Record Information
Version 1.0
Update Date 1/22/2018 12:54:53 PM
Metabolite IDPAMDB000001
Identification
Name: 2-Ketobutyric acid
Description:2-Ketobutyric acid (alpha ketobutyric acid) is involved in the metabolism of many amino acids (glycine, cysteine, methionine, valine, leucine, serine, threonine, isoleucine). It also plays a role in propanoate metabolism and C-5 branched dibasic acid metabolism. More specifically, alpha-ketobutyric acid can be produced through the lysis of cystathionine (via cystathionine gamma lyase) leading to the production of cysteine and alpha-ketobutyric acid. It is also one of the degradation products of threonine. It can be converted to propionyl-CoA (and subsequently methylmalonyl CoA, which can be converted to succinyl CoA, a citric acid cycle intermediate), and thus enter the citric acid cycle.
Structure
Thumb
Synonyms:
  • α-ketobutyrate
  • α-ketobutyric acid
  • α-oxobutyrate
  • α-oxobutyric acid
  • 2-Keto-butyrate
  • 2-Keto-butyric acid
  • 2-Ketobutanoate
  • 2-Ketobutanoic acid
  • 2-Ketobutyrate
  • 2-Ketobutyric acid
  • 2-OBA
  • 2-Oxo-Butanoate
  • 2-Oxo-Butanoic acid
  • 2-Oxo-Butyrate
  • 2-Oxo-Butyric acid
  • 2-Oxo-N-butyrate
  • 2-Oxo-N-butyric acid
  • 2-Oxobutanoate
  • 2-Oxobutanoic acid
  • 2-Oxobutyrate
  • 2-Oxobutyric acid
  • 3-Methylpyruvate
  • 3-Methylpyruvic acid
  • A-Keto-N-Butyrate
  • A-Keto-N-Butyric acid
  • a-Ketobutrate
  • a-Ketobutric acid
  • A-Ketobutyrate
  • A-Ketobutyric acid
  • A-Oxo-N-butyrate
  • A-Oxo-N-butyric acid
  • A-Oxobutyrate
  • A-Oxobutyric acid
  • Alpha-Keto-N-butyrate
  • Alpha-Keto-N-butyric acid
  • Alpha-Ketobutrate
  • Alpha-Ketobutric acid
  • Alpha-Ketobutyrate
  • Alpha-Ketobutyric acid
  • Alpha-Oxo-N-butyrate
  • Alpha-Oxo-N-butyric acid
  • Alpha-Oxobutyrate
  • Alpha-Oxobutyric acid
  • Methyl-Pyruvate
  • Methyl-Pyruvic acid
  • Propionyl-formate
  • Propionyl-formic acid
  • α-keto-N-Butyrate
  • α-keto-N-Butyric acid
  • α-Ketobutrate
  • α-Ketobutric acid
  • α-Ketobutyrate
  • α-Ketobutyric acid
  • α-oxo-N-Butyrate
  • α-oxo-N-Butyric acid
  • α-Oxobutyrate
  • α-Oxobutyric acid
Chemical Formula: C4H6O3
Average Molecular Weight: 102.0886
Monoisotopic Molecular Weight: 102.031694058
InChI Key: TYEYBOSBBBHJIV-UHFFFAOYSA-N
InChI:InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
CAS number: 600-18-0
IUPAC Name:2-oxobutanoic acid
Traditional IUPAC Name: 2-oxobutanoic acid
SMILES:CCC(=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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 ClassOrganic acids and derivatives
Class Keto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct Parent Short-chain keto acids and derivatives
Alternative Parents
Substituents
  • Short-chain keto acid
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 33°C [Suante, H.; Oxidation Communications 2004, V27(2), P344-348]
Experimental Properties:
PropertyValueSource
Water Solubility:119 mg/mL [HMP experimental]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility79.2 mg/mLALOGPS
logP0.07ALOGPS
logP0.77ChemAxon
logS-0.11ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.62 m3·mol-1ChemAxon
Polarizability9.2 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0gbj-1900000000-8daa299f5bc38a7f9b3eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014s-1910000000-d01bcd7b41fdcc634eeaView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9200000000-3b3816ffee5771215904View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-6910000000-5b264d5f7e53f3e80b12View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-6950000000-db7f6a0f03a8cce59baeView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0pb9-9600000000-53ebb7164f74d7d92a4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0zfr-5900000000-1db864754705beb79b55View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0udi-9800000000-5ba5b9ede5b1bc389b87View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-bfdcad5bc3ed586bdedeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0k9i-9400000000-0061f4635858d851f127View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-b943445194fb5f8e3a0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-bc5920b9bd140be6b06dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-5900000000-f7dfb4554f0b9e1499c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-9200000000-e54106ad5bf45a9f072cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-7bbba57578cf720974e3View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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
  • Sprague CL, Elfarra AA: Detection of carboxylic acids and inhibition of hippuric acid formation in rats treated with 3-butene-1,2-diol, a major metabolite of 1,3-butadiene. Drug Metab Dispos. 2003 Aug;31(8):986-92. Pubmed: 12867486
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Yaegaki K, Sanada K: Biochemical and clinical factors influencing oral malodor in periodontal patients. J Periodontol. 1992 Sep;63(9):783-9. Pubmed: 1474480
  • Yaegaki K, Sanada K: Effects of a two-phase oil-water mouthwash on halitosis. Clin Prev Dent. 1992 Jan-Feb;14(1):5-9. Pubmed: 1499240
  • Yang W, Roth KS: Defect in alpha-ketobutyrate metabolism: a new inborn error. Clin Chim Acta. 1985 Jan 30;145(2):173-82. Pubmed: 3918815
Synthesis Reference: Figge, Rainer; Lux, Fabien; Raynaud, Celine; Soucaille, Philippe. Production of a-ketobutyrate by engineered Escherichia coli.PCT Int. Appl. (2006), 31pp.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID16763
HMDB IDHMDB00005
Pubchem Compound ID58
Kegg IDC00109
ChemSpider ID57
WikipediaAlpha-ketobutyric_acid
BioCyc ID2-OXOBUTANOATE
EcoCyc ID2-OXOBUTANOATE
Ligand Expo2KT