Classification Term: 2324
Gamma-keto acids and derivatives (ontology term: CHEMONTID:0001115)
Organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom." []
found 22 associated metabolites at sub_class
metabolite taxonomy ontology rank level.
Ancestor: Keto acids and derivatives
Child Taxonomies: 3-Acylpyruvic acids
3-Succinoylpyridine
3-succinoylpyridine is the byproduct of tobacco-specific N-nitrosamines generated by the enzyme cytochrome P 450 which catalyzes methylnitrosaminopyridylbutanone hydroxylation. (PMID: 11368333). This nicotine metabolite is commonly found in the urine of smokers. (PMID: 14581070). 3-succinoylpyridine is the byproduct of tobacco-specific N-nitrosamines generated by the enzyme cytochrome P 450 which catalyzes methylnitrosaminopyridylbutanone hydroxylation. (PMID: 11368333)
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
Prephenate
Prephenate (CAS: 126-49-8), also known as prephenic acid, 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. Prephenic acid is an example of an achiral (optically inactive) molecule which has two pseudoasymmetric atoms (i.e. stereogenic but not chirotopic centers): the C1 and the C4 cyclohexadiene ring atoms. Prephenate exists in all living species, ranging from bacteria to humans. Prephenate has been detected, but not quantified, in several different foods, such as American pokeweeds, breadnut tree seeds, common wheats, swiss chards, and breadfruits. The other stereoisomer, i.e. trans or, better, (1r, 4r), is called epiprephenic acid. It has been shown that of the two possible diastereoisomers, the natural prephenic acid is one that has both substituents at higher priority (according to CIP rules) on the two pseudoasymmetric carbons, i.e. the carboxyl and the hydroxyl groups, in the cis configuration, or (1s, 4s) according to the new IUPAC stereochemistry rules (2013). It is biosynthesized by a [3,3]-sigmatropic Claisen rearrangement of chorismate. Prephenic acid, commonly also known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine, as well as of a large number of secondary metabolites of the shikimate pathway. Prephenic acid, more commonly known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine. [HMDB]. Prephenate is found in many foods, some of which are alaska wild rhubarb, chinese chestnut, kai-lan, and globe artichoke.
4-Hydroxy-2-oxoglutaric acid
4-Hydroxy-2-ketoglutaric acid is a substrate for Fructose-bisphosphate aldolase A. [HMDB] 4-Hydroxy-2-ketoglutaric acid is a substrate for Fructose-bisphosphate aldolase A.
Gamma-delta-Dioxovaleric acid
gamma-delta-Dioxovaleric acid (DOVA) is the final oxidation product of 5-aminolevulinic acid, a precursor of porphyrin in the biosynthesis of heme. It can accumulate in liver, brain, and other organs under pathological conditions such as acute intermittent porphyria. [HMDB] Gamma-delta-Dioxovaleric acid (DOVA) is the final oxidation product of 5-aminolevulinic acid, a precursor of porphyrin in the biosynthesis of heme. It can accumulate in liver, brain, and other organs under pathological conditions such as acute intermittent porphyria.
(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate
(1r,6r)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate, also known as shchc, belongs to gamma-keto acids and derivatives class of compounds. Those are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom (1r,6r)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate is slightly soluble (in water) and a weakly acidic compound (based on its pKa). (1r,6r)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate can be found in a number of food items such as kiwi, muskmelon, purple laver, and lima bean, which makes (1r,6r)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate a potential biomarker for the consumption of these food products (1r,6r)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate may be a unique E.coli metabolite.
2-Methylene-4-oxopentanedioic acid
2-Oxo-4-methylenepentanedioic acid is found in nuts. 2-Oxo-4-methylenepentanedioic acid is found in peanut (Arachis hypogaea).
2-n-Propyl-4-oxopentanoic acid
2-n-Propyl-4-oxopentanoic acid is a metabolite of valproic acid. Valproic acid (VPA) is a chemical compound and an acid that has found clinical use as an anticonvulsant and mood-stabilizing drug, primarily in the treatment of epilepsy, bipolar disorder, and, less commonly, major depression. It is also used to treat migraine headaches and schizophrenia. VPA is a liquid at room temperature, but it can be reacted with a base such as sodium hydroxide to form the salt sodium valproate, which is a solid. (Wikipedia)
D-4-Hydroxy-2-oxoglutarate
This compound belongs to the family of Gamma Keto-Acids and Derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom
Levulinic acid
Found in beet, caramel etcand is also reported in papaya (Carica papaya), wheat bread, rice bran, sake and Chinese quince fruit (Chaenomeles legenaria)and is also production by lychee (Litchi chinensis), Malabar spinach (Basella rubra) and Phyllophora subspecies Flavour ingredient. Levulinic acid is a crystalline keto acid prepared from levulose, inulin, starch, etc., by boiling them with dilute hydrochloric or sulfuric acids. D004791 - Enzyme Inhibitors Levulinic acid is a precursor for the synthesis of biofuels, such as ethyl levulinate. Levulinic acid is a precursor for the synthesis of biofuels, such as ethyl levulinate.
Ethyl levulinate
Ethyl levulinate is a flavouring ingredient. Flavouring ingredient
2-Hydroxy-4-oxopentanoic acid
2-Hydroxy-4-oxopentanoic acid is found in alcoholic beverages. 2-Hydroxy-4-oxopentanoic acid is formed in beer wort fermentation Alitretinoin (9-cis-retinoic acid) is a naturally-occurring endogenous retinoid indicated for topical treatment of cutaneous lesions in patients with AIDS-related Kaposis sarcoma. Alitretinoin inhibits the growth of Kaposis sarcoma (KS) cells in vitro. Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately control anterior/posterior patterning in early developmental stages. Retinoic acid acts by binding to heterodimers of the retinoic acid receptor (RAR) and the retinoid X receptor (RXR), which then bind to retinoic acid response elements (RAREs) in the regulatory regions of direct targets (including Hox genes), thereby activating gene transcription. Retinoic acid receptors mediate transcription of different sets of genes of cell differentiation, thus it also depends on the target cells. 2-Hydroxy-4-oxopentanoic acid is one of the target genes is the gene of the retinoic acid receptor itself which occurs during positive regulation. Control of retinoic acid levels is maintained by a suite of proteins. Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID: 17495912). It is an important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth and embryonic development. 2-Hydroxy-4-oxopentanoic acid is an excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute). Formed in beer wort fermentation
Diplodiatoxin
Diplodiatoxin is a metabolite of Diplodia maydis (parasite of sweet corn). Toxin causing diplodiosis disease of cattle and shee
2-Methyl-4-oxopentanedioic acid
2-Methyl-4-oxopentanedioic acid is found in fruits. 2-Methyl-4-oxopentanedioic acid is a constituent of Tamarindus indica (tamarind). Constituent of Tamarindus indica (tamarind). 2-Methyl-4-oxopentanedioic acid is found in fruits.
Sedanonic acid
Sedanonic acid is found in green vegetables. Sedanonic acid is isolated from celery oil (Apium graveolens) after hydrolysis. Isolated from celery oil (Apium graveolens) after hydrolysis Sedanonic acid is found in green vegetables.
Methyl levulinate
Methyl levulinate is a caramellic flavouring agent [CCD]. Caramellic flavouring agent [CCD]
Butyl levulinate
Butyl levulinate is a flavouring agent. Flavouring agent
Propyl levulinate
Propyl levulinate is a caramellic flavouring agent. [CCD]. Caramellic flavouring agent [CCD]
Dimethyl 2-oxoglutarate
Dimethyl-2-oxoglutarate (MOG) is a key intermediate in the Krebs cycle and an important nitrogen transporter in the metabolic pathways in biological processes (PMID: 19766063).