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17215925 ChemSpider 937 ChemSpider NADH 439153 PubChem-compound SMILES O SMP00025 SMPDB 1.0 Vaccenic acid SMP00039 SMPDB Acyl-CoA thioesterase I NAD Palmitoleic acid 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 PW000048 PathWhiz 1038 PubChem-compound cis-Δ3-decenoyl-ACP 3-oxoacyl-[acyl-carrier-protein] synthase 1 CHEBI:16474 ChEBI Palmitoleic acid GO:0005829 GENE ONTOLOGY HMDB59597 HMDB 1.0 274 ChemSpider HMDB00902 HMDB 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 C16H32O2 Palmitic acid 256.24023 C21H29N7O17P3 NADP 744.08325 SMP00054 SMPDB 1.0 1.0 NADPH BioCyc 1.0 Hydrogen Ion a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] trans-Δ3-cis-Δ9-hexadecenoyl-[acp] HMDB00217 HMDB 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 ReactionCatalysis2738 ACTIVATION ReactionCatalysis2737 ACTIVATION 124-38-9 CAS (R)-3-hydroxy-cis-vaccenoyl-[acp] ReactionCatalysis2730 ACTIVATION HMDB00221 HMDB 2.0 a holo-[acyl-carrier protein] C00249 KEGG Compound C00006 KEGG Compound a malonyl-[acp] 1.0 a 3R-hydroxy cis Δ7-tetradecenoyl-[acp] CHEBI:18009 ChEBI C00001 KEGG Compound SMP00919 SMPDB ReactionCatalysis2739 ACTIVATION 1.0 C00005 KEGG Compound 2.0 C00004 KEGG Compound C00003 KEGG Compound HMDB00220 HMDB 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 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 SMILES CCCCCCCCCCCCCCCC(O)=O 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 C16H30O2 Palmitoleic acid 254.22458 1.0 C18H34O2 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 H Hydrogen Ion 1.007825 393216 ChemSpider CHEBI:15756 ChEBI 1.0 53-84-9 CAS SMP00817 SMPDB trans-Δ3-cis-Δ5-dodecenoyl-[acp] 445638 PubChem-compound GO:0005615 GENE ONTOLOGY GO:0005737 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 Fatty acid Metabolism a 3-oxo-cis-Δ7-tetradecenoyl-[acp]  1.0 CPD-8475 BioCyc cis-vaccen-2-enoyl-[acp] a cis-vaccenoyl-[acp] 5675 ChemSpider cis-Δ5-dodecenoyl-[acp]  cis-Δ7-tetradecenoyl-[acp]  Cytoplasm 1.0 HMDB03229 HMDB Vaccenic acid 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 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 57-10-3 CAS 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 Palmitic acid SubPathwayOutput SubPathwayInput PW000796 PathWhiz CHEBI:16526 ChEBI a palmitoleoyl-[acp]  1.0 a trans-Δ2-decenoyl-[acp]  HMDB03231 HMDB 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 HMDB01967 HMDB 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 PW000144 PathWhiz a cis-vaccenoyl-[acp] PW000022 PathWhiz 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 HMDB02111 HMDB 3.1.2.- false 3.1.2.- a cis-vaccenoyl-[acp] + Water → Hydrogen Ion + Vaccenic acid + a holo-[acyl-carrier protein] LEFT_TO_RIGHT C00080 KEGG Compound C08367 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 Vaccenic acid (→) Transport: Escherichia coli, Periplasmic Space to Escherichia coli, Cytosol LEFT_TO_RIGHT Transport439 false 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 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 Glycerolipid Metabolism SubPathway Fatty Acid Elongation In Mitochondria SubPathway 5886 PubChem-compound 3-oxo-cis-vaccenoyl-[acp]  cis-Δ7-tetradecenoyl-[acp]  3-oxo-cis-Δ5-dodecenoyl-[acp]  3-oxo-cis-Δ9-hexadecenoyl-[acp]  fatty acid biosynthesis SubPathway 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 960 ChemSpider 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 HMDB01487 HMDB 985 PubChem-compound a palmitoleoyl-[acp]  a trans-Δ2-decenoyl-[acp]  Phospholipid Biosynthesis SubPathway SubPathwayInteraction1149 SubPathwayReaction SubPathway1149Reaction SubPathwayInteraction1148 SubPathwayReaction SubPathway1148Reaction Palmitoleic acid SubPathwayInteraction1386 SubPathway1386Reaction SubPathwayReaction SubPathwayInteraction1150 SubPathwayReaction SubPathway1150Reaction 22833512 PubChem-compound H2O Water 18.010565 Vaccenic acid 2.0 NADH BioCyc NAD BioCyc CPD-724 BioCyc 1.0 a 3R-hydroxy cis Δ7-tetradecenoyl-[acp] Carbon dioxide 1.0 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 Vaccenic acid Vaccenic acid Palmitoleic acid Palmitoleic acid Vaccenic acid 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 + 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 http://identifiers.org/smpdb/SMP00025 SMPDB 1.0 Vaccenic acid http://identifiers.org/smpdb/SMP00039 SMPDB Acyl-CoA thioesterase I NAD Palmitoleic acid Vaccenic acid Palmitoleic acid Fatty Acid Elongation In Mitochondria SubPathway 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 PW000048 PathWhiz 1038 PubChem-compound cis-Δ3-decenoyl-ACP 3-oxoacyl-[acyl-carrier-protein] synthase 1 CHEBI:16474 ChEBI Palmitoleic acid GO:0005829 GENE ONTOLOGY HMDB59597 HMDB 1.0 274 ChemSpider HMDB00902 HMDB 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 C16H32O2 Palmitic acid 256.24023 C21H29N7O17P3 NADP 744.08325 http://identifiers.org/smpdb/SMP00054 SMPDB 1.0 1.0 NADPH BioCyc 1.0 Hydrogen Ion a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] trans-Δ3-cis-Δ9-hexadecenoyl-[acp] HMDB00217 HMDB 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 ReactionCatalysis2738 ACTIVATION ReactionCatalysis2737 ACTIVATION 124-38-9 CAS (R)-3-hydroxy-cis-vaccenoyl-[acp] ReactionCatalysis2730 ACTIVATION HMDB00221 HMDB 2.0 a holo-[acyl-carrier protein] C00249 KEGG Compound C00006 KEGG Compound a malonyl-[acp] 1.0 a 3R-hydroxy cis Δ7-tetradecenoyl-[acp] CHEBI:18009 ChEBI C00001 KEGG Compound http://identifiers.org/smpdb/SMP00919 SMPDB ReactionCatalysis2739 ACTIVATION 1.0 C00005 KEGG Compound 2.0 C00004 KEGG Compound C00003 KEGG Compound HMDB00220 HMDB 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 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 SMILES CCCCCCCCCCCCCCCC(O)=O 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 C16H30O2 Palmitoleic acid 254.22458 1.0 C18H34O2 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 H Hydrogen Ion 1.007825 393216 ChemSpider CHEBI:15756 ChEBI 1.0 53-84-9 CAS http://identifiers.org/smpdb/SMP00817 SMPDB trans-Δ3-cis-Δ5-dodecenoyl-[acp] 445638 PubChem-compound GO:0005615 GENE ONTOLOGY GO:0005737 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 Fatty acid Metabolism a 3-oxo-cis-Δ7-tetradecenoyl-[acp]  1.0 CPD-8475 BioCyc cis-vaccen-2-enoyl-[acp] a cis-vaccenoyl-[acp] 5675 ChemSpider cis-Δ5-dodecenoyl-[acp]  cis-Δ7-tetradecenoyl-[acp]  Cytoplasm 1.0 HMDB03229 HMDB Vaccenic acid 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 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 57-10-3 CAS 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 Palmitic acid SubPathwayOutput SubPathwayInput PW000796 PathWhiz CHEBI:16526 ChEBI a palmitoleoyl-[acp]  1.0 a trans-Δ2-decenoyl-[acp]  HMDB03231 HMDB 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 HMDB01967 HMDB 1.0 Glycerolipid Metabolism SubPathway 1.0 multifunctional acyl-CoA thioesterase I and protease I and lysophospholipase L1 enoyl-[acyl-carrier-protein] reductase(NAD) KASII 962 PubChem-compound PW000144 PathWhiz a cis-vaccenoyl-[acp] PW000022 PathWhiz 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 HMDB02111 HMDB 3.1.2.- false 3.1.2.- a cis-vaccenoyl-[acp] + Water → Hydrogen Ion + Vaccenic acid + a holo-[acyl-carrier protein] LEFT_TO_RIGHT C00080 KEGG Compound C08367 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 Vaccenic acid (→) Transport: Escherichia coli, Periplasmic Space to Escherichia coli, Cytosol LEFT_TO_RIGHT Transport439 false 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 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 960 ChemSpider 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 HMDB01487 HMDB 985 PubChem-compound a palmitoleoyl-[acp]  a trans-Δ2-decenoyl-[acp]  SubPathwayInteraction1149 SubPathwayReaction SubPathway1149Reaction SubPathwayInteraction1148 SubPathwayReaction SubPathway1148Reaction Palmitoleic acid SubPathwayInteraction1386 SubPathway1386Reaction SubPathwayReaction SubPathwayInteraction1150 SubPathwayReaction SubPathway1150Reaction 22833512 PubChem-compound H2O Water 18.010565 Vaccenic acid 2.0 NADH BioCyc NAD BioCyc CPD-724 BioCyc fatty acid biosynthesis SubPathway 1.0 a 3R-hydroxy cis Δ7-tetradecenoyl-[acp] Carbon dioxide 1.0 1.0 506-17-2 CAS an (R)-3-hydroxydecanoyl-[acp]  Phospholipid Biosynthesis SubPathway 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 Vaccenic acid Vaccenic acid Palmitoleic acid Palmitoleic acid Vaccenic acid 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 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