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http://identifiers.org/smpdb/SMP01911 SMPDB P17109 UniProt C02730 KEGG Compound 937 ChemSpider HMDB00250 HMDB 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase 2-succinylbenzoate--CoA ligase Hydrogenase-1 small chain SMILES O Pyrophosphate C10H14N5O7P Adenosine monophosphate 347.06308 50 ChemSpider 1.0 58838673 PubChem-compound isochorismate 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate CHEBI:18325 ChEBI CHEBI:16027 ChEBI ATP BioCyc 2-succinylbenzoate Hydrogenase-1 large chain 1,4-dihydroxy-2-naphthoyl-CoA 1,4-dihydroxy-2-naphthoate 5.4.4.2 false 5.4.4.2 Chorismate → isochorismate LEFT_TO_RIGHT 1.0 6816 PubChem-compound 1.0 51 PubChem-compound Pyruvic acid 559142 ChemSpider P29208 UniProt 4.0 45479636 PubChem-compound C3H4O3 Pyruvic acid 88.016045 HMDB00939 HMDB 4.0 C15H23N6O5S S-Adenosylmethionine 399.14505 C10H8O6 isochorismate 224.03319 C14H16O9 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate 328.07944 C11H10O6 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 238.04883 C11H8O5 2-succinylbenzoate 220.03827 C32H38N7O19P3S 1,4-dihydroxy-2-naphthoyl-CoA 949.1178 5742 ChemSpider C32H38N7O19P3S 1,4-dihydroxy-2-naphthoate 949.1178 1038 PubChem-compound 4444251 ChemSpider SMILES O[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O P0ACD8 UniProt ALPHA-GLUCOSE-16-BISPHOSPHATE BioCyc HMDB59597 HMDB 274 ChemSpider Adenosine monophosphate C5H6O5 Oxoglutaric acid 146.02153 5376004 PubChem-compound CHEBI:61873 ChEBI HMDB00243 HMDB 5858 ChemSpider ADENOSYL-HOMO-CYS BioCyc 1,4-dihydroxy-2-naphthoyl-CoA thioesterase 2.0 Isochorismate synthase entC P0AEJ2 UniProt C04146 KEGG Compound CHEBI:17333 ChEBI 1010 ChemSpider SMILES CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCS ReactionCatalysis5834 ACTIVATION 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase 1.12.99.6 false 1.12.99.6 2-Demethylmenaquinone 8 + Hydrogen + 2 Hydrogen Ion → 2-Demethylmenaquinone 8 + 2 Hydrogen Ion LEFT_TO_RIGHT PPI BioCyc CHEBI:29780 ChEBI SMILES [H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=C(O)C2=CC=CC=C2C(O)=C1C)=C(\C)CCC=C(C)C 1.0 HMDB01423 HMDB Hydrogen Ion SMILES C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12 979-92-0 CAS CHEBI:58897 ChEBI o-succinylbenzoate synthase Adenosine triphosphate Ubiquinone/menaquinone biosynthesis methyltransferase ubiE C14H20N6O5S S-Adenosylhomocysteine 384.12158 P0A887 UniProt SMILES OC(=O)CCC(=O)C(O)=O HMDB00208 HMDB CHEBI:30915 ChEBI 124-38-9 CAS ReactionCatalysis5201 ACTIVATION 1.0 6.0 SMILES [H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])COP([O-])(=O)OP([O-])([O-])=O)=C(\C)CCC=C(C)C CHEBI:11173 ChEBI CHEBI:15414 ChEBI C05817 KEGG Compound C00001 KEGG Compound CHEBI:18361 ChEBI 126279 PubChem-compound 1031 ChemSpider C00002 KEGG Compound Naphthoate synthase Hydrogen Menaquinol 8 C51H74O2 Menaquinol 8 718.5689 45479277 PubChem-compound H2 Hydrogen 2.01565 C00019 KEGG Compound P0AAM1 UniProt P32166 UniProt 1.0 C00011 KEGG Compound SMILES O=C=O S-ADENOSYLMETHIONINE BioCyc C00010 KEGG Compound C00251 KEGG Compound CHEBI:16275 ChEBI C00013 KEGG Compound O7P2 Pyrophosphate 173.91193 CHEBI:50271 ChEBI 5957 PubChem-compound Probable Ni/Fe-hydrogenase 1 B-type cytochrome subunit H Hydrogen Ion 1.007825 SMILES [H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=C(O)C2=CC=CC=C2C(O)=C1)=C(\C)CCC=C(C)C 388301 ChemSpider S-Adenosylhomocysteine SMILES [H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=CC(=O)C2=CC=CC=C2C1=O)=C(\C)CCC=C(C)C HMDB01094 HMDB C00022 KEGG Compound 56-65-5 CAS C00021 KEGG Compound C00020 KEGG Compound C03657 KEGG Compound C00026 KEGG Compound CHEBI:58689 ChEBI 1,4-dihydroxy-2-naphthoate octaprenyltransferase Octaprenyl diphosphate 1.0 SMILES [H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)C1=CC=CC=C1C(=O)CCC(O)=O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O C40H68O7P2 Octaprenyl diphosphate 722.44403 CHEBI:15509 ChEBI SMILES [H][C@]1(O)C(=CC=C[C@]1([H])OC(=C)C([O-])=O)C([O-])=O 1.0 1.0 SMILES [O-]C(=O)CCC(=O)C1=CC=CC=C1C([O-])=O SMILES [H][C@@]1(O)C=CC=C(C(=O)CCC([O-])=O)[C@@]1([H])C([O-])=O SMILES [H][C@@]1(O)[C@@]([H])(OC(=C)C(O)=O)C=C[C@]([H])(C(=O)CCC(O)=O)[C@@]1([H])C(O)=O SMILES [H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)C1=C([O-])C2=CC=CC=C2C([O-])=C1)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O SMILES [H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)C1=C([O-])C2=CC=CC=C2C([O-])=C1)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O HMDB01185 HMDB CHEBI:18276 ChEBI 328-50-7 CAS 4.2.99.20 false 4.2.99.20 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate → (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acid LEFT_TO_RIGHT CHEBI:1146900 ChEBI 4.2.1.113 false 4.2.1.113 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate → 2-succinylbenzoate + Water LEFT_TO_RIGHT Water AMP BioCyc C00282 KEGG Compound Menaquinol biosythesis P37355 UniProt P37353 UniProt SMILES [O-]P([O-])(=O)OP([O-])([O-])=O 1.0 2.2.1.9 false 2.2.1.9 Hydrogen Ion + Oxoglutaric acid + isochorismate → 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide LEFT_TO_RIGHT 14000-31-8 CAS CO-A BioCyc C50H72O2 2-Demethylmenaquinol 8 704.5532 C50H70O2 2-Demethylmenaquinone 8 702.5376 C10H10O6 Chorismate 226.04774 HMDB12199 HMDB Coenzyme A C21H36N7O16P3S Coenzyme A 767.11523 1.0 762 ChemSpider SMILES CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O HMDB00538 HMDB 2-Succinylbenzoyl-CoA 11542 ChemSpider C32H44N7O20P3S 2-Succinylbenzoyl-CoA 971.1575 PW001897 PathWhiz CHEBI:15422 ChEBI 6557 ChemSpider ReactionCatalysis2391 ACTIVATION 1.0 1.0 7732-18-5 CAS Naphthoate synthase 1,4-dihydroxy-2-naphthoyl-CoA thioesterase Chorismate 61-19-8 CAS Reaction5237 false 1,4-dihydroxy-2-naphthoate + Hydrogen Ion + Octaprenyl diphosphate → 2-Demethylmenaquinol 8 + Carbon dioxide + Pyrophosphate LEFT_TO_RIGHT 617-12-9 CAS SMILES NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1 1.0 127-17-3 CAS 1.0 Probable Ni/Fe-hydrogenase 1 B-type cytochrome subunit C16519 KEGG Compound P69739 UniProt 3.1.2.28 false 3.1.2.28 1,4-dihydroxy-2-naphthoyl-CoA + Water → 1,4-dihydroxy-2-naphthoate + Coenzyme A + Hydrogen Ion LEFT_TO_RIGHT C15547 KEGG Compound 2.5.1.74 false 2.5.1.74 1,4-dihydroxy-2-naphthoate + Farnesylfarnesylgeranyl-PP + Hydrogen Ion → 2-Demethylmenaquinol 8 + Carbon dioxide + Pyrophosphate LEFT_TO_RIGHT hydrogenase C10H16N5O13P3 Adenosine triphosphate 506.99576 1.0 CHEBI:16526 ChEBI 1.0 1.0 SMILES CC(=O)C(O)=O 4.1.3.36 false 4.1.3.36 2-Succinylbenzoyl-CoA + Hydrogen Ion → 1,4-dihydroxy-2-naphthoyl-CoA + Water LEFT_TO_RIGHT 1.0 5280651 PubChem-compound 1.0 HMDB01967 HMDB 6.2.1.26 false 6.2.1.26 2-succinylbenzoate + Adenosine triphosphate + Coenzyme A → 2-Succinylbenzoyl-CoA + Adenosine monophosphate + Pyrophosphate LEFT_TO_RIGHT 51090848 PubChem-compound 962 PubChem-compound CPD-9517 BioCyc 31983 ChemSpider 1333-74-0 CAS 2-KETOGLUTARATE BioCyc CO2 Carbon dioxide 43.98983 1,4-dihydroxy-2-naphthoate octaprenyltransferase HMDB02111 HMDB C00080 KEGG Compound Hydrogenase-1 large chain Oxoglutaric acid Farnesylfarnesylgeranyl-PP P0ABU0 UniProt CHEBI:32816 ChEBI 2-succinylbenzoate--CoA ligase Hydrogenase-1 small chain 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase CHEBI:48455 ChEBI CHEBI:15377 ChEBI CHEBI:15378 ChEBI SMILES [H+] ReactionCatalysis5175 ACTIVATION PYRUVATE BioCyc SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O C00885 KEGG Compound S-Adenosylmethionine 1.0 280 PubChem-compound ReactionCatalysis5178 ACTIVATION 2.1.1.163 false 2.1.1.163 2-Demethylmenaquinol 8 + S-Adenosylmethionine → Hydrogen Ion + Menaquinol 8 + S-Adenosylhomocysteine LEFT_TO_RIGHT ReactionCatalysis5177 ACTIVATION ReactionCatalysis5182 ACTIVATION 644102 PubChem-compound 2-Demethylmenaquinol 8 6083 PubChem-compound SMILES N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12)C(O)=O HMDB01362 HMDB 2-Demethylmenaquinone 8 25246222 PubChem-compound 1.0 Isochorismate synthase entC H2O Water 18.010565 C40H65O7P2 Farnesylfarnesylgeranyl-PP 719.42053 ReactionCatalysis5188 ACTIVATION 29908-03-0 CAS 2.0 1060 PubChem-compound HMDB00045 HMDB P77781 UniProt ReactionCatalysis5192 ACTIVATION 1.0 ReactionCatalysis5196 ACTIVATION Carbon dioxide CHEBI:16680 ChEBI 12039 PubChem-compound 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase 24762165 PubChem-compound o-succinylbenzoate synthase Ubiquinone/menaquinone biosynthesis methyltransferase ubiE 1.0 85-61-0 CAS ReactionCatalysis5198 ACTIVATION OCTAPRENYL-DIPHOSPHATE BioCyc 1,4-dihydroxy-2-naphthoyl-CoA synthase 1,4-dihydroxy-2-naphthoyl-CoA thioesterase SMILES [H][H] 1.0 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase o-succinylbenzoate-CoA ligase CHEBI:61684 ChEBI Isochorismate synthase entC 2-succinyl-5- enolpyruvyl- 6-hydroxy-3- cyclohexene- 1-carboxylate synthase 2-succinyl-6- hydroxy-2,4- cyclohexadiene- 1-carboxylate synthase o- succinylbenzoate synthase 2- succinylbenzoate- -CoA ligase Naphthoate synthase 1,4- dihydroxy-2- naphthoyl-CoA thioesterase 1,4- dihydroxy-2- naphthoate octaprenyltransferase 1,4- dihydroxy-2- naphthoate octaprenyltransferase Ubiquinone/menaquinone biosynthesis methyltransferase ubiE Hydrogenase-1 small chain Hydrogenase-1 large chain Probable Ni/Fe- hydrogenase 1 B-type cytochrome subunit Chorismate isochorismate Oxoglutaric acid H + CO 2 2-succinyl-5- enolpyruvyl- 6-hydroxy-3- cyclohexene- 1-carboxylate (1R,6R)-6- hydroxy-2- succinylcyclohexa- 2,4-diene-1- carboxylate Pyruvic acid 2- succinylbenzoate H 2 O CoA ATP 2- Succinylbenzoyl- CoA PP i AMP H + H 2 O 1,4- dihydroxy-2- naphthoyl-CoA H 2 O CoA H + 1,4- dihydroxy-2- naphthoate H + Farnesylfarnesylgeranyl- PP CO 2 PP i 2- Demethylmenaquinol 8 Octaprenyl diphosphate H + CO 2 PP i 2- Demethylmenaquinol 8 S- Adenosylmethionine H + S- Adenosylhomocysteine Menaquinol 8 Hydrogen H + 2- Demethylmenaquinone 8 2- Demethylmenaquinone 8 H +
http://identifiers.org/smpdb/SMP01911 SMPDB P17109 UniProt C02730 KEGG Compound 937 ChemSpider HMDB00250 HMDB 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase 2-succinylbenzoate--CoA ligase Hydrogenase-1 small chain SMILES O Pyrophosphate C10H14N5O7P Adenosine monophosphate 347.06308 50 ChemSpider 1.0 58838673 PubChem-compound isochorismate 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate CHEBI:18325 ChEBI CHEBI:16027 ChEBI ATP BioCyc 2-succinylbenzoate Hydrogenase-1 large chain 1,4-dihydroxy-2-naphthoyl-CoA 1,4-dihydroxy-2-naphthoate 5.4.4.2 false 5.4.4.2 Chorismate → isochorismate LEFT_TO_RIGHT 1.0 6816 PubChem-compound 1.0 51 PubChem-compound Pyruvic acid 559142 ChemSpider P29208 UniProt 4.0 45479636 PubChem-compound C3H4O3 Pyruvic acid 88.016045 HMDB00939 HMDB 4.0 C15H23N6O5S S-Adenosylmethionine 399.14505 C10H8O6 isochorismate 224.03319 C14H16O9 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate 328.07944 C11H10O6 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 238.04883 C11H8O5 2-succinylbenzoate 220.03827 C32H38N7O19P3S 1,4-dihydroxy-2-naphthoyl-CoA 949.1178 5742 ChemSpider C32H38N7O19P3S 1,4-dihydroxy-2-naphthoate 949.1178 1038 PubChem-compound 4444251 ChemSpider SMILES O[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O P0ACD8 UniProt ALPHA-GLUCOSE-16-BISPHOSPHATE BioCyc HMDB59597 HMDB 274 ChemSpider Adenosine monophosphate C5H6O5 Oxoglutaric acid 146.02153 5376004 PubChem-compound CHEBI:61873 ChEBI HMDB00243 HMDB 5858 ChemSpider ADENOSYL-HOMO-CYS BioCyc 1,4-dihydroxy-2-naphthoyl-CoA thioesterase 2.0 Isochorismate synthase entC P0AEJ2 UniProt C04146 KEGG Compound CHEBI:17333 ChEBI 1010 ChemSpider SMILES CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCS ReactionCatalysis5834 ACTIVATION 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase 1.12.99.6 false 1.12.99.6 2-Demethylmenaquinone 8 + Hydrogen + 2 Hydrogen Ion → 2-Demethylmenaquinone 8 + 2 Hydrogen Ion LEFT_TO_RIGHT PPI BioCyc CHEBI:29780 ChEBI SMILES [H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=C(O)C2=CC=CC=C2C(O)=C1C)=C(\C)CCC=C(C)C 1.0 HMDB01423 HMDB Hydrogen Ion SMILES C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12 979-92-0 CAS CHEBI:58897 ChEBI o-succinylbenzoate synthase Adenosine triphosphate Ubiquinone/menaquinone biosynthesis methyltransferase ubiE C14H20N6O5S S-Adenosylhomocysteine 384.12158 P0A887 UniProt SMILES OC(=O)CCC(=O)C(O)=O HMDB00208 HMDB CHEBI:30915 ChEBI 124-38-9 CAS ReactionCatalysis5201 ACTIVATION 1.0 6.0 SMILES [H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])COP([O-])(=O)OP([O-])([O-])=O)=C(\C)CCC=C(C)C CHEBI:11173 ChEBI CHEBI:15414 ChEBI C05817 KEGG Compound C00001 KEGG Compound CHEBI:18361 ChEBI 126279 PubChem-compound 1031 ChemSpider C00002 KEGG Compound Naphthoate synthase Hydrogen Menaquinol 8 C51H74O2 Menaquinol 8 718.5689 45479277 PubChem-compound H2 Hydrogen 2.01565 C00019 KEGG Compound P0AAM1 UniProt P32166 UniProt 1.0 C00011 KEGG Compound SMILES O=C=O S-ADENOSYLMETHIONINE BioCyc C00010 KEGG Compound C00251 KEGG Compound CHEBI:16275 ChEBI C00013 KEGG Compound O7P2 Pyrophosphate 173.91193 CHEBI:50271 ChEBI 5957 PubChem-compound Probable Ni/Fe-hydrogenase 1 B-type cytochrome subunit H Hydrogen Ion 1.007825 SMILES [H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=C(O)C2=CC=CC=C2C(O)=C1)=C(\C)CCC=C(C)C 388301 ChemSpider S-Adenosylhomocysteine SMILES [H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=CC(=O)C2=CC=CC=C2C1=O)=C(\C)CCC=C(C)C HMDB01094 HMDB C00022 KEGG Compound 56-65-5 CAS C00021 KEGG Compound C00020 KEGG Compound C03657 KEGG Compound C00026 KEGG Compound CHEBI:58689 ChEBI 1,4-dihydroxy-2-naphthoate octaprenyltransferase Octaprenyl diphosphate 1.0 SMILES [H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)C1=CC=CC=C1C(=O)CCC(O)=O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O C40H68O7P2 Octaprenyl diphosphate 722.44403 CHEBI:15509 ChEBI SMILES [H][C@]1(O)C(=CC=C[C@]1([H])OC(=C)C([O-])=O)C([O-])=O 1.0 1.0 SMILES [O-]C(=O)CCC(=O)C1=CC=CC=C1C([O-])=O SMILES [H][C@@]1(O)C=CC=C(C(=O)CCC([O-])=O)[C@@]1([H])C([O-])=O SMILES [H][C@@]1(O)[C@@]([H])(OC(=C)C(O)=O)C=C[C@]([H])(C(=O)CCC(O)=O)[C@@]1([H])C(O)=O SMILES [H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)C1=C([O-])C2=CC=CC=C2C([O-])=C1)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O SMILES [H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)C1=C([O-])C2=CC=CC=C2C([O-])=C1)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O HMDB01185 HMDB CHEBI:18276 ChEBI 328-50-7 CAS 4.2.99.20 false 4.2.99.20 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate → (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acid LEFT_TO_RIGHT CHEBI:1146900 ChEBI 4.2.1.113 false 4.2.1.113 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate → 2-succinylbenzoate + Water LEFT_TO_RIGHT Water AMP BioCyc C00282 KEGG Compound Menaquinol biosythesis P37355 UniProt P37353 UniProt SMILES [O-]P([O-])(=O)OP([O-])([O-])=O 1.0 2.2.1.9 false 2.2.1.9 Hydrogen Ion + Oxoglutaric acid + isochorismate → 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide LEFT_TO_RIGHT 14000-31-8 CAS CO-A BioCyc C50H72O2 2-Demethylmenaquinol 8 704.5532 C50H70O2 2-Demethylmenaquinone 8 702.5376 C10H10O6 Chorismate 226.04774 HMDB12199 HMDB Coenzyme A C21H36N7O16P3S Coenzyme A 767.11523 1.0 762 ChemSpider SMILES CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O HMDB00538 HMDB 2-Succinylbenzoyl-CoA 11542 ChemSpider C32H44N7O20P3S 2-Succinylbenzoyl-CoA 971.1575 PW001897 PathWhiz CHEBI:15422 ChEBI 6557 ChemSpider ReactionCatalysis2391 ACTIVATION 1.0 1.0 7732-18-5 CAS Naphthoate synthase 1,4-dihydroxy-2-naphthoyl-CoA thioesterase Chorismate 61-19-8 CAS Reaction5237 false 1,4-dihydroxy-2-naphthoate + Hydrogen Ion + Octaprenyl diphosphate → 2-Demethylmenaquinol 8 + Carbon dioxide + Pyrophosphate LEFT_TO_RIGHT 617-12-9 CAS SMILES NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1 1.0 127-17-3 CAS 1.0 Probable Ni/Fe-hydrogenase 1 B-type cytochrome subunit C16519 KEGG Compound P69739 UniProt 3.1.2.28 false 3.1.2.28 1,4-dihydroxy-2-naphthoyl-CoA + Water → 1,4-dihydroxy-2-naphthoate + Coenzyme A + Hydrogen Ion LEFT_TO_RIGHT C15547 KEGG Compound 2.5.1.74 false 2.5.1.74 1,4-dihydroxy-2-naphthoate + Farnesylfarnesylgeranyl-PP + Hydrogen Ion → 2-Demethylmenaquinol 8 + Carbon dioxide + Pyrophosphate LEFT_TO_RIGHT hydrogenase C10H16N5O13P3 Adenosine triphosphate 506.99576 1.0 CHEBI:16526 ChEBI 1.0 1.0 SMILES CC(=O)C(O)=O 4.1.3.36 false 4.1.3.36 2-Succinylbenzoyl-CoA + Hydrogen Ion → 1,4-dihydroxy-2-naphthoyl-CoA + Water LEFT_TO_RIGHT 1.0 5280651 PubChem-compound 1.0 HMDB01967 HMDB 6.2.1.26 false 6.2.1.26 2-succinylbenzoate + Adenosine triphosphate + Coenzyme A → 2-Succinylbenzoyl-CoA + Adenosine monophosphate + Pyrophosphate LEFT_TO_RIGHT 51090848 PubChem-compound 962 PubChem-compound CPD-9517 BioCyc 31983 ChemSpider 1333-74-0 CAS 2-KETOGLUTARATE BioCyc CO2 Carbon dioxide 43.98983 1,4-dihydroxy-2-naphthoate octaprenyltransferase HMDB02111 HMDB C00080 KEGG Compound Hydrogenase-1 large chain Oxoglutaric acid Farnesylfarnesylgeranyl-PP P0ABU0 UniProt CHEBI:32816 ChEBI 2-succinylbenzoate--CoA ligase Hydrogenase-1 small chain 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase CHEBI:48455 ChEBI CHEBI:15377 ChEBI CHEBI:15378 ChEBI SMILES [H+] ReactionCatalysis5175 ACTIVATION PYRUVATE BioCyc SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O C00885 KEGG Compound S-Adenosylmethionine 1.0 280 PubChem-compound ReactionCatalysis5178 ACTIVATION 2.1.1.163 false 2.1.1.163 2-Demethylmenaquinol 8 + S-Adenosylmethionine → Hydrogen Ion + Menaquinol 8 + S-Adenosylhomocysteine LEFT_TO_RIGHT ReactionCatalysis5177 ACTIVATION ReactionCatalysis5182 ACTIVATION 644102 PubChem-compound 2-Demethylmenaquinol 8 6083 PubChem-compound SMILES N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12)C(O)=O HMDB01362 HMDB 2-Demethylmenaquinone 8 25246222 PubChem-compound 1.0 Isochorismate synthase entC H2O Water 18.010565 C40H65O7P2 Farnesylfarnesylgeranyl-PP 719.42053 ReactionCatalysis5188 ACTIVATION 29908-03-0 CAS 2.0 1060 PubChem-compound HMDB00045 HMDB P77781 UniProt ReactionCatalysis5192 ACTIVATION 1.0 ReactionCatalysis5196 ACTIVATION Carbon dioxide CHEBI:16680 ChEBI 12039 PubChem-compound 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase 24762165 PubChem-compound o-succinylbenzoate synthase Ubiquinone/menaquinone biosynthesis methyltransferase ubiE 1.0 85-61-0 CAS ReactionCatalysis5198 ACTIVATION OCTAPRENYL-DIPHOSPHATE BioCyc 1,4-dihydroxy-2-naphthoyl-CoA synthase 1,4-dihydroxy-2-naphthoyl-CoA thioesterase SMILES [H][H] 1.0 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase o-succinylbenzoate-CoA ligase CHEBI:61684 ChEBI entC menD menH menC menE menB menI menA menA ubiE hyaA hyaB hyaC Chorismate isochorismate Oxoglutaric acid Hydrogen Ion Carbon dioxide 2-succinyl-5- enolpyruvyl- 6-hydroxy-3- cyclohexene- 1-carboxylate (1R,6R)-6- hydroxy-2- succinylcyclohexa- 2,4-diene-1- carboxylate Pyruvic acid 2- succinylbenzoate Water Coenzyme A Adenosine triphosphate 2- Succinylbenzoyl- CoA Pyrophosphate Adenosine monophosphate Hydrogen Ion Water 1,4- dihydroxy-2- naphthoyl-CoA Water Coenzyme A Hydrogen Ion 1,4- dihydroxy-2- naphthoate Hydrogen Ion Farnesylfarnesylgeranyl- PP Carbon dioxide Pyrophosphate 2- Demethylmenaquinol 8 Octaprenyl diphosphate Hydrogen Ion Carbon dioxide Pyrophosphate 2- Demethylmenaquinol 8 S- Adenosylmethionine Hydrogen Ion S- Adenosylhomocysteine Menaquinol 8 Hydrogen