2-Aceto-2-hydroxy-butyrate (PAMDB000549)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000549
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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 146.1412
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acids and conjugates
Direct Parent Hydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Short-chain keto acid
  • Branched fatty acid
  • Beta-keto acid
  • Keto acid
  • Hydroxy acid
  • Beta-hydroxy ketone
  • Alpha-hydroxy acid
  • Acyloin
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility259.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.11 m3·mol-1ChemAxon
Polarizability13.72 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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-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 > 2-Aceto-2-hydroxy-butyrate + NADPH
2-Aceto-2-hydroxy-butyrate + NADPH + Hydrogen ion + NADPH > NADP + (R) 2,3-Dihydroxy-3-methylvalerate
Pathways:
  • Valine, leucine and isoleucine biosynthesis pae00290
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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
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 IDHMDB06900
Pubchem Compound ID8279
Kegg IDC06006
ChemSpider ID389708
Wikipedia IDNot Available
BioCyc ID2-ACETO-2-HYDROXY-BUTYRATE
EcoCyc ID2-ACETO-2-HYDROXY-BUTYRATE