Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110761
Identification
Name: pyruvate
Description:A 2-oxo monocarboxylic acid anion that is the conjugate base of pyruvic acid, arising from deprotonation of the carboxy group.
Structure
Thumb
Synonyms:
  • alpha-ketopropionic acid
  • BTS
  • α-ketopropionic acid
  • acetylformic acid
  • pyroracemic acid
  • 2-oxopropanoic acid
  • pyruvic acid
  • 2-oxopropanoate
  • 2-oxo-propionic acid
Chemical Formula: C3H3O3
Average Molecular Weight: 87.055
Monoisotopic Molecular Weight: 88.0160439947
InChI Key: LCTONWCANYUPML-UHFFFAOYSA-M
InChI: InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)/p-1
CAS number: 127-17-3
IUPAC Name:2-oxopropanoate
Traditional IUPAC Name: pyruvic acid
SMILES:CC(=O)C(=O)[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Keto acids and derivatives
Sub ClassAlpha-keto acids and derivatives
Direct Parent Alpha-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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Liquid
Charge:-1
Melting point: 13.8 °C
Experimental Properties:
PropertyValueReference
Melting Point13.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility134.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.99 m3·mol-1ChemAxon
Polarizability7.31 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00dr-4900000000-f26ef76666e40ab9fe61View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-00di-5900000000-b8e81f82572d4796e944View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-5970000000-154bf9ad168a12593fccView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-a2cf85a5e1d2379d26dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-dd49835da8355fb6e625View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-f09d8e3d7a774b255d89View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-7d91f6f626cab1a366fdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-8ae98cdb3e142034e52aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-e04e6c68013983e1b6dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-f315d0752893e7d0c657View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Salek RM, Maguire ML, Bentley E, Rubtsov DV, Hough T, Cheeseman M, Nunez D, Sweatman BC, Haselden JN, Cox RD, Connor SC, Griffin JL (2007)A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human. Physiological genomics 29, Pubmed: 17190852
  • Janich MA, Menzel MI, Wiesinger F, Weidl E, Khegai O, Ardenkjaer-Larsen JH, Glaser SJ, Haase A, Schulte RF, Schwaiger M (2012)Effects of pyruvate dose on in vivo metabolism and quantification of hyperpolarized ¹³C spectra. NMR in biomedicine 25, Pubmed: 21823181
  • Shetty PK, Sadgrove MP, Galeffi F, Turner DA (2012)Pyruvate incubation enhances glycogen stores and sustains neuronal function during subsequent glucose deprivation. Neurobiology of disease 45, Pubmed: 21854850
  • Kao CC, Hsu JW, Bandi V, Hanania NA, Kheradmand F, Jahoor F (2012)Glucose and pyruvate metabolism in severe chronic obstructive pulmonary disease. Journal of applied physiology (Bethesda, Md. : 1985) 112, Pubmed: 22016370
  • Zhou D, Qian J, Chang H, Xi B, Sun RP (2012)Pyruvate administered to newborn rats with insulin-induced hypoglycemic brain injury reduces neuronal death and cognitive impairment. European journal of pediatrics 171, Pubmed: 21603897
  • Saito K, Matsumoto S, Devasahayam N, Subramanian S, Munasinghe JP, Morris HD, Lizak MJ, Ardenkjaer-Larsen JH, Mitchell JB, Krishna MC (2012)Transient decrease in tumor oxygenation after intravenous administration of pyruvate. Magnetic resonance in medicine 67, Pubmed: 22006570
  • Ojima Y, Suryadarma P, Tsuchida K, Taya M (2012)Accumulation of pyruvate by changing the redox status in Escherichia coli. Biotechnology letters 34, Pubmed: 22215378
  • Diers AR, Broniowska KA, Chang CF, Hogg N (2012)Pyruvate fuels mitochondrial respiration and proliferation of breast cancer cells: effect of monocarboxylate transporter inhibition. The Biochemical journal 444, Pubmed: 22458763
  • Biagi S, Ghimenti S, Onor M, Bramanti E (2012)Simultaneous determination of lactate and pyruvate in human sweat using reversed-phase high-performance liquid chromatography: a noninvasive approach. Biomedical chromatography : BMC 26, Pubmed: 22311625
  • Wang X, Takata T, Bai X, Ou F, Yokono K, Sakurai T (2012)Pyruvate prevents the inhibition of the long-term potentiation induced by amyloid-ß through protein phosphatase 2A inactivation. Journal of Alzheimer's disease : JAD 30, Pubmed: 22451307
Synthesis Reference: Xiang, Wei; Okita, Motomu. Preparation of pyruvic acid. Jpn. Kokai Tokkyo Koho (2003), 5 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS127-17-3
ChEBI15361
ChemSpider96901
HMDBHMDB00243
IAF126033546
KEGGC00022
KNApSAcKC00001200
MetaboLightsMTBLC15361
PubChem107735
UMBBD-Compoundsc0159