2-Amino-3-oxo-4-phosphonooxybutyrate (PAMDB000885)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000885
Identification
Name: 2-Amino-3-oxo-4-phosphonooxybutyrate
Description:2-amino-3-oxo-4-phosphonooxybutyrate is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2S)-2-Amino-3-oxo-4-phosphonooxybutanoate
  • (2S)-2-Amino-3-oxo-4-phosphonooxybutanoic acid
  • 2-amino-3-oxo-4-phosphonooxybutyrate
  • 2-Amino-3-oxo-4-phosphonooxybutyric acid
  • L-2-Amino-3-oxo-4-phosphonooxybutyrate
  • L-2-Amino-3-oxo-4-phosphonooxybutyric acid
Chemical Formula: C4H8NO7P
Average Molecular Weight: 213.0826
Monoisotopic Molecular Weight: 213.003838127
InChI Key: LMKSRFWSQAKTOE-VKHMYHEASA-N
InChI:InChI=1S/C4H8NO7P/c5-3(4(7)8)2(6)1-12-13(9,10)11/h3H,1,5H2,(H,7,8)(H2,9,10,11)/t3-/m0/s1
CAS number: Not Available
IUPAC Name:(2S)-2-amino-3-oxo-4-(phosphonooxy)butanoic acid
Traditional IUPAC Name: (2S)-2-amino-3-oxo-4-(phosphonooxy)butanoic acid
SMILES:[H][C@@](N)(C(O)=O)C(=O)COP(O)(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent D-alpha-amino acids
Alternative Parents
Substituents
  • D-alpha-amino acid
  • Monoalkyl phosphate
  • Short-chain keto acid
  • Beta-keto acid
  • Amino fatty acid
  • Fatty acyl
  • Alkyl phosphate
  • 1,3-dicarbonyl compound
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Keto acid
  • Beta-hydroxy ketone
  • Alpha-aminoketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility16.6 mg/mLALOGPS
logP-1.8ALOGPS
logP-3.3ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.03ChemAxon
pKa (Strongest Basic)7.23ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area147.15 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.11 m3·mol-1ChemAxon
Polarizability16.03 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
O-Phospho-4-hydroxy-L-threonine + NAD <> 2-Amino-3-oxo-4-phosphonooxybutyrate + NADH + Hydrogen ion
2-Amino-3-oxo-4-phosphonooxybutyrate + Hydrogen ion > 1-Amino-propan-2-one-3-phosphate + Carbon dioxide
NAD + 2-Amino-3-oxo-4-phosphonooxybutyrate + O-Phospho-4-hydroxy-L-threonine <> 3-Amino-2-oxopropyl phosphate + Carbon dioxide + NADH + Hydrogen ion
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0292-4930000000-5d03d45aa354832df1caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-9800000000-1651e4804966f49060f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-9100000000-de1b0969b556dea6c460View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-9860000000-4aae0dd934f15993c083View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-4a5986983776a835b113View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8918b9d07cb95a5132b4View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID16273
HMDB IDNot Available
Pubchem Compound ID441260
Kegg IDC07335
ChemSpider ID390031
Wikipedia IDNot Available
BioCyc ID2-AMINO-3-OXO-4-PHOSPHONOOXYBUTYRATE
EcoCyc ID2-AMINO-3-OXO-4-PHOSPHONOOXYBUTYRATE