4-methyleneglutamic acid profile

4-methyleneglutamic acid, also known as 4-methylene-L-glutamate, is a non-proteinogenic amino acid that is a potent inhibitor of glutamate dehydrogenase (GDH). GDH is an enzyme that catalyzes the reversible oxidative deamination of glutamate to α-ketoglutarate, an important step in the citric acid cycle. By inhibiting GDH, 4-methyleneglutamic acid can affect the regulation of glutamate metabolism and neurotransmission. It is studied as a potential therapeutic agent for various neurological disorders, such as epilepsy, stroke, and Alzheimer's disease, due to its ability to modulate glutamate levels in the brain. Additionally, it has been investigated as a tool to explore the role of GDH in various physiological processes. It can be synthesized using different chemical methods, involving reactions with glutamate derivatives and specific reagents. The synthesis process typically involves multiple steps to achieve the desired structure.'

4-methyleneglutamic acid: RN given refers to (DL-Glu)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	96407
CHEMBL ID	38817
CHEBI ID	48029
SCHEMBL ID	1476505
MeSH ID	M0097692

Synonym
7150-74-5
nsc-72472
nsc72472
4-methyleneglutamic acid
4-methylene-dl-glutamic acid
gamma-methylene glutamic acid
2-amino-4-methylidenepentanedioic acid
CHEBI:48029 ,
CHEMBL38817
gamma-methylene-dl-glutamic acid
FT-0694727
AKOS006271851
SCHEMBL1476505
nsc 72472
dl-glutamic acid, 4-methylene-
glutamic acid,4-methylene-
h-gamma-methylene-dl-glutamic acid
EN300-6394085
h-gamma-methylene-dl-glu-oh
mfcd00082373
4-methylene glutamic acid
l-2-amino-4-methylenepentanedioic acid
4-methylidene glutamic acid
h--methylene-dl-glu-oh
h-g-methylene-dl-glu-oh
2-amino-4-methylenepentanedioic acid
Q27120911
DTXSID301347258

Class	Description
non-proteinogenic alpha-amino acid	Any alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids.
[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
AID108506	Ratio between EC50 of compound and glutamate measured against metabotropic glutamate receptor 1	1999	Journal of medicinal chemistry, May-06, Volume: 42, Issue:9	Agonist selectivity of mGluR1 and mGluR2 metabotropic receptors: a different environment but similar recognition of an extended glutamate conformation.
AID108985	Ratio between EC50 of compound and glutamate measured against Metabotropic glutamate receptor 2	1999	Journal of medicinal chemistry, May-06, Volume: 42, Issue:9	Agonist selectivity of mGluR1 and mGluR2 metabotropic receptors: a different environment but similar recognition of an extended glutamate conformation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	15 (78.95)	18.7374
1990's	3 (15.79)	18.2507
2000's	1 (5.26)	29.6817
2010's	0 (0.00)	24.3611
2020's	0 (0.00)	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	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	19 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	1.96	1	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	1.96	1	metal allergen; nickel group element atom	epitope; micronutrient
cycloleucine Cycloleucine: An amino acid formed by cyclization of leucine. It has cytostatic, immunosuppressive and antineoplastic activities.. 1-aminocyclopentanecarboxylic acid : A non-proteinogenic alpha-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups.	1.98	1	non-proteinogenic alpha-amino acid	EC 2.5.1.6 (methionine adenosyltransferase) inhibitor
4-methylglutamic acid 4-methylglutamic acid : A glutamic acid derivative that is glutamic acid substituted by a methyl group at position 4.	2.68	3	amino dicarboxylic acid; glutamic acid derivative
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	1.96	1	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
cysteamine Cysteamine: A mercaptoethylamine compound that is endogenously derived from the COENZYME A degradative pathway. The fact that cysteamine is readily transported into LYSOSOMES where it reacts with CYSTINE to form cysteine-cysteamine disulfide and CYSTEINE has led to its use in CYSTINE DEPLETING AGENTS for the treatment of CYSTINOSIS.. cysteamine : An amine that consists of an ethane skeleton substituted with a thiol group at C-1 and an amino group at C-2.	1.96	1	amine; thiol	geroprotector; human metabolite; mouse metabolite; radiation protective agent
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	1.98	1	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
5-fluorotryptophan 5-fluorotryptophan: RN given refers to cpd with unspecified isomeric designation. 5-fluorotryptophan : A non-proteinogenic alpha-amino acid that is tryptophan in which the hydrogen at position 5 on the indole ring is replaced by a fluoro group.	1.98	1	non-proteinogenic alpha-amino acid; organofluorine compound; tryptophan derivative
diethyl acetamidomalonic acid diethyl acetamidomalonic acid: RN given refers to unlabeled parent cpd	1.96	1
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	1.96	1	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
mercury Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.	1.96	1	elemental mercury; zinc group element atom	neurotoxin
fluorides [no description available]	1.96	1	halide anion; monoatomic fluorine
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.	7.9	4	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
quisqualic acid Quisqualic Acid: An agonist at two subsets of excitatory amino acid receptors, ionotropic receptors that directly control membrane channels and metabotropic receptors that indirectly mediate calcium mobilization from intracellular stores. The compound is obtained from the seeds and fruit of Quisqualis chinensis.	2	1	non-proteinogenic alpha-amino acid
1-carboxyglutamic acid 1-Carboxyglutamic Acid: Found in various tissues, particularly in four blood-clotting proteins including prothrombin, in kidney protein, in bone protein, and in the protein present in various ectopic calcifications.	2.37	2
diethylmalonic acid diethylmalonic acid: isomer of diethyl malonate which is a di-ester	1.96	1
1-amino-1,3-dicarboxycyclopentane, (trans)-isomer [no description available]	2	1
2-methylglutamic acid 2-methylglutamic acid: RN given refers to parent cpd without isomeric designation	2	1
sym 2081 [no description available]	2	1
1-amino-1,3-dicarboxycyclopentane 1-amino-1,3-dicarboxycyclopentane: RN given refers to (cis)-isomer	2.39	2
s-sulphocysteine S-sulphocysteine: residues in physiologically significant proteins treated with sulfite; RN given refers to parent cpd; structure. S-sulfo-L-cysteine : An S-substituted L-cysteine where the S-substituent is specified as a sulfo group.	1.98	1	organic thiosulfate; S-substituted L-cysteine	human metabolite; plant metabolite
azetidine-2,4-dicarboxylic acid azetidine-2,4-dicarboxylic acid: activates neuronal metabotropic receptors; RN given refers to (trans-isomer); RN for cpd without isomeric designation not avail 10/93	2	1
beta-methyleneaspartate beta-methyleneaspartate: inhibits glutamate-aspartate transaminase; structure in first source	1.96	1
eglumetad eglumetad: LY-354740 is the active isomer, LY-366563 is the inactive isomer, and LY 314582 is the racemate; structure given in first source	2	1	L-alpha-amino acid
3,5-dihydroxyphenylglycine (S)-3,5-dihydroxyphenylglycine : A glycine derivative that is L-alpha-phenylglycine substituted at positions 3 and 5 on the phenyl ring by hydroxy groups.	2	1	amino acid zwitterion; non-proteinogenic L-alpha-amino acid; resorcinols
4-methylglutamic acid, threo-(l)-isomer [no description available]	2	1
l-2-(carboxypropyl)glycine [no description available]	2	1
2-(2,3-dicarboxycyclopropyl)glycine [no description available]	2	1
2r,4r-4-aminopyrrolidine-2,4-dicarboxylate [no description available]	2	1	pyrrolidinedicarboxylic acid
upf 596 UPF 596: structure in first source	2	1
4-carboxy-3-hydroxyphenylglycine [no description available]	2	1
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	2.37	2	cysteinium	fundamental metabolite
1-amino-1,3-dicarboxycyclopentane, cis-(1s,3s)-isomer [no description available]	2	1
1-aminocyclopentane-1,3,4-tricarboxylic acid 1-aminocyclopentane-1,3,4-tricarboxylic acid: metabolic glutamate receptor (mGluR) antagonist; structure in first source	2	1

Condition	Indicated	Relationship Strength	Studies	Trials
Deficiency, Vitamin K [description not available]	0	1.96	1	0
Vitamin K Deficiency A nutritional condition produced by a deficiency of VITAMIN K in the diet, characterized by an increased tendency to hemorrhage (HEMORRHAGIC DISORDERS). Such bleeding episodes may be particularly severe in newborn infants. (From Cecil Textbook of Medicine, 19th ed, p1182)	0	1.96	1	0

4-methyleneglutamic acid

Description

Cross-References

Synonyms (28)

Drug Classes (1)

Bioassays (2)

Research

Studies (19)

Market Indicators

Research Demand Index: 11.02

Study Types