Record Information
Version3.6
Creation Date2007-05-23 09:48:15 UTC
Update Date2013-02-09 00:14:49 UTC
HMDB IDHMDB06454
Secondary Accession NumbersNone
Metabolite Identification
Common NameL-2-Amino-3-oxobutanoic acid
DescriptionL-2-Amino-3-oxobutanoic acid or L-2-amino acetic acid is involved in glycine/serine metabolism and is a breakdown product from glycine. It spontaneously decomposes to aminoacetone. Delta-aminolevuliinate synthase is the enzyme that catalyzes the interconversion between glycine and L-2-amino-3-oxobutanoic acid. Glycine C-acetyltransferase is also capable of catalyzing this reaction.
Structure
Thumb
Synonyms
  1. (2S)-2-amino-3-oxobutanoate
  2. (2S)-2-amino-3-oxobutanoic acid
  3. (S)-2-Amino-3-oxobutanoate
  4. (S)-2-Amino-3-oxobutanoic acid
  5. 2-Amino-3-oxobutanoate
  6. 2-Amino-3-oxobutanoic acid
  7. L-2-Amino acetic acid
  8. L-2-Amino-3-oxobutanoate
  9. L-2-Amino-3-oxobutanoic acid
  10. L-2-Amino-acetoacetate
Chemical FormulaC4H7NO3
Average Molecular Weight117.1033
Monoisotopic Molecular Weight117.042593095
IUPAC Name(2S)-2-amino-3-oxobutanoic acid
Traditional IUPAC Name(2S)-2-amino-3-oxobutanoic acid
CAS Registry NumberNot Available
SMILES
CC(=O)[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C4H7NO3/c1-2(6)3(5)4(7)8/h3H,5H2,1H3,(H,7,8)/t3-/m0/s1
InChI KeySAUCHDKDCUROAO-VKHMYHEASA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • 2-amino-3-oxobutanoic acid(ChEBI)
  • Aliphatic Acyclic Compounds
  • L-alpha-amino acid(ChEBI)
  • Oxo fatty acids(KEGG)
  • Oxo fatty acids(Lipidmaps)
Substituents
  • Alpha Aminoketone
  • Beta Keto Acid
  • Carboxylic Acid
  • Ketone
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
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 solubility206 g/LALOGPS
logP-2.6ALOGPS
logP-3.1ChemAxon
logS0.25ALOGPS
pKa (strongest acidic)1.87ChemAxon
pKa (strongest basic)7.25ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area80.39ChemAxon
rotatable bond count2ChemAxon
refractivity25.53ChemAxon
polarizability10.51ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Glycine and Serine MetabolismSMP00004map00260
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 IDFDB023915
KNApSAcK IDNot Available
Chemspider ID389046
KEGG Compound IDC03508
BioCyc IDAMINO-OXOBUT
BiGG ID41986
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06454
Metagene LinkHMDB06454
METLIN IDNot Available
PubChem Compound440033
PDB IDAKB
ChEBI ID40673
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
GCAT
Uniprot ID:
O75600
Reactions
Acetyl-CoA + Glycine unknown Coenzyme A + L-2-Amino-3-oxobutanoic aciddetails
Acetyl-CoA + Glycine unknown Coenzyme A + L-2-Amino-3-oxobutanoic aciddetails