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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:40 UTC
HMDB IDHMDB0001024
Secondary Accession Numbers
  • HMDB0060175
  • HMDB01024
  • HMDB60175
Metabolite Identification
Common NamePhosphohydroxypyruvic acid
DescriptionPhosphohydroxypyruvic acid, also known as 3-phosphooxypyruvate or hydroxypyruvic acid phosphate, belongs to the class of organic compounds 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. Phosphohydroxypyruvic acid is a moderately acidic compound (based on its pKa). Phosphohydroxypyruvic acid exists in all living species, ranging from bacteria to humans. Within humans, phosphohydroxypyruvic acid participates in a number of enzymatic reactions. In particular, phosphohydroxypyruvic acid can be biosynthesized from 3-phosphoglyceric acid; which is mediated by the enzyme D-3-phosphoglycerate dehydrogenase. In addition, phosphohydroxypyruvic acid and L-glutamic acid can be converted into phosphoserine and oxoglutaric acid through its interaction with the enzyme phosphoserine aminotransferase. In humans, phosphohydroxypyruvic acid is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. Phosphohydroxypyruvic acid is an intermediate in the synthesis of serine.
Structure
Data?1563860680
Synonyms
ValueSource
3-Phosphohydroxypyruvic acidChEBI
Hydroxypyruvic acid phosphateChEBI
3-Phosphonooxypyruvic acidKegg
3-PhosphohydroxypyruvateKegg
3-PhosphooxypyruvateKegg
Hydroxypyruvate phosphateGenerator
Hydroxypyruvic acid phosphoric acidGenerator
3-PhosphonooxypyruvateGenerator
3-Phosphooxypyruvic acidGenerator
PhosphohydroxypyruvateGenerator
2-oxo-3-(Phosphonooxy)-propanoateHMDB
2-oxo-3-(Phosphonooxy)-propanoic acidHMDB
3-PhosphonatooxypyruvateHMDB
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
Description belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl 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

Source:

Biological location:

Process

Naturally occurring process:

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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9300000000-33ff06735f8214248ea3JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-9510000000-f67b2feb11cbb37fdf47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-4411ba8f6713e6b68f94JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00s9-0900000000-457227604cff5cdecb73JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05g0-6900000000-5ced177e050ba3272f0fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-3900000000-22820af5ec79da81207bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-0127ef53c9426c592779JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4ba77bd112070310c576JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022377
KNApSAcK IDC00019657
Chemspider ID103
KEGG Compound IDC03232
BioCyc IDNot Available
BiGG ID41453
Wikipedia LinkPhosphohydroxypyruvic acid
METLIN ID484
PubChem Compound105
PDB IDNot Available
ChEBI ID30933
Food Biomarker OntologyNot Available
VMH IDNot Available
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