2.02012-05-31 13:03:26 -06002015-06-03 15:53:39 -0600ECMDB01011M2MDB000225Methacrylyl-CoAMethacrylyl-CoA is a metabolite in the valine, leucine and isoleucine degradation pathway and is highly reactive with free thiol compounds (PMID 14684172; KEGG). 2-Methylprop-2-enoyl-CoA2-Methylprop-2-enoyl-Coenzyme AMethacrylyl CoAMethacrylyl Coenzyme AMethacrylyl-CoAMethacrylyl-coenzyme aMethylacrylyl-CoAMethylacrylyl-Coenzyme AS-(2-methyl-2-propenoateS-(2-Methyl-2-propenoate)S-(2-Methyl-2-propenoate) CoAS-(2-Methyl-2-propenoate) Coenzyme AS-(2-methyl-2-propenoic acidS-(2-Methyl-2-propenoic acid)S-(2-Methyl-2-propenoic acid) CoAS-(2-Methyl-2-propenoic acid) coenzyme AC25H40N7O17P3S835.608835.141423115{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylprop-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylprop-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid6008-91-9CC(=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=C1N=CN=C2NInChI=1S/C25H40N7O17P3S/c1-13(2)24(37)53-8-7-27-15(33)5-6-28-22(36)19(35)25(3,4)10-46-52(43,44)49-51(41,42)45-9-14-18(48-50(38,39)40)17(34)23(47-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-12,14,17-19,23,34-35H,1,5-10H2,2-4H3,(H,27,33)(H,28,36)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,17-,18-,19?,23-/m1/s1NPALUEYCDZWBOV-NNYIDDMCSA-NSolidCytoplasmPeriplasmlogp-0.23logs-2.16solubility5.82e+00 g/llogp-4.5pka_strongest_acidic0.82pka_strongest_basic4.01iupac{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylprop-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acidaverage_mass835.608mono_mass835.141423115smilesCC(=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=C1N=CN=C2NformulaC25H40N7O17P3SinchiInChI=1S/C25H40N7O17P3S/c1-13(2)24(37)53-8-7-27-15(33)5-6-28-22(36)19(35)25(3,4)10-46-52(43,44)49-51(41,42)45-9-14-18(48-50(38,39)40)17(34)23(47-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-12,14,17-19,23,34-35H,1,5-10H2,2-4H3,(H,27,33)(H,28,36)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,17-,18-,19?,23-/m1/s1inchikeyNPALUEYCDZWBOV-NNYIDDMCSA-Npolar_surface_area363.63refractivity181.21polarizability73.72rotatable_bond_count21acceptor_count17donor_count9physiological_charge-4formal_charge0Valine, leucine and isoleucine degradationec00280Specdb::NmrOneD330682Specdb::NmrOneD330683Specdb::NmrOneD330684Specdb::NmrOneD330685Specdb::NmrOneD330686Specdb::NmrOneD330687Specdb::NmrOneD330688Specdb::NmrOneD330689Specdb::NmrOneD330690Specdb::NmrOneD330691Specdb::NmrOneD330692Specdb::NmrOneD330693Specdb::NmrOneD330694Specdb::NmrOneD330695Specdb::NmrOneD330696Specdb::NmrOneD330697Specdb::NmrOneD330698Specdb::NmrOneD330699Specdb::NmrOneD330700Specdb::NmrOneD330701Specdb::MsMs23813Specdb::MsMs23814Specdb::MsMs23815Specdb::MsMs30611Specdb::MsMs30612Specdb::MsMs30613HMDB01011440021389035C0346027754METHACRYLYL-COAKanehisa, 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-D114.22080510Shimomura, Y., Honda, T., Goto, H., Nonami, T., Kurokawa, T., Nagasaki, M., Murakami, T. (2004). "Effects of liver failure on the enzymes in the branched-chain amino acid catabolic pathway." Biochem Biophys Res Commun 313:381-385.14684172Lehnert W, Sass JO: Glutaconyl-CoA is the main toxic agent in glutaryl-CoA dehydrogenase deficiency (glutaric aciduria type I). Med Hypotheses. 2005;65(2):330-3.15922108Taniguchi K, Nonami T, Nakao A, Harada A, Kurokawa T, Sugiyama S, Fujitsuka N, Shimomura Y, Hutson SM, Harris RA, Takagi H: The valine catabolic pathway in human liver: effect of cirrhosis on enzyme activities. Hepatology. 1996 Dec;24(6):1395-8.8938168Hawes, John W.; Harper, Edwin T. Synthesis of methacrylyl-CoA and (R)- and (S)-3-hydroxyisobutyryl-CoA. Methods in Enzymology (2 Fatty 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.xmlMethacrylyl-CoA + Water <> (S)-3-Hydroxyisobutyryl-CoAR04224