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2-Amino-3-oxo-4-phosphonooxybutyrate (M2MDB000885)

Record Information
Version2.0
Creation Date2012-05-31 14:24:05 -0600
Update Date2015-06-03 17:19:10 -0600
Secondary Accession Numbers
  • ECMDB20036
Identification
Name:2-Amino-3-oxo-4-phosphonooxybutyrate
Description2-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
MOLSDFPDBSMILESInChI
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
Weight:Average: 213.0826
Monoisotopic: 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
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
  • Monoalkyl phosphate
  • Beta-hydroxy ketone
  • Keto acid
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • 1,3-dicarbonyl compound
  • Alkyl phosphate
  • Alpha-aminoketone
  • Amino acid
  • Ketone
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility16.6 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.11 m³·mol⁻¹ChemAxon
Polarizability16.03 ųChemAxon
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
O-Phospho-4-hydroxy-L-threonine + NAD > Hydrogen ion + NADH + 2-Amino-3-oxo-4-phosphonooxybutyrate
NAD + 2-Amino-3-oxo-4-phosphonooxybutyrate + O-Phospho-4-hydroxy-L-threonine <> 3-Amino-2-oxopropyl phosphate + Carbon dioxide + NADH + Hydrogen ion
O-Phospho-4-hydroxy-L-threonine + NAD <>2 2-Amino-3-oxo-4-phosphonooxybutyrate + NADH + Hydrogen ion
O-Phospho-4-hydroxy-L-threonine + NAD <>2 2-Amino-3-oxo-4-phosphonooxybutyrate + NADH + Hydrogen ion
SMPDB Pathways:
Vitamin B6 1430936196PW000891 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9300000000-67f6d576df6ecedda3a5View in MoNA
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
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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

Enzymes

Protein Details
1. 4-hydroxythreonine-4-phosphate dehydrogenase
General function:
Involved in 4-hydroxythreonine-4-phosphate dehydrogenase activity
Specific function:
Catalyzes the NAD(P)-dependent oxidation of 4- (phosphohydroxy)-L-threonine (HTP) into 2-amino-3-oxo-4- (phosphohydroxy)butyric acid which spontaneously decarboxylates to form 3-amino-2-oxopropyl phosphate (AHAP)
Gene Name:
pdxA
Uniprot ID:
P19624
Molecular weight:
35114
Reactions
4-(phosphonooxy)-L-threonine + NAD(+) = (2S)-2-amino-3-oxo-4-phosphonooxybutanoate + NADH.