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17215925 ChemSpider 937 ChemSpider NADH 439153 PubChem-compound SMILES O 1.0 cis-Vaccenic acid Acyl-CoA thioesterase I NAD Palmitoleic acid cis-Vaccenic acid Palmitoleic acid trans-Δ3-cis-Δ7-tetradecenoyl-[acp] trans-Δ3-cis-Δ9-hexadecenoyl-[acp] (R)-3-hydroxy-cis-vaccenoyl-[acp] 1.0 3-oxoacyl-[acyl-carrier-protein] synthase 2 CHEBI:15846 ChEBI 1.0 53-59-8 CAS 1.0 HMDB0240219 HMDB 1038 PubChem-compound cis-Δ3-decenoyl-ACP 3-oxoacyl-[acyl-carrier-protein] synthase 1 CHEBI:16474 ChEBI Palmitoleic acid GO:0005829 GENE ONTOLOGY 1.0 274 ChemSpider CHEBI:16908 ChEBI NADPH 1.0 trans-Δ3-cis-Δ5-dodecenoyl-[acp] 1010 ChemSpider Enoyl-[acyl-carrier-protein] reductase [NADH] 3-oxoacyl-[acyl-carrier-protein] reductase NADP C21H30N7O17P3 NADPH 745.0911 C21H29N7O17P3 NADP 744.08325 1.0 1.0 NADPH BioCyc 1.0 Hydrogen Ion a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] trans-Δ3-cis-Δ9-hexadecenoyl-[acp] trans-Δ3-cis-Δ7-tetradecenoyl-[acp] ReactionCatalysis2729 ACTIVATION CHEBI:28716 ChEBI 3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase ReactionCatalysis2728 ACTIVATION Cytosol 58-68-4 CAS 373-49-9 CAS ReactionCatalysis2731 ACTIVATION ReactionCatalysis2734 ACTIVATION ReactionCatalysis2733 ACTIVATION ReactionCatalysis2735 ACTIVATION HMDB0000217 HMDB ReactionCatalysis2738 ACTIVATION ReactionCatalysis2737 ACTIVATION 124-38-9 CAS (R)-3-hydroxy-cis-vaccenoyl-[acp] ReactionCatalysis2730 ACTIVATION 2.0 Fatty Acid Biosynthesis SubPathway a holo-[acyl-carrier protein] C00006 KEGG Compound a malonyl-[acp] 1.0 a 3R-hydroxy cis Δ7-tetradecenoyl-[acp] CHEBI:18009 ChEBI C00001 KEGG Compound ReactionCatalysis2739 ACTIVATION 1.0 C00005 KEGG Compound 2.0 C00004 KEGG Compound C00003 KEGG Compound SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O ReactionCatalysis2743 ACTIVATION HMDB0000221 HMDB P0ADA1 UniProt ReactionCatalysis2742 ACTIVATION ReactionCatalysis2745 ACTIVATION SMILES NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O ReactionCatalysis2741 ACTIVATION ReactionCatalysis2740 ACTIVATION 1.0 53-57-6 CAS C21H28N7O14P2 NAD 664.11694 C00011 KEGG Compound SMILES O=C=O 6.0 3-oxoacyl-[acyl-carrier-protein] synthase 2 HMDB0000902 HMDB C16H30O2 Palmitoleic acid 254.22458 1.0 C18H34O2 cis-Vaccenic acid 282.2559 a malonyl-[acp] a holo-[acyl-carrier protein] Extracellular Space NAD(P) BioCyc C21H29N7O14P2 NADH 665.12476 5282761 PubChem-compound GO:0005620 GENE ONTOLOGY 562 TAXONOMY H Hydrogen Ion 1.007825 Fatty Acid Metabolism 393216 ChemSpider 1.0 53-84-9 CAS trans-Δ3-cis-Δ5-dodecenoyl-[acp] 445638 PubChem-compound GO:0005615 GENE ONTOLOGY 1.0 1.0 3-oxo-cis-Δ5-dodecenoyl-[acp]  1.0 3-oxo-cis-vaccenoyl-[acp]  3-oxo-cis-Δ9-hexadecenoyl-[acp]  SMILES CCCCCC\C=C/CCCCCCCCCC(O)=O SMILES CCCCCC\C=C/CCCCCCCC(O)=O SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O 5682 ChemSpider SMILES NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O Water cis-Δ3-decenoyl-ACP Reaction3395 false a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] → Water + trans-Δ3-cis-Δ5-dodecenoyl-[acp] LEFT_TO_RIGHT P0A6Q3 UniProt 1.1.1.100 false 1.1.1.100 3-oxo-cis-Δ5-dodecenoyl-[acp]  + Hydrogen Ion + NADPH → NADP + a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] LEFT_TO_RIGHT P0A6Q6 UniProt (3R)-hydroxymyristoyl-[acyl-carrier-protein] dehydratase 4445888 ChemSpider 1.0 4.0 3R-hydroxy cis Δ9-hexadecenoyl-[acp] 1.0 a 3-oxo-cis-Δ7-tetradecenoyl-[acp]  1.0 cis-vaccen-2-enoyl-[acp] a cis-vaccenoyl-[acp] 5675 ChemSpider SMP0000817 SMPDB cis-Δ5-dodecenoyl-[acp]  cis-Δ7-tetradecenoyl-[acp]  1.0 cis-Vaccenic acid Escherichia coli P0AAI5 UniProt 7732-18-5 CAS 388299 ChemSpider CHEBI:50464 ChEBI 4.2.1.59 false 4.2.1.59 an (R)-3-hydroxydecanoyl-[acp]  → Water + a trans-Δ2-decenoyl-[acp]  LEFT_TO_RIGHT HMDB0001487 HMDB 4.2.1.59 false 4.2.1.59 a trans-Δ2-decenoyl-[acp]  → cis-Δ3-decenoyl-ACP LEFT_TO_RIGHT 1.0 1.0 ReactionCatalysis3363 ACTIVATION 4.2.1.59 false 4.2.1.59 a 3R-hydroxy cis Δ7-tetradecenoyl-[acp] → trans-Δ3-cis-Δ7-tetradecenoyl-[acp] + Water LEFT_TO_RIGHT 2.3.1.41 false 2.3.1.41 Hydrogen Ion + a malonyl-[acp] + cis-Δ5-dodecenoyl-[acp]  → Carbon dioxide + a 3-oxo-cis-Δ7-tetradecenoyl-[acp]  + a holo-[acyl-carrier protein] LEFT_TO_RIGHT ReactionCatalysis3362 ACTIVATION 1.1.1.100 false 1.1.1.100 Hydrogen Ion + NADPH + a 3-oxo-cis-Δ7-tetradecenoyl-[acp]  → NADP + a 3R-hydroxy cis Δ7-tetradecenoyl-[acp] LEFT_TO_RIGHT 1.3.1.9 false 1.3.1.9 Hydrogen Ion + NADH + trans-Δ3-cis-Δ5-dodecenoyl-[acp] → NAD + cis-Δ5-dodecenoyl-[acp]  LEFT_TO_RIGHT 2.3.1.41 false 2.3.1.41 Hydrogen Ion + a malonyl-[acp] + cis-Δ3-decenoyl-ACP → 3-oxo-cis-Δ5-dodecenoyl-[acp]  + Carbon dioxide + a holo-[acyl-carrier protein] LEFT_TO_RIGHT PW000796 PathWhiz CHEBI:16526 ChEBI a palmitoleoyl-[acp]  1.0 a trans-Δ2-decenoyl-[acp]  1.0 3-hydroxydecanoyl-[acp] dehydrase ReactionCatalysis2723 ACTIVATION KASI 3-hydroxy-acyl-[acyl-carrier-protein] dehydratase ReactionCatalysis2722 ACTIVATION ReactionCatalysis2725 ACTIVATION an (R)-3-hydroxydecanoyl-[acp]  ReactionCatalysis2724 ACTIVATION 1.0 1.0 multifunctional acyl-CoA thioesterase I and protease I and lysophospholipase L1 enoyl-[acyl-carrier-protein] reductase(NAD) KASII 962 PubChem-compound a cis-vaccenoyl-[acp] cis-vaccen-2-enoyl-[acp] 4.0 a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] P0AEK2 UniProt 3R-hydroxy cis Δ9-hexadecenoyl-[acp] CO2 Carbon dioxide 43.98983 P0AEK4 UniProt Acyl-CoA thioesterase I 1.0 a 3-oxo-cis-Δ7-tetradecenoyl-[acp]  5893 PubChem-compound 3.1.2.- false 3.1.2.- a cis-vaccenoyl-[acp] + Water → Hydrogen Ion + a holo-[acyl-carrier protein] + cis-Vaccenic acid LEFT_TO_RIGHT C00080 KEGG Compound 1.3.1.9 false 1.3.1.9 Hydrogen Ion + NADH + cis-vaccen-2-enoyl-[acp] → a cis-vaccenoyl-[acp] + NAD LEFT_TO_RIGHT Periplasmic Space C08362 KEGG Compound (3R)-hydroxymyristoyl-[acyl-carrier-protein] dehydratase Transport436 false cis-Vaccenic acid (→) Transport: Escherichia coli, Periplasmic Space to Escherichia coli, Cytosol LEFT_TO_RIGHT Transport439 false cis-Vaccenic acid (→) Transport: Escherichia coli, Extracellular Space to Escherichia coli, Periplasmic Space LEFT_TO_RIGHT Transport438 false Palmitoleic acid (→) Transport: Escherichia coli, Extracellular Space to Escherichia coli, Periplasmic Space LEFT_TO_RIGHT 1.0 HMDB0002111 HMDB Transport435 false Palmitoleic acid (→) Transport: Escherichia coli, Periplasmic Space to Escherichia coli, Cytosol LEFT_TO_RIGHT CHEBI:15377 ChEBI CHEBI:15378 ChEBI SMILES [H+] 1.0 cis-Δ5-dodecenoyl-[acp]  1.0 5886 PubChem-compound 3-oxo-cis-vaccenoyl-[acp]  cis-Δ7-tetradecenoyl-[acp]  3-oxo-cis-Δ5-dodecenoyl-[acp]  3-oxo-cis-Δ9-hexadecenoyl-[acp]  2.3.1.41 false 2.3.1.41 Hydrogen Ion + a malonyl-[acp] + cis-Δ7-tetradecenoyl-[acp]  → 3-oxo-cis-Δ9-hexadecenoyl-[acp]  + Carbon dioxide + a holo-[acyl-carrier protein] LEFT_TO_RIGHT 1.1.1.100 false 1.1.1.100 3-oxo-cis-Δ9-hexadecenoyl-[acp]  + Hydrogen Ion + NADPH → 3R-hydroxy cis Δ9-hexadecenoyl-[acp] + NADP LEFT_TO_RIGHT 3-oxoacyl-[acyl-carrier-protein] synthase 1 1.0 1.3.1.9 false 1.3.1.9 trans-Δ3-cis-Δ7-tetradecenoyl-[acp] + Hydrogen Ion + NADH → NAD + cis-Δ7-tetradecenoyl-[acp]  LEFT_TO_RIGHT 280 PubChem-compound 4.2.1.59 false 4.2.1.59 (R)-3-hydroxy-cis-vaccenoyl-[acp] → Water + cis-vaccen-2-enoyl-[acp] LEFT_TO_RIGHT 2.3.1.179 false 2.3.1.179 Hydrogen Ion + a malonyl-[acp] + a palmitoleoyl-[acp]  → 3-oxo-cis-vaccenoyl-[acp]  + Carbon dioxide + a holo-[acyl-carrier protein] LEFT_TO_RIGHT 1.1.1.100 false 1.1.1.100 3-oxo-cis-vaccenoyl-[acp]  + Hydrogen Ion + NADPH → (R)-3-hydroxy-cis-vaccenoyl-[acp] + NADP LEFT_TO_RIGHT 1.3.1.9 false 1.3.1.9 Hydrogen Ion + NADH + trans-Δ3-cis-Δ9-hexadecenoyl-[acp] → NAD + a palmitoleoyl-[acp]  LEFT_TO_RIGHT 3.1.2.- false 3.1.2.- Water + a palmitoleoyl-[acp]  → Hydrogen Ion + Palmitoleic acid + a holo-[acyl-carrier protein] LEFT_TO_RIGHT 4.2.1.59 false 4.2.1.59 3R-hydroxy cis Δ9-hexadecenoyl-[acp] → Water + trans-Δ3-cis-Δ9-hexadecenoyl-[acp] LEFT_TO_RIGHT a palmitoleoyl-[acp]  a trans-Δ2-decenoyl-[acp]  Palmitoleic acid SubPathwayInteraction1386 SubPathway1386Reaction SubPathwayReaction 22833512 PubChem-compound H2O Water 18.010565 cis-Vaccenic acid HMDB0003229 HMDB 2.0 NADH BioCyc NAD BioCyc CPD-724 BioCyc 1.0 HMDB0059597 HMDB a 3R-hydroxy cis Δ7-tetradecenoyl-[acp] Carbon dioxide HMDB0001967 HMDB 1.0 SMP0000919 SMPDB 1.0 506-17-2 CAS an (R)-3-hydroxydecanoyl-[acp]  P0A953 UniProt 3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase 1.0 PW000900 PathWhiz 3-oxoacyl-[acyl-carrier-protein] reductase Enoyl-[acyl-carrier-protein] reductase [NADH] 3- hydroxydecanoyl- [acyl- carrier- protein] dehydratase 3-oxoacyl- [acyl- carrier- protein] synthase 1 3-oxoacyl- [acyl- carrier- protein] reductase (3R)- hydroxymyristoyl- [acyl- carrier- protein] dehydratase Enoyl-[acyl- carrier- protein] reductase [NADH] 3-oxoacyl- [acyl- carrier- protein] synthase 1 3-oxoacyl- [acyl- carrier- protein] reductase (3R)- hydroxymyristoyl- [acyl- carrier- protein] dehydratase Enoyl-[acyl- carrier- protein] reductase [NADH] 3-oxoacyl- [acyl- carrier- protein] synthase 1 3-oxoacyl- [acyl- carrier- protein] reductase (3R)- hydroxymyristoyl- [acyl- carrier- protein] dehydratase Enoyl-[acyl- carrier- protein] reductase [NADH] Acyl-CoA thioesterase I 3-oxoacyl- [acyl- carrier- protein] synthase 2 3-oxoacyl- [acyl- carrier- protein] reductase (3R)- hydroxymyristoyl- [acyl- carrier- protein] dehydratase Enoyl-[acyl- carrier- protein] reductase [NADH] Acyl-CoA thioesterase I Palmitoleic acid Palmitoleic acid cis-Vaccenic acid cis-Vaccenic acid Palmitoleic acid Palmitoleic acid cis-Vaccenic acid cis-Vaccenic acid H 2 O H + CO 2 H + NADPH NADP H 2 O H + NADH NAD H + CO 2 H + NADPH NADP H 2 O H + NADH NAD H + CO 2 H + NADPH NADP H 2 O H + NADH NAD H 2 O H + Palmitoleic acid H + CO 2 H + NADPH NADP H 2 O H + NADH NAD H 2 O H + cis-Vaccenic acid an (R)-3- hydroxydecanoyl- [acp] a trans-Δ2- decenoyl- [acp] cis-Δ3- decenoyl-ACP a malonyl-[acp] a holo-[acyl- carrier protein] 3-oxo-cis-Δ5- dodecenoyl- [acp] a (3R)-hydroxy cis Δ5- dodecenoyl- [acp] trans-Δ3-cis- Δ5- dodecenoyl- [acp] cis-Δ5- dodecenoyl- [acp] a malonyl-[acp] a 3-oxo-cis-Δ7- tetradecenoyl- [acp] a holo-[acyl- carrier protein] a 3R-hydroxy cis Δ7- tetradecenoyl- [acp] trans-Δ3-cis- Δ7- tetradecenoyl- [acp] cis-Δ7- tetradecenoyl- [acp] a malonyl-[acp] a holo-[acyl- carrier protein] 3-oxo-cis-Δ9- hexadecenoyl- [acp] 3R-hydroxy cis Δ9- hexadecenoyl- [acp] trans-Δ3-cis- Δ9- hexadecenoyl- [acp] a palmitoleoyl- [acp] a holo-[acyl- carrier protein] a malonyl-[acp] a holo-[acyl- carrier protein] 3-oxo-cis- vaccenoyl- [acp] (R)-3- hydroxy-cis- vaccenoyl- [acp] cis-vaccen-2- enoyl-[acp] a cis- vaccenoyl- [acp] a holo-[acyl- carrier protein] Fatty Acid Biosynthesis Fatty Acid Biosynthesis (3R)- hydroxymyristoyl- [acyl- carrier- protein] dehydratase 3- hydroxydecanoyl- [acyl- carrier- protein] dehydratase
17215925 ChemSpider 937 ChemSpider NADH 439153 PubChem-compound SMILES O 1.0 cis-Vaccenic acid Acyl-CoA thioesterase I NAD Palmitoleic acid cis-Vaccenic acid Palmitoleic acid trans-Δ3-cis-Δ7-tetradecenoyl-[acp] trans-Δ3-cis-Δ9-hexadecenoyl-[acp] (R)-3-hydroxy-cis-vaccenoyl-[acp] 1.0 3-oxoacyl-[acyl-carrier-protein] synthase 2 CHEBI:15846 ChEBI 1.0 53-59-8 CAS 1.0 HMDB0240219 HMDB 1038 PubChem-compound cis-Δ3-decenoyl-ACP 3-oxoacyl-[acyl-carrier-protein] synthase 1 CHEBI:16474 ChEBI Palmitoleic acid GO:0005829 GENE ONTOLOGY 1.0 274 ChemSpider CHEBI:16908 ChEBI NADPH 1.0 trans-Δ3-cis-Δ5-dodecenoyl-[acp] 1010 ChemSpider Enoyl-[acyl-carrier-protein] reductase [NADH] 3-oxoacyl-[acyl-carrier-protein] reductase NADP C21H30N7O17P3 NADPH 745.0911 C21H29N7O17P3 NADP 744.08325 1.0 1.0 NADPH BioCyc 1.0 Hydrogen Ion a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] trans-Δ3-cis-Δ9-hexadecenoyl-[acp] trans-Δ3-cis-Δ7-tetradecenoyl-[acp] ReactionCatalysis2729 ACTIVATION CHEBI:28716 ChEBI 3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase ReactionCatalysis2728 ACTIVATION Cytosol 58-68-4 CAS 373-49-9 CAS ReactionCatalysis2731 ACTIVATION ReactionCatalysis2734 ACTIVATION ReactionCatalysis2733 ACTIVATION ReactionCatalysis2735 ACTIVATION HMDB0000217 HMDB ReactionCatalysis2738 ACTIVATION ReactionCatalysis2737 ACTIVATION 124-38-9 CAS (R)-3-hydroxy-cis-vaccenoyl-[acp] ReactionCatalysis2730 ACTIVATION 2.0 Fatty Acid Biosynthesis SubPathway a holo-[acyl-carrier protein] C00006 KEGG Compound a malonyl-[acp] 1.0 a 3R-hydroxy cis Δ7-tetradecenoyl-[acp] CHEBI:18009 ChEBI C00001 KEGG Compound ReactionCatalysis2739 ACTIVATION 1.0 C00005 KEGG Compound 2.0 C00004 KEGG Compound C00003 KEGG Compound SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O ReactionCatalysis2743 ACTIVATION HMDB0000221 HMDB P0ADA1 UniProt ReactionCatalysis2742 ACTIVATION ReactionCatalysis2745 ACTIVATION SMILES NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O ReactionCatalysis2741 ACTIVATION ReactionCatalysis2740 ACTIVATION 1.0 53-57-6 CAS C21H28N7O14P2 NAD 664.11694 C00011 KEGG Compound SMILES O=C=O 6.0 3-oxoacyl-[acyl-carrier-protein] synthase 2 HMDB0000902 HMDB C16H30O2 Palmitoleic acid 254.22458 1.0 C18H34O2 cis-Vaccenic acid 282.2559 a malonyl-[acp] a holo-[acyl-carrier protein] Extracellular Space NAD(P) BioCyc C21H29N7O14P2 NADH 665.12476 5282761 PubChem-compound GO:0005620 GENE ONTOLOGY 562 TAXONOMY H Hydrogen Ion 1.007825 Fatty Acid Metabolism 393216 ChemSpider 1.0 53-84-9 CAS trans-Δ3-cis-Δ5-dodecenoyl-[acp] 445638 PubChem-compound GO:0005615 GENE ONTOLOGY 1.0 1.0 3-oxo-cis-Δ5-dodecenoyl-[acp]  1.0 3-oxo-cis-vaccenoyl-[acp]  3-oxo-cis-Δ9-hexadecenoyl-[acp]  SMILES CCCCCC\C=C/CCCCCCCCCC(O)=O SMILES CCCCCC\C=C/CCCCCCCC(O)=O SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O 5682 ChemSpider SMILES NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O Water cis-Δ3-decenoyl-ACP Reaction3395 false a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] → Water + trans-Δ3-cis-Δ5-dodecenoyl-[acp] LEFT_TO_RIGHT P0A6Q3 UniProt 1.1.1.100 false 1.1.1.100 3-oxo-cis-Δ5-dodecenoyl-[acp]  + Hydrogen Ion + NADPH → NADP + a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] LEFT_TO_RIGHT P0A6Q6 UniProt (3R)-hydroxymyristoyl-[acyl-carrier-protein] dehydratase 4445888 ChemSpider 1.0 4.0 3R-hydroxy cis Δ9-hexadecenoyl-[acp] 1.0 a 3-oxo-cis-Δ7-tetradecenoyl-[acp]  1.0 cis-vaccen-2-enoyl-[acp] a cis-vaccenoyl-[acp] 5675 ChemSpider SMP0000817 SMPDB cis-Δ5-dodecenoyl-[acp]  cis-Δ7-tetradecenoyl-[acp]  1.0 cis-Vaccenic acid Escherichia coli P0AAI5 UniProt 7732-18-5 CAS 388299 ChemSpider CHEBI:50464 ChEBI 4.2.1.59 false 4.2.1.59 an (R)-3-hydroxydecanoyl-[acp]  → Water + a trans-Δ2-decenoyl-[acp]  LEFT_TO_RIGHT HMDB0001487 HMDB 4.2.1.59 false 4.2.1.59 a trans-Δ2-decenoyl-[acp]  → cis-Δ3-decenoyl-ACP LEFT_TO_RIGHT 1.0 1.0 ReactionCatalysis3363 ACTIVATION 4.2.1.59 false 4.2.1.59 a 3R-hydroxy cis Δ7-tetradecenoyl-[acp] → trans-Δ3-cis-Δ7-tetradecenoyl-[acp] + Water LEFT_TO_RIGHT 2.3.1.41 false 2.3.1.41 Hydrogen Ion + a malonyl-[acp] + cis-Δ5-dodecenoyl-[acp]  → Carbon dioxide + a 3-oxo-cis-Δ7-tetradecenoyl-[acp]  + a holo-[acyl-carrier protein] LEFT_TO_RIGHT ReactionCatalysis3362 ACTIVATION 1.1.1.100 false 1.1.1.100 Hydrogen Ion + NADPH + a 3-oxo-cis-Δ7-tetradecenoyl-[acp]  → NADP + a 3R-hydroxy cis Δ7-tetradecenoyl-[acp] LEFT_TO_RIGHT 1.3.1.9 false 1.3.1.9 Hydrogen Ion + NADH + trans-Δ3-cis-Δ5-dodecenoyl-[acp] → NAD + cis-Δ5-dodecenoyl-[acp]  LEFT_TO_RIGHT 2.3.1.41 false 2.3.1.41 Hydrogen Ion + a malonyl-[acp] + cis-Δ3-decenoyl-ACP → 3-oxo-cis-Δ5-dodecenoyl-[acp]  + Carbon dioxide + a holo-[acyl-carrier protein] LEFT_TO_RIGHT PW000796 PathWhiz CHEBI:16526 ChEBI a palmitoleoyl-[acp]  1.0 a trans-Δ2-decenoyl-[acp]  1.0 3-hydroxydecanoyl-[acp] dehydrase ReactionCatalysis2723 ACTIVATION KASI 3-hydroxy-acyl-[acyl-carrier-protein] dehydratase ReactionCatalysis2722 ACTIVATION ReactionCatalysis2725 ACTIVATION an (R)-3-hydroxydecanoyl-[acp]  ReactionCatalysis2724 ACTIVATION 1.0 1.0 multifunctional acyl-CoA thioesterase I and protease I and lysophospholipase L1 enoyl-[acyl-carrier-protein] reductase(NAD) KASII 962 PubChem-compound a cis-vaccenoyl-[acp] cis-vaccen-2-enoyl-[acp] 4.0 a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] P0AEK2 UniProt 3R-hydroxy cis Δ9-hexadecenoyl-[acp] CO2 Carbon dioxide 43.98983 P0AEK4 UniProt Acyl-CoA thioesterase I 1.0 a 3-oxo-cis-Δ7-tetradecenoyl-[acp]  5893 PubChem-compound 3.1.2.- false 3.1.2.- a cis-vaccenoyl-[acp] + Water → Hydrogen Ion + a holo-[acyl-carrier protein] + cis-Vaccenic acid LEFT_TO_RIGHT C00080 KEGG Compound 1.3.1.9 false 1.3.1.9 Hydrogen Ion + NADH + cis-vaccen-2-enoyl-[acp] → a cis-vaccenoyl-[acp] + NAD LEFT_TO_RIGHT Periplasmic Space C08362 KEGG Compound (3R)-hydroxymyristoyl-[acyl-carrier-protein] dehydratase Transport436 false cis-Vaccenic acid (→) Transport: Escherichia coli, Periplasmic Space to Escherichia coli, Cytosol LEFT_TO_RIGHT Transport439 false cis-Vaccenic acid (→) Transport: Escherichia coli, Extracellular Space to Escherichia coli, Periplasmic Space LEFT_TO_RIGHT Transport438 false Palmitoleic acid (→) Transport: Escherichia coli, Extracellular Space to Escherichia coli, Periplasmic Space LEFT_TO_RIGHT 1.0 HMDB0002111 HMDB Transport435 false Palmitoleic acid (→) Transport: Escherichia coli, Periplasmic Space to Escherichia coli, Cytosol LEFT_TO_RIGHT CHEBI:15377 ChEBI CHEBI:15378 ChEBI SMILES [H+] 1.0 cis-Δ5-dodecenoyl-[acp]  1.0 5886 PubChem-compound 3-oxo-cis-vaccenoyl-[acp]  cis-Δ7-tetradecenoyl-[acp]  3-oxo-cis-Δ5-dodecenoyl-[acp]  3-oxo-cis-Δ9-hexadecenoyl-[acp]  2.3.1.41 false 2.3.1.41 Hydrogen Ion + a malonyl-[acp] + cis-Δ7-tetradecenoyl-[acp]  → 3-oxo-cis-Δ9-hexadecenoyl-[acp]  + Carbon dioxide + a holo-[acyl-carrier protein] LEFT_TO_RIGHT 1.1.1.100 false 1.1.1.100 3-oxo-cis-Δ9-hexadecenoyl-[acp]  + Hydrogen Ion + NADPH → 3R-hydroxy cis Δ9-hexadecenoyl-[acp] + NADP LEFT_TO_RIGHT 3-oxoacyl-[acyl-carrier-protein] synthase 1 1.0 1.3.1.9 false 1.3.1.9 trans-Δ3-cis-Δ7-tetradecenoyl-[acp] + Hydrogen Ion + NADH → NAD + cis-Δ7-tetradecenoyl-[acp]  LEFT_TO_RIGHT 280 PubChem-compound 4.2.1.59 false 4.2.1.59 (R)-3-hydroxy-cis-vaccenoyl-[acp] → Water + cis-vaccen-2-enoyl-[acp] LEFT_TO_RIGHT 2.3.1.179 false 2.3.1.179 Hydrogen Ion + a malonyl-[acp] + a palmitoleoyl-[acp]  → 3-oxo-cis-vaccenoyl-[acp]  + Carbon dioxide + a holo-[acyl-carrier protein] LEFT_TO_RIGHT 1.1.1.100 false 1.1.1.100 3-oxo-cis-vaccenoyl-[acp]  + Hydrogen Ion + NADPH → (R)-3-hydroxy-cis-vaccenoyl-[acp] + NADP LEFT_TO_RIGHT 1.3.1.9 false 1.3.1.9 Hydrogen Ion + NADH + trans-Δ3-cis-Δ9-hexadecenoyl-[acp] → NAD + a palmitoleoyl-[acp]  LEFT_TO_RIGHT 3.1.2.- false 3.1.2.- Water + a palmitoleoyl-[acp]  → Hydrogen Ion + Palmitoleic acid + a holo-[acyl-carrier protein] LEFT_TO_RIGHT 4.2.1.59 false 4.2.1.59 3R-hydroxy cis Δ9-hexadecenoyl-[acp] → Water + trans-Δ3-cis-Δ9-hexadecenoyl-[acp] LEFT_TO_RIGHT a palmitoleoyl-[acp]  a trans-Δ2-decenoyl-[acp]  Palmitoleic acid SubPathwayInteraction1386 SubPathway1386Reaction SubPathwayReaction 22833512 PubChem-compound H2O Water 18.010565 cis-Vaccenic acid HMDB0003229 HMDB 2.0 NADH BioCyc NAD BioCyc CPD-724 BioCyc 1.0 HMDB0059597 HMDB a 3R-hydroxy cis Δ7-tetradecenoyl-[acp] Carbon dioxide HMDB0001967 HMDB 1.0 SMP0000919 SMPDB 1.0 506-17-2 CAS an (R)-3-hydroxydecanoyl-[acp]  P0A953 UniProt 3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase 1.0 PW000900 PathWhiz 3-oxoacyl-[acyl-carrier-protein] reductase Enoyl-[acyl-carrier-protein] reductase [NADH] fabA fabB fabG fabZ fabI fabB fabG fabZ fabI fabB fabG fabZ fabI tesA fabF fabG fabZ fabI tesA Palmitoleic acid Palmitoleic acid cis-Vaccenic acid cis-Vaccenic acid Palmitoleic acid Palmitoleic acid cis-Vaccenic acid cis-Vaccenic acid Water Hydrogen Ion Carbon dioxide Hydrogen Ion NADPH NADP Water Hydrogen Ion NADH NAD Hydrogen Ion Carbon dioxide Hydrogen Ion NADPH NADP Water Hydrogen Ion NADH NAD Hydrogen Ion Carbon dioxide Hydrogen Ion NADPH NADP Water Hydrogen Ion NADH NAD Water Hydrogen Ion Palmitoleic acid Hydrogen Ion Carbon dioxide Hydrogen Ion NADPH NADP Water Hydrogen Ion NADH NAD Water Hydrogen Ion cis-Vaccenic acid an (R)-3- hydroxydecanoyl- [acp] a trans-Δ2- decenoyl- [acp] cis-Δ3- decenoyl-ACP a malonyl-[acp] a holo-[acyl- carrier protein] 3-oxo-cis-Δ5- dodecenoyl- [acp] a (3R)-hydroxy cis Δ5- dodecenoyl- [acp] trans-Δ3-cis- Δ5- dodecenoyl- [acp] cis-Δ5- dodecenoyl- [acp] a malonyl-[acp] a 3-oxo-cis-Δ7- tetradecenoyl- [acp] a holo-[acyl- carrier protein] a 3R-hydroxy cis Δ7- tetradecenoyl- [acp] trans-Δ3-cis- Δ7- tetradecenoyl- [acp] cis-Δ7- tetradecenoyl- [acp] a malonyl-[acp] a holo-[acyl- carrier protein] 3-oxo-cis-Δ9- hexadecenoyl- [acp] 3R-hydroxy cis Δ9- hexadecenoyl- [acp] trans-Δ3-cis- Δ9- hexadecenoyl- [acp] a palmitoleoyl- [acp] a holo-[acyl- carrier protein] a malonyl-[acp] a holo-[acyl- carrier protein] 3-oxo-cis- vaccenoyl- [acp] (R)-3- hydroxy-cis- vaccenoyl- [acp] cis-vaccen-2- enoyl-[acp] a cis- vaccenoyl- [acp] a holo-[acyl- carrier protein] Fatty Acid Biosynthesis Fatty Acid Biosynthesis fabZ fabA