Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-06 02:44:43 UTC
NP-MRD IDNP0000944
Secondary Accession NumbersNone
Natural Product Identification
Common NamePyruvic acid
DescriptionPyruvic acid or pyruvate is a simple alpha-keto acid. It is a three-carbon molecule containing a carboxylic acid group and a ketone functional group. Pyruvate is the simplest alpha-keto acid and according to official nomenclature by IUPAC, it is called alpha-keto propanoic acid. Like other keto acids, pyruvic acid can tautomerize from its ketone form to its enol form, containing a double bond and an alcohol. Pyruvate is found in all living organisms ranging from bacteria to plants to humans. It is intermediate compound in the metabolism of carbohydrates, proteins, and fats. Pyruvate is a key intermediate in several metabolic pathways throughout the cell. In particular, 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. Pyruvic acid supplies energy to cells through the citric acid cycle (TCA or Krebs cycle) when oxygen is present (aerobic respiration), and alternatively ferments to produce lactate when oxygen is lacking (lactic acid). In glycolysis, phosphoenolpyruvate (PEP) is converted to pyruvate by pyruvate kinase. This reaction is strongly exergonic and irreversible. In gluconeogenesis, it takes two enzymes, pyruvate carboxylase and PEP carboxykinase, to catalyze the reverse transformation of pyruvate to PEP. Pyruvic acid is also a metabolite of Corynebacterium (PMID: 27872963 ).
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, pyruvicHMDB
alpha-Ketopropanoic acidHMDB
Α-ketopropanoic acidHMDB
Pyruvic acidHMDB
Chemical FormulaC3H4O3
Average Mass88.0621 Da
Monoisotopic Mass88.01604 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-07-25View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-06View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-02-06View Spectrum
Species
Species of Origin
Species NameSourceReference
Allium cepaFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
    • Harvey J. Gold, Charles W. Wilson III The Volatile Flavor Substances of Celery. Journal of Food S...
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaKNApSAcK Database
Bauhinia purpureaKNApSAcK Database
Cannabis sativaCannabisDB
      Not Available
Capsella bursa-pastorisKNApSAcK Database
Capsicum annuumKNApSAcK Database
Cicer arietinumKNApSAcK Database
Delonix regiaKNApSAcK Database
Ginkgo bilobaFooDB
Malus pumilaKNApSAcK Database
Musa x paradisiacaFooDB
Oxalis corniculataKNApSAcK Database
Panax ginsengKNApSAcK Database
Pisum sativumKNApSAcK Database
Polygonum hydropiperKNApSAcK Database
Polygonum persicariaKNApSAcK Database
Sebertia acuminataKNApSAcK Database
Solanum lycopersicum var. lycopersicumFooDB
Stevia rebaudianaKNApSAcK Database
Trigonella caeruleaKNApSAcK Database
Trigonella ceruleaKNApSAcK Database
Typha latifoliaKNApSAcK Database
Zea mays L.FooDB
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Homo sapiens (Serum)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point13.8 °CNot Available
Boiling Point164.00 to 166.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mLNot Available
LogP-1.240 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility134 g/LALOGPS
logP10(-0.38) g/LALOGPS
logP10(0.066) g/LChemAxon
logS10(0.18) 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000243
DrugBank IDDB00119
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031141
KNApSAcK IDC00001200
Chemspider ID1031
KEGG Compound IDC00022
BioCyc IDPYRUVATE
BiGG IDNot Available
Wikipedia LinkPyruvic_acid
METLIN IDNot Available
PubChem Compound1060
PDB IDNot Available
ChEBI ID32816
Good Scents IDrw1034261
References
General References
  1. Tsuchiya H, Hashizume I, Tokunaga T, Tatsumi M, Takagi N, Hayashi T: High-performance liquid chromatography of alpha-keto acids in human saliva. Arch Oral Biol. 1983;28(11):989-92. [PubMed:6581765 ]
  2. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  3. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
  4. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
  5. Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. [PubMed:15627241 ]
  6. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
  7. Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. [PubMed:8579834 ]
  8. Foster KJ, Alberti KG, Hinks L, Lloyd B, Postle A, Smythe P, Turnell DC, Walton R: Blood intermediary metabolite and insulin concentrations after an overnight fast: reference ranges for adults, and interrelations. Clin Chem. 1978 Sep;24(9):1568-72. [PubMed:688619 ]
  9. Nielsen J, Ytrebo LM, Borud O: Lactate and pyruvate concentrations in capillary blood from newborns. Acta Paediatr. 1994 Sep;83(9):920-2. [PubMed:7819686 ]
  10. Ka T, Yamamoto T, Moriwaki Y, Kaya M, Tsujita J, Takahashi S, Tsutsumi Z, Fukuchi M, Hada T: Effect of exercise and beer on the plasma concentration and urinary excretion of purine bases. J Rheumatol. 2003 May;30(5):1036-42. [PubMed:12734903 ]
  11. Talseth T, Haegele KD, McNay JL, Skrdlant HB, Clementi WA, Shepherd AM: Pharmacokinetics and cardiovascular effects in rabbits of a major hydralazine metabolite, the hydralazine pyruvic-acid hydrazone. J Pharmacol Exp Ther. 1979 Dec;211(3):509-13. [PubMed:512915 ]
  12. Reece PA, Cozamanis I, Zacest R: Selective high-performance liquid chromatographic assays for hydralazine and its metabolites in plasma of man. J Chromatogr. 1980 Mar 14;181(3-4):427-40. [PubMed:7391156 ]
  13. Meijer-Severs GJ, Van Santen E, Meijer BC: Short-chain fatty acid and organic acid concentrations in feces of healthy human volunteers and their correlations with anaerobe cultural counts during systemic ceftriaxone administration. Scand J Gastroenterol. 1990 Jul;25(7):698-704. [PubMed:2396083 ]
  14. Elling D, Bader K: [Biochemical changes in cervix mucus in stepwise malignant transformation of cervix epithelium]. Zentralbl Gynakol. 1990;112(9):555-60. [PubMed:2378186 ]
  15. Mongan PD, Capacchione J, West S, Karaian J, Dubois D, Keneally R, Sharma P: Pyruvate improves redox status and decreases indicators of hepatic apoptosis during hemorrhagic shock in swine. Am J Physiol Heart Circ Physiol. 2002 Oct;283(4):H1634-44. Epub 2002 Jun 20. [PubMed:12234818 ]
  16. Wendisch VF: Microbial Production of Amino Acid-Related Compounds. Adv Biochem Eng Biotechnol. 2017;159:255-269. doi: 10.1007/10_2016_34. [PubMed:27872963 ]
  17. Alizadeh T, Nayeri S: An enzyme-free sensing platform based on molecularly imprinted polymer/MWCNT composite for sub-micromolar-level determination of pyruvic acid as a cancer biomarker. Anal Bioanal Chem. 2020 Jan;412(3):657-667. doi: 10.1007/s00216-019-02273-4. Epub 2019 Dec 11. [PubMed:31828373 ]