2.0 2012-05-31 14:20:01 -0600 2015-09-18 13:41:03 -0600 ECMDB11120 M2MDB000809 trans-2-Enoyl-OPC4-CoA trans-2-Enoyl-OPC4-CoA participates in alpha-linolenic acid metabolism. trans-2-Enoyl-OPC4-CoA is converted from OPC4-CoA via acyl-CoA oxidase [EC:1.3.3.6] C35H54N7O18P3S 985.826 985.245888185 (2R)-4-({[({[(2R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-{2-[(2-{[(2E)-4-[(1S,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]but-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}butanimidic acid (2R)-4-[({[(2R,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-{2-[(2-{[(2E)-4-[(1S,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]but-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}butanimidic acid CC\C=C/C[C@@H]1C(=O)CCC1C\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/C35H54N7O18P3S/c1-4-5-6-9-22-21(11-12-23(22)43)8-7-10-26(45)64-16-15-37-25(44)13-14-38-33(48)30(47)35(2,3)18-57-63(54,55)60-62(52,53)56-17-24-29(59-61(49,50)51)28(46)34(58-24)42-20-41-27-31(36)39-19-40-32(27)42/h5-7,10,19-22,24,28-30,34,46-47H,4,8-9,11-18H2,1-3H3,(H,37,44)(H,38,48)(H,52,53)(H,54,55)(H2,36,39,40)(H2,49,50,51)/b6-5-,10-7+/t21?,22-,24+,28?,29-,30-,34+/m0/s1 QSAQFDYWYNLXEC-XIFSABRGSA-N Solid Cytoplasm Periplasm logp 1.44 ALOGPS logs -2.33 ALOGPS solubility 4.63e+00 g/l ALOGPS logp -1.6 ChemAxon pka_strongest_acidic 0.83 ChemAxon pka_strongest_basic 4.79 ChemAxon iupac (2R)-4-({[({[(2R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-{2-[(2-{[(2E)-4-[(1S,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]but-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}butanimidic acid ChemAxon average_mass 985.826 ChemAxon mono_mass 985.245888185 ChemAxon smiles CC\C=C/C[C@@H]1C(=O)CCC1C\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 C35H54N7O18P3S ChemAxon inchi InChI=1S/C35H54N7O18P3S/c1-4-5-6-9-22-21(11-12-23(22)43)8-7-10-26(45)64-16-15-37-25(44)13-14-38-33(48)30(47)35(2,3)18-57-63(54,55)60-62(52,53)56-17-24-29(59-61(49,50)51)28(46)34(58-24)42-20-41-27-31(36)39-19-40-32(27)42/h5-7,10,19-22,24,28-30,34,46-47H,4,8-9,11-18H2,1-3H3,(H,37,44)(H,38,48)(H,52,53)(H,54,55)(H2,36,39,40)(H2,49,50,51)/b6-5-,10-7+/t21?,22-,24+,28?,29-,30-,34+/m0/s1 ChemAxon inchikey QSAQFDYWYNLXEC-XIFSABRGSA-N ChemAxon polar_surface_area 387.68 ChemAxon refractivity 229.46 ChemAxon polarizability 93.32 ChemAxon rotatable_bond_count 26 ChemAxon acceptor_count 20 ChemAxon donor_count 9 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon alpha-Linolenic acid metabolism ec00592 fatty acid oxidation 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 PW000758 Metabolic Specdb::MsMs 1302241 Specdb::MsMs 1302242 Specdb::MsMs 1302243 Specdb::MsMs 1416820 Specdb::MsMs 1416821 Specdb::MsMs 1416822 HMDB11120 C16336 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510