2.0 2012-05-31 14:25:54 -0600 2015-06-03 17:19:15 -0600 ECMDB20070 M2MDB000919 3-Hydroxy-3-methyl-2-oxobutanoic acid 3-hydroxy-3-methyl-2-oxobutanoic acid belongs to the class of Branched Fatty Acids. These are fatty acids containing a branched chain. (inferred from compound structure)α-Acetolactic acid (α-acetolactate) is a precursor in the biosynthesis of the branched chain amino acids valine and leucine. α-Acetolactic acid is produced from two molecules of pyruvic acid by acetolactate synthase. α-Acetolactic acid can also be decarboxylated by alpha-acetolactate decarboxylase to produce acetoin. (WikiPedia) 2-Oxo-3-hydroxyisovalerate 2-Oxo-3-hydroxyisovaleric acid 3-Hydroxy-3-methyl-2-oxo-butanoate 3-Hydroxy-3-methyl-2-oxo-butanoic acid 3-Hydroxy-3-methyl-2-oxobutanoate C5H8O4 132.1146 132.042258744 3-hydroxy-3-methyl-2-oxobutanoic acid 2-oxo-3-hydroxyisovaleric acid CC(C)(O)C(=O)C(O)=O InChI=1S/C5H8O4/c1-5(2,9)3(6)4(7)8/h9H,1-2H3,(H,7,8) DNOPJXBPONYBLB-UHFFFAOYSA-N Outer membrane Inner membrane logp -0.45 ALOGPS logs 0.04 ALOGPS solubility 1.44e+02 g/l ALOGPS logp 0.25 ChemAxon pka_strongest_acidic 3.01 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac 3-hydroxy-3-methyl-2-oxobutanoic acid ChemAxon average_mass 132.1146 ChemAxon mono_mass 132.042258744 ChemAxon smiles CC(C)(O)C(=O)C(O)=O ChemAxon formula C5H8O4 ChemAxon inchi InChI=1S/C5H8O4/c1-5(2,9)3(6)4(7)8/h9H,1-2H3,(H,7,8) ChemAxon inchikey DNOPJXBPONYBLB-UHFFFAOYSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 28.9 ChemAxon polarizability 11.82 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Valine, leucine and isoleucine biosynthesis ec00290 Secondary Metabolites: Valine and I-leucine biosynthesis from pyruvate The biosynthesis of Valine and L-leucine from pyruvic acid starts with pyruvic acid interacting with a hydrogen ion through a acetolactate synthase / acetohydroxybutanoate synthase resulting in a release of a carbon dioxide, a (S)-2-acetolactate. The latter compound then interacts with a hydrogen ion through a NADPH-driven acetohydroxy acid isomeroreductase resulting in the release of a NADP, a (R) 2,3-dihydroxy-3-methylvalerate. The latter compound is then dehydrated by a dihydroxy acid dehydratase resulting in the release of a water molecule an 3-methyl-2-oxovaleric acid. The 3-methyl-2-oxovaleric acid can produce an L-valine by interacting with a L-glutamic acid through a Valine Transaminase resulting in the release of a Oxoglutaric acid and a L-valine. The 3-methyl-2-oxovaleric acid then interacts with an acetyl-CoA and a water molecule through a 2-isopropylmalate synthase resulting in the release of a hydrogen ion, a Coenzyme A and a 2-Isopropylmalic acid. The isopropylimalic acid is then hydrated by interacting with a isopropylmalate isomerase resulting in a 3-isopropylmalate. This compound then interacts with an NAD driven 3-isopropylmalate dehydrogenase resulting in a NADH, a hydrogen ion and a 2-isopropyl-3-oxosuccinate. The latter compound then interacts with hydrogen ion spontaneously resulting in a carbon dioxide and a ketoleucine. The ketoleucine then interacts with a L-glutamic acid through a branched-chain amino-acid aminotransferase resulting in the oxoglutaric acid and L-leucine. PW000978 Metabolic Specdb::CMs 80444 Specdb::NmrOneD 289675 Specdb::NmrOneD 289676 Specdb::NmrOneD 289677 Specdb::NmrOneD 289678 Specdb::NmrOneD 289679 Specdb::NmrOneD 289680 Specdb::NmrOneD 289681 Specdb::NmrOneD 289682 Specdb::NmrOneD 289683 Specdb::NmrOneD 289684 Specdb::NmrOneD 289685 Specdb::NmrOneD 289686 Specdb::NmrOneD 289687 Specdb::NmrOneD 289688 Specdb::NmrOneD 289689 Specdb::NmrOneD 289690 Specdb::NmrOneD 289691 Specdb::NmrOneD 289692 Specdb::NmrOneD 289693 Specdb::NmrOneD 289694 Specdb::MsMs 26402 Specdb::MsMs 26403 Specdb::MsMs 26404 Specdb::MsMs 32960 Specdb::MsMs 32961 Specdb::MsMs 32962 440248 389229 C04181 17667 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 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A Ketol-acid reductoisomerase P05793 ILVC_ECOLI ilvC http://ecmdb.ca/proteins/P05793.xml (R)-2,3-Dihydroxy-isovalerate + NADP <> 3-Hydroxy-3-methyl-2-oxobutanoic acid + NADPH + Hydrogen ion R04440 (S)-2-Acetolactate <> 3-Hydroxy-3-methyl-2-oxobutanoic acid R05071