2.0 2012-05-31 14:01:40 -0600 2015-06-03 15:54:35 -0600 ECMDB04001 M2MDB000549 2-Aceto-2-hydroxy-butyrate (S)-2-Aceto-2-hydroxybutanoic acid is an intermediate in branched chain amino acid metabolism. It is converted from 2-oxobutanoate or 2-hydoxyethyl ThPP via acetolactate synthase. α-aceto-α-hydroxybutyrate α-aceto-α-hydroxybutyric acid (2S)-2-ethyl-2-hydroxy-3-oxobutanoate (2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid (S)-2-Aceto-2-hydroxybutanoate (S)-2-Aceto-2-hydroxybutanoic acid (S)-2-Hydroxy-2-ethyl-3-oxobutanoate (S)-2-Hydroxy-2-ethyl-3-oxobutanoic acid 2-aceto-2-hydroxy-butyrate 2-Aceto-2-hydroxy-butyric acid a-aceto-a-Hydroxybutyrate a-aceto-a-Hydroxybutyric acid Acetohydroxybutanoate Acetohydroxybutanoic acid Acetohydroxybutyrate Acetohydroxybutyric acid Alpha-Aceto-alpha-hydroxybutyrate Alpha-Aceto-alpha-hydroxybutyric acid α-aceto-α-Hydroxybutyrate α-aceto-α-Hydroxybutyric acid C6H10O4 146.1412 146.057908808 (2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid (2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid 3142-65-2 CC[C@](O)(C(C)=O)C(O)=O InChI=1S/C6H10O4/c1-3-6(10,4(2)7)5(8)9/h10H,3H2,1-2H3,(H,8,9)/t6-/m0/s1 VUQLHQFKACOHNZ-LURJTMIESA-N Solid Cytosol logp -0.58 ALOGPS logs 0.25 ALOGPS solubility 2.59e+02 g/l ALOGPS logp 0.24 ChemAxon pka_strongest_acidic 3.6 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac (2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid ChemAxon average_mass 146.1412 ChemAxon mono_mass 146.057908808 ChemAxon smiles CC[C@](O)(C(C)=O)C(O)=O ChemAxon formula C6H10O4 ChemAxon inchi InChI=1S/C6H10O4/c1-3-6(10,4(2)7)5(8)9/h10H,3H2,1-2H3,(H,8,9)/t6-/m0/s1 ChemAxon inchikey VUQLHQFKACOHNZ-LURJTMIESA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 33.11 ChemAxon polarizability 13.72 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Valine, leucine and isoleucine biosynthesis ec00290 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::CMs 2771 Specdb::CMs 39138 Specdb::CMs 158252 Specdb::NmrOneD 11242 Specdb::NmrOneD 11243 Specdb::NmrOneD 11244 Specdb::NmrOneD 11245 Specdb::NmrOneD 11246 Specdb::NmrOneD 11247 Specdb::NmrOneD 11248 Specdb::NmrOneD 11249 Specdb::NmrOneD 11250 Specdb::NmrOneD 11251 Specdb::NmrOneD 11252 Specdb::NmrOneD 11253 Specdb::NmrOneD 11254 Specdb::NmrOneD 11255 Specdb::NmrOneD 11256 Specdb::NmrOneD 11257 Specdb::NmrOneD 11258 Specdb::NmrOneD 11259 Specdb::NmrOneD 11260 Specdb::NmrOneD 11261 Specdb::MsMs 23747 Specdb::MsMs 23748 Specdb::MsMs 23749 Specdb::MsMs 30545 Specdb::MsMs 30546 Specdb::MsMs 30547 Specdb::MsMs 2764814 Specdb::MsMs 2764815 Specdb::MsMs 2764816 Specdb::MsMs 2944006 Specdb::MsMs 2944007 Specdb::MsMs 2944008 8279 389708 C06006 2-ACETO-2-HYDROXY-BUTYRATE 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 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 Acetolactate synthase isozyme 3 large subunit P00893 ILVI_ECOLI ilvI http://ecmdb.ca/proteins/P00893.xml Acetolactate synthase isozyme 3 small subunit P00894 ILVH_ECOLI ilvH http://ecmdb.ca/proteins/P00894.xml Ketol-acid reductoisomerase P05793 ILVC_ECOLI ilvC http://ecmdb.ca/proteins/P05793.xml Acetolactate synthase isozyme 1 large subunit P08142 ILVB_ECOLI ilvB http://ecmdb.ca/proteins/P08142.xml Acetolactate synthase isozyme 1 small subunit P0ADF8 ILVN_ECOLI ilvN http://ecmdb.ca/proteins/P0ADF8.xml Acetolactate synthase isozyme 2 small subunit P0ADG1 ILVM_ECOLI ilvM http://ecmdb.ca/proteins/P0ADG1.xml 2-Ketobutyric acid + Hydrogen ion + Pyruvic acid > 2-Aceto-2-hydroxy-butyrate + Carbon dioxide R08648 ACETOOHBUTSYN-RXN 2-Aceto-2-hydroxy-butyrate + Hydrogen ion + NADPH <> (R) 2,3-Dihydroxy-3-methylvalerate + NADP ACETOOHBUTREDUCTOISOM-RXN 2-Ketobutyric acid + 2-(a-Hydroxyethyl)thiamine diphosphate <> 2-Aceto-2-hydroxy-butyrate + Thiamine pyrophosphate R04673 2-Aceto-2-hydroxy-butyrate <> (R)-3-Hydroxy-3-methyl-2-oxopentanoate R05069 Pyruvic acid + 2-Ketobutyric acid <> 2-Aceto-2-hydroxy-butyrate + Carbon dioxide R08648 (R) 2,3-Dihydroxy-3-methylvalerate + NADP <> Hydrogen ion + 2-Aceto-2-hydroxy-butyrate + NADPH ACETOOHBUTREDUCTOISOM-RXN (R) 2,3-Dihydroxy-3-methylvalerate + NADP > 2-Aceto-2-hydroxy-butyrate + NADPH 2-Aceto-2-hydroxy-butyrate + NADPH + Hydrogen ion + NADPH > NADP + (R) 2,3-Dihydroxy-3-methylvalerate PW_R002926 2 2-Ketobutyric acid + Hydrogen ion + Pyruvic acid >2 2-Aceto-2-hydroxy-butyrate + Carbon dioxide 2 2-Ketobutyric acid + Hydrogen ion + Pyruvic acid >2 2-Aceto-2-hydroxy-butyrate + Carbon dioxide