2.0 2012-05-31 13:53:30 -0600 2015-06-03 15:54:09 -0600 ECMDB01493 M2MDB000401 3-Methylcrotonyl-CoA 3-Methylcrotonyl-CoA is an essential metabolite for leucine metabolism. β-methylcrotonoyl-CoA 3-Methylbut-2-enoyl-CoA 3-Methylbut-2-enoyl-Coenzyme A 3-Methylcrotonoyl-CoA 3-Methylcrotonoyl-Coenzyme A 3-Methylcrotonyl-CoA 3-Methylcrotonyl-Coenzyme A b-Methylcrotonoyl-CoA b-Methylcrotonoyl-coenzyme A b-Methylcrotonyl-CoA B-Methylcrotonyl-CoA (HMDB01493 B-Methylcrotonyl-Coenzyme A B-Methylcrotonyl-Coenzyme A (HMDB01493 Beta-Methylcrotonoyl-CoA Beta-Methylcrotonoyl-Coenzyme A Beta-Methylcrotonyl-CoA Beta-Methylcrotonyl-CoA (HMDB01493 Beta-Methylcrotonyl-Coenzyme A Beta-Methylcrotonyl-Coenzyme A (HMDB01493 Dimethylacryloyl-CoA Dimethylacryloyl-Coenzyme A β-Methylcrotonoyl-CoA β-Methylcrotonoyl-coenzyme A β-Methylcrotonyl-CoA β-Methylcrotonyl-CoA (HMDB01493 β-Methylcrotonyl-coenzyme A β-Methylcrotonyl-coenzyme A (HMDB01493 C26H42N7O17P3S 849.635 849.157073179 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-methylbut-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-[(3-methylbut-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid 793193-48-3 CC(C)=CC(=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/C26H42N7O17P3S/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h9,12-13,15,19-21,25,36-37H,5-8,10-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21?,25-/m1/s1 BXIPALATIYNHJN-TVCSPYKZSA-N Solid Cytoplasm Periplasm logp -0.13 ALOGPS logs -2.19 ALOGPS solubility 5.51e+00 g/l ALOGPS logp -4.3 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-[(3-methylbut-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid ChemAxon average_mass 849.635 ChemAxon mono_mass 849.157073179 ChemAxon smiles CC(C)=CC(=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 C26H42N7O17P3S ChemAxon inchi InChI=1S/C26H42N7O17P3S/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h9,12-13,15,19-21,25,36-37H,5-8,10-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21?,25-/m1/s1 ChemAxon inchikey BXIPALATIYNHJN-TVCSPYKZSA-N ChemAxon polar_surface_area 363.63 ChemAxon refractivity 186.81 ChemAxon polarizability 75.87 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 Geraniol degradation ec00281 Specdb::EiMs 2696 Specdb::NmrOneD 328192 Specdb::NmrOneD 328193 Specdb::NmrOneD 328194 Specdb::NmrOneD 328195 Specdb::NmrOneD 328196 Specdb::NmrOneD 328197 Specdb::NmrOneD 328198 Specdb::NmrOneD 328199 Specdb::NmrOneD 328200 Specdb::NmrOneD 328201 Specdb::NmrOneD 328202 Specdb::NmrOneD 328203 Specdb::NmrOneD 328204 Specdb::NmrOneD 328205 Specdb::NmrOneD 328206 Specdb::NmrOneD 328207 Specdb::NmrOneD 328208 Specdb::NmrOneD 328209 Specdb::NmrOneD 328210 Specdb::NmrOneD 328211 Specdb::MsMs 25223 Specdb::MsMs 25224 Specdb::MsMs 25225 Specdb::MsMs 31781 Specdb::MsMs 31782 Specdb::MsMs 31783 HMDB01493 439869 388909 C03069 15486 3-METHYL-CROTONYL-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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Wysocki SJ, Hahnel R: 3-Methylcrotonylglycine excretion in 3-hydroxy-3-methylglutaric aciduria. Clin Chim Acta. 1978 May 16;86(1):101-8. 657530 3-ketoacyl-CoA thiolase P21151 FADA_ECOLI fadA http://ecmdb.ca/proteins/P21151.xml 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 3-ketoacyl-CoA thiolase_ P76503 FADI_ECOLI fadI http://ecmdb.ca/proteins/P76503.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 3-Hydroxyisovaleryl-CoA <> 3-Methylcrotonyl-CoA + Water R04137 5-Methyl-3-oxo-4-hexenoyl-CoA + Coenzyme A <> 3-Methylcrotonyl-CoA + Acetyl-CoA R08095 Isovaleryl-CoA + ETF-Oxidized 3-Methylcrotonyl-CoA + ETF-Reduced RXN0-2301 Coenzyme A + 5-Methyl-3-oxo-4-hexenoyl-CoA > Acetyl-CoA + 3-Methylcrotonyl-CoA PW_R002507