2.02012-05-31 14:00:52 -06002015-06-03 15:54:33 -0600ECMDB03938M2MDB000534(S)-Hydroxydecanoyl-CoA(S)-Hydroxydecanoyl-CoA has a role in the synthesis and oxidation of fatty acids. It is involved in fatty acid elongation. In this pathway 3-Oxodecanoyl-CoA is acted upon by two enzymes, 3-hydroxyacyl-CoA dehydrogenase and long-chain-3-hydroxyacyl-CoA dehydrogenase to produce (S)-Hydroxydecanoyl-CoA. Since coenzyme A is chemically a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group it is usually referred to as CoASH or HSCoA.(<i>S</i>)-3-hydroxydecanoyl-CoA(S)-3-Hydroxydecanoyl-CoA(S)-3-Hydroxydecanoyl-Coenzyme A3-Hydroxydecanoyl-CoA3-Hydroxydecanoyl-Coenzyme A3S-Hydroxy-decanoyl-CoA3S-Hydroxy-decanoyl-Coenzyme AB-Hydroxydecanoyl coenzyme ABeta-Hydroxydecanoyl coenzyme ADL-b-Hydroxydecanoyl coenzyme ADL-beta-Hydroxydecanoyl coenzyme ADL-β-Hydroxydecanoyl coenzyme AS-(3-hydroxydecanoateS-(3-Hydroxydecanoate)S-(3-Hydroxydecanoate) CoAS-(3-Hydroxydecanoate) Coenzyme AS-(3-Hydroxydecanoate)CoAS-(3-Hydroxydecanoate)Coenzyme AS-(3-hydroxydecanoic acidS-(3-Hydroxydecanoic acid)S-(3-Hydroxydecanoic acid) CoAS-(3-Hydroxydecanoic acid) coenzyme AS-(3-Hydroxydecanoic acid)CoAS-(3-Hydroxydecanoic acid)coenzyme Aβ-Hydroxydecanoyl coenzyme AC31H54N7O18P3S937.783937.245888185{[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxydecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid(S)-3-hydroxydecanoyl-coa6245-70-1CCCCCCC[C@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)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=C(N)N=CN=C12InChI=1S/C31H54N7O18P3S/c1-4-5-6-7-8-9-19(39)14-22(41)60-13-12-33-21(40)10-11-34-29(44)26(43)31(2,3)16-53-59(50,51)56-58(48,49)52-15-20-25(55-57(45,46)47)24(42)30(54-20)38-18-37-23-27(32)35-17-36-28(23)38/h17-20,24-26,30,39,42-43H,4-16H2,1-3H3,(H,33,40)(H,34,44)(H,48,49)(H,50,51)(H2,32,35,36)(H2,45,46,47)/t19-,20+,24?,25-,26-,30+/m0/s1HIVSMYZAMUNFKZ-WQUYVQPTSA-NSolidCytosollogp0.31logs-2.46solubility3.25e+00 g/llogp-4.4pka_strongest_acidic0.83pka_strongest_basic4.95iupac{[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxydecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acidaverage_mass937.783mono_mass937.245888185smilesCCCCCCC[C@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)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=C(N)N=CN=C12formulaC31H54N7O18P3SinchiInChI=1S/C31H54N7O18P3S/c1-4-5-6-7-8-9-19(39)14-22(41)60-13-12-33-21(40)10-11-34-29(44)26(43)31(2,3)16-53-59(50,51)56-58(48,49)52-15-20-25(55-57(45,46)47)24(42)30(54-20)38-18-37-23-27(32)35-17-36-28(23)38/h17-20,24-26,30,39,42-43H,4-16H2,1-3H3,(H,33,40)(H,34,44)(H,48,49)(H,50,51)(H2,32,35,36)(H2,45,46,47)/t19-,20+,24?,25-,26-,30+/m0/s1inchikeyHIVSMYZAMUNFKZ-WQUYVQPTSA-Npolar_surface_area383.86refractivity210.56polarizability87.9rotatable_bond_count28acceptor_count18donor_count10physiological_charge-4formal_charge0Fatty acid metabolismThis 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 thioesterasePW000796ec00071Metabolicfatty 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 thiolasePW001018MetabolicSpecdb::EiMs2205Specdb::NmrOneD149740Specdb::NmrOneD149741Specdb::NmrOneD149742Specdb::NmrOneD149743Specdb::NmrOneD149744Specdb::NmrOneD149745Specdb::NmrOneD149746Specdb::NmrOneD149747Specdb::NmrOneD149748Specdb::NmrOneD149749Specdb::NmrOneD149750Specdb::NmrOneD149751Specdb::NmrOneD149752Specdb::NmrOneD149753Specdb::NmrOneD149754Specdb::NmrOneD149755Specdb::NmrOneD149756Specdb::NmrOneD149757Specdb::NmrOneD149758Specdb::NmrOneD149759Specdb::MsMs28829Specdb::MsMs28830Specdb::MsMs28831Specdb::MsMs35387Specdb::MsMs35388Specdb::MsMs35389Specdb::MsMs2356260Specdb::MsMs2356261Specdb::MsMs2356262Specdb::MsMs2609384Specdb::MsMs2609385Specdb::MsMs2609386HMDB039381606115917220838C0526428325CPD0-2244Keseler, 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-D590.21097882Kanehisa, 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-D114.22080510Qi, Q.; Steinbuchel, A.; Rehm, B. H. A. In vitro synthesis of poly(3-hydroxydecanoate): purification and enzymatic characterization of type II polyhydroxyalkanoate synthases PhaC1 and PhaC2 from Pseudomonas aeruginosa. Applied Microbiology and BiotechFatty 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.xmlFatty acid oxidation complex subunit alphaP21177FADB_ECOLIfadBhttp://ecmdb.ca/proteins/P21177.xml(S)-Hydroxydecanoyl-CoA <> (2E)-Decenoyl-CoA + WaterR047443-Oxodecanoyl-CoA + Hydrogen ion + NADH <> (S)-Hydroxydecanoyl-CoA + NAD(2E)-Decenoyl-CoA > Water + (S)-Hydroxydecanoyl-CoAPW_R003773(S)-Hydroxydecanoyl-CoA + NAD > NADH + Hydrogen ion + 3-Oxodecanoyl-CoAPW_R003774(S)-Hydroxydecanoyl-CoA <> (2E)-Decenoyl-CoA + WaterPW_R002473(S)-Hydroxydecanoyl-CoA + NAD <> 3-Oxodecanoyl-CoA + Hydrogen ion + NADHPW_R002474(S)-Hydroxydecanoyl-CoA > (2E)-Decenoyl-CoAPW_R003772