Common NamePyruvate
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
Molecular FormulaC3H4O3
Average Mass88.06210
Monoisotopic Mass88.01604
IUPAC Name2-oxopropanoic acid
Traditional NamePyruvic acid
CAS Registry Number127-17-3
SMILESCC(=O)C(=O)[O-]
InChI IdentifierInChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
InChI KeyLCTONWCANYUPML-UHFFFAOYSA-N
CHEBI IDCHEBI:15361
HMDB IDHMDB0000243
Pathways
NameSMPDB/PathBank
Glycine, serine and threonine metabolism
Pyruvate metabolism
Alanine, aspartate and glutamate metabolism
Nitrogen metabolism
Citrullinemia Type I
Carbamoyl Phosphate Synthetase Deficiency
Argininosuccinic Aciduria
Cysteine Metabolism
Glycolysis
Amino Sugar Metabolism
Citric Acid Cycle
Urea Cycle
Glutamate Metabolism
Glucose-Alanine Cycle
Gluconeogenesis
2-Hydroxyglutric Aciduria (D And L Form)
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)
Leigh Syndrome
Ornithine Transcarbamylase Deficiency (OTC Deficiency)
Pyruvate Dehydrogenase Complex Deficiency
Sialuria or French Type Sialuria
Non Ketotic Hyperglycinemia
Salla Disease/Infantile Sialic Acid Storage Disease
Dimethylglycine Dehydrogenase Deficiency
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency
Sarcosinemia
Lactic Acidemia
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)
Hyperinsulinism-Hyperammonemia Syndrome
Pyruvate Carboxylase Deficiency
Primary Hyperoxaluria Type I
Argininemia
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease
Homocarnosinosis
Tay-Sachs Disease
Pyruvaldehyde Degradation
Transfer of Acetyl Groups into Mitochondria
Dimethylglycine Dehydrogenase Deficiency
Hyperglycinemia, non-ketotic
Beta-mercaptolactate-cysteine disulfiduria
Glycogenosis, Type VII. Tarui disease
G(M2)-Gangliosidosis: Variant B, Tay-sachs disease
Congenital lactic acidosis
Fumarase deficiency
Mitochondrial complex II deficiency
2-ketoglutarate dehydrogenase complex deficiency
Pyruvate dehydrogenase deficiency (E3)
Pyruvate dehydrogenase deficiency (E2)
Primary hyperoxaluria II, PH2
Pyruvate kinase deficiency
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)
Fructose-1,6-diphosphatase deficiency
Triosephosphate isomerase
Succinic semialdehyde dehydrogenase deficiency
Fanconi-bickel syndrome
Glycogenosis, Type IB
Glycogenosis, Type IC
Glycogenosis, Type IA. Von gierke disease
Warburg Effect
3-Phosphoglycerate dehydrogenase deficiency
Cystinosis, ocular nonnephropathic
The oncogenic action of 2-hydroxyglutarate
The Oncogenic Action of Succinate
The Oncogenic Action of Fumarate
Glutaminolysis and Cancer
The oncogenic action of L-2-hydroxyglutarate in Hydroxygluaricaciduria
The oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria
StateLiquid
Water Solubility1.34e+02 g/l
logP-0.38
logS0.18
pKa (Strongest Acidic)2.93
pKa (Strongest Basic)-9.58
Hydrogen Acceptor Count3
Hydrogen Donor Count1
Polar Surface Area54.37 Ų
Rotatable Bond Count1
Physiological Charge-1
Formal Charge0
Refractivity17.99 m³·mol⁻¹
Polarizability7.32

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