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Identification
YMDB IDYMDB00695
NameL-2-amino-3-oxobutanoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-2-Amino-3-oxobutanoic acid, also known as (S)-2-amino-3-oxobutanoate or L-2-amino-acetoacetate, 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.
Structure
Thumb
Synonyms
  • (2S)-2-amino-3-oxobutanoate
  • (2S)-2-amino-3-oxobutanoic acid
  • (S)-2-Amino-3-oxobutanoate
  • (S)-2-Amino-3-oxobutanoic acid
  • 2-AMINO-3-KETOBUTYRIC ACID
  • 2-amino-3-oxobutanoate
  • 2-amino-3-oxobutanoic acid
  • L-2-amino acetic acid
  • L-2-Amino-3-oxobutanoate
  • L-2-Amino-3-oxobutanoic acid
  • l-2-amino-acetoacetate
  • 2-AMINO-3-ketobutyrate
  • L-2-Amino-acetoacetic acid
CAS numberNot Available
WeightAverage: 117.1033
Monoisotopic: 117.042593095
InChI KeySAUCHDKDCUROAO-VKHMYHEASA-N
InChIInChI=1S/C4H7NO3/c1-2(6)3(5)4(7)8/h3H,5H2,1H3,(H,7,8)/t3-/m0/s1
IUPAC Name(2S)-2-amino-3-oxobutanoic acid
Traditional IUPAC Name2-amino-3-ketobutyric acid
Chemical FormulaC4H7NO3
SMILESCC(=O)[C@H](N)C(O)=O
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Glycine, serine and threonine metabolismec00260 Map00260
SMPDB Reactions
L-Threonine + NADhydron + NADH + L-2-amino-3-oxobutanoic acid
L-2-amino-3-oxobutanoic acid + Coenzyme AAcetyl-CoA + Glycine
KEGG Reactions
L-2-amino-3-oxobutanoic acid + Coenzyme AGlycine + Acetyl-CoA
L-2-amino-3-oxobutanoic acid + hydronAminoacetone + Carbon dioxide
NADP + L-AllothreonineL-2-amino-3-oxobutanoic acid + NADPH + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Fujisawa, H., Nagata, S., Misono, H. (2003). "Characterization of short-chain dehydrogenase/reductase homologues of Escherichia coli (YdfG) and Saccharomyces cerevisiae (YMR226C)." Biochim Biophys Acta 1645:89-94.12535615
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID40673
HMDB IDHMDB06454
Pubchem Compound ID5460100
Kegg IDC03508
ChemSpider ID389046
FOODB IDFDB023915
Wikipedia IDNot Available
BioCyc IDAMINO-OXOBUT

Enzymes

General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Component of serine palmitoyltransferase (SPT), which catalyzes the committed step in the synthesis of sphingolipids, the condensation of serine with palmitoyl CoA to form the long chain base 3-ketosphinganine
Gene Name:
LCB1
Uniprot ID:
P25045
Molecular weight:
62206.60156
Reactions
Palmitoyl-CoA + L-serine → CoA + 3-dehydro-D-sphinganine + CO(2).
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q05016
Molecular weight:
29158.09961
Reactions
L-serine + NADP+ → 2-ammoniomalonate semialdehyde + NADPH + H+
General function:
Involved in zinc ion binding
Specific function:
NADP-dependent alcohol dehydrogenase with a broad substrate specificity
Gene Name:
ADH6
Uniprot ID:
Q04894
Molecular weight:
39617.30078
Reactions
An alcohol + NADP(+) → an aldehyde + NADPH.