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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-
CAS number600-18-0
WeightAverage: 102.0886
Monoisotopic: 102.031694058
InChI KeyInChIKey=TYEYBOSBBBHJIV-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
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acids and Conjugates
Sub ClassStraight Chain Fatty Acids
Other Descriptors
  • Organic Oxonium Compounds
  • Saturated Fatty Acids
  • Short-chain Fatty Acids
Substituents
  • Organic Oxonium Compounds
  • Saturated Fatty Acids
  • Short-chain Fatty Acids
Physical Properties
StateSolid
Charge0
Melting point33°C
Experimental Properties
PropertyValueReference
Water Solubility119 mg/mL [HMP experimental]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
water solubility7.92e+01 g/lALOGPS
logP0.07ALOGPS
logP0.77ChemAxon
logS-0.11ALOGPS
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area54.37ChemAxon
rotatable bond count2ChemAxon
refractivity22.62ChemAxon
polarizability9.2ChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Pathways
  • Propanoate metabolism ‐ 00640
  • Cysteine and methionine metabolism ‐ 00270
  • Valine, leucine and isoleucine biosynthesis ‐ 00290
  • Glycine, serine and threonine metabolism ‐ 00260
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
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 ID:30831
HMDB ID:HMDB00005
Pubchem Compound ID:58
Kegg ID:C00109
ChemSpider ID:57
Wikipedia:Alpha-ketobutyric_acid
BioCyc ID:2-OXOBUTANOATE

Enzymes

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
O(4)-succinyl-L-homoserine + L-cysteine = L-cystathionine + succinate.
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
L-cystathionine + H(2)O = L-cysteine + NH(3) + 2-oxobutanoate.
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
L-threonine = 2-oxobutanoate + NH(3).
General function:
Involved in catalytic activity
Specific function:
L-serine = pyruvate + NH(3)
Gene Name:
CHA1
Uniprot ID:
P25379
Molecular weight:
39301.0
Reactions
L-serine = pyruvate + NH(3).
L-threonine = 2-oxobutanoate + NH(3).
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
2 pyruvate = 2-acetolactate + CO(2).