Chemical Formula: C5H6O5
Chemical Formula C5H6O5
Found 39 metabolite its formula value is C5H6O5
Oxoglutaric acid
Oxoglutaric 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). [Spectral] 2-Oxoglutarate (exact mass = 146.02152) and S-Adenosyl-L-homocysteine (exact mass = 384.12159) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] 2-Oxoglutarate (exact mass = 146.02152) and (S)-Malate (exact mass = 134.02152) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Flavouring ingredient
3-Oxoglutaric acid
3-oxoglutaric acid or acetonedicarboxylic acid is a simple carboxylic acid, which may be used as a building block in organic chemistry. It has been found to be a microbial metabolite.
Methoxymalic acid
Methoxymalic acid, also known as methoxymalate, belongs to dicarboxylic acids and derivatives class of compounds. Those are organic compounds containing exactly two carboxylic acid groups. Methoxymalic acid is soluble (in water) and an extremely strong acidic compound (based on its pKa). Methoxymalic acid can be found in oat, which makes methoxymalic acid a potential biomarker for the consumption of this food product.
2-Oxoglutaric acid
An oxo dicarboxylic acid that consists of glutaric acid bearing an oxo substituent at position 2. It is an intermediate metabolite in Krebs cycle.
Dehydro-D-arabinono-1,4-lactone
A gamma-lactone that is 5-(hydroxymethyl)furan-2(5H)-one substituted at positions 3 and 4 by hydroxy groups (the 5R-stereoisomer).
citramalate(2-)
A dicarboxylic acid dianion that is obtained by removal of a proton from both of the carboxylic acid groups of citramalic acid.
L-citramalate(2-)
A citramalate(2-) that is the conjugate acid of L-citramalic acid.
2-hydroxyglutarate(2-)
A dicarboxylic acid dianion resulting from the removal of a proton from both of the carboxylic acid groups of 2-hydroxyglutaric acid.
3-hydroxyglutarate(2-)
A dicarboxylic acid dianion resulting from the deprotonation of the two carboxy groups of 3-hydroxyglutaric acid; major species at pH 7.3.
(S)-2-hydroxyglutarate(2-)
A 2-hydroxyglutarate(2-) that has (2S)-configuration.
D-citramalate(2-)
A citramalate(2-) that is the conjugate base of D-citramalic acid.
3-methylmalate(2-)
A dicarboxylic acid dianion obtained by deprotonation of both carboxy groups of 3-methylmalic acid; major microspecies at pH 7.3
(R)-2-hydroxyglutarate(2-)
A 2-hydroxyglutarate(2-) that has (2R)-configuration.