2.02012-05-31 14:02:41 -06002015-06-03 15:54:38 -0600ECMDB04029M2MDB0005673-Carboxy-3-hydroxy-isocaproate3-carboxy-3-hydroxy-isocaproate is a member of the chemical class known as Dicarboxylic Acids and Derivatives. These are organic compounds containing exactly two carboxylic acid groups. Alpha isopropylmalate is involved in the biosynthesis of leucine. The protein product of MJ0720 was found to be alpha-isopropylmalate dehydrogenase (LeuB) and was found to catalyze the NAD-dependent decarboxylation of one isomer of DL-threo-isopropylmalate to 2-ketoisocaproate; thus, it is involved in the biosynthesis of leucine. (PMID 10940051)α-isopropylmalateα-isopropylmalic acid(2S)-2-isopropylmalate(2S)-2-isopropylmalic acid2IPMA3-Carboxy-3-hydroxy-4-methylpentanoate3-Carboxy-3-hydroxy-4-methylpentanoic acid3-carboxy-3-hydroxy-isocaproate3-Carboxy-3-hydroxy-isocaproic acid3-Hydroxy-4-methyl-3-carboxypentanoate3-Hydroxy-4-methyl-3-carboxypentanoic acida-Isopropylmalatea-Isopropylmalic acidAlpha-IsopropylmalateAlpha-Isopropylmalic acidα-Isopropylmalateα-Isopropylmalic acidC7H10O5174.1513174.052823432-hydroxy-2-(propan-2-yl)butanedioate2-isopropylmalateCC(C)C(O)(CC([O-])=O)C([O-])=OInChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/p-2BITYXLXUCSKTJS-UHFFFAOYSA-LOuter membraneInner membranelogp-0.10logs-0.71solubility4.13e+01 g/llogp0.21pka_strongest_acidic3.63pka_strongest_basic-4.1iupac2-hydroxy-2-(propan-2-yl)butanedioateaverage_mass174.1513mono_mass174.05282343smilesCC(C)C(O)(CC([O-])=O)C([O-])=OformulaC7H10O5inchiInChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/p-2inchikeyBITYXLXUCSKTJS-UHFFFAOYSA-Lpolar_surface_area100.49refractivity60.26polarizability15.49rotatable_bond_count4acceptor_count5donor_count1physiological_charge-2formal_charge-2Pyruvate metabolismec00620Valine, leucine and isoleucine biosynthesisec00290isoleucine biosynthesis I (from threonine)LEUSYN-PWYSpecdb::NmrOneD258208Specdb::NmrOneD258209Specdb::NmrOneD258210Specdb::NmrOneD258211Specdb::NmrOneD258212Specdb::NmrOneD258213Specdb::NmrOneD258214Specdb::NmrOneD258215Specdb::NmrOneD258216Specdb::NmrOneD258217Specdb::NmrOneD258218Specdb::NmrOneD258219Specdb::NmrOneD258220Specdb::NmrOneD258221Specdb::NmrOneD258222Specdb::NmrOneD258223Specdb::NmrOneD258224Specdb::NmrOneD258225Specdb::NmrOneD258226Specdb::NmrOneD258227Specdb::MsMs23033Specdb::MsMs23034Specdb::MsMs23035Specdb::MsMs29831Specdb::MsMs29832Specdb::MsMs2983364197264925359C02504351293-CARBOXY-3-HYDROXY-ISOCAPROATEKeseler, 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-D114.22080510van 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 370:17-25.17765195Howell, D. M., Graupner, M., Xu, H., White, R. H. (2000). "Identification of enzymes homologous to isocitrate dehydrogenase that are involved in coenzyme B and leucine biosynthesis in methanoarchaea." J Bacteriol 182:5013-5016.109400512-isopropylmalate synthaseP09151LEU1_ECOLIleuAhttp://ecmdb.ca/proteins/P09151.xmlalpha-Ketoisovaleric acid + Acetyl-CoA + Water > Hydrogen ion + 3-Carboxy-3-hydroxy-isocaproate + Coenzyme A2-ISOPROPYLMALATESYN-RXN3-Carboxy-3-hydroxy-isocaproate <> Isopropylmaleate + Water3-ISOPROPYLMALISOM-RXN