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Identification
YMDB IDYMDB01041
NameL-3-Oxoalanine
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-Aminomalonate semialdehyde, also known as L-alpha-formylglycine, 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. 2-Aminomalonate semialdehyde is a very strong basic compound (based on its pKa). 2-Aminomalonate semialdehyde exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
Synonyms
  • 2-Aminomalonate semialdehyde
  • 2-Ammoniomalonate semialdehyde
  • L-alpha-formylglycine
  • 2-Ammoniomalonic acid semialdehyde
  • L-a-Formylglycine
  • L-Α-formylglycine
  • 2-Aminomalonic acid semialdehyde
  • C(alpha)-Formylglycine
  • 3-oxo-L-Alanine
  • 2-Amino-3-oxopropanoic acid
  • alpha-Formylglycine
  • 3-Oxoalanine
CAS numberNot Available
WeightAverage: 103.0767
Monoisotopic: 103.026943031
InChI KeyXMTCKNXTTXDPJX-REOHCLBHSA-N
InChIInChI=1S/C3H5NO3/c4-2(1-5)3(6)7/h1-2H,4H2,(H,6,7)/t2-/m0/s1
IUPAC Name(2S)-2-amino-3-oxopropanoic acid
Traditional IUPAC Name2-aminomalonate semialdehyde
Chemical FormulaC3H5NO3
SMILES[H]C(=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
  • 1,3-dicarbonyl compound
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Aldehyde
  • Carbonyl group
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility242 g/LALOGPS
logP-2.8ALOGPS
logP-3.6ChemAxon
logS0.37ALOGPS
pKa (Strongest Acidic)1.66ChemAxon
pKa (Strongest Basic)7.18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity21.06 m³·mol⁻¹ChemAxon
Polarizability8.51 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 PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
NADP + L-SerineNADPH + hydron + L-3-Oxoalanine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-129e33e49404ea4ec543JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0k9i-9300000000-1a42eb4f596f6dcd8e32JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-bb288560905cc883049bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-005758ce9275f75a9c80JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-4900000000-32e8e76f27ffbb43d6c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zgi-9500000000-c8b763e487f04ffaa17dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-d3736532a9a9202b1aa9JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • 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 ID37012
HMDB IDNot Available
Pubchem Compound ID5232345
Kegg IDC11822
ChemSpider ID391645
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available