ContaminantDB: Pyruvic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (17)XML

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00dr-4900000000-f26ef76666e40ab9fe61	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-00di-5900000000-b8e81f82572d4796e944	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014i-5970000000-154bf9ad168a12593fcc	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-a2cf85a5e1d2379d26df	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-4900000000-f26ef76666e40ab9fe61	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-5900000000-b8e81f82572d4796e944	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-5970000000-154bf9ad168a12593fcc	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-5900000000-5b1f470d4ff91420618c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-5417b44aa241a7ba27e8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dm-9400000000-6db65a709bdc47e3adf7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-a2cf85a5e1d2379d26df	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-dd49835da8355fb6e625	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-f09d8e3d7a774b255d89	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9000000000-7d91f6f626cab1a366fd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-8ae98cdb3e142034e52a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-e04e6c68013983e1b6dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-dd49835da8355fb6e625	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-f09d8e3d7a774b255d89	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-7d91f6f626cab1a366fd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-8ae98cdb3e142034e52a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-e04e6c68013983e1b6dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000f-9000000000-f24c93ecfd3928827154	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0udj-9000000000-fc3b9ad0c57f44261fba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9000000000-f3444f8b94ee5a0a9f74	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 33V, Negative	splash10-0avr-9000000000-dc40a6a1b9b166d6e68a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 33V, Negative	splash10-016r-9000000000-efac7b176bb77118ecb8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-d0defa72b09503c6d6d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000f-9000000000-c25fa150e9c490319a2a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-ccb42b4c05ddd001990f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-faf36ff70d6205370270	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-60c1a02aabf80f51050f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9000000000-ca5f4a2f06787d8b62a0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-0eb1fb2cdd24bdc78601	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-87bbaed151efac084591	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-87bbaed151efac084591	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-f315d0752893e7d0c657	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

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