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6022 PubChem-compound 17215925 ChemSpider C23H38N7O17P3S Acetyl-CoA 809.1258 937 ChemSpider HMDB01341 HMDB NADH 439153 PubChem-compound Acetyl-coenzyme A carboxylase carboxyl transferase subunit beta SMILES O 1.0 NAD B1IUH4 UniProt ATP BioCyc (3R)-3-hydroxyacyl-[acyl-carrier protein] trans-2-enoyl-[acyl-carrier protein] 1.0 Malonyl CoA-acyl carrier protein transacylase 6816 PubChem-compound SMILES OC([O-])=O 3-oxoacyl-[acyl-carrier-protein] synthase 2 CHEBI:15846 ChEBI ADP BioCyc HMDB00595 HMDB 1.0 53-59-8 CAS 1.0 1.0 HMDB01206 HMDB HCO3 BioCyc 1.0 5742 ChemSpider an acetyl-[acp] 1038 PubChem-compound cis-Δ3-decenoyl-ACP 3-oxoacyl-[acyl-carrier-protein] synthase 1 CHEBI:16474 ChEBI 1.0 HMDB59597 HMDB 274 ChemSpider P0A9Q5 UniProt HMDB00902 HMDB CHEBI:16908 ChEBI O4P Phosphate 94.95342 Acetyl-CoA NADPH 1.0 trans-Δ3-cis-Δ5-dodecenoyl-[acp] 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 Enoyl-[acyl-carrier-protein] reductase [NADH] 3-oxoacyl-[acyl-carrier-protein] reductase NADP C21H30N7O17P3 NADPH 745.0911 C21H29N7O17P3 NADP 744.08325 1.0 HMDB01423 HMDB NADPH BioCyc 1.0 trans-2-enoyl-[acyl-carrier protein] (3R)-3-hydroxyacyl-[acyl-carrier protein] Hydrogen Ion a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] PW000785 PathWhiz HMDB00217 HMDB 3-oxoacyl-[acyl-carrier-protein] synthase 3 3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase ReactionCatalysis2728 ACTIVATION 2.0 Adenosine triphosphate 58-68-4 CAS 1.0 SMILES [O-]P([O-])([O-])=O acetyl-CoA carboxylase KASIII Acetyl-coenzyme A carboxylase carboxyl transferase subunit alpha 124-38-9 CAS Biotin carboxyl carrier protein of acetyl-CoA carboxylase Beta-ketoacyl-ACP synthase C00009 KEGG Compound CHEBI:15531 ChEBI HMDB00221 HMDB 2.0 C00008 KEGG Compound a holo-[acyl-carrier protein] a malonyl-[acp] C00006 KEGG Compound CHEBI:18009 ChEBI SMP00919 SMPDB C00001 KEGG Compound 1.0 Acetyl-coenzyme A carboxylase carboxyl transferase subunit beta C00005 KEGG Compound CHEBI:18367 ChEBI 2.0 C00004 KEGG Compound 1032 ChemSpider C00003 KEGG Compound C00002 KEGG Compound 3-oxoacyl-[acyl-carrier-protein] synthase 3 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 ReactionCatalysis2746 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 ReactionCatalysis2749 ACTIVATION HMDB01429 HMDB 53-57-6 CAS C21H28N7O14P2 NAD 664.11694 C00011 KEGG Compound SMILES O=C=O 6.0 Malonyl CoA-acyl carrier protein transacylase C00010 KEGG Compound 3-oxoacyl-[acyl-carrier-protein] synthase 2 a malonyl-[acp] SMP00807 SMPDB a holo-[acyl-carrier protein] ReactionCatalysis2754 ACTIVATION ReactionCatalysis2755 ACTIVATION NAD(P) BioCyc C21H29N7O14P2 NADH 665.12476 5957 PubChem-compound ReactionCatalysis2750 ACTIVATION ReactionCatalysis2752 ACTIVATION H Hydrogen Ion 1.007825 56-65-5 CAS 53-84-9 CAS SMP00817 SMPDB C00024 KEGG Compound 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)NCCSC(=O)CC(O)=O Adenosine diphosphate trans-Δ3-cis-Δ5-dodecenoyl-[acp] C10H15N5O10P2 Adenosine diphosphate 427.02942 1.0 1.0 1.0 2.0 1.0 3-oxo-cis-Δ5-dodecenoyl-[acp]  769 PubChem-compound CPD-8587 BioCyc 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 2,3,4-saturated fatty acyl-[acp] 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 CHEBI:1146900 ChEBI an acetyl-[acp] Water Biotin carboxyl carrier protein of acetyl-CoA carboxylase cis-Δ3-decenoyl-ACP Reaction3395 false a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] → Water + trans-Δ3-cis-Δ5-dodecenoyl-[acp] LEFT_TO_RIGHT Acetyl-coenzyme A carboxylase carboxyl transferase subunit alpha 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 Reaction3393 false (3R)-3-hydroxyacyl-[acyl-carrier protein] → an (R)-3-hydroxydecanoyl-[acp]  LEFT_TO_RIGHT Reaction3392 false Hydrogen Ion + a malonyl-[acp] + an acetyl-[acp] → Carbon dioxide + a holo-[acyl-carrier protein] + acetoacetyl-[acp] LEFT_TO_RIGHT P0A6Q6 UniProt (3R)-hydroxymyristoyl-[acyl-carrier-protein] dehydratase 4.0 3-oxoacyl-[acp]  1.0 CO-A BioCyc 1.0 5675 ChemSpider 72-89-9 CAS C00288 KEGG Compound SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O Coenzyme A cis-Δ5-dodecenoyl-[acp]  P0A6R0 UniProt Reaction3387 false Hydrogen Ion + a malonyl-[acp] → Carbon dioxide + an acetyl-[acp] LEFT_TO_RIGHT Reaction3386 false Acetyl-CoA + a holo-[acyl-carrier protein] → Coenzyme A + an acetyl-[acp] LEFT_TO_RIGHT C21H36N7O16P3S Coenzyme A 767.11523 2.3.1.180 false 2.3.1.180 Acetyl-CoA + Hydrogen Ion + a malonyl-[acp] → Carbon dioxide + Coenzyme A + acetoacetyl-[acp] LEFT_TO_RIGHT 2.3.1.39 false 2.3.1.39 Malonyl-CoA + a holo-[acyl-carrier protein] → Coenzyme A + a malonyl-[acp] LEFT_TO_RIGHT HMDB00538 HMDB ReactionCatalysis3353 ACTIVATION 2.0 ReactionCatalysis3356 ACTIVATION ReactionCatalysis3354 ACTIVATION 10213 ChemSpider ReactionCatalysis3355 ACTIVATION 1.0 P24182 UniProt CHEBI:15422 ChEBI 3-oxoacyl-[acyl-carrier-protein] synthase 3 ReactionCatalysis3360 ACTIVATION 2.0 6557 ChemSpider P0AAI5 UniProt SMILES CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(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 524-14-1 CAS 7732-18-5 CAS 388299 ChemSpider P0AAI9 UniProt 4.2.1.59 false 4.2.1.59 an (R)-3-hydroxydecanoyl-[acp]  → Water + a trans-Δ2-decenoyl-[acp]  LEFT_TO_RIGHT Biotin carboxylase 4.2.1.59 false 4.2.1.59 a trans-Δ2-decenoyl-[acp]  → cis-Δ3-decenoyl-ACP LEFT_TO_RIGHT 1.0 ReactionCatalysis3363 ACTIVATION ReactionCatalysis3361 ACTIVATION ReactionCatalysis3362 ACTIVATION 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 fatty acid biosynthesis C10H16N5O13P3 Adenosine triphosphate 506.99576 1.0 PW000796 PathWhiz CHEBI:16526 ChEBI 1.0 HMDB01175 HMDB a trans-Δ2-decenoyl-[acp]  CHEBI:16761 ChEBI 1.0 3-hydroxydecanoyl-[acp] dehydrase acetoacetyl-[acp] KASI ReactionCatalysis2723 ACTIVATION 3-hydroxy-acyl-[acyl-carrier-protein] dehydratase ReactionCatalysis2722 ACTIVATION ReactionCatalysis2725 ACTIVATION an (R)-3-hydroxydecanoyl-[acp]  ReactionCatalysis2724 ACTIVATION HMDB01967 HMDB 1.0 enoyl-[acyl-carrier-protein] reductase(NAD) KASII 962 PubChem-compound CHEBI:17544 ChEBI 392413 ChemSpider 5800 ChemSpider a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] 3-oxoacyl-[acp]  P0AEK2 UniProt CO2 Carbon dioxide 43.98983 P0AEK4 UniProt Phosphate 1.0 5893 PubChem-compound HMDB02111 HMDB P0ABD5 UniProt 6.4.1.2 false 6.4.1.2 Acetyl-CoA + Adenosine triphosphate + Hydrogen carbonate → Adenosine diphosphate + Hydrogen Ion + Malonyl-CoA + Phosphate LEFT_TO_RIGHT C00080 KEGG Compound P0ABD8 UniProt C00083 KEGG Compound (3R)-hydroxymyristoyl-[acyl-carrier-protein] dehydratase 4.2.1.59 false 4.2.1.59 (3R)-3-hydroxyacyl-[acyl-carrier protein] → trans-2-enoyl-[acyl-carrier protein] + Water LEFT_TO_RIGHT 1.3.1.9 false 1.3.1.9 trans-2-enoyl-[acyl-carrier protein] + Hydrogen Ion + NADH → 2,3,4-saturated fatty acyl-[acp] + NAD LEFT_TO_RIGHT 1.0 Reaction2786 false acetoacetyl-[acp] → 3-oxoacyl-[acp]  LEFT_TO_RIGHT 1.1.1.100 false 1.1.1.100 3-oxoacyl-[acp]  + Hydrogen Ion + NADPH → (3R)-3-hydroxyacyl-[acyl-carrier protein] + NADP LEFT_TO_RIGHT CHEBI:15377 ChEBI C24H38N7O19P3S Malonyl-CoA 853.1156 14265-44-2 CAS CHEBI:15378 ChEBI SMILES [H+] 58-64-0 CAS cis-Δ5-dodecenoyl-[acp]  2.0 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 5886 PubChem-compound 3-oxo-cis-Δ5-dodecenoyl-[acp]  Fatty acid Metabolism SubPathway glycolysis and pyruvate dehydrogenase SubPathway 3-oxoacyl-[acyl-carrier-protein] synthase 1 1.0 280 PubChem-compound HMDB01487 HMDB 444493 PubChem-compound a trans-Δ2-decenoyl-[acp]  SubPathwayInteraction1388 SubPathwayReaction SubPathway1388Reaction Malonyl-CoA SubPathwayInteraction1387 SubPathway1387Reaction SubPathwayReaction 10663 PubChem-compound 22833512 PubChem-compound ACETYL-COA BioCyc 1.0 1.0 H2O Water 18.010565 2,3,4-saturated fatty acyl-[acp] 2.0 NADH BioCyc NAD BioCyc 1061 PubChem-compound 2.0 Carbon dioxide 749 ChemSpider acetoacetyl-[acp] 3-oxoacyl-[acyl-carrier-protein] synthase 3 71-52-3 CAS CHEBI:15351 ChEBI Biotin carboxylase an (R)-3-hydroxydecanoyl-[acp]  2.3.1.41 false 2.3.1.41 2,3,4-saturated fatty acyl-[acp] + Hydrogen Ion + a malonyl-[acp] → 3-oxoacyl-[acp]  + Carbon dioxide + a holo-[acyl-carrier protein] LEFT_TO_RIGHT P0A953 UniProt Hydrogen carbonate 3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase PW000900 PathWhiz 85-61-0 CAS CHO3 Hydrogen carbonate 60.99257 MALONYL-COA BioCyc 3-oxoacyl-[acyl-carrier-protein] reductase Enoyl-[acyl-carrier-protein] reductase [NADH] Acetyl-coenzyme A carboxylase carboxyl transferase subunit alpha Acetyl-coenzyme A carboxylase carboxyl transferase subunit beta Biotin carboxylase Biotin carboxyl carrier protein of acetyl-CoA carboxylase Malonyl CoA-acyl carrier protein transacylase 3-oxoacyl- [acyl- carrier- protein] synthase 3 3-oxoacyl- [acyl- carrier- protein] synthase 3 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- hydroxydecanoyl- [acyl- carrier- protein] dehydratase 3-oxoacyl- [acyl- carrier- protein] synthase 1 (3R)- hydroxymyristoyl- [acyl- carrier- protein] dehydratase 3-oxoacyl- [acyl- carrier- protein] reductase Enoyl-[acyl- carrier- protein] reductase [NADH] Acetyl-CoA HCO 3 - ATP ADP P i H + Malonyl-CoA CoA H + Acetyl-CoA CO 2 CoA CoA H + CO 2 H + CO 2 H + NADPH NADP H 2 O H + NADH NAD H + CO 2 H 2 O H + CO 2 H 2 O H + NADPH NADP H + NADH NAD a holo-[acyl- carrier protein] a malonyl-[acp] acetoacetyl- [acp] a holo-[acyl- carrier protein] an acetyl-[acp] an acetyl-[acp] an acetyl-[acp] a holo-[acyl- carrier protein] acetoacetyl- [acp] 3-oxoacyl-[acp] 3-oxoacyl-[acp] (3R)-3- hydroxyacyl- [acyl-carrier protein] trans-2- enoyl-[acyl- carrier protein] 2,3,4-saturated fatty acyl-[acp] a malonyl-[acp] a holo-[acyl- carrier protein] 3-oxoacyl-[acp] 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] a (3R)-hydroxy cis Δ5- dodecenoyl- [acp] cis-Δ5- dodecenoyl- [acp] Fatty acid Metabolism glycolysis and pyruvate dehydrogenase Fatty acid Metabolism 3-oxoacyl- [acyl- carrier- protein] synthase 2 3-oxoacyl- [acyl- carrier- protein] synthase 2 (3R)- hydroxymyristoyl- [acyl- carrier- protein] dehydratase 3- hydroxydecanoyl- [acyl- carrier- protein] dehydratase 3-oxoacyl- [acyl- carrier- protein] synthase 1 3-oxoacyl- [acyl- carrier- protein] synthase 1
6022 PubChem-compound 17215925 ChemSpider C23H38N7O17P3S Acetyl-CoA 809.1258 937 ChemSpider HMDB01341 HMDB NADH 439153 PubChem-compound Acetyl-coenzyme A carboxylase carboxyl transferase subunit beta SMILES O 1.0 NAD B1IUH4 UniProt ATP BioCyc (3R)-3-hydroxyacyl-[acyl-carrier protein] trans-2-enoyl-[acyl-carrier protein] 1.0 Malonyl CoA-acyl carrier protein transacylase 6816 PubChem-compound SMILES OC([O-])=O 3-oxoacyl-[acyl-carrier-protein] synthase 2 CHEBI:15846 ChEBI ADP BioCyc HMDB00595 HMDB 1.0 53-59-8 CAS 1.0 1.0 HMDB01206 HMDB HCO3 BioCyc 1.0 5742 ChemSpider an acetyl-[acp] 1038 PubChem-compound cis-Δ3-decenoyl-ACP 3-oxoacyl-[acyl-carrier-protein] synthase 1 CHEBI:16474 ChEBI 1.0 HMDB59597 HMDB 274 ChemSpider P0A9Q5 UniProt HMDB00902 HMDB CHEBI:16908 ChEBI O4P Phosphate 94.95342 Acetyl-CoA NADPH 1.0 trans-Δ3-cis-Δ5-dodecenoyl-[acp] 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 Enoyl-[acyl-carrier-protein] reductase [NADH] 3-oxoacyl-[acyl-carrier-protein] reductase NADP C21H30N7O17P3 NADPH 745.0911 C21H29N7O17P3 NADP 744.08325 glycolysis and pyruvate dehydrogenase SubPathway 1.0 HMDB01423 HMDB NADPH BioCyc 1.0 trans-2-enoyl-[acyl-carrier protein] (3R)-3-hydroxyacyl-[acyl-carrier protein] Hydrogen Ion a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] PW000785 PathWhiz HMDB00217 HMDB 3-oxoacyl-[acyl-carrier-protein] synthase 3 3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase ReactionCatalysis2728 ACTIVATION 2.0 Adenosine triphosphate 58-68-4 CAS 1.0 SMILES [O-]P([O-])([O-])=O acetyl-CoA carboxylase KASIII Acetyl-coenzyme A carboxylase carboxyl transferase subunit alpha 124-38-9 CAS Biotin carboxyl carrier protein of acetyl-CoA carboxylase Beta-ketoacyl-ACP synthase C00009 KEGG Compound CHEBI:15531 ChEBI HMDB00221 HMDB 2.0 C00008 KEGG Compound a holo-[acyl-carrier protein] a malonyl-[acp] C00006 KEGG Compound CHEBI:18009 ChEBI http://identifiers.org/smpdb/SMP00919 SMPDB C00001 KEGG Compound 1.0 Acetyl-coenzyme A carboxylase carboxyl transferase subunit beta C00005 KEGG Compound CHEBI:18367 ChEBI 2.0 C00004 KEGG Compound 1032 ChemSpider C00003 KEGG Compound C00002 KEGG Compound 3-oxoacyl-[acyl-carrier-protein] synthase 3 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 ReactionCatalysis2746 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 ReactionCatalysis2749 ACTIVATION HMDB01429 HMDB 53-57-6 CAS C21H28N7O14P2 NAD 664.11694 C00011 KEGG Compound SMILES O=C=O 6.0 Malonyl CoA-acyl carrier protein transacylase C00010 KEGG Compound 3-oxoacyl-[acyl-carrier-protein] synthase 2 a malonyl-[acp] http://identifiers.org/smpdb/SMP00807 SMPDB a holo-[acyl-carrier protein] ReactionCatalysis2754 ACTIVATION ReactionCatalysis2755 ACTIVATION NAD(P) BioCyc C21H29N7O14P2 NADH 665.12476 5957 PubChem-compound ReactionCatalysis2750 ACTIVATION ReactionCatalysis2752 ACTIVATION H Hydrogen Ion 1.007825 56-65-5 CAS 53-84-9 CAS http://identifiers.org/smpdb/SMP00817 SMPDB C00024 KEGG Compound 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)NCCSC(=O)CC(O)=O Adenosine diphosphate trans-Δ3-cis-Δ5-dodecenoyl-[acp] C10H15N5O10P2 Adenosine diphosphate 427.02942 1.0 1.0 1.0 2.0 1.0 3-oxo-cis-Δ5-dodecenoyl-[acp]  769 PubChem-compound CPD-8587 BioCyc 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 2,3,4-saturated fatty acyl-[acp] 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 CHEBI:1146900 ChEBI an acetyl-[acp] Water Biotin carboxyl carrier protein of acetyl-CoA carboxylase cis-Δ3-decenoyl-ACP Reaction3395 false a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] → Water + trans-Δ3-cis-Δ5-dodecenoyl-[acp] LEFT_TO_RIGHT Acetyl-coenzyme A carboxylase carboxyl transferase subunit alpha 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 Reaction3393 false (3R)-3-hydroxyacyl-[acyl-carrier protein] → an (R)-3-hydroxydecanoyl-[acp]  LEFT_TO_RIGHT Reaction3392 false Hydrogen Ion + a malonyl-[acp] + an acetyl-[acp] → Carbon dioxide + a holo-[acyl-carrier protein] + acetoacetyl-[acp] LEFT_TO_RIGHT P0A6Q6 UniProt (3R)-hydroxymyristoyl-[acyl-carrier-protein] dehydratase 4.0 3-oxoacyl-[acp]  1.0 CO-A BioCyc 1.0 5675 ChemSpider 72-89-9 CAS C00288 KEGG Compound SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O Coenzyme A cis-Δ5-dodecenoyl-[acp]  P0A6R0 UniProt Reaction3387 false Hydrogen Ion + a malonyl-[acp] → Carbon dioxide + an acetyl-[acp] LEFT_TO_RIGHT Reaction3386 false Acetyl-CoA + a holo-[acyl-carrier protein] → Coenzyme A + an acetyl-[acp] LEFT_TO_RIGHT C21H36N7O16P3S Coenzyme A 767.11523 2.3.1.180 false 2.3.1.180 Acetyl-CoA + Hydrogen Ion + a malonyl-[acp] → Carbon dioxide + Coenzyme A + acetoacetyl-[acp] LEFT_TO_RIGHT 2.3.1.39 false 2.3.1.39 Malonyl-CoA + a holo-[acyl-carrier protein] → Coenzyme A + a malonyl-[acp] LEFT_TO_RIGHT HMDB00538 HMDB ReactionCatalysis3353 ACTIVATION 2.0 ReactionCatalysis3356 ACTIVATION ReactionCatalysis3354 ACTIVATION 10213 ChemSpider ReactionCatalysis3355 ACTIVATION 1.0 P24182 UniProt CHEBI:15422 ChEBI 3-oxoacyl-[acyl-carrier-protein] synthase 3 ReactionCatalysis3360 ACTIVATION 2.0 6557 ChemSpider P0AAI5 UniProt SMILES CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(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 524-14-1 CAS 7732-18-5 CAS 388299 ChemSpider P0AAI9 UniProt 4.2.1.59 false 4.2.1.59 an (R)-3-hydroxydecanoyl-[acp]  → Water + a trans-Δ2-decenoyl-[acp]  LEFT_TO_RIGHT Biotin carboxylase 4.2.1.59 false 4.2.1.59 a trans-Δ2-decenoyl-[acp]  → cis-Δ3-decenoyl-ACP LEFT_TO_RIGHT 1.0 ReactionCatalysis3363 ACTIVATION ReactionCatalysis3361 ACTIVATION ReactionCatalysis3362 ACTIVATION 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 fatty acid biosynthesis C10H16N5O13P3 Adenosine triphosphate 506.99576 1.0 PW000796 PathWhiz CHEBI:16526 ChEBI 1.0 HMDB01175 HMDB a trans-Δ2-decenoyl-[acp]  CHEBI:16761 ChEBI 1.0 3-hydroxydecanoyl-[acp] dehydrase acetoacetyl-[acp] KASI ReactionCatalysis2723 ACTIVATION 3-hydroxy-acyl-[acyl-carrier-protein] dehydratase ReactionCatalysis2722 ACTIVATION ReactionCatalysis2725 ACTIVATION an (R)-3-hydroxydecanoyl-[acp]  ReactionCatalysis2724 ACTIVATION HMDB01967 HMDB 1.0 enoyl-[acyl-carrier-protein] reductase(NAD) KASII 962 PubChem-compound CHEBI:17544 ChEBI 392413 ChemSpider 5800 ChemSpider a (3R)-hydroxy cis Δ5-dodecenoyl-[acp] 3-oxoacyl-[acp]  P0AEK2 UniProt CO2 Carbon dioxide 43.98983 P0AEK4 UniProt Phosphate 1.0 5893 PubChem-compound HMDB02111 HMDB P0ABD5 UniProt 6.4.1.2 false 6.4.1.2 Acetyl-CoA + Adenosine triphosphate + Hydrogen carbonate → Adenosine diphosphate + Hydrogen Ion + Malonyl-CoA + Phosphate LEFT_TO_RIGHT C00080 KEGG Compound P0ABD8 UniProt C00083 KEGG Compound (3R)-hydroxymyristoyl-[acyl-carrier-protein] dehydratase 4.2.1.59 false 4.2.1.59 (3R)-3-hydroxyacyl-[acyl-carrier protein] → trans-2-enoyl-[acyl-carrier protein] + Water LEFT_TO_RIGHT 1.3.1.9 false 1.3.1.9 trans-2-enoyl-[acyl-carrier protein] + Hydrogen Ion + NADH → 2,3,4-saturated fatty acyl-[acp] + NAD LEFT_TO_RIGHT 1.0 Reaction2786 false acetoacetyl-[acp] → 3-oxoacyl-[acp]  LEFT_TO_RIGHT Fatty acid Metabolism SubPathway 1.1.1.100 false 1.1.1.100 3-oxoacyl-[acp]  + Hydrogen Ion + NADPH → (3R)-3-hydroxyacyl-[acyl-carrier protein] + NADP LEFT_TO_RIGHT CHEBI:15377 ChEBI C24H38N7O19P3S Malonyl-CoA 853.1156 14265-44-2 CAS CHEBI:15378 ChEBI SMILES [H+] 58-64-0 CAS cis-Δ5-dodecenoyl-[acp]  2.0 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 5886 PubChem-compound 3-oxo-cis-Δ5-dodecenoyl-[acp]  3-oxoacyl-[acyl-carrier-protein] synthase 1 1.0 280 PubChem-compound HMDB01487 HMDB 444493 PubChem-compound a trans-Δ2-decenoyl-[acp]  SubPathwayInteraction1388 SubPathwayReaction SubPathway1388Reaction Malonyl-CoA SubPathwayInteraction1387 SubPathway1387Reaction SubPathwayReaction 10663 PubChem-compound 22833512 PubChem-compound ACETYL-COA BioCyc 1.0 1.0 H2O Water 18.010565 2,3,4-saturated fatty acyl-[acp] 2.0 NADH BioCyc NAD BioCyc 1061 PubChem-compound 2.0 Carbon dioxide 749 ChemSpider acetoacetyl-[acp] 3-oxoacyl-[acyl-carrier-protein] synthase 3 71-52-3 CAS CHEBI:15351 ChEBI Biotin carboxylase an (R)-3-hydroxydecanoyl-[acp]  2.3.1.41 false 2.3.1.41 2,3,4-saturated fatty acyl-[acp] + Hydrogen Ion + a malonyl-[acp] → 3-oxoacyl-[acp]  + Carbon dioxide + a holo-[acyl-carrier protein] LEFT_TO_RIGHT P0A953 UniProt Hydrogen carbonate 3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase PW000900 PathWhiz 85-61-0 CAS CHO3 Hydrogen carbonate 60.99257 MALONYL-COA BioCyc 3-oxoacyl-[acyl-carrier-protein] reductase Enoyl-[acyl-carrier-protein] reductase [NADH] accA accD accC accB fabD fabH fabH fabB fabG fabZ fabI fabA fabB fabZ fabG fabI Acetyl-CoA Hydrogen carbonate Adenosine triphosphate Adenosine diphosphate Phosphate Hydrogen Ion Malonyl-CoA Coenzyme A Hydrogen Ion Acetyl-CoA Carbon dioxide Coenzyme A Coenzyme A Hydrogen Ion Carbon dioxide Hydrogen Ion Carbon dioxide Hydrogen Ion NADPH NADP Water Hydrogen Ion NADH NAD Hydrogen Ion Carbon dioxide Water Hydrogen Ion Carbon dioxide Water Hydrogen Ion NADPH NADP Hydrogen Ion NADH NAD a holo-[acyl- carrier protein] a malonyl-[acp] acetoacetyl- [acp] a holo-[acyl- carrier protein] an acetyl-[acp] an acetyl-[acp] an acetyl-[acp] a holo-[acyl- carrier protein] acetoacetyl- [acp] 3-oxoacyl-[acp] 3-oxoacyl-[acp] (3R)-3- hydroxyacyl- [acyl-carrier protein] trans-2- enoyl-[acyl- carrier protein] 2,3,4-saturated fatty acyl-[acp] a malonyl-[acp] a holo-[acyl- carrier protein] 3-oxoacyl-[acp] 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] a (3R)-hydroxy cis Δ5- dodecenoyl- [acp] cis-Δ5- dodecenoyl- [acp] Fatty acid Metabolism glycolysis and pyruvate dehydrogenase Fatty acid Metabolism fabF fabF fabZ fabA fabB fabB