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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:14 UTC
HMDB IDHMDB0001352
Secondary Accession Numbers
  • HMDB01352
Metabolite Identification
Common NameHydroxypyruvic acid
DescriptionHydroxypyruvic acid, also known as 3-hydroxypyruvate or OH-pyr, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Hydroxypyruvic acid is a drug. Hydroxypyruvic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Hydroxypyruvic acid exists in all living organisms, ranging from bacteria to humans. hydroxypyruvic acid and L-alanine can be biosynthesized from pyruvic acid and L-serine; which is catalyzed by the enzyme serine--pyruvate aminotransferase. In humans, hydroxypyruvic acid is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. Hydroxypyruvic acid is a cabbage, radish, and sour. Outside of the human body, hydroxypyruvic acid has been detected, but not quantified in, a few different foods, such as alcoholic beverages, cocoa and cocoa products, and milk and milk products. This could make hydroxypyruvic acid a potential biomarker for the consumption of these foods.
Structure
Data?1582752194
Synonyms
ValueSource
3-HydroxypyruvateKegg
3-Hydroxypyruvic acidKegg
HydroxypyruvateGenerator
3-Hydroxy-2-oxopropanoateHMDB
3-Hydroxy-2-oxopropanoic acidHMDB
beta-HydroxypyruvateHMDB
OH-PyrHMDB
OH-PyruvateHMDB
Hydroxypyruvic acid, lithium saltHMDB
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
Description belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy 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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0iki-3910000000-c702dadd4b10b9c2e21cSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-03ei-8930000000-6f1615bef5d93f87b361Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gvk-1920000000-c10a7388ab610f99688dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dj-1930000000-91df46c8a6c638ffe0f6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03ds-2910000000-bc634dfde6ae74b517bfSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gvt-2900000000-37fc3d3c38147e1d8cd8Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0iki-3910000000-c702dadd4b10b9c2e21cSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03ei-8930000000-6f1615bef5d93f87b361Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03dj-1920000000-408d150435ee3edcc7d1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gvt-2900000000-fc662023f269ec21b82eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9000000000-b7c06a28c87e687f07a8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ac-9440000000-afd8c910b7b1f49d2e62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-9600000000-12ab714e9a2767f1b0b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-c1a1da67ff71584bbd6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-cafdd074d8a05bebf155Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-7900000000-f2aeab79489832ab6fcaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-9200000000-f62ce4a7bd46da93fc09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1f52435889596b02dbf5Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified10.8 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    Associated Disorders and Diseases
    Disease References
    Colorectal cancer
    1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
    Associated OMIM IDs
    DrugBank IDDB02951
    Phenol Explorer Compound IDNot Available
    FooDB IDFDB008112
    KNApSAcK IDC00007563
    Chemspider ID939
    KEGG Compound IDC00168
    BioCyc IDNot Available
    BiGG ID34120
    Wikipedia LinkHydroxypyruvic_acid
    METLIN ID482
    PubChem Compound964
    PDB IDNot Available
    ChEBI ID30841
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    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