2.02012-07-30 14:55:30 -06002015-09-17 15:41:20 -0600ECMDB21363M2MDB001759Trans-Octadec-2-enoyl-CoAtrans-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 A3'-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-CoAElaidate coenzyme aElaidic acid coenzyme aTrans-2,3-Dihydro-stearenoyl-CoATrans-Octadec-2-enoyl-CoATrans-Octadec-2-enoyl-coenzyme AC39H68N7O17P3S1031.981031.360524011{[(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 acidtrans-octadec-2-enoyl-coaCCCCCCCCCCCCCCC\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=C2NInChI=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/s1NBCCUIHOHUKBMK-XCRBYWPRSA-NSolidCytosollogp2.87logs-3.10solubility8.16e-01 g/llogp1.72pka_strongest_acidic0.82pka_strongest_basic4.01iupac{[(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 acidaverage_mass1031.98mono_mass1031.360524011smilesCCCCCCCCCCCCCCC\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=C2NformulaC39H68N7O17P3SinchiInChI=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/s1inchikeyNBCCUIHOHUKBMK-XCRBYWPRSA-Npolar_surface_area363.63refractivity246.94polarizability105.18rotatable_bond_count35acceptor_count17donor_count9physiological_charge-4formal_charge0fatty 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 thiolasePW001024MetabolicSpecdb::NmrOneD255768Specdb::NmrOneD255769Specdb::NmrOneD255770Specdb::NmrOneD255771Specdb::NmrOneD255772Specdb::NmrOneD255773Specdb::NmrOneD255774Specdb::NmrOneD255775Specdb::NmrOneD255776Specdb::NmrOneD255777Specdb::NmrOneD255778Specdb::NmrOneD255779Specdb::NmrOneD255780Specdb::NmrOneD255781Specdb::NmrOneD255782Specdb::NmrOneD255783Specdb::NmrOneD255784Specdb::NmrOneD255785Specdb::NmrOneD255786Specdb::NmrOneD255787Specdb::MsMs36644Specdb::MsMs36645Specdb::MsMs36646Specdb::MsMs39092Specdb::MsMs39093Specdb::MsMs39094Specdb::MsMs2670975Specdb::MsMs2670976Specdb::MsMs2670977Specdb::MsMs3010839Specdb::MsMs3010840Specdb::MsMs3010841HMDB065292372466221865759C1621850570CPD-10262Fatty acid oxidation complex subunit alphaP21177FADB_ECOLIfadBhttp://ecmdb.ca/proteins/P21177.xmlProbable enoyl-CoA hydratase paaFP76082PAAF_ECOLIpaaFhttp://ecmdb.ca/proteins/P76082.xmlFatty acid oxidation complex subunit alpha_P77399FADJ_ECOLIfadJhttp://ecmdb.ca/proteins/P77399.xmlAcyl-coenzyme A dehydrogenaseQ47146FADE_ECOLIfadEhttp://ecmdb.ca/proteins/Q47146.xmlAcyl-CoA thioesterase 2P0AGG2TESB_ECOLItesBhttp://ecmdb.ca/proteins/P0AGG2.xmlFatty acid oxidation complex subunit alphaP21177FADB_ECOLIfadBhttp://ecmdb.ca/proteins/P21177.xml(S)-3-Hydroxyoctadecanoyl-CoA <> Water + Trans-Octadec-2-enoyl-CoAFAD + Stearoyl-CoA <> FADH2 + Trans-Octadec-2-enoyl-CoAOctadecenoyl-CoA (N-C18:1CoA) <> Trans-Octadec-2-enoyl-CoAtrans-Octadec-2-enoyl-CoA + Trans-Octadec-2-enoyl-CoA > (S)-3-Hydroxyoctadecanoyl-CoA + WaterPW_R003803(S)-3-Hydroxyoctadecanoyl-CoA > trans-Octadec-2-enoyl-CoA + Trans-Octadec-2-enoyl-CoAPW_R003802trans-Octadec-2-enoyl-CoA + Water + Trans-Octadec-2-enoyl-CoA > Coenzyme A + Hydrogen ion + Elaidic acidPW_R003838