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Record Information
Version1.0
Creation Date2016-07-13 19:42:37 UTC
Update Date2021-04-30 20:57:58 UTC
LmdbLMDB00112
Secondary Accession NumbersNone
Metabolite Identification
Common NamePyruvic acid
DescriptionPyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed.) Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds).
Structure
Thumb
Synonyms
ValueSource
2-Ketopropionic acidChEBI
2-Oxopropanoic acidChEBI
2-OxopropansaeureChEBI
2-OxopropionsaeureChEBI
Acetylformic acidChEBI
Acide pyruviqueChEBI
alpha-Ketopropionic acidChEBI
alpha-OxopropionsaeureChEBI
BrenztraubensaeureChEBI
BTSChEBI
CH3COCOOHChEBI
Pyroracemic acidChEBI
2-OxopropanoateKegg
2-KetopropionateGenerator
AcetylformateGenerator
a-KetopropionateGenerator
a-Ketopropionic acidGenerator
alpha-KetopropionateGenerator
Α-ketopropionateGenerator
Α-ketopropionic acidGenerator
a-OxopropionsaeureGenerator
Α-oxopropionsaeureGenerator
PyroracemateGenerator
PyruvateGenerator
2-OxopropionateHMDB
2-Oxopropionic acidHMDB
Acid, pyruvicMeSH, HMDB
Pyruvic acidHMDB
alpha-Ketopropanoic acidHMDB
α-Ketopropanoic acidHMDB
Chemical FormulaC3H4O3
Average Molecular Weight88.0621
Monoisotopic Molecular Weight88.016043994
IUPAC Name2-oxopropanoic acid
Traditional Namepyruvic acid
CAS Registry Number127-17-3
SMILES
CC(=O)C(O)=O
InChI Identifier
InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
InChI KeyLCTONWCANYUPML-UHFFFAOYSA-N
Chemical Taxonomy
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
Substituents
  • 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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.38ALOGPS
logP0.066ChemAxon
logS0.18ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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-f26ef76666e40ab9fe61Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-00di-5900000000-b8e81f82572d4796e944Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-5970000000-154bf9ad168a12593fccSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a2cf85a5e1d2379d26dfSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-4900000000-f26ef76666e40ab9fe61Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-5900000000-b8e81f82572d4796e944Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-5970000000-154bf9ad168a12593fccSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-5900000000-5b1f470d4ff91420618cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-5417b44aa241a7ba27e8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dm-9400000000-6db65a709bdc47e3adf7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-a2cf85a5e1d2379d26dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-dd49835da8355fb6e625Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-f09d8e3d7a774b255d89Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-7d91f6f626cab1a366fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-8ae98cdb3e142034e52aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-e04e6c68013983e1b6dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-dd49835da8355fb6e625Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-f09d8e3d7a774b255d89Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-7d91f6f626cab1a366fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-8ae98cdb3e142034e52aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-e04e6c68013983e1b6dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000f-9000000000-f24c93ecfd3928827154Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0udj-9000000000-fc3b9ad0c57f44261fbaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-f3444f8b94ee5a0a9f74Spectrum
LC-MS/MSLC-MS/MS Spectrum - 33V, Negativesplash10-0avr-9000000000-dc40a6a1b9b166d6e68aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 33V, Negativesplash10-016r-9000000000-efac7b176bb77118ecb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-d0defa72b09503c6d6d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9000000000-c25fa150e9c490319a2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-ccb42b4c05ddd001990fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-faf36ff70d6205370270Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-60c1a02aabf80f51050fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9000000000-ca5f4a2f06787d8b62a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-0eb1fb2cdd24bdc78601Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-87bbaed151efac084591Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-87bbaed151efac084591Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-f315d0752893e7d0c657Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Kidney perfusate
  • Milk
  • Plasma
  • Serum
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Kidney perfusateDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected and Quantified2-188 uMNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableEquine details
SerumDetected and Quantified75.5292 +/- 27.4786 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified72.2206 +/- 25.8504 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified95.4965 +/- 37.7377 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified93.0998 +/- 21.9312 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified88.5155 +/- 36.2373 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified74.1914 +/- 27.0193 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified92.8532 +/- 31.9096 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified79.731 +/- 33.9397 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified67.22 +/- 30.06 uMNot AvailableOvine
    • Candidate serum m...
details
SerumDetected and Quantified79.4106 +/- 34.1811 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified63.6618 +/- 20.5312 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified81.7588 +/- 39.4988 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected and Quantified81.7556 +/- 28.9683 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected and Quantified87.4524 +/- 28.8199 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified69.61 +/- 20.5526 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified71.9101 +/- 23.1035 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified84.0034 +/- 34.2403 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified71.1684 +/- 27.9301 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified75.7639 +/- 15.5665 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified82.7807 +/- 26.2653 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified91.0729 +/- 38.4339 uM
Normal
Ovine
    • Goldansaz et al.,...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailableBovine details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDDB00119
HMDB IDHMDB0000243
FooDB IDFDB031141
Phenol Explorer IDNot Available
KNApSAcK IDC00001200
BiGG IDNot Available
BioCyc IDPYRUVATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPyruvic_acid
Chemspider IDNot Available
ChEBI ID32816
PubChem Compound ID1060
Kegg Compound IDC00022
YMDB IDYMDB00175
ECMDB IDECMDB00243
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available