Record Information
Creation date2015-05-07 21:08:21 UTC
Update date2019-11-26 03:22:10 UTC
Primary IDFDB031141
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namepyruvate
DescriptionPyruvic acid, also known as 2-oxopropanoic acid or alpha-ketopropionic acid, belongs to alpha-keto acids and derivatives class of compounds. Those are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. Thus, pyruvic acid is considered to be a fatty acid lipid molecule. Pyruvic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Pyruvic acid can be synthesized from propionic acid. Pyruvic acid is also a parent compound for other transformation products, including but not limited to, 4-hydroxy-3-iodophenylpyruvate, 3-acylpyruvic acid, and methyl pyruvate. Pyruvic acid can be found in a number of food items such as kumquat, groundcherry, coconut, and prunus (cherry, plum), which makes pyruvic acid a potential biomarker for the consumption of these food products. Pyruvic acid can be found primarily in most biofluids, including sweat, blood, urine, and feces, as well as throughout most human tissues. Pyruvic acid exists in all living species, ranging from bacteria to humans. In humans, pyruvic acid is involved in several metabolic pathways, some of which include glycogenosis, type IB, glycolysis, urea cycle, and gluconeogenesis. Pyruvic acid is also involved in several metabolic disorders, some of which include non ketotic hyperglycinemia, pyruvate dehydrogenase complex deficiency, fructose-1,6-diphosphatase deficiency, and 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency. Moreover, pyruvic acid is found to be associated with anoxia, schizophrenia, fumarase deficiency, and meningitis. Pyruvic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Pyruvic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalanc. Pyruvic acid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or to fatty acids through a reaction with acetyl-CoA. It can also be used to construct the amino acid alanine and can be converted into ethanol or lactic acid via fermentation . Those taking large doses of supplemental pyruvate—usually greater than 5 grams daily—have reported gastrointestinal symptoms, including abdominal discomfort and bloating, gas and diarrhea. One child receiving pyruvate intravenously for restrictive cardiomyopathy died (DrugBank). Pyruvate serves as a biological fuel by being converted to acetyl coenzyme A, which enters the tricarboxylic acid or Krebs cycle where it is metabolized to produce ATP aerobically. Energy can also be obtained anaerobically from pyruvate via its conversion to lactate. Pyruvate injections or perfusions increase contractile function of hearts when metabolizing glucose or fatty acids. This inotropic effect is striking in hearts stunned by ischemia/reperfusion. The inotropic effect of pyruvate requires intracoronary infusion. Among possible mechanisms for this effect are increased generation of ATP and an increase in ATP phosphorylation potential. Another is activation of pyruvate dehydrogenase, promoting its own oxidation by inhibiting pyruvate dehydrogenase kinase. Pyruvate dehydrogenase is inactivated in ischemia myocardium. Yet another is reduction of cytosolic inorganic phosphate concentration. Pyruvate, as an antioxidant, is known to scavenge such reactive oxygen species as hydrogen peroxide and lipid peroxides. Indirectly, supraphysiological levels of pyruvate may increase cellular reduced glutathione (T3DB).
CAS Number127-17-3
2-Ketopropionic acidChEBI
2-Oxopropanoic acidChEBI
Acetylformic acidChEBI
Acide pyruviqueChEBI
alpha-Ketopropionic acidChEBI
Pyroracemic acidChEBI
a-Ketopropionic acidGenerator
Α-ketopropionic acidGenerator
2-Oxopropionic acidHMDB
Acid, pyruvicHMDB
alpha-Ketopropanoic acidHMDB
Α-ketopropanoic acidHMDB
Pyruvic acidHMDB
Predicted Properties
Water Solubility134 g/LALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.99 m³·mol⁻¹ChemAxon
Polarizability7.31 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC3H4O3
IUPAC name2-oxopropanoic acid
InChI IdentifierInChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
Isomeric SMILESCC(=O)C(O)=O
Average Molecular Weight88.0621
Monoisotopic Molecular Weight88.016043994
Description belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassAlpha-keto acids and derivatives
Direct ParentAlpha-keto acids and derivatives
Alternative Parents
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physiological effect

Health effect:


Route of exposure:


Biological location:


Industrial application:

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Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00dr-4900000000-f26ef76666e40ab9fe61JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-00di-5900000000-b8e81f82572d4796e944JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-5970000000-154bf9ad168a12593fccJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a2cf85a5e1d2379d26dfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-4900000000-f26ef76666e40ab9fe61JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-5900000000-b8e81f82572d4796e944JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-5970000000-154bf9ad168a12593fccJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-5900000000-5b1f470d4ff91420618cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-5417b44aa241a7ba27e8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dm-9400000000-6db65a709bdc47e3adf7JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-a2cf85a5e1d2379d26dfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-dd49835da8355fb6e625JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-f09d8e3d7a774b255d89JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-7d91f6f626cab1a366fdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-8ae98cdb3e142034e52aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-e04e6c68013983e1b6dcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-dd49835da8355fb6e625JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-f09d8e3d7a774b255d89JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-7d91f6f626cab1a366fdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-8ae98cdb3e142034e52aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-e04e6c68013983e1b6dcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-d0defa72b09503c6d6d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9000000000-c25fa150e9c490319a2aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-ccb42b4c05ddd001990fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-faf36ff70d6205370270JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-60c1a02aabf80f51050fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9000000000-ca5f4a2f06787d8b62a0JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-f315d0752893e7d0c657JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
MSDSNot Available
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference