dimethyl alpha-ketoglutarate profile

Dimethyl alpha-ketoglutarate (DMKG) is a synthetic derivative of alpha-ketoglutarate, a key intermediate in the citric acid cycle. It has been investigated for its potential therapeutic properties in a variety of conditions, including cancer, neurodegenerative diseases, and metabolic disorders. DMKG is thought to exert its effects through several mechanisms, including: 1) acting as a precursor to alpha-ketoglutarate, which can enhance the activity of enzymes involved in energy production and detoxification. 2) modulating the activity of specific enzymes, such as histone demethylases, which play a role in gene expression. 3) acting as an antioxidant, protecting cells from oxidative stress. DMKG is generally well-tolerated in animal studies, although further research is needed to evaluate its safety and efficacy in humans. Research on DMKG is ongoing to explore its potential as a therapeutic agent in a variety of conditions. Its ability to modulate key metabolic pathways and cellular processes makes it a promising target for drug development.'

ID Source	ID
PubMed CID	25775
CHEMBL ID	4877741
CHEBI ID	173796
SCHEMBL ID	9543
MeSH ID	M0537075

Synonym
CHEBI:173796
dimethyl 2-oxopentanedioate
dimethyl-alpha-ketoglutarate
13192-04-6
dimethyl 2-oxoglutarate, 96%
2-oxopentanedioic acid, dimethyl ether
2-oxoglutaric acid dimethyl ester
dimethyl 2-ketoglutarate
2-ketoglutaric acid dimethyl ester
K0013
dimethyl 2-oxoglutarate
A806333
dimethyl 2-oxidanylidenepentanedioate
2-oxopentanedioic acid dimethyl ester
FT-0612735
AKOS015851605
SCHEMBL9543
dimethyl 2-oxopentanedioate #
dimethyl-.alpha.-ketoglutarate
glutaric acid, 2-oxo-, dimethyl ester
pentanedioic acid, 2-oxo-, dimethyl ester
dimethyl 2-ketoglutaconate
DTXSID10157251
mfcd00048052
J-006086
dimethyl alpha-ketoglutarate
dimethyl2-oxoglutarate
SY004319
BCP24128
AS-47656
Q65707091
AMY20457
SB32822
pentanedioic acid, 2-oxo-, 1,5-dimethyl ester
F14954
nsc-783840
nsc783840
CS-0103277
EN300-1661000
1,5-dimethyl 2-oxopentanedioate
CHEMBL4877741

Class	Description
oxo carboxylic acid	Any compound that has an aldehydic or ketonic group as well as a carboxylic acid group in the same molecule.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Assay ID	Title	Year	Journal	Article
AID1763200	Inhibition of TET in human THP-1 cells assessed as reduction in 5hmc/5mc level at 50 uM incubated for 12 hrs by dot blot analysis relative to control	2021	Bioorganic & medicinal chemistry, 06-01, Volume: 39	SAR insights into TET2 catalytic domain inhibition: Synthesis of 2-Hydroxy-4-Methylene-pentanedicarboxylates.
AID1763199	Inhibition of TET in human THP-1 cells assessed as reduction in 5hmc/5mc level at 25 uM incubated for 12 hrs by dot blot analysis relative to control	2021	Bioorganic & medicinal chemistry, 06-01, Volume: 39	SAR insights into TET2 catalytic domain inhibition: Synthesis of 2-Hydroxy-4-Methylene-pentanedicarboxylates.
AID1763201	Inhibition of TET in human THP-1 cells assessed as reduction in 5hmc/5mc level at 100 uM incubated for 12 hrs by dot blot analysis relative to control	2021	Bioorganic & medicinal chemistry, 06-01, Volume: 39	SAR insights into TET2 catalytic domain inhibition: Synthesis of 2-Hydroxy-4-Methylene-pentanedicarboxylates.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	1 (6.67)	29.6817
2010's	7 (46.67)	24.3611
2020's	7 (46.67)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (6.67%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	14 (93.33%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
alpha-hydroxyglutarate 2-hydroxyglutarate : A dicarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of 2-hydroxyglutaric acid.. 2-hydroxyglutaric acid : A 2-hydroxydicarboxylic acid that is glutaric acid in which one hydrogen alpha- to a carboxylic acid group is substituted by a hydroxy group.	2.31	1	2-hydroxydicarboxylic acid; dicarboxylic fatty acid	metabolite; mouse metabolite
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	2.41	1	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	2.31	1	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	2.31	1	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	2.13	1	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	2.72	2	amino acid zwitterion; glutamine family amino acid; glutamine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.05	1	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
ornithine Ornithine: An amino acid produced in the urea cycle by the splitting off of urea from arginine.. ornithine : An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5.	2.41	1	non-proteinogenic L-alpha-amino acid; ornithine	algal metabolite; hepatoprotective agent; mouse metabolite
dimethyl succinate dimethyl succinate: potent insulin secretagogue	2.31	1	fatty acid methyl ester
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.25	1	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
n-acetyldehydroalanine methyl ester N-acetyldehydroalanine methyl ester: modifies amino & sulfhydryl groups in amino acids & proteins; structure	2.31	1
d-2-hydroxyglutarate (R)-2-hydroxyglutaric acid : The (R)-enantiomer of 2-hydroxyglutaric acid.	2.31	1	2-hydroxyglutaric acid	algal metabolite
alpha-hydroxyglutarate, (l)-isomer [no description available]	2.31	1	2-hydroxyglutaric acid
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	2.1	1	acyl-CoA	acyl donor; coenzyme; effector; fundamental metabolite
fumaric acid fumaric acid: see also record for ferrous fumarate; use FUMARATES for general fumaric acid esters. fumaric acid : A butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.	2.31	1	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
dimethyloxalylglycine dimethyloxallyl glycine: structure in first source	2.31	1	glycine derivative; methyl ester; secondary carboxamide	EC 1.14.11.29 (hypoxia-inducible factor-proline dioxygenase) inhibitor; neuroprotective agent
dimethyl fumarate [no description available]	2.31	1	diester; enoate ester; methyl ester	antipsoriatic; immunomodulator
nadp [no description available]	2.05	1
oxalylglycine oxalylglycine: structure given in first source. N-oxalylglycine : An amino dicarboxylic acid that is iminodiacetic acid with an oxo substituent. It is used as an inhibitor of alpha-ketoglutarate dependent (EC 1.14.11.*) enzymes.	2.31	1	amino dicarboxylic acid; N-acylglycine	EC 1.14.11.* (oxidoreductase acting on paired donors, 2-oxoglutarate as one donor, incorporating 1 atom each of oxygen into both donors) inhibitor
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	3.71	2
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	2.31	1
glutaminase [no description available]	2.66	2

Condition	Relationship Strength	Studies
Deficiency Disease, Ornithine Carbamoyltransferase [description not available]	2.41	1
Ornithine Carbamoyltransferase Deficiency Disease An inherited urea cycle disorder associated with deficiency of the enzyme ORNITHINE CARBAMOYLTRANSFERASE, transmitted as an X-linked trait and featuring elevations of amino acids and ammonia in the serum. Clinical features, which are more prominent in males, include seizures, behavioral alterations, episodic vomiting, lethargy, and coma. (Menkes, Textbook of Child Neurology, 5th ed, pp49-50)	2.41	1
Hyperammonemia Elevated level of AMMONIA in the blood. It is a sign of defective CATABOLISM of AMINO ACIDS or ammonia to UREA.	2.41	1
Brain Stem Neoplasms, Primary [description not available]	2.6	1
DIPG Brain Tumors [description not available]	2.6	1
Glial Cell Tumors [description not available]	2.6	1
Diffuse Intrinsic Pontine Glioma A rare, aggressive brain tumor that forms in the GLIAL CELLS in the PONS.	7.6	1
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	7.6	1
Brain Stem Neoplasms Benign and malignant intra-axial tumors of the MESENCEPHALON; PONS; or MEDULLA OBLONGATA of the BRAIN STEM. Primary and metastatic neoplasms may occur in this location. Clinical features include ATAXIA, cranial neuropathies (see CRANIAL NERVE DISEASES), NAUSEA, hemiparesis (see HEMIPLEGIA), and quadriparesis. Primary brain stem neoplasms are more frequent in children. Histologic subtypes include GLIOMA; HEMANGIOBLASTOMA; GANGLIOGLIOMA; and EPENDYMOMA.	2.6	1
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	3.12	1
Benign Neoplasms [description not available]	3.12	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.12	1
Hospital-Acquired Condition [description not available]	2.25	1
Cirrhosis [description not available]	2.25	1
Acquired Laryngeal Stenosis [description not available]	2.25	1
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	2.25	1
Enterovirus Infections Diseases caused by ENTEROVIRUS.	2.25	1
Cardiomyopathy, Congestive [description not available]	2.1	1
Cardiomyopathy, Dilated A form of CARDIAC MUSCLE disease that is characterized by ventricular dilation, VENTRICULAR DYSFUNCTION, and HEART FAILURE. Risk factors include SMOKING; ALCOHOL DRINKING; HYPERTENSION; INFECTION; PREGNANCY; and mutations in the LMNA gene encoding LAMIN TYPE A, a NUCLEAR LAMINA protein.	2.1	1
Hypertrophy General increase in bulk of a part or organ due to CELL ENLARGEMENT and accumulation of FLUIDS AND SECRETIONS, not due to tumor formation, nor to an increase in the number of cells (HYPERPLASIA).	2.1	1
Cirrhosis, Liver [description not available]	2.52	2
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	2.52	2

dimethyl alpha-ketoglutarate

Cross-References

Synonyms (41)

Drug Classes (1)

Bioassays (3)

Research

Studies (15)

Market Indicators

Research Demand Index: 28.70

Study Types