2-Oxo-3-hydroxy-4-phosphobutanoic acid (PAMDB000690)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000690
Identification
Name: 2-Oxo-3-hydroxy-4-phosphobutanoic acid
Description:2-Oxo-3-hydroxy-4-phosphobutanoic acid is involved in the interconversion of O-phospho-4-hydroxy-L-threonine. This reaction is catalyzed by phosphoserine aminotransferase 1. These amino acid derivatives are sometimes considered to be part of the vitamin B6 pathway.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (3R)-3-hydroxy-2-oxo-4 phosphonooxybutanoate
  • (3R)-3-hydroxy-2-oxo-4 phosphonooxybutanoic acid
  • (3R)-3-Hydroxy-2-oxo-4-phosphonooxybutanoate
  • (3R)-3-Hydroxy-2-oxo-4-phosphonooxybutanoic acid
  • 2-Oxo-3-hydroxy-4-phosphobutanoate
  • 2-Oxo-3-hydroxy-4-phosphobutanoic acid
  • 3-hydroxy-4-phospho-hydroxy-α-ketobutyrate
  • 3-Hydroxy-4-phospho-hydroxy-α-ketobutyric acid
  • 3-Hydroxy-4-phospho-hydroxy-a-ketobutyrate
  • 3-Hydroxy-4-phospho-hydroxy-a-ketobutyric acid
  • 3-Hydroxy-4-phospho-hydroxy-alpha-ketobutyrate
  • 3-Hydroxy-4-phospho-hydroxy-alpha-ketobutyric acid
  • 3-Hydroxy-4-phospho-hydroxy-α-ketobutyrate
  • 3-Hydroxy-4-phospho-hydroxy-α-ketobutyric acid
  • a-keto-3-Hydroxy-4-phosphobutyrate
  • a-keto-3-Hydroxy-4-phosphobutyric acid
  • Alpha-Keto-3-hydroxy-4-phosphobutyrate
  • Alpha-Keto-3-hydroxy-4-phosphobutyric acid
  • α-keto-3-Hydroxy-4-phosphobutyrate
  • α-keto-3-Hydroxy-4-phosphobutyric acid
Chemical Formula: C4H7O8P
Average Molecular Weight: 214.0673
Monoisotopic Molecular Weight: 213.987853712
InChI Key: MZJFVXDTNBHTKZ-UWTATZPHSA-N
InChI:InChI=1S/C4H7O8P/c5-2(3(6)4(7)8)1-12-13(9,10)11/h2,5H,1H2,(H,7,8)(H2,9,10,11)/t2-/m1/s1
CAS number: Not Available
IUPAC Name:(3R)-3-hydroxy-2-oxo-4-(phosphonooxy)butanoic acid
Traditional IUPAC Name: (3R)-3-hydroxy-2-oxo-4-(phosphonooxy)butanoic acid
SMILES:O[C@H](COP(O)(O)=O)C(=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Keto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct Parent Short-chain keto acids and derivatives
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Short-chain keto acid
  • Beta-hydroxy acid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydroxy acid
  • Beta-ketoaldehyde
  • Alpha-keto acid
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility16.2 mg/mLALOGPS
logP-2ALOGPS
logP-1.4ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.34ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area141.36 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.6 m3·mol-1ChemAxon
Polarizability15.26 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
L-Glutamate + 2-Oxo-3-hydroxy-4-phosphobutanoic acid <> alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine
4-Phospho-D-erythronate + NAD <> Hydrogen ion + NADH + 2-Oxo-3-hydroxy-4-phosphobutanoic acid
2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamate <> O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid
4-Phospho-D-erythronate + NAD > 2-Oxo-3-hydroxy-4-phosphobutanoic acid + NADH
Phosphoserine + alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine <> Phosphohydroxypyruvic acid + L-Glutamate + 2-Oxo-3-hydroxy-4-phosphobutanoic acid
2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic acid + L-Glutamate <> A-Ketoglutaric acid oxime + O-Phospho-4-hydroxy-L-threonine
2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic acid + L-Glutamate <> O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1930000000-9c3c35aa2de551b4bbf2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ke-4900000000-162b52e552d9157d3bbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9300000000-abe9d170b8c46a45e858View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0329-9730000000-c5dda701292450f19043View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-1880b6c8035cdbc2520fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8b44e7c9ed6f8dcaee86View 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 ID27951
HMDB IDHMDB06801
Pubchem Compound ID21145142
Kegg IDC06054
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc ID3OH-4P-OH-ALPHA-KETOBUTYRATE
EcoCyc ID3OH-4P-OH-ALPHA-KETOBUTYRATE