2.0 2012-07-30 14:55:30 -0600 2015-09-17 15:41:20 -0600 ECMDB21363 M2MDB001759 Trans-Octadec-2-enoyl-CoA trans-Octadec-2-enoyl-CoA is an intermediate in Biosynthesis of unsaturated fatty acids. trans-Octadec-2-enoyl-CoA is produced from 3-Hydroxyoctadecanoyl-CoA and then converted to Stearoyl-CoA via enzymatic reaction. (2<i>E</i>)-octadecenoyl-CoA (2E)-Octadecenoyl-CoA (2E)-Octadecenoyl-Coenzyme A (E)-2-octadecenoyl-CoA (E)-2-octadecenoyl-coenzyme A (E)-octadec-2-enoyl-CoA (E)-octadec-2-enoyl-coenzyme A 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-octadec-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphate} 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-octadec-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphoric acid} 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-octadec-2-enoyl]sulphanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphate} 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-octadec-2-enoyl]sulphanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphoric acid} <i>trans</i>-2,3-dihydro-stearenoyl-CoA Elaidate coenzyme a Elaidic acid coenzyme a Trans-2,3-Dihydro-stearenoyl-CoA Trans-Octadec-2-enoyl-CoA Trans-Octadec-2-enoyl-coenzyme A C39H68N7O17P3S 1031.98 1031.360524011 {[(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-[(2E)-octadec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid trans-octadec-2-enoyl-coa CCCCCCCCCCCCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)[C@@](O)([H])C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@H](C(O)[C@H]1OP(=O)(O)O)N1C=NC2=C1N=CN=C2N InChI=1S/C39H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h18-19,26-28,32-34,38,49-50H,4-17,20-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b19-18+/t28-,32?,33+,34+,38-/m1/s1 NBCCUIHOHUKBMK-XCRBYWPRSA-N Solid Cytosol logp 2.87 ALOGPS logs -3.10 ALOGPS solubility 8.16e-01 g/l ALOGPS logp 1.72 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-[(2E)-octadec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid ChemAxon average_mass 1031.98 ChemAxon mono_mass 1031.360524011 ChemAxon smiles CCCCCCCCCCCCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)[C@@](O)([H])C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@H](C(O)[C@H]1OP(=O)(O)O)N1C=NC2=C1N=CN=C2N ChemAxon formula C39H68N7O17P3S ChemAxon inchi InChI=1S/C39H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h18-19,26-28,32-34,38,49-50H,4-17,20-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b19-18+/t28-,32?,33+,34+,38-/m1/s1 ChemAxon inchikey NBCCUIHOHUKBMK-XCRBYWPRSA-N ChemAxon polar_surface_area 363.63 ChemAxon refractivity 246.94 ChemAxon polarizability 105.18 ChemAxon rotatable_bond_count 35 ChemAxon acceptor_count 17 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::NmrOneD 255768 Specdb::NmrOneD 255769 Specdb::NmrOneD 255770 Specdb::NmrOneD 255771 Specdb::NmrOneD 255772 Specdb::NmrOneD 255773 Specdb::NmrOneD 255774 Specdb::NmrOneD 255775 Specdb::NmrOneD 255776 Specdb::NmrOneD 255777 Specdb::NmrOneD 255778 Specdb::NmrOneD 255779 Specdb::NmrOneD 255780 Specdb::NmrOneD 255781 Specdb::NmrOneD 255782 Specdb::NmrOneD 255783 Specdb::NmrOneD 255784 Specdb::NmrOneD 255785 Specdb::NmrOneD 255786 Specdb::NmrOneD 255787 Specdb::MsMs 36644 Specdb::MsMs 36645 Specdb::MsMs 36646 Specdb::MsMs 39092 Specdb::MsMs 39093 Specdb::MsMs 39094 Specdb::MsMs 2670975 Specdb::MsMs 2670976 Specdb::MsMs 2670977 Specdb::MsMs 3010839 Specdb::MsMs 3010840 Specdb::MsMs 3010841 HMDB06529 23724662 21865759 C16218 50570 CPD-10262 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 Acyl-coenzyme A dehydrogenase Q47146 FADE_ECOLI fadE http://ecmdb.ca/proteins/Q47146.xml Acyl-CoA thioesterase 2 P0AGG2 TESB_ECOLI tesB http://ecmdb.ca/proteins/P0AGG2.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 FAD + Stearoyl-CoA <> FADH2 + Trans-Octadec-2-enoyl-CoA Octadecenoyl-CoA (N-C18:1CoA) <> Trans-Octadec-2-enoyl-CoA trans-Octadec-2-enoyl-CoA + Trans-Octadec-2-enoyl-CoA > (S)-3-Hydroxyoctadecanoyl-CoA + Water PW_R003803 (S)-3-Hydroxyoctadecanoyl-CoA > trans-Octadec-2-enoyl-CoA + Trans-Octadec-2-enoyl-CoA PW_R003802 trans-Octadec-2-enoyl-CoA + Water + Trans-Octadec-2-enoyl-CoA > Coenzyme A + Hydrogen ion + Elaidic acid PW_R003838