Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:29:11 UTC
Update Date2024-04-30 19:30:58 UTC
Metabolite IDMMDBc0000067
Metabolite Identification
Common NameOxoglutaric acid
DescriptionOxoglutaric acid, also known as alpha-ketoglutarate, alpha-ketoglutaric acid, AKG, or 2-oxoglutaric acid, is classified as a gamma-keto acid or a gamma-keto acid derivative. gamma-Keto acids are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. alpha-Ketoglutarate is considered to be soluble (in water) and acidic. alpha-Ketoglutarate is a key molecule in the TCA cycle, playing a fundamental role in determining the overall rate of this important metabolic process (PMID: 26759695 ). In the TCA cycle, AKG is decarboxylated to succinyl-CoA and carbon dioxide by AKG dehydrogenase, which functions as a key control point of the TCA cycle. Additionally, AKG can be generated from isocitrate by oxidative decarboxylation catalyzed by the enzyme known as isocitrate dehydrogenase (IDH). In addition to these routes of production, AKG can be produced from glutamate by oxidative deamination via glutamate dehydrogenase, and as a product of pyridoxal phosphate-dependent transamination reactions (mediated by branched-chain amino acid transaminases) in which glutamate is a common amino donor. AKG is a nitrogen scavenger and a source of glutamate and glutamine that stimulates protein synthesis and inhibits protein degradation in muscles. In particular, AKG can decrease protein catabolism and increase protein synthesis to enhance bone tissue formation in skeletal muscles (PMID: 26759695 ). Interestingly, enteric feeding of AKG supplements can significantly increase circulating plasma levels of hormones such as insulin, growth hormone, and insulin-like growth factor-1 (PMID: 26759695 ). It has recently been shown that AKG can extend the lifespan of adult C. elegans by inhibiting ATP synthase and TOR (PMID: 24828042 ). In combination with molecular oxygen, alpha-ketoglutarate is required for the hydroxylation of proline to hydroxyproline in the production of type I collagen. A recent study has shown that alpha-ketoglutarate promotes TH1 differentiation along with the depletion of glutamine thereby favouring Treg (regulatory T-cell) differentiation (PMID: 26420908 ). alpha-Ketoglutarate has been found to be associated with fumarase deficiency, 2-ketoglutarate dehydrogenase complex deficiency, and D-2-hydroxyglutaric aciduria, which are all inborn errors of metabolism (PMID: 8338207 ). Oxoglutaric acid has been found to be a metabolite produced by Corynebacterium and yeast (PMID: 27872963 ) (YMDB).
Structure
Synonyms
ValueSource
2-Ketoglutaric acidChEBI
alpha-Ketoglutaric acidChEBI
2-KetoglutarateGenerator
a-KetoglutarateGenerator
a-Ketoglutaric acidGenerator
alpha-KetoglutarateGenerator
Α-ketoglutarateGenerator
Α-ketoglutaric acidGenerator
OxoglutarateGenerator
2-oxo-1,5-PentanedioateHMDB
2-oxo-1,5-Pentanedioic acidHMDB
2-OxoglutarateHMDB
2-Oxoglutaric acidHMDB
2-OxopentanedioateHMDB
2-Oxopentanedioic acidHMDB
alpha-OxoglutarateHMDB
Oxogluric acidHMDB
2 Oxoglutaric acidHMDB
Ketoglutaric acidHMDB
alpha Ketoglutaric acidHMDB
2 Ketoglutaric acidHMDB
alpha KetoglutarateHMDB
alpha OxoglutarateHMDB
2 KetoglutarateHMDB
2 OxoglutarateHMDB
alpha-Oxoglutaric acidHMDB
alpha-Oxopentanedioic acidHMDB
alpha-Keto-glutaric acidHMDB
Α-oxoglutaric acidHMDB
Α-oxopentanedioic acidHMDB
Α-keto-glutaric acidHMDB
Molecular FormulaC5H6O5
Average Mass146.0981
Monoisotopic Mass146.021523302
IUPAC Name2-oxopentanedioic acid
Traditional Nameoxoglutarate
CAS Registry Number328-50-7
SMILES
OC(=O)CCC(=O)C(O)=O
InChI Identifier
InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)
InChI KeyKPGXRSRHYNQIFN-UHFFFAOYSA-N