Structure via PubChem · Public domain (PubChem)
alpha-ketoglutaric acid
Sign in to saveAlso known as α-ketoglutarate, 2-ketoglutarate, oxoglutarate, 2-oxoglutarate, oxoglutaric acid, Α-Ketoglutaric acid, 2-Oxo-1,5-pentanedioate, 2-ketoglutaric acid
chemical compound
Chemical data
- Formula
- C5H6O5
- Molecular weight
- 146.1 g/mol
- IUPAC name
- 2-oxopentanedioic acid
- SMILES
- C(CC(=O)O)C(=O)C(=O)O
- InChIKey
- KPGXRSRHYNQIFN-UHFFFAOYSA-N
- XLogP
- -0.9
- Polar surface area
- 91.7 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Has part
- carbon
- Mass
- 146.022
Show 6 more facts
- found in taxon
- tomato
- chemical formula
- C₅H₆O₅
- canonical SMILES
- C(CC(=O)O)C(=O)C(=O)O
- melting point
- 115.0
- Commons category
- Alpha-ketoglutaric acid
- medical condition treated
- kidney failure
Sources (7)
via Wikidata · CC0
~23 min read
Encyclopedic overview
α-Ketoglutaric acid (AKG) is an organic compound with the formula HO2CCO(CH2)2CO2H. A white, nontoxic solid, it is a common dicarboxylic acid. Relevant to its biological roles, it exists in water as its conjugate base α-ketoglutarate. It is also classified as a 2-ketocarboxylic acid. β-Ketoglutaric acid is an isomer. "Ketoglutaric acid" and "ketoglutarate", when not qualified as α or β, almost always refers respectively to α-ketoglutaric acid or α-ketoglutarate.
α-Ketoglutarate is an intermediate in the citric acid cycle, a set of cyclic reactions that supplies energy to cells. It is also an intermediate in or product of several other metabolic pathways. These include its being a component of metabolic pathways that: make amino acids and in the process regulate the cellular levels of carbon, nitrogen, and ammonia; reduce the cellular levels of potentially toxic reactive oxygen species; and synthesize the neurotransmitter γ-aminobutyric acid (GABA).
Excerpted from Wikipedia’s “alpha-ketoglutaric acid” article, available under the CC BY-SA 4.0 licence.