Page last updated: 2024-12-04

2,4-methanoglutamate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2,4-methanoglutamate: structure given in first source; selective N-methyl-D-aspartate receptor agonist; inhibits high affinity L-glutamic acid uptake into rat cortical synaptosomes; RN given for (trans)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1214
CHEMBL ID1437288
CHEMBL ID1555263
CHEMBL ID1316912
SCHEMBL ID7530916
SCHEMBL ID1064244
SCHEMBL ID1063416
SCHEMBL ID1263461
MeSH IDM0181998

Synonyms (70)

Synonym
HMS3266E13
JEG ,
nsc621814
cis-1-amino-cyclobutane-1,4-methanoglutamic acid)
nsc-621814
1,3-cyclobutanedicarboxylic acid, 1-amino-, trans-, hydrate
2,4-methanoglutamate
cis-1-amino-1,3-cyclobutanedicarboxylic acid
1,3-cyclobutanedicarboxylic acid, 1-amino-, cis-, hydrate
trans-1-aminocyclobutane-1,3-dicarboxylic acid hydrate
cis-1-aminocyclobutane-1,3-dicarboxylic acid hydrate
BIOMOL-NT_000172
tocris-0271
NCGC00024521-01
BPBIO1_001136
NCGC00024521-02
NCGC00163685-01
NCGC00092272-01
1-aminocyclobutane-1,3-dicarboxylic acid
73550-55-7
FT-0694339
117488-23-0
A803777
(1s,3s)-1-aminocyclobutane-1,3-dicarboxylic acid
NCGC00024521-04
NCGC00024521-03
SCHEMBL7530916
AKOS006239813
AKOS006230090
AKOS006239508
CHEMBL1437288
FT-0642876
164225-42-7
1-aminocyclobutane-cis-1,3-dicarboxylic acid
SCHEMBL1064244
SCHEMBL1063416
SCHEMBL1263461
trans-1-aminocyclobutane-1,3-dicarboxylic acid
Z1270392248
1-aminocyclobutane-cis -1,3-dicarboxylic acid
cis-1-aminocyclobutane-1,3-dicarboxylic acid
cis-acbd
CHEMBL1555263
CHEMBL1316912
2,4-methanoglutamic acid
trans-abcd
cis-abcd
sr-01000597724
SR-01000597724-1
1-aminocyclobutane-trans-1,3-dicarboxylic acid
DTXSID60922431
BCP18258
trans-1-aminocyclobutane-1,3-dicarboxylic acid; trans acbd; transacbd
BCP18259
Q27461686
ethyl(r)-(-)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-trans-2-propenoate
trans-acbd
cis-2,4-methanoglutamate
1,3-cyclobutanedicarboxylicacid,1-amino-(9ci)
EN300-63952
(1r,3r)-1-aminocyclobutane-1,3-dicarboxylic acid
1,3-cyclobutanedicarboxylic acid, 1-amino-, cis-
HY-100616
AB86519
AB86481
DTXSID601312880
EN300-144924
EN300-296162
cis-1-aminocyclobutane-1,3-dicarboxylicacid
PD065319

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Dose-response showed that DL-(tetrazol-5-yl)glycine was about 100 and 500 times more potent than cis-methanoglutamate and NMDA, respectively."( The NMDA receptor agonist DL-(tetrazol-5-yl)glycine is a highly potent excitotoxin.
Lunn, WH; McDonald, JW; Salhoff, CR; Schoepp, DD, 1994
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (15)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency100.00000.003245.467312,589.2998AID2517
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency5.61010.140911.194039.8107AID2451
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency33.99720.177814.390939.8107AID2147
15-lipoxygenase, partialHomo sapiens (human)Potency19.95260.012610.691788.5700AID887
phosphopantetheinyl transferaseBacillus subtilisPotency42.08620.141337.9142100.0000AID1490
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency28.18380.011212.4002100.0000AID1030
Polyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)Potency39.81070.316212.765731.6228AID881
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency39.81070.00638.235039.8107AID881
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)IC50 (µMol)0.16300.00071.600310.0000AID144612
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)IC50 (µMol)0.16300.00071.630610.0000AID144612
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)IC50 (µMol)0.16300.00061.525710.0000AID144612
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)IC50 (µMol)0.16300.00071.747210.0000AID144612
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)IC50 (µMol)0.16300.00071.741110.0000AID144612
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)IC50 (µMol)0.16300.00071.741110.0000AID144612
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)IC50 (µMol)0.16300.00071.741110.0000AID144612
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)EC50 (µMol)8.34000.00301.29038.3000AID144321; AID144322
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)EC50 (µMol)8.34000.00301.02226.8600AID144321; AID144322
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)EC50 (µMol)8.34000.00300.86696.8600AID144321; AID144322
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)EC50 (µMol)8.34000.00301.11276.8600AID144321; AID144322
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)EC50 (µMol)8.34000.00301.39378.3000AID144321; AID144322
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)EC50 (µMol)8.34000.00300.90516.8600AID144321; AID144322
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)EC50 (µMol)8.34000.00300.90516.8600AID144321; AID144322
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (21)

Processvia Protein(s)Taxonomy
lipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
phospholipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
apoptotic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell population proliferationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of macrophage derived foam cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell migrationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
prostate gland developmentPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
regulation of epithelial cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of chemokine productionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of peroxisome proliferator activated receptor signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of keratinocyte differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell cyclePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of growthPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
hepoxilin biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
endocannabinoid signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cannabinoid biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxin A4 biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid oxidationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxygenase pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
iron ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
calcium ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
protein bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 13S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 8(S)-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 15-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 9S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
nucleusPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytosolPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytoskeletonPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
plasma membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
adherens junctionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
focal adhesionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
extracellular exosomePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID144321Compound was evaluated for the inhibition of [3H]MK-801 binding at N-methyl-D-aspartate glutamate receptor1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
DL-tetrazol-5-ylglycine, a highly potent NMDA agonist: its synthesis and NMDA receptor efficacy.
AID144322Compound was evaluated for the inhibition of [3H]norepinephrine binding at N-methyl-D-aspartate glutamate receptor1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
DL-tetrazol-5-ylglycine, a highly potent NMDA agonist: its synthesis and NMDA receptor efficacy.
AID144612Compound was evaluated for the inhibition of [3H]-CGS-19,755 binding at N-methyl-D-aspartate glutamate receptor1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
DL-tetrazol-5-ylglycine, a highly potent NMDA agonist: its synthesis and NMDA receptor efficacy.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (24)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's16 (66.67)18.2507
2000's5 (20.83)29.6817
2010's1 (4.17)24.3611
2020's2 (8.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.15

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.15 (24.57)
Research Supply Index3.26 (2.92)
Research Growth Index4.40 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.15)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (4.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (96.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]