2.0 2012-07-30 14:54:44 -0600 2015-09-17 15:41:19 -0600 ECMDB21170 M2MDB001579 3-Oxooctadecanoyl-CoA 3-Oxooctadecanoyl-CoA is a metabolite intermediate in the microsomal fatty acid chain elongation system. Microsomal electron-transport components NADPH-cytochrome P450 reductase (EC 1.6.2.4) and cytochrome b5 (EC 1.6.2.2) participate in the conversion from 3-Oxooctadecanoyl-CoA to beta-hydroxystearoyl-CoA, the first reductive step of the microsomal chain elongating system initiated by NADPH. (PMID: 6404652) 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxooctadecanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphate} 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxooctadecanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphoric acid} 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxooctadecanoyl)sulphanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphate} 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxooctadecanoyl)sulphanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphoric acid} 3-Ketostearoyl-coa 3-Ketostearoyl-coenzyme A 3-Oxooctadecanoyl-CoA 3-Oxooctadecanoyl-coenzyme A 3-Oxostearoyl-CoA 3-Oxostearoyl-Coenzyme A b-Ketostearoyl-CoA b-Ketostearoyl-coenzyme A Beta-Ketostearoyl-CoA Beta-Ketostearoyl-Coenzyme A β-Ketostearoyl-CoA β-Ketostearoyl-coenzyme A C39H66N7O18P3S 1045.964 1045.339788569 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxooctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid 3-oxooctadecanoyl-coa 86370-20-9 CCCCCCCCCCCCCCCC(=O)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 InChI=1S/C39H68N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(47)22-30(49)68-21-20-41-29(48)18-19-42-37(52)34(51)39(2,3)24-61-67(58,59)64-66(56,57)60-23-28-33(63-65(53,54)55)32(50)38(62-28)46-26-45-31-35(40)43-25-44-36(31)46/h25-26,28,32-34,38,50-51H,4-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55)/p-2/t28-,32-,33-,34+,38-/m1/s1 LGOGWHDPDVAUNY-LFZQUHGESA-L Solid Cytosol Membrane logp 2.43 ALOGPS logs -2.81 ALOGPS solubility 1.61e+00 g/l ALOGPS logp 0.82 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic 4.01 ChemAxon iupac {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxooctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid ChemAxon average_mass 1045.964 ChemAxon mono_mass 1045.339788569 ChemAxon smiles CCCCCCCCCCCCCCCC(=O)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 ChemAxon formula C39H66N7O18P3S ChemAxon inchi InChI=1S/C39H68N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(47)22-30(49)68-21-20-41-29(48)18-19-42-37(52)34(51)39(2,3)24-61-67(58,59)64-66(56,57)60-23-28-33(63-65(53,54)55)32(50)38(62-28)46-26-45-31-35(40)43-25-44-36(31)46/h25-26,28,32-34,38,50-51H,4-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55)/p-2/t28-,32-,33-,34+,38-/m1/s1 ChemAxon inchikey LGOGWHDPDVAUNY-LFZQUHGESA-L ChemAxon polar_surface_area 380.7 ChemAxon refractivity 246.54 ChemAxon polarizability 105.18 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 18 ChemAxon donor_count 9 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon fatty acid oxidation (steareate) Although enzymes of the pathway handle both short and long chain fatty acids, it is the long chain compounds that induce the enzymes of the pathway . Each turn of the cycle removes two carbon atoms until only two or three remain. When even-numbered fatty acids are broken down, a two-carbon compound remains, acetyl-CoA. When odd number fatty acids are broken down, a three-carbon residue results, propionylCoA. Unsaturated fatty acids, with cis double bonds located at odd-numbered carbon atoms, enter the main pathway of saturated fatty acid degradation by converting related metabolites of cis configuration and D stereoisomers, derived from breakdown of unsaturated fatty acids, to the trans- or L isomers of saturated fatty acid breakdown by an isomerase and an epimerase, respectively. When cis double bonds are located at even-numbered carbon atoms, such as linoleic acid (cis,cis(9,12)-octadecadienoic acid), after the fatty acid is degraded to the ten carbon stage an extra step is required to deal with the resulting compound, trans,δ(2)-cis,δ(4)decadienoyl-CoA. The enzyme 2,4-dienoyl-CoA reductase, converts this to trans,δ(2)decenoyl-CoA which enters the normal cycle at the point of the isomerase. The order of the reaction is as follows: a 2,3,4 saturated fatty acid is transformed into a 2,3,4 saturated fatty acyl CoA through a Long and short chain fatty acid CoA ligase. The 2,3,4 saturated fatty acyl CoA is then transformed into a trans 2 enoyl CoA. This enoyl can also be produced from a cis 3 enoyl CoA through a fatty acid oxidation protein complex. The trans 2 enoyl is transformed into a 3s 3 hydroxyacyl CoA through a 2,3 dehydroadipyl CoA hydratase. This same enzyme turns the product into a 3-oxoacyl-CoA. This is followed by the last step in the reaction when the oxoacyl-coa is turn into an acetyl coa+ a 2,3,4 saturated fatty acyl CoA through a 3-ketoacyl-CoA thiolase PW001024 Metabolic Specdb::MsMs 36332 Specdb::MsMs 36333 Specdb::MsMs 36334 Specdb::MsMs 38780 Specdb::MsMs 38781 Specdb::MsMs 38782 HMDB06498 23724660 21865760 C16216 50571 CPD-10260 Nagao, M., Ishibashi, T., Okayasu, T., Imai, Y. (1983). "Possible involvement of NADPH-cytochrome P450 reductase and cytochrome b5 on beta-ketostearoyl-CoA reduction in microsomal fatty acid chain elongation supported by NADPH." FEBS Lett 155:11-14. 6404652 3-oxoacyl-[acyl-carrier-protein] reductase P0AEK2 FABG_ECOLI fabG http://ecmdb.ca/proteins/P0AEK2.xml 3-ketoacyl-CoA thiolase P21151 FADA_ECOLI fadA http://ecmdb.ca/proteins/P21151.xml Fatty acid oxidation complex subunit alpha P21177 FADB_ECOLI fadB http://ecmdb.ca/proteins/P21177.xml Probable enoyl-CoA hydratase paaF P76082 PAAF_ECOLI paaF http://ecmdb.ca/proteins/P76082.xml 3-ketoacyl-CoA thiolase_ P76503 FADI_ECOLI fadI http://ecmdb.ca/proteins/P76503.xml Fatty acid oxidation complex subunit alpha_ P77399 FADJ_ECOLI fadJ http://ecmdb.ca/proteins/P77399.xml Fatty acid oxidation complex subunit alpha P21177 FADB_ECOLI fadB http://ecmdb.ca/proteins/P21177.xml 3-Oxooctadecanoyl-CoA + Coenzyme A <> Acetyl-CoA + Palmityl-CoA 3-Oxooctadecanoyl-CoA + Hydrogen ion + NADH <> (S)-3-Hydroxyoctadecanoyl-CoA + NAD 3-Oxooctadecanoyl-CoA + NADPH + Hydrogen ion <> 3-Hydroxyoctadecanoyl-CoA + NADP R07759 (S)-3-Hydroxyoctadecanoyl-CoA + NAD > NADH + Hydrogen ion + 3-Oxooctadecanoyl-CoA + 3-Oxooctadecanoyl-CoA PW_R003804 3-Oxooctadecanoyl-CoA + Coenzyme A + 3-Oxooctadecanoyl-CoA > Acetyl-CoA + Stearoyl-CoA + Stearoyl-CoA PW_R003805