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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:23 UTC
HMDB IDHMDB01352
Secondary Accession NumbersNone
Metabolite Identification
Common NameHydroxypyruvic acid
DescriptionHydroxypyruvic acid is an intermediate in the metabolism of Glycine, serine and threonine. It is a substrate for Serine--pyruvate aminotransferase and Glyoxylate reductase/hydroxypyruvate reductase.
Structure
Thumb
Synonyms
  1. 3-Hydroxy-2-oxopropanoate
  2. 3-Hydroxy-2-oxopropanoic acid
  3. 3-Hydroxypyruvate
  4. 3-Hydroxypyruvic acid
  5. beta-Hydroxypyruvate
  6. Hydroxypyruvate
  7. OH-pyr
  8. OH-pyruvate
Chemical FormulaC3H4O4
Average Molecular Weight104.0615
Monoisotopic Molecular Weight104.010958616
IUPAC Name3-hydroxy-2-oxopropanoic acid
Traditional Name3-hydroxypyruvic acid
CAS Registry Number1113-60-6
SMILES
OCC(=O)C(O)=O
InChI Identifier
InChI=1S/C3H4O4/c4-1-2(5)3(6)7/h4H,1H2,(H,6,7)
InChI KeyHHDDCCUIIUWNGJ-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassOrganic Acids and Derivatives
ClassHydroxy Acids and Derivatives
Sub ClassBeta Hydroxy Acids and Derivatives
Other Descriptors
  • 2-oxo monocarboxylic acid(ChEBI)
  • 3-hydroxy monocarboxylic acid(ChEBI)
  • Aliphatic Acyclic Compounds
Substituents
  • Alpha Keto Acid
  • Alpha Ketoaldehyde
  • Carboxylic Acid
  • Ketone
  • Primary Alcohol
  • Saccharide
  • Triose Monosaccharide
Direct ParentBeta Hydroxy Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycine, serine and threonine metabolism
ApplicationNot Available
Cellular locations
  • Mitochondria
  • Peroxisome
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 Solubility209.0ALOGPS
logP-1.4ALOGPS
logP-0.75ChemAxon
logS0.3ALOGPS
pKa (Strongest Acidic)2.57ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.69 m3·mol-1ChemAxon
Polarizability8.18 Å3ChemAxon
Spectra
SpectraGC-MS
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Glycine and Serine MetabolismSMP00004map00260
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified10.8 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02951
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008112
KNApSAcK IDC00007563
Chemspider ID939
KEGG Compound IDC00168
BioCyc IDOH-PYR
BiGG ID34120
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01352
Metagene LinkHMDB01352
METLIN ID482
PubChem Compound964
PDB ID3PY
ChEBI ID30841
References
Synthesis ReferenceBehal, Francis J. Hydroxypyruvic acid formation in Aspergillus niger. Archives of Biochemistry and Biophysics (1960), 88 110-12.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kolvraa S, Rasmussen K, Brandt NJ: D-glyceric acidemia: biohcemical studies of a new syndrome. Pediatr Res. 1976 Oct;10(10):825-30. Pubmed: 972784

Enzymes

General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Enzyme with hydroxy-pyruvate reductase, glyoxylate reductase and D-glycerate dehydrogenase enzymatic activities. Reduces hydroxypyruvate to D-glycerate, glyoxylate to glycolate oxidizes D-glycerate to hydroxypyruvate.
Gene Name:
GRHPR
Uniprot ID:
Q9UBQ7
Molecular weight:
35667.875
Reactions
Glyceric acid + NAD(P)(+) → Hydroxypyruvic acid + NAD(P)Hdetails
Glyceric acid + NAD → Hydroxypyruvic acid + NADH + Hydrogen Iondetails
Glyceric acid + NADP → Hydroxypyruvic acid + NADPH + Hydrogen Iondetails
General function:
Involved in metabolic process
Specific function:
Not Available
Gene Name:
AGXT
Uniprot ID:
P21549
Molecular weight:
43009.535
Reactions
L-Serine + Pyruvic acid → Hydroxypyruvic acid + L-Alaninedetails
L-Serine + Glyoxylic acid → Hydroxypyruvic acid + Glycinedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes the reversible isomerization between hydroxypyruvate and 2-hydroxy-3-oxopropanoate (also termed tartronate semialdehyde) (By similarity).
Gene Name:
HYI
Uniprot ID:
Q5T013
Molecular weight:
30405.4
Reactions
Hydroxypyruvic acid → Tartronate semialdehydedetails