Record Information
Version2.0
Creation Date2012-05-31 09:55:11 -0600
Update Date2015-06-03 15:00:41 -0600
Secondary Accession Numbers
  • ECMDB00005
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
Weight:Average: 102.0886
Monoisotopic: 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
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.
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
  • Short-chain keto acid
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic 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:
2-Ketobutyric acid + Coenzyme A > Formic acid + Propionyl-CoA
2-Ketobutyric acid + Hydrogen ion + Pyruvic acid > 2-Aceto-2-hydroxy-butyrate + Carbon dioxide
L-Threonine > 2-Ketobutyric acid + Ammonium
2-Ketobutyric acid + Carbon dioxide + NADH + Hydrogen ion <> D-Erythro-3-Methylmalate + NAD
L-Threonine <> 2-Ketobutyric acid + Ammonia
O-Succinyl-L-homoserine + Water <> 2-Ketobutyric acid + Succinic acid + Ammonia
2-Ketobutyric acid + 2-(a-Hydroxyethyl)thiamine diphosphate <> 2-Aceto-2-hydroxy-butyrate + Thiamine pyrophosphate
2-Ketobutyric acid + Coenzyme A <> Propionyl-CoA + Formic acid
Pyruvic acid + 2-Ketobutyric acid <> 2-Aceto-2-hydroxy-butyrate + Carbon dioxide
Hydrogen ion + Pyruvic acid + 2-Ketobutyric acid > 2-Aceto-2-hydroxy-butyrate + Carbon dioxide
2-Ketobutyric acid + Coenzyme A > Propionyl-CoA + Formic acid
Hydrogen ion + 2-Ketobutyric acid + Succinic acid + Ammonia O-Succinyl-L-homoserine + Water
an aminated amine donor + 2-Ketobutyric acid + Hydrogen ion 2-aminobutyrate + a deaminated amine donor
L-Threonine > Hydrogen ion + 2-Ketobutyric acid + Ammonia
L-Threonine > 2-Ketobutyric acid + Ammonia
Iminobutyrate + Water > 2-Ketobutyric acid + Ammonia
L-Threonine > 2-Ketobutyric acid + Ammonia
Propionyl-CoA + Formic acid > CoA + 2-Ketobutyric acid
L-Threonine + 2-Aminobut-2-enoate + 2-Iminobutanoate + Water <> 2-Ketobutyric acid + Ammonia
2-Ketobutyric acid + Hydrogen ion + Pyruvic acid > Carbon dioxide + 2-Aceto-2-hydroxy-butyrate
2-Ketobutyric acid + Coenzyme A > Formic acid + Propionyl-CoA + Propionyl-CoA
SMPDB Pathways:
Propanoate metabolismPW000940 Pw000940Pw000940 greyscalePw000940 simple
isoleucine biosynthesisPW000818 Pw000818Pw000818 greyscalePw000818 simple
KEGG Pathways:
  • C5-Branched dibasic acid metabolism ec00660
  • Cysteine and methionine metabolism ec00270
  • Glycine, serine and threonine metabolism ec00260
  • Metabolic pathways eco01100
  • Propanoate metabolism ec00640
  • Valine, leucine and isoleucine biosynthesis ec00290
EcoCyc Pathways:
Concentrations
Not Available
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-MSsplash10-0a6r-9000000000-32269ef3ef778c482f99View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0ftb-0920000000-a6c93d8761ef15f7f7d4View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-0920000000-406fe70e72dbd9c3f274View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0gbj-1900000000-8daa299f5bc38a7f9b3eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-014s-1910000000-d01bcd7b41fdcc634eeaView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-000i-9200000000-3b3816ffee5771215904View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-000i-6910000000-5b264d5f7e53f3e80b12View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-001i-6950000000-db7f6a0f03a8cce59baeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-000i-8900000000-97bab6630de4df095a7fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-000i-9200000000-0ebb2354fe3f935fe177View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0adi-9200000000-f92941e9f326d8ccf3e4View in MoNA
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , 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

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 pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
metB
Uniprot ID:
P00935
Molecular weight:
41550
Reactions
O(4)-succinyl-L-homoserine + L-cysteine = L-cystathionine + succinate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the formation of alpha-ketobutyrate from threonine in a two-step reaction. The first step is a dehydration of threonine, followed by rehydration and liberation of ammonia. Deaminates L-threonine, but also L-serine to a lesser extent
Gene Name:
ilvA
Uniprot ID:
P04968
Molecular weight:
56195
Reactions
L-threonine = 2-oxobutanoate + NH(3).
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 transferase activity
Specific function:
L-valine + pyruvate = 3-methyl-2-oxobutanoate + L-alanine
Gene Name:
avtA
Uniprot ID:
P09053
Molecular weight:
46711
Reactions
L-valine + pyruvate = 3-methyl-2-oxobutanoate + L-alanine.
General function:
Involved in formate C-acetyltransferase activity
Specific function:
Acetyl-CoA + formate = CoA + pyruvate
Gene Name:
pflB
Uniprot ID:
P09373
Molecular weight:
85357
Reactions
Acetyl-CoA + formate = CoA + pyruvate.
General function:
Involved in catalytic activity
Specific function:
Activation of pyruvate formate-lyase 1 under anaerobic conditions by generation of an organic free radical, using S- adenosylmethionine and reduced flavodoxin as cosubstrates to produce 5'-deoxy-adenosine
Gene Name:
pflA
Uniprot ID:
P0A9N4
Molecular weight:
28204
Reactions
S-adenosyl-L-methionine + dihydroflavodoxin + [formate C-acetyltransferase]-glycine = 5'-deoxyadenosine + L-methionine + flavodoxin semiquinone + [formate C-acetyltransferase]-glycin-2-yl radical.
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).
General function:
Involved in catalytic activity
Specific function:
Acts on both serine and threonine, and properly considered as a hydroxy amino acid deaminase
Gene Name:
tdcB
Uniprot ID:
P0AGF6
Molecular weight:
35232
Reactions
L-threonine = 2-oxobutanoate + NH(3).
L-serine = pyruvate + NH(3).
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the oxidation of 3-carboxy-2-hydroxy-4- methylpentanoate (3-isopropylmalate) to 3-carboxy-4-methyl-2- oxopentanoate. The product decarboxylates to 4-methyl-2 oxopentanoate
Gene Name:
leuB
Uniprot ID:
P30125
Molecular weight:
39517
Reactions
(2R,3S)-3-isopropylmalate + NAD(+) = 4-methyl-2-oxopentanoate + CO(2) + NADH.
General function:
Involved in catalytic activity
Specific function:
Acetyl-CoA + formate = CoA + pyruvate
Gene Name:
pflD
Uniprot ID:
P32674
Molecular weight:
85959
Reactions
Acetyl-CoA + formate = CoA + pyruvate.
General function:
Involved in formate C-acetyltransferase activity
Specific function:
Specific function unknown
Gene Name:
tdcE
Uniprot ID:
P42632
Molecular weight:
85935
Reactions
Propionyl-CoA + formate = CoA + 2-oxobutanoate.
Acetyl-CoA + formate = CoA + pyruvate.
General function:
Involved in catalytic activity
Specific function:
Acetyl-CoA + formate = CoA + pyruvate
Gene Name:
ybiW
Uniprot ID:
P75793
Molecular weight:
90125
Reactions
Acetyl-CoA + formate = CoA + pyruvate.
General function:
Involved in catalytic activity
Specific function:
Acts as a radical domain for damaged PFL and possibly other radical proteins
Gene Name:
grcA
Uniprot ID:
P68066
Molecular weight:
14284
General function:
Translation, ribosomal structure and biogenesis
Specific function:
May have a phosphotransferase activity
Gene Name:
yjgF
Uniprot ID:
P0AF93
Molecular weight:
13612
Reactions
Iminobutyrate + H(2)O = 2-oxobutanoate + NH(3).