SynCED: Pyruvic acid

Record Information

Version

1.0

Creation Date

2014-08-29 06:27:15 UTC

Update Date

2026-05-14 16:24:02 UTC

Accession Number

CHEM003285

Identification

Common Name

Pyruvic acid

Class

Small Molecule

Description

Pyruvic 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.

Contaminant Sources

EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Animal Toxin
Dietary Supplement
Drug
Food Toxin
Metabolite
Micronutrient
Natural Compound
Nutraceutical
Organic Compound
Supplement

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Ketopropionic acid	ChEBI
2-Oxopropanoic acid	ChEBI
2-Oxopropansaeure	ChEBI
2-Oxopropionsaeure	ChEBI
Acetylformic acid	ChEBI
Acide pyruvique	ChEBI
alpha-Ketopropionic acid	ChEBI
alpha-Oxopropionsaeure	ChEBI
Brenztraubensaeure	ChEBI
BTS	ChEBI
CH3COCOOH	ChEBI
Pyroracemic acid	ChEBI
2-Oxopropanoate	Kegg
2-Ketopropionate	Generator
Acetylformate	Generator
a-Ketopropionate	Generator
a-Ketopropionic acid	Generator
alpha-Ketopropionate	Generator
Α-ketopropionate	Generator
Α-ketopropionic acid	Generator
a-Oxopropionsaeure	Generator
Α-oxopropionsaeure	Generator
Pyroracemate	Generator
Pyruvate	Generator
2-Oxopropionate	HMDB
2-Oxopropionic acid	HMDB
Acid, pyruvic	MeSH, HMDB
Pyruvic acid	HMDB
alpha-Ketopropanoic acid	HMDB
α-Ketopropanoic acid	HMDB

Chemical Formula

C₃H₄O₃

Average Molecular Mass

88.062 g/mol

Monoisotopic Mass

88.016 g/mol

CAS Registry Number

127-17-3

IUPAC Name

2-oxopropanoic acid

Traditional Name

pyruvic acid

SMILES

CC(=O)C(O)=O

InChI Identifier

InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)

InChI Key

LCTONWCANYUPML-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Alpha-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

2-oxo monocarboxylic acid (CHEBI:32816 )
Oxo fatty acids (LMFA01060077 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Mitochondria
Peroxisome

Biofluid Locations

Not Available

Tissue Locations

Adipose Tissue
Brain
Fibroblasts
Kidney
Liver
Muscle
Myocardium
Neuron
Pancreas
Skeletal Muscle
Spleen
Testes
Thyroid Gland

Pathways

Name	SMPDB Link	KEGG Link
Alanine Metabolism	SMP00055	map00250
Amino Sugar Metabolism	SMP00045	map00520
Ammonia Recycling	SMP00009	map00910
Citric Acid Cycle	SMP00057	map00020
Cysteine Metabolism	SMP00013	map00270
Gluconeogenesis	SMP00128	Not Available
Glucose-Alanine Cycle	SMP00127	Not Available
Glycine and Serine Metabolism	SMP00004	map00260
Glycolysis	SMP00040	Not Available
Pyruvaldehyde Degradation	SMP00459	Not Available
Pyruvate Metabolism	SMP00060	map00620
Transfer of Acetyl Groups into Mitochondria	SMP00466	Not Available
Urea Cycle	SMP00059	Not Available
Congenital lactic acidosis	SMP00546	Not Available
Pyruvate Carboxylase Deficiency	SMP00350	Not Available
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)	SMP00334	Not Available
Pyruvate Dehydrogenase Complex Deficiency	SMP00212	Not Available
Pyruvate dehydrogenase deficiency (E3)	SMP00550	Not Available

Applications

Not Available

Biological Roles

metabolite

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	13.8°C
Boiling Point	54°C at 1.00E+01 mm Hg
Solubility	1E+006 mg/L (at 20°C)

Predicted Properties

Property	Value	Source
Water Solubility	134 g/L	ALOGPS
logP	-0.38	ALOGPS
logP	0.066	ChemAxon
logS	0.18	ALOGPS
pKa (Strongest Acidic)	2.93	ChemAxon
pKa (Strongest Basic)	-9.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	17.99 m³·mol⁻¹	ChemAxon
Polarizability	7.31 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Pyruvate is absorbed from the gastrointestinal tract from whence it is transported to the liver via the portal circulation.

Mechanism of Toxicity

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.

Metabolism

In the liver, pyruvate is metabolized via several pathways.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For nutritional supplementation, also for treating dietary shortage or imbalance

Minimum Risk Level

Not Available