ChemFOnt: Showing chemical card for Pyruvic acid (CFc000000164)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:29 UTC

Chemfont ID

CFc000000164

Molecule Identification

Common Name

Pyruvic acid

Definition

Pyruvic 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Pyruvate	Generator

Chemical Formula

C₆H₈O₆

Average Molecular Weight

176.1241

Monoisotopic Molecular Weight

176.032087988

IUPAC Name

2-hydroxyprop-2-enoic acid; 2-oxopropanoic acid

Traditional Name

2-hydroxyprop-2-enoic acid; pyruvic acid

CAS Registry Number

127-17-3

SMILES

CC(=O)C(O)=O.OC(=C)C(O)=O

InChI Identifier

InChI=1S/2C3H4O3/c2*1-2(4)3(5)6/h1H3,(H,5,6);4H,1H2,(H,5,6)

InChI Key

UNMYEGNJYFQDES-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

Not Available

External Descriptors

Not Available

Functional Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Organoleptic effect

Odor

Taste

Sour

Adipose tissue (HMDB: HMDB0000243)

Muscle tissue

Skeletal muscle (HMDB: HMDB0000243)
Cardiac muscle (HMDB: HMDB0000243)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 7819686)
Breast milk (PMID: 24027187)
Cerebrospinal Fluid (CSF) (PMID: 15627241)
Saliva (PMID: 12097436)
Cellular Cytoplasm (PMID: 15882454)

Organ

Gland

Thyroid gland (HMDB: HMDB0000243)

Cell

Fibroblasts (HMDB: HMDB0000243)
Neuron (HMDB: HMDB0000243)

Excreta

Biofluid or Excreta

Urine (PMID: 12234818)
Feces (PMID: 18085514)
Sweat (PMID: 26755145)

Cellular substructure

Extracellular (HMDB: HMDB0000243)
Cytoplasm (HMDB: HMDB0000243)

Organelle

Mitochondrion (HMDB: HMDB0000243)
Peroxisome (HMDB: HMDB0000243)

Tissue substructure

Muscle (HMDB: HMDB0000243)

Source

Exogenous

Exogenous (HMDB: HMDB0000243)

Food

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Fortified wines

Port wine (FooDB: FOOD00630)

Fruit

Pome

Apple (FooDB: FOOD00105)

Tropical fruit

French plantain (FooDB: FOOD00436)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)

Fruit vegetable

Garden tomato (var.) (FooDB: FOOD00173)

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Other seed

Ginkgo nuts (FooDB: FOOD00367)

Herbs and Spices (FooDB: FOOD00866)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Nut

Peanut (FooDB: FOOD00016)

Pulse

Pea

Chickpea (FooDB: FOOD00047)
Common pea (FooDB: FOOD00141)

Pulses (FooDB: FOOD00867)

Endogenous

Endogenous (HMDB: HMDB0000243)

Process

Naturally occurring process

Congenital Lactic Acidosis (HMDB: HMDB0000243)
Pyruvate Carboxylase Deficiency (HMDB: HMDB0000243)
Pyruvate Dehydrogenase Complex Deficiency (HMDB: HMDB0000243)
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency) (HMDB: HMDB0000243)
Pyruvate Dehydrogenase Deficiency (E3) (HMDB: HMDB0000243)
The Oncogenic Action of Succinate (PathBank: SMP0002292)
Glutaminolysis and Cancer (PathBank: SMP0108773)
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120445)
Sarcosinemia (PathBank: SMP0120521)
Salla Disease/Infantile Sialic Acid Storage Disease (PathBank: SMP0120524)
G(M2)-Gangliosidosis: Variant B, Tay-Sachs Disease (PathBank: SMP0120599)
Fructose-1,6-diphosphatase Deficiency (PathBank: SMP0120626)
Succinic Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120631)
Fanconi-Bickel Syndrome (PathBank: SMP0120636)
Argininemia (PathBank: SMP0120676)
Argininosuccinic Aciduria (PathBank: SMP0120677)
Carbamoyl Phosphate Synthetase Deficiency (PathBank: SMP0120682)
Dihydropyrimidine Dehydrogenase Deficiency (DHPD) (PathBank: SMP0120694)
Leigh Syndrome (PathBank: SMP0120726)
Ornithine Transcarbamylase Deficiency (OTC Deficiency) (PathBank: SMP0120762)
Beta-Mercaptolactate-Cysteine Disulfiduria (PathBank: SMP0120783)
Glycogenosis, Type VII. Tarui Disease (PathBank: SMP0120815)
Pyruvate Dehydrogenase Deficiency (E2) (PathBank: SMP0120834)
Glycogenosis, Type IC (PathBank: SMP0120857)
Glycogenosis, Type IA. Von Gierke Disease (PathBank: SMP0120864)
Sialuria or French Type Sialuria (PathBank: SMP0000216)
The Oncogenic Action of 2-Hydroxyglutarate (PathBank: SMP0002291)
Non-Ketotic Hyperglycinemia (PathBank: SMP0120534)
Primary Hyperoxaluria Type I (PathBank: SMP0120543)
Tay-Sachs Disease (PathBank: SMP0120545)
Pyruvate Kinase Deficiency (PathBank: SMP0120623)
Lactic Acidemia (PathBank: SMP0120724)
2-Ketoglutarate Dehydrogenase Complex Deficiency (PathBank: SMP0120832)
Primary Hyperoxaluria II, PH2 (PathBank: SMP0120841)
Phosphoenolpyruvate Carboxykinase Deficiency 1 (PEPCK1) (PathBank: SMP0120843)
Triosephosphate Isomerase Deficiency (PathBank: SMP0120846)
3-Phosphoglycerate Dehydrogenase Deficiency (PathBank: SMP0120872)
Citrullinemia Type I (PathBank: SMP0120686)
Glycogenosis, Type IB (PathBank: SMP0120637)
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease (PathBank: SMP0120488)
Homocarnosinosis (PathBank: SMP0120494)
Fumarase Deficiency (PathBank: SMP0120611)
2-Hydroxyglutric Aciduria (D and L Form) (PathBank: SMP0120659)
Dimethylglycine Dehydrogenase Deficiency (PathBank: SMP0120695)
Hyperglycinemia, Non-Ketotic (PathBank: SMP0120770)
Mitochondrial Complex II Deficiency (PathBank: SMP0120831)
The Oncogenic Action of Fumarate (PathBank: SMP0002295)
Hyperinsulinism-Hyperammonemia Syndrome (PathBank: SMP0120496)
Cystinosis, Ocular Nonnephropathic (PathBank: SMP0120654)
The Oncogenic Action of L-2-Hydroxyglutarate in Hydroxygluaricaciduria (PathBank: SMP0002358)
The Oncogenic Action of D-2-Hydroxyglutarate in Hydroxygluaricaciduria (PathBank: SMP0002359)

Protein pathway

LPS and Citrate Signaling and Inflammation (PathBank: SMP0120946)

Role

Biological role

Metabolite (HMDB: HMDB0000243)
Waste product (PMID: 35448883)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavor (HMDB: HMDB0000243)

Pharmaceutical industry

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00000118)
Lewy Body Dementia (MarkerDB: MDB00000118)
Meningitis (MarkerDB: MDB00000118)
Pyruvate Dehydrogenase Phosphatase Deficiency (MarkerDB: MDB00000118)
Pearson Marrow Pancreas Syndrome (MarkerDB: MDB00000118)
Pyruvate Dehydrogenase Deficiency (MarkerDB: MDB00000118)
Fumarase deficiency (MarkerDB: MDB00000118)
Leigh syndrome (MarkerDB: MDB00000118)
G.R.A.C.I.L.E. Syndrome (MarkerDB: MDB00000118)
Hereditary Myopathy With Lactic Acidosis (MarkerDB: MDB00000118)
Fructose 1,6 Bisphosphatase Deficiency (MarkerDB: MDB00000118)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	139 g/L	ALOGPS
logP	-0.09	ALOGPS
logP	0.066	ChemAxon
logS	0.2	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	2	ChemAxon
Refractivity	17.99 m³·mol⁻¹	ChemAxon
Polarizability	7.32 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008293

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pyruvic acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Xiang, Wei; Okita, Motomu. Preparation of pyruvic acid. Jpn. Kokai Tokkyo Koho (2003), 5 pp.

Showing chemical card for Pyruvic acid (CFc000000164)

MOL for CFc000000164 (Pyruvic acid)

3D MOL for CFc000000164 (Pyruvic acid)

3D SDF for CFc000000164 (Pyruvic acid)

3D-SDF for CFc000000164 (Pyruvic acid)

PDB for CFc000000164 (Pyruvic acid)

3D PDB for CFc000000164 (Pyruvic acid)

SMILES for CFc000000164 (Pyruvic acid)

INCHI for CFc000000164 (Pyruvic acid)

Structure for CFc000000164 (Pyruvic acid)

3D Structure for CFc000000164 (Pyruvic acid)