2.0 2012-05-31 14:01:21 -0600 2015-06-03 15:54:35 -0600 ECMDB03948 M2MDB000543 (2E)-Decenoyl-CoA (2E)-Decenoyl-CoAis a beta-oxidation intermediate derivative of palmitoyl-CoA and the substrate of the enzyme long chain-fatty acyl-CoA Ligase. This enzyme catalyzes the esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. This compound is also a substrate for 3-ketoacyl-CoA thiolase. This enzyme catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. (E)-S-2-decenoate (E)-S-2-decenoate CoA (E)-S-2-decenoate Coenzyme A (E)-S-2-decenoic acid (E)-S-2-decenoic acid CoA (E)-S-2-decenoic acid Coenzyme A 2-trans-Decenoyl-CoA 2-trans-Decenoyl-Coenzyme A S-(2E)-2-Decenoate S-(2E)-2-Decenoate CoA S-(2E)-2-Decenoate Coenzyme A S-(2E)-2-Decenoic acid S-(2E)-2-Decenoic acid CoA S-(2E)-2-Decenoic acid Coenzyme A Trans-2-Decenoylcoenzyme A Trans-D2,3-Decenoyl-CoA Trans-D2,3-Decenoyl-Coenzyme A Trans-Dec-2-enoyl-CoA Trans-Dec-2-enoyl-Coenzyme A C31H52N7O17P3S 919.768 919.235323499 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-{[({[(3-{[2-({2-[(2E)-dec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxy}phosphonic acid [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-({[(3-{[2-({2-[(2E)-dec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxyphosphonic acid 10018-95-8 CCCCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)C(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=C(N)N=CN=C12 InChI=1S/C31H52N7O17P3S/c1-4-5-6-7-8-9-10-11-22(40)59-15-14-33-21(39)12-13-34-29(43)26(42)31(2,3)17-52-58(49,50)55-57(47,48)51-16-20-25(54-56(44,45)46)24(41)30(53-20)38-19-37-23-27(32)35-18-36-28(23)38/h10-11,18-20,24-26,30,41-42H,4-9,12-17H2,1-3H3,(H,33,39)(H,34,43)(H,47,48)(H,49,50)(H2,32,35,36)(H2,44,45,46)/b11-10+/t20-,24-,25-,26?,30-/m1/s1 MGNBGCRQQFMNBM-VHTAIFHGSA-N Solid Cytosol logp 0.92 ALOGPS logs -2.53 ALOGPS solubility 2.71e+00 g/l ALOGPS logp -2.9 ChemAxon pka_strongest_acidic 0.83 ChemAxon pka_strongest_basic 4.95 ChemAxon iupac {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-{[({[(3-{[2-({2-[(2E)-dec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxy}phosphonic acid ChemAxon average_mass 919.768 ChemAxon mono_mass 919.235323499 ChemAxon smiles CCCCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)C(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=C(N)N=CN=C12 ChemAxon formula C31H52N7O17P3S ChemAxon inchi InChI=1S/C31H52N7O17P3S/c1-4-5-6-7-8-9-10-11-22(40)59-15-14-33-21(39)12-13-34-29(43)26(42)31(2,3)17-52-58(49,50)55-57(47,48)51-16-20-25(54-56(44,45)46)24(41)30(53-20)38-19-37-23-27(32)35-18-36-28(23)38/h10-11,18-20,24-26,30,41-42H,4-9,12-17H2,1-3H3,(H,33,39)(H,34,43)(H,47,48)(H,49,50)(H2,32,35,36)(H2,44,45,46)/b11-10+/t20-,24-,25-,26?,30-/m1/s1 ChemAxon inchikey MGNBGCRQQFMNBM-VHTAIFHGSA-N ChemAxon polar_surface_area 363.63 ChemAxon refractivity 210.14 ChemAxon polarizability 87.08 ChemAxon rotatable_bond_count 27 ChemAxon acceptor_count 17 ChemAxon donor_count 9 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Fatty acid metabolism This pathway depicts the degradation of palmitic acid (C16:0). Fatty acid degradation and synthesis are relatively simple processes that are essentially the reverse of each other. The process of fatty acid degradation, also known as Beta-Oxidation, converts an aliphatic compound into a set of activated acetyl units (acetyl CoA) that can be processed by the citric acid cycle. An activated fatty acid is first oxidized to introduce a double bond; the double bond is then hydrated to introduce an oxygen; the alcohol is then oxidized to a ketone; and, finally, the four carbon fragment is cleaved by coenzyme A to yield acetyl CoA and a fatty acid chain two carbons shorter. If the fatty acid has an even number of carbon atoms and is saturated, the process is simply repeated until the fatty acid is completely converted into acetyl CoA units. Fatty acid synthesis is essentially the reverse of this process. Because the result is a polymer, the process starts with monomers—in this case with activated acyl group and malonyl units. The malonyl unit is condensed with the acetyl unit to form a four-carbon fragment. To produce the required hydrocarbon chain, the carbonyl must be reduced. The fragment is reduced, dehydrated, and reduced again, exactly the opposite of degradation, to bring the carbonyl group to the level of a methylene group with the formation of butyryl CoA. Another activated malonyl group condenses with the butyryl unit and the process is repeated until a C16 fatty acid is synthesized. The first step converts the hydroxydecanoyl into a trans 2decenoyl acp through a protein complex conformed of a hydroxomyristoyl dehydratase and a hydroxydecanoyl dehydratase. The second step leads to the production of a cis 3 decenoyl acp through a 3-hydroxydecanoyl acp dehydratase. For the third step the cis 3 decenoyl acp enters a cycle involving a synthase, reductase, dehydratase and an enoyl reductase which in turn produce a cis x enoyl-acp, hydroxy cis x enoyl, trans x-2 cis x enoyl acp and cis x enoyl respectively.This is done until a palmitoleoyl is produce. In said case the pathway procedes in two different directions. It can either produce a palmitoleic acid through a acyl-coa thioesterase, or produce a Vaccenic acid through a different set of reactions. This process is achieved through a 3-oxoacyl acp synthase, a 3-oxoacyl acp reductase, a 3r hydroxymyristoyl dehydratase and an enoyl acp reductase that produces a transition through 3-oxo cis vaccenoyl acp, 3 hydroxy cis vaccenoyl acp, cis vaccen 2 enoyl acp and a cis vaccenoyl acp respectively. At this point it goes through one final reaction to produce a Vaccenic acid, through an acyl-CoA thioesterase PW000796 ec00071 Metabolic Collection of Reactions without pathways PW001891 Metabolic fatty acid oxidation (Decanoate) 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 PW001018 Metabolic Specdb::EiMs 2055 Specdb::NmrOneD 35142 Specdb::NmrOneD 35143 Specdb::NmrOneD 35144 Specdb::NmrOneD 35145 Specdb::NmrOneD 35146 Specdb::NmrOneD 35147 Specdb::NmrOneD 35148 Specdb::NmrOneD 35149 Specdb::NmrOneD 35150 Specdb::NmrOneD 35151 Specdb::NmrOneD 35152 Specdb::NmrOneD 35153 Specdb::NmrOneD 35154 Specdb::NmrOneD 35155 Specdb::NmrOneD 35156 Specdb::NmrOneD 35157 Specdb::NmrOneD 35158 Specdb::NmrOneD 35159 Specdb::NmrOneD 35160 Specdb::NmrOneD 35161 Specdb::MsMs 28238 Specdb::MsMs 28239 Specdb::MsMs 28240 Specdb::MsMs 34796 Specdb::MsMs 34797 Specdb::MsMs 34798 Specdb::MsMs 2707742 Specdb::MsMs 2707743 Specdb::MsMs 2707744 Specdb::MsMs 3000511 Specdb::MsMs 3000512 Specdb::MsMs 3000513 HMDB03948 5280768 4444334 C05275 10723 T2-DECENOYL-COA Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 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 Hunt MC, Solaas K, Kase BF, Alexson SE: Characterization of an acyl-coA thioesterase that functions as a major regulator of peroxisomal lipid metabolism. J Biol Chem. 2002 Jan 11;277(2):1128-38. Epub 2001 Oct 22. 11673457 Fatty acid oxidation complex subunit alpha P21177 FADB_ECOLI fadB http://ecmdb.ca/proteins/P21177.xml 2,4-dienoyl-CoA reductase [NADPH] P42593 FADH_ECOLI fadH http://ecmdb.ca/proteins/P42593.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 Fatty acid oxidation complex subunit alpha P21177 FADB_ECOLI fadB http://ecmdb.ca/proteins/P21177.xml (S)-Hydroxydecanoyl-CoA <> (2E)-Decenoyl-CoA + Water R04744 Decanoyl-CoA (N-C10:0CoA) + FAD <> (2E)-Decenoyl-CoA + FADH2 R04754 (2E)-Decenoyl-CoA + NADP <> Hydrogen ion + trans-Delta2, cis-delta4-decadienoyl-CoA + NADPH DIENOYLCOAREDUCT-RXN (2E)-Decenoyl-CoA > Water + (S)-Hydroxydecanoyl-CoA PW_R003773 (S)-Hydroxydecanoyl-CoA <> (2E)-Decenoyl-CoA + Water PW_R002473 Decanoyl-CoA (n-C10:0CoA) + electron-transfer flavoprotein + Decanoyl-CoA (N-C10:0CoA) > (2E)-Decenoyl-CoA + Reduced electron-transfer flavoprotein PW_R002489 (S)-Hydroxydecanoyl-CoA > (2E)-Decenoyl-CoA PW_R003772 trans-Delta2, cis-delta4-decadienoyl-CoA + NADPH + Hydrogen ion > (2E)-Decenoyl-CoA + NADP PW_R005912