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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 08:00:14 UTC
HMDB IDHMDB0001024
Secondary Accession Numbers
  • HMDB01024
  • HMDB60175
Metabolite Identification
Common NamePhosphohydroxypyruvic acid
DescriptionPhosphohydroxypyruvic acid is a prduct of both enzyme phosphoglycerate dehydrogenase [EC 1.1.1.95] and phosphoserine transaminase [EC 2.6.1.52] in glycine, serine and threonine metabolism pathway (KEGG). This compound belongs to the family of Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group.
Structure
Thumb
Synonyms
ValueSource
3-Phosphohydroxypyruvic acidChEBI
Hydroxypyruvic acid phosphateChEBI
3-PhosphohydroxypyruvateGenerator
PhosphohydroxypyruvateGenerator
Hydroxypyruvate phosphateGenerator
Hydroxypyruvic acid phosphoric acidGenerator
2-oxo-3-(Phosphonooxy)-propanoateHMDB
2-oxo-3-(Phosphonooxy)-propanoic acidHMDB
3-PhosphonatooxypyruvateHMDB
3-PhosphonooxypyruvateHMDB
3-Phosphonooxypyruvic acidHMDB
Chemical FormulaC3H5O7P
Average Molecular Weight184.0414
Monoisotopic Molecular Weight183.977289026
IUPAC Name2-oxo-3-(phosphonooxy)propanoic acid
Traditional Namephosphohydroxypyruvate
CAS Registry Number3913-50-6
SMILES
OC(=O)C(=O)COP(O)(O)=O
InChI Identifier
InChI=1S/C3H5O7P/c4-2(3(5)6)1-10-11(7,8)9/h1H2,(H,5,6)(H2,7,8,9)
InChI KeyLFLUCDOSQPJJBE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as glycerone phosphates. These are organic compounds containing a glycerone moiety that carries a phosphate group at the O-1 or O-2 position.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentGlycerone phosphates
Alternative Parents
Substituents
  • Glycerone phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Keto acid
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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 Solubility13.4 g/LALOGPS
logP-1.8ALOGPS
logP-0.87ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.02ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.56 m³·mol⁻¹ChemAxon
Polarizability12.69 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9300000000-33ff06735f8214248ea3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-9510000000-f67b2feb11cbb37fdf47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-4411ba8f6713e6b68f94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00s9-0900000000-457227604cff5cdecb73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05g0-6900000000-5ced177e050ba3272f0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-3900000000-22820af5ec79da81207bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-0127ef53c9426c592779View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4ba77bd112070310c576View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
3-Phosphoglycerate dehydrogenase deficiencyPw000698Pw000698 greyscalePw000698 simpleNot Available
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)Pw000198Pw000198 greyscalePw000198 simpleNot Available
Dimethylglycine Dehydrogenase DeficiencyPw000197Pw000197 greyscalePw000197 simpleNot Available
Glycine and Serine MetabolismPw000157Pw000157 greyscalePw000157 simpleMap00260
Hyperglycinemia, non-ketoticPw000461Pw000461 greyscalePw000461 simpleNot Available
Displaying entries 1 - 5 of 7 in total
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 IDFDB022377
KNApSAcK IDNot Available
Chemspider ID103
KEGG Compound IDC03232
BioCyc ID3-P-HYDROXYPYRUVATE
BiGG ID41453
Wikipedia LinkPhosphohydroxypyruvic acid
METLIN ID484
PubChem Compound105
PDB IDHPV
ChEBI ID30933
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhao G, Winkler ME: A novel alpha-ketoglutarate reductase activity of the serA-encoded 3-phosphoglycerate dehydrogenase of Escherichia coli K-12 and its possible implications for human 2-hydroxyglutaric aciduria. J Bacteriol. 1996 Jan;178(1):232-9. [PubMed:8550422 ]
  2. Achouri Y, Rider MH, Schaftingen EV, Robbi M: Cloning, sequencing and expression of rat liver 3-phosphoglycerate dehydrogenase. Biochem J. 1997 Apr 15;323 ( Pt 2):365-70. [PubMed:9163325 ]
  3. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

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
Phosphoserine + Oxoglutaric acid → Phosphohydroxypyruvic acid + L-Glutamic aciddetails
General function:
Involved in phosphoglycerate dehydrogenase activity
Specific function:
Not Available
Gene Name:
PHGDH
Uniprot ID:
O43175
Molecular weight:
56650.03
Reactions
3-Phosphoglyceric acid + NAD → Phosphohydroxypyruvic acid + NADHdetails
3-Phosphoglyceric acid + NAD → Phosphohydroxypyruvic acid + NADH + Hydrogen Iondetails