2.0 2012-05-31 14:04:44 -0600 2015-06-03 15:54:43 -0600 ECMDB04091 M2MDB000605 2-Keto-3-methyl-valerate 3-Methyl-2-oxovaleric acid is a metabolite of isoleucine in man, animals and bacteria. It is the alpha-keto acid analogue of isoleucine. 3-Methyl-2-oxovaleric acid is produced from isoleucine by cytosolic branched chain aminotransferase 1 (EC:2.6.1.42), whereupon it is further degraded by branched chain keto acid dehydrogenase E1 to 2-Methyl-1-hydroxybutyl-ThPP. α-keto-β-methyl-valerate α-keto-β-methyl-valeric acid α-keto-methylvalerate α-keto-methylvaleric acid (3S)-3-Methyl-2-oxopentanoate (3R)-3-Methyl-2-oxopentanoate (3R)-3-Methyl-2-oxopentanoic acid (3S)-3-methyl-2-oxopentanoate (3S)-3-methyl-2-oxopentanoic acid (S)-2-oxo-3-methylpentanoate (S)-3-methyl-2-oxopentanoate (R)-3-methyl-2-oxopentanoate (R)-3-methyl-2-oxopentanoic acid (S)-2-oxo-3-methylpentanoate (S)-2-oxo-3-methylpentanoic acid (S)-3-methyl-2-oxopentanoate (S)-3-methyl-2-oxopentanoic acid (S)-3-methyl-2-oxovalerate (S)-3-methyl-2-oxovaleric acid 2-keto-3-methyl-valerate 2-Keto-3-methyl-valeric acid 2-keto-3-methylvalerate 2-keto-3-methylvaleric acid 2-Oxo-3-methyl-N-valerate 2-Oxo-3-methyl-N-valeric acid 2-Oxo-3-methylpentanoate 2-Oxo-3-methylpentanoic acid 2-Oxo-3-methylvalerate 2-Oxo-3-methylvaleric acid 2-Oxoisoleucine 2-Oxokolavenate 2-Oxokolavenic acid 3-Methyl-2-oxo-pentanoate 3-Methyl-2-oxo-pentanoic acid 3-Methyl-2-oxo-Valerate 3-Methyl-2-oxo-Valeric acid 3-Methyl-2-oxopentanoate 3-Methyl-2-oxopentanoic acid 3-Methyl-2-oxovalerate 3-Methyl-2-oxovaleric 3-Methyl-2-oxovaleric acid A-Keto-b-methyl-N-valerate A-Keto-b-methyl-N-valeric acid a-keto-b-Methyl-valerate a-keto-b-Methyl-valeric acid A-Keto-b-methylvalerate A-Keto-b-methylvaleric acid a-keto-Methylvalerate a-keto-Methylvaleric acid A-Oxo-b-methyl-N-valerate A-Oxo-b-methyl-N-valeric acid A-Oxo-b-methylvalerate A-Oxo-b-methylvaleric acid Alpha-Keto-beta-methyl-N-valerate Alpha-Keto-beta-methyl-N-valeric acid Alpha-Keto-beta-methyl-valerate Alpha-Keto-beta-methyl-valeric acid Alpha-Keto-beta-methylvalerate Alpha-Keto-beta-methylvaleric acid Alpha-Keto-methylvalerate Alpha-Keto-methylvaleric acid Alpha-Oxo-beta-methyl-N-valerate Alpha-Oxo-beta-methyl-N-valeric acid Alpha-Oxo-beta-methylvalerate Alpha-Oxo-beta-methylvaleric acid α-keto-Methylvalerate α-keto-Methylvaleric acid α-keto-β-Methyl-N-valerate α-keto-β-Methyl-N-valeric acid α-keto-β-Methyl-valerate α-keto-β-Methyl-valeric acid α-keto-β-Methylvalerate α-keto-β-Methylvaleric acid α-oxo-β-Methyl-N-valerate α-oxo-β-Methyl-N-valeric acid α-oxo-β-Methylvalerate α-oxo-β-Methylvaleric acid C6H9O3 129.1339 129.055169154 (3S)-3-methyl-2-oxopentanoate (S)-3-methyl-2-oxopentanoate 1460-34-0 CC[C@H](C)C(=O)C([O-])=O InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)/p-1/t4-/m0/s1 JVQYSWDUAOAHFM-BYPYZUCNSA-M Solid Outer membrane Inner membrane logp 0.90 ALOGPS logs -1.07 ALOGPS solubility 1.25e+01 g/l ALOGPS logp 1.75 ChemAxon pka_strongest_acidic 3.52 ChemAxon pka_strongest_basic -9.7 ChemAxon iupac (3S)-3-methyl-2-oxopentanoate ChemAxon average_mass 129.1339 ChemAxon mono_mass 129.055169154 ChemAxon smiles CC[C@H](C)C(=O)C([O-])=O ChemAxon formula C6H9O3 ChemAxon inchi InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)/p-1/t4-/m0/s1 ChemAxon inchikey JVQYSWDUAOAHFM-BYPYZUCNSA-M ChemAxon polar_surface_area 57.2 ChemAxon refractivity 42.63 ChemAxon polarizability 12.57 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 0 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon Valine, leucine and isoleucine biosynthesis ec00290 Valine, leucine and isoleucine degradation ec00280 isoleucine biosynthesis Isoleucine biosynthesis begins with L-threonine from the threonine biosynthesis pathway. L-threonine interacts with a threonine dehydratase biosynthetic releasing water, a hydrogen ion and (2Z)-2-aminobut-2-enoate. This compound is isomerized into a 2-iminobutanoate which interacts with water and a hydrogen ion spontaneously, resulting in the release of ammonium and 2-ketobutyric acid. This compound reacts with pyruvic acid and hydrogen ion through an acetohydroxybutanoate synthase / acetolactate synthase 2 resulting in carbon dioxide and (S)-2-Aceto-2-hydroxybutanoic acid. The latter compound is reduced by an NADPH driven acetohydroxy acid isomeroreductase releasing NADP and acetohydroxy acid isomeroreductase. The latter compound is dehydrated by a dihydroxy acid dehydratase resulting in 3-methyl-2-oxovaleric acid.This compound reacts in a reversible reaction with L-glutamic acid through a Branched-chain-amino-acid aminotransferase resulting in oxoglutaric acid and L-isoleucine. L-isoleucine can also be transported into the cytoplasm through two different methods: a branched chain amino acid ABC transporter or a branched chain amino acid transporter BrnQ y. PW000818 Metabolic isoleucine biosynthesis I (from threonine) ILEUSYN-PWY Specdb::NmrOneD 257588 Specdb::NmrOneD 257589 Specdb::NmrOneD 257590 Specdb::NmrOneD 257591 Specdb::NmrOneD 257592 Specdb::NmrOneD 257593 Specdb::NmrOneD 257594 Specdb::NmrOneD 257595 Specdb::NmrOneD 257596 Specdb::NmrOneD 257597 Specdb::NmrOneD 257598 Specdb::NmrOneD 257599 Specdb::NmrOneD 257600 Specdb::NmrOneD 257601 Specdb::NmrOneD 257602 Specdb::NmrOneD 257603 Specdb::NmrOneD 257604 Specdb::NmrOneD 257605 Specdb::NmrOneD 257606 Specdb::NmrOneD 257607 Specdb::MsMs 23210 Specdb::MsMs 23211 Specdb::MsMs 23212 Specdb::MsMs 30008 Specdb::MsMs 30009 Specdb::MsMs 30010 HMDB00491 6857401 19951083 C00671 35146 2-KETO-3-METHYL-VALERATE 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 Dihydroxy-acid dehydratase P05791 ILVD_ECOLI ilvD http://ecmdb.ca/proteins/P05791.xml Branched-chain-amino-acid aminotransferase P0AB80 ILVE_ECOLI ilvE http://ecmdb.ca/proteins/P0AB80.xml