Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:01 UTC
HMDB IDHMDB01172
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Methyl-3-oxopropanoic acid
Description2-Methyl-3-oxopropanoic acid is an intermediate in the metabolism of Propanoate. It is a substrate for 3-hydroxyisobutyrate dehydrogenase (mitochondrial), Alanine--glyoxylate aminotransferase 2 (mitochondrial) and Methylmalonate-semialdehyde dehydrogenase (mitochondrial).
Structure
Thumb
Synonyms
  1. 2-Methyl-3-oxopropanoate
  2. 2-Methyl-3-oxopropanoic acid
  3. 3-Oxo-2-methylpropanoate
  4. 3-Oxo-2-methylpropanoic acid
  5. Ch3-malonate-semialdehyde
  6. Methylmalonate semialdehyde
  7. Methylmalonate-semialdehyde
Chemical FormulaC4H6O3
Average Molecular Weight102.0886
Monoisotopic Molecular Weight102.031694058
IUPAC Name2-methyl-3-oxopropanoic acid
Traditional IUPAC Name2-methyl-3-oxopropanoic acid
CAS Registry Number6236-08-4
SMILES
CC(C=O)C(O)=O
InChI Identifier
InChI=1S/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7)
InChI KeyVOKUMXABRRXHAR-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
Sub ClassCarboxylic Acid Derivatives
Other Descriptors
  • 2-methyl-3-oxopropanoic acid(ChEBI)
  • Aliphatic Acyclic Compounds
  • Oxo fatty acids(Lipidmaps)
  • semialdehyde(ChEBI)
Substituents
  • Aldehyde
Direct ParentCarboxylic Acids
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Inositol metabolism
  • Component of Propanoate metabolism
ApplicationNot Available
Cellular locations
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility266 g/LALOGPS
logP0ALOGPS
logP0.053ChemAxon
logS0.42ALOGPS
pKa (strongest acidic)3.98ChemAxon
pKa (strongest basic)-7.2ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area54.37ChemAxon
rotatable bond count2ChemAxon
refractivity22.64ChemAxon
polarizability9.15ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022464
KNApSAcK IDNot Available
Chemspider ID290
KEGG Compound IDC00349
BioCyc IDCH3-MALONATE-S-ALD
BiGG ID34698
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01172
Metagene LinkHMDB01172
METLIN ID6053
PubChem Compound296
PDB IDNot Available
ChEBI ID16256
References
Synthesis ReferenceRobinson, Wm. G.; Coon, Minor J. Purification and properties of b-hydroxyisobutyric dehydrogenase. Journal of Biological Chemistry (1957), 225 511-21.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
ALDH6A1
Uniprot ID:
Q02252
Reactions
2-Methyl-3-oxopropanoic acid + Coenzyme A + Water + NAD unknown Propionyl-CoA + Carbonic acid + NADHdetails
Gene Name:
AOX1
Uniprot ID:
Q06278
Gene Name:
ABAT
Uniprot ID:
P80404
Reactions
(S)-b-aminoisobutyric acid + Oxoglutaric acid unknown 2-Methyl-3-oxopropanoic acid + L-Glutamic aciddetails
Gene Name:
EHHADH
Uniprot ID:
Q08426
Gene Name:
HIBADH
Uniprot ID:
P31937
Reactions
(S)-3-Hydroxyisobutyric acid + NAD unknown 2-Methyl-3-oxopropanoic acid + NADHdetails
Gene Name:
AGXT2
Uniprot ID:
Q9BYV1
Reactions
(R)-b-aminoisobutyric acid + Pyruvic acid unknown 2-Methyl-3-oxopropanoic acid + L-Alaninedetails