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Record Information
Version3.6
Creation Date2008-08-12 13:13:41 UTC
Update Date2016-02-11 01:07:57 UTC
HMDB IDHMDB06801
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-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
ValueSource
(3R)-3-Hydroxy-2-oxo-4-phosphonooxybutanoateChEBI
2-oxo-3-Hydroxy-4-phosphobutanoateChEBI
alpha-keto-3-Hydroxy-4-phosphobutyrateChEBI
2-oxo-3-Hydroxy-4-phosphobutanoic acidGenerator
a-keto-3-Hydroxy-4-phosphobutyrateGenerator
a-keto-3-Hydroxy-4-phosphobutyric acidGenerator
alpha-keto-3-Hydroxy-4-phosphobutyric acidGenerator
α-keto-3-hydroxy-4-phosphobutyrateGenerator
α-keto-3-hydroxy-4-phosphobutyric acidGenerator
Chemical FormulaC4H7O8P
Average Molecular Weight214.0673
Monoisotopic Molecular Weight213.987853712
IUPAC Name(3R)-3-hydroxy-2-oxo-4-(phosphonooxy)butanoic acid
Traditional Name(3R)-3-hydroxy-2-oxo-4-(phosphonooxy)butanoic acid
CAS Registry NumberNot Available
SMILES
O[C@H](COP(O)(O)=O)C(=O)C(O)=O
InChI Identifier
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
InChI KeyInChIKey=MZJFVXDTNBHTKZ-UWTATZPHSA-N
Chemical 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.
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
  • 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB024087
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06054
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06801
Metagene LinkHMDB06801
METLIN IDNot Available
PubChem Compound21145142
PDB IDNot Available
ChEBI ID27951
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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 (By similarity).
Gene Name:
PSAT1
Uniprot ID:
Q9Y617
Molecular weight:
35188.305
Reactions
O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid → 2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic aciddetails