Identification
YMDB ID: YMDB00071
Name: 2-Ketobutyric acid
Species: Saccharomyces cerevisiae
Strain: Baker's yeast
Description: Alpha-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
Download: MOL | SDF | SMILES | InChI
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-
Chemical Formula:
C4H6O3
Weight: Average: 102.0886
Monoisotopic: 102.031694058
InChI Key: InChIKey=TYEYBOSBBBHJIV-UHFFFAOYSA-N
InChI:
InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
Plain Text
CAS number: 600-18-0
IUPAC Name:
2-oxobutanoic acid
Traditional IUPAC Name:
2-oxobutanoic acid
SMILES:
[H]OC(=O)C(=O)C([H])([H])C([H])([H])[H]
Plain Text
Chemical Taxonomy
Kingdom: Organic Compounds
Super Class: Lipids
Class: Fatty Acids and Conjugates
Sub Class: Straight Chain Fatty Acids
Other Descriptors:
  • Organic Oxonium Compounds
  • Saturated Fatty Acids
  • Short-chain Fatty Acids
Substituents:
  • alpha_keto-acid
  • ketone
  • carboxylic acid
Physical Properties
State: Solid
Charge: 0
Melting point: 33°C
Experimental Properties:
Property Value Source
Water Solubility: 119 mg/mL [HMP experimental] PhysProp
Predicted Properties:
Property Value Source
Water Solubility: 7.92e+01 g/l ALOGPS
LogP: 0.07 ALOGPS
LogP: 0.7664098003333332 ChemAxon Molconvert
LogS: -0.11 ALOGPS
pKa: Not Available ChemAxon Molconvert
Hydrogen Acceptor Count: 3 ChemAxon Molconvert
Hydrogen Donor Count: 1 ChemAxon Molconvert
Polar Surface Area: 54.37 A2 ChemAxon Molconvert
Rotatable Bond Count: 2 ChemAxon Molconvert
Refractivity: 22.6 ChemAxon Molconvert
Polarizability: 9.2 ChemAxon Molconvert
Biological Properties
Cellular Locations:
  • mitochondrion
  • cytoplasm
Pathways:
  • Propanoate metabolism 00640 Link_out
  • Cysteine and methionine metabolism 00270 Link_out
  • Valine, leucine and isoleucine biosynthesis 00290 Link_out
  • Glycine, serine and threonine metabolism 00260 Link_out
Concentrations
Not Available
Details describing the conversion of literature concentrations can be found here.
Spectra
Experimental Low Energy QqQ MS/MS Spectrum view
Experimental Medium Energy QqQ MS/MS Spectrum view
Experimental High Energy QqQ MS/MS Spectrum view
Experimental 13C HSQC Spectrum view
Experimental 1H NMR Spectrum view
Experimental 2D TOCSY Spectrum view
Experimental 13C NMR Spectrum view
Experimental GC-EI-TOF MS/MS Spectrum view
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219. Pubmed: 21051339 Link_out
  • 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. Pubmed: 18846089 Link_out
  • 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. Pubmed: 14607989 Link_out
  • 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. Pubmed: 8972574 Link_out
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:
Resource Link
CHEBI ID: 30831 Link_out
HMDB ID: HMDB00005 Link_out
Pubchem Compound ID: 58 Link_out
Kegg ID: C00109 Link_out
ChemSpider ID: 57 Link_out
Wikipedia: Alpha-ketobutyric_acid Link_out
BioCyc ID: 2-OXOBUTANOATE Link_out
Enzymes
Name: Putative cystathionine gamma-synthase YML082W
Reactions:
  • O(4)-succinyl-L-homoserine + L-cysteine = L-cystathionine + succinate.
Gene Name:
Uniprot ID: Q04533 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cystathionine gamma-lyase
Reactions:
  • L-cystathionine + H(2)O = L-cysteine + NH(3) + 2-oxobutanoate.
Gene Name: CYS3 Link_out
Uniprot ID: P31373 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Threonine dehydratase, mitochondrial
Reactions:
  • L-threonine = 2-oxobutanoate + NH(3).
Gene Name: ILV1 Link_out
Uniprot ID: P00927 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Catabolic L-serine/threonine dehydratase
Reactions:
  • L-serine = pyruvate + NH(3).
  • L-threonine = 2-oxobutanoate + NH(3).
Gene Name: CHA1 Link_out
Uniprot ID: P25379 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acetolactate synthase catalytic subunit, mitochondrial
Reactions:
  • 2 pyruvate = 2-acetolactate + CO(2).
Gene Name: ILV2 Link_out
Uniprot ID: P07342 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Not Available