Compounds > 1-amino-1,3-dicarboxycyclopentane, cis-(1s,3s)-isomer
Page last updated: 2024-08-02 04:21:35

1-amino-1,3-dicarboxycyclopentane, cis-(1s,3s)-isomer

Description

Cross-References

ID SourceID
PubMed CID6604704
CHEMBL ID29726
SCHEMBL ID481144
MeSH IDM0320552

Synonyms (30)

Synonym
NCGC00024488-02
tocris-0284
NCGC00024487-01
NCGC00024488-01
tocris-0187
tocris-0186
1r,3s-acpd
inchi=1/c7h11no4/c8-7(6(11)12)2-1-4(3-7)5(9)10/h4h,1-3,8h2,(h,9,10)(h,11,12)/t4-,7-/m0/s1
yfynowxbibkghb-ffwsuholsa-
CHEMBL29726 ,
(1s,3s)-1-amino-cyclopentane-1,3-dicarboxylic acid
1r,3r-acpd
bdbm50004863
(1s,3s)-1-aminocyclopentane-1,3-dicarboxylic acid
1-amino-cyclopentane-1,3-dicarboxylic acid(cis-(1s,3s)-acpd)
1-amino-cyclopentane-1,3-dicarboxylic acid (apcd)
AKOS006273106
M01251
A824378
477331-06-9
1,3-cyclopentanedicarboxylicacid, 1-amino-, (1s,3s)-
111900-31-3
SCHEMBL481144
SR-01000597676-1
sr-01000597676
1-aminocyclopentane-cis-1,3-dicarboxylic acid
1s,3s-acpd
Q27458657
cis-1-aminocyclopentane-1,3-dicarboxylic acid
mfcd00153759

Protein Targets (13)

Potency Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency0.6310AID485290
15-lipoxygenase, partialHomo sapiens (human)Potency12.5893AID887
phosphopantetheinyl transferaseBacillus subtilisPotency94.5626AID1490
USP1 protein, partialHomo sapiens (human)Potency34.8936AID504865
regulator of G-protein signaling 4Homo sapiens (human)Potency5.3233AID504845
cytochrome P450 2C19 precursorHomo sapiens (human)Potency19.9526AID899
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency31.6228AID2551

Activation Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Metabotropic glutamate receptor 4Rattus norvegicus (Norway rat)EC50100.0000AID246705
Metabotropic glutamate receptor 5Homo sapiens (human)EC50300.0000AID107083
Metabotropic glutamate receptor 1Homo sapiens (human)EC50300.0000AID108355; AID108647
Metabotropic glutamate receptor 2Homo sapiens (human)EC5013.0000AID108672; AID109004
Metabotropic glutamate receptor 3Homo sapiens (human)EC5030.0000AID109318
Metabotropic glutamate receptor 4Homo sapiens (human)EC5049.0000AID109326; AID109477

Bioassays (17)

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
ISSN: 1091-6490		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
ISSN: 2211-1247		A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID107083Compound was tested for the inhibition of Metabotropic glutamate receptor 51998Journal of medicinal chemistry, May-07, Volume: 41, Issue:10
ISSN: 0022-2623		Synthesis and biology of the conformationally restricted ACPD analogue, 2-aminobicyclo[2.1.1]hexane-2,5-dicarboxylic acid-I, a potent mGluR agonist.
AID246705Stimulation of [3H]phosphatidylinositol accumulation by rat Metabotropic glutamate receptor 4 co-expressed with Gqi9 protein in HEK 293 cells; Inactive2005Journal of medicinal chemistry, Apr-07, Volume: 48, Issue:7
ISSN: 0022-2623		Virtual screening workflow development guided by the "receiver operating characteristic" curve approach. Application to high-throughput docking on metabotropic glutamate receptor subtype 4.
AID205942Repolarization time for compound was measured by pattern firing by APN and KVN blockade1988Journal of medicinal chemistry, Apr, Volume: 31, Issue:4
ISSN: 0022-2623		Synthesis, resolution, and absolute configuration of the isomers of the neuronal excitant 1-amino-1,3-cyclopentanedicarboxylic acid.
AID108985Ratio between EC50 of compound and glutamate measured against Metabotropic glutamate receptor 21999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
ISSN: 0022-2623		Agonist selectivity of mGluR1 and mGluR2 metabotropic receptors: a different environment but similar recognition of an extended glutamate conformation.
AID108647Compound was tested for the inhibition of Metabotropic glutamate receptor 11998Journal of medicinal chemistry, May-07, Volume: 41, Issue:10
ISSN: 0022-2623		Synthesis and biology of the conformationally restricted ACPD analogue, 2-aminobicyclo[2.1.1]hexane-2,5-dicarboxylic acid-I, a potent mGluR agonist.
AID109318Compound was tested for the inhibition of Metabotropic glutamate receptor 3 (mGluR3)1998Journal of medicinal chemistry, May-07, Volume: 41, Issue:10
ISSN: 0022-2623		Synthesis and biology of the conformationally restricted ACPD analogue, 2-aminobicyclo[2.1.1]hexane-2,5-dicarboxylic acid-I, a potent mGluR agonist.
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
ISSN: 0022-2623		Synthesis and pharmacological characterization of aminocyclopentanetricarboxylic acids: new tools to discriminate between metabotropic glutamate receptor subtypes.
AID75015The effective concentration for 50% glutamate response was measured on Group I Metabotropic glutamate receptor1999Journal of medicinal chemistry, Jul-29, Volume: 42, Issue:15
ISSN: 0022-2623		Pharmacophore models of group I and group II metabotropic glutamate receptor agonists. Analysis of conformational, steric, and topological parameters affecting potency and selectivity.
AID75021The effective concentration for 50% glutamate response was measured on Group II Metabotropic glutamate receptor1999Journal of medicinal chemistry, Jul-29, Volume: 42, Issue:15
ISSN: 0022-2623		Pharmacophore models of group I and group II metabotropic glutamate receptor agonists. Analysis of conformational, steric, and topological parameters affecting potency and selectivity.
AID108506Ratio between EC50 of compound and glutamate measured against metabotropic glutamate receptor 11999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
ISSN: 0022-2623		Agonist selectivity of mGluR1 and mGluR2 metabotropic receptors: a different environment but similar recognition of an extended glutamate conformation.
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
ISSN: 0022-2623		Synthesis and pharmacological characterization of aminocyclopentanetricarboxylic acids: new tools to discriminate between metabotropic glutamate receptor subtypes.
AID109477Compound was tested for the inhibition of Metabotropic glutamate receptor 41998Journal of medicinal chemistry, May-07, Volume: 41, Issue:10
ISSN: 0022-2623		Synthesis and biology of the conformationally restricted ACPD analogue, 2-aminobicyclo[2.1.1]hexane-2,5-dicarboxylic acid-I, a potent mGluR agonist.
AID109004Compound was tested for the inhibition of metabotropic glutamate receptor 2 (mGluR2).1998Journal of medicinal chemistry, May-07, Volume: 41, Issue:10
ISSN: 0022-2623		Synthesis and biology of the conformationally restricted ACPD analogue, 2-aminobicyclo[2.1.1]hexane-2,5-dicarboxylic acid-I, a potent mGluR agonist.
AID144456Displacement of [3H]CPP from N-methyl-D-aspartate glutamate receptor in rat brain membrane1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
ISSN: 0022-2623		Generation of N-methyl-D-aspartate agonist and competitive antagonist pharmacophore models. Design and synthesis of phosphonoalkyl-substituted tetrahydroisoquinolines as novel antagonists.
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
ISSN: 0022-2623		Synthesis and pharmacological characterization of aminocyclopentanetricarboxylic acids: new tools to discriminate between metabotropic glutamate receptor subtypes.

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (11.11)18.7374
1990's5 (55.56)18.2507
2000's1 (11.11)29.6817
2010's0 (0.00)24.3611
2020's2 (22.22)2.80

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%
Other9 (100.00%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
2-aminoadipic acid
1
amino dicarboxylic acid;
dicarboxylic fatty acid;
non-proteinogenic alpha-amino acid		Caenorhabditis elegans metabolite;
mammalian metabolite		1992199232.0low001000
quinolinic acid
1
pyridinedicarboxylic acidEscherichia coli metabolite;
human metabolite;
mouse metabolite;
NMDA receptor agonist		1992199232.0low001000
2-amino-5-phosphonovalerate
1
non-proteinogenic alpha-amino acidNMDA receptor antagonist1992199232.0low001000
alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
1
non-proteinogenic alpha-amino acid1998199826.0low001000
3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid
1
1992199232.0low001000
ibotenic acid
1
non-proteinogenic alpha-amino acidneurotoxin1992199232.0low001000
2-amino-4-phosphonobutyric acid
2
1992199829.0low002000
2-amino-6-phosphonohexanoic acid
1
1992199232.0medium001000
2-amino-7-phosphonoheptanoic acid
1
1992199232.0low001000
4-methylglutamic acid
1
amino dicarboxylic acid;
glutamic acid derivative		1999199925.0low001000
aspartic acid
1
aspartate family amino acid;
aspartic acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
mouse metabolite;
neurotransmitter		1992199232.0low001000
kainic acid
2
dicarboxylic acid;
L-proline derivative;
non-proteinogenic L-alpha-amino acid;
pyrrolidinecarboxylic acid		antinematodal drug;
excitatory amino acid agonist		1988199831.0low011000
n-methylaspartate
2
amino dicarboxylic acid;
D-alpha-amino acid;
D-aspartic acid derivative;
secondary amino compound		neurotransmitter agent1988199831.0low011000
d-glutamate
1
D-alpha-amino acid;
glutamic acid		Escherichia coli metabolite;
mouse metabolite		2005200519.0low000100
glutamic acid
4
glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical		1992199927.0low004000
quisqualic acid
4
non-proteinogenic alpha-amino acid1988200526.2low012100
selfotel
1
non-proteinogenic alpha-amino acid1992199232.0low001000
plasmenylserine
1
O-phosphoserineEC 1.4.7.1 [glutamate synthase (ferredoxin)] inhibitor;
EC 2.5.1.49 (O-acetylhomoserine aminocarboxypropyltransferase) inhibitor;
EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite		2005200519.0low000100
1-amino-1,3-dicarboxycyclopentane, (trans)-isomer
4
1988199928.2high013000
d-aspartic acid
1
aspartic acid;
D-alpha-amino acid		mouse metabolite1992199232.0low001000
2-methylglutamic acid
1
1999199925.0low001000
sym 2081
1
1999199925.0medium001000
4-methyleneglutamic acid
1
non-proteinogenic alpha-amino acid1999199925.0low001000
1-amino-1,3-dicarboxycyclopentane
5
1997200524.4low004100
azetidine-2,4-dicarboxylic acid
2
1999199925.0medium002000
alpha-amino-3-(hydroxy)-5-methyl-4-isoxazoleacetic acid
1
1992199232.0medium001000
homocysteic acid
1
homocysteic acidNMDA receptor agonist2005200519.0low000100
2-amino-4-phosphonobutyric acid
1
non-proteinogenic L-alpha-amino acid;
phosphonic acids		metabotropic glutamate receptor agonist2005200519.0low000100
dizocilpine
1
secondary amino compound;
tetracyclic antidepressant		anaesthetic;
anticonvulsant;
neuroprotective agent;
nicotinic antagonist;
NMDA receptor antagonist		1998199826.0low001000
alpha,alpha'-diaminosuberic acid
1
1992199232.0high001000
eglumetad
4
L-alpha-amino acid1998200523.8low003100
3,5-dihydroxyphenylglycine
3
amino acid zwitterion;
non-proteinogenic L-alpha-amino acid;
resorcinols		1999200523.0medium002100
homoquinolinic acid
1
1992199232.0low001000
4-methylglutamic acid, threo-(l)-isomer
1
1999199925.0high001000
2,3-dioxo-6-nitro-7-sulfamoylbenzo(f)quinoxaline
1
naphthalenes;
sulfonic acid derivative		1998199826.0low001000
l-2-(carboxypropyl)glycine
1
1999199925.0low001000
l-ccg iii
1
1992199232.0high001000
(alpha-carboxycyclopropyl)glycine, (1r-(1alpha(s*),2alpha))-isomer
1
1992199232.0medium001000
2-(2,3-dicarboxycyclopropyl)glycine
1
1999199925.0low001000
2r,4r-4-aminopyrrolidine-2,4-dicarboxylate
3
pyrrolidinedicarboxylic acid1999200523.0high002100
upf 596
2
1999200522.0medium001100
4-carboxy-3-hydroxyphenylglycine
2
1999200522.0high001100
cgp 37849
1
1992199232.0low001000
1-aminocyclopentane-1,3,4-tricarboxylic acid
3
1997200523.7high002100
3,4-dicarboxyphenylglycine
1
2005200519.0high000100
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Congenital Zika Syndrome0
1
202020204.0high000010
Disease Models, Animal0
1
202020204.0high000010
Zika Virus Infection0
1
202020204.0high000010