Showing metabocard for L-2-Amino-3-oxobutanoic acid (BMDB0006454)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:22:02 UTC
Update Date2020-05-21 16:28:59 UTC
BMDB IDBMDB0006454
Secondary Accession Numbers
  • BMDB06454
Metabolite Identification
Common NameL-2-Amino-3-oxobutanoic acid
DescriptionL-2-Amino-3-oxobutanoic acid, also known as (S)-L-L-l-2-amino-3-oxobutanoic acid or L-L-l-2-amino-3-oxobutanoic acid, 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 L-L-l-2-amino-3-oxobutanoic acid coenzyme A ligase, mitochondrial. In cattle, L-L-l-2-amino-3-oxobutanoic acid is involved in the metabolic pathway called the glycine and serine metabolism pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • 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
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9000000000-22150e9e4fa3d3433203View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006y-9300000000-b1976cb0fd0e419923c4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gi0-5900000000-1565f4db4a91c43d6697View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-9200000000-1dcade0f25d1eaa7da38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9100000000-ef438e90f9a367453dd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9800000000-e0bdda855b20afe7598cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9200000000-95fb6afa14c1b9b751e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-210f3affcabb1713c4e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-b0afa4195d3cbff82f87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-c542fb4af78140fc2eaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-5136afe8f7ab28631fe4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-4900000000-cbd7caa68b545994551bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dj-9200000000-45cde5b7b6c52af1dee2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1e9dea60f3fc6a6303f7View in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006454
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial
General function:
Coenzyme transport and metabolism
Specific function:
Not Available
Gene Name:
GCAT
Uniprot ID:
Q0P5L8
Molecular weight:
45166.0
Reactions
Acetyl-CoA + Glycine → L-2-Amino-3-oxobutanoic acid + Coenzyme Adetails