Showing Metabocard for 2-oxobutanoate (BASm0000730)

Common Name2-oxobutanoate
Description2-Ketobutyric acid, also known as alpha-ketobutyrate or 2-oxobutyrate, 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. 2-Ketobutyric acid is a substance that 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 is also one of the degradation products of threonine. It can be converted into propionyl-CoA (and subsequently methylmalonyl CoA, which can be converted into succinyl CoA, a citric acid cycle intermediate), and thus enter the citric acid cycle. More specifically, 2-ketobutyric acid is a product of the lysis of cystathionine.
Structure
Molecular FormulaC4H6O3
Average Mass102.08860
Monoisotopic Mass102.03169
IUPAC Name2-oxobutanoic acid
Traditional Name2-oxobutanoic acid
CAS Registry Number600-18-0
SMILESCCC(=O)C(=O)[O-]
InChI IdentifierInChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
InChI KeyTYEYBOSBBBHJIV-UHFFFAOYSA-N
CHEBI IDCHEBI:16763
HMDB IDHMDB0000005
Pathways
NameSMPDB/PathBank
Glycine, serine and threonine metabolism
Selenocompound metabolism
Propanoate metabolism
Methionine Metabolism
Cystathionine Beta-Synthase Deficiency
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)
Malonic Aciduria
Methylmalonic Aciduria Due to Cobalamin-Related Disorders
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency
Methionine Adenosyltransferase Deficiency
Glycine N-methyltransferase Deficiency
Non Ketotic Hyperglycinemia
Dimethylglycine Dehydrogenase Deficiency
Sarcosinemia
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)
Hypermethioninemia
Threonine and 2-Oxobutanoate Degradation
Homocysteine Degradation
Dimethylglycine Dehydrogenase Deficiency
Hyperglycinemia, non-ketotic
Malonyl-coa decarboxylase deficiency
Gamma-cystathionase deficiency (CTH)
Homocystinuria, cystathionine beta-synthase deficiency
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation type
3-Phosphoglycerate dehydrogenase deficiency
StateNot Available
Water Solubility7.92e+01 g/l
logP0.07
logS-0.11
pKa (Strongest Acidic)3.19
pKa (Strongest Basic)-9.65
Hydrogen Acceptor Count3
Hydrogen Donor Count1
Polar Surface Area54.37 Ų
Rotatable Bond Count2
Physiological Charge-1
Formal Charge0
Refractivity22.62 m³·mol⁻¹
Polarizability9.21

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