Human Metabolome Database Version 3.5

Showing metabocard for L-2-Amino-3-oxobutanoic acid (HMDB06454)

Record Information
Version 3.5
Creation Date 2007-05-23 03:48:15 -0600
Update Date 2013-02-08 17:14:49 -0700
HMDB ID HMDB06454
Secondary Accession Numbers None
Metabolite Identification
Common Name L-2-Amino-3-oxobutanoic acid
Description L-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C4H7NO3
Average Molecular Weight 117.1033
Monoisotopic Molecular Weight 117.042593095
IUPAC Name (2S)-2-amino-3-oxobutanoic acid
Traditional IUPAC Name (2S)-2-amino-3-oxobutanoic acid
CAS Registry Number Not 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 Key SAUCHDKDCUROAO-VKHMYHEASA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha 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 Parent Alpha Amino Acids and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 206 g/L ALOGPS
LogP -2.63 ALOGPS
LogP -3.1 ChemAxon
LogS 0.25 ALOGPS
pKa (strongest acidic) 1.87 ChemAxon
pKa (strongest basic) 7.25 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 80.39 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 25.53 ChemAxon
Polarizability 10.51 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Glycine and Serine Metabolism SMP00004 map00260 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023915
KNApSAcK ID Not Available
Chemspider ID 389046 Link_out
KEGG Compound ID C03508 Link_out
BioCyc ID AMINO-OXOBUT Link_out
BiGG ID 41986 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06454 Link_out
Metagene Link HMDB06454 Link_out
METLIN ID Not Available
PubChem Compound 440033 Link_out
PDB ID AKB Link_out
ChEBI ID 40673 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: 5-aminolevulinate synthase, nonspecific, mitochondrial
Reactions: Not Available
Gene Name: ALAS1
Uniprot ID: P13196 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial
Reactions:
Acetyl-CoA + Glycine unknown Coenzyme A + L-2-Amino-3-oxobutanoic acid details
Acetyl-CoA + Glycine unknown Coenzyme A + L-2-Amino-3-oxobutanoic acid details
Gene Name: GCAT
Uniprot ID: O75600 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA