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Compound Detail

CHEMBL298826

(-)-EPIBATIDINE
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Clc1ccc([C@H]2C[C@@H]3CC[C@H]2N3)cn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL298826
Name (-)-EPIBATIDINE
Phase Preclinical
Structure Type MOL
InChI Key NLPRAJRHRHZCQQ-IVZWLZJFSA-N
7
Targets
21
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

208.7
MW (Da)
2.34
ALogP
2
HBA
1
HBD
24.9
PSA (Ų)
0.72
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C11H13ClN2
MW 208.69
Aromatic Rings 1
Heavy Atoms 14
NP-Likeness 0.83

Activity Summary

Ki 18 meas. best 11.0
Kd 2 meas. best 10.52
IC50 1 meas. best 5.87

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
 Ki 11.0 10.4556 0.0 9
Unchecked
CHEMBL612545
 Ki 10.74 10.74 0.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
 Kd 10.52 10.52 0.0 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
 Ki 9.82 9.82 0.1 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
 Kd 9.52 9.52 0.3 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL4980
 Ki 8.15 7.55 7.0 3
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 Ki 7.66 7.29 22.0 2
Nicotinic acetylcholine receptor alpha 5 subunit
CHEMBL2366408
 IC50 5.87 5.87 1340.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.01 nM 11.0 Inhibition of alpha beta[3H]epibatidine binding to Nicotinic acetylcholine recep... 15317468
Unchecked Ki = 0.018 nM 10.74 Inhibition of [3H]epibatidine binding at the alpha beta nicotinic AChR in male r... 11708907
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.018 nM 10.74 Inhibition of [3H]epibatidine binding at the nicotinic acetylcholine receptor al... 11405659
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.018 nM 10.74 Displacement of [3H]epibatidine from alpha-4-beta-2 nACHR in rat cerebral cortex 16722642
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.02 nM 10.7 Displacement of [3H]Nicotine from alpha4beta2 nAChR in rat cortical membranes 16934977
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.026 nM 10.59 Inhibition of [3H]epibatidine binding to Nicotinic acetylcholine receptor alpha4... 15050621
Neuronal acetylcholine receptor; alpha4/beta2 Kd = 0.03 nM 10.52 Binding affinity to alpha4beta2 nACh receptor (unknown origin) expressed in Xeno... 26706350
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.055 nM 10.26 Inhibition of [3H]nicotine binding to Nicotinic acetylcholine receptor alpha4-be... 15050621
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.058 nM 10.24 Non-specific binding in presence of 300 uM nicotine at nicotinic acetylcholine r... 11405659
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.058 nM 10.24 Inhibition of [3H]nicotine binding to Nicotinic acetylcholine receptor alpha4-be... 15050621
Neuronal acetylcholine receptor; alpha3/beta4 Ki = 0.15 nM 9.82 Displacement of [3H]epibatidine from human alpha3beta4 nAChR transfected in HEK2... 31299587
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.26 nM 9.59 Inhibition of [3H]nicotine binding to Nicotinic acetylcholine receptor alpha4-be... 15050621
Neuronal acetylcholine receptor; alpha3/beta4 Kd = 0.3 nM 9.52 Binding affinity to alpha3beta4 nACh receptor (unknown origin) expressed in Xeno... 26706350
Neuronal acetylcholine receptor subunit alpha-7 Ki = 7.0 nM 8.15 Displacement of [125I-alpha]-Bungarotoxin from alpha-7 nAChR in rat hippocampal ... 16934977
Neuronal acetylcholine receptor subunit alpha-7 Ki = 16.0 nM 7.8 Displacement of [125I] alpha bungarotoxin from rat alpha7 nACh receptor expresse... 26706350
Neuronal acetylcholine receptor subunit alpha-7 Ki = 22.0 nM 7.66 Displacement of [125I] alpha bungarotoxin from human alpha7 nACh receptor incuba... 26706350
Neuronal acetylcholine receptor subunit alpha-7 Ki = 120.0 nM 6.92 Displacement of [125I] alpha bungarotoxin from human neuronal alpha7 nAChR expre... 32447198
Neuronal acetylcholine receptor subunit alpha-7 Ki = 198.0 nM 6.7 Inhibition of [125I]MLA binding to Nicotinic acetylcholine receptor alpha7 from ... 15050621
Nicotinic acetylcholine receptor alpha 5 subunit IC50 = 1340.0 nM 5.87 Displacement of [3HIMI from nicotinic acetylcholine receptor in Musca domestica ... 12834274

Literature References

PubMed DOI Target Context # Activities
15050621 10.1016/j.bmcl.2004.02.007 Mus musculus 6
15050621 10.1016/j.bmcl.2004.02.007 Neuronal acetylcholine receptor; alpha4/beta2 4
16722642 10.1021/jm060122n Mus musculus 4
15317468 10.1021/jm040078g Mus musculus 3
11405659 10.1021/jm0100178 Neuronal acetylcholine receptor; alpha4/beta2 2
26706350 10.1016/j.ejmech.2015.11.045 Neuronal acetylcholine receptor subunit alpha-7 2
26706350 10.1016/j.ejmech.2015.11.045 Unchecked 2
32447198 10.1016/j.ejmech.2020.112403 Neuronal acetylcholine receptor; alpha4/beta2 1
11708907 10.1021/jm015561v Unchecked 1
26706350 10.1016/j.ejmech.2015.11.045 Neuronal acetylcholine receptor; alpha4/beta2 1
26706350 10.1016/j.ejmech.2015.11.045 Neuronal acetylcholine receptor; alpha3/beta4 1
12834274 10.1271/bbb.67.980 Nicotinic acetylcholine receptor alpha 5 subunit 1
16934977 10.1016/j.bmcl.2006.08.049 Unchecked 1
16934977 10.1016/j.bmcl.2006.08.049 Neuronal acetylcholine receptor; alpha4/beta2 1
16934977 10.1016/j.bmcl.2006.08.049 Neuronal acetylcholine receptor subunit alpha-7 1
16722642 10.1021/jm060122n Neuronal acetylcholine receptor; alpha4/beta2 1
15317468 10.1021/jm040078g Neuronal acetylcholine receptor subunit alpha-7 1
15317468 10.1021/jm040078g Neuronal acetylcholine receptor; alpha4/beta2 1
15050621 10.1016/j.bmcl.2004.02.007 Neuronal acetylcholine receptor subunit alpha-7 1
11405659 10.1021/jm0100178 Mus musculus 1

Data from ChEMBL 36 via Core Engine