Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-07-09 14:21:24 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 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 mediated by the enzyme serine--pyruvate aminotransferase. In humans, hydroxypyruvic acid is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. Outside of the human body, Hydroxypyruvic acid has been detected, but not quantified in, several different foods, such as elderberries, summer savories, fireweeds, garland chrysanthemums, and shiitakes. This could make hydroxypyruvic acid a potential biomarker for the consumption of these foods.
Structure
Data?1594304484
Synonyms
ValueSource
3-HydroxypyruvateKegg
3-Hydroxypyruvic acidKegg
HydroxypyruvateGenerator
3-Hydroxy-2-oxopropanoateHMDB
3-Hydroxy-2-oxopropanoic acidHMDB
beta-HydroxypyruvateHMDB
OH-PyrHMDB
OH-PyruvateHMDB
2-Oxo-3-hydroxypropanoic acidHMDB
2-Oxo-3-hydroxypropionic acidHMDB
3-Hydroxy-2-oxopropionic acidHMDB
Hydroxypyruvic acidHMDB
beta-Hydroxypyruvic acidHMDB
β-Hydroxypyruvic acidHMDB
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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility209 g/LALOGPS
logP10(-1.4) g/LALOGPS
logP10(-0.75) g/LChemAxon
logS10(0.3) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+120.77931661259
DarkChem[M-H]-113.03131661259
AllCCS[M+H]+126.332859911
AllCCS[M-H]-119.45632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Hydroxypyruvic acidOCC(=O)C(O)=O1771.3Standard polar33892256
Hydroxypyruvic acidOCC(=O)C(O)=O1448.8Standard non polar33892256
Hydroxypyruvic acidOCC(=O)C(O)=O951.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hydroxypyruvic acid,1TMS,isomer #1C[Si](C)(C)OCC(=O)C(=O)O1143.6Semi standard non polar33892256
Hydroxypyruvic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C(=O)CO1064.0Semi standard non polar33892256
Hydroxypyruvic acid,1TMS,isomer #3C[Si](C)(C)OC(=CO)C(=O)O1201.0Semi standard non polar33892256
Hydroxypyruvic acid,2TMS,isomer #1C[Si](C)(C)OCC(=O)C(=O)O[Si](C)(C)C1292.9Semi standard non polar33892256
Hydroxypyruvic acid,2TMS,isomer #2C[Si](C)(C)OC=C(O[Si](C)(C)C)C(=O)O1315.1Semi standard non polar33892256
Hydroxypyruvic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C(=CO)O[Si](C)(C)C1228.3Semi standard non polar33892256
Hydroxypyruvic acid,3TMS,isomer #1C[Si](C)(C)OC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1396.4Semi standard non polar33892256
Hydroxypyruvic acid,3TMS,isomer #1C[Si](C)(C)OC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1305.1Standard non polar33892256
Hydroxypyruvic acid,3TMS,isomer #1C[Si](C)(C)OC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1352.9Standard polar33892256
Hydroxypyruvic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)C(=O)O1418.9Semi standard non polar33892256
Hydroxypyruvic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=O)CO1334.7Semi standard non polar33892256
Hydroxypyruvic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CO)C(=O)O1434.3Semi standard non polar33892256
Hydroxypyruvic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)C(=O)O[Si](C)(C)C(C)(C)C1710.0Semi standard non polar33892256
Hydroxypyruvic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C(=O)O1788.5Semi standard non polar33892256
Hydroxypyruvic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(=CO)O[Si](C)(C)C(C)(C)C1730.1Semi standard non polar33892256
Hydroxypyruvic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1999.0Semi standard non polar33892256
Hydroxypyruvic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1886.9Standard non polar33892256
Hydroxypyruvic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1784.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Hydroxypyruvic acid GC-MS (1 MEOX; 2 TMS)splash10-0iki-3910000000-c702dadd4b10b9c2e21c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxypyruvic acid GC-MS (1 MEOX; 2 TMS)splash10-03ei-8930000000-6f1615bef5d93f87b3612014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxypyruvic acid EI-B (Non-derivatized)splash10-0gvk-1920000000-c10a7388ab610f99688d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxypyruvic acid EI-B (Non-derivatized)splash10-03dj-1930000000-91df46c8a6c638ffe0f62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxypyruvic acid GC-EI-TOF (Non-derivatized)splash10-03ds-2910000000-bc634dfde6ae74b517bf2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxypyruvic acid GC-EI-TOF (Non-derivatized)splash10-0gvt-2900000000-37fc3d3c38147e1d8cd82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxypyruvic acid GC-MS (Non-derivatized)splash10-0iki-3910000000-c702dadd4b10b9c2e21c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxypyruvic acid GC-MS (Non-derivatized)splash10-03ei-8930000000-6f1615bef5d93f87b3612017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxypyruvic acid GC-EI-TOF (Non-derivatized)splash10-03dj-1920000000-408d150435ee3edcc7d12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxypyruvic acid GC-EI-TOF (Non-derivatized)splash10-0gvt-2900000000-fc662023f269ec21b82e2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxypyruvic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9000000000-b7c06a28c87e687f07a82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxypyruvic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00ac-9440000000-afd8c910b7b1f49d2e622017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxypyruvic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxypyruvic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxypyruvic acid 35V, Negative-QTOFsplash10-0a4i-9000000000-d1755e284e492b01243a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxypyruvic acid 10V, Positive-QTOFsplash10-0a4r-9600000000-12ab714e9a2767f1b0b52015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxypyruvic acid 20V, Positive-QTOFsplash10-0a4r-9100000000-c1a1da67ff71584bbd6a2015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxypyruvic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-cafdd074d8a05bebf1552015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxypyruvic acid 10V, Negative-QTOFsplash10-0udi-7900000000-f2aeab79489832ab6fca2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxypyruvic acid 20V, Negative-QTOFsplash10-0pc0-9200000000-f62ce4a7bd46da93fc092015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxypyruvic acid 40V, Negative-QTOFsplash10-0a4i-9000000000-1f52435889596b02dbf52015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxypyruvic acid 10V, Negative-QTOFsplash10-0k96-9200000000-cd93a4168536c1a376db2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxypyruvic acid 20V, Negative-QTOFsplash10-0006-9000000000-3cb0c9f5ca761bc8f1912021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxypyruvic acid 40V, Negative-QTOFsplash10-0006-9000000000-6ffb9541e24882de3fac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxypyruvic acid 10V, Positive-QTOFsplash10-052u-9100000000-697deb69236e2f95e74f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxypyruvic acid 20V, Positive-QTOFsplash10-052f-9000000000-ebcddbdd296882eee9ff2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxypyruvic acid 40V, Positive-QTOFsplash10-0006-9000000000-7c612a451346078594a22021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified10.8 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>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 IDFDB030913
KNApSAcK IDC00007563
Chemspider ID939
KEGG Compound IDC00168
BioCyc IDOH-PYR
BiGG ID34120
Wikipedia LinkHydroxypyruvic_acid
METLIN ID482
PubChem Compound964
PDB IDNot Available
ChEBI ID30841
Food Biomarker OntologyNot Available
VMH IDHPYR
MarkerDB IDNot Available
Good Scents 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