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Record Information
Version	2.0
Creation Date	2012-05-31 14:01:40 -0600
Update Date	2015-06-03 15:54:35 -0600
Secondary Accession Numbers	ECMDB04001
Identification
Name:	2-Aceto-2-hydroxy-butyrate
Description	(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.
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xb65ce444> Close
Synonyms:	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
Chemical Formula:	C6H10O4
Weight:	Average: 146.1412 Monoisotopic: 146.057908808
InChI Key:	VUQLHQFKACOHNZ-LURJTMIESA-N
InChI:	InChI=1S/C6H10O4/c1-3-6(10,4(2)7)5(8)9/h10H,3H2,1-2H3,(H,8,9)/t6-/m0/s1
CAS number:	3142-65-2
IUPAC Name:	(2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid
Traditional IUPAC Name:	(2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid
SMILES:	CC[C@](O)(C(C)=O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Keto acids and derivatives
Sub Class	Short-chain keto acids and derivatives
Direct Parent	Short-chain keto acids and derivatives
Alternative Parents	Hydroxy fatty acids Branched fatty acids Beta-keto acids and derivatives Beta-hydroxy ketones Alpha hydroxy acids and derivatives Acyloins Tertiary alcohols Alpha-hydroxy ketones Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
Substituents	Beta-keto acid Branched fatty acid Hydroxy fatty acid Short-chain keto acid Alpha-hydroxy acid Fatty acyl Acyloin Beta-hydroxy ketone Hydroxy acid Tertiary alcohol Alpha-hydroxy ketone Ketone Carboxylic acid derivative Monocarboxylic acid or derivatives Carboxylic acid Carbonyl group Alcohol Organic oxygen compound Organooxygen compound Hydrocarbon derivative Organic oxide Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	hydroxy monocarboxylic acid (CHEBI:27681 ) 3-oxo monocarboxylic acid (CHEBI:27681 ) Hydroxy fatty acids (LMFA01050383 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 259 g/L ALOGPS logP -0.58 ALOGPS logP 0.24 ChemAxon logS 0.25 ALOGPS pKa (Strongest Acidic) 3.6 ChemAxon pKa (Strongest Basic) -4.7 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 74.6 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 33.11 m³·mol⁻¹ ChemAxon Polarizability 13.72 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	2-Ketobutyric acid + Hydrogen ion + Pyruvic acid > 2-Aceto-2-hydroxy-butyrate + Carbon dioxide 2-Aceto-2-hydroxy-butyrate + Hydrogen ion + NADPH <> (R) 2,3-Dihydroxy-3-methylvalerate + NADP 2-Ketobutyric acid + 2-(a-Hydroxyethyl)thiamine diphosphate <> 2-Aceto-2-hydroxy-butyrate + Thiamine pyrophosphate 2-Aceto-2-hydroxy-butyrate <> (R)-3-Hydroxy-3-methyl-2-oxopentanoate Pyruvic acid + 2-Ketobutyric acid <> 2-Aceto-2-hydroxy-butyrate + Carbon dioxide (R) 2,3-Dihydroxy-3-methylvalerate + NADP <> Hydrogen ion + 2-Aceto-2-hydroxy-butyrate + NADPH (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 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
SMPDB Pathways:	isoleucine biosynthesis PW000818
KEGG Pathways:	Valine, leucine and isoleucine biosynthesis ec00290
EcoCyc Pathways:	isoleucine biosynthesis I (from threonine) ILEUSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0006-9300000000-4a32387e4d1a3c2518e2 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-004i-9260000000-03d854f5c6e2c1cd66cc View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0002-1900000000-58139948a2d318b20cd3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-004i-7900000000-5d95d041962e4d0c29c2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-9400000000-54a124cdee1ab9c9f382 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0udi-3900000000-c26fd82bd80ef12ed78a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0pb9-9500000000-79a2c717c39914d90709 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0ab9-9000000000-14cfb3f09136a8d1b1fd View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0udj-0900000000-e31b2e7070d5d06bb420 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0kam-9200000000-8e85855717b408d3368e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9000000000-0a3fed2352239366e095 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0kal-9600000000-fd5ff61bfd773a3d7ff1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0006-9000000000-775b97d756977d989ad0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-001r-9000000000-287791e86291cbac2749 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer
References
References:	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. Pubmed: 22080510 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. Pubmed: 21097882 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. Pubmed: 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 27681 HMDB ID HMDB0006900 Pubchem Compound ID 8279 Kegg ID C06006 ChemSpider ID 389708 Wikipedia ID Not Available BioCyc ID 2-ACETO-2-HYDROXY-BUTYRATE EcoCyc ID 2-ACETO-2-HYDROXY-BUTYRATE

Enzymes