You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-23 09:48:15 UTC
Update Date2020-02-26 21:26:24 UTC
HMDB IDHMDB0006454
Secondary Accession Numbers
  • HMDB06454
Metabolite Identification
Common NameL-2-Amino-3-oxobutanoic acid
DescriptionL-2-Amino-3-oxobutanoic acid, also known as L-2-amino-acetoacetate or (S)-2-amino-3-oxobutanoate, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-2-Amino-3-oxobutanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. L-2-Amino-3-oxobutanoic acid exists in all living species, ranging from bacteria to humans. L-2-amino-3-oxobutanoic acid can be biosynthesized from acetyl-CoA and glycine through the action of the enzyme 2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial. In humans, L-2-amino-3-oxobutanoic acid is involved in glycine and serine metabolism. It spontaneously decomposes to aminoacetone.
Structure
Data?1582752384
Synonyms
ValueSource
(S)-2-Amino-3-oxobutanoic acidChEBI
2-AMINO-3-ketobutyrIC ACIDChEBI
L-2-Amino-3-oxobutanoateChEBI
L-2-Amino-acetoacetateChEBI
(S)-2-Amino-3-oxobutanoateGenerator
2-AMINO-3-ketobutyrateGenerator
L-2-Amino-acetoacetic acidGenerator
(2S)-2-Amino-3-oxobutanoateHMDB
(2S)-2-Amino-3-oxobutanoic acidHMDB
2-Amino-3-oxobutanoateHMDB
2-Amino-3-oxobutanoic acidHMDB
L-2-Amino acetic acidHMDB
Chemical FormulaC4H7NO3
Average Molecular Weight117.1033
Monoisotopic Molecular Weight117.042593095
IUPAC Name(2S)-2-amino-3-oxobutanoic acid
Traditional Name2-amino-3-ketobutyric 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
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Beta-keto acid
  • Short-chain keto acid
  • Beta-hydroxy ketone
  • Keto acid
  • 1,3-dicarbonyl compound
  • Alpha-aminoketone
  • Amino acid
  • Ketone
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary aliphatic amine
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 Area80.39 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.53 m³·mol⁻¹ChemAxon
Polarizability10.47 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9000000000-22150e9e4fa3d3433203Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006y-9300000000-b1976cb0fd0e419923c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gi0-5900000000-1565f4db4a91c43d6697Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-9200000000-1dcade0f25d1eaa7da38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9100000000-ef438e90f9a367453dd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9800000000-e0bdda855b20afe7598cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9200000000-95fb6afa14c1b9b751e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-210f3affcabb1713c4e3Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03915
Phenol Explorer Compound IDNot Available
FooDB IDFDB023915
KNApSAcK IDNot Available
Chemspider ID389046
KEGG Compound IDC03508
BioCyc IDAMINO-OXOBUT
BiGG ID41986
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440033
PDB IDAKB
ChEBI ID40673
Food Biomarker OntologyNot Available
VMH ID2AOBUT
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Not Available
Gene Name:
ALAS1
Uniprot ID:
P13196
Molecular weight:
70580.325
General function:
Involved in glycine C-acetyltransferase activity
Specific function:
Not Available
Gene Name:
GCAT
Uniprot ID:
O75600
Molecular weight:
47973.79
Reactions
Acetyl-CoA + Glycine → Coenzyme A + L-2-Amino-3-oxobutanoic aciddetails
Acetyl-CoA + Glycine → Coenzyme A + L-2-Amino-3-oxobutanoic aciddetails