Record Information
Version2.0
Creation Date2012-05-31 14:01:40 -0600
Update Date2015-06-03 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
Thumb
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility259 g/LALOGPS
logP-0.58ALOGPS
logP0.24ChemAxon
logS0.25ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.11 m³·mol⁻¹ChemAxon
Polarizability13.72 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
isoleucine biosynthesisPW000818 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Valine, leucine and isoleucine biosynthesis ec00290
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-4a32387e4d1a3c2518e2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-9260000000-03d854f5c6e2c1cd66ccView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-58139948a2d318b20cd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-7900000000-5d95d041962e4d0c29c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9400000000-54a124cdee1ab9c9f382View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-c26fd82bd80ef12ed78aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9500000000-79a2c717c39914d90709View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-14cfb3f09136a8d1b1fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-0900000000-e31b2e7070d5d06bb420View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kam-9200000000-8e85855717b408d3368eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-0a3fed2352239366e095View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kal-9600000000-fd5ff61bfd773a3d7ff1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-775b97d756977d989ad0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-9000000000-287791e86291cbac2749View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView 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
External Links:
ResourceLink
CHEBI ID27681
HMDB IDHMDB0006900
Pubchem Compound ID8279
Kegg IDC06006
ChemSpider ID389708
Wikipedia IDNot Available
BioCyc ID2-ACETO-2-HYDROXY-BUTYRATE
EcoCyc ID2-ACETO-2-HYDROXY-BUTYRATE

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
2 pyruvate = 2-acetolactate + CO(2)
Gene Name:
ilvI
Uniprot ID:
P00893
Molecular weight:
62984
Reactions
2 pyruvate = 2-acetolactate + CO(2).
General function:
Involved in acetolactate synthase activity
Specific function:
2 pyruvate = 2-acetolactate + CO(2)
Gene Name:
ilvH
Uniprot ID:
P00894
Molecular weight:
17977
Reactions
2 pyruvate = 2-acetolactate + CO(2).
General function:
Involved in oxidation-reduction process
Specific function:
(R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) = (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH
Gene Name:
ilvC
Uniprot ID:
P05793
Molecular weight:
54069
Reactions
(R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) = (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH.
(2R,3R)-2,3-dihydroxy-3-methylpentanoate + NADP(+) = (S)-2-hydroxy-2-ethyl-3-oxobutanoate + NADPH.
General function:
Involved in magnesium ion binding
Specific function:
2 pyruvate = 2-acetolactate + CO(2)
Gene Name:
ilvB
Uniprot ID:
P08142
Molecular weight:
60440
Reactions
2 pyruvate = 2-acetolactate + CO(2).
General function:
Involved in amino acid binding
Specific function:
2 pyruvate = 2-acetolactate + CO(2)
Gene Name:
ilvN
Uniprot ID:
P0ADF8
Molecular weight:
11106
Reactions
2 pyruvate = 2-acetolactate + CO(2).
General function:
Involved in acetolactate synthase activity
Specific function:
2 pyruvate = 2-acetolactate + CO(2)
Gene Name:
ilvM
Uniprot ID:
P0ADG1
Molecular weight:
9703
Reactions
2 pyruvate = 2-acetolactate + CO(2).