Compounds > 1-amino-1,3-dicarboxycyclopentane, (trans)-isomer
Page last updated: 2024-12-06

1-amino-1,3-dicarboxycyclopentane, (trans)-isomer

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

1-amino-1,3-dicarboxycyclopentane, (trans)-isomer, also known as **trans-1-aminocyclopentane-1,3-dicarboxylic acid (trans-ACPD)**, is a non-proteinogenic amino acid with a cyclic structure.

Here's why it's important for research:

**1. Neurotransmitter Receptor Modulation:**

* **NMDA Receptor Antagonist:** Trans-ACPD acts as a selective antagonist of the NMDA receptor, a key type of glutamate receptor involved in learning, memory, and neuronal plasticity.
* **Potential for Neurological Disorders:** This antagonism has implications for studying and potentially treating neurological disorders like epilepsy, stroke, and Alzheimer's disease.

**2. Pharmacological Activity:**

* **Analgesic Effects:** Trans-ACPD exhibits analgesic effects in animal models, suggesting potential use in pain management.
* **Anti-Inflammatory Properties:** Studies have shown its ability to suppress inflammatory responses, making it a potential candidate for treating inflammatory conditions.

**3. Structural Properties:**

* **Cyclopentane Ring:** The cyclopentane ring provides rigidity and specific spatial arrangement of functional groups, allowing for interactions with receptor sites.
* **Trans Isomer:** The trans configuration refers to the specific arrangement of the amino and carboxyl groups on the cyclopentane ring, which influences its biological activity.

**4. Research Applications:**

* **Neurobiology:** Used to investigate the role of NMDA receptors in various neuronal functions.
* **Pharmacology:** Explored as a potential drug lead for the development of analgesics, anti-inflammatory drugs, and treatments for neurological disorders.
* **Chemistry:** Serves as a model compound for studying structure-activity relationships and the synthesis of novel cyclic amino acids.

**Overall, trans-ACPD is a fascinating molecule with significant potential for advancing research in various fields, particularly neurobiology, pharmacology, and drug development.**

**Note:** It's important to remember that research on trans-ACPD is ongoing, and its precise mechanisms of action and potential therapeutic applications are still under investigation.

Cross-References

ID SourceID
PubMed CID73537
CHEMBL ID36988
SCHEMBL ID4835874
MeSH IDM0320556

Synonyms (23)

Synonym
trans-(+/-)-acpd monohydrate
nsc 27386
1,3-cyclopentanedicarboxylic acid, 1-amino-, trans-
t-acpd
CHEMBL36988 ,
(1r,3s)-1-aminocyclopentane-1,3-dicarboxylic acid
(1r,3s)-1-amino-cyclopentane-1,3-dicarboxylic acid
bdbm50060136
1-amino-cyclopentane-1,3-dicarboxylic acid(trans-(1r,3r)-acpd)
1-amino-cyclopentane-1,3-dicarboxylic acid(trans-acpd)
AKOS006272258
89253-38-3
SCHEMBL4835874
HY-19434
CS-5853
AJ-190/40848563
( inverted exclamation marka)-trans-acpd
(1r,3s)-acpd
1,3-cyclopentanedicarboxylic acid, 1-amino-, (1r,3s)-rel-
BCP18261
trans-( inverted exclamation marka)-acp
DTXSID201017343
trans-1-aminocyclopentane-1,3-dicarboxylic acid
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Vesicular glutamate transporter 3Rattus norvegicus (Norway rat)Ki700.00000.04000.11500.1900AID216240
[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)
Metabotropic glutamate receptor 1Homo sapiens (human)EC50 (µMol)127.00000.20004.41009.3000AID108355
Metabotropic glutamate receptor 2Homo sapiens (human)EC50 (µMol)110.00000.00061.17848.5000AID108672
Metabotropic glutamate receptor 4Homo sapiens (human)EC50 (µMol)1,000.00000.00401.71939.8000AID109326
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (28)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayMetabotropic glutamate receptor 1Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 1Homo sapiens (human)
phospholipase C-activating G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 1Homo sapiens (human)
chemical synaptic transmissionMetabotropic glutamate receptor 1Homo sapiens (human)
locomotory behaviorMetabotropic glutamate receptor 1Homo sapiens (human)
sensory perception of painMetabotropic glutamate receptor 1Homo sapiens (human)
positive regulation of MAPK cascadeMetabotropic glutamate receptor 1Homo sapiens (human)
regulation of sensory perception of painMetabotropic glutamate receptor 1Homo sapiens (human)
regulation of postsynaptic membrane potentialMetabotropic glutamate receptor 1Homo sapiens (human)
cellular response to electrical stimulusMetabotropic glutamate receptor 1Homo sapiens (human)
L-glutamate import across plasma membraneMetabotropic glutamate receptor 1Homo sapiens (human)
regulation of postsynaptic cytosolic calcium ion concentrationMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 1Homo sapiens (human)
regulation of synaptic transmission, glutamatergicMetabotropic glutamate receptor 1Homo sapiens (human)
negative regulation of adenylate cyclase activityMetabotropic glutamate receptor 2Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 2Homo sapiens (human)
chemical synaptic transmissionMetabotropic glutamate receptor 2Homo sapiens (human)
gene expressionMetabotropic glutamate receptor 2Homo sapiens (human)
glutamate secretionMetabotropic glutamate receptor 2Homo sapiens (human)
regulation of glutamate secretionMetabotropic glutamate receptor 2Homo sapiens (human)
regulation of dopamine secretionMetabotropic glutamate receptor 2Homo sapiens (human)
behavioral response to nicotineMetabotropic glutamate receptor 2Homo sapiens (human)
response to cocaineMetabotropic glutamate receptor 2Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionMetabotropic glutamate receptor 2Homo sapiens (human)
long-term synaptic depressionMetabotropic glutamate receptor 2Homo sapiens (human)
intracellular glutamate homeostasisMetabotropic glutamate receptor 2Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionMetabotropic glutamate receptor 2Homo sapiens (human)
regulation of response to drugMetabotropic glutamate receptor 2Homo sapiens (human)
G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 2Homo sapiens (human)
regulation of synaptic transmission, glutamatergicMetabotropic glutamate receptor 2Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 4Homo sapiens (human)
chemical synaptic transmissionMetabotropic glutamate receptor 4Homo sapiens (human)
neurotransmitter secretionMetabotropic glutamate receptor 4Homo sapiens (human)
positive regulation of MAPK cascadeMetabotropic glutamate receptor 4Homo sapiens (human)
regulation of neuron apoptotic processMetabotropic glutamate receptor 4Homo sapiens (human)
regulation of synaptic transmission, glutamatergicMetabotropic glutamate receptor 4Homo sapiens (human)
G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
G protein-coupled receptor activityMetabotropic glutamate receptor 1Homo sapiens (human)
protein bindingMetabotropic glutamate receptor 1Homo sapiens (human)
glutamate receptor activityMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled neurotransmitter receptor activity involved in regulation of postsynaptic cytosolic calcium ion concentrationMetabotropic glutamate receptor 1Homo sapiens (human)
adenylate cyclase inhibiting G protein-coupled glutamate receptor activityMetabotropic glutamate receptor 1Homo sapiens (human)
neurotransmitter receptor activity involved in regulation of postsynaptic cytosolic calcium ion concentrationMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled receptor activity involved in regulation of postsynaptic membrane potentialMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled receptor activityMetabotropic glutamate receptor 2Homo sapiens (human)
calcium channel regulator activityMetabotropic glutamate receptor 2Homo sapiens (human)
protein bindingMetabotropic glutamate receptor 2Homo sapiens (human)
glutamate receptor activityMetabotropic glutamate receptor 2Homo sapiens (human)
scaffold protein bindingMetabotropic glutamate receptor 2Homo sapiens (human)
group II metabotropic glutamate receptor activityMetabotropic glutamate receptor 2Homo sapiens (human)
G protein-coupled receptor activityMetabotropic glutamate receptor 4Homo sapiens (human)
glutamate receptor activityMetabotropic glutamate receptor 4Homo sapiens (human)
adenylate cyclase inhibiting G protein-coupled glutamate receptor activityMetabotropic glutamate receptor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
nucleusMetabotropic glutamate receptor 1Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 1Homo sapiens (human)
dendriteMetabotropic glutamate receptor 1Homo sapiens (human)
Schaffer collateral - CA1 synapseMetabotropic glutamate receptor 1Homo sapiens (human)
glutamatergic synapseMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled receptor dimeric complexMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled receptor homodimeric complexMetabotropic glutamate receptor 1Homo sapiens (human)
postsynaptic density membraneMetabotropic glutamate receptor 1Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 1Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 2Homo sapiens (human)
axonMetabotropic glutamate receptor 2Homo sapiens (human)
dendriteMetabotropic glutamate receptor 2Homo sapiens (human)
presynaptic membraneMetabotropic glutamate receptor 2Homo sapiens (human)
astrocyte projectionMetabotropic glutamate receptor 2Homo sapiens (human)
glutamatergic synapseMetabotropic glutamate receptor 2Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 2Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 4Homo sapiens (human)
cytoplasmic vesicleMetabotropic glutamate receptor 4Homo sapiens (human)
presynapseMetabotropic glutamate receptor 4Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID205942Repolarization time for compound was measured by pattern firing by APN and KVN blockade1988Journal of medicinal chemistry, Apr, Volume: 31, Issue:4
Synthesis, resolution, and absolute configuration of the isomers of the neuronal excitant 1-amino-1,3-cyclopentanedicarboxylic acid.
AID108506Ratio between EC50 of compound and glutamate measured against metabotropic glutamate receptor 11999Journal 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.
AID216240Evaluated for competitive inhibition against Vesicular glutamate transporter (VGLUT), and Ki value was reported.2002Journal of medicinal chemistry, May-23, Volume: 45, Issue:11
Synthesis and in vitro pharmacology of substituted quinoline-2,4-dicarboxylic acids as inhibitors of vesicular glutamate transport.
AID75015The effective concentration for 50% glutamate response was measured on Group I Metabotropic glutamate receptor1999Journal of medicinal chemistry, Jul-29, Volume: 42, Issue:15
Pharmacophore models of group I and group II metabotropic glutamate receptor agonists. Analysis of conformational, steric, and topological parameters affecting potency and selectivity.
AID108672Agonist activity against Metabotropic glutamate receptor 2 expressed in HEK 293 cells was evaluated by measuring total inositol phosphate accumulation1997Journal of medicinal chemistry, Sep-12, Volume: 40, Issue:19
Synthesis and pharmacological characterization of aminocyclopentanetricarboxylic acids: new tools to discriminate between metabotropic glutamate receptor subtypes.
AID108355Agonist activity against Metabotropic glutamate receptor 1 expressed in HEK 293 cells was evaluated by measuring total inositol phosphate accumulation1997Journal of medicinal chemistry, Sep-12, Volume: 40, Issue:19
Synthesis and pharmacological characterization of aminocyclopentanetricarboxylic acids: new tools to discriminate between metabotropic glutamate receptor subtypes.
AID108985Ratio between EC50 of compound and glutamate measured against Metabotropic glutamate receptor 21999Journal 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.
AID109326Agonist activity against Metabotropic glutamate receptor 4 expressed in HEK 293 cells was evaluated by measuring total inositol phosphate accumulation1997Journal of medicinal chemistry, Sep-12, Volume: 40, Issue:19
Synthesis and pharmacological characterization of aminocyclopentanetricarboxylic acids: new tools to discriminate between metabotropic glutamate receptor subtypes.
AID75021The effective concentration for 50% glutamate response was measured on Group II Metabotropic glutamate receptor1999Journal of medicinal chemistry, Jul-29, Volume: 42, Issue:15
Pharmacophore models of group I and group II metabotropic glutamate receptor agonists. Analysis of conformational, steric, and topological parameters affecting potency and selectivity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (20.00)18.7374
1990's3 (60.00)18.2507
2000's1 (20.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
7-chlorokynurenic acid
7-chlorokynurenic acid: selective antagonist at the glycine modulatory site of the N-methyl-D-aspartate receptor complex; structure given in first source. 7-chlorokynurenic acid : A quinolinemonocarboxylic acid that is quinaldic acid which is substituted by a hydroxy group at position 4 and by a chlorine at position 7. It is a potent NMDA glutamate receptor antagonist which antagonizes the strychnine-insensitive glycine site of the NMDA receptor. It also prevents neurodegeneration produced by quinolinic acid.		2.0110organochlorine compound;
quinolinemonocarboxylic acid		neuroprotective agent;
NMDA receptor antagonist
kynurenic acid
Kynurenic Acid: A broad-spectrum excitatory amino acid antagonist used as a research tool.. kynurenic acid : A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by a hydroxy group at C-4.		2.0110monohydroxyquinoline;
quinolinemonocarboxylic acid		G-protein-coupled receptor agonist;
human metabolite;
neuroprotective agent;
nicotinic antagonist;
NMDA receptor antagonist;
Saccharomyces cerevisiae metabolite
4-methylglutamic acid
4-methylglutamic acid : A glutamic acid derivative that is glutamic acid substituted by a methyl group at position 4.		210amino dicarboxylic acid;
glutamic acid derivative
xanthurenic acid
xanthurenic acid : A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by hydroxy groups at C-4 and C-8.		2.0110dihydroxyquinoline;
quinolinemonocarboxylic acid		animal metabolite;
iron chelator;
metabotropic glutamate receptor agonist;
vesicular glutamate transport inhibitor
evans blue
Evans Blue: An azo dye used in blood volume and cardiac output measurement by the dye dilution method. It is very soluble, strongly bound to plasma albumin, and disappears very slowly.. Evans blue : An organic sodium salt that is the tetrasodium salt of 6,6'-{(3,3'-dimethyl[1,1'-biphenyl]-4,4'-diyl)bis[diazene-2,1-diyl]}bis(4-amino-5-hydroxynaphthalene-1,3-disulfonate). It is sometimes used as a counterstain, especially in fluorescent methods to suppress background autofluorescence.		2.0110organic sodium saltfluorochrome;
histological dye;
sodium channel blocker;
teratogenic agent
kainic acid
Kainic Acid: (2S-(2 alpha,3 beta,4 beta))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid. Ascaricide obtained from the red alga Digenea simplex. It is a potent excitatory amino acid agonist at some types of excitatory amino acid receptors and has been used to discriminate among receptor types. Like many excitatory amino acid agonists it can cause neurotoxicity and has been used experimentally for that purpose.		1.9710dicarboxylic acid;
L-proline derivative;
non-proteinogenic L-alpha-amino acid;
pyrrolidinecarboxylic acid		antinematodal drug;
excitatory amino acid agonist
c.i. direct blue 1
[no description available]		2.0110
n-methylaspartate
N-Methylaspartate: An amino acid that, as the D-isomer, is the defining agonist for the NMDA receptor subtype of glutamate receptors (RECEPTORS, NMDA).. N-methyl-D-aspartic acid : An aspartic acid derivative having an N-methyl substituent and D-configuration.		1.9710amino dicarboxylic acid;
D-alpha-amino acid;
D-aspartic acid derivative;
secondary amino compound		neurotransmitter agent
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.		2.420glutamic 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.		2.6830non-proteinogenic alpha-amino acid
2-methylglutamic acid
2-methylglutamic acid: RN given refers to parent cpd without isomeric designation		210
sym 2081
[no description available]		210
4-methyleneglutamic acid
4-methyleneglutamic acid: RN given refers to (DL-Glu)-isomer		210non-proteinogenic alpha-amino acid
1-amino-1,3-dicarboxycyclopentane
1-amino-1,3-dicarboxycyclopentane: RN given refers to (cis)-isomer		2.6930
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		2.420
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		2.420L-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.		2.420amino acid zwitterion;
non-proteinogenic L-alpha-amino acid;
resorcinols
4-methylglutamic acid, threo-(l)-isomer
[no description available]		210
l-2-(carboxypropyl)glycine
[no description available]		210
2-(2,3-dicarboxycyclopropyl)glycine
[no description available]		210
2r,4r-4-aminopyrrolidine-2,4-dicarboxylate
[no description available]		2.420pyrrolidinedicarboxylic acid
upf 596
UPF 596: structure in first source		210
4-carboxy-3-hydroxyphenylglycine
[no description available]		210
1-amino-1,3-dicarboxycyclopentane, cis-(1s,3s)-isomer
[no description available]		2.940
1-aminocyclopentane-1,3,4-tricarboxylic acid
1-aminocyclopentane-1,3,4-tricarboxylic acid: metabolic glutamate receptor (mGluR) antagonist; structure in first source		2.420
ConditionIndicatedRelationship StrengthStudiesTrials