FComEx: 2-Oxopentanedioic acid (PC000123)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:39 UTC

Update date

2017-01-19 02:36:13 UTC

FoodComEx ID

PC000123

FoodDB Record

FDB003361

Chemical Information

Name

2-Oxopentanedioic acid

Description

Oxoglutaric acid, also known as oxoglutarate or alpha-ketoglutarate, belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Oxoglutaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Oxoglutaric acid exists in all living species, ranging from bacteria to humans. Within humans, oxoglutaric acid participates in a number of enzymatic reactions. In particular, oxoglutaric acid can be biosynthesized from isocitric acid; which is mediated by the enzyme isocitrate dehydrogenase. In addition, oxoglutaric acid can be converted into succinyl-CoA; which is mediated by the enzyme oxoglutarate dehydrogenase complex. In humans, oxoglutaric acid is involved in the oncogenic action of fumarate. Oxoglutaric acid is an odorless tasting compound. Outside of the human body, Oxoglutaric acid is found, on average, in the highest concentration within star fruits and milk (cow). Oxoglutaric acid has also been detected, but not quantified in, several different foods, such as common chokecherries, red beetroots, adzuki beans, buffalo currants, and grapefruit/pummelo hybrids. This could make oxoglutaric acid a potential biomarker for the consumption of these foods. Oxoglutaric acid is a potentially toxic compound. An oxo dicarboxylic acid that consists of glutaric acid bearing an oxo substituent at position 2.

CAS Number

328-50-7

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
α-ketoglutaric acid	biospider
α-oxoglutaric acid	biospider
2-Ketoglutarate	biospider
2-Ketoglutaric acid	biospider
2-Oxo-1,5-dipentanedioic acid	biospider
2-Oxo-1,5-pentanedioate	biospider
2-Oxo-1,5-pentanedioic acid	biospider
2-Oxo-Glutaric Acid	biospider
2-Oxoglutarate	biospider
2-Oxoglutaric acid	db_source
2-Oxopentanedioate	biospider
2-oxopentanedionate	biospider
2-oxopentanedionic acid	biospider
2-Oxyglutaric Acid	biospider
305-72-6 (di-hydrochloride salt)	biospider
997-43-3 (mono-potassium salt)	biospider
a-Ketoglutarate	Generator
a-Ketoglutaric acid	db_source
AKG	biospider
Alpha ketoglutarate	biospider
Alpha-keto-glutaric acid	biospider
Alpha-ketoglutarate	biospider
alpha-Ketoglutaric acid	biospider
Alpha-ketoglutaric acid alpha	biospider
Alpha-oxoglutarate	biospider
alpha-Oxoglutaric acid	biospider
Alpha-oxopentanedioic acid	biospider
Alphaketoglutaric acid	biospider
Bis(L-arginin)-2-oxoglutarat	biospider
FEMA 3891	db_source
Glutaric acid, &alpha	biospider
Glutaric acid, 2-oxo-	biospider
Glutaric acid, 2-oxo- (8CI)	biospider
Glutaric acid, alpha keto	biospider
keto	biospider
Ketoglutarate	biospider
Oxoglutarate	biospider
Oxoglutaric acid	biospider
Pentanedioic acid, 2-oxo-	biospider
Pentanedioic acid, 2-oxo- (9CI)	biospider
α-ketoglutarate	Generator
α-ketoglutaric acid	Generator

Chemical Formula

C5H6O5

IUPAC name

2-oxopentanedioic acid

InChI Identifier

InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)

InChI Key

KPGXRSRHYNQIFN-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CCC(=O)C(O)=O

Average Molecular Weight

146.0981

Monoisotopic Molecular Weight

146.021523302

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-keto acids and derivatives

Alternative Parents