2.0 2012-07-30 14:54:38 -0600 2015-06-03 17:20:38 -0600 ECMDB21101 M2MDB001510 (S)-3-Hydroxyoctadecanoyl-CoA (s)-3-hydroxyoctadecanoyl-coa belongs to the class of Acyl CoAs. These are organic compounds contaning a coenzyme A substructure linked to another moeity through an ester bond. (inferred from compound structure) 3-Hydroxyoctadecanoyl-CoA 3-Hydroxyoctadecanoyl-coenzyme A b-Hydroxy stearyl-CoA b-Hydroxystearoyl-CoA beta-Hydroxy stearyl-CoA beta-Hydroxystearoyl-CoA β-Hydroxy stearyl-CoA β-Hydroxystearoyl-CoA C39H70N7O18P3S 1049.995 1049.371088697 {[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxyoctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid [5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxyoctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid CCCCCCCCCCCCCCCC(O)CC(=O)SCCN=C(O)CCN=C(O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12 InChI=1S/C39H70N7O18P3S/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/h25-28,32-34,38,47,50-51H,4-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55) WZMAIEGYXCOYSH-UHFFFAOYSA-N Cytosol logp 2.19 ALOGPS logs -2.80 ALOGPS solubility 1.66e+00 g/l ALOGPS logp 0.26 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic 4.01 ChemAxon iupac {[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxyoctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid ChemAxon average_mass 1049.995 ChemAxon mono_mass 1049.371088697 ChemAxon smiles CCCCCCCCCCCCCCCC(O)CC(=O)SCCN=C(O)CCN=C(O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12 ChemAxon formula C39H70N7O18P3S ChemAxon inchi InChI=1S/C39H70N7O18P3S/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/h25-28,32-34,38,47,50-51H,4-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55) ChemAxon inchikey WZMAIEGYXCOYSH-UHFFFAOYSA-N ChemAxon polar_surface_area 383.86 ChemAxon refractivity 247.37 ChemAxon polarizability 105.07 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 18 ChemAxon donor_count 10 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::EiMs 4115 Specdb::NmrOneD 278118 Specdb::NmrOneD 278119 Specdb::NmrOneD 278120 Specdb::NmrOneD 278121 Specdb::NmrOneD 278122 Specdb::NmrOneD 278123 Specdb::NmrOneD 278124 Specdb::NmrOneD 278125 Specdb::NmrOneD 278126 Specdb::NmrOneD 278127 Specdb::NmrOneD 278128 Specdb::NmrOneD 278129 Specdb::NmrOneD 278130 Specdb::NmrOneD 278131 Specdb::NmrOneD 278132 Specdb::NmrOneD 278133 Specdb::NmrOneD 278134 Specdb::NmrOneD 278135 Specdb::NmrOneD 278136 Specdb::NmrOneD 278137 Specdb::MsMs 38504 Specdb::MsMs 38505 Specdb::MsMs 38506 Specdb::MsMs 40952 Specdb::MsMs 40953 Specdb::MsMs 40954 Specdb::MsMs 2780758 Specdb::MsMs 2780759 Specdb::MsMs 2780760 Specdb::MsMs 2924293 Specdb::MsMs 2924294 Specdb::MsMs 2924295 193824 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 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 (S)-3-Hydroxyoctadecanoyl-CoA <> Water + Trans-Octadec-2-enoyl-CoA 3-Oxooctadecanoyl-CoA + Hydrogen ion + NADH <> (S)-3-Hydroxyoctadecanoyl-CoA + NAD trans-Octadec-2-enoyl-CoA + Trans-Octadec-2-enoyl-CoA > (S)-3-Hydroxyoctadecanoyl-CoA + Water PW_R003803 (S)-3-Hydroxyoctadecanoyl-CoA + NAD > NADH + Hydrogen ion + 3-Oxooctadecanoyl-CoA + 3-Oxooctadecanoyl-CoA PW_R003804 (S)-3-Hydroxyoctadecanoyl-CoA > trans-Octadec-2-enoyl-CoA + Trans-Octadec-2-enoyl-CoA PW_R003802