Human Metabolome Database Version 3.5

Showing metabocard for Hydroxypyruvic acid (HMDB01352)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:23 -0700
HMDB ID HMDB01352
Secondary Accession Numbers None
Metabolite Identification
Common Name Hydroxypyruvic acid
Description Hydroxypyruvic 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C3H4O4
Average Molecular Weight 104.0615
Monoisotopic Molecular Weight 104.010958616
IUPAC Name 3-hydroxy-2-oxopropanoic acid
Traditional IUPAC Name 3-hydroxypyruvic acid
CAS Registry Number 1113-60-6
SMILES OCC(=O)C(O)=O
InChI Identifier InChI=1S/C3H4O4/c4-1-2(5)3(6)7/h4H,1H2,(H,6,7)
InChI Key HHDDCCUIIUWNGJ-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Hydroxy Acids and Derivatives
Sub Class Beta 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 Parent Beta Hydroxy Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycine, serine and threonine metabolism
Application Not Available
Cellular locations
  • Mitochondria
  • Peroxisome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 209 g/L ALOGPS
LogP -1.43 ALOGPS
LogP -0.75 ChemAxon
LogS 0.30 ALOGPS
pKa (strongest acidic) 2.57 ChemAxon
pKa (strongest basic) -3.4 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 74.6 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 19.69 ChemAxon
Polarizability 8.18 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Glycine and Serine Metabolism SMP00004 map00260 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Comment Normal
  • Not Applicable
Urine Detected and Quantified
10.8 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB02951 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB008112
KNApSAcK ID C00007563 Link_out
Chemspider ID 939 Link_out
KEGG Compound ID C00168 Link_out
BioCyc ID OH-PYR Link_out
BiGG ID 34120 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB01352 Link_out
Metagene Link HMDB01352 Link_out
METLIN ID 482 Link_out
PubChem Compound 964 Link_out
PDB ID 3PY Link_out
ChEBI ID 30841 Link_out
References
Synthesis Reference Behal, 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 Link_out

Enzymes
Name: Glyoxylate reductase/hydroxypyruvate reductase
Reactions:
Glyceric acid + NAD(P)(+) unknown Hydroxypyruvic acid + NAD(P)H details
Glyceric acid + NAD unknown Hydroxypyruvic acid + NADH + Hydrogen Ion details
Glyceric acid + NADP unknown Hydroxypyruvic acid + NADPH + Hydrogen Ion details
Gene Name: GRHPR
Uniprot ID: Q9UBQ7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serine--pyruvate aminotransferase
Reactions:
L-Serine + Pyruvic acid unknown Hydroxypyruvic acid + L-Alanine details
L-Serine + Glyoxylic acid unknown Hydroxypyruvic acid + Glycine details
Gene Name: AGXT
Uniprot ID: P21549 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative hydroxypyruvate isomerase
Reactions:
Hydroxypyruvic acid unknown Tartronate semialdehyde details
Gene Name: HYI
Uniprot ID: Q5T013 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA