of pyrimidine deoxyribonucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 ATP + L-serine + 2,3-dihydroxybenzoate = enterobactin + diphosphate + AMP enterobactin biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.89 thiamin + ATP = thiamine-phosphate + ADP thiamine biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.11 L-serine + ATP = diphosphate + AMP selenocysteine biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.8 L-alanine + UDP-N-acetylmuramate + ATP = UDP-N-acetylmuramoyl-L-alanine + ADP peptidoglycan biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.21 L-histidine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.14 ATP + CMP = ADP + CDP salvage pathways of purine and pyrimidine nucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.14 ATP + CMP = ADP + CDP salvage pathways of pyrimidine ribonucleotides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = ADP + 5-aminoimidazole ribonucleotide purine nucleotides de novo biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = ADP + 5-aminoimidazole ribonucleotide purine nucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.3 pantetheine 4'-phosphate + ATP = dephospho-CoA + diphosphate coenzyme A biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.6 GDP + ATP = GTP + ADP purine nucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.19 D-ribulose-5-phosphate + ATP = ADP Calvin cycle ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.36 (R)-mevalonate + ATP = mevalonate-5P + ADP mevalonate pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.91 phytosphingosine-1-P + ADP = ATP + 4-hydroxysphinganine sphingolipid metabolism ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.12 L-aspartate + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.1 L-tyrosine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.100 ATP + 5-methylthioribose = ADP + 5-methylthioribose-1-phosphate methionine salvage pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.18 5-aminoimidazole ribonucleotide + ATP + HCO3- = N5-carboxyaminoimidazole ribonucleotide + ADP purine nucleotides de novo biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.25 adenosine 5'-phosphosulfate + ATP = phosphoadenosine-5'-phosphosulfate + ADP sulfate reduction I (assimilatory) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.25 adenosine 5'-phosphosulfate + ATP = phosphoadenosine-5'-phosphosulfate + ADP sulfate activation for sulfonation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 D-myo-inositol (3)-monophosphate + ATP = D-myo-inositol (3,4)-bisphosphate + ADP lipid-independent phytate biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.16 thiamine-phosphate + ATP = thiamine diphosphate + ADP thiamine biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.4.1.2 ATP + acetyl-CoA + HCO3- + H+ = ADP + malonyl-CoA fatty acid biosynthesis - initial steps ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.1.1.7 L-alanine + ATP = diphosphate + AMP tRNA charging pathway ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.12 coenzyme A + 4-coumarate + ATP = coumaroyl-CoA + diphosphate + AMP flavonoid biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.12 coenzyme A + 4-coumarate + ATP = coumaroyl-CoA + diphosphate + AMP phenylpropanoid biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.73 guanosine + ATP = GMP + ADP salvage pathways of purine nucleosides ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.73 guanosine + ATP = GMP + ADP salvage pathways of purine nucleosides II (plant) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.2.2 L-cysteine + L-glutamate + ATP = L-γ-glutamylcysteine + ADP glutathione biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = dethiobiotin + ADP biotin biosynthesis II ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = dethiobiotin + ADP biotin biosynthesis I ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.2.1.12 ferulate + coenzyme A + ATP = feruloyl-CoA + AMP + diphosphate suberin biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 6.3.4.14 CO2 + ATP = ADP biotin-carboxyl carrier protein ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.7 hydroxymethylpyrimidine phosphate + ATP = 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate + ADP thiamine biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.51 L-fuculose + ATP = fuculose-1-phosphate + ADP fucose degradation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.26 riboflavin + ATP = FMN + ADP flavin biosynthesis ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.1.91 sphinganine + ATP = sphinganine 1-phosphate + ADP sphingolipid metabolism ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate reduction II (assimilatory) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfite oxidation III ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate reduction I (assimilatory) ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate activation for sulfonation ATP adenylpyrophosphate*adenosine-triphosphate*adenosine-5'-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00002:*CAS:56-65-5 2.7.4.6 UDP + ATP = UTP + ADP de novo biosynthesis of pyrimidine ribonucleotides inositol-P-ceramide IPC 2.4.1.- inositol phosphate = inositol-P-ceramide sphingolipid metabolism inositol-P-ceramide IPC 2.4.1.- inositol-P-ceramide + GDP-D-mannose = mannosyl-inositol-phosphorylceramide sphingolipid metabolism GA44 gibberellin A44*gibberellin A44*GA44*GA44 open lactone form*gibberellin A44 open lactone form*GA44 free alcohol form*gibberellin A44 free alcohol form 364.438 C20 H28 O6 CC1([CH]4(C(CCC1)(CO)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA44 + α-ketoglutarate + O2 = GA98 + succinate + CO2 gibberellin inactivation GA44 gibberellin A44*gibberellin A44*GA44*GA44 open lactone form*gibberellin A44 open lactone form*GA44 free alcohol form*gibberellin A44 free alcohol form 364.438 C20 H28 O6 CC1([CH]4(C(CCC1)(CO)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA44 + α-ketoglutarate + O2 = GA38 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) GA44 gibberellin A44*gibberellin A44*GA44*GA44 open lactone form*gibberellin A44 open lactone form*GA44 free alcohol form*gibberellin A44 free alcohol form 364.438 C20 H28 O6 CC1([CH]4(C(CCC1)(CO)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA53 + O2 + α-ketoglutarate = GA44 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) GA44 gibberellin A44*gibberellin A44*GA44*GA44 open lactone form*gibberellin A44 open lactone form*GA44 free alcohol form*gibberellin A44 free alcohol form 364.438 C20 H28 O6 CC1([CH]4(C(CCC1)(CO)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.12 GA44 + α-ketoglutarate + O2 = GA19 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) calycosin 3'-hydroxyformononetin 284.268 C16 H12 O5 C2(=C(c1(ccc(c(c1)O)OC))C(=O)c3(c(O2)cc(O)cc3)) CAS:20575-57-9: 1.14.13.52 formononetin + NADPH + O2 = calycosin + NADP+ + H2O maackiain biosynthesis calycosin 3'-hydroxyformononetin 284.268 C16 H12 O5 C2(=C(c1(ccc(c(c1)O)OC))C(=O)c3(c(O2)cc(O)cc3)) CAS:20575-57-9: calycosin + NADPH + O2 = pseudobaptigenin + NADP+ + H2O maackiain biosynthesis glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = glutathione + ADP glutathione biosynthesis glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 6.1.1.14 glycine + ATP = diphosphate + AMP tRNA charging pathway glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 3.4.11.2 [Cys-Gly]-S-conjugate + H2O = glycine glutathione-mediated detoxification glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 3.4.11.2 Cys-Gly + H2O = L-cysteine + glycine γ-glutamyl cycle glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 2.6.1.4 α-ketoglutarate + glycine = L-glutamate + glyoxylate photorespiration glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = ADP + 5-phospho-ribosyl-glycineamide purine nucleotides de novo biosynthesis II glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = ADP + 5-phospho-ribosyl-glycineamide purine nucleotides de novo biosynthesis I glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH folate transformations glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH formylTHF biosynthesis II glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH formylTHF biosynthesis I glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH photorespiration glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 1.5.3.1 O2 + H2O + sarcosine = H2O2 + formaldehyde + glycine glycine betaine degradation glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN 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)CN LIGAND-CPD:C00037:*CAS:56-40-6 m-chlorobenzoate + glycine = m-chlorohippurate + H2O bupropion degradation glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate glycine biosynthesis I glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate folate polyglutamylation I glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate folate transformations glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate glycine betaine degradation glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate formylTHF biosynthesis II glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate formylTHF biosynthesis I glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate photorespiration glycine G*aminoacetic acid*gly 75.067 C2 H5 N1 O2 C(=O)(O)CN LIGAND-CPD:C00037:*CAS:56-40-6 2.3.1.29 glycine + acetyl-CoA = 2-amino-3-oxobutanoate + coenzyme A threonine degradation II 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol 426.681 C29 H46 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C=O)C(O)CC4)))) 1.14.13.72 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol 426.681 C29 H46 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C=O)C(O)CC4)))) 1.14.13.72 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol 426.681 C29 H46 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C=O)C(O)CC4)))) 1.14.13.72 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol 426.681 C29 H46 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C=O)C(O)CC4)))) 1.14.13.72 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) 3-isopropylmalate 2-D-threo-hydroxy-3-carboxy-isocaproate*3-carboxy-2-hydroxy-4-methylpentanoate*β-isopropylmalate 176.169 C7 H12 O5 C(O)(=O)C(O)C(C(C)C)C(=O)O LIGAND-CPD:C04411: 1.1.1.85 3-isopropylmalate + NAD+ = 2-isopropyl-3-oxosuccinate + NADH + H+ leucine biosynthesis 3-isopropylmalate 2-D-threo-hydroxy-3-carboxy-isocaproate*3-carboxy-2-hydroxy-4-methylpentanoate*β-isopropylmalate 176.169 C7 H12 O5 C(O)(=O)C(O)C(C(C)C)C(=O)O LIGAND-CPD:C04411: 4.2.1.33 2-isopropylmalate = 3-isopropylmalate leucine biosynthesis indole-3-acetaldoxime 3-indoleacetaldoxime*indole-3-acetaldehyde oxime 174.202 C10 H10 N2 O1 c1(c(CC=NO)c2(c([nH]1)cccc2)) 1.14.13.- L-tryptophan + NADPH + O2 = indole-3-acetaldoxime + CO2 + NADP+ + H2O IAA biosynthesis I indole-3-acetaldoxime 3-indoleacetaldoxime*indole-3-acetaldehyde oxime 174.202 C10 H10 N2 O1 c1(c(CC=NO)c2(c([nH]1)cccc2)) N-hydroxyl-tryptamine = indole-3-acetaldoxime IAA biosynthesis I indole-3-acetaldoxime 3-indoleacetaldoxime*indole-3-acetaldehyde oxime 174.202 C10 H10 N2 O1 c1(c(CC=NO)c2(c([nH]1)cccc2)) 4.99.1.6 indole-3-acetaldoxime = indole-3-acetonitrile + H2O IAA biosynthesis I 4-hydroxy-4-(3-pyridyl)-butanoate 4-hydroxy-4-(3-pyridyl)-butanoic acid*γ-(3-pyridyl)-γ-hydroxybutyric acid*4-(3-pyridyl)-4-hydroxybutyric acid 181.191 C9 H11 N1 O3 c1(ncc(cc1)C(O)CCC(O)=O) 4-hydroxy-4-(3-pyridyl)-butanoate = 4-(3-pyridyl)-3-butenoate nicotine degradation II 4-hydroxy-4-(3-pyridyl)-butanoate 4-hydroxy-4-(3-pyridyl)-butanoic acid*γ-(3-pyridyl)-γ-hydroxybutyric acid*4-(3-pyridyl)-4-hydroxybutyric acid 181.191 C9 H11 N1 O3 c1(ncc(cc1)C(O)CCC(O)=O) 4-hydroxy-4-(3-pyridyl)-butanoate = 4-(3-pyridyl)-3-butenoate nicotine degradation III 4-hydroxy-4-(3-pyridyl)-butanoate 4-hydroxy-4-(3-pyridyl)-butanoic acid*γ-(3-pyridyl)-γ-hydroxybutyric acid*4-(3-pyridyl)-4-hydroxybutyric acid 181.191 C9 H11 N1 O3 c1(ncc(cc1)C(O)CCC(O)=O) 4-oxo-4-(3-pyridyl)-butanoate = 4-hydroxy-4-(3-pyridyl)-butanoate nicotine degradation II 4-hydroxy-4-(3-pyridyl)-butanoate 4-hydroxy-4-(3-pyridyl)-butanoic acid*γ-(3-pyridyl)-γ-hydroxybutyric acid*4-(3-pyridyl)-4-hydroxybutyric acid 181.191 C9 H11 N1 O3 c1(ncc(cc1)C(O)CCC(O)=O) 4-oxo-4-(3-pyridyl)-butanoate = 4-hydroxy-4-(3-pyridyl)-butanoate nicotine degradation III DIMBOA 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 211.174 C9 H9 N1 O5 C1(C(O)Oc2(c(N(O)1)ccc(c2)OC))(=O) 3.2.1.21 DIMBOA-Glc + H2O = DIMBOA + β-D-glucose DIMBOA-glucoside degradation UDP-N-acetylmuramoyl-L-alanine 750.5 C23 H36 N4 O20 P2 CC(=O)NC1(C(OC(CO)C(O)C1OC(C)C(=O)NC(C)C(O)=O)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c(=O)[nH]c(=O)cc3))) LIGAND-CPD:C01212: 6.3.2.9 UDP-N-acetylmuramoyl-L-alanine + D-glutamate + ATP = UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + ADP peptidoglycan biosynthesis I UDP-N-acetylmuramoyl-L-alanine 750.5 C23 H36 N4 O20 P2 CC(=O)NC1(C(OC(CO)C(O)C1OC(C)C(=O)NC(C)C(O)=O)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c(=O)[nH]c(=O)cc3))) LIGAND-CPD:C01212: 6.3.2.8 L-alanine + UDP-N-acetylmuramate + ATP = UDP-N-acetylmuramoyl-L-alanine + ADP peptidoglycan biosynthesis I HX LIGAND-CPD:C01318: 2.5.1.18 glutathione + RX = HX glutathione-mediated detoxification 9-mercaptodethiobiotin 9-mercaptodesthiobiotin 246.324 C10 H18 N2 O3 S1 C(=O)(O)CCCCCC1(C(CS)NC(=O)N1) 2.8.1.6 9-mercaptodethiobiotin = biotin biotin biosynthesis II 9-mercaptodethiobiotin 9-mercaptodesthiobiotin 246.324 C10 H18 N2 O3 S1 C(=O)(O)CCCCCC1(C(CS)NC(=O)N1) 2.8.1.6 dethiobiotin + sulfur donor = 9-mercaptodethiobiotin biotin biosynthesis II ethanolamine 2-aminoethanol*monoethanolamine*colamine*ethanol-amine 61.083 C2 H7 N1 O1 C(O)CN LIGAND:C00189:*LIGAND-CPD:C00189:*CAS:141-43-5 2.7.1.82 ethanolamine + ATP = phosphoryl-ethanolamine + ADP choline biosynthesis I ethanolamine 2-aminoethanol*monoethanolamine*colamine*ethanol-amine 61.083 C2 H7 N1 O1 C(O)CN LIGAND:C00189:*LIGAND-CPD:C00189:*CAS:141-43-5 2.7.1.82 ethanolamine + ATP = phosphoryl-ethanolamine + ADP phospholipid biosynthesis II ethanolamine 2-aminoethanol*monoethanolamine*colamine*ethanol-amine 61.083 C2 H7 N1 O1 C(O)CN LIGAND:C00189:*LIGAND-CPD:C00189:*CAS:141-43-5 4.1.1.- L-serine = ethanolamine + CO2 choline biosynthesis I ethanolamine 2-aminoethanol*monoethanolamine*colamine*ethanol-amine 61.083 C2 H7 N1 O1 C(O)CN LIGAND:C00189:*LIGAND-CPD:C00189:*CAS:141-43-5 3.5.1.4 anandamide + H2O = arachidonate + ethanolamine anandamide degradation ethanolamine 2-aminoethanol*monoethanolamine*colamine*ethanol-amine 61.083 C2 H7 N1 O1 C(O)CN LIGAND:C00189:*LIGAND-CPD:C00189:*CAS:141-43-5 2.7.8.- L-serine = ethanolamine phospholipid biosynthesis II isovaleryl-CoA 3-methylbutyryl-CoA*3-methylbutanoyl-CoA*isovaleryl-coenzyme A*iso-valeryl-CoA 851.652 C26 H44 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(C)C) CAS:6244-91-3 1.3.99.10 isovaleryl-CoA + FAD = 3-methylcrotonyl-CoA + FADH2 leucine degradation I isovaleryl-CoA 3-methylbutyryl-CoA*3-methylbutanoyl-CoA*isovaleryl-coenzyme A*iso-valeryl-CoA 851.652 C26 H44 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(C)C) CAS:6244-91-3 2-ketoisocaproate + coenzyme A + NAD+ = isovaleryl-CoA + CO2 + NADH leucine degradation I isovaleryl-CoA 3-methylbutyryl-CoA*3-methylbutanoyl-CoA*isovaleryl-coenzyme A*iso-valeryl-CoA 851.652 C26 H44 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(C)C) CAS:6244-91-3 2.3.1.156 malonyl-CoA + isovaleryl-CoA = phlorisovalerophenone + CO2 + coenzyme A humulone biosynthesis O2- Superoxide anion*peroxide radical*O2(.-)*superoxide 31.999 O2 O=[O-] LIGAND-CPD:C00704: 1.15.1.1 O2- + H+ = H2O2 + O2 removal of superoxide radicals octaprenyl diphosphate farnesylfarnesylgeranyl-PP*octaprenyl pyrophosphate*OPP*farnesylfarnesylgeraniol*all-trans-octaprenyl diphosphate 722.92 C40 H68 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 LIGAND-CPD:C04146: octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate = demethylmenaquinone-8 + diphosphate + CO2 menaquinone biosynthesis coproporphyrinogen III coproporphyrinogen 660.766 C36 H40 N4 O8 Cc5(c(CCC(=O)O)c4(Cc1(nc(c(C)c1CCC(=O)O)Cc2(nc(c(c2C)CCC(=O)O)Cc3(c(C)c(c(n3)Cc(n4)5)CCC(O)=O))))) LIGAND-CPD:C03263:*CAS:2624-63-7 4.1.1.37 uroporphyrinogen-III = CO2 + coproporphyrinogen III heme biosynthesis II coproporphyrinogen III coproporphyrinogen 660.766 C36 H40 N4 O8 Cc5(c(CCC(=O)O)c4(Cc1(nc(c(C)c1CCC(=O)O)Cc2(nc(c(c2C)CCC(=O)O)Cc3(c(C)c(c(n3)Cc(n4)5)CCC(O)=O))))) LIGAND-CPD:C03263:*CAS:2624-63-7 4.1.1.37 uroporphyrinogen-III = CO2 + coproporphyrinogen III chlorophyllide a biosynthesis coproporphyrinogen III coproporphyrinogen 660.766 C36 H40 N4 O8 Cc5(c(CCC(=O)O)c4(Cc1(nc(c(C)c1CCC(=O)O)Cc2(nc(c(c2C)CCC(=O)O)Cc3(c(C)c(c(n3)Cc(n4)5)CCC(O)=O))))) LIGAND-CPD:C03263:*CAS:2624-63-7 1.3.3.3 coproporphyrinogen III + O2 + H+ = protoporphyrinogen IX + CO2 + H2O heme biosynthesis II coproporphyrinogen III coproporphyrinogen 660.766 C36 H40 N4 O8 Cc5(c(CCC(=O)O)c4(Cc1(nc(c(C)c1CCC(=O)O)Cc2(nc(c(c2C)CCC(=O)O)Cc3(c(C)c(c(n3)Cc(n4)5)CCC(O)=O))))) LIGAND-CPD:C03263:*CAS:2624-63-7 1.3.3.3 coproporphyrinogen III + O2 + H+ = protoporphyrinogen IX + CO2 + H2O chlorophyllide a biosynthesis 6,7-dimethyl-8-(1-D-ribityl)lumazine 326.308 C13 H18 N4 O6 CC1(N(CC(O)C(O)C(O)CO)C2(C(=NC(C)=1)C(=O)NC(N=2)=O)) LIGAND-CPD:C04332: 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione + 3,4-dihydroxy-2-butanone-4-P = 6,7-dimethyl-8-(1-D-ribityl)lumazine + H2O flavin biosynthesis 6,7-dimethyl-8-(1-D-ribityl)lumazine 326.308 C13 H18 N4 O6 CC1(N(CC(O)C(O)C(O)CO)C2(C(=NC(C)=1)C(=O)NC(N=2)=O)) LIGAND-CPD:C04332: 2.5.1.9 6,7-dimethyl-8-(1-D-ribityl)lumazine = 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione + riboflavin flavin biosynthesis glutamate-1-semialdehyde (S)-4-amino-5-oxopentanoate*L-Glutamate 1-semialdehyde 131.131 C5 H9 N1 O3 [CH](=O)C(N)CCC(=O)O LIGAND-CPD:C03741: 1.2.1.70 glutamate-1-semialdehyde + NADP+ = NADPH + H+ tetrapyrrole biosynthesis I glutamate-1-semialdehyde (S)-4-amino-5-oxopentanoate*L-Glutamate 1-semialdehyde 131.131 C5 H9 N1 O3 [CH](=O)C(N)CCC(=O)O LIGAND-CPD:C03741: 5.4.3.8 glutamate-1-semialdehyde = 5-amino-levulinate tetrapyrrole biosynthesis I GA25 gibberellin A25*gibberellin A25*GA25 362.422 C20 H26 O6 CC1([CH]4(C(CCC1)(C(=O)O)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA25 + α-ketoglutarate + O2 = GA13 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) GA25 gibberellin A25*gibberellin A25*GA25 362.422 C20 H26 O6 CC1([CH]4(C(CCC1)(C(=O)O)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA24 + O2 + α-ketoglutarate = GA25 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) glyoxylate glyoxalate*glyox*glyoxylic acid 74.036 C2 H2 O3 C(=O)(O)[CH]=O LIGAND-CPD:C00048:*CAS:298-12-4 1.1.3.15 glycolate + O2 = glyoxylate + H2O2 photorespiration glyoxylate glyoxalate*glyox*glyoxylic acid 74.036 C2 H2 O3 C(=O)(O)[CH]=O LIGAND-CPD:C00048:*CAS:298-12-4 3.5.3.19 H2O + (S)-ureidoglycolate = ammonia + CO2 + glyoxylate allantoin degradation I glyoxylate glyoxalate*glyox*glyoxylic acid 74.036 C2 H2 O3 C(=O)(O)[CH]=O LIGAND-CPD:C00048:*CAS:298-12-4 2.6.1.4 α-ketoglutarate + glycine = L-glutamate + glyoxylate photorespiration glyoxylate glyoxalate*glyox*glyoxylic acid 74.036 C2 H2 O3 C(=O)(O)[CH]=O LIGAND-CPD:C00048:*CAS:298-12-4 4.1.3.16 D-4-hydroxy-2-keto-glutarate = glyoxylate + pyruvate 4-hydroxyproline degradation I glyoxylate glyoxalate*glyox*glyoxylic acid 74.036 C2 H2 O3 C(=O)(O)[CH]=O LIGAND-CPD:C00048:*CAS:298-12-4 2.3.3.9 acetyl-CoA + H2O + glyoxylate = malate + coenzyme A TCA cycle variation I glyoxylate glyoxalate*glyox*glyoxylic acid 74.036 C2 H2 O3 C(=O)(O)[CH]=O LIGAND-CPD:C00048:*CAS:298-12-4 1.1.99.14 glycolate = glyoxylate glycolate and glyoxylate degradation I glyoxylate glyoxalate*glyox*glyoxylic acid 74.036 C2 H2 O3 C(=O)(O)[CH]=O LIGAND-CPD:C00048:*CAS:298-12-4 4.1.1.47 glyoxylate = CO2 + tartronate semialdehyde glycolate and glyoxylate degradation I glyoxylate glyoxalate*glyox*glyoxylic acid 74.036 C2 H2 O3 C(=O)(O)[CH]=O LIGAND-CPD:C00048:*CAS:298-12-4 4.1.1.47 glyoxylate = CO2 + tartronate semialdehyde allantoin degradation I glyoxylate glyoxalate*glyox*glyoxylic acid 74.036 C2 H2 O3 C(=O)(O)[CH]=O LIGAND-CPD:C00048:*CAS:298-12-4 4.1.3.1 TCA cycle variation I glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 307.321 C10 H17 N3 O6 S1 C(=O)(O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O LIGAND-CPD:C00051:*CAS:70-18-8 4.4.1.5 S-lactoyl-glutathione = methylglyoxal + glutathione methylglyoxal degradation I glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 307.321 C10 H17 N3 O6 S1 C(=O)(O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O LIGAND-CPD:C00051:*CAS:70-18-8 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = glutathione + ADP glutathione biosynthesis glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 307.321 C10 H17 N3 O6 S1 C(=O)(O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O 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 307.321 C10 H17 N3 O6 S1 C(=O)(O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O LIGAND-CPD:C00051:*CAS:70-18-8 1.8.4.9 sulfite + AMP + glutathione disulfide = adenosine 5'-phosphosulfate + glutathione sulfate reduction II (assimilatory) glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 307.321 C10 H17 N3 O6 S1 C(=O)(O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O 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 307.321 C10 H17 N3 O6 S1 C(=O)(O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O 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 307.321 C10 H17 N3 O6 S1 C(=O)(O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O LIGAND-CPD:C00051:*CAS:70-18-8 1.8.1.7 glutathione + NADP+ = glutathione disulfide + NADPH + H+ ascorbate glutathione cycle glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 307.321 C10 H17 N3 O6 S1 C(=O)(O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O LIGAND-CPD:C00051:*CAS:70-18-8 1.11.1.9 H2O2 + glutathione = glutathione disulfide + H2O glutathione redox reactions I glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 307.321 C10 H17 N3 O6 S1 C(=O)(O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O LIGAND-CPD:C00051:*CAS:70-18-8 3.1.2.6 S-lactoyl-glutathione + H2O = glutathione + D-lactate methylglyoxal degradation I glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 307.321 C10 H17 N3 O6 S1 C(=O)(O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O LIGAND-CPD:C00051:*CAS:70-18-8 1.8.5.1 L-dehydro-ascorbate + glutathione = glutathione disulfide + L-ascorbate ascorbate glutathione cycle glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 307.321 C10 H17 N3 O6 S1 C(=O)(O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O LIGAND-CPD:C00051:*CAS:70-18-8 1.11.1.12 glutathione + a lipid hydroperoxide = glutathione disulfide + lipid + H2O glutathione redox reactions I glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 307.321 C10 H17 N3 O6 S1 C(=O)(O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O LIGAND-CPD:C00051:*CAS:70-18-8 2.3.2.2 (5-L-glutamyl)-L-amino acid + Cys-Gly = glutathione γ-glutamyl cycle glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 307.321 C10 H17 N3 O6 S1 C(=O)(O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O LIGAND-CPD:C00051:*CAS:70-18-8 2.5.1.18 glutathione + RX = HX glutathione-mediated detoxification glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 307.321 C10 H17 N3 O6 S1 C(=O)(O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O LIGAND-CPD:C00051:*CAS:70-18-8 3.1.2.12 S-formylglutathione + H2O = formate + glutathione formaldehyde oxidation II (glutathione-dependent) glutathione γ-L-glutamyl-L-cysteinyl-glycine*glutathione red*GSH*reduced glutathione 307.321 C10 H17 N3 O6 S1 C(=O)(O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O LIGAND-CPD:C00051:*CAS:70-18-8 4.4.1.22 S-hydroxymethylglutathione = formaldehyde + glutathione formaldehyde oxidation II (glutathione-dependent) ent-cassa-12,15-diene-3α-ol-11-keto ent-cassa-12,15-diene-3alpha-ol-11-keto*ent-cassadiene-3α-ol-11-keto*ent-cassadiene-3alpha-ol-11-keto 302.456 C20 H30 O2 CC1(C)(C(O)CCC2(C)(C3([CH](CC[CH]12)C(C)C(C=C)=CC(=O)3))) ent-cassa-12,15-diene-3α-ol = ent-cassa-12,15-diene-3α-ol-11-keto phytocassane biosynthesis ent-cassa-12,15-diene-3α-ol-11-keto ent-cassa-12,15-diene-3alpha-ol-11-keto*ent-cassadiene-3α-ol-11-keto*ent-cassadiene-3alpha-ol-11-keto 302.456 C20 H30 O2 CC1(C)(C(O)CCC2(C)(C3([CH](CC[CH]12)C(C)C(C=C)=CC(=O)3))) ent-cassa-12,15-diene-3α-ol-11-keto = phytocassane C phytocassane biosynthesis ent-cassa-12,15-diene-3α-ol-11-keto ent-cassa-12,15-diene-3alpha-ol-11-keto*ent-cassadiene-3α-ol-11-keto*ent-cassadiene-3alpha-ol-11-keto 302.456 C20 H30 O2 CC1(C)(C(O)CCC2(C)(C3([CH](CC[CH]12)C(C)C(C=C)=CC(=O)3))) ent-cassa-12,15-diene-3α-ol-11-keto = ent-cassa-12,15-diene-2,3α-ol-11-keto phytocassane biosynthesis dATP 2'-deoxyadenosine triphosphate*deoxy-ATP*deoxyadenosine-triphosphate*2'-deoxyadenosine-5'-triphosphate 491.184 C10 H16 N5 O12 P3 C(OP(O)(=O)OP(O)(=O)OP(O)(O)=O)C1(OC(CC(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00131:*CAS:1927-31-7 ATP = dATP + H2O purine nucleotides de novo biosynthesis I dATP 2'-deoxyadenosine triphosphate*deoxy-ATP*deoxyadenosine-triphosphate*2'-deoxyadenosine-5'-triphosphate 491.184 C10 H16 N5 O12 P3 C(OP(O)(=O)OP(O)(=O)OP(O)(O)=O)C1(OC(CC(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00131:*CAS:1927-31-7 2.7.4.6 dADP + ATP = dATP + ADP purine nucleotides de novo biosynthesis I N-formylkynurenine N-Formyl-L-kynurenine 236.227 C11 H12 N2 O4 C(=O)(O)C(N)CC(=O)c1(c(NC=O)cccc1) CAS:1022-31-7 3.5.1.9 N-formylkynurenine + H2O = kynurenine + formate tryptophan degradation III (eukaryotic) GA1 gibberellin A1*gibberellin A1*GA1 348.395 C19 H24 O6 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(C(O)CC3)(C)[CH]4C5C(=O)O)))(O)) 1.14.11.15 GA20 + α-ketoglutarate + O2 = GA1 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) GA1 gibberellin A1*gibberellin A1*GA1 348.395 C19 H24 O6 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(C(O)CC3)(C)[CH]4C5C(=O)O)))(O)) 1.14.11.13 GA1 + α-ketoglutarate + O2 = GA8 + succinate + CO2 gibberellin inactivation CDP-choline citicoline*citicholine*cidifos*cyticholine*cytidine 5'-diphosphocholine*cytidine diphosphate choline 489.335 C14 H27 N4 O11 P2 C(OP(O)(=O)OP(O)(=O)OCC[N+](C)(C)C)C1(OC(C(O)C1O)n2(c(=O)nc(N)cc2)) CAS:987-78-0 2.7.8.2 CDP-choline = CMP phospholipid biosynthesis II CDP-choline citicoline*citicholine*cidifos*cyticholine*cytidine 5'-diphosphocholine*cytidine diphosphate choline 489.335 C14 H27 N4 O11 P2 C(OP(O)(=O)OP(O)(=O)OCC[N+](C)(C)C)C1(OC(C(O)C1O)n2(c(=O)nc(N)cc2)) CAS:987-78-0 2.7.8.2 CDP-choline = CMP choline biosynthesis III CDP-choline citicoline*citicholine*cidifos*cyticholine*cytidine 5'-diphosphocholine*cytidine diphosphate choline 489.335 C14 H27 N4 O11 P2 C(OP(O)(=O)OP(O)(=O)OCC[N+](C)(C)C)C1(OC(C(O)C1O)n2(c(=O)nc(N)cc2)) CAS:987-78-0 2.7.7.15 phosphoryl-choline + CTP = CDP-choline + diphosphate phospholipid biosynthesis II CDP-choline citicoline*citicholine*cidifos*cyticholine*cytidine 5'-diphosphocholine*cytidine diphosphate choline 489.335 C14 H27 N4 O11 P2 C(OP(O)(=O)OP(O)(=O)OCC[N+](C)(C)C)C1(OC(C(O)C1O)n2(c(=O)nc(N)cc2)) CAS:987-78-0 2.7.7.15 phosphoryl-choline + CTP = CDP-choline + diphosphate choline biosynthesis III mannosyl-diinositol-phosphorylceramide MIP2C*M(IP)2C*mannose-(inositol phosphate)2-ceramide 2.4.1.- mannosyl-inositol-phosphorylceramide + inositol phosphate = mannosyl-diinositol-phosphorylceramide sphingolipid metabolism phytocassane C 318.455 C20 H30 O3 CC2(C(C=C)=CC(=O)[CH]1(C3([CH](CC[CH]12)C(C)(C)C(O)CC(O)3)(C))) phytocassane C = phytocassane B phytocassane biosynthesis phytocassane C 318.455 C20 H30 O3 CC2(C(C=C)=CC(=O)[CH]1(C3([CH](CC[CH]12)C(C)(C)C(O)CC(O)3)(C))) ent-cassa-12,15-diene-3α-ol-11-keto = phytocassane C phytocassane biosynthesis phytocassane C 318.455 C20 H30 O3 CC2(C(C=C)=CC(=O)[CH]1(C3([CH](CC[CH]12)C(C)(C)C(O)CC(O)3)(C))) phytocassane C = phytocassane E phytocassane biosynthesis 4α-carboxy-5α-cholesta-8-en-3β-ol 430.67 C28 H46 O3 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(C(=O)O)C(O)CC4)(C)))(C)) 1.1.1.170 4α-carboxy-5α-cholesta-8-en-3β-ol = 5α-cholesta-8-en-3-one + CO2 cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 4α-carboxy-5α-cholesta-8-en-3β-ol 430.67 C28 H46 O3 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(C(=O)O)C(O)CC4)(C)))(C)) 1.14.13.72 4α-formyl-5α-cholesta-8-en-3β-ol + O2 = 4α-carboxy-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 18:1-16:2-MGDG 1-18:1-2-16:2-monogalactosyldiacylglycerol*1-(9Z-octadecenoyl)-2-(7Z,10Z-hexadecadienoyl)-3-O-beta-D-galactosyl-sn-glycerol 753.067 C43 H76 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC 1.14.99.- 18:1-16:1-MGDG = 18:1-16:2-MGDG glycolipid desaturation 18:1-16:2-MGDG 1-18:1-2-16:2-monogalactosyldiacylglycerol*1-(9Z-octadecenoyl)-2-(7Z,10Z-hexadecadienoyl)-3-O-beta-D-galactosyl-sn-glycerol 753.067 C43 H76 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC 1.14.99.- 18:1-16:2-MGDG = 18:2-16:2-MGDG glycolipid desaturation 18:1-16:2-MGDG 1-18:1-2-16:2-monogalactosyldiacylglycerol*1-(9Z-octadecenoyl)-2-(7Z,10Z-hexadecadienoyl)-3-O-beta-D-galactosyl-sn-glycerol 753.067 C43 H76 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC 1.14.99.- 18:1-16:2-MGDG = 18:1-16:3-MGDG glycolipid desaturation dTTP thymidine triphosphate*thymidine 5'-triphosphate*TTP 482.171 C10 H17 N2 O14 P3 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00459:*CAS:365-08-2: 2.7.4.6 dTDP + ATP = dTTP + ADP de novo biosynthesis of pyrimidine deoxyribonucleotides dTTP thymidine triphosphate*thymidine 5'-triphosphate*TTP 482.171 C10 H17 N2 O14 P3 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00459:*CAS:365-08-2: 2.7.7.24 α-D-glucose 1-phosphate + dTTP = dTDP-D-glucose + diphosphate dTDP-L-rhamnose biosynthesis I tetrahydromethanopterin THMPT*5,6,7,8-tetrahydromethanopterin*H4MPT 775.682 C30 H44 N6 O16 P1 C[CH]([CH]1([CH](C)[NH]c2(c([NH]1)c(=O)[nH]c(n2)N)))Nc3(ccc(cc3)CC(O)C(O)C(O)COC4(OC(C(O)C4O)COP(=O)([O-])OC(C(O)=O)CCC(O)=O)) 2.3.1.101 tetrahydromethanopterin = 5-formyl-tetrahydromethanopterin methanogenesis from CO2 tetrahydromethanopterin THMPT*5,6,7,8-tetrahydromethanopterin*H4MPT 775.682 C30 H44 N6 O16 P1 C[CH]([CH]1([CH](C)[NH]c2(c([NH]1)c(=O)[nH]c(n2)N)))Nc3(ccc(cc3)CC(O)C(O)C(O)COC4(OC(C(O)C4O)COP(=O)([O-])OC(C(O)=O)CCC(O)=O)) 2.1.1.86 5-methyl-tetrahydromethanopterin = tetrahydromethanopterin methanogenesis from CO2 secologanin (-)-secologanin 388.371 C17 H24 O10 C=C[CH]1(C(OC=C(C(=O)OC)[CH]1CC=O)OC2(C(O)C(O)C(O)C(O2)CO)) LIGAND-CPD:C01852: 4.3.3.2 tryptamine + secologanin = strictosidine + H2O secologanin and strictosidine biosynthesis secologanin (-)-secologanin 388.371 C17 H24 O10 C=C[CH]1(C(OC=C(C(=O)OC)[CH]1CC=O)OC2(C(O)C(O)C(O)C(O2)CO)) LIGAND-CPD:C01852: 1.3.3.9 O2 + NADPH + loganin = H2O + NADP+ + secologanin secologanin and strictosidine biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH gluconeogenesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH sucrose degradation to ethanol and lactate (anaerobic) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH fructose degradation to pyruvate and lactate (anaerobic) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH glucose fermentation to lactate II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH glycolysis I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.77 NADH + L-lactaldehyde = NAD+ fucose degradation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ mixed acid fermentation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ sucrose degradation to ethanol and lactate (anaerobic) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ ethanol fermentation to acetate NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ oxidative ethanol degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.27 NAD+ + L-lactate = NADH + pyruvate sucrose degradation to ethanol and lactate (anaerobic) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.27 NAD+ + L-lactate = NADH + pyruvate fructose degradation to pyruvate and lactate (anaerobic) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.27 NAD+ + L-lactate = NADH + pyruvate glucose fermentation to lactate II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: α-ketoglutarate + coenzyme A + NAD+ = succinyl-CoA + CO2 + NADH TCA cycle NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.27 NAD+ + coenzyme A + methylmalonate-semialdehyde = NADH + CO2 + propionyl-CoA valine degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.5.1.12 NAD+ + H2O = L-glutamate + NADH proline degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.5.1.12 NAD+ + H2O = 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.3.99.3 NADH + acrylyl-CoA = NAD+ + propionyl-CoA D-lactate fermentation to propionate and acetate NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: α-ketoadipate + 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: α-ketoadipate + NAD+ + coenzyme A = CO2 + NADH + glutaryl-CoA tryptophan degradation III (eukaryotic) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.8 betaine aldehyde + NAD+ + H2O = 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.32 H2O + NAD+ + 2-aminomuconate semialdehyde = NADH + 2-amino-muconate tryptophan degradation III (eukaryotic) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.103 L-threonine + NAD+ = 2-amino-3-oxobutanoate + NADH threonine degradation II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.103 L-threonine + NAD+ = 2-amino-3-oxobutanoate + NADH threonine degradation III (to methylglyoxal) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.103 L-threonine + NAD+ = 2-amino-3-oxobutanoate + NADH aminopropanol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.5.1.15 5,10-methylene-THF + NAD+ = NADH folate transformations NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.16.1.7 Fe2+ + NAD+ = Fe3+ + NADH 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.38 NAD+ + malate = NADH + CO2 + pyruvate gluconeogenesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 2-ketoisocaproate + 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ purine degradation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ salvage pathways of adenine, hypoxanthine, and their nucleosides NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ ureide biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.87 homoisocitrate + NAD+ = α-ketoadipate + CO2 + NADH + H+ lysine biosynthesis IV NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.8.1.4 NAD+ = NADH + H+ branched-chain α-keto acid dehydrogenase complex NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.5.1.9 H2O + NAD+ + saccharopine = L-glutamate + NADH + 2-aminoadipate-6-semialdehyde lysine degradation II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.6.5.3 ubiquinone-8 + NADH = ubiquinol-8 + NAD+ aerobic respiration -- electron donors reaction list NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.6.5.3 ubiquinone-8 + NADH = ubiquinol-8 + NAD+ respiration (anaerobic)-- electron donors reaction list NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.6.5.3 ubiquinone-8 + NADH = ubiquinol-8 + 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 2-keto-3-methyl-valerate + NAD+ + coenzyme A = S-2-methyl-butyryl-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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.99.8 indole-3-glyoxal + NADH + H+ = indole-3-ketol + NAD+ tryptophan degradation V (side chain pathway) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.22 UDP-D-glucose + H2O + NAD+ = UDP-D-glucuronate + NADH UDP-D-xylose biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.22 UDP-D-glucose + H2O + NAD+ = UDP-D-glucuronate + NADH galactose degradation II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.1 3-methylbutanal + NADH = isoamyl alcohol + NAD+ leucine degradation III NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.3.1.28 NAD+ + 2,3-dihydro-2,3-dihydroxybenzoate = NADH + 2,3-dihydroxybenzoate enterobactin biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.- L-galactose + NAD+ = L-galactono-1,4-lactone + NADH ascorbate biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 2-amino-muconate + H2O + NADH = NH(4)OH + α-ketoadipate + NAD+ tryptophan degradation III (eukaryotic) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.88 (R)-mevalonate + NAD+ + coenzyme A = 3-hydroxy-3-methyl-glutaryl-CoA + NADH + H+ mevalonate degradation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.5.1.7 H2O + NAD+ + saccharopine = NADH + α-ketoglutarate + L-lysine lysine biosynthesis IV NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.1 3-methylthiopropanal + NADH + H+ = methionol + NAD+ methionine degradation III NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.262 4-(phosphonooxy)-threonine + NAD+ = NADH + (2S)-2-amino-3-oxo-4-phosphonooxybutanoate pyridoxal 5'-phosphate biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.3.1.- crotonyl-CoA + NADH = butyryl-CoA + NAD+ ethanol fermentation to acetate NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.22 H2O + NAD+ + L-lactaldehyde = NADH + L-lactate fucose degradation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.25 NAD+ + coenzyme A + 2-keto-isovalerate = NADH + CO2 + isobutyryl-CoA valine degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.85 3-isopropylmalate + NAD+ = 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.99.8 indole-3-glycol aldehyde + NADH + H+ = indole-3-glycol + NAD+ tryptophan degradation V (side chain pathway) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.223 NAD+ + (-)-trans-Isopiperitenol = NADH + (-)-isopiperitenone menthol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.35 NAD+ = NADH fatty acid β-oxidation IV (plant, unsaturated, even number) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.35 NAD+ = NADH fatty acid β-oxidation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.35 NAD+ = NADH fatty acid β-oxidation II (plant, saturated) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.3.1.9 NAD+ = NADH fatty acid elongation -- saturated NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.72 D-erythrose-4-phosphate + NAD+ + H2O = erythronate-4-phosphate + NADH + H+ pyridoxal 5'-phosphate biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.- N2-succinyl-L-glutamate 5-semialdehyde + NAD+ + H2O = N2-succinylglutamate + NADH arginine degradation II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.178 NAD+ + 2-methyl-3-hydroxybutyryl-CoA = 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.31 NAD+ + 3-hydroxy-isobutyrate = NADH + 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.1 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.8.1.4 NAD+ = NADH + H+ pyruvate dehydrogenase complex NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 4.3.1.12 L-ornithine + NAD+ = L-proline + ammonia + NADH + H+ arginine degradation VII (arginase 3 pathway) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.24 H2O + NAD+ + succinate semialdehyde = NADH + succinate glutamate degradation III NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.29 glycerate + NAD+ = hydroxypyruvate + NADH photorespiration NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.23 histidinal + NAD+ + H2O = L-histidine + NADH histidine biosynthesis I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.1 phenylacetaldehyde + NADH = 2-phenylethanol + NAD+ phenylalanine degradation III NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.6.5.3 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.6.5.3 NADH = NAD+ aerobic respiration -- electron donor III NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ purine degradation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ salvage pathways of purine nucleosides II (plant) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.10 NAD+ + coenzyme A + acetaldehyde = NADH + acetyl-CoA mixed acid fermentation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.10 NAD+ + coenzyme A + acetaldehyde = NADH + acetyl-CoA ethanol fermentation to acetate NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 2.7.1.86 NADH + ATP = 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH folate transformations NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH formylTHF biosynthesis II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH formylTHF biosynthesis I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH photorespiration NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.23 histidinol + NAD+ = histidinal + NADH histidine biosynthesis I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.57 NAD+ + D-mannonate = NADH + fructuronate β-D-glucuronide degradation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.21 H2O + NAD+ + glycolaldehyde = NADH + glycolate ethylene glycol degradation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: NAD+ = dipicolinate + NADH + H+ lysine biosynthesis II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH purine degradation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH salvage pathways of purine nucleosides NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH ureide biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH salvage pathways of purine nucleosides II (plant) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH purine nucleotides de novo biosynthesis I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.35 acetoacetyl-CoA + NADH = 3-hydroxybutyryl-CoA + NAD+ acetyl CoA fermentation to butyrate NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.35 acetoacetyl-CoA + NADH = 3-hydroxybutyryl-CoA + NAD+ glutaryl-CoA degradation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.59 NAD+ + 3-hydroxy-propionate = NADH + malonate semialdehyde β-alanine biosynthesis II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.- pyruvate + coenzyme A + NAD+ = acetyl-CoA + CO2 + NADH respiration (anaerobic) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: NAD+ + ethylene glycol = glycolaldehyde + NADH ethylene glycol degradation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.37 malate + NAD+ = oxaloacetate + NADH mixed acid fermentation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.37 malate + NAD+ = oxaloacetate + NADH TCA cycle variation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.37 malate + NAD+ = oxaloacetate + NADH reductive TCA cycle I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.37 malate + NAD+ = oxaloacetate + NADH gluconeogenesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.37 malate + NAD+ = oxaloacetate + NADH respiration (anaerobic) NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.37 malate + NAD+ = 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.37 malate + NAD+ = oxaloacetate + NADH TCA cycle NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.290 erythronate-4-phosphate + NAD+ = 2-oxo-3-hydroxy-4-phosphobutanoate + NADH + H+ pyridoxal 5'-phosphate biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.31 2-aminoadipate-6-semialdehyde + H2O + NAD+ = α-aminoadipate + NADH lysine degradation II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.1 2-methylbutanal + NADH = 2-methylbutanol + NAD+ isoleucine degradation II NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.8.1.4 NAD+ = NADH + H+ 2-keto glutarate dehydrogenase complex NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.28 NAD+ + D-lactate = NADH + pyruvate mixed acid fermentation NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.28 NAD+ + D-lactate = NADH + pyruvate D-lactate fermentation to propionate and acetate NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.75 1-amino-propan-2-ol + NAD+ = aminoacetone + NADH aminopropanol biosynthesis NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.3 acetaldehyde + NAD+ + H2O = NADH + acetate oxidative ethanol degradation III NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.2.1.3 acetaldehyde + NAD+ + H2O = NADH + acetate oxidative ethanol degradation I NADH NADH2*NADH2*dihydrodiphosphopyridine nucleotide*diphosphopyridine nucleotide reduced*dihydronicotinamide adenine dinucleotide*nicotinamide adenine dinucleotide reduced*NAD-reduced*NADH+H+*DPNH 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.1.1.95 3-phosphoglycerate + NAD+ = 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 665.446 C21 H29 N7 O14 P2 C([CH]1(O[CH]([CH](O)[CH]1O)N2(C=C(C(=O)N)[CH2]C=C2)))OP(=O)(O)OP(=O)(O)OC[CH]3(O[CH]([CH](O)[CH](O)3)n4(c5(c(nc4)c(N)ncn5))) CAS:53-84-9:*LIGAND-CPD:C00004: 1.5.1.12 pyrroline-hydroxy-carboxylate + NAD+ + H2O = L-erythro-4-hydroxy-glutamate + NADH 4-hydroxyproline degradation I dTDP-α-L-rhamnose dTDP-6-deoxy-L-mannose*dTDP-L-rhamnose*dTDP-rhamnose 548.333 C16 H26 N2 O15 P2 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)C(O3)C))) CAS:572-96-3:*LIGAND-CPD:C03319: 1.1.1.133 NADP+ + dTDP-α-L-rhamnose = NADPH + dTDP-4-dehydro-6-deoxy-L-mannose dTDP-L-rhamnose biosynthesis I indole-3-glycol aldehyde 2-hydroxy-2-(1H-indol-3-yl)acetaldehyde*3-indoleglycol aldehyde 175.187 C10 H9 N1 O2 C(=O)C(O)c1(c2(c([nH]c1)cccc2)) PUBCHEM:439951: indole-3-glycol aldehyde = indole-3-glyoxal tryptophan degradation V (side chain pathway) indole-3-glycol aldehyde 2-hydroxy-2-(1H-indol-3-yl)acetaldehyde*3-indoleglycol aldehyde 175.187 C10 H9 N1 O2 C(=O)C(O)c1(c2(c([nH]c1)cccc2)) PUBCHEM:439951: 1.2.1.5 indole-3-glycol aldehyde + H2O + an oxidized acceptor = indole-3-glycolate tryptophan degradation V (side chain pathway) indole-3-glycol aldehyde 2-hydroxy-2-(1H-indol-3-yl)acetaldehyde*3-indoleglycol aldehyde 175.187 C10 H9 N1 O2 C(=O)C(O)c1(c2(c([nH]c1)cccc2)) PUBCHEM:439951: 1.13.99.3 indole acetaldehyde + O2 = indole-3-glycol aldehyde tryptophan degradation V (side chain pathway) indole-3-glycol aldehyde 2-hydroxy-2-(1H-indol-3-yl)acetaldehyde*3-indoleglycol aldehyde 175.187 C10 H9 N1 O2 C(=O)C(O)c1(c2(c([nH]c1)cccc2)) PUBCHEM:439951: 1.1.99.8 indole-3-glycol aldehyde + NADH + H+ = indole-3-glycol + NAD+ tryptophan degradation V (side chain pathway) 1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate phosphatidyl-myo-inositol 4,5-biphosphate C11 H19 O19 R2 P3 3.1.4.11 phospholipases (4α)-methyl-(5α)-ergosta-8,14,24(28)-trien-3β-ol 410.682 C29 H46 O1 CC(C)C(=C)CCC(C)C1(C2(C)(C(=CC1)C3(=C(CC2)C4([CH](CC3)C(C)C(O)CC4)(C)))) LIGAND-CPD:C11508: 1.14.13.70 NADPH + O2 + obtusifoliol + H+ = H2O + NADP+ + formate + (4α)-methyl-(5α)-ergosta-8,14,24(28)-trien-3β-ol sterol biosynthesis (4α)-methyl-(5α)-ergosta-8,14,24(28)-trien-3β-ol 410.682 C29 H46 O1 CC(C)C(=C)CCC(C)C1(C2(C)(C(=CC1)C3(=C(CC2)C4([CH](CC3)C(C)C(O)CC4)(C)))) LIGAND-CPD:C11508: 1.3.1.70 (4α)-methyl-(5α)-ergosta-8,14,24(28)-trien-3β-ol + NADPH = 4α-methylfecosterol + NADP+ sterol biosynthesis 2-phenylethanol benzeneethanol*phenethanol 122.166 C8 H10 O1 C(O)Cc1(ccccc1) PUBCHEM:6054: 1.1.1.1 phenylacetaldehyde + NADH = 2-phenylethanol + NAD+ phenylalanine degradation III protoheme IX heme*hemin*ferroprotoporphyrin*protoheme*heme b*hematin*haemin 616.498 C34 H32 N4 O4 FE1 Cc4(c2(C=C8(N7([Fe]35(N1(=C(C(C)=C(CCC(O)=O)C1=Cc(n23)c4CCC(O)=O)C=c6(n5c(c(C=C)c(C)6)=CC=7C(C)=C8C=C))))))) LIGAND-CPD:C00032:*CAS:14875-96-8 4.99.1.1 Fe2+ + protoporphyrin IX = H+ + protoheme IX heme biosynthesis II L-fuculose fuculose 164.158 C6 H12 O5 C[CH](O)[CH](O)[CH](O)C(=O)CO LIGAND-CPD:C01721:*CAS:13074-08-3 2.7.1.51 L-fuculose + ATP = fuculose-1-phosphate + ADP fucose degradation L-fuculose fuculose 164.158 C6 H12 O5 C[CH](O)[CH](O)[CH](O)C(=O)CO LIGAND-CPD:C01721:*CAS:13074-08-3 5.3.1.25 L-fucose = L-fuculose fucose degradation linolenate linolenic acid*(9,12,15)-linolenic acid*α-linolenic acid*9Z,12Z,15Z-octadecatrienoate*9Z,12Z,15Z-octadecatrienoic acid*(9,12,15)-linolenate 278.434 C18 H30 O2 CCC=CCC=CCC=CCCCCCCCC(O)=O CAS:463-40-1 1.13.11.- linolenate + O2 = 9-HPOT 9-LOX and 9-HPL pathway linolenate linolenic acid*(9,12,15)-linolenic acid*α-linolenic acid*9Z,12Z,15Z-octadecatrienoate*9Z,12Z,15Z-octadecatrienoic acid*(9,12,15)-linolenate 278.434 C18 H30 O2 CCC=CCC=CCC=CCCCCCCCC(O)=O CAS:463-40-1 1.13.11.12 O2 + linolenate = 13-HPOT 13-LOX and 13-HPL pathway linolenate linolenic acid*(9,12,15)-linolenic acid*α-linolenic acid*9Z,12Z,15Z-octadecatrienoate*9Z,12Z,15Z-octadecatrienoic acid*(9,12,15)-linolenate 278.434 C18 H30 O2 CCC=CCC=CCC=CCCCCCCCC(O)=O CAS:463-40-1 1.13.11.12 O2 + linolenate = 13-HPOT jasmonic acid biosynthesis linolenate linolenic acid*(9,12,15)-linolenic acid*α-linolenic acid*9Z,12Z,15Z-octadecatrienoate*9Z,12Z,15Z-octadecatrienoic acid*(9,12,15)-linolenate 278.434 C18 H30 O2 CCC=CCC=CCC=CCCCCCCCC(O)=O CAS:463-40-1 3.1.1.4 H2O = linolenate jasmonic acid biosynthesis maltooligosyl-trehalose 1-α-D-{(1,4)-α-D-glucosyl}(n-1)-α-D-glucopyranoside 5.4.99.15 maltodextrin = maltooligosyl-trehalose trehalose biosynthesis V maltooligosyl-trehalose 1-α-D-{(1,4)-α-D-glucosyl}(n-1)-α-D-glucopyranoside 3.2.1.141 maltooligosyl-trehalose = maltodextrin + trehalose trehalose biosynthesis V δ-selinene 204.355 C15 H24 CC12(CCCC(C)=C(C=C(C(C)C)CC1)2) 4.2.3.- trans, trans-farnesyl diphosphate = δ-selinene + diphosphate oleoresin sesquiterpene volatiles biosynthesis linamarin 247.247 C10 H17 N1 O6 CC(C)(C#N)OC1(C(O)C(O)C(O)C(O1)CO) LIGAND-CPD:C01594:*CAS:554-35-8 3.2.1.21 linamarin + H2O = acetone cyanohydrin + β-D-glucose linamarin degradation 2-oxo-4-methylthiobutanoate 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 148.176 C5 H8 O3 S1 C(SC)CC(=O)C(=O)O 2-oxo-4-methylthiobutanoate = 3-methylthiopropanal + CO2 methionine degradation III 2-oxo-4-methylthiobutanoate 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 148.176 C5 H8 O3 S1 C(SC)CC(=O)C(=O)O 2.3.3.- 2-oxo-4-methylthiobutanoate + acetyl-CoA + H2O = 2-(2'-methylthio)ethylmalic-acid + coenzyme A homomethionine biosynthesis 2-oxo-4-methylthiobutanoate 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 148.176 C5 H8 O3 S1 C(SC)CC(=O)C(=O)O 2.6.1.5 2-oxo-4-methylthiobutanoate = L-methionine methionine salvage pathway 2-oxo-4-methylthiobutanoate 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 148.176 C5 H8 O3 S1 C(SC)CC(=O)C(=O)O L-methionine + phenylpyruvate = 2-oxo-4-methylthiobutanoate + L-phenylalanine methionine degradation III 2-oxo-4-methylthiobutanoate 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 148.176 C5 H8 O3 S1 C(SC)CC(=O)C(=O)O 1.13.11.54 1,2-dihydroxy-3-keto-5-methylthiopentene + O2 = 2-oxo-4-methylthiobutanoate + formate methionine salvage pathway 2-oxo-4-methylthiobutanoate 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 148.176 C5 H8 O3 S1 C(SC)CC(=O)C(=O)O 2.6.1.- L-methionine = 2-oxo-4-methylthiobutanoate homomethionine biosynthesis 1-deoxy-D-xylulose 5-phosphate DXP*deoxyxylulose-5-phosphate*D-1-deoxyxylulose-5-P*1-deoxy-D-threo-pentulose 5-phosphate*DOXP 214.111 C5 H11 O7 P1 C(OP(=O)(O)O)C(O)C(O)C(C)=O LIGAND-CPD:C11437: 2.6.99.2 1-deoxy-D-xylulose 5-phosphate + 1-amino-propan-2-one-3-phosphate = pyridoxine-5'-phosphate + H2O pyridoxal 5'-phosphate biosynthesis 1-deoxy-D-xylulose 5-phosphate DXP*deoxyxylulose-5-phosphate*D-1-deoxyxylulose-5-P*1-deoxy-D-threo-pentulose 5-phosphate*DOXP 214.111 C5 H11 O7 P1 C(OP(=O)(O)O)C(O)C(O)C(C)=O LIGAND-CPD:C11437: 1.1.1.267 2-C-methyl-D-erythritol-4-phosphate + NADP+ = 1-deoxy-D-xylulose 5-phosphate + NADPH 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 214.111 C5 H11 O7 P1 C(OP(=O)(O)O)C(O)C(O)C(C)=O LIGAND-CPD:C11437: 2.2.1.7 pyruvate + D-glyceraldehyde-3-phosphate = 1-deoxy-D-xylulose 5-phosphate + CO2 pyridoxal 5'-phosphate biosynthesis 1-deoxy-D-xylulose 5-phosphate DXP*deoxyxylulose-5-phosphate*D-1-deoxyxylulose-5-P*1-deoxy-D-threo-pentulose 5-phosphate*DOXP 214.111 C5 H11 O7 P1 C(OP(=O)(O)O)C(O)C(O)C(C)=O LIGAND-CPD:C11437: 2.2.1.7 pyruvate + D-glyceraldehyde-3-phosphate = 1-deoxy-D-xylulose 5-phosphate + CO2 thiamine biosynthesis 1-deoxy-D-xylulose 5-phosphate DXP*deoxyxylulose-5-phosphate*D-1-deoxyxylulose-5-P*1-deoxy-D-threo-pentulose 5-phosphate*DOXP 214.111 C5 H11 O7 P1 C(OP(=O)(O)O)C(O)C(O)C(C)=O LIGAND-CPD:C11437: 2.2.1.7 pyruvate + D-glyceraldehyde-3-phosphate = 1-deoxy-D-xylulose 5-phosphate + CO2 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 214.111 C5 H11 O7 P1 C(OP(=O)(O)O)C(O)C(O)C(C)=O LIGAND-CPD:C11437: L-tyrosine + 1-deoxy-D-xylulose 5-phosphate = 4-methyl-5-(β-hydroxyethyl)thiazole phosphate + 4-hydroxybenzyl alcohol thiamine biosynthesis E-pyridine-3-aldoxime 122.126 C6 H6 N2 O1 C(=NO)C1(C=NC=CC=1) 4.2.1.- E-pyridine-3-aldoxime = 3-cyanopyridine + H2O aldoxime degradation 6-deoxocathasterone deoxocathasterone 418.702 C28 H50 O2 CC(C)C(C)CC(O)C(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC3)CC(O)CC4)(C)))) 1.14.-.- 6-deoxocathasterone + O2 = 6-deoxoteasterone + H2O brassinosteroid biosynthesis II 6-deoxocathasterone deoxocathasterone 418.702 C28 H50 O2 CC(C)C(C)CC(O)C(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC3)CC(O)CC4)(C)))) (22α)-hydroxy-5α-campestan-3-one = 6-deoxocathasterone brassinosteroid biosynthesis II 6-deoxocathasterone deoxocathasterone 418.702 C28 H50 O2 CC(C)C(C)CC(O)C(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC3)CC(O)CC4)(C)))) 1.14.13.- campestanol + O2 + NADPH = 6-deoxocathasterone + H2O + NADP+ brassinosteroid biosynthesis II 3-carboxyhex-2-enedioate 3-carboxyhex-2-enedioate*But-1-ene-1,2,4-tricarboxylate 188.137 C7 H8 O6 C(=O)(O)CCC(C(=O)O)=CC(=O)O 4.2.1.36 homocitrate = H2O + 3-carboxyhex-2-enedioate lysine biosynthesis IV 3-carboxyhex-2-enedioate 3-carboxyhex-2-enedioate*But-1-ene-1,2,4-tricarboxylate 188.137 C7 H8 O6 C(=O)(O)CCC(C(=O)O)=CC(=O)O 4.2.1.36 homoisocitrate = H2O + 3-carboxyhex-2-enedioate lysine biosynthesis IV oryzalexin D 3, 7-Dihydroxy-(+)-sandaracopimaradiene 304.472 C20 H32 O2 C=CC1(C=C2([CH](CC1)C3([CH](CC(O)2)C(C)(C)C(O)CC3)(C)))(C) oryzalexin D = oryzalexin B oryzalexin A-F biosynthesis oryzalexin D 3, 7-Dihydroxy-(+)-sandaracopimaradiene 304.472 C20 H32 O2 C=CC1(C=C2([CH](CC1)C3([CH](CC(O)2)C(C)(C)C(O)CC3)(C)))(C) ent-sandaracopimaradiene-3α-ol = oryzalexin D oryzalexin A-F biosynthesis oryzalexin D 3, 7-Dihydroxy-(+)-sandaracopimaradiene 304.472 C20 H32 O2 C=CC1(C=C2([CH](CC1)C3([CH](CC(O)2)C(C)(C)C(O)CC3)(C)))(C) oryzalexin D = oryzalexin A oryzalexin A-F biosynthesis nicotine-Glucuronide 339.367 C16 H23 N2 O6 c2([n+](C1(C(O)C(O)C(O)C(O1)C(O)=O))cc(cc2)[CH]3(N(C)CCC3)) 2.4.1.17 nicotine + UDP-D-glucuronate = nicotine-Glucuronide + UDP nicotine degradation II luteone 6-isopentenyl-2'-hydroxygenistein 354.359 C20 H18 O6 CC(C)=CCc2(c(O)c1(C(=O)C(=COc1cc(O)2)c3(c(O)cc(O)cc3))) 2.5.1.1 2'-hydroxygenistein + dimethylallyl-PP = luteone + diphosphate wighteone and luteone biosynthesis RX LIGAND-CPD:C01322: 2.5.1.18 glutathione + RX = HX glutathione-mediated detoxification nitrite NO2*NO2- 46.005 N1 O2 N(=O)[O-] CAS:7697-37-2:*LIGAND-CPD:C00088:*CAS:14797-65-0 1.7.99.4 nitrite = NO3- nitrate reduction I nitrite NO2*NO2- 46.005 N1 O2 N(=O)[O-] CAS:7697-37-2:*LIGAND-CPD:C00088:*CAS:14797-65-0 1.7.7.- nitrite = ammonia + H2O nitrate reduction II (assimilatory) glutathione disulfide glutathione oxidized*glutathione ox*GSSG*glutathione*GSH*ox. glutathione*oxidized glutathione 612.626 C20 H32 N6 O12 S2 C(=O)(CCC(N)C(O)=O)NC(C(=O)NCC(O)=O)CSSCC(C(=O)NCC(O)=O)NC(=O)CCC(N)C(=O)O LIGAND-CPD:C00127:*CAS:27025-41-8 1.8.5.1 L-dehydro-ascorbate + glutathione = glutathione disulfide + L-ascorbate ascorbate glutathione cycle glutathione disulfide glutathione oxidized*glutathione ox*GSSG*glutathione*GSH*ox. glutathione*oxidized glutathione 612.626 C20 H32 N6 O12 S2 C(=O)(CCC(N)C(O)=O)NC(C(=O)NCC(O)=O)CSSCC(C(=O)NCC(O)=O)NC(=O)CCC(N)C(=O)O 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 612.626 C20 H32 N6 O12 S2 C(=O)(CCC(N)C(O)=O)NC(C(=O)NCC(O)=O)CSSCC(C(=O)NCC(O)=O)NC(=O)CCC(N)C(=O)O LIGAND-CPD:C00127:*CAS:27025-41-8 1.8.4.9 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 612.626 C20 H32 N6 O12 S2 C(=O)(CCC(N)C(O)=O)NC(C(=O)NCC(O)=O)CSSCC(C(=O)NCC(O)=O)NC(=O)CCC(N)C(=O)O 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 612.626 C20 H32 N6 O12 S2 C(=O)(CCC(N)C(O)=O)NC(C(=O)NCC(O)=O)CSSCC(C(=O)NCC(O)=O)NC(=O)CCC(N)C(=O)O 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 612.626 C20 H32 N6 O12 S2 C(=O)(CCC(N)C(O)=O)NC(C(=O)NCC(O)=O)CSSCC(C(=O)NCC(O)=O)NC(=O)CCC(N)C(=O)O LIGAND-CPD:C00127:*CAS:27025-41-8 1.8.1.7 glutathione + NADP+ = glutathione disulfide + NADPH + H+ ascorbate glutathione cycle glutathione disulfide glutathione oxidized*glutathione ox*GSSG*glutathione*GSH*ox. glutathione*oxidized glutathione 612.626 C20 H32 N6 O12 S2 C(=O)(CCC(N)C(O)=O)NC(C(=O)NCC(O)=O)CSSCC(C(=O)NCC(O)=O)NC(=O)CCC(N)C(=O)O LIGAND-CPD:C00127:*CAS:27025-41-8 1.11.1.9 H2O2 + glutathione = glutathione disulfide + H2O glutathione redox reactions I glutathione disulfide glutathione oxidized*glutathione ox*GSSG*glutathione*GSH*ox. glutathione*oxidized glutathione 612.626 C20 H32 N6 O12 S2 C(=O)(CCC(N)C(O)=O)NC(C(=O)NCC(O)=O)CSSCC(C(=O)NCC(O)=O)NC(=O)CCC(N)C(=O)O LIGAND-CPD:C00127:*CAS:27025-41-8 1.11.1.12 glutathione + a lipid hydroperoxide = glutathione disulfide + lipid + H2O glutathione redox reactions I L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C(=O)(O)C(N)Cc1(ccccc1) LIGAND-CPD:C00079:*CAS:63-91-2 2.6.1.57 phenylpyruvate + L-glutamate = L-phenylalanine + α-ketoglutarate phenylalanine degradation III L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C(=O)(O)C(N)Cc1(ccccc1) LIGAND-CPD:C00079:*CAS:63-91-2 2.6.1.57 phenylpyruvate + L-glutamate = L-phenylalanine + α-ketoglutarate phenylalanine biosynthesis I L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C(=O)(O)C(N)Cc1(ccccc1) LIGAND-CPD:C00079:*CAS:63-91-2 4.3.1.5 L-phenylalanine = ammonia + trans-cinnamate suberin biosynthesis L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C(=O)(O)C(N)Cc1(ccccc1) LIGAND-CPD:C00079:*CAS:63-91-2 4.3.1.5 L-phenylalanine = ammonia + trans-cinnamate phenylpropanoid biosynthesis, initial reactions L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C(=O)(O)C(N)Cc1(ccccc1) LIGAND-CPD:C00079:*CAS:63-91-2 4.3.1.5 L-phenylalanine = ammonia + trans-cinnamate salicylate biosynthesis L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C(=O)(O)C(N)Cc1(ccccc1) LIGAND-CPD:C00079:*CAS:63-91-2 L-methionine + phenylpyruvate = 2-oxo-4-methylthiobutanoate + L-phenylalanine methionine degradation III L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C(=O)(O)C(N)Cc1(ccccc1) LIGAND-CPD:C00079:*CAS:63-91-2 2.6.1.58 pyruvate + L-phenylalanine = phenylpyruvate + L-alanine phenylalanine degradation III L-phenylalanine F*endophenyl*phenylalanine*phe 165.191 C9 H11 N1 O2 C(=O)(O)C(N)Cc1(ccccc1) LIGAND-CPD:C00079:*CAS:63-91-2 6.1.1.20 L-phenylalanine + ATP = diphosphate + AMP tRNA charging pathway squalene 410.725 C30 H50 CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:111-02-4 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis I squalene 410.725 C30 H50 CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:111-02-4 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) squalene 410.725 C30 H50 CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:111-02-4 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) squalene 410.725 C30 H50 CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:111-02-4 2.5.1.21 presqualene diphosphate = squalene + diphosphate cholesterol biosynthesis I squalene 410.725 C30 H50 CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:111-02-4 2.5.1.21 presqualene diphosphate = squalene + diphosphate cholesterol biosynthesis III (via desmosterol) squalene 410.725 C30 H50 CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:111-02-4 2.5.1.21 presqualene diphosphate = squalene + diphosphate cholesterol biosynthesis II (via 24,25-dihydrolanosterol) squalene 410.725 C30 H50 CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:111-02-4 2.5.1.21 presqualene diphosphate = squalene + diphosphate sterol biosynthesis squalene 410.725 C30 H50 CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:111-02-4 1.14.99.7 O2 + squalene = (S)-2,3-Epoxysqualene + H2O sterol 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 601.291 C14 H26 N3 O17 P3 CC(CO)(OP(O)(O)=O)C(O)COP(=O)(O)OP(=O)(O)OCC1(OC(C(O)C1O)n2(c(=O)nc(N)cc2)) 2.7.1.148 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + ATP = 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 601.291 C14 H26 N3 O17 P3 CC(CO)(OP(O)(O)=O)C(O)COP(=O)(O)OP(=O)(O)OCC1(OC(C(O)C1O)n2(c(=O)nc(N)cc2)) 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 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 338.213 C9 H15 N4 O8 P1 C(OP(=O)(O)O)[CH]1(O[CH]([CH](O)[CH](O)1)n2(c(N)c(C(=O)N)nc2)) LIGAND-CPD:C04677:*CAS:3031-94-5 2.1.2.3 N10-formyl-THF + AICAR = tetrahydrofolate + phosphoribosyl-formamido-carboxamide purine nucleotides de novo biosynthesis II 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 338.213 C9 H15 N4 O8 P1 C(OP(=O)(O)O)[CH]1(O[CH]([CH](O)[CH](O)1)n2(c(N)c(C(=O)N)nc2)) LIGAND-CPD:C04677:*CAS:3031-94-5 2.1.2.3 N10-formyl-THF + AICAR = tetrahydrofolate + phosphoribosyl-formamido-carboxamide purine nucleotides de novo biosynthesis I 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 338.213 C9 H15 N4 O8 P1 C(OP(=O)(O)O)[CH]1(O[CH]([CH](O)[CH](O)1)n2(c(N)c(C(=O)N)nc2)) LIGAND-CPD:C04677:*CAS:3031-94-5 4.3.2.2 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole = fumarate + AICAR purine nucleotides de novo biosynthesis II 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 338.213 C9 H15 N4 O8 P1 C(OP(=O)(O)O)[CH]1(O[CH]([CH](O)[CH](O)1)n2(c(N)c(C(=O)N)nc2)) LIGAND-CPD:C04677:*CAS:3031-94-5 4.3.2.2 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole = fumarate + AICAR purine nucleotides de novo biosynthesis I 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 338.213 C9 H15 N4 O8 P1 C(OP(=O)(O)O)[CH]1(O[CH]([CH](O)[CH](O)1)n2(c(N)c(C(=O)N)nc2)) LIGAND-CPD:C04677:*CAS:3031-94-5 2.4.2.- phosphoribulosylformimino-AICAR-P + L-glutamine = L-glutamate + D-erythro-imidazole-glycerol-phosphate + AICAR histidine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ NAD salvage pathway 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.17 L-glutamate + ATP = ADP formylTHF 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.17 L-glutamate + ATP = ADP formylTHF 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 L-glutamate + ATP + NADPH = ADP + L-glutamate γ-semialdehyde + NADP+ arginine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate glutamine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate asparagine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate aspartate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.1 L-aspartate + α-ketoglutarate = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.8 L-glutamine + chorismate = L-glutamate + 4-amino-4-deoxychorismate tetrahydrofolate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.8 L-glutamine + chorismate = L-glutamate + 4-amino-4-deoxychorismate tetrahydrofolate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine purine nucleotides de novo 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 3.5.1.- N2-succinylglutamate + H2O = L-glutamate + succinate arginine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 3.4.19.9 glutathione-mediated detoxification 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.17 tetrahydrofolate + L-glutamate + ATP = THF-L-glutamate + ADP tetrahydrofolate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP formylTHF 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP tetrahydrofolate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP formylTHF 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP tetrahydrofolate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phosphoribosyl 1-pyrophosphate + L-glutamine + H2O 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phosphoribosyl 1-pyrophosphate + L-glutamine + H2O purine nucleotides de novo 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.39 α-ketoglutarate + α-aminoadipate = L-glutamate + α-ketoadipate lysine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.39 α-ketoglutarate + α-aminoadipate = L-glutamate + α-ketoadipate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 1.5.1.12 NAD+ + H2O = L-glutamate + NADH proline 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 1.5.1.12 NAD+ + H2O = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 4.1.3.27 chorismate + L-glutamine = L-glutamate + anthranilate + 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 3.4.19.9 folate polyglutamylation 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.5 L-tyrosine + α-ketoglutarate = L-glutamate + p-hydroxyphenylpyruvate tyrosine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.17 α-ketoglutarate = L-glutamate + N-succinyl-2-amino-6-ketopimelate lysine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.1 3-sulfinoalanine + α-ketoglutarate = L-glutamate + 3-sulfinyl-pyruvate L-cysteine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP glutamine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 3.5.1.2 L-glutamine + H2O = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.4 α-ketoglutarate + 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.80 nicotianamine + α-ketoglutarate = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.27 α-ketoglutarate + 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate de novo biosynthesis of pyrimidine ribonucleotides 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.5 ATP + L-glutamine + CO2 + H2O = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.5 ATP + L-glutamine + CO2 + H2O = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 1.5.1.9 H2O + NAD+ + saccharopine = L-glutamate + NADH + 2-aminoadipate-6-semialdehyde 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.3.1.1 L-glutamate + acetyl-CoA = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.3.1.1 L-glutamate + acetyl-CoA = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.17 ATP + L-glutamate = ADP folate polyglutamylation 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.17 ATP + L-glutamate = ADP formylTHF 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.17 ATP + L-glutamate = ADP tetrahydrofolate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.11 N2-succinyl-L-ornithine + α-ketoglutarate = L-glutamate + N2-succinyl-L-glutamate 5-semialdehyde arginine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 4.1.1.15 L-glutamate = CO2 + 4-aminobutyrate glutamate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.7.2.11 L-glutamate + ATP = L-glutamate-5-phosphate + ADP proline 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.23 α-ketoglutarate + L-erythro-4-hydroxy-glutamate = L-glutamate + D-4-hydroxy-2-keto-glutarate 4-hydroxyproline 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.3 α-ketoglutarate + L-cysteine = L-glutamate + 3-mercaptopyruvate L-cysteine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.2 α-ketoglutarate + 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.2 α-ketoglutarate + L-alanine = L-glutamate + pyruvate alanine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 1.5.1.10 2-aminoadipate-6-semialdehyde + NADPH + L-glutamate = saccharopine + NADP+ + H2O lysine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 1.4.1.13 L-glutamate + NADP+ = L-glutamine + α-ketoglutarate + NADPH glutamine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 1.4.1.13 L-glutamate + NADP+ = L-glutamine + α-ketoglutarate + NADPH glutamate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.52 2-oxo-3-hydroxy-4-phosphobutanoate + L-glutamate = 4-(phosphonooxy)-threonine + α-ketoglutarate pyridoxal 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 indole-3-acetate + L-glutamate = indole-3-acetyl-glu + H2O IAA conjugate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 1.5.1.12 H2O = L-glutamate + H+ proline 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.57 phenylpyruvate + L-glutamate = L-phenylalanine + α-ketoglutarate phenylalanine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.57 phenylpyruvate + L-glutamate = L-phenylalanine + α-ketoglutarate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.2.2 L-cysteine + L-glutamate + ATP = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.52 3-phospho-serine + α-ketoglutarate = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 L-2-acetamido-6-oxoheptanedioate + L-glutamate = N-acetyl-L,L-2,6-diaminopimelate + α-ketoglutarate lysine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate pantothenate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.4.2 ATP + UTP + L-glutamine + H2O = ADP + CTP + L-glutamate de novo biosynthesis of pyrimidine ribonucleotides 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.19 α-ketoglutarate + 4-aminobutyrate = L-glutamate + succinate semialdehyde glutamate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.- tetrahydrodipicolinate + L-glutamate + H2O = L,L-diaminopimelate + α-ketoglutarate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.11 N-acetyl-L-ornithine + α-ketoglutarate = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.11 N-acetyl-L-ornithine + α-ketoglutarate = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.16 fructose-6-phosphate + L-glutamine = L-glutamate + D-glucosamine-6-phosphate UDP-N-acetylgalactosamine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.9 imidazole acetol-phosphate + L-glutamate = L-histidinol-phosphate + α-ketoglutarate histidine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.13 L-ornithine + α-ketoglutarate = L-glutamate + L-glutamate γ-semialdehyde proline biosynthesis V (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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.13 L-ornithine + α-ketoglutarate = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.13 L-ornithine + α-ketoglutarate = L-glutamate + L-glutamate γ-semialdehyde arginine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.13 L-ornithine + α-ketoglutarate = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.13 L-ornithine + α-ketoglutarate = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 L-serine + α-ketoglutarate = L-glutamate + hydroxypyruvate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-isoleucine + α-ketoglutarate = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-isoleucine + α-ketoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine biosynthesis 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-isoleucine + α-ketoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.4.2.- phosphoribulosylformimino-AICAR-P + L-glutamine = L-glutamate + D-erythro-imidazole-glycerol-phosphate + AICAR histidine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 1.4.1.4 L-glutamate + H2O + NADP+ = ammonia + α-ketoglutarate + NADPH 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-leucine + α-ketoglutarate = L-glutamate + 2-ketoisocaproate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-leucine + α-ketoglutarate = L-glutamate + 2-ketoisocaproate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 2.6.1.42 L-leucine + α-ketoglutarate = L-glutamate + 2-ketoisocaproate 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = L-glutamate + L-asparagine + diphosphate + AMP asparagine 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = 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 147.13 C5 H9 N1 O4 C(=O)(O)C(N)CCC(O)=O CAS:6893-26-1*LIGAND-CPD:C00025:*CAS:56-86-0 5.1.1.3 L-glutamate = D-glutamate peptidoglycan biosynthesis I 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol 4,4-dimethyl-cholesta-8,12,24-trienol*17-(1,5-dimethylhex-4-enyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7, 10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol*4,4-dimethyl-5α-cholesta-8,14,24-trien-3β-ol 410.682 C29 H46 O1 CC(C)=CCCC(C)C1(C2(C)(C(=CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADP+ + H2O + formate cholesterol biosynthesis I 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol 4,4-dimethyl-cholesta-8,12,24-trienol*17-(1,5-dimethylhex-4-enyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7, 10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol*4,4-dimethyl-5α-cholesta-8,14,24-trien-3β-ol 410.682 C29 H46 O1 CC(C)=CCCC(C)C1(C2(C)(C(=CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADP+ + H2O + formate cholesterol biosynthesis III (via desmosterol) 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol 4,4-dimethyl-cholesta-8,12,24-trienol*17-(1,5-dimethylhex-4-enyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7, 10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol*4,4-dimethyl-5α-cholesta-8,14,24-trien-3β-ol 410.682 C29 H46 O1 CC(C)=CCCC(C)C1(C2(C)(C(=CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.3.1.70 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADPH = 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + NADP+ cholesterol biosynthesis I 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol 4,4-dimethyl-cholesta-8,12,24-trienol*17-(1,5-dimethylhex-4-enyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7, 10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol*4,4-dimethyl-5α-cholesta-8,14,24-trien-3β-ol 410.682 C29 H46 O1 CC(C)=CCCC(C)C1(C2(C)(C(=CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.3.1.70 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADPH = 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + NADP+ cholesterol biosynthesis III (via desmosterol) 1-pyrroline 69.106 C4 H7 N1 C1(CCC=N1) 4-aminobutanal = 1-pyrroline + H2O β-alanine biosynthesis I 2-C-methyl-D-erythritol-4-phosphate MEP 216.127 C5 H13 O7 P1 C(OP(O)(=O)O)C(O)C(O)(C)CO LIGAND-CPD:C11434: 2.7.7.60 2-C-methyl-D-erythritol-4-phosphate + CTP = 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + diphosphate methylerythritol phosphate pathway 2-C-methyl-D-erythritol-4-phosphate MEP 216.127 C5 H13 O7 P1 C(OP(O)(=O)O)C(O)C(O)(C)CO LIGAND-CPD:C11434: 1.1.1.267 2-C-methyl-D-erythritol-4-phosphate + NADP+ = 1-deoxy-D-xylulose 5-phosphate + NADPH methylerythritol phosphate pathway benzyladenine-9-N-glucoside 387.394 C18 H21 N5 O5 c1(c2(c(ncn1)N(C=N2)C3(OC(CO)C(O)C(O)C(O)3)))(NCc4(ccccc4)) 2.4.1.- benzyladenine + UDP-D-glucose = benzyladenine-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis 6-hydroxymethyl-dihydropterin dihydropterin-CH2OH*2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine 195.18 C7 H9 N5 O2 C2(C(CO)=Nc1(c(O)nc(N)nc1N2)) 2.7.6.3 6-hydroxymethyl-dihydropterin + ATP = 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + AMP tetrahydrofolate biosynthesis I 6-hydroxymethyl-dihydropterin dihydropterin-CH2OH*2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine 195.18 C7 H9 N5 O2 C2(C(CO)=Nc1(c(O)nc(N)nc1N2)) 2.7.6.3 6-hydroxymethyl-dihydropterin + ATP = 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + AMP tetrahydrofolate biosynthesis II 6-hydroxymethyl-dihydropterin dihydropterin-CH2OH*2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine 195.18 C7 H9 N5 O2 C2(C(CO)=Nc1(c(O)nc(N)nc1N2)) 4.1.2.25 dihydro-neo-pterin = glycolaldehyde + 6-hydroxymethyl-dihydropterin tetrahydrofolate biosynthesis I 6-hydroxymethyl-dihydropterin dihydropterin-CH2OH*2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine 195.18 C7 H9 N5 O2 C2(C(CO)=Nc1(c(O)nc(N)nc1N2)) 4.1.2.25 dihydro-neo-pterin = glycolaldehyde + 6-hydroxymethyl-dihydropterin tetrahydrofolate biosynthesis II lanosterol 4,4,14α-trimethyl-5α-cholesta-8,24-dien-3β-ol 426.724 C30 H50 O1 CC(C)=CCCC(C)C1(C2(C)(C(C)(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) CAS:79-63-0 1.3.1.72 lanosterol + NADPH = 24,25-dihydrolanosterol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) lanosterol 4,4,14α-trimethyl-5α-cholesta-8,24-dien-3β-ol 426.724 C30 H50 O1 CC(C)=CCCC(C)C1(C2(C)(C(C)(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) CAS:79-63-0 5.4.99.7 (S)-2,3-Epoxysqualene = lanosterol cholesterol biosynthesis I lanosterol 4,4,14α-trimethyl-5α-cholesta-8,24-dien-3β-ol 426.724 C30 H50 O1 CC(C)=CCCC(C)C1(C2(C)(C(C)(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) CAS:79-63-0 5.4.99.7 (S)-2,3-Epoxysqualene = lanosterol cholesterol biosynthesis III (via desmosterol) lanosterol 4,4,14α-trimethyl-5α-cholesta-8,24-dien-3β-ol 426.724 C30 H50 O1 CC(C)=CCCC(C)C1(C2(C)(C(C)(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) CAS:79-63-0 5.4.99.7 (S)-2,3-Epoxysqualene = lanosterol cholesterol biosynthesis II (via 24,25-dihydrolanosterol) lanosterol 4,4,14α-trimethyl-5α-cholesta-8,24-dien-3β-ol 426.724 C30 H50 O1 CC(C)=CCCC(C)C1(C2(C)(C(C)(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) CAS:79-63-0 1.14.13.70 lanosterol + NADPH + O2 = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis I lanosterol 4,4,14α-trimethyl-5α-cholesta-8,24-dien-3β-ol 426.724 C30 H50 O1 CC(C)=CCCC(C)C1(C2(C)(C(C)(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) CAS:79-63-0 1.14.13.70 lanosterol + NADPH + O2 = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) histidinol histidol*histidinol*L-histidinol 141.172 C6 H11 N3 O1 c1(c(nc[nH]1)CC(N)CO) LIGAND-CPD:C00860:*CAS:501-28-0 1.1.1.23 histidinol + NAD+ = histidinal + NADH histidine biosynthesis I histidinol histidol*histidinol*L-histidinol 141.172 C6 H11 N3 O1 c1(c(nc[nH]1)CC(N)CO) LIGAND-CPD:C00860:*CAS:501-28-0 3.1.3.15 L-histidinol-phosphate + H2O = histidinol histidine biosynthesis I (-)-β-phellandrene β-phellandrene 136.236 C10 H16 C=C1(C=CC(C(C)C)CC1) 4.2.3.- geranyl-PP = (-)-β-phellandrene + diphosphate oleoresin monoterpene volatiles biosynthesis urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(N)(N)=O 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(N)(N)=O 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(N)(N)=O LIGAND-CPD:C00086:*CAS:57-13-6 3.5.3.1 H2O + L-arginine = urea + L-ornithine arginine degradation VII (arginase 3 pathway) urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(N)(N)=O 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(N)(N)=O 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(N)(N)=O LIGAND-CPD:C00086:*CAS:57-13-6 3.5.1.5 H2O + urea = ammonia + CO2 canavanine degradation urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(N)(N)=O LIGAND-CPD:C00086:*CAS:57-13-6 3.5.1.5 H2O + urea = ammonia + CO2 arginine degradation VII (arginase 3 pathway) urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(N)(N)=O LIGAND-CPD:C00086:*CAS:57-13-6 3.5.3.1 canavanine + H2O = L-canaline + urea canavanine degradation urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(N)(N)=O 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(N)(N)=O LIGAND-CPD:C00086:*CAS:57-13-6 3.5.3.11 H2O + agmatine = urea + putrescine putrescine biosynthesis I urea bromisovalum*carmol*basodexan*carbamide 60.055 C1 H4 N2 O1 C(N)(N)=O 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(N)(N)=O LIGAND-CPD:C00086:*CAS:57-13-6 3.5.3.4 H2O + allantoate = (S)-ureidoglycolate + urea allantoin degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.- dihydroneopterin phosphate + H2O = dihydro-neo-pterin tetrahydrofolate biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.- dihydroneopterin phosphate + H2O = dihydro-neo-pterin tetrahydrofolate biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 isopentenyladenosine-5'-triphosphate + NADPH + H2O = trans-zeatin riboside triphosphate + NADP+ trans-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.7.2 guanosine 5'-diphosphate,3'-diphosphate + H2O = diphosphate + GDP ppGpp biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.2.2 pyruvate + ubiquinone-8 + H2O = ubiquinol-8 + acetate + CO2 mixed acid fermentation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.- 18-oxooleate + NADP+ + H2O = octadec-9-ene-1,18-dioic-acid + NADPH suberin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.2.5 H2O + allantoin = allantoate ureide biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.2.5 H2O + allantoin = allantoate allantoin degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.4.3.6 tryptamine + H2O + O2 = ammonia + indole acetaldehyde + H2O2 IAA biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.3 leucopelargonidin + NADPH = afzelechin + NADP+ + H2O proanthocyanidin biosynthesis from flavanols H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 liquiritigenin + NADPH + O2 = 6,7,4'-trihydroxyflavanone + NADP+ + H2O 6,7,4'-trihydroxyisoflavone biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- dihydrokaempferol + NADPH + O2 = dihydromyricetin + NADP+ + H2O leucodelphinidin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.3.10 acetoacetyl-CoA + H2O + acetyl-CoA = coenzyme A + 3-hydroxy-3-methyl-glutaryl-CoA mevalonate pathway H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*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 H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.32 H2O + NAD+ + 2-aminomuconate semialdehyde = NADH + 2-amino-muconate tryptophan degradation III (eukaryotic) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 indole-3-acetate + L-leucine = indole-3-acetyl-leu + H2O IAA conjugate biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.4 acrylamide + H2O = ammonia + acrylate + H+ acrylonitrile degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.27 5,10-methenyltetrahydromethanopterin + H2O = 5-formyl-tetrahydromethanopterin methanogenesis from CO2 H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol + O2 = 4α-formyl-4β-methyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- GA8 + α-ketoglutarate + O2 = GA8-catabolite + succinate + CO2 + H2O gibberellin inactivation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 benzoyl-CoA + H2O = benzoate + coenzyme A salicylate biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ purine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ salvage pathways of adenine, hypoxanthine, and their nucleosides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ ureide biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4α-formyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4α-formyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 (E)-cinnamoyl-CoA + H2O = hydroxycinnamoyl-CoA salicylate biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.1 H2O + L-arginine = urea + L-ornithine urea cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*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 H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.1 H2O + L-arginine = urea + L-ornithine arginine degradation VII (arginase 3 pathway) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*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 H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.1 H2O + L-arginine = urea + L-ornithine citrulline biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.11 H2O = methanol homogalacturonan degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.7.3.3 urate + O2 + H2O = 5-hydroxyisourate + H2O2 ureide biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.99.12 trans-zeatin riboside + H2O + FAD = adenosine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2-amino-muconate + H2O + NADH = NH(4)OH + α-ketoadipate + NAD+ tryptophan degradation III (eukaryotic) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.3 3-phospho-serine + H2O = L-serine serine biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.10 3-dehydroquinate = H2O + 3-dehydro-shikimate quinate degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.10 3-dehydroquinate = H2O + 3-dehydro-shikimate chorismate biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.1.48 1-(o-carboxyphenylamino)-1'-deoxyribulose-5'-phosphate = indole-3-glycerol-phosphate + CO2 + H2O tryptophan biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 chlorophyll b + H2O + NADP+ = 7-hydroxy-chlorophyll a + O2 + NADPH chlorophyll cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.1.7 H2O + NAD+ + saccharopine = NADH + α-ketoglutarate + L-lysine lysine biosynthesis IV H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.60 fatty acid elongation -- saturated H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 isopentenyladenosine-5'-monophosphate + H2O = isopentenyl adenosine trans-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- GA29 + α-ketoglutarate + O2 = GA29-catabolite + succinate + CO2 + H2O gibberellin inactivation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.22 L-homocysteine + L-serine = H2O + cystathionine homocysteine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.22 L-homocysteine + L-serine = H2O + cystathionine homocysteine and cysteine interconversion H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 H2O + UDP-2,3-bis(3-hydroxymyristoyl)glucosamine = 2,3-bis(3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate + UMP lipid-A-precursor biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.11 trans-cinnamate + O2 + NADPH = H2O + NADP+ + 4-coumarate suberin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.11 trans-cinnamate + O2 + NADPH = H2O + NADP+ + 4-coumarate phenylpropanoid biosynthesis, initial reactions H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.- α-carotene + NADPH + O2 = zeinoxanthin + NADP+ + H2O carotenoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1-(3-aminopropyl)-4-aminobutanal = 1-(3-aminopropyl)-pyrrolinium + H2O β-alanine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.9 H2O = N10-formyl-THF folate transformations H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.9 H2O = N10-formyl-THF formylTHF biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.9 H2O = N10-formyl-THF tetrahydrofolate biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.9 H2O = N10-formyl-THF formylTHF biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.- N2-succinyl-L-arginine + H2O = ammonia + N2-succinyl-L-ornithine + CO2 arginine degradation II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate glycine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate folate polyglutamylation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate folate transformations H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate glycine betaine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate formylTHF biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate formylTHF biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate photorespiration H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.4.2 ATP + UTP + L-glutamine + H2O = ADP + CTP + L-glutamate de novo biosynthesis of pyrimidine ribonucleotides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.4.46 H2O = sn-glycerol-3-phosphate glycerol degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.31 D-glucono-δ-lactone-6-phosphate + H2O = 6-phospho-D-gluconate pentose phosphate pathway (oxidative branch) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.13.12.1 O2 + L-arginine = 4-guanidinobutyramide + H2O + CO2 arginine degradation X (arginine monooxygenase pathway) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.6.1.- tetrahydrodipicolinate + L-glutamate + H2O = L,L-diaminopimelate + α-ketoglutarate lysine biosynthesis VI H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.5 inosine-5'-phosphate + H2O = inosine purine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.5 inosine-5'-phosphate + H2O = inosine salvage pathways of purine nucleosides II (plant) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.4 indole-3-acetamide + H2O = indole-3-acetate + ammonia IAA biosynthesis VI (via indole-3-acetamide) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.4 indole-3-acetamide + H2O = indole-3-acetate + ammonia IAA biosynthesis IV H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.1 xanthosine + H2O = xanthine + D-ribose purine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.1 xanthosine + H2O = xanthine + D-ribose salvage pathways of purine nucleosides II (plant) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.11.1.12 glutathione + a lipid hydroperoxide = glutathione disulfide + lipid + H2O glutathione redox reactions I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.19 phosphoribosyl-AMP + H2O = phosphoribosylformiminoAICAR-phosphate histidine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.14.1 cotinine + NADPH + O2 = N'-hydroxymethyl-norcotinine + NADP+ + H2O nicotine degradation III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.1.- H2O + coumaroyl-CoA + malonyl-CoA = coenzyme A + CO2 + p-coumaroyltriacetate resveratrol biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.2.9 D-xylulose-5-phosphate = H2O + D-glyceraldehyde-3-phosphate + acetylphosphate glucose fermentation to lactate II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.5 H2O + cytidine = ammonia + uridine salvage pathways of purine and pyrimidine nucleotides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.5 H2O + cytidine = ammonia + uridine (deoxy)ribose phosphate degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.5 H2O + cytidine = ammonia + uridine salvage pathways of pyrimidine ribonucleotides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.14 acyl-ACP thioesterase pathway H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.8.1.2 H2O + NADP+ + hydrogen sulfide = sulfite + NADPH sulfate reduction I (assimilatory) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- GA15 + α-ketoglutarate + O2 = GA24 + succinate + CO2 + H2O gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ purine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ salvage pathways of purine nucleosides II (plant) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.7.9.3 H2O + selenide + ATP = selenophosphate + AMP selenocysteine biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.30 O2 + neurosporene = H2O + trans-lycopene carotenoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- oleate + NADPH + O2 = 18-hydroxyoleate + NADP+ + H2O cutin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- oleate + NADPH + O2 = 18-hydroxyoleate + NADP+ + H2O suberin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*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 H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*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 H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.- nicotinate nucleotide + H2O = nicotinate + D-ribose-5-phosphate pyridine nucleotide cycling (plants) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.10.3.3 L-ascorbate + O2 = monodehydroascorbate + H2O ascorbate glutathione cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.20 indole + L-serine = L-tryptophan + H2O tryptophan biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.11.1.6 H2O2 = H2O + O2 removal of superoxide radicals H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.10.99.3 antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O carotenoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.10.99.3 antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.- NADPH + H2O = NADH NAD/NADH phosphorylation and dephosphorylation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 salicyloyl-CoA + H2O = salicylate + coenzyme A salicylate biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 iminoaspartate + dihydroxy-acetone-phosphate = quinolinate + H2O NAD biosynthesis I (from aspartate) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.3 citrate = cis-aconitate + H2O TCA cycle variation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.3 citrate = cis-aconitate + H2O reductive TCA cycle I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.3 citrate = cis-aconitate + H2O respiration (anaerobic) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.3 citrate = cis-aconitate + H2O TCA cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.88 dihydroquercetin + NADPH + O2 = dihydromyricetin + NADP+ + H2O leucodelphinidin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- palmitate + NADPH + O2 = 16-hydroxypalmitate + NADP+ + H2O cutin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.14.1 N'-hydroxymethyl-norcotinine + NADPH + O2 = norcotinine + NADP+ + H2O nicotine degradation III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.18 H2O = L,L-diaminopimelate + succinate lysine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.1.8 H2O + NADP+ + saccharopine = NADPH + α-ketoglutarate + L-lysine lysine degradation II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.5 indole acetaldehyde + H2O = indole-3-acetate + H+ tryptophan degradation V (side chain pathway) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.51 prephenate = phenylpyruvate + H2O + CO2 phenylalanine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 isopentenyladenine + H2O = trans-zeatin + H+ trans-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3-deoxy-capsidiol + O2 + NADPH = capsidiol + H2O + NADP+ capsidiol biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.36 homoisocitrate = H2O + 3-carboxyhex-2-enedioate lysine biosynthesis IV H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.246 (-)-sophorol + NADPH = (-)-maackiain + NADP+ + H2O maackiain biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 acrylyl-CoA + H2O = 3-hydroxypropionyl-CoA β-alanine biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.16 N-acetyl-L-ornithine + H2O = L-ornithine + acetate ornithine biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 5-amino-6-(5'-phosphoribitylamino)uracil + H2O = 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione flavin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.60 fatty acid elongation -- unsaturated II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.14 nicotinamide mononucleotide + H2O = D-ribose-5-phosphate + nicotinamide NAD salvage pathway I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.14 nicotinamide mononucleotide + H2O = D-ribose-5-phosphate + nicotinamide pyridine nucleotide cycling (plants) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine S-adenosylmethionine biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine methionine salvage pathway H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*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 H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*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 H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*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 H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*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 H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 hypoxanthine + H2O = H+ + xanthine salvage pathways of adenine, hypoxanthine, and their nucleosides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.8 D-mannonate = H2O + 2-dehydro-3-deoxy-D-gluconate β-D-glucuronide degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O gluconeogenesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O sucrose degradation to ethanol and lactate (anaerobic) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O respiration (anaerobic) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O glycolysis IV (plant cytosol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O fructose degradation to pyruvate and lactate (anaerobic) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O glucose fermentation to lactate II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O glycolysis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*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 H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.11 H2O + agmatine = urea + putrescine putrescine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.31 2-aminoadipate-6-semialdehyde + H2O + NAD+ = α-aminoadipate + NADH lysine degradation II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.- phytoene + O2 = phytofluene + H2O carotenoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.12 H2O + agmatine = ammonia + N-carbamoylputrescine putrescine biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.12 H2O + agmatine = ammonia + N-carbamoylputrescine arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 L-4-hydroxy-proline + O2 = pyrroline-hydroxy-carboxylate + H2O 4-hydroxyproline degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.15 L-histidinol-phosphate + H2O = histidinol histidine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.3 acetaldehyde + NAD+ + H2O = NADH + acetate oxidative ethanol degradation III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.3 acetaldehyde + NAD+ + H2O = NADH + acetate oxidative ethanol degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- eriodictyol + NADPH + O2 = 3',4',5'-pentahydroxyflavanone + NADP+ + H2O leucodelphinidin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.26 H2O + 2,5-diamino-6-(ribosylamino)-4-(3H)-pyrimidinone 5'-phosphate = 5-amino-6-(5'-phosphoribosylamino)uracil + ammonia flavin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.32 phospholipases H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate = O-succinylbenzoate + H2O menaquinone biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate = O-succinylbenzoate + H2O phylloquinone biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.4 H2O + 3-hydroxy-isobutyryl-CoA = 3-hydroxy-isobutyrate + coenzyme A valine degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 coumarinate = coumarin + H2O coumarin biosynthesis (via 2-coumarate) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.3 3-aminopropionaldehyde + H2O = β-alanine β-alanine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.14.1 cotinine + NADPH + O2 = trans-3'-hydroxycotinine + NADP+ + H2O nicotine degradation III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 GDP = dGDP + H2O purine nucleotides de novo biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine purine nucleotides de novo biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine purine nucleotides de novo biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.37 H2O = D-sedoheptulose-7-phosphate Calvin cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.54 D-lactoyl-CoA = H2O + acrylyl-CoA D-lactate fermentation to propionate and acetate H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.3.3.3 coproporphyrinogen III + O2 + H+ = protoporphyrinogen IX + CO2 + H2O heme biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.3.3.3 coproporphyrinogen III + O2 + H+ = protoporphyrinogen IX + CO2 + H2O chlorophyllide a biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 7,2'-dihydroxy-4'-methoxy-isoflavanol-quinonemethide-intermediate-2 = (-)-medicarpin + H2O medicarpin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.14.1 bupropion + NADPH + O2 = hydroxybupropion + NADP+ + H2O bupropion degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.92 13-HPOT = H2O + 12,13(S)-epoxylinolenate jasmonic acid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.1.117 H2O + tetrahydrodipicolinate + succinyl-CoA = N-succinyl-2-amino-6-ketopimelate + coenzyme A lysine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.14.1 acetone + NADPH + O2 = acetol + NADP+ + H2O acetone degradation (to methylglyoxal) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.- zeinoxanthin + NADPH + O2 = lutein + NADP+ + H2O carotenoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.5 indole-3-glyoxal + H2O + an oxidized acceptor = indole-3-glyoxylate tryptophan degradation V (side chain pathway) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 7,2'-dihydroxy-4'-methoxy-isoflavanol carbocation intermediate 2 = (-)-medicarpin + H2O medicarpin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.1.12 NAD+ + H2O = L-glutamate + NADH proline degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.1.12 NAD+ + H2O = L-glutamate + NADH arginine degradation I (arginase pathway) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.1 H2CO3 = H2O + CO2 cyanate degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4,4-dimethyl-5α-cholesta-8-en-3-β-ol + O2 = 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.99.3 crocetin dialdehyde + H2O = crocetin crocetin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 p-coumaroyltriacetate = p-coumaroyltriacetic acid lactone + H2O resveratrol biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 diprenylphlorisovalerophenone + O2 = humulone + H2O humulone biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.3.- geranyl-PP + H2O = geraniol + diphosphate secologanin and strictosidine biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.2 L-glutamine + H2O = L-glutamate + ammonia citrulline biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.99.12 isopentenyladenine + FAD + H2O = 3-methyl-2-butenal + adenine + FADH2 cytokinins degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 H2O + deoxyadenosine = ammonia + deoxyinosine salvage pathways of adenine, hypoxanthine, and their nucleosides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 fatty acid β-oxidation IV (plant, unsaturated, even number) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.15 homogalacturonan degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.7 H2O + adenosine = D-ribose + adenine salvage pathways of purine nucleosides II (plant) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 isopentenyladenosine-5'-diphosphate + H2O = isopentenyladenosine-5'-monophosphate trans-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.3 H2O + guanine = ammonia + xanthine purine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.3 H2O + guanine = ammonia + xanthine salvage pathways of purine nucleosides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.3 H2O + guanine = ammonia + xanthine salvage pathways of purine nucleosides II (plant) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.22 UDP-D-glucose + H2O + NAD+ = UDP-D-glucuronate + NADH UDP-D-xylose biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.22 UDP-D-glucose + H2O + NAD+ = UDP-D-glucuronate + NADH galactose degradation II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.70 NADPH + O2 + obtusifoliol + H+ = H2O + NADP+ + formate + (4α)-methyl-(5α)-ergosta-8,14,24(28)-trien-3β-ol sterol biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.75 hydroxymethylbilane = uroporphyrinogen-III + H2O tetrapyrrole biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.2 malate = fumarate + H2O mixed acid fermentation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.2 malate = fumarate + H2O TCA cycle variation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.2 malate = fumarate + H2O reductive TCA cycle I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.2 malate = fumarate + H2O respiration (anaerobic) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.2 malate = fumarate + H2O TCA cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 ferulate + NADPH + O2 = 5-hydroxy-ferulic-acid + H2O + NADP+ free phenylpropanoid acid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.-.- sphinganine + O2 + NADPH = 4-hydroxysphinganine + H2O + NADP+ sphingolipid metabolism H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.- 7,8-dihydroneopterin 3'-triphosphate + H2O = dihydroneopterin phosphate + diphosphate tetrahydrofolate biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.- 7,8-dihydroneopterin 3'-triphosphate + H2O = dihydroneopterin phosphate + diphosphate tetrahydrofolate biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.1.10 2-aminoadipate-6-semialdehyde + NADPH + L-glutamate = saccharopine + NADP+ + H2O lysine biosynthesis IV H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 demethylsuberosin + O2 + NADPH = marmesin + NADP+ + H2O linear furanocoumarin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.2 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H+ = H2O methylerythritol phosphate pathway H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.53 N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia putrescine biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.53 N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.1.12 H2O = L-glutamate + H+ proline degradation II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.4 H2O + allantoate = (S)-ureidoglycolate + urea allantoin degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.26 sucrose + H2O = α-D-glucose + fructose sucrose degradation III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.22 H2O + NAD+ + L-lactaldehyde = NADH + L-lactate fucose degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 isopentenyladenosine-5'-monophosphate + H2O = isopentenyladenine + D-ribose-5-phosphate trans-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.5 AMP + H2O = adenosine salvage pathways of purine nucleosides II (plant) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 mixed acid fermentation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 reductive TCA cycle I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 gluconeogenesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 respiration (anaerobic) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.4 H2O + adenosine = ammonia + inosine salvage pathways of adenine, hypoxanthine, and their nucleosides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.4 H2O + adenosine = ammonia + inosine salvage pathways of purine nucleosides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.21 linamarin + H2O = acetone cyanohydrin + β-D-glucose linamarin degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.6 AMP + H2O = inosine-5'-phosphate + ammonia purine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.6 AMP + H2O = inosine-5'-phosphate + ammonia salvage pathways of purine nucleosides II (plant) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.23 dihydroquercetin + α-ketoglutarate + O2 = quercetin + succinate + CO2 + H2O flavonol biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 indole-3-acetate + L-glutamine = indole-3-acetyl-gln + H2O IAA conjugate biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.19 H2O + (S)-ureidoglycolate = ammonia + CO2 + glyoxylate allantoin degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.2.3 dihydroorotate + H2O = N-carbamoyl-L-aspartate de novo biosynthesis of pyrimidine ribonucleotides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 trans-zeatin riboside monophosphate + H2O = trans-zeatin riboside trans-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.1 canavanine + H2O = L-canaline + urea canavanine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.- 6G,6-kestotetraose + H2O = 6G-kestotriose + fructose fructan degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.3.7 indole acetaldehyde + O2 + H2O = indole-3-acetate + H2O2 IAA biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.2 inosine + H2O = hypoxanthine + D-ribose purine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.2 inosine + H2O = hypoxanthine + D-ribose salvage pathways of purine nucleosides II (plant) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- benzoate + NADPH + O2 = salicylate + NADP+ + H2O salicylate biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.70 lanosterol + NADPH + O2 = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.70 lanosterol + NADPH + O2 = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 nicotine + H2O = nornicotine + formaldehyde nicotine degradation II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.4 4-guanidinobutyramide + H2O = ammonia + 4-guanidinobutyrate arginine degradation X (arginine monooxygenase pathway) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.14 trans-cinnamate + O2 + NADPH = H2O + NADP+ + 2-coumarate coumarin biosynthesis (via 2-coumarate) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.84 3-cyanopyridine + H2O = nicotinamide aldoxime degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.23 histidinal + NAD+ + H2O = L-histidine + NADH histidine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.17.4 L-ascorbate + 1-aminocyclopropane-1-carboxylate + O2 = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.4.1.8 cystathionine + H2O = ammonia + pyruvate + L-homocysteine methionine biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.4.1.8 cystathionine + H2O = ammonia + pyruvate + L-homocysteine methionine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.4.1.8 cystathionine + H2O = ammonia + pyruvate + L-homocysteine homocysteine and cysteine interconversion H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.4 AMP + H2O = D-ribose-5-phosphate + adenine salvage pathways of adenine, hypoxanthine, and their nucleosides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 16-hydroxypalmitate + NADPH + O2 = 10,16-dihydroxypalmitate + NADP+ + H2O cutin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.11.1.11 L-ascorbate + H2O2 = monodehydroascorbate + H2O ascorbate glutathione cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.99.12 trans-zeatin + H2O + FAD = adenine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.9.3.1 O2 = H2O aerobic respiration -- electron donor II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- GA37 + α-ketoglutarate + O2 = GA36 + succinate + CO2 + H2O gibberellin biosynthesis II (early C-3 hydroxylation) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.3.6 H2O + L-arginine = ammonia + citrulline proline biosynthesis V (from arginine) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.3.14 α-ketoglutarate + H2O + acetyl-CoA = homocitrate + coenzyme A lysine biosynthesis IV H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 GDP-D-mannose + H2O = GDP + mannose GDP-mannose metabolism H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*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 H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.2 H2O = coenzyme A acyl-CoA thioesterase pathway H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- leucodelphinidin + O2 + α-ketoglutarate = delphinidin + H2O + CO2 + succinate anthocyanin biosynthesis (delphinidin 3-O-glucoside) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.5 indole-3-glycol aldehyde + H2O + an oxidized acceptor = indole-3-glycolate tryptophan degradation V (side chain pathway) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 5-methylthioribulose-1-phosphate = 2,3-diketo-5-methylthio-1-phosphopentane + H2O methionine salvage pathway H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.4 cellulose biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 CTP = dCTP + H2O de novo biosynthesis of pyrimidine deoxyribonucleotides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*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 H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.90 antheraxanthin + H+ + O2 = violaxanthin + H2O carotenoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.90 antheraxanthin + H+ + O2 = violaxanthin + H2O xanthophyll cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.25 H2O + GTP = diphosphate + 2,5-diamino-6-(ribosylamino)-4-(3H)-pyrimidinone 5'-phosphate + formate flavin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 m-chlorobenzoate + glycine = m-chlorohippurate + H2O bupropion degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.47 H2O + N-acetyl-L,L-2,6-diaminopimelate = L,L-diaminopimelate + acetate lysine biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.21 DIMBOA-Glc + H2O = DIMBOA + β-D-glucose DIMBOA-glucoside degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.36 4-coumaroylquinate + NADPH + O2 = caffeoylquinate + NADP+ + H2O phenylpropanoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.93 (+)-abscisate + NADPH + O2 = 8'-hydroxyabscisate + NADP+ + H2O phaseic acid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 trans-zeatin riboside + H2O = trans-zeatin + D-ribose trans-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.4.- dCDP + H2O = CDP de novo biosynthesis of pyrimidine deoxyribonucleotides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.42 nicotinamide mononucleotide + H2O = ammonia + nicotinate nucleotide NAD salvage pathway I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4α-hydroxymethyl-5α-cholesta-8-en-3β-ol + O2 = 4α-formyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.5 H2O + deoxycytidine = ammonia + deoxyuridine (deoxy)ribose phosphate degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.5 H2O + deoxycytidine = ammonia + deoxyuridine salvage pathways of pyrimidine deoxyribonucleotides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.28 trehalose + H2O = β-D-glucose trehalose degradation II (high osmolarity) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.11.1.9 H2O2 + glutathione = glutathione disulfide + H2O glutathione redox reactions I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 ADP = dADP + H2O purine nucleotides de novo biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.13.12.3 O2 + L-tryptophan = indole-3-acetamide + H2O + CO2 IAA biosynthesis VI (via indole-3-acetamide) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.3.9 acetyl-CoA + H2O + glyoxylate = malate + coenzyme A TCA cycle variation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 indole-3-acetate + L-aspartate = indole-3-acetyl-asp + H2O IAA conjugate biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.1.12 pyrroline-hydroxy-carboxylate + NAD+ + H2O = L-erythro-4-hydroxy-glutamate + NADH 4-hydroxyproline degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- L-tryptophan + NADPH + O2 = indole-3-acetaldoxime + CO2 + NADP+ + H2O IAA biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1-deoxy-capsidiol + O2 + NADPH = capsidiol + H2O + NADP+ capsidiol biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.4 phospholipid biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.4 triacylglycerol biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.3.11 spermine + O2 + H2O = 1-(3-aminopropyl)-4-aminobutanal + 1,3-diaminopropane + H2O2 β-alanine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.3 leucocyanidin + NADPH = 2,3-trans-catechin + NADP+ + H2O proanthocyanidin biosynthesis from flavanols H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.8 nicotine + NADPH + O2 = nicotine-1'-N-oxide + NADP+ + H2O nicotine degradation II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.30 ζ-carotene + O2 = neurosporene + H2O carotenoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- leucopelargonidin + α-ketoglutarate + O2 = pelargonidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- coniferyl aldehyde + NADPH + O2 = 5-hydroxy-coniferaldehyde + NADP+ + H2O phenylpropanoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.2.1.- trans-cinnamate + coenzyme A = (E)-cinnamoyl-CoA + H2O salicylate biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- GA34 + α-ketoglutarate + O2 = GA34-catabolite + succinate + CO2 + H2O gibberellin inactivation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.23 H2O + dUTP = diphosphate + dUMP de novo biosynthesis of pyrimidine deoxyribonucleotides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.9 N-formylkynurenine + H2O = kynurenine + formate tryptophan degradation III (eukaryotic) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.3.1 nicotine-Δ1'5'-iminium ion + O2 + H2O = cotinine + H2O2 nicotine degradation II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.3.1 nicotine-Δ1'5'-iminium ion + O2 + H2O = cotinine + H2O2 nicotine degradation III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 H2O = N5-formyl-THF formylTHF biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 calycosin + NADPH + O2 = pseudobaptigenin + NADP+ + H2O maackiain biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.5 H2O + NAD+ = ADP-ribose + nicotinamide NAD salvage pathway I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- GA51 + α-ketoglutarate + O2 = GA51-catabolite + succinate + CO2 + H2O gibberellin inactivation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.8 betaine aldehyde + NAD+ + H2O = glycine betaine + NADH glycine betaine biosynthesis III (plants) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.52 pyruvate + L-aspartate-semialdehyde = H2O lysine biosynthesis VI H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.52 pyruvate + L-aspartate-semialdehyde = H2O lysine biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.52 pyruvate + L-aspartate-semialdehyde = H2O lysine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.5 H2O + urea = ammonia + CO2 canavanine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.5 H2O + urea = ammonia + CO2 arginine degradation VII (arginase 3 pathway) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.-.- 6-deoxocathasterone + O2 = 6-deoxoteasterone + H2O brassinosteroid biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.79 ent-kaurenoate + O2 + NADPH = ent-7-α-hydroxykaurenoate + H2O + NADP+ GA12 biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 L-glutamate γ-semialdehyde = H2O proline biosynthesis V (from arginine) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 L-glutamate γ-semialdehyde = H2O proline biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 L-glutamate γ-semialdehyde = H2O arginine degradation VI (arginase 2 pathway) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 L-glutamate γ-semialdehyde = H2O arginine degradation I (arginase pathway) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 L-glutamate γ-semialdehyde = H2O proline biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 L-glutamate γ-semialdehyde = H2O citrulline biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate de novo biosynthesis of pyrimidine ribonucleotides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis II (acetyl cycle) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 isopentenyladenosine-5'-diphosphate + NADPH + H2O = trans-zeatin riboside diphosphate + NADP+ trans-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.99.5 H2O = CO2 methanogenesis from CO2 H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.2 NADP+ + H2O = NAD+ NAD salvage pathway II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.5.1 indole-3-acetonitrile + H2O = ammonia + indole-3-acetate IAA biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.1.170 coumaroyl-CoA + malonyl-CoA + NADPH = isoliquiritigenin + coenzyme A + CO2 + NADP+ + H2O flavonoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 O2 + H+ = trimethylamine + D,L-malic semialdehyde + H2O carnitine degradation III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.21 dihydrokaempferol + NADPH + O2 = dihydroquercetin + NADP+ + H2O leucopelargonidin and leucocyanidin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.21 dihydrokaempferol + NADPH + O2 = dihydroquercetin + NADP+ + H2O leucodelphinidin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.21 dihydrokaempferol + NADPH + O2 = dihydroquercetin + NADP+ + H2O flavonol biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.7.1.2 H2O + 4-fumaryl-acetoacetate = fumarate + acetoacetate tyrosine degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.5 nicotinamide mononucleotide + H2O = nicotinamide riboside NAD salvage pathway II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.5 nicotinamide mononucleotide + H2O = nicotinamide riboside pyridine nucleotide cycling (plants) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.11.1.7 betanidin + H2O2 = betanidin + betanidin quinone + H2O betanidin degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.11 fructose-1,6-bisphosphate + H2O = fructose-6-phosphate xylulose-monophosphate cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.11 fructose-1,6-bisphosphate + H2O = fructose-6-phosphate Calvin cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.11 fructose-1,6-bisphosphate + H2O = fructose-6-phosphate gluconeogenesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.11 fructose-1,6-bisphosphate + H2O = fructose-6-phosphate glycolysis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.4.1 dUDP + H2O = UDP de novo biosynthesis of pyrimidine deoxyribonucleotides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 tiglyl-CoA + H2O = 2-methyl-3-hydroxybutyryl-CoA isoleucine degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.23 dihydrokaempferol + α-ketoglutarate + O2 = kaempferol + succinate + CO2 + H2O flavonol biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.4.3.6 1,3-diaminopropane + H2O + O2 = 3-aminopropionaldehyde + ammonia + H2O2 β-alanine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.18 3-hydroxy-3-methyl-glutaryl-CoA = H2O + 3-methylglutaconyl-CoA leucine degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.11 5,10-methylene-THF + 2-keto-isovalerate + H2O = tetrahydrofolate + 2-dehydropantoate pantothenate biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.1.2.11 5,10-methylene-THF + 2-keto-isovalerate + H2O = tetrahydrofolate + 2-dehydropantoate pantothenate biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.3.3.9 O2 + NADPH + loganin = H2O + NADP+ + secologanin secologanin and strictosidine biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 GDP-L-galactose + H2O = L-galactose + GMP ascorbate biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.- indole-3-acetyl-ala + H2O = indole-3-acetate + L-alanine IAA biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.4.4 H2O = choline phospholipases H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.4.4 H2O = choline choline biosynthesis III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.12 trehalose 6-phosphate + H2O = trehalose trehalose biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.3.3.2 tryptamine + secologanin = strictosidine + H2O secologanin and strictosidine biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.84 indole-3-acetonitrile + H2O = indole-3-acetamide IAA biosynthesis IV H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.9 2,3-dihydroxy-isovalerate = 2-keto-isovalerate + H2O valine biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.4.11.2 Cys-Gly + H2O = L-cysteine + glycine γ-glutamyl cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.2.22 fructose-6-phosphate = H2O + D-erythrose-4-phosphate + acetylphosphate glucose fermentation to lactate II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.40 H2O + guanosine 3'-diphosphate 5'-triphosphate = guanosine 5'-diphosphate,3'-diphosphate ppGpp biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4α-methyl-cholesta-8-enol + O2 = 4α-hydroxymethyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.4.11 phospholipases H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.4.1.1 H2O = pyruvate + ammonia glutathione-mediated detoxification H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.- β-cryptoxanthin + O2 = zeaxanthin + H2O carotenoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.7.1.3 3-hydroxy-L-kynurenine + H2O = 3-hydroxy-anthranilate + L-alanine tryptophan degradation III (eukaryotic) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol + O2 + NADPH = 4,4-dimethyl-5-α-cholesta-8,14-dien-3-β-ol + formate + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADP+ + H2O + formate cholesterol biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADP+ + H2O + formate cholesterol biosynthesis III (via desmosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 betaine aldehyde hydrate = betaine aldehyde + H2O glycine betaine biosynthesis III (plants) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.19 D-erythro-imidazole-glycerol-phosphate = imidazole acetol-phosphate + H2O histidine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2,7-dihydroxy-4'-methoxyisoflavanone = formononetin + H2O pterocarpan biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.5 xanthosine-5-phosphate + H2O = xanthosine purine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.5 xanthosine-5-phosphate + H2O = xanthosine ureide biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.5 xanthosine-5-phosphate + H2O = xanthosine salvage pathways of purine nucleosides II (plant) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 7-hydroxy-chlorophyllide a + O2 + NADPH = chlorophyllide b + H2O + NADP+ chlorophyll cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.4.3.5 O2 + H2O + pyridoxamine 5'-phosphate = ammonia + H2O2 + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.- 2,6,7,4'-tetrahydroxyisoflavanone = 6,7,4'-trihydroxyisoflavone + H2O 6,7,4'-trihydroxyisoflavone biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.7.99.6 N2 + H2O = nitrous oxide nitrate reduction I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.23 H2O = 4-hydroxysphinganine sphingolipid metabolism H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.24 sucrose-6-phosphate + H2O = sucrose sucrose biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.11.- leucocyanidin + α-ketoglutarate + O2 = cyanidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol + O2 + NADPH = 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.31 2-aminoadipate-6-semialdehyde + H2O = α-aminoadipate + H+ lysine biosynthesis IV H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 9,10-epoxy-18-hydroxystearate + H2O = 9,10,18-trihydroxystearate cutin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- (5α)-campestan-3-one + O2 + NADPH = (22α)-hydroxy-5α-campestan-3-one + H2O + NADP+ brassinosteroid biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.1 UDP-glucose conversion H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.9 O2 + NADPH + kynurenine = H2O + NADP+ + 3-hydroxy-L-kynurenine tryptophan degradation III (eukaryotic) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH purine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH salvage pathways of purine nucleosides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH ureide biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH salvage pathways of purine nucleosides II (plant) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH purine nucleotides de novo biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.1.1.205 H2O + NAD+ + inosine-5'-phosphate = xanthosine-5-phosphate + NADH purine nucleotides de novo biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.19.2 O2 = H2O stearoyl-ACP desaturation pathway H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.2 H2O = α-maltose starch degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 trans-zeatin riboside triphosphate + H2O = trans-zeatin riboside diphosphate trans-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.5 GMP + H2O = guanosine purine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.5 GMP + H2O = guanosine salvage pathways of purine nucleosides II (plant) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 indole-3-acetate + L-glutamate = indole-3-acetyl-glu + H2O IAA conjugate biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.4.3 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H2O = 2-C-methyl-D-erythritol-2,4-cyclodiphosphate methylerythritol phosphate pathway H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- campestanol + O2 + NADPH = 6-deoxocathasterone + H2O + NADP+ brassinosteroid biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.5 D,L-malic semialdehyde + H2O = malate + H+ carnitine degradation III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.99.1.6 indole-3-acetaldoxime = indole-3-acetonitrile + H2O IAA biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.3.1 O2 + H2O + sarcosine = H2O2 + formaldehyde + glycine glycine betaine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.- β-carotene + O2 = β-cryptoxanthin + H2O carotenoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 isopentenyladenosine-5'-monophosphate + NADPH + H2O = trans-zeatin riboside monophosphate + NADP+ trans-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.- H2O + NADP+ = NAD+ NAD/NADH phosphorylation and dephosphorylation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.19 nicotinamide + H2O = ammonia + nicotinate NAD salvage pathway I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.19 nicotinamide + H2O = ammonia + nicotinate pyridine nucleotide cycling (plants) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 UTP = dUTP + H2O de novo biosynthesis of pyrimidine deoxyribonucleotides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.2.17 5-hydroxyisourate + H2O = 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate ureide biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.4.3.6 aminoacetone + H2O + O2 = ammonia + methylglyoxal + H2O2 threonine degradation III (to methylglyoxal) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.6.1.1 ATP + protoporphyrin IX + Mg2+ + H2O = Mg-protoporphyrin + ADP + H+ chlorophyllide a biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.81 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = divinyl protochlorophyllide a + NADP+ + H2O chlorophyllide a biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 marmesin + NADPH + O2 = psoralen + NADP+ + acetone + H2O linear furanocoumarin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 nornicotine + H2O = norcotinine nicotine degradation II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 very long chain fatty acid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.6 H2O + 3-ureidopropionate = ammonia + CO2 + β-alanine β-alanine biosynthesis III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 ATP = dATP + H2O purine nucleotides de novo biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.80 1-kestotriose + H2O = fructose + sucrose fructan degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 5-epi-aristolochene + O2 + NADPH = 3-deoxy-capsidiol + H2O + NADP+ capsidiol biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.21.6 lathosterol + O2 = 7-dehydro-cholesterol + H2O cholesterol biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.21.6 lathosterol + O2 = 7-dehydro-cholesterol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.31 H2O = glucuronate β-D-glucuronide degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2-hydroxy-3-keto-5-methylthio-1-phosphopentene + H2O = 1,2-dihydroxy-3-keto-5-methylthiopentene methionine salvage pathway H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.4.1.4 L-glutamate + H2O + NADP+ = ammonia + α-ketoglutarate + NADPH proline biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 fatty acid β-oxidation IV (plant, unsaturated, even number) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 fatty acid β-oxidation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 fatty acid β-oxidation II (plant, saturated) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.3 triacylglycerol degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ NAD salvage pathway I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ pyridine nucleotide cycling (plants) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.2.2 H2O + dihydrouracil = 3-ureidopropionate β-alanine biosynthesis III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*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 H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.- N2-succinylglutamate + H2O = L-glutamate + succinate arginine degradation II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 trans-zeatin riboside diphosphate + H2O = trans-zeatin riboside monophosphate trans-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.79 GA12-aldehyde + NADPH + O2 = GA12 + NADP+ + H2O GA12 biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.7.99.7 nitrous oxide + H2O = nitric oxide nitrate reduction I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.78 ent-kaur-16-en-19-ol + NADPH + H+ + O2 = ent-kaur-16-en-19-al + NADP+ + H2O GA12 biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.20 α-maltose + H2O = α-D-glucose starch degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phosphoribosyl 1-pyrophosphate + L-glutamine + H2O purine nucleotides de novo biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phosphoribosyl 1-pyrophosphate + L-glutamine + H2O purine nucleotides de novo biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.15.7 choline + O2 + H+ = betaine aldehyde hydrate + H2O glycine betaine biosynthesis III (plants) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.- E-pyridine-3-aldoxime = 3-cyanopyridine + H2O aldoxime degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.11.1.6 ethanol + H2O2 = H2O + acetaldehyde oxidative ethanol degradation III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- 6,7,4'-trihydroxyflavanone + NADPH + O2 = 2,6,7,4'-tetrahydroxyisoflavanone + NADP+ + H2O 6,7,4'-trihydroxyisoflavone biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.70 24,25-dihydrolanosterol + O2 + NADPH = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + O2 = 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + O2 = 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.14.1 cotinine + NADPH + O2 = 5'-hydroxycotinine + NADP+ + H2O nicotine degradation III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.3.14 abscisic aldehyde + H2O + O2 = (+)-abscisate + H2O2 abscisic acid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.99.12 isopentenyl adenosine + H2O + FAD = adenosine + 3-methyl-2-butenal + FADH2 cytokinins degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 isopentenyladenosine-5'-triphosphate + H2O = isopentenyladenosine-5'-diphosphate trans-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4α-formyl-5α-cholesta-8-en-3β-ol + O2 = 4α-carboxy-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 methylacrylyl-CoA + H2O = 3-hydroxy-isobutyryl-CoA valine degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.-.-.- O2 = H2O aerobic respiration -- electron donor III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.3.3.4 protoporphyrinogen IX + O2 = protoporphyrin IX + H2O heme biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.3.3.4 protoporphyrinogen IX + O2 = protoporphyrin IX + H2O chlorophyllide a biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.5.1.61 H2O + porphobilinogen = ammonia + hydroxymethylbilane tetrapyrrole biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.52 formononetin + NADPH + O2 = calycosin + NADP+ + H2O maackiain biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.1.2 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H+ = dimethylallyl-PP + H2O methylerythritol phosphate pathway H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.13 H2O + dCTP = ammonia + dUTP de novo biosynthesis of pyrimidine deoxyribonucleotides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.16 succinate semialdehyde + NADP+ + H2O = NADPH + succinate TCA cycle variation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.4 nicotinamide + H2O = ammonia + nicotinate aldoxime degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 isopentenyl adenosine + H2O = trans-zeatin riboside + H+ trans-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.99.12 cis-zeatin + H2O + FAD = 3-methyl-4-cis-hydroxy-2-butenal + adenine + FADH2 cytokinins degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 13-HPOD = etheroleate + H2O divinyl ether biosynthesis II (13-LOX) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.13.99.1 O2 + myo-inositol = H2O + glucuronate UDP-D-glucuronate biosynthesis (from myo-inositol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.1 guanosine + H2O = guanine + D-ribose purine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.1 guanosine + H2O = guanine + D-ribose salvage pathways of purine nucleosides II (plant) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 GTP = dGTP + H2O purine nucleotides de novo biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.1.9 H2O + NAD+ + saccharopine = L-glutamate + NADH + 2-aminoadipate-6-semialdehyde lysine degradation II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.3 TCA cycle variation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.3 reductive TCA cycle I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.3 respiration (anaerobic) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.3 TCA cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = citrate + coenzyme A TCA cycle variation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = citrate + coenzyme A respiration (anaerobic) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = citrate + coenzyme A TCA cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.4.1.1 cystathionine + H2O = ammonia + 2-oxobutanoate + L-cysteine homocysteine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.4.1.1 cystathionine + H2O = ammonia + 2-oxobutanoate + L-cysteine homocysteine and cysteine interconversion H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.13.1.1 sulfite + UDP-D-glucose = UDP-sulfoquinovose + H2O glycolipid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 tryptamine + O2 + NADPH = N-hydroxyl-tryptamine + H2O + NADP+ IAA biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.16 GTP + H2O = formate + 7,8-dihydroneopterin 3'-triphosphate tetrahydrofolate biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.16 GTP + H2O = formate + 7,8-dihydroneopterin 3'-triphosphate tetrahydrofolate biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3-sulfinyl-pyruvate + H2O = sulfite + pyruvate L-cysteine degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.18 H2O + 2-phosphoglycolate = glycolate photorespiration H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 GA12 + O2 = GA53 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.105 2-hydroxyisoflavanone = daidzein + H2O pterocarpan biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.- H2O = 2-monoacylglycerol triacylglycerol degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.9.1.1 selenophosphate = H2O selenocysteine biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 3-hydroxybutyryl-CoA = crotonyl-CoA + H2O gallate degradation III (anaerobic) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4-aminobutanal = 1-pyrroline + H2O β-alanine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.3.13 2-keto-isovalerate + acetyl-CoA + H2O = 2-isopropylmalate + coenzyme A leucine biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.84 acrylonitrile + H2O = acrylamide acrylonitrile degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.4.1 dCDP + H2O = CDP de novo biosynthesis of pyrimidine deoxyribonucleotides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.1 H2O + cytosine = ammonia + uracil salvage pathways of pyrimidine ribonucleotides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- campesterol + O2 + NADPH = (22α)-hydroxy-campesterol + H2O + NADP+ brassinosteroid biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*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 from threonine H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.90 zeaxanthin + H+ + O2 = antheraxanthin + H2O carotenoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.90 zeaxanthin + H+ + O2 = antheraxanthin + H2O xanthophyll cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.36 homocitrate = H2O + 3-carboxyhex-2-enedioate lysine biosynthesis IV H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.10 H2O + N10-formyl-THF = tetrahydrofolate + formate folate transformations H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.10 H2O + N10-formyl-THF = tetrahydrofolate + formate formylTHF biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 7-hydroxy-chlorophyll a + H2O + NADP+ = chlorophyll a + O2 + NADPH chlorophyll cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.78 ent-kaur-16-en-19-al + NADPH + H+ + O2 = ent-kaurenoate + NADP+ + H2O GA12 biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.89 genistein + NADPH + O2 = 2'-hydroxygenistein + NADP+ + H2O wighteone and luteone biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.23 H2O + 1-monoacylglycerol = glycerol triacylglycerol degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 indole-3-acetate + L-alanine = indole-3-acetyl-ala + H2O IAA conjugate biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 6.3.4.16 ammonia + H2O + CO2 + ATP = carbamoyl-phosphate + ADP urea cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.4.1.11 L-methionine + H2O = methanethiol + ammonia + 2-oxobutanoate methionine degradation II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.72 D-erythrose-4-phosphate + NAD+ + H2O = erythronate-4-phosphate + NADH + H+ pyridoxal 5'-phosphate biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.4 H2O = linolenate jasmonic acid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.55 3-hydroxybutyryl-CoA = H2O + crotonyl-CoA acetyl CoA fermentation to butyrate H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.55 3-hydroxybutyryl-CoA = H2O + crotonyl-CoA glutaryl-CoA degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.55 3-hydroxybutyryl-CoA = H2O + crotonyl-CoA ethanol fermentation to acetate H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.27 phospholipid biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.27 phospholipid biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.27 cardiolipin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.79 ent-7-α-hydroxykaurenoate + NADPH + H+ + O2 = GA12-aldehyde + NADP+ + H2O GA12 biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.- N2-succinyl-L-glutamate 5-semialdehyde + NAD+ + H2O = N2-succinylglutamate + NADH arginine degradation II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.16 5'-methylthioadenosine + H2O = 5-methylthioribose + adenine methionine salvage pathway H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.26 H2O + sucrose-6-phosphate = β-D-glucose-6-phosphate + fructose sucrose degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.3.- 2-oxo-4-methylthiobutanoate + acetyl-CoA + H2O = 2-(2'-methylthio)ethylmalic-acid + coenzyme A homomethionine biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.3.- geranyl-PP + H2O = (-)-α-terpineol + diphosphate monoterpene biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.4 phospholipases H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 18-hydroxyoleate + NADPH + O2 = 9,10-epoxy-18-hydroxystearate + NADP+ + H2O cutin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.81 Mg-protoporphyrin monomethyl ester + NADPH + H+ + O2 = 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.9 tetrahydrofolate biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.7.9.2 H2O + pyruvate + ATP = phosphoenolpyruvate + AMP reductive TCA cycle I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.7.9.2 H2O + pyruvate + ATP = phosphoenolpyruvate + AMP gluconeogenesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.7.9.2 H2O + pyruvate + ATP = phosphoenolpyruvate + AMP glycolysis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 cis-zeatin riboside monophosphate + H2O = cis-zeatin riboside cis-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 chlorophyllide a + O2 + NADPH = 7-hydroxy-chlorophyllide a + H2O + NADP+ chlorophyll cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.1.21 coumarinic acid-β-D-glucoside + H2O = coumarinate + β-D-glucose coumarin biosynthesis (via 2-coumarate) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.24 H2O + NAD+ + succinate semialdehyde = NADH + succinate glutamate degradation III H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.3.2.1 H2O + isochorismate = pyruvate + 2,3-dihydro-2,3-dihydroxybenzoate enterobactin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*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 H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 UDP-3-O-(3-hydroxymyristoyl)-N-acetylglucosamine + H2O = UDP-3-O-(3-hydroxymyristoyl)glucosamine + acetate lipid-A-precursor biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.78 ent-kaur-16-ene + O2 + NADPH = H2O + NADP+ + ent-kaur-16-en-19-ol GA12 biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4α-formyl-4β-methyl-5α-cholesta-8-en-3β-ol + O2 = 4α-carboxy-4β-methyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.21.6 5α-cholesta-7,24-dien-3β-ol + O2 = 7-dehydrodesmosterol + H2O cholesterol biosynthesis III (via desmosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.99.2 dimethylglycine + H2O = formaldehyde + sarcosine glycine betaine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.14.1 nicotine + NADPH + O2 = 2'-hydroxynicotine + NADP+ + H2O nicotine degradation II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.1.14 chlorophyll a + H2O = chlorophyllide a + phytol chlorophyll a degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 cis-zeatin riboside + H2O = cis-zeatin + D-ribose cis-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.- indole-3-acetyl-leu + H2O = indole-3-acetate + L-leucine IAA biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.- campest-4-en-3-one + O2 + NADPH = (22α)-hydroxy-campest-4-en-3-one + H2O + NADP+ brassinosteroid biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.12 S-formylglutathione + H2O = formate + glutathione formaldehyde oxidation II (glutathione-dependent) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.4.1 dGDP + H2O = GDP purine nucleotides de novo biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.3.1.89 acetyl-CoA + tetrahydrodipicolinate + H2O = coenzyme A + L-2-acetamido-6-oxoheptanedioate lysine biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.4.- UDP = dUDP + H2O de novo biosynthesis of pyrimidine deoxyribonucleotides H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.2.2.1 nicotinamide riboside + H2O = nicotinamide + D-ribose pyridine nucleotide cycling (plants) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.53 pseudobaptigenin + NADPH + O2 = 2'-hydroxypseudobaptigenin + NADP+ + H2O maackiain biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.7 O2 + squalene = (S)-2,3-Epoxysqualene + H2O sterol biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.4 anandamide + H2O = arachidonate + ethanolamine anandamide degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.4 3-hydroxypropionyl-CoA + H2O = 3-hydroxy-propionate + coenzyme A β-alanine biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.9 D-glyceraldehyde-3-phosphate + NADP+ + H2O = 3-phosphoglycerate + NADPH glycolysis IV (plant cytosol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.22 H2O + NAD+ = nicotinamide mononucleotide + AMP NAD salvage pathway II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.22 H2O + NAD+ = nicotinamide mononucleotide + AMP NAD salvage pathway I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.22 H2O + NAD+ = nicotinamide mononucleotide + AMP pyridine nucleotide cycling (plants) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 diprenylphlorisobutyrophenone + O2 = cohumulone + H2O cohumulone biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.- ε-carotene + O2 = ε,ε-carotene-3-diol + H2O lactucaxanthin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.2.1.21 H2O + NAD+ + glycolaldehyde = NADH + glycolate ethylene glycol degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.47 GDP-D-mannose = H2O + GDP-4-dehydro-6-deoxy-D-mannose GDP-D-rhamnose biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.47 GDP-D-mannose = H2O + GDP-4-dehydro-6-deoxy-D-mannose GDP-L-fucose biosynthesis I (from GDP-D-mannose) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.17.4.1 dADP + H2O = ADP purine nucleotides de novo biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.1.1.39 CO2 + H2O = 3-phosphoglycerate + H+ Calvin cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.- ε,ε-carotene-3-diol + O2 = lactucaxanthin + H2O lactucaxanthin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 fatty acid elongation -- unsaturated II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 2.6.99.2 1-deoxy-D-xylulose 5-phosphate + 1-amino-propan-2-one-3-phosphate = pyridoxine-5'-phosphate + H2O pyridoxal 5'-phosphate biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.74 O2 + NADPH + 7-deoxyloganin = H2O + NADP+ + loganin secologanin and strictosidine biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 5-epi-aristolochene + O2 + NADPH = 1-deoxy-capsidiol + H2O + NADP+ capsidiol biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.4.11.2 [Cys-Gly]-S-conjugate + H2O = glycine glutathione-mediated detoxification H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 isopentenyl adenosine + H2O = isopentenyladenine + D-ribose trans-zeatin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 (+)-pulegone + NADPH + O2 = (+)-menthofuran + NADP+ + H2O menthol biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.5.99.6 H2O + spermidine = 4-aminobutanal + 1,3-diaminopropane β-alanine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.5.7 acrylonitrile + H2O = acrylate + ammonia acrylonitrile degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.20 citrulline + H2O = L-ornithine + CO2 + ammonia proline biosynthesis V (from arginine) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.2.6 S-lactoyl-glutathione + H2O = glutathione + D-lactate methylglyoxal degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4-coumarate + NADPH + O2 = H2O + caffeate + NADP+ suberin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4-coumarate + NADPH + O2 = H2O + caffeate + NADP+ free phenylpropanoid acid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.17 fatty acid β-oxidation IV (plant, unsaturated, even number) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.99.- phytofluene + O2 = ζ-carotene + H2O carotenoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 H2O = H+ + e- + O2 photosynthesis, light reaction H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.46 dTDP-D-glucose = H2O + dTDP-4-dehydro-6-deoxy-D-glucose dTDP-L-rhamnose biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.10 inosine-5'-phosphate + H2O = phosphoribosyl-formamido-carboxamide purine nucleotides de novo biosynthesis II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.10 inosine-5'-phosphate + H2O = phosphoribosyl-formamido-carboxamide purine nucleotides de novo biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.-.-.- pheophorbide a + O2 = RCC + H2O chlorophyll a degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.36 4-coumaroylshikimate + NADPH + O2 = caffeoylshikimate + NADP+ + H2O phenylpropanoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.1.3.75 phosphoryl-choline + H2O = choline choline biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.6.1.31 phosphoribosyl-ATP + H2O = phosphoribosyl-AMP + diphosphate histidine biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.1 L-asparagine + H2O = ammonia + L-aspartate asparagine degradation I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.1.1 L-asparagine + H2O = ammonia + L-aspartate asparagine degradation II H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3-dehydro-shikimate = H2O quinate degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.81 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 4.2.1.24 5-amino-levulinate = H2O + porphobilinogen tetrapyrrole biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 psoralen + NADPH + H2O = bergaptol + NADP+ linear furanocoumarin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione + 3,4-dihydroxy-2-butanone-4-P = 6,7-dimethyl-8-(1-D-ribityl)lumazine + H2O flavin biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.10.99.3 violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O carotenoid biosynthesis H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.10.99.3 violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.15 H2O + guanosine = ammonia + xanthosine purine degradation H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 3.5.4.15 H2O + guanosine = ammonia + xanthosine salvage pathways of purine nucleosides II (plant) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.7.7.- nitrite = ammonia + H2O nitrate reduction II (assimilatory) H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4-α-methyl zymosterol + O2 = 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I H2O H20*hydrogen oxide*water 18.015 H2 O1 [OH2] CHEBI:15377*LIGAND-CPD:C00001*PUBCHEM:962*LIGAND-CPD:C00001:*CAS:7732-18-5 1.14.13.72 4-α-methyl zymosterol + O2 = 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) kinetin-9-N-glucoside 377.356 C16 H19 N5 O6 c1(c2(c(ncn1)N(C=N2)C3(OC(CO)C(O)C(O)C(O)3)))(NCc4(occc4)) 2.4.1.- kinetin + UDP-D-glucose = kinetin-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis oryzalexin F 304.472 C20 H32 O2 C=CC1(C)(C=C2(C(CC1)C3(C)([CH](CC2)C(CO)(C)C(O)CC3))) ent-sandaracopimaradiene-3α-ol = oryzalexin F oryzalexin A-F biosynthesis 13-HPOD (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate*13(S)-hydroperoxyoctadeca-9,11-dienoate 312.448 C18 H32 O4 CCCCCC(OO)C=CC=CCCCCCCCC(O)=O 1.13.11.12 linoleate + O2 = 13-HPOD 13-LOX and 13-HPL pathway 13-HPOD (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate*13(S)-hydroperoxyoctadeca-9,11-dienoate 312.448 C18 H32 O4 CCCCCC(OO)C=CC=CCCCCCCCC(O)=O 1.13.11.12 linoleate + O2 = 13-HPOD divinyl ether biosynthesis II (13-LOX) 13-HPOD (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate*13(S)-hydroperoxyoctadeca-9,11-dienoate 312.448 C18 H32 O4 CCCCCC(OO)C=CC=CCCCCCCCC(O)=O 13-HPOD = etheroleate + H2O divinyl ether biosynthesis II (13-LOX) 13-HPOD (9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate*13(S)-hydroperoxyoctadeca-9,11-dienoate 312.448 C18 H32 O4 CCCCCC(OO)C=CC=CCCCCCCCC(O)=O 13-HPOD = 12-oxo-cis-9-dodecenoate + hexanal 13-LOX and 13-HPL pathway deoxyinosine 2-deoxyinosine 252.229 C10 H12 N4 O4 c1(=O)(c2(c(nc[nH]1)n(cn2)[CH]3(O[CH]([CH]([CH2]3)O)CO))) CAS:890-38-0:*LIGAND-CPD:C05512: deoxyinosine = hypoxanthine + deoxyribose-1-phosphate salvage pathways of adenine, hypoxanthine, and their nucleosides deoxyinosine 2-deoxyinosine 252.229 C10 H12 N4 O4 c1(=O)(c2(c(nc[nH]1)n(cn2)[CH]3(O[CH]([CH]([CH2]3)O)CO))) CAS:890-38-0:*LIGAND-CPD:C05512: H2O + deoxyadenosine = ammonia + deoxyinosine salvage pathways of adenine, hypoxanthine, and their nucleosides 4-amino-4-deoxychorismate 225.201 C10 H11 N1 O5 C=C(C(O)=O)OC1(C(N)C=CC(=C1)C(O)=O) LIGAND-CPD:C11355:*CAS:97279-79-3 6.3.5.8 L-glutamine + chorismate = L-glutamate + 4-amino-4-deoxychorismate tetrahydrofolate biosynthesis I 4-amino-4-deoxychorismate 225.201 C10 H11 N1 O5 C=C(C(O)=O)OC1(C(N)C=CC(=C1)C(O)=O) LIGAND-CPD:C11355:*CAS:97279-79-3 6.3.5.8 L-glutamine + chorismate = L-glutamate + 4-amino-4-deoxychorismate tetrahydrofolate biosynthesis II 4-amino-4-deoxychorismate 225.201 C10 H11 N1 O5 C=C(C(O)=O)OC1(C(N)C=CC(=C1)C(O)=O) LIGAND-CPD:C11355:*CAS:97279-79-3 4.1.3.38 4-amino-4-deoxychorismate = p-aminobenzoate + pyruvate tetrahydrofolate biosynthesis I 4-amino-4-deoxychorismate 225.201 C10 H11 N1 O5 C=C(C(O)=O)OC1(C(N)C=CC(=C1)C(O)=O) LIGAND-CPD:C11355:*CAS:97279-79-3 4.1.3.38 4-amino-4-deoxychorismate = p-aminobenzoate + pyruvate tetrahydrofolate biosynthesis II β-cryptoxanthin β,β-carotene-3-ol 552.882 C40 H56 O1 CC(C=CC1(=C(C)CC(O)CC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)(C)CCCC(C)=2) 1.14.99.- β-cryptoxanthin + O2 = zeaxanthin + H2O carotenoid biosynthesis β-cryptoxanthin β,β-carotene-3-ol 552.882 C40 H56 O1 CC(C=CC1(=C(C)CC(O)CC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)(C)CCCC(C)=2) 1.14.99.- β-carotene + O2 = β-cryptoxanthin + H2O carotenoid biosynthesis 4-oxo-4-(3-pyridyl)-N-methylbutanamide 4-(3-pyridyl)-4-oxo-N-methylbutyramide*γ-(3-pyridyl)-γ-oxo-N-methylbutyramide 192.217 C10 H12 N2 O2 c1(ncc(cc1)C(=O)CCC(=O)NC) 4-oxo-4-(3-pyridyl)-N-methylbutanamide = 4-oxo-4-(3-pyridyl)-butanoate nicotine degradation III 4-oxo-4-(3-pyridyl)-N-methylbutanamide 4-(3-pyridyl)-4-oxo-N-methylbutyramide*γ-(3-pyridyl)-γ-oxo-N-methylbutyramide 192.217 C10 H12 N2 O2 c1(ncc(cc1)C(=O)CCC(=O)NC) 5'-hydroxycotinine = 4-oxo-4-(3-pyridyl)-N-methylbutanamide nicotine degradation III 4,4-dimethyl-5α-cholesta-8-en-3-β-ol 414.713 C29 H50 O1 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(C)(C)C(O)CC4)(C)))(C)) 1.3.1.70 4,4-dimethyl-5-α-cholesta-8,14-dien-3-β-ol + NADPH = 4,4-dimethyl-5α-cholesta-8-en-3-β-ol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 4,4-dimethyl-5α-cholesta-8-en-3-β-ol 414.713 C29 H50 O1 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(C)(C)C(O)CC4)(C)))(C)) 1.14.13.72 4,4-dimethyl-5α-cholesta-8-en-3-β-ol + O2 = 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) NO3- NO3*nitrate 62.005 N1 O3 [N+]([O-])([O-])=O LIGAND-CPD:C00244:*CAS:14797-55-8 1.7.99.4 nitrite = NO3- nitrate reduction I coumaryl-alcohol 150.177 C9 H10 O2 C(O)C=Cc1(ccc(O)cc1) 1.1.1.195 coumaraldehyde + NADPH = coumaryl-alcohol + NADP+ phenylpropanoid biosynthesis cyanidin 287.248 C15 H11 O6 C3(=C(O)C(c1(ccc(O)c(c1)O))=Oc2(cc(O)cc(c23)O)) 1.14.11.- leucocyanidin + α-ketoglutarate + O2 = cyanidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) cyanidin 287.248 C15 H11 O6 C3(=C(O)C(c1(ccc(O)c(c1)O))=Oc2(cc(O)cc(c23)O)) 2.4.1.115 UDP-D-glucose + cyanidin = UDP + cyanidin-3-O-β-D-glucoside anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) O-succinyl-L-homoserine O-succinyl-homoserine*o-succinyl-L-homoserine*succinyl-homoserine 219.194 C8 H13 N1 O6 C(=O)(O)C(N)CCOC(=O)CCC(=O)O LIGAND-CPD:C01118:*CAS:1492-23-5 2.3.1.46 homoserine + succinyl-CoA = O-succinyl-L-homoserine + coenzyme A methionine biosynthesis I O-succinyl-L-homoserine O-succinyl-homoserine*o-succinyl-L-homoserine*succinyl-homoserine 219.194 C8 H13 N1 O6 C(=O)(O)C(N)CCOC(=O)CCC(=O)O LIGAND-CPD:C01118:*CAS:1492-23-5 2.5.1.48 L-cysteine + O-succinyl-L-homoserine = succinate + cystathionine methionine biosynthesis I dCDP 2'-deoxycytidine diphosphate*2'-deoxycytidine-5'-diphosphate*deoxycytidine-diphosphate 387.179 C9 H15 N3 O10 P2 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C2)COP(O)(=O)OP(O)(O)=O)) LIGAND-CPD:C00705:*CAS:800-73-7 1.17.4.- dCDP + H2O = CDP de novo biosynthesis of pyrimidine deoxyribonucleotides dCDP 2'-deoxycytidine diphosphate*2'-deoxycytidine-5'-diphosphate*deoxycytidine-diphosphate 387.179 C9 H15 N3 O10 P2 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C2)COP(O)(=O)OP(O)(O)=O)) LIGAND-CPD:C00705:*CAS:800-73-7 1.17.4.1 dCDP + H2O = CDP de novo biosynthesis of pyrimidine deoxyribonucleotides dCDP 2'-deoxycytidine diphosphate*2'-deoxycytidine-5'-diphosphate*deoxycytidine-diphosphate 387.179 C9 H15 N3 O10 P2 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C2)COP(O)(=O)OP(O)(O)=O)) LIGAND-CPD:C00705:*CAS:800-73-7 2.7.4.6 dCDP + ATP = dCTP + ADP de novo biosynthesis of pyrimidine deoxyribonucleotides OH- hydroxyl*hydroxyl ion*OH*hydroxide*hydroxide ion 17.007 H1 O1 [OH-] CAS:14280-30-9 3.7.1.- dihydrophloroglucinol + OH- = 3-hydroxy-5-oxohexanoate gallate degradation III (anaerobic) ζ-carotene 540.914 C40 H60 CC(C)=CCCC(C)=CCCC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)CCC=C(C)CCC=C(C)C 1.14.99.- phytofluene + O2 = ζ-carotene + H2O carotenoid biosynthesis ζ-carotene 540.914 C40 H60 CC(C)=CCCC(C)=CCCC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)CCC=C(C)CCC=C(C)C 1.14.99.30 ζ-carotene + O2 = neurosporene + H2O carotenoid biosynthesis 3,4-dihydroxy-2-butanone-4-P 3,4-dihydroxy-2-butanone-4-phosphate*tetrolose phosphate 184.085 C4 H9 O6 P1 CC(=O)C(O)COP(O)(O)=O 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione + 3,4-dihydroxy-2-butanone-4-P = 6,7-dimethyl-8-(1-D-ribityl)lumazine + H2O flavin biosynthesis 3,4-dihydroxy-2-butanone-4-P 3,4-dihydroxy-2-butanone-4-phosphate*tetrolose phosphate 184.085 C4 H9 O6 P1 CC(=O)C(O)COP(O)(O)=O D-ribulose-5-phosphate = 3,4-dihydroxy-2-butanone-4-P + formate flavin biosynthesis acrylamide 71.079 C3 H5 N1 O1 C(=O)(N)C=C NCI:7785 3.5.1.4 acrylamide + H2O = ammonia + acrylate + H+ acrylonitrile degradation acrylamide 71.079 C3 H5 N1 O1 C(=O)(N)C=C NCI:7785 4.2.1.84 acrylonitrile + H2O = acrylamide acrylonitrile degradation indole-3-glycolate 191.186 C10 H9 N1 O3 c1(c(C(O)C(O)=O)c2(c([nH]1)cccc2)) 1.2.1.5 indole-3-glycol aldehyde + H2O + an oxidized acceptor = indole-3-glycolate tryptophan degradation V (side chain pathway) indole-3-glycolate 191.186 C10 H9 N1 O3 c1(c(C(O)C(O)=O)c2(c([nH]1)cccc2)) 1.13.99.3 indole-3-glycolate = indole-3-glyoxylate tryptophan degradation V (side chain pathway) indole-3-glycolate 191.186 C10 H9 N1 O3 c1(c(C(O)C(O)=O)c2(c([nH]1)cccc2)) 1.13.99.3 indole-3-acetate + O2 = indole-3-glycolate tryptophan degradation V (side chain pathway) CDP cytidine-diphosphate*cytidine-5'-diphosphate 403.179 C9 H15 N3 O11 P2 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)OP(O)(=O)O)) LIGAND-CPD:C00112:*CAS:63-38-7 2.7.4.6 CDP + ATP = CTP + ADP de novo biosynthesis of pyrimidine ribonucleotides CDP cytidine-diphosphate*cytidine-5'-diphosphate 403.179 C9 H15 N3 O11 P2 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)OP(O)(=O)O)) 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 403.179 C9 H15 N3 O11 P2 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)OP(O)(=O)O)) LIGAND-CPD:C00112:*CAS:63-38-7 1.17.4.- dCDP + H2O = CDP de novo biosynthesis of pyrimidine deoxyribonucleotides CDP cytidine-diphosphate*cytidine-5'-diphosphate 403.179 C9 H15 N3 O11 P2 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)OP(O)(=O)O)) LIGAND-CPD:C00112:*CAS:63-38-7 1.17.4.1 dCDP + H2O = CDP de novo biosynthesis of pyrimidine deoxyribonucleotides CDP cytidine-diphosphate*cytidine-5'-diphosphate 403.179 C9 H15 N3 O11 P2 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)OP(O)(=O)O)) LIGAND-CPD:C00112:*CAS:63-38-7 2.7.4.14 ATP + CMP = ADP + CDP salvage pathways of purine and pyrimidine nucleotides CDP cytidine-diphosphate*cytidine-5'-diphosphate 403.179 C9 H15 N3 O11 P2 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)OP(O)(=O)O)) LIGAND-CPD:C00112:*CAS:63-38-7 2.7.4.14 ATP + CMP = ADP + CDP salvage pathways of pyrimidine ribonucleotides CDP cytidine-diphosphate*cytidine-5'-diphosphate 403.179 C9 H15 N3 O11 P2 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)OP(O)(=O)O)) LIGAND-CPD:C00112:*CAS:63-38-7 2.7.1.108 dolichol + CTP = dolichyl-phosphate + CDP dolichyl-diphosphooligosaccharide biosynthesis trimethyl sulfonium 77.164 C3 H9 S1 C[S+](C)C CAS:2181-42-2 2.1.1.19 tetrahydrofolate + trimethyl sulfonium = dimethylsulfide + 5-methyl-THF folate transformations 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 473.444 C20 H23 N7 O7 C([CH]1(N(C=O)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) CAS:58-05-9 H2O = N5-formyl-THF formylTHF biosynthesis II 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 473.444 C20 H23 N7 O7 C([CH]1(N(C=O)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) CAS:58-05-9 6.3.3.2 N5-formyl-THF + ATP = ADP folate transformations 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 473.444 C20 H23 N7 O7 C([CH]1(N(C=O)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) CAS:58-05-9 6.3.3.2 N5-formyl-THF + ATP = ADP formylTHF biosynthesis II 18:2-18:1-PC 1-18:2-2-18:1-phosphatidylcholine 785.115 C44 H83 N1 O8 P1 C(OP(=O)(O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-18:1-PC = 18:2-18:2-PC phospholipid desaturation 18:2-18:1-PC 1-18:2-2-18:1-phosphatidylcholine 785.115 C44 H83 N1 O8 P1 C(OP(=O)(O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-18:1-PC = 18:3-18:1-PC phospholipid desaturation 18:2-18:1-PC 1-18:2-2-18:1-phosphatidylcholine 785.115 C44 H83 N1 O8 P1 C(OP(=O)(O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:1-18:1-PC = 18:2-18:1-PC phospholipid desaturation 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate HMBDP*(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate 262.093 C5 H12 O8 P2 CC(CO)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C11811: 1.17.1.2 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H+ = dimethylallyl-PP + H2O methylerythritol phosphate pathway 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate HMBDP*(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate 262.093 C5 H12 O8 P2 CC(CO)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C11811: 1.17.1.2 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H+ = H2O methylerythritol phosphate pathway 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate HMBDP*(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate 262.093 C5 H12 O8 P2 CC(CO)=CCOP(=O)(O)OP(=O)(O)O LIGAND-CPD:C11811: 1.17.4.3 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 294.433 C18 H30 O3 CCCCC=COC=CC=CCCCCCCCC(=O)O 13-HPOD = etheroleate + H2O divinyl ether biosynthesis II (13-LOX) 3-methylglutaconyl-CoA trans-3-methylglutaconyl-CoA 893.646 C27 H42 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(=O)O)COP(=O)(O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=C(C)CC(O)=O) 6.4.1.4 ATP + 3-methylcrotonyl-CoA + HCO3- = ADP + 3-methylglutaconyl-CoA leucine degradation I 3-methylglutaconyl-CoA trans-3-methylglutaconyl-CoA 893.646 C27 H42 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(=O)O)COP(=O)(O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=C(C)CC(O)=O) 4.2.1.18 3-hydroxy-3-methyl-glutaryl-CoA = H2O + 3-methylglutaconyl-CoA leucine degradation I indole-3-acetyl-leu indole-3-acetyl-leucine 288.346 C16 H20 N2 O3 C(=O)(NC(C(O)=O)CC(C)C)Cc2(c[nH]c1(ccccc12)) 3.5.1.- indole-3-acetyl-leu + H2O = indole-3-acetate + L-leucine IAA biosynthesis II indole-3-acetyl-leu indole-3-acetyl-leucine 288.346 C16 H20 N2 O3 C(=O)(NC(C(O)=O)CC(C)C)Cc2(c[nH]c1(ccccc12)) indole-3-acetate + L-leucine = indole-3-acetyl-leu + H2O IAA conjugate biosynthesis II phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.9.2 H2O + pyruvate + ATP = phosphoenolpyruvate + AMP reductive TCA cycle I phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.9.2 H2O + pyruvate + ATP = phosphoenolpyruvate + AMP gluconeogenesis phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.9.2 H2O + pyruvate + ATP = phosphoenolpyruvate + AMP glycolysis I phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*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-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O gluconeogenesis phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O sucrose degradation to ethanol and lactate (anaerobic) phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O respiration (anaerobic) phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O glycolysis IV (plant cytosol) phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O fructose degradation to pyruvate and lactate (anaerobic) phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O glucose fermentation to lactate II phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O glycolysis I phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.1.1.49 oxaloacetate + ATP = CO2 + phosphoenolpyruvate + ADP gluconeogenesis phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.5.1.7 UDP-N-acetyl-D-glucosamine + phosphoenolpyruvate = UDP-GlcNAc-enolpyruvate peptidoglycan biosynthesis I phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate mixed acid fermentation phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate sucrose degradation to ethanol and lactate (anaerobic) phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate respiration (anaerobic) phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate glycolysis IV (plant cytosol) phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate fructose degradation to pyruvate and lactate (anaerobic) phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate glucose fermentation to lactate II phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate glycolysis I phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*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 phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.1.1.32 oxaloacetate + GTP = CO2 + phosphoenolpyruvate + GDP asparagine degradation I phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 mixed acid fermentation phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 reductive TCA cycle I phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 gluconeogenesis phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 respiration (anaerobic) phosphoenolpyruvate P-enol-pyruvate*P-enol-pyr*PEP 168.043 C3 H5 O6 P1 C=C(C(=O)O)OP(O)(=O)O CAS:73-89-2*LIGAND-CPD:c00074:*CAS:138-08-9:*LIGAND-CPD:C00074: 2.5.1.19 shikimate-3-phosphate + phosphoenolpyruvate = 5-enolpyruvyl-shikimate-3-phosphate chorismate biosynthesis 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(c(CO)c(N)nc(C)n1) LIGAND-CPD:C01279:*CAS:73-67-6: 2.7.1.49 ATP + hydroxymethylpyrimidine = ADP + hydroxymethylpyrimidine phosphate thiamine biosynthesis 2-methylbutanal 2-methylbutyraldehyde 86.133 C5 H10 O1 CCC(C)[CH]=O CAS:96-17-3 4.1.1.72 2-keto-3-methyl-valerate = 2-methylbutanal + CO2 isoleucine degradation II 2-methylbutanal 2-methylbutyraldehyde 86.133 C5 H10 O1 CCC(C)[CH]=O CAS:96-17-3 1.1.1.1 2-methylbutanal + NADH = 2-methylbutanol + NAD+ isoleucine degradation II β-L-arabinose 1-phosphate β-L-arabinose 1-P 230.111 C5 H11 O8 P1 C1(OC(OP(O)(=O)O)C(O)C(O)C(O)1) 2.7.7.37 β-L-arabinose 1-phosphate + UTP = UDP-L-arabinose + diphosphate UDP-L-arabinose biosynthesis II (from L-arabinose) β-L-arabinose 1-phosphate β-L-arabinose 1-P 230.111 C5 H11 O8 P1 C1(OC(OP(O)(=O)O)C(O)C(O)C(O)1) 2.7.1.46 ATP = β-L-arabinose 1-phosphate + ADP UDP-L-arabinose biosynthesis II (from L-arabinose) 18:3-18:3-MGDG 1-18:3-2-18:3-monogalactosyldiacylglycerol*1,2-(9Z,12Z,15Z-octadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerol 791.073 C45 H74 O11 C(OC1(C(O)C(O)C(OO)C(O1)CO))C(OC(=O)CCCCCCCC=CCC=CCC=CCC)COC(=O)CCCCCCCC=CCC=CCC=CCC PUBCHEM:5771744: 1.14.99.- 18:3-18:2-MGDG = 18:3-18:3-MGDG glycolipid desaturation 18:3-18:3-MGDG 1-18:3-2-18:3-monogalactosyldiacylglycerol*1,2-(9Z,12Z,15Z-octadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerol 791.073 C45 H74 O11 C(OC1(C(O)C(O)C(OO)C(O1)CO))C(OC(=O)CCCCCCCC=CCC=CCC=CCC)COC(=O)CCCCCCCC=CCC=CCC=CCC PUBCHEM:5771744: 1.14.99.- 18:2-18:3-MGDG = 18:3-18:3-MGDG glycolipid desaturation myo-inositol mesoinositol*chiro-inositol*meso-inositol*inositol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O)C(O)1)(O) CAS:6917-35-7:*LIGAND:C00137:*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 mesoinositol*chiro-inositol*meso-inositol*inositol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O)C(O)1)(O) CAS:6917-35-7:*LIGAND:C00137:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.4.1.- D-pinitol + galactinol = galactopinitol B + myo-inositol galactosylcyclitol biosynthesis myo-inositol mesoinositol*chiro-inositol*meso-inositol*inositol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O)C(O)1)(O) CAS:6917-35-7:*LIGAND:C00137:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.7.1.64 myo-inositol + ATP = D-myo-inositol (3)-monophosphate + ADP lipid-independent phytate biosynthesis myo-inositol mesoinositol*chiro-inositol*meso-inositol*inositol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O)C(O)1)(O) CAS:6917-35-7:*LIGAND:C00137:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.4.1.123 myo-inositol + UDP-galactose = galactinol + UDP stachyose biosynthesis myo-inositol mesoinositol*chiro-inositol*meso-inositol*inositol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O)C(O)1)(O) CAS:6917-35-7:*LIGAND:C00137:*CAS:87-89-8:*LIGAND-CPD:C00137: 1.13.99.1 O2 + myo-inositol = H2O + glucuronate UDP-D-glucuronate biosynthesis (from myo-inositol) myo-inositol mesoinositol*chiro-inositol*meso-inositol*inositol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O)C(O)1)(O) CAS:6917-35-7:*LIGAND:C00137:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.4.1.67 galactinol + raffinose = myo-inositol + stachyose stachyose biosynthesis myo-inositol mesoinositol*chiro-inositol*meso-inositol*inositol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O)C(O)1)(O) CAS:6917-35-7:*LIGAND:C00137:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.4.1.- D-pinitol + galactinol = galactopinitol A + myo-inositol galactosylcyclitol biosynthesis myo-inositol mesoinositol*chiro-inositol*meso-inositol*inositol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O)C(O)1)(O) CAS:6917-35-7:*LIGAND:C00137:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.4.1.82 galactinol + sucrose = myo-inositol + raffinose stachyose biosynthesis myo-inositol mesoinositol*chiro-inositol*meso-inositol*inositol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O)C(O)1)(O) CAS:6917-35-7:*LIGAND:C00137:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.4.1.- galactopinitol A + galactinol = ciceritol + myo-inositol galactosylcyclitol biosynthesis myo-inositol mesoinositol*chiro-inositol*meso-inositol*inositol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O)C(O)1)(O) CAS:6917-35-7:*LIGAND:C00137:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.4.1.- D-ononitol + galactinol = D-galactosylononitol + myo-inositol galactosylcyclitol biosynthesis myo-inositol mesoinositol*chiro-inositol*meso-inositol*inositol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O)C(O)1)(O) CAS:6917-35-7:*LIGAND:C00137:*CAS:87-89-8:*LIGAND-CPD:C00137: 2.7.8.11 myo-inositol = CMP phospholipid biosynthesis II 3-dehydroquinate 3-dehydroquinic acid*5-dehydroquinic acid*5-dehydroquinate*5-de-H-quinate 190.152 C7 H10 O6 C(O)(=O)C1([CH2]C(=O)[CH](O)[CH]([CH2]1)O)(O) LIGAND-CPD:C00944:*CAS:10534-44-8 4.2.1.10 3-dehydroquinate = H2O + 3-dehydro-shikimate quinate degradation 3-dehydroquinate 3-dehydroquinic acid*5-dehydroquinic acid*5-dehydroquinate*5-de-H-quinate 190.152 C7 H10 O6 C(O)(=O)C1([CH2]C(=O)[CH](O)[CH]([CH2]1)O)(O) LIGAND-CPD:C00944:*CAS:10534-44-8 4.2.1.10 3-dehydroquinate = H2O + 3-dehydro-shikimate chorismate biosynthesis 3-dehydroquinate 3-dehydroquinic acid*5-dehydroquinic acid*5-dehydroquinate*5-de-H-quinate 190.152 C7 H10 O6 C(O)(=O)C1([CH2]C(=O)[CH](O)[CH]([CH2]1)O)(O) LIGAND-CPD:C00944:*CAS:10534-44-8 4.2.3.4 3-deoxy-D-arabino-heptulosonate-7-phosphate = 3-dehydroquinate chorismate biosynthesis 3-dehydroquinate 3-dehydroquinic acid*5-dehydroquinic acid*5-dehydroquinate*5-de-H-quinate 190.152 C7 H10 O6 C(O)(=O)C1([CH2]C(=O)[CH](O)[CH]([CH2]1)O)(O) LIGAND-CPD:C00944:*CAS:10534-44-8 1.1.99.25 quinate + pyrroloquinoline quinone = 3-dehydroquinate + reduced pyrroloquinoline-quinone quinate degradation umbelliferone 7-oxycoumarin*skimmetin*hydrangin 162.145 C9 H6 O3 c1(=O)(ccc2(c(o1)cc(O)cc2)) PUBCHEM:5281426: 2.5.1.- umbelliferone + dimethylallyl-PP = demethylsuberosin + diphosphate linear furanocoumarin biosynthesis indole-3-acetyl-β-1-D-glucose 1-O-indol-3-ylacetyl-β-D-glucose 337.329 C16 H19 N1 O7 c1(c(c2(c([nH]1)cccc2))CC(=O)OC3(C(O)C(O)C(O)C(O3)CO)) 2.4.1.121 indole-3-acetate + UDP-D-glucose = indole-3-acetyl-β-1-D-glucose + UDP IAA conjugate biosynthesis II indole-3-acetyl-β-1-D-glucose 1-O-indol-3-ylacetyl-β-D-glucose 337.329 C16 H19 N1 O7 c1(c(c2(c([nH]1)cccc2))CC(=O)OC3(C(O)C(O)C(O)C(O3)CO)) 2.4.1.121 indole-3-acetate + UDP-D-glucose = 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 337.329 C16 H19 N1 O7 c1(c(c2(c([nH]1)cccc2))CC(=O)OC3(C(O)C(O)C(O)C(O3)CO)) 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 tricyclene 136.236 C10 H16 CC1(C)(C2(CC3(C(C)1C(C2)3))) 4.2.3.- geranyl-PP = tricyclene + diphosphate oleoresin monoterpene volatiles biosynthesis sabinene (-)-(1S)-sabinene 136.236 C10 H16 C=C2(C1(C(C(C)C)(C1)CC2)) 4.2.3.- geranyl-PP = sabinene + diphosphate monoterpene biosynthesis 3-deoxy-D-manno-octulosonate deoxy-manno-octulosonate*2-dehydro-3-deoxy-D-octonate*KDO*ketodeoxyoctonate 238.194 C8 H14 O8 C(O)(=O)C(=O)CC(O)C(O)C(O)C(O)CO 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 deoxy-manno-octulosonate*2-dehydro-3-deoxy-D-octonate*KDO*ketodeoxyoctonate 238.194 C8 H14 O8 C(O)(=O)C(=O)CC(O)C(O)C(O)C(O)CO 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 247.144 C8 H10 N1 O6 P1 c1(c(COP(O)(O)=O)c(C=O)c(O)c(C)n1) LIGAND-CPD:C00018:*CAS:54-47-7 2.7.1.35 ATP + pyridoxal = ADP + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway pyridoxal 5'-phosphate PLP*pyridoxal phosphate*pyridoxal-5P*pyridoxal 5-phosphate*pyridoxal-P 247.144 C8 H10 N1 O6 P1 c1(c(COP(O)(O)=O)c(C=O)c(O)c(C)n1) LIGAND-CPD:C00018:*CAS:54-47-7 2.7.1.35 ATP + pyridoxal = ADP + pyridoxal 5'-phosphate pyridoxamine anabolism pyridoxal 5'-phosphate PLP*pyridoxal phosphate*pyridoxal-5P*pyridoxal 5-phosphate*pyridoxal-P 247.144 C8 H10 N1 O6 P1 c1(c(COP(O)(O)=O)c(C=O)c(O)c(C)n1) LIGAND-CPD:C00018:*CAS:54-47-7 1.4.3.5 O2 + H2O + pyridoxamine 5'-phosphate = ammonia + H2O2 + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway pyridoxal 5'-phosphate PLP*pyridoxal phosphate*pyridoxal-5P*pyridoxal 5-phosphate*pyridoxal-P 247.144 C8 H10 N1 O6 P1 c1(c(COP(O)(O)=O)c(C=O)c(O)c(C)n1) LIGAND-CPD:C00018:*CAS:54-47-7 1.4.3.5 O2 + pyridoxine-5'-phosphate = H2O2 + pyridoxal 5'-phosphate pyridoxal 5'-phosphate biosynthesis pyridoxal 5'-phosphate PLP*pyridoxal phosphate*pyridoxal-5P*pyridoxal 5-phosphate*pyridoxal-P 247.144 C8 H10 N1 O6 P1 c1(c(COP(O)(O)=O)c(C=O)c(O)c(C)n1) LIGAND-CPD:C00018:*CAS:54-47-7 1.4.3.5 O2 + pyridoxine-5'-phosphate = H2O2 + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway dihydrozeatin-9-N-glucoside-O-glucoside 545.545 C22 H35 N5 O11 c1(c2(c(ncn1)N(C=N2)C3(OC(CO)C(O)C(O)C(O)3)))(NCCC(C)COC4(OC(CO)C(O)C(O)C(O)4)) 2.4.1.- dihydrozeatin-9-N-glucoside + UDP-D-glucose = dihydrozeatin-9-N-glucoside-O-glucoside + UDP cytokinins-O-glucoside biosynthesis bupropion (-)-2-(tert-butylamino)-3'-chloropropiophenone*1-propanone, 1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-,(+-)-*(+-)-1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone*amfebutamonum*α-(tert-butylamino)-m-chloropropiophenone 239.744 C13 H18 N1 O1 CL1 CC(NC(C)(C)C)C(=O)c1(cc(Cl)ccc1) bupropion = threohydrobupropion bupropion degradation bupropion (-)-2-(tert-butylamino)-3'-chloropropiophenone*1-propanone, 1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-,(+-)-*(+-)-1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone*amfebutamonum*α-(tert-butylamino)-m-chloropropiophenone 239.744 C13 H18 N1 O1 CL1 CC(NC(C)(C)C)C(=O)c1(cc(Cl)ccc1) bupropion = m-chlorobenzoate bupropion degradation bupropion (-)-2-(tert-butylamino)-3'-chloropropiophenone*1-propanone, 1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-,(+-)-*(+-)-1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone*amfebutamonum*α-(tert-butylamino)-m-chloropropiophenone 239.744 C13 H18 N1 O1 CL1 CC(NC(C)(C)C)C(=O)c1(cc(Cl)ccc1) bupropion = erythrohydrobupropion bupropion degradation bupropion (-)-2-(tert-butylamino)-3'-chloropropiophenone*1-propanone, 1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-,(+-)-*(+-)-1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone*amfebutamonum*α-(tert-butylamino)-m-chloropropiophenone 239.744 C13 H18 N1 O1 CL1 CC(NC(C)(C)C)C(=O)c1(cc(Cl)ccc1) 1.14.14.1 bupropion + NADPH + O2 = hydroxybupropion + NADP+ + H2O bupropion degradation dihydrogeranylgeranyl-chlorophyll a dihydrogeranylgeranyl-chl a*dihydroGG-chl a*dihydroGG-chlorophyll a 889.471 C55 H68 N4 O5 MG1 CC(CCCC(C)CCC=C(C)CCC=C(C)C)=CCOC(=O)CCC6(C4(C1(C(C(=O)OC)C(=O)c2(c(C)c7(n(c=12)[Mg]58(n3(c(c(C=C)c(C)c3C=C(N=45)C(C)6)C=C9(C(C)=C(CC)C(C=7)=N89)))))))) 1.3.1.- 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 CC(CCCC(C)CCC=C(C)CCC=C(C)C)=CCOC(=O)CCC6(C4(C1(C(C(=O)OC)C(=O)c2(c(C)c7(n(c=12)[Mg]58(n3(c(c(C=C)c(C)c3C=C(N=45)C(C)6)C=C9(C(C)=C(CC)C(C=7)=N89)))))))) 1.3.1.- geranylgeranyl-chlorophyll a + NADPH = dihydrogeranylgeranyl-chlorophyll a + NADP+ chlorophyll a biosynthesis II ent-kaurenoate ent-kaur-16-en-19-oate*ent-kaurenoic acid 302.456 C20 H30 O2 CC1([CH]2(C(CCC1)(C)[CH]4(C3(CC2)(CC(C(=C)C3)CC4))))(C(=O)O) 1.14.13.79 ent-kaurenoate + O2 + NADPH = ent-7-α-hydroxykaurenoate + H2O + NADP+ GA12 biosynthesis ent-kaurenoate ent-kaur-16-en-19-oate*ent-kaurenoic acid 302.456 C20 H30 O2 CC1([CH]2(C(CCC1)(C)[CH]4(C3(CC2)(CC(C(=C)C3)CC4))))(C(=O)O) 1.14.13.78 ent-kaur-16-en-19-al + NADPH + H+ + O2 = ent-kaurenoate + NADP+ + H2O GA12 biosynthesis palmitate Hexadecanoate (n-C16:0)*palmitic acid*hexadecanoate 256.428 C16 H32 O2 C(=O)(O)CCCCCCCCCCCCCCC LIGAND-CPD:C00249:*PUBCHEM:985:*CAS:57-10-3 1.14.13.- palmitate + NADPH + O2 = 16-hydroxypalmitate + NADP+ + H2O cutin biosynthesis 5'-phosphoribosyl-N-formylglycineamide 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 314.188 C8 H15 N2 O9 P1 C(=O)(CNC=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(=O)(O)O) PUBCHEM:440313:*LIGAND-CPD:C04376: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine purine nucleotides de novo biosynthesis II 5'-phosphoribosyl-N-formylglycineamide 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 314.188 C8 H15 N2 O9 P1 C(=O)(CNC=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(=O)(O)O) PUBCHEM:440313:*LIGAND-CPD:C04376: 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine purine nucleotides de novo biosynthesis I 5'-phosphoribosyl-N-formylglycineamide 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 314.188 C8 H15 N2 O9 P1 C(=O)(CNC=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(=O)(O)O) PUBCHEM:440313:*LIGAND-CPD:C04376: 2.1.2.2 N10-formyl-THF + 5-phospho-ribosyl-glycineamide = tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide purine nucleotides de novo biosynthesis II 5'-phosphoribosyl-N-formylglycineamide 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 314.188 C8 H15 N2 O9 P1 C(=O)(CNC=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(=O)(O)O) PUBCHEM:440313:*LIGAND-CPD:C04376: 2.1.2.2 N10-formyl-THF + 5-phospho-ribosyl-glycineamide = tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide tetrahydrofolate biosynthesis I 5'-phosphoribosyl-N-formylglycineamide 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 314.188 C8 H15 N2 O9 P1 C(=O)(CNC=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(=O)(O)O) PUBCHEM:440313:*LIGAND-CPD:C04376: 2.1.2.2 N10-formyl-THF + 5-phospho-ribosyl-glycineamide = tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide purine nucleotides de novo biosynthesis I 5'-phosphoribosyl-N-formylglycineamide 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 314.188 C8 H15 N2 O9 P1 C(=O)(CNC=O)N[CH]1(O[CH]([CH](O)[CH](O)1)COP(=O)(O)O) PUBCHEM:440313:*LIGAND-CPD:C04376: 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = 5'-phosphoribosyl-N-formylglycineamide + ADP purine nucleotides de novo biosynthesis I 18:2-18:3-PC 1-18:2-2-18:3-phosphatidylcholine*1-(9Z,12Z-octadecadienoyl)-2-(9Z,12Z,15Z-octadecatrienoyl)-sn-glycero-3-phosphocholine 781.084 C44 H79 N1 O8 P1 C(OC(=O)CCCCCCCC=CCC=CCCCCC)C(COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:2-18:3-PC = 18:3-18:3-PC phospholipid desaturation 18:2-18:3-PC 1-18:2-2-18:3-phosphatidylcholine*1-(9Z,12Z-octadecadienoyl)-2-(9Z,12Z,15Z-octadecatrienoyl)-sn-glycero-3-phosphocholine 781.084 C44 H79 N1 O8 P1 C(OC(=O)CCCCCCCC=CCC=CCCCCC)C(COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:1-18:3-PC = 18:2-18:3-PC phospholipid desaturation 18:2-18:3-PC 1-18:2-2-18:3-phosphatidylcholine*1-(9Z,12Z-octadecadienoyl)-2-(9Z,12Z,15Z-octadecatrienoyl)-sn-glycero-3-phosphocholine 781.084 C44 H79 N1 O8 P1 C(OC(=O)CCCCCCCC=CCC=CCCCCC)C(COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:2-18:2-PC = 18:2-18:3-PC phospholipid desaturation α-longipinene 204.355 C15 H24 CC1(C2(C3(C(CC=1)C2C(C)(C)CCC3)(C))) 4.2.3.- trans, trans-farnesyl diphosphate = α-longipinene + diphosphate oleoresin sesquiterpene volatiles biosynthesis ribose-1-phosphate D-ribose-1-phosphate*α-D-ribose-1P*α-D-ribofuranose 1-phosphate*α-D-ribose-1-phosphate 230.111 C5 H11 O8 P1 C(O)[CH]1(O[CH](OP(O)(O)=O)[CH](O)[CH](O)1) CAS:58459-37-3:*LIGAND-CPD:C00442:*CAS:14075-00-4 2.4.2.15 guanosine = ribose-1-phosphate + guanine salvage pathways of purine nucleosides ribose-1-phosphate D-ribose-1-phosphate*α-D-ribose-1P*α-D-ribofuranose 1-phosphate*α-D-ribose-1-phosphate 230.111 C5 H11 O8 P1 C(O)[CH]1(O[CH](OP(O)(O)=O)[CH](O)[CH](O)1) CAS:58459-37-3:*LIGAND-CPD:C00442:*CAS:14075-00-4 2.4.2.15 guanosine = ribose-1-phosphate + guanine salvage pathways of purine and pyrimidine nucleotides ribose-1-phosphate D-ribose-1-phosphate*α-D-ribose-1P*α-D-ribofuranose 1-phosphate*α-D-ribose-1-phosphate 230.111 C5 H11 O8 P1 C(O)[CH]1(O[CH](OP(O)(O)=O)[CH](O)[CH](O)1) CAS:58459-37-3:*LIGAND-CPD:C00442:*CAS:14075-00-4 2.4.2.- adenosine = ribose-1-phosphate + adenine salvage pathways of adenine, hypoxanthine, and their nucleosides ribose-1-phosphate D-ribose-1-phosphate*α-D-ribose-1P*α-D-ribofuranose 1-phosphate*α-D-ribose-1-phosphate 230.111 C5 H11 O8 P1 C(O)[CH]1(O[CH](OP(O)(O)=O)[CH](O)[CH](O)1) CAS:58459-37-3:*LIGAND-CPD:C00442:*CAS:14075-00-4 2.4.2.- adenosine = ribose-1-phosphate + adenine salvage pathways of purine nucleosides ribose-1-phosphate D-ribose-1-phosphate*α-D-ribose-1P*α-D-ribofuranose 1-phosphate*α-D-ribose-1-phosphate 230.111 C5 H11 O8 P1 C(O)[CH]1(O[CH](OP(O)(O)=O)[CH](O)[CH](O)1) CAS:58459-37-3:*LIGAND-CPD:C00442:*CAS:14075-00-4 2.4.2.- adenosine = ribose-1-phosphate + adenine salvage pathways of purine and pyrimidine nucleotides ribose-1-phosphate D-ribose-1-phosphate*α-D-ribose-1P*α-D-ribofuranose 1-phosphate*α-D-ribose-1-phosphate 230.111 C5 H11 O8 P1 C(O)[CH]1(O[CH](OP(O)(O)=O)[CH](O)[CH](O)1) CAS:58459-37-3:*LIGAND-CPD:C00442:*CAS:14075-00-4 2.4.2.3 uridine = ribose-1-phosphate + uracil (deoxy)ribose phosphate degradation ribose-1-phosphate D-ribose-1-phosphate*α-D-ribose-1P*α-D-ribofuranose 1-phosphate*α-D-ribose-1-phosphate 230.111 C5 H11 O8 P1 C(O)[CH]1(O[CH](OP(O)(O)=O)[CH](O)[CH](O)1) CAS:58459-37-3:*LIGAND-CPD:C00442:*CAS:14075-00-4 2.4.2.3 uridine = ribose-1-phosphate + uracil salvage pathways of pyrimidine ribonucleotides ribose-1-phosphate D-ribose-1-phosphate*α-D-ribose-1P*α-D-ribofuranose 1-phosphate*α-D-ribose-1-phosphate 230.111 C5 H11 O8 P1 C(O)[CH]1(O[CH](OP(O)(O)=O)[CH](O)[CH](O)1) CAS:58459-37-3:*LIGAND-CPD:C00442:*CAS:14075-00-4 5.4.2.7 ribose-1-phosphate = D-ribose-5-phosphate (deoxy)ribose phosphate degradation ribose-1-phosphate D-ribose-1-phosphate*α-D-ribose-1P*α-D-ribofuranose 1-phosphate*α-D-ribose-1-phosphate 230.111 C5 H11 O8 P1 C(O)[CH]1(O[CH](OP(O)(O)=O)[CH](O)[CH](O)1) CAS:58459-37-3:*LIGAND-CPD:C00442:*CAS:14075-00-4 2.4.2.- inosine = ribose-1-phosphate + hypoxanthine salvage pathways of adenine, hypoxanthine, and their nucleosides ribose-1-phosphate D-ribose-1-phosphate*α-D-ribose-1P*α-D-ribofuranose 1-phosphate*α-D-ribose-1-phosphate 230.111 C5 H11 O8 P1 C(O)[CH]1(O[CH](OP(O)(O)=O)[CH](O)[CH](O)1) CAS:58459-37-3:*LIGAND-CPD:C00442:*CAS:14075-00-4 2.4.2.- inosine = ribose-1-phosphate + hypoxanthine salvage pathways of purine nucleosides ribose-1-phosphate D-ribose-1-phosphate*α-D-ribose-1P*α-D-ribofuranose 1-phosphate*α-D-ribose-1-phosphate 230.111 C5 H11 O8 P1 C(O)[CH]1(O[CH](OP(O)(O)=O)[CH](O)[CH](O)1) CAS:58459-37-3:*LIGAND-CPD:C00442:*CAS:14075-00-4 xanthosine = ribose-1-phosphate + xanthine ureide biosynthesis hydroxypyruvate OH-pyruvate*OH-pyr*3-hydroxypyruvate 104.062 C3 H4 O4 C(O)(=O)C(=O)CO LIGAND-CPD:C00168:*CAS:1113-60-6 1.1.1.29 glycerate + NAD+ = hydroxypyruvate + NADH photorespiration hydroxypyruvate OH-pyruvate*OH-pyr*3-hydroxypyruvate 104.062 C3 H4 O4 C(O)(=O)C(=O)CO LIGAND-CPD:C00168:*CAS:1113-60-6 L-serine + α-ketoglutarate = L-glutamate + hydroxypyruvate photorespiration 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 575.017 C6 H12 O21 P5 C1(C(OP(O)([O-])=O)C(OP(O)([O-])=O)C(OP(O)([O-])=O)C(C(O)1)OP(O)([O-])=O)(OP(O)([O-])=O) 2.7.1.- D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = phytate + ADP lipid-independent phytate 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 575.017 C6 H12 O21 P5 C1(C(OP(O)([O-])=O)C(OP(O)([O-])=O)C(OP(O)([O-])=O)C(C(O)1)OP(O)([O-])=O)(OP(O)([O-])=O) 2.7.1.134 D-myo-inositol (3,4,5,6)-tetrakisphosphate + ATP = D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-independent phytate biosynthesis phaseoluteone licoisoflavone A*3'-prenyl-5,7,2',4'-tetrahydroxyisoflavone 354.359 C20 H18 O6 C2(=C(C(=O)c1(c(O)cc(O)cc1O2))c3(c(O)c(c(O)cc3)CC=C(C)C)) 2.5.1.1 2'-hydroxygenistein + dimethylallyl-PP = phaseoluteone + diphosphate wighteone and luteone biosynthesis trimethylamine (CH3)3NH*(CH3)3NH+ 59.111 C3 H9 N1 CN(C)C LIGAND-CPD:C00565:*CAS:75-50-3 O2 + H+ = trimethylamine + D,L-malic semialdehyde + H2O carnitine degradation III thiamin thiamine*vitamin B1 265.352 C12 H17 N4 O1 S1 c1(c(cnc(C)n1)C[n+]2(c(C)c(sc2)CCO))(N) CAS:67-03-8:*LIGAND-CPD:C00378:*CAS:59-43-8 2.7.1.89 thiamin + ATP = thiamine-phosphate + ADP thiamine biosynthesis UDP-galactose UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 566.305 C15 H24 N2 O17 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)C(O3)CO))) LIGAND-CPD:C00052:*CAS:2956-16-3 2.7.7.10 α-D-galactose 1-phosphate + UTP = UDP-galactose + diphosphate galactose degradation II UDP-galactose UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 566.305 C15 H24 N2 O17 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)C(O3)CO))) LIGAND-CPD:C00052:*CAS:2956-16-3 2.4.1.123 myo-inositol + UDP-galactose = galactinol + UDP stachyose biosynthesis UDP-galactose UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 566.305 C15 H24 N2 O17 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)C(O3)CO))) LIGAND-CPD:C00052:*CAS:2956-16-3 2.4.1.156 indol-3-yl-acetyl-myo-inositol + UDP-galactose = 5-O-(indol-3-ylacetyl-myo-inositol) D-galactoside + UDP IAA conjugate biosynthesis I UDP-galactose UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 566.305 C15 H24 N2 O17 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)C(O3)CO))) LIGAND-CPD:C00052:*CAS:2956-16-3 2.4.1.241 UDP-galactose = UDP glycolipid biosynthesis UDP-galactose UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 566.305 C15 H24 N2 O17 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)C(O3)CO))) LIGAND-CPD:C00052:*CAS:2956-16-3 5.4.99.9 UDP-galactose = UDP-D-galacto-1,4-furanose O-antigen biosynthesis UDP-galactose UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 566.305 C15 H24 N2 O17 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)C(O3)CO))) LIGAND-CPD:C00052:*CAS:2956-16-3 5.1.3.2 UDP-D-glucose = UDP-galactose galactose degradation II UDP-galactose UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 566.305 C15 H24 N2 O17 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)C(O3)CO))) LIGAND-CPD:C00052:*CAS:2956-16-3 5.1.3.2 UDP-D-glucose = UDP-galactose UDP-glucose conversion UDP-galactose UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 566.305 C15 H24 N2 O17 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)C(O3)CO))) LIGAND-CPD:C00052:*CAS:2956-16-3 5.1.3.2 UDP-D-glucose = UDP-galactose UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) UDP-galactose UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 566.305 C15 H24 N2 O17 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)C(O3)CO))) LIGAND-CPD:C00052:*CAS:2956-16-3 2.4.1.46 UDP-galactose = UDP glycolipid biosynthesis UDP-galactose UDP-D-galactopyranose*UDP-D-galactose*uridine diphosphate galactose 566.305 C15 H24 N2 O17 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)C(O3)CO))) LIGAND-CPD:C00052:*CAS:2956-16-3 2.7.7.12 UDP-D-glucose + α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-galactose UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) hydroxycinnamoyl-CoA 915.695 C30 H44 N7 O18 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)c1(ccccc1))COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(O)=O)n3(c4(c(nc3)c(N)ncn4))) LIGAND-CPD:C06362: hydroxycinnamoyl-CoA + NADP+ = oxocinnamoyl-CoA + NADPH salicylate biosynthesis hydroxycinnamoyl-CoA 915.695 C30 H44 N7 O18 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)c1(ccccc1))COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(O)=O)n3(c4(c(nc3)c(N)ncn4))) LIGAND-CPD:C06362: (E)-cinnamoyl-CoA + H2O = hydroxycinnamoyl-CoA salicylate biosynthesis L-valine V*val*valine 117.147 C5 H11 N1 O2 CC(C)C(N)C(=O)O LIGAND-CPD:C00183:*CAS:72-18-4 6.1.1.9 L-valine + ATP = diphosphate + AMP tRNA charging pathway L-valine V*val*valine 117.147 C5 H11 N1 O2 CC(C)C(N)C(=O)O LIGAND-CPD:C00183:*CAS:72-18-4 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate valine degradation I L-valine V*val*valine 117.147 C5 H11 N1 O2 CC(C)C(N)C(=O)O LIGAND-CPD:C00183:*CAS:72-18-4 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate valine biosynthesis L-valine V*val*valine 117.147 C5 H11 N1 O2 CC(C)C(N)C(=O)O LIGAND-CPD:C00183:*CAS:72-18-4 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate pantothenate biosynthesis I L-valine V*val*valine 117.147 C5 H11 N1 O2 CC(C)C(N)C(=O)O LIGAND-CPD:C00183:*CAS:72-18-4 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate valine degradation II L-valine V*val*valine 117.147 C5 H11 N1 O2 CC(C)C(N)C(=O)O LIGAND-CPD:C00183:*CAS:72-18-4 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate pantothenate biosynthesis II cis-zeatin-O-glucoside 381.388 C16 H23 N5 O6 c2(c1(c(N=CN1)ncn2))NCC=C(C)COC3(OC(CO)C(O)C(O)C(O)3) 2.4.1.215 cis-zeatin + UDP-D-glucose = cis-zeatin-O-glucoside + UDP cytokinins-O-glucoside 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 260.198 C6 H13 O7 P1 S1 C(SC)C(O)C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C04582:*PUBCHEM:329: 5.3.1.23 5-methylthioribose-1-phosphate = 5-methylthioribulose-1-phosphate methionine salvage pathway 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 260.198 C6 H13 O7 P1 S1 C(SC)C(O)C(O)C(=O)COP(O)(=O)O LIGAND-CPD:C04582:*PUBCHEM:329: 5-methylthioribulose-1-phosphate = 2,3-diketo-5-methylthio-1-phosphopentane + H2O methionine salvage pathway crinosterol 398.671 C28 H46 O1 CC(C(C)C)C=CC(C)C1(C2(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))(C)) 1.3.1.- campesterol + NADP+ = crinosterol + NADPH sterol biosynthesis riboflavin vitamin B2 376.368 C17 H20 N4 O6 C(O)C(O)C(O)C(O)Cn2(c1(c(C(=O)NC(N=1)=O)=nc3(c2cc(C)c(C)c3))) PUBCHEM:6759:*LIGAND-CPD:C00255:*CAS:83-88-5 2.7.1.26 riboflavin + ATP = FMN + ADP flavin biosynthesis riboflavin vitamin B2 376.368 C17 H20 N4 O6 C(O)C(O)C(O)C(O)Cn2(c1(c(C(=O)NC(N=1)=O)=nc3(c2cc(C)c(C)c3))) PUBCHEM:6759:*LIGAND-CPD:C00255:*CAS:83-88-5 2.5.1.9 6,7-dimethyl-8-(1-D-ribityl)lumazine = 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione + riboflavin flavin biosynthesis N-carbamoyl-L-aspartate carbamyul-L-aspartate*N-carbamoyl-L-aspartate*carbamyul-aspartate*carbamoyl-aspartate*carbamyl-aspartate*carbamyl-L-aspartate 176.129 C5 H8 N2 O5 C(=O)(O)CC(C(O)=O)NC(N)=O LIGAND-CPD:C00438:*CAS:16649-79-9 3.5.2.3 dihydroorotate + H2O = N-carbamoyl-L-aspartate de novo biosynthesis of pyrimidine ribonucleotides N-carbamoyl-L-aspartate carbamyul-L-aspartate*N-carbamoyl-L-aspartate*carbamyul-aspartate*carbamoyl-aspartate*carbamyl-aspartate*carbamyl-L-aspartate 176.129 C5 H8 N2 O5 C(=O)(O)CC(C(O)=O)NC(N)=O LIGAND-CPD:C00438:*CAS:16649-79-9 2.1.3.2 L-aspartate + carbamoyl-phosphate = N-carbamoyl-L-aspartate de novo biosynthesis of pyrimidine ribonucleotides 18:3-16:1-MGDG 1-18:3-2-16:1-monogalactosyldiacylglycerol*1-(9Z,12Z,15Z-octadecatrienoyl)-2-(7Z-hexadecenoyl)-3-O-beta-D-galactosyl-sn-glycerol 751.052 C43 H74 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:2-16:1-MGDG = 18:3-16:1-MGDG glycolipid desaturation 18:3-16:1-MGDG 1-18:3-2-16:1-monogalactosyldiacylglycerol*1-(9Z,12Z,15Z-octadecatrienoyl)-2-(7Z-hexadecenoyl)-3-O-beta-D-galactosyl-sn-glycerol 751.052 C43 H74 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:3-16:0-MGDG = 18:3-16:1-MGDG glycolipid desaturation 18:3-16:1-MGDG 1-18:3-2-16:1-monogalactosyldiacylglycerol*1-(9Z,12Z,15Z-octadecatrienoyl)-2-(7Z-hexadecenoyl)-3-O-beta-D-galactosyl-sn-glycerol 751.052 C43 H74 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:3-16:1-MGDG = 18:3-16:2-MGDG glycolipid desaturation cis-zeatin-7-N-glucoside 381.388 C16 H23 N5 O6 c2(c1(N(C=Nc1ncn2)C3(OC(CO)C(O)C(O)C(O)3)))(NCC=C(C)CO) 2.4.1.- cis-zeatin + UDP-D-glucose = cis-zeatin-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis GA13 gibberellin A13*gibberellin A13*GA13 378.421 C20 H26 O7 CC1([CH]4(C(CCC(O)1)(C(=O)O)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA25 + α-ketoglutarate + O2 = GA13 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) indole-3-ketol 175.187 C10 H9 N1 O2 c1(c(C(=O)CO)c2(c([nH]1)cccc2)) 1.13.99.3 indole-3-glycol = indole-3-ketol tryptophan degradation V (side chain pathway) indole-3-ketol 175.187 C10 H9 N1 O2 c1(c(C(=O)CO)c2(c([nH]1)cccc2)) 1.1.99.8 indole-3-glyoxal + NADH + H+ = indole-3-ketol + NAD+ tryptophan degradation V (side chain pathway) 18:1-18:1-PC 1-18:1-2-18:1-sn-glycerol-3-phosphocholine*1,2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine 787.131 C44 H85 N1 O8 P1 C(OP(O)(=O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PUBCHEM:5313476: 1.14.99.- 18:1-18:1-PC = 18:1-18:2-PC phospholipid desaturation 18:1-18:1-PC 1-18:1-2-18:1-sn-glycerol-3-phosphocholine*1,2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine 787.131 C44 H85 N1 O8 P1 C(OP(O)(=O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PUBCHEM:5313476: 1.14.99.- 18:1-18:1-PC = 18:2-18:1-PC phospholipid desaturation 2-aceto-2-hydroxy-butyrate α-aceto-α-hydroxybutyrate 146.143 C6 H10 O4 CC(=O)C(O)(C(O)=O)CC LIGAND-CPD:C06006:*PUBCHEM:21:*CAS:3142-65-2 2.2.1.6 pyruvate + 2-oxobutanoate = 2-aceto-2-hydroxy-butyrate + CO2 isoleucine biosynthesis from threonine 2-aceto-2-hydroxy-butyrate α-aceto-α-hydroxybutyrate 146.143 C6 H10 O4 CC(=O)C(O)(C(O)=O)CC LIGAND-CPD:C06006:*PUBCHEM:21:*CAS:3142-65-2 1.1.1.86 2-aceto-2-hydroxy-butyrate + NADPH = 2,3-dihydroxy-3-methylvalerate + NADP+ isoleucine biosynthesis from threonine 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine*4-(1-D-ribitylamino)-5-aminouracil*compound 6 276.249 C9 H16 N4 O6 C(O)C(O)C(O)C(O)CNc1(c(N)c(=O)[nH]c([nH]1)=O) LIGAND-CPD:C04732: 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione + 3,4-dihydroxy-2-butanone-4-P = 6,7-dimethyl-8-(1-D-ribityl)lumazine + H2O flavin biosynthesis 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine*4-(1-D-ribitylamino)-5-aminouracil*compound 6 276.249 C9 H16 N4 O6 C(O)C(O)C(O)C(O)CNc1(c(N)c(=O)[nH]c([nH]1)=O) LIGAND-CPD:C04732: 2.5.1.9 6,7-dimethyl-8-(1-D-ribityl)lumazine = 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione + riboflavin flavin biosynthesis 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine*4-(1-D-ribitylamino)-5-aminouracil*compound 6 276.249 C9 H16 N4 O6 C(O)C(O)C(O)C(O)CNc1(c(N)c(=O)[nH]c([nH]1)=O) LIGAND-CPD:C04732: 5-amino-6-(5'-phosphoribitylamino)uracil + H2O = 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione flavin biosynthesis bergaptol 5-hydroxyfuranocoumarin*5-hydroxypsoralen 202.166 C11 H6 O4 C2(=CC1(C(O)=C3(C(=CC=1O2)OC(=O)C=C3))) PUBCHEM:5280371:*NCI:341958*CAS:486-60-2 psoralen + NADPH + H2O = bergaptol + NADP+ linear furanocoumarin biosynthesis bergaptol 5-hydroxyfuranocoumarin*5-hydroxypsoralen 202.166 C11 H6 O4 C2(=CC1(C(O)=C3(C(=CC=1O2)OC(=O)C=C3))) PUBCHEM:5280371:*NCI:341958*CAS:486-60-2 2.1.1.69 bergaptol + S-adenosyl-L-methionine = bergapten + S-adenosyl-L-homocysteine linear furanocoumarin biosynthesis cotinine methonium ion N-methylcotininium ion*cotinine methonium ion 191.252 C11 H15 N2 O1 c1([n+](C)cc(cc1)[CH]2(N(C)C(=O)CC2)) cotinine = cotinine methonium ion nicotine degradation III pyrroloquinoline quinone PQQ*methoxatin 330.21 C14 H6 N2 O8 C(=O)(O)c2(cc(C(O)=O)c1(c3(c(C(=O)C(=O)c1n2)cc([nH]3)C(O)=O))) CAS:72909-34-3: 1.1.99.25 quinate + pyrroloquinoline quinone = 3-dehydroquinate + reduced pyrroloquinoline-quinone quinate degradation cyanate cyanic acid*hydrogen cyanate 43.025 C1 H1 N1 O1 C(#N)O LIGAND-CPD:C01417:*CAS:420-05-3 4.3.99.1 HCO3- + cyanate = carbamate + CO2 cyanate degradation methylglyoxal oxopropanal*acetylformaldehyde*pyruvic aldehyde*pyruvaldehyde*methyl-glyoxal*2-oxo-propanal 72.063 C3 H4 O2 C(=O)C(C)=O LIGAND-CPD:C00546:*CAS:78-98-8 4.4.1.5 S-lactoyl-glutathione = methylglyoxal + glutathione methylglyoxal degradation I methylglyoxal oxopropanal*acetylformaldehyde*pyruvic aldehyde*pyruvaldehyde*methyl-glyoxal*2-oxo-propanal 72.063 C3 H4 O2 C(=O)C(C)=O LIGAND-CPD:C00546:*CAS:78-98-8 1.4.3.6 aminoacetone + H2O + O2 = ammonia + methylglyoxal + H2O2 threonine degradation III (to methylglyoxal) methylglyoxal oxopropanal*acetylformaldehyde*pyruvic aldehyde*pyruvaldehyde*methyl-glyoxal*2-oxo-propanal 72.063 C3 H4 O2 C(=O)C(C)=O LIGAND-CPD:C00546:*CAS:78-98-8 methylglyoxal + NADPH = acetol + NADP+ acetone degradation (to methylglyoxal) cotinine N-oxide (5s)-1-methyl-5-(1-oxido-3-pyridinyl)-2-pyrrolidinone*2-pyrrolidinone, 1-methyl-5-(1-oxido-3-pyridinyl)-, (5S)-*2-pyrrolidinone, 1-methyl-5-(3-pyridinyl)-, N-oxide, (S)- 192.217 C10 H12 N2 O2 c1(n(=O)cc(cc1)[CH]2(N(C)C(=O)CC2)) cotinine = cotinine N-oxide nicotine degradation III D-galactosylononitol O-α-D-galactopyranosyl-(1,3)-4O-methyl-D-myo-inositol 356.326 C13 H24 O11 C1(C(O)C(O)C(O)C(O1)CO)OC2(C(OC)C(O)C(O)C(O)C(O)2) 2.4.1.- D-ononitol + galactinol = D-galactosylononitol + myo-inositol galactosylcyclitol biosynthesis GDP-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C(O)1)OP(O)(=O)OP(O)(=O)OCC2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4)))) LIGAND-CPD:C00096: (mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)3-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C(O)1)OP(O)(=O)OP(O)(=O)OCC2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4)))) LIGAND-CPD:C00096: 2.4.1.- inositol-P-ceramide + GDP-D-mannose = mannosyl-inositol-phosphorylceramide sphingolipid metabolism GDP-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C(O)1)OP(O)(=O)OP(O)(=O)OCC2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4)))) LIGAND-CPD:C00096: 5.1.3.- GDP-D-mannose = GDP-L-gulose ascorbate biosynthesis GDP-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C(O)1)OP(O)(=O)OP(O)(=O)OCC2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4)))) LIGAND-CPD:C00096: (mannosyl)3-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)4-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C(O)1)OP(O)(=O)OP(O)(=O)OCC2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4)))) LIGAND-CPD:C00096: 2.7.7.22 α-D-mannose 1-phosphate + GDP = GDP-D-mannose GDP-mannose metabolism GDP-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C(O)1)OP(O)(=O)OP(O)(=O)OCC2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4)))) LIGAND-CPD:C00096: 4.2.1.47 GDP-D-mannose = H2O + GDP-4-dehydro-6-deoxy-D-mannose GDP-D-rhamnose biosynthesis GDP-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C(O)1)OP(O)(=O)OP(O)(=O)OCC2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4)))) LIGAND-CPD:C00096: 4.2.1.47 GDP-D-mannose = H2O + GDP-4-dehydro-6-deoxy-D-mannose GDP-L-fucose biosynthesis I (from GDP-D-mannose) GDP-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C(O)1)OP(O)(=O)OP(O)(=O)OCC2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4)))) LIGAND-CPD:C00096: GDP-D-mannose + H2O = GDP + mannose GDP-mannose metabolism GDP-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C(O)1)OP(O)(=O)OP(O)(=O)OCC2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4)))) LIGAND-CPD:C00096: 2.4.1.132 mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C(O)1)OP(O)(=O)OP(O)(=O)OCC2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4)))) LIGAND-CPD:C00096: 2.4.1.83 dolichyl-phosphate + GDP-D-mannose = dolichyl β-D-mannosyl phosphate + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C(O)1)OP(O)(=O)OP(O)(=O)OCC2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4)))) LIGAND-CPD:C00096: (mannosyl)4-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C(O)1)OP(O)(=O)OP(O)(=O)OCC2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4)))) LIGAND-CPD:C00096: 2.4.1.142 (N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP-D-mannose guanosine pyrophosphate mannose*guanosine diphosphomannose*guanosine diphosphate mannose*GDP-mannose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C(O)1)OP(O)(=O)OP(O)(=O)OCC2(OC(C(O)C(O)2)n3(c4(c(nc3)c(=O)[nH]c(N)n4)))) LIGAND-CPD:C00096: 2.7.7.13 α-D-mannose 1-phosphate + GTP = GDP-D-mannose + diphosphate ascorbate 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 CC(C)C(=C)CCC(C)C1(C2(C)(C(C)(CC1)C3(=C(CC2)C4([CH](CC3)C(C)C(O)CC4)(C)))) LIGAND-CPD:C01943: 1.14.13.70 NADPH + O2 + obtusifoliol + H+ = H2O + NADP+ + formate + (4α)-methyl-(5α)-ergosta-8,14,24(28)-trien-3β-ol 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 CC(C)C(=C)CCC(C)C1(C2(C)(C(C)(CC1)C3(=C(CC2)C4([CH](CC3)C(C)C(O)CC4)(C)))) LIGAND-CPD:C01943: 5.5.1.9 cycloeucalenol = obtusifoliol sterol biosynthesis indole-3-acetyl-glu indole-3-acetyl-glutamate 304.302 C15 H16 N2 O5 C(NC(C(O)=O)CCC(O)=O)(=O)Cc1(c2(c([nH]c1)cccc2)) indole-3-acetate + L-glutamate = indole-3-acetyl-glu + H2O IAA conjugate biosynthesis II demethylsuberosin 7-demethylsuberosin 230.263 C14 H14 O3 CC(C)=CCc1(c(O)cc2(c(c1)ccc(=O)o2)) PUBCHEM:5316525: demethylsuberosin + O2 + NADPH = marmesin + NADP+ + H2O linear furanocoumarin biosynthesis demethylsuberosin 7-demethylsuberosin 230.263 C14 H14 O3 CC(C)=CCc1(c(O)cc2(c(c1)ccc(=O)o2)) PUBCHEM:5316525: 2.5.1.- umbelliferone + dimethylallyl-PP = demethylsuberosin + diphosphate linear furanocoumarin biosynthesis tryptamine 3-(2-aminoethyl)indole 160.218 C10 H12 N2 C(N)Cc1(c2(c([nH]c1)cccc2)) CAS:61-54-1 1.4.3.6 tryptamine + H2O + O2 = ammonia + indole acetaldehyde + H2O2 IAA biosynthesis I tryptamine 3-(2-aminoethyl)indole 160.218 C10 H12 N2 C(N)Cc1(c2(c([nH]c1)cccc2)) CAS:61-54-1 4.3.3.2 tryptamine + secologanin = strictosidine + H2O secologanin and strictosidine biosynthesis tryptamine 3-(2-aminoethyl)indole 160.218 C10 H12 N2 C(N)Cc1(c2(c([nH]c1)cccc2)) CAS:61-54-1 4.1.1.28 L-tryptophan = CO2 + tryptamine IAA biosynthesis I tryptamine 3-(2-aminoethyl)indole 160.218 C10 H12 N2 C(N)Cc1(c2(c([nH]c1)cccc2)) CAS:61-54-1 4.1.1.28 L-tryptophan = CO2 + tryptamine secologanin and strictosidine biosynthesis tryptamine 3-(2-aminoethyl)indole 160.218 C10 H12 N2 C(N)Cc1(c2(c([nH]c1)cccc2)) CAS:61-54-1 tryptamine + O2 + 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 322.211 C10 H15 N2 O8 P1 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(O)(O)=O)) LIGAND-CPD:C00364:*CAS:365-07-1 2.7.1.21 thymidine + ATP = dTMP + ADP salvage pathways of purine and pyrimidine nucleotides 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 322.211 C10 H15 N2 O8 P1 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(O)(O)=O)) LIGAND-CPD:C00364:*CAS:365-07-1 2.7.1.21 thymidine + ATP = dTMP + ADP salvage pathways of pyrimidine deoxyribonucleotides 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 322.211 C10 H15 N2 O8 P1 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(O)(O)=O)) LIGAND-CPD:C00364:*CAS:365-07-1 2.7.4.9 ATP + dTMP = ADP + dTDP salvage pathways of purine and pyrimidine nucleotides 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 322.211 C10 H15 N2 O8 P1 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(O)(O)=O)) LIGAND-CPD:C00364:*CAS:365-07-1 2.7.4.9 ATP + dTMP = ADP + dTDP de novo biosynthesis of pyrimidine deoxyribonucleotides 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 322.211 C10 H15 N2 O8 P1 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(O)(O)=O)) LIGAND-CPD:C00364:*CAS:365-07-1 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate salvage pathways of purine and pyrimidine nucleotides 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 322.211 C10 H15 N2 O8 P1 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(O)(O)=O)) LIGAND-CPD:C00364:*CAS:365-07-1 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate de novo biosynthesis of pyrimidine deoxyribonucleotides 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 322.211 C10 H15 N2 O8 P1 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(O)(O)=O)) LIGAND-CPD:C00364:*CAS:365-07-1 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate formylTHF biosynthesis II 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 322.211 C10 H15 N2 O8 P1 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(O)(O)=O)) LIGAND-CPD:C00364:*CAS:365-07-1 2.1.1.45 5,10-methylene-THF + dUMP = dTMP + 7,8-dihydrofolate formylTHF biosynthesis I 3-(2'-methylthio)ethylmalic-acid 208.229 C7 H12 O5 S1 C(SC)CC(C(O)=O)C(O)C(=O)O 5.4.4.- 2-(2'-methylthio)ethylmalic-acid = 3-(2'-methylthio)ethylmalic-acid homomethionine biosynthesis 3-(2'-methylthio)ethylmalic-acid 208.229 C7 H12 O5 S1 C(SC)CC(C(O)=O)C(O)C(=O)O 1.1.1.- 3-(2'-methylthio)ethylmalic-acid = 2-oxo-5-methylthiopentanoic-acid + CO2 homomethionine biosynthesis adenosine 5'-phosphosulfate adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 427.282 C10 H14 N5 O10 P1 S1 C(OP(=O)(O)OS(=O)(O)=O)[CH]1(O[CH](C(O)C1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00224:*PUBCHEM:10238:*CAS:485-84-7 2.7.1.25 adenosine 5'-phosphosulfate + ATP = phosphoadenosine-5'-phosphosulfate + ADP sulfate reduction I (assimilatory) adenosine 5'-phosphosulfate adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 427.282 C10 H14 N5 O10 P1 S1 C(OP(=O)(O)OS(=O)(O)=O)[CH]1(O[CH](C(O)C1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00224:*PUBCHEM:10238:*CAS:485-84-7 2.7.1.25 adenosine 5'-phosphosulfate + ATP = phosphoadenosine-5'-phosphosulfate + ADP sulfate activation for sulfonation adenosine 5'-phosphosulfate adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 427.282 C10 H14 N5 O10 P1 S1 C(OP(=O)(O)OS(=O)(O)=O)[CH]1(O[CH](C(O)C1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00224:*PUBCHEM:10238:*CAS:485-84-7 1.8.4.9 sulfite + AMP + glutathione disulfide = adenosine 5'-phosphosulfate + glutathione sulfate reduction II (assimilatory) adenosine 5'-phosphosulfate adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 427.282 C10 H14 N5 O10 P1 S1 C(OP(=O)(O)OS(=O)(O)=O)[CH]1(O[CH](C(O)C1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00224:*PUBCHEM:10238:*CAS:485-84-7 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate reduction II (assimilatory) adenosine 5'-phosphosulfate adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 427.282 C10 H14 N5 O10 P1 S1 C(OP(=O)(O)OS(=O)(O)=O)[CH]1(O[CH](C(O)C1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00224:*PUBCHEM:10238:*CAS:485-84-7 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfite oxidation III adenosine 5'-phosphosulfate adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 427.282 C10 H14 N5 O10 P1 S1 C(OP(=O)(O)OS(=O)(O)=O)[CH]1(O[CH](C(O)C1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00224:*PUBCHEM:10238:*CAS:485-84-7 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate reduction I (assimilatory) adenosine 5'-phosphosulfate adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 427.282 C10 H14 N5 O10 P1 S1 C(OP(=O)(O)OS(=O)(O)=O)[CH]1(O[CH](C(O)C1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00224:*PUBCHEM:10238:*CAS:485-84-7 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate activation for sulfonation adenosine 5'-phosphosulfate adenylyl-sulfate*APS*adenosine phosphosulfate*adenosine 5'-sulphatophosphate 427.282 C10 H14 N5 O10 P1 S1 C(OP(=O)(O)OS(=O)(O)=O)[CH]1(O[CH](C(O)C1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00224:*PUBCHEM:10238:*CAS:485-84-7 1.8.99.2 sulfite + AMP = adenosine 5'-phosphosulfate sulfite oxidation III geranylgeranyl-chlorophyll a geranylgeranyl-chl a*GG-chl a*GG-chlorophyll a 887.455 C55 H66 N4 O5 MG1 CC(CCC=C(C)CCC=C(C)CCC=C(C)C)=CCOC(=O)CCC6(C4(C1(C(C(=O)OC)C(=O)c2(c(C)c7(n(c=12)[Mg]58(n3(c(c(C=C)c(C)c3C=C(N=45)C(C)6)C=C9(C(C)=C(CC)C(C=7)=N89)))))))) 1.3.1.- 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 CC(CCC=C(C)CCC=C(C)CCC=C(C)C)=CCOC(=O)CCC6(C4(C1(C(C(=O)OC)C(=O)c2(c(C)c7(n(c=12)[Mg]58(n3(c(c(C=C)c(C)c3C=C(N=45)C(C)6)C=C9(C(C)=C(CC)C(C=7)=N89)))))))) 2.5.1.- chlorophyllide a + geranylgeranyl diphosphate = geranylgeranyl-chlorophyll a + diphosphate chlorophyll a biosynthesis II dTDP-4-dehydro-6-deoxy-D-glucose TDP-4-keto-6-deoxy-D-glucose*TDP-4-oxo-6-deoxy-D-glucose*dTDP-4-oxo-6-deoxy-D-glucose 546.317 C16 H24 N2 O15 P2 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(=O)C(O3)C))) LIGAND-CPD:C00687: 5.1.3.13 dTDP-4-dehydro-6-deoxy-D-glucose = dTDP-4-dehydro-6-deoxy-L-mannose dTDP-L-rhamnose biosynthesis I dTDP-4-dehydro-6-deoxy-D-glucose TDP-4-keto-6-deoxy-D-glucose*TDP-4-oxo-6-deoxy-D-glucose*dTDP-4-oxo-6-deoxy-D-glucose 546.317 C16 H24 N2 O15 P2 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(=O)C(O3)C))) LIGAND-CPD:C00687: 4.2.1.46 dTDP-D-glucose = H2O + dTDP-4-dehydro-6-deoxy-D-glucose dTDP-L-rhamnose biosynthesis I dTDP-D-glucose dTDP-glucose 564.333 C16 H26 N2 O16 P2 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)C(O3)CO))) CAS:2009-24-7:*LIGAND-CPD:C00842: 4.2.1.46 dTDP-D-glucose = H2O + dTDP-4-dehydro-6-deoxy-D-glucose dTDP-L-rhamnose biosynthesis I dTDP-D-glucose dTDP-glucose 564.333 C16 H26 N2 O16 P2 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)C(O3)CO))) CAS:2009-24-7:*LIGAND-CPD:C00842: 2.7.7.24 α-D-glucose 1-phosphate + dTTP = dTDP-D-glucose + diphosphate dTDP-L-rhamnose biosynthesis I (+)-cis-isopulegone 152.236 C10 H16 O1 C=C(C)C1(C(=O)CC(C)CC1) (+)-cis-isopulegone + NADP+ = (+)-pulegone + NADPH menthol biosynthesis (+)-cis-isopulegone 152.236 C10 H16 O1 C=C(C)C1(C(=O)CC(C)CC1) (-)-isopiperitenone + NADP+ = (+)-cis-isopulegone + NADPH menthol biosynthesis N-succinyl-2-amino-6-ketopimelate N-Succinyl-2-L-amino-6-oxoheptanedioate*N-succinyl-L-2-amino-6-oxoheptanedioate*succinyl-ε-keto-α-aminopimelate 289.241 C11 H15 N1 O8 C(O)(=O)C(=O)CCCC(C(=O)O)NC(=O)CCC(=O)O PUBCHEM:440349:*LIGAND-CPD:C04462: 2.6.1.17 α-ketoglutarate = L-glutamate + N-succinyl-2-amino-6-ketopimelate lysine biosynthesis I N-succinyl-2-amino-6-ketopimelate N-Succinyl-2-L-amino-6-oxoheptanedioate*N-succinyl-L-2-amino-6-oxoheptanedioate*succinyl-ε-keto-α-aminopimelate 289.241 C11 H15 N1 O8 C(O)(=O)C(=O)CCCC(C(=O)O)NC(=O)CCC(=O)O PUBCHEM:440349:*LIGAND-CPD:C04462: 2.3.1.117 H2O + tetrahydrodipicolinate + succinyl-CoA = N-succinyl-2-amino-6-ketopimelate + coenzyme A lysine biosynthesis I pantoyl lactone (R)-pantolactone*(R)-Pantoyl lactone*(3R)-dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone 130.143 C6 H10 O3 C1(C(C)(C)C(O)C(=O)O1) CAS:599-04-2 6.3.2.1 pantoyl lactone + β-alanine = pantothenate pantothenate biosynthesis III pantoyl lactone (R)-pantolactone*(R)-Pantoyl lactone*(3R)-dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone 130.143 C6 H10 O3 C1(C(C)(C)C(O)C(=O)O1) CAS:599-04-2 1.1.1.168 NADP+ + pantoyl lactone = NADPH + 2-oxopantoyl lactone pantothenate biosynthesis III trans-zeatin-O-glucoside O-β-D-Glucosylzeatin 381.388 C16 H23 N5 O6 c2(c1(c(NC=N1)ncn2))NCC=C(C)COC3(OC(CO)C(O)C(O)C(O)3) 2.4.1.203 trans-zeatin + UDP-D-glucose = trans-zeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis trans-zeatin-O-glucoside O-β-D-Glucosylzeatin 381.388 C16 H23 N5 O6 c2(c1(c(NC=N1)ncn2))NCC=C(C)COC3(OC(CO)C(O)C(O)C(O)3) 2.4.1.- trans-zeatin-O-glucoside + UDP-D-glucose = trans-zeatin-O-glucoside-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis isoamyl alcohol isopentanol 88.149 C5 H12 O1 CC(C)CCO PUBCHEM:31260: 1.1.1.1 3-methylbutanal + NADH = isoamyl alcohol + NAD+ leucine degradation III isopentenyladenine N6-Δ2-isopentenyladenine*iP 202.238 C10 H12 N5 c2(ncnc1(c(ncn1)2))(NCC=C(C)C) CAS:2365-40-4:*NCI:|106958|: isopentenyladenosine-5'-monophosphate + H2O = isopentenyladenine + D-ribose-5-phosphate trans-zeatin biosynthesis isopentenyladenine N6-Δ2-isopentenyladenine*iP 202.238 C10 H12 N5 c2(ncnc1(c(ncn1)2))(NCC=C(C)C) CAS:2365-40-4:*NCI:|106958|: isopentenyladenine + H2O = trans-zeatin + H+ trans-zeatin biosynthesis isopentenyladenine N6-Δ2-isopentenyladenine*iP 202.238 C10 H12 N5 c2(ncnc1(c(ncn1)2))(NCC=C(C)C) CAS:2365-40-4:*NCI:|106958|: isopentenyl adenosine + H2O = isopentenyladenine + D-ribose trans-zeatin biosynthesis isopentenyladenine N6-Δ2-isopentenyladenine*iP 202.238 C10 H12 N5 c2(ncnc1(c(ncn1)2))(NCC=C(C)C) CAS:2365-40-4:*NCI:|106958|: 1.5.99.12 isopentenyladenine + FAD + H2O = 3-methyl-2-butenal + adenine + FADH2 cytokinins degradation isopentenyladenine N6-Δ2-isopentenyladenine*iP 202.238 C10 H12 N5 c2(ncnc1(c(ncn1)2))(NCC=C(C)C) CAS:2365-40-4:*NCI:|106958|: 2.4.1.- isopentenyladenine + UDP-D-glucose = isopentenyladenine-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis isopentenyladenine N6-Δ2-isopentenyladenine*iP 202.238 C10 H12 N5 c2(ncnc1(c(ncn1)2))(NCC=C(C)C) CAS:2365-40-4:*NCI:|106958|: 2.4.1.- isopentenyladenine + UDP-D-glucose = isopentenyladenine-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis deoxyuridine 2'-deoxyuridine 228.204 C9 H12 N2 O5 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)CO)) LIGAND-CPD:C00526:*CAS:951-78-0 3.5.4.5 H2O + deoxycytidine = ammonia + deoxyuridine (deoxy)ribose phosphate degradation deoxyuridine 2'-deoxyuridine 228.204 C9 H12 N2 O5 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)CO)) LIGAND-CPD:C00526:*CAS:951-78-0 3.5.4.5 H2O + deoxycytidine = ammonia + deoxyuridine salvage pathways of pyrimidine deoxyribonucleotides deoxyuridine 2'-deoxyuridine 228.204 C9 H12 N2 O5 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)CO)) LIGAND-CPD:C00526:*CAS:951-78-0 2.7.1.21 deoxyuridine + ATP = dUMP + ADP salvage pathways of pyrimidine deoxyribonucleotides deoxyuridine 2'-deoxyuridine 228.204 C9 H12 N2 O5 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)CO)) LIGAND-CPD:C00526:*CAS:951-78-0 deoxyuridine = deoxyribose-1-phosphate + uracil (deoxy)ribose phosphate degradation deoxyuridine 2'-deoxyuridine 228.204 C9 H12 N2 O5 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)CO)) LIGAND-CPD:C00526:*CAS:951-78-0 deoxyuridine = deoxyribose-1-phosphate + uracil salvage pathways of pyrimidine deoxyribonucleotides glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-glucosyl-(1->3)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1,6)]-α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 3297.691 C156 H260 N2 O67 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC3(C(O)C(C(O)C(O3)COC6(OC(COC4(C(C(O)C(O)C(O4)CO)OC5(OC(CO)C(O)C(O)C(O)5)))C(O)C(C(O)6)OC7(C(C(O)C(O)C(O7)CO)OC8(OC(CO)C(O)C(O)C(O)8))))OC9(C(C(O)C(O)C(O9)CO)OC10(C(C(O)C(O)C(O10)CO)OC11(C(O)C(C(O)C(O11)CO)OC12(OC(CO)C(O)C(O)C(O)12))))))) glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-glucosyl phosphate = (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-glucosyl-(1->3)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1,6)]-α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 3297.691 C156 H260 N2 O67 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC3(C(O)C(C(O)C(O3)COC6(OC(COC4(C(C(O)C(O)C(O4)CO)OC5(OC(CO)C(O)C(O)C(O)5)))C(O)C(C(O)6)OC7(C(C(O)C(O)C(O7)CO)OC8(OC(CO)C(O)C(O)C(O)8))))OC9(C(C(O)C(O)C(O9)CO)OC10(C(C(O)C(O)C(O10)CO)OC11(C(O)C(C(O)C(O11)CO)OC12(OC(CO)C(O)C(O)C(O)12))))))) (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-glucosyl phosphate = glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis lupiwighteone 8-prenyl-5,7,4'-trihydroxyisoflavone 338.359 C20 H18 O5 CC(C)=CCc3(c2(OC=C(c1(ccc(O)cc1))C(=O)c2c(O)cc3O)) 2.5.1.1 genistein + dimethylallyl-PP = lupiwighteone + diphosphate wighteone and luteone biosynthesis 8'-hydroxyabscisate 8´-HOABA 280.32 C15 H20 O5 CC1(C(C(C)=CC(=O)C1)(O)C=CC(C)=CC(=O)O)(CO) 8'-hydroxyabscisate = phaseic acid phaseic acid biosynthesis 8'-hydroxyabscisate 8´-HOABA 280.32 C15 H20 O5 CC1(C(C(C)=CC(=O)C1)(O)C=CC(C)=CC(=O)O)(CO) 1.14.13.93 (+)-abscisate + NADPH + O2 = 8'-hydroxyabscisate + NADP+ + H2O phaseic acid biosynthesis L-canaline L-a-amino-g-(aminooxy)-n-butyric acid*L-2-amino-4-(aminooxy)butyric acid*L-2-amino-4-(aminooxy)butyrate 134.135 C4 H10 N2 O3 C(ON)CC(N)C(O)=O CAS:496-93-5 3.5.3.1 canavanine + H2O = L-canaline + urea canavanine degradation L-canaline L-a-amino-g-(aminooxy)-n-butyric acid*L-2-amino-4-(aminooxy)butyric acid*L-2-amino-4-(aminooxy)butyrate 134.135 C4 H10 N2 O3 C(ON)CC(N)C(O)=O CAS:496-93-5 1.6.6.- L-canaline + NADPH = homoserine + ammonia + NADP+ canavanine degradation L-canaline L-a-amino-g-(aminooxy)-n-butyric acid*L-2-amino-4-(aminooxy)butyric acid*L-2-amino-4-(aminooxy)butyrate 134.135 C4 H10 N2 O3 C(ON)CC(N)C(O)=O CAS:496-93-5 2.1.3.3 L-canaline + carbamoyl-phosphate = O-ureidohomoserine canavanine biosynthesis L-canaline L-a-amino-g-(aminooxy)-n-butyric acid*L-2-amino-4-(aminooxy)butyric acid*L-2-amino-4-(aminooxy)butyrate 134.135 C4 H10 N2 O3 C(ON)CC(N)C(O)=O CAS:496-93-5 homoserine + ammonia = L-canaline canavanine biosynthesis anandamide arachidonylethanolamide*AnNH*arachidonoyl-EA*N-arachidonoyl ethanolamine 347.54 C22 H37 N1 O2 C(=O)(NCCO)CCCC=CCC=CCC=CCC=CCCCCC CAS:94421-68-8: 3.5.1.4 anandamide + H2O = arachidonate + ethanolamine anandamide degradation dUDP 2'-deoxyuridine-5'-diphosphate*deoxyuridine-diphosphate 388.164 C9 H14 N2 O11 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C01346: 2.7.4.6 dUDP + ATP = dUTP + ADP de novo biosynthesis of pyrimidine deoxyribonucleotides dUDP 2'-deoxyuridine-5'-diphosphate*deoxyuridine-diphosphate 388.164 C9 H14 N2 O11 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C01346: 1.17.4.1 dUDP + H2O = UDP de novo biosynthesis of pyrimidine deoxyribonucleotides dUDP 2'-deoxyuridine-5'-diphosphate*deoxyuridine-diphosphate 388.164 C9 H14 N2 O11 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C01346: 1.17.4.- UDP = dUDP + H2O de novo biosynthesis of pyrimidine deoxyribonucleotides 2-aminoadipate-6-semialdehyde L-2-aminoadipate 6-semialdehyde*2-aminoadipate 6-semialdehyde*α-aminoadipate 6-semialdehyde*2-aminoadipate semialdehyde*allysine 145.158 C6 H11 N1 O3 C(=O)(O)C(N)CCCC=O CAS:1962-83-0 1.5.1.9 H2O + NAD+ + saccharopine = L-glutamate + NADH + 2-aminoadipate-6-semialdehyde lysine degradation II 2-aminoadipate-6-semialdehyde L-2-aminoadipate 6-semialdehyde*2-aminoadipate 6-semialdehyde*α-aminoadipate 6-semialdehyde*2-aminoadipate semialdehyde*allysine 145.158 C6 H11 N1 O3 C(=O)(O)C(N)CCCC=O CAS:1962-83-0 1.2.1.31 2-aminoadipate-6-semialdehyde + H2O = α-aminoadipate + H+ lysine biosynthesis IV 2-aminoadipate-6-semialdehyde L-2-aminoadipate 6-semialdehyde*2-aminoadipate 6-semialdehyde*α-aminoadipate 6-semialdehyde*2-aminoadipate semialdehyde*allysine 145.158 C6 H11 N1 O3 C(=O)(O)C(N)CCCC=O CAS:1962-83-0 1.2.1.31 2-aminoadipate-6-semialdehyde + H2O + NAD+ = α-aminoadipate + NADH lysine degradation II 2-aminoadipate-6-semialdehyde L-2-aminoadipate 6-semialdehyde*2-aminoadipate 6-semialdehyde*α-aminoadipate 6-semialdehyde*2-aminoadipate semialdehyde*allysine 145.158 C6 H11 N1 O3 C(=O)(O)C(N)CCCC=O CAS:1962-83-0 1.5.1.10 2-aminoadipate-6-semialdehyde + NADPH + L-glutamate = saccharopine + NADP+ + H2O lysine biosynthesis IV D-glucosamine-6-phosphate D-glucosamine phosphate*D-glucosamine 6-phosphate*D-glucosamine-6-P*glucosamine-6-P*glucosamine-6-phosphate 259.152 C6 H14 N1 O8 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(N)C(O1)O) LIGAND-CPD:C00352:*CAS:3616-42-0 2.6.1.16 fructose-6-phosphate + L-glutamine = L-glutamate + D-glucosamine-6-phosphate UDP-N-acetylgalactosamine biosynthesis D-glucosamine-6-phosphate D-glucosamine phosphate*D-glucosamine 6-phosphate*D-glucosamine-6-P*glucosamine-6-P*glucosamine-6-phosphate 259.152 C6 H14 N1 O8 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(N)C(O1)O) LIGAND-CPD:C00352:*CAS:3616-42-0 2.3.1.4 D-glucosamine-6-phosphate + acetyl-CoA = N-acetyl-D-glucosamine-6-phosphate + coenzyme A UDP-N-acetylgalactosamine biosynthesis L-lysine K*lysine*L-lys*lys*2,6-diaminohexanoic acid*lysine acid 146.189 C6 H14 N2 O2 C(=O)(O)C(N)CCCCN LIGAND-CPD:C00047:*CAS:56-87-1 4.1.1.20 meso-diaminopimelate = CO2 + L-lysine lysine biosynthesis VI L-lysine K*lysine*L-lys*lys*2,6-diaminohexanoic acid*lysine acid 146.189 C6 H14 N2 O2 C(=O)(O)C(N)CCCCN LIGAND-CPD:C00047:*CAS:56-87-1 4.1.1.20 meso-diaminopimelate = CO2 + L-lysine lysine biosynthesis II L-lysine K*lysine*L-lys*lys*2,6-diaminohexanoic acid*lysine acid 146.189 C6 H14 N2 O2 C(=O)(O)C(N)CCCCN LIGAND-CPD:C00047:*CAS:56-87-1 4.1.1.20 meso-diaminopimelate = CO2 + L-lysine lysine biosynthesis I L-lysine K*lysine*L-lys*lys*2,6-diaminohexanoic acid*lysine acid 146.189 C6 H14 N2 O2 C(=O)(O)C(N)CCCCN LIGAND-CPD:C00047:*CAS:56-87-1 1.5.1.7 H2O + NAD+ + saccharopine = NADH + α-ketoglutarate + L-lysine lysine biosynthesis IV L-lysine K*lysine*L-lys*lys*2,6-diaminohexanoic acid*lysine acid 146.189 C6 H14 N2 O2 C(=O)(O)C(N)CCCCN LIGAND-CPD:C00047:*CAS:56-87-1 6.1.1.6 L-lysine + ATP = diphosphate + AMP tRNA charging pathway L-lysine K*lysine*L-lys*lys*2,6-diaminohexanoic acid*lysine acid 146.189 C6 H14 N2 O2 C(=O)(O)C(N)CCCCN LIGAND-CPD:C00047:*CAS:56-87-1 4.1.1.18 L-lysine = CO2 + cadaverine lysine degradation I L-lysine K*lysine*L-lys*lys*2,6-diaminohexanoic acid*lysine acid 146.189 C6 H14 N2 O2 C(=O)(O)C(N)CCCCN LIGAND-CPD:C00047:*CAS:56-87-1 1.5.1.8 H2O + NADP+ + saccharopine = NADPH + α-ketoglutarate + L-lysine lysine degradation II biotin vitamin H*coenzyme R*d-biotin 244.308 C10 H16 N2 O3 S1 C1(SC([CH]2([CH]1NC(N2)=O))CCCCC(O)=O) LIGAND-CPD:C00120:*CAS:58-85-5 6.3.4.15 biotin + ATP = diphosphate + AMP biotin-carboxyl carrier protein biotin vitamin H*coenzyme R*d-biotin 244.308 C10 H16 N2 O3 S1 C1(SC([CH]2([CH]1NC(N2)=O))CCCCC(O)=O) LIGAND-CPD:C00120:*CAS:58-85-5 2.8.1.6 9-mercaptodethiobiotin = biotin biotin biosynthesis II biotin vitamin H*coenzyme R*d-biotin 244.308 C10 H16 N2 O3 S1 C1(SC([CH]2([CH]1NC(N2)=O))CCCCC(O)=O) LIGAND-CPD:C00120:*CAS:58-85-5 2.8.1.6 dethiobiotin + S-adenosyl-L-methionine + sulfur donor = biotin + 5'-deoxyadenosine + L-methionine biotin biosynthesis I phosphoryl-choline choline phosphate*phosphocholine*N-Trimethyl-2-aminoethylphosphonate*O-Phosphocholine 184.152 C5 H15 N1 O4 P1 C([N+](C)(C)C)COP(O)(=O)O CAS:107-73-3 2.1.1.103 N-dimethylethanolamine phosphate + S-adenosyl-L-methionine = phosphoryl-choline + S-adenosyl-L-homocysteine choline biosynthesis I phosphoryl-choline choline phosphate*phosphocholine*N-Trimethyl-2-aminoethylphosphonate*O-Phosphocholine 184.152 C5 H15 N1 O4 P1 C([N+](C)(C)C)COP(O)(=O)O CAS:107-73-3 3.1.3.75 phosphoryl-choline + H2O = choline choline biosynthesis I phosphoryl-choline choline phosphate*phosphocholine*N-Trimethyl-2-aminoethylphosphonate*O-Phosphocholine 184.152 C5 H15 N1 O4 P1 C([N+](C)(C)C)COP(O)(=O)O CAS:107-73-3 2.7.1.32 choline + ATP = phosphoryl-choline + ADP phospholipid biosynthesis II phosphoryl-choline choline phosphate*phosphocholine*N-Trimethyl-2-aminoethylphosphonate*O-Phosphocholine 184.152 C5 H15 N1 O4 P1 C([N+](C)(C)C)COP(O)(=O)O CAS:107-73-3 2.7.7.15 phosphoryl-choline + CTP = CDP-choline + diphosphate phospholipid biosynthesis II phosphoryl-choline choline phosphate*phosphocholine*N-Trimethyl-2-aminoethylphosphonate*O-Phosphocholine 184.152 C5 H15 N1 O4 P1 C([N+](C)(C)C)COP(O)(=O)O CAS:107-73-3 2.7.7.15 phosphoryl-choline + CTP = CDP-choline + diphosphate choline biosynthesis III 3-hydroxy-5- oxohexanoyl-CoA 895.661 C27 H44 N7 O19 P3 S1 C(CSC(=O)CC(O)CC(=O)C)NC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)n2(c3(c(nc2)c(N)ncn3))) UM-BBD-CPD:c0029: 2.8.3.- 3-hydroxy-5-oxohexanoate + acetyl-CoA = 3-hydroxy-5- oxohexanoyl-CoA + acetate gallate degradation III (anaerobic) 3-hydroxy-5- oxohexanoyl-CoA 895.661 C27 H44 N7 O19 P3 S1 C(CSC(=O)CC(O)CC(=O)C)NC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)n2(c3(c(nc2)c(N)ncn3))) UM-BBD-CPD:c0029: 2.3.1.- 3-hydroxy-5- oxohexanoyl-CoA + coenzyme A = 3-hydroxybutyryl-CoA + acetyl-CoA gallate degradation III (anaerobic) uridine 244.204 C9 H12 N2 O6 c1(n(c(=O)[nH]c(c1)=O)C2(C(O)C(O)C(O2)CO)) LIGAND-CPD:C00299:*CAS:58-96-8 3.5.4.5 H2O + cytidine = ammonia + uridine salvage pathways of purine and pyrimidine nucleotides uridine 244.204 C9 H12 N2 O6 c1(n(c(=O)[nH]c(c1)=O)C2(C(O)C(O)C(O2)CO)) LIGAND-CPD:C00299:*CAS:58-96-8 3.5.4.5 H2O + cytidine = ammonia + uridine (deoxy)ribose phosphate degradation uridine 244.204 C9 H12 N2 O6 c1(n(c(=O)[nH]c(c1)=O)C2(C(O)C(O)C(O2)CO)) LIGAND-CPD:C00299:*CAS:58-96-8 3.5.4.5 H2O + cytidine = ammonia + uridine salvage pathways of pyrimidine ribonucleotides uridine 244.204 C9 H12 N2 O6 c1(n(c(=O)[nH]c(c1)=O)C2(C(O)C(O)C(O2)CO)) LIGAND-CPD:C00299:*CAS:58-96-8 2.7.1.48 uridine + GTP = UMP + GDP salvage pathways of pyrimidine ribonucleotides uridine 244.204 C9 H12 N2 O6 c1(n(c(=O)[nH]c(c1)=O)C2(C(O)C(O)C(O2)CO)) LIGAND-CPD:C00299:*CAS:58-96-8 2.7.1.48 uridine + ATP = UMP + ADP salvage pathways of purine and pyrimidine nucleotides uridine 244.204 C9 H12 N2 O6 c1(n(c(=O)[nH]c(c1)=O)C2(C(O)C(O)C(O2)CO)) LIGAND-CPD:C00299:*CAS:58-96-8 2.4.2.3 uridine = ribose-1-phosphate + uracil (deoxy)ribose phosphate degradation uridine 244.204 C9 H12 N2 O6 c1(n(c(=O)[nH]c(c1)=O)C2(C(O)C(O)C(O2)CO)) LIGAND-CPD:C00299:*CAS:58-96-8 2.4.2.3 uridine = ribose-1-phosphate + uracil salvage pathways of pyrimidine ribonucleotides 4-oxo-4-(3-pyridyl)-butanoate 4-oxo-4-(3-pyridyl)-butanoic acid*3-succinoylpyridine*γ-oxo-3-pyridinebutanoic acid*γ-oxo-3-pyridinebutanoate 179.175 C9 H9 N1 O3 c1(ncc(cc1)C(=O)CCC(O)=O) 4-oxo-4-(3-pyridyl)-N-methylbutanamide = 4-oxo-4-(3-pyridyl)-butanoate nicotine degradation III 4-oxo-4-(3-pyridyl)-butanoate 4-oxo-4-(3-pyridyl)-butanoic acid*3-succinoylpyridine*γ-oxo-3-pyridinebutanoic acid*γ-oxo-3-pyridinebutanoate 179.175 C9 H9 N1 O3 c1(ncc(cc1)C(=O)CCC(O)=O) 4-(methylamino)-1-(3-pyridyl)-1-butanone = 4-oxo-4-(3-pyridyl)-butanoate nicotine degradation II 4-oxo-4-(3-pyridyl)-butanoate 4-oxo-4-(3-pyridyl)-butanoic acid*3-succinoylpyridine*γ-oxo-3-pyridinebutanoic acid*γ-oxo-3-pyridinebutanoate 179.175 C9 H9 N1 O3 c1(ncc(cc1)C(=O)CCC(O)=O) 4-oxo-4-(3-pyridyl)-butanoate = 4-hydroxy-4-(3-pyridyl)-butanoate nicotine degradation II 4-oxo-4-(3-pyridyl)-butanoate 4-oxo-4-(3-pyridyl)-butanoic acid*3-succinoylpyridine*γ-oxo-3-pyridinebutanoic acid*γ-oxo-3-pyridinebutanoate 179.175 C9 H9 N1 O3 c1(ncc(cc1)C(=O)CCC(O)=O) 4-oxo-4-(3-pyridyl)-butanoate = 4-hydroxy-4-(3-pyridyl)-butanoate nicotine degradation III 4-oxo-4-(3-pyridyl)-butanoate 4-oxo-4-(3-pyridyl)-butanoic acid*3-succinoylpyridine*γ-oxo-3-pyridinebutanoic acid*γ-oxo-3-pyridinebutanoate 179.175 C9 H9 N1 O3 c1(ncc(cc1)C(=O)CCC(O)=O) 4-oxo-4-(3-pyridyl)-butanamide = 4-oxo-4-(3-pyridyl)-butanoate nicotine degradation II 4-oxo-4-(3-pyridyl)-butanoate 4-oxo-4-(3-pyridyl)-butanoic acid*3-succinoylpyridine*γ-oxo-3-pyridinebutanoic acid*γ-oxo-3-pyridinebutanoate 179.175 C9 H9 N1 O3 c1(ncc(cc1)C(=O)CCC(O)=O) 4-oxo-4-(3-pyridyl)-butanamide = 4-oxo-4-(3-pyridyl)-butanoate nicotine 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(=O)(O)C(N)CC(C)C LIGAND-CPD:C00123:*NCI:46709*CAS:61-90-5 6.1.1.4 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(=O)(O)C(N)CC(C)C LIGAND-CPD:C00123:*NCI:46709*CAS:61-90-5 3.5.1.- indole-3-acetyl-leu + 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(=O)(O)C(N)CC(C)C LIGAND-CPD:C00123:*NCI:46709*CAS:61-90-5 2.6.1.42 L-leucine + α-ketoglutarate = L-glutamate + 2-ketoisocaproate 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(=O)(O)C(N)CC(C)C LIGAND-CPD:C00123:*NCI:46709*CAS:61-90-5 2.6.1.42 L-leucine + α-ketoglutarate = L-glutamate + 2-ketoisocaproate 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(=O)(O)C(N)CC(C)C LIGAND-CPD:C00123:*NCI:46709*CAS:61-90-5 2.6.1.42 L-leucine + α-ketoglutarate = L-glutamate + 2-ketoisocaproate leucine degradation I 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(=O)(O)C(N)CC(C)C LIGAND-CPD:C00123:*NCI:46709*CAS:61-90-5 indole-3-acetate + L-leucine = indole-3-acetyl-leu + H2O IAA conjugate biosynthesis II 3-hydroxy-L-kynurenine L-3-hydroxykynurenine*3-hydroxy-kynurenine 224.216 C10 H12 N2 O4 C(=O)(O)C(N)CC(=O)c1(c(N)c(O)ccc1) CAS:606-14-4 1.14.13.9 O2 + NADPH + kynurenine = H2O + NADP+ + 3-hydroxy-L-kynurenine tryptophan degradation III (eukaryotic) 3-hydroxy-L-kynurenine L-3-hydroxykynurenine*3-hydroxy-kynurenine 224.216 C10 H12 N2 O4 C(=O)(O)C(N)CC(=O)c1(c(N)c(O)ccc1) CAS:606-14-4 3.7.1.3 3-hydroxy-L-kynurenine + H2O = 3-hydroxy-anthranilate + L-alanine tryptophan degradation III (eukaryotic) 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 349.233 C12 H16 N1 O9 P1 C(OP(O)(O)=O)C(O)C(O)C(=O)CNc1(c(C(O)=O)cccc1) LIGAND-CPD:C01302: 4.1.1.48 1-(o-carboxyphenylamino)-1'-deoxyribulose-5'-phosphate = indole-3-glycerol-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 349.233 C12 H16 N1 O9 P1 C(OP(O)(O)=O)C(O)C(O)C(=O)CNc1(c(C(O)=O)cccc1) LIGAND-CPD:C01302: 5.3.1.24 tryptophan biosynthesis 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol 414.67 C28 H46 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(CO)C(O)CC4)))) 1.14.13.72 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol 414.67 C28 H46 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(CO)C(O)CC4)))) 1.14.13.72 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-formyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol 414.67 C28 H46 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(CO)C(O)CC4)))) 1.14.13.72 4-α-methyl zymosterol + O2 = 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol 414.67 C28 H46 O2 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(CO)C(O)CC4)))) 1.14.13.72 4-α-methyl zymosterol + O2 = 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) calystegine A3 159.185 C7 H13 N1 O3 C12(NC(CC1)(O)C(O)C(O)C2) unknown = calystegine A3 calystegine biosynthesis GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 2.7.1.48 uridine + GTP = UMP + GDP salvage pathways of pyrimidine ribonucleotides GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 GDP = dGDP + H2O purine nucleotides de novo biosynthesis I GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 (mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)3-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 3.1.7.2 guanosine 5'-diphosphate,3'-diphosphate + H2O = diphosphate + GDP ppGpp biosynthesis GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 2.7.7.22 α-D-mannose 1-phosphate + GDP = GDP-D-mannose GDP-mannose metabolism GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 2.7.6.5 ATP + GDP = AMP + guanosine 5'-diphosphate,3'-diphosphate ppGpp biosynthesis GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = adenylo-succinate + GDP salvage pathways of purine nucleosides GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = adenylo-succinate + GDP purine nucleotides de novo biosynthesis II GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = adenylo-succinate + GDP purine nucleotides de novo biosynthesis I GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 1.17.4.1 dGDP + H2O = GDP purine nucleotides de novo biosynthesis I GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 2.4.1.83 dolichyl-phosphate + GDP-D-mannose = dolichyl β-D-mannosyl phosphate + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 (mannosyl)4-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 2.7.4.6 GDP + ATP = GTP + ADP purine nucleotides de novo biosynthesis I GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 (mannosyl)3-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)4-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 GDP-D-mannose + H2O = GDP + mannose GDP-mannose metabolism GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 4.1.1.32 oxaloacetate + GTP = CO2 + phosphoenolpyruvate + GDP asparagine degradation I GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 2.4.1.132 mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 2.7.1.- cytidine + GTP = CMP + GDP salvage pathways of pyrimidine ribonucleotides GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 2.4.1.142 (N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 2.7.4.8 GMP + ATP = GDP + ADP salvage pathways of purine and pyrimidine nucleotides GDP ppG*guanosine-5'-diphosphate*guanosine-diphosphate 443.203 C10 H15 N5 O11 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00035:*CAS:146-91-8 2.7.4.8 GMP + ATP = GDP + ADP purine nucleotides de novo biosynthesis I sphinganine dihydrosphingosine*sphinganine*erythro-D-sphinganine*DHS 301.512 C18 H39 N1 O2 CCCCCCCCCCCCCCCC(O)C(N)CO CAS:764-22-7 1.14.-.- sphinganine + O2 + NADPH = 4-hydroxysphinganine + H2O + NADP+ sphingolipid metabolism sphinganine dihydrosphingosine*sphinganine*erythro-D-sphinganine*DHS 301.512 C18 H39 N1 O2 CCCCCCCCCCCCCCCC(O)C(N)CO CAS:764-22-7 2.7.1.91 sphinganine + ATP = sphinganine 1-phosphate + ADP sphingolipid metabolism sphinganine dihydrosphingosine*sphinganine*erythro-D-sphinganine*DHS 301.512 C18 H39 N1 O2 CCCCCCCCCCCCCCCC(O)C(N)CO CAS:764-22-7 2.7.1.91 sphinganine + ATP = sphinganine 1-phosphate + ADP sphingolipid metabolism sphinganine dihydrosphingosine*sphinganine*erythro-D-sphinganine*DHS 301.512 C18 H39 N1 O2 CCCCCCCCCCCCCCCC(O)C(N)CO CAS:764-22-7 1.1.1.102 NADP+ + sphinganine = NADPH + 3-dehydrosphinganine sphingolipid metabolism capsidiol 236.353 C15 H24 O2 CC12(C(=CCC(C1)C(=C)C)C(O)CC(O)C(C)2) 1-deoxy-capsidiol + O2 + NADPH = capsidiol + H2O + NADP+ capsidiol biosynthesis capsidiol 236.353 C15 H24 O2 CC12(C(=CCC(C1)C(=C)C)C(O)CC(O)C(C)2) 3-deoxy-capsidiol + O2 + NADPH = capsidiol + H2O + NADP+ capsidiol biosynthesis ε,ε-carotene-3-diol 552.882 C40 H56 O1 CC(C=CC1(C(C)(C)CC(O)C=C1C))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)=CCCC(C)2C) 1.14.99.- ε,ε-carotene-3-diol + O2 = lactucaxanthin + H2O lactucaxanthin biosynthesis ε,ε-carotene-3-diol 552.882 C40 H56 O1 CC(C=CC1(C(C)(C)CC(O)C=C1C))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)=CCCC(C)2C) 1.14.99.- ε-carotene + O2 = ε,ε-carotene-3-diol + H2O lactucaxanthin biosynthesis 16:0-18:3-DGDG 1-16:0-2-18:3-digalactosyldiacylglycerol*1-hexadecanoyl-2-(9Z,12Z,15Z-octadecatrienoyl)-3-O-[alpha-D-galactosyl-(1>6)-O-beta-D-galactosyl]-sn-glycerol 915.209 C49 H86 O15 C(OC1(OC(C(O)C(O)C1O)COC2(C(O)C(O)C(O)C(O2)CO)))C(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 16:0-18:2-DGDG = 16:0-18:3-DGDG glycolipid desaturation Fe(III)-PS iron-PS*iron-phytosiderophore*Fe(III)-phytosiderophore Fe(III)-PS = Fe(III)-PS Fe(III)-phytosiderophore transport H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.15.1.1 O2- + H+ = H2O2 + O2 removal of superoxide radicals H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.86 2,3-dihydroxy-isovalerate + NADP+ = 2-acetolactate + NADPH + H+ valine biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.3.3 coproporphyrinogen III + O2 + H+ = protoporphyrinogen IX + CO2 + H2O heme biosynthesis II H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.3.3 coproporphyrinogen III + O2 + H+ = protoporphyrinogen IX + CO2 + H2O chlorophyllide a biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.78 ent-kaur-16-en-19-ol + NADPH + H+ + O2 = ent-kaur-16-en-19-al + NADP+ + H2O GA12 biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: (2S)-2-amino-3-oxo-4-phosphonooxybutanoate + H+ = 1-amino-propan-2-one-3-phosphate + CO2 pyridoxal 5'-phosphate biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.15.7 choline + O2 + H+ = betaine aldehyde hydrate + H2O glycine betaine biosynthesis III (plants) H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.12.98.2 5,10-methenyltetrahydromethanopterin + H2 = 5,10-methylene-tetrahydromethanopterin + H+ methanogenesis from CO2 H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.243 (-)-trans-carveol + NADP+ = (-)-carvone + NADPH + H+ menthol biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.- O2 = 2-phosphoglycolate + 3-phosphoglycerate + H+ photorespiration H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.94 sn-glycerol-3-phosphate = dihydroxy-acetone-phosphate + H+ phospholipid biosynthesis I H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.51 dalbergioidin + NADP+ = 2'-hydroxygenistein + NADPH + H+ kievitone biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 3.5.1.4 acrylamide + H2O = ammonia + acrylate + H+ acrylonitrile degradation H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.2 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H+ = dimethylallyl-PP + H2O methylerythritol phosphate pathway H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ purine degradation H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ salvage pathways of adenine, hypoxanthine, and their nucleosides H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ ureide biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: isopentenyl adenosine + H2O = trans-zeatin riboside + H+ trans-zeatin biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.3 homoserine = L-aspartate-semialdehyde + H+ homoserine biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.87 homoisocitrate + NAD+ = α-ketoadipate + CO2 + NADH + H+ lysine biosynthesis IV H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.2 L-proline = H+ proline biosynthesis V (from arginine) H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.2 L-proline = H+ proline biosynthesis II H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.2 L-proline = H+ arginine degradation VI (arginase 2 pathway) H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.2 L-proline = H+ proline biosynthesis I H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.8.1.4 NAD+ = NADH + H+ branched-chain α-keto acid dehydrogenase complex H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.187 GDP-D-rhamnose = GDP-4-dehydro-6-deoxy-D-mannose + H+ GDP-D-rhamnose biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.70 NADPH + O2 + obtusifoliol + H+ = H2O + NADP+ + formate + (4α)-methyl-(5α)-ergosta-8,14,24(28)-trien-3β-ol sterol biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.99.8 indole-3-glyoxal + NADH + H+ = indole-3-ketol + NAD+ tryptophan degradation V (side chain pathway) H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.20 5-methyl-THF = 5,10-methylene-THF + H+ folate transformations H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.20 5-methyl-THF = 5,10-methylene-THF + H+ formylTHF biosynthesis II H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.20 5-methyl-THF = 5,10-methylene-THF + H+ formylTHF biosynthesis I H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.88 (R)-mevalonate + NAD+ + coenzyme A = 3-hydroxy-3-methyl-glutaryl-CoA + NADH + H+ mevalonate degradation H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.12.99.6 H2 = H+ respiration (anaerobic)-- electron donors reaction list H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.26 tetrahydrodipicolinate = H+ lysine biosynthesis VI H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.26 tetrahydrodipicolinate = H+ lysine biosynthesis II H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.26 tetrahydrodipicolinate = H+ lysine biosynthesis I H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.1 3-methylthiopropanal + NADH + H+ = methionol + NAD+ methionine degradation III H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.4 acetoacetate + H+ = acetone + CO2 acetone degradation (to methylglyoxal) H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.70 glutamate-1-semialdehyde + NADP+ = NADPH + H+ tetrapyrrole biosynthesis I H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: O2 + H+ = trimethylamine + D,L-malic semialdehyde + H2O carnitine degradation III H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.2 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + H+ = H2O methylerythritol phosphate pathway H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.5.1.12 H2O = L-glutamate + H+ proline degradation II H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.193 5-amino-6-(5'-phosphoribitylamino)uracil + NADP+ = 5-amino-6-(5'-phosphoribosylamino)uracil + NADPH + H+ flavin biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.90 zeaxanthin + H+ + O2 = antheraxanthin + H2O carotenoid biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.90 zeaxanthin + H+ + O2 = antheraxanthin + H2O xanthophyll cycle H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.85 3-isopropylmalate + NAD+ = 2-isopropyl-3-oxosuccinate + NADH + H+ leucine biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.78 ent-kaur-16-en-19-al + NADPH + H+ + O2 = ent-kaurenoate + NADP+ + H2O GA12 biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.99.8 indole-3-glycol aldehyde + NADH + H+ = indole-3-glycol + NAD+ tryptophan degradation V (side chain pathway) H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.8.1.9 NADP+ = NADPH + H+ thioredoxin pathway H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.72 D-erythrose-4-phosphate + NAD+ + H2O = erythronate-4-phosphate + NADH + H+ pyridoxal 5'-phosphate biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.1.75 divinyl protochlorophyllide a + NADPH + H+ + H+ = monovinyl protochlorophyllide a + NADP+ chlorophyllide a biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.79 ent-7-α-hydroxykaurenoate + NADPH + H+ + O2 = GA12-aldehyde + NADP+ + H2O GA12 biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.5.- fumarate + menaquinol + H+ = succinate + menaquinone-8 mixed acid fermentation H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.3.5.- fumarate + menaquinol + H+ = succinate + menaquinone-8 respiration (anaerobic) H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.60 glycerate = tartronate semialdehyde + H+ glycolate and glyoxylate degradation I H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.60 glycerate = tartronate semialdehyde + H+ allantoin degradation I H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.284 S-hydroxymethylglutathione = S-formylglutathione + H+ formaldehyde oxidation II (glutathione-dependent) H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.81 Mg-protoporphyrin monomethyl ester + NADPH + H+ + O2 = 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.8.1.4 NAD+ = NADH + H+ pyruvate dehydrogenase complex H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 4.3.1.12 L-ornithine + NAD+ = L-proline + ammonia + NADH + H+ arginine degradation VII (arginase 3 pathway) H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.12.7.2 H2 = H+ glutamate degradation VII (to butyrate) H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: photosynthesis, light reaction H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.49 β-D-glucose-6-phosphate + NADP+ = D-glucono-δ-lactone-6-phosphate + NADPH + H+ pentose phosphate pathway (oxidative branch) H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.8.1.4 NAD+ = NADH + H+ glycine cleavage complex H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ purine degradation H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ salvage pathways of purine nucleosides II (plant) H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.-.-.- RCC + H+ = pFCC chlorophyll a degradation H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.246 (-)-vestitone + NADPH + H+ = 7,2'-dihydroxy-4'-methoxy-isoflavanol + NADP+ medicarpin biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.41 L-glutamate γ-semialdehyde + NADP+ = L-glutamate-5-phosphate + NADPH + H+ proline biosynthesis II H+ hydrogen ion*proton*H 1.008 H1 [H+] 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 1.008 H1 [H+] 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 1.008 H1 [H+] 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 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 4.99.1.1 Fe2+ + protoporphyrin IX = H+ + protoheme IX heme biosynthesis II H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.31 2-aminoadipate-6-semialdehyde + H2O = α-aminoadipate + H+ lysine biosynthesis IV H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: NAD+ = dipicolinate + NADH + H+ lysine biosynthesis II H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.282 shikimate = 3-dehydro-shikimate + H+ chorismate biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 4.1.1.39 CO2 + H2O = 3-phosphoglycerate + H+ Calvin cycle H+ hydrogen ion*proton*H 1.008 H1 [H+] 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 1.008 H1 [H+] 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 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.8.1.7 glutathione + NADP+ = glutathione disulfide + NADPH + H+ ascorbate glutathione cycle H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 6.4.1.2 ATP + acetyl-CoA + HCO3- + H+ = ADP + malonyl-CoA fatty acid biosynthesis - initial steps H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.5 D,L-malic semialdehyde + H2O = malate + H+ carnitine degradation III H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.90 antheraxanthin + H+ + O2 = violaxanthin + H2O carotenoid biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.90 antheraxanthin + H+ + O2 = violaxanthin + H2O xanthophyll cycle H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.2.1.5 indole acetaldehyde + H2O = indole-3-acetate + H+ tryptophan degradation V (side chain pathway) H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: isopentenyladenine + H2O = trans-zeatin + H+ trans-zeatin biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: H2O = H+ + e- + O2 photosynthesis, light reaction H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.1.1.290 erythronate-4-phosphate + NAD+ = 2-oxo-3-hydroxy-4-phosphobutanoate + NADH + H+ pyridoxal 5'-phosphate biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: hypoxanthine + H2O = H+ + xanthine salvage pathways of adenine, hypoxanthine, and their nucleosides H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 6.6.1.1 ATP + protoporphyrin IX + Mg2+ + H2O = Mg-protoporphyrin + ADP + H+ chlorophyllide a biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.81 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = divinyl protochlorophyllide a + NADP+ + H2O chlorophyllide a biosynthesis H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.8.1.4 NAD+ = NADH + H+ 2-keto glutarate dehydrogenase complex H+ hydrogen ion*proton*H 1.008 H1 [H+] CAS:12408-02-5:*LIGAND-CPD:C00080: 1.14.13.81 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis L-idonate L-idonic acid 196.157 C6 H12 O7 C(O)C(O)C(O)C(O)C(O)C(=O)O LIGAND-CPD:C00770:*CAS:1114-17-6 1.1.1.264 L-idonate = 5-ketogluconate L-idonate degradation GA8 gibberellin A8*gibberellin A8*GA8 364.394 C19 H24 O7 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(C(O)C(O)C3)(C)[CH]4C5C(=O)O)))(O)) 1.14.11.- GA8 + α-ketoglutarate + O2 = GA8-catabolite + succinate + CO2 + H2O gibberellin inactivation GA8 gibberellin A8*gibberellin A8*GA8 364.394 C19 H24 O7 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(C(O)C(O)C3)(C)[CH]4C5C(=O)O)))(O)) 1.14.11.13 GA1 + α-ketoglutarate + O2 = GA8 + succinate + CO2 gibberellin inactivation protein-S-sulfanylcysteine [enzyme]-S-sulfanylcysteine C3 H5 N1 O1 |Protein|2 S2 2.8.1.7 L-cysteine = L-alanine + protein-S-sulfanylcysteine alanine biosynthesis III polypeptide LIGAND-CPD:C00403: indole-3-acetate + polypeptide = indole-3-acetyl-polypeptide IAA conjugate biosynthesis II zymosterol 5α-cholesta-8,24-dien-3β-ol*δ8, 24-cholestadien-3β-ol 384.644 C27 H44 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)CC(O)CC4)))) LIGAND-CPD:C05437:*CAS:128-33-6 1.1.1.270 5α-cholesta-8,24-dien-3-one + NADPH = zymosterol + NADP+ cholesterol biosynthesis I zymosterol 5α-cholesta-8,24-dien-3β-ol*δ8, 24-cholestadien-3β-ol 384.644 C27 H44 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)CC(O)CC4)))) LIGAND-CPD:C05437:*CAS:128-33-6 1.1.1.270 5α-cholesta-8,24-dien-3-one + NADPH = zymosterol + NADP+ cholesterol biosynthesis III (via desmosterol) zymosterol 5α-cholesta-8,24-dien-3β-ol*δ8, 24-cholestadien-3β-ol 384.644 C27 H44 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)CC(O)CC4)))) LIGAND-CPD:C05437:*CAS:128-33-6 5.3.3.5 zymosterol = 5α-cholesta-7,24-dien-3β-ol cholesterol biosynthesis I zymosterol 5α-cholesta-8,24-dien-3β-ol*δ8, 24-cholestadien-3β-ol 384.644 C27 H44 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)CC(O)CC4)))) LIGAND-CPD:C05437:*CAS:128-33-6 5.3.3.5 zymosterol = 5α-cholesta-7,24-dien-3β-ol cholesterol biosynthesis III (via desmosterol) 18:2-18:2-MGDG 1-18:2-2-18:2-monogalactosyldiacylglycerol*1,2-(9Z,12Z-octadecadienoyl)-3-O-beta-D-galactosyl-sn-glycerol 795.105 C45 H78 O11 C(OC1(C(O)C(O)C(OO)C(O1)CO))C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-18:2-MGDG = 18:3-18:2-MGDG glycolipid desaturation 18:2-18:2-MGDG 1-18:2-2-18:2-monogalactosyldiacylglycerol*1,2-(9Z,12Z-octadecadienoyl)-3-O-beta-D-galactosyl-sn-glycerol 795.105 C45 H78 O11 C(OC1(C(O)C(O)C(OO)C(O1)CO))C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-18:2-MGDG = 18:2-18:3-MGDG glycolipid desaturation dihydroxyphaseic acid (-)-dihydroxyphaseic acid*DPA 282.336 C15 H22 O5 CC12(C(C(C)(OC1)CC(O)C2)(O)C=CC(C)=CC(=O)O) 1.-.-.- phaseic acid = dihydroxyphaseic acid + an oxidized acceptor phaseic acid biosynthesis menaquinone-8 vitamin K2*MK-8*menaquinone 717.129 C51 H72 O2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(=C(C)C(=O)c2(c(C(=O)1)cccc2)) CAS:84-81-1:*LIGAND-CPD:C00828: 1.3.5.- fumarate + menaquinol + H+ = succinate + menaquinone-8 mixed acid fermentation menaquinone-8 vitamin K2*MK-8*menaquinone 717.129 C51 H72 O2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(=C(C)C(=O)c2(c(C(=O)1)cccc2)) CAS:84-81-1:*LIGAND-CPD:C00828: 1.3.5.- fumarate + menaquinol + H+ = succinate + menaquinone-8 respiration (anaerobic) menaquinone-8 vitamin K2*MK-8*menaquinone 717.129 C51 H72 O2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(=C(C)C(=O)c2(c(C(=O)1)cccc2)) CAS:84-81-1:*LIGAND-CPD:C00828: demethylmenaquinone-8 + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + menaquinone-8 menaquinone biosynthesis menaquinone-8 vitamin K2*MK-8*menaquinone 717.129 C51 H72 O2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(=C(C)C(=O)c2(c(C(=O)1)cccc2)) CAS:84-81-1:*LIGAND-CPD:C00828: 1.2.1.2 formate + menaquinone-8 = CO2 + menaquinol respiration (anaerobic)-- electron donors reaction list menaquinone-8 vitamin K2*MK-8*menaquinone 717.129 C51 H72 O2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(=C(C)C(=O)c2(c(C(=O)1)cccc2)) CAS:84-81-1:*LIGAND-CPD:C00828: 1.2.1.2 formate + menaquinone-8 = CO2 + menaquinol formate oxidation to CO2 acetone cyanohydrin 2-hydroxy-2-methylpropanenitrile*2-hydroxyisobutyronitrile 85.105 C4 H7 N1 O1 C(#N)C(C)(C)O NCI:131093*CAS:75-86-5 4.1.2.37 acetone cyanohydrin = acetone + hydrogen cyanide linamarin degradation acetone cyanohydrin 2-hydroxy-2-methylpropanenitrile*2-hydroxyisobutyronitrile 85.105 C4 H7 N1 O1 C(#N)C(C)(C)O NCI:131093*CAS:75-86-5 3.2.1.21 linamarin + H2O = acetone cyanohydrin + β-D-glucose linamarin degradation ubiquinol-8 ubiquinol(8) 731.153 C49 H78 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(O)C(OC)=C(OC)C(O)C=1C) LIGAND-CPD:C00390: 1.6.5.3 ubiquinone-8 + NADH = ubiquinol-8 + NAD+ aerobic respiration -- electron donors reaction list ubiquinol-8 ubiquinol(8) 731.153 C49 H78 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(O)C(OC)=C(OC)C(O)C=1C) LIGAND-CPD:C00390: 1.6.5.3 ubiquinone-8 + NADH = ubiquinol-8 + NAD+ respiration (anaerobic)-- electron donors reaction list ubiquinol-8 ubiquinol(8) 731.153 C49 H78 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(O)C(OC)=C(OC)C(O)C=1C) LIGAND-CPD:C00390: 1.6.5.3 ubiquinone-8 + NADH = ubiquinol-8 + NAD+ NAD/NADH phosphorylation and dephosphorylation ubiquinol-8 ubiquinol(8) 731.153 C49 H78 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(O)C(OC)=C(OC)C(O)C=1C) LIGAND-CPD:C00390: 1.2.2.2 pyruvate + ubiquinone-8 + H2O = ubiquinol-8 + acetate + CO2 mixed acid fermentation ubiquinol-8 ubiquinol(8) 731.153 C49 H78 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(O)C(OC)=C(OC)C(O)C=1C) LIGAND-CPD:C00390: 1.1.99.5 sn-glycerol-3-phosphate + ubiquinone-8 = dihydroxy-acetone-phosphate + ubiquinol-8 aerobic respiration -- electron donors reaction list ubiquinol-8 ubiquinol(8) 731.153 C49 H78 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(O)C(OC)=C(OC)C(O)C=1C) LIGAND-CPD:C00390: 1.1.99.5 sn-glycerol-3-phosphate + ubiquinone-8 = dihydroxy-acetone-phosphate + ubiquinol-8 respiration (anaerobic)-- electron donors reaction list ubiquinol-8 ubiquinol(8) 731.153 C49 H78 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(O)C(OC)=C(OC)C(O)C=1C) LIGAND-CPD:C00390: 1.1.99.5 sn-glycerol-3-phosphate + ubiquinone-8 = dihydroxy-acetone-phosphate + ubiquinol-8 glycerol 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(C(C)(O1)C)CC2) (-)-α-terpineol = 1,8-cineole monoterpene biosynthesis 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(OC(CSC)C(O)C(O)1)(O) LIGAND-CPD:C03089:*PUBCHEM:494: 3.2.2.16 5'-methylthioadenosine + H2O = 5-methylthioribose + adenine methionine salvage pathway 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(OC(CSC)C(O)C(O)1)(O) LIGAND-CPD:C03089:*PUBCHEM:494: 2.7.1.100 ATP + 5-methylthioribose = ADP + 5-methylthioribose-1-phosphate methionine salvage pathway 5-methyl-tetrahydromethanopterin 5-methyl-5,6,7,8-tetrahydromethanopterin*N5-methyl-5,6,7,8-tetrahydromethanopterin*5-methyl-H4MPT*methyl-H4MPT*5-methyl-THMPT 789.709 C31 H46 N6 O16 P1 C[CH]([CH]1([CH](C)[NH]c2(c(N1C)c(=O)[nH]c(n2)N)))Nc3(ccc(cc3)CC(O)C(O)C(O)COC4(OC(C(O)C4O)COP(=O)([O-])OC(C(O)=O)CCC(O)=O)) 2.1.1.86 5-methyl-tetrahydromethanopterin = tetrahydromethanopterin methanogenesis from CO2 5-methyl-tetrahydromethanopterin 5-methyl-5,6,7,8-tetrahydromethanopterin*N5-methyl-5,6,7,8-tetrahydromethanopterin*5-methyl-H4MPT*methyl-H4MPT*5-methyl-THMPT 789.709 C31 H46 N6 O16 P1 C[CH]([CH]1([CH](C)[NH]c2(c(N1C)c(=O)[nH]c(n2)N)))Nc3(ccc(cc3)CC(O)C(O)C(O)COC4(OC(C(O)C4O)COP(=O)([O-])OC(C(O)=O)CCC(O)=O)) 1.5.99.11 5-methyl-tetrahydromethanopterin = 5,10-methylene-tetrahydromethanopterin methanogenesis from CO2 GA29-catabolite gibberellin A29-catabolite*gibberellin A29-catabolite*GA29-catabolite 346.379 C19 H22 O6 CC1([CH]4(C(=CC(=O)C1)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA29 + α-ketoglutarate + O2 = GA29-catabolite + succinate + CO2 + H2O gibberellin inactivation phytocassane E 1β-hydroxy-12,15-cassadien-3,11-dione*1beta-hydroxy-12,15-cassadien-3,11-dione 316.439 C20 H28 O3 CC1(C(C=C)=CC(=O)[CH]2(C3(C)([CH](CC[CH]12)C(C)(C)C(=O)CC3O))) phytocassane C = phytocassane E phytocassane biosynthesis an oxidized acceptor 1.2.1.5 indole-3-glyoxal + H2O + an oxidized acceptor = indole-3-glyoxylate tryptophan degradation V (side chain pathway) an oxidized acceptor 1.2.1.5 indole-3-glycol aldehyde + H2O + an oxidized acceptor = indole-3-glycolate tryptophan degradation V (side chain pathway) an oxidized acceptor 1.-.-.- phaseic acid = dihydroxyphaseic acid + an oxidized acceptor phaseic 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 292.417 C18 H28 O3 C(O)(=O)CCCCCCCC1(C(C(=O)C=C1)CC=CCC) 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 292.417 C18 H28 O3 C(O)(=O)CCCCCCCC1(C(C(=O)C=C1)CC=CCC) 1.3.1.42 NADP+ + 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate = NADPH + 12-oxo-cis-10,15-phytodienoate jasmonic acid biosynthesis lipid LIGAND-CPD:C01356: 1.11.1.12 glutathione + a lipid hydroperoxide = glutathione disulfide + lipid + H2O glutathione redox reactions I 5-hydroxy-ferulic-acid 5-hydroxy ferulate 210.186 C10 H10 O5 C(O)(=O)C=Cc1(cc(OC)c(O)c(O)c1) ferulate + NADPH + O2 = 5-hydroxy-ferulic-acid + H2O + NADP+ free phenylpropanoid acid biosynthesis 5-hydroxy-ferulic-acid 5-hydroxy ferulate 210.186 C10 H10 O5 C(O)(=O)C=Cc1(cc(OC)c(O)c(O)c1) 2.1.1.68 5-hydroxy-ferulic-acid + S-adenosyl-L-methionine = sinapate + S-adenosyl-L-homocysteine free phenylpropanoid acid biosynthesis UDP-3-O-(3-hydroxymyristoyl)glucosamine UDP-3-O-(3-hydroxytetradecanoyl)-D-glucosamine*UDP-3-O-(3-hydroxytetradecanoyl)glucosamine 791.679 C29 H51 N3 O18 P2 CCCCCCCCCCCC(O)CC(=O)OC1(C(N)C(OC(C1O)CO)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c(=O)[nH]c(=O)cc3))) LIGAND-CPD:C06022: 2.3.1.- UDP-3-O-(3-hydroxymyristoyl)glucosamine = UDP-2,3-bis(3-hydroxymyristoyl)glucosamine lipid-A-precursor biosynthesis UDP-3-O-(3-hydroxymyristoyl)glucosamine UDP-3-O-(3-hydroxytetradecanoyl)-D-glucosamine*UDP-3-O-(3-hydroxytetradecanoyl)glucosamine 791.679 C29 H51 N3 O18 P2 CCCCCCCCCCCC(O)CC(=O)OC1(C(N)C(OC(C1O)CO)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c(=O)[nH]c(=O)cc3))) LIGAND-CPD:C06022: UDP-3-O-(3-hydroxymyristoyl)-N-acetylglucosamine + H2O = UDP-3-O-(3-hydroxymyristoyl)glucosamine + acetate lipid-A-precursor biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 p-aminobenzoate + UDP-D-glucose = p-aminobenzoate-β-D-glucopyranosyl ester + UDP tetrahydrofolate biosynthesis II UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.117 dolichyl-phosphate + UDP-D-glucose = dolichyl β-D-glucosyl phosphate + UDP dolichyl-diphosphooligosaccharide biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.15 UDP-D-glucose + α-D-glucose 6-phosphate = UDP + trehalose 6-phosphate trehalose biosynthesis I UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- isopentenyladenine + UDP-D-glucose = isopentenyladenine-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- trans-zeatin + UDP-D-glucose = trans-zeatin-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- dihydrozeatin + UDP-D-glucose = dihydrozeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate sucrose degradation III UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate sucrose degradation to ethanol and lactate (anaerobic) UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate galactose degradation II UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate UDP-glucose conversion UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate sucrose biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- trans-zeatin-O-glucoside + UDP-D-glucose = trans-zeatin-O-glucoside-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.7.7.12 UDP-D-glucose + α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-galactose UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP sucrose degradation III UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP sucrose degradation to ethanol and lactate (anaerobic) UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP galactose degradation II UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP sucrose biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- cis-zeatin + UDP-D-glucose = cis-zeatin-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.114 2-coumarate + UDP-D-glucose = trans-β-D-Glucosyl-2-hydroxycinnamate + UDP coumarin biosynthesis (via 2-coumarate) UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.115 UDP-D-glucose + pelargonidin = UDP + pelargonidin-3-O-β-D-glucoside anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- kinetin + UDP-D-glucose = kinetin-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- trans-zeatin + UDP-D-glucose = trans-zeatin-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.14 fructose-6-phosphate + UDP-D-glucose = sucrose-6-phosphate + UDP sucrose biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.115 UDP-D-glucose + delphinidin = UDP + delphinidin-3-O-β-D-glucoside anthocyanin biosynthesis (delphinidin 3-O-glucoside) UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 1.1.1.22 UDP-D-glucose + H2O + NAD+ = UDP-D-glucuronate + NADH UDP-D-xylose biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 1.1.1.22 UDP-D-glucose + H2O + NAD+ = UDP-D-glucuronate + NADH galactose degradation II UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 3.13.1.1 sulfite + UDP-D-glucose = UDP-sulfoquinovose + H2O glycolipid biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- dihydrozeatin + UDP-D-glucose = dihydrozeatin-7-N-dihydrozeatin + UDP cytokinins 7-N-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- benzyladenine + UDP-D-glucose = benzyladenine-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.238 delphinidin-3,5-diglucoside + UDP-D-glucose = delphinidin 3,5,3'-triglucoside + UDP gentiodelphin biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- delphinidin 3-O-glucosyl-5-O-caffeoylglucoside + UDP-D-glucose = delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + UDP gentiodelphin biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 5.1.3.2 UDP-D-glucose = UDP-galactose galactose degradation II UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 5.1.3.2 UDP-D-glucose = UDP-galactose UDP-glucose conversion UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 5.1.3.2 UDP-D-glucose = UDP-galactose UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.203 trans-zeatin + UDP-D-glucose = trans-zeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- dihydrozeatin + UDP-D-glucose = dihydrozeatin-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- hydroxy-β-cyclocitral + UDP-D-glucose = picrocrocin + UDP crocetin biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.215 cis-zeatin + UDP-D-glucose = cis-zeatin-O-glucoside + UDP cytokinins-O-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- dihydrozeatin-9-N-glucoside + UDP-D-glucose = dihydrozeatin-9-N-glucoside-O-glucoside + UDP cytokinins-O-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.121 indole-3-acetate + UDP-D-glucose = indole-3-acetyl-β-1-D-glucose + UDP IAA conjugate biosynthesis II UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.121 indole-3-acetate + UDP-D-glucose = indole-3-acetyl-β-1-D-glucose + UDP IAA conjugate biosynthesis I UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- kinetin + UDP-D-glucose = kinetin-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- cis-zeatin + UDP-D-glucose = cis-zeatin-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- isopentenyladenine + UDP-D-glucose = isopentenyladenine-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.115 UDP-D-glucose + cyanidin = UDP + cyanidin-3-O-β-D-glucoside anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- benzyladenine + UDP-D-glucose = benzyladenine-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis UDP-D-glucose UDPG*UDP-glucose 566.305 C15 H24 N2 O17 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(O)(=O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(c(=O)[nH]c(=O)cc3)) LIGAND-CPD:C00029:*CAS:133-89-1 2.4.1.- delphinidin-3-O-β-D-glucoside + UDP-D-glucose = delphinidin-3,5-diglucoside + UDP gentiodelphin biosynthesis 6-kestotriose 6-kestose 504.441 C18 H32 O16 C(O)C1(OC(C(O)C(O)1)COC2(C(O)C(O)C(O2)CO)(CO))(OC3(C(O)C(O)C(O)C(O3)CO)) 2.4.1.10 sucrose + sucrose = 6-kestotriose + β-D-glucose fructan biosynthesis trans-2-hexenal 98.144 C6 H10 O1 CCCC=CC=O CAS:6728-26-3 trans-2-hexenal = trans-2-hexenol 13-LOX and 13-HPL pathway trans-2-hexenal 98.144 C6 H10 O1 CCCC=CC=O CAS:6728-26-3 cis-3-hexenal = trans-2-hexenal 13-LOX and 13-HPL pathway oryzalexin B 3-Hydroxy-7-oxy-sandaracopimaradien*3-Hydroxy-7-oxy-sandaracopimaradiene 302.456 C20 H30 O2 C=CC2(C)(CCC3(C1(C)([CH](C(C)(C)C(=O)CC1)CC(O)C(=C2)3))) oryzalexin D = oryzalexin B oryzalexin A-F biosynthesis oryzalexin B 3-Hydroxy-7-oxy-sandaracopimaradien*3-Hydroxy-7-oxy-sandaracopimaradiene 302.456 C20 H30 O2 C=CC2(C)(CCC3(C1(C)([CH](C(C)(C)C(=O)CC1)CC(O)C(=C2)3))) oryzalexin B = oryzalexin C oryzalexin A-F biosynthesis C25-allenic-apo-aldehyde 384.558 C25 H36 O3 CC(=CC=CC=C(C)CO)C=CC=C(C)C=C=C1(C(C)(C)CC(O)CC(C)(O)1) 1.13.11.51 9'-cis-neoxanthin + O2 = 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 167.104 C5 H3 N4 O3 c2(=O)([nH]c([O-])nc1([nH]c(=O)[nH]c12)) LIGAND-CPD:C00366:*CAS:69-93-2 1.7.3.3 urate + O2 + H2O = 5-hydroxyisourate + H2O2 ureide biosynthesis urate 8-hydroxyxanthine*2,6,8-trihydroxypurine*trioxopurine*2,6,8-trioxypurine*purine-2,6,8-(1H,3H,9H)-trione*uric acid 167.104 C5 H3 N4 O3 c2(=O)([nH]c([O-])nc1([nH]c(=O)[nH]c12)) LIGAND-CPD:C00366:*CAS:69-93-2 1.7.3.3 urate + O2 = allantoin + CO2 + H2O2 purine degradation urate 8-hydroxyxanthine*2,6,8-trihydroxypurine*trioxopurine*2,6,8-trioxypurine*purine-2,6,8-(1H,3H,9H)-trione*uric acid 167.104 C5 H3 N4 O3 c2(=O)([nH]c([O-])nc1([nH]c(=O)[nH]c12)) LIGAND-CPD:C00366:*CAS:69-93-2 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ purine degradation urate 8-hydroxyxanthine*2,6,8-trihydroxypurine*trioxopurine*2,6,8-trioxypurine*purine-2,6,8-(1H,3H,9H)-trione*uric acid 167.104 C5 H3 N4 O3 c2(=O)([nH]c([O-])nc1([nH]c(=O)[nH]c12)) LIGAND-CPD:C00366:*CAS:69-93-2 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ salvage pathways of adenine, hypoxanthine, and their nucleosides urate 8-hydroxyxanthine*2,6,8-trihydroxypurine*trioxopurine*2,6,8-trioxypurine*purine-2,6,8-(1H,3H,9H)-trione*uric acid 167.104 C5 H3 N4 O3 c2(=O)([nH]c([O-])nc1([nH]c(=O)[nH]c12)) LIGAND-CPD:C00366:*CAS:69-93-2 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ ureide biosynthesis uroporphyrinogen-III 836.805 C40 H40 N4 O16 C(=O)(O)CCc4(c3(Cc1(nc(c(CC(O)=O)c1CCC(=O)O)Cc2(nc(c(CC(=O)O)c2CCC(O)=O)Cc5(nc(Cc(n3)c4CC(=O)O)c(CC(O)=O)c5CCC(=O)O))))) LIGAND-CPD:C01051:*CAS:1976-85-8 4.2.1.75 hydroxymethylbilane = uroporphyrinogen-III + H2O tetrapyrrole biosynthesis I uroporphyrinogen-III 836.805 C40 H40 N4 O16 C(=O)(O)CCc4(c3(Cc1(nc(c(CC(O)=O)c1CCC(=O)O)Cc2(nc(c(CC(=O)O)c2CCC(O)=O)Cc5(nc(Cc(n3)c4CC(=O)O)c(CC(O)=O)c5CCC(=O)O))))) LIGAND-CPD:C01051:*CAS:1976-85-8 4.1.1.37 uroporphyrinogen-III = CO2 + coproporphyrinogen III heme biosynthesis II uroporphyrinogen-III 836.805 C40 H40 N4 O16 C(=O)(O)CCc4(c3(Cc1(nc(c(CC(O)=O)c1CCC(=O)O)Cc2(nc(c(CC(=O)O)c2CCC(O)=O)Cc5(nc(Cc(n3)c4CC(=O)O)c(CC(O)=O)c5CCC(=O)O))))) LIGAND-CPD:C01051:*CAS:1976-85-8 4.1.1.37 uroporphyrinogen-III = CO2 + coproporphyrinogen III chlorophyllide a biosynthesis oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 4.1.1.32 oxaloacetate + GTP = CO2 + phosphoenolpyruvate + GDP asparagine degradation I oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate glutamine degradation III oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate asparagine degradation I oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate aspartate biosynthesis I oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate aspartate degradation II oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate asparagine biosynthesis I oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = citrate + coenzyme A TCA cycle variation I oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = citrate + coenzyme A respiration (anaerobic) oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = citrate + coenzyme A TCA cycle oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 4.1.1.49 oxaloacetate + ATP = CO2 + phosphoenolpyruvate + ADP gluconeogenesis oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 mixed acid fermentation oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 reductive TCA cycle I oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 gluconeogenesis oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 4.1.1.31 oxaloacetate = phosphoenolpyruvate + H2O + CO2 respiration (anaerobic) oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 1.1.1.37 malate + NAD+ = oxaloacetate + NADH mixed acid fermentation oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 1.1.1.37 malate + NAD+ = oxaloacetate + NADH TCA cycle variation I oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 1.1.1.37 malate + NAD+ = oxaloacetate + NADH reductive TCA cycle I oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 1.1.1.37 malate + NAD+ = oxaloacetate + NADH gluconeogenesis oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 1.1.1.37 malate + NAD+ = oxaloacetate + NADH respiration (anaerobic) oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 1.1.1.37 malate + NAD+ = oxaloacetate + NADH aspartate degradation II oxaloacetate keto-oxaloacetate*oxaloacetic acid*oxalacetic acid*oxaloacetate*oxalacetate 132.073 C4 H4 O5 C(O)(=O)CC(=O)C(=O)O LIGAND-CPD:C00036:*CAS:328-42-7 1.1.1.37 malate + NAD+ = oxaloacetate + NADH TCA cycle gluconate D-gluconate*D-gluconoate*gluconic acid*D-gluconic acid*dextronic acid*aldonic acid*maltonic acid 196.157 C6 H12 O7 C(O)(=O)[CH](O)[CH](O)[CH](O)[CH](O)CO LIGAND-CPD:C00257:*CAS:526-95-4 2.7.1.12 ATP + gluconate = 6-phospho-D-gluconate + ADP L-idonate degradation gluconate D-gluconate*D-gluconoate*gluconic acid*D-gluconic acid*dextronic acid*aldonic acid*maltonic acid 196.157 C6 H12 O7 C(O)(=O)[CH](O)[CH](O)[CH](O)[CH](O)CO LIGAND-CPD:C00257:*CAS:526-95-4 1.1.1.69 gluconate = 5-ketogluconate L-idonate degradation CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.5 sn-glycerol-3-phosphate = CMP phospholipid biosynthesis I CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.5 sn-glycerol-3-phosphate = CMP phospholipid biosynthesis II CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.5 sn-glycerol-3-phosphate = CMP cardiolipin biosynthesis CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 6.3.2.5 D-4'-phosphopantothenate + L-cysteine + CTP = 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 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.2 CDP-choline = CMP phospholipid biosynthesis II CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.2 CDP-choline = CMP choline biosynthesis III CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.8 L-serine = CMP phospholipid biosynthesis I CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.8 L-serine = CMP phospholipid biosynthesis II CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.1 CDP-ethanolamine = CMP phospholipid biosynthesis II CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.1.- cytidine + ATP = CMP + ADP salvage pathways of purine and pyrimidine nucleotides CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.4.14 ATP + CMP = ADP + CDP salvage pathways of purine and pyrimidine nucleotides CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.4.14 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 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.1.- cytidine + GTP = 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 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: cardiolipin biosynthesis CMP 5'-cytidylic acid*cytidine-5'-monophosphate*cytidylate*cytidylic acid*C*cytidine-P*cytidine-monophosphate*cytidine-phosphate*cytidine-5'-phosphate 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) 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 323.199 C9 H14 N3 O8 P1 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)O)) CAS:84-52-6:*LIGAND-CPD:C00055:*CAS:63-37-6*PUBCHEM:6131: 2.7.8.11 myo-inositol = CMP phospholipid biosynthesis II nicotine-1'-N-oxide nicotine N'-oxide 178.233 C10 H14 N2 O1 c1(ncc(cc1)[CH]2(N(C)(=O)CCC2)) 1.14.13.8 nicotine + NADPH + O2 = nicotine-1'-N-oxide + NADP+ + H2O nicotine degradation II 1-aminocyclopropane-1-carboxylate 1-Aminocyclopropane-1-carboxylic acid 101.105 C4 H7 N1 O2 C(O)(=O)C1(CC1)(N) CAS:22059-21-8 1.14.17.4 L-ascorbate + 1-aminocyclopropane-1-carboxylate + O2 = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine 1-aminocyclopropane-1-carboxylate 1-Aminocyclopropane-1-carboxylic acid 101.105 C4 H7 N1 O2 C(O)(=O)C1(CC1)(N) CAS:22059-21-8 4.4.1.14 S-adenosyl-L-methionine = 5'-methylthioadenosine + 1-aminocyclopropane-1-carboxylate methionine salvage pathway 1-aminocyclopropane-1-carboxylate 1-Aminocyclopropane-1-carboxylic acid 101.105 C4 H7 N1 O2 C(O)(=O)C1(CC1)(N) CAS:22059-21-8 4.4.1.14 S-adenosyl-L-methionine = 5'-methylthioadenosine + 1-aminocyclopropane-1-carboxylate ethylene biosynthesis from methionine reduced pyrroloquinoline-quinone PQQH2 332.226 C14 H8 N2 O8 C(=O)(O)c1(cc2(c([nH]1)c3(c(c(O)c(O)2)nc(C(O)=O)cc3C(=O)O))) 1.1.99.25 quinate + pyrroloquinoline quinone = 3-dehydroquinate + reduced pyrroloquinoline-quinone quinate degradation cis-aconitate 174.11 C6 H6 O6 C(=O)(O)CC(C(=O)O)=CC(O)=O CAS:585-84-2 4.2.1.3 TCA cycle variation I cis-aconitate 174.11 C6 H6 O6 C(=O)(O)CC(C(=O)O)=CC(O)=O CAS:585-84-2 4.2.1.3 reductive TCA cycle I cis-aconitate 174.11 C6 H6 O6 C(=O)(O)CC(C(=O)O)=CC(O)=O CAS:585-84-2 4.2.1.3 respiration (anaerobic) cis-aconitate 174.11 C6 H6 O6 C(=O)(O)CC(C(=O)O)=CC(O)=O CAS:585-84-2 4.2.1.3 TCA cycle cis-aconitate 174.11 C6 H6 O6 C(=O)(O)CC(C(=O)O)=CC(O)=O CAS:585-84-2 4.2.1.3 citrate = cis-aconitate + H2O TCA cycle variation I cis-aconitate 174.11 C6 H6 O6 C(=O)(O)CC(C(=O)O)=CC(O)=O CAS:585-84-2 4.2.1.3 citrate = cis-aconitate + H2O reductive TCA cycle I cis-aconitate 174.11 C6 H6 O6 C(=O)(O)CC(C(=O)O)=CC(O)=O CAS:585-84-2 4.2.1.3 citrate = cis-aconitate + H2O respiration (anaerobic) cis-aconitate 174.11 C6 H6 O6 C(=O)(O)CC(C(=O)O)=CC(O)=O CAS:585-84-2 4.2.1.3 citrate = cis-aconitate + H2O TCA cycle protoporphyrinogen IX protoporphyrinogen 568.714 C34 H36 N4 O4 Cc3(c(CCC(=O)O)c4(Cc1(nc(c(C)c1CCC(O)=O)Cc2(nc(c(C=C)c(C)2)Cc5(nc(Cc3n4)c(C=C)c(C)5))))) LIGAND-CPD:C01079:*CAS:7412-77-3 1.3.3.4 protoporphyrinogen IX + O2 = protoporphyrin IX + H2O heme biosynthesis II protoporphyrinogen IX protoporphyrinogen 568.714 C34 H36 N4 O4 Cc3(c(CCC(=O)O)c4(Cc1(nc(c(C)c1CCC(O)=O)Cc2(nc(c(C=C)c(C)2)Cc5(nc(Cc3n4)c(C=C)c(C)5))))) LIGAND-CPD:C01079:*CAS:7412-77-3 1.3.3.4 protoporphyrinogen IX + O2 = protoporphyrin IX + H2O chlorophyllide a biosynthesis protoporphyrinogen IX protoporphyrinogen 568.714 C34 H36 N4 O4 Cc3(c(CCC(=O)O)c4(Cc1(nc(c(C)c1CCC(O)=O)Cc2(nc(c(C=C)c(C)2)Cc5(nc(Cc3n4)c(C=C)c(C)5))))) LIGAND-CPD:C01079:*CAS:7412-77-3 1.3.3.3 coproporphyrinogen III + O2 + H+ = protoporphyrinogen IX + CO2 + H2O heme biosynthesis II protoporphyrinogen IX protoporphyrinogen 568.714 C34 H36 N4 O4 Cc3(c(CCC(=O)O)c4(Cc1(nc(c(C)c1CCC(O)=O)Cc2(nc(c(C=C)c(C)2)Cc5(nc(Cc3n4)c(C=C)c(C)5))))) LIGAND-CPD:C01079:*CAS:7412-77-3 1.3.3.3 coproporphyrinogen III + O2 + H+ = protoporphyrinogen IX + CO2 + H2O chlorophyllide a biosynthesis adenylo-succinate N6-(1,2-dicarboxyethyl)-AMP*adenylo-succ 463.297 C14 H18 N5 O11 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(ncn3)N[CH](C(O)=O)CC(O)=O))) LIGAND-CPD:C03794:*CAS:19240-42-7 4.3.2.2 adenylo-succinate = fumarate + AMP salvage pathways of purine nucleosides adenylo-succinate N6-(1,2-dicarboxyethyl)-AMP*adenylo-succ 463.297 C14 H18 N5 O11 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(ncn3)N[CH](C(O)=O)CC(O)=O))) 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*adenylo-succ 463.297 C14 H18 N5 O11 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(ncn3)N[CH](C(O)=O)CC(O)=O))) LIGAND-CPD:C03794:*CAS:19240-42-7 4.3.2.2 adenylo-succinate = fumarate + AMP purine nucleotides de novo biosynthesis I adenylo-succinate N6-(1,2-dicarboxyethyl)-AMP*adenylo-succ 463.297 C14 H18 N5 O11 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(ncn3)N[CH](C(O)=O)CC(O)=O))) LIGAND-CPD:C03794:*CAS:19240-42-7 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = adenylo-succinate + GDP salvage pathways of purine nucleosides adenylo-succinate N6-(1,2-dicarboxyethyl)-AMP*adenylo-succ 463.297 C14 H18 N5 O11 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(ncn3)N[CH](C(O)=O)CC(O)=O))) LIGAND-CPD:C03794:*CAS:19240-42-7 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = adenylo-succinate + GDP purine nucleotides de novo biosynthesis II adenylo-succinate N6-(1,2-dicarboxyethyl)-AMP*adenylo-succ 463.297 C14 H18 N5 O11 P1 C(OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(ncn3)N[CH](C(O)=O)CC(O)=O))) LIGAND-CPD:C03794:*CAS:19240-42-7 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = adenylo-succinate + GDP purine nucleotides de novo biosynthesis I N-methyl-Δ1-pyrrolinium cation 1-methyl-Δ1-pyrrolinium ion 84.141 C5 H10 N1 C1([N+](C)=CCC1) N-methyl-Δ1-pyrrolinium cation = hygrine calystegine biosynthesis nicotinamide riboside N-ribosyl-nicotinamide*nicotinamide ribonucleoside*nicotinamide ribose*nicotinamide-β-riboside*ribosylnicotinamide 255.25 C11 H15 N2 O5 c1([n+](cccc1C(N)=O)[CH]2([CH](O)[CH](O)[CH](O2)CO)) CAS:1341-23-7 2.7.1.22 nicotinamide riboside + ATP = nicotinamide mononucleotide + ADP NAD salvage pathway II nicotinamide riboside N-ribosyl-nicotinamide*nicotinamide ribonucleoside*nicotinamide ribose*nicotinamide-β-riboside*ribosylnicotinamide 255.25 C11 H15 N2 O5 c1([n+](cccc1C(N)=O)[CH]2([CH](O)[CH](O)[CH](O2)CO)) CAS:1341-23-7 3.1.3.5 nicotinamide mononucleotide + H2O = nicotinamide riboside NAD salvage pathway II nicotinamide riboside N-ribosyl-nicotinamide*nicotinamide ribonucleoside*nicotinamide ribose*nicotinamide-β-riboside*ribosylnicotinamide 255.25 C11 H15 N2 O5 c1([n+](cccc1C(N)=O)[CH]2([CH](O)[CH](O)[CH](O2)CO)) 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([n+](cccc1C(N)=O)[CH]2([CH](O)[CH](O)[CH](O2)CO)) CAS:1341-23-7 3.2.2.1 nicotinamide riboside + H2O = nicotinamide + D-ribose pyridine nucleotide cycling (plants) resveratrol 3,5,4'-trihydroxystilbene 228.247 C14 H12 O3 c1(c(cc(O)cc(O)1)C=Cc2(ccc(O)cc2)) 2.3.1.95 malonyl-CoA + coumaroyl-CoA = resveratrol + coenzyme A + CO2 resveratrol biosynthesis 3-hydroxypropionyl-CoA 3-hydroxypropionyl-coenzyme A*3-Hydroxypropanoyl-CoA*3-Hydroxypropanoyl coenzymeA 839.597 C24 H40 N7 O18 P3 S1 c1(c2(c(ncn1)n(cn2)C3(OC(C(C(O)3)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCO)))(N) 4.2.1.17 acrylyl-CoA + H2O = 3-hydroxypropionyl-CoA β-alanine biosynthesis II 3-hydroxypropionyl-CoA 3-hydroxypropionyl-coenzyme A*3-Hydroxypropanoyl-CoA*3-Hydroxypropanoyl coenzymeA 839.597 C24 H40 N7 O18 P3 S1 c1(c2(c(ncn1)n(cn2)C3(OC(C(C(O)3)OP(O)(=O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCO)))(N) 3.1.2.4 3-hydroxypropionyl-CoA + H2O = 3-hydroxy-propionate + coenzyme A β-alanine biosynthesis II pimeloyl-CoA 6-carboxyhexanoyl-CoA*pimelyl-CoA 909.688 C28 H46 N7 O19 P3 S1 C(O)(=O)CCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(O)(=O)OCC1(OC(C(O)C1OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C01063: 2.3.1.47 pimeloyl-CoA + L-alanine = CO2 + coenzyme A + 7-keto-8-aminopelargonate biotin biosynthesis II pimeloyl-CoA 6-carboxyhexanoyl-CoA*pimelyl-CoA 909.688 C28 H46 N7 O19 P3 S1 C(O)(=O)CCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(O)(=O)OCC1(OC(C(O)C1OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C01063: 2.3.1.47 pimeloyl-CoA + L-alanine = CO2 + coenzyme A + 7-keto-8-aminopelargonate biotin biosynthesis I thymine 5-methyluracil*5-methyl-2,4(1H,3H)-pyrimidinedione 126.115 C5 H6 N2 O2 c1(c(C)c(=O)[nH]c(=O)[nH]1) LIGAND-CPD:C00178:*CAS:65-71-4: 2.4.2.4 thymidine = deoxyribose-1-phosphate + thymine salvage pathways of purine and pyrimidine nucleotides thymine 5-methyluracil*5-methyl-2,4(1H,3H)-pyrimidinedione 126.115 C5 H6 N2 O2 c1(c(C)c(=O)[nH]c(=O)[nH]1) LIGAND-CPD:C00178:*CAS:65-71-4: 2.4.2.4 thymidine = deoxyribose-1-phosphate + thymine (deoxy)ribose phosphate degradation thymine 5-methyluracil*5-methyl-2,4(1H,3H)-pyrimidinedione 126.115 C5 H6 N2 O2 c1(c(C)c(=O)[nH]c(=O)[nH]1) LIGAND-CPD:C00178:*CAS:65-71-4: 2.4.2.4 thymidine = deoxyribose-1-phosphate + thymine salvage pathways of pyrimidine deoxyribonucleotides methionol 3-methylthiopropanol*3-methylmercapto-1-propanol*3-hydroxypropyl methyl sulfide*γ-methylmercaptopropyl alcohol*3-methylsulfanyl-1-propanol 106.182 C4 H10 O1 S1 C(SC)CCO PUBCHEM::10448: 1.1.1.1 3-methylthiopropanal + NADH + H+ = methionol + NAD+ methionine 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 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*LIGAND-CPD:C01172: 5.3.1.9 β-D-glucose-6-phosphate = fructose-6-phosphate ascorbate 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 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*LIGAND-CPD:C01172: 5.3.1.9 β-D-glucose-6-phosphate = 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 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*LIGAND-CPD:C01172: 5.3.1.9 β-D-glucose-6-phosphate = fructose-6-phosphate gluconeogenesis β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*LIGAND-CPD:C01172: 5.3.1.9 β-D-glucose-6-phosphate = 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 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*LIGAND-CPD:C01172: 5.3.1.9 β-D-glucose-6-phosphate = fructose-6-phosphate glucose fermentation to lactate II β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*LIGAND-CPD:C01172: 5.3.1.9 β-D-glucose-6-phosphate = 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 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*LIGAND-CPD:C01172: 5.5.1.4 β-D-glucose-6-phosphate = D-myo-inositol (3)-monophosphate myo-inositol 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 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*LIGAND-CPD:C01172: 5.5.1.4 β-D-glucose-6-phosphate = D-myo-inositol (3)-monophosphate lipid-independent phytate 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 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*LIGAND-CPD:C01172: 3.2.1.26 H2O + sucrose-6-phosphate = β-D-glucose-6-phosphate + fructose 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 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*LIGAND-CPD:C01172: 2.7.1.2 β-D-glucose + ATP = β-D-glucose-6-phosphate + ADP trehalose degradation II (high osmolarity) β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*LIGAND-CPD:C01172: 1.1.1.49 β-D-glucose-6-phosphate + NADP+ = D-glucono-δ-lactone-6-phosphate + 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 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*LIGAND-CPD:C01172: 2.7.1.1 β-D-glucose + ATP = β-D-glucose-6-phosphate + ADP glucose fermentation to lactate II β-D-glucose-6-phosphate D-glucose-6-P*glucose-6-P*glucose-6-phosphate*β-D-glucose-6-P*D-glucose-6-phosphate 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*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 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*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 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*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 260.137 C6 H13 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(O) CAS:56-73-5*LIGAND:C00092:*LIGAND-CPD:C01172: 5.1.3.15 α-D-glucose 6-phosphate = β-D-glucose-6-phosphate sucrose biosynthesis 4α-formyl-4β-methyl-5α-cholesta-8-en-3β-ol 428.697 C29 H48 O2 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(C=O)(C)C(O)CC4)(C)))(C)) 1.14.13.72 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol + O2 = 4α-formyl-4β-methyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 4α-formyl-4β-methyl-5α-cholesta-8-en-3β-ol 428.697 C29 H48 O2 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(C=O)(C)C(O)CC4)(C)))(C)) 1.14.13.72 4α-formyl-4β-methyl-5α-cholesta-8-en-3β-ol + O2 = 4α-carboxy-4β-methyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) demethylmenaquinone-8 DMK-8*demethylmenaquinone 703.102 C50 H70 O2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(=O)c2(c(C(C=1)=O)cccc2)) LIGAND-CPD:C05818: demethylmenaquinone-8 + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + menaquinone-8 menaquinone biosynthesis demethylmenaquinone-8 DMK-8*demethylmenaquinone 703.102 C50 H70 O2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(=O)c2(c(C(C=1)=O)cccc2)) LIGAND-CPD:C05818: octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate = demethylmenaquinone-8 + diphosphate + CO2 menaquinone 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 280.32 C15 H20 O5 CC12(C(C(C)(OC1)CC(=O)C2)(O)C=CC(C)=CC(=O)O) PUBCHEM:442386: 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 280.32 C15 H20 O5 CC12(C(C(C)(OC1)CC(=O)C2)(O)C=CC(C)=CC(=O)O) PUBCHEM:442386: 1.-.-.- phaseic acid = dihydroxyphaseic acid + an oxidized acceptor phaseic acid biosynthesis pFCC primary fluorescent catabolite 628.724 C35 H38 N4 O7 CCc1(c(nc([CH]=O)c(C)1)Cc2(c(C)c3(c(n2)C(C(C(=O)3)C(=O)OC)=C4(N=C(C(C)C4CCC(=O)O)CC5(C(C)=C(C=C)C(=O)N5))))) 1.-.-.- RCC + H+ = pFCC chlorophyll a degradation 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 288.147 C7 H13 O10 P1 C(=O)(O)C(=O)CC(O)C(O)C(O)COP(O)(=O)O LIGAND-CPD:C04691:*CAS:2627-73-8 4.2.3.4 3-deoxy-D-arabino-heptulosonate-7-phosphate = 3-dehydroquinate chorismate biosynthesis 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 288.147 C7 H13 O10 P1 C(=O)(O)C(=O)CC(O)C(O)C(O)COP(O)(=O)O 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 7,8-dihydroneopterin 3'-triphosphate 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*H2NTP*2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphate*dihydroneopterin triphosphate 494.164 C9 H15 N5 O13 P3 C2(C(=Nc1(c(=O)nc(N)nc1N2))C(O)C(O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C04895: 3.6.1.- 7,8-dihydroneopterin 3'-triphosphate + H2O = dihydroneopterin phosphate + diphosphate tetrahydrofolate biosynthesis I 7,8-dihydroneopterin 3'-triphosphate 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*H2NTP*2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphate*dihydroneopterin triphosphate 494.164 C9 H15 N5 O13 P3 C2(C(=Nc1(c(=O)nc(N)nc1N2))C(O)C(O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C04895: 3.6.1.- 7,8-dihydroneopterin 3'-triphosphate + H2O = dihydroneopterin phosphate + diphosphate tetrahydrofolate biosynthesis II 7,8-dihydroneopterin 3'-triphosphate 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*H2NTP*2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphate*dihydroneopterin triphosphate 494.164 C9 H15 N5 O13 P3 C2(C(=Nc1(c(=O)nc(N)nc1N2))C(O)C(O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C04895: 3.5.4.16 GTP + H2O = formate + 7,8-dihydroneopterin 3'-triphosphate tetrahydrofolate biosynthesis I 7,8-dihydroneopterin 3'-triphosphate 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*H2NTP*2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphate*dihydroneopterin triphosphate 494.164 C9 H15 N5 O13 P3 C2(C(=Nc1(c(=O)nc(N)nc1N2))C(O)C(O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O) LIGAND-CPD:C04895: 3.5.4.16 GTP + H2O = formate + 7,8-dihydroneopterin 3'-triphosphate tetrahydrofolate biosynthesis II indole-3-acetyl-gln indole-3-acetyl-glutamine 303.317 C15 H17 N3 O4 C(=O)(NC(C(=O)O)CCC(N)=O)Cc1(c[nH]c2(c1cccc2)) indole-3-acetate + L-glutamine = indole-3-acetyl-gln + H2O IAA conjugate biosynthesis II O-acetyl-L-serine O3-acetyl-L-serine*acetylserine*O-acetylserine 147.13 C5 H9 N1 O4 C([CH](N)C(O)=O)OC(C)=O 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*acetylserine*O-acetylserine 147.13 C5 H9 N1 O4 C([CH](N)C(O)=O)OC(C)=O LIGAND-CPD:C00979:*CAS:66638-22-0 2.5.1.47 O-acetyl-L-serine + hydrogen sulfide = L-cysteine + acetate cysteine biosynthesis I propionyl-CoA propanoyl-CoA*propionyl-coenzyme A 823.598 C24 H40 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC) LIGAND-CPD:C00100:*CAS:317-66-8 2.8.3.1 propionate + acetyl-CoA = propionyl-CoA + acetate D-lactate fermentation to propionate and acetate propionyl-CoA propanoyl-CoA*propionyl-coenzyme A 823.598 C24 H40 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC) LIGAND-CPD:C00100:*CAS:317-66-8 1.2.1.27 NAD+ + coenzyme A + methylmalonate-semialdehyde = NADH + CO2 + propionyl-CoA valine degradation I propionyl-CoA propanoyl-CoA*propionyl-coenzyme A 823.598 C24 H40 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC) LIGAND-CPD:C00100:*CAS:317-66-8 2.3.1.9 2-methylacetoacetyl-CoA + coenzyme A = propionyl-CoA + acetyl-CoA isoleucine degradation I propionyl-CoA propanoyl-CoA*propionyl-coenzyme A 823.598 C24 H40 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC) LIGAND-CPD:C00100:*CAS:317-66-8 6.2.1.17 coenzyme A + propionate + ATP = propionyl-CoA + diphosphate + AMP β-alanine biosynthesis II propionyl-CoA propanoyl-CoA*propionyl-coenzyme A 823.598 C24 H40 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC) LIGAND-CPD:C00100:*CAS:317-66-8 1.3.99.3 FADH2 + acrylyl-CoA = FAD + propionyl-CoA β-alanine biosynthesis II propionyl-CoA propanoyl-CoA*propionyl-coenzyme A 823.598 C24 H40 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC) LIGAND-CPD:C00100:*CAS:317-66-8 1.3.99.3 NADH + acrylyl-CoA = NAD+ + propionyl-CoA D-lactate fermentation to propionate and acetate propionyl-CoA propanoyl-CoA*propionyl-coenzyme A 823.598 C24 H40 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC) LIGAND-CPD:C00100:*CAS:317-66-8 2.8.3.- D-lactate + propionyl-CoA = D-lactoyl-CoA + propionate D-lactate fermentation to propionate and acetate pyridoxine vitamin B6*2-methyl-3-hydroxy-4,5-bis(hydroxy-methyl) pyridine 169.18 C8 H11 N1 O3 C(O)c1(c(CO)cnc(C)c(O)1) LIGAND-CPD:C00314:*CAS:65-23-6 2.7.1.- ATP + pyridoxine = ADP + pyridoxine-5'-phosphate pyridoxal 5'-phosphate salvage pathway ent-cassa-12,15-diene ent-cassa-12,15-diene*ent-cassadiene 274.489 C20 H34 CC1(C)([CH]2(C(C)(CCC1)[CH]3([CH](CC2)C(C)C(C=C)CC3))) ent-copalyl diphosphate = ent-cassa-12,15-diene + diphosphate phytocassane biosynthesis ent-cassa-12,15-diene ent-cassa-12,15-diene*ent-cassadiene 274.489 C20 H34 CC1(C)([CH]2(C(C)(CCC1)[CH]3([CH](CC2)C(C)C(C=C)CC3))) ent-cassa-12,15-diene = ent-cassa-12,15-diene-3α-ol phytocassane biosynthesis p-coumaroyltriacetic acid lactone p-coumaroyltriacetate lactone 272.257 C15 H12 O5 C1(=O)(OC(=CC(O)=C1)CC(=O)C=Cc2(ccc(O)cc2)) p-coumaroyltriacetate = p-coumaroyltriacetic acid lactone + H2O resveratrol biosynthesis pheophorbide a pheide a 592.693 C35 H34 N4 O5 CCC6(=C(C)C5(=Cc1(nc(c(C)c1C=C)C=C2(N=C(C(C(C)2)CCC(=O)O)C3(C(C(=O)OC)C(=O)c4(c(C)c(nc=34)=CC(=N5)6)))))) chlorophyllide a = pheophorbide a + Mg2+ chlorophyll a degradation pheophorbide a pheide a 592.693 C35 H34 N4 O5 CCC6(=C(C)C5(=Cc1(nc(c(C)c1C=C)C=C2(N=C(C(C(C)2)CCC(=O)O)C3(C(C(=O)OC)C(=O)c4(c(C)c(nc=34)=CC(=N5)6)))))) 1.-.-.- pheophorbide a + O2 = RCC + H2O chlorophyll a degradation 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 c3(c2(O=C(c1(ccc(O)cc1))C(O)=Cc2c(O)cc(O)3)) CAS:134-04-3 2.4.1.115 UDP-D-glucose + pelargonidin = 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 c3(c2(O=C(c1(ccc(O)cc1))C(O)=Cc2c(O)cc(O)3)) CAS:134-04-3 1.14.11.- leucopelargonidin + α-ketoglutarate + O2 = pelargonidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) 4α-formyl-5α-cholesta-8-en-3β-ol 414.67 C28 H46 O2 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(C=O)C(O)CC4)(C)))(C)) 1.14.13.72 4α-hydroxymethyl-5α-cholesta-8-en-3β-ol + O2 = 4α-formyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 4α-formyl-5α-cholesta-8-en-3β-ol 414.67 C28 H46 O2 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(C=O)C(O)CC4)(C)))(C)) 1.14.13.72 4α-formyl-5α-cholesta-8-en-3β-ol + O2 = 4α-carboxy-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 2-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(O)C(C(O)=O)OP(O)(O)=O LIGAND-CPD:C00631:*CAS:2553-59-5 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O gluconeogenesis 2-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(O)C(C(O)=O)OP(O)(O)=O LIGAND-CPD:C00631:*CAS:2553-59-5 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O sucrose degradation to ethanol and lactate (anaerobic) 2-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(O)C(C(O)=O)OP(O)(O)=O LIGAND-CPD:C00631:*CAS:2553-59-5 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O respiration (anaerobic) 2-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(O)C(C(O)=O)OP(O)(O)=O LIGAND-CPD:C00631:*CAS:2553-59-5 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O glycolysis IV (plant cytosol) 2-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(O)C(C(O)=O)OP(O)(O)=O LIGAND-CPD:C00631:*CAS:2553-59-5 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O fructose degradation to pyruvate and lactate (anaerobic) 2-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(O)C(C(O)=O)OP(O)(O)=O LIGAND-CPD:C00631:*CAS:2553-59-5 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O glucose fermentation to lactate II 2-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(O)C(C(O)=O)OP(O)(O)=O LIGAND-CPD:C00631:*CAS:2553-59-5 4.2.1.11 2-phosphoglycerate = phosphoenolpyruvate + H2O glycolysis I 2-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(O)C(C(O)=O)OP(O)(O)=O LIGAND-CPD:C00631:*CAS:2553-59-5 5.4.2.1 3-phosphoglycerate = 2-phosphoglycerate gluconeogenesis 2-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(O)C(C(O)=O)OP(O)(O)=O LIGAND-CPD:C00631:*CAS:2553-59-5 5.4.2.1 3-phosphoglycerate = 2-phosphoglycerate sucrose degradation to ethanol and lactate (anaerobic) 2-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(O)C(C(O)=O)OP(O)(O)=O LIGAND-CPD:C00631:*CAS:2553-59-5 5.4.2.1 3-phosphoglycerate = 2-phosphoglycerate glycolysis IV (plant cytosol) 2-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(O)C(C(O)=O)OP(O)(O)=O LIGAND-CPD:C00631:*CAS:2553-59-5 5.4.2.1 3-phosphoglycerate = 2-phosphoglycerate fructose degradation to pyruvate and lactate (anaerobic) 2-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(O)C(C(O)=O)OP(O)(O)=O LIGAND-CPD:C00631:*CAS:2553-59-5 5.4.2.1 3-phosphoglycerate = 2-phosphoglycerate glucose fermentation to lactate II 2-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(O)C(C(O)=O)OP(O)(O)=O LIGAND-CPD:C00631:*CAS:2553-59-5 5.4.2.1 3-phosphoglycerate = 2-phosphoglycerate glycolysis I indole-3-acetyl-polypeptide indole-3-acetate + polypeptide = indole-3-acetyl-polypeptide IAA conjugate biosynthesis II leucopelargonidin cis 3,4-leucopelargonidin 290.272 C15 H14 O6 c3(c2(OC(c1(ccc(O)cc1))C(O)C(O)c2c(O)cc(O)3)) 1.17.1.3 leucopelargonidin + NADPH = afzelechin + NADP+ + H2O proanthocyanidin biosynthesis from flavanols leucopelargonidin cis 3,4-leucopelargonidin 290.272 C15 H14 O6 c3(c2(OC(c1(ccc(O)cc1))C(O)C(O)c2c(O)cc(O)3)) 1.1.1.219 dihydrokaempferol + NADPH = leucopelargonidin + NADP+ leucopelargonidin and leucocyanidin biosynthesis leucopelargonidin cis 3,4-leucopelargonidin 290.272 C15 H14 O6 c3(c2(OC(c1(ccc(O)cc1))C(O)C(O)c2c(O)cc(O)3)) 1.14.11.- leucopelargonidin + α-ketoglutarate + O2 = pelargonidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol 440.708 C30 H48 O2 CC(C)=CCCC(C)C1(C2(C)(C(C=O)(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADP+ + H2O + formate cholesterol biosynthesis I 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol 440.708 C30 H48 O2 CC(C)=CCCC(C)C1(C2(C)(C(C=O)(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADP+ + H2O + formate cholesterol biosynthesis III (via desmosterol) 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol 440.708 C30 H48 O2 CC(C)=CCCC(C)C1(C2(C)(C(C=O)(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis I 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol 440.708 C30 H48 O2 CC(C)=CCCC(C)C1(C2(C)(C(C=O)(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C)C(O)CC4)))) 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) isopentenyladenine-7-N-glucoside 365.388 C16 H23 N5 O5 c2(c1(N(C=Nc1ncn2)C3(OC(CO)C(O)C(O)C(O)3)))(NCC=C(C)C) 2.4.1.- isopentenyladenine + UDP-D-glucose = isopentenyladenine-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis mevalonate-5-PP mevalonate-diphosphate*(R)-5-Diphosphomevalonate 308.118 C6 H14 O10 P2 CC(CC(=O)O)(O)CCOP(O)(=O)OP(O)(=O)O CAS:4872-34-8 4.1.1.33 mevalonate-5-PP + ATP = CO2 + ADP mevalonate pathway mevalonate-5-PP mevalonate-diphosphate*(R)-5-Diphosphomevalonate 308.118 C6 H14 O10 P2 CC(CC(=O)O)(O)CCOP(O)(=O)OP(O)(=O)O CAS:4872-34-8 2.7.4.2 mevalonate-5P + ATP = mevalonate-5-PP + ADP mevalonate pathway isopentenyl adenosine iPA 335.362 C15 H21 N5 O4 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(ncn3)NCC=C(C)C)) isopentenyl adenosine + H2O = isopentenyladenine + D-ribose trans-zeatin biosynthesis isopentenyl adenosine iPA 335.362 C15 H21 N5 O4 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(ncn3)NCC=C(C)C)) isopentenyladenosine-5'-monophosphate + H2O = isopentenyl adenosine trans-zeatin biosynthesis isopentenyl adenosine iPA 335.362 C15 H21 N5 O4 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(ncn3)NCC=C(C)C)) isopentenyl adenosine + H2O = trans-zeatin riboside + H+ trans-zeatin biosynthesis isopentenyl adenosine iPA 335.362 C15 H21 N5 O4 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(ncn3)NCC=C(C)C)) 1.5.99.12 isopentenyl adenosine + H2O + FAD = adenosine + 3-methyl-2-butenal + FADH2 cytokinins degradation momilactone B 330.423 C20 H26 O4 CC1(C=C)(CC5([CH](CC1)C23([CH]4(C(C(OC2)(O)CC3)(C)C(=O)O[CH]4C=5)))) momilactone A = momilactone B momilactone biosynthesis 18:3-18:2-PC 1-18:3-2-18:2-phosphatidylcholine 781.084 C44 H79 N1 O8 P1 C(OP(=O)(O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:3-18:2-PC = 18:3-18:3-PC phospholipid desaturation 18:3-18:2-PC 1-18:3-2-18:2-phosphatidylcholine 781.084 C44 H79 N1 O8 P1 C(OP(=O)(O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:3-18:1-PC = 18:3-18:2-PC phospholipid desaturation 18:3-18:2-PC 1-18:3-2-18:2-phosphatidylcholine 781.084 C44 H79 N1 O8 P1 C(OP(=O)(O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:2-18:2-PC = 18:3-18:2-PC phospholipid desaturation 24-ethylidenelophenol (Z)-24-ethylidenelophenol*citrostadienol 426.724 C30 H50 O1 CC=C(C(C)C)CC[CH](C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C)([CH](CC=3)C(C)C(O)CC4)))) 2.1.1.- 24-ethylidenelophenol = avenasterol sterol biosynthesis 24-ethylidenelophenol (Z)-24-ethylidenelophenol*citrostadienol 426.724 C30 H50 O1 CC=C(C(C)C)CC[CH](C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C)([CH](CC=3)C(C)C(O)CC4)))) 2.1.1.143 24-methylenelophenol + S-adenosyl-L-methionine = 24-ethylidenelophenol + S-adenosyl-L-homocysteine sterol biosynthesis 5-methyl-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 459.461 C20 H25 N7 O6 C(C1(N(C)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00440:*CAS:134-35-0 2.1.1.19 tetrahydrofolate + trimethyl sulfonium = dimethylsulfide + 5-methyl-THF folate transformations 5-methyl-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 459.461 C20 H25 N7 O6 C(C1(N(C)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00440:*CAS:134-35-0 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate S-adenosylmethionine biosynthesis 5-methyl-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 459.461 C20 H25 N7 O6 C(C1(N(C)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00440:*CAS:134-35-0 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate methionine biosynthesis I 5-methyl-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 459.461 C20 H25 N7 O6 C(C1(N(C)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00440:*CAS:134-35-0 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate folate transformations 5-methyl-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 459.461 C20 H25 N7 O6 C(C1(N(C)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00440:*CAS:134-35-0 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate formylTHF biosynthesis II 5-methyl-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 459.461 C20 H25 N7 O6 C(C1(N(C)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00440:*CAS:134-35-0 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate formylTHF biosynthesis I 5-methyl-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 459.461 C20 H25 N7 O6 C(C1(N(C)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00440:*CAS:134-35-0 1.5.7.1 5-methyl-THF = 5,10-methylene-THF folate transformations 5-methyl-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 459.461 C20 H25 N7 O6 C(C1(N(C)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00440:*CAS:134-35-0 1.5.1.20 5-methyl-THF = 5,10-methylene-THF + H+ folate transformations 5-methyl-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 459.461 C20 H25 N7 O6 C(C1(N(C)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00440:*CAS:134-35-0 1.5.1.20 5-methyl-THF = 5,10-methylene-THF + H+ formylTHF biosynthesis II 5-methyl-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 459.461 C20 H25 N7 O6 C(C1(N(C)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O) LIGAND-CPD:C00440:*CAS:134-35-0 1.5.1.20 5-methyl-THF = 5,10-methylene-THF + H+ formylTHF biosynthesis I (mannosyl)3-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->3)-[α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 2162.697 C114 H190 N2 O32 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC4(OC(COC3(OC(CO)C(O)C(O)C(O)3))C(O)C(C(O)4)OC5(OC(CO)C(O)C(O)C(O)5)))) (mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)3-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis (mannosyl)3-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->3)-[α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 2162.697 C114 H190 N2 O32 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC4(OC(COC3(OC(CO)C(O)C(O)C(O)3))C(O)C(C(O)4)OC5(OC(CO)C(O)C(O)C(O)5)))) (mannosyl)3-(N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = (mannosyl)4-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis 7,8-diaminopelargonate 7,8-diaminononanoate*DAPA 188.269 C9 H20 N2 O2 CC(N)C(N)CCCCCC(=O)O 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 II 7,8-diaminopelargonate 7,8-diaminononanoate*DAPA 188.269 C9 H20 N2 O2 CC(N)C(N)CCCCCC(=O)O 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 I 7,8-diaminopelargonate 7,8-diaminononanoate*DAPA 188.269 C9 H20 N2 O2 CC(N)C(N)CCCCCC(=O)O LIGAND-CPD:C01037: 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = dethiobiotin + ADP biotin biosynthesis II 7,8-diaminopelargonate 7,8-diaminononanoate*DAPA 188.269 C9 H20 N2 O2 CC(N)C(N)CCCCCC(=O)O LIGAND-CPD:C01037: 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = dethiobiotin + ADP biotin biosynthesis I 1,2-dihydroxy-3-keto-5-methylthiopentene 1,2-dihydroxy-3-keto-5-methylthiopentene anion*1,2-dihydroxy-3-keto-5-methylthiopentane 162.203 C6 H10 O3 S1 C(O)=C(O)C(=O)CCSC 1.13.11.54 1,2-dihydroxy-3-keto-5-methylthiopentene + O2 = 2-oxo-4-methylthiobutanoate + formate methionine salvage pathway 1,2-dihydroxy-3-keto-5-methylthiopentene 1,2-dihydroxy-3-keto-5-methylthiopentene anion*1,2-dihydroxy-3-keto-5-methylthiopentane 162.203 C6 H10 O3 S1 C(O)=C(O)C(=O)CCSC 2-hydroxy-3-keto-5-methylthio-1-phosphopentene + H2O = 1,2-dihydroxy-3-keto-5-methylthiopentene methionine salvage pathway 3-methylcrotonyl-CoA β-methylcrotonoyl-CoA*3-methylbut-2-enoyl-CoA 849.636 C26 H42 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(=O)(O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=C(C)C) 1.3.99.10 isovaleryl-CoA + FAD = 3-methylcrotonyl-CoA + FADH2 leucine degradation I 3-methylcrotonyl-CoA β-methylcrotonoyl-CoA*3-methylbut-2-enoyl-CoA 849.636 C26 H42 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(=O)(O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=C(C)C) 6.4.1.4 ATP + 3-methylcrotonyl-CoA + HCO3- = ADP + 3-methylglutaconyl-CoA leucine degradation I 4-coumaroylquinate trans-(p-coumaroyl)-quinate*trans-5-O-(4-coumaroyl)quinate 338.313 C16 H18 O8 C(=O)(OC1(C(O)C(O)CC(O)(C1)C(O)=O))C=Cc2(ccc(O)cc2) 1.14.13.36 4-coumaroylquinate + NADPH + O2 = caffeoylquinate + NADP+ + H2O phenylpropanoid biosynthesis 4-coumaroylquinate trans-(p-coumaroyl)-quinate*trans-5-O-(4-coumaroyl)quinate 338.313 C16 H18 O8 C(=O)(OC1(C(O)C(O)CC(O)(C1)C(O)=O))C=Cc2(ccc(O)cc2) 2.3.1.133 quinate + coumaroyl-CoA = 4-coumaroylquinate + coenzyme A phenylpropanoid biosynthesis 18:3-18:3-PC 1-18:3-2-18:3-phosphatidylcholine*1-18:3-2-18:3-sn-glycerol-3-phosphocholine*1,2-(9Z,12Z,15Z-octadecatrienoyl)-sn-glycero-3-phosphocholine 779.068 C44 H77 N1 O8 P1 C(OC(=O)CCCCCCCC=CCC=CCC=CCC)C(COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCC=CCC PUBCHEM:5313540: 1.14.99.- 18:2-18:3-PC = 18:3-18:3-PC phospholipid desaturation 18:3-18:3-PC 1-18:3-2-18:3-phosphatidylcholine*1-18:3-2-18:3-sn-glycerol-3-phosphocholine*1,2-(9Z,12Z,15Z-octadecatrienoyl)-sn-glycero-3-phosphocholine 779.068 C44 H77 N1 O8 P1 C(OC(=O)CCCCCCCC=CCC=CCC=CCC)C(COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCC=CCC PUBCHEM:5313540: 1.14.99.- 18:3-18:2-PC = 18:3-18:3-PC phospholipid desaturation phytyl-PP phytyl pyrophosphate 456.495 C20 H42 O7 P2 CC(=CCOP(O)(=O)OP(O)(=O)O)CCCC(C)CCCC(C)CCCC(C)C 1.3.1.- tetrahydrogeranylgeranyl-PP + NADPH = phytyl-PP + NADP+ phytyl-PP biosynthesis phytyl-PP phytyl pyrophosphate 456.495 C20 H42 O7 P2 CC(=CCOP(O)(=O)OP(O)(=O)O)CCCC(C)CCCC(C)CCCC(C)C 1,4-dihydroxy-2-naphthoate + phytyl-PP = demethylphylloquinone + CO2 + diphosphate phylloquinone biosynthesis phytyl-PP phytyl pyrophosphate 456.495 C20 H42 O7 P2 CC(=CCOP(O)(=O)OP(O)(=O)O)CCCC(C)CCCC(C)CCCC(C)C homogentisate + phytyl-PP = 2-methyl-6-phytyl-1,4-benzoquinone + CO2 + diphosphate vitamin E biosynthesis phytyl-PP phytyl pyrophosphate 456.495 C20 H42 O7 P2 CC(=CCOP(O)(=O)OP(O)(=O)O)CCCC(C)CCCC(C)CCCC(C)C 2.5.1.62 chlorophyllide a + phytyl-PP = chlorophyll a + diphosphate chlorophyll cycle phytyl-PP phytyl pyrophosphate 456.495 C20 H42 O7 P2 CC(=CCOP(O)(=O)OP(O)(=O)O)CCCC(C)CCCC(C)CCCC(C)C 2.5.1.62 chlorophyllide a + phytyl-PP = chlorophyll a + diphosphate chlorophyll a biosynthesis I phytyl-PP phytyl pyrophosphate 456.495 C20 H42 O7 P2 CC(=CCOP(O)(=O)OP(O)(=O)O)CCCC(C)CCCC(C)CCCC(C)C 2.5.1.- chlorophyllide b + phytyl-PP = chlorophyll b + diphosphate chlorophyll cycle Mg2+ magnesium*Mg+2*Mg++*magnesium ion 24.305 MG1 [Mg++] LIGAND-CPD:C00305: chlorophyllide a = pheophorbide a + Mg2+ chlorophyll a degradation Mg2+ magnesium*Mg+2*Mg++*magnesium ion 24.305 MG1 [Mg++] LIGAND-CPD:C00305: 6.6.1.1 ATP + protoporphyrin IX + Mg2+ + H2O = Mg-protoporphyrin + ADP + H+ chlorophyllide a biosynthesis 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (1S,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 240.212 C11 H12 O6 C(=O)(O)CCC(=O)C1(C(C(O)=O)C(O)C=CC=1) LIGAND-CPD:C05817: 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate = O-succinylbenzoate + H2O menaquinone biosynthesis 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (1S,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 240.212 C11 H12 O6 C(=O)(O)CCC(=O)C1(C(C(O)=O)C(O)C=CC=1) LIGAND-CPD:C05817: 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate = O-succinylbenzoate + H2O phylloquinone biosynthesis 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (1S,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 240.212 C11 H12 O6 C(=O)(O)CCC(=O)C1(C(C(O)=O)C(O)C=CC=1) LIGAND-CPD:C05817: succinate-semialdehyde-thiamine PPi + isochorismate = 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate + thiamine diphosphate + pyruvate menaquinone biosynthesis 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (1S,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 240.212 C11 H12 O6 C(=O)(O)CCC(=O)C1(C(C(O)=O)C(O)C=CC=1) LIGAND-CPD:C05817: succinate-semialdehyde-thiamine PPi + isochorismate = 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate + thiamine diphosphate + pyruvate phylloquinone biosynthesis S-adenosyl-L-methioninamine 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 355.434 C14 H23 N6 O3 S1 C(N)CC[S+](C)CC1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C01137: 2.5.1.22 spermidine + S-adenosyl-L-methioninamine = spermine + 5'-methylthioadenosine spermine biosynthesis S-adenosyl-L-methioninamine 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 355.434 C14 H23 N6 O3 S1 C(N)CC[S+](C)CC1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C01137: 4.1.1.50 S-adenosyl-L-methionine = CO2 + S-adenosyl-L-methioninamine spermidine biosynthesis S-adenosyl-L-methioninamine 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 355.434 C14 H23 N6 O3 S1 C(N)CC[S+](C)CC1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C01137: 4.1.1.50 S-adenosyl-L-methionine = CO2 + S-adenosyl-L-methioninamine spermine biosynthesis S-adenosyl-L-methioninamine 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 355.434 C14 H23 N6 O3 S1 C(N)CC[S+](C)CC1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C01137: 2.5.1.16 putrescine + S-adenosyl-L-methioninamine = spermidine + 5'-methylthioadenosine spermidine biosynthesis L-γ-glutamylcysteine γ-glutamylcysteine*γ-L-glutamyl-L-cysteine 250.269 C8 H14 N2 O5 S1 C(O)(=O)C(N)CCC(=O)NC(CS)C(O)=O LIGAND-CPD:C00669:*CAS:686-58-8 6.3.2.2 L-cysteine + L-glutamate + ATP = L-γ-glutamylcysteine + ADP glutathione biosynthesis L-γ-glutamylcysteine γ-glutamylcysteine*γ-L-glutamyl-L-cysteine 250.269 C8 H14 N2 O5 S1 C(O)(=O)C(N)CCC(=O)NC(CS)C(O)=O LIGAND-CPD:C00669:*CAS:686-58-8 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = glutathione + ADP glutathione biosynthesis GA20 gibberellin A20*gibberellin A20*GA20 332.396 C19 H24 O5 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(CCC3)(C)[CH]4C5C(=O)O)))(O)) 1.14.11.- GA20 + α-ketoglutarate + O2 = GA29 + succinate + CO2 gibberellin inactivation GA20 gibberellin A20*gibberellin A20*GA20 332.396 C19 H24 O5 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(CCC3)(C)[CH]4C5C(=O)O)))(O)) 1.14.11.- GA19 + O2 + α-ketoglutarate = GA20 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) GA20 gibberellin A20*gibberellin A20*GA20 332.396 C19 H24 O5 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(CCC3)(C)[CH]4C5C(=O)O)))(O)) 1.14.11.15 GA20 + α-ketoglutarate + O2 = GA1 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) hypoxanthine 136.113 C5 H4 N4 O1 c12(c(nc[nH]1)c(=O)[nH]cn2) LIGAND-CPD:C00262:*CAS:68-94-0 5-phosphoribosyl 1-pyrophosphate + hypoxanthine = inosine-5'-phosphate + diphosphate salvage pathways of adenine, hypoxanthine, and their nucleosides hypoxanthine 136.113 C5 H4 N4 O1 c12(c(nc[nH]1)c(=O)[nH]cn2) LIGAND-CPD:C00262:*CAS:68-94-0 deoxyinosine = hypoxanthine + deoxyribose-1-phosphate salvage pathways of adenine, hypoxanthine, and their nucleosides hypoxanthine 136.113 C5 H4 N4 O1 c12(c(nc[nH]1)c(=O)[nH]cn2) LIGAND-CPD:C00262:*CAS:68-94-0 hypoxanthine + H2O = H+ + xanthine salvage pathways of adenine, hypoxanthine, and their nucleosides hypoxanthine 136.113 C5 H4 N4 O1 c12(c(nc[nH]1)c(=O)[nH]cn2) LIGAND-CPD:C00262:*CAS:68-94-0 2.4.2.8 diphosphate + inosine-5'-phosphate = 5-phosphoribosyl 1-pyrophosphate + hypoxanthine salvage pathways of purine nucleosides hypoxanthine 136.113 C5 H4 N4 O1 c12(c(nc[nH]1)c(=O)[nH]cn2) LIGAND-CPD:C00262:*CAS:68-94-0 2.4.2.8 diphosphate + inosine-5'-phosphate = 5-phosphoribosyl 1-pyrophosphate + hypoxanthine salvage pathways of purine nucleosides II (plant) hypoxanthine 136.113 C5 H4 N4 O1 c12(c(nc[nH]1)c(=O)[nH]cn2) LIGAND-CPD:C00262:*CAS:68-94-0 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ purine degradation hypoxanthine 136.113 C5 H4 N4 O1 c12(c(nc[nH]1)c(=O)[nH]cn2) LIGAND-CPD:C00262:*CAS:68-94-0 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ salvage pathways of purine nucleosides II (plant) hypoxanthine 136.113 C5 H4 N4 O1 c12(c(nc[nH]1)c(=O)[nH]cn2) LIGAND-CPD:C00262:*CAS:68-94-0 3.2.2.2 inosine + H2O = hypoxanthine + D-ribose purine degradation hypoxanthine 136.113 C5 H4 N4 O1 c12(c(nc[nH]1)c(=O)[nH]cn2) LIGAND-CPD:C00262:*CAS:68-94-0 3.2.2.2 inosine + H2O = hypoxanthine + D-ribose salvage pathways of purine nucleosides II (plant) hypoxanthine 136.113 C5 H4 N4 O1 c12(c(nc[nH]1)c(=O)[nH]cn2) LIGAND-CPD:C00262:*CAS:68-94-0 2.4.2.- inosine = ribose-1-phosphate + hypoxanthine salvage pathways of adenine, hypoxanthine, and their nucleosides hypoxanthine 136.113 C5 H4 N4 O1 c12(c(nc[nH]1)c(=O)[nH]cn2) LIGAND-CPD:C00262:*CAS:68-94-0 2.4.2.- inosine = ribose-1-phosphate + hypoxanthine salvage pathways of purine nucleosides α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) CAS:56-73-5*LIGAND:C00092:*CAS:56-73-5:*LIGAND-CPD:C00668: 2.7.1.1 α-D-glucose + ATP = α-D-glucose 6-phosphate + ADP sucrose degradation III α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) CAS:56-73-5*LIGAND:C00092:*CAS:56-73-5:*LIGAND-CPD:C00668: 2.7.1.1 α-D-glucose + ATP = α-D-glucose 6-phosphate + ADP starch degradation α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) CAS:56-73-5*LIGAND:C00092:*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 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) CAS:56-73-5*LIGAND:C00092:*CAS:56-73-5:*LIGAND-CPD:C00668: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate sucrose degradation to ethanol and lactate (anaerobic) α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) CAS:56-73-5*LIGAND:C00092:*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 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) CAS:56-73-5*LIGAND:C00092:*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 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) CAS:56-73-5*LIGAND:C00092:*CAS:56-73-5:*LIGAND-CPD:C00668: 5.4.2.2 α-D-glucose 1-phosphate = α-D-glucose 6-phosphate UDP-glucose conversion α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) CAS:56-73-5*LIGAND:C00092:*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 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) CAS:56-73-5*LIGAND:C00092:*CAS:56-73-5:*LIGAND-CPD:C00668: 2.4.1.15 UDP-D-glucose + α-D-glucose 6-phosphate = UDP + trehalose 6-phosphate trehalose biosynthesis I α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) CAS:56-73-5*LIGAND:C00092:*CAS:56-73-5:*LIGAND-CPD:C00668: 5.3.1.9 α-D-glucose 6-phosphate = fructose-6-phosphate sucrose degradation to ethanol and lactate (anaerobic) α-D-glucose 6-phosphate α-glucose-6-phosphate*α-D-glucose-6-P 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) CAS:56-73-5*LIGAND:C00092:*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 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) CAS:56-73-5*LIGAND:C00092:*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 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) CAS:56-73-5*LIGAND:C00092:*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 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) CAS:56-73-5*LIGAND:C00092:*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-glyceride*2-acylglycerol C4 H7 O4 R1 3.1.1.- H2O = 2-monoacylglycerol triacylglycerol degradation 2-monoacylglycerol 2-glyceride*2-acylglycerol C4 H7 O4 R1 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 213.083 C4 H8 N1 O7 P1 C(=O)(OP(=O)(O)O)CC(N)C(O)=O 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 213.083 C4 H8 N1 O7 P1 C(=O)(OP(=O)(O)O)CC(N)C(O)=O LIGAND-CPD:C03082:*CAS:22138-53-0 2.7.2.4 L-aspartate + ATP = L-aspartyl-4-phosphate + ADP lysine biosynthesis II 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 213.083 C4 H8 N1 O7 P1 C(=O)(OP(=O)(O)O)CC(N)C(O)=O LIGAND-CPD:C03082:*CAS:22138-53-0 2.7.2.4 L-aspartate + ATP = L-aspartyl-4-phosphate + ADP lysine biosynthesis I 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 213.083 C4 H8 N1 O7 P1 C(=O)(OP(=O)(O)O)CC(N)C(O)=O 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 213.083 C4 H8 N1 O7 P1 C(=O)(OP(=O)(O)O)CC(N)C(O)=O LIGAND-CPD:C03082:*CAS:22138-53-0 1.2.1.11 NADP+ + L-aspartate-semialdehyde = 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 213.083 C4 H8 N1 O7 P1 C(=O)(OP(=O)(O)O)CC(N)C(O)=O LIGAND-CPD:C03082:*CAS:22138-53-0 1.2.1.11 NADP+ + L-aspartate-semialdehyde = NADPH + L-aspartyl-4-phosphate lysine biosynthesis II 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 213.083 C4 H8 N1 O7 P1 C(=O)(OP(=O)(O)O)CC(N)C(O)=O LIGAND-CPD:C03082:*CAS:22138-53-0 1.2.1.11 NADP+ + L-aspartate-semialdehyde = NADPH + L-aspartyl-4-phosphate lysine biosynthesis I 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 213.083 C4 H8 N1 O7 P1 C(=O)(OP(=O)(O)O)CC(N)C(O)=O LIGAND-CPD:C03082:*CAS:22138-53-0 1.2.1.11 NADP+ + L-aspartate-semialdehyde = NADPH + L-aspartyl-4-phosphate homoserine biosynthesis glutaconyl-CoA glutaconyl-coenzyme A*pent-2-enoyl-CoA*glutaconyl-1-CoA*4-carboxybut-2-enoyl-CoA 879.619 C26 H40 N7 O19 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)C=CCC(=O)O)COP(O)(=O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)n2(c3(c(nc2)c(N)ncn3))) CAS:6712-05-6 4.1.1.70 glutaconyl-CoA = CO2 + crotonyl-CoA glutaryl-CoA degradation glutaconyl-CoA glutaconyl-coenzyme A*pent-2-enoyl-CoA*glutaconyl-1-CoA*4-carboxybut-2-enoyl-CoA 879.619 C26 H40 N7 O19 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)C=CCC(=O)O)COP(O)(=O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)n2(c3(c(nc2)c(N)ncn3))) CAS:6712-05-6 glutaryl-CoA + FAD = glutaconyl-CoA + FADH2 glutaryl-CoA degradation hydrogen sulfide sulfide*H2S 34.076 H2 S1 [SH2] CAS:06/04/7783:*LIGAND-CPD:C00283: 1.8.1.2 H2O + NADP+ + hydrogen sulfide = sulfite + NADPH sulfate reduction I (assimilatory) hydrogen sulfide sulfide*H2S 34.076 H2 S1 [SH2] CAS:06/04/7783:*LIGAND-CPD:C00283: 2.5.1.47 O-acetyl-L-serine + hydrogen sulfide = L-cysteine + acetate cysteine biosynthesis I hydrogen sulfide sulfide*H2S 34.076 H2 S1 [SH2] CAS:06/04/7783:*LIGAND-CPD:C00283: 2.5.1.49 O-acetyl-L-homoserine + hydrogen sulfide = L-homocysteine + acetate homocysteine biosynthesis Cys-Gly 178.206 C5 H10 N2 O3 S1 C(O)(=O)CNC(=O)C(N)CS 3.4.11.2 Cys-Gly + H2O = L-cysteine + glycine γ-glutamyl cycle Cys-Gly 178.206 C5 H10 N2 O3 S1 C(O)(=O)CNC(=O)C(N)CS 2.3.2.2 (5-L-glutamyl)-L-amino acid + Cys-Gly = glutathione γ-glutamyl cycle 18:3-16:2-MGDG 1-18:3-2-16:2-monogalactosyldiacylglycerol*1-(9Z,12Z,15Z-octadecatrienoyl)-2-(7Z,10Z-hexadecadienoyl)-3-O-beta-D-galactosyl-sn-glycerol 749.036 C43 H72 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:3-16:1-MGDG = 18:3-16:2-MGDG glycolipid desaturation 18:3-16:2-MGDG 1-18:3-2-16:2-monogalactosyldiacylglycerol*1-(9Z,12Z,15Z-octadecatrienoyl)-2-(7Z,10Z-hexadecadienoyl)-3-O-beta-D-galactosyl-sn-glycerol 749.036 C43 H72 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:3-16:2-MGDG = 18:3-16:3-MGDG glycolipid desaturation 18:3-16:2-MGDG 1-18:3-2-16:2-monogalactosyldiacylglycerol*1-(9Z,12Z,15Z-octadecatrienoyl)-2-(7Z,10Z-hexadecadienoyl)-3-O-beta-D-galactosyl-sn-glycerol 749.036 C43 H72 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:2-16:2-MGDG = 18:3-16:2-MGDG glycolipid desaturation GDP-L-gulose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C1O)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c4(c(nc3)c(=O)[nH]c(n4)N)))) 5.1.3.- GDP-L-gulose = GDP-L-galactose ascorbate biosynthesis GDP-L-gulose 605.345 C16 H25 N5 O16 P2 C(O)C1(OC(C(O)C(O)C1O)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c4(c(nc3)c(=O)[nH]c(n4)N)))) 5.1.3.- GDP-D-mannose = GDP-L-gulose ascorbate biosynthesis tetrahydrogeranylgeranyl-PP tetrahydroGGPP*tetrahydrogeranylgeranyl pyrophosphate*tetrahydrogeranylgeranyl diphosphate 454.479 C20 H40 O7 P2 CC(C)=CCCC(C)CCCC(C)CCCC(C)=CCOP(O)(=O)OP(=O)(O)O 1.3.1.- tetrahydrogeranylgeranyl-PP + NADPH = phytyl-PP + NADP+ phytyl-PP biosynthesis tetrahydrogeranylgeranyl-PP tetrahydroGGPP*tetrahydrogeranylgeranyl pyrophosphate*tetrahydrogeranylgeranyl diphosphate 454.479 C20 H40 O7 P2 CC(C)=CCCC(C)CCCC(C)CCCC(C)=CCOP(O)(=O)OP(=O)(O)O 1.3.1.- dihydrogeranylgeranyl-PP + NADPH = tetrahydrogeranylgeranyl-PP + NADP+ phytyl-PP biosynthesis 24-methylenelophenol cpd-4101*cdp-4101*4α-methyl-5α-ergosta-7,24-dien-3β-ol 412.698 C29 H48 O1 CC(C)C(=C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC=3)C(C)C(O)CC4)(C)))) 2.1.1.- 24-methylenelophenol = episterol sterol biosynthesis 24-methylenelophenol cpd-4101*cdp-4101*4α-methyl-5α-ergosta-7,24-dien-3β-ol 412.698 C29 H48 O1 CC(C)C(=C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC=3)C(C)C(O)CC4)(C)))) 5.3.3.5 4α-methylfecosterol = 24-methylenelophenol sterol biosynthesis 24-methylenelophenol cpd-4101*cdp-4101*4α-methyl-5α-ergosta-7,24-dien-3β-ol 412.698 C29 H48 O1 CC(C)C(=C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC=3)C(C)C(O)CC4)(C)))) 2.1.1.143 24-methylenelophenol + S-adenosyl-L-methionine = 24-ethylidenelophenol + S-adenosyl-L-homocysteine sterol biosynthesis 4-hydroxysphinganine PHS*phytosphingosine 317.511 C18 H39 N1 O3 CCCCCCCCCCCCCCC(O)C(O)C(N)CO 2.7.1.91 4-hydroxysphinganine + ATP = phytosphingosine-1-P + ADP sphingolipid metabolism 4-hydroxysphinganine PHS*phytosphingosine 317.511 C18 H39 N1 O3 CCCCCCCCCCCCCCC(O)C(O)C(N)CO 1.14.-.- sphinganine + O2 + NADPH = 4-hydroxysphinganine + H2O + NADP+ sphingolipid metabolism 4-hydroxysphinganine PHS*phytosphingosine 317.511 C18 H39 N1 O3 CCCCCCCCCCCCCCC(O)C(O)C(N)CO sphingolipid metabolism 4-hydroxysphinganine PHS*phytosphingosine 317.511 C18 H39 N1 O3 CCCCCCCCCCCCCCC(O)C(O)C(N)CO 2.7.1.91 phytosphingosine-1-P + ADP = ATP + 4-hydroxysphinganine sphingolipid metabolism 4-hydroxysphinganine PHS*phytosphingosine 317.511 C18 H39 N1 O3 CCCCCCCCCCCCCCC(O)C(O)C(N)CO 3.5.1.23 H2O = 4-hydroxysphinganine sphingolipid metabolism 7-dehydro-cholesterol 7-dehydro-cholesterol*cholesta-5,7-dien-3 β-ol*cholesta-5,7-dienol*7-dehydrocholesterol*cholesta-5,7-dien-3β-ol 384.644 C27 H44 O1 CC(C)CCCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC=3)CC(O)CC4)(C)))) CAS:434-16-2 1.14.21.6 lathosterol + O2 = 7-dehydro-cholesterol + H2O cholesterol biosynthesis I 7-dehydro-cholesterol 7-dehydro-cholesterol*cholesta-5,7-dien-3 β-ol*cholesta-5,7-dienol*7-dehydrocholesterol*cholesta-5,7-dien-3β-ol 384.644 C27 H44 O1 CC(C)CCCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC=3)CC(O)CC4)(C)))) CAS:434-16-2 1.14.21.6 lathosterol + O2 = 7-dehydro-cholesterol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 7-dehydro-cholesterol 7-dehydro-cholesterol*cholesta-5,7-dien-3 β-ol*cholesta-5,7-dienol*7-dehydrocholesterol*cholesta-5,7-dien-3β-ol 384.644 C27 H44 O1 CC(C)CCCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC=3)CC(O)CC4)(C)))) CAS:434-16-2 1.3.1.21 7-dehydro-cholesterol + NADPH = cholesterol + NADP+ cholesterol biosynthesis I 7-dehydro-cholesterol 7-dehydro-cholesterol*cholesta-5,7-dien-3 β-ol*cholesta-5,7-dienol*7-dehydrocholesterol*cholesta-5,7-dien-3β-ol 384.644 C27 H44 O1 CC(C)CCCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC=3)CC(O)CC4)(C)))) CAS:434-16-2 1.3.1.21 7-dehydro-cholesterol + NADPH = cholesterol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 2,3-bis(3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate 2,3-diacyl-glucosamine 1-phosphate*2,3-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphate*2,3-bis(β-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate*lipid X 711.869 C34 H66 N1 O12 P1 CCCCCCCCCCCC(O)CC(=O)NC1(C(C(O)C(CO)OC1OP(O)(O)=O)OC(=O)CC(O)CCCCCCCCCCC) LIGAND-CPD:C04824: 2.4.1.182 2,3-bis(3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate + UDP-2,3-bis(3-hydroxymyristoyl)glucosamine = lipid A disaccharide + UDP lipid-A-precursor biosynthesis 2,3-bis(3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate 2,3-diacyl-glucosamine 1-phosphate*2,3-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphate*2,3-bis(β-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate*lipid X 711.869 C34 H66 N1 O12 P1 CCCCCCCCCCCC(O)CC(=O)NC1(C(C(O)C(CO)OC1OP(O)(O)=O)OC(=O)CC(O)CCCCCCCCCCC) LIGAND-CPD:C04824: H2O + UDP-2,3-bis(3-hydroxymyristoyl)glucosamine = 2,3-bis(3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate + UMP lipid-A-precursor biosynthesis sinapate 224.213 C11 H12 O5 C(O)(=O)C=CC1(=CC(OC)=C(O)C(=C1)OC) NCI:59261*CAS:530-59-6 2.1.1.68 5-hydroxy-ferulic-acid + S-adenosyl-L-methionine = sinapate + S-adenosyl-L-homocysteine free phenylpropanoid acid biosynthesis glycerol 1,2,3-trihydroxypropane*glycerin*1,2,3-trihydroxypropanol 92.094 C3 H8 O3 C(O)C(O)CO LIGAND-CPD:C00116:*CAS:56-81-5 3.1.1.23 H2O + 1-monoacylglycerol = glycerol triacylglycerol degradation glycerol 1,2,3-trihydroxypropane*glycerin*1,2,3-trihydroxypropanol 92.094 C3 H8 O3 C(O)C(O)CO LIGAND-CPD:C00116:*CAS:56-81-5 2.7.8.- phospholipid biosynthesis I glycerol 1,2,3-trihydroxypropane*glycerin*1,2,3-trihydroxypropanol 92.094 C3 H8 O3 C(O)C(O)CO LIGAND-CPD:C00116:*CAS:56-81-5 2.7.1.30 glycerol + ATP = sn-glycerol-3-phosphate + ADP glycerol degradation IV glycerol 1,2,3-trihydroxypropane*glycerin*1,2,3-trihydroxypropanol 92.094 C3 H8 O3 C(O)C(O)CO LIGAND-CPD:C00116:*CAS:56-81-5 2.7.1.30 glycerol + ATP = sn-glycerol-3-phosphate + ADP glycerol degradation I trans-neoxanthin 600.88 C40 H56 O4 CC(C=C=C1(C(C)(O)CC(O)CC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC23(C(C)(O2)CC(O)CC(C)(C)3) 5.3.99.9 violaxanthin = trans-neoxanthin carotenoid biosynthesis trans-neoxanthin 600.88 C40 H56 O4 CC(C=C=C1(C(C)(O)CC(O)CC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC23(C(C)(O2)CC(O)CC(C)(C)3) trans-neoxanthin = 9'-cis-neoxanthin abscisic acid biosynthesis phosphoadenosine-5'-phosphosulfate PAPS*phosphoadenosine phosphosulfate*3'-phosphoadenosine-5'-phosphosulfate*3'-phosphoadenylyl-sulfate 507.262 C10 H15 N5 O13 P2 S1 [CH]1(O[CH](C(C(O)1)OP(=O)(O)O)COP(O)(=O)OS(O)(=O)=O)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00053:*CAS:482-67-7 2.7.1.25 adenosine 5'-phosphosulfate + ATP = phosphoadenosine-5'-phosphosulfate + ADP sulfate reduction I (assimilatory) phosphoadenosine-5'-phosphosulfate PAPS*phosphoadenosine phosphosulfate*3'-phosphoadenosine-5'-phosphosulfate*3'-phosphoadenylyl-sulfate 507.262 C10 H15 N5 O13 P2 S1 [CH]1(O[CH](C(C(O)1)OP(=O)(O)O)COP(O)(=O)OS(O)(=O)=O)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00053:*CAS:482-67-7 2.7.1.25 adenosine 5'-phosphosulfate + ATP = phosphoadenosine-5'-phosphosulfate + ADP sulfate activation for sulfonation phosphoadenosine-5'-phosphosulfate PAPS*phosphoadenosine phosphosulfate*3'-phosphoadenosine-5'-phosphosulfate*3'-phosphoadenylyl-sulfate 507.262 C10 H15 N5 O13 P2 S1 [CH]1(O[CH](C(C(O)1)OP(=O)(O)O)COP(O)(=O)OS(O)(=O)=O)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00053:*CAS:482-67-7 1.8.4.8 sulfite + adenosine-3',5'-bisphosphate = phosphoadenosine-5'-phosphosulfate sulfate reduction I (assimilatory) GA19 gibberellin A19*gibberellin A19*GA19 362.422 C20 H26 O6 CC1([CH]4(C(CCC1)(C=O)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA19 + O2 + α-ketoglutarate = GA20 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) GA19 gibberellin A19*gibberellin A19*GA19 362.422 C20 H26 O6 CC1([CH]4(C(CCC1)(C=O)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA19 + O2 + α-ketoglutarate = GA17 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) GA19 gibberellin A19*gibberellin A19*GA19 362.422 C20 H26 O6 CC1([CH]4(C(CCC1)(C=O)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.12 GA44 + α-ketoglutarate + O2 = GA19 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) mannosyl-inositol-phosphorylceramide MIPC 2.4.1.- mannosyl-inositol-phosphorylceramide + inositol phosphate = mannosyl-diinositol-phosphorylceramide sphingolipid metabolism mannosyl-inositol-phosphorylceramide MIPC 2.4.1.- inositol-P-ceramide + GDP-D-mannose = mannosyl-inositol-phosphorylceramide sphingolipid metabolism zymostenol 5α-cholesta-8-en-3β-ol*cholestenol 386.66 C27 H46 O1 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)CC(O)CC4)(C)))(C)) PUBCHEM:101770: 5.3.3.5 zymostenol = lathosterol cholesterol biosynthesis II (via 24,25-dihydrolanosterol) zymostenol 5α-cholesta-8-en-3β-ol*cholestenol 386.66 C27 H46 O1 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)CC(O)CC4)(C)))(C)) PUBCHEM:101770: 1.1.1.270 5α-cholesta-8-en-3-one + NADPH = zymostenol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 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 219.136 C6 H10 N3 O4 P1 Cc1(nc(N)c(cn1)COP(O)(O)=O) LIGAND-CPD:C04556: 5-aminoimidazole ribonucleotide = hydroxymethylpyrimidine phosphate thiamine biosynthesis 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 219.136 C6 H10 N3 O4 P1 Cc1(nc(N)c(cn1)COP(O)(O)=O) LIGAND-CPD:C04556: 2.7.4.7 hydroxymethylpyrimidine phosphate + ATP = 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate + ADP thiamine biosynthesis 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 219.136 C6 H10 N3 O4 P1 Cc1(nc(N)c(cn1)COP(O)(O)=O) LIGAND-CPD:C04556: 2.7.1.49 ATP + hydroxymethylpyrimidine = ADP + hydroxymethylpyrimidine phosphate thiamine biosynthesis feruloyl-CoA 943.705 C31 H44 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(=O)(O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc4(cc(OC)c(O)cc4)) 2.3.1.110 feruloyl-CoA + tyramine = N-feruloyltyramine + coenzyme A suberin biosynthesis feruloyl-CoA 943.705 C31 H44 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(=O)(O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc4(cc(OC)c(O)cc4)) 6.2.1.12 ferulate + coenzyme A + ATP = feruloyl-CoA + AMP + diphosphate suberin biosynthesis feruloyl-CoA 943.705 C31 H44 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(=O)(O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc4(cc(OC)c(O)cc4)) 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + feruloyl-CoA suberin biosynthesis feruloyl-CoA 943.705 C31 H44 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(=O)(O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc4(cc(OC)c(O)cc4)) 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + feruloyl-CoA phenylpropanoid biosynthesis feruloyl-CoA 943.705 C31 H44 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(=O)(O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc4(cc(OC)c(O)cc4)) 1.2.1.44 feruloyl-CoA + NADPH = coniferyl aldehyde + NADP+ + coenzyme A phenylpropanoid biosynthesis 2-amino-muconate 2-Aminomuconate 157.126 C6 H7 N1 O4 C(O)(=O)C(N)=CC=CC(O)=O 1.2.1.32 H2O + NAD+ + 2-aminomuconate semialdehyde = NADH + 2-amino-muconate tryptophan degradation III (eukaryotic) 2-amino-muconate 2-Aminomuconate 157.126 C6 H7 N1 O4 C(O)(=O)C(N)=CC=CC(O)=O 2-amino-muconate + H2O + NADH = NH(4)OH + α-ketoadipate + NAD+ tryptophan degradation III (eukaryotic) xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 c12(c([nH]cn1)c(=O)[nH]c(=O)[nH]2) LIGAND-CPD:C00385:*CAS:69-89-6 hypoxanthine + H2O = H+ + xanthine salvage pathways of adenine, hypoxanthine, and their nucleosides xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 c12(c([nH]cn1)c(=O)[nH]c(=O)[nH]2) LIGAND-CPD:C00385:*CAS:69-89-6 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ purine degradation xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 c12(c([nH]cn1)c(=O)[nH]c(=O)[nH]2) LIGAND-CPD:C00385:*CAS:69-89-6 1.17.1.4 hypoxanthine + NAD+ + H2O = xanthine + NADH + H+ salvage pathways of purine nucleosides II (plant) xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 c12(c([nH]cn1)c(=O)[nH]c(=O)[nH]2) LIGAND-CPD:C00385:*CAS:69-89-6 3.5.4.3 H2O + guanine = ammonia + xanthine purine degradation xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 c12(c([nH]cn1)c(=O)[nH]c(=O)[nH]2) LIGAND-CPD:C00385:*CAS:69-89-6 3.5.4.3 H2O + guanine = ammonia + xanthine salvage pathways of purine nucleosides xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 c12(c([nH]cn1)c(=O)[nH]c(=O)[nH]2) LIGAND-CPD:C00385:*CAS:69-89-6 3.5.4.3 H2O + guanine = ammonia + xanthine salvage pathways of purine nucleosides II (plant) xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 c12(c([nH]cn1)c(=O)[nH]c(=O)[nH]2) LIGAND-CPD:C00385:*CAS:69-89-6 3.2.2.1 xanthosine + H2O = xanthine + D-ribose purine degradation xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 c12(c([nH]cn1)c(=O)[nH]c(=O)[nH]2) LIGAND-CPD:C00385:*CAS:69-89-6 3.2.2.1 xanthosine + H2O = xanthine + D-ribose salvage pathways of purine nucleosides II (plant) xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 c12(c([nH]cn1)c(=O)[nH]c(=O)[nH]2) LIGAND-CPD:C00385:*CAS:69-89-6 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ purine degradation xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 c12(c([nH]cn1)c(=O)[nH]c(=O)[nH]2) LIGAND-CPD:C00385:*CAS:69-89-6 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ salvage pathways of adenine, hypoxanthine, and their nucleosides xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 c12(c([nH]cn1)c(=O)[nH]c(=O)[nH]2) LIGAND-CPD:C00385:*CAS:69-89-6 1.17.1.4 xanthine + NAD+ + H2O = urate + NADH + H+ ureide biosynthesis xanthine 2,6-dioxopurine 152.112 C5 H4 N4 O2 c12(c([nH]cn1)c(=O)[nH]c(=O)[nH]2) LIGAND-CPD:C00385:*CAS:69-89-6 xanthosine = ribose-1-phosphate + xanthine ureide biosynthesis acetoacetate 3-ketobutyrate*3-oxobutanate*oxobutyrate*acetoacetic acid*3-oxobutyric acid*3-oxobutanoic acid*diacetic acid*β-ketobutyric acid 102.09 C4 H6 O3 C(O)(=O)CC(=O)C LIGAND-CPD:C00164:*CAS:541-50-4 4.1.1.4 acetoacetate + H+ = acetone + CO2 acetone degradation (to methylglyoxal) acetoacetate 3-ketobutyrate*3-oxobutanate*oxobutyrate*acetoacetic acid*3-oxobutyric acid*3-oxobutanoic acid*diacetic acid*β-ketobutyric acid 102.09 C4 H6 O3 C(O)(=O)CC(=O)C LIGAND-CPD:C00164:*CAS:541-50-4 3.7.1.2 H2O + 4-fumaryl-acetoacetate = fumarate + acetoacetate tyrosine degradation I acetoacetate 3-ketobutyrate*3-oxobutanate*oxobutyrate*acetoacetic acid*3-oxobutyric acid*3-oxobutanoic acid*diacetic acid*β-ketobutyric acid 102.09 C4 H6 O3 C(O)(=O)CC(=O)C LIGAND-CPD:C00164:*CAS:541-50-4 4.1.3.4 3-hydroxy-3-methyl-glutaryl-CoA = acetoacetate + acetyl-CoA mevalonate degradation acetoacetate 3-ketobutyrate*3-oxobutanate*oxobutyrate*acetoacetic acid*3-oxobutyric acid*3-oxobutanoic acid*diacetic acid*β-ketobutyric acid 102.09 C4 H6 O3 C(O)(=O)CC(=O)C LIGAND-CPD:C00164:*CAS:541-50-4 4.1.3.4 3-hydroxy-3-methyl-glutaryl-CoA = acetoacetate + acetyl-CoA leucine degradation I 2-methyl-6-solanyl-1,4-benzoquinone 739.219 C52 H82 O2 CC(=CCCC(C)=CCCC(C)=CCC1(C(O)C(C)=CC(C=1)O))CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C homogentisate + solanyl pyrophosphate = 2-methyl-6-solanyl-1,4-benzoquinone + CO2 + diphosphate plastoquinone biosynthesis 2-methyl-6-solanyl-1,4-benzoquinone 739.219 C52 H82 O2 CC(=CCCC(C)=CCCC(C)=CCC1(C(O)C(C)=CC(C=1)O))CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C 2.1.1.- 2-methyl-6-solanyl-1,4-benzoquinone + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine plastoquinone biosynthesis (-)-α-terpineol (-)-(4S)-α-terpineol 154.252 C10 H18 O1 CC1(=CCC(C(C)(C)O)CC1) (-)-α-terpineol = 1,8-cineole monoterpene biosynthesis (-)-α-terpineol (-)-(4S)-α-terpineol 154.252 C10 H18 O1 CC1(=CCC(C(C)(C)O)CC1) 4.2.3.- geranyl-PP + H2O = (-)-α-terpineol + diphosphate monoterpene biosynthesis 24-methyldesmosterol 398.671 C28 H46 O1 CC(C)=C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) 1.3.-.- 24-methyldesmosterol = 24-epi-campesterol sterol biosynthesis 24-methyldesmosterol 398.671 C28 H46 O1 CC(C)=C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) 24-methylenecholesterol = 24-methyldesmosterol sterol biosynthesis 24-methyldesmosterol 398.671 C28 H46 O1 CC(C)=C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) 1.3.-.- 24-methyldesmosterol = campesterol sterol biosynthesis mannose-6-phosphate D-mannose-6-phosphate*α-D-mannose-6-phosphate*α-D-mannose-6-P 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) LIGAND-CPD:C00275:*CAS:3672-15-9 5.3.1.8 mannose-6-phosphate = fructose-6-phosphate ascorbate biosynthesis mannose-6-phosphate D-mannose-6-phosphate*α-D-mannose-6-phosphate*α-D-mannose-6-P 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) LIGAND-CPD:C00275:*CAS:3672-15-9 5.3.1.8 mannose-6-phosphate = fructose-6-phosphate GDP-mannose metabolism mannose-6-phosphate D-mannose-6-phosphate*α-D-mannose-6-phosphate*α-D-mannose-6-P 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) LIGAND-CPD:C00275:*CAS:3672-15-9 5.3.1.8 mannose-6-phosphate = fructose-6-phosphate mannose degradation mannose-6-phosphate D-mannose-6-phosphate*α-D-mannose-6-phosphate*α-D-mannose-6-P 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) LIGAND-CPD:C00275:*CAS:3672-15-9 2.7.1.7 mannose + ATP = mannose-6-phosphate + ADP GDP-mannose metabolism mannose-6-phosphate D-mannose-6-phosphate*α-D-mannose-6-phosphate*α-D-mannose-6-P 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) LIGAND-CPD:C00275:*CAS:3672-15-9 2.7.1.7 mannose + ATP = mannose-6-phosphate + ADP mannose degradation mannose-6-phosphate D-mannose-6-phosphate*α-D-mannose-6-phosphate*α-D-mannose-6-P 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) LIGAND-CPD:C00275:*CAS:3672-15-9 5.4.2.8 α-D-mannose 1-phosphate = mannose-6-phosphate ascorbate biosynthesis mannose-6-phosphate D-mannose-6-phosphate*α-D-mannose-6-phosphate*α-D-mannose-6-P 260.137 C6 H13 O9 P1 C(OP(O)(O)=O)C1(C(O)C(O)C(O)C(O1)O) LIGAND-CPD:C00275:*CAS:3672-15-9 5.4.2.8 α-D-mannose 1-phosphate = mannose-6-phosphate GDP-mannose metabolism trehalose 6-phosphate α,α-trehalose 6-phosphate 422.279 C12 H23 O14 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(OC2(OC(CO)C(O)C(O)C(O)2)) 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 422.279 C12 H23 O14 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(OC2(OC(CO)C(O)C(O)C(O)2)) LIGAND-CPD:C00689:*CAS:4484-88-2 2.4.1.15 UDP-D-glucose + α-D-glucose 6-phosphate = UDP + trehalose 6-phosphate trehalose biosynthesis I formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 formate = CO2 + H2 mixed acid fermentation formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 formate = CO2 + H2 respiration (anaerobic) formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 3.5.1.9 N-formylkynurenine + H2O = kynurenine + formate tryptophan degradation III (eukaryotic) formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF folate polyglutamylation I formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF folate transformations formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF formylTHF biosynthesis II formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF formylTHF biosynthesis I formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 3.5.4.25 H2O + GTP = diphosphate + 2,5-diamino-6-(ribosylamino)-4-(3H)-pyrimidinone 5'-phosphate + formate flavin biosynthesis formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol + O2 + NADPH = 4,4-dimethyl-5-α-cholesta-8,14-dien-3-β-ol + formate + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADP+ + H2O + formate cholesterol biosynthesis I formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADP+ + H2O + formate cholesterol biosynthesis III (via desmosterol) formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 3.5.1.10 H2O + N10-formyl-THF = tetrahydrofolate + formate folate transformations formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 3.5.1.10 H2O + N10-formyl-THF = tetrahydrofolate + formate formylTHF biosynthesis I formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 3.1.2.12 S-formylglutathione + H2O = formate + glutathione formaldehyde oxidation II (glutathione-dependent) formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 D-ribulose-5-phosphate = 3,4-dihydroxy-2-butanone-4-P + formate flavin biosynthesis formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 1.13.11.54 1,2-dihydroxy-3-keto-5-methylthiopentene + O2 = 2-oxo-4-methylthiobutanoate + formate methionine salvage pathway formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 2.3.1.54 formate + acetyl-CoA = pyruvate + coenzyme A mixed acid fermentation formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 2.3.1.54 formate + acetyl-CoA = pyruvate + coenzyme A respiration (anaerobic) formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 6.3.4.3 ADP = ATP + formate tetrahydrofolate biosynthesis II formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = 5'-phosphoribosyl-N-formylglycineamide + ADP purine nucleotides de novo biosynthesis I formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 1.14.13.70 NADPH + O2 + obtusifoliol + H+ = H2O + NADP+ + formate + (4α)-methyl-(5α)-ergosta-8,14,24(28)-trien-3β-ol sterol biosynthesis formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 1.2.1.2 formate + menaquinone-8 = CO2 + menaquinol respiration (anaerobic)-- electron donors reaction list formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 1.2.1.2 formate + menaquinone-8 = CO2 + menaquinol formate oxidation to CO2 formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 3.5.4.16 GTP + H2O = formate + 7,8-dihydroneopterin 3'-triphosphate tetrahydrofolate biosynthesis I formate formic acid 46.026 C1 H2 O2 [CH](=O)O LIGAND-CPD:C00058:*CAS:64-18-6 3.5.4.16 GTP + H2O = formate + 7,8-dihydroneopterin 3'-triphosphate tetrahydrofolate biosynthesis II δ-carotene ε,ψ-carotene 536.882 C40 H56 CC(C=CC1(C(C)=CCCC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC=C(C)CCC=C(C)C 5.5.1.- δ-carotene = ε-carotene lactucaxanthin biosynthesis δ-carotene ε,ψ-carotene 536.882 C40 H56 CC(C=CC1(C(C)=CCCC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC=C(C)CCC=C(C)C 5.5.1.- δ-carotene = α-carotene carotenoid biosynthesis δ-carotene ε,ψ-carotene 536.882 C40 H56 CC(C=CC1(C(C)=CCCC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC=C(C)CCC=C(C)C 5.5.1.- trans-lycopene = δ-carotene carotenoid biosynthesis (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->2)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1,6)]-α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 3135.549 C150 H250 N2 O62 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC8(OC(COC5(OC(COC3(C(C(O)C(O)C(O3)CO)OC4(OC(CO)C(O)C(O)C(O)4)))C(O)C(C(O)5)OC6(C(C(O)C(O)C(O6)CO)OC7(OC(CO)C(O)C(O)C(O)7))))C(O)C(C(O)8)OC9(C(C(O)C(O)C(O9)CO)OC10(C(C(O)C(O)C(O10)CO)OC11(OC(CO)C(O)C(O)C(O)11)))))) (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol {α-D-mannosyl-(1->2)-α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1->3)-[α-D-mannosyl-(1->2)-α-D-mannosyl-(1,6)]-α-D-mannosyl-(1,6)]-β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 3135.549 C150 H250 N2 O62 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(OC(CO)C(C(O)C2NC(C)=O)OC8(OC(COC5(OC(COC3(C(C(O)C(O)C(O3)CO)OC4(OC(CO)C(O)C(O)C(O)4)))C(O)C(C(O)5)OC6(C(C(O)C(O)C(O6)CO)OC7(OC(CO)C(O)C(O)C(O)7))))C(O)C(C(O)8)OC9(C(C(O)C(O)C(O9)CO)OC10(C(C(O)C(O)C(O10)CO)OC11(OC(CO)C(O)C(O)C(O)11)))))) (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-glucosyl phosphate = glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis dephospho-CoA 3-dephospho-CoA*dephosphocoenzyme A 687.554 C21 H35 N7 O13 P2 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OCC1(OC(C(O)C1O)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00882:*CAS:3633-59-8 2.7.1.24 dephospho-CoA + ATP = coenzyme A + ADP coenzyme A biosynthesis dephospho-CoA 3-dephospho-CoA*dephosphocoenzyme A 687.554 C21 H35 N7 O13 P2 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OCC1(OC(C(O)C1O)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00882:*CAS:3633-59-8 2.7.7.3 pantetheine 4'-phosphate + ATP = dephospho-CoA + diphosphate coenzyme A biosynthesis UDP-sulfoquinovose UDP-6-sulfoquinovose 630.364 C15 H24 N2 O19 P2 S1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(OC(CS(=O)(O)=O)C(O)C(O)C3O))) UDP-sulfoquinovose = sulfoquinovosyldiacylglycerol + UDP glycolipid biosynthesis UDP-sulfoquinovose UDP-6-sulfoquinovose 630.364 C15 H24 N2 O19 P2 S1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(OC(CS(=O)(O)=O)C(O)C(O)C3O))) 3.13.1.1 sulfite + UDP-D-glucose = UDP-sulfoquinovose + H2O glycolipid biosynthesis D-lactoyl-CoA 839.597 C24 H40 N7 O18 P3 S1 C([CH]1(O[CH]([CH](O)[CH]1OP(=O)(O)O)n2(c3(c(nc2)c(N)ncn3))))OP(=O)(O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(O)C 4.2.1.54 D-lactoyl-CoA = H2O + acrylyl-CoA D-lactate fermentation to propionate and acetate D-lactoyl-CoA 839.597 C24 H40 N7 O18 P3 S1 C([CH]1(O[CH]([CH](O)[CH]1OP(=O)(O)O)n2(c3(c(nc2)c(N)ncn3))))OP(=O)(O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(O)C 2.8.3.- D-lactate + propionyl-CoA = D-lactoyl-CoA + propionate D-lactate fermentation to propionate and acetate 16-hydroxypalmitate 272.427 C16 H32 O3 C(O)(=O)CCCCCCCCCCCCCCCO 16-hydroxypalmitate + NADPH + O2 = 10,16-dihydroxypalmitate + NADP+ + H2O cutin biosynthesis 16-hydroxypalmitate 272.427 C16 H32 O3 C(O)(=O)CCCCCCCCCCCCCCCO 1.14.13.- palmitate + NADPH + O2 = 16-hydroxypalmitate + NADP+ + H2O cutin biosynthesis pyridoxamine PM 168.195 C8 H12 N2 O2 C(N)c1(c(CO)cnc(C)c1O) LIGAND-CPD:C00534:*CAS:85-87-0 2.6.1.30 pyruvate + pyridoxamine = L-alanine + pyridoxal pyridoxamine anabolism pyridoxamine PM 168.195 C8 H12 N2 O2 C(N)c1(c(CO)cnc(C)c1O) LIGAND-CPD:C00534:*CAS:85-87-0 2.7.1.35 ATP + pyridoxamine = ADP + pyridoxamine 5'-phosphate pyridoxal 5'-phosphate salvage pathway protoporphyrin IX protoporphyrin 562.667 C34 H32 N4 O4 Cc5(c(CCC(=O)O)c4(C=C1(N=C(C(C)=C1CCC(=O)O)C=c2(nc(c(c2C)C=C)=CC3(=NC(C(=C3C)C=C)=Cc(n4)5))))) LIGAND-CPD:C02191:*CAS:553-12-8 1.3.3.4 protoporphyrinogen IX + O2 = protoporphyrin IX + H2O heme biosynthesis II protoporphyrin IX protoporphyrin 562.667 C34 H32 N4 O4 Cc5(c(CCC(=O)O)c4(C=C1(N=C(C(C)=C1CCC(=O)O)C=c2(nc(c(c2C)C=C)=CC3(=NC(C(=C3C)C=C)=Cc(n4)5))))) LIGAND-CPD:C02191:*CAS:553-12-8 1.3.3.4 protoporphyrinogen IX + O2 = protoporphyrin IX + H2O chlorophyllide a biosynthesis protoporphyrin IX protoporphyrin 562.667 C34 H32 N4 O4 Cc5(c(CCC(=O)O)c4(C=C1(N=C(C(C)=C1CCC(=O)O)C=c2(nc(c(c2C)C=C)=CC3(=NC(C(=C3C)C=C)=Cc(n4)5))))) LIGAND-CPD:C02191:*CAS:553-12-8 4.99.1.1 Fe2+ + protoporphyrin IX = H+ + protoheme IX heme biosynthesis II protoporphyrin IX protoporphyrin 562.667 C34 H32 N4 O4 Cc5(c(CCC(=O)O)c4(C=C1(N=C(C(C)=C1CCC(=O)O)C=c2(nc(c(c2C)C=C)=CC3(=NC(C(=C3C)C=C)=Cc(n4)5))))) LIGAND-CPD:C02191:*CAS:553-12-8 6.6.1.1 ATP + protoporphyrin IX + Mg2+ + H2O = Mg-protoporphyrin + ADP + H+ chlorophyllide a 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 269.147 C7 H12 N1 O8 P1 CC(=O)NC(C(O)=O)CCC(=O)OP(O)(O)=O PUBCHEM:440236:*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 269.147 C7 H12 N1 O8 P1 CC(=O)NC(C(O)=O)CCC(=O)OP(O)(O)=O PUBCHEM:440236:*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 269.147 C7 H12 N1 O8 P1 CC(=O)NC(C(O)=O)CCC(=O)OP(O)(O)=O PUBCHEM:440236:*LIGAND-CPD:C04133: 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = 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 269.147 C7 H12 N1 O8 P1 CC(=O)NC(C(O)=O)CCC(=O)OP(O)(O)=O PUBCHEM:440236:*LIGAND-CPD:C04133: 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = N-acetylglutamyl-phosphate + NADPH ornithine biosynthesis oxalurate oxaluric acid*monooxalylurea*oxalureate*ureido(oxo)acetic acid 132.076 C3 H4 N2 O4 C(=O)(C(=O)O)NC(N)=O PUBCHEM:456:*LIGAND-CPD:C00802:*CAS:585-05-7 1.1.1.154 (S)-ureidoglycolate = oxalurate allantoin degradation I homomethionine 163.234 C6 H13 N1 O2 S1 C(O)(=O)C(N)CCCSC 2.6.1.- 2-oxo-5-methylthiopentanoic-acid = homomethionine homomethionine biosynthesis nicotianamine NA 303.314 C12 H21 N3 O6 C1(N(C(C1)C(=O)O)CC[CH](C(=O)O)NCC[CH](N)C(=O)O) CAS:34441-14-0 2.5.1.43 S-adenosyl-L-methionine = nicotianamine + 5'-methylthioadenosine 2'-deoxymugineic acid phytosiderophore biosynthesis nicotianamine NA 303.314 C12 H21 N3 O6 C1(N(C(C1)C(=O)O)CC[CH](C(=O)O)NCC[CH](N)C(=O)O) CAS:34441-14-0 2.6.1.80 nicotianamine + α-ketoglutarate = 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 CC(C)C(C)CC(O)C(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(CC3)=CC(=O)CC4)(C)))) 1.3.99.- (22α)-hydroxy-campest-4-en-3-one + NADPH = (22α)-hydroxy-5α-campestan-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 CC(C)C(C)CC(O)C(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(CC3)=CC(=O)CC4)(C)))) 1.14.13.- campest-4-en-3-one + O2 + 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 CC(C)C(C)CC(O)C(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(CC3)=CC(=O)CC4)(C)))) (22α)-hydroxy-campesterol = (22α)-hydroxy-campest-4-en-3-one brassinosteroid biosynthesis II dGTP 2'-deoxyguanosine-5'-triphosphate*deoxy-GTP*deoxyguanosine-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(CC1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00286:*CAS:2564-35-4 GTP = dGTP + H2O purine nucleotides de novo biosynthesis I dGTP 2'-deoxyguanosine-5'-triphosphate*deoxy-GTP*deoxyguanosine-triphosphate 507.183 C10 H16 N5 O13 P3 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(CC1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00286:*CAS:2564-35-4 2.7.4.6 dGDP + ATP = dGTP + ADP purine nucleotides de novo biosynthesis I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA44 + α-ketoglutarate + O2 = GA98 + succinate + CO2 gibberellin inactivation α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate glutamine degradation III α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate asparagine degradation I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate aspartate biosynthesis I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate aspartate degradation II α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.1 L-aspartate + α-ketoglutarate = L-glutamate + oxaloacetate asparagine biosynthesis I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA12 + α-ketoglutarate + O2 = GA110 + succinate + CO2 gibberellin inactivation α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA34 + α-ketoglutarate + O2 = GA34-catabolite + succinate + CO2 + H2O gibberellin inactivation α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 α-ketoglutarate + coenzyme A + NAD+ = succinyl-CoA + CO2 + NADH TCA cycle α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.5 L-tyrosine + α-ketoglutarate = L-glutamate + p-hydroxyphenylpyruvate tyrosine degradation I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA51 + α-ketoglutarate + O2 = GA51-catabolite + succinate + CO2 + H2O gibberellin inactivation α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.1 3-sulfinoalanine + α-ketoglutarate = L-glutamate + 3-sulfinyl-pyruvate L-cysteine degradation I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.4 α-ketoglutarate + glycine = L-glutamate + glyoxylate photorespiration α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA8 + α-ketoglutarate + O2 = GA8-catabolite + succinate + CO2 + H2O gibberellin inactivation α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.80 nicotianamine + α-ketoglutarate = L-glutamate + 3''-deamino-3''-oxonicotianamine 2'-deoxymugineic acid phytosiderophore biosynthesis α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.1.1.42 NADP+ = NADPH + α-ketoglutarate + CO2 TCA cycle variation I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.1.1.42 NADP+ = NADPH + α-ketoglutarate + CO2 respiration (anaerobic) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.1.1.42 NADP+ = NADPH + α-ketoglutarate + CO2 TCA cycle α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA9 + α-ketoglutarate + O2 = GA51 + succinate + CO2 gibberellin inactivation α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 3',4',5'-pentahydroxyflavanone + α-ketoglutarate + O2 = dihydromyricetin + succinate + CO2 leucodelphinidin biosynthesis α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.11 N2-succinyl-L-ornithine + α-ketoglutarate = L-glutamate + N2-succinyl-L-glutamate 5-semialdehyde arginine degradation II α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA53 + α-ketoglutarate + O2 = GA97 + succinate + CO2 gibberellin inactivation α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.23 α-ketoglutarate + L-erythro-4-hydroxy-glutamate = L-glutamate + D-4-hydroxy-2-keto-glutarate 4-hydroxyproline degradation I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.3 α-ketoglutarate + L-cysteine = L-glutamate + 3-mercaptopyruvate L-cysteine degradation III α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.5.1.7 H2O + NAD+ + saccharopine = NADH + α-ketoglutarate + L-lysine lysine biosynthesis IV α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.52 2-oxo-3-hydroxy-4-phosphobutanoate + L-glutamate = 4-(phosphonooxy)-threonine + α-ketoglutarate pyridoxal 5'-phosphate biosynthesis α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA29 + α-ketoglutarate + O2 = GA29-catabolite + succinate + CO2 + H2O gibberellin inactivation α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.57 phenylpyruvate + L-glutamate = L-phenylalanine + α-ketoglutarate phenylalanine degradation III α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.57 phenylpyruvate + L-glutamate = L-phenylalanine + α-ketoglutarate phenylalanine biosynthesis I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate valine degradation I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate valine biosynthesis α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate pantothenate biosynthesis I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate valine degradation II α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate pantothenate biosynthesis II α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 L-2-acetamido-6-oxoheptanedioate + L-glutamate = N-acetyl-L,L-2,6-diaminopimelate + α-ketoglutarate lysine biosynthesis II α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.- tetrahydrodipicolinate + L-glutamate + H2O = L,L-diaminopimelate + α-ketoglutarate lysine biosynthesis VI α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.23 dihydrokaempferol + α-ketoglutarate + O2 = kaempferol + succinate + CO2 + H2O flavonol biosynthesis α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.13 GA1 + α-ketoglutarate + O2 = GA8 + succinate + CO2 gibberellin inactivation α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.23 dihydroquercetin + α-ketoglutarate + O2 = quercetin + succinate + CO2 + H2O flavonol biosynthesis α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA12 + O2 + α-ketoglutarate = GA15 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA24 + α-ketoglutarate + O2 = GA36 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.9 eriodictyol + O2 + α-ketoglutarate = dihydroquercetin + CO2 + succinate leucopelargonidin and leucocyanidin biosynthesis α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.9 eriodictyol + O2 + α-ketoglutarate = dihydroquercetin + CO2 + succinate leucodelphinidin biosynthesis α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-isoleucine + α-ketoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine degradation I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-isoleucine + α-ketoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine biosynthesis from threonine α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-isoleucine + α-ketoglutarate = L-glutamate + 2-keto-3-methyl-valerate isoleucine degradation II α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-leucine + α-ketoglutarate = L-glutamate + 2-ketoisocaproate leucine degradation III α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-leucine + α-ketoglutarate = L-glutamate + 2-ketoisocaproate leucine biosynthesis α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.42 L-leucine + α-ketoglutarate = L-glutamate + 2-ketoisocaproate leucine degradation I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA4 + α-ketoglutarate + O2 = GA34 + succinate + CO2 gibberellin inactivation α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA9 + α-ketoglutarate + O2 = GA4 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA36 + O2 + α-ketoglutarate = GA4 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA15 + α-ketoglutarate + O2 = GA24 + succinate + CO2 + H2O gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.39 α-ketoglutarate + α-aminoadipate = L-glutamate + α-ketoadipate lysine biosynthesis IV α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.39 α-ketoglutarate + α-aminoadipate = L-glutamate + α-ketoadipate lysine degradation II α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA19 + O2 + α-ketoglutarate = GA20 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.12 GA44 + α-ketoglutarate + O2 = GA19 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.17 α-ketoglutarate = L-glutamate + N-succinyl-2-amino-6-ketopimelate lysine biosynthesis I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.2.4.2 α-ketoglutarate = CO2 2-keto glutarate dehydrogenase complex α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 4.1.1.71 α-ketoglutarate = succinate semialdehyde + CO2 TCA cycle variation I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA53 + O2 + α-ketoglutarate = GA44 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.27 α-ketoglutarate + L-tryptophan = L-glutamate + indole-3-pyruvate IAA biosynthesis I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- leucocyanidin + α-ketoglutarate + O2 = cyanidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA37 + α-ketoglutarate + O2 = GA36 + succinate + CO2 + H2O gibberellin biosynthesis II (early C-3 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 4.1.1.71 α-ketoglutarate + thiamine diphosphate = succinate-semialdehyde-thiamine PPi + CO2 menaquinone biosynthesis α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA20 + α-ketoglutarate + O2 = GA29 + succinate + CO2 gibberellin inactivation α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.3.3.14 α-ketoglutarate + H2O + acetyl-CoA = homocitrate + coenzyme A lysine biosynthesis IV α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA19 + O2 + α-ketoglutarate = GA17 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA24 + O2 + α-ketoglutarate = GA9 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.9 naringenin + O2 + α-ketoglutarate = CO2 + succinate + dihydrokaempferol flavonoid biosynthesis α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.2.7.3 α-ketoglutarate + coenzyme A = succinyl-CoA + CO2 reductive TCA cycle I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA15 + α-ketoglutarate + O2 = GA37 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.9 (2S)-pinocembrin + O2 + α-ketoglutarate = (2R,3R)-pinobanksin + CO2 + succinate pinobanksin biosynthesis α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- leucodelphinidin + O2 + α-ketoglutarate = delphinidin + H2O + CO2 + succinate anthocyanin biosynthesis (delphinidin 3-O-glucoside) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA44 + α-ketoglutarate + O2 = GA38 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.2 α-ketoglutarate + L-alanine = L-glutamate + pyruvate alanine biosynthesis II α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.2 α-ketoglutarate + L-alanine = L-glutamate + pyruvate alanine degradation III α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.4.1.13 L-glutamate + NADP+ = L-glutamine + α-ketoglutarate + NADPH glutamine degradation III α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.4.1.13 L-glutamate + NADP+ = L-glutamine + α-ketoglutarate + NADPH glutamate biosynthesis I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA12 + α-ketoglutarate + O2 = GA14 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.5.1.8 H2O + NADP+ + saccharopine = NADPH + α-ketoglutarate + L-lysine lysine degradation II α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.52 3-phospho-serine + α-ketoglutarate = L-glutamate + 3-phospho-hydroxypyruvate serine biosynthesis α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.19 α-ketoglutarate + 4-aminobutyrate = L-glutamate + succinate semialdehyde glutamate degradation III α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 reductive TCA cycle I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.11 N-acetyl-L-ornithine + α-ketoglutarate = L-glutamate + N-acetyl-L-glutamate 5-semialdehyde arginine biosynthesis II (acetyl cycle) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.11 N-acetyl-L-ornithine + α-ketoglutarate = L-glutamate + N-acetyl-L-glutamate 5-semialdehyde ornithine biosynthesis α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.13 L-ornithine + α-ketoglutarate = L-glutamate + L-glutamate γ-semialdehyde proline biosynthesis V (from arginine) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.13 L-ornithine + α-ketoglutarate = L-glutamate + L-glutamate γ-semialdehyde arginine degradation VI (arginase 2 pathway) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.13 L-ornithine + α-ketoglutarate = L-glutamate + L-glutamate γ-semialdehyde arginine biosynthesis IV α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.13 L-ornithine + α-ketoglutarate = L-glutamate + L-glutamate γ-semialdehyde arginine degradation I (arginase pathway) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 2.6.1.13 L-ornithine + α-ketoglutarate = L-glutamate + L-glutamate γ-semialdehyde citrulline biosynthesis α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA24 + O2 + α-ketoglutarate = GA25 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O 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 + α-ketoglutarate histidine biosynthesis I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 L-serine + α-ketoglutarate = L-glutamate + hydroxypyruvate photorespiration α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.15 GA20 + α-ketoglutarate + O2 = GA1 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA14 + O2 + α-ketoglutarate = GA37 + CO2 + succinate gibberellin biosynthesis II (early C-3 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- GA25 + α-ketoglutarate + O2 = GA13 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.4.1.4 L-glutamate + H2O + NADP+ = ammonia + α-ketoglutarate + NADPH proline biosynthesis I α-ketoglutarate ketoglutarate*α-ketoglutarate*2-oxoglutaric acid*α-ketoglutaric acid*α-oxoglutarate*2-oxoglutarate*2-ketoglutaric acid*2-ketoglutarate*2-oxopentanedionic acid*2-oxopentanedionate 146.099 C5 H6 O5 C(O)(=O)C(=O)CCC(=O)O CHEBI:30915*LIGAND-CPD:C00026*PUBCHEM:51*LIGAND-CPD:C00026:*CAS:328-50-7 1.14.11.- leucopelargonidin + α-ketoglutarate + O2 = pelargonidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) GA53 gibberellin A53*gibberellin A53*GA53 348.438 C20 H28 O5 CC1([CH]4(C(CCC1)(C)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) GA12 + O2 = GA53 + H2O gibberellin biosynthesis III (early C-13 hydroxylation) GA53 gibberellin A53*gibberellin A53*GA53 348.438 C20 H28 O5 CC1([CH]4(C(CCC1)(C)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA53 + O2 + α-ketoglutarate = GA44 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) GA53 gibberellin A53*gibberellin A53*GA53 348.438 C20 H28 O5 CC1([CH]4(C(CCC1)(C)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA53 + α-ketoglutarate + O2 = GA97 + succinate + CO2 gibberellin inactivation 18:2-18:3-DGDG 1-18:2-2-18:3-digalactosyldiacylglycerol*1-(9Z,12Z-octadecenoyl)-2-(9Z,12Z,15Z-octadecatrienoyl)-3-O-[alpha-D-galactosyl-(1>6)-O-beta-D-galactosyl]-sn-glycerol 939.231 C51 H86 O15 C(OC1(OC(C(O)C(O)C1O)COC2(C(O)C(O)C(O)C(O2)CO)))C(OC(=O)CCCCCCCC=CCC=CCC=CCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-18:2-DGDG = 18:2-18:3-DGDG glycolipid desaturation 18:2-18:3-DGDG 1-18:2-2-18:3-digalactosyldiacylglycerol*1-(9Z,12Z-octadecenoyl)-2-(9Z,12Z,15Z-octadecatrienoyl)-3-O-[alpha-D-galactosyl-(1>6)-O-beta-D-galactosyl]-sn-glycerol 939.231 C51 H86 O15 C(OC1(OC(C(O)C(O)C1O)COC2(C(O)C(O)C(O)C(O2)CO)))C(OC(=O)CCCCCCCC=CCC=CCC=CCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-18:3-DGDG = 18:3-18:3-DGDG glycolipid desaturation 3-sulfinoalanine 3-sulfino-L-alanine*L-cysteinesulfinic acid*3-sulphino-L-alanine 153.153 C3 H7 N1 O4 S1 C(=O)(O)C(N)CS(=O)O LIGAND-CPD:C00606:*CAS:1115-65-7 1.13.11.20 O2 + L-cysteine = 3-sulfinoalanine L-cysteine degradation I 3-sulfinoalanine 3-sulfino-L-alanine*L-cysteinesulfinic acid*3-sulphino-L-alanine 153.153 C3 H7 N1 O4 S1 C(=O)(O)C(N)CS(=O)O LIGAND-CPD:C00606:*CAS:1115-65-7 2.6.1.1 3-sulfinoalanine + α-ketoglutarate = L-glutamate + 3-sulfinyl-pyruvate L-cysteine degradation I lipid A disaccharide 2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-β-phosphate*2,3-bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate*2'-3'-diacyl-GlcN(β-1'-6)2,3-diacyl-GlcN-1-P*2,3,2',3'-tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1-phosphate*2,3-bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphate*[2-N,3-O-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl]-(1 => 6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl phosphate] 1325.742 C68 H129 N2 O20 P1 CCCCCCCCCCCC(O)CC(=O)NC1(C(OP(=O)(O)O)OC(C(O)C1OC(=O)CC(O)CCCCCCCCCCC)COC2(C(NC(=O)CC(O)CCCCCCCCCCC)C(C(O)C(O2)CO)OC(=O)CC(O)CCCCCCCCCCC)) LIGAND-CPD:C04932: 2.7.1.130 lipid A disaccharide + ATP = lipid IVA + ADP lipid-A-precursor biosynthesis lipid A disaccharide 2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-β-phosphate*2,3-bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate*2'-3'-diacyl-GlcN(β-1'-6)2,3-diacyl-GlcN-1-P*2,3,2',3'-tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1-phosphate*2,3-bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphate*[2-N,3-O-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl]-(1 => 6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl phosphate] 1325.742 C68 H129 N2 O20 P1 CCCCCCCCCCCC(O)CC(=O)NC1(C(OP(=O)(O)O)OC(C(O)C1OC(=O)CC(O)CCCCCCCCCCC)COC2(C(NC(=O)CC(O)CCCCCCCCCCC)C(C(O)C(O2)CO)OC(=O)CC(O)CCCCCCCCCCC)) LIGAND-CPD:C04932: 2.4.1.182 2,3-bis(3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate + UDP-2,3-bis(3-hydroxymyristoyl)glucosamine = lipid A disaccharide + UDP lipid-A-precursor biosynthesis 3-hydroxy-isobutyrate 3-Hydroxy-2-methylpropanoate*3-Hydroxyisobutyric acid*3-OH-iso-but*3-OH-isobutyrate 104.105 C4 H8 O3 C(O)(=O)C(C)CO CAS:2068-83-9 1.1.1.31 NAD+ + 3-hydroxy-isobutyrate = NADH + methylmalonate-semialdehyde valine degradation I 3-hydroxy-isobutyrate 3-Hydroxy-2-methylpropanoate*3-Hydroxyisobutyric acid*3-OH-iso-but*3-OH-isobutyrate 104.105 C4 H8 O3 C(O)(=O)C(C)CO CAS:2068-83-9 3.1.2.4 H2O + 3-hydroxy-isobutyryl-CoA = 3-hydroxy-isobutyrate + coenzyme A valine degradation I chorismate chorismic acid 226.185 C10 H10 O6 C=C(C(O)=O)OC1(C(O)C=CC(=C1)C(O)=O) CAS:55508-12-8:*LIGAND-CPD:C00251: 6.3.5.8 L-glutamine + chorismate = L-glutamate + 4-amino-4-deoxychorismate tetrahydrofolate biosynthesis I chorismate chorismic acid 226.185 C10 H10 O6 C=C(C(O)=O)OC1(C(O)C=CC(=C1)C(O)=O) CAS:55508-12-8:*LIGAND-CPD:C00251: 6.3.5.8 L-glutamine + chorismate = L-glutamate + 4-amino-4-deoxychorismate tetrahydrofolate biosynthesis II chorismate chorismic acid 226.185 C10 H10 O6 C=C(C(O)=O)OC1(C(O)C=CC(=C1)C(O)=O) CAS:55508-12-8:*LIGAND-CPD:C00251: 5.4.4.2 chorismate = isochorismate menaquinone biosynthesis chorismate chorismic acid 226.185 C10 H10 O6 C=C(C(O)=O)OC1(C(O)C=CC(=C1)C(O)=O) CAS:55508-12-8:*LIGAND-CPD:C00251: 5.4.4.2 chorismate = isochorismate phylloquinone biosynthesis chorismate chorismic acid 226.185 C10 H10 O6 C=C(C(O)=O)OC1(C(O)C=CC(=C1)C(O)=O) CAS:55508-12-8:*LIGAND-CPD:C00251: 5.4.4.2 chorismate = isochorismate enterobactin biosynthesis chorismate chorismic acid 226.185 C10 H10 O6 C=C(C(O)=O)OC1(C(O)C=CC(=C1)C(O)=O) CAS:55508-12-8:*LIGAND-CPD:C00251: 5.4.4.2 chorismate = isochorismate salicylate biosynthesis chorismate chorismic acid 226.185 C10 H10 O6 C=C(C(O)=O)OC1(C(O)C=CC(=C1)C(O)=O) CAS:55508-12-8:*LIGAND-CPD:C00251: 4.2.3.5 5-enolpyruvyl-shikimate-3-phosphate = chorismate chorismate biosynthesis chorismate chorismic acid 226.185 C10 H10 O6 C=C(C(O)=O)OC1(C(O)C=CC(=C1)C(O)=O) CAS:55508-12-8:*LIGAND-CPD:C00251: 5.4.99.5 chorismate = prephenate phenylalanine biosynthesis I chorismate chorismic acid 226.185 C10 H10 O6 C=C(C(O)=O)OC1(C(O)C=CC(=C1)C(O)=O) CAS:55508-12-8:*LIGAND-CPD:C00251: 4.1.3.27 chorismate + L-glutamine = L-glutamate + anthranilate + pyruvate tryptophan biosynthesis selenophosphate SePO3 160.956 H3 O3 P1 SE1 OP(O)(=[Se])O CAS:16561-29-8:*LIGAND-CPD:C05172: 2.9.1.1 selenophosphate = H2O selenocysteine biosynthesis selenophosphate SePO3 160.956 H3 O3 P1 SE1 OP(O)(=[Se])O CAS:16561-29-8:*LIGAND-CPD:C05172: 2.7.9.3 H2O + selenide + ATP = selenophosphate + AMP selenocysteine biosynthesis ent-kaur-16-en-19-al 286.456 C20 H30 O1 C=C1(C2(CC3(C1)([CH](CC2)C4(C)([CH](CC3)C(C)(C=O)CCC4)))) 1.14.13.78 ent-kaur-16-en-19-ol + NADPH + H+ + O2 = ent-kaur-16-en-19-al + NADP+ + H2O GA12 biosynthesis ent-kaur-16-en-19-al 286.456 C20 H30 O1 C=C1(C2(CC3(C1)([CH](CC2)C4(C)([CH](CC3)C(C)(C=O)CCC4)))) 1.14.13.78 ent-kaur-16-en-19-al + NADPH + H+ + O2 = ent-kaurenoate + NADP+ + H2O GA12 biosynthesis 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester 612.967 C35 H32 N4 O5 MG1 Cc6(c(C(=O)CC(=O)OC)c1(n7([Mg]35(n4(c(C=C2(C(C)=C(C(C=1)=N23)CCC(O)=O))c(C)c(C=C)c4C=C8(N5=C(C=c67)C(C=C)=C(C)8)))))) 1.14.13.81 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester 612.967 C35 H32 N4 O5 MG1 Cc6(c(C(=O)CC(=O)OC)c1(n7([Mg]35(n4(c(C=C2(C(C)=C(C(C=1)=N23)CCC(O)=O))c(C)c(C=C)c4C=C8(N5=C(C=c67)C(C=C)=C(C)8)))))) 1.14.13.81 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = divinyl protochlorophyllide a + NADP+ + H2O chlorophyllide a biosynthesis tetrahydrodipicolinate 2,3,4,5-Tetrahydrodipicolinate*L-2,3,4,5-tetrahydrodipicolinate*Δ1-piperideine-2,6-dicarboxylate 171.152 C7 H9 N1 O4 C(O)(=O)C1(=NC(C(=O)O)CCC1) CAS:52-52-8:*PUBCHEM:440179:*LIGAND-CPD:C03972: 1.3.1.26 tetrahydrodipicolinate = H+ lysine biosynthesis VI tetrahydrodipicolinate 2,3,4,5-Tetrahydrodipicolinate*L-2,3,4,5-tetrahydrodipicolinate*Δ1-piperideine-2,6-dicarboxylate 171.152 C7 H9 N1 O4 C(O)(=O)C1(=NC(C(=O)O)CCC1) CAS:52-52-8:*PUBCHEM:440179:*LIGAND-CPD:C03972: 1.3.1.26 tetrahydrodipicolinate = H+ lysine biosynthesis II tetrahydrodipicolinate 2,3,4,5-Tetrahydrodipicolinate*L-2,3,4,5-tetrahydrodipicolinate*Δ1-piperideine-2,6-dicarboxylate 171.152 C7 H9 N1 O4 C(O)(=O)C1(=NC(C(=O)O)CCC1) CAS:52-52-8:*PUBCHEM:440179:*LIGAND-CPD:C03972: 1.3.1.26 tetrahydrodipicolinate = H+ lysine biosynthesis I tetrahydrodipicolinate 2,3,4,5-Tetrahydrodipicolinate*L-2,3,4,5-tetrahydrodipicolinate*Δ1-piperideine-2,6-dicarboxylate 171.152 C7 H9 N1 O4 C(O)(=O)C1(=NC(C(=O)O)CCC1) CAS:52-52-8:*PUBCHEM:440179:*LIGAND-CPD:C03972: 2.6.1.- tetrahydrodipicolinate + L-glutamate + H2O = L,L-diaminopimelate + α-ketoglutarate lysine biosynthesis VI tetrahydrodipicolinate 2,3,4,5-Tetrahydrodipicolinate*L-2,3,4,5-tetrahydrodipicolinate*Δ1-piperideine-2,6-dicarboxylate 171.152 C7 H9 N1 O4 C(O)(=O)C1(=NC(C(=O)O)CCC1) CAS:52-52-8:*PUBCHEM:440179:*LIGAND-CPD:C03972: 2.3.1.89 acetyl-CoA + tetrahydrodipicolinate + H2O = coenzyme A + L-2-acetamido-6-oxoheptanedioate lysine biosynthesis II tetrahydrodipicolinate 2,3,4,5-Tetrahydrodipicolinate*L-2,3,4,5-tetrahydrodipicolinate*Δ1-piperideine-2,6-dicarboxylate 171.152 C7 H9 N1 O4 C(O)(=O)C1(=NC(C(=O)O)CCC1) CAS:52-52-8:*PUBCHEM:440179:*LIGAND-CPD:C03972: 2.3.1.117 H2O + tetrahydrodipicolinate + succinyl-CoA = N-succinyl-2-amino-6-ketopimelate + coenzyme A lysine biosynthesis I L-galactono-1,4-lactone L-galactono-γ-lactone 178.141 C6 H10 O6 C1(OC(C(O)CO)C(O)C(O)1)(=O) CAS:1668-08-2 1.3.2.3 L-galactono-1,4-lactone = L-ascorbate ascorbate biosynthesis L-galactono-1,4-lactone L-galactono-γ-lactone 178.141 C6 H10 O6 C1(OC(C(O)CO)C(O)C(O)1)(=O) CAS:1668-08-2 1.1.1.- L-galactose + NAD+ = L-galactono-1,4-lactone + NADH ascorbate biosynthesis D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = 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 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = fructose-6-phosphate + D-glyceraldehyde-3-phosphate xylulose-monophosphate cycle D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = fructose-6-phosphate + D-glyceraldehyde-3-phosphate Calvin cycle D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = 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 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*LIGAND-CPD:C00231:*CAS:60802-29-1 4.1.2.9 D-xylulose-5-phosphate = H2O + D-glyceraldehyde-3-phosphate + acetylphosphate glucose fermentation to lactate II D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.3 formaldehyde + D-xylulose-5-phosphate = dihydroxy-acetone + D-glyceraldehyde-3-phosphate xylulose-monophosphate cycle D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*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 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*LIGAND-CPD:C00231:*CAS:60802-29-1 5.1.3.1 D-ribulose-5-phosphate = D-xylulose-5-phosphate Calvin cycle D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*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 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*LIGAND-CPD:C00231:*CAS:60802-29-1 5.1.3.1 D-ribulose-5-phosphate = D-xylulose-5-phosphate glucose fermentation to lactate II D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.7.1.17 D-xylulose + ATP = D-xylulose-5-phosphate + ADP xylose degradation D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate pentose phosphate pathway (partial) D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate Calvin cycle D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-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 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate (deoxy)ribose phosphate degradation D-xylulose-5-phosphate xylulose-5-phosphate*xylulose-phosphate*D-xylulose-5-P*xylulose-P 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(O)=O PUBCHEM:439190:*LIGAND-CPD:C00231:*CAS:60802-29-1 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate glucose fermentation to lactate II L-glutamate-5-phosphate L-γ-glutamyl-5-phosphate*L-γ-glutamyl-5-P*L-glutamyl-5-phosphate 227.11 C5 H10 N1 O7 P1 C(=O)(O)C(N)CCC(=O)OP(O)(O)=O LIGAND-CPD:C03287: 1.2.1.41 L-glutamate γ-semialdehyde + NADP+ = L-glutamate-5-phosphate + NADPH + H+ proline biosynthesis II L-glutamate-5-phosphate L-γ-glutamyl-5-phosphate*L-γ-glutamyl-5-P*L-glutamyl-5-phosphate 227.11 C5 H10 N1 O7 P1 C(=O)(O)C(N)CCC(=O)OP(O)(O)=O 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 227.11 C5 H10 N1 O7 P1 C(=O)(O)C(N)CCC(=O)OP(O)(O)=O 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 227.11 C5 H10 N1 O7 P1 C(=O)(O)C(N)CCC(=O)OP(O)(O)=O LIGAND-CPD:C03287: 2.7.2.11 L-glutamate + ATP = L-glutamate-5-phosphate + ADP proline biosynthesis II L-glutamate-5-phosphate L-γ-glutamyl-5-phosphate*L-γ-glutamyl-5-P*L-glutamyl-5-phosphate 227.11 C5 H10 N1 O7 P1 C(=O)(O)C(N)CCC(=O)OP(O)(O)=O 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 227.11 C5 H10 N1 O7 P1 C(=O)(O)C(N)CCC(=O)OP(O)(O)=O LIGAND-CPD:C03287: 2.7.2.11 L-glutamate + ATP = L-glutamate-5-phosphate + ADP citrulline biosynthesis adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00212:*CAS:58-61-7 3.1.3.5 AMP + H2O = adenosine salvage pathways of purine nucleosides II (plant) adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00212:*CAS:58-61-7 2.7.1.20 adenosine + ATP = AMP + ADP salvage pathways of purine nucleosides II (plant) adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00212:*CAS:58-61-7 2.4.2.- adenosine = ribose-1-phosphate + adenine salvage pathways of adenine, hypoxanthine, and their nucleosides adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00212:*CAS:58-61-7 2.4.2.- adenosine = ribose-1-phosphate + adenine salvage pathways of purine nucleosides adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00212:*CAS:58-61-7 2.4.2.- adenosine = ribose-1-phosphate + adenine salvage pathways of purine and pyrimidine nucleotides adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00212:*CAS:58-61-7 3.5.4.4 H2O + adenosine = ammonia + inosine salvage pathways of adenine, hypoxanthine, and their nucleosides adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00212:*CAS:58-61-7 3.5.4.4 H2O + adenosine = ammonia + inosine salvage pathways of purine nucleosides adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00212:*CAS:58-61-7 1.5.99.12 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 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(N)ncn3)) 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 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00212:*CAS:58-61-7 3.3.1.1 S-adenosyl-L-homocysteine + H2O = L-homocysteine + adenosine S-adenosyl-L-methionine cycle adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00212:*CAS:58-61-7 3.2.2.7 H2O + adenosine = D-ribose + adenine salvage pathways of purine nucleosides II (plant) adenosine adenine-D-ribose 267.244 C10 H13 N5 O4 C1(C(O)C(O)C(O1)CO)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00212:*CAS:58-61-7 1.5.99.12 isopentenyl adenosine + H2O + FAD = adenosine + 3-methyl-2-butenal + FADH2 cytokinins degradation 7,2'-dihydroxy-4'-methoxy-isoflavanol-quinonemethide-intermediate-1 289.307 C16 H17 O5 C2([CH](c1(c(O)cc(OC)cc1))[CH]([OH2])c3(c(O2)cc([OH])cc3)) 7,2'-dihydroxy-4'-methoxy-isoflavanol-quinonemethide-intermediate-1 = 7,2'-dihydroxy-4'-methoxy-isoflavanol-quinonemethide-intermediate-2 medicarpin biosynthesis 7,2'-dihydroxy-4'-methoxy-isoflavanol-quinonemethide-intermediate-1 289.307 C16 H17 O5 C2([CH](c1(c(O)cc(OC)cc1))[CH]([OH2])c3(c(O2)cc([OH])cc3)) 7,2'-dihydroxy-4'-methoxy-isoflavanol = 7,2'-dihydroxy-4'-methoxy-isoflavanol-quinonemethide-intermediate-1 medicarpin biosynthesis 18:3-18:2-DGDG 1-18:3-2-18:2-digalactosyldiacylglycerol 939.231 C51 H86 O15 C(OC1(OC(C(O)C(O)C1O)COC2(C(O)C(O)C(O)C(O2)CO)))C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:2-18:2-DGDG = 18:3-18:2-DGDG glycolipid desaturation 18:3-18:2-DGDG 1-18:3-2-18:2-digalactosyldiacylglycerol 939.231 C51 H86 O15 C(OC1(OC(C(O)C(O)C1O)COC2(C(O)C(O)C(O)C(O2)CO)))C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:3-18:2-DGDG = 18:3-18:3-DGDG glycolipid desaturation D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 200.085 C4 H9 O7 P1 C(OP(O)(=O)O)C(O)C(O)C=O PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = 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 200.085 C4 H9 O7 P1 C(OP(O)(=O)O)C(O)C(O)C=O PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = fructose-6-phosphate + D-glyceraldehyde-3-phosphate xylulose-monophosphate cycle D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 200.085 C4 H9 O7 P1 C(OP(O)(=O)O)C(O)C(O)C=O PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = fructose-6-phosphate + D-glyceraldehyde-3-phosphate Calvin cycle D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 200.085 C4 H9 O7 P1 C(OP(O)(=O)O)C(O)C(O)C=O PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = 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 200.085 C4 H9 O7 P1 C(OP(O)(=O)O)C(O)C(O)C=O PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = 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 200.085 C4 H9 O7 P1 C(OP(O)(=O)O)C(O)C(O)C=O PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = fructose-6-phosphate + D-erythrose-4-phosphate glucose fermentation to lactate II D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 200.085 C4 H9 O7 P1 C(OP(O)(=O)O)C(O)C(O)C=O PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 4.1.2.- Calvin cycle D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 200.085 C4 H9 O7 P1 C(OP(O)(=O)O)C(O)C(O)C=O PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 1.2.1.72 D-erythrose-4-phosphate + NAD+ + H2O = erythronate-4-phosphate + NADH + H+ pyridoxal 5'-phosphate biosynthesis D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 200.085 C4 H9 O7 P1 C(OP(O)(=O)O)C(O)C(O)C=O PUBCHEM:122357:*LIGAND-CPD:C00279:*CAS:585-18-2 4.1.2.22 fructose-6-phosphate = H2O + D-erythrose-4-phosphate + acetylphosphate glucose fermentation to lactate II D-erythrose-4-phosphate erythrose-4P*threose 4-phosphate*erythrose-4-phosphate*erythrose-4-P*D-erythrose-4-P 200.085 C4 H9 O7 P1 C(OP(O)(=O)O)C(O)C(O)C=O 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 lipid IVA 2,3,2'3'-Tetrakis(β-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphate*2,3,2',3'-tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphate*2,3,2',3'-tetrakis-(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-glucosamine-1,4'-bisphosphate*[2-N,3-O-bis(3-hydroxytetradecanoyl)-4-O-phosphono-β-D-glucosaminyl]-(1 => 6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl phosphate] 1405.722 C68 H130 N2 O23 P2 CCCCCCCCCCCC(O)CC(=O)NC1(C(OP(=O)(O)O)OC(C(O)C1OC(=O)CC(O)CCCCCCCCCCC)COC2(C(NC(=O)CC(O)CCCCCCCCCCC)C(C(C(O2)CO)OP(O)(O)=O)OC(=O)CC(O)CCCCCCCCCCC)) 2.7.1.130 lipid A disaccharide + ATP = lipid IVA + ADP lipid-A-precursor biosynthesis (N-acetylglucosaminyl)2-diphosphodolichol chitobiosyldiphosphodolichol*N,N'-diacetylchitobiosyldiphosphodolichol*{N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 1676.271 C96 H160 N2 O17 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(C(NC(C)=O)C(O)C(O)C(O2)CO)) 2.4.1.141 N-acetylglucosaminyl-diphosphodolichol + UDP-N-acetyl-D-glucosamine = (N-acetylglucosaminyl)2-diphosphodolichol + UDP dolichyl-diphosphooligosaccharide biosynthesis (N-acetylglucosaminyl)2-diphosphodolichol chitobiosyldiphosphodolichol*N,N'-diacetylchitobiosyldiphosphodolichol*{N-acetyl-β-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolichol 1676.271 C96 H160 N2 O17 P2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OP(=O)(O)OC1(C(NC(=O)C)C(O)C(C(O1)CO)OC2(C(NC(C)=O)C(O)C(O)C(O2)CO)) 2.4.1.142 (N-acetylglucosaminyl)2-diphosphodolichol + GDP-D-mannose = mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol + GDP dolichyl-diphosphooligosaccharide biosynthesis 18:1-16:1-MGDG 1-18:1-2-16:1-monogalactosyldiacylglycerol*1-(9Z-octadecenoyl)-2-(7Z-hexadecenoyl)-3-O-beta-D-galactosyl-sn-glycerol, 755.083 C43 H78 O10 C1(OC(CO)C(O)C(O)C(O)1)OCC(OC(=O)CCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC 1.14.99.- 18:1-16:1-MGDG = 18:1-16:2-MGDG glycolipid desaturation 18:1-16:1-MGDG 1-18:1-2-16:1-monogalactosyldiacylglycerol*1-(9Z-octadecenoyl)-2-(7Z-hexadecenoyl)-3-O-beta-D-galactosyl-sn-glycerol, 755.083 C43 H78 O10 C1(OC(CO)C(O)C(O)C(O)1)OCC(OC(=O)CCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC 1.14.99.- 18:1-16:1-MGDG = 18:2-16:1-MGDG glycolipid desaturation 18:1-16:1-MGDG 1-18:1-2-16:1-monogalactosyldiacylglycerol*1-(9Z-octadecenoyl)-2-(7Z-hexadecenoyl)-3-O-beta-D-galactosyl-sn-glycerol, 755.083 C43 H78 O10 C1(OC(CO)C(O)C(O)C(O)1)OCC(OC(=O)CCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC 1.14.99.- 18:1-16:0-MGDG = 18:1-16:1-MGDG glycolipid desaturation betanidin 2,6-Pyridinedicarboxylic acid 389.341 C18 H17 N2 O8 C(C=C1(C=C(C(O)=O)NC(C1)C(=O)O))=[N+]2([CH](C(=O)O)Cc3(c2cc(O)c(O)c3)) PUBCHEM:6451365: 1.11.1.7 betanidin + H2O2 = betanidin + betanidin quinone + H2O betanidin degradation GA38 gibberellin A38*gibberellin A38*GA38 380.437 C20 H28 O7 CC1([CH]4(C(CCC(O)1)(CO)[CH]3(C2(CC(C(=C)C2)(O)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA44 + α-ketoglutarate + O2 = GA38 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) p-hydroxyphenylpyruvate p-hydroxyphenylpyruvic acid*3-(4-hydroxyphenyl)pyruvate*hydroxyphenylpyruvate*4-hydroxyphenylpyruvate 180.16 C9 H8 O4 C(=O)(O)C(=O)Cc1(ccc(O)cc1) CAS:156-39-8*PUBCHEM:979:*LIGAND-CPD:C01179: 1.13.11.27 p-hydroxyphenylpyruvate + O2 = CO2 + homogentisate vitamin E biosynthesis p-hydroxyphenylpyruvate p-hydroxyphenylpyruvic acid*3-(4-hydroxyphenyl)pyruvate*hydroxyphenylpyruvate*4-hydroxyphenylpyruvate 180.16 C9 H8 O4 C(=O)(O)C(=O)Cc1(ccc(O)cc1) CAS:156-39-8*PUBCHEM:979:*LIGAND-CPD:C01179: 1.13.11.27 p-hydroxyphenylpyruvate + O2 = CO2 + homogentisate tyrosine degradation I p-hydroxyphenylpyruvate p-hydroxyphenylpyruvic acid*3-(4-hydroxyphenyl)pyruvate*hydroxyphenylpyruvate*4-hydroxyphenylpyruvate 180.16 C9 H8 O4 C(=O)(O)C(=O)Cc1(ccc(O)cc1) CAS:156-39-8*PUBCHEM:979:*LIGAND-CPD:C01179: 1.13.11.27 p-hydroxyphenylpyruvate + O2 = CO2 + homogentisate plastoquinone biosynthesis p-hydroxyphenylpyruvate p-hydroxyphenylpyruvic acid*3-(4-hydroxyphenyl)pyruvate*hydroxyphenylpyruvate*4-hydroxyphenylpyruvate 180.16 C9 H8 O4 C(=O)(O)C(=O)Cc1(ccc(O)cc1) CAS:156-39-8*PUBCHEM:979:*LIGAND-CPD:C01179: 2.6.1.5 L-tyrosine + α-ketoglutarate = L-glutamate + p-hydroxyphenylpyruvate tyrosine degradation I 18-oxooleate 18-oxooctadec-9-enoic acid 296.449 C18 H32 O3 C(=O)CCCCCCCC=CCCCCCCCC(O)=O 1.1.1.- 18-hydroxyoleate + NADP+ = 18-oxooleate + NADPH suberin biosynthesis 18-oxooleate 18-oxooctadec-9-enoic acid 296.449 C18 H32 O3 C(=O)CCCCCCCC=CCCCCCCCC(O)=O 1.1.1.- 18-oxooleate + NADP+ + H2O = octadec-9-ene-1,18-dioic-acid + NADPH suberin biosynthesis 3-deoxy-capsidiol 1β-hydroxy-5-epiaristolochene 220.354 C15 H24 O1 CC12(C(=CCC(C1)C(=C)C)C(O)CCC(C)2) 5-epi-aristolochene + O2 + NADPH = 3-deoxy-capsidiol + H2O + NADP+ capsidiol biosynthesis 3-deoxy-capsidiol 1β-hydroxy-5-epiaristolochene 220.354 C15 H24 O1 CC12(C(=CCC(C1)C(=C)C)C(O)CCC(C)2) 3-deoxy-capsidiol + O2 + NADPH = capsidiol + H2O + NADP+ capsidiol 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 173.168 C7 H11 N1 O4 C(O)(=O)C(NC(=O)C)CC[CH]=O LIGAND-CPD:C01250: 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = 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 173.168 C7 H11 N1 O4 C(O)(=O)C(NC(=O)C)CC[CH]=O LIGAND-CPD:C01250: 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = 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 173.168 C7 H11 N1 O4 C(O)(=O)C(NC(=O)C)CC[CH]=O LIGAND-CPD:C01250: 2.6.1.11 N-acetyl-L-ornithine + α-ketoglutarate = 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 173.168 C7 H11 N1 O4 C(O)(=O)C(NC(=O)C)CC[CH]=O LIGAND-CPD:C01250: 2.6.1.11 N-acetyl-L-ornithine + α-ketoglutarate = L-glutamate + N-acetyl-L-glutamate 5-semialdehyde ornithine biosynthesis saccharopine N6-(L-1,3-dicarboxypropyl)-L-lysine*ε-N-(L-glutar-2-yl)-L-lysine 276.289 C11 H20 N2 O6 C(=O)(O)C(CCC(O)=O)NCCCCC(N)C(=O)O CAS:997-68-2 1.5.1.9 H2O + NAD+ + saccharopine = L-glutamate + NADH + 2-aminoadipate-6-semialdehyde lysine degradation II saccharopine N6-(L-1,3-dicarboxypropyl)-L-lysine*ε-N-(L-glutar-2-yl)-L-lysine 276.289 C11 H20 N2 O6 C(=O)(O)C(CCC(O)=O)NCCCCC(N)C(=O)O CAS:997-68-2 1.5.1.7 H2O + NAD+ + saccharopine = NADH + α-ketoglutarate + L-lysine lysine biosynthesis IV saccharopine N6-(L-1,3-dicarboxypropyl)-L-lysine*ε-N-(L-glutar-2-yl)-L-lysine 276.289 C11 H20 N2 O6 C(=O)(O)C(CCC(O)=O)NCCCCC(N)C(=O)O CAS:997-68-2 1.5.1.10 2-aminoadipate-6-semialdehyde + NADPH + L-glutamate = saccharopine + NADP+ + H2O lysine biosynthesis IV saccharopine N6-(L-1,3-dicarboxypropyl)-L-lysine*ε-N-(L-glutar-2-yl)-L-lysine 276.289 C11 H20 N2 O6 C(=O)(O)C(CCC(O)=O)NCCCCC(N)C(=O)O CAS:997-68-2 1.5.1.8 H2O + NADP+ + saccharopine = NADPH + α-ketoglutarate + L-lysine lysine degradation II α-ketoadipate 2-ketoadipate*2-oxoadipate*2-keto-adipate*2-oxohexanedionic acid 160.126 C6 H8 O5 C(=O)(O)C(=O)CCCC(O)=O CAS:3184-35-8 2.6.1.39 α-ketoglutarate + α-aminoadipate = L-glutamate + α-ketoadipate lysine biosynthesis IV α-ketoadipate 2-ketoadipate*2-oxoadipate*2-keto-adipate*2-oxohexanedionic acid 160.126 C6 H8 O5 C(=O)(O)C(=O)CCCC(O)=O CAS:3184-35-8 2.6.1.39 α-ketoglutarate + α-aminoadipate = L-glutamate + α-ketoadipate lysine degradation II α-ketoadipate 2-ketoadipate*2-oxoadipate*2-keto-adipate*2-oxohexanedionic acid 160.126 C6 H8 O5 C(=O)(O)C(=O)CCCC(O)=O CAS:3184-35-8 α-ketoadipate + NAD+ + coenzyme A = CO2 + NADH + glutaryl-CoA lysine degradation II α-ketoadipate 2-ketoadipate*2-oxoadipate*2-keto-adipate*2-oxohexanedionic acid 160.126 C6 H8 O5 C(=O)(O)C(=O)CCCC(O)=O CAS:3184-35-8 α-ketoadipate + NAD+ + coenzyme A = CO2 + NADH + glutaryl-CoA tryptophan degradation III (eukaryotic) α-ketoadipate 2-ketoadipate*2-oxoadipate*2-keto-adipate*2-oxohexanedionic acid 160.126 C6 H8 O5 C(=O)(O)C(=O)CCCC(O)=O CAS:3184-35-8 2-amino-muconate + H2O + NADH = NH(4)OH + α-ketoadipate + NAD+ tryptophan degradation III (eukaryotic) α-ketoadipate 2-ketoadipate*2-oxoadipate*2-keto-adipate*2-oxohexanedionic acid 160.126 C6 H8 O5 C(=O)(O)C(=O)CCCC(O)=O CAS:3184-35-8 1.1.1.87 homoisocitrate + NAD+ = α-ketoadipate + CO2 + NADH + H+ lysine biosynthesis IV FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 787.572 C27 H35 N9 O15 P2 Cc3(cc2(N(c1(c(c(=O)[nH]c(=O)[nH]1)[NH]c2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH]4O)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C01352:*CAS:1910-41-4 1.5.99.12 trans-zeatin + H2O + FAD = adenine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 cytokinins degradation FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 787.572 C27 H35 N9 O15 P2 Cc3(cc2(N(c1(c(c(=O)[nH]c(=O)[nH]1)[NH]c2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH]4O)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C01352:*CAS:1910-41-4 1.5.99.12 isopentenyladenine + FAD + H2O = 3-methyl-2-butenal + adenine + FADH2 cytokinins degradation FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 787.572 C27 H35 N9 O15 P2 Cc3(cc2(N(c1(c(c(=O)[nH]c(=O)[nH]1)[NH]c2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH]4O)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C01352:*CAS:1910-41-4 1.5.99.12 cis-zeatin + H2O + FAD = 3-methyl-4-cis-hydroxy-2-butenal + adenine + FADH2 cytokinins degradation FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 787.572 C27 H35 N9 O15 P2 Cc3(cc2(N(c1(c(c(=O)[nH]c(=O)[nH]1)[NH]c2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH]4O)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C01352:*CAS:1910-41-4 1.1.99.5 sn-glycerol-3-phosphate + FAD = dihydroxy-acetone-phosphate + FADH2 glycerol degradation IV FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 787.572 C27 H35 N9 O15 P2 Cc3(cc2(N(c1(c(c(=O)[nH]c(=O)[nH]1)[NH]c2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH]4O)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C01352:*CAS:1910-41-4 1.3.99.10 isovaleryl-CoA + FAD = 3-methylcrotonyl-CoA + FADH2 leucine degradation I FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 787.572 C27 H35 N9 O15 P2 Cc3(cc2(N(c1(c(c(=O)[nH]c(=O)[nH]1)[NH]c2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH]4O)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C01352:*CAS:1910-41-4 1.3.99.12 isobutyryl-CoA + FAD = methylacrylyl-CoA + FADH2 valine degradation I FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 787.572 C27 H35 N9 O15 P2 Cc3(cc2(N(c1(c(c(=O)[nH]c(=O)[nH]1)[NH]c2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH]4O)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C01352:*CAS:1910-41-4 1.3.99.12 S-2-methyl-butyryl-CoA + FAD = tiglyl-CoA + FADH2 isoleucine degradation I FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 787.572 C27 H35 N9 O15 P2 Cc3(cc2(N(c1(c(c(=O)[nH]c(=O)[nH]1)[NH]c2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH]4O)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C01352:*CAS:1910-41-4 1.5.99.8 L-proline + FAD = FADH2 proline degradation I FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 787.572 C27 H35 N9 O15 P2 Cc3(cc2(N(c1(c(c(=O)[nH]c(=O)[nH]1)[NH]c2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH]4O)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C01352:*CAS:1910-41-4 1.5.99.8 L-proline + FAD = FADH2 citrulline biosynthesis FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 787.572 C27 H35 N9 O15 P2 Cc3(cc2(N(c1(c(c(=O)[nH]c(=O)[nH]1)[NH]c2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH]4O)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C01352:*CAS:1910-41-4 1.3.99.3 FADH2 + acrylyl-CoA = FAD + propionyl-CoA β-alanine biosynthesis II FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 787.572 C27 H35 N9 O15 P2 Cc3(cc2(N(c1(c(c(=O)[nH]c(=O)[nH]1)[NH]c2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH]4O)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C01352:*CAS:1910-41-4 1.3.99.3 FAD = FADH2 fatty acid β-oxidation I FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 787.572 C27 H35 N9 O15 P2 Cc3(cc2(N(c1(c(c(=O)[nH]c(=O)[nH]1)[NH]c2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH]4O)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C01352:*CAS:1910-41-4 1.5.99.12 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 787.572 C27 H35 N9 O15 P2 Cc3(cc2(N(c1(c(c(=O)[nH]c(=O)[nH]1)[NH]c2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH]4O)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C01352:*CAS:1910-41-4 1.5.99.12 isopentenyl adenosine + H2O + FAD = adenosine + 3-methyl-2-butenal + FADH2 cytokinins degradation FADH2 flavin adenine dinucleotide reduced*1,5-dihydro-FAD 787.572 C27 H35 N9 O15 P2 Cc3(cc2(N(c1(c(c(=O)[nH]c(=O)[nH]1)[NH]c2cc(C)3))CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4(O[CH]([CH](O)[CH]4O)n5(c6(c(nc5)c(N)ncn6))))) LIGAND-CPD:C01352:*CAS:1910-41-4 glutaryl-CoA + FAD = glutaconyl-CoA + FADH2 glutaryl-CoA degradation delphinidin 3,5,3'-triglucoside 789.674 C33 H41 O22 C1(OC(CO)C(O)C(O)C(O)1)OC4(C(c2(cc(c(O)c(O)c2)OC3(C(O)C(O)C(O)C(O3)CO)))=Oc5(c(C=4)c(cc(O)c5)OC6(OC(CO)C(O)C(O)C(O)6))) 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 789.674 C33 H41 O22 C1(OC(CO)C(O)C(O)C(O)1)OC4(C(c2(cc(c(O)c(O)c2)OC3(C(O)C(O)C(O)C(O3)CO)))=Oc5(c(C=4)c(cc(O)c5)OC6(OC(CO)C(O)C(O)C(O)6))) 2.4.1.238 delphinidin-3,5-diglucoside + UDP-D-glucose = delphinidin 3,5,3'-triglucoside + UDP gentiodelphin biosynthesis citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 C(O)(=O)C(N)CCCNC(=O)N LIGAND-CPD:C00327:*CAS:372-75-8 3.5.3.6 H2O + L-arginine = ammonia + citrulline proline biosynthesis V (from arginine) citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 C(O)(=O)C(N)CCCNC(=O)N LIGAND-CPD:C00327:*CAS:372-75-8 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP urea cycle citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 C(O)(=O)C(N)CCCNC(=O)N LIGAND-CPD:C00327:*CAS:372-75-8 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis II (acetyl cycle) citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 C(O)(=O)C(N)CCCNC(=O)N LIGAND-CPD:C00327:*CAS:372-75-8 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP citrulline-nitric oxide cycle citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 C(O)(=O)C(N)CCCNC(=O)N LIGAND-CPD:C00327:*CAS:372-75-8 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis IV citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 C(O)(=O)C(N)CCCNC(=O)N LIGAND-CPD:C00327:*CAS:372-75-8 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis I citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 C(O)(=O)C(N)CCCNC(=O)N LIGAND-CPD:C00327:*CAS:372-75-8 1.14.13.39 O2 + NADPH + L-arginine = citrulline + NADP+ + nitric oxide citrulline-nitric oxide cycle citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 C(O)(=O)C(N)CCCNC(=O)N LIGAND-CPD:C00327:*CAS:372-75-8 3.5.1.20 citrulline + H2O = L-ornithine + CO2 + ammonia proline biosynthesis V (from arginine) citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 C(O)(=O)C(N)CCCNC(=O)N LIGAND-CPD:C00327:*CAS:372-75-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline urea cycle citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 C(O)(=O)C(N)CCCNC(=O)N LIGAND-CPD:C00327:*CAS:372-75-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline proline biosynthesis V (from arginine) citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 C(O)(=O)C(N)CCCNC(=O)N LIGAND-CPD:C00327:*CAS:372-75-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline arginine biosynthesis II (acetyl cycle) citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 C(O)(=O)C(N)CCCNC(=O)N LIGAND-CPD:C00327:*CAS:372-75-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline arginine biosynthesis IV citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 C(O)(=O)C(N)CCCNC(=O)N LIGAND-CPD:C00327:*CAS:372-75-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline citrulline degradation citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 C(O)(=O)C(N)CCCNC(=O)N LIGAND-CPD:C00327:*CAS:372-75-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline arginine biosynthesis I citrulline Nγ-carbamylornithine*α-amino-γ-ureidovaleric acid*γureidonorvaline*N5-(Aminocarbonyl)-L-ornithine*L-citrulline 175.187 C6 H13 N3 O3 C(O)(=O)C(N)CCCNC(=O)N LIGAND-CPD:C00327:*CAS:372-75-8 2.1.3.3 L-ornithine + carbamoyl-phosphate = citrulline citrulline biosynthesis isopentenyladenosine-5'-triphosphate iPTP*isopentenyladenosine riboside-5'-triphosphate*iPRTP 575.302 C15 H24 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(ncn3)NCC=C(C)C))) 2.5.1.- dimethylallyl-PP + ATP = isopentenyladenosine-5'-triphosphate + diphosphate trans-zeatin biosynthesis isopentenyladenosine-5'-triphosphate iPTP*isopentenyladenosine riboside-5'-triphosphate*iPRTP 575.302 C15 H24 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(ncn3)NCC=C(C)C))) isopentenyladenosine-5'-triphosphate + NADPH + H2O = trans-zeatin riboside triphosphate + NADP+ trans-zeatin biosynthesis isopentenyladenosine-5'-triphosphate iPTP*isopentenyladenosine riboside-5'-triphosphate*iPRTP 575.302 C15 H24 N5 O13 P3 C(OP(O)(=O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(ncn3)NCC=C(C)C))) isopentenyladenosine-5'-triphosphate + H2O = isopentenyladenosine-5'-diphosphate trans-zeatin biosynthesis ubiquinone-8 ubiquinone(9)*coenzyme-Q8*Q-9 727.121 C49 H74 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(=O)C(OC)=C(OC)C(=O)C=1C) CAS:1339-63-5:*LIGAND-CPD:C00399: 1.6.5.3 ubiquinone-8 + NADH = ubiquinol-8 + NAD+ aerobic respiration -- electron donors reaction list ubiquinone-8 ubiquinone(9)*coenzyme-Q8*Q-9 727.121 C49 H74 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(=O)C(OC)=C(OC)C(=O)C=1C) CAS:1339-63-5:*LIGAND-CPD:C00399: 1.6.5.3 ubiquinone-8 + NADH = ubiquinol-8 + NAD+ respiration (anaerobic)-- electron donors reaction list ubiquinone-8 ubiquinone(9)*coenzyme-Q8*Q-9 727.121 C49 H74 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(=O)C(OC)=C(OC)C(=O)C=1C) CAS:1339-63-5:*LIGAND-CPD:C00399: 1.6.5.3 ubiquinone-8 + NADH = ubiquinol-8 + NAD+ NAD/NADH phosphorylation and dephosphorylation ubiquinone-8 ubiquinone(9)*coenzyme-Q8*Q-9 727.121 C49 H74 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(=O)C(OC)=C(OC)C(=O)C=1C) CAS:1339-63-5:*LIGAND-CPD:C00399: 1.2.2.2 pyruvate + ubiquinone-8 + H2O = ubiquinol-8 + acetate + CO2 mixed acid fermentation ubiquinone-8 ubiquinone(9)*coenzyme-Q8*Q-9 727.121 C49 H74 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(=O)C(OC)=C(OC)C(=O)C=1C) CAS:1339-63-5:*LIGAND-CPD:C00399: 1.1.99.5 sn-glycerol-3-phosphate + ubiquinone-8 = dihydroxy-acetone-phosphate + ubiquinol-8 aerobic respiration -- electron donors reaction list ubiquinone-8 ubiquinone(9)*coenzyme-Q8*Q-9 727.121 C49 H74 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(=O)C(OC)=C(OC)C(=O)C=1C) CAS:1339-63-5:*LIGAND-CPD:C00399: 1.1.99.5 sn-glycerol-3-phosphate + ubiquinone-8 = dihydroxy-acetone-phosphate + ubiquinol-8 respiration (anaerobic)-- electron donors reaction list ubiquinone-8 ubiquinone(9)*coenzyme-Q8*Q-9 727.121 C49 H74 O4 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(=O)C(OC)=C(OC)C(=O)C=1C) CAS:1339-63-5:*LIGAND-CPD:C00399: 1.1.99.5 sn-glycerol-3-phosphate + ubiquinone-8 = dihydroxy-acetone-phosphate + ubiquinol-8 glycerol degradation I (2R,3R)-pinobanksin 272.257 C15 H12 O5 c3(c2(OC(c1(ccccc1))C(O)C(=O)c2c(O)cc(O)3)) 1.14.11.9 (2S)-pinocembrin + O2 + α-ketoglutarate = (2R,3R)-pinobanksin + CO2 + succinate pinobanksin biosynthesis betaine aldehyde hydrate 120.171 C5 H14 N1 O2 C(C=O)[N+](C)(C)C betaine aldehyde hydrate = betaine aldehyde + H2O glycine betaine biosynthesis III (plants) betaine aldehyde hydrate 120.171 C5 H14 N1 O2 C(C=O)[N+](C)(C)C 1.14.15.7 choline + O2 + H+ = betaine aldehyde hydrate + H2O glycine betaine biosynthesis III (plants) genistein isoflavone*5,7,4'-trihydroxyisoflavone 270.241 C15 H10 O5 C3(=C(c1(ccc(O)cc1))C(=O)c2(c(O)cc(O)cc2O3)) 2.5.1.1 genistein + dimethylallyl-PP = lupiwighteone + diphosphate wighteone and luteone biosynthesis genistein isoflavone*5,7,4'-trihydroxyisoflavone 270.241 C15 H10 O5 C3(=C(c1(ccc(O)cc1))C(=O)c2(c(O)cc(O)cc2O3)) 2.5.1.1 genistein + dimethylallyl-PP = wighteone + diphosphate wighteone and luteone biosynthesis genistein isoflavone*5,7,4'-trihydroxyisoflavone 270.241 C15 H10 O5 C3(=C(c1(ccc(O)cc1))C(=O)c2(c(O)cc(O)cc2O3)) 2.5.1.1 genistein + dimethylallyl-PP = isowighteone + diphosphate wighteone and luteone biosynthesis genistein isoflavone*5,7,4'-trihydroxyisoflavone 270.241 C15 H10 O5 C3(=C(c1(ccc(O)cc1))C(=O)c2(c(O)cc(O)cc2O3)) 1.14.13.89 genistein + NADPH + O2 = 2'-hydroxygenistein + NADP+ + H2O wighteone and luteone biosynthesis 9-HPOD 9(S)-hydroperoxy-10(E),12(Z)-octadecadienoic acid 312.448 C18 H32 O4 CCCCCC=CC=CC(OO)CCCCCCCC(=O)O 9-HPOD = (3Z)-nonenal + 9-oxo-nonanoate 9-LOX and 9-HPL pathway 9-HPOD 9(S)-hydroperoxy-10(E),12(Z)-octadecadienoic acid 312.448 C18 H32 O4 CCCCCC=CC=CC(OO)CCCCCCCC(=O)O 1.13.11.- linoleate + O2 = 9-HPOD 9-LOX and 9-HPL 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.72 lanosterol + NADPH = 24,25-dihydrolanosterol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.38 NADPH = NADP+ 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.25 NADP+ + shikimate = NADPH + 3-dehydro-shikimate chorismate 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.86 2,3-dihydroxy-isovalerate + NADP+ = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 L-glutamate + ATP + NADPH = ADP + L-glutamate γ-semialdehyde + NADP+ arginine biosynthesis IV NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- coniferyl aldehyde + NADPH + O2 = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 isopentenyladenosine-5'-triphosphate + NADPH + H2O = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) 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 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.86 2-aceto-2-hydroxy-butyrate + NADPH = 2,3-dihydroxy-3-methylvalerate + NADP+ isoleucine biosynthesis 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.- 18-oxooleate + NADP+ + H2O = octadec-9-ene-1,18-dioic-acid + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.17.1.3 leucopelargonidin + NADPH = afzelechin + NADP+ + H2O proanthocyanidin biosynthesis from flavanols NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 liquiritigenin + NADPH + O2 = 6,7,4'-trihydroxyflavanone + NADP+ + H2O 6,7,4'-trihydroxyisoflavone 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- dihydrokaempferol + NADPH + O2 = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 calycosin + NADPH + O2 = pseudobaptigenin + NADP+ + H2O maackiain 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.51 dalbergioidin + NADP+ = 2'-hydroxygenistein + NADPH + H+ kievitone 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate formylTHF 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate tetrahydrofolate 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate formylTHF 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate tetrahydrofolate 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.79 ent-kaurenoate + O2 + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 (+)-isomenthone + NADPH = (+)-isomenthol + NADP+ menthol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 2.7.1.23 NAD+ + ATP = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.42 NADP+ = NADPH + α-ketoglutarate + CO2 TCA cycle variation 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.42 NADP+ = NADPH + α-ketoglutarate + CO2 respiration (anaerobic) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.42 NADP+ = NADPH + α-ketoglutarate + CO2 TCA 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 isopentenyladenosine-5'-diphosphate + NADPH + H2O = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 3.1.3.2 NADP+ + H2O = NAD+ NAD salvage pathway 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 chlorophyll b + H2O + NADP+ = 7-hydroxy-chlorophyll a + O2 + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 2.3.1.170 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.70 glutamate-1-semialdehyde + NADP+ = NADPH + H+ 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.36 NADPH = NADP+ 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.21 dihydrokaempferol + NADPH + O2 = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.21 dihydrokaempferol + NADPH + O2 = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.21 dihydrokaempferol + NADPH + O2 = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.70 4,4-dimethyl-5-α-cholesta-8,14-dien-3-β-ol + NADPH = 4,4-dimethyl-5α-cholesta-8-en-3-β-ol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.21 5-dehydro episterol + NADPH = 24-methylenecholesterol + NADP+ 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.11 trans-cinnamate + O2 + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.11 trans-cinnamate + O2 + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.99.- α-carotene + NADPH + O2 = zeinoxanthin + NADP+ + H2O carotenoid 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.193 5-amino-6-(5'-phosphoribitylamino)uracil + NADP+ = 5-amino-6-(5'-phosphoribosylamino)uracil + NADPH + H+ flavin 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.219 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 (+)-cis-isopulegone + NADP+ = (+)-pulegone + NADPH menthol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.75 divinyl protochlorophyllide a + NADPH + H+ + H+ = monovinyl protochlorophyllide a + NADP+ chlorophyllide a 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.3.9 O2 + NADPH + loganin = H2O + NADP+ + secologanin secologanin and strictosidine 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- sitosterol + NADP+ = stigmasterol + NADPH 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.270 4α-methyl-5α-cholesta-8-en-3-one + NADPH = 4α-methyl-cholesta-8-enol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.14.1 cotinine + NADPH + O2 = N'-hydroxymethyl-norcotinine + NADP+ + H2O nicotine degradation 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.6.5.4 monodehydroascorbate + NADPH = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 (+)-pulegone + NADPH = (+)-isomenthone + NADP+ menthol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.271 NADP+ + GDP-L-fucose = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.49 β-D-glucose-6-phosphate + NADP+ = D-glucono-δ-lactone-6-phosphate + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.169 L-pantoate + NADP+ = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.169 L-pantoate + NADP+ = 2-dehydropantoate + NADPH pantothenate 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 2,3-dehydrokievitone + NADPH = kievitone + NADP+ kievitone 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.8.1.2 H2O + NADP+ + hydrogen sulfide = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 hydroxycinnamoyl-CoA + NADP+ = oxocinnamoyl-CoA + NADPH salicylate 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADP+ + H2O + formate cholesterol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADP+ + H2O + formate cholesterol biosynthesis III (via desmosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol + O2 + NADPH = 4,4-dimethyl-5-α-cholesta-8,14-dien-3-β-ol + formate + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.236 NADP+ + pseudotropine = NADPH + tropinone calystegine 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.41 L-glutamate γ-semialdehyde + NADP+ = L-glutamate-5-phosphate + NADPH + H+ proline 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 7-hydroxy-chlorophyllide a + O2 + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- oleate + NADPH + O2 = 18-hydroxyoleate + NADP+ + H2O cutin 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- oleate + NADPH + O2 = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.11 NADP+ + L-aspartate-semialdehyde = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.11 NADP+ + L-aspartate-semialdehyde = NADPH + L-aspartyl-4-phosphate lysine 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.11 NADP+ + L-aspartate-semialdehyde = NADPH + L-aspartyl-4-phosphate lysine 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.11 NADP+ + L-aspartate-semialdehyde = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol + O2 + NADPH = 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.21 7-dehydrodesmosterol + NADPH = desmosterol + NADP+ cholesterol biosynthesis III (via desmosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 NADPH = NADP+ fatty acid elongation -- unsaturated 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- (5α)-campestan-3-one + O2 + NADPH = (22α)-hydroxy-5α-campestan-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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.219 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- geranylgeranyl diphosphate + NADPH = dihydrogeranylgeranyl-PP + NADP+ phytyl-PP 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.9 O2 + NADPH + kynurenine = H2O + NADP+ + 3-hydroxy-L-kynurenine tryptophan degradation III (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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.8.1.7 glutathione + NADP+ = glutathione disulfide + NADPH + H+ 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.44 coumaroyl-CoA + NADPH = coumaraldehyde + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.88 dihydroquercetin + NADPH + O2 = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- palmitate + NADPH + O2 = 16-hydroxypalmitate + NADP+ + H2O cutin 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.195 coniferyl aldehyde + NADPH = coniferyl 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.14.1 N'-hydroxymethyl-norcotinine + NADPH + O2 = norcotinine + NADP+ + H2O nicotine degradation 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- campestanol + O2 + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 (-)-isopiperitenone + NADP+ = (+)-cis-isopulegone + NADPH menthol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.5.1.8 H2O + NADP+ + saccharopine = NADPH + α-ketoglutarate + L-lysine 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 (+)-isomenthone + NADPH = (+)-neoisomenthol + NADP+ menthol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 3-deoxy-capsidiol + O2 + NADPH = capsidiol + H2O + NADP+ capsidiol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 isopentenyladenosine-5'-monophosphate + NADPH + H2O = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.246 (-)-sophorol + NADPH = (-)-maackiain + NADP+ + H2O maackiain 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 3.1.3.- H2O + NADP+ = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.219 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 marmesin + NADPH + O2 = psoralen + NADP+ + acetone + H2O linear furanocoumarin 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.81 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = divinyl protochlorophyllide a + NADP+ + H2O chlorophyllide a 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.44 feruloyl-CoA + NADPH = coniferyl aldehyde + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- eriodictyol + NADPH + O2 = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.39 O2 + NADPH + L-arginine = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 5-epi-aristolochene + O2 + NADPH = 3-deoxy-capsidiol + H2O + NADP+ capsidiol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.4.1.4 L-glutamate + H2O + NADP+ = ammonia + α-ketoglutarate + NADPH 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.21 5-dehydroavenasterol + NADPH = isofucosterol + NADP+ 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.14.1 cotinine + NADPH + O2 = trans-3'-hydroxycotinine + NADP+ + H2O nicotine degradation 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.79 GA12-aldehyde + NADPH + O2 = GA12 + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.78 ent-kaur-16-en-19-ol + NADPH + H+ + O2 = ent-kaur-16-en-19-al + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.14.1 bupropion + NADPH + O2 = hydroxybupropion + NADP+ + H2O bupropion 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.14.1 acetone + NADPH + O2 = acetol + NADP+ + H2O acetone degradation (to methylglyoxal) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.99.- zeinoxanthin + NADPH + O2 = lutein + NADP+ + H2O carotenoid 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.243 (-)-trans-carveol + NADP+ = (-)-carvone + NADPH + H+ menthol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- 6,7,4'-trihydroxyflavanone + NADPH + O2 = 2,6,7,4'-tetrahydroxyisoflavanone + NADP+ + H2O 6,7,4'-trihydroxyisoflavone 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.14.1 nicotine + NADPH = nicotine-Δ1'5'-iminium ion + NADP+ nicotine 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.14.1 nicotine + NADPH = nicotine-Δ1'5'-iminium ion + NADP+ nicotine degradation 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.70 24,25-dihydrolanosterol + O2 + NADPH = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.14.1 cotinine + NADPH + O2 = 5'-hydroxycotinine + NADP+ + H2O nicotine degradation 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- 24-epi-campesterol + NADP+ = brassicasterol + NADPH 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.133 NADP+ + dTDP-α-L-rhamnose = NADPH + dTDP-4-dehydro-6-deoxy-L-mannose dTDP-L-rhamnose 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.45 2-hydroxyformononetin + NADPH = (-)-vestitone + NADP+ medicarpin 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.52 formononetin + NADPH + O2 = calycosin + NADP+ + H2O maackiain 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.16 succinate semialdehyde + NADP+ + H2O = NADPH + succinate TCA cycle variation 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.100 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.34 NADP+ + coenzyme A + (R)-mevalonate = NADPH + 3-hydroxy-3-methyl-glutaryl-CoA mevalonate 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.36 acetoacetyl-CoA + NADPH = 3-hydroxybutyryl-CoA + NADP+ ethanol fermentation to acetate NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.70 NADPH + O2 + obtusifoliol + H+ = H2O + NADP+ + formate + (4α)-methyl-(5α)-ergosta-8,14,24(28)-trien-3β-ol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 tryptamine + O2 + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.270 5α-cholesta-8-en-3-one + NADPH = zymostenol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.270 4α-methyl-5α-cholesta-8,24-dien-3-one + NADPH = 4-α-methyl zymosterol + NADP+ cholesterol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.270 4α-methyl-5α-cholesta-8,24-dien-3-one + NADPH = 4-α-methyl zymosterol + NADP+ cholesterol biosynthesis III (via desmosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.70 (4α)-methyl-(5α)-ergosta-8,14,24(28)-trien-3β-ol + NADPH = 4α-methylfecosterol + NADP+ 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.102 NADP+ + sphinganine = NADPH + 3-dehydrosphinganine sphingolipid metabolism NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.72 5α-cholesta-7,24-dien-3β-ol + NADPH = lathosterol + NADP+ cholesterol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- campesterol + NADP+ = crinosterol + NADPH 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 ferulate + NADPH + O2 = 5-hydroxy-ferulic-acid + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.-.- sphinganine + O2 + NADPH = 4-hydroxysphinganine + H2O + NADP+ sphingolipid metabolism NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.5.1.10 2-aminoadipate-6-semialdehyde + NADPH + L-glutamate = saccharopine + NADP+ + H2O lysine biosynthesis IV NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 demethylsuberosin + O2 + NADPH = marmesin + NADP+ + H2O linear furanocoumarin 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.40 NADP+ + malate = NADPH + CO2 + pyruvate gluconeogenesis NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- campesterol + O2 + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 methylglyoxal + NADPH = acetol + NADP+ acetone degradation (to methylglyoxal) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 7-hydroxy-chlorophyll a + H2O + NADP+ = chlorophyll a + O2 + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.78 ent-kaur-16-en-19-al + NADPH + H+ + O2 = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.89 genistein + NADPH + O2 = 2'-hydroxygenistein + NADP+ + H2O wighteone and luteone 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.34 NADPH = NADP+ fatty acid β-oxidation IV (plant, 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.99.- 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.79 ent-7-α-hydroxykaurenoate + NADPH + H+ + O2 = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- benzoate + NADPH + O2 = salicylate + NADP+ + H2O salicylate 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 18-hydroxyoleate + NADPH + O2 = 9,10-epoxy-18-hydroxystearate + NADP+ + H2O cutin 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.45 2'-hydroxypseudobaptigenin + NADPH = (-)-sophorol + NADP+ maackiain 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.70 lanosterol + NADPH + O2 = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.70 lanosterol + NADPH + O2 = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.81 Mg-protoporphyrin monomethyl ester + NADPH + H+ + O2 = 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.57 dihydrophloroglucinol + NADP+ = phloroglucinol + NADPH gallate degradation III (anaerobic) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.195 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.14 trans-cinnamate + O2 + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 chlorophyllide a + O2 + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 NADPH = NADP+ fatty acid elongation -- unsaturated 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.70 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADPH = 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + NADP+ cholesterol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.70 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADPH = 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + NADP+ cholesterol biosynthesis III (via desmosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.78 ent-kaur-16-ene + O2 + NADPH = H2O + NADP+ + ent-kaur-16-en-19-ol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.14.1 nicotine + NADPH + O2 = 2'-hydroxynicotine + NADP+ + H2O nicotine 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 16-hydroxypalmitate + NADPH + O2 = 10,16-dihydroxypalmitate + NADP+ + H2O cutin 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- campest-4-en-3-one + O2 + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.72 desmosterol + NADPH = cholesterol + NADP+ cholesterol biosynthesis III (via desmosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.- 18-hydroxyoleate + NADP+ = 18-oxooleate + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.53 pseudobaptigenin + NADPH + O2 = 2'-hydroxypseudobaptigenin + NADP+ + H2O maackiain 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.270 5α-cholesta-8,24-dien-3-one + NADPH = zymosterol + NADP+ cholesterol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.270 5α-cholesta-8,24-dien-3-one + NADPH = zymosterol + NADP+ cholesterol biosynthesis III (via desmosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.246 (-)-vestitone + NADPH + H+ = 7,2'-dihydroxy-4'-methoxy-isoflavanol + NADP+ medicarpin 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.2.1.9 D-glyceraldehyde-3-phosphate + NADP+ + H2O = 3-phosphoglycerate + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.2 NADP+ + dihydrouracil = NADPH + uracil β-alanine 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- dihydrogeranylgeranyl-PP + NADPH = tetrahydrogeranylgeranyl-PP + NADP+ phytyl-PP 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.6.6.- L-canaline + NADPH = homoserine + ammonia + NADP+ canavanine 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.42 NADP+ + 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 5-epi-aristolochene + O2 + NADPH = 1-deoxy-capsidiol + H2O + NADP+ capsidiol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.74 O2 + NADPH + 7-deoxyloganin = H2O + NADP+ + loganin secologanin and strictosidine 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 (+)-pulegone + NADPH + O2 = (+)-menthofuran + NADP+ + H2O menthol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.4.1.13 L-glutamate + NADP+ = L-glutamine + α-ketoglutarate + NADPH glutamine degradation 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.4.1.13 L-glutamate + NADP+ = L-glutamine + α-ketoglutarate + NADPH glutamate 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.195 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 4-coumarate + NADPH + O2 = H2O + caffeate + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 4-coumarate + NADPH + O2 = H2O + caffeate + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.158 NADP+ + UDP-N-acetylmuramate = NADPH + UDP-GlcNAc-enolpyruvate peptidoglycan 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.21 7-dehydro-cholesterol + NADPH = cholesterol + NADP+ cholesterol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.21 7-dehydro-cholesterol + NADPH = cholesterol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- tetrahydrogeranylgeranyl-PP + NADPH = phytyl-PP + NADP+ phytyl-PP 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.36 4-coumaroylquinate + NADPH + O2 = caffeoylquinate + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.93 (+)-abscisate + NADPH + O2 = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 (+)-pulegone + NADPH = (-)-menthone + NADP+ menthol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.36 4-coumaroylshikimate + NADPH + O2 = 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.99.- (22α)-hydroxy-campest-4-en-3-one + NADPH = (22α)-hydroxy-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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.1.1.168 NADP+ + pantoyl lactone = NADPH + 2-oxopantoyl lactone pantothenate 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.3.1.- 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.81 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 psoralen + NADPH + H2O = bergaptol + NADP+ linear furanocoumarin 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.- L-tryptophan + NADPH + O2 = indole-3-acetaldoxime + CO2 + 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1-deoxy-capsidiol + O2 + NADPH = capsidiol + H2O + NADP+ capsidiol 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.5.1.5 5,10-methylene-THF + NADP+ = NADPH folate transformations NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.5.1.5 5,10-methylene-THF + NADP+ = NADPH formylTHF 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.5.1.5 5,10-methylene-THF + NADP+ = NADPH formylTHF 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.17.1.3 leucocyanidin + NADPH = 2,3-trans-catechin + NADP+ + H2O proanthocyanidin biosynthesis from flavanols NADP+ coenzyme II*triphosphopyridine nucleotide*nicotinamide adenine dinucleotide phosphate*NADP-oxidized*NADP-ox*NADP+*TPN*TPN+*TPN-ox*nicotinamide adenine dinucleotide-P*NADP(+)*NADP 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 1.14.13.8 nicotine + NADPH + O2 = nicotine-1'-N-oxide + NADP+ + H2O nicotine 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 744.418 C21 H29 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)[n+]5(cc(C(N)=O)ccc5)) LIGAND-CPD:C00006:*CAS:53-59-8 monovinyl protochlorophyllide a + NADPH = NADP+ + chlorophyllide a chlorophyllide a biosynthesis 18:3-16:3-MGDG 1-18:3-2-16:3-monogalactosyldiacylglycerol*1-(9Z,12Z,15Z-octadecatrienoyl)-2-(7Z,10Z,13Z-hexadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerol 747.02 C43 H70 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCC=CCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:2-16:3-MGDG = 18:3-16:3-MGDG glycolipid desaturation 18:3-16:3-MGDG 1-18:3-2-16:3-monogalactosyldiacylglycerol*1-(9Z,12Z,15Z-octadecatrienoyl)-2-(7Z,10Z,13Z-hexadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerol 747.02 C43 H70 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCC=CCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:3-16:2-MGDG = 18:3-16:3-MGDG glycolipid desaturation sarcosine N-methylglycine 89.094 C3 H7 N1 O2 C(=O)(O)CNC LIGAND-CPD:C00213:*CAS:107-97-1 1.5.99.2 dimethylglycine + H2O = formaldehyde + sarcosine glycine betaine degradation sarcosine N-methylglycine 89.094 C3 H7 N1 O2 C(=O)(O)CNC LIGAND-CPD:C00213:*CAS:107-97-1 1.5.3.1 O2 + H2O + sarcosine = H2O2 + formaldehyde + glycine glycine betaine degradation 24,25-dihydrolanosterol 4,4,14α-trimethyl-5α-cholesta-8-en-3β-ol*5alpha-lanost-8-en-3beta-ol 428.74 C30 H52 O1 CC(C)CCCC(C)C1(C2(C(CC1)(C)C3(=C(CC2)C4(C(CC3)C(C)(C)C(O)CC4)(C)))(C)) PUBCHEM:440560: 1.3.1.72 lanosterol + NADPH = 24,25-dihydrolanosterol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 24,25-dihydrolanosterol 4,4,14α-trimethyl-5α-cholesta-8-en-3β-ol*5alpha-lanost-8-en-3beta-ol 428.74 C30 H52 O1 CC(C)CCCC(C)C1(C2(C(CC1)(C)C3(=C(CC2)C4(C(CC3)C(C)(C)C(O)CC4)(C)))(C)) PUBCHEM:440560: 1.14.13.70 24,25-dihydrolanosterol + O2 + NADPH = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 18:3-18:3-DGDG 1-18:3-2-18:3-digalactosyldiacylglycerol*1,2-(9Z,12Z,15Z-octadecatrienoyl)-3-O-[alpha-D-galactosyl-(1>6)-O-beta-D-galactosyl]-sn-glycerol 937.216 C51 H84 O15 C(OC1(OC(C(O)C(O)C1O)COC2(C(O)C(O)C(O)C(O2)CO)))C(OC(=O)CCCCCCCC=CCC=CCC=CCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:3-18:2-DGDG = 18:3-18:3-DGDG glycolipid desaturation 18:3-18:3-DGDG 1-18:3-2-18:3-digalactosyldiacylglycerol*1,2-(9Z,12Z,15Z-octadecatrienoyl)-3-O-[alpha-D-galactosyl-(1>6)-O-beta-D-galactosyl]-sn-glycerol 937.216 C51 H84 O15 C(OC1(OC(C(O)C(O)C1O)COC2(C(O)C(O)C(O)C(O2)CO)))C(OC(=O)CCCCCCCC=CCC=CCC=CCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:2-18:3-DGDG = 18:3-18:3-DGDG glycolipid desaturation D-xylulose xylulose*D-threo-pentulose 150.131 C5 H10 O5 C(O)C(O)C(O)C(=O)CO LIGAND-CPD:C00310:*CAS:551-84-8 5.3.1.5 D-xylose = D-xylulose xylose degradation D-xylulose xylulose*D-threo-pentulose 150.131 C5 H10 O5 C(O)C(O)C(O)C(=O)CO LIGAND-CPD:C00310:*CAS:551-84-8 2.7.1.17 D-xylulose + ATP = D-xylulose-5-phosphate + ADP xylose degradation oryzalexin A 3-Hydroxy-7-oxo-sandaracopimaradien*3-Hydroxy-7-oxo-sandaracopimaradiene 302.456 C20 H30 O2 CC1(C=C2([CH](CC1)C3([CH](CC(=O)2)C(C)(C)C(O)CC3)(C)))(C=C) oryzalexin D = oryzalexin A oryzalexin A-F biosynthesis oryzalexin A 3-Hydroxy-7-oxo-sandaracopimaradien*3-Hydroxy-7-oxo-sandaracopimaradiene 302.456 C20 H30 O2 CC1(C=C2([CH](CC1)C3([CH](CC(=O)2)C(C)(C)C(O)CC3)(C)))(C=C) oryzalexin A = oryzalexin C oryzalexin A-F biosynthesis tartronate semialdehyde 2-hydroxy-3-oxopropanoate*tartronic semialdehyde*hydroxymalonaldehydic acid*tartronate-S-ald 104.062 C3 H4 O4 C(=O)(O)C(O)C=O LIGAND-CPD:C01146:*CAS:2480-77-5 1.1.1.60 glycerate = tartronate semialdehyde + H+ glycolate and glyoxylate degradation I tartronate semialdehyde 2-hydroxy-3-oxopropanoate*tartronic semialdehyde*hydroxymalonaldehydic acid*tartronate-S-ald 104.062 C3 H4 O4 C(=O)(O)C(O)C=O LIGAND-CPD:C01146:*CAS:2480-77-5 1.1.1.60 glycerate = tartronate semialdehyde + H+ allantoin degradation I tartronate semialdehyde 2-hydroxy-3-oxopropanoate*tartronic semialdehyde*hydroxymalonaldehydic acid*tartronate-S-ald 104.062 C3 H4 O4 C(=O)(O)C(O)C=O LIGAND-CPD:C01146:*CAS:2480-77-5 4.1.1.47 glyoxylate = CO2 + tartronate semialdehyde glycolate and glyoxylate degradation I tartronate semialdehyde 2-hydroxy-3-oxopropanoate*tartronic semialdehyde*hydroxymalonaldehydic acid*tartronate-S-ald 104.062 C3 H4 O4 C(=O)(O)C(O)C=O LIGAND-CPD:C01146:*CAS:2480-77-5 4.1.1.47 glyoxylate = CO2 + tartronate semialdehyde allantoin degradation I palmitaldehyde palmitoyl aldehyde*palmitaldehyde*hexadecanal 240.428 C16 H32 O1 C(=O)CCCCCCCCCCCCCCC CAS:629-80-1 4.1.2.27 sphinganine 1-phosphate = palmitaldehyde + phosphoryl-ethanolamine sphingolipid metabolism UDP-GlcNAc-enolpyruvate UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine*UDP-N-acetylglucosamine-3-O-pyruvate ether*UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine*UDP-GlcNAc-pyruvate enol ether 677.405 C20 H29 N3 O19 P2 C=C(C(O)=O)OC1(C(NC(=O)C)C(OC(C1O)CO)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c(=O)[nH]c(=O)cc3))) LIGAND-CPD:C04631: 2.5.1.7 UDP-N-acetyl-D-glucosamine + phosphoenolpyruvate = UDP-GlcNAc-enolpyruvate peptidoglycan biosynthesis I UDP-GlcNAc-enolpyruvate UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine*UDP-N-acetylglucosamine-3-O-pyruvate ether*UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine*UDP-GlcNAc-pyruvate enol ether 677.405 C20 H29 N3 O19 P2 C=C(C(O)=O)OC1(C(NC(=O)C)C(OC(C1O)CO)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c(=O)[nH]c(=O)cc3))) LIGAND-CPD:C04631: 1.1.1.158 NADP+ + UDP-N-acetylmuramate = NADPH + UDP-GlcNAc-enolpyruvate peptidoglycan biosynthesis I delphinidin-3-O-β-D-glucoside delfinidin-3-O-glucoside 465.39 C21 H21 O12 C1(OC(CO)C(O)C(O)C(O)1)OC3(C(c2(cc(O)c(O)c(O)c2))=Oc4(c(C=3)c(O)cc(O)c4)) 2.4.1.115 UDP-D-glucose + delphinidin = UDP + delphinidin-3-O-β-D-glucoside anthocyanin biosynthesis (delphinidin 3-O-glucoside) delphinidin-3-O-β-D-glucoside delfinidin-3-O-glucoside 465.39 C21 H21 O12 C1(OC(CO)C(O)C(O)C(O)1)OC3(C(c2(cc(O)c(O)c(O)c2))=Oc4(c(C=3)c(O)cc(O)c4)) 2.4.1.- delphinidin-3-O-β-D-glucoside + UDP-D-glucose = delphinidin-3,5-diglucoside + UDP gentiodelphin biosynthesis indole-3-glycerol-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 287.208 C11 H14 N1 O6 P1 C(OP(=O)(O)O)C(O)C(O)c1(c2(c([nH]c1)cccc2)) LIGAND-CPD:C03506: 4.1.1.48 1-(o-carboxyphenylamino)-1'-deoxyribulose-5'-phosphate = indole-3-glycerol-phosphate + CO2 + H2O tryptophan biosynthesis indole-3-glycerol-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 287.208 C11 H14 N1 O6 P1 C(OP(=O)(O)O)C(O)C(O)c1(c2(c([nH]c1)cccc2)) LIGAND-CPD:C03506: indole-3-glycerol-phosphate = indole + sn-glycerol-3-phosphate IAA biosynthesis I indole-3-glycerol-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 287.208 C11 H14 N1 O6 P1 C(OP(=O)(O)O)C(O)C(O)c1(c2(c([nH]c1)cccc2)) LIGAND-CPD:C03506: indole-3-glycerol-phosphate = indole + D-glyceraldehyde-3-phosphate tryptophan biosynthesis 9-HPOT 9(S)-hydroperoxy-10(E),12(Z),15(Z)-octadecatrienoic acid 310.433 C18 H30 O4 CCC=CCC=CC=CC(OO)CCCCCCCC(=O)O 1.13.11.- linolenate + O2 = 9-HPOT 9-LOX and 9-HPL pathway 9-HPOT 9(S)-hydroperoxy-10(E),12(Z),15(Z)-octadecatrienoic acid 310.433 C18 H30 O4 CCC=CCC=CC=CC(OO)CCCCCCCC(=O)O 9-HPOT = (3Z,6Z)-nonadienal + 9-oxo-nonanoate 9-LOX and 9-HPL pathway thiamine diphosphate thiamine pyrophosphate*Thaimine pyrophosphate*TPP*thiamin-PPi*thiamin pyrophosphate*thiamin diphosphate*thiamine-PPi*ThPP 425.312 C12 H19 N4 O7 P2 S1 C(c1(c(N)nc(C)nc1))[n+]2(c(C)c(sc2)CCOP(O)(=O)OP(O)(=O)O) CAS:154-87-0:*LIGAND-CPD:C00068: 2.7.4.16 thiamine-phosphate + ATP = thiamine diphosphate + ADP thiamine biosynthesis thiamine diphosphate thiamine pyrophosphate*Thaimine pyrophosphate*TPP*thiamin-PPi*thiamin pyrophosphate*thiamin diphosphate*thiamine-PPi*ThPP 425.312 C12 H19 N4 O7 P2 S1 C(c1(c(N)nc(C)nc1))[n+]2(c(C)c(sc2)CCOP(O)(=O)OP(O)(=O)O) CAS:154-87-0:*LIGAND-CPD:C00068: succinate-semialdehyde-thiamine PPi + isochorismate = 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate + thiamine diphosphate + pyruvate menaquinone biosynthesis thiamine diphosphate thiamine pyrophosphate*Thaimine pyrophosphate*TPP*thiamin-PPi*thiamin pyrophosphate*thiamin diphosphate*thiamine-PPi*ThPP 425.312 C12 H19 N4 O7 P2 S1 C(c1(c(N)nc(C)nc1))[n+]2(c(C)c(sc2)CCOP(O)(=O)OP(O)(=O)O) CAS:154-87-0:*LIGAND-CPD:C00068: succinate-semialdehyde-thiamine PPi + isochorismate = 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate + thiamine diphosphate + pyruvate phylloquinone biosynthesis thiamine diphosphate thiamine pyrophosphate*Thaimine pyrophosphate*TPP*thiamin-PPi*thiamin pyrophosphate*thiamin diphosphate*thiamine-PPi*ThPP 425.312 C12 H19 N4 O7 P2 S1 C(c1(c(N)nc(C)nc1))[n+]2(c(C)c(sc2)CCOP(O)(=O)OP(O)(=O)O) CAS:154-87-0:*LIGAND-CPD:C00068: 4.1.1.71 α-ketoglutarate + thiamine diphosphate = succinate-semialdehyde-thiamine PPi + CO2 menaquinone biosynthesis coumarinic acid-β-D-glucoside coumarinic acid glucoside*coumarinate glucoside 326.302 C15 H18 O8 C1(C(O)C(O)C(O)C(O1)CO)Oc2(c(C=CC(O)=O)cccc2) 5.2.1.- trans-β-D-Glucosyl-2-hydroxycinnamate = coumarinic acid-β-D-glucoside coumarin biosynthesis (via 2-coumarate) coumarinic acid-β-D-glucoside coumarinic acid glucoside*coumarinate glucoside 326.302 C15 H18 O8 C1(C(O)C(O)C(O)C(O1)CO)Oc2(c(C=CC(O)=O)cccc2) 3.2.1.21 coumarinic acid-β-D-glucoside + H2O = coumarinate + β-D-glucose coumarin biosynthesis (via 2-coumarate) D-myo-inositol (3,4,6)-trisphosphate 1D-myo-inositol (3,4,6)-trisphosphate*Ins(3,4,6)P3*I(3,4,6)P3 417.073 C6 H12 O15 P3 C1(C(OP(O)([O-])=O)C(O)C(OP(O)([O-])=O)C(O)C(O)1)(OP(O)([O-])=O) D-myo-inositol (3,4,6)-trisphosphate + ATP = D-myo-inositol (3,4,5,6)-tetrakisphosphate + ADP lipid-independent phytate biosynthesis D-myo-inositol (3,4,6)-trisphosphate 1D-myo-inositol (3,4,6)-trisphosphate*Ins(3,4,6)P3*I(3,4,6)P3 417.073 C6 H12 O15 P3 C1(C(OP(O)([O-])=O)C(O)C(OP(O)([O-])=O)C(O)C(O)1)(OP(O)([O-])=O) D-myo-inositol (3,4)-bisphosphate + ATP = D-myo-inositol (3,4,6)-trisphosphate + ADP lipid-independent phytate biosynthesis allantoin 158.116 C4 H6 N4 O3 C1(NC(N)=O)(C(=O)NC(N1)=O) LIGAND-CPD:C01551:*CAS:97-59-6 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate = allantoin + CO2 ureide biosynthesis allantoin 158.116 C4 H6 N4 O3 C1(NC(N)=O)(C(=O)NC(N1)=O) LIGAND-CPD:C01551:*CAS:97-59-6 1.7.3.3 urate + O2 = allantoin + CO2 + H2O2 purine degradation allantoin 158.116 C4 H6 N4 O3 C1(NC(N)=O)(C(=O)NC(N1)=O) LIGAND-CPD:C01551:*CAS:97-59-6 3.5.2.5 H2O + allantoin = allantoate ureide biosynthesis allantoin 158.116 C4 H6 N4 O3 C1(NC(N)=O)(C(=O)NC(N1)=O) LIGAND-CPD:C01551:*CAS:97-59-6 3.5.2.5 H2O + allantoin = allantoate allantoin degradation I 18:1-16:0-PG 1-18:1-2-16:0-phosphatidylglycerol 749.016 C40 H77 O10 P1 C(OP(=O)(O)OCC(O)CO)C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC 1.14.99.- 18:1-16:0-PG = 18:1-t16:1-PG phospholipid desaturation 18:1-16:0-PG 1-18:1-2-16:0-phosphatidylglycerol 749.016 C40 H77 O10 P1 C(OP(=O)(O)OCC(O)CO)C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC 1.14.99.- 18:1-16:0-PG = 18:2-16:0-PG phospholipid desaturation O-acetyl-L-homoserine acetylhomoserine*O-acetylhomoserine 161.157 C6 H11 N1 O4 C(C)(=O)OCCC(N)C(=O)O 2.3.1.31 homoserine + acetyl-CoA = O-acetyl-L-homoserine + coenzyme A homocysteine biosynthesis O-acetyl-L-homoserine acetylhomoserine*O-acetylhomoserine 161.157 C6 H11 N1 O4 C(C)(=O)OCCC(N)C(=O)O O-acetyl-L-homoserine + L-cysteine = cystathionine + acetate homocysteine and cysteine interconversion O-acetyl-L-homoserine acetylhomoserine*O-acetylhomoserine 161.157 C6 H11 N1 O4 C(C)(=O)OCCC(N)C(=O)O 2.5.1.49 O-acetyl-L-homoserine + hydrogen sulfide = L-homocysteine + acetate homocysteine biosynthesis D-alanine 89.094 C3 H7 N1 O2 C(O)(=O)C(N)C LIGAND-CPD:C00133:*CAS:338-69-2 6.3.2.4 D-alanine + ATP = D-alanyl-D-alanine + ADP peptidoglycan biosynthesis I indole-3-yl-acetyl-myo-inositol L-arabinoside indole-3-yl-acetyl-myo-inositol 3-L-arabinoside 469.444 C21 H26 N1 O11 c1(c(c2(c(n1)cccc2))CC(=O)OC3(C(O)C(O)C(C(O)C3O)OC4(C(O)C(O)C(O)CO4))) LIGAND-CPD:C04611: 2.4.2.34 UDP-L-arabinose + indol-3-yl-acetyl-myo-inositol = UDP + indole-3-yl-acetyl-myo-inositol L-arabinoside IAA conjugate biosynthesis I 4α-hydroxymethyl-5α-cholesta-8-en-3β-ol 416.686 C28 H48 O2 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(CO)C(O)CC4)(C)))(C)) 1.14.13.72 4α-hydroxymethyl-5α-cholesta-8-en-3β-ol + O2 = 4α-formyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 4α-hydroxymethyl-5α-cholesta-8-en-3β-ol 416.686 C28 H48 O2 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(CO)C(O)CC4)(C)))(C)) 1.14.13.72 4α-methyl-cholesta-8-enol + O2 = 4α-hydroxymethyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) dihydroquercetin (+)-taxifolin*(+)-dihydroquercetin*taxifolin 304.256 C15 H12 O7 c1(cc(cc(O)c1O)C2(C(O)C(=O)c3(c(O2)cc(O)cc3O))) LIGAND-CPD:C01617:*CAS:480-18-2 1.14.11.23 dihydroquercetin + α-ketoglutarate + O2 = quercetin + succinate + CO2 + H2O flavonol biosynthesis dihydroquercetin (+)-taxifolin*(+)-dihydroquercetin*taxifolin 304.256 C15 H12 O7 c1(cc(cc(O)c1O)C2(C(O)C(=O)c3(c(O2)cc(O)cc3O))) LIGAND-CPD:C01617:*CAS:480-18-2 1.14.13.21 dihydrokaempferol + NADPH + O2 = dihydroquercetin + NADP+ + H2O leucopelargonidin and leucocyanidin biosynthesis dihydroquercetin (+)-taxifolin*(+)-dihydroquercetin*taxifolin 304.256 C15 H12 O7 c1(cc(cc(O)c1O)C2(C(O)C(=O)c3(c(O2)cc(O)cc3O))) LIGAND-CPD:C01617:*CAS:480-18-2 1.14.13.21 dihydrokaempferol + NADPH + O2 = dihydroquercetin + NADP+ + H2O leucodelphinidin biosynthesis dihydroquercetin (+)-taxifolin*(+)-dihydroquercetin*taxifolin 304.256 C15 H12 O7 c1(cc(cc(O)c1O)C2(C(O)C(=O)c3(c(O2)cc(O)cc3O))) LIGAND-CPD:C01617:*CAS:480-18-2 1.14.13.21 dihydrokaempferol + NADPH + O2 = dihydroquercetin + NADP+ + H2O flavonol biosynthesis dihydroquercetin (+)-taxifolin*(+)-dihydroquercetin*taxifolin 304.256 C15 H12 O7 c1(cc(cc(O)c1O)C2(C(O)C(=O)c3(c(O2)cc(O)cc3O))) LIGAND-CPD:C01617:*CAS:480-18-2 1.14.13.88 dihydroquercetin + NADPH + O2 = dihydromyricetin + NADP+ + H2O leucodelphinidin biosynthesis dihydroquercetin (+)-taxifolin*(+)-dihydroquercetin*taxifolin 304.256 C15 H12 O7 c1(cc(cc(O)c1O)C2(C(O)C(=O)c3(c(O2)cc(O)cc3O))) LIGAND-CPD:C01617:*CAS:480-18-2 1.14.11.9 eriodictyol + O2 + α-ketoglutarate = dihydroquercetin + CO2 + succinate leucopelargonidin and leucocyanidin biosynthesis dihydroquercetin (+)-taxifolin*(+)-dihydroquercetin*taxifolin 304.256 C15 H12 O7 c1(cc(cc(O)c1O)C2(C(O)C(=O)c3(c(O2)cc(O)cc3O))) LIGAND-CPD:C01617:*CAS:480-18-2 1.14.11.9 eriodictyol + O2 + α-ketoglutarate = dihydroquercetin + CO2 + succinate leucodelphinidin biosynthesis dihydroquercetin (+)-taxifolin*(+)-dihydroquercetin*taxifolin 304.256 C15 H12 O7 c1(cc(cc(O)c1O)C2(C(O)C(=O)c3(c(O2)cc(O)cc3O))) LIGAND-CPD:C01617:*CAS:480-18-2 1.1.1.219 dihydroquercetin + NADPH = leucocyanidin + NADP+ leucopelargonidin and leucocyanidin biosynthesis L-tryptophan W*tryptacin*trofan*trp*tryptophan*2-amino-3-indolylpropanic acid 204.228 C11 H12 N2 O2 c1(c(CC(N)C(=O)O)c2(c([nH]1)cccc2)) LIGAND-CPD:C00078:*CAS:73-22-3 6.1.1.2 ATP + L-tryptophan = AMP + diphosphate tRNA charging pathway L-tryptophan W*tryptacin*trofan*trp*tryptophan*2-amino-3-indolylpropanic acid 204.228 C11 H12 N2 O2 c1(c(CC(N)C(=O)O)c2(c([nH]1)cccc2)) LIGAND-CPD:C00078:*CAS:73-22-3 1.13.99.3 L-tryptophan + O2 = indole acetaldehyde + ammonia + CO2 tryptophan degradation V (side chain pathway) L-tryptophan W*tryptacin*trofan*trp*tryptophan*2-amino-3-indolylpropanic acid 204.228 C11 H12 N2 O2 c1(c(CC(N)C(=O)O)c2(c([nH]1)cccc2)) LIGAND-CPD:C00078:*CAS:73-22-3 1.14.13.- L-tryptophan + NADPH + O2 = indole-3-acetaldoxime + CO2 + NADP+ + H2O IAA biosynthesis I L-tryptophan W*tryptacin*trofan*trp*tryptophan*2-amino-3-indolylpropanic acid 204.228 C11 H12 N2 O2 c1(c(CC(N)C(=O)O)c2(c([nH]1)cccc2)) LIGAND-CPD:C00078:*CAS:73-22-3 4.1.1.28 L-tryptophan = CO2 + tryptamine IAA biosynthesis I L-tryptophan W*tryptacin*trofan*trp*tryptophan*2-amino-3-indolylpropanic acid 204.228 C11 H12 N2 O2 c1(c(CC(N)C(=O)O)c2(c([nH]1)cccc2)) LIGAND-CPD:C00078:*CAS:73-22-3 4.1.1.28 L-tryptophan = CO2 + tryptamine secologanin and strictosidine biosynthesis L-tryptophan W*tryptacin*trofan*trp*tryptophan*2-amino-3-indolylpropanic acid 204.228 C11 H12 N2 O2 c1(c(CC(N)C(=O)O)c2(c([nH]1)cccc2)) LIGAND-CPD:C00078:*CAS:73-22-3 2.6.1.27 α-ketoglutarate + L-tryptophan = L-glutamate + indole-3-pyruvate IAA biosynthesis I L-tryptophan W*tryptacin*trofan*trp*tryptophan*2-amino-3-indolylpropanic acid 204.228 C11 H12 N2 O2 c1(c(CC(N)C(=O)O)c2(c([nH]1)cccc2)) LIGAND-CPD:C00078:*CAS:73-22-3 4.2.1.20 indole + L-serine = L-tryptophan + H2O tryptophan biosynthesis L-tryptophan W*tryptacin*trofan*trp*tryptophan*2-amino-3-indolylpropanic acid 204.228 C11 H12 N2 O2 c1(c(CC(N)C(=O)O)c2(c([nH]1)cccc2)) LIGAND-CPD:C00078:*CAS:73-22-3 1.13.12.3 O2 + L-tryptophan = indole-3-acetamide + H2O + CO2 IAA biosynthesis VI (via indole-3-acetamide) 18:3-16:0-DGDG 1-18:3-2-16:0-digalactosyldiacylglycerol 915.209 C49 H86 O15 C(OC1(OC(C(O)C(O)C1O)COC2(C(O)C(O)C(O)C(O2)CO)))C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:2-16:0-DGDG = 18:3-16:0-DGDG glycolipid desaturation dolichyl β-D-mannosyl phosphate dolichol monophosphate mannose*β-D-mannopyranose, 1-ester with dolichol dihydrogen phosphate*D-mannose, ester with dolichol dihydrogen phosphate*mannosyl phosphoryl dolichol*mannolipid*dolichyl mannosyl phosphate*dolichyl mannopyranosyl phosphate*dolichol, β-D-mannopyranose deriv.*dolichyl phosphate D-mannose*dolichyl D-mannosyl phosphate 1352.044 C86 H143 O9 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OC1(C(O)C(O)C(O)C(O1)CO) PUBCHEM:41482:*CAS:55598-56-6: (mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis dolichyl β-D-mannosyl phosphate dolichol monophosphate mannose*β-D-mannopyranose, 1-ester with dolichol dihydrogen phosphate*D-mannose, ester with dolichol dihydrogen phosphate*mannosyl phosphoryl dolichol*mannolipid*dolichyl mannosyl phosphate*dolichyl mannopyranosyl phosphate*dolichol, β-D-mannopyranose deriv.*dolichyl phosphate D-mannose*dolichyl D-mannosyl phosphate 1352.044 C86 H143 O9 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OC1(C(O)C(O)C(O)C(O1)CO) PUBCHEM:41482:*CAS:55598-56-6: (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis dolichyl β-D-mannosyl phosphate dolichol monophosphate mannose*β-D-mannopyranose, 1-ester with dolichol dihydrogen phosphate*D-mannose, ester with dolichol dihydrogen phosphate*mannosyl phosphoryl dolichol*mannolipid*dolichyl mannosyl phosphate*dolichyl mannopyranosyl phosphate*dolichol, β-D-mannopyranose deriv.*dolichyl phosphate D-mannose*dolichyl D-mannosyl phosphate 1352.044 C86 H143 O9 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OC1(C(O)C(O)C(O)C(O1)CO) PUBCHEM:41482:*CAS:55598-56-6: 2.4.1.83 dolichyl-phosphate + GDP-D-mannose = dolichyl β-D-mannosyl phosphate + GDP dolichyl-diphosphooligosaccharide biosynthesis dolichyl β-D-mannosyl phosphate dolichol monophosphate mannose*β-D-mannopyranose, 1-ester with dolichol dihydrogen phosphate*D-mannose, ester with dolichol dihydrogen phosphate*mannosyl phosphoryl dolichol*mannolipid*dolichyl mannosyl phosphate*dolichyl mannopyranosyl phosphate*dolichol, β-D-mannopyranose deriv.*dolichyl phosphate D-mannose*dolichyl D-mannosyl phosphate 1352.044 C86 H143 O9 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OC1(C(O)C(O)C(O)C(O1)CO) PUBCHEM:41482:*CAS:55598-56-6: (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis dolichyl β-D-mannosyl phosphate dolichol monophosphate mannose*β-D-mannopyranose, 1-ester with dolichol dihydrogen phosphate*D-mannose, ester with dolichol dihydrogen phosphate*mannosyl phosphoryl dolichol*mannolipid*dolichyl mannosyl phosphate*dolichyl mannopyranosyl phosphate*dolichol, β-D-mannopyranose deriv.*dolichyl phosphate D-mannose*dolichyl D-mannosyl phosphate 1352.044 C86 H143 O9 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OC1(C(O)C(O)C(O)C(O1)CO) PUBCHEM:41482:*CAS:55598-56-6: (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis indole-3-glyoxylate 189.17 C10 H7 N1 O3 c1(c(C(=O)C(O)=O)c2(c([nH]1)cccc2)) 1.2.1.5 indole-3-glyoxal + H2O + an oxidized acceptor = indole-3-glyoxylate tryptophan degradation V (side chain pathway) indole-3-glyoxylate 189.17 C10 H7 N1 O3 c1(c(C(=O)C(O)=O)c2(c([nH]1)cccc2)) 1.13.99.3 indole-3-glycolate = indole-3-glyoxylate tryptophan degradation V (side chain pathway) D,L-malic semialdehyde 118.089 C4 H6 O4 C(=O)C(O)CC(O)=O O2 + H+ = trimethylamine + D,L-malic semialdehyde + H2O carnitine degradation III D,L-malic semialdehyde 118.089 C4 H6 O4 C(=O)C(O)CC(O)=O 1.2.1.5 D,L-malic semialdehyde + H2O = malate + H+ carnitine degradation III γ-humulene 204.355 C15 H24 CC1(=CCCC(=C)C=CC(C)(C)CCC1) 4.2.3.- trans, trans-farnesyl diphosphate = γ-humulene + diphosphate oleoresin sesquiterpene volatiles 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate formylTHF 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate tetrahydrofolate 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate formylTHF 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate tetrahydrofolate 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 6.3.2.17 tetrahydrofolate + L-glutamate + ATP = THF-L-glutamate + ADP tetrahydrofolate 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.10 tetrahydrofolate = 5,10-methylene-THF + 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.11 5,10-methylene-THF + 2-keto-isovalerate + H2O = tetrahydrofolate + 2-dehydropantoate 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.11 5,10-methylene-THF + 2-keto-isovalerate + H2O = tetrahydrofolate + 2-dehydropantoate pantothenate 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH folate transformations 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH formylTHF 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + CO2 + NADH formylTHF 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 glycine + tetrahydrofolate + NAD+ = ammonia + 5,10-methylene-THF + 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.3 N10-formyl-THF + AICAR = tetrahydrofolate + phosphoribosyl-formamido-carboxamide purine nucleotides de novo 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.3 N10-formyl-THF + AICAR = tetrahydrofolate + phosphoribosyl-formamido-carboxamide purine nucleotides de novo 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF folate polyglutamylation 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF folate transformations 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF formylTHF 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF formylTHF 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate folate polyglutamylation 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate folate transformations 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate glycine betaine degradation 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate formylTHF 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate formylTHF 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.1 5,10-methylene-THF + glycine + H2O = L-serine + tetrahydrofolate 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.1.19 tetrahydrofolate + trimethyl sulfonium = dimethylsulfide + 5-methyl-THF folate transformations 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.2 N10-formyl-THF + 5-phospho-ribosyl-glycineamide = tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide purine nucleotides de novo 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.2 N10-formyl-THF + 5-phospho-ribosyl-glycineamide = tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide tetrahydrofolate 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.2.2 N10-formyl-THF + 5-phospho-ribosyl-glycineamide = tetrahydrofolate + 5'-phosphoribosyl-N-formylglycineamide purine nucleotides de novo 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 3.5.1.10 H2O + N10-formyl-THF = tetrahydrofolate + formate folate transformations 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 3.5.1.10 H2O + N10-formyl-THF = tetrahydrofolate + formate formylTHF 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate S-adenosylmethionine 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate methionine 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate folate transformations 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate formylTHF 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 445.434 C19 H23 N7 O6 C2([CH](Nc1(c(=O)[nH]c(N)nc1N2))C[NH]c3(ccc(cc3)C(=O)NC(C(O)=O)CCC(O)=O)) CAS:135-16-0:*LIGAND-CPD:C00101:*CAS:29347-89-5 2.1.1.13 L-homocysteine + 5-methyl-THF = L-methionine + tetrahydrofolate formylTHF biosynthesis I campest-4-en-3β-ol methylcholestenol*(24R)-24-methyl-cholest-4-en-3β-ol 400.687 C28 H48 O1 CC(C)C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(CC3)=CC(O)CC4)(C)))) 1.1.1.145 campest-4-en-3β-ol = 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 CC(C)C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(CC3)=CC(O)CC4)(C)))) 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([O-])(=O)C[N+](C)(C)C LIGAND-CPD:C00719:*CAS:107-43-7 1.2.1.8 betaine aldehyde + NAD+ + H2O = glycine betaine + NADH glycine betaine biosynthesis III (plants) glycine betaine oxyneurine*lycine*acidin-pepsin*betaine*trimethylammonioacetate*N,N,N-trimethylglycine 117.147 C5 H11 N1 O2 C([O-])(=O)C[N+](C)(C)C LIGAND-CPD:C00719:*CAS:107-43-7 2.1.1.5 L-homocysteine + glycine betaine = L-methionine + dimethylglycine glycine betaine degradation crocetin dialdehyde 2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-septene-1,16-dial 296.408 C20 H24 O2 CC(C=O)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=O 1.2.99.3 crocetin dialdehyde + H2O = crocetin crocetin biosynthesis crocetin dialdehyde 2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-septene-1,16-dial 296.408 C20 H24 O2 CC(C=O)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=O 1.14.99.- zeaxanthin + O2 = crocetin dialdehyde + hydroxy-β-cyclocitral crocetin biosynthesis (-)-sophorol 300.267 C16 H12 O6 C1([CH](C(=O)c2(c(O1)cc(O)cc2))c3(c(O)cc4(c(c3)OCO4))) 1.1.1.246 (-)-sophorol + NADPH = (-)-maackiain + NADP+ + H2O maackiain biosynthesis (-)-sophorol 300.267 C16 H12 O6 C1([CH](C(=O)c2(c(O1)cc(O)cc2))c3(c(O)cc4(c(c3)OCO4))) 1.3.1.45 2'-hydroxypseudobaptigenin + NADPH = (-)-sophorol + NADP+ maackiain biosynthesis delphinidin-3,5-diglucoside 627.532 C27 H31 O17 C1(OC(CO)C(O)C(O)C(O)1)OC3(C(c2(cc(O)c(O)c(O)c2))=Oc4(c(C=3)c(cc(O)c4)OC5(OC(CO)C(O)C(O)C(O)5))) 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 627.532 C27 H31 O17 C1(OC(CO)C(O)C(O)C(O)1)OC3(C(c2(cc(O)c(O)c(O)c2))=Oc4(c(C=3)c(cc(O)c4)OC5(OC(CO)C(O)C(O)C(O)5))) 2.4.1.- delphinidin-3-O-β-D-glucoside + UDP-D-glucose = delphinidin-3,5-diglucoside + UDP gentiodelphin biosynthesis delphinidin-3,5-diglucoside 627.532 C27 H31 O17 C1(OC(CO)C(O)C(O)C(O)1)OC3(C(c2(cc(O)c(O)c(O)c2))=Oc4(c(C=3)c(cc(O)c4)OC5(OC(CO)C(O)C(O)C(O)5))) 2.4.1.238 delphinidin-3,5-diglucoside + UDP-D-glucose = delphinidin 3,5,3'-triglucoside + UDP gentiodelphin biosynthesis phloroglucinol 1,3,5-trihydroxybenzene*1,3,5-benzenetriol*1,3,5-THB 126.11 C6 H6 O3 C1(=CC(O)=CC(=C1)O)(O) LIGAND-CPD:c02183:*UM-BBD-CPD:c0026:*NCI:1572*CAS:108-73-6 1.3.1.57 dihydrophloroglucinol + NADP+ = phloroglucinol + NADPH gallate degradation III (anaerobic) phloroglucinol 1,3,5-trihydroxybenzene*1,3,5-benzenetriol*1,3,5-THB 126.11 C6 H6 O3 C1(=CC(O)=CC(=C1)O)(O) LIGAND-CPD:c02183:*UM-BBD-CPD:c0026:*NCI:1572*CAS:108-73-6 1.97.1.2 1,2,3,5-tetrahydroxybenzene + pyrogallol = 1,2,3,5-tetrahydroxybenzene + phloroglucinol gallate degradation III (anaerobic) N-dimethylethanolamine phosphate P-DME 169.117 C4 H12 N1 O4 P1 C(CN(C)C)OP(=O)(O)O 2.1.1.103 N-dimethylethanolamine phosphate + S-adenosyl-L-methionine = phosphoryl-choline + S-adenosyl-L-homocysteine choline biosynthesis I N-dimethylethanolamine phosphate P-DME 169.117 C4 H12 N1 O4 P1 C(CN(C)C)OP(=O)(O)O 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine choline biosynthesis I 2-oxo-5-methylthiopentanoic-acid 2-oxo-5-methylthiopentanoate*5-methylthio-2-oxopentanoate 162.203 C6 H10 O3 S1 C(=O)(O)C(=O)CCCSC 2.6.1.- 2-oxo-5-methylthiopentanoic-acid = homomethionine homomethionine biosynthesis 2-oxo-5-methylthiopentanoic-acid 2-oxo-5-methylthiopentanoate*5-methylthio-2-oxopentanoate 162.203 C6 H10 O3 S1 C(=O)(O)C(=O)CCCSC 1.1.1.- 3-(2'-methylthio)ethylmalic-acid = 2-oxo-5-methylthiopentanoic-acid + CO2 homomethionine biosynthesis 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate 201.118 C5 H5 N4 O5 C1(C(O)(C([O-])=O)[NH]C(=O)N=1)(NC(N)=O) 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate = allantoin + CO2 ureide biosynthesis 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate 201.118 C5 H5 N4 O5 C1(C(O)(C([O-])=O)[NH]C(=O)N=1)(NC(N)=O) 3.5.2.17 5-hydroxyisourate + H2O = 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate ureide biosynthesis N-acetyl-L,L-2,6-diaminopimelate N6-acetyl-L,L-2,6-diaminopimelate*N-acetyl-L,L-2,6-diaminoheptanedioate*N6-acetyl-L,L-2,6-diaminoheptanedioate*N2-acetyl-L,L-2,6-diaminoheptanedioate*N6-acetyl-L-2,6-diaminoheptanedioate*N-acetyl-L,L-DAP 232.236 C9 H16 N2 O5 CC(=O)NC(C(O)=O)CCCC(N)C(O)=O L-2-acetamido-6-oxoheptanedioate + L-glutamate = N-acetyl-L,L-2,6-diaminopimelate + α-ketoglutarate lysine biosynthesis II N-acetyl-L,L-2,6-diaminopimelate N6-acetyl-L,L-2,6-diaminopimelate*N-acetyl-L,L-2,6-diaminoheptanedioate*N6-acetyl-L,L-2,6-diaminoheptanedioate*N2-acetyl-L,L-2,6-diaminoheptanedioate*N6-acetyl-L-2,6-diaminoheptanedioate*N-acetyl-L,L-DAP 232.236 C9 H16 N2 O5 CC(=O)NC(C(O)=O)CCCC(N)C(O)=O 3.5.1.47 H2O + N-acetyl-L,L-2,6-diaminopimelate = L,L-diaminopimelate + acetate lysine biosynthesis II 7,2'-dihydroxy-4'-methoxy-isoflavanol carbocation intermediate 1 289.307 C16 H17 O5 C2([CH](c1(c(O)cc(OC)cc1))[CH]([OH2+])c3(c(O2)cc(O)cc3)) 7,2'-dihydroxy-4'-methoxy-isoflavanol = 7,2'-dihydroxy-4'-methoxy-isoflavanol carbocation intermediate 1 medicarpin biosynthesis 7,2'-dihydroxy-4'-methoxy-isoflavanol carbocation intermediate 1 289.307 C16 H17 O5 C2([CH](c1(c(O)cc(OC)cc1))[CH]([OH2+])c3(c(O2)cc(O)cc3)) 7,2'-dihydroxy-4'-methoxy-isoflavanol carbocation intermediate 1 = 7,2'-dihydroxy-4'-methoxy-isoflavanol carbocation intermediate 2 medicarpin biosynthesis 16:0-18:2-PC 1-16:0-2-18:2-phosphatidylcholine*1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine 759.078 C42 H81 N1 O8 P1 C(OP(=O)(O)OCC[N+](C)(C)C)C(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCC=CCC=CCCCCC PUBCHEM:5313191: 1.14.99.- 16:0-18:1-PC = 16:0-18:2-PC phospholipid desaturation 16:0-18:2-PC 1-16:0-2-18:2-phosphatidylcholine*1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine 759.078 C42 H81 N1 O8 P1 C(OP(=O)(O)OCC[N+](C)(C)C)C(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCC=CCC=CCCCCC PUBCHEM:5313191: 16:0-18:2-PC = 16:0-18:3-PC phospholipid desaturation (+)-3-carene (+)-Δ3-carene*3,7,7-trimethyl bicyclohept-3-ene 136.236 C10 H16 CC2(C)(C1(CC(C)=CCC12)) 4.2.3.- geranyl-PP = (+)-3-carene + diphosphate oleoresin monoterpene volatiles biosynthesis indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 indole-3-acetate + L-alanine = indole-3-acetyl-ala + H2O IAA conjugate biosynthesis II indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 3.5.5.1 indole-3-acetonitrile + H2O = ammonia + indole-3-acetate IAA biosynthesis I indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 2.4.1.121 indole-3-acetate + UDP-D-glucose = indole-3-acetyl-β-1-D-glucose + UDP IAA conjugate biosynthesis II indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 2.4.1.121 indole-3-acetate + UDP-D-glucose = indole-3-acetyl-β-1-D-glucose + UDP IAA conjugate biosynthesis I indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 indole-3-acetate + L-glutamine = indole-3-acetyl-gln + H2O IAA conjugate biosynthesis II indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 indole-3-acetate + L-glutamate = indole-3-acetyl-glu + H2O IAA conjugate biosynthesis II indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 1.13.99.3 indole-3-acetate + O2 = indole-3-glycolate tryptophan degradation V (side chain pathway) indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 1.2.1.5 indole acetaldehyde + H2O = indole-3-acetate + H+ tryptophan degradation V (side chain pathway) indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 3.5.1.4 indole-3-acetamide + H2O = indole-3-acetate + ammonia IAA biosynthesis VI (via indole-3-acetamide) indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 3.5.1.4 indole-3-acetamide + H2O = indole-3-acetate + ammonia IAA biosynthesis IV indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 indole-3-acetate + L-aspartate = indole-3-acetyl-asp + H2O IAA conjugate biosynthesis II indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 3.5.1.- indole-3-acetyl-ala + H2O = indole-3-acetate + L-alanine IAA biosynthesis II indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 1.2.3.7 indole acetaldehyde + O2 + H2O = indole-3-acetate + H2O2 IAA biosynthesis I indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 indole + acetate = indole-3-acetate IAA biosynthesis I indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 3.5.1.- indole-3-acetyl-leu + H2O = indole-3-acetate + L-leucine IAA biosynthesis II indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 indole-3-acetate + polypeptide = indole-3-acetyl-polypeptide IAA conjugate biosynthesis II indole-3-acetate IAA*indole-3-acetic acid*indoleacetic acid*auxin*indoleacetate 175.187 C10 H9 N1 O2 c1(c(CC(=O)O)c2(c([nH]1)cccc2)) CAS:87-51-4 indole-3-acetate + L-leucine = indole-3-acetyl-leu + H2O IAA conjugate biosynthesis II (5-L-glutamyl)-L-amino acid L-γ-glutamyl-L-amino acid C7 H11 N2 O5 R1 2.3.2.2 (5-L-glutamyl)-L-amino acid + Cys-Gly = glutathione γ-glutamyl cycle (5-L-glutamyl)-L-amino acid L-γ-glutamyl-L-amino acid C7 H11 N2 O5 R1 2.3.2.4 (5-L-glutamyl)-L-amino acid = L-2-amino-acid + 5-oxoproline γ-glutamyl cycle shikimate-3-phosphate shikimate-5-phosphate*shikimate-5-P*3-phosphoshikimate*5-phosphoshikimate*shikimate-3-P 254.133 C7 H11 O8 P1 C(O)(=O)C1(=[CH][CH]([CH](O)[CH]([CH2]1)O)OP(O)(O)=O) LIGAND-CPD:C03175: 2.7.1.71 shikimate + ATP = shikimate-3-phosphate + ADP chorismate biosynthesis shikimate-3-phosphate shikimate-5-phosphate*shikimate-5-P*3-phosphoshikimate*5-phosphoshikimate*shikimate-3-P 254.133 C7 H11 O8 P1 C(O)(=O)C1(=[CH][CH]([CH](O)[CH]([CH2]1)O)OP(O)(O)=O) LIGAND-CPD:C03175: 2.5.1.19 shikimate-3-phosphate + phosphoenolpyruvate = 5-enolpyruvyl-shikimate-3-phosphate chorismate biosynthesis L-tyrosine Y*tyr*tyrosine 181.191 C9 H11 N1 O3 C(=O)(O)C(N)Cc1(ccc(O)cc1) LIGAND-CPD:C00082:*CAS:60-18-4 2.6.1.5 L-tyrosine + α-ketoglutarate = L-glutamate + p-hydroxyphenylpyruvate tyrosine degradation I L-tyrosine Y*tyr*tyrosine 181.191 C9 H11 N1 O3 C(=O)(O)C(N)Cc1(ccc(O)cc1) LIGAND-CPD:C00082:*CAS:60-18-4 6.1.1.1 L-tyrosine + ATP = diphosphate + AMP tRNA charging pathway L-tyrosine Y*tyr*tyrosine 181.191 C9 H11 N1 O3 C(=O)(O)C(N)Cc1(ccc(O)cc1) LIGAND-CPD:C00082:*CAS:60-18-4 L-tyrosine + 1-deoxy-D-xylulose 5-phosphate = 4-methyl-5-(β-hydroxyethyl)thiazole phosphate + 4-hydroxybenzyl alcohol thiamine biosynthesis ADP-D-glucose adenosine diphosphate glucose*ADP-glucose 589.345 C16 H25 N5 O15 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(cnc4(c3c(N)ncn4))) LIGAND-CPD:C00498:*CAS:2140-58-1 2.7.7.27 α-D-glucose 1-phosphate + ATP = ADP-D-glucose + diphosphate starch biosynthesis ADP-D-glucose adenosine diphosphate glucose*ADP-glucose 589.345 C16 H25 N5 O15 P2 C1(C(O)C(O)C(O)C(O1)CO)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C(O)2)n3(cnc4(c3c(N)ncn4))) LIGAND-CPD:C00498:*CAS:2140-58-1 2.4.1.21 ADP-D-glucose = ADP starch biosynthesis N5-carboxyaminoimidazole ribonucleotide 5-phosphoribosyl-5-carboxyaminoimidazole*N5-CAIR 338.19 C9 H13 N3 O9 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c(NC(=O)[O-])cnc2)) 6.3.4.18 5-aminoimidazole ribonucleotide + ATP + HCO3- = N5-carboxyaminoimidazole ribonucleotide + ADP purine nucleotides de novo biosynthesis I N5-carboxyaminoimidazole ribonucleotide 5-phosphoribosyl-5-carboxyaminoimidazole*N5-CAIR 338.19 C9 H13 N3 O9 P1 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n2(c(NC(=O)[O-])cnc2)) N5-carboxyaminoimidazole ribonucleotide = 4-carboxyaminoimidazole ribonucleotide purine nucleotides de novo biosynthesis I L-4-hydroxy-proline hydroxy-L-proline*L-4-hydroxyproline*oxyproline*4-hydroxyproline*cis-4-hydroxyproline*OH-pro*hydroxyproline 131.131 C5 H9 N1 O3 C1(C(O)CC(N1)C(=O)O) CAS:51-35-4 L-4-hydroxy-proline + O2 = pyrroline-hydroxy-carboxylate + H2O 4-hydroxyproline degradation I abscisic aldehyde ABA aldehyde*abscisic acid aldehyde 248.321 C15 H20 O3 CC1(C(C(C)=CC(=O)C1)(O)C=CC(C)=CC=O)(C) 1.2.3.14 abscisic aldehyde + H2O + O2 = (+)-abscisate + H2O2 abscisic acid biosynthesis abscisic aldehyde ABA aldehyde*abscisic acid aldehyde 248.321 C15 H20 O3 CC1(C(C(C)=CC(=O)C1)(O)C=CC(C)=CC=O)(C) 1.1.1.288 xanthoxin + NAD+ = abscisic aldehyde + NADH + H+ abscisic acid 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = fructose-6-phosphate + D-glyceraldehyde-3-phosphate xylulose-monophosphate 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = fructose-6-phosphate + D-glyceraldehyde-3-phosphate Calvin 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-erythrose-4-phosphate + D-xylulose-5-phosphate = 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH gluconeogenesis 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH sucrose degradation to ethanol and lactate (anaerobic) 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH fructose degradation to pyruvate and lactate (anaerobic) 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH glucose fermentation to lactate II 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.2 D-glyceraldehyde-3-phosphate + D-sedoheptulose-7-phosphate = fructose-6-phosphate + D-erythrose-4-phosphate glucose fermentation to lactate II 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.9 D-xylulose-5-phosphate = H2O + D-glyceraldehyde-3-phosphate + acetylphosphate glucose fermentation to lactate II 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.3 formaldehyde + D-xylulose-5-phosphate = dihydroxy-acetone + D-glyceraldehyde-3-phosphate xylulose-monophosphate 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 1.2.1.59 D-glyceraldehyde-3-phosphate = 1,3-diphosphateglycerate Calvin 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.7 pyruvate + D-glyceraldehyde-3-phosphate = 1-deoxy-D-xylulose 5-phosphate + CO2 pyridoxal 5'-phosphate 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.7 pyruvate + D-glyceraldehyde-3-phosphate = 1-deoxy-D-xylulose 5-phosphate + CO2 thiamine 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.7 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate Calvin 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate (deoxy)ribose phosphate degradation 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 2.2.1.1 D-ribose-5-phosphate + D-xylulose-5-phosphate = D-sedoheptulose-7-phosphate + D-glyceraldehyde-3-phosphate glucose fermentation to lactate II 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 indole-3-glycerol-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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 1.2.1.9 D-glyceraldehyde-3-phosphate + NADP+ + H2O = 3-phosphoglycerate + 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxy-acetone-phosphate Calvin 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxy-acetone-phosphate sucrose degradation to ethanol and lactate (anaerobic) 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxy-acetone-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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxy-acetone-phosphate fructose degradation to pyruvate and lactate (anaerobic) 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 5.3.1.1 D-glyceraldehyde-3-phosphate = dihydroxy-acetone-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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate xylulose-monophosphate 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate Calvin 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate gluconeogenesis 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate sucrose degradation to ethanol and lactate (anaerobic) 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate fructose degradation to pyruvate and lactate (anaerobic) 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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-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 170.058 C3 H7 O6 P1 C(=O)[CH](O)COP(O)(O)=O LIGAND-CPD:C00661:*CAS:142-10-9 4.1.2.4 deoxyribose-5-phosphate = acetaldehyde + D-glyceraldehyde-3-phosphate (deoxy)ribose phosphate degradation deamido-NAD Deamino-NAD+*NaADN*deamido-NAD+*deamidonicotinamide adenine dinucleoetide*nicotinate adenine dinucleotide*NAAD 665.423 C21 H27 N6 O15 P2 C(O)(=O)c1(c[n+](ccc1)[CH]2(O[CH]([CH](O)[CH](O)2)COP(=O)(O)OP(O)(=O)OC[CH]3(O[CH]([CH](O)[CH]3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00857:*CAS:6450-77-7 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) deamido-NAD Deamino-NAD+*NaADN*deamido-NAD+*deamidonicotinamide adenine dinucleoetide*nicotinate adenine dinucleotide*NAAD 665.423 C21 H27 N6 O15 P2 C(O)(=O)c1(c[n+](ccc1)[CH]2(O[CH]([CH](O)[CH](O)2)COP(=O)(O)OP(O)(=O)OC[CH]3(O[CH]([CH](O)[CH]3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00857:*CAS:6450-77-7 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ NAD salvage pathway I deamido-NAD Deamino-NAD+*NaADN*deamido-NAD+*deamidonicotinamide adenine dinucleoetide*nicotinate adenine dinucleotide*NAAD 665.423 C21 H27 N6 O15 P2 C(O)(=O)c1(c[n+](ccc1)[CH]2(O[CH]([CH](O)[CH](O)2)COP(=O)(O)OP(O)(=O)OC[CH]3(O[CH]([CH](O)[CH]3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00857:*CAS:6450-77-7 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ pyridine nucleotide cycling (plants) deamido-NAD Deamino-NAD+*NaADN*deamido-NAD+*deamidonicotinamide adenine dinucleoetide*nicotinate adenine dinucleotide*NAAD 665.423 C21 H27 N6 O15 P2 C(O)(=O)c1(c[n+](ccc1)[CH]2(O[CH]([CH](O)[CH](O)2)COP(=O)(O)OP(O)(=O)OC[CH]3(O[CH]([CH](O)[CH]3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00857:*CAS:6450-77-7 2.7.7.18 ATP + nicotinate nucleotide = diphosphate + deamido-NAD NAD biosynthesis I (from aspartate) deamido-NAD Deamino-NAD+*NaADN*deamido-NAD+*deamidonicotinamide adenine dinucleoetide*nicotinate adenine dinucleotide*NAAD 665.423 C21 H27 N6 O15 P2 C(O)(=O)c1(c[n+](ccc1)[CH]2(O[CH]([CH](O)[CH](O)2)COP(=O)(O)OP(O)(=O)OC[CH]3(O[CH]([CH](O)[CH]3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00857:*CAS:6450-77-7 2.7.7.18 ATP + nicotinate nucleotide = diphosphate + deamido-NAD NAD salvage pathway I deamido-NAD Deamino-NAD+*NaADN*deamido-NAD+*deamidonicotinamide adenine dinucleoetide*nicotinate adenine dinucleotide*NAAD 665.423 C21 H27 N6 O15 P2 C(O)(=O)c1(c[n+](ccc1)[CH]2(O[CH]([CH](O)[CH](O)2)COP(=O)(O)OP(O)(=O)OC[CH]3(O[CH]([CH](O)[CH]3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00857:*CAS:6450-77-7 2.7.7.18 ATP + nicotinate nucleotide = diphosphate + deamido-NAD pyridine nucleotide cycling (plants) deamido-NAD Deamino-NAD+*NaADN*deamido-NAD+*deamidonicotinamide adenine dinucleoetide*nicotinate adenine dinucleotide*NAAD 665.423 C21 H27 N6 O15 P2 C(O)(=O)c1(c[n+](ccc1)[CH]2(O[CH]([CH](O)[CH](O)2)COP(=O)(O)OP(O)(=O)OC[CH]3(O[CH]([CH](O)[CH]3O)n4(c5(c(nc4)c(N)ncn5))))) LIGAND-CPD:C00857:*CAS:6450-77-7 6.3.1.5 ammonia + ATP + deamido-NAD = AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) homogentisate 2,5-dihydroxyphenylacetate 168.149 C8 H8 O4 C(O)(=O)Cc1(c(O)ccc(O)c1) homogentisate + solanyl pyrophosphate = 2-methyl-6-solanyl-1,4-benzoquinone + CO2 + diphosphate plastoquinone biosynthesis homogentisate 2,5-dihydroxyphenylacetate 168.149 C8 H8 O4 C(O)(=O)Cc1(c(O)ccc(O)c1) 1.13.11.27 p-hydroxyphenylpyruvate + O2 = CO2 + homogentisate vitamin E biosynthesis homogentisate 2,5-dihydroxyphenylacetate 168.149 C8 H8 O4 C(O)(=O)Cc1(c(O)ccc(O)c1) 1.13.11.27 p-hydroxyphenylpyruvate + O2 = CO2 + homogentisate tyrosine degradation I homogentisate 2,5-dihydroxyphenylacetate 168.149 C8 H8 O4 C(O)(=O)Cc1(c(O)ccc(O)c1) 1.13.11.27 p-hydroxyphenylpyruvate + O2 = CO2 + homogentisate plastoquinone biosynthesis homogentisate 2,5-dihydroxyphenylacetate 168.149 C8 H8 O4 C(O)(=O)Cc1(c(O)ccc(O)c1) homogentisate + phytyl-PP = 2-methyl-6-phytyl-1,4-benzoquinone + CO2 + diphosphate vitamin E biosynthesis porphobilinogen 226.232 C10 H13 N2 O4 c1(c(CCC(O)=O)c(CC(O)=O)c(n1)CN) LIGAND-CPD:C00931:*CAS:487-90-1 4.2.1.24 5-amino-levulinate = H2O + porphobilinogen tetrapyrrole biosynthesis I porphobilinogen 226.232 C10 H13 N2 O4 c1(c(CCC(O)=O)c(CC(O)=O)c(n1)CN) LIGAND-CPD:C00931:*CAS:487-90-1 2.5.1.61 H2O + porphobilinogen = ammonia + hydroxymethylbilane tetrapyrrole biosynthesis I L-aspartate-semialdehyde L-aspartic 4-semialdehyde*L-aspartate-4-semialdehyde*L-aspartate β-semialdehyde 117.104 C4 H7 N1 O3 [CH](=O)CC(N)C(O)=O LIGAND-CPD:C00441:*CAS:15106-57-7 1.2.1.11 NADP+ + L-aspartate-semialdehyde = 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 [CH](=O)CC(N)C(O)=O LIGAND-CPD:C00441:*CAS:15106-57-7 1.2.1.11 NADP+ + L-aspartate-semialdehyde = NADPH + L-aspartyl-4-phosphate lysine biosynthesis II L-aspartate-semialdehyde L-aspartic 4-semialdehyde*L-aspartate-4-semialdehyde*L-aspartate β-semialdehyde 117.104 C4 H7 N1 O3 [CH](=O)CC(N)C(O)=O LIGAND-CPD:C00441:*CAS:15106-57-7 1.2.1.11 NADP+ + L-aspartate-semialdehyde = NADPH + L-aspartyl-4-phosphate lysine biosynthesis I L-aspartate-semialdehyde L-aspartic 4-semialdehyde*L-aspartate-4-semialdehyde*L-aspartate β-semialdehyde 117.104 C4 H7 N1 O3 [CH](=O)CC(N)C(O)=O LIGAND-CPD:C00441:*CAS:15106-57-7 1.2.1.11 NADP+ + L-aspartate-semialdehyde = 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 [CH](=O)CC(N)C(O)=O LIGAND-CPD:C00441:*CAS:15106-57-7 4.2.1.52 pyruvate + L-aspartate-semialdehyde = H2O lysine biosynthesis VI L-aspartate-semialdehyde L-aspartic 4-semialdehyde*L-aspartate-4-semialdehyde*L-aspartate β-semialdehyde 117.104 C4 H7 N1 O3 [CH](=O)CC(N)C(O)=O LIGAND-CPD:C00441:*CAS:15106-57-7 4.2.1.52 pyruvate + L-aspartate-semialdehyde = H2O lysine biosynthesis II L-aspartate-semialdehyde L-aspartic 4-semialdehyde*L-aspartate-4-semialdehyde*L-aspartate β-semialdehyde 117.104 C4 H7 N1 O3 [CH](=O)CC(N)C(O)=O LIGAND-CPD:C00441:*CAS:15106-57-7 4.2.1.52 pyruvate + L-aspartate-semialdehyde = H2O lysine biosynthesis I L-aspartate-semialdehyde L-aspartic 4-semialdehyde*L-aspartate-4-semialdehyde*L-aspartate β-semialdehyde 117.104 C4 H7 N1 O3 [CH](=O)CC(N)C(O)=O LIGAND-CPD:C00441:*CAS:15106-57-7 1.1.1.3 homoserine = L-aspartate-semialdehyde + H+ homoserine biosynthesis 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP Calvin cycle 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP gluconeogenesis 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP sucrose degradation to ethanol and lactate (anaerobic) 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP glycolysis IV (plant cytosol) 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP fructose degradation to pyruvate and lactate (anaerobic) 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP glucose fermentation to lactate II 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP glycolysis I 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 1.1.1.95 3-phosphoglycerate + NAD+ = 3-phospho-hydroxypyruvate + NADH serine biosynthesis 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 2.7.1.31 glycerate + ATP = 3-phosphoglycerate + ADP glycolate and glyoxylate degradation I 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 2.7.1.31 glycerate + ATP = 3-phosphoglycerate + ADP allantoin degradation I 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 2.7.1.31 glycerate + ATP = 3-phosphoglycerate + ADP photorespiration 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 5.4.2.1 3-phosphoglycerate = 2-phosphoglycerate gluconeogenesis 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 5.4.2.1 3-phosphoglycerate = 2-phosphoglycerate sucrose degradation to ethanol and lactate (anaerobic) 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 5.4.2.1 3-phosphoglycerate = 2-phosphoglycerate glycolysis IV (plant cytosol) 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 5.4.2.1 3-phosphoglycerate = 2-phosphoglycerate fructose degradation to pyruvate and lactate (anaerobic) 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 5.4.2.1 3-phosphoglycerate = 2-phosphoglycerate glucose fermentation to lactate II 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 5.4.2.1 3-phosphoglycerate = 2-phosphoglycerate glycolysis I 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 4.1.1.- O2 = 2-phosphoglycolate + 3-phosphoglycerate + H+ photorespiration 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 4.1.1.39 CO2 + H2O = 3-phosphoglycerate + H+ Calvin cycle 3-phosphoglycerate 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 186.058 C3 H7 O7 P1 C(C(O)C(O)=O)OP(O)(O)=O LIGAND-CPD:C00197:*CAS:820-11-1 1.2.1.9 D-glyceraldehyde-3-phosphate + NADP+ + H2O = 3-phosphoglycerate + NADPH glycolysis IV (plant cytosol) benzyladenine 225.252 C12 H11 N5 c2(ncnc1(c(N=CN1)2))(NCc3(ccccc3)) 2.4.1.- benzyladenine + UDP-D-glucose = benzyladenine-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis benzyladenine 225.252 C12 H11 N5 c2(ncnc1(c(N=CN1)2))(NCc3(ccccc3)) 2.4.1.- benzyladenine + UDP-D-glucose = benzyladenine-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis α-D-glucose glucose*D-glucose*α-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O1)CO)(O) 3.2.1.26 sucrose + H2O = α-D-glucose + fructose sucrose degradation III α-D-glucose glucose*D-glucose*α-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O1)CO)(O) 2.7.1.1 α-D-glucose + ATP = α-D-glucose 6-phosphate + ADP sucrose degradation III α-D-glucose glucose*D-glucose*α-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O1)CO)(O) 2.7.1.1 α-D-glucose + ATP = α-D-glucose 6-phosphate + ADP starch degradation α-D-glucose glucose*D-glucose*α-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O1)CO)(O) 2.4.1.25 starch degradation α-D-glucose glucose*D-glucose*α-glucose*6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 180.157 C6 H12 O6 C1(C(O)C(O)C(O)C(O1)CO)(O) 3.2.1.20 α-maltose + H2O = α-D-glucose starch degradation isowighteone 3'-prenyl-5,7,4'-trihydroxyisoflavone 338.359 C20 H18 O5 CC(C)=CCc1(cc(ccc1O)C2(C(=O)c3(c(OC=2)cc(O)cc(O)3))) 2.5.1.1 genistein + dimethylallyl-PP = isowighteone + diphosphate wighteone and luteone biosynthesis gallate Gallic acid*3,4,5-Trihydroxybenzoic acid*3,4,5-Trihydroxybenzoate*Pyrogallol-5-carboxylic acid 170.121 C7 H6 O5 C(O)(=O)c1(cc(O)c(O)c(O)c1) LIGAND-CPD:c01424:*UM-BBD-CPD:c0006:*CAS:149-91-7 4.1.1.59 gallate = CO2 + pyrogallol gallate degradation III (anaerobic) UDP-N-acetyl-D-galactosamine UDP-N-acetylgalactosamine*uridine diphosphate N-acetylgalactosamine 607.358 C17 H27 N3 O17 P2 CC(=O)NC1(C(OC(CO)C(O)C1O)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c(=O)[nH]c(=O)cc3))) LIGAND-CPD:C00203:*CAS:7277-98-7 5.1.3.7 UDP-N-acetyl-D-glucosamine = UDP-N-acetyl-D-galactosamine UDP-N-acetylgalactosamine biosynthesis fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 1.3.5.- fumarate + menaquinol + H+ = succinate + menaquinone-8 mixed acid fermentation fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 1.3.5.- fumarate + menaquinol + H+ = succinate + menaquinone-8 respiration (anaerobic) fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 4.2.1.2 malate = fumarate + H2O mixed acid fermentation fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 4.2.1.2 malate = fumarate + H2O TCA cycle variation I fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 4.2.1.2 malate = fumarate + H2O reductive TCA cycle I fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 4.2.1.2 malate = fumarate + H2O respiration (anaerobic) fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 4.2.1.2 malate = fumarate + H2O TCA cycle fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 4.3.2.2 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole = fumarate + AICAR purine nucleotides de novo biosynthesis II fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 4.3.2.2 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole = fumarate + AICAR purine nucleotides de novo biosynthesis I fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 4.3.1.1 L-aspartate = ammonia + fumarate glutamine degradation III fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 1.3.99.1 succinate = fumarate TCA cycle variation I fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 1.3.99.1 succinate = fumarate reductive TCA cycle I fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 4.3.2.2 adenylo-succinate = fumarate + AMP salvage pathways of purine nucleosides fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O 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 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 4.3.2.2 adenylo-succinate = fumarate + AMP purine nucleotides de novo biosynthesis I fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 3.7.1.2 H2O + 4-fumaryl-acetoacetate = fumarate + acetoacetate tyrosine degradation I fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 4.3.2.1 canavaninosuccinate = canavanine + fumarate canavanine biosynthesis fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 4.3.2.1 L-arginino-succinate = L-arginine + fumarate urea cycle fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O 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 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O 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 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 4.3.2.1 L-arginino-succinate = L-arginine + fumarate arginine biosynthesis IV fumarate fum*fumaric acid 116.073 C4 H4 O4 C(O)(=O)C=CC(O)=O LIGAND-CPD:C00122:*CAS:110-17-8 4.3.2.1 L-arginino-succinate = L-arginine + fumarate arginine biosynthesis I glutaryl-CoA glutaryl-coenzyme A 881.635 C26 H42 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(O)=O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCCC(O)=O) α-ketoadipate + NAD+ + coenzyme A = CO2 + NADH + glutaryl-CoA lysine degradation II glutaryl-CoA glutaryl-coenzyme A 881.635 C26 H42 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(O)=O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCCC(O)=O) α-ketoadipate + NAD+ + coenzyme A = CO2 + NADH + glutaryl-CoA tryptophan degradation III (eukaryotic) glutaryl-CoA glutaryl-coenzyme A 881.635 C26 H42 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(O)(O)=O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCCC(O)=O) glutaryl-CoA + FAD = glutaconyl-CoA + FADH2 glutaryl-CoA degradation inositol phosphate 2.4.1.- mannosyl-inositol-phosphorylceramide + inositol phosphate = mannosyl-diinositol-phosphorylceramide sphingolipid metabolism inositol phosphate 2.4.1.- inositol phosphate = inositol-P-ceramide sphingolipid metabolism 2,3-trans-catechin Cianidanol*catechin 290.272 C15 H14 O6 c3(c2(OC(c1(cc(O)c(O)cc1))C(O)Cc2c(O)cc(O)3)) 1.17.1.3 leucocyanidin + NADPH = 2,3-trans-catechin + NADP+ + H2O proanthocyanidin biosynthesis from flavanols 2,3-trans-catechin Cianidanol*catechin 290.272 C15 H14 O6 c3(c2(OC(c1(cc(O)c(O)cc1))C(O)Cc2c(O)cc(O)3)) afzelechin + 2,3-trans-catechin = 2,3-cis-proanthocyanidin proanthocyanidin biosynthesis from flavanols 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 430.713 C29 H50 O2 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(CO)(C)C(O)CC4)(C)))(C)) 1.14.13.72 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol + O2 = 4α-formyl-4β-methyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 430.713 C29 H50 O2 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(CO)(C)C(O)CC4)(C)))(C)) 1.14.13.72 4,4-dimethyl-5α-cholesta-8-en-3-β-ol + O2 = 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) phytate phytic acid*myo-inositol hexakisphosphate*1D-myo-Inositol 1,2,3,4,5,6-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 653.989 C6 H12 O24 P6 C1(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)(OP(O)([O-])=O) LIGAND-CPD:C01204: 2.7.1.- D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = phytate + ADP lipid-independent phytate biosynthesis D-glucono-δ-lactone-6-phosphate 6-phosphogluconolactone*D-6-phosphoglucono-δ-lactone*D-6-P-glucono-δ-lactone*D-glucono-1,5-lactone-6-phosphate*6-phospho-D-glucono-1,5-lactone*D-6-phospho-glucono-δ-lactone 258.121 C6 H11 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(=O) LIGAND-CPD:C01236:*CAS:2641-81-8 3.1.1.31 D-glucono-δ-lactone-6-phosphate + H2O = 6-phospho-D-gluconate pentose phosphate pathway (oxidative branch) D-glucono-δ-lactone-6-phosphate 6-phosphogluconolactone*D-6-phosphoglucono-δ-lactone*D-6-P-glucono-δ-lactone*D-glucono-1,5-lactone-6-phosphate*6-phospho-D-glucono-1,5-lactone*D-6-phospho-glucono-δ-lactone 258.121 C6 H11 O9 P1 C1(OC(COP(O)(=O)O)C(O)C(O)C(O)1)(=O) LIGAND-CPD:C01236:*CAS:2641-81-8 1.1.1.49 β-D-glucose-6-phosphate + NADP+ = D-glucono-δ-lactone-6-phosphate + NADPH + H+ pentose phosphate pathway (oxidative branch) (E)-cinnamoyl-CoA 897.68 C30 H42 N7 O17 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc1(ccccc1))COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(O)=O)n3(c4(c(nc3)c(N)ncn4))) 2.3.1.- malonyl-CoA + (E)-cinnamoyl-CoA = pinocembrin chalcone + coenzyme A + CO2 pinobanksin biosynthesis (E)-cinnamoyl-CoA 897.68 C30 H42 N7 O17 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc1(ccccc1))COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(O)=O)n3(c4(c(nc3)c(N)ncn4))) 6.2.1.- trans-cinnamate + coenzyme A = (E)-cinnamoyl-CoA + H2O salicylate biosynthesis (E)-cinnamoyl-CoA 897.68 C30 H42 N7 O17 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc1(ccccc1))COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(O)=O)n3(c4(c(nc3)c(N)ncn4))) (E)-cinnamoyl-CoA + H2O = hydroxycinnamoyl-CoA salicylate biosynthesis α-carotene 536.882 C40 H56 CC1(C(=C(C)CCC1)C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)(C)CCC=C(C)2))(C) 1.14.99.- α-carotene + NADPH + O2 = zeinoxanthin + NADP+ + H2O carotenoid biosynthesis α-carotene 536.882 C40 H56 CC1(C(=C(C)CCC1)C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)(C)CCC=C(C)2))(C) 5.5.1.- δ-carotene = α-carotene carotenoid biosynthesis 3-mercaptopyruvate mercaptopyruvate*3-mercaptopyruvic acid*β-thiopyruvate*β-mercaptopyruvate 120.123 C3 H4 O3 S1 C(=O)(O)C(=O)CS LIGAND-CPD:C00957:*CAS:2464-23-5 2.6.1.3 α-ketoglutarate + L-cysteine = L-glutamate + 3-mercaptopyruvate L-cysteine degradation III 3-mercaptopyruvate mercaptopyruvate*3-mercaptopyruvic acid*β-thiopyruvate*β-mercaptopyruvate 120.123 C3 H4 O3 S1 C(=O)(O)C(=O)CS LIGAND-CPD:C00957:*CAS:2464-23-5 2.8.1.2 hydrogen cyanide + 3-mercaptopyruvate = pyruvate + thiocyanate L-cysteine degradation III 4-(phosphonooxy)-threonine 4-phosphonooxy-L-threonine*4-phospho-hydroxy-threonine*4-phospho-hydroxy-L-threonine*O-phospho-4-hydroxy-L-threonine*phospho-hydroxy-threonine*4-(Phosphonooxy)-L-threonine 214.091 C4 H9 N1 O7 P1 C(=O)([O-])C(N)C(O)COP(=O)(O)O PUBCHEM:440901:*LIGAND-CPD:C06055: 1.1.1.262 4-(phosphonooxy)-threonine + NAD+ = NADH + (2S)-2-amino-3-oxo-4-phosphonooxybutanoate pyridoxal 5'-phosphate biosynthesis 4-(phosphonooxy)-threonine 4-phosphonooxy-L-threonine*4-phospho-hydroxy-threonine*4-phospho-hydroxy-L-threonine*O-phospho-4-hydroxy-L-threonine*phospho-hydroxy-threonine*4-(Phosphonooxy)-L-threonine 214.091 C4 H9 N1 O7 P1 C(=O)([O-])C(N)C(O)COP(=O)(O)O PUBCHEM:440901:*LIGAND-CPD:C06055: 2.6.1.52 2-oxo-3-hydroxy-4-phosphobutanoate + L-glutamate = 4-(phosphonooxy)-threonine + α-ketoglutarate pyridoxal 5'-phosphate biosynthesis kinetin-7-N-glucoside 377.356 C16 H19 N5 O6 c2(c1(N(C=Nc1ncn2)C3(OC(CO)C(O)C(O)C(O)3)))(NCc4(occc4)) 2.4.1.- kinetin + UDP-D-glucose = kinetin-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis 5-methyltetrahydropteroyltri-L-glutamate 701.692 C30 H39 N9 O11 C(C1(N(C)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(=O)NC(C(O)=O)CCC(=O)NC(C(O)=O)CCC=O) LIGAND-CPD:C04489: 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine S-adenosylmethionine biosynthesis 5-methyltetrahydropteroyltri-L-glutamate 701.692 C30 H39 N9 O11 C(C1(N(C)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(=O)NC(C(O)=O)CCC(=O)NC(C(O)=O)CCC=O) LIGAND-CPD:C04489: 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine methionine biosynthesis II 5-methyltetrahydropteroyltri-L-glutamate 701.692 C30 H39 N9 O11 C(C1(N(C)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(=O)NC(C(O)=O)CCC(=O)NC(C(O)=O)CCC=O) LIGAND-CPD:C04489: 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine methionine biosynthesis I 5-methyltetrahydropteroyltri-L-glutamate 701.692 C30 H39 N9 O11 C(C1(N(C)c2(c(NC1)nc(N)[nH]c2=O)))Nc3(ccc(cc3)C(=O)NC(C(O)=O)CCC(=O)NC(C(O)=O)CCC(=O)NC(C(O)=O)CCC=O) LIGAND-CPD:C04489: 2.1.1.14 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine S-adenosyl-L-methionine cycle dethiobiotin Desthiobiotin*DTB 214.264 C10 H18 N2 O3 C(=O)(O)CCCCCC1(C(C)NC(N1)=O) LIGAND-CPD:C01909:*CAS:533-48-2 2.8.1.6 dethiobiotin + sulfur donor = 9-mercaptodethiobiotin biotin biosynthesis II dethiobiotin Desthiobiotin*DTB 214.264 C10 H18 N2 O3 C(=O)(O)CCCCCC1(C(C)NC(N1)=O) LIGAND-CPD:C01909:*CAS:533-48-2 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = dethiobiotin + ADP biotin biosynthesis II dethiobiotin Desthiobiotin*DTB 214.264 C10 H18 N2 O3 C(=O)(O)CCCCCC1(C(C)NC(N1)=O) LIGAND-CPD:C01909:*CAS:533-48-2 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = dethiobiotin + ADP biotin biosynthesis I dethiobiotin Desthiobiotin*DTB 214.264 C10 H18 N2 O3 C(=O)(O)CCCCCC1(C(C)NC(N1)=O) LIGAND-CPD:C01909:*CAS:533-48-2 2.8.1.6 dethiobiotin + S-adenosyl-L-methionine + sulfur donor = biotin + 5'-deoxyadenosine + L-methionine biotin biosynthesis I Δ24-25-sitosterol 412.698 C29 H48 O1 CC(C)=C(CC)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) isofucosterol = Δ24-25-sitosterol sterol biosynthesis Δ24-25-sitosterol 412.698 C29 H48 O1 CC(C)=C(CC)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) Δ24-25-sitosterol = sitosterol sterol biosynthesis dADP deoxyadenosine-diphosphate*2'-deoxyadenosine-5'-diphosphate 411.204 C10 H15 N5 O9 P2 C(OP(O)(=O)OP(O)(=O)O)C1(OC(CC(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00206:*CAS:2793-06-8 1.17.4.1 dADP + H2O = ADP purine nucleotides de novo biosynthesis I dADP deoxyadenosine-diphosphate*2'-deoxyadenosine-5'-diphosphate 411.204 C10 H15 N5 O9 P2 C(OP(O)(=O)OP(O)(=O)O)C1(OC(CC(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00206:*CAS:2793-06-8 2.7.4.6 dADP + ATP = dATP + ADP purine nucleotides de novo biosynthesis I dADP deoxyadenosine-diphosphate*2'-deoxyadenosine-5'-diphosphate 411.204 C10 H15 N5 O9 P2 C(OP(O)(=O)OP(O)(=O)O)C1(OC(CC(O)1)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00206:*CAS:2793-06-8 ADP = dADP + H2O purine nucleotides de novo biosynthesis I phosphoribosyl-formamido-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 366.224 C10 H15 N4 O9 P1 c1(n(cnc(C(N)=O)1)[CH]2(O[CH]([CH](O)[CH]2O)COP(=O)(O)O))(NC=O) LIGAND-CPD:C04734: 2.1.2.3 N10-formyl-THF + AICAR = tetrahydrofolate + phosphoribosyl-formamido-carboxamide purine nucleotides de novo biosynthesis II phosphoribosyl-formamido-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 366.224 C10 H15 N4 O9 P1 c1(n(cnc(C(N)=O)1)[CH]2(O[CH]([CH](O)[CH]2O)COP(=O)(O)O))(NC=O) LIGAND-CPD:C04734: 2.1.2.3 N10-formyl-THF + AICAR = tetrahydrofolate + phosphoribosyl-formamido-carboxamide purine nucleotides de novo biosynthesis I phosphoribosyl-formamido-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 366.224 C10 H15 N4 O9 P1 c1(n(cnc(C(N)=O)1)[CH]2(O[CH]([CH](O)[CH]2O)COP(=O)(O)O))(NC=O) LIGAND-CPD:C04734: 3.5.4.10 inosine-5'-phosphate + H2O = phosphoribosyl-formamido-carboxamide purine nucleotides de novo biosynthesis II phosphoribosyl-formamido-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 366.224 C10 H15 N4 O9 P1 c1(n(cnc(C(N)=O)1)[CH]2(O[CH]([CH](O)[CH]2O)COP(=O)(O)O))(NC=O) LIGAND-CPD:C04734: 3.5.4.10 inosine-5'-phosphate + H2O = phosphoribosyl-formamido-carboxamide purine nucleotides de novo biosynthesis I β-tocopherol 416.686 C28 H48 O2 CC(C)CCCC(C)CCCC(C)CCCC1(C)(OC2(C(CC1)=C(C)C(O)=CC=2C)) 2.1.1.95 δ-tocopherol + S-adenosyl-L-methionine = β-tocopherol + S-adenosyl-L-homocysteine vitamin E biosynthesis erythronate-4-phosphate 4-Phospho-D-erythronate*4-phosphoerythronate*erythronate-4P*D-erythronate-4-phosphate*D-erythronate-4P 215.076 C4 H8 O8 P1 C([O-])(=O)C(O)C(O)COP(O)(O)=O LIGAND-CPD:C03393: 1.2.1.72 D-erythrose-4-phosphate + NAD+ + H2O = erythronate-4-phosphate + NADH + H+ pyridoxal 5'-phosphate biosynthesis erythronate-4-phosphate 4-Phospho-D-erythronate*4-phosphoerythronate*erythronate-4P*D-erythronate-4-phosphate*D-erythronate-4P 215.076 C4 H8 O8 P1 C([O-])(=O)C(O)C(O)COP(O)(O)=O LIGAND-CPD:C03393: 1.1.1.290 erythronate-4-phosphate + NAD+ = 2-oxo-3-hydroxy-4-phosphobutanoate + NADH + H+ pyridoxal 5'-phosphate 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 180.203 C10 H12 O3 C(O)C=Cc1(cc(OC)c(O)cc1) CAS:458-35-5 1.1.1.195 coniferyl aldehyde + NADPH = coniferyl alcohol + NADP+ phenylpropanoid biosynthesis trans-β-D-Glucosyl-2-hydroxycinnamate β-D-Glucosyl-2-coumarate 326.302 C15 H18 O8 C1(C(O)C(O)C(O)C(O1)CO)Oc2(c(C=CC(=O)O)cccc2) 5.2.1.- trans-β-D-Glucosyl-2-hydroxycinnamate = coumarinic acid-β-D-glucoside coumarin biosynthesis (via 2-coumarate) trans-β-D-Glucosyl-2-hydroxycinnamate β-D-Glucosyl-2-coumarate 326.302 C15 H18 O8 C1(C(O)C(O)C(O)C(O1)CO)Oc2(c(C=CC(=O)O)cccc2) 2.4.1.114 2-coumarate + UDP-D-glucose = trans-β-D-Glucosyl-2-hydroxycinnamate + UDP coumarin biosynthesis (via 2-coumarate) oxocinnamoyl-CoA 913.679 C30 H42 N7 O18 P3 S1 CC(C(O)C(=O)NCCC(=O)NCCSC(=O)CC(=O)c1(ccccc1))(C)COP(O)(=O)OP(O)(=O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(=O)O)n3(c4(c(nc3)c(N)ncn4))) oxocinnamoyl-CoA + coenzyme A = benzoyl-CoA + acetyl-CoA salicylate biosynthesis oxocinnamoyl-CoA 913.679 C30 H42 N7 O18 P3 S1 CC(C(O)C(=O)NCCC(=O)NCCSC(=O)CC(=O)c1(ccccc1))(C)COP(O)(=O)OP(O)(=O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(=O)O)n3(c4(c(nc3)c(N)ncn4))) hydroxycinnamoyl-CoA + NADP+ = oxocinnamoyl-CoA + NADPH salicylate biosynthesis 4α-methyl-cholesta-8-enol 400.687 C28 H48 O1 CC(C)CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C(CC3)C(C)C(O)CC4)(C)))) 1.1.1.270 4α-methyl-5α-cholesta-8-en-3-one + NADPH = 4α-methyl-cholesta-8-enol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 4α-methyl-cholesta-8-enol 400.687 C28 H48 O1 CC(C)CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C(CC3)C(C)C(O)CC4)(C)))) 1.14.13.72 4α-methyl-cholesta-8-enol + O2 = 4α-hydroxymethyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 18:3-18:2-MGDG 1-18:3-2-18:2-monogalactosyldiacylglycerol 793.089 C45 H76 O11 C(OC1(C(O)C(O)C(OO)C(O1)CO))C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:3-18:2-MGDG = 18:3-18:3-MGDG glycolipid desaturation 18:3-18:2-MGDG 1-18:3-2-18:2-monogalactosyldiacylglycerol 793.089 C45 H76 O11 C(OC1(C(O)C(O)C(OO)C(O1)CO))C(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:2-18:2-MGDG = 18:3-18:2-MGDG glycolipid desaturation 3-methyl-4-cis-hydroxy-2-butenal 100.117 C5 H8 O2 C(=O)C=C(C)CO 1.5.99.12 cis-zeatin + H2O + FAD = 3-methyl-4-cis-hydroxy-2-butenal + adenine + FADH2 cytokinins degradation β-myrcene myrcene 136.236 C10 H16 C=CC(=C)CCC=C(C)C 4.2.3.15 geranyl-PP = β-myrcene + diphosphate oleoresin monoterpene volatiles biosynthesis β-myrcene myrcene 136.236 C10 H16 C=CC(=C)CCC=C(C)C 4.2.3.15 geranyl-PP = β-myrcene + diphosphate monoterpene biosynthesis acetol hydroxyacetone*acetylmethanol*1-hydroxyacetone 74.079 C3 H6 O2 CC(=O)CO methylglyoxal + NADPH = acetol + NADP+ acetone degradation (to methylglyoxal) acetol hydroxyacetone*acetylmethanol*1-hydroxyacetone 74.079 C3 H6 O2 CC(=O)CO 1.14.14.1 acetone + NADPH + O2 = acetol + NADP+ + H2O acetone degradation (to methylglyoxal) UDP-D-galacto-1,4-furanose UDP-galactofuranose 566.305 C15 H24 N2 O17 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(O[CH](C(O)C3O)C(O)CO))) CAS:638-23-3:*LIGAND-CPD:C03733: 5.4.99.9 UDP-galactose = UDP-D-galacto-1,4-furanose O-antigen biosynthesis citrate citr*cit*citric acid*2-hydroxy-1,2,3-propanetricarboxylic acid 192.125 C6 H8 O7 C(=O)(O)CC(C(O)=O)(O)CC(O)=O LIGAND-CPD:C00158:*CAS:77-92-9 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = citrate + coenzyme A TCA cycle variation I citrate citr*cit*citric acid*2-hydroxy-1,2,3-propanetricarboxylic acid 192.125 C6 H8 O7 C(=O)(O)CC(C(O)=O)(O)CC(O)=O LIGAND-CPD:C00158:*CAS:77-92-9 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = citrate + coenzyme A respiration (anaerobic) citrate citr*cit*citric acid*2-hydroxy-1,2,3-propanetricarboxylic acid 192.125 C6 H8 O7 C(=O)(O)CC(C(O)=O)(O)CC(O)=O LIGAND-CPD:C00158:*CAS:77-92-9 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = citrate + coenzyme A TCA cycle citrate citr*cit*citric acid*2-hydroxy-1,2,3-propanetricarboxylic acid 192.125 C6 H8 O7 C(=O)(O)CC(C(O)=O)(O)CC(O)=O LIGAND-CPD:C00158:*CAS:77-92-9 4.2.1.3 citrate = cis-aconitate + H2O TCA cycle variation I citrate citr*cit*citric acid*2-hydroxy-1,2,3-propanetricarboxylic acid 192.125 C6 H8 O7 C(=O)(O)CC(C(O)=O)(O)CC(O)=O LIGAND-CPD:C00158:*CAS:77-92-9 4.2.1.3 citrate = cis-aconitate + H2O reductive TCA cycle I citrate citr*cit*citric acid*2-hydroxy-1,2,3-propanetricarboxylic acid 192.125 C6 H8 O7 C(=O)(O)CC(C(O)=O)(O)CC(O)=O LIGAND-CPD:C00158:*CAS:77-92-9 4.2.1.3 citrate = cis-aconitate + H2O respiration (anaerobic) citrate citr*cit*citric acid*2-hydroxy-1,2,3-propanetricarboxylic acid 192.125 C6 H8 O7 C(=O)(O)CC(C(O)=O)(O)CC(O)=O LIGAND-CPD:C00158:*CAS:77-92-9 4.2.1.3 citrate = cis-aconitate + H2O TCA cycle diprenylphlorisobutyrophenone deoxycohumulone 332.439 C20 H28 O4 CC(C)C(=O)c1(c(O)c(CC=C(C)C)c(O)c(c(O)1)CC=C(C)C) 2.5.1.- 4-prenylphlorisobutyrophenone + dimethylallyl-PP = diprenylphlorisobutyrophenone + diphosphate cohumulone biosynthesis diprenylphlorisobutyrophenone deoxycohumulone 332.439 C20 H28 O4 CC(C)C(=O)c1(c(O)c(CC=C(C)C)c(O)c(c(O)1)CC=C(C)C) diprenylphlorisobutyrophenone + O2 = cohumulone + H2O cohumulone biosynthesis isopentenyladenosine-5'-diphosphate iPDP*isopentenyladenosine riboside-5'-diphosphate*iPRDP 495.322 C15 H23 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(ncn3)NCC=C(C)C))) isopentenyladenosine-5'-diphosphate + H2O = isopentenyladenosine-5'-monophosphate trans-zeatin biosynthesis isopentenyladenosine-5'-diphosphate iPDP*isopentenyladenosine riboside-5'-diphosphate*iPRDP 495.322 C15 H23 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(ncn3)NCC=C(C)C))) isopentenyladenosine-5'-diphosphate + NADPH + H2O = trans-zeatin riboside diphosphate + NADP+ trans-zeatin biosynthesis isopentenyladenosine-5'-diphosphate iPDP*isopentenyladenosine riboside-5'-diphosphate*iPRDP 495.322 C15 H23 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(ncn3)NCC=C(C)C))) 2.5.1.- dimethylallyl-PP + ADP = isopentenyladenosine-5'-diphosphate + diphosphate trans-zeatin biosynthesis isopentenyladenosine-5'-diphosphate iPDP*isopentenyladenosine riboside-5'-diphosphate*iPRDP 495.322 C15 H23 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(ncn3)NCC=C(C)C))) isopentenyladenosine-5'-triphosphate + H2O = isopentenyladenosine-5'-diphosphate trans-zeatin biosynthesis agmatine 130.192 C5 H14 N4 C(NC(N)=N)CCCN LIGAND-CPD:C00179:*CAS:306-60-5 4.1.1.19 L-arginine = CO2 + agmatine arginine degradation III (arginine decarboxylase/agmatinase pathway) agmatine 130.192 C5 H14 N4 C(NC(N)=N)CCCN LIGAND-CPD:C00179:*CAS:306-60-5 4.1.1.19 L-arginine = CO2 + agmatine putrescine biosynthesis I agmatine 130.192 C5 H14 N4 C(NC(N)=N)CCCN LIGAND-CPD:C00179:*CAS:306-60-5 4.1.1.19 L-arginine = CO2 + agmatine putrescine biosynthesis II agmatine 130.192 C5 H14 N4 C(NC(N)=N)CCCN LIGAND-CPD:C00179:*CAS:306-60-5 4.1.1.19 L-arginine = CO2 + agmatine arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) agmatine 130.192 C5 H14 N4 C(NC(N)=N)CCCN LIGAND-CPD:C00179:*CAS:306-60-5 3.5.3.11 H2O + agmatine = urea + putrescine arginine degradation III (arginine decarboxylase/agmatinase pathway) agmatine 130.192 C5 H14 N4 C(NC(N)=N)CCCN LIGAND-CPD:C00179:*CAS:306-60-5 3.5.3.11 H2O + agmatine = urea + putrescine putrescine biosynthesis I agmatine 130.192 C5 H14 N4 C(NC(N)=N)CCCN LIGAND-CPD:C00179:*CAS:306-60-5 3.5.3.12 H2O + agmatine = ammonia + N-carbamoylputrescine putrescine biosynthesis II agmatine 130.192 C5 H14 N4 C(NC(N)=N)CCCN LIGAND-CPD:C00179:*CAS:306-60-5 3.5.3.12 H2O + agmatine = ammonia + N-carbamoylputrescine arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) glycolate hydroxyacetic acid*glycolic acid 76.052 C2 H4 O3 C(=O)(O)CO LIGAND-CPD:C00160:*CAS:79-14-1 1.2.1.21 H2O + NAD+ + glycolaldehyde = NADH + glycolate ethylene glycol degradation glycolate hydroxyacetic acid*glycolic acid 76.052 C2 H4 O3 C(=O)(O)CO LIGAND-CPD:C00160:*CAS:79-14-1 1.1.3.15 glycolate + O2 = glyoxylate + H2O2 photorespiration glycolate hydroxyacetic acid*glycolic acid 76.052 C2 H4 O3 C(=O)(O)CO LIGAND-CPD:C00160:*CAS:79-14-1 1.1.99.14 glycolate = glyoxylate glycolate and glyoxylate degradation I glycolate hydroxyacetic acid*glycolic acid 76.052 C2 H4 O3 C(=O)(O)CO LIGAND-CPD:C00160:*CAS:79-14-1 3.1.3.18 H2O + 2-phosphoglycolate = glycolate photorespiration 2-keto-isovalerate 2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-oxoisovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 116.116 C5 H8 O3 CC(C)C(=O)C(=O)O LIGAND-CPD:C00141:*CAS:759-05-7 4.2.1.9 2,3-dihydroxy-isovalerate = 2-keto-isovalerate + H2O valine biosynthesis 2-keto-isovalerate 2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-oxoisovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 116.116 C5 H8 O3 CC(C)C(=O)C(=O)O LIGAND-CPD:C00141:*CAS:759-05-7 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate valine degradation I 2-keto-isovalerate 2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-oxoisovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 116.116 C5 H8 O3 CC(C)C(=O)C(=O)O LIGAND-CPD:C00141:*CAS:759-05-7 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate valine biosynthesis 2-keto-isovalerate 2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-oxoisovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 116.116 C5 H8 O3 CC(C)C(=O)C(=O)O LIGAND-CPD:C00141:*CAS:759-05-7 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate pantothenate biosynthesis I 2-keto-isovalerate 2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-oxoisovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 116.116 C5 H8 O3 CC(C)C(=O)C(=O)O LIGAND-CPD:C00141:*CAS:759-05-7 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate valine degradation II 2-keto-isovalerate 2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-oxoisovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 116.116 C5 H8 O3 CC(C)C(=O)C(=O)O LIGAND-CPD:C00141:*CAS:759-05-7 2.6.1.42 L-valine + α-ketoglutarate = L-glutamate + 2-keto-isovalerate pantothenate biosynthesis II 2-keto-isovalerate 2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-oxoisovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 116.116 C5 H8 O3 CC(C)C(=O)C(=O)O LIGAND-CPD:C00141:*CAS:759-05-7 1.2.1.25 NAD+ + coenzyme A + 2-keto-isovalerate = NADH + CO2 + isobutyryl-CoA valine degradation I 2-keto-isovalerate 2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-oxoisovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 116.116 C5 H8 O3 CC(C)C(=O)C(=O)O LIGAND-CPD:C00141:*CAS:759-05-7 4.1.1.1 2-keto-isovalerate = isobutanal + CO2 valine degradation II 2-keto-isovalerate 2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-oxoisovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 116.116 C5 H8 O3 CC(C)C(=O)C(=O)O LIGAND-CPD:C00141:*CAS:759-05-7 2.3.3.13 2-keto-isovalerate + acetyl-CoA + H2O = 2-isopropylmalate + coenzyme A leucine biosynthesis 2-keto-isovalerate 2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-oxoisovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 116.116 C5 H8 O3 CC(C)C(=O)C(=O)O LIGAND-CPD:C00141:*CAS:759-05-7 2.1.2.11 5,10-methylene-THF + 2-keto-isovalerate + H2O = tetrahydrofolate + 2-dehydropantoate pantothenate biosynthesis I 2-keto-isovalerate 2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-oxoisovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 116.116 C5 H8 O3 CC(C)C(=O)C(=O)O LIGAND-CPD:C00141:*CAS:759-05-7 2.1.2.11 5,10-methylene-THF + 2-keto-isovalerate + H2O = tetrahydrofolate + 2-dehydropantoate pantothenate biosynthesis II 2-keto-isovalerate 2-oxo-3-methylbutanoate*3-methyl-2-oxobutanoate*α-keto-isovaleric acid*α-ketoisopentanoic acid*α-keto-isovalerate*α-oxoisovalerate*α-ketovaline*2-oxoisovalerate*2-ketovaline*α-keto-valine*2-oxoisopentanoate*2-keto-3-methylbutyric acid 116.116 C5 H8 O3 CC(C)C(=O)C(=O)O LIGAND-CPD:C00141:*CAS:759-05-7 1.2.4.4 2-keto-isovalerate = CO2 branched-chain α-keto acid dehydrogenase complex guanosine 3'-diphosphate 5'-triphosphate guanosine pentaphosphate*pppGpp*guanosine 5'-triphosphate,3'-diphosphate 683.142 C10 H18 N5 O20 P5 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1OP(=O)(O)OP(O)(O)=O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C04494: 2.7.6.5 GTP + ATP = guanosine 3'-diphosphate 5'-triphosphate + AMP ppGpp biosynthesis guanosine 3'-diphosphate 5'-triphosphate guanosine pentaphosphate*pppGpp*guanosine 5'-triphosphate,3'-diphosphate 683.142 C10 H18 N5 O20 P5 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1OP(=O)(O)OP(O)(O)=O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C04494: 3.6.1.40 H2O + guanosine 3'-diphosphate 5'-triphosphate = guanosine 5'-diphosphate,3'-diphosphate ppGpp biosynthesis 5-dehydro episterol 396.655 C28 H44 O1 CC(C)C(=C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC=3)CC(O)CC4)(C)))) 1.3.3.- episterol = 5-dehydro episterol sterol biosynthesis 5-dehydro episterol 396.655 C28 H44 O1 CC(C)C(=C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC=3)CC(O)CC4)(C)))) 1.3.1.21 5-dehydro episterol + NADPH = 24-methylenecholesterol + NADP+ sterol biosynthesis desmosterol desmosterol*24-dehydrocholesterol*Δ5,24-cholestadien-3-β-ol*desmesterol*24-dehydrocholesterol 384.644 C27 H44 O1 CC(C)=CCCC(C)[CH]1(C2(C)([CH](CC1)[CH]3([CH](CC2)C4(C)(C(=CC3)CC(O)CC4)))) CAS:313-04-2 1.3.1.72 desmosterol + NADPH = cholesterol + NADP+ cholesterol biosynthesis III (via desmosterol) desmosterol desmosterol*24-dehydrocholesterol*Δ5,24-cholestadien-3-β-ol*desmesterol*24-dehydrocholesterol 384.644 C27 H44 O1 CC(C)=CCCC(C)[CH]1(C2(C)([CH](CC1)[CH]3([CH](CC2)C4(C)(C(=CC3)CC(O)CC4)))) CAS:313-04-2 1.3.1.21 7-dehydrodesmosterol + NADPH = desmosterol + NADP+ cholesterol biosynthesis III (via desmosterol) acetylphosphate acetyl-P 140.032 C2 H5 O5 P1 CC(=O)OP(=O)(O)O CAS:19926-71-7:*LIGAND-CPD:C00227: 4.1.2.9 D-xylulose-5-phosphate = H2O + D-glyceraldehyde-3-phosphate + acetylphosphate glucose fermentation to lactate II acetylphosphate acetyl-P 140.032 C2 H5 O5 P1 CC(=O)OP(=O)(O)O CAS:19926-71-7:*LIGAND-CPD:C00227: 4.1.2.22 fructose-6-phosphate = H2O + D-erythrose-4-phosphate + acetylphosphate glucose fermentation to lactate II acetylphosphate acetyl-P 140.032 C2 H5 O5 P1 CC(=O)OP(=O)(O)O CAS:19926-71-7:*LIGAND-CPD:C00227: 2.3.1.8 acetyl-CoA = acetylphosphate + coenzyme A mixed acid fermentation acetylphosphate acetyl-P 140.032 C2 H5 O5 P1 CC(=O)OP(=O)(O)O CAS:19926-71-7:*LIGAND-CPD:C00227: 2.3.1.8 acetyl-CoA = acetylphosphate + coenzyme A D-lactate fermentation to propionate and acetate acetylphosphate acetyl-P 140.032 C2 H5 O5 P1 CC(=O)OP(=O)(O)O CAS:19926-71-7:*LIGAND-CPD:C00227: 2.3.1.8 acetyl-CoA = acetylphosphate + coenzyme A ethanol fermentation to acetate acetylphosphate acetyl-P 140.032 C2 H5 O5 P1 CC(=O)OP(=O)(O)O CAS:19926-71-7:*LIGAND-CPD:C00227: 2.3.1.8 acetyl-CoA = acetylphosphate + coenzyme A gallate degradation III (anaerobic) acetylphosphate acetyl-P 140.032 C2 H5 O5 P1 CC(=O)OP(=O)(O)O CAS:19926-71-7:*LIGAND-CPD:C00227: 2.7.2.1 ATP + acetate = ADP + acetylphosphate mixed acid fermentation acetylphosphate acetyl-P 140.032 C2 H5 O5 P1 CC(=O)OP(=O)(O)O CAS:19926-71-7:*LIGAND-CPD:C00227: 2.7.2.1 ATP + acetate = ADP + acetylphosphate D-lactate fermentation to propionate and acetate acetylphosphate acetyl-P 140.032 C2 H5 O5 P1 CC(=O)OP(=O)(O)O CAS:19926-71-7:*LIGAND-CPD:C00227: 2.7.2.1 ATP + acetate = ADP + acetylphosphate ethanol fermentation to acetate acetylphosphate acetyl-P 140.032 C2 H5 O5 P1 CC(=O)OP(=O)(O)O CAS:19926-71-7:*LIGAND-CPD:C00227: 2.7.2.1 ATP + acetate = ADP + acetylphosphate glucose fermentation to lactate II acetylphosphate acetyl-P 140.032 C2 H5 O5 P1 CC(=O)OP(=O)(O)O CAS:19926-71-7:*LIGAND-CPD:C00227: 2.7.2.1 ATP + acetate = ADP + acetylphosphate gallate degradation III (anaerobic) dalbergioidin 288.256 C15 H12 O6 C2(C(c1(c(O)cc(O)cc1))C(=O)c3(c(O2)cc(O)cc(O)3)) dalbergioidin + dimethylallyl-PP = kievitone + diphosphate kievitone biosynthesis dalbergioidin 288.256 C15 H12 O6 C2(C(c1(c(O)cc(O)cc1))C(=O)c3(c(O2)cc(O)cc(O)3)) 1.3.1.51 dalbergioidin + NADP+ = 2'-hydroxygenistein + NADPH + H+ kievitone biosynthesis canavaninosuccinate 292.248 C9 H16 N4 O7 C(O)(=O)C(N)CCONC(=N)NC(C(O)=O)CC(O)=O 6.3.4.5 O-ureidohomoserine + L-aspartate + ATP = canavaninosuccinate + AMP + diphosphate canavanine biosynthesis canavaninosuccinate 292.248 C9 H16 N4 O7 C(O)(=O)C(N)CCONC(=N)NC(C(O)=O)CC(O)=O 4.3.2.1 canavaninosuccinate = canavanine + fumarate canavanine biosynthesis 2,3-dihydroxybenzoate 2,3-Dihydroxybenzoic acid 154.122 C7 H6 O4 C(O)(=O)c1(c(O)c(O)ccc1) LIGAND-CPD:C00196:*CAS:303-38-8 ATP + L-serine + 2,3-dihydroxybenzoate = enterobactin + diphosphate + AMP enterobactin biosynthesis 2,3-dihydroxybenzoate 2,3-Dihydroxybenzoic acid 154.122 C7 H6 O4 C(O)(=O)c1(c(O)c(O)ccc1) LIGAND-CPD:C00196:*CAS:303-38-8 1.3.1.28 NAD+ + 2,3-dihydro-2,3-dihydroxybenzoate = NADH + 2,3-dihydroxybenzoate enterobactin biosynthesis D-ribulose-1-phosphate D-ribulose-1-P 230.111 C5 H11 O8 P1 C(O)C(O)C(O)C(=O)COP(O)(O)=O 2.4.2.1 nicotinate + D-ribulose-1-phosphate = nicotinate riboside pyridine nucleotide cycling (plants) terpinolene 136.236 C10 H16 CC1(=CCC(=C(C)C)CC1) 4.2.3.- geranyl-PP = terpinolene + diphosphate monoterpene biosynthesis 4α-methyl-5α-cholesta-8-en-3-one 398.671 C28 H46 O1 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(C)C(=O)CC4)(C)))(C)) 1.1.1.270 4α-methyl-5α-cholesta-8-en-3-one + NADPH = 4α-methyl-cholesta-8-enol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 4α-methyl-5α-cholesta-8-en-3-one 398.671 C28 H46 O1 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(C)C(=O)CC4)(C)))(C)) 1.1.1.170 4α-carboxy-4β-methyl-5α-cholesta-8-en-3β-ol = 4α-methyl-5α-cholesta-8-en-3-one + CO2 cholesterol biosynthesis II (via 24,25-dihydrolanosterol) antheraxanthin 584.881 C40 H56 O3 CC(C=CC12(C(C)(C)CC(O)CC(C)(O1)2))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC3(C(C)(C)CC(O)CC(C)=3) 1.14.13.90 antheraxanthin + H+ + O2 = violaxanthin + H2O carotenoid biosynthesis antheraxanthin 584.881 C40 H56 O3 CC(C=CC12(C(C)(C)CC(O)CC(C)(O1)2))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC3(C(C)(C)CC(O)CC(C)=3) 1.14.13.90 antheraxanthin + H+ + O2 = violaxanthin + H2O xanthophyll cycle antheraxanthin 584.881 C40 H56 O3 CC(C=CC12(C(C)(C)CC(O)CC(C)(O1)2))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC3(C(C)(C)CC(O)CC(C)=3) 1.10.99.3 violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O carotenoid biosynthesis antheraxanthin 584.881 C40 H56 O3 CC(C=CC12(C(C)(C)CC(O)CC(C)(O1)2))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC3(C(C)(C)CC(O)CC(C)=3) 1.10.99.3 violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle antheraxanthin 584.881 C40 H56 O3 CC(C=CC12(C(C)(C)CC(O)CC(C)(O1)2))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC3(C(C)(C)CC(O)CC(C)=3) 1.14.13.90 zeaxanthin + H+ + O2 = antheraxanthin + H2O carotenoid biosynthesis antheraxanthin 584.881 C40 H56 O3 CC(C=CC12(C(C)(C)CC(O)CC(C)(O1)2))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC3(C(C)(C)CC(O)CC(C)=3) 1.14.13.90 zeaxanthin + H+ + O2 = antheraxanthin + H2O xanthophyll cycle antheraxanthin 584.881 C40 H56 O3 CC(C=CC12(C(C)(C)CC(O)CC(C)(O1)2))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC3(C(C)(C)CC(O)CC(C)=3) 1.10.99.3 antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O carotenoid biosynthesis antheraxanthin 584.881 C40 H56 O3 CC(C=CC12(C(C)(C)CC(O)CC(C)(O1)2))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC3(C(C)(C)CC(O)CC(C)=3) 1.10.99.3 antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle 18:2-16:3-MGDG 1-18:2-2-16:3-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(7Z,10Z,13Z-hexadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerol 749.036 C43 H72 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCC=CCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:1-16:3-MGDG = 18:2-16:3-MGDG glycolipid desaturation 18:2-16:3-MGDG 1-18:2-2-16:3-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(7Z,10Z,13Z-hexadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerol 749.036 C43 H72 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCC=CCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-16:3-MGDG = 18:3-16:3-MGDG glycolipid desaturation 18:2-16:3-MGDG 1-18:2-2-16:3-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(7Z,10Z,13Z-hexadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerol 749.036 C43 H72 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCC=CCC=CCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-16:2-MGDG = 18:2-16:3-MGDG glycolipid desaturation fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate sucrose degradation to ethanol and lactate (anaerobic) fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate glycolysis IV (plant cytosol) fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate fructose degradation to pyruvate and lactate (anaerobic) fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate glycolysis I fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 3.1.3.11 fructose-1,6-bisphosphate + H2O = fructose-6-phosphate xylulose-monophosphate cycle fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 3.1.3.11 fructose-1,6-bisphosphate + H2O = fructose-6-phosphate Calvin cycle fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 3.1.3.11 fructose-1,6-bisphosphate + H2O = fructose-6-phosphate gluconeogenesis fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 3.1.3.11 fructose-1,6-bisphosphate + H2O = fructose-6-phosphate glycolysis I fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 2.7.1.90 fructose-6-phosphate + diphosphate = fructose-1,6-bisphosphate glycolysis IV (plant cytosol) fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate xylulose-monophosphate cycle fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate Calvin cycle fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate gluconeogenesis fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate sucrose degradation to ethanol and lactate (anaerobic) fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate glycolysis IV (plant cytosol) fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate fructose degradation to pyruvate and lactate (anaerobic) fructose-1,6-bisphosphate 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 340.117 C6 H14 O12 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)(O)COP(O)(=O)O) LIGAND-CPD:C00354:*CAS:488-69-7 4.1.2.13 fructose-1,6-bisphosphate = dihydroxy-acetone-phosphate + D-glyceraldehyde-3-phosphate glycolysis I isobutanal isobutyraldehyde 72.107 C4 H8 O1 CC(C)C=O 1.1.1.1 isobutanal + NADH = isobutanol + NAD+ valine degradation II isobutanal isobutyraldehyde 72.107 C4 H8 O1 CC(C)C=O 4.1.1.1 2-keto-isovalerate = isobutanal + CO2 valine degradation II dTDP-4-dehydro-6-deoxy-L-mannose dTDP-4-oxo-6-deoxy-L-mannose*dTDP-4-oxo-L-rhamnose*dTDP-4-dehydro-L-rhamnose 546.317 C16 H24 N2 O15 P2 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(=O)C(O3)C))) LIGAND-CPD:C00688: 5.1.3.13 dTDP-4-dehydro-6-deoxy-D-glucose = dTDP-4-dehydro-6-deoxy-L-mannose dTDP-L-rhamnose biosynthesis I dTDP-4-dehydro-6-deoxy-L-mannose dTDP-4-oxo-6-deoxy-L-mannose*dTDP-4-oxo-L-rhamnose*dTDP-4-dehydro-L-rhamnose 546.317 C16 H24 N2 O15 P2 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(=O)C(O3)C))) LIGAND-CPD:C00688: 1.1.1.133 NADP+ + dTDP-α-L-rhamnose = NADPH + dTDP-4-dehydro-6-deoxy-L-mannose dTDP-L-rhamnose biosynthesis I [Cys-Gly]-S-conjugate C5 H9 N2 O3 R1 S1 3.4.11.2 [Cys-Gly]-S-conjugate + H2O = glycine glutathione-mediated detoxification [Cys-Gly]-S-conjugate C5 H9 N2 O3 R1 S1 3.4.19.9 glutathione-mediated detoxification 2-hydroxy-3-keto-5-methylthio-1-phosphopentene 1-phosphoryloxyl-2-hydroxy-3-keto-5-methylthiopentene 242.183 C6 H11 O6 P1 S1 C(OP(O)(O)=O)=C(O)C(=O)CCSC 2-hydroxy-3-keto-5-methylthio-1-phosphopentene + H2O = 1,2-dihydroxy-3-keto-5-methylthiopentene methionine salvage pathway 2-hydroxy-3-keto-5-methylthio-1-phosphopentene 1-phosphoryloxyl-2-hydroxy-3-keto-5-methylthiopentene 242.183 C6 H11 O6 P1 S1 C(OP(O)(O)=O)=C(O)C(=O)CCSC 2,3-diketo-5-methylthio-1-phosphopentane = 2-hydroxy-3-keto-5-methylthio-1-phosphopentene methionine salvage pathway ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.17 L-glutamate + ATP = ADP formylTHF biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.17 L-glutamate + ATP = ADP formylTHF biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 L-glutamate + ATP + NADPH = ADP + L-glutamate γ-semialdehyde + NADP+ arginine biosynthesis IV ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.6 ATP + 4-carboxyaminoimidazole ribonucleotide + L-aspartate = ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole purine nucleotides de novo biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.6 ATP + 4-carboxyaminoimidazole ribonucleotide + L-aspartate = ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole purine nucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine purine nucleotides de novo biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.5.3 ATP + 5'-phosphoribosyl-N-formylglycineamide + L-glutamine + H2O = L-glutamate + ADP + 5-phosphoribosyl-N-formylglycineamidine purine nucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.2 ammonia + CO2 + ATP = carbamoyl-phosphate + ADP citrulline degradation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP formylTHF biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP tetrahydrofolate biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP formylTHF biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.12 L-glutamate + ATP = 7,8-dihydrofolate + ADP tetrahydrofolate biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.1 ATP + acetate = ADP + acetylphosphate mixed acid fermentation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.1 ATP + acetate = ADP + acetylphosphate D-lactate fermentation to propionate and acetate ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.1 ATP + acetate = ADP + acetylphosphate ethanol fermentation to acetate ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.1 ATP + acetate = ADP + acetylphosphate glucose fermentation to lactate II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.1 ATP + acetate = ADP + acetylphosphate gallate degradation III (anaerobic) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.3 AMP + ATP = ADP salvage pathways of purine and pyrimidine nucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.3 AMP + ATP = ADP purine nucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.6 dADP + ATP = dATP + ADP purine nucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.71 shikimate + ATP = shikimate-3-phosphate + ADP chorismate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.33 pantothenate + ATP = D-4'-phosphopantothenate + ADP coenzyme A biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.- nicotinate riboside + ATP = nicotinate nucleotide + ADP pyridine nucleotide cycling (plants) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.1.2 ammonia + L-glutamate + ATP = L-glutamine + ADP glutamine biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.15 D-ribose + ATP = D-ribose-5-phosphate + ADP ribose degradation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.45 2-dehydro-3-deoxy-D-gluconate + ATP = 2-keto-3-deoxy-6-phospho-gluconate + ADP β-D-glucuronide degradation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.- ATP + pyridoxine = ADP + pyridoxine-5'-phosphate pyridoxal 5'-phosphate salvage pathway ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.23 NAD+ + ATP = NADP+ + ADP NAD/NADH phosphorylation and dephosphorylation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.49 ATP + hydroxymethylpyrimidine = ADP + hydroxymethylpyrimidine phosphate thiamine biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate de novo biosynthesis of pyrimidine ribonucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis II (acetyl cycle) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.5.5 ATP + L-glutamine + CO2 + H2O = L-glutamate + ADP + carbamoyl-phosphate arginine biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.91 4-hydroxysphinganine + ATP = phytosphingosine-1-P + ADP sphingolipid metabolism ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.17 ATP + L-glutamate = ADP folate polyglutamylation I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.17 ATP + L-glutamate = ADP formylTHF biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.17 ATP + L-glutamate = ADP tetrahydrofolate biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.20 adenosine + ATP = AMP + ADP salvage pathways of purine nucleosides II (plant) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.30 glycerol + ATP = sn-glycerol-3-phosphate + ADP glycerol degradation IV ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.30 glycerol + ATP = sn-glycerol-3-phosphate + ADP glycerol degradation I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.1.2.- 5-phospho-ribosyl-glycineamide + formate + ATP = 5'-phosphoribosyl-N-formylglycineamide + ADP purine nucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.50 ATP + 4-methyl-5-(β-hydroxyethyl)thiazole = ADP + 4-methyl-5-(β-hydroxyethyl)thiazole phosphate thiamine biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 D-myo-inositol (3,4,6)-trisphosphate + ATP = D-myo-inositol (3,4,5,6)-tetrakisphosphate + ADP lipid-independent phytate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate sucrose degradation to ethanol and lactate (anaerobic) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate glycolysis IV (plant cytosol) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate fructose degradation to pyruvate and lactate (anaerobic) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.11 ATP + fructose-6-phosphate = ADP + fructose-1,6-bisphosphate glycolysis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.2.1.5 succinate + coenzyme A + ATP = succinyl-CoA + ADP reductive TCA cycle I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.2.1.5 succinate + coenzyme A + ATP = succinyl-CoA + ADP TCA cycle ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.6 dGDP + ATP = dGTP + ADP purine nucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.2 β-D-glucose + ATP = β-D-glucose-6-phosphate + ADP trehalose degradation II (high osmolarity) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = ADP + 5-phospho-ribosyl-glycineamide purine nucleotides de novo biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.13 5-phospho-β-D-ribosyl-amine + ATP + glycine = ADP + 5-phospho-ribosyl-glycineamide purine nucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.6 dCDP + ATP = dCTP + ADP de novo biosynthesis of pyrimidine deoxyribonucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.6 CDP + ATP = CTP + ADP de novo biosynthesis of pyrimidine ribonucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.130 lipid A disaccharide + ATP = lipid IVA + ADP lipid-A-precursor biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.12 ATP + gluconate = 6-phospho-D-gluconate + ADP L-idonate degradation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.22 nicotinamide riboside + ATP = nicotinamide mononucleotide + ADP NAD salvage pathway II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.31 glycerate + ATP = 3-phosphoglycerate + ADP glycolate and glyoxylate degradation I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.31 glycerate + ATP = 3-phosphoglycerate + ADP allantoin degradation I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.31 glycerate + ATP = 3-phosphoglycerate + ADP photorespiration ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.- cytidine + ATP = CMP + ADP salvage pathways of purine and pyrimidine nucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP sucrose degradation III ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP sucrose degradation I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP sucrose degradation to ethanol and lactate (anaerobic) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.4 fructose + ATP = fructose-6-phosphate + ADP fructose degradation to pyruvate and lactate (anaerobic) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.2 ATP + UTP + L-glutamine + H2O = ADP + CTP + L-glutamate de novo biosynthesis of pyrimidine ribonucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.3.2 N5-formyl-THF + ATP = ADP folate transformations ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.3.2 N5-formyl-THF + ATP = ADP formylTHF biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.91 sphinganine + ATP = sphinganine 1-phosphate + ADP sphingolipid metabolism ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.17 D-xylulose + ATP = D-xylulose-5-phosphate + ADP xylose degradation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.82 ethanolamine + ATP = phosphoryl-ethanolamine + ADP choline biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.82 ethanolamine + ATP = phosphoryl-ethanolamine + ADP phospholipid biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.16 ammonia + H2O + CO2 + ATP = carbamoyl-phosphate + ADP urea cycle ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.3 glycine + L-γ-glutamylcysteine + ATP = glutathione + ADP glutathione biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 = 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 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.6 ATP = α-D-galactose 1-phosphate + ADP galactose degradation II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.6 ATP = 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 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.4 D-alanine + ATP = D-alanyl-D-alanine + ADP peptidoglycan biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.6 dTDP + ATP = dTTP + ADP de novo biosynthesis of pyrimidine deoxyribonucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.7 butyrate + ATP = butyryl phosphate + ADP acetyl CoA fermentation to butyrate ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate mixed acid fermentation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate sucrose degradation to ethanol and lactate (anaerobic) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate respiration (anaerobic) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate glycolysis IV (plant cytosol) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate fructose degradation to pyruvate and lactate (anaerobic) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate glucose fermentation to lactate II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.40 ATP + pyruvate = ADP + phosphoenolpyruvate glycolysis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.64 myo-inositol + ATP = D-myo-inositol (3)-monophosphate + ADP lipid-independent phytate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.1 α-D-glucose + ATP = α-D-glucose 6-phosphate + ADP sucrose degradation III ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.1 α-D-glucose + ATP = α-D-glucose 6-phosphate + ADP starch degradation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.39 homoserine + ATP = O-phospho-L-homoserine + ADP threonine biosynthesis from homoserine ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.39 homoserine + ATP = O-phospho-L-homoserine + ADP methionine biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.- ATP + UMP = ADP + UDP de novo biosynthesis of pyrimidine ribonucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.- ATP + UMP = ADP + UDP salvage pathways of purine and pyrimidine nucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.3 ADP = ATP + formate tetrahydrofolate biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.7 mannose + ATP = mannose-6-phosphate + ADP GDP-mannose metabolism ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.7 mannose + ATP = mannose-6-phosphate + ADP mannose degradation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.8 GMP + ATP = GDP + ADP salvage pathways of purine and pyrimidine nucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.8 GMP + ATP = GDP + ADP purine nucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.21 thymidine + ATP = dTMP + ADP salvage pathways of purine and pyrimidine nucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.21 thymidine + ATP = dTMP + ADP salvage pathways of pyrimidine deoxyribonucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.4.1.4 ATP + 3-methylcrotonyl-CoA + HCO3- = ADP + 3-methylglutaconyl-CoA leucine degradation I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.17 tetrahydrofolate + L-glutamate + ATP = THF-L-glutamate + ADP tetrahydrofolate biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.24 dephospho-CoA + ATP = coenzyme A + ADP coenzyme A biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.21 deoxyuridine + ATP = dUMP + ADP salvage pathways of pyrimidine deoxyribonucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.89 thiamin + ATP = thiamine-phosphate + ADP thiamine biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF folate polyglutamylation I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF folate transformations ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF formylTHF biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.3 ATP + formate + tetrahydrofolate = ADP + N10-formyl-THF formylTHF biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.6 dUDP + ATP = dUTP + ADP de novo biosynthesis of pyrimidine deoxyribonucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.8 L-alanine + UDP-N-acetylmuramate + ATP = UDP-N-acetylmuramoyl-L-alanine + ADP peptidoglycan biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.14 ATP + CMP = ADP + CDP salvage pathways of purine and pyrimidine nucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.14 ATP + CMP = ADP + CDP salvage pathways of pyrimidine ribonucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.32 choline + ATP = phosphoryl-choline + ADP phospholipid biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = ADP + 5-aminoimidazole ribonucleotide purine nucleotides de novo biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = ADP + 5-aminoimidazole ribonucleotide purine nucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.6 GDP + ATP = GTP + ADP purine nucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.19 D-ribulose-5-phosphate + ATP = ADP Calvin cycle ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.48 uridine + ATP = UMP + ADP salvage pathways of purine and pyrimidine nucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.36 (R)-mevalonate + ATP = mevalonate-5P + ADP mevalonate pathway ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.134 D-myo-inositol (3,4,5,6)-tetrakisphosphate + ATP = D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ADP lipid-independent phytate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.91 phytosphingosine-1-P + ADP = ATP + 4-hydroxysphinganine sphingolipid metabolism ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.4.1.21 ADP-D-glucose = ADP starch biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.86 NADH + ATP = NADPH + ADP NAD/NADH phosphorylation and dephosphorylation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.100 ATP + 5-methylthioribose = ADP + 5-methylthioribose-1-phosphate methionine salvage pathway ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.18 5-aminoimidazole ribonucleotide + ATP + HCO3- = N5-carboxyaminoimidazole ribonucleotide + ADP purine nucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.25 adenosine 5'-phosphosulfate + ATP = phosphoadenosine-5'-phosphosulfate + ADP sulfate reduction I (assimilatory) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.25 adenosine 5'-phosphosulfate + ATP = phosphoadenosine-5'-phosphosulfate + ADP sulfate activation for sulfonation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 1.17.4.1 dADP + H2O = ADP purine nucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.10 UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + D-alanyl-D-alanine + ATP = ADP peptidoglycan biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.1 β-D-glucose + ATP = β-D-glucose-6-phosphate + ADP glucose fermentation to lactate II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 D-myo-inositol (3)-monophosphate + ATP = D-myo-inositol (3,4)-bisphosphate + ADP lipid-independent phytate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.- D-myo-inositol (1,3,4,5,6)-pentakisphosphate + ATP = phytate + ADP lipid-independent phytate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.16 thiamine-phosphate + ATP = thiamine diphosphate + ADP thiamine biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.4.1.2 ATP + acetyl-CoA + HCO3- + H+ = ADP + malonyl-CoA fatty acid biosynthesis - initial steps ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.17 L-glutamate + ATP = ADP folate polyglutamylation II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.73 guanosine + ATP = GMP + ADP salvage pathways of purine nucleosides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.73 guanosine + ATP = GMP + ADP salvage pathways of purine nucleosides II (plant) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 D-myo-inositol (3,4)-bisphosphate + ATP = D-myo-inositol (3,4,6)-trisphosphate + ADP lipid-independent phytate biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.43 glucuronate + ATP = 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 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.13 UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + meso-diaminopimelate + ATP = UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + ADP peptidoglycan biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.2 L-cysteine + L-glutamate + ATP = L-γ-glutamylcysteine + ADP glutathione biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = dethiobiotin + ADP biotin biosynthesis II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.3.3 CO2 + 7,8-diaminopelargonate + ATP = dethiobiotin + ADP biotin biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.4.14 CO2 + ATP = ADP biotin-carboxyl carrier protein ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.2 mevalonate-5P + ATP = mevalonate-5-PP + ADP mevalonate pathway ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.9 ATP + dTMP = ADP + dTDP salvage pathways of purine and pyrimidine nucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.9 ATP + dTMP = ADP + dTDP de novo biosynthesis of pyrimidine deoxyribonucleotides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.35 ATP + pyridoxamine = ADP + pyridoxamine 5'-phosphate pyridoxal 5'-phosphate salvage pathway ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP Calvin cycle ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP gluconeogenesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP sucrose degradation to ethanol and lactate (anaerobic) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP glycolysis IV (plant cytosol) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP fructose degradation to pyruvate and lactate (anaerobic) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP glucose fermentation to lactate II ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP glycolysis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.29 dihydroxy-acetone + ATP = dihydroxy-acetone-phosphate + ADP xylulose-monophosphate cycle ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.3.2.9 UDP-N-acetylmuramoyl-L-alanine + D-glutamate + ATP = UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + ADP peptidoglycan biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.51 L-fuculose + ATP = fuculose-1-phosphate + ADP fucose degradation ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 4.1.1.49 oxaloacetate + ATP = CO2 + phosphoenolpyruvate + ADP gluconeogenesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 6.6.1.1 ATP + protoporphyrin IX + Mg2+ + H2O = Mg-protoporphyrin + ADP + H+ chlorophyllide a biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.35 ATP + pyridoxal = ADP + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.35 ATP + pyridoxal = ADP + pyridoxal 5'-phosphate pyridoxamine anabolism ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 ADP = dADP + H2O purine nucleotides de novo biosynthesis I ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 4.1.1.33 mevalonate-5-PP + ATP = CO2 + ADP mevalonate pathway ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.26 riboflavin + ATP = FMN + ADP flavin biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.91 sphinganine + ATP = sphinganine 1-phosphate + ADP sphingolipid metabolism ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.73 inosine + ATP = inosine-5'-phosphate + ADP salvage pathways of adenine, hypoxanthine, and their nucleosides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.73 inosine + ATP = inosine-5'-phosphate + ADP salvage pathways of purine nucleosides ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.1.73 inosine + ATP = inosine-5'-phosphate + ADP salvage pathways of purine nucleosides II (plant) ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.5.1.- dimethylallyl-PP + ADP = isopentenyladenosine-5'-diphosphate + diphosphate trans-zeatin biosynthesis ADP adenosine pyrophosphate*adenosine 5'-pyrophosphate*adenosine-5'-diphosphate*adenosine-diphosphate*adenosine-5-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(O)(=O)OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) CAS:20398-34-9:*LIGAND-CPD:C00008:*CAS:58-64-0 2.7.4.6 UDP + ATP = UTP + ADP de novo biosynthesis of pyrimidine ribonucleotides N-feruloyltyramine 313.352 C18 H19 N1 O4 C(Cc1(ccc(O)cc1))NC(=O)C=Cc2(cc(OC)c(O)cc2) 2.3.1.110 feruloyl-CoA + tyramine = N-feruloyltyramine + coenzyme A suberin biosynthesis menaquinol Menaquinol 8*reduced menaquinone*vitamin K2 721.16 C51 H76 O2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(O)c2(c(C(O)C=1C)cccc2)) LIGAND-CPD:C05819: 1.3.5.- fumarate + menaquinol + H+ = succinate + menaquinone-8 mixed acid fermentation menaquinol Menaquinol 8*reduced menaquinone*vitamin K2 721.16 C51 H76 O2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(O)c2(c(C(O)C=1C)cccc2)) LIGAND-CPD:C05819: 1.3.5.- fumarate + menaquinol + H+ = succinate + menaquinone-8 respiration (anaerobic) menaquinol Menaquinol 8*reduced menaquinone*vitamin K2 721.16 C51 H76 O2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(O)c2(c(C(O)C=1C)cccc2)) LIGAND-CPD:C05819: 1.2.1.2 formate + menaquinone-8 = CO2 + menaquinol respiration (anaerobic)-- electron donors reaction list menaquinol Menaquinol 8*reduced menaquinone*vitamin K2 721.16 C51 H76 O2 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCC1(C(O)c2(c(C(O)C=1C)cccc2)) LIGAND-CPD:C05819: 1.2.1.2 formate + menaquinone-8 = CO2 + menaquinol formate oxidation to CO2 S-methyl-L-methionine S-methylmethionine 164.242 C6 H14 N1 O2 S1 C(=O)(O)C(N)CC[S+](C)C CAS:4289-98-9:*LIGAND-CPD:C03172:*CAS:4727-40-6 2.1.1.10 S-methyl-L-methionine + L-homocysteine = L-methionine methionine biosynthesis II S-methyl-L-methionine S-methylmethionine 164.242 C6 H14 N1 O2 S1 C(=O)(O)C(N)CC[S+](C)C CAS:4289-98-9:*LIGAND-CPD:C03172:*CAS:4727-40-6 2.1.1.10 S-methyl-L-methionine + L-homocysteine = L-methionine S-methylmethionine cycle S-methyl-L-methionine S-methylmethionine 164.242 C6 H14 N1 O2 S1 C(=O)(O)C(N)CC[S+](C)C CAS:4289-98-9:*LIGAND-CPD:C03172:*CAS:4727-40-6 2.1.1.12 L-methionine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine S-methylmethionine cycle 2-dehydropantoate ketopantoate*2-keto-pantoate 146.143 C6 H10 O4 C(O)(=O)C(=O)C(C)(C)CO LIGAND-CPD:C00966: 2.1.2.11 5,10-methylene-THF + 2-keto-isovalerate + H2O = tetrahydrofolate + 2-dehydropantoate pantothenate biosynthesis I 2-dehydropantoate ketopantoate*2-keto-pantoate 146.143 C6 H10 O4 C(O)(=O)C(=O)C(C)(C)CO LIGAND-CPD:C00966: 2.1.2.11 5,10-methylene-THF + 2-keto-isovalerate + H2O = tetrahydrofolate + 2-dehydropantoate pantothenate biosynthesis II 2-dehydropantoate ketopantoate*2-keto-pantoate 146.143 C6 H10 O4 C(O)(=O)C(=O)C(C)(C)CO LIGAND-CPD:C00966: 1.1.1.169 L-pantoate + NADP+ = 2-dehydropantoate + NADPH pantothenate biosynthesis I 2-dehydropantoate ketopantoate*2-keto-pantoate 146.143 C6 H10 O4 C(O)(=O)C(=O)C(C)(C)CO LIGAND-CPD:C00966: 1.1.1.169 L-pantoate + NADP+ = 2-dehydropantoate + NADPH pantothenate biosynthesis II (S)-2,3-Epoxysqualene Squalene 2,3-epoxide*Squalene 2,3-oxide*(S)-Squalene-2,3-epoxide*2,3-EDSQ*2,3-epoxisqualene*oxidosqualene 426.724 C30 H50 O1 CC(CCC1(C(O1)(C)C))=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:9029-62-3 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis I (S)-2,3-Epoxysqualene Squalene 2,3-epoxide*Squalene 2,3-oxide*(S)-Squalene-2,3-epoxide*2,3-EDSQ*2,3-epoxisqualene*oxidosqualene 426.724 C30 H50 O1 CC(CCC1(C(O1)(C)C))=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:9029-62-3 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) (S)-2,3-Epoxysqualene Squalene 2,3-epoxide*Squalene 2,3-oxide*(S)-Squalene-2,3-epoxide*2,3-EDSQ*2,3-epoxisqualene*oxidosqualene 426.724 C30 H50 O1 CC(CCC1(C(O1)(C)C))=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:9029-62-3 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) (S)-2,3-Epoxysqualene Squalene 2,3-epoxide*Squalene 2,3-oxide*(S)-Squalene-2,3-epoxide*2,3-EDSQ*2,3-epoxisqualene*oxidosqualene 426.724 C30 H50 O1 CC(CCC1(C(O1)(C)C))=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:9029-62-3 5.4.99.7 (S)-2,3-Epoxysqualene = lanosterol cholesterol biosynthesis I (S)-2,3-Epoxysqualene Squalene 2,3-epoxide*Squalene 2,3-oxide*(S)-Squalene-2,3-epoxide*2,3-EDSQ*2,3-epoxisqualene*oxidosqualene 426.724 C30 H50 O1 CC(CCC1(C(O1)(C)C))=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:9029-62-3 5.4.99.7 (S)-2,3-Epoxysqualene = lanosterol cholesterol biosynthesis III (via desmosterol) (S)-2,3-Epoxysqualene Squalene 2,3-epoxide*Squalene 2,3-oxide*(S)-Squalene-2,3-epoxide*2,3-EDSQ*2,3-epoxisqualene*oxidosqualene 426.724 C30 H50 O1 CC(CCC1(C(O1)(C)C))=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:9029-62-3 5.4.99.7 (S)-2,3-Epoxysqualene = lanosterol cholesterol biosynthesis II (via 24,25-dihydrolanosterol) (S)-2,3-Epoxysqualene Squalene 2,3-epoxide*Squalene 2,3-oxide*(S)-Squalene-2,3-epoxide*2,3-EDSQ*2,3-epoxisqualene*oxidosqualene 426.724 C30 H50 O1 CC(CCC1(C(O1)(C)C))=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:9029-62-3 5.4.99.8 (S)-2,3-Epoxysqualene = cycloartenol 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 426.724 C30 H50 O1 CC(CCC1(C(O1)(C)C))=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C CAS:9029-62-3 1.14.99.7 O2 + squalene = (S)-2,3-Epoxysqualene + H2O sterol biosynthesis pseudobaptigenin 282.252 C16 H10 O5 C1(=C(C(=O)c2(c(O1)cc(O)cc2))c3(ccc4(c(c3)OCO4))) 1.14.13.53 pseudobaptigenin + NADPH + O2 = 2'-hydroxypseudobaptigenin + NADP+ + H2O maackiain biosynthesis pseudobaptigenin 282.252 C16 H10 O5 C1(=C(C(=O)c2(c(O1)cc(O)cc2))c3(ccc4(c(c3)OCO4))) calycosin + NADPH + O2 = pseudobaptigenin + NADP+ + H2O maackiain biosynthesis sucrose sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C(O)C1(OC(CO)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND:C00089:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.99 sucrose + sucrose = 1-kestotriose + β-D-glucose fructan biosynthesis sucrose sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C(O)C1(OC(CO)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND:C00089:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.7.1.69 sucrose = sucrose-6-phosphate sucrose degradation I sucrose sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C(O)C1(OC(CO)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND:C00089:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.10 sucrose + sucrose = 6-kestotriose + β-D-glucose fructan biosynthesis sucrose sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C(O)C1(OC(CO)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND:C00089:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.- 1-kestotriose + sucrose = 6G-kestotriose + sucrose fructan biosynthesis sucrose sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C(O)C1(OC(CO)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND:C00089:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP sucrose degradation III sucrose sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C(O)C1(OC(CO)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND:C00089:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP sucrose degradation to ethanol and lactate (anaerobic) sucrose sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C(O)C1(OC(CO)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND:C00089:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP galactose degradation II sucrose sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C(O)C1(OC(CO)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND:C00089:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.13 fructose + UDP-D-glucose = sucrose + UDP sucrose biosynthesis sucrose sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C(O)C1(OC(CO)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND:C00089:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 3.1.3.24 sucrose-6-phosphate + H2O = sucrose sucrose biosynthesis sucrose sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C(O)C1(OC(CO)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND:C00089:*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 sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C(O)C1(OC(CO)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND:C00089:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 3.2.1.26 sucrose + H2O = α-D-glucose + fructose sucrose degradation III sucrose sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C(O)C1(OC(CO)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND:C00089:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 3.2.1.80 1-kestotriose + H2O = fructose + sucrose fructan degradation sucrose sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C(O)C1(OC(CO)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND:C00089:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.82 galactinol + sucrose = myo-inositol + raffinose stachyose biosynthesis sucrose sugar*saccharose*Glc(α1<->2β)Fru*α-D-glucopyranosyl β-D-fructofuranoside 342.299 C12 H22 O11 C(O)C1(OC(CO)C(O)C(O)1)OC2(C(O)C(O)C(O)C(O2)CO) LIGAND:C00089:*LIGAND-CPD:C00089:*CAS:57-50-1*NCI:406942 2.4.1.100 1-kestotriose + 1-kestotriose = 1,1-kestotetraose + sucrose fructan biosynthesis benzoate benzoic acid*benzenecarboxylic acid*phenylformic acid 122.123 C7 H6 O2 C(O)(=O)c1(ccccc1) CAS:65-85-0 benzoyl-CoA + H2O = benzoate + coenzyme A salicylate biosynthesis benzoate benzoic acid*benzenecarboxylic acid*phenylformic acid 122.123 C7 H6 O2 C(O)(=O)c1(ccccc1) CAS:65-85-0 1.14.13.- benzoate + NADPH + O2 = salicylate + NADP+ + H2O salicylate biosynthesis (R)-mevalonate mevalonate*mevalonic acid 148.158 C6 H12 O4 C(O)CC(C)(O)CC(O)=O CAS:150-97-0 1.1.1.34 NADP+ + coenzyme A + (R)-mevalonate = NADPH + 3-hydroxy-3-methyl-glutaryl-CoA mevalonate pathway (R)-mevalonate mevalonate*mevalonic acid 148.158 C6 H12 O4 C(O)CC(C)(O)CC(O)=O CAS:150-97-0 2.7.1.36 (R)-mevalonate + ATP = mevalonate-5P + ADP mevalonate pathway (R)-mevalonate mevalonate*mevalonic acid 148.158 C6 H12 O4 C(O)CC(C)(O)CC(O)=O CAS:150-97-0 1.1.1.88 (R)-mevalonate + NAD+ + coenzyme A = 3-hydroxy-3-methyl-glutaryl-CoA + NADH + H+ mevalonate degradation hexanal 100.16 C6 H12 O1 CCCCC[CH]=O CAS:66-25-1 13-HPOD = 12-oxo-cis-9-dodecenoate + hexanal 13-LOX and 13-HPL pathway succinate-semialdehyde-thiamine PPi Succinate semialdehyde-thiamin diphosphate anion*succinate-semialdehyde-thiamine pyrophosphate*succinate-semialdehyde-thiamin pyrophosphate*succinate-semialdehyde-thiamin PPi 527.402 C16 H25 N4 O10 P2 S1 c1(c(c(N)nc(n1)C)C[n+]2(c(C)c(sc2)CCOP(=O)(O)OP(O)(=O)OC(O)CCC(=O)O)) LIGAND-CPD:C05816: succinate-semialdehyde-thiamine PPi + isochorismate = 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate + thiamine diphosphate + pyruvate menaquinone biosynthesis succinate-semialdehyde-thiamine PPi Succinate semialdehyde-thiamin diphosphate anion*succinate-semialdehyde-thiamine pyrophosphate*succinate-semialdehyde-thiamin pyrophosphate*succinate-semialdehyde-thiamin PPi 527.402 C16 H25 N4 O10 P2 S1 c1(c(c(N)nc(n1)C)C[n+]2(c(C)c(sc2)CCOP(=O)(O)OP(O)(=O)OC(O)CCC(=O)O)) LIGAND-CPD:C05816: succinate-semialdehyde-thiamine PPi + isochorismate = 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate + thiamine diphosphate + pyruvate phylloquinone biosynthesis succinate-semialdehyde-thiamine PPi Succinate semialdehyde-thiamin diphosphate anion*succinate-semialdehyde-thiamine pyrophosphate*succinate-semialdehyde-thiamin pyrophosphate*succinate-semialdehyde-thiamin PPi 527.402 C16 H25 N4 O10 P2 S1 c1(c(c(N)nc(n1)C)C[n+]2(c(C)c(sc2)CCOP(=O)(O)OP(O)(=O)OC(O)CCC(=O)O)) LIGAND-CPD:C05816: 4.1.1.71 α-ketoglutarate + thiamine diphosphate = succinate-semialdehyde-thiamine PPi + CO2 menaquinone biosynthesis UDP-3-O-(3-hydroxymyristoyl)-N-acetylglucosamine UDP-3-O-(3-hydroxytetradecanoyl)-N-acetylglucosamine 833.716 C31 H53 N3 O19 P2 CCCCCCCCCCCC(O)CC(=O)OC1(C(NC(=O)C)C(OC(C1O)CO)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c(=O)[nH]c(=O)cc3))) LIGAND-CPD:C04738: 2.3.1.129 UDP-N-acetyl-D-glucosamine = UDP-3-O-(3-hydroxymyristoyl)-N-acetylglucosamine lipid-A-precursor biosynthesis UDP-3-O-(3-hydroxymyristoyl)-N-acetylglucosamine UDP-3-O-(3-hydroxytetradecanoyl)-N-acetylglucosamine 833.716 C31 H53 N3 O19 P2 CCCCCCCCCCCC(O)CC(=O)OC1(C(NC(=O)C)C(OC(C1O)CO)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c(=O)[nH]c(=O)cc3))) LIGAND-CPD:C04738: UDP-3-O-(3-hydroxymyristoyl)-N-acetylglucosamine + H2O = UDP-3-O-(3-hydroxymyristoyl)glucosamine + acetate lipid-A-precursor biosynthesis indole-3-pyruvate indole-pyr*indolepyruvic acid*(indol-3-yl)pyruvate*indolepyruvate*3-(indol-3-yl)pyruvate 203.197 C11 H9 N1 O3 C(O)(=O)C(=O)Cc2(c[nH]c1(ccccc12)) CAS:35656-49-6 4.1.1.74 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 203.197 C11 H9 N1 O3 C(O)(=O)C(=O)Cc2(c[nH]c1(ccccc12)) CAS:35656-49-6 2.6.1.27 α-ketoglutarate + L-tryptophan = L-glutamate + indole-3-pyruvate IAA biosynthesis I 2,5-diamino-6-(ribosylamino)-4-(3H)-pyrimidinone 5'-phosphate 2,5-diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine*DARP 353.228 C9 H16 N5 O8 P1 c1(=O)(c(N)c(nc([nH]1)N)NC2(OC(C(O)C2O)COP(O)(O)=O)) 3.5.4.25 H2O + GTP = diphosphate + 2,5-diamino-6-(ribosylamino)-4-(3H)-pyrimidinone 5'-phosphate + formate flavin biosynthesis 2,5-diamino-6-(ribosylamino)-4-(3H)-pyrimidinone 5'-phosphate 2,5-diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine*DARP 353.228 C9 H16 N5 O8 P1 c1(=O)(c(N)c(nc([nH]1)N)NC2(OC(C(O)C2O)COP(O)(O)=O)) 3.5.4.26 H2O + 2,5-diamino-6-(ribosylamino)-4-(3H)-pyrimidinone 5'-phosphate = 5-amino-6-(5'-phosphoribosylamino)uracil + ammonia flavin biosynthesis galactopinitol A O-α-D-galactopyranosyl-(1->2)-4-O-methyl-chiro-inositol 356.326 C13 H24 O11 C1(OC(CO)C(O)C(O)C(O)1)OC2(C(O)C(OC)C(O)C(O)C(O)2) 2.4.1.- D-pinitol + galactinol = galactopinitol A + myo-inositol galactosylcyclitol biosynthesis galactopinitol A O-α-D-galactopyranosyl-(1->2)-4-O-methyl-chiro-inositol 356.326 C13 H24 O11 C1(OC(CO)C(O)C(O)C(O)1)OC2(C(O)C(OC)C(O)C(O)C(O)2) 2.4.1.- galactopinitol A + galactinol = ciceritol + myo-inositol galactosylcyclitol biosynthesis α-D-galactose 1-phosphate galactose-1P*galactose-1-P*D-galactose-1-phosphate*galactose-1-phosphate 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) LIGAND-CPD:C00446:*CAS:2255-14-3 2.7.7.10 α-D-galactose 1-phosphate + UTP = UDP-galactose + diphosphate galactose degradation II α-D-galactose 1-phosphate galactose-1P*galactose-1-P*D-galactose-1-phosphate*galactose-1-phosphate 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) LIGAND-CPD:C00446:*CAS:2255-14-3 2.7.1.6 ATP = α-D-galactose 1-phosphate + ADP galactose degradation II α-D-galactose 1-phosphate galactose-1P*galactose-1-P*D-galactose-1-phosphate*galactose-1-phosphate 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) LIGAND-CPD:C00446:*CAS:2255-14-3 2.7.1.6 ATP = α-D-galactose 1-phosphate + ADP UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) α-D-galactose 1-phosphate galactose-1P*galactose-1-P*D-galactose-1-phosphate*galactose-1-phosphate 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) LIGAND-CPD:C00446:*CAS:2255-14-3 2.7.7.12 UDP-D-glucose + α-D-galactose 1-phosphate = α-D-glucose 1-phosphate + UDP-galactose UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) deoxyadenosine 2'-deoxyadenosine 251.244 C10 H13 N5 O3 [CH]1([CH2][CH](O)[CH](O1)CO)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00559:*CAS:958-09-8: H2O + deoxyadenosine = ammonia + deoxyinosine salvage pathways of adenine, hypoxanthine, and their nucleosides deoxyadenosine 2'-deoxyadenosine 251.244 C10 H13 N5 O3 [CH]1([CH2][CH](O)[CH](O1)CO)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00559:*CAS:958-09-8: adenine + deoxyribose-1-phosphate = deoxyadenosine salvage pathways of adenine, hypoxanthine, and their nucleosides indole-3-acetonitrile indole-3-ylacetonitrile*3-indoleacetonitrile*(indole-3-yl)acetonitrile 156.187 C10 H8 N2 c1(c(CC#N)c2(c([nH]1)cccc2)) 4.2.1.84 indole-3-acetonitrile + H2O = indole-3-acetamide IAA biosynthesis IV indole-3-acetonitrile indole-3-ylacetonitrile*3-indoleacetonitrile*(indole-3-yl)acetonitrile 156.187 C10 H8 N2 c1(c(CC#N)c2(c([nH]1)cccc2)) 3.5.5.1 indole-3-acetonitrile + H2O = ammonia + indole-3-acetate IAA biosynthesis I indole-3-acetonitrile indole-3-ylacetonitrile*3-indoleacetonitrile*(indole-3-yl)acetonitrile 156.187 C10 H8 N2 c1(c(CC#N)c2(c([nH]1)cccc2)) 4.99.1.6 indole-3-acetaldoxime = indole-3-acetonitrile + H2O IAA biosynthesis I CDP-ethanolamine cytidine diphosphate ethanolamine 446.247 C11 H20 N4 O11 P2 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)OP(O)(=O)OCCN)) LIGAND-CPD:C00570:*CAS:3036-18-8 2.7.7.14 phosphoryl-ethanolamine + CTP = CDP-ethanolamine + diphosphate phospholipid biosynthesis II CDP-ethanolamine cytidine diphosphate ethanolamine 446.247 C11 H20 N4 O11 P2 c1(n(c(=O)nc(N)c1)C2(OC(C(O)C(O)2)COP(O)(=O)OP(O)(=O)OCCN)) LIGAND-CPD:C00570:*CAS:3036-18-8 2.7.8.1 CDP-ethanolamine = CMP phospholipid biosynthesis II 2-acetolactate (S)-2-hydroxy-2-methyl-3-oxobutanoate*α-acetolactate 132.116 C5 H8 O4 CC(=O)C(C)(O)C(O)=O PUBCHEM:440878:*LIGAND-CPD:C06010: 1.1.1.86 2,3-dihydroxy-isovalerate + NADP+ = 2-acetolactate + NADPH + H+ valine biosynthesis 2-acetolactate (S)-2-hydroxy-2-methyl-3-oxobutanoate*α-acetolactate 132.116 C5 H8 O4 CC(=O)C(C)(O)C(O)=O PUBCHEM:440878:*LIGAND-CPD:C06010: 2.2.1.6 pyruvate = 2-acetolactate + CO2 valine biosynthesis acetoacetyl-CoA acetoacetyl-S-CoA 851.608 C25 H40 N7 O18 P3 S1 CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00332:*CAS:1420-36-6 1.1.1.35 acetoacetyl-CoA + NADH = 3-hydroxybutyryl-CoA + NAD+ acetyl CoA fermentation to butyrate acetoacetyl-CoA acetoacetyl-S-CoA 851.608 C25 H40 N7 O18 P3 S1 CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00332:*CAS:1420-36-6 1.1.1.35 acetoacetyl-CoA + NADH = 3-hydroxybutyryl-CoA + NAD+ glutaryl-CoA degradation acetoacetyl-CoA acetoacetyl-S-CoA 851.608 C25 H40 N7 O18 P3 S1 CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00332:*CAS:1420-36-6 1.1.1.36 acetoacetyl-CoA + NADPH = 3-hydroxybutyryl-CoA + NADP+ ethanol fermentation to acetate acetoacetyl-CoA acetoacetyl-S-CoA 851.608 C25 H40 N7 O18 P3 S1 CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00332:*CAS:1420-36-6 2.3.1.9 acetyl-CoA = acetoacetyl-CoA + coenzyme A acetyl CoA fermentation to butyrate acetoacetyl-CoA acetoacetyl-S-CoA 851.608 C25 H40 N7 O18 P3 S1 CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00332:*CAS:1420-36-6 2.3.1.9 acetyl-CoA = acetoacetyl-CoA + coenzyme A mevalonate pathway acetoacetyl-CoA acetoacetyl-S-CoA 851.608 C25 H40 N7 O18 P3 S1 CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00332:*CAS:1420-36-6 2.3.1.9 acetyl-CoA = acetoacetyl-CoA + coenzyme A glutaryl-CoA degradation acetoacetyl-CoA acetoacetyl-S-CoA 851.608 C25 H40 N7 O18 P3 S1 CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00332:*CAS:1420-36-6 2.3.1.9 acetyl-CoA = acetoacetyl-CoA + coenzyme A ethanol fermentation to acetate acetoacetyl-CoA acetoacetyl-S-CoA 851.608 C25 H40 N7 O18 P3 S1 CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C00332:*CAS:1420-36-6 2.3.3.10 acetoacetyl-CoA + H2O + acetyl-CoA = coenzyme A + 3-hydroxy-3-methyl-glutaryl-CoA mevalonate pathway 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 299.116 C6 H11 N3 O7 P2 c1(c(c(N)nc(C)n1)COP(O)(=O)OP(O)(=O)O) CAS:745-65-3:*LIGAND-CPD:C04752:*CAS:841-01-0 2.5.1.3 4-methyl-5-(β-hydroxyethyl)thiazole phosphate + 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate = thiamine-phosphate + diphosphate thiamine biosynthesis 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 299.116 C6 H11 N3 O7 P2 c1(c(c(N)nc(C)n1)COP(O)(=O)OP(O)(=O)O) 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 L-2-amino-acid L-Amino acid C2 H4 N1 O2 R1 LIGAND-CPD:C00151: 2.3.2.4 (5-L-glutamyl)-L-amino acid = L-2-amino-acid + 5-oxoproline γ-glutamyl cycle acrylonitrile 53.063 C3 H3 N1 C(#N)C=C NCI:6362*CAS:107-13-1 3.5.5.7 acrylonitrile + H2O = acrylate + ammonia acrylonitrile degradation acrylonitrile 53.063 C3 H3 N1 C(#N)C=C NCI:6362*CAS:107-13-1 4.2.1.84 acrylonitrile + H2O = acrylamide acrylonitrile degradation cycloartenol 9β,19-cyclo-24-lanosten-3β-ol 426.724 C30 H50 O1 CC(C)=CCCC(C)C1(C5(C)(C(C)(CC1)C2(C4(C3([CH](CC2)C(C)(C)C(O)CC3)(C4))(CC5)))) CAS:469-38-5 5.4.99.8 (S)-2,3-Epoxysqualene = cycloartenol sterol biosynthesis cycloartenol 9β,19-cyclo-24-lanosten-3β-ol 426.724 C30 H50 O1 CC(C)=CCCC(C)C1(C5(C)(C(C)(CC1)C2(C4(C3([CH](CC2)C(C)(C)C(O)CC3)(C4))(CC5)))) CAS:469-38-5 2.1.1.41 S-adenosyl-L-methionine + cycloartenol = S-adenosyl-L-homocysteine + 24-methylenecycloartenol sterol biosynthesis inosine hypoxanthine-ribose*iso-prinosine*riboxine 268.229 C10 H12 N4 O5 C(O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) LIGAND-CPD:C00294:*CAS:58-63-9 3.5.4.4 H2O + adenosine = ammonia + inosine salvage pathways of adenine, hypoxanthine, and their nucleosides inosine hypoxanthine-ribose*iso-prinosine*riboxine 268.229 C10 H12 N4 O5 C(O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) LIGAND-CPD:C00294:*CAS:58-63-9 3.5.4.4 H2O + adenosine = ammonia + inosine salvage pathways of purine nucleosides inosine hypoxanthine-ribose*iso-prinosine*riboxine 268.229 C10 H12 N4 O5 C(O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) LIGAND-CPD:C00294:*CAS:58-63-9 3.2.2.2 inosine + H2O = hypoxanthine + D-ribose purine degradation inosine hypoxanthine-ribose*iso-prinosine*riboxine 268.229 C10 H12 N4 O5 C(O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) LIGAND-CPD:C00294:*CAS:58-63-9 3.2.2.2 inosine + H2O = hypoxanthine + D-ribose salvage pathways of purine nucleosides II (plant) inosine hypoxanthine-ribose*iso-prinosine*riboxine 268.229 C10 H12 N4 O5 C(O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) LIGAND-CPD:C00294:*CAS:58-63-9 2.7.1.73 inosine + ATP = inosine-5'-phosphate + ADP salvage pathways of adenine, hypoxanthine, and their nucleosides inosine hypoxanthine-ribose*iso-prinosine*riboxine 268.229 C10 H12 N4 O5 C(O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) LIGAND-CPD:C00294:*CAS:58-63-9 2.7.1.73 inosine + ATP = inosine-5'-phosphate + ADP salvage pathways of purine nucleosides inosine hypoxanthine-ribose*iso-prinosine*riboxine 268.229 C10 H12 N4 O5 C(O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) LIGAND-CPD:C00294:*CAS:58-63-9 2.7.1.73 inosine + ATP = inosine-5'-phosphate + ADP salvage pathways of purine nucleosides II (plant) inosine hypoxanthine-ribose*iso-prinosine*riboxine 268.229 C10 H12 N4 O5 C(O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) LIGAND-CPD:C00294:*CAS:58-63-9 2.4.2.- inosine = ribose-1-phosphate + hypoxanthine salvage pathways of adenine, hypoxanthine, and their nucleosides inosine hypoxanthine-ribose*iso-prinosine*riboxine 268.229 C10 H12 N4 O5 C(O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) LIGAND-CPD:C00294:*CAS:58-63-9 2.4.2.- inosine = ribose-1-phosphate + hypoxanthine salvage pathways of purine nucleosides inosine hypoxanthine-ribose*iso-prinosine*riboxine 268.229 C10 H12 N4 O5 C(O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) LIGAND-CPD:C00294:*CAS:58-63-9 3.1.3.5 inosine-5'-phosphate + H2O = inosine purine degradation inosine hypoxanthine-ribose*iso-prinosine*riboxine 268.229 C10 H12 N4 O5 C(O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]cn3))) LIGAND-CPD:C00294:*CAS:58-63-9 3.1.3.5 inosine-5'-phosphate + H2O = inosine salvage pathways of purine nucleosides II (plant) dolichyl-phosphate dolichol-phosphate*Dolychol phosphate 1189.902 C80 H133 O4 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(O)(=O)O 2.4.1.117 dolichyl-phosphate + UDP-D-glucose = dolichyl β-D-glucosyl phosphate + UDP dolichyl-diphosphooligosaccharide biosynthesis dolichyl-phosphate dolichol-phosphate*Dolychol phosphate 1189.902 C80 H133 O4 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(O)(=O)O glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-glucosyl phosphate = (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis dolichyl-phosphate dolichol-phosphate*Dolychol phosphate 1189.902 C80 H133 O4 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(O)(=O)O (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis dolichyl-phosphate dolichol-phosphate*Dolychol phosphate 1189.902 C80 H133 O4 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(O)(=O)O 2.7.1.108 dolichol + CTP = dolichyl-phosphate + CDP dolichyl-diphosphooligosaccharide biosynthesis dolichyl-phosphate dolichol-phosphate*Dolychol phosphate 1189.902 C80 H133 O4 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(O)(=O)O (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-glucosyl phosphate = glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis dolichyl-phosphate dolichol-phosphate*Dolychol phosphate 1189.902 C80 H133 O4 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(O)(=O)O (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis dolichyl-phosphate dolichol-phosphate*Dolychol phosphate 1189.902 C80 H133 O4 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(O)(=O)O (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis dolichyl-phosphate dolichol-phosphate*Dolychol phosphate 1189.902 C80 H133 O4 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(O)(=O)O (mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate = (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis dolichyl-phosphate dolichol-phosphate*Dolychol phosphate 1189.902 C80 H133 O4 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(O)(=O)O 2.7.8.15 dolichyl-phosphate + UDP-N-acetyl-D-glucosamine = N-acetylglucosaminyl-diphosphodolichol + UMP dolichyl-diphosphooligosaccharide biosynthesis dolichyl-phosphate dolichol-phosphate*Dolychol phosphate 1189.902 C80 H133 O4 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(O)(=O)O (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-glucosyl phosphate = oligosaccharide-diphosphodolichol + dolichyl-phosphate dolichyl-diphosphooligosaccharide biosynthesis dolichyl-phosphate dolichol-phosphate*Dolychol phosphate 1189.902 C80 H133 O4 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(O)(=O)O 2.4.1.83 dolichyl-phosphate + GDP-D-mannose = dolichyl β-D-mannosyl phosphate + GDP dolichyl-diphosphooligosaccharide biosynthesis thiosulfate S2O3*S2O32-*S2O3-2 112.118 O3 S2 S([O-])([S-])(=O)=O LIGAND-CPD:C00320: 2.8.1.1 thiosulfate + hydrogen cyanide = sulfite + thiocyanate thiosulfate disproportionation III (rhodanese) UDP-2,3-bis(3-hydroxymyristoyl)glucosamine UDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine*UDP-2,3-diacyl-glucosamine 1018.037 C43 H77 N3 O20 P2 CCCCCCCCCCCC(O)CC(=O)NC3(C(OP(O)(=O)OP(O)(=O)OCC1(OC(C(O)C(O)1)n2(c(=O)[nH]c(=O)cc2)))OC(CO)C(O)C3OC(=O)CC(O)CCCCCCCCCCC) LIGAND-CPD:C04652: 2.4.1.182 2,3-bis(3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate + UDP-2,3-bis(3-hydroxymyristoyl)glucosamine = lipid A disaccharide + UDP lipid-A-precursor biosynthesis UDP-2,3-bis(3-hydroxymyristoyl)glucosamine UDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine*UDP-2,3-diacyl-glucosamine 1018.037 C43 H77 N3 O20 P2 CCCCCCCCCCCC(O)CC(=O)NC3(C(OP(O)(=O)OP(O)(=O)OCC1(OC(C(O)C(O)1)n2(c(=O)[nH]c(=O)cc2)))OC(CO)C(O)C3OC(=O)CC(O)CCCCCCCCCCC) LIGAND-CPD:C04652: 2.3.1.- UDP-3-O-(3-hydroxymyristoyl)glucosamine = UDP-2,3-bis(3-hydroxymyristoyl)glucosamine lipid-A-precursor biosynthesis UDP-2,3-bis(3-hydroxymyristoyl)glucosamine UDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine*UDP-2,3-diacyl-glucosamine 1018.037 C43 H77 N3 O20 P2 CCCCCCCCCCCC(O)CC(=O)NC3(C(OP(O)(=O)OP(O)(=O)OCC1(OC(C(O)C(O)1)n2(c(=O)[nH]c(=O)cc2)))OC(CO)C(O)C3OC(=O)CC(O)CCCCCCCCCCC) LIGAND-CPD:C04652: H2O + UDP-2,3-bis(3-hydroxymyristoyl)glucosamine = 2,3-bis(3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate + UMP lipid-A-precursor biosynthesis 18:2-16:0-MGDG 1-18:2-2-16:0-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-hexadecanoyl-3-O-beta-D-galactosyl-sn-glycerol 755.083 C43 H78 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-16:0-MGDG = 18:3-16:0-MGDG glycolipid desaturation 18:2-16:0-MGDG 1-18:2-2-16:0-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-hexadecanoyl-3-O-beta-D-galactosyl-sn-glycerol 755.083 C43 H78 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-16:0-MGDG = 18:2-16:1-MGDG glycolipid desaturation 18:2-16:0-MGDG 1-18:2-2-16:0-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-hexadecanoyl-3-O-beta-D-galactosyl-sn-glycerol 755.083 C43 H78 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:1-16:0-MGDG = 18:2-16:0-MGDG glycolipid desaturation 1,4-dihydroxy-2-naphthoate DHNA 204.182 C11 H8 O4 C(=O)(O)c1(c(O)c2(c(c(O)c1)cccc2)) LIGAND-CPD:C03657: 1,4-dihydroxy-2-naphthoate + phytyl-PP = demethylphylloquinone + CO2 + diphosphate phylloquinone biosynthesis 1,4-dihydroxy-2-naphthoate DHNA 204.182 C11 H8 O4 C(=O)(O)c1(c(O)c2(c(c(O)c1)cccc2)) LIGAND-CPD:C03657: 4.1.3.36 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA = coenzyme A + 1,4-dihydroxy-2-naphthoate phylloquinone biosynthesis 1,4-dihydroxy-2-naphthoate DHNA 204.182 C11 H8 O4 C(=O)(O)c1(c(O)c2(c(c(O)c1)cccc2)) LIGAND-CPD:C03657: octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate = demethylmenaquinone-8 + diphosphate + CO2 menaquinone biosynthesis 1,4-dihydroxy-2-naphthoate DHNA 204.182 C11 H8 O4 C(=O)(O)c1(c(O)c2(c(c(O)c1)cccc2)) LIGAND-CPD:C03657: 4.1.3.36 O-succinylbenzoyl-CoA = coenzyme A + 1,4-dihydroxy-2-naphthoate menaquinone biosynthesis 7-deoxyloganin 374.387 C17 H26 O9 CC2([CH]1(C(OC=C([CH]1CC2)C(=O)OC)OC3(C(O)C(O)C(O)C(O3)CO))) 1.14.13.74 O2 + NADPH + 7-deoxyloganin = H2O + NADP+ + loganin secologanin and strictosidine biosynthesis 7-deoxyloganin 374.387 C17 H26 O9 CC2([CH]1(C(OC=C([CH]1CC2)C(=O)OC)OC3(C(O)C(O)C(O)C(O3)CO))) unknown = 7-deoxyloganin secologanin and strictosidine biosynthesis indole 117.15 C8 H7 N1 c1([nH]c2(c(c1)cccc2)) LIGAND-CPD:C00463:*CAS:120-72-9 indole + acetate = indole-3-acetate IAA biosynthesis I indole 117.15 C8 H7 N1 c1([nH]c2(c(c1)cccc2)) LIGAND-CPD:C00463:*CAS:120-72-9 indole-3-glycerol-phosphate = indole + sn-glycerol-3-phosphate IAA biosynthesis I indole 117.15 C8 H7 N1 c1([nH]c2(c(c1)cccc2)) LIGAND-CPD:C00463:*CAS:120-72-9 indole-3-glycerol-phosphate = indole + D-glyceraldehyde-3-phosphate tryptophan biosynthesis indole 117.15 C8 H7 N1 c1([nH]c2(c(c1)cccc2)) LIGAND-CPD:C00463:*CAS:120-72-9 4.2.1.20 indole + L-serine = L-tryptophan + H2O tryptophan biosynthesis fuculose-1-phosphate L-fuculose-1-phosphate*fuculose-1-P*L-fuculose-1-P 244.138 C6 H13 O8 P1 C1(C(O)C(O)C(O)C(C)O1)(OP(O)(=O)O) LIGAND-CPD:C01099:*CAS:92418-41-2 4.1.2.17 fuculose-1-phosphate = L-lactaldehyde + dihydroxy-acetone-phosphate fucose degradation fuculose-1-phosphate L-fuculose-1-phosphate*fuculose-1-P*L-fuculose-1-P 244.138 C6 H13 O8 P1 C1(C(O)C(O)C(O)C(C)O1)(OP(O)(=O)O) LIGAND-CPD:C01099:*CAS:92418-41-2 2.7.1.51 L-fuculose + ATP = fuculose-1-phosphate + ADP fucose degradation S-adenosyl-4-methylthio-2-oxobutanoate 398.413 C15 H20 N5 O6 S1 C(CC(=O)C(=O)O)[S+](C)CC1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 II S-adenosyl-4-methylthio-2-oxobutanoate 398.413 C15 H20 N5 O6 S1 C(CC(=O)C(=O)O)[S+](C)CC1(OC(C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3))) 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 I psoralen phytoalexin*7H-Furo[3,2-g][1]benzopyran-7-one*6-hydroxy-5-benzofuranacrylic acid γ-lactone*ficusin*furocoumarin 186.167 C11 H6 O3 C1(OC2(=C(C=C1)C=C3(C(=C2)OC=C3)))(=O) NCI:404562 psoralen + NADPH + H2O = bergaptol + NADP+ linear furanocoumarin biosynthesis psoralen phytoalexin*7H-Furo[3,2-g][1]benzopyran-7-one*6-hydroxy-5-benzofuranacrylic acid γ-lactone*ficusin*furocoumarin 186.167 C11 H6 O3 C1(OC2(=C(C=C1)C=C3(C(=C2)OC=C3)))(=O) NCI:404562 marmesin + NADPH + O2 = psoralen + NADP+ + acetone + H2O linear furanocoumarin biosynthesis GA9 gibberellin A9*gibberellin A9*GA9 316.396 C19 H24 O4 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(CCC3)(C)[CH]4C5C(=O)O)))) 1.14.11.- GA9 + α-ketoglutarate + O2 = GA51 + succinate + CO2 gibberellin inactivation GA9 gibberellin A9*gibberellin A9*GA9 316.396 C19 H24 O4 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(CCC3)(C)[CH]4C5C(=O)O)))) 1.14.11.- GA9 + α-ketoglutarate + O2 = GA4 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) GA9 gibberellin A9*gibberellin A9*GA9 316.396 C19 H24 O4 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(CCC3)(C)[CH]4C5C(=O)O)))) 1.14.11.- GA24 + O2 + α-ketoglutarate = GA9 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) phytocassane D 316.439 C20 H28 O3 CC2(C(C=C)=CC(=O)[CH]1(C3([CH](CC[CH]12)C(C)(C)C(O)C(C3)=O)(C))) ent-cassa-12,15-diene-2,3α-ol-11-keto = phytocassane D phytocassane biosynthesis UDP-L-arabinose UDP-arabinose*UDP-β-L-arabinose 536.279 C14 H22 N2 O16 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)CO3))) 2.7.7.37 β-L-arabinose 1-phosphate + UTP = UDP-L-arabinose + diphosphate UDP-L-arabinose biosynthesis II (from L-arabinose) UDP-L-arabinose UDP-arabinose*UDP-β-L-arabinose 536.279 C14 H22 N2 O16 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)CO3))) 2.4.2.34 UDP-L-arabinose + indol-3-yl-acetyl-myo-inositol = UDP + indole-3-yl-acetyl-myo-inositol L-arabinoside IAA conjugate biosynthesis I UDP-L-arabinose UDP-arabinose*UDP-β-L-arabinose 536.279 C14 H22 N2 O16 P2 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OC3(C(O)C(O)C(O)CO3))) 5.1.3.5 UDP-L-arabinose = UDP-D-xylose UDP-L-arabinose biosynthesis I (from UDP-xylose) 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.10 L-homocysteine + S-adenosyl-L-methionine = 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- 2-methyl-6-phytyl-1,4-benzoquinone + S-adenosyl-L-methionine = 2,3-dimethyl-6-phytyl-1,4-benzoquinone + 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.68 5-hydroxy-coniferaldehyde + S-adenosyl-L-methionine = 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.11 Mg-protoporphyrin + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + Mg-protoporphyrin monomethyl ester chlorophyllide a 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- N-methyl-β-alanine + S-adenosyl-L-methionine = N,N-dimethyl-β-alanine + S-adenosyl-L-homocysteine β-alanine betaine 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- N,N-dimethyl-β-alanine + S-adenosyl-L-methionine = β-alanine betaine + S-adenosyl-L-homocysteine β-alanine betaine 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.103 N-dimethylethanolamine phosphate + S-adenosyl-L-methionine = 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- 2-methyl-6-solanyl-1,4-benzoquinone + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine plastoquinone 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 demethylphylloquinone + S-adenosyl-L-methionine = phylloquinone + S-adenosyl-L-homocysteine phylloquinone 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.49 nicotine + S-adenosyl-L-methionine = nicotine isomethonium ion + S-adenosyl-L-homocysteine nicotine degradation 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.46 daidzein + S-adenosyl-L-methionine = formononetin + S-adenosyl-L-homocysteine pterocarpan 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.95 δ-tocopherol + S-adenosyl-L-methionine = 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.143 24-methylenelophenol + S-adenosyl-L-methionine = 24-ethylidenelophenol + S-adenosyl-L-homocysteine 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.69 bergaptol + S-adenosyl-L-methionine = bergapten + S-adenosyl-L-homocysteine linear furanocoumarin 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 demethylmenaquinone-8 + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + menaquinone-8 menaquinone 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 3.3.1.1 S-adenosyl-L-homocysteine + H2O = L-homocysteine + adenosine S-adenosyl-L-methionine 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- quercetin + S-adenosyl-L-methionine = isorhamnetin + S-adenosyl-L-homocysteine flavonol 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.49 β-alanine + S-adenosyl-L-methionine = N-methyl-β-alanine + S-adenosyl-L-homocysteine β-alanine betaine 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.79 oleate + S-adenosyl-L-methionine = 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.68 caffeate + S-adenosyl-L-methionine = 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.68 caffeate + S-adenosyl-L-methionine = 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.141 (-)-jasmonate + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + (-)-jasmonic acid methyl ester jasmonic 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.68 5-hydroxy-ferulic-acid + S-adenosyl-L-methionine = 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2-hydroxyisoflavanone + S-adenosyl-L-methionine = 2,7-dihydroxy-4'-methoxyisoflavanone + S-adenosyl-L-homocysteine pterocarpan 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.41 S-adenosyl-L-methionine + cycloartenol = S-adenosyl-L-homocysteine + 24-methylenecycloartenol 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + feruloyl-CoA 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.104 caffeoyl-CoA + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + feruloyl-CoA 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.- S-adenosyl-L-methionine = S-adenosyl-L-homocysteine S-adenosyl-L-methionine 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 C(CC(N)C(O)=O)SC[CH]1(O[CH]([CH](O)[CH]1O)N2(c3(c(N=C2)c(N)ncn3))) LIGAND-CPD:C00021:*CAS:979-92-0 2.1.1.95 γ-tocopherol + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + α-tocopherol vitamin E biosynthesis methanethiol methyl-mercaptan*methanethiol*methylmercaptan*mercaptomethane*thiomethane*methyl sulfhydrate*thiomethyl alcohol 48.103 C1 H4 S1 CS PUBCHEM:878: 4.4.1.11 L-methionine + H2O = methanethiol + ammonia + 2-oxobutanoate methionine degradation II pyrroline-hydroxy-carboxylate L-Δ1-pyrroline 3-hydroxy-5-carboxylate 129.115 C5 H7 N1 O3 C(O)(=O)C1(N=CC(O)C1) 1.5.1.12 pyrroline-hydroxy-carboxylate + NAD+ + H2O = L-erythro-4-hydroxy-glutamate + NADH 4-hydroxyproline degradation I pyrroline-hydroxy-carboxylate L-Δ1-pyrroline 3-hydroxy-5-carboxylate 129.115 C5 H7 N1 O3 C(O)(=O)C1(N=CC(O)C1) L-4-hydroxy-proline + O2 = pyrroline-hydroxy-carboxylate + H2O 4-hydroxyproline degradation I 2'-hydroxynicotine 178.233 C10 H14 N2 O1 c1(ncc(cc1)C2(O)(N(C)CCC2)) 1.14.14.1 nicotine + NADPH + O2 = 2'-hydroxynicotine + NADP+ + H2O nicotine degradation II 2'-hydroxynicotine 178.233 C10 H14 N2 O1 c1(ncc(cc1)C2(O)(N(C)CCC2)) 2'-hydroxynicotine = 4-(methylamino)-1-(3-pyridyl)-1-butanone nicotine degradation II D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(=O)O PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 2.7.1.19 D-ribulose-5-phosphate + ATP = ADP Calvin cycle D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(=O)O PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 D-ribulose-5-phosphate = 3,4-dihydroxy-2-butanone-4-P + formate flavin biosynthesis D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(=O)O 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 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(=O)O PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 5.1.3.1 D-ribulose-5-phosphate = D-xylulose-5-phosphate Calvin cycle D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(=O)O 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 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(=O)O PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 5.1.3.1 D-ribulose-5-phosphate = D-xylulose-5-phosphate glucose fermentation to lactate II D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(=O)O PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 5.3.1.6 D-ribose-5-phosphate = D-ribulose-5-phosphate Calvin cycle D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(=O)O 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 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(=O)O PUBCHEM:439184:*LIGAND-CPD:C00199:*CAS:4151-19-3 5.3.1.6 D-ribose-5-phosphate = D-ribulose-5-phosphate glucose fermentation to lactate II D-ribulose-5-phosphate ribulose-5P*D-ribulose-5-P*ribulose-5-P*ribulose-5-phosphate 230.111 C5 H11 O8 P1 C(O)C(=O)C(O)C(O)COP(O)(=O)O 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 483.158 C9 H16 N3 O14 P3 c1(n(c(=O)nc(c1)N)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00063:*CAS:65-47-4 6.3.2.5 D-4'-phosphopantothenate + L-cysteine + CTP = R-4'-phosphopantothenoyl-L-cysteine + diphosphate + CMP coenzyme A biosynthesis CTP cytidine-triphosphate*cytidine-5'-triphosphate 483.158 C9 H16 N3 O14 P3 c1(n(c(=O)nc(c1)N)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.14 phosphoryl-ethanolamine + CTP = CDP-ethanolamine + diphosphate phospholipid biosynthesis II CTP cytidine-triphosphate*cytidine-5'-triphosphate 483.158 C9 H16 N3 O14 P3 c1(n(c(=O)nc(c1)N)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00063:*CAS:65-47-4 2.7.1.108 dolichol + CTP = dolichyl-phosphate + CDP dolichyl-diphosphooligosaccharide biosynthesis CTP cytidine-triphosphate*cytidine-5'-triphosphate 483.158 C9 H16 N3 O14 P3 c1(n(c(=O)nc(c1)N)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00063:*CAS:65-47-4 CTP = dCTP + H2O de novo biosynthesis of pyrimidine deoxyribonucleotides CTP cytidine-triphosphate*cytidine-5'-triphosphate 483.158 C9 H16 N3 O14 P3 c1(n(c(=O)nc(c1)N)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.15 phosphoryl-choline + CTP = CDP-choline + diphosphate phospholipid biosynthesis II CTP cytidine-triphosphate*cytidine-5'-triphosphate 483.158 C9 H16 N3 O14 P3 c1(n(c(=O)nc(c1)N)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.15 phosphoryl-choline + CTP = CDP-choline + diphosphate choline biosynthesis III CTP cytidine-triphosphate*cytidine-5'-triphosphate 483.158 C9 H16 N3 O14 P3 c1(n(c(=O)nc(c1)N)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00063:*CAS:65-47-4 2.7.4.6 CDP + ATP = CTP + ADP de novo biosynthesis of pyrimidine ribonucleotides CTP cytidine-triphosphate*cytidine-5'-triphosphate 483.158 C9 H16 N3 O14 P3 c1(n(c(=O)nc(c1)N)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) 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 483.158 C9 H16 N3 O14 P3 c1(n(c(=O)nc(c1)N)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.41 CTP = diphosphate phospholipid biosynthesis I CTP cytidine-triphosphate*cytidine-5'-triphosphate 483.158 C9 H16 N3 O14 P3 c1(n(c(=O)nc(c1)N)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.41 CTP = diphosphate phospholipid biosynthesis II CTP cytidine-triphosphate*cytidine-5'-triphosphate 483.158 C9 H16 N3 O14 P3 c1(n(c(=O)nc(c1)N)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.41 CTP = diphosphate cardiolipin biosynthesis CTP cytidine-triphosphate*cytidine-5'-triphosphate 483.158 C9 H16 N3 O14 P3 c1(n(c(=O)nc(c1)N)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) 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 483.158 C9 H16 N3 O14 P3 c1(n(c(=O)nc(c1)N)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00063:*CAS:65-47-4 2.7.7.60 2-C-methyl-D-erythritol-4-phosphate + CTP = 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + diphosphate methylerythritol phosphate pathway CTP cytidine-triphosphate*cytidine-5'-triphosphate 483.158 C9 H16 N3 O14 P3 c1(n(c(=O)nc(c1)N)C2(OC(C(O)C2O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00063:*CAS:65-47-4 6.3.4.2 ATP + UTP + L-glutamine + H2O = ADP + CTP + L-glutamate de novo biosynthesis of pyrimidine ribonucleotides 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.72 lanosterol + NADPH = 24,25-dihydrolanosterol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.38 NADPH = NADP+ 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.25 NADP+ + shikimate = NADPH + 3-dehydro-shikimate chorismate 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.86 2,3-dihydroxy-isovalerate + NADP+ = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: L-glutamate + ATP + NADPH = ADP + L-glutamate γ-semialdehyde + NADP+ arginine biosynthesis IV 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- coniferyl aldehyde + NADPH + O2 = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.99.7 squalene + NADPH + O2 = (S)-2,3-Epoxysqualene + NADP+ + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: isopentenyladenosine-5'-triphosphate + NADPH + H2O = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) 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 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.86 2-aceto-2-hydroxy-butyrate + NADPH = 2,3-dihydroxy-3-methylvalerate + NADP+ isoleucine biosynthesis 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.- 18-oxooleate + NADP+ + H2O = octadec-9-ene-1,18-dioic-acid + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.17.1.3 leucopelargonidin + NADPH = afzelechin + NADP+ + H2O proanthocyanidin biosynthesis from flavanols 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: liquiritigenin + NADPH + O2 = 6,7,4'-trihydroxyflavanone + NADP+ + H2O 6,7,4'-trihydroxyisoflavone 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- dihydrokaempferol + NADPH + O2 = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: calycosin + NADPH + O2 = pseudobaptigenin + NADP+ + H2O maackiain 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.51 dalbergioidin + NADP+ = 2'-hydroxygenistein + NADPH + H+ kievitone 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate formylTHF 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate tetrahydrofolate 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate formylTHF 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.5.1.3 NADP+ + tetrahydrofolate = NADPH + 7,8-dihydrofolate tetrahydrofolate 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.79 ent-kaurenoate + O2 + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: (+)-isomenthone + NADPH = (+)-isomenthol + NADP+ menthol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.42 NADP+ = NADPH + α-ketoglutarate + CO2 TCA cycle variation 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.42 NADP+ = NADPH + α-ketoglutarate + CO2 respiration (anaerobic) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.42 NADP+ = NADPH + α-ketoglutarate + CO2 TCA 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: isopentenyladenosine-5'-diphosphate + NADPH + H2O = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: chlorophyll b + H2O + NADP+ = 7-hydroxy-chlorophyll a + O2 + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 2.3.1.170 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.70 glutamate-1-semialdehyde + NADP+ = NADPH + H+ 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.36 NADPH = NADP+ 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.21 dihydrokaempferol + NADPH + O2 = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.21 dihydrokaempferol + NADPH + O2 = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.21 dihydrokaempferol + NADPH + O2 = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.70 4,4-dimethyl-5-α-cholesta-8,14-dien-3-β-ol + NADPH = 4,4-dimethyl-5α-cholesta-8-en-3-β-ol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.21 5-dehydro episterol + NADPH = 24-methylenecholesterol + NADP+ 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.11 trans-cinnamate + O2 + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.11 trans-cinnamate + O2 + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.99.- α-carotene + NADPH + O2 = zeinoxanthin + NADP+ + H2O carotenoid 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.38 N-acetyl-L-glutamate 5-semialdehyde + NADP+ = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.193 5-amino-6-(5'-phosphoribitylamino)uracil + NADP+ = 5-amino-6-(5'-phosphoribosylamino)uracil + NADPH + H+ flavin 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.219 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: (+)-cis-isopulegone + NADP+ = (+)-pulegone + NADPH menthol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.75 divinyl protochlorophyllide a + NADPH + H+ + H+ = monovinyl protochlorophyllide a + NADP+ chlorophyllide a 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.3.9 O2 + NADPH + loganin = H2O + NADP+ + secologanin secologanin and strictosidine 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- sitosterol + NADP+ = stigmasterol + NADPH 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.270 4α-methyl-5α-cholesta-8-en-3-one + NADPH = 4α-methyl-cholesta-8-enol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.14.1 cotinine + NADPH + O2 = N'-hydroxymethyl-norcotinine + NADP+ + H2O nicotine degradation 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.6.5.4 monodehydroascorbate + NADPH = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: (+)-pulegone + NADPH = (+)-isomenthone + NADP+ menthol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.271 NADP+ + GDP-L-fucose = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.49 β-D-glucose-6-phosphate + NADP+ = D-glucono-δ-lactone-6-phosphate + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.169 L-pantoate + NADP+ = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.169 L-pantoate + NADP+ = 2-dehydropantoate + NADPH pantothenate 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 2,3-dehydrokievitone + NADPH = kievitone + NADP+ kievitone 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.8.1.2 H2O + NADP+ + hydrogen sulfide = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: hydroxycinnamoyl-CoA + NADP+ = oxocinnamoyl-CoA + NADPH salicylate 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADP+ + H2O + formate cholesterol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADP+ + H2O + formate cholesterol biosynthesis III (via desmosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.70 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol + O2 + NADPH = 4,4-dimethyl-5-α-cholesta-8,14-dien-3-β-ol + formate + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.236 NADP+ + pseudotropine = NADPH + tropinone calystegine 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.41 L-glutamate γ-semialdehyde + NADP+ = L-glutamate-5-phosphate + NADPH + H+ proline 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 7-hydroxy-chlorophyllide a + O2 + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- oleate + NADPH + O2 = 18-hydroxyoleate + NADP+ + H2O cutin 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- oleate + NADPH + O2 = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 2.7.1.86 NADH + ATP = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.11 NADP+ + L-aspartate-semialdehyde = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.11 NADP+ + L-aspartate-semialdehyde = NADPH + L-aspartyl-4-phosphate lysine 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.11 NADP+ + L-aspartate-semialdehyde = NADPH + L-aspartyl-4-phosphate lysine 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.11 NADP+ + L-aspartate-semialdehyde = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol + O2 + NADPH = 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.21 7-dehydrodesmosterol + NADPH = desmosterol + NADP+ cholesterol biosynthesis III (via desmosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: NADPH = NADP+ fatty acid elongation -- unsaturated 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- (5α)-campestan-3-one + O2 + NADPH = (22α)-hydroxy-5α-campestan-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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.219 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- geranylgeranyl diphosphate + NADPH = dihydrogeranylgeranyl-PP + NADP+ phytyl-PP 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.9 O2 + NADPH + kynurenine = H2O + NADP+ + 3-hydroxy-L-kynurenine tryptophan degradation III (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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.8.1.7 glutathione + NADP+ = glutathione disulfide + NADPH + H+ 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.44 coumaroyl-CoA + NADPH = coumaraldehyde + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.88 dihydroquercetin + NADPH + O2 = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- palmitate + NADPH + O2 = 16-hydroxypalmitate + NADP+ + H2O cutin 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.195 coniferyl aldehyde + NADPH = coniferyl 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.14.1 N'-hydroxymethyl-norcotinine + NADPH + O2 = norcotinine + NADP+ + H2O nicotine degradation 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- campestanol + O2 + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: (-)-isopiperitenone + NADP+ = (+)-cis-isopulegone + NADPH menthol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.5.1.8 H2O + NADP+ + saccharopine = NADPH + α-ketoglutarate + L-lysine 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: (+)-isomenthone + NADPH = (+)-neoisomenthol + NADP+ menthol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 3-deoxy-capsidiol + O2 + NADPH = capsidiol + H2O + NADP+ capsidiol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: isopentenyladenosine-5'-monophosphate + NADPH + H2O = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.246 (-)-sophorol + NADPH = (-)-maackiain + NADP+ + H2O maackiain 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.219 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: marmesin + NADPH + O2 = psoralen + NADP+ + acetone + H2O linear furanocoumarin 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.81 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = divinyl protochlorophyllide a + NADP+ + H2O chlorophyllide a 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.44 feruloyl-CoA + NADPH = coniferyl aldehyde + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- eriodictyol + NADPH + O2 = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.39 O2 + NADPH + L-arginine = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 5-epi-aristolochene + O2 + NADPH = 3-deoxy-capsidiol + H2O + NADP+ capsidiol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.4.1.4 L-glutamate + H2O + NADP+ = ammonia + α-ketoglutarate + NADPH 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.21 5-dehydroavenasterol + NADPH = isofucosterol + NADP+ 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.14.1 cotinine + NADPH + O2 = trans-3'-hydroxycotinine + NADP+ + H2O nicotine degradation 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.79 GA12-aldehyde + NADPH + O2 = GA12 + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.78 ent-kaur-16-en-19-ol + NADPH + H+ + O2 = ent-kaur-16-en-19-al + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.14.1 bupropion + NADPH + O2 = hydroxybupropion + NADP+ + H2O bupropion 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.14.1 acetone + NADPH + O2 = acetol + NADP+ + H2O acetone degradation (to methylglyoxal) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.99.- zeinoxanthin + NADPH + O2 = lutein + NADP+ + H2O carotenoid 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.243 (-)-trans-carveol + NADP+ = (-)-carvone + NADPH + H+ menthol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- 6,7,4'-trihydroxyflavanone + NADPH + O2 = 2,6,7,4'-tetrahydroxyisoflavanone + NADP+ + H2O 6,7,4'-trihydroxyisoflavone 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.14.1 nicotine + NADPH = nicotine-Δ1'5'-iminium ion + NADP+ nicotine 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.14.1 nicotine + NADPH = nicotine-Δ1'5'-iminium ion + NADP+ nicotine degradation 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.70 24,25-dihydrolanosterol + O2 + NADPH = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol + H2O + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.14.1 cotinine + NADPH + O2 = 5'-hydroxycotinine + NADP+ + H2O nicotine degradation 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- 24-epi-campesterol + NADP+ = brassicasterol + NADPH 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.133 NADP+ + dTDP-α-L-rhamnose = NADPH + dTDP-4-dehydro-6-deoxy-L-mannose dTDP-L-rhamnose 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.45 2-hydroxyformononetin + NADPH = (-)-vestitone + NADP+ medicarpin 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.52 formononetin + NADPH + O2 = calycosin + NADP+ + H2O maackiain 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.16 succinate semialdehyde + NADP+ + H2O = NADPH + succinate TCA cycle variation 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.100 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.34 NADP+ + coenzyme A + (R)-mevalonate = NADPH + 3-hydroxy-3-methyl-glutaryl-CoA mevalonate 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.36 acetoacetyl-CoA + NADPH = 3-hydroxybutyryl-CoA + NADP+ ethanol fermentation to acetate 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.70 NADPH + O2 + obtusifoliol + H+ = H2O + NADP+ + formate + (4α)-methyl-(5α)-ergosta-8,14,24(28)-trien-3β-ol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: tryptamine + O2 + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.270 5α-cholesta-8-en-3-one + NADPH = zymostenol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.270 4α-methyl-5α-cholesta-8,24-dien-3-one + NADPH = 4-α-methyl zymosterol + NADP+ cholesterol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.270 4α-methyl-5α-cholesta-8,24-dien-3-one + NADPH = 4-α-methyl zymosterol + NADP+ cholesterol biosynthesis III (via desmosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.70 (4α)-methyl-(5α)-ergosta-8,14,24(28)-trien-3β-ol + NADPH = 4α-methylfecosterol + NADP+ 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.102 NADP+ + sphinganine = NADPH + 3-dehydrosphinganine sphingolipid metabolism 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.72 5α-cholesta-7,24-dien-3β-ol + NADPH = lathosterol + NADP+ cholesterol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- campesterol + NADP+ = crinosterol + NADPH 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: ferulate + NADPH + O2 = 5-hydroxy-ferulic-acid + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.-.- sphinganine + O2 + NADPH = 4-hydroxysphinganine + H2O + NADP+ sphingolipid metabolism 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.5.1.10 2-aminoadipate-6-semialdehyde + NADPH + L-glutamate = saccharopine + NADP+ + H2O lysine biosynthesis IV 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: demethylsuberosin + O2 + NADPH = marmesin + NADP+ + H2O linear furanocoumarin 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.40 NADP+ + malate = NADPH + CO2 + pyruvate gluconeogenesis 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- campesterol + O2 + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: methylglyoxal + NADPH = acetol + NADP+ acetone degradation (to methylglyoxal) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 7-hydroxy-chlorophyll a + H2O + NADP+ = chlorophyll a + O2 + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.78 ent-kaur-16-en-19-al + NADPH + H+ + O2 = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.89 genistein + NADPH + O2 = 2'-hydroxygenistein + NADP+ + H2O wighteone and luteone 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.34 NADPH = NADP+ fatty acid β-oxidation IV (plant, 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.99.- 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.79 ent-7-α-hydroxykaurenoate + NADPH + H+ + O2 = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- benzoate + NADPH + O2 = salicylate + NADP+ + H2O salicylate 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 18-hydroxyoleate + NADPH + O2 = 9,10-epoxy-18-hydroxystearate + NADP+ + H2O cutin 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.45 2'-hydroxypseudobaptigenin + NADPH = (-)-sophorol + NADP+ maackiain 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.70 lanosterol + NADPH + O2 = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.70 lanosterol + NADPH + O2 = 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.81 Mg-protoporphyrin monomethyl ester + NADPH + H+ + O2 = 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.57 dihydrophloroglucinol + NADP+ = phloroglucinol + NADPH gallate degradation III (anaerobic) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.195 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.14 trans-cinnamate + O2 + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: chlorophyllide a + O2 + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: NADPH = NADP+ fatty acid elongation -- unsaturated 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.70 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADPH = 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + NADP+ cholesterol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.70 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADPH = 4,4-dimethyl-5α-cholesta-8,24-dien-3-β-ol + NADP+ cholesterol biosynthesis III (via desmosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.78 ent-kaur-16-ene + O2 + NADPH = H2O + NADP+ + ent-kaur-16-en-19-ol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.14.1 nicotine + NADPH + O2 = 2'-hydroxynicotine + NADP+ + H2O nicotine 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 16-hydroxypalmitate + NADPH + O2 = 10,16-dihydroxypalmitate + NADP+ + H2O cutin 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- campest-4-en-3-one + O2 + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.72 desmosterol + NADPH = cholesterol + NADP+ cholesterol biosynthesis III (via desmosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.- 18-hydroxyoleate + NADP+ = 18-oxooleate + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.53 pseudobaptigenin + NADPH + O2 = 2'-hydroxypseudobaptigenin + NADP+ + H2O maackiain 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.270 5α-cholesta-8,24-dien-3-one + NADPH = zymosterol + NADP+ cholesterol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.270 5α-cholesta-8,24-dien-3-one + NADPH = zymosterol + NADP+ cholesterol biosynthesis III (via desmosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.246 (-)-vestitone + NADPH + H+ = 7,2'-dihydroxy-4'-methoxy-isoflavanol + NADP+ medicarpin 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.2.1.9 D-glyceraldehyde-3-phosphate + NADP+ + H2O = 3-phosphoglycerate + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.2 NADP+ + dihydrouracil = NADPH + uracil β-alanine 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- dihydrogeranylgeranyl-PP + NADPH = tetrahydrogeranylgeranyl-PP + NADP+ phytyl-PP 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.6.6.- L-canaline + NADPH = homoserine + ammonia + NADP+ canavanine 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.42 NADP+ + 3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 5-epi-aristolochene + O2 + NADPH = 1-deoxy-capsidiol + H2O + NADP+ capsidiol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.74 O2 + NADPH + 7-deoxyloganin = H2O + NADP+ + loganin secologanin and strictosidine 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: (+)-pulegone + NADPH + O2 = (+)-menthofuran + NADP+ + H2O menthol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.4.1.13 L-glutamate + NADP+ = L-glutamine + α-ketoglutarate + NADPH glutamine degradation 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.4.1.13 L-glutamate + NADP+ = L-glutamine + α-ketoglutarate + NADPH glutamate 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.195 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 4-coumarate + NADPH + O2 = H2O + caffeate + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 4-coumarate + NADPH + O2 = H2O + caffeate + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.158 NADP+ + UDP-N-acetylmuramate = NADPH + UDP-GlcNAc-enolpyruvate peptidoglycan 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.21 7-dehydro-cholesterol + NADPH = cholesterol + NADP+ cholesterol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.21 7-dehydro-cholesterol + NADPH = cholesterol + NADP+ cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- tetrahydrogeranylgeranyl-PP + NADPH = phytyl-PP + NADP+ phytyl-PP 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.36 4-coumaroylquinate + NADPH + O2 = caffeoylquinate + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.93 (+)-abscisate + NADPH + O2 = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.70 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADPH + O2 = 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol + NADP+ + H2O cholesterol biosynthesis III (via desmosterol) 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: (+)-pulegone + NADPH = (-)-menthone + NADP+ menthol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.36 4-coumaroylshikimate + NADPH + O2 = 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.99.- (22α)-hydroxy-campest-4-en-3-one + NADPH = (22α)-hydroxy-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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.1.1.168 NADP+ + pantoyl lactone = NADPH + 2-oxopantoyl lactone pantothenate 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.3.1.- 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.81 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: psoralen + NADPH + H2O = bergaptol + NADP+ linear furanocoumarin 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.- L-tryptophan + NADPH + O2 = indole-3-acetaldoxime + CO2 + 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1-deoxy-capsidiol + O2 + NADPH = capsidiol + H2O + NADP+ capsidiol 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.5.1.5 5,10-methylene-THF + NADP+ = NADPH folate transformations 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.5.1.5 5,10-methylene-THF + NADP+ = NADPH formylTHF 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.5.1.5 5,10-methylene-THF + NADP+ = NADPH formylTHF 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.17.1.3 leucocyanidin + NADPH = 2,3-trans-catechin + NADP+ + H2O proanthocyanidin biosynthesis from flavanols 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: 1.14.13.8 nicotine + NADPH + O2 = nicotine-1'-N-oxide + NADP+ + H2O nicotine 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) 745.426 C21 H30 N7 O17 P3 C(C1(OC(C(C(O)1)OP(O)(=O)O)n2(c3(c(nc2)c(N)ncn3))))OP(O)(=O)OP(=O)(O)OCC4(OC(C(O)C(O)4)N5(C=C(C(N)=O)CC=C5)) CAS:2646-71-1:*LIGAND-CPD:C00005: monovinyl protochlorophyllide a + NADPH = NADP+ + chlorophyllide a chlorophyllide a biosynthesis Fe2+ Fe(II)*Fe+2*Fe++*ferrous iron*Fe+2*Fe2+ 55.847 FE1 [Fe++] LIGAND-CPD:C00023: 4.99.1.1 Fe2+ + protoporphyrin IX = H+ + protoheme IX heme biosynthesis II Fe2+ Fe(II)*Fe+2*Fe++*ferrous iron*Fe+2*Fe2+ 55.847 FE1 [Fe++] LIGAND-CPD:C00023: 1.16.1.7 Fe2+ + NAD+ = Fe3+ + NADH Fe(III)-reduction and Fe(II) transport Fe2+ Fe(II)*Fe+2*Fe++*ferrous iron*Fe+2*Fe2+ 55.847 FE1 [Fe++] LIGAND-CPD:C00023: Fe2+ = Fe2+ Fe(III)-reduction and Fe(II) transport GA24 gibberellin A24*gibberellin A24*GA24 346.422 C20 H26 O5 CC1([CH]4(C(CCC1)(C=O)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA15 + α-ketoglutarate + O2 = GA24 + succinate + CO2 + H2O gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) GA24 gibberellin A24*gibberellin A24*GA24 346.422 C20 H26 O5 CC1([CH]4(C(CCC1)(C=O)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA24 + O2 + α-ketoglutarate = GA25 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) GA24 gibberellin A24*gibberellin A24*GA24 346.422 C20 H26 O5 CC1([CH]4(C(CCC1)(C=O)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA24 + O2 + α-ketoglutarate = GA9 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) GA24 gibberellin A24*gibberellin A24*GA24 346.422 C20 H26 O5 CC1([CH]4(C(CCC1)(C=O)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA24 + α-ketoglutarate + O2 = GA36 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) γ-carotene β,ψ-carotene 536.882 C40 H56 CC(C=CC1(=C(C)CCCC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC=C(C)CCC=C(C)C 5.5.1.- γ-carotene = β-carotene carotenoid biosynthesis γ-carotene β,ψ-carotene 536.882 C40 H56 CC(C=CC1(=C(C)CCCC(C)(C)1))=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC=C(C)CCC=C(C)C 5.5.1.- trans-lycopene = γ-carotene carotenoid biosynthesis 12-oxo-trans-10-dodecenoate traumatin 212.288 C12 H20 O3 C(=O)(O)CCCCCCCCC=CC=O 12-oxo-cis-9-dodecenoate = 12-oxo-trans-10-dodecenoate 13-LOX and 13-HPL pathway cotinine-glucuronide 353.351 C16 H21 N2 O7 c2([n+](C1(C(O)C(O)C(O)C(O1)C(O)=O))cc(cc2)[CH]3(N(C)C(=O)CC3)) 2.4.1.17 cotinine + UDP-D-glucuronate = cotinine-glucuronide + UDP nicotine degradation III isofucosterol 412.698 C29 H48 O1 CC(C)C(=CC)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) isofucosterol = Δ24-25-sitosterol sterol biosynthesis isofucosterol 412.698 C29 H48 O1 CC(C)C(=CC)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4(C(=CC3)CC(O)CC4)(C)))) 1.3.1.21 5-dehydroavenasterol + NADPH = isofucosterol + NADP+ sterol biosynthesis 2,3-dihydro-2,3-dihydroxybenzoate 2,3-Dihydroxy-2,3-dihydrobenzoate 156.138 C7 H8 O4 C(O)(=O)C1(C(O)C(O)C=CC=1) LIGAND-CPD:C04171: 3.3.2.1 H2O + isochorismate = pyruvate + 2,3-dihydro-2,3-dihydroxybenzoate enterobactin biosynthesis 2,3-dihydro-2,3-dihydroxybenzoate 2,3-Dihydroxy-2,3-dihydrobenzoate 156.138 C7 H8 O4 C(O)(=O)C1(C(O)C(O)C=CC=1) LIGAND-CPD:C04171: 1.3.1.28 NAD+ + 2,3-dihydro-2,3-dihydroxybenzoate = NADH + 2,3-dihydroxybenzoate enterobactin 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 238.136 C6 H11 N2 O6 P1 C(OP(O)(=O)O)C(O)C(O)c1(c[nH]cn1) LIGAND-CPD:C04666: 2.4.2.- phosphoribulosylformimino-AICAR-P + L-glutamine = L-glutamate + D-erythro-imidazole-glycerol-phosphate + AICAR histidine biosynthesis I 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 238.136 C6 H11 N2 O6 P1 C(OP(O)(=O)O)C(O)C(O)c1(c[nH]cn1) LIGAND-CPD:C04666: 4.2.1.19 D-erythro-imidazole-glycerol-phosphate = imidazole acetol-phosphate + H2O histidine biosynthesis I zeinoxanthin β,ε-carotene-3-ol 552.882 C40 H56 O1 CC1(C(=C(C)CC(O)C1)C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)(C)CCC=C(C)2))(C) 1.14.99.- zeinoxanthin + NADPH + O2 = lutein + NADP+ + H2O carotenoid biosynthesis zeinoxanthin β,ε-carotene-3-ol 552.882 C40 H56 O1 CC1(C(=C(C)CC(O)C1)C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC2(C(C)(C)CCC=C(C)2))(C) 1.14.99.- α-carotene + NADPH + O2 = zeinoxanthin + NADP+ + H2O carotenoid biosynthesis GMP guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 363.223 C10 H14 N5 O8 P1 C(OP(=O)(O)O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00144:*CAS:85-32-5 6.3.4.1 ammonia + xanthosine-5-phosphate + ATP = AMP + diphosphate + GMP salvage pathways of purine nucleosides II (plant) GMP guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 363.223 C10 H14 N5 O8 P1 C(OP(=O)(O)O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00144:*CAS:85-32-5 6.3.4.1 ammonia + xanthosine-5-phosphate + ATP = AMP + diphosphate + GMP purine nucleotides de novo biosynthesis I GMP guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 363.223 C10 H14 N5 O8 P1 C(OP(=O)(O)O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00144:*CAS:85-32-5 GDP-L-galactose + H2O = L-galactose + GMP ascorbate biosynthesis GMP guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 363.223 C10 H14 N5 O8 P1 C(OP(=O)(O)O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00144:*CAS:85-32-5 2.4.2.8 5-phosphoribosyl 1-pyrophosphate + guanine = diphosphate + GMP salvage pathways of purine nucleosides GMP guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 363.223 C10 H14 N5 O8 P1 C(OP(=O)(O)O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00144:*CAS:85-32-5 2.4.2.8 5-phosphoribosyl 1-pyrophosphate + guanine = diphosphate + GMP salvage pathways of purine and pyrimidine nucleotides GMP guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 363.223 C10 H14 N5 O8 P1 C(OP(=O)(O)O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00144:*CAS:85-32-5 2.4.2.8 5-phosphoribosyl 1-pyrophosphate + guanine = diphosphate + GMP salvage pathways of purine nucleosides II (plant) GMP guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 363.223 C10 H14 N5 O8 P1 C(OP(=O)(O)O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00144:*CAS:85-32-5 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis II GMP guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 363.223 C10 H14 N5 O8 P1 C(OP(=O)(O)O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00144:*CAS:85-32-5 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis I GMP guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 363.223 C10 H14 N5 O8 P1 C(OP(=O)(O)O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00144:*CAS:85-32-5 3.1.3.5 GMP + H2O = guanosine purine degradation GMP guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 363.223 C10 H14 N5 O8 P1 C(OP(=O)(O)O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00144:*CAS:85-32-5 3.1.3.5 GMP + H2O = guanosine salvage pathways of purine nucleosides II (plant) GMP guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 363.223 C10 H14 N5 O8 P1 C(OP(=O)(O)O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00144:*CAS:85-32-5 2.7.1.73 guanosine + ATP = GMP + ADP salvage pathways of purine nucleosides GMP guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 363.223 C10 H14 N5 O8 P1 C(OP(=O)(O)O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00144:*CAS:85-32-5 2.7.1.73 guanosine + ATP = GMP + ADP salvage pathways of purine nucleosides II (plant) GMP guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 363.223 C10 H14 N5 O8 P1 C(OP(=O)(O)O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00144:*CAS:85-32-5 2.7.4.8 GMP + ATP = GDP + ADP salvage pathways of purine and pyrimidine nucleotides GMP guanylate*G*guanylic acid*guanosine-phosphate*guanosine-5'-phosphate*guanosine-monophosphate*guanosine monophosphate*guanosine-5'-monophosphate 363.223 C10 H14 N5 O8 P1 C(OP(=O)(O)O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00144:*CAS:85-32-5 2.7.4.8 GMP + ATP = GDP + ADP purine nucleotides de novo biosynthesis I dihydrokaempferol aromadendrin*(+)-aromadendrin*(+)-Dihydrokaempferol 288.256 C15 H12 O6 c1(cc(ccc(O)1)C2(C(O)C(=O)c3(c(O)cc(O)cc(O2)3))) CAS:480-20-6 1.14.13.- dihydrokaempferol + NADPH + O2 = dihydromyricetin + NADP+ + H2O leucodelphinidin biosynthesis dihydrokaempferol aromadendrin*(+)-aromadendrin*(+)-Dihydrokaempferol 288.256 C15 H12 O6 c1(cc(ccc(O)1)C2(C(O)C(=O)c3(c(O)cc(O)cc(O2)3))) CAS:480-20-6 1.14.13.21 dihydrokaempferol + NADPH + O2 = dihydroquercetin + NADP+ + H2O leucopelargonidin and leucocyanidin biosynthesis dihydrokaempferol aromadendrin*(+)-aromadendrin*(+)-Dihydrokaempferol 288.256 C15 H12 O6 c1(cc(ccc(O)1)C2(C(O)C(=O)c3(c(O)cc(O)cc(O2)3))) CAS:480-20-6 1.14.13.21 dihydrokaempferol + NADPH + O2 = dihydroquercetin + NADP+ + H2O leucodelphinidin biosynthesis dihydrokaempferol aromadendrin*(+)-aromadendrin*(+)-Dihydrokaempferol 288.256 C15 H12 O6 c1(cc(ccc(O)1)C2(C(O)C(=O)c3(c(O)cc(O)cc(O2)3))) CAS:480-20-6 1.14.13.21 dihydrokaempferol + NADPH + O2 = dihydroquercetin + NADP+ + H2O flavonol biosynthesis dihydrokaempferol aromadendrin*(+)-aromadendrin*(+)-Dihydrokaempferol 288.256 C15 H12 O6 c1(cc(ccc(O)1)C2(C(O)C(=O)c3(c(O)cc(O)cc(O2)3))) CAS:480-20-6 1.14.11.23 dihydrokaempferol + α-ketoglutarate + O2 = kaempferol + succinate + CO2 + H2O flavonol biosynthesis dihydrokaempferol aromadendrin*(+)-aromadendrin*(+)-Dihydrokaempferol 288.256 C15 H12 O6 c1(cc(ccc(O)1)C2(C(O)C(=O)c3(c(O)cc(O)cc(O2)3))) CAS:480-20-6 1.14.11.9 naringenin + O2 + α-ketoglutarate = CO2 + succinate + dihydrokaempferol flavonoid biosynthesis dihydrokaempferol aromadendrin*(+)-aromadendrin*(+)-Dihydrokaempferol 288.256 C15 H12 O6 c1(cc(ccc(O)1)C2(C(O)C(=O)c3(c(O)cc(O)cc(O2)3))) CAS:480-20-6 1.1.1.219 dihydrokaempferol + NADPH = leucopelargonidin + NADP+ leucopelargonidin and leucocyanidin biosynthesis 9β-pimara-7,15-diene 9beta-pimara-7,15-diene*9beta-hydroxy-pimara-7,15-diene 272.473 C20 H32 CC1([CH]2(C(CCC1)(C)[CH]3(C(=CC2)CC(C=C)(C)CC3)))(C) syn-copalyl diphosphate = 9β-pimara-7,15-diene momilactone biosynthesis 9β-pimara-7,15-diene 9beta-pimara-7,15-diene*9beta-hydroxy-pimara-7,15-diene 272.473 C20 H32 CC1([CH]2(C(CCC1)(C)[CH]3(C(=CC2)CC(C=C)(C)CC3)))(C) 1.14.14.1 9β-pimara-7,15-diene = 3β-Hydroxy-9β-pimara-7,15-diene-19,6β-olide momilactone biosynthesis D-4-hydroxy-2-keto-glutarate 4-hydroxy-2-oxoglutarate*D-4-hydroxy-2-ketoglutarate*2-k-4-OH-glutarate*2-keto-4-hydroxyglutarate*2-Oxo-4-hydroxyglutarate*4-hydroxy-2-ketoglutarate 162.099 C5 H6 O6 C(O)(=O)C(O)CC(=O)C(=O)O CAS:1187-99-1 4.1.3.16 D-4-hydroxy-2-keto-glutarate = glyoxylate + pyruvate 4-hydroxyproline degradation I D-4-hydroxy-2-keto-glutarate 4-hydroxy-2-oxoglutarate*D-4-hydroxy-2-ketoglutarate*2-k-4-OH-glutarate*2-keto-4-hydroxyglutarate*2-Oxo-4-hydroxyglutarate*4-hydroxy-2-ketoglutarate 162.099 C5 H6 O6 C(O)(=O)C(O)CC(=O)C(=O)O CAS:1187-99-1 2.6.1.23 α-ketoglutarate + L-erythro-4-hydroxy-glutamate = L-glutamate + D-4-hydroxy-2-keto-glutarate 4-hydroxyproline degradation I uracil 112.088 C4 H4 N2 O2 c1(=O)(cc[nH]c([nH]1)=O) LIGAND-CPD:C00106:*CAS:66-22-8 2.4.2.9 diphosphate + UMP = 5-phosphoribosyl 1-pyrophosphate + uracil salvage pathways of purine and pyrimidine nucleotides uracil 112.088 C4 H4 N2 O2 c1(=O)(cc[nH]c([nH]1)=O) LIGAND-CPD:C00106:*CAS:66-22-8 2.4.2.9 diphosphate + UMP = 5-phosphoribosyl 1-pyrophosphate + uracil salvage pathways of pyrimidine ribonucleotides uracil 112.088 C4 H4 N2 O2 c1(=O)(cc[nH]c([nH]1)=O) LIGAND-CPD:C00106:*CAS:66-22-8 1.3.1.2 NADP+ + dihydrouracil = NADPH + uracil β-alanine biosynthesis III uracil 112.088 C4 H4 N2 O2 c1(=O)(cc[nH]c([nH]1)=O) 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(=O)(cc[nH]c([nH]1)=O) LIGAND-CPD:C00106:*CAS:66-22-8 2.4.2.3 uridine = ribose-1-phosphate + uracil (deoxy)ribose phosphate degradation uracil 112.088 C4 H4 N2 O2 c1(=O)(cc[nH]c([nH]1)=O) LIGAND-CPD:C00106:*CAS:66-22-8 2.4.2.3 uridine = ribose-1-phosphate + uracil salvage pathways of pyrimidine ribonucleotides uracil 112.088 C4 H4 N2 O2 c1(=O)(cc[nH]c([nH]1)=O) LIGAND-CPD:C00106:*CAS:66-22-8 deoxyuridine = deoxyribose-1-phosphate + uracil (deoxy)ribose phosphate degradation uracil 112.088 C4 H4 N2 O2 c1(=O)(cc[nH]c([nH]1)=O) LIGAND-CPD:C00106:*CAS:66-22-8 deoxyuridine = deoxyribose-1-phosphate + uracil salvage pathways of pyrimidine deoxyribonucleotides (3Z,6Z)-nonadienal 138.209 C9 H14 O1 CCC=CCC=CCC=O 9-HPOT = (3Z,6Z)-nonadienal + 9-oxo-nonanoate 9-LOX and 9-HPL pathway 2-aminomuconate semialdehyde 2-Aminomuconate 6-semialdehyde*2-aminomuconic semialdehyde 141.126 C6 H7 N1 O3 [CH](=O)C=CC=C(N)C(O)=O 4.1.1.45 2-amino-3-carboxymuconate semialdehyde = CO2 + 2-aminomuconate semialdehyde tryptophan degradation III (eukaryotic) 2-aminomuconate semialdehyde 2-Aminomuconate 6-semialdehyde*2-aminomuconic semialdehyde 141.126 C6 H7 N1 O3 [CH](=O)C=CC=C(N)C(O)=O 1.2.1.32 H2O + NAD+ + 2-aminomuconate semialdehyde = NADH + 2-amino-muconate tryptophan degradation III (eukaryotic) α-D-mannose 1-phosphate mannose-1-phosphate*D-mannose-1-phosphate*mannose-1-P 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) LIGAND-CPD:C03812:*CAS:27251-84-9 5.4.2.8 α-D-mannose 1-phosphate = mannose-6-phosphate ascorbate biosynthesis α-D-mannose 1-phosphate mannose-1-phosphate*D-mannose-1-phosphate*mannose-1-P 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) LIGAND-CPD:C03812:*CAS:27251-84-9 5.4.2.8 α-D-mannose 1-phosphate = mannose-6-phosphate GDP-mannose metabolism α-D-mannose 1-phosphate mannose-1-phosphate*D-mannose-1-phosphate*mannose-1-P 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) LIGAND-CPD:C03812:*CAS:27251-84-9 2.7.7.22 α-D-mannose 1-phosphate + GDP = GDP-D-mannose GDP-mannose metabolism α-D-mannose 1-phosphate mannose-1-phosphate*D-mannose-1-phosphate*mannose-1-P 260.137 C6 H13 O9 P1 C(O)C1(OC(OP(O)(O)=O)C(O)C(O)C1O) LIGAND-CPD:C03812:*CAS:27251-84-9 2.7.7.13 α-D-mannose 1-phosphate + GTP = GDP-D-mannose + diphosphate ascorbate 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 402.355 C12 H23 N2 O9 P1 S1 CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(=O)NC(C(O)=O)CS LIGAND-CPD:C04352: 4.1.1.36 R-4'-phosphopantothenoyl-L-cysteine = pantetheine 4'-phosphate + 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 402.355 C12 H23 N2 O9 P1 S1 CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(=O)NC(C(O)=O)CS LIGAND-CPD:C04352: 6.3.2.5 D-4'-phosphopantothenate + L-cysteine + CTP = R-4'-phosphopantothenoyl-L-cysteine + diphosphate + CMP coenzyme A biosynthesis H2CO3 carbonic acid 62.025 C1 H2 O3 C(=O)(O)O CAS:463-79-6 4.2.1.1 H2CO3 = H2O + CO2 cyanate degradation CO carbon monoxide*carbon monooxide 28.01 C1 O1 [C-]#[O+] CAS:630-08-0 4.1.99.5 epicuticular wax biosynthesis 2-oxo-3-hydroxy-4-phosphobutanoate 3-hydroxy-4-phospho-hydroxy-α-ketobutyrate 213.06 C4 H6 O8 P1 C([O-])(=O)C(=O)C(O)COP(=O)(O)O PUBCHEM:440900:*LIGAND-CPD:C06054: 2.6.1.52 2-oxo-3-hydroxy-4-phosphobutanoate + L-glutamate = 4-(phosphonooxy)-threonine + α-ketoglutarate pyridoxal 5'-phosphate biosynthesis 2-oxo-3-hydroxy-4-phosphobutanoate 3-hydroxy-4-phospho-hydroxy-α-ketobutyrate 213.06 C4 H6 O8 P1 C([O-])(=O)C(=O)C(O)COP(=O)(O)O PUBCHEM:440900:*LIGAND-CPD:C06054: 1.1.1.290 erythronate-4-phosphate + NAD+ = 2-oxo-3-hydroxy-4-phosphobutanoate + NADH + H+ pyridoxal 5'-phosphate biosynthesis deoxycytidine d-cytidine*2'-deoxycytidine 227.219 C9 H13 N3 O4 c1(n(c(=O)nc(c1)N)C2(OC(C(C2)O)CO)) LIGAND-CPD:C00881:*CAS:951-77-9 3.5.4.5 H2O + deoxycytidine = ammonia + deoxyuridine (deoxy)ribose phosphate degradation deoxycytidine d-cytidine*2'-deoxycytidine 227.219 C9 H13 N3 O4 c1(n(c(=O)nc(c1)N)C2(OC(C(C2)O)CO)) LIGAND-CPD:C00881:*CAS:951-77-9 3.5.4.5 H2O + deoxycytidine = ammonia + deoxyuridine salvage pathways of pyrimidine deoxyribonucleotides dihydrozeatin-9-N-glucoside 383.403 C16 H25 N5 O6 c1(c2(c(ncn1)N(C=N2)C3(OC(CO)C(O)C(O)C(O)3)))(NCCC(C)CO) 2.4.1.- dihydrozeatin + UDP-D-glucose = dihydrozeatin-9-N-glucoside + UDP cytokinins 9-N-glucoside biosynthesis dihydrozeatin-9-N-glucoside 383.403 C16 H25 N5 O6 c1(c2(c(ncn1)N(C=N2)C3(OC(CO)C(O)C(O)C(O)3)))(NCCC(C)CO) 2.4.1.- dihydrozeatin-9-N-glucoside + UDP-D-glucose = dihydrozeatin-9-N-glucoside-O-glucoside + UDP cytokinins-O-glucoside biosynthesis N-methylethanolamine phosphate P-MME 155.09 C3 H10 N1 O4 P1 C(NC)COP(O)(O)=O 2.1.1.103 N-methylethanolamine phosphate + S-adenosyl-L-methionine = N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine choline biosynthesis I N-methylethanolamine phosphate P-MME 155.09 C3 H10 N1 O4 P1 C(NC)COP(O)(O)=O 2.1.1.103 phosphoryl-ethanolamine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + N-methylethanolamine phosphate choline biosynthesis I α-tocopherol 430.713 C29 H50 O2 CC2(=C1(OC(CCC1=C(C)C(O)=C2C)(C)CCCC(C)CCCC(C)CCCC(C)C)) NCI:82623*CAS:2074-53-5 2.1.1.95 γ-tocopherol + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + α-tocopherol vitamin E biosynthesis indole acetaldehyde indole-3-acetaldehyde*2-(indol-3-yl)acetaldehyde 159.187 C10 H9 N1 O1 c1(c(CC=O)c2(c([nH]1)cccc2)) CAS:2591-98-2 1.4.3.6 tryptamine + H2O + O2 = ammonia + indole acetaldehyde + H2O2 IAA biosynthesis I indole acetaldehyde indole-3-acetaldehyde*2-(indol-3-yl)acetaldehyde 159.187 C10 H9 N1 O1 c1(c(CC=O)c2(c([nH]1)cccc2)) CAS:2591-98-2 1.2.1.5 indole acetaldehyde + H2O = indole-3-acetate + H+ tryptophan degradation V (side chain pathway) indole acetaldehyde indole-3-acetaldehyde*2-(indol-3-yl)acetaldehyde 159.187 C10 H9 N1 O1 c1(c(CC=O)c2(c([nH]1)cccc2)) CAS:2591-98-2 1.13.99.3 L-tryptophan + O2 = indole acetaldehyde + ammonia + CO2 tryptophan degradation V (side chain pathway) indole acetaldehyde indole-3-acetaldehyde*2-(indol-3-yl)acetaldehyde 159.187 C10 H9 N1 O1 c1(c(CC=O)c2(c([nH]1)cccc2)) CAS:2591-98-2 1.2.3.7 indole acetaldehyde + O2 + H2O = indole-3-acetate + H2O2 IAA biosynthesis I indole acetaldehyde indole-3-acetaldehyde*2-(indol-3-yl)acetaldehyde 159.187 C10 H9 N1 O1 c1(c(CC=O)c2(c([nH]1)cccc2)) CAS:2591-98-2 1.13.99.3 indole acetaldehyde + O2 = indole-3-glycol aldehyde tryptophan degradation V (side chain pathway) indole acetaldehyde indole-3-acetaldehyde*2-(indol-3-yl)acetaldehyde 159.187 C10 H9 N1 O1 c1(c(CC=O)c2(c([nH]1)cccc2)) CAS:2591-98-2 4.1.1.74 indole-3-pyruvate = CO2 + indole acetaldehyde IAA biosynthesis I indole acetaldehyde indole-3-acetaldehyde*2-(indol-3-yl)acetaldehyde 159.187 C10 H9 N1 O1 c1(c(CC=O)c2(c([nH]1)cccc2)) CAS:2591-98-2 1.1.99.8 indole-3-ethanol = indole acetaldehyde tryptophan degradation V (side chain pathway) 3-methylthiopropanal methional*3-methylthiopropional*3-methylthio-propionaldehyde*3-methylsulfanyl-propanal*3-methylmercapto-propionaldehyde 104.167 C4 H8 O1 S1 C(SC)CC=O PUBCHEM:18635: 2-oxo-4-methylthiobutanoate = 3-methylthiopropanal + CO2 methionine degradation III 3-methylthiopropanal methional*3-methylthiopropional*3-methylthio-propionaldehyde*3-methylsulfanyl-propanal*3-methylmercapto-propionaldehyde 104.167 C4 H8 O1 S1 C(SC)CC=O PUBCHEM:18635: 1.1.1.1 3-methylthiopropanal + NADH + H+ = methionol + NAD+ methionine degradation III D-ribose α-D-ribose*ribose*α-D-ribose-5 150.131 C5 H10 O5 C(O)C1(C(O)C(O)C(O1)O) LIGAND:C00121:*LIGAND-CPD:C00121:*CAS:50-69-1 2.7.1.15 D-ribose + ATP = D-ribose-5-phosphate + ADP ribose degradation D-ribose α-D-ribose*ribose*α-D-ribose-5 150.131 C5 H10 O5 C(O)C1(C(O)C(O)C(O1)O) LIGAND:C00121:*LIGAND-CPD:C00121:*CAS:50-69-1 isopentenyl adenosine + H2O = isopentenyladenine + D-ribose trans-zeatin biosynthesis D-ribose α-D-ribose*ribose*α-D-ribose-5 150.131 C5 H10 O5 C(O)C1(C(O)C(O)C(O1)O) LIGAND:C00121:*LIGAND-CPD:C00121:*CAS:50-69-1 3.2.2.7 H2O + adenosine = D-ribose + adenine salvage pathways of purine nucleosides II (plant) D-ribose α-D-ribose*ribose*α-D-ribose-5 150.131 C5 H10 O5 C(O)C1(C(O)C(O)C(O1)O) LIGAND:C00121:*LIGAND-CPD:C00121:*CAS:50-69-1 3.2.2.1 guanosine + H2O = guanine + D-ribose purine degradation D-ribose α-D-ribose*ribose*α-D-ribose-5 150.131 C5 H10 O5 C(O)C1(C(O)C(O)C(O1)O) LIGAND:C00121:*LIGAND-CPD:C00121:*CAS:50-69-1 3.2.2.1 guanosine + H2O = guanine + D-ribose salvage pathways of purine nucleosides II (plant) D-ribose α-D-ribose*ribose*α-D-ribose-5 150.131 C5 H10 O5 C(O)C1(C(O)C(O)C(O1)O) LIGAND:C00121:*LIGAND-CPD:C00121:*CAS:50-69-1 cis-zeatin riboside + H2O = cis-zeatin + D-ribose cis-zeatin biosynthesis D-ribose α-D-ribose*ribose*α-D-ribose-5 150.131 C5 H10 O5 C(O)C1(C(O)C(O)C(O1)O) LIGAND:C00121:*LIGAND-CPD:C00121:*CAS:50-69-1 3.2.2.2 inosine + H2O = hypoxanthine + D-ribose purine degradation D-ribose α-D-ribose*ribose*α-D-ribose-5 150.131 C5 H10 O5 C(O)C1(C(O)C(O)C(O1)O) LIGAND:C00121:*LIGAND-CPD:C00121:*CAS:50-69-1 3.2.2.2 inosine + H2O = hypoxanthine + D-ribose salvage pathways of purine nucleosides II (plant) D-ribose α-D-ribose*ribose*α-D-ribose-5 150.131 C5 H10 O5 C(O)C1(C(O)C(O)C(O1)O) LIGAND:C00121:*LIGAND-CPD:C00121:*CAS:50-69-1 3.2.2.1 xanthosine + H2O = xanthine + D-ribose purine degradation D-ribose α-D-ribose*ribose*α-D-ribose-5 150.131 C5 H10 O5 C(O)C1(C(O)C(O)C(O1)O) LIGAND:C00121:*LIGAND-CPD:C00121:*CAS:50-69-1 3.2.2.1 xanthosine + H2O = xanthine + D-ribose salvage pathways of purine nucleosides II (plant) D-ribose α-D-ribose*ribose*α-D-ribose-5 150.131 C5 H10 O5 C(O)C1(C(O)C(O)C(O1)O) LIGAND:C00121:*LIGAND-CPD:C00121:*CAS:50-69-1 trans-zeatin riboside + H2O = trans-zeatin + D-ribose trans-zeatin biosynthesis D-ribose α-D-ribose*ribose*α-D-ribose-5 150.131 C5 H10 O5 C(O)C1(C(O)C(O)C(O1)O) LIGAND:C00121:*LIGAND-CPD:C00121:*CAS:50-69-1 3.2.2.1 nicotinamide riboside + H2O = nicotinamide + D-ribose pyridine nucleotide cycling (plants) N-acetyl-L-glutamate N-acetylglutamic acid*acetyl-glu*N-acetyl-glutamate*acetyl-glutamate*N-acetyl L-glutamic acid*NAG 189.168 C7 H11 N1 O5 CC(=O)NC(C(O)=O)CCC(O)=O 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 N-acetylglutamic acid*acetyl-glu*N-acetyl-glutamate*acetyl-glutamate*N-acetyl L-glutamic acid*NAG 189.168 C7 H11 N1 O5 CC(=O)NC(C(O)=O)CCC(O)=O 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 N-acetylglutamic acid*acetyl-glu*N-acetyl-glutamate*acetyl-glutamate*N-acetyl L-glutamic acid*NAG 189.168 C7 H11 N1 O5 CC(=O)NC(C(O)=O)CCC(O)=O LIGAND-CPD:C00624:*CAS:1188-37-0 2.3.1.1 L-glutamate + acetyl-CoA = N-acetyl-L-glutamate + coenzyme A arginine biosynthesis II (acetyl cycle) N-acetyl-L-glutamate N-acetylglutamic acid*acetyl-glu*N-acetyl-glutamate*acetyl-glutamate*N-acetyl L-glutamic acid*NAG 189.168 C7 H11 N1 O5 CC(=O)NC(C(O)=O)CCC(O)=O LIGAND-CPD:C00624:*CAS:1188-37-0 2.3.1.1 L-glutamate + acetyl-CoA = N-acetyl-L-glutamate + coenzyme A ornithine biosynthesis N-acetyl-L-glutamate N-acetylglutamic acid*acetyl-glu*N-acetyl-glutamate*acetyl-glutamate*N-acetyl L-glutamic acid*NAG 189.168 C7 H11 N1 O5 CC(=O)NC(C(O)=O)CCC(O)=O 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 sulphate*SO4-2*SO42-*SO4-- 96.058 O4 S1 O=S([O-])([O-])=O CAS:7664-93-9:*LIGAND-CPD:C00059:*CAS:14808-79-8 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate reduction II (assimilatory) sulfate sulphate*SO4-2*SO42-*SO4-- 96.058 O4 S1 O=S([O-])([O-])=O CAS:7664-93-9:*LIGAND-CPD:C00059:*CAS:14808-79-8 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfite oxidation III sulfate sulphate*SO4-2*SO42-*SO4-- 96.058 O4 S1 O=S([O-])([O-])=O CAS:7664-93-9:*LIGAND-CPD:C00059:*CAS:14808-79-8 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate reduction I (assimilatory) sulfate sulphate*SO4-2*SO42-*SO4-- 96.058 O4 S1 O=S([O-])([O-])=O CAS:7664-93-9:*LIGAND-CPD:C00059:*CAS:14808-79-8 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate activation for sulfonation hydroxymethylbilane 854.82 C40 H42 N4 O17 c1(nc(c(CCC(O)=O)c1CC(=O)O)Cc2(nc(c(CC(O)=O)c2CCC(=O)O)Cc3(nc(c(CC(=O)O)c3CCC(O)=O)Cc4(c(CCC(=O)O)c(CC(O)=O)c(n4)CO)))) LIGAND-CPD:C01024:*CAS:73023-76-4 4.2.1.75 hydroxymethylbilane = uroporphyrinogen-III + H2O tetrapyrrole biosynthesis I hydroxymethylbilane 854.82 C40 H42 N4 O17 c1(nc(c(CCC(O)=O)c1CC(=O)O)Cc2(nc(c(CC(O)=O)c2CCC(=O)O)Cc3(nc(c(CC(=O)O)c3CCC(O)=O)Cc4(c(CCC(=O)O)c(CC(O)=O)c(n4)CO)))) LIGAND-CPD:C01024:*CAS:73023-76-4 2.5.1.61 H2O + porphobilinogen = ammonia + hydroxymethylbilane tetrapyrrole biosynthesis I (S)-ureidoglycolate (-)-ureidoglycolate*ureidoglycolate 134.091 C3 H6 N2 O4 C(C(=O)O)(O)NC(N)=O LIGAND-CPD:C00603:*CAS:2017665 1.1.1.154 (S)-ureidoglycolate = oxalurate allantoin degradation I (S)-ureidoglycolate (-)-ureidoglycolate*ureidoglycolate 134.091 C3 H6 N2 O4 C(C(=O)O)(O)NC(N)=O LIGAND-CPD:C00603:*CAS:2017665 3.5.3.19 H2O + (S)-ureidoglycolate = ammonia + CO2 + glyoxylate allantoin degradation I (S)-ureidoglycolate (-)-ureidoglycolate*ureidoglycolate 134.091 C3 H6 N2 O4 C(C(=O)O)(O)NC(N)=O LIGAND-CPD:C00603:*CAS:2017665 3.5.3.4 H2O + allantoate = (S)-ureidoglycolate + urea allantoin degradation I nicotine 162.234 C10 H14 N2 c1(ncc(cc1)[CH]2(N(C)CCC2)) NCI:5065 2.4.1.17 nicotine + UDP-D-glucuronate = nicotine-Glucuronide + UDP nicotine degradation II nicotine 162.234 C10 H14 N2 c1(ncc(cc1)[CH]2(N(C)CCC2)) NCI:5065 1.14.14.1 nicotine + NADPH + O2 = 2'-hydroxynicotine + NADP+ + H2O nicotine degradation II nicotine 162.234 C10 H14 N2 c1(ncc(cc1)[CH]2(N(C)CCC2)) NCI:5065 1.14.14.1 nicotine + NADPH = nicotine-Δ1'5'-iminium ion + NADP+ nicotine degradation II nicotine 162.234 C10 H14 N2 c1(ncc(cc1)[CH]2(N(C)CCC2)) NCI:5065 1.14.14.1 nicotine + NADPH = nicotine-Δ1'5'-iminium ion + NADP+ nicotine degradation III nicotine 162.234 C10 H14 N2 c1(ncc(cc1)[CH]2(N(C)CCC2)) NCI:5065 2.1.1.49 nicotine + S-adenosyl-L-methionine = nicotine isomethonium ion + S-adenosyl-L-homocysteine nicotine degradation II nicotine 162.234 C10 H14 N2 c1(ncc(cc1)[CH]2(N(C)CCC2)) NCI:5065 1.14.13.8 nicotine + NADPH + O2 = nicotine-1'-N-oxide + NADP+ + H2O nicotine degradation II nicotine 162.234 C10 H14 N2 c1(ncc(cc1)[CH]2(N(C)CCC2)) NCI:5065 nicotine + H2O = nornicotine + formaldehyde nicotine degradation II choline 104.172 C5 H14 N1 O1 C(O)C[N+](C)(C)C 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(O)C[N+](C)(C)C 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(O)C[N+](C)(C)C 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(O)C[N+](C)(C)C CAS:62-49-7*CAS:123-41-1:*LIGAND-CPD:C00114: 2.7.1.32 choline + ATP = phosphoryl-choline + ADP phospholipid biosynthesis II choline 104.172 C5 H14 N1 O1 C(O)C[N+](C)(C)C CAS:62-49-7*CAS:123-41-1:*LIGAND-CPD:C00114: 1.14.15.7 choline + O2 + H+ = betaine aldehyde hydrate + H2O glycine betaine biosynthesis III (plants) geraniol 154.252 C10 H18 O1 CC(=CCO)CCC=C(C)C NCI:9279*CAS:106-24-1 geraniol = 10-hydroxygeraniol secologanin and strictosidine biosynthesis geraniol 154.252 C10 H18 O1 CC(=CCO)CCC=C(C)C NCI:9279*CAS:106-24-1 4.2.3.- geranyl-PP + H2O = geraniol + diphosphate secologanin and strictosidine biosynthesis 4-methyl-5-(β-hydroxyethyl)thiazole phosphate 4-4-methyl-5-(2-phosphonooxyethyl)-thiazole*4-methyl-5-(2-phosphoethyl)-thiazole*THZ-P*4-Methyl-5-(2-phosphono-oxyethyl)-thiazole 223.183 C6 H10 N1 O4 P1 S1 Cc1(c(scn1)CCOP(O)(=O)O) LIGAND-CPD:C04327: 2.5.1.3 4-methyl-5-(β-hydroxyethyl)thiazole phosphate + 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate = thiamine-phosphate + diphosphate thiamine biosynthesis 4-methyl-5-(β-hydroxyethyl)thiazole phosphate 4-4-methyl-5-(2-phosphonooxyethyl)-thiazole*4-methyl-5-(2-phosphoethyl)-thiazole*THZ-P*4-Methyl-5-(2-phosphono-oxyethyl)-thiazole 223.183 C6 H10 N1 O4 P1 S1 Cc1(c(scn1)CCOP(O)(=O)O) LIGAND-CPD:C04327: 2.7.1.50 ATP + 4-methyl-5-(β-hydroxyethyl)thiazole = ADP + 4-methyl-5-(β-hydroxyethyl)thiazole phosphate thiamine biosynthesis 4-methyl-5-(β-hydroxyethyl)thiazole phosphate 4-4-methyl-5-(2-phosphonooxyethyl)-thiazole*4-methyl-5-(2-phosphoethyl)-thiazole*THZ-P*4-Methyl-5-(2-phosphono-oxyethyl)-thiazole 223.183 C6 H10 N1 O4 P1 S1 Cc1(c(scn1)CCOP(O)(=O)O) LIGAND-CPD:C04327: L-tyrosine + 1-deoxy-D-xylulose 5-phosphate = 4-methyl-5-(β-hydroxyethyl)thiazole phosphate + 4-hydroxybenzyl alcohol thiamine biosynthesis L-dehydro-ascorbate dehydroascorbate 174.11 C6 H6 O6 C1(OC(C(O)CO)C(=O)C(=O)1)(=O) 1.8.5.1 L-dehydro-ascorbate + glutathione = glutathione disulfide + L-ascorbate ascorbate glutathione cycle L-dehydro-ascorbate dehydroascorbate 174.11 C6 H6 O6 C1(OC(C(O)CO)C(=O)C(=O)1)(=O) 1.14.17.4 L-ascorbate + 1-aminocyclopropane-1-carboxylate + O2 = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine L-dehydro-ascorbate dehydroascorbate 174.11 C6 H6 O6 C1(OC(C(O)CO)C(=O)C(=O)1)(=O) 1.10.99.3 violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O carotenoid biosynthesis L-dehydro-ascorbate dehydroascorbate 174.11 C6 H6 O6 C1(OC(C(O)CO)C(=O)C(=O)1)(=O) 1.10.99.3 violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle L-dehydro-ascorbate dehydroascorbate 174.11 C6 H6 O6 C1(OC(C(O)CO)C(=O)C(=O)1)(=O) 1.10.99.3 antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O carotenoid biosynthesis L-dehydro-ascorbate dehydroascorbate 174.11 C6 H6 O6 C1(OC(C(O)CO)C(=O)C(=O)1)(=O) 1.10.99.3 antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle L-dehydro-ascorbate dehydroascorbate 174.11 C6 H6 O6 C1(OC(C(O)CO)C(=O)C(=O)1)(=O) monodehydroascorbate = L-ascorbate + L-dehydro-ascorbate ascorbate glutathione cycle GA34-catabolite gibberellin A34-catabolite*gibberellin A34-catabolite*GA34-catabolite 346.379 C19 H22 O6 CC1([CH]4(C(=CC(=O)C(O)1)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA34 + α-ketoglutarate + O2 = GA34-catabolite + succinate + CO2 + H2O gibberellin inactivation dTDP TDP*thymidine 5'-(trihydrogen diphosphate) (9CI)*deoxy-TDP*thymidine-5'-diphosphate*thymidine-diphosphate 402.191 C10 H16 N2 O11 P2 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00363:*CAS:491-97-4 2.7.4.9 ATP + dTMP = ADP + dTDP salvage pathways of purine and pyrimidine nucleotides dTDP TDP*thymidine 5'-(trihydrogen diphosphate) (9CI)*deoxy-TDP*thymidine-5'-diphosphate*thymidine-diphosphate 402.191 C10 H16 N2 O11 P2 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00363:*CAS:491-97-4 2.7.4.9 ATP + dTMP = ADP + dTDP de novo biosynthesis of pyrimidine deoxyribonucleotides dTDP TDP*thymidine 5'-(trihydrogen diphosphate) (9CI)*deoxy-TDP*thymidine-5'-diphosphate*thymidine-diphosphate 402.191 C10 H16 N2 O11 P2 Cc1(cn(c(=O)[nH]c1=O)C2(OC(C(C2)O)COP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00363:*CAS:491-97-4 2.7.4.6 dTDP + ATP = dTTP + ADP de novo biosynthesis of pyrimidine deoxyribonucleotides α-D-glucuronate 1-phosphate glucuronate-1-P*glucuronate-1-phosphate*D-glucuronate-1-P*D-glucuronate-1-phosphate*1-phospho-α-D-glucuronate 274.121 C6 H11 O10 P1 C1(OC(C(=O)O)C(O)C(O)C(O)1)(OP(O)(=O)O) CAS:583-08-4:*LIGAND-CPD:C05385: 2.7.7.44 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 274.121 C6 H11 O10 P1 C1(OC(C(=O)O)C(O)C(O)C(O)1)(OP(O)(=O)O) CAS:583-08-4:*LIGAND-CPD:C05385: 2.7.1.43 glucuronate + ATP = α-D-glucuronate 1-phosphate + ADP UDP-D-glucuronate biosynthesis (from myo-inositol) 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 132.119 C4 H8 N2 O3 C(=O)(O)C(N)CC(N)=O LIGAND-CPD:C00152:*CAS:70-47-3 6.1.1.22 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 132.119 C4 H8 N2 O3 C(=O)(O)C(N)CC(N)=O LIGAND-CPD:C00152:*CAS:70-47-3 3.5.1.1 L-asparagine + H2O = ammonia + L-aspartate 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 132.119 C4 H8 N2 O3 C(=O)(O)C(N)CC(N)=O LIGAND-CPD:C00152:*CAS:70-47-3 3.5.1.1 L-asparagine + H2O = ammonia + L-aspartate asparagine degradation II 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 132.119 C4 H8 N2 O3 C(=O)(O)C(N)CC(N)=O LIGAND-CPD:C00152:*CAS:70-47-3 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis III 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 132.119 C4 H8 N2 O3 C(=O)(O)C(N)CC(N)=O LIGAND-CPD:C00152:*CAS:70-47-3 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = 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 132.119 C4 H8 N2 O3 C(=O)(O)C(N)CC(N)=O LIGAND-CPD:C00152:*CAS:70-47-3 6.3.1.1 ammonia + L-aspartate + ATP = L-asparagine + diphosphate + AMP asparagine biosynthesis III glycolaldehyde 2-OH-acetaldehyde*glycolaldehyde*hydroxyacetaldehyde*2-hydroxyethanal 60.052 C2 H4 O2 C(O)C=O LIGAND-CPD:C00266:*CAS:141-46-8 1.2.1.21 H2O + NAD+ + glycolaldehyde = NADH + glycolate ethylene glycol degradation glycolaldehyde 2-OH-acetaldehyde*glycolaldehyde*hydroxyacetaldehyde*2-hydroxyethanal 60.052 C2 H4 O2 C(O)C=O LIGAND-CPD:C00266:*CAS:141-46-8 NAD+ + ethylene glycol = glycolaldehyde + NADH ethylene glycol degradation glycolaldehyde 2-OH-acetaldehyde*glycolaldehyde*hydroxyacetaldehyde*2-hydroxyethanal 60.052 C2 H4 O2 C(O)C=O LIGAND-CPD:C00266:*CAS:141-46-8 4.1.2.25 dihydro-neo-pterin = glycolaldehyde + 6-hydroxymethyl-dihydropterin tetrahydrofolate biosynthesis I glycolaldehyde 2-OH-acetaldehyde*glycolaldehyde*hydroxyacetaldehyde*2-hydroxyethanal 60.052 C2 H4 O2 C(O)C=O LIGAND-CPD:C00266:*CAS:141-46-8 4.1.2.25 dihydro-neo-pterin = glycolaldehyde + 6-hydroxymethyl-dihydropterin tetrahydrofolate biosynthesis II m-chlorobenzoate m-chlorobenzoic acid*3-chlorobenzoic acid 156.568 C7 H5 O2 CL1 C(=O)(O)c1(cc(Cl)ccc1) m-chlorobenzoate + glycine = m-chlorohippurate + H2O bupropion degradation m-chlorobenzoate m-chlorobenzoic acid*3-chlorobenzoic acid 156.568 C7 H5 O2 CL1 C(=O)(O)c1(cc(Cl)ccc1) bupropion = m-chlorobenzoate bupropion degradation 1-deoxy-capsidiol 3α-hydroxy-5-epiaristolochene 220.354 C15 H24 O1 CC12(C(=CCC(C1)C(=C)C)CCC(O)C(C)2) 5-epi-aristolochene + O2 + NADPH = 1-deoxy-capsidiol + H2O + NADP+ capsidiol biosynthesis 1-deoxy-capsidiol 3α-hydroxy-5-epiaristolochene 220.354 C15 H24 O1 CC12(C(=CCC(C1)C(=C)C)CCC(O)C(C)2) 1-deoxy-capsidiol + O2 + NADPH = capsidiol + H2O + NADP+ capsidiol biosynthesis indole-3-glycol 177.202 C10 H11 N1 O2 c1(c(C(O)CO)c2(c([nH]1)cccc2)) 1.13.99.3 indole-3-glycol = indole-3-ketol tryptophan degradation V (side chain pathway) indole-3-glycol 177.202 C10 H11 N1 O2 c1(c(C(O)CO)c2(c([nH]1)cccc2)) 1.13.99.3 indole-3-ethanol + O2 = indole-3-glycol tryptophan degradation V (side chain pathway) indole-3-glycol 177.202 C10 H11 N1 O2 c1(c(C(O)CO)c2(c([nH]1)cccc2)) 1.1.99.8 indole-3-glycol aldehyde + NADH + H+ = indole-3-glycol + NAD+ tryptophan degradation V (side chain pathway) octadec-9-ene-1,18-dioic-acid 312.448 C18 H32 O4 C(=O)(O)CCCCCCCC=CCCCCCCCC(O)=O 1.1.1.- 18-oxooleate + NADP+ + H2O = octadec-9-ene-1,18-dioic-acid + NADPH suberin biosynthesis oryzalexin E 304.472 C20 H32 O2 C=CC1(C=C2(C(CC1)(O)C3([CH](CC2)C(C)(C)C(O)CC3)(C)))(C) ent-sandaracopimaradiene-3α-ol = oryzalexin E oryzalexin A-F biosynthesis UMP uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 324.183 C9 H13 N2 O9 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(O)(O)=O)) LIGAND-CPD:C00105:*CAS:58-97-9 2.7.1.48 uridine + GTP = UMP + GDP salvage pathways of pyrimidine ribonucleotides UMP uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 324.183 C9 H13 N2 O9 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(O)(O)=O)) LIGAND-CPD:C00105:*CAS:58-97-9 2.7.1.48 uridine + ATP = UMP + ADP salvage pathways of purine and pyrimidine nucleotides UMP uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 324.183 C9 H13 N2 O9 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(O)(O)=O)) LIGAND-CPD:C00105:*CAS:58-97-9 2.7.8.13 undecaprenyl phosphate = UMP peptidoglycan biosynthesis I UMP uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 324.183 C9 H13 N2 O9 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(O)(O)=O)) LIGAND-CPD:C00105:*CAS:58-97-9 H2O + UDP-2,3-bis(3-hydroxymyristoyl)glucosamine = 2,3-bis(3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate + UMP lipid-A-precursor biosynthesis UMP uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 324.183 C9 H13 N2 O9 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(O)(O)=O)) LIGAND-CPD:C00105:*CAS:58-97-9 2.4.2.9 diphosphate + UMP = 5-phosphoribosyl 1-pyrophosphate + uracil salvage pathways of purine and pyrimidine nucleotides UMP uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 324.183 C9 H13 N2 O9 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(O)(O)=O)) LIGAND-CPD:C00105:*CAS:58-97-9 2.4.2.9 diphosphate + UMP = 5-phosphoribosyl 1-pyrophosphate + uracil salvage pathways of pyrimidine ribonucleotides UMP uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 324.183 C9 H13 N2 O9 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(O)(O)=O)) LIGAND-CPD:C00105:*CAS:58-97-9 2.7.4.- ATP + UMP = ADP + UDP de novo biosynthesis of pyrimidine ribonucleotides UMP uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 324.183 C9 H13 N2 O9 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(O)(O)=O)) LIGAND-CPD:C00105:*CAS:58-97-9 2.7.4.- ATP + UMP = ADP + UDP salvage pathways of purine and pyrimidine nucleotides UMP uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 324.183 C9 H13 N2 O9 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(O)(O)=O)) LIGAND-CPD:C00105:*CAS:58-97-9 4.1.1.23 orotidine-5'-phosphate = CO2 + UMP de novo biosynthesis of pyrimidine ribonucleotides UMP uridylate*5'-UMP*U*uridine-5'-monophosphate*5'-uridylic acid (8CI)(9CI)*uridine-monophosphate*uridine-5'-phosphate*uridine-phosphate 324.183 C9 H13 N2 O9 P1 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(O)C2O)COP(O)(O)=O)) LIGAND-CPD:C00105:*CAS:58-97-9 2.7.8.15 dolichyl-phosphate + UDP-N-acetyl-D-glucosamine = N-acetylglucosaminyl-diphosphodolichol + UMP dolichyl-diphosphooligosaccharide biosynthesis phosphoribosyl-AMP 1-(5-Phosphoribosyl)-AMP*N1-(5-phospho-D-ribosyl)-AMP*5-phosphoribosyl-AMP*N-(5-phospho-D-ribosyl)-AMP*N-(5'-phospho-D-ribosyl)-AMP 559.319 C15 H23 N5 O14 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n3(c2(ncn(c(=N)c2nc3)C4(OC(C(O)C(O)4)COP(O)(=O)O)))) LIGAND-CPD:C02741: 3.6.1.31 phosphoribosyl-ATP + H2O = phosphoribosyl-AMP + diphosphate histidine biosynthesis I phosphoribosyl-AMP 1-(5-Phosphoribosyl)-AMP*N1-(5-phospho-D-ribosyl)-AMP*5-phosphoribosyl-AMP*N-(5-phospho-D-ribosyl)-AMP*N-(5'-phospho-D-ribosyl)-AMP 559.319 C15 H23 N5 O14 P2 C(OP(O)(=O)O)C1(OC(C(O)C(O)1)n3(c2(ncn(c(=N)c2nc3)C4(OC(C(O)C(O)4)COP(O)(=O)O)))) LIGAND-CPD:C02741: 3.5.4.19 phosphoribosyl-AMP + H2O = phosphoribosylformiminoAICAR-phosphate histidine biosynthesis I S-formylglutathione 335.331 C11 H17 N3 O7 S1 C(CCC(N)C(=O)O)(=O)NC(CS[CH]=O)C(=O)NCC(=O)O LIGAND-CPD:C01031: 1.1.1.284 S-hydroxymethylglutathione = S-formylglutathione + H+ formaldehyde oxidation II (glutathione-dependent) S-formylglutathione 335.331 C11 H17 N3 O7 S1 C(CCC(N)C(=O)O)(=O)NC(CS[CH]=O)C(=O)NCC(=O)O LIGAND-CPD:C01031: 3.1.2.12 S-formylglutathione + H2O = formate + glutathione formaldehyde oxidation II (glutathione-dependent) indole-3-acetyl-asp indole-3-acetyl-aspartic acid*indole-3-acetyl-aspartate 290.275 C14 H14 N2 O5 C(=O)(O)CC(C(=O)O)NC(=O)Cc1(c2(c([nH]c1)cccc2)) indole-3-acetate + L-aspartate = indole-3-acetyl-asp + H2O IAA conjugate biosynthesis II isobutanol butanol 74.122 C4 H10 O1 CC(C)CO 1.1.1.1 isobutanal + NADH = isobutanol + NAD+ valine degradation II 1-(3-aminopropyl)-pyrrolinium 127.209 C7 H15 N2 C(N)CC[N+]1(CCCC=1) 1-(3-aminopropyl)-4-aminobutanal = 1-(3-aminopropyl)-pyrrolinium + H2O β-alanine biosynthesis I 1-(3-aminopropyl)-pyrrolinium 127.209 C7 H15 N2 C(N)CC[N+]1(CCCC=1) 1-(3-aminopropyl)-pyrrolinium = 1,5-diazabicyclononane β-alanine biosynthesis I tiglyl-CoA 2-methylbut-2-enoyl-CoA*trans-2-methylbut-2-enoyl-CoA*tigloyl-CoA*tiglyl-CoA*methylcrotonyl-CoA 849.636 C26 H42 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(=O)(O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)=CC) CAS:6247-62-7 1.3.99.12 S-2-methyl-butyryl-CoA + FAD = tiglyl-CoA + FADH2 isoleucine degradation I tiglyl-CoA 2-methylbut-2-enoyl-CoA*trans-2-methylbut-2-enoyl-CoA*tigloyl-CoA*tiglyl-CoA*methylcrotonyl-CoA 849.636 C26 H42 N7 O17 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(=O)(O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C(C)=CC) CAS:6247-62-7 4.2.1.17 tiglyl-CoA + H2O = 2-methyl-3-hydroxybutyryl-CoA isoleucine degradation I phytofluene 2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,12,14,16,18,22,26,30-decaene*7,8,11,12,7',8'-hexahydro-ψ,ψ-carotene 542.93 C40 H62 CC(C)=CCCC(C)=CCCC(C)=CC=CC(C)=CC=CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C 1.14.99.- phytoene + O2 = phytofluene + H2O carotenoid biosynthesis phytofluene 2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,12,14,16,18,22,26,30-decaene*7,8,11,12,7',8'-hexahydro-ψ,ψ-carotene 542.93 C40 H62 CC(C)=CCCC(C)=CCCC(C)=CC=CC(C)=CC=CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C 1.14.99.- phytofluene + O2 = ζ-carotene + H2O carotenoid biosynthesis 2,3-dehydrokievitone 354.359 C20 H18 O6 CC(C)=CCc2(c1(OC=C(C(=O)c1c(O)cc2O)c3(c(O)cc(O)cc3))) 2.5.1.1 2'-hydroxygenistein + dimethylallyl-PP = 2,3-dehydrokievitone + diphosphate kievitone biosynthesis 2,3-dehydrokievitone 354.359 C20 H18 O6 CC(C)=CCc2(c1(OC=C(C(=O)c1c(O)cc2O)c3(c(O)cc(O)cc3))) 2,3-dehydrokievitone + NADPH = kievitone + NADP+ kievitone biosynthesis deoxyribose-1-phosphate 2-deoxy-D-ribose-1-phosphate*2-deoxy-α-D-ribose 1-phosphate 214.111 C5 H11 O7 P1 [CH]1(O[CH](CO)[CH](O)[CH2]1)(OP(O)(O)=O) LIGAND-CPD:C00672:*CAS:17210-42-3 deoxyinosine = hypoxanthine + deoxyribose-1-phosphate salvage pathways of adenine, hypoxanthine, and their nucleosides deoxyribose-1-phosphate 2-deoxy-D-ribose-1-phosphate*2-deoxy-α-D-ribose 1-phosphate 214.111 C5 H11 O7 P1 [CH]1(O[CH](CO)[CH](O)[CH2]1)(OP(O)(O)=O) LIGAND-CPD:C00672:*CAS:17210-42-3 5.4.2.7 deoxyribose-1-phosphate = deoxyribose-5-phosphate (deoxy)ribose phosphate degradation deoxyribose-1-phosphate 2-deoxy-D-ribose-1-phosphate*2-deoxy-α-D-ribose 1-phosphate 214.111 C5 H11 O7 P1 [CH]1(O[CH](CO)[CH](O)[CH2]1)(OP(O)(O)=O) LIGAND-CPD:C00672:*CAS:17210-42-3 2.4.2.4 thymidine = deoxyribose-1-phosphate + thymine salvage pathways of purine and pyrimidine nucleotides deoxyribose-1-phosphate 2-deoxy-D-ribose-1-phosphate*2-deoxy-α-D-ribose 1-phosphate 214.111 C5 H11 O7 P1 [CH]1(O[CH](CO)[CH](O)[CH2]1)(OP(O)(O)=O) LIGAND-CPD:C00672:*CAS:17210-42-3 2.4.2.4 thymidine = deoxyribose-1-phosphate + thymine (deoxy)ribose phosphate degradation deoxyribose-1-phosphate 2-deoxy-D-ribose-1-phosphate*2-deoxy-α-D-ribose 1-phosphate 214.111 C5 H11 O7 P1 [CH]1(O[CH](CO)[CH](O)[CH2]1)(OP(O)(O)=O) LIGAND-CPD:C00672:*CAS:17210-42-3 2.4.2.4 thymidine = deoxyribose-1-phosphate + thymine salvage pathways of pyrimidine deoxyribonucleotides deoxyribose-1-phosphate 2-deoxy-D-ribose-1-phosphate*2-deoxy-α-D-ribose 1-phosphate 214.111 C5 H11 O7 P1 [CH]1(O[CH](CO)[CH](O)[CH2]1)(OP(O)(O)=O) LIGAND-CPD:C00672:*CAS:17210-42-3 adenine + deoxyribose-1-phosphate = deoxyadenosine salvage pathways of adenine, hypoxanthine, and their nucleosides deoxyribose-1-phosphate 2-deoxy-D-ribose-1-phosphate*2-deoxy-α-D-ribose 1-phosphate 214.111 C5 H11 O7 P1 [CH]1(O[CH](CO)[CH](O)[CH2]1)(OP(O)(O)=O) LIGAND-CPD:C00672:*CAS:17210-42-3 deoxyuridine = deoxyribose-1-phosphate + uracil (deoxy)ribose phosphate degradation deoxyribose-1-phosphate 2-deoxy-D-ribose-1-phosphate*2-deoxy-α-D-ribose 1-phosphate 214.111 C5 H11 O7 P1 [CH]1(O[CH](CO)[CH](O)[CH2]1)(OP(O)(O)=O) LIGAND-CPD:C00672:*CAS:17210-42-3 deoxyuridine = deoxyribose-1-phosphate + uracil salvage pathways of pyrimidine deoxyribonucleotides 4-carboxyaminoimidazole ribonucleotide 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*5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate*phosphoribosyl-carboxy-aminoimidazole 339.198 C9 H14 N3 O9 P1 C(OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c(N)c(C(O)=O)nc2)) LIGAND-CPD:C04751: 6.3.2.6 ATP + 4-carboxyaminoimidazole ribonucleotide + L-aspartate = ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole purine nucleotides de novo biosynthesis II 4-carboxyaminoimidazole ribonucleotide 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*5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate*phosphoribosyl-carboxy-aminoimidazole 339.198 C9 H14 N3 O9 P1 C(OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c(N)c(C(O)=O)nc2)) LIGAND-CPD:C04751: 6.3.2.6 ATP + 4-carboxyaminoimidazole ribonucleotide + L-aspartate = ADP + 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole purine nucleotides de novo biosynthesis I 4-carboxyaminoimidazole ribonucleotide 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*5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate*phosphoribosyl-carboxy-aminoimidazole 339.198 C9 H14 N3 O9 P1 C(OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c(N)c(C(O)=O)nc2)) LIGAND-CPD:C04751: N5-carboxyaminoimidazole ribonucleotide = 4-carboxyaminoimidazole ribonucleotide purine nucleotides de novo biosynthesis I 4-carboxyaminoimidazole ribonucleotide 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*5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate*phosphoribosyl-carboxy-aminoimidazole 339.198 C9 H14 N3 O9 P1 C(OP(O)(O)=O)C1(OC(C(O)C(O)1)n2(c(N)c(C(O)=O)nc2)) LIGAND-CPD:C04751: 4.1.1.21 4-carboxyaminoimidazole ribonucleotide = 5-aminoimidazole ribonucleotide + CO2 purine nucleotides de novo biosynthesis II dihydromyricetin ampelopsin 320.255 C15 H12 O8 c3(c2(OC(c1(cc(O)c(O)c(O)c1))C(O)C(=O)c2c(O)cc(O)3)) 3',4',5'-pentahydroxyflavanone + α-ketoglutarate + O2 = dihydromyricetin + succinate + CO2 leucodelphinidin biosynthesis dihydromyricetin ampelopsin 320.255 C15 H12 O8 c3(c2(OC(c1(cc(O)c(O)c(O)c1))C(O)C(=O)c2c(O)cc(O)3)) 1.14.13.- dihydrokaempferol + NADPH + O2 = dihydromyricetin + NADP+ + H2O leucodelphinidin biosynthesis dihydromyricetin ampelopsin 320.255 C15 H12 O8 c3(c2(OC(c1(cc(O)c(O)c(O)c1))C(O)C(=O)c2c(O)cc(O)3)) 1.14.13.88 dihydroquercetin + NADPH + O2 = dihydromyricetin + NADP+ + H2O leucodelphinidin biosynthesis dihydromyricetin ampelopsin 320.255 C15 H12 O8 c3(c2(OC(c1(cc(O)c(O)c(O)c1))C(O)C(=O)c2c(O)cc(O)3)) 1.1.1.219 dihydromyricetin + NADPH = leucodelphinidin + NADP+ leucodelphinidin biosynthesis 6G,6-kestotetraose kestotetraose 666.583 C24 H42 O21 C(O)C1(OC(C(O)C(O)1)(CO)OCC2(OC(C(O)C2O)(CO)OCC3(OC(C(O)C(O)C3O)OC4(CO)(OC(CO)C(O)C(O)4)))) 3.2.1.- 6G,6-kestotetraose + H2O = 6G-kestotriose + fructose fructan degradation benzyladenine-7-N-glucoside 387.394 C18 H21 N5 O5 c2(c1(N(C=Nc1ncn2)C3(OC(CO)C(O)C(O)C(O)3)))(NCc4(ccccc4)) 2.4.1.- benzyladenine + UDP-D-glucose = benzyladenine-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis 1,3-diphosphateglycerate 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 266.038 C3 H8 O10 P2 C(OP(O)(O)=O)(=O)C(O)COP(O)(O)=O LIGAND-CPD:C00236:*CAS:1981-49-3 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP Calvin cycle 1,3-diphosphateglycerate 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 266.038 C3 H8 O10 P2 C(OP(O)(O)=O)(=O)C(O)COP(O)(O)=O LIGAND-CPD:C00236:*CAS:1981-49-3 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP gluconeogenesis 1,3-diphosphateglycerate 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 266.038 C3 H8 O10 P2 C(OP(O)(O)=O)(=O)C(O)COP(O)(O)=O LIGAND-CPD:C00236:*CAS:1981-49-3 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP sucrose degradation to ethanol and lactate (anaerobic) 1,3-diphosphateglycerate 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 266.038 C3 H8 O10 P2 C(OP(O)(O)=O)(=O)C(O)COP(O)(O)=O LIGAND-CPD:C00236:*CAS:1981-49-3 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP glycolysis IV (plant cytosol) 1,3-diphosphateglycerate 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 266.038 C3 H8 O10 P2 C(OP(O)(O)=O)(=O)C(O)COP(O)(O)=O LIGAND-CPD:C00236:*CAS:1981-49-3 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP fructose degradation to pyruvate and lactate (anaerobic) 1,3-diphosphateglycerate 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 266.038 C3 H8 O10 P2 C(OP(O)(O)=O)(=O)C(O)COP(O)(O)=O LIGAND-CPD:C00236:*CAS:1981-49-3 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP glucose fermentation to lactate II 1,3-diphosphateglycerate 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 266.038 C3 H8 O10 P2 C(OP(O)(O)=O)(=O)C(O)COP(O)(O)=O LIGAND-CPD:C00236:*CAS:1981-49-3 2.7.2.3 3-phosphoglycerate + ATP = 1,3-diphosphateglycerate + ADP glycolysis I 1,3-diphosphateglycerate 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 266.038 C3 H8 O10 P2 C(OP(O)(O)=O)(=O)C(O)COP(O)(O)=O LIGAND-CPD:C00236:*CAS:1981-49-3 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH gluconeogenesis 1,3-diphosphateglycerate 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 266.038 C3 H8 O10 P2 C(OP(O)(O)=O)(=O)C(O)COP(O)(O)=O LIGAND-CPD:C00236:*CAS:1981-49-3 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH sucrose degradation to ethanol and lactate (anaerobic) 1,3-diphosphateglycerate 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 266.038 C3 H8 O10 P2 C(OP(O)(O)=O)(=O)C(O)COP(O)(O)=O LIGAND-CPD:C00236:*CAS:1981-49-3 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH glycolysis IV (plant cytosol) 1,3-diphosphateglycerate 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 266.038 C3 H8 O10 P2 C(OP(O)(O)=O)(=O)C(O)COP(O)(O)=O LIGAND-CPD:C00236:*CAS:1981-49-3 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH fructose degradation to pyruvate and lactate (anaerobic) 1,3-diphosphateglycerate 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 266.038 C3 H8 O10 P2 C(OP(O)(O)=O)(=O)C(O)COP(O)(O)=O LIGAND-CPD:C00236:*CAS:1981-49-3 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH glucose fermentation to lactate II 1,3-diphosphateglycerate 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 266.038 C3 H8 O10 P2 C(OP(O)(O)=O)(=O)C(O)COP(O)(O)=O LIGAND-CPD:C00236:*CAS:1981-49-3 1.2.1.12 D-glyceraldehyde-3-phosphate + NAD+ = 1,3-diphosphateglycerate + NADH glycolysis I 1,3-diphosphateglycerate 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 266.038 C3 H8 O10 P2 C(OP(O)(O)=O)(=O)C(O)COP(O)(O)=O LIGAND-CPD:C00236:*CAS:1981-49-3 1.2.1.59 D-glyceraldehyde-3-phosphate = 1,3-diphosphateglycerate Calvin cycle 2-amino-3-oxobutanoate 2-amino-acetoacetate*2-amino-3-ketobutyrate*2-amino-3-oxobutyrate*α-amino-β-ketobutyrate*L-2-amino-3-oxobutanoate 117.104 C4 H7 N1 O3 C(O)(=O)C(N)C(=O)C LIGAND-CPD:C03508: 2-amino-3-oxobutanoate = aminoacetone + CO2 threonine degradation III (to methylglyoxal) 2-amino-3-oxobutanoate 2-amino-acetoacetate*2-amino-3-ketobutyrate*2-amino-3-oxobutyrate*α-amino-β-ketobutyrate*L-2-amino-3-oxobutanoate 117.104 C4 H7 N1 O3 C(O)(=O)C(N)C(=O)C LIGAND-CPD:C03508: 2-amino-3-oxobutanoate = aminoacetone + CO2 aminopropanol biosynthesis 2-amino-3-oxobutanoate 2-amino-acetoacetate*2-amino-3-ketobutyrate*2-amino-3-oxobutyrate*α-amino-β-ketobutyrate*L-2-amino-3-oxobutanoate 117.104 C4 H7 N1 O3 C(O)(=O)C(N)C(=O)C LIGAND-CPD:C03508: 2.3.1.29 glycine + acetyl-CoA = 2-amino-3-oxobutanoate + coenzyme A threonine degradation II 2-amino-3-oxobutanoate 2-amino-acetoacetate*2-amino-3-ketobutyrate*2-amino-3-oxobutyrate*α-amino-β-ketobutyrate*L-2-amino-3-oxobutanoate 117.104 C4 H7 N1 O3 C(O)(=O)C(N)C(=O)C LIGAND-CPD:C03508: 1.1.1.103 L-threonine + NAD+ = 2-amino-3-oxobutanoate + NADH threonine degradation II 2-amino-3-oxobutanoate 2-amino-acetoacetate*2-amino-3-ketobutyrate*2-amino-3-oxobutyrate*α-amino-β-ketobutyrate*L-2-amino-3-oxobutanoate 117.104 C4 H7 N1 O3 C(O)(=O)C(N)C(=O)C LIGAND-CPD:C03508: 1.1.1.103 L-threonine + NAD+ = 2-amino-3-oxobutanoate + NADH threonine degradation III (to methylglyoxal) 2-amino-3-oxobutanoate 2-amino-acetoacetate*2-amino-3-ketobutyrate*2-amino-3-oxobutyrate*α-amino-β-ketobutyrate*L-2-amino-3-oxobutanoate 117.104 C4 H7 N1 O3 C(O)(=O)C(N)C(=O)C LIGAND-CPD:C03508: 1.1.1.103 L-threonine + NAD+ = 2-amino-3-oxobutanoate + NADH aminopropanol biosynthesis D-xylose xylose*α-D-xylose*wood sugar 150.131 C5 H10 O5 C1(C(O)C(O)C(O)C(O1)O) PUBCHEM:6027:*LIGAND-CPD:C00181:*CAS:58-86-6 5.3.1.5 D-xylose = D-xylulose xylose degradation 18:3-t16:1-PG 1-18:3-2-trans-16:1-phosphatidylglycerol*1-(9Z,12Z,15Z-octadecatrienoyl)-2-(3E-hexadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) 742.969 C40 H71 O10 P1 C(OP(=O)(O)OCC(O)CO)C(OC(=O)CC=CCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:2-t16:1-PG = 18:3-t16:1-PG phospholipid desaturation 18:3-t16:1-PG 1-18:3-2-trans-16:1-phosphatidylglycerol*1-(9Z,12Z,15Z-octadecatrienoyl)-2-(3E-hexadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) 742.969 C40 H71 O10 P1 C(OP(=O)(O)OCC(O)CO)C(OC(=O)CC=CCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:3-16:0-PG = 18:3-t16:1-PG phospholipid desaturation prephenate 226.185 C10 H10 O6 C(=O)(O)C(=O)CC1(C(O)=O)(C=C[CH](O)C=C1) LIGAND-CPD:C00254:*CAS:126-49-8 4.2.1.51 prephenate = phenylpyruvate + H2O + CO2 phenylalanine biosynthesis I prephenate 226.185 C10 H10 O6 C(=O)(O)C(=O)CC1(C(O)=O)(C=C[CH](O)C=C1) LIGAND-CPD:C00254:*CAS:126-49-8 5.4.99.5 chorismate = prephenate phenylalanine biosynthesis I guanine 151.127 C5 H5 N5 O1 c12([nH]cnc(c(=O)[nH]c(N)n1)2) LIGAND-CPD:C00242:*CAS:73-40-5 3.2.2.1 guanosine + H2O = guanine + D-ribose purine degradation guanine 151.127 C5 H5 N5 O1 c12([nH]cnc(c(=O)[nH]c(N)n1)2) LIGAND-CPD:C00242:*CAS:73-40-5 3.2.2.1 guanosine + H2O = guanine + D-ribose salvage pathways of purine nucleosides II (plant) guanine 151.127 C5 H5 N5 O1 c12([nH]cnc(c(=O)[nH]c(N)n1)2) LIGAND-CPD:C00242:*CAS:73-40-5 2.4.2.8 5-phosphoribosyl 1-pyrophosphate + guanine = diphosphate + GMP salvage pathways of purine nucleosides guanine 151.127 C5 H5 N5 O1 c12([nH]cnc(c(=O)[nH]c(N)n1)2) LIGAND-CPD:C00242:*CAS:73-40-5 2.4.2.8 5-phosphoribosyl 1-pyrophosphate + guanine = diphosphate + GMP salvage pathways of purine and pyrimidine nucleotides guanine 151.127 C5 H5 N5 O1 c12([nH]cnc(c(=O)[nH]c(N)n1)2) LIGAND-CPD:C00242:*CAS:73-40-5 2.4.2.8 5-phosphoribosyl 1-pyrophosphate + guanine = diphosphate + GMP salvage pathways of purine nucleosides II (plant) guanine 151.127 C5 H5 N5 O1 c12([nH]cnc(c(=O)[nH]c(N)n1)2) LIGAND-CPD:C00242:*CAS:73-40-5 2.4.2.15 guanosine = ribose-1-phosphate + guanine salvage pathways of purine nucleosides guanine 151.127 C5 H5 N5 O1 c12([nH]cnc(c(=O)[nH]c(N)n1)2) LIGAND-CPD:C00242:*CAS:73-40-5 2.4.2.15 guanosine = ribose-1-phosphate + guanine salvage pathways of purine and pyrimidine nucleotides guanine 151.127 C5 H5 N5 O1 c12([nH]cnc(c(=O)[nH]c(N)n1)2) LIGAND-CPD:C00242:*CAS:73-40-5 3.5.4.3 H2O + guanine = ammonia + xanthine purine degradation guanine 151.127 C5 H5 N5 O1 c12([nH]cnc(c(=O)[nH]c(N)n1)2) LIGAND-CPD:C00242:*CAS:73-40-5 3.5.4.3 H2O + guanine = ammonia + xanthine salvage pathways of purine nucleosides guanine 151.127 C5 H5 N5 O1 c12([nH]cnc(c(=O)[nH]c(N)n1)2) LIGAND-CPD:C00242:*CAS:73-40-5 3.5.4.3 H2O + guanine = ammonia + xanthine salvage pathways of purine nucleosides II (plant) isoliquiritigenin 42'4'-trihydroxychalcone 256.257 C15 H12 O4 C(c1(ccc(O)cc1))=CC(=O)c2(c(O)cc(O)cc2) 2.3.1.170 coumaroyl-CoA + malonyl-CoA + NADPH = isoliquiritigenin + coenzyme A + CO2 + NADP+ + H2O flavonoid biosynthesis (-)-α-pinene (-)-(1S,5S)-α-pinene 136.236 C10 H16 CC1(C2(CC1C(C)=CC2))(C) 4.2.3.14 geranyl-PP = (-)-α-pinene + diphosphate oleoresin monoterpene volatiles biosynthesis (-)-α-pinene (-)-(1S,5S)-α-pinene 136.236 C10 H16 CC1(C2(CC1C(C)=CC2))(C) 4.2.3.14 geranyl-PP = (-)-α-pinene + diphosphate monoterpene biosynthesis coumarinate coumarinic acid 164.16 C9 H8 O3 C(=O)(O)C=Cc1(c(O)cccc1) coumarinate = coumarin + H2O coumarin biosynthesis (via 2-coumarate) coumarinate coumarinic acid 164.16 C9 H8 O3 C(=O)(O)C=Cc1(c(O)cccc1) 3.2.1.21 coumarinic acid-β-D-glucoside + H2O = coumarinate + β-D-glucose coumarin biosynthesis (via 2-coumarate) 5-hydroxy-coniferaldehyde 194.187 C10 H10 O4 C(=O)C=Cc1(cc(OC)c(O)c(c1)O) 1.14.13.- coniferyl aldehyde + NADPH + O2 = 5-hydroxy-coniferaldehyde + NADP+ + H2O phenylpropanoid biosynthesis 5-hydroxy-coniferaldehyde 194.187 C10 H10 O4 C(=O)C=Cc1(cc(OC)c(O)c(c1)O) 2.1.1.68 5-hydroxy-coniferaldehyde + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + sinapaldehyde phenylpropanoid biosynthesis trans-lycopene ψ,ψ-carotene 536.882 C40 H56 CC(C)=CCCC(C)=CC=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC=C(C)CCC=C(C)C 5.5.1.- trans-lycopene = γ-carotene carotenoid biosynthesis trans-lycopene ψ,ψ-carotene 536.882 C40 H56 CC(C)=CCCC(C)=CC=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC=C(C)CCC=C(C)C 1.14.99.30 O2 + neurosporene = H2O + trans-lycopene carotenoid biosynthesis trans-lycopene ψ,ψ-carotene 536.882 C40 H56 CC(C)=CCCC(C)=CC=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC=C(C)CCC=C(C)C 5.5.1.- trans-lycopene = δ-carotene carotenoid biosynthesis coumaraldehyde 148.161 C9 H8 O2 C(=O)C=Cc1(ccc(O)cc1) 1.1.1.195 coumaraldehyde + NADPH = coumaryl-alcohol + NADP+ phenylpropanoid biosynthesis coumaraldehyde 148.161 C9 H8 O2 C(=O)C=Cc1(ccc(O)cc1) 1.2.1.44 coumaroyl-CoA + NADPH = coumaraldehyde + NADP+ + coenzyme A phenylpropanoid biosynthesis THF-L-glutamate tetrahydrofolate glutamate 573.541 C24 H29 N8 O9 C(=O)(O)C(CCC(O)=O)NC(=O)CCC(C(=O)O)NC(=O)c1(ccc(cc1)NC[CH]2(Nc3(c(NC2)nc(N)nc3=O))) 6.3.2.17 tetrahydrofolate + L-glutamate + ATP = THF-L-glutamate + ADP tetrahydrofolate biosynthesis II 9-oxo-nonanoate 9-oxo-nonanoic acid 172.224 C9 H16 O3 C(=O)CCCCCCCC(O)=O 9-HPOT = (3Z,6Z)-nonadienal + 9-oxo-nonanoate 9-LOX and 9-HPL pathway 9-oxo-nonanoate 9-oxo-nonanoic acid 172.224 C9 H16 O3 C(=O)CCCCCCCC(O)=O 9-HPOD = (3Z)-nonenal + 9-oxo-nonanoate 9-LOX and 9-HPL pathway 2,3-diketo-5-methylthio-1-phosphopentane DKM-1-P*1-phospho-2,3-diketo-5-methylthiopentane*1-phosphoryloxy-2,3-diketo-5-methylthiopentane 242.183 C6 H11 O6 P1 S1 C(SC)CC(=O)C(=O)COP(O)(=O)O 2,3-diketo-5-methylthio-1-phosphopentane = 2-hydroxy-3-keto-5-methylthio-1-phosphopentene methionine salvage pathway 2,3-diketo-5-methylthio-1-phosphopentane DKM-1-P*1-phospho-2,3-diketo-5-methylthiopentane*1-phosphoryloxy-2,3-diketo-5-methylthiopentane 242.183 C6 H11 O6 P1 S1 C(SC)CC(=O)C(=O)COP(O)(=O)O 5-methylthioribulose-1-phosphate = 2,3-diketo-5-methylthio-1-phosphopentane + H2O methionine salvage pathway 18:3-18:1-PC 1-18:3-2-18:1-phosphatidylcholine 783.1 C44 H81 N1 O8 P1 C(OP(=O)(O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:2-18:1-PC = 18:3-18:1-PC phospholipid desaturation 18:3-18:1-PC 1-18:3-2-18:1-phosphatidylcholine 783.1 C44 H81 N1 O8 P1 C(OP(=O)(O)OCC[N+](C)(C)C)C(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 1.14.99.- 18:3-18:1-PC = 18:3-18:2-PC phospholipid desaturation N2-succinylglutamate N2-Succinyl-L-glutamate*N2-succinylglutamatic acid*N2-succinylglutamic acid 247.204 C9 H13 N1 O7 C(=O)(O)CCC(=O)NC(C(O)=O)CCC(O)=O CAS:33981-72-5:*LIGAND-CPD:C05931: 1.2.1.- N2-succinyl-L-glutamate 5-semialdehyde + NAD+ + H2O = N2-succinylglutamate + NADH arginine degradation II N2-succinylglutamate N2-Succinyl-L-glutamate*N2-succinylglutamatic acid*N2-succinylglutamic acid 247.204 C9 H13 N1 O7 C(=O)(O)CCC(=O)NC(C(O)=O)CCC(O)=O CAS:33981-72-5:*LIGAND-CPD:C05931: 3.5.1.- N2-succinylglutamate + H2O = L-glutamate + succinate arginine degradation 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 295.188 C8 H14 N3 O7 P1 c1(c(N)n(cn1)C2(OC(C(O)C2O)COP(O)(O)=O)) CAS:25635-88-5:*LIGAND-CPD:C03373: 6.3.4.18 5-aminoimidazole ribonucleotide + ATP + HCO3- = N5-carboxyaminoimidazole ribonucleotide + ADP purine nucleotides de novo 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 295.188 C8 H14 N3 O7 P1 c1(c(N)n(cn1)C2(OC(C(O)C2O)COP(O)(O)=O)) CAS:25635-88-5:*LIGAND-CPD:C03373: 5-aminoimidazole ribonucleotide = hydroxymethylpyrimidine phosphate thiamine 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 295.188 C8 H14 N3 O7 P1 c1(c(N)n(cn1)C2(OC(C(O)C2O)COP(O)(O)=O)) CAS:25635-88-5:*LIGAND-CPD:C03373: 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = ADP + 5-aminoimidazole ribonucleotide purine nucleotides de novo 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 295.188 C8 H14 N3 O7 P1 c1(c(N)n(cn1)C2(OC(C(O)C2O)COP(O)(O)=O)) CAS:25635-88-5:*LIGAND-CPD:C03373: 6.3.3.1 ATP + 5-phosphoribosyl-N-formylglycineamidine = ADP + 5-aminoimidazole ribonucleotide purine nucleotides de novo 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 295.188 C8 H14 N3 O7 P1 c1(c(N)n(cn1)C2(OC(C(O)C2O)COP(O)(O)=O)) CAS:25635-88-5:*LIGAND-CPD:C03373: 4.1.1.21 4-carboxyaminoimidazole ribonucleotide = 5-aminoimidazole ribonucleotide + CO2 purine nucleotides de novo biosynthesis II threohydrobupropion 241.76 C13 H20 N1 O1 CL1 CC(NC(C)(C)C)C(O)c1(cc(Cl)ccc1) bupropion = threohydrobupropion bupropion degradation (-)-medicarpin (6aR,11aR)-medicarpin*demethylhomopterocarpin 270.284 C16 H14 O4 C1([CH]3([CH](c2(c(O1)cc(O)cc2))Oc4(cc(OC)ccc34))) 7,2'-dihydroxy-4'-methoxy-isoflavanol carbocation intermediate 2 = (-)-medicarpin + H2O medicarpin biosynthesis (-)-medicarpin (6aR,11aR)-medicarpin*demethylhomopterocarpin 270.284 C16 H14 O4 C1([CH]3([CH](c2(c(O1)cc(O)cc2))Oc4(cc(OC)ccc34))) 7,2'-dihydroxy-4'-methoxy-isoflavanol-quinonemethide-intermediate-2 = (-)-medicarpin + H2O medicarpin biosynthesis 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester 131-hydroxy-Mg-protoporphyrin IX 13-monomethyl ester 614.982 C35 H34 N4 O5 MG1 Cc6(c(C(O)CC(=O)OC)c1(n7([Mg]35(n4(c(C=C2(C(C)=C(C(C=1)=N23)CCC(O)=O))c(C)c(C=C)c4C=C8(N5=C(C=c67)C(C=C)=C(C)8)))))) 1.14.13.81 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester 131-hydroxy-Mg-protoporphyrin IX 13-monomethyl ester 614.982 C35 H34 N4 O5 MG1 Cc6(c(C(O)CC(=O)OC)c1(n7([Mg]35(n4(c(C=C2(C(C)=C(C(C=1)=N23)CCC(O)=O))c(C)c(C=C)c4C=C8(N5=C(C=c67)C(C=C)=C(C)8)))))) 1.14.13.81 Mg-protoporphyrin monomethyl ester + NADPH + H+ + O2 = 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis 4α-carboxy-4β-methyl-5α-cholesta-8-en-3β-ol 444.696 C29 H48 O3 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(C(=O)O)(C)C(O)CC4)(C)))(C)) 1.1.1.170 4α-carboxy-4β-methyl-5α-cholesta-8-en-3β-ol = 4α-methyl-5α-cholesta-8-en-3-one + CO2 cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 4α-carboxy-4β-methyl-5α-cholesta-8-en-3β-ol 444.696 C29 H48 O3 CC(C)CCCC(C)C1(C2(C(CC1)C3(=C(CC2)C4(C(CC3)C(C(=O)O)(C)C(O)CC4)(C)))(C)) 1.14.13.72 4α-formyl-4β-methyl-5α-cholesta-8-en-3β-ol + O2 = 4α-carboxy-4β-methyl-5α-cholesta-8-en-3β-ol + H2O cholesterol biosynthesis II (via 24,25-dihydrolanosterol) 2'-deoxymugineic acid 1-azetidinebutanoic acid 304.299 C12 H20 N2 O7 C(O)(=O)C1(N(CC1)CCC(C(=O)O)NCCC(O)C(=O)O) LIGAND-CPD:C15485:*PUBCHEM:189811: 1.1.1.285 3''-deamino-3''-oxonicotianamine = 2'-deoxymugineic acid 2'-deoxymugineic acid phytosiderophore biosynthesis thiamine-phosphate thiamin monophosphate*thiamin phosphate*thiamin-P*thiamine-Pi*ThP*thiamine monophosphate 345.332 C12 H18 N4 O4 P1 S1 c1(c(cnc(n1)C)C[n+]2(c(C)c(sc2)CCOP(=O)(O)O))(N) CAS:532-40-1:*LIGAND-CPD:C01081: 2.7.4.16 thiamine-phosphate + ATP = thiamine diphosphate + ADP thiamine biosynthesis thiamine-phosphate thiamin monophosphate*thiamin phosphate*thiamin-P*thiamine-Pi*ThP*thiamine monophosphate 345.332 C12 H18 N4 O4 P1 S1 c1(c(cnc(n1)C)C[n+]2(c(C)c(sc2)CCOP(=O)(O)O))(N) CAS:532-40-1:*LIGAND-CPD:C01081: 2.5.1.3 4-methyl-5-(β-hydroxyethyl)thiazole phosphate + 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate = thiamine-phosphate + diphosphate thiamine biosynthesis thiamine-phosphate thiamin monophosphate*thiamin phosphate*thiamin-P*thiamine-Pi*ThP*thiamine monophosphate 345.332 C12 H18 N4 O4 P1 S1 c1(c(cnc(n1)C)C[n+]2(c(C)c(sc2)CCOP(=O)(O)O))(N) CAS:532-40-1:*LIGAND-CPD:C01081: 2.7.1.89 thiamin + ATP = thiamine-phosphate + ADP thiamine biosynthesis 3-hydroxy-5-oxohexanoate 146.143 C6 H10 O4 C(=O)(O)CC(O)CC(=O)C UM-BBD-CPD:c0028:*CAS:109138-72-9 3.7.1.- dihydrophloroglucinol + OH- = 3-hydroxy-5-oxohexanoate gallate degradation III (anaerobic) 3-hydroxy-5-oxohexanoate 146.143 C6 H10 O4 C(=O)(O)CC(O)CC(=O)C UM-BBD-CPD:c0028:*CAS:109138-72-9 2.8.3.- 3-hydroxy-5-oxohexanoate + acetyl-CoA = 3-hydroxy-5- oxohexanoyl-CoA + acetate gallate degradation III (anaerobic) N-carbamoylputrescine 131.177 C5 H13 N3 O1 C(N)CCCNC(=O)N CAS:6851-51-0 3.5.3.12 H2O + agmatine = ammonia + N-carbamoylputrescine putrescine biosynthesis II N-carbamoylputrescine 131.177 C5 H13 N3 O1 C(N)CCCNC(=O)N CAS:6851-51-0 3.5.3.12 H2O + agmatine = ammonia + N-carbamoylputrescine arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) N-carbamoylputrescine 131.177 C5 H13 N3 O1 C(N)CCCNC(=O)N CAS:6851-51-0 3.5.1.53 N-carbamoylputrescine + H2O = putrescine + CO2 + ammonia putrescine biosynthesis II N-carbamoylputrescine 131.177 C5 H13 N3 O1 C(N)CCCNC(=O)N CAS:6851-51-0 3.5.1.53 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 CC1(O[CH]([CH](O)[CH]1O)n2(c3(c(nc2)c(N)ncn3))) LIGAND-CPD:C05198: 2.8.1.6 dethiobiotin + S-adenosyl-L-methionine + sulfur donor = biotin + 5'-deoxyadenosine + L-methionine biotin biosynthesis I nicotinate 3-pyridinecarboxylic acid*nicotinic acid*wampocap*nicolar*nicocap*nicobid*nico-400-*nicamin*niacin*niacine*vitamin B3 122.103 C6 H4 N1 O2 c1(ccc(C([O-])=O)cn1) LIGAND-CPD:C00253:*CAS:59-67-6 2.4.2.1 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 122.103 C6 H4 N1 O2 c1(ccc(C([O-])=O)cn1) LIGAND-CPD:C00253:*CAS:59-67-6 2.4.2.11 nicotinate nucleotide + diphosphate = nicotinate + 5-phosphoribosyl 1-pyrophosphate NAD salvage pathway I nicotinate 3-pyridinecarboxylic acid*nicotinic acid*wampocap*nicolar*nicocap*nicobid*nico-400-*nicamin*niacin*niacine*vitamin B3 122.103 C6 H4 N1 O2 c1(ccc(C([O-])=O)cn1) LIGAND-CPD:C00253:*CAS:59-67-6 2.4.2.11 nicotinate nucleotide + diphosphate = nicotinate + 5-phosphoribosyl 1-pyrophosphate pyridine nucleotide cycling (plants) nicotinate 3-pyridinecarboxylic acid*nicotinic acid*wampocap*nicolar*nicocap*nicobid*nico-400-*nicamin*niacin*niacine*vitamin B3 122.103 C6 H4 N1 O2 c1(ccc(C([O-])=O)cn1) LIGAND-CPD:C00253:*CAS:59-67-6 3.2.2.- nicotinate nucleotide + H2O = 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 122.103 C6 H4 N1 O2 c1(ccc(C([O-])=O)cn1) LIGAND-CPD:C00253:*CAS:59-67-6 3.5.1.4 nicotinamide + H2O = ammonia + nicotinate aldoxime degradation nicotinate 3-pyridinecarboxylic acid*nicotinic acid*wampocap*nicolar*nicocap*nicobid*nico-400-*nicamin*niacin*niacine*vitamin B3 122.103 C6 H4 N1 O2 c1(ccc(C([O-])=O)cn1) LIGAND-CPD:C00253:*CAS:59-67-6 3.5.1.19 nicotinamide + H2O = ammonia + nicotinate NAD salvage pathway I nicotinate 3-pyridinecarboxylic acid*nicotinic acid*wampocap*nicolar*nicocap*nicobid*nico-400-*nicamin*niacin*niacine*vitamin B3 122.103 C6 H4 N1 O2 c1(ccc(C([O-])=O)cn1) LIGAND-CPD:C00253:*CAS:59-67-6 3.5.1.19 nicotinamide + H2O = ammonia + nicotinate pyridine nucleotide cycling (plants) chlorophyllide b 628.966 C35 H32 N4 O6 MG1 CCC9(C1(=N8([Mg]46(N5(=C(C2(C(C(=O)OC)C(=O)c3(c(C)c(=C1)n(c=23)4)))C(CCC(=O)O)C(C)C5=Cc7(n6c(c(C=C)c(C)7)C=C8C=9C=O)))))) 7-hydroxy-chlorophyllide a + O2 + NADPH = chlorophyllide b + H2O + NADP+ chlorophyll cycle chlorophyllide b 628.966 C35 H32 N4 O6 MG1 CCC9(C1(=N8([Mg]46(N5(=C(C2(C(C(=O)OC)C(=O)c3(c(C)c(=C1)n(c=23)4)))C(CCC(=O)O)C(C)C5=Cc7(n6c(c(C=C)c(C)7)C=C8C=9C=O)))))) 2.5.1.- chlorophyllide b + phytyl-PP = chlorophyll b + diphosphate chlorophyll cycle campestanol 5α-campestanol 402.702 C28 H50 O1 CC(C)C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC3)CC(O)CC4)(C)))) (5α)-campestan-3-one = campestanol brassinosteroid biosynthesis II campestanol 5α-campestanol 402.702 C28 H50 O1 CC(C)C(C)CCC(C)C1(C2(C)(C(CC1)C3(C(CC2)C4([CH](CC3)CC(O)CC4)(C)))) 1.14.13.- campestanol + O2 + NADPH = 6-deoxocathasterone + H2O + NADP+ brassinosteroid biosynthesis II iminoaspartate α-iminosuccinate 131.088 C4 H5 N1 O4 C(=O)(O)C(=N)CC(O)=O LIGAND-CPD:C05840: iminoaspartate + dihydroxy-acetone-phosphate = quinolinate + H2O NAD biosynthesis I (from aspartate) iminoaspartate α-iminosuccinate 131.088 C4 H5 N1 O4 C(=O)(O)C(=N)CC(O)=O LIGAND-CPD:C05840: 1.4.3.- O2 + L-aspartate = H2O2 + iminoaspartate NAD biosynthesis I (from aspartate) xanthosine 9 β-D-ribofuranosylxanthine 284.228 C10 H12 N4 O6 c1(c2(c([nH]c([nH]1)=O)n(cn2)[CH]3([CH](O)[CH](O)[CH](O3)CO)))(=O) LIGAND-CPD:C01762:*CAS:146-80-5 3.1.3.5 xanthosine-5-phosphate + H2O = xanthosine purine degradation xanthosine 9 β-D-ribofuranosylxanthine 284.228 C10 H12 N4 O6 c1(c2(c([nH]c([nH]1)=O)n(cn2)[CH]3([CH](O)[CH](O)[CH](O3)CO)))(=O) LIGAND-CPD:C01762:*CAS:146-80-5 3.1.3.5 xanthosine-5-phosphate + H2O = xanthosine ureide biosynthesis xanthosine 9 β-D-ribofuranosylxanthine 284.228 C10 H12 N4 O6 c1(c2(c([nH]c([nH]1)=O)n(cn2)[CH]3([CH](O)[CH](O)[CH](O3)CO)))(=O) LIGAND-CPD:C01762:*CAS:146-80-5 3.1.3.5 xanthosine-5-phosphate + H2O = xanthosine salvage pathways of purine nucleosides II (plant) xanthosine 9 β-D-ribofuranosylxanthine 284.228 C10 H12 N4 O6 c1(c2(c([nH]c([nH]1)=O)n(cn2)[CH]3([CH](O)[CH](O)[CH](O3)CO)))(=O) LIGAND-CPD:C01762:*CAS:146-80-5 3.5.4.15 H2O + guanosine = ammonia + xanthosine purine degradation xanthosine 9 β-D-ribofuranosylxanthine 284.228 C10 H12 N4 O6 c1(c2(c([nH]c([nH]1)=O)n(cn2)[CH]3([CH](O)[CH](O)[CH](O3)CO)))(=O) LIGAND-CPD:C01762:*CAS:146-80-5 3.5.4.15 H2O + guanosine = ammonia + xanthosine salvage pathways of purine nucleosides II (plant) xanthosine 9 β-D-ribofuranosylxanthine 284.228 C10 H12 N4 O6 c1(c2(c([nH]c([nH]1)=O)n(cn2)[CH]3([CH](O)[CH](O)[CH](O3)CO)))(=O) LIGAND-CPD:C01762:*CAS:146-80-5 3.2.2.1 xanthosine + H2O = xanthine + D-ribose purine degradation xanthosine 9 β-D-ribofuranosylxanthine 284.228 C10 H12 N4 O6 c1(c2(c([nH]c([nH]1)=O)n(cn2)[CH]3([CH](O)[CH](O)[CH](O3)CO)))(=O) LIGAND-CPD:C01762:*CAS:146-80-5 3.2.2.1 xanthosine + H2O = xanthine + D-ribose salvage pathways of purine nucleosides II (plant) xanthosine 9 β-D-ribofuranosylxanthine 284.228 C10 H12 N4 O6 c1(c2(c([nH]c([nH]1)=O)n(cn2)[CH]3([CH](O)[CH](O)[CH](O3)CO)))(=O) LIGAND-CPD:C01762:*CAS:146-80-5 xanthosine = ribose-1-phosphate + xanthine ureide biosynthesis 2-hydroxyisoflavanone 2,7,4'-trihydroxyisoflavanone 272.257 C15 H12 O5 C2(O)(C(c1(ccc(O)cc1))C(=O)c3(c(O2)cc(O)cc3)) 4.2.1.105 2-hydroxyisoflavanone = daidzein + H2O pterocarpan biosynthesis 2-hydroxyisoflavanone 2,7,4'-trihydroxyisoflavanone 272.257 C15 H12 O5 C2(O)(C(c1(ccc(O)cc1))C(=O)c3(c(O2)cc(O)cc3)) 2-hydroxyisoflavanone + S-adenosyl-L-methionine = 2,7-dihydroxy-4'-methoxyisoflavanone + S-adenosyl-L-homocysteine pterocarpan biosynthesis pinocembrin chalcone 256.257 C15 H12 O4 c1(c(O)c(c(O)cc(O)1)C(=O)C=Cc2(ccccc2)) 2.3.1.- malonyl-CoA + (E)-cinnamoyl-CoA = pinocembrin chalcone + coenzyme A + CO2 pinobanksin biosynthesis pinocembrin chalcone 256.257 C15 H12 O4 c1(c(O)c(c(O)cc(O)1)C(=O)C=Cc2(ccccc2)) 5.5.1.6 pinocembrin chalcone = (2S)-pinocembrin pinobanksin biosynthesis erythrohydrobupropion 241.76 C13 H20 N1 O1 CL1 CC(NC(C)(C)C)C(O)c1(cc(Cl)ccc1) bupropion = erythrohydrobupropion bupropion degradation 1-monoacylglycerol monoglyceride*1-acylglycerol C4 H7 O4 R1 3.1.1.23 H2O + 1-monoacylglycerol = glycerol triacylglycerol degradation 1-monoacylglycerol monoglyceride*1-acylglycerol C4 H7 O4 R1 2-monoacylglycerol = 1-monoacylglycerol triacylglycerol degradation 4-hydroxybenzyl alcohol 124.139 C7 H8 O2 C(O)C1(=CC=C(O)C=C1) NCI:227926*CAS:623-05-2 L-tyrosine + 1-deoxy-D-xylulose 5-phosphate = 4-methyl-5-(β-hydroxyethyl)thiazole phosphate + 4-hydroxybenzyl alcohol thiamine biosynthesis O-succinylbenzoate 2-succinylbenzoate*succinylbenzoate 222.197 C11 H10 O5 C(=O)(O)CCC(=O)c1(c(C(O)=O)cccc1) LIGAND-CPD:C02730: 6.2.1.26 ATP + O-succinylbenzoate + coenzyme A = AMP + diphosphate + O-succinylbenzoyl-CoA menaquinone biosynthesis O-succinylbenzoate 2-succinylbenzoate*succinylbenzoate 222.197 C11 H10 O5 C(=O)(O)CCC(=O)c1(c(C(O)=O)cccc1) LIGAND-CPD:C02730: 6.2.1.26 ATP + O-succinylbenzoate + coenzyme A = 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA + AMP + diphosphate phylloquinone biosynthesis O-succinylbenzoate 2-succinylbenzoate*succinylbenzoate 222.197 C11 H10 O5 C(=O)(O)CCC(=O)c1(c(C(O)=O)cccc1) LIGAND-CPD:C02730: 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate = O-succinylbenzoate + H2O menaquinone biosynthesis O-succinylbenzoate 2-succinylbenzoate*succinylbenzoate 222.197 C11 H10 O5 C(=O)(O)CCC(=O)c1(c(C(O)=O)cccc1) LIGAND-CPD:C02730: 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate = O-succinylbenzoate + H2O phylloquinone biosynthesis phlorisovalerophenone 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one*PIVP 210.229 C11 H14 O4 CC(C)CC(=O)c1(c(O)cc(O)cc(O)1) PUBCHEM:441269: 2.5.1.- phlorisovalerophenone + dimethylallyl-PP = 4-prenylphlorisovalerophenone + diphosphate humulone biosynthesis phlorisovalerophenone 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one*PIVP 210.229 C11 H14 O4 CC(C)CC(=O)c1(c(O)cc(O)cc(O)1) PUBCHEM:441269: 2.3.1.156 malonyl-CoA + isovaleryl-CoA = phlorisovalerophenone + CO2 + coenzyme A humulone biosynthesis pyridoxamine 5'-phosphate pyridoxamine phosphate 248.175 C8 H13 N2 O5 P1 C(N)c1(c(COP(O)(=O)O)cnc(C)c(O)1) CAS:529-96-4:*LIGAND-CPD:C00647: 1.4.3.5 O2 + H2O + pyridoxamine 5'-phosphate = ammonia + H2O2 + pyridoxal 5'-phosphate pyridoxal 5'-phosphate salvage pathway pyridoxamine 5'-phosphate pyridoxamine phosphate 248.175 C8 H13 N2 O5 P1 C(N)c1(c(COP(O)(=O)O)cnc(C)c(O)1) CAS:529-96-4:*LIGAND-CPD:C00647: 2.7.1.35 ATP + pyridoxamine = ADP + pyridoxamine 5'-phosphate pyridoxal 5'-phosphate salvage pathway GA37 gibberellin A37*gibberellin A37*GA37 364.438 C20 H28 O6 CC1([CH]4(C(CCC(O)1)(CO)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA37 + α-ketoglutarate + O2 = GA36 + succinate + CO2 + H2O gibberellin biosynthesis II (early C-3 hydroxylation) GA37 gibberellin A37*gibberellin A37*GA37 364.438 C20 H28 O6 CC1([CH]4(C(CCC(O)1)(CO)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA14 + O2 + α-ketoglutarate = GA37 + CO2 + succinate gibberellin biosynthesis II (early C-3 hydroxylation) GA37 gibberellin A37*gibberellin A37*GA37 364.438 C20 H28 O6 CC1([CH]4(C(CCC(O)1)(CO)[CH]3(C2(CC(C(=C)C2)CC3)(C4C(=O)O))))(C(=O)O) 1.14.11.- GA15 + α-ketoglutarate + O2 = GA37 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) spermidine 145.247 C7 H19 N3 C(N)CCCNCCCN LIGAND-CPD:C00315:*CAS:124-20-9 2.5.1.22 spermidine + S-adenosyl-L-methioninamine = spermine + 5'-methylthioadenosine spermine biosynthesis spermidine 145.247 C7 H19 N3 C(N)CCCNCCCN LIGAND-CPD:C00315:*CAS:124-20-9 1.5.99.6 H2O + spermidine = 4-aminobutanal + 1,3-diaminopropane β-alanine biosynthesis I spermidine 145.247 C7 H19 N3 C(N)CCCNCCCN LIGAND-CPD:C00315:*CAS:124-20-9 2.5.1.16 putrescine + S-adenosyl-L-methioninamine = spermidine + 5'-methylthioadenosine spermidine biosynthesis trans-zeatin-O-glucoside-7-N-glucoside 543.53 C22 H33 N5 O11 c1(c2(c(ncn1)N(C=N2)C3(OC(CO)C(O)C(O)C(O)3)))(NCC=C(C)COC4(OC(CO)C(O)C(O)C(O)4)) 2.4.1.- trans-zeatin-O-glucoside + UDP-D-glucose = trans-zeatin-O-glucoside-7-N-glucoside + UDP cytokinins 7-N-glucoside biosynthesis UDP-N-acetylmuramate uridine diphosphate N-acetylmuramic acid*UDP-N-acetylmuramic acid*UDP-N-acetyl-D-muramate*UDP-MurNAc*UDP-N-acetylmuramoyl 679.421 C20 H31 N3 O19 P2 CC(=O)NC1(C(OC(CO)C(O)C1OC(C)C(O)=O)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c(=O)[nH]c(=O)cc3))) LIGAND-CPD:C01050: 6.3.2.8 L-alanine + UDP-N-acetylmuramate + ATP = UDP-N-acetylmuramoyl-L-alanine + ADP peptidoglycan biosynthesis I UDP-N-acetylmuramate uridine diphosphate N-acetylmuramic acid*UDP-N-acetylmuramic acid*UDP-N-acetyl-D-muramate*UDP-MurNAc*UDP-N-acetylmuramoyl 679.421 C20 H31 N3 O19 P2 CC(=O)NC1(C(OC(CO)C(O)C1OC(C)C(O)=O)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c(=O)[nH]c(=O)cc3))) LIGAND-CPD:C01050: 1.1.1.158 NADP+ + UDP-N-acetylmuramate = NADPH + UDP-GlcNAc-enolpyruvate peptidoglycan biosynthesis I 4-methyl-5-(β-hydroxyethyl)thiazole 4-methyl-5-(2-hydroxyethyl)-thiazole*THZ*5-(2-Hydroxyethyl)-4-methylthiazole*HET 143.203 C6 H9 N1 O1 S1 Cc1(c(CCO)scn1) LIGAND-CPD:C04294:*CAS:137-00-8 2.7.1.50 ATP + 4-methyl-5-(β-hydroxyethyl)thiazole = ADP + 4-methyl-5-(β-hydroxyethyl)thiazole phosphate thiamine biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.3 coenzyme A + ATP = diphosphate + AMP acyl-CoA synthetase pathway coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.- trans-cinnamate + coenzyme A = (E)-cinnamoyl-CoA + H2O salicylate biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.26 ATP + O-succinylbenzoate + coenzyme A = AMP + diphosphate + O-succinylbenzoyl-CoA menaquinone biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) 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 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.117 H2O + tetrahydrodipicolinate + succinyl-CoA = N-succinyl-2-amino-6-ketopimelate + coenzyme A lysine biosynthesis I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: α-ketoglutarate + coenzyme A + NAD+ = succinyl-CoA + CO2 + NADH TCA cycle coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 1.2.1.27 NAD+ + coenzyme A + methylmalonate-semialdehyde = NADH + CO2 + propionyl-CoA valine degradation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.109 L-arginine + succinyl-CoA = N2-succinyl-L-arginine + coenzyme A arginine degradation II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.110 feruloyl-CoA + tyramine = N-feruloyltyramine + coenzyme A suberin biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.10 acetoacetyl-CoA + H2O + acetyl-CoA = coenzyme A + 3-hydroxy-3-methyl-glutaryl-CoA mevalonate pathway coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: α-ketoadipate + NAD+ + coenzyme A = CO2 + NADH + glutaryl-CoA lysine degradation II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: α-ketoadipate + NAD+ + coenzyme A = CO2 + NADH + glutaryl-CoA tryptophan degradation III (eukaryotic) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.12 acetyl-CoA = coenzyme A pyruvate dehydrogenase complex coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: benzoyl-CoA + H2O = benzoate + coenzyme A salicylate biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2-ketoisocaproate + coenzyme A + NAD+ = isovaleryl-CoA + CO2 + NADH leucine degradation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.54 formate + acetyl-CoA = pyruvate + coenzyme A mixed acid fermentation coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.54 formate + acetyl-CoA = pyruvate + coenzyme A respiration (anaerobic) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.8 acetyl-CoA = acetylphosphate + coenzyme A mixed acid fermentation coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.8 acetyl-CoA = acetylphosphate + coenzyme A D-lactate fermentation to propionate and acetate coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.8 acetyl-CoA = acetylphosphate + coenzyme A ethanol fermentation to acetate coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.8 acetyl-CoA = acetylphosphate + coenzyme A gallate degradation III (anaerobic) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.- 3-hydroxy-5- oxohexanoyl-CoA + coenzyme A = 3-hydroxybutyryl-CoA + acetyl-CoA gallate degradation III (anaerobic) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.80 acetyl-CoA = coenzyme A glutathione-mediated detoxification coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = citrate + coenzyme A TCA cycle variation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = citrate + coenzyme A respiration (anaerobic) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.1 oxaloacetate + acetyl-CoA + H2O = citrate + coenzyme A TCA cycle coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 1.1.1.34 NADP+ + coenzyme A + (R)-mevalonate = NADPH + 3-hydroxy-3-methyl-glutaryl-CoA mevalonate pathway coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2-keto-3-methyl-valerate + NAD+ + coenzyme A = S-2-methyl-butyryl-CoA + NADH + CO2 isoleucine degradation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.9 acetyl-CoA = acetoacetyl-CoA + coenzyme A acetyl CoA fermentation to butyrate coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.9 acetyl-CoA = acetoacetyl-CoA + coenzyme A mevalonate pathway coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.9 acetyl-CoA = acetoacetyl-CoA + coenzyme A glutaryl-CoA degradation coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.9 acetyl-CoA = acetoacetyl-CoA + coenzyme A ethanol fermentation to acetate coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 1.2.7.1 pyruvate + coenzyme A = acetyl-CoA + CO2 reductive TCA cycle I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 1.2.7.1 pyruvate + coenzyme A = acetyl-CoA + CO2 D-lactate fermentation to propionate and acetate coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 1.2.7.1 pyruvate + coenzyme A = acetyl-CoA + CO2 glutamate degradation VII (to butyrate) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 1.1.1.88 (R)-mevalonate + NAD+ + coenzyme A = 3-hydroxy-3-methyl-glutaryl-CoA + NADH + H+ mevalonate degradation coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.5 succinate + coenzyme A + ATP = succinyl-CoA + ADP reductive TCA cycle I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.5 succinate + coenzyme A + ATP = succinyl-CoA + ADP TCA cycle coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.170 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 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.9 2-methylacetoacetyl-CoA + coenzyme A = propionyl-CoA + acetyl-CoA isoleucine degradation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.50 L-serine + palmitoyl CoA = CO2 + 3-dehydrosphinganine + coenzyme A sphingolipid metabolism coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.16 acetyl-CoA = coenzyme A fatty acid β-oxidation IV (plant, unsaturated, even number) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.16 acetyl-CoA = coenzyme A fatty acid β-oxidation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.16 acetyl-CoA = coenzyme A fatty acid β-oxidation II (plant, saturated) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.4 D-glucosamine-6-phosphate + acetyl-CoA = N-acetyl-D-glucosamine-6-phosphate + coenzyme A UDP-N-acetylgalactosamine biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.26 ATP + O-succinylbenzoate + coenzyme A = 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA + AMP + diphosphate phylloquinone biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.13 2-keto-isovalerate + acetyl-CoA + H2O = 2-isopropylmalate + coenzyme A leucine biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 4.1.3.36 O-succinylbenzoyl-CoA = coenzyme A + 1,4-dihydroxy-2-naphthoate menaquinone biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 1.2.1.25 NAD+ + coenzyme A + 2-keto-isovalerate = NADH + CO2 + isobutyryl-CoA valine degradation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.74 coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A flavonoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) 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 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.39 malonyl-CoA = coenzyme A fatty acid biosynthesis - initial steps coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.- 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 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: oxocinnamoyl-CoA + coenzyme A = benzoyl-CoA + acetyl-CoA salicylate biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid β-oxidation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid β-oxidation II (plant, saturated) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.- 2-oxo-4-methylthiobutanoate + acetyl-CoA + H2O = 2-(2'-methylthio)ethylmalic-acid + coenzyme A homomethionine biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.- H2O + coumaroyl-CoA + malonyl-CoA = coenzyme A + CO2 + p-coumaroyltriacetate resveratrol biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP oxidative ethanol degradation III coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP glutamate degradation VII (to butyrate) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP oxidative ethanol degradation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.- acetyl-CoA = coenzyme A + CO2 fatty acid biosynthesis - initial steps coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) 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 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.51 phospholipid biosynthesis II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) 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 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.7.1.24 dephospho-CoA + ATP = coenzyme A + ADP coenzyme A biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.133 quinate + coumaroyl-CoA = 4-coumaroylquinate + coenzyme A phenylpropanoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.61 succinyl-CoA = coenzyme A 2-keto glutarate dehydrogenase complex coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.89 acetyl-CoA + tetrahydrodipicolinate + H2O = coenzyme A + L-2-acetamido-6-oxoheptanedioate lysine biosynthesis II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 1.2.1.10 NAD+ + coenzyme A + acetaldehyde = NADH + acetyl-CoA mixed acid fermentation coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 1.2.1.10 NAD+ + coenzyme A + acetaldehyde = NADH + acetyl-CoA ethanol fermentation to acetate coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.17 coenzyme A + propionate + ATP = propionyl-CoA + diphosphate + AMP β-alanine biosynthesis II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 4.1.3.36 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA = coenzyme A + 1,4-dihydroxy-2-naphthoate phylloquinone biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.19 butyryl-CoA = butyryl phosphate + coenzyme A acetyl CoA fermentation to butyrate coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.12 caffeate + coenzyme A + ATP = caffeoyl-CoA + AMP + diphosphate suberin biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.4 3-hydroxypropionyl-CoA + H2O = 3-hydroxy-propionate + coenzyme A β-alanine biosynthesis II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.133 shikimate + coumaroyl-CoA = 4-coumaroylshikimate + coenzyme A phenylpropanoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) 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 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.1 L-glutamate + acetyl-CoA = N-acetyl-L-glutamate + coenzyme A arginine biosynthesis II (acetyl cycle) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.1 L-glutamate + acetyl-CoA = N-acetyl-L-glutamate + coenzyme A ornithine biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.156 malonyl-CoA + isobutyryl-CoA = phlorisobutyrophenone + CO2 + coenzyme A cohumulone biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.14 α-ketoglutarate + H2O + acetyl-CoA = homocitrate + coenzyme A lysine biosynthesis IV coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.2 H2O = coenzyme A acyl-CoA thioesterase pathway coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.31 homoserine + acetyl-CoA = O-acetyl-L-homoserine + coenzyme A homocysteine biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) 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 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) 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 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.168 coenzyme A = isobutyryl-CoA branched-chain α-keto acid dehydrogenase complex coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 1.2.7.3 α-ketoglutarate + coenzyme A = succinyl-CoA + CO2 reductive TCA cycle I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: salicyloyl-CoA + H2O = salicylate + coenzyme A salicylate biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.15 sn-glycerol-3-phosphate = coenzyme A phospholipid biosynthesis II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) 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 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.46 homoserine + succinyl-CoA = O-succinyl-L-homoserine + coenzyme A methionine biosynthesis I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 1.2.1.44 coumaroyl-CoA + NADPH = coumaraldehyde + NADP+ + coenzyme A phenylpropanoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.12 coenzyme A + 4-coumarate + ATP = coumaroyl-CoA + diphosphate + AMP flavonoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.12 coenzyme A + 4-coumarate + ATP = coumaroyl-CoA + diphosphate + AMP phenylpropanoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 1.2.1.- pyruvate + coenzyme A + NAD+ = acetyl-CoA + CO2 + NADH respiration (anaerobic) coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.- coumaroyl-CoA + malonyl-CoA = bis-noryangonin + coenzyme A + CO2 resveratrol biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.- caffeoylquinate + coenzyme A = caffeoyl-CoA + quinate phenylpropanoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.95 malonyl-CoA + coumaroyl-CoA = resveratrol + coenzyme A + CO2 resveratrol biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 6.2.1.12 ferulate + coenzyme A + ATP = feruloyl-CoA + AMP + diphosphate suberin biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.156 malonyl-CoA + isovaleryl-CoA = phlorisovalerophenone + CO2 + coenzyme A humulone biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 1.2.1.44 feruloyl-CoA + NADPH = coniferyl aldehyde + NADP+ + coenzyme A phenylpropanoid biosynthesis coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.38 acetyl-CoA = coenzyme A fatty acid biosynthesis - initial steps coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.3.9 acetyl-CoA + H2O + glyoxylate = malate + coenzyme A TCA cycle variation I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.47 pimeloyl-CoA + L-alanine = CO2 + coenzyme A + 7-keto-8-aminopelargonate biotin biosynthesis II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.47 pimeloyl-CoA + L-alanine = CO2 + coenzyme A + 7-keto-8-aminopelargonate biotin biosynthesis I coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) 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 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 2.3.1.29 glycine + acetyl-CoA = 2-amino-3-oxobutanoate + coenzyme A threonine degradation II coenzyme A CoA*co-A-SH*co-enzyme-A*co-A*HS-CoA 767.534 C21 H36 N7 O16 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(O)OP(=O)(O)OC[CH]1(O[CH]([CH](O)[CH]1OP(O)(O)=O)N2(c3(c(N=C2)c(N)ncn3))) CAS:85-61-0*LIGAND-CPD:C00010: 3.1.2.4 H2O + 3-hydroxy-isobutyryl-CoA = 3-hydroxy-isobutyrate + coenzyme A valine 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 102.09 C4 H6 O3 C(O)(=O)C(=O)CC LIGAND-CPD:C00109:*CAS:600-18-0 4.3.1.19 L-threonine = 2-oxobutanoate + ammonia isoleucine biosynthesis 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 102.09 C4 H6 O3 C(O)(=O)C(=O)CC LIGAND-CPD:C00109:*CAS:600-18-0 4.4.1.11 L-methionine + H2O = 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 102.09 C4 H6 O3 C(O)(=O)C(=O)CC LIGAND-CPD:C00109:*CAS:600-18-0 4.4.1.1 cystathionine + H2O = ammonia + 2-oxobutanoate + L-cysteine homocysteine degradation 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 102.09 C4 H6 O3 C(O)(=O)C(=O)CC LIGAND-CPD:C00109:*CAS:600-18-0 4.4.1.1 cystathionine + H2O = 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 102.09 C4 H6 O3 C(O)(=O)C(=O)CC LIGAND-CPD:C00109:*CAS:600-18-0 2.2.1.6 pyruvate + 2-oxobutanoate = 2-aceto-2-hydroxy-butyrate + CO2 isoleucine biosynthesis from threonine 18:2-16:0-PG 1-18:2-2-16:0-phosphatidylglycerol*1-(9Z,12Z-octadecadienoyl)-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) 747. C40 H75 O10 P1 C(OP(=O)(O)OCC(O)CO)C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-16:0-PG = 18:3-16:0-PG phospholipid desaturation 18:2-16:0-PG 1-18:2-2-16:0-phosphatidylglycerol*1-(9Z,12Z-octadecadienoyl)-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) 747. C40 H75 O10 P1 C(OP(=O)(O)OCC(O)CO)C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:1-16:0-PG = 18:2-16:0-PG phospholipid desaturation 18:2-16:0-PG 1-18:2-2-16:0-phosphatidylglycerol*1-(9Z,12Z-octadecadienoyl)-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) 747. C40 H75 O10 P1 C(OP(=O)(O)OCC(O)CO)C(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-16:0-PG = 18:2-t16:1-PG phospholipid desaturation coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA 913.679 C30 H42 N7 O18 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc1(ccc(O)cc1))COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(O)=O)n3(c4(c(nc3)c(N)ncn4))) 2.3.1.170 coumaroyl-CoA + malonyl-CoA + NADPH = isoliquiritigenin + coenzyme A + CO2 + NADP+ + H2O flavonoid biosynthesis coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA 913.679 C30 H42 N7 O18 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc1(ccc(O)cc1))COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(O)=O)n3(c4(c(nc3)c(N)ncn4))) 1.2.1.44 coumaroyl-CoA + NADPH = coumaraldehyde + NADP+ + coenzyme A phenylpropanoid biosynthesis coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA 913.679 C30 H42 N7 O18 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc1(ccc(O)cc1))COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(O)=O)n3(c4(c(nc3)c(N)ncn4))) 6.2.1.12 coenzyme A + 4-coumarate + ATP = coumaroyl-CoA + diphosphate + AMP flavonoid biosynthesis coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA 913.679 C30 H42 N7 O18 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc1(ccc(O)cc1))COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(O)=O)n3(c4(c(nc3)c(N)ncn4))) 6.2.1.12 coenzyme A + 4-coumarate + ATP = coumaroyl-CoA + diphosphate + AMP phenylpropanoid biosynthesis coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA 913.679 C30 H42 N7 O18 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc1(ccc(O)cc1))COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(O)=O)n3(c4(c(nc3)c(N)ncn4))) 2.3.1.- coumaroyl-CoA + malonyl-CoA = bis-noryangonin + coenzyme A + CO2 resveratrol biosynthesis coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA 913.679 C30 H42 N7 O18 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc1(ccc(O)cc1))COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(O)=O)n3(c4(c(nc3)c(N)ncn4))) 2.3.1.133 quinate + coumaroyl-CoA = 4-coumaroylquinate + coenzyme A phenylpropanoid biosynthesis coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA 913.679 C30 H42 N7 O18 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc1(ccc(O)cc1))COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(O)=O)n3(c4(c(nc3)c(N)ncn4))) 2.3.1.133 shikimate + coumaroyl-CoA = 4-coumaroylshikimate + coenzyme A phenylpropanoid biosynthesis coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA 913.679 C30 H42 N7 O18 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc1(ccc(O)cc1))COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(O)=O)n3(c4(c(nc3)c(N)ncn4))) 2.3.1.95 malonyl-CoA + coumaroyl-CoA = resveratrol + coenzyme A + CO2 resveratrol biosynthesis coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA 913.679 C30 H42 N7 O18 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc1(ccc(O)cc1))COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(O)=O)n3(c4(c(nc3)c(N)ncn4))) 2.3.1.74 coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A flavonoid biosynthesis coumaroyl-CoA p-coumaryl-CoA*4-coumaroyl-CoA 913.679 C30 H42 N7 O18 P3 S1 CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)C=Cc1(ccc(O)cc1))COP(=O)(O)OP(=O)(O)OC[CH]2(O[CH]([CH](O)[CH]2OP(O)(O)=O)n3(c4(c(nc3)c(N)ncn4))) 2.3.1.- H2O + coumaroyl-CoA + malonyl-CoA = coenzyme A + CO2 + p-coumaroyltriacetate resveratrol biosynthesis L-proline 2-pyrrolidinecarboxylic acid*P*proline*prol*pro 115.132 C5 H9 N1 O2 C(=O)(O)C1(CCCN1) LIGAND-CPD:C00148:*CAS:147-85-3 1.5.1.2 L-proline = H+ proline biosynthesis V (from arginine) L-proline 2-pyrrolidinecarboxylic acid*P*proline*prol*pro 115.132 C5 H9 N1 O2 C(=O)(O)C1(CCCN1) LIGAND-CPD:C00148:*CAS:147-85-3 1.5.1.2 L-proline = H+ proline biosynthesis II L-proline 2-pyrrolidinecarboxylic acid*P*proline*prol*pro 115.132 C5 H9 N1 O2 C(=O)(O)C1(CCCN1) LIGAND-CPD:C00148:*CAS:147-85-3 1.5.1.2 L-proline = H+ arginine degradation VI (arginase 2 pathway) L-proline 2-pyrrolidinecarboxylic acid*P*proline*prol*pro 115.132 C5 H9 N1 O2 C(=O)(O)C1(CCCN1) LIGAND-CPD:C00148:*CAS:147-85-3 1.5.1.2 L-proline = H+ proline biosynthesis I L-proline 2-pyrrolidinecarboxylic acid*P*proline*prol*pro 115.132 C5 H9 N1 O2 C(=O)(O)C1(CCCN1) LIGAND-CPD:C00148:*CAS:147-85-3 6.1.1.15 L-proline + ATP = diphosphate + AMP tRNA charging pathway L-proline 2-pyrrolidinecarboxylic acid*P*proline*prol*pro 115.132 C5 H9 N1 O2 C(=O)(O)C1(CCCN1) LIGAND-CPD:C00148:*CAS:147-85-3 4.3.1.12 L-ornithine + NAD+ = L-proline + ammonia + NADH + H+ arginine degradation VII (arginase 3 pathway) L-proline 2-pyrrolidinecarboxylic acid*P*proline*prol*pro 115.132 C5 H9 N1 O2 C(=O)(O)C1(CCCN1) LIGAND-CPD:C00148:*CAS:147-85-3 1.5.99.8 L-proline + FAD = FADH2 proline degradation I L-proline 2-pyrrolidinecarboxylic acid*P*proline*prol*pro 115.132 C5 H9 N1 O2 C(=O)(O)C1(CCCN1) LIGAND-CPD:C00148:*CAS:147-85-3 1.5.99.8 L-proline + FAD = FADH2 citrulline biosynthesis L-proline 2-pyrrolidinecarboxylic acid*P*proline*prol*pro 115.132 C5 H9 N1 O2 C(=O)(O)C1(CCCN1) LIGAND-CPD:C00148:*CAS:147-85-3 1.5.99.8 proline degradation II undecaprenyl phosphate 847.295 C55 H91 O4 P1 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(O)(=O)O LIGAND-CPD:C00348: 2.7.8.13 undecaprenyl phosphate = UMP peptidoglycan biosynthesis I dUTP deoxy-UTP*2'-deoxyuridine-5'-triphosphate*deoxyuridine-triphosphate 468.144 C9 H15 N2 O14 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00460:*CAS:1173-82-6 UTP = dUTP + H2O de novo biosynthesis of pyrimidine deoxyribonucleotides dUTP deoxy-UTP*2'-deoxyuridine-5'-triphosphate*deoxyuridine-triphosphate 468.144 C9 H15 N2 O14 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00460:*CAS:1173-82-6 2.7.4.6 dUDP + ATP = dUTP + ADP de novo biosynthesis of pyrimidine deoxyribonucleotides dUTP deoxy-UTP*2'-deoxyuridine-5'-triphosphate*deoxyuridine-triphosphate 468.144 C9 H15 N2 O14 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00460:*CAS:1173-82-6 3.5.4.13 H2O + dCTP = ammonia + dUTP de novo biosynthesis of pyrimidine deoxyribonucleotides dUTP deoxy-UTP*2'-deoxyuridine-5'-triphosphate*deoxyuridine-triphosphate 468.144 C9 H15 N2 O14 P3 c1(n(c(=O)[nH]c(c1)=O)C2(OC(C(C2)O)COP(=O)(O)OP(=O)(O)OP(O)(O)=O)) LIGAND-CPD:C00460:*CAS:1173-82-6 3.6.1.23 H2O + dUTP = diphosphate + dUMP de novo biosynthesis of pyrimidine deoxyribonucleotides homocitrate homocit*2-Hydroxybutane-1,2,4-tricarboxylate*Homocitric acid*3-Hydroxy-3-carboxyadipic acid 206.152 C7 H10 O7 C(=O)(O)CCC(O)(C(O)=O)CC(O)=O CAS:3562-74-1 2.3.3.14 α-ketoglutarate + H2O + acetyl-CoA = homocitrate + coenzyme A lysine biosynthesis IV homocitrate homocit*2-Hydroxybutane-1,2,4-tricarboxylate*Homocitric acid*3-Hydroxy-3-carboxyadipic acid 206.152 C7 H10 O7 C(=O)(O)CCC(O)(C(O)=O)CC(O)=O CAS:3562-74-1 4.2.1.36 homocitrate = H2O + 3-carboxyhex-2-enedioate lysine biosynthesis IV D-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*1D-myo-inositol 3-monophosphate*myo-inositol 1-monophosphate*Ins3P*1L-myo-inositol 1-phosphate*myo-inositol phosphate 259.129 C6 H12 O9 P1 C1(C(O)C(O)C(O)C(O)C(O)1)(OP(O)([O-])=O) D-myo-inositol (3)-monophosphate + ATP = D-myo-inositol (3,4)-bisphosphate + ADP lipid-independent phytate biosynthesis D-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*1D-myo-inositol 3-monophosphate*myo-inositol 1-monophosphate*Ins3P*1L-myo-inositol 1-phosphate*myo-inositol phosphate 259.129 C6 H12 O9 P1 C1(C(O)C(O)C(O)C(O)C(O)1)(OP(O)([O-])=O) 5.5.1.4 β-D-glucose-6-phosphate = D-myo-inositol (3)-monophosphate myo-inositol biosynthesis D-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*1D-myo-inositol 3-monophosphate*myo-inositol 1-monophosphate*Ins3P*1L-myo-inositol 1-phosphate*myo-inositol phosphate 259.129 C6 H12 O9 P1 C1(C(O)C(O)C(O)C(O)C(O)1)(OP(O)([O-])=O) 5.5.1.4 β-D-glucose-6-phosphate = D-myo-inositol (3)-monophosphate lipid-independent phytate biosynthesis D-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*1D-myo-inositol 3-monophosphate*myo-inositol 1-monophosphate*Ins3P*1L-myo-inositol 1-phosphate*myo-inositol phosphate 259.129 C6 H12 O9 P1 C1(C(O)C(O)C(O)C(O)C(O)1)(OP(O)([O-])=O) 2.7.1.64 myo-inositol + ATP = D-myo-inositol (3)-monophosphate + ADP lipid-independent phytate biosynthesis ciceritol O-α-D-galactopyranosyl-(1->6)-O-α-D-galactopyranosyl-(1->2)-4-O-methyl-chiro-inositol 518.468 C19 H34 O16 C1(OC(C(O)C(O)C(O)1)COC2(OC(CO)C(O)C(O)C(O)2))(OC3(C(O)C(OC)C(O)C(O)C(O)3)) 2.4.1.- galactopinitol A + galactinol = ciceritol + myo-inositol galactosylcyclitol biosynthesis cis-3-hexenol 100.16 C6 H12 O1 C(O)CC=CCC NCI:74451*CAS:928-96-1 cis-3-hexenal = cis-3-hexenol 13-LOX and 13-HPL pathway 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(OC(CO)C(O)C(O)C(O)1)OC3(C(c2(ccc(O)cc2))=Oc4(c(C=3)c(O)cc(O)c4)) 2.4.1.115 UDP-D-glucose + pelargonidin = UDP + pelargonidin-3-O-β-D-glucoside 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 c3(c2(OC(c1(cc(O)c(O)cc1))C(O)C(O)c2c(O)cc(O)3)) 1.17.1.3 leucocyanidin + NADPH = 2,3-trans-catechin + NADP+ + H2O proanthocyanidin biosynthesis from flavanols leucocyanidin a flavan-3,4-diol*2,3-trans-3,4-cis-leucocyanidin 306.271 C15 H14 O7 c3(c2(OC(c1(cc(O)c(O)cc1))C(O)C(O)c2c(O)cc(O)3)) 1.14.11.- leucocyanidin + α-ketoglutarate + O2 = 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 c3(c2(OC(c1(cc(O)c(O)cc1))C(O)C(O)c2c(O)cc(O)3)) 1.1.1.219 dihydroquercetin + NADPH = leucocyanidin + NADP+ leucopelargonidin and leucocyanidin biosynthesis dihydrosterculate dihydrosterculic acid 296.492 C19 H36 O2 CCCCCCCCC1(C(C1)CCCCCCCC(O)=O) 2.1.1.79 oleate + S-adenosyl-L-methionine = dihydrosterculate + S-adenosyl-L-homocysteine cyclopropane and cyclopropene fatty acid biosynthesis dihydrosterculate dihydrosterculic acid 296.492 C19 H36 O2 CCCCCCCCC1(C(C1)CCCCCCCC(O)=O) dihydrosterculate = sterculate cyclopropane and cyclopropene fatty acid biosynthesis 5α-cholesta-8,24-dien-3-one 382.628 C27 H42 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)CC(=O)CC4)))) 1.1.1.270 5α-cholesta-8,24-dien-3-one + NADPH = zymosterol + NADP+ cholesterol biosynthesis I 5α-cholesta-8,24-dien-3-one 382.628 C27 H42 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)CC(=O)CC4)))) 1.1.1.270 5α-cholesta-8,24-dien-3-one + NADPH = zymosterol + NADP+ cholesterol biosynthesis III (via desmosterol) 5α-cholesta-8,24-dien-3-one 382.628 C27 H42 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)CC(=O)CC4)))) 1.1.1.170 4α-carboxy-5α-cholesta-8,24-dien-3β-ol = 5α-cholesta-8,24-dien-3-one + CO2 cholesterol biosynthesis I 5α-cholesta-8,24-dien-3-one 382.628 C27 H42 O1 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)CC(=O)CC4)))) 1.1.1.170 4α-carboxy-5α-cholesta-8,24-dien-3β-ol = 5α-cholesta-8,24-dien-3-one + CO2 cholesterol biosynthesis III (via desmosterol) gentiodelphin delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-caffeoylglucoside 1113.963 C51 H53 O28 C1(OC(C(O)C(O)C(O)1)COC(=O)C=Cc2(ccc(O)c(O)c2))Oc5(c4(C=C(OC3(OC(CO)C(O)C(O)C(O)3))C(=Oc4cc(O)c5)c6(cc(c(O)c(O)c6)OC7(OC(C(O)C(O)C(O)7)COC(=O)C=Cc8(ccc(O)c(O)c8))))) 2.3.1.- delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + caffeoyl-CoA = gentiodelphin + coenzyme A gentiodelphin biosynthesis GA12-aldehyde gibberellin A12-aldehyde*gibberellin A12-aldehyde*GA12-aldehyde 316.439 C20 H28 O3 CC1([CH]4(C(CCC1)(C)[CH]3(C2(CC(C(=C)C2)CC3)(C4C=O))))(C(=O)O) 1.14.13.79 GA12-aldehyde + NADPH + O2 = GA12 + NADP+ + H2O GA12 biosynthesis GA12-aldehyde gibberellin A12-aldehyde*gibberellin A12-aldehyde*GA12-aldehyde 316.439 C20 H28 O3 CC1([CH]4(C(CCC1)(C)[CH]3(C2(CC(C(=C)C2)CC3)(C4C=O))))(C(=O)O) 1.14.13.79 ent-7-α-hydroxykaurenoate + NADPH + H+ + O2 = GA12-aldehyde + NADP+ + H2O GA12 biosynthesis γ-tocopherol 416.686 C28 H48 O2 Cc2(c1(OC(C)(CCc1cc(O)c(C)2)CCCC(C)CCCC(C)CCCC(C)C)) 2,3-dimethyl-6-phytyl-1,4-benzoquinone = γ-tocopherol vitamin E biosynthesis γ-tocopherol 416.686 C28 H48 O2 Cc2(c1(OC(C)(CCc1cc(O)c(C)2)CCCC(C)CCCC(C)CCCC(C)C)) 2.1.1.95 γ-tocopherol + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + α-tocopherol vitamin E biosynthesis 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 c1(c(c2(c([nH]1)cccc2))CC(=O)OC3(C(O)C(O)C(O)C(O)C3O)) 2.4.2.34 UDP-L-arabinose + indol-3-yl-acetyl-myo-inositol = 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 c1(c(c2(c([nH]1)cccc2))CC(=O)OC3(C(O)C(O)C(O)C(O)C3O)) 2.4.1.156 indol-3-yl-acetyl-myo-inositol + UDP-galactose = 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 c1(c(c2(c([nH]1)cccc2))CC(=O)OC3(C(O)C(O)C(O)C(O)C3O)) 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 anthranilate anthranilic acid*2-aminobenzoic acid*vitamin L1*o-aminobenzoic acid*2-aminobenzoate 137.138 C7 H7 N1 O2 C(=O)(O)c1(c(N)cccc1) LIGAND-CPD:C00108:*CAS:118-92-3 2.4.2.18 diphosphate = anthranilate + 5-phosphoribosyl 1-pyrophosphate tryptophan biosynthesis anthranilate anthranilic acid*2-aminobenzoic acid*vitamin L1*o-aminobenzoic acid*2-aminobenzoate 137.138 C7 H7 N1 O2 C(=O)(O)c1(c(N)cccc1) LIGAND-CPD:C00108:*CAS:118-92-3 4.1.3.27 chorismate + L-glutamine = L-glutamate + anthranilate + pyruvate tryptophan biosynthesis malonyl-CoA malonylCoenzyme A 853.581 C24 H38 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O) LIGAND-CPD:C00083:*CAS:524-14-1 6.4.1.2 acetyl-CoA = malonyl-CoA biotin-carboxyl carrier protein malonyl-CoA malonylCoenzyme A 853.581 C24 H38 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O) 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 853.581 C24 H38 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O) LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.170 coumaroyl-CoA + malonyl-CoA + NADPH = isoliquiritigenin + coenzyme A + CO2 + NADP+ + H2O flavonoid biosynthesis malonyl-CoA malonylCoenzyme A 853.581 C24 H38 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O) LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.39 malonyl-CoA = coenzyme A fatty acid biosynthesis - initial steps malonyl-CoA malonylCoenzyme A 853.581 C24 H38 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O) LIGAND-CPD:C00083:*CAS:524-14-1 6.4.1.2 ATP + acetyl-CoA + HCO3- + H+ = ADP + malonyl-CoA fatty acid biosynthesis - initial steps malonyl-CoA malonylCoenzyme A 853.581 C24 H38 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O) LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.- coumaroyl-CoA + malonyl-CoA = bis-noryangonin + coenzyme A + CO2 resveratrol biosynthesis malonyl-CoA malonylCoenzyme A 853.581 C24 H38 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O) LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.- malonyl-CoA + (E)-cinnamoyl-CoA = pinocembrin chalcone + coenzyme A + CO2 pinobanksin biosynthesis malonyl-CoA malonylCoenzyme A 853.581 C24 H38 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O) LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.156 malonyl-CoA + isobutyryl-CoA = phlorisobutyrophenone + CO2 + coenzyme A cohumulone biosynthesis malonyl-CoA malonylCoenzyme A 853.581 C24 H38 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O) LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.95 malonyl-CoA + coumaroyl-CoA = resveratrol + coenzyme A + CO2 resveratrol biosynthesis malonyl-CoA malonylCoenzyme A 853.581 C24 H38 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O) LIGAND-CPD:C00083:*CAS:524-14-1 malonyl-CoA = CO2 epicuticular wax biosynthesis malonyl-CoA malonylCoenzyme A 853.581 C24 H38 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O) LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.74 coumaroyl-CoA + malonyl-CoA = naringenin chalcone + CO2 + coenzyme A flavonoid biosynthesis malonyl-CoA malonylCoenzyme A 853.581 C24 H38 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O) LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.156 malonyl-CoA + isovaleryl-CoA = phlorisovalerophenone + CO2 + coenzyme A humulone biosynthesis malonyl-CoA malonylCoenzyme A 853.581 C24 H38 N7 O19 P3 S1 [CH]3(n1(c2(c(nc1)c(N)ncn2)))(O[CH]([CH]([CH](O)3)OP(=O)(O)O)COP(O)(=O)OP(=O)(O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O) LIGAND-CPD:C00083:*CAS:524-14-1 2.3.1.- H2O + coumaroyl-CoA + malonyl-CoA = coenzyme A + CO2 + p-coumaroyltriacetate resveratrol biosynthesis L-ascorbate vitamin C*ascorbate*L-ascorbate (vitamin C)*ascorbic acid 176.126 C6 H8 O6 C1(O[CH](C(O)CO)C(=O)C(O)=1)(O) LIGAND-CPD:C00072:*CAS:50-81-7 1.6.5.4 monodehydroascorbate + NADPH = L-ascorbate + NADP+ ascorbate glutathione cycle L-ascorbate vitamin C*ascorbate*L-ascorbate (vitamin C)*ascorbic acid 176.126 C6 H8 O6 C1(O[CH](C(O)CO)C(=O)C(O)=1)(O) LIGAND-CPD:C00072:*CAS:50-81-7 1.3.2.3 L-galactono-1,4-lactone = L-ascorbate ascorbate biosynthesis L-ascorbate vitamin C*ascorbate*L-ascorbate (vitamin C)*ascorbic acid 176.126 C6 H8 O6 C1(O[CH](C(O)CO)C(=O)C(O)=1)(O) LIGAND-CPD:C00072:*CAS:50-81-7 monodehydroascorbate = L-ascorbate + L-dehydro-ascorbate ascorbate glutathione cycle L-ascorbate vitamin C*ascorbate*L-ascorbate (vitamin C)*ascorbic acid 176.126 C6 H8 O6 C1(O[CH](C(O)CO)C(=O)C(O)=1)(O) LIGAND-CPD:C00072:*CAS:50-81-7 1.8.5.1 L-dehydro-ascorbate + glutathione = glutathione disulfide + L-ascorbate ascorbate glutathione cycle L-ascorbate vitamin C*ascorbate*L-ascorbate (vitamin C)*ascorbic acid 176.126 C6 H8 O6 C1(O[CH](C(O)CO)C(=O)C(O)=1)(O) LIGAND-CPD:C00072:*CAS:50-81-7 1.14.17.4 L-ascorbate + 1-aminocyclopropane-1-carboxylate + O2 = H2O + ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 ethylene biosynthesis from methionine L-ascorbate vitamin C*ascorbate*L-ascorbate (vitamin C)*ascorbic acid 176.126 C6 H8 O6 C1(O[CH](C(O)CO)C(=O)C(O)=1)(O) LIGAND-CPD:C00072:*CAS:50-81-7 1.10.99.3 violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O carotenoid biosynthesis L-ascorbate vitamin C*ascorbate*L-ascorbate (vitamin C)*ascorbic acid 176.126 C6 H8 O6 C1(O[CH](C(O)CO)C(=O)C(O)=1)(O) LIGAND-CPD:C00072:*CAS:50-81-7 1.10.99.3 violaxanthin + L-ascorbate = antheraxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle L-ascorbate vitamin C*ascorbate*L-ascorbate (vitamin C)*ascorbic acid 176.126 C6 H8 O6 C1(O[CH](C(O)CO)C(=O)C(O)=1)(O) LIGAND-CPD:C00072:*CAS:50-81-7 1.11.1.11 L-ascorbate + H2O2 = monodehydroascorbate + H2O ascorbate glutathione cycle L-ascorbate vitamin C*ascorbate*L-ascorbate (vitamin C)*ascorbic acid 176.126 C6 H8 O6 C1(O[CH](C(O)CO)C(=O)C(O)=1)(O) LIGAND-CPD:C00072:*CAS:50-81-7 1.10.3.3 L-ascorbate + O2 = monodehydroascorbate + H2O ascorbate glutathione cycle L-ascorbate vitamin C*ascorbate*L-ascorbate (vitamin C)*ascorbic acid 176.126 C6 H8 O6 C1(O[CH](C(O)CO)C(=O)C(O)=1)(O) LIGAND-CPD:C00072:*CAS:50-81-7 1.10.99.3 antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O carotenoid biosynthesis L-ascorbate vitamin C*ascorbate*L-ascorbate (vitamin C)*ascorbic acid 176.126 C6 H8 O6 C1(O[CH](C(O)CO)C(=O)C(O)=1)(O) LIGAND-CPD:C00072:*CAS:50-81-7 1.10.99.3 antheraxanthin + L-ascorbate = zeaxanthin + L-dehydro-ascorbate + H2O xanthophyll cycle L-histidinol-phosphate L-histidinol-phosphate*histidinol-P*L-histidinol-p*histidinol-phosphate 221.152 C6 H12 N3 O4 P1 c1(c(nc[nH]1)CC(N)COP(O)(O)=O) LIGAND-CPD:C01100:*CAS:25679-93-0 2.6.1.9 imidazole acetol-phosphate + L-glutamate = L-histidinol-phosphate + α-ketoglutarate histidine biosynthesis I L-histidinol-phosphate L-histidinol-phosphate*histidinol-P*L-histidinol-p*histidinol-phosphate 221.152 C6 H12 N3 O4 P1 c1(c(nc[nH]1)CC(N)COP(O)(O)=O) LIGAND-CPD:C01100:*CAS:25679-93-0 3.1.3.15 L-histidinol-phosphate + H2O = histidinol histidine biosynthesis I kaempferol 286.24 C15 H10 O6 c1(O)(ccc(cc1)C2(=C(O)C(=O)c3(c(O2)cc(O)cc3O))) 1.14.11.23 dihydrokaempferol + α-ketoglutarate + O2 = kaempferol + succinate + CO2 + H2O flavonol biosynthesis cadaverine 1,5-Diaminopentane*1,5-pentanediamine*pentamethylenediamine*BioDex 1-*cadaverine 102.179 C5 H14 N2 C(N)CCCCN PUBCHEM:273:*LIGAND-CPD:C01672:*CAS:462-94-2 4.1.1.18 L-lysine = CO2 + cadaverine lysine degradation I nitrous oxide N2O 44.013 N2 O1 N#N=O LIGAND-CPD:C00887:*CAS:10024-97-2 1.7.99.7 nitrous oxide + H2O = nitric oxide nitrate reduction I nitrous oxide N2O 44.013 N2 O1 N#N=O LIGAND-CPD:C00887:*CAS:10024-97-2 1.7.99.6 N2 + H2O = nitrous oxide nitrate reduction I 1-amino-propan-2-one-3-phosphate 169.074 C3 H8 N1 O5 P1 C(N)C(=O)COP(O)(O)=O 2.6.99.2 1-deoxy-D-xylulose 5-phosphate + 1-amino-propan-2-one-3-phosphate = pyridoxine-5'-phosphate + H2O pyridoxal 5'-phosphate biosynthesis 1-amino-propan-2-one-3-phosphate 169.074 C3 H8 N1 O5 P1 C(N)C(=O)COP(O)(O)=O (2S)-2-amino-3-oxo-4-phosphonooxybutanoate + H+ = 1-amino-propan-2-one-3-phosphate + CO2 pyridoxal 5'-phosphate biosynthesis GDP-D-rhamnose GDP-6-deoxy-D-mannose 589.345 C16 H25 N5 O15 P2 CC1(OC(C(O)C(O)C1O)OP(=O)(O)OP(=O)(O)OCC2(OC(C(O)C2O)n3(c4(c(nc3)c(=O)[nH]c(n4)N)))) 1.1.1.187 GDP-D-rhamnose = GDP-4-dehydro-6-deoxy-D-mannose + H+ GDP-D-rhamnose biosynthesis delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside 951.818 C42 H47 O25 C1(OC(C(O)C(O)C(O)1)COC(=O)C=Cc2(ccc(O)c(O)c2))Oc5(c4(C=C(OC3(OC(CO)C(O)C(O)C(O)3))C(=Oc4cc(O)c5)c6(cc(c(O)c(O)c6)OC7(C(O)C(O)C(O)C(O7)CO)))) 2.4.1.- delphinidin 3-O-glucosyl-5-O-caffeoylglucoside + UDP-D-glucose = delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + UDP gentiodelphin biosynthesis delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside 951.818 C42 H47 O25 C1(OC(C(O)C(O)C(O)1)COC(=O)C=Cc2(ccc(O)c(O)c2))Oc5(c4(C=C(OC3(OC(CO)C(O)C(O)C(O)3))C(=Oc4cc(O)c5)c6(cc(c(O)c(O)c6)OC7(C(O)C(O)C(O)C(O7)CO)))) 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 951.818 C42 H47 O25 C1(OC(C(O)C(O)C(O)1)COC(=O)C=Cc2(ccc(O)c(O)c2))Oc5(c4(C=C(OC3(OC(CO)C(O)C(O)C(O)3))C(=Oc4cc(O)c5)c6(cc(c(O)c(O)c6)OC7(C(O)C(O)C(O)C(O7)CO)))) 2.3.1.- delphinidin 3,5,3'-triglucoside + caffeoyl-CoA = delphinidin 3-O-glucosyl-5-O-caffeoylglucoside-3'-O-glucoside + coenzyme A gentiodelphin biosynthesis 2,3-cis-proanthocyanidin proanthocyanidin 578.528 C30 H26 O12 c1(c2(c(c(O)cc(O)1)C(C(O)C(O2)c3(cc(O)c(O)cc3))c6(c5(OC(c4(cc(O)c(O)cc4))C(O)Cc5c(O)cc(O)6)))) afzelechin + 2,3-trans-catechin = 2,3-cis-proanthocyanidin proanthocyanidin biosynthesis from flavanols cis-zeatin riboside cZR 351.361 C15 H21 N5 O5 C1(O[CH](CO)C(O)C(O)1)N2(c3(c(N=C2)c(ncn3)NCC=C(C)CO)) cis-zeatin riboside monophosphate + H2O = cis-zeatin riboside cis-zeatin biosynthesis cis-zeatin riboside cZR 351.361 C15 H21 N5 O5 C1(O[CH](CO)C(O)C(O)1)N2(c3(c(N=C2)c(ncn3)NCC=C(C)CO)) cis-zeatin riboside + H2O = cis-zeatin + D-ribose cis-zeatin biosynthesis L-alanine alanine*L-α-alanine 89.094 C3 H7 N1 O2 C(=O)(O)C(C)N LIGAND-CPD:C00041:*CAS:56-41-7 indole-3-acetate + L-alanine = indole-3-acetyl-ala + H2O IAA conjugate biosynthesis II L-alanine alanine*L-α-alanine 89.094 C3 H7 N1 O2 C(=O)(O)C(C)N LIGAND-CPD:C00041:*CAS:56-41-7 2.6.1.2 α-ketoglutarate + L-alanine = L-glutamate + pyruvate alanine biosynthesis II L-alanine alanine*L-α-alanine 89.094 C3 H7 N1 O2 C(=O)(O)C(C)N LIGAND-CPD:C00041:*CAS:56-41-7 2.6.1.2 α-ketoglutarate + L-alanine = L-glutamate + pyruvate alanine degradation III L-alanine alanine*L-α-alanine 89.094 C3 H7 N1 O2 C(=O)(O)C(C)N LIGAND-CPD:C00041:*CAS:56-41-7 2.8.1.7 L-cysteine = L-alanine + protein-S-sulfanylcysteine alanine biosynthesis III L-alanine alanine*L-α-alanine 89.094 C3 H7 N1 O2 C(=O)(O)C(C)N LIGAND-CPD:C00041:*CAS:56-41-7 2.6.1.30 pyruvate + pyridoxamine = L-alanine + pyridoxal pyridoxamine anabolism L-alanine alanine*L-α-alanine 89.094 C3 H7 N1 O2 C(=O)(O)C(C)N LIGAND-CPD:C00041:*CAS:56-41-7 6.1.1.7 L-alanine + ATP = diphosphate + AMP tRNA charging pathway L-alanine alanine*L-α-alanine 89.094 C3 H7 N1 O2 C(=O)(O)C(C)N LIGAND-CPD:C00041:*CAS:56-41-7 2.6.1.18 malonate semialdehyde + L-alanine = β-alanine + pyruvate β-alanine biosynthesis II L-alanine alanine*L-α-alanine 89.094 C3 H7 N1 O2 C(=O)(O)C(C)N LIGAND-CPD:C00041:*CAS:56-41-7 2.3.1.47 pimeloyl-CoA + L-alanine = CO2 + coenzyme A + 7-keto-8-aminopelargonate biotin biosynthesis II L-alanine alanine*L-α-alanine 89.094 C3 H7 N1 O2 C(=O)(O)C(C)N LIGAND-CPD:C00041:*CAS:56-41-7 2.3.1.47 pimeloyl-CoA + L-alanine = CO2 + coenzyme A + 7-keto-8-aminopelargonate biotin biosynthesis I L-alanine alanine*L-α-alanine 89.094 C3 H7 N1 O2 C(=O)(O)C(C)N LIGAND-CPD:C00041:*CAS:56-41-7 6.3.2.8 L-alanine + UDP-N-acetylmuramate + ATP = UDP-N-acetylmuramoyl-L-alanine + ADP peptidoglycan biosynthesis I L-alanine alanine*L-α-alanine 89.094 C3 H7 N1 O2 C(=O)(O)C(C)N LIGAND-CPD:C00041:*CAS:56-41-7 3.7.1.3 3-hydroxy-L-kynurenine + H2O = 3-hydroxy-anthranilate + L-alanine tryptophan degradation III (eukaryotic) L-alanine alanine*L-α-alanine 89.094 C3 H7 N1 O2 C(=O)(O)C(C)N LIGAND-CPD:C00041:*CAS:56-41-7 3.5.1.- indole-3-acetyl-ala + H2O = indole-3-acetate + L-alanine IAA biosynthesis II L-alanine alanine*L-α-alanine 89.094 C3 H7 N1 O2 C(=O)(O)C(C)N LIGAND-CPD:C00041:*CAS:56-41-7 2.6.1.58 pyruvate + L-phenylalanine = phenylpyruvate + L-alanine phenylalanine degradation III phytocassane B 334.455 C20 H30 O4 CC1(C(C=C)=CC(=O)[CH]2(C3(C)([CH](CC[CH]12)C(C)(C)C(O)C(O)C(O)3))) phytocassane C = phytocassane B phytocassane biosynthesis phytocassane B 334.455 C20 H30 O4 CC1(C(C=C)=CC(=O)[CH]2(C3(C)([CH](CC[CH]12)C(C)(C)C(O)C(O)C(O)3))) ent-cassa-12,15-diene-2,3α-ol-11-keto = phytocassane B phytocassane biosynthesis (+)-isomenthone 154.252 C10 H18 O1 CC(C)C1(C(=O)CC(C)CC1) (+)-isomenthone + NADPH = (+)-neoisomenthol + NADP+ menthol biosynthesis (+)-isomenthone 154.252 C10 H18 O1 CC(C)C1(C(=O)CC(C)CC1) (+)-pulegone + NADPH = (+)-isomenthone + NADP+ menthol biosynthesis (+)-isomenthone 154.252 C10 H18 O1 CC(C)C1(C(=O)CC(C)CC1) (+)-isomenthone + NADPH = (+)-isomenthol + NADP+ menthol biosynthesis FMN flavin mononucleotide 456.348 C17 H21 N4 O9 P1 C1(c2(c(=NC(=O)N1)n(c3(c(n2)cc(C)c(c3)C))CC(O)C(O)C(O)COP(=O)(O)O))(=O) PUBCHEM:710:*LIGAND-CPD:C00061:*CAS:146-17-8 2.7.1.26 riboflavin + ATP = FMN + ADP flavin biosynthesis FMN flavin mononucleotide 456.348 C17 H21 N4 O9 P1 C1(c2(c(=NC(=O)N1)n(c3(c(n2)cc(C)c(c3)C))CC(O)C(O)C(O)COP(=O)(O)O))(=O) PUBCHEM:710:*LIGAND-CPD:C00061:*CAS:146-17-8 2.7.7.2 FMN + ATP = FAD + diphosphate flavin biosynthesis 5-methylthioribose-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 260.198 C6 H13 O7 P1 S1 C1(OC(CSC)C(O)C(O)1)(OP(O)(=O)O) PUBCHEM:440251:*LIGAND-CPD:C04188: 5.3.1.23 5-methylthioribose-1-phosphate = 5-methylthioribulose-1-phosphate methionine salvage pathway 5-methylthioribose-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 260.198 C6 H13 O7 P1 S1 C1(OC(CSC)C(O)C(O)1)(OP(O)(=O)O) PUBCHEM:440251:*LIGAND-CPD:C04188: 2.7.1.100 ATP + 5-methylthioribose = ADP + 5-methylthioribose-1-phosphate methionine salvage pathway Mg-protoporphyrin 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 598.983 C35 H34 N4 O4 MG1 Cc6(c(CCC(=O)OC)c1(n7([Mg]35(n4(c(C=C2(C(C)=C(C(C=1)=N23)CCC(O)=O))c(C)c(C=C)c4C=C8(N5=C(C=c67)C(C=C)=C(C)8)))))) 2.1.1.11 Mg-protoporphyrin + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + Mg-protoporphyrin monomethyl ester chlorophyllide a biosynthesis Mg-protoporphyrin 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 598.983 C35 H34 N4 O4 MG1 Cc6(c(CCC(=O)OC)c1(n7([Mg]35(n4(c(C=C2(C(C)=C(C(C=1)=N23)CCC(O)=O))c(C)c(C=C)c4C=C8(N5=C(C=c67)C(C=C)=C(C)8)))))) 1.14.13.81 Mg-protoporphyrin monomethyl ester + NADPH + H+ + O2 = 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O chlorophyllide a biosynthesis 4-oxo-4-(3-pyridyl)-butanamide 4-(3-pyridyl)-4-oxobutyramide 178.19 C9 H10 N2 O2 c1(ncc(cc1)C(=O)CCC(=O)N) norcotinine = 4-oxo-4-(3-pyridyl)-butanamide nicotine degradation II 4-oxo-4-(3-pyridyl)-butanamide 4-(3-pyridyl)-4-oxobutyramide 178.19 C9 H10 N2 O2 c1(ncc(cc1)C(=O)CCC(=O)N) norcotinine = 4-oxo-4-(3-pyridyl)-butanamide nicotine degradation III 4-oxo-4-(3-pyridyl)-butanamide 4-(3-pyridyl)-4-oxobutyramide 178.19 C9 H10 N2 O2 c1(ncc(cc1)C(=O)CCC(=O)N) 4-oxo-4-(3-pyridyl)-butanamide = 4-oxo-4-(3-pyridyl)-butanoate nicotine degradation II 4-oxo-4-(3-pyridyl)-butanamide 4-(3-pyridyl)-4-oxobutyramide 178.19 C9 H10 N2 O2 c1(ncc(cc1)C(=O)CCC(=O)N) 4-oxo-4-(3-pyridyl)-butanamide = 4-oxo-4-(3-pyridyl)-butanoate nicotine degradation III GA51 gibberellin A51*gibberellin A51*GA51 332.396 C19 H24 O5 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(CC(O)C3)(C)[CH]4C5C(=O)O)))) 1.14.11.- GA9 + α-ketoglutarate + O2 = GA51 + succinate + CO2 gibberellin inactivation GA51 gibberellin A51*gibberellin A51*GA51 332.396 C19 H24 O5 C=C1(C2(CC5(C1)([CH](CC2)C34(OC(=O)C(CC(O)C3)(C)[CH]4C5C(=O)O)))) 1.14.11.- GA51 + α-ketoglutarate + O2 = GA51-catabolite + succinate + CO2 + H2O gibberellin inactivation prephytoene diphosphate 722.92 C40 H68 O7 P2 CC(CCC=C(C)CCC=C(C)C)=CCCC1([CH]([CH]1COP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)(C) 2.5.1.32 prephytoene diphosphate = phytoene + diphosphate carotenoid biosynthesis prephytoene diphosphate 722.92 C40 H68 O7 P2 CC(CCC=C(C)CCC=C(C)C)=CCCC1([CH]([CH]1COP(O)(=O)OP(O)(O)=O)C=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)(C) 2.5.1.32 geranylgeranyl diphosphate = prephytoene diphosphate + diphosphate carotenoid biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 3.1.7.2 guanosine 5'-diphosphate,3'-diphosphate + H2O = diphosphate + GDP ppGpp biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.23 N-acetyl-glucosamine-1-phosphate + UTP = UDP-N-acetyl-D-glucosamine + diphosphate UDP-N-acetylgalactosamine biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.15 p-aminobenzoate + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate = diphosphate tetrahydrofolate biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.15 p-aminobenzoate + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate = diphosphate tetrahydrofolate biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 3.6.1.23 H2O + dUTP = diphosphate + dUMP de novo biosynthesis of pyrimidine deoxyribonucleotides diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.24 α-D-glucose 1-phosphate + dTTP = dTDP-D-glucose + diphosphate dTDP-L-rhamnose biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.- chlorophyllide a + geranylgeranyl diphosphate = geranylgeranyl-chlorophyll a + diphosphate chlorophyll a biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.29 trans, trans-farnesyl diphosphate = geranylgeranyl diphosphate + diphosphate geranylgeranyldiphosphate biosynthesis II (plastidic) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.60 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 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- geranyl-PP = terpinolene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.1.1 ammonia + L-aspartate + ATP = L-asparagine + diphosphate + AMP asparagine biosynthesis III diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.15 L-proline + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- geranyl-PP = tricyclene + diphosphate oleoresin monoterpene volatiles biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.14 geranyl-PP = (-)-β-pinene + diphosphate oleoresin monoterpene volatiles biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.14 geranyl-PP = (-)-β-pinene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.4.15 biotin + ATP = diphosphate + AMP biotin-carboxyl carrier protein diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- trans, trans-farnesyl diphosphate = (E)-α-bisabolene + diphosphate oleoresin sesquiterpene volatiles biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.2 FMN + ATP = FAD + diphosphate flavin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.1 2'-hydroxygenistein + dimethylallyl-PP = phaseoluteone + diphosphate wighteone and luteone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- geranyl-PP = (-)-β-phellandrene + diphosphate oleoresin monoterpene volatiles biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.26 ATP + O-succinylbenzoate + coenzyme A = 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA + AMP + diphosphate phylloquinone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.1 genistein + dimethylallyl-PP = wighteone + diphosphate wighteone and luteone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- geranyl-PP = (Z)-β-ocimene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.- umbelliferone + dimethylallyl-PP = demethylsuberosin + diphosphate linear furanocoumarin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.15 geranyl-PP = β-myrcene + diphosphate oleoresin monoterpene volatiles biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.15 geranyl-PP = β-myrcene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.10 L-methionine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- trans, trans-farnesyl diphosphate = longifolene + diphosphate oleoresin sesquiterpene volatiles biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.31 trans, trans-farnesyl diphosphate = 2-cis,6-trans,10-trans-geranylgeranyl diphosphate + diphosphate polyisoprenoid biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 ent-copalyl diphosphate = ent-sandaracopimaradiene + diphosphate oryzalexin A-F biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.16 L-cysteine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 5-phosphoribosyl 1-pyrophosphate + hypoxanthine = inosine-5'-phosphate + diphosphate salvage pathways of adenine, hypoxanthine, and their nucleosides diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.11 L-serine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.16 geranyl-PP = (-)-limonene + diphosphate oleoresin monoterpene volatiles biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.16 geranyl-PP = (-)-limonene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.16 geranyl-PP = (-)-limonene + diphosphate menthol biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- geranyl-PP = (+)-3-carene + diphosphate oleoresin monoterpene volatiles biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.14 phosphoryl-ethanolamine + CTP = CDP-ethanolamine + diphosphate phospholipid biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.62 chlorophyllide a + phytyl-PP = chlorophyll a + diphosphate chlorophyll cycle diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.62 chlorophyllide a + phytyl-PP = chlorophyll a + diphosphate chlorophyll a biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.- chlorophyllide b + phytyl-PP = chlorophyll b + diphosphate chlorophyll cycle diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.9 L-valine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.10 orotidine-5'-phosphate + diphosphate = 5-phosphoribosyl 1-pyrophosphate + orotate de novo biosynthesis of pyrimidine ribonucleotides diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.17 phosphoribosyl-ATP + diphosphate = ATP + 5-phosphoribosyl 1-pyrophosphate histidine biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.5.2 xanthosine-5-phosphate + H2O + L-glutamine + ATP = L-glutamate + GMP + diphosphate + AMP purine nucleotides de novo biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.5 L-isoleucine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.13 α-D-mannose 1-phosphate + GTP = GDP-D-mannose + diphosphate ascorbate biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP oxidative ethanol degradation III diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP glutamate degradation VII (to butyrate) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.1 coenzyme A + acetate + ATP = acetyl-CoA + diphosphate + AMP oxidative ethanol degradation I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.27 α-D-glucose 1-phosphate + ATP = ADP-D-glucose + diphosphate starch biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.18 ATP + nicotinate nucleotide = diphosphate + deamido-NAD NAD biosynthesis I (from aspartate) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.18 ATP + nicotinate nucleotide = diphosphate + deamido-NAD NAD salvage pathway I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.18 ATP + nicotinate nucleotide = diphosphate + deamido-NAD pyridine nucleotide cycling (plants) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.6 L-lysine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.21 trans, trans-farnesyl diphosphate = presqualene diphosphate + diphosphate cholesterol biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.21 trans, trans-farnesyl diphosphate = presqualene diphosphate + diphosphate cholesterol biosynthesis III (via desmosterol) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.21 trans, trans-farnesyl diphosphate = presqualene diphosphate + diphosphate cholesterol biosynthesis II (via 24,25-dihydrolanosterol) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.21 trans, trans-farnesyl diphosphate = presqualene diphosphate + diphosphate sterol biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.8 dimethylallyl-PP = diphosphate cis-zeatin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.- 4-prenylphlorisovalerophenone + dimethylallyl-PP = diprenylphlorisovalerophenone + diphosphate humulone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.18 diphosphate = anthranilate + 5-phosphoribosyl 1-pyrophosphate tryptophan biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.41 CTP = diphosphate phospholipid biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.41 CTP = diphosphate phospholipid biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.41 CTP = diphosphate cardiolipin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.4.1 ammonia + xanthosine-5-phosphate + ATP = AMP + diphosphate + GMP salvage pathways of purine nucleosides II (plant) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.4.1 ammonia + xanthosine-5-phosphate + ATP = AMP + diphosphate + GMP purine nucleotides de novo biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.17 coenzyme A + propionate + ATP = propionyl-CoA + diphosphate + AMP β-alanine biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.12 caffeate + coenzyme A + ATP = caffeoyl-CoA + AMP + diphosphate suberin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.18 L-glutamine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.22 L-asparagine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 dalbergioidin + dimethylallyl-PP = kievitone + diphosphate kievitone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.2.1 β-alanine + L-pantoate + ATP = pantothenate + diphosphate + AMP pantothenate biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.2.1 β-alanine + L-pantoate + ATP = pantothenate + diphosphate + AMP pantothenate biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.21 presqualene diphosphate = squalene + diphosphate cholesterol biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.21 presqualene diphosphate = squalene + diphosphate cholesterol biosynthesis III (via desmosterol) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.21 presqualene diphosphate = squalene + diphosphate cholesterol biosynthesis II (via 24,25-dihydrolanosterol) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.21 presqualene diphosphate = squalene + diphosphate sterol biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 3.6.1.1 UDP-glucose conversion diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.1.5 ammonia + ATP + deamido-NAD = AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- trans, trans-farnesyl diphosphate = δ-selinene + diphosphate oleoresin sesquiterpene volatiles biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 polyisoprenoid biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine S-adenosylmethionine biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.6 ATP + L-methionine + H2O = diphosphate + S-adenosyl-L-methionine methionine salvage pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*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 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*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 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*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 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*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 diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- geranyl-PP = (E)-β-ocimene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.- phlorisobutyrophenone + dimethylallyl-PP = 4-prenylphlorisobutyrophenone + diphosphate cohumulone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.1 genistein + dimethylallyl-PP = isowighteone + diphosphate wighteone and luteone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.19 ent-copalyl diphosphate = diphosphate + ent-kaur-16-ene ent-kaurene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.37 β-L-arabinose 1-phosphate + UTP = UDP-L-arabinose + diphosphate UDP-L-arabinose biosynthesis II (from L-arabinose) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.9 diphosphate + UMP = 5-phosphoribosyl 1-pyrophosphate + uracil salvage pathways of purine and pyrimidine nucleotides diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.9 diphosphate + UMP = 5-phosphoribosyl 1-pyrophosphate + uracil salvage pathways of pyrimidine ribonucleotides diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.8 diphosphate + inosine-5'-phosphate = 5-phosphoribosyl 1-pyrophosphate + hypoxanthine salvage pathways of purine nucleosides diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.8 diphosphate + inosine-5'-phosphate = 5-phosphoribosyl 1-pyrophosphate + hypoxanthine salvage pathways of purine nucleosides II (plant) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.3 L-threonine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis III diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.5.4 L-glutamine + L-aspartate + ATP + H2O = L-glutamate + L-asparagine + diphosphate + AMP asparagine biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.19 CO2 + diphosphate + nicotinate nucleotide = 5-phosphoribosyl 1-pyrophosphate + quinolinate NAD biosynthesis I (from aspartate) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.1 nicotinamide mononucleotide + ATP = NAD+ + diphosphate NAD salvage pathway II diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ NAD biosynthesis I (from aspartate) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ NAD salvage pathway I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.5.1 ATP + deamido-NAD + L-glutamine + H2O = L-glutamate + AMP + diphosphate + NAD+ pyridine nucleotide cycling (plants) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.4 L-leucine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.3 coenzyme A + ATP = diphosphate + AMP acyl-CoA synthetase pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 homogentisate + phytyl-PP = 2-methyl-6-phytyl-1,4-benzoquinone + CO2 + diphosphate vitamin E biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.26 ATP + O-succinylbenzoate + coenzyme A = AMP + diphosphate + O-succinylbenzoyl-CoA menaquinone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.27 dimethylallyl-PP + AMP = isopentenyladenosine-5'-monophosphate + diphosphate trans-zeatin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phosphoribosyl 1-pyrophosphate + L-glutamine + H2O purine nucleotides de novo biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.14 5-phospho-β-D-ribosyl-amine + diphosphate + L-glutamate = 5-phosphoribosyl 1-pyrophosphate + L-glutamine + H2O purine nucleotides de novo biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 homogentisate + solanyl pyrophosphate = 2-methyl-6-solanyl-1,4-benzoquinone + CO2 + diphosphate plastoquinone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.44 α-D-glucuronate 1-phosphate + UTP = UDP-D-glucuronate + diphosphate UDP-D-glucuronate biosynthesis (from myo-inositol) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.- dimethylallyl-PP + ATP = isopentenyladenosine-5'-triphosphate + diphosphate trans-zeatin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.1 2'-hydroxygenistein + dimethylallyl-PP = luteone + diphosphate wighteone and luteone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.14 glycine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- geranyl-PP + H2O = geraniol + diphosphate secologanin and strictosidine biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.14 geranyl-PP = (-)-α-pinene + diphosphate oleoresin monoterpene volatiles biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.14 geranyl-PP = (-)-α-pinene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 ent-copalyl diphosphate = ent-cassa-12,15-diene + diphosphate phytocassane biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 3.6.1.- 7,8-dihydroneopterin 3'-triphosphate + H2O = dihydroneopterin phosphate + diphosphate tetrahydrofolate biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 3.6.1.- 7,8-dihydroneopterin 3'-triphosphate + H2O = dihydroneopterin phosphate + diphosphate tetrahydrofolate biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.1.90 fructose-6-phosphate + diphosphate = fructose-1,6-bisphosphate glycolysis IV (plant cytosol) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate = demethylmenaquinone-8 + diphosphate + CO2 menaquinone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- trans, trans-farnesyl diphosphate = γ-humulene + diphosphate oleoresin sesquiterpene volatiles biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.15 phosphoryl-choline + CTP = CDP-choline + diphosphate phospholipid biosynthesis II diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.15 phosphoryl-choline + CTP = CDP-choline + diphosphate choline biosynthesis III diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.20 L-phenylalanine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- geranyl-PP = sabinene + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.4.5 O-ureidohomoserine + L-aspartate + ATP = canavaninosuccinate + AMP + diphosphate canavanine biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP urea cycle diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis II (acetyl cycle) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP citrulline-nitric oxide cycle diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis IV diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.4.5 L-aspartate + citrulline + ATP = L-arginino-succinate + diphosphate + AMP arginine biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- geranyl-PP = (-)-camphene + diphosphate oleoresin monoterpene volatiles biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.- phlorisovalerophenone + dimethylallyl-PP = 4-prenylphlorisovalerophenone + diphosphate humulone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.10 α-D-galactose 1-phosphate + UTP = UDP-galactose + diphosphate galactose degradation II diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.19 L-arginine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.1 dimethylallyl-PP = diphosphate + geranyl-PP geranylgeranyldiphosphate biosynthesis II (plastidic) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.1 dimethylallyl-PP = diphosphate + geranyl-PP polyisoprenoid biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.1 dimethylallyl-PP = diphosphate + geranyl-PP geranyldiphosphate biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.1 dimethylallyl-PP = diphosphate + geranyl-PP trans,trans-farnesyl diphosphate biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid β-oxidation I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.3 coenzyme A + ATP = diphosphate + AMP fatty acid β-oxidation II (plant, saturated) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.1 genistein + dimethylallyl-PP = lupiwighteone + diphosphate wighteone and luteone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- geranyl-PP + H2O = (-)-α-terpineol + diphosphate monoterpene biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- trans, trans-farnesyl diphosphate = α-longipinene + diphosphate oleoresin sesquiterpene volatiles biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.2 ATP + L-tryptophan = AMP + diphosphate tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.10 geranyl-PP = diphosphate + trans, trans-farnesyl diphosphate geranylgeranyldiphosphate biosynthesis II (plastidic) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.10 geranyl-PP = diphosphate + trans, trans-farnesyl diphosphate polyisoprenoid biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.10 geranyl-PP = diphosphate + trans, trans-farnesyl diphosphate trans,trans-farnesyl diphosphate biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.32 prephytoene diphosphate = phytoene + diphosphate carotenoid biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.3 4-methyl-5-(β-hydroxyethyl)thiazole phosphate + 4-amino-5-hydroxymethyl-2-methylpyrimidine-pyrophosphate = thiamine-phosphate + diphosphate thiamine biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.32 geranylgeranyl diphosphate = prephytoene diphosphate + diphosphate carotenoid biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 ATP + L-serine + 2,3-dihydroxybenzoate = enterobactin + diphosphate + AMP enterobactin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate sucrose degradation III diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate sucrose degradation to ethanol and lactate (anaerobic) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate galactose degradation II diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate UDP-glucose conversion diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate UDP-galactose biosynthesis (salvage pathway from galactose using UDP-glucose) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.9 α-D-glucose 1-phosphate + UTP = UDP-D-glucose + diphosphate sucrose biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.11 L-serine + ATP = diphosphate + AMP selenocysteine biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.21 L-histidine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of adenine, hypoxanthine, and their nucleosides diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of purine nucleosides diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of purine and pyrimidine nucleotides diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.7 AMP + diphosphate = 5-phosphoribosyl 1-pyrophosphate + adenine salvage pathways of purine nucleosides II (plant) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.3 pantetheine 4'-phosphate + ATP = dephospho-CoA + diphosphate coenzyme A biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.3.2.5 D-4'-phosphopantothenate + L-cysteine + CTP = R-4'-phosphopantothenoyl-L-cysteine + diphosphate + CMP coenzyme A biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.9 trans, trans-farnesyl diphosphate = 5-epi-aristolochene + diphosphate capsidiol biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.12 L-aspartate + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.1 L-tyrosine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 1,4-dihydroxy-2-naphthoate + phytyl-PP = demethylphylloquinone + CO2 + diphosphate phylloquinone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.1 2'-hydroxygenistein + dimethylallyl-PP = 2,3-dehydrokievitone + diphosphate kievitone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.- polyisoprenoid biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.7 L-alanine + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.12 coenzyme A + 4-coumarate + ATP = coumaroyl-CoA + diphosphate + AMP flavonoid biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.12 coenzyme A + 4-coumarate + ATP = coumaroyl-CoA + diphosphate + AMP phenylpropanoid biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 3.5.4.25 H2O + GTP = diphosphate + 2,5-diamino-6-(ribosylamino)-4-(3H)-pyrimidinone 5'-phosphate + formate flavin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*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 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.- 4-prenylphlorisobutyrophenone + dimethylallyl-PP = diprenylphlorisobutyrophenone + diphosphate cohumulone biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.2.1.12 ferulate + coenzyme A + ATP = feruloyl-CoA + AMP + diphosphate suberin biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 4.2.3.- trans, trans-farnesyl diphosphate = (E)-β-caryophyllene + diphosphate oleoresin sesquiterpene volatiles biosynthesis diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.17 L-glutamate + ATP = diphosphate + AMP tRNA charging pathway diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 6.1.1.17 L-glutamate + ATP = diphosphate + AMP tetrapyrrole biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.8 5-phosphoribosyl 1-pyrophosphate + guanine = diphosphate + GMP salvage pathways of purine nucleosides diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.8 5-phosphoribosyl 1-pyrophosphate + guanine = diphosphate + GMP salvage pathways of purine and pyrimidine nucleotides diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.8 5-phosphoribosyl 1-pyrophosphate + guanine = diphosphate + GMP salvage pathways of purine nucleosides II (plant) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 3.6.1.31 phosphoribosyl-ATP + H2O = phosphoribosyl-AMP + diphosphate histidine biosynthesis I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.11 nicotinate nucleotide + diphosphate = nicotinate + 5-phosphoribosyl 1-pyrophosphate NAD salvage pathway I diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.4.2.11 nicotinate nucleotide + diphosphate = nicotinate + 5-phosphoribosyl 1-pyrophosphate pyridine nucleotide cycling (plants) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate reduction II (assimilatory) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfite oxidation III diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate reduction I (assimilatory) diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.7.7.4 sulfate + ATP = adenosine 5'-phosphosulfate + diphosphate sulfate activation for sulfonation diphosphate diphosphate*PPi*PP*pyrophosphate 177.975 H4 O7 P2 O(P(O)(O)=O)P(O)(=O)O CAS:09/03/2466:*LIGAND-CPD:C00013:*CAS:2466-09-3 2.5.1.- dimethylallyl-PP + ADP = isopentenyladenosine-5'-diphosphate + diphosphate trans-zeatin biosynthesis phosphoribosylformiminoAICAR-phosphate 1-(5-Phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide*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 577.334 C15 H25 N5 O15 P2 C(OP(=O)(O)O)[CH]1(O[CH]([CH](O)[CH]1O)NC=Nc2(n(cnc2C(=O)N)[CH]3(O[CH]([CH](O)[CH](O)3)COP(=O)(O)O))) PUBCHEM:440534:*LIGAND-CPD:C04896: 5.3.1.16 phosphoribosylformiminoAICAR-phosphate = phosphoribulosylformimino-AICAR-P histidine biosynthesis I phosphoribosylformiminoAICAR-phosphate 1-(5-Phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide*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 577.334 C15 H25 N5 O15 P2 C(OP(=O)(O)O)[CH]1(O[CH]([CH](O)[CH]1O)NC=Nc2(n(cnc2C(=O)N)[CH]3(O[CH]([CH](O)[CH](O)3)COP(=O)(O)O))) PUBCHEM:440534:*LIGAND-CPD:C04896: 3.5.4.19 phosphoribosyl-AMP + H2O = phosphoribosylformiminoAICAR-phosphate histidine biosynthesis I dGDP 2'-deoxyguanosine-5'-diphosphate*deoxyguanosine-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(CC1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00361:*CAS:102783-74-4 GDP = dGDP + H2O purine nucleotides de novo biosynthesis I dGDP 2'-deoxyguanosine-5'-diphosphate*deoxyguanosine-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(CC1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00361:*CAS:102783-74-4 2.7.4.6 dGDP + ATP = dGTP + ADP purine nucleotides de novo biosynthesis I dGDP 2'-deoxyguanosine-5'-diphosphate*deoxyguanosine-diphosphate 427.203 C10 H15 N5 O10 P2 C(OP(=O)(O)OP(O)(O)=O)C1(OC(CC1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00361:*CAS:102783-74-4 1.17.4.1 dGDP + H2O = GDP purine nucleotides de novo biosynthesis I N2-succinyl-L-arginine N2-succinylarginine 274.276 C10 H18 N4 O5 C(=O)(CCC(=O)O)NC(C(O)=O)CCCNC(N)=N CAS:1758-80-1:*LIGAND-CPD:C03296: 3.5.3.- N2-succinyl-L-arginine + H2O = ammonia + N2-succinyl-L-ornithine + CO2 arginine degradation II N2-succinyl-L-arginine N2-succinylarginine 274.276 C10 H18 N4 O5 C(=O)(CCC(=O)O)NC(C(O)=O)CCCNC(N)=N CAS:1758-80-1:*LIGAND-CPD:C03296: 2.3.1.109 L-arginine + succinyl-CoA = N2-succinyl-L-arginine + coenzyme A arginine degradation II pantothenate (R)-pantothenate*vitamin B5*pantothenic acid*D-pantothenic acid 219.237 C9 H17 N1 O5 CC(C)(CO)C(O)C(=O)NCCC(O)=O LIGAND-CPD:C00864:*CAS:79-83-4 6.3.2.1 pantoyl lactone + β-alanine = pantothenate pantothenate biosynthesis III pantothenate (R)-pantothenate*vitamin B5*pantothenic acid*D-pantothenic acid 219.237 C9 H17 N1 O5 CC(C)(CO)C(O)C(=O)NCCC(O)=O LIGAND-CPD:C00864:*CAS:79-83-4 6.3.2.1 β-alanine + L-pantoate + ATP = pantothenate + diphosphate + AMP pantothenate biosynthesis I pantothenate (R)-pantothenate*vitamin B5*pantothenic acid*D-pantothenic acid 219.237 C9 H17 N1 O5 CC(C)(CO)C(O)C(=O)NCCC(O)=O LIGAND-CPD:C00864:*CAS:79-83-4 6.3.2.1 β-alanine + L-pantoate + ATP = pantothenate + diphosphate + AMP pantothenate biosynthesis II pantothenate (R)-pantothenate*vitamin B5*pantothenic acid*D-pantothenic acid 219.237 C9 H17 N1 O5 CC(C)(CO)C(O)C(=O)NCCC(O)=O LIGAND-CPD:C00864:*CAS:79-83-4 2.7.1.33 pantothenate + ATP = D-4'-phosphopantothenate + ADP coenzyme A biosynthesis 4-(3-pyridyl)-butanoate 4-(3-pyridyl)-butanoic acid 165.191 C9 H11 N1 O2 c1(ncc(cc1)CCCC(O)=O) 4-(3-pyridyl)-3-butenoate = 4-(3-pyridyl)-butanoate nicotine degradation II 4-(3-pyridyl)-butanoate 4-(3-pyridyl)-butanoic acid 165.191 C9 H11 N1 O2 c1(ncc(cc1)CCCC(O)=O) 4-(3-pyridyl)-3-butenoate = 4-(3-pyridyl)-butanoate nicotine degradation III 4-(3-pyridyl)-butanoate 4-(3-pyridyl)-butanoic acid 165.191 C9 H11 N1 O2 c1(ncc(cc1)CCCC(O)=O) 4-(3-pyridyl)-butanoate = 3-pyridylacetate nicotine degradation II 4-(3-pyridyl)-butanoate 4-(3-pyridyl)-butanoic acid 165.191 C9 H11 N1 O2 c1(ncc(cc1)CCCC(O)=O) 4-(3-pyridyl)-butanoate = 3-pyridylacetate nicotine degradation III 5-oxoproline L-5-pyrrolidone-2-carboxylic acid*L-pyroglutamic acid*5-oxo-L-proline*pyroglutamic acid*pyroglutamate*5-pyrrolidone-2-carboxylic acid 129.115 C5 H7 N1 O3 C1(NC(C(O)=O)CC1)(=O) LIGAND-CPD:C02238:*LIGAND-CPD:C01879:*CAS:98-79-3 2.3.2.4 (5-L-glutamyl)-L-amino acid = L-2-amino-acid + 5-oxoproline γ-glutamyl cycle 5-O-(indol-3-ylacetyl-myo-inositol) D-galactoside 499.471 C22 H28 N1 O12 c1(c(c2(c(n1)cccc2))CC(=O)OC3(C(O)C(C(O)C(O)C3O)OC4(C(O)C(O)C(O)C(O4)CO))) LIGAND-CPD:C04695: 2.4.1.156 indol-3-yl-acetyl-myo-inositol + UDP-galactose = 5-O-(indol-3-ylacetyl-myo-inositol) D-galactoside + UDP IAA conjugate biosynthesis I 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 442.681 C29 H46 O3 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C(O)=O)C(O)CC4)))) 1.14.13.72 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 442.681 C29 H46 O3 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C(O)=O)C(O)CC4)))) 1.14.13.72 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 442.681 C29 H46 O3 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C(O)=O)C(O)CC4)))) 1.1.1.170 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol = 4α-methyl-5α-cholesta-8,24-dien-3-one + CO2 cholesterol biosynthesis I 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 442.681 C29 H46 O3 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C)(C(O)=O)C(O)CC4)))) 1.1.1.170 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol = 4α-methyl-5α-cholesta-8,24-dien-3-one + CO2 cholesterol biosynthesis III (via desmosterol) nitric oxide NO*nitrogen monoxide*nitrogen protoxide 31.014 H1 N1 O1 N=O LIGAND-CPD:C00533:*CAS:10102-43-9 1.14.13.39 O2 + NADPH + L-arginine = citrulline + NADP+ + nitric oxide citrulline-nitric oxide cycle nitric oxide NO*nitrogen monoxide*nitrogen protoxide 31.014 H1 N1 O1 N=O LIGAND-CPD:C00533:*CAS:10102-43-9 1.7.99.7 nitrous oxide + H2O = nitric oxide nitrate reduction I (-)-trans-carveol 152.236 C10 H16 O1 C=C(C)C1(CC=C(C)C(O)C1) 1.1.1.243 (-)-trans-carveol + NADP+ = (-)-carvone + NADPH + H+ menthol biosynthesis 3β-Hydroxy-9β-pimara-7,15-diene-19,6β-olide 3beta-Hydroxy-9beta-pimara-7,15-diene-19,6beta-olide*3β-Hydroxy-9β-pimara-7,15-dien-19,6β-olide*3beta-Hydroxy-9beta-pimara-7,15-dien-19,6beta-olide 316.439 C20 H28 O3 CC1(CC3([CH](CC1)C2([CH]4(C(C)(C(O)CC2)C(=O)O[CH](C=3)4))(C)))(C=C) 3β-Hydroxy-9β-pimara-7,15-diene-19,6β-olide = momilactone A momilactone biosynthesis 3β-Hydroxy-9β-pimara-7,15-diene-19,6β-olide 3beta-Hydroxy-9beta-pimara-7,15-diene-19,6beta-olide*3β-Hydroxy-9β-pimara-7,15-dien-19,6β-olide*3beta-Hydroxy-9beta-pimara-7,15-dien-19,6beta-olide 316.439 C20 H28 O3 CC1(CC3([CH](CC1)C2([CH]4(C(C)(C(O)CC2)C(=O)O[CH](C=3)4))(C)))(C=C) 1.14.14.1 9β-pimara-7,15-diene = 3β-Hydroxy-9β-pimara-7,15-diene-19,6β-olide momilactone biosynthesis indole-3-acetamide 1H-indole-3-acetamide*indole-3-acetamide*indoleacetamide 174.202 C10 H10 N2 O1 c1(c(CC(N)=O)c2(c([nH]1)cccc2)) CAS:879-37-8 4.2.1.84 indole-3-acetonitrile + H2O = indole-3-acetamide IAA biosynthesis IV indole-3-acetamide 1H-indole-3-acetamide*indole-3-acetamide*indoleacetamide 174.202 C10 H10 N2 O1 c1(c(CC(N)=O)c2(c([nH]1)cccc2)) CAS:879-37-8 3.5.1.4 indole-3-acetamide + H2O = indole-3-acetate + ammonia IAA biosynthesis VI (via indole-3-acetamide) indole-3-acetamide 1H-indole-3-acetamide*indole-3-acetamide*indoleacetamide 174.202 C10 H10 N2 O1 c1(c(CC(N)=O)c2(c([nH]1)cccc2)) CAS:879-37-8 3.5.1.4 indole-3-acetamide + H2O = indole-3-acetate + ammonia IAA biosynthesis IV indole-3-acetamide 1H-indole-3-acetamide*indole-3-acetamide*indoleacetamide 174.202 C10 H10 N2 O1 c1(c(CC(N)=O)c2(c([nH]1)cccc2)) CAS:879-37-8 1.13.12.3 O2 + L-tryptophan = indole-3-acetamide + H2O + CO2 IAA biosynthesis VI (via indole-3-acetamide) 5'-methylthioadenosine 5'-methylthioadenosine*methylthioadenosine*S-methyl-5'-thioadenosine*5'-S-methyl-5'-thioadenosine*MTA*S-methyl-adenosine 297.331 C11 H15 N5 O3 S1 C1(OC(CSC)C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00170:*CAS:2457-80-9 3.2.2.16 5'-methylthioadenosine + H2O = 5-methylthioribose + adenine methionine salvage pathway 5'-methylthioadenosine 5'-methylthioadenosine*methylthioadenosine*S-methyl-5'-thioadenosine*5'-S-methyl-5'-thioadenosine*MTA*S-methyl-adenosine 297.331 C11 H15 N5 O3 S1 C1(OC(CSC)C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00170:*CAS:2457-80-9 2.5.1.22 spermidine + S-adenosyl-L-methioninamine = spermine + 5'-methylthioadenosine spermine biosynthesis 5'-methylthioadenosine 5'-methylthioadenosine*methylthioadenosine*S-methyl-5'-thioadenosine*5'-S-methyl-5'-thioadenosine*MTA*S-methyl-adenosine 297.331 C11 H15 N5 O3 S1 C1(OC(CSC)C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00170:*CAS:2457-80-9 2.5.1.43 S-adenosyl-L-methionine = nicotianamine + 5'-methylthioadenosine 2'-deoxymugineic acid phytosiderophore biosynthesis 5'-methylthioadenosine 5'-methylthioadenosine*methylthioadenosine*S-methyl-5'-thioadenosine*5'-S-methyl-5'-thioadenosine*MTA*S-methyl-adenosine 297.331 C11 H15 N5 O3 S1 C1(OC(CSC)C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00170:*CAS:2457-80-9 4.4.1.14 S-adenosyl-L-methionine = 5'-methylthioadenosine + 1-aminocyclopropane-1-carboxylate methionine salvage pathway 5'-methylthioadenosine 5'-methylthioadenosine*methylthioadenosine*S-methyl-5'-thioadenosine*5'-S-methyl-5'-thioadenosine*MTA*S-methyl-adenosine 297.331 C11 H15 N5 O3 S1 C1(OC(CSC)C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00170:*CAS:2457-80-9 4.4.1.14 S-adenosyl-L-methionine = 5'-methylthioadenosine + 1-aminocyclopropane-1-carboxylate ethylene biosynthesis from methionine 5'-methylthioadenosine 5'-methylthioadenosine*methylthioadenosine*S-methyl-5'-thioadenosine*5'-S-methyl-5'-thioadenosine*MTA*S-methyl-adenosine 297.331 C11 H15 N5 O3 S1 C1(OC(CSC)C(O)C(O)1)n2(c3(c(nc2)c(N)ncn3)) LIGAND-CPD:C00170:*CAS:2457-80-9 2.5.1.16 putrescine + S-adenosyl-L-methioninamine = spermidine + 5'-methylthioadenosine spermidine biosynthesis betanidin quinone 387.325 C18 H15 N2 O8 C(C=C1(C=C(C(O)=O)NC(C1)C(=O)O))=[N+]2([CH](C(=O)O)CC3(C2=CC(=O)C(=O)C=3)) 1.11.1.7 betanidin + H2O2 = betanidin + betanidin quinone + H2O betanidin degradation 1,6-kestotetraose bifurcose 666.583 C24 H42 O21 C(OC1(CO)(C(O)C(O)C(O1)CO))C2(OC(C(O)C(O)2)COC3(CO)(C(O)C(O)C(O3)CO))(OC4(OC(CO)C(O)C(O)C(O)4)) 2.4.1.10 1-kestotriose + sucrose = 1,6-kestotetraose + β-D-glucose fructan biosynthesis sulfur donor (S) H2 S1 S NCI:403664*CAS:7704-34-9 2.8.1.6 dethiobiotin + sulfur donor = 9-mercaptodethiobiotin biotin biosynthesis II sulfur donor (S) H2 S1 S NCI:403664*CAS:7704-34-9 2.8.1.6 dethiobiotin + S-adenosyl-L-methionine + sulfur donor = biotin + 5'-deoxyadenosine + L-methionine biotin biosynthesis I 18:2-16:1-MGDG 1-18:2-2-16:1-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(7Z-hexadecenoyl)-3-O-beta-D-galactosyl-sn-glycerol 753.067 C43 H76 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:1-16:1-MGDG = 18:2-16:1-MGDG glycolipid desaturation 18:2-16:1-MGDG 1-18:2-2-16:1-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(7Z-hexadecenoyl)-3-O-beta-D-galactosyl-sn-glycerol 753.067 C43 H76 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-16:0-MGDG = 18:2-16:1-MGDG glycolipid desaturation 18:2-16:1-MGDG 1-18:2-2-16:1-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(7Z-hexadecenoyl)-3-O-beta-D-galactosyl-sn-glycerol 753.067 C43 H76 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-16:1-MGDG = 18:3-16:1-MGDG glycolipid desaturation 18:2-16:1-MGDG 1-18:2-2-16:1-monogalactosyldiacylglycerol*1-(9Z,12Z-octadecadienoyl)-2-(7Z-hexadecenoyl)-3-O-beta-D-galactosyl-sn-glycerol 753.067 C43 H76 O10 C(OC1(C(O)C(O)C(O)C(O1)CO))C(OC(=O)CCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC 1.14.99.- 18:2-16:1-MGDG = 18:2-16:2-MGDG glycolipid desaturation ent-cassa-12,15-diene-3α-ol ent-cassa-12,15-diene-3alpha-ol*ent-cassadiene-3α-ol*ent-cassadiene-3alpha-ol 288.472 C20 H32 O1 CC1([CH]2(C(CCC(O)1)(C)C3([CH](CC2)C(C)C(=CC3)C=C)))(C) ent-cassa-12,15-diene-3α-ol = ent-cassa-12,15-diene-3α-ol-11-keto phytocassane biosynthesis ent-cassa-12,15-diene-3α-ol ent-cassa-12,15-diene-3alpha-ol*ent-cassadiene-3α-ol*ent-cassadiene-3alpha-ol 288.472 C20 H32 O1 CC1([CH]2(C(CCC(O)1)(C)C3([CH](CC2)C(C)C(=CC3)C=C)))(C) ent-cassa-12,15-diene = ent-cassa-12,15-diene-3α-ol phytocassane biosynthesis 5,10-methenyl-H4PteGlu(n) C8 H10 N6 O1 R1 3.5.4.9 tetrahydrofolate biosynthesis II 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 318.174 C8 H15 O11 P1 C(OP(O)(O)=O)C(O)C(O)C(O)C(O)CC(=O)C(O)=O 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 318.174 C8 H15 O11 P1 C(OP(O)(O)=O)C(O)C(O)C(O)C(O)CC(=O)C(O)=O 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*trans-2-hydroxycinnamate*o-coumarate 164.16 C9 H8 O3 C(O)(=O)C=Cc1(c(O)cccc1) 1.14.13.14 trans-cinnamate + O2 + NADPH = H2O + NADP+ + 2-coumarate coumarin biosynthesis (via 2-coumarate) 2-coumarate 2-Hydroxycinnamate*trans-2-hydroxycinnamate*o-coumarate 164.16 C9 H8 O3 C(O)(=O)C=Cc1(c(O)cccc1) 2.4.1.114 2-coumarate + UDP-D-glucose = trans-β-D-Glucosyl-2-hydroxycinnamate + UDP coumarin biosynthesis (via 2-coumarate) trans-3-hydroxycotinine-glucuronide 368.343 C16 H20 N2 O8 c1(ncc(cc1)[CH]2(C[CH](C(=O)N2C)OC3(C(O)C(O)C(O)C(O3)C(O)=O))) 2.4.1.17 trans-3'-hydroxycotinine + UDP-D-glucuronate = trans-3-hydroxycotinine-glucuronide + UDP nicotine degradation III 6,7,4'-trihydroxyisoflavone 270.241 C15 H10 O5 C2(=C(c1(ccc(O)cc1))C(=O)c3(c(O2)cc(O)c(c3)O)) 4.2.1.- 2,6,7,4'-tetrahydroxyisoflavanone = 6,7,4'-trihydroxyisoflavone + H2O 6,7,4'-trihydroxyisoflavone biosynthesis homoisocitrate (-)-1-hydroxy-1,2,4-butanetricarboxylate*homo-I-cit*1-Hydroxy-1,2,4-butanetricarboxylate*2-hydroxy-3-carboxyadipate*homo-iso-citrate*1-(R)-hydroxy-2-(S)-1,2,4-butanetricarboxylic acid*1-Hydroxybutane-1,2,4-tricarboxylate*(1R,2S)-1-hydroxybutane-1,2,4-tricarboxylate 206.152 C7 H10 O7 C(=O)(O)CCC(C(O)=O)C(O)C(O)=O 4.2.1.36 homoisocitrate = H2O + 3-carboxyhex-2-enedioate lysine biosynthesis IV homoisocitrate (-)-1-hydroxy-1,2,4-butanetricarboxylate*homo-I-cit*1-Hydroxy-1,2,4-butanetricarboxylate*2-hydroxy-3-carboxyadipate*homo-iso-citrate*1-(R)-hydroxy-2-(S)-1,2,4-butanetricarboxylic acid*1-Hydroxybutane-1,2,4-tricarboxylate*(1R,2S)-1-hydroxybutane-1,2,4-tricarboxylate 206.152 C7 H10 O7 C(=O)(O)CCC(C(O)=O)C(O)C(O)=O 1.1.1.87 homoisocitrate + NAD+ = α-ketoadipate + CO2 + NADH + H+ lysine biosynthesis IV isopentenyladenosine-5'-monophosphate iPMP*isopentenyladenosine riboside-5'-monophosphate*iPRMP 415.342 C15 H22 N5 O7 P1 C1(C(O)C(O)C(O1)COP(O)(O)=O)n2(c3(c(nc2)c(ncn3)NCC=C(C)C)) isopentenyladenosine-5'-monophosphate + H2O = isopentenyladenine + D-ribose-5-phosphate trans-zeatin biosynthesis isopentenyladenosine-5'-monophosphate iPMP*isopentenyladenosine riboside-5'-monophosphate*iPRMP 415.342 C15 H22 N5 O7 P1 C1(C(O)C(O)C(O1)COP(O)(O)=O)n2(c3(c(nc2)c(ncn3)NCC=C(C)C)) isopentenyladenosine-5'-diphosphate + H2O = isopentenyladenosine-5'-monophosphate trans-zeatin biosynthesis isopentenyladenosine-5'-monophosphate iPMP*isopentenyladenosine riboside-5'-monophosphate*iPRMP 415.342 C15 H22 N5 O7 P1 C1(C(O)C(O)C(O1)COP(O)(O)=O)n2(c3(c(nc2)c(ncn3)NCC=C(C)C)) isopentenyladenosine-5'-monophosphate + H2O = isopentenyl adenosine trans-zeatin biosynthesis isopentenyladenosine-5'-monophosphate iPMP*isopentenyladenosine riboside-5'-monophosphate*iPRMP 415.342 C15 H22 N5 O7 P1 C1(C(O)C(O)C(O1)COP(O)(O)=O)n2(c3(c(nc2)c(ncn3)NCC=C(C)C)) isopentenyladenosine-5'-monophosphate + NADPH + H2O = trans-zeatin riboside monophosphate + NADP+ trans-zeatin biosynthesis isopentenyladenosine-5'-monophosphate iPMP*isopentenyladenosine riboside-5'-monophosphate*iPRMP 415.342 C15 H22 N5 O7 P1 C1(C(O)C(O)C(O1)COP(O)(O)=O)n2(c3(c(nc2)c(ncn3)NCC=C(C)C)) 2.5.1.27 dimethylallyl-PP + AMP = isopentenyladenosine-5'-monophosphate + diphosphate trans-zeatin biosynthesis 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- 158.113 C5 H6 N2 O4 C1(=O)(CC(C(O)=O)NC(N1)=O) CAS:5988-19-2:*LIGAND-CPD:C00337:*CAS:155-54-4 1.3.3.1 O2 + dihydroorotate = H2O2 + orotate de novo biosynthesis of pyrimidine ribonucleotides 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- 158.113 C5 H6 N2 O4 C1(=O)(CC(C(O)=O)NC(N1)=O) CAS:5988-19-2:*LIGAND-CPD:C00337:*CAS:155-54-4 3.5.2.3 dihydroorotate + H2O = N-carbamoyl-L-aspartate de novo biosynthesis of pyrimidine ribonucleotides 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 428.654 C28 H44 O3 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C(O)=O)C(O)CC4)))) 1.1.1.170 4α-carboxy-5α-cholesta-8,24-dien-3β-ol = 5α-cholesta-8,24-dien-3-one + CO2 cholesterol biosynthesis I 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 428.654 C28 H44 O3 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C(O)=O)C(O)CC4)))) 1.1.1.170 4α-carboxy-5α-cholesta-8,24-dien-3β-ol = 5α-cholesta-8,24-dien-3-one + CO2 cholesterol biosynthesis III (via desmosterol) 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 428.654 C28 H44 O3 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C(O)=O)C(O)CC4)))) 1.14.13.72 4α-formyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis I 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 428.654 C28 H44 O3 CC(C)=CCCC(C)C1(C2(C)(C(CC1)C3(=C(CC2)C4(C)(C(CC3)C(C(O)=O)C(O)CC4)))) 1.14.13.72 4α-formyl-5α-cholesta-8,24-dien-3β-ol + O2 = 4α-carboxy-5α-cholesta-8,24-dien-3β-ol + H2O cholesterol biosynthesis III (via desmosterol) diprenylphlorisovalerophenone deoxyhumulone 346.466 C21 H30 O4 CC(C)=CCc1(c(O)c(CC=C(C)C)c(O)c(c(O)1)C(=O)CC(C)C) 2.5.1.- 4-prenylphlorisovalerophenone + dimethylallyl-PP = diprenylphlorisovalerophenone + diphosphate humulone biosynthesis diprenylphlorisovalerophenone deoxyhumulone 346.466 C21 H30 O4 CC(C)=CCc1(c(O)c(CC=C(C)C)c(O)c(c(O)1)C(=O)CC(C)C) diprenylphlorisovalerophenone + O2 = humulone + H2O humulone biosynthesis caffeate caffeic acid 180.16 C9 H8 O4 C(O)(=O)C=Cc1(cc(O)c(O)cc1) 2.1.1.68 caffeate + S-adenosyl-L-methionine = ferulate + S-adenosyl-L-homocysteine suberin biosynthesis caffeate caffeic acid 180.16 C9 H8 O4 C(O)(=O)C=Cc1(cc(O)c(O)cc1) 2.1.1.68 caffeate + S-adenosyl-L-methionine = ferulate + S-adenosyl-L-homocysteine free phenylpropanoid acid biosynthesis caffeate caffeic acid 180.16 C9 H8 O4 C(O)(=O)C=Cc1(cc(O)c(O)cc1) 6.2.1.12 caffeate + coenzyme A + ATP = caffeoyl-CoA + AMP + diphosphate suberin biosynthesis caffeate caffeic acid 180.16 C9 H8 O4 C(O)(=O)C=Cc1(cc(O)c(O)cc1) 4-coumarate + NADPH + O2 = H2O + caffeate + NADP+ suberin biosynthesis caffeate caffeic acid 180.16 C9 H8 O4 C(O)(=O)C=Cc1(cc(O)c(O)cc1) 4-coumarate + NADPH + O2 = H2O + caffeate + NADP+ free phenylpropanoid acid biosynthesis 1,2,3,5-tetrahydroxybenzene 142.111 C6 H6 O4 C1(O)(C=C(O)C(O)=C(O)C=1) LIGAND-CPD:c03743:*CAS:634-94-6 1.97.1.2 1,2,3,5-tetrahydroxybenzene + pyrogallol = 1,2,3,5-tetrahydroxybenzene + phloroglucinol gallate degradation III (anaerobic) chlorophyllide a chlorophyllide a 614.982 C35 H34 N4 O5 MG1 CCC8(C3(=N7([Mg]59(n2(c1(=C(C(C(=O)OC)C(=O)c1c(C)c2=C3)C4(=N(C(C(C)C4CCC(=O)O)=Cc6(n5c(c(C=C)c(C)6)C=C7C(C)=8))9))))))) chlorophyllide a + O2 + NADPH = 7-hydroxy-chlorophyllide a + H2O + NADP+ chlorophyll cycle chlorophyllide a chlorophyllide a 614.982 C35 H34 N4 O5 MG1 CCC8(C3(=N7([Mg]59(n2(c1(=C(C(C(=O)OC)C(=O)c1c(C)c2=C3)C4(=N(C(C(C)C4CCC(=O)O)=Cc6(n5c(c(C=C)c(C)6)C=C7C(C)=8))9))))))) chlorophyllide a = pheophorbide a + Mg2+ chlorophyll a degradation chlorophyllide a chlorophyllide a 614.982 C35 H34 N4 O5 MG1 CCC8(C3(=N7([Mg]59(n2(c1(=C(C(C(=O)OC)C(=O)c1c(C)c2=C3)C4(=N(C(C(C)C4CCC(=O)O)=Cc6(n5c(c(C=C)c(C)6)C=C7C(C)=8))9))))))) 3.1.1.14 chlorophyll a + H2O = chlorophyllide a + phytol chlorophyll a degradation chlorophyllide a chlorophyllide a 614.982 C35 H34 N4 O5 MG1 CCC8(C3(=N7([Mg]59(n2(c1(=C(C(C(=O)OC)C(=O)c1c(C)c2=C3)C4(=N(C(C(C)C4CCC(=O)O)=Cc6(n5c(c(C=C)c(C)6)C=C7C(C)=8))9))))))) 2.5.1.62 chlorophyllide a + phytyl-PP = chlorophyll a + diphosphate chlorophyll cycle chlorophyllide a chlorophyllide a 614.982 C35 H34 N4 O5 MG1 CCC8(C3(=N7([Mg]59(n2(c1(=C(C(C(=O)OC)C(=O)c1c(C)c2=C3)C4(=N(C(C(C)C4CCC(=O)O)=Cc6(n5c(c(C=C)c(C)6)C=C7C(C)=8))9))))))) 2.5.1.62 chlorophyllide a + phytyl-PP = chlorophyll a + diphosphate chlorophyll a biosynthesis I chlorophyllide a chlorophyllide a 614.982 C35 H34 N4 O5 MG1 CCC8(C3(=N7([Mg]59(n2(c1(=C(C(C(=O)OC)C(=O)c1c(C)c2=C3)C4(=N(C(C(C)C4CCC(=O)O)=Cc6(n5c(c(C=C)c(C)6)C=C7C(C)=8))9))))))) 2.5.1.- chlorophyllide a + geranylgeranyl diphosphate = geranylgeranyl-chlorophyll a + diphosphate chlorophyll a biosynthesis II chlorophyllide a chlorophyllide a 614.982 C35 H34 N4 O5 MG1 CCC8(C3(=N7([Mg]59(n2(c1(=C(C(C(=O)OC)C(=O)c1c(C)c2=C3)C4(=N(C(C(C)C4CCC(=O)O)=Cc6(n5c(c(C=C)c(C)6)C=C7C(C)=8))9))))))) monovinyl protochlorophyllide a + NADPH = NADP+ + chlorophyllide a chlorophyllide a biosynthesis GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 523.183 C10 H16 N5 O14 P3 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 2.7.4.6 GDP + ATP = GTP + ADP purine nucleotides de novo biosynthesis I GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 523.183 C10 H16 N5 O14 P3 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 2.7.1.48 uridine + GTP = UMP + GDP salvage pathways of pyrimidine ribonucleotides GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 523.183 C10 H16 N5 O14 P3 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 2.7.6.5 GTP + ATP = guanosine 3'-diphosphate 5'-triphosphate + AMP ppGpp biosynthesis GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 523.183 C10 H16 N5 O14 P3 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 GTP = dGTP + H2O purine nucleotides de novo biosynthesis I GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 523.183 C10 H16 N5 O14 P3 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 3.5.4.25 H2O + GTP = diphosphate + 2,5-diamino-6-(ribosylamino)-4-(3H)-pyrimidinone 5'-phosphate + formate flavin biosynthesis GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 523.183 C10 H16 N5 O14 P3 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 4.1.1.32 oxaloacetate + GTP = CO2 + phosphoenolpyruvate + GDP asparagine degradation I GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 523.183 C10 H16 N5 O14 P3 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = adenylo-succinate + GDP salvage pathways of purine nucleosides GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 523.183 C10 H16 N5 O14 P3 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = adenylo-succinate + GDP purine nucleotides de novo biosynthesis II GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 523.183 C10 H16 N5 O14 P3 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 6.3.4.4 L-aspartate + inosine-5'-phosphate + GTP = adenylo-succinate + GDP purine nucleotides de novo biosynthesis I GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 523.183 C10 H16 N5 O14 P3 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 2.7.1.- cytidine + GTP = CMP + GDP salvage pathways of pyrimidine ribonucleotides GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 523.183 C10 H16 N5 O14 P3 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 3.5.4.16 GTP + H2O = formate + 7,8-dihydroneopterin 3'-triphosphate tetrahydrofolate biosynthesis I GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 523.183 C10 H16 N5 O14 P3 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 3.5.4.16 GTP + H2O = formate + 7,8-dihydroneopterin 3'-triphosphate tetrahydrofolate biosynthesis II GTP guanylyl imidodiphosphate*guanosine 5'-triphosphate*guanosine-triphosphate 523.183 C10 H16 N5 O14 P3 C(OP(=O)(O)OP(=O)(O)OP(O)(O)=O)C1(OC(C(O)C1O)n2(c3(c(nc2)c(=O)[nH]c(n3)N))) LIGAND-CPD:C00044:*LIGAND-CPD:c00044:*CAS:86-01-1 2.7.7.13 α-D-mannose 1-phosphate + GTP = GDP-D-mannose + diphosphate ascorbate biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA4 + α-ketoglutarate + O2 = GA34 + succinate + CO2 gibberellin inactivation succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA44 + α-ketoglutarate + O2 = GA98 + succinate + CO2 gibberellin inactivation succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.2.1.24 H2O + NAD+ + succinate semialdehyde = NADH + succinate glutamate degradation III succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 3.5.1.- N2-succinylglutamate + H2O = L-glutamate + succinate arginine degradation II succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.3.99.1 succinate = fumarate TCA cycle variation I succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.3.99.1 succinate = fumarate reductive TCA cycle I succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA9 + α-ketoglutarate + O2 = GA4 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA12 + α-ketoglutarate + O2 = GA110 + succinate + CO2 gibberellin inactivation succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA34 + α-ketoglutarate + O2 = GA34-catabolite + succinate + CO2 + H2O gibberellin inactivation succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA36 + O2 + α-ketoglutarate = GA4 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA15 + α-ketoglutarate + O2 = GA24 + succinate + CO2 + H2O gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA19 + O2 + α-ketoglutarate = GA20 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA51 + α-ketoglutarate + O2 = GA51-catabolite + succinate + CO2 + H2O gibberellin inactivation succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.12 GA44 + α-ketoglutarate + O2 = GA19 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.2.1.16 succinate semialdehyde + NADP+ + H2O = NADPH + succinate TCA cycle variation I succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA53 + O2 + α-ketoglutarate = GA44 + CO2 + succinate gibberellin biosynthesis III (early C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA8 + α-ketoglutarate + O2 = GA8-catabolite + succinate + CO2 + H2O gibberellin inactivation succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA37 + α-ketoglutarate + O2 = GA36 + succinate + CO2 + H2O gibberellin biosynthesis II (early C-3 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- leucocyanidin + α-ketoglutarate + O2 = cyanidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA9 + α-ketoglutarate + O2 = GA51 + succinate + CO2 gibberellin inactivation succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA20 + α-ketoglutarate + O2 = GA29 + succinate + CO2 gibberellin inactivation succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 3',4',5'-pentahydroxyflavanone + α-ketoglutarate + O2 = dihydromyricetin + succinate + CO2 leucodelphinidin biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA19 + O2 + α-ketoglutarate = GA17 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA24 + O2 + α-ketoglutarate = GA9 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA53 + α-ketoglutarate + O2 = GA97 + succinate + CO2 gibberellin inactivation succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.9 naringenin + O2 + α-ketoglutarate = CO2 + succinate + dihydrokaempferol flavonoid biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 2.5.1.48 L-cysteine + O-succinyl-L-homoserine = succinate + cystathionine methionine biosynthesis I succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.9 (2S)-pinocembrin + O2 + α-ketoglutarate = (2R,3R)-pinobanksin + CO2 + succinate pinobanksin biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA15 + α-ketoglutarate + O2 = GA37 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 6.2.1.5 succinate + coenzyme A + ATP = succinyl-CoA + ADP reductive TCA cycle I succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 6.2.1.5 succinate + coenzyme A + ATP = succinyl-CoA + ADP TCA cycle succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA44 + α-ketoglutarate + O2 = GA38 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- leucodelphinidin + O2 + α-ketoglutarate = delphinidin + H2O + CO2 + succinate anthocyanin biosynthesis (delphinidin 3-O-glucoside) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA29 + α-ketoglutarate + O2 = GA29-catabolite + succinate + CO2 + H2O gibberellin inactivation succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 3.5.1.18 H2O = L,L-diaminopimelate + succinate lysine biosynthesis I succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA12 + α-ketoglutarate + O2 = GA14 + succinate + CO2 gibberellin biosynthesis II (early C-3 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.23 dihydrokaempferol + α-ketoglutarate + O2 = kaempferol + succinate + CO2 + H2O flavonol biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.13 GA1 + α-ketoglutarate + O2 = GA8 + succinate + CO2 gibberellin inactivation succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.23 dihydroquercetin + α-ketoglutarate + O2 = quercetin + succinate + CO2 + H2O flavonol biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA12 + O2 + α-ketoglutarate = GA15 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA24 + O2 + α-ketoglutarate = GA25 + CO2 + succinate gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.15 GA20 + α-ketoglutarate + O2 = GA1 + succinate + CO2 gibberellin biosynthesis III (early C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA14 + O2 + α-ketoglutarate = GA37 + CO2 + succinate gibberellin biosynthesis II (early C-3 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA24 + α-ketoglutarate + O2 = GA36 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.9 eriodictyol + O2 + α-ketoglutarate = dihydroquercetin + CO2 + succinate leucopelargonidin and leucocyanidin biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.9 eriodictyol + O2 + α-ketoglutarate = dihydroquercetin + CO2 + succinate leucodelphinidin biosynthesis succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.3.5.- fumarate + menaquinol + H+ = succinate + menaquinone-8 mixed acid fermentation succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.3.5.- fumarate + menaquinol + H+ = succinate + menaquinone-8 respiration (anaerobic) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- GA25 + α-ketoglutarate + O2 = GA13 + succinate + CO2 gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 4.1.3.1 TCA cycle variation I succinate succinic acid*suc*succ*butanedioic acid*ethylenesuccinic acid 118.089 C4 H6 O4 C(O)(=O)CCC(=O)O LIGAND-CPD:C00042:*CAS:110-15-6 1.14.11.- leucopelargonidin + α-ketoglutarate + O2 = pelargonidin + succinate + CO2 + H2O anthocyanin biosynthesis (pelargonidin 3-O-glucoside, cyanidin 3-O-glucoside) pyrogallol 1,2,3-trihydroxybenzene*1,2,3-benzenetriol*C.I. Oxidation Base 32*C.I. 76515*fouramine base ap*Fouramine Brown AP*fourrine 85*fourrine PG*Piral*Pyro*pyrogallic acid 126.112 C6 H6 O3 c1(c(O)c(O)c(O)cc1) LIGAND-CPD:c01108:*UM-BBD-CPD:c0025: 1.97.1.2 1,2,3,5-tetrahydroxybenzene + pyrogallol = 1,2,3,5-tetrahydroxybenzene + phloroglucinol gallate degradation III (anaerobic) pyrogallol 1,2,3-trihydroxybenzene*1,2,3-benzenetriol*C.I. Oxidation Base 32*C.I. 76515*fouramine base ap*Fouramine Brown AP*fourrine 85*fourrine PG*Piral*Pyro*pyrogallic acid 126.112 C6 H6 O3 c1(c(O)c(O)c(O)cc1) LIGAND-CPD:c01108:*UM-BBD-CPD:c0025: 4.1.1.59 gallate = CO2 + pyrogallol gallate degradation III (anaerobic) nicotinate riboside 256.235 C11 H14 N1 O6 c2([n+]([CH]1(O[CH](CO)[CH](O)[CH]1O))cccc2C(=O)O) 2.7.1.- nicotinate riboside + ATP = nicotinate nucleotide + ADP pyridine nucleotide cycling (plants) nicotinate riboside 256.235 C11 H14 N1 O6 c2([n+]([CH]1(O[CH](CO)[CH](O)[CH]1O))cccc2C(=O)O) 2.4.2.1 nicotinate + D-ribulose-1-phosphate = nicotinate riboside pyridine nucleotide cycling (plants) ethanol absolute alcohol*alcohol*EtOH*eth*ethyl alcohol*grain alcohol 46.069 C2 H6 O1 C(C)[OH] LIGAND-CPD:C00469:*CAS:64-17-5 1.11.1.6 ethanol + H2O2 = H2O + acetaldehyde oxidative ethanol degradation III ethanol absolute alcohol*alcohol*EtOH*eth*ethyl alcohol*grain alcohol 46.069 C2 H6 O1 C(C)[OH] LIGAND-CPD:C00469:*CAS:64-17-5 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ mixed acid fermentation ethanol absolute alcohol*alcohol*EtOH*eth*ethyl alcohol*grain alcohol 46.069 C2 H6 O1 C(C)[OH] LIGAND-CPD:C00469:*CAS:64-17-5 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ sucrose degradation to ethanol and lactate (anaerobic) ethanol absolute alcohol*alcohol*EtOH*eth*ethyl alcohol*grain alcohol 46.069 C2 H6 O1 C(C)[OH] LIGAND-CPD:C00469:*CAS:64-17-5 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ ethanol fermentation to acetate ethanol absolute alcohol*alcohol*EtOH*eth*ethyl alcohol*grain alcohol 46.069 C2 H6 O1 C(C)[OH] LIGAND-CPD:C00469:*CAS:64-17-5 1.1.1.1 acetaldehyde + NADH = ethanol + NAD+ oxidative ethanol degradation I phytol 296.535 C20 H40 O1 CC(=CCO)CCCC(C)CCCC(C)CCCC(C)C 3.1.1.14 chlorophyll a + H2O = 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 577.334 C15 H25 N5 O15 P2 C(N)(=O)c1(c(n(cn1)[CH]2(O[CH]([CH](O)[CH](O)2)COP(O)(=O)O))N=CNCC(=O)[CH](O)[CH](O)COP(O)(O)=O) PUBCHEM:193735:*LIGAND-CPD:C04916: 5.3.1.16 phosphoribosylformiminoAICAR-phosphate = phosphoribulosylformimino-AICAR-P histidine biosynthesis I 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 577.334 C15 H25 N5 O15 P2 C(N)(=O)c1(c(n(cn1)[CH]2(O[CH]([CH](O)[CH](O)2)COP(O)(=O)O))N=CNCC(=O)[CH](O)[CH](O)COP(O)(O)=O) PUBCHEM:193735:*LIGAND-CPD:C04916: 2.4.2.- phosphoribulosylformimino-AICAR-P + L-glutamine = L-glutamate + D-erythro-imidazole-glycerol-phosphate + AICAR histidine biosynthesis I 3',4',5'-pentahydroxyflavanone dihydrotricetin*5,7,3',4',5'-pentahydroxyflavanone 304.256 C15 H12 O7 c3(c2(OC(c1(cc(O)c(O)c(O)c1))CC(=O)c2c(O)cc(O)3)) 3',4',5'-pentahydroxyflavanone + α-ketoglutarate + O2 = dihydromyricetin + succinate + CO2 leucodelphinidin biosynthesis 3',4',5'-pentahydroxyflavanone dihydrotricetin*5,7,3',4',5'-pentahydroxyflavanone 304.256 C15 H12 O7 c3(c2(OC(c1(cc(O)c(O)c(O)c1))CC(=O)c2c(O)cc(O)3)) 1.14.13.- eriodictyol + NADPH + O2 = 3',4',5'-pentahydroxyflavanone + NADP+ + H2O leucodelphinidin biosynthesis