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2-Oxo-3-hydroxy-4-phosphobutanoic acid (FDB024087)

Record Information
Version1.0
Creation date2011-09-21 00:39:44 UTC
Update date2020-09-17 15:41:39 UTC
Primary IDFDB024087
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Oxo-3-hydroxy-4-phosphobutanoic acid
Description2-Oxo-3-hydroxy-4-phosphobutanoic acid, also known as (3R)-3-hydroxy-2-oxo-4-phosphonooxybutanoate or alpha-keto-3-hydroxy-4-phosphobutyrate, 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. 2-Oxo-3-hydroxy-4-phosphobutanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Oxo-3-hydroxy-4-phosphobutanoic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, 2-Oxo-3-hydroxy-4-phosphobutanoic acid has been detected, but not quantified in, several different foods, such as peanuts, breakfast cereals, kai-lans, common beans, and cardoons. This could make 2-oxo-3-hydroxy-4-phosphobutanoic acid a potential biomarker for the consumption of these foods. A 2-oxo monocarboxylic acid that is 2-oxobutanoic acid which is substituted by a phosphonooxy group at position 4 and a hydroxy group at the 3-pro-R position.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H7O8P
IUPAC name(3R)-3-hydroxy-2-oxo-4-(phosphonooxy)butanoic acid
InChI IdentifierInChI=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 KeyMZJFVXDTNBHTKZ-UWTATZPHSA-N
Isomeric SMILESO[C@H](COP(O)(O)=O)C(=O)C(O)=O
Average Molecular Weight214.0673
Monoisotopic Molecular Weight213.987853712
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-Oxo-3-hydroxy-4-phosphobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9300000000-db85b7397058e1ec03b8Spectrum
Predicted GC-MS2-Oxo-3-hydroxy-4-phosphobutanoic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0005-9121000000-aee0eaf4d81dbd99259bSpectrum
Predicted GC-MS2-Oxo-3-hydroxy-4-phosphobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1930000000-9c3c35aa2de551b4bbf22015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ke-4900000000-162b52e552d9157d3bbb2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9300000000-abe9d170b8c46a45e8582015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0329-9730000000-c5dda701292450f190432015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-1880b6c8035cdbc2520f2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8b44e7c9ed6f8dcaee862015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9020000000-7708f7e46e45e30974c62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-e2b487fed3fe6cdfcc082021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9100000000-3541ae70498a829692b22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000w-9000000000-51318a1b7c455a5670bb2021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC06054
Pubchem Compound ID21145142
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06801
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Phosphoserine aminotransferasePSAT1Q9Y617
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference