Record Information
Version2.0
Creation Date2012-05-31 14:09:24 -0600
Update Date2015-06-03 15:54:54 -0600
Secondary Accession Numbers
  • ECMDB06801
Identification
Name:2-Oxo-3-hydroxy-4-phosphobutanoic acid
Description2-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
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
Weight:Average: 214.0673
Monoisotopic: 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
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Short-chain keto acid
  • Beta-hydroxy acid
  • Acyloin
  • Alpha-keto acid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Hydroxy acid
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility16.2 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.6 m³·mol⁻¹ChemAxon
Polarizability15.26 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
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-db85b7397058e1ec03b8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0005-9121000000-aee0eaf4d81dbd99259bView in MoNA
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

Enzymes

General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Catalyzes the oxidation of erythronate-4-phosphate to 3- hydroxy-2-oxo-4-phosphonooxybutanoate
Gene Name:
pdxB
Uniprot ID:
P05459
Molecular weight:
41367
Reactions
4-phospho-D-erythronate + NAD(+) = (3R)-3-hydroxy-2-oxo-4-phosphonooxybutanoate + NADH.
General function:
Involved in metabolic process
Specific function:
Catalyzes the reversible conversion of 3- phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4- phosphonooxybutanoate to phosphohydroxythreonine. Is involved in both pyridoxine and serine biosynthesis
Gene Name:
serC
Uniprot ID:
P23721
Molecular weight:
39783
Reactions
O-phospho-L-serine + 2-oxoglutarate = 3-phosphonooxypyruvate + L-glutamate.
4-phosphonooxy-L-threonine + 2-oxoglutarate = (3R)-3-hydroxy-2-oxo-4-phosphonooxybutanoate + L-glutamate.