2.0 2012-05-31 13:03:26 -0600 2015-06-03 15:53:39 -0600 ECMDB01011 M2MDB000225 Methacrylyl-CoA Methacrylyl-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-CoA 2-Methylprop-2-enoyl-Coenzyme A Methacrylyl CoA Methacrylyl Coenzyme A Methacrylyl-CoA Methacrylyl-coenzyme a Methylacrylyl-CoA Methylacrylyl-Coenzyme A S-(2-methyl-2-propenoate S-(2-Methyl-2-propenoate) S-(2-Methyl-2-propenoate) CoA S-(2-Methyl-2-propenoate) Coenzyme A S-(2-methyl-2-propenoic acid S-(2-Methyl-2-propenoic acid) S-(2-Methyl-2-propenoic acid) CoA S-(2-Methyl-2-propenoic acid) coenzyme A C25H40N7O17P3S 835.608 835.141423115 {[(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 acid 6008-91-9 CC(=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=C2N InChI=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/s1 NPALUEYCDZWBOV-NNYIDDMCSA-N Solid Cytoplasm Periplasm logp -0.23 ALOGPS logs -2.16 ALOGPS solubility 5.82e+00 g/l ALOGPS logp -4.5 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic 4.01 ChemAxon iupac {[(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 ChemAxon average_mass 835.608 ChemAxon mono_mass 835.141423115 ChemAxon smiles CC(=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=C2N ChemAxon formula C25H40N7O17P3S ChemAxon inchi InChI=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/s1 ChemAxon inchikey NPALUEYCDZWBOV-NNYIDDMCSA-N ChemAxon polar_surface_area 363.63 ChemAxon refractivity 181.21 ChemAxon polarizability 73.72 ChemAxon rotatable_bond_count 21 ChemAxon acceptor_count 17 ChemAxon donor_count 9 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Valine, leucine and isoleucine degradation ec00280 Specdb::NmrOneD 330682 Specdb::NmrOneD 330683 Specdb::NmrOneD 330684 Specdb::NmrOneD 330685 Specdb::NmrOneD 330686 Specdb::NmrOneD 330687 Specdb::NmrOneD 330688 Specdb::NmrOneD 330689 Specdb::NmrOneD 330690 Specdb::NmrOneD 330691 Specdb::NmrOneD 330692 Specdb::NmrOneD 330693 Specdb::NmrOneD 330694 Specdb::NmrOneD 330695 Specdb::NmrOneD 330696 Specdb::NmrOneD 330697 Specdb::NmrOneD 330698 Specdb::NmrOneD 330699 Specdb::NmrOneD 330700 Specdb::NmrOneD 330701 Specdb::MsMs 23813 Specdb::MsMs 23814 Specdb::MsMs 23815 Specdb::MsMs 30611 Specdb::MsMs 30612 Specdb::MsMs 30613 HMDB01011 440021 389035 C03460 27754 METHACRYLYL-COA 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 Shimomura, 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. 14684172 Lehnert 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. 15922108 Taniguchi 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. 8938168 Hawes, 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 alpha P21177 FADB_ECOLI fadB http://ecmdb.ca/proteins/P21177.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 Fatty acid oxidation complex subunit alpha P21177 FADB_ECOLI fadB http://ecmdb.ca/proteins/P21177.xml Methacrylyl-CoA + Water <> (S)-3-Hydroxyisobutyryl-CoA R04224