Showing Compound Card for 2-Oxo-3-hydroxy-4-phosphobutanoic acid (CDB005287)

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Record Information
Version1.0
Created at2020-04-17 19:28:03 UTC
Updated at2020-11-18 16:39:40 UTC
CannabisDB IDCDB005287
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. 2-Oxo-3-hydroxy-4-phosphobutanoic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3R)-3-Hydroxy-2-oxo-4-phosphonooxybutanoateChEBI
2-oxo-3-Hydroxy-4-phosphobutanoateChEBI
alpha-Keto-3-hydroxy-4-phosphobutyrateChEBI
(3R)-3-Hydroxy-2-oxo-4-phosphooxybutanoateKegg
(3R)-3-Hydroxy-2-oxo-4-phosphonooxybutanoic 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
(3R)-3-Hydroxy-2-oxo-4-phosphooxybutanoic acidGenerator
Chemical FormulaC4H7O8P
Average Molecular Weight214.07
Monoisotopic Molecular Weight213.9879
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 KeyMZJFVXDTNBHTKZ-UWTATZPHSA-N
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
Ontology
Disposition

Route of exposure:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Phosphoserine aminotransferasePSAT19q21.2Q9Y617 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0006801
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030351
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06054
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21145142
PDB IDNot Available
ChEBI ID27951
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Phosphoserine aminotransferase
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