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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:27:39 UTC
HMDB IDHMDB0001352
Secondary Accession Numbers
  • HMDB01352
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
ValueSource
3-Hydroxy-2-oxopropanoateHMDB
3-Hydroxy-2-oxopropanoic acidHMDB
3-HydroxypyruvateHMDB
3-Hydroxypyruvic acidHMDB
beta-HydroxypyruvateHMDB
HydroxypyruvateHMDB
OH-PyrHMDB
OH-PyruvateHMDB
Hydroxypyruvic acid, lithium saltMeSH
Chemical FormulaC3H4O4
Average Molecular Weight104.0615
Monoisotopic Molecular Weight104.010958616
IUPAC Name3-hydroxy-2-oxopropanoic acid
Traditional Namehydroxypyruvic 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
DescriptionThis compound belongs to the class of chemical entities known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassHydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Alpha-keto acid
  • Keto acid
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.69 m³·mol⁻¹ChemAxon
Polarizability8.17 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0iki-3910000000-c702dadd4b10b9c2e21cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-03ei-8930000000-6f1615bef5d93f87b361View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gvk-1920000000-c10a7388ab610f99688dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dj-1930000000-91df46c8a6c638ffe0f6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03ds-2910000000-bc634dfde6ae74b517bfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gvt-2900000000-37fc3d3c38147e1d8cd8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0iki-3910000000-c702dadd4b10b9c2e21cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03ei-8930000000-6f1615bef5d93f87b361View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03dj-1920000000-408d150435ee3edcc7d1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gvt-2900000000-fc662023f269ec21b82eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9000000000-b7c06a28c87e687f07a8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ac-9440000000-afd8c910b7b1f49d2e62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-9600000000-12ab714e9a2767f1b0b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-c1a1da67ff71584bbd6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-cafdd074d8a05bebf155View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-7900000000-f2aeab79489832ab6fcaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-9200000000-f62ce4a7bd46da93fc09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1f52435889596b02dbf5View in MoNA
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Blood
  • Urine
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
Dimethylglycine Dehydrogenase DeficiencyPw000460Pw000460 greyscalePw000460 simpleNot Available
Glycine and Serine MetabolismPw000157Pw000157 greyscalePw000157 simpleMap00260
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    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 LinkHydroxypyruvic_acid
    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