You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00071
Name2-Ketobutyric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAlpha-Ketoglutaric acid (2-oxobutanoate, 2-keto-butyrate) is a key intermediate in the Krebs cycle. It is involved in the metabolism of many amino acids (glycine, methionine, valine, leucine, serine, threonine, isoleucine) as well as propanoate metabolism and C-5 branched dibasic acid metabolism. It can be converted to propionyl-CoA and thus enter the citric acid cycle.
Structure
Thumb
Synonyms
  • 2-Ketobutanoate
  • 2-Ketobutanoic acid
  • 2-ketobutyrate
  • 2-ketobutyric acid
  • 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-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-Ketobutric acid
  • alpha-Ketobutyrate
  • alpha-Ketobutyric acid
  • alpha-Oxo-n-butyrate
  • alpha-Oxo-n-butyric acid
  • alpha-Oxobutyrate
  • alpha-Oxobutyric acid
  • Butanoic acid, 2-oxo-
  • Butyric acid, 2-oxo-
  • Formic acid, propionyl-
  • Ketobutyrate
  • methyl-Pyruvate
  • methyl-Pyruvic acid
  • Oxobutyrate
  • propionyl-formate
  • propionyl-formic acid
  • Pyruvic acid, methyl-
  • 3-Methyl pyruvic acid
  • 3-Methyl pyruvate
  • α-ketobutyrate
  • α-ketobutyric acid
  • α-oxo-N-butyrate
  • α-oxo-N-butyric acid
CAS number600-18-0
WeightAverage: 102.0886
Monoisotopic: 102.031694058
InChI KeyTYEYBOSBBBHJIV-UHFFFAOYSA-N
InChIInChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
IUPAC Name2-oxobutanoic acid
Traditional IUPAC Name2-oxobutanoic acid
Chemical FormulaC4H6O3
SMILES[H]OC(=O)C(=O)C([H])([H])C([H])([H])[H]
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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point33°C
Experimental Properties
PropertyValueReference
Water Solubility119 mg/mL [HMP experimental]PhysProp
LogPNot AvailablePhysProp
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
  • mitochondrion
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
BrownFDB003359
CaramelFDB003359
CreamyFDB003359
LactonicFDB003359
SweetFDB003359
SMPDB Pathways
Cysteine MetabolismPW002383 Pw002383Pw002383 greyscalePw002383 simple
Methionine metabolism and salvagePW002384 Pw002384Pw002384 greyscalePw002384 simple
Selenocompound metabolismPW002472 Pw002472Pw002472 greyscalePw002472 simple
Sulfur metabolismPW002483 Pw002483Pw002483 greyscalePw002483 simple
isoleucine biosynthesisPW002476 Pw002476Pw002476 greyscalePw002476 simple
KEGG Pathways
Cysteine and methionine metabolismec00270 Map00270
Glycine, serine and threonine metabolismec00260 Map00260
Propanoate metabolismec00640 Map00640
Selenocompound metabolismec00450 Map00450
Sulfur metabolismec00920 Map00920
SMPDB Reactions
water + L-CystathionineAmmonium + L-Cysteine + 2-Ketobutyric acid
4-Methylthio-2-oxobutanoate + L-PhenylalanineL-Methionine + 2-Ketobutyric acid
2-Ketobutyric acid + hydron + Pyruvic acidCarbon dioxide + (S)-2-Aceto-2-hydroxybutanoic acid
Selenomethionine + watermethylselenol + Ammonia + 2-Ketobutyric acid
KEGG Reactions
Pyruvic acid + hydron + 2-Ketobutyric acidCarbon dioxide + (S)-2-acetyl-2-hydroxybutanoate
NAD + 2-hydroxybutyric acidNADH + hydron + 2-Ketobutyric acid
NAD + Coenzyme A + 2-Ketobutyric acidNADH + propionyl-CoA + Carbon dioxide
L-Cystathionine + waterL-Cysteine + Ammonium + 2-Ketobutyric acid
L-ThreonineAmmonium + 2-Ketobutyric acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot 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
Predicted GC-MSPredicted GC-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:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Yamagata, S., Yasugahira, T., Okuda, Y., Iwama, T. (2003). "Conversion of the aminocrotonate intermediate limits the rate of gamma-elimination reaction catalyzed by L-cystathionine gamma-lyase of the yeast Saccharomyces cerevisiae." J Biochem 134:607-613.14607989
  • Cullin, C., Baudin-Baillieu, A., Guillemet, E., Ozier-Kalogeropoulos, O. (1996). "Functional analysis of YCL09C: evidence for a role as the regulatory subunit of acetolactate synthase." Yeast 12:1511-1518.8972574
Synthesis Reference:Figge, Rainer; Lux, Fabien; Raynaud, Celine; Soucaille, Philippe. Production of a-ketobutyrate by engineered Escherichia coli.PCT Int. Appl. (2006), 31pp.
External Links:
ResourceLink
CHEBI ID30831
HMDB IDHMDB00005
Pubchem Compound ID58
Kegg IDC00109
ChemSpider ID57
FOODB IDFDB003359
WikipediaAlpha-ketobutyric_acid
BioCyc ID2-OXOBUTANOATE

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Minor of three pyruvate decarboxylases (PDC1, PDC5, PDC6) implicated in the nonoxidative conversion of pyruvate to acetaldehyde and carbon dioxide during alcoholic fermentation. Most of the produced acetaldehyde is subsequently reduced to ethanol, but some is required for cytosolic acetyl-CoA production for biosynthetic pathways. The enzyme is also one of five 2-oxo acid decarboxylases (PDC1, PDC5, PDC6, ARO10, and THI3) able to decarboxylate more complex 2-oxo acids (alpha-keto-acids) than pyruvate, which seem mainly involved in amino acid catabolism. Here the enzyme catalyzes the decarboxylation of amino acids, which, in a first step, have been transaminated to the corresponding 2-oxo acids. In a third step, the resulting aldehydes are reduced to alcohols, collectively referred to as fusel oils or alcohols. Its preferred substrates are the transaminated amino acids valine, isoleucine, phenylalanine, and tryptophan, whereas leucine is no substrate. In a side-reaction the carbanionic intermediate (or active aldehyde) generated by decarboxylation or by activation of an aldehyde can react with an aldehyde via condensation (or carboligation) yielding a 2-hydroxy ketone, collectively called acyloins. The expression level of this protein in the presence of fermentable carbon sources is so low that it can not compensate for the other two pyruvate decarboxylases to sustain fermentation
Gene Name:
PDC6
Uniprot ID:
P26263
Molecular weight:
61579.89844
Reactions
#<Reaction::ActiveRecord_Associations_CollectionProxy:0xa5f05514>
General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
Not Available
Uniprot ID:
Q04533
Molecular weight:
74312.70313
Reactions
#<Reaction::ActiveRecord_Associations_CollectionProxy:0xaed9a5f4>
General function:
Involved in pyridoxal phosphate binding
Specific function:
L-cystathionine + H(2)O = L-cysteine + NH(3) + 2-oxobutanoate
Gene Name:
CYS3
Uniprot ID:
P31373
Molecular weight:
42541.69922
Reactions
#<Reaction::ActiveRecord_Associations_CollectionProxy:0xa7843738>
General function:
Involved in catalytic activity
Specific function:
L-threonine = 2-oxobutanoate + NH(3)
Gene Name:
ILV1
Uniprot ID:
P00927
Molecular weight:
63830.69922
Reactions
#<Reaction::ActiveRecord_Associations_CollectionProxy:0xa78408a8>
General function:
Involved in catalytic activity
Specific function:
L-serine = pyruvate + NH(3)
Gene Name:
CHA1
Uniprot ID:
P25379
Molecular weight:
39301.0
Reactions
#<Reaction::ActiveRecord_Associations_CollectionProxy:0xa8a0d9c8>
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Has aromatic amino acid transaminase activity and kynurenine aminotransferase activity
Gene Name:
ARO9
Uniprot ID:
P38840
Molecular weight:
58527.0
Reactions
#<Reaction::ActiveRecord_Associations_CollectionProxy:0x921a6b10>
General function:
Involved in magnesium ion binding
Specific function:
2 pyruvate = 2-acetolactate + CO(2)
Gene Name:
ILV2
Uniprot ID:
P07342
Molecular weight:
74936.29688
Reactions
#<Reaction::ActiveRecord_Associations_CollectionProxy:0x90523c40>