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Compound Detail

CHEMBL298517

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

Basic Information

ChEMBL ID CHEMBL298517
Name (+)-EPIBATIDINE
Phase Preclinical
Structure Type MOL
InChI Key NLPRAJRHRHZCQQ-UTLUCORTSA-N
7
Targets
23
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 19 meas. best 10.74
EC50 3 meas. best 8.89
IC50 1 meas. best 5.55

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
 Ki 10.74 10.4775 0.0 12
Unchecked
CHEMBL612545
 Ki 10.74 10.555 0.0 2
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
 Ki 10.59 10.47 0.0 2
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907593
 Ki 9.42 9.42 0.4 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
 EC50 8.89 8.89 1.3 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL4980
 Ki 8.31 8.31 4.9 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 EC50 7.4 7.4 39.8 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907593
 EC50 6.16 6.16 700.0 1
Nicotinic acetylcholine receptor alpha 5 subunit
CHEMBL2366408
 IC50 5.55 5.55 2790.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.018 nM 10.74 Inhibition of [3H]nicotine binding to alpha4-beta2 nACh receptor from rat membra... 15050621
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.018 nM 10.74 Displacement of [3H]epibatidine from alpha4beta2 nAChR in rat cerebral cortex af... 20038125
Unchecked Ki = 0.018 nM 10.74 [3H]Epibatidine Binding Assay: Adult male rat cerebral cortices (Pelfreeze Biolo... -
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.019 nM 10.72 Displacement of [3H]Nicotine from alpha4beta2 nAChR in rat cortical membranes 16934977
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.02 nM 10.7 Inhibition of alpha beta[3H]epibatidine binding to Nicotinic acetylcholine recep... 15317468
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.026 nM 10.59 Inhibition of [3H]epibatidine binding at the nicotinic acetylcholine receptor al... 11405659
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.026 nM 10.59 Displacement of [3H]epibatidine from alpha-4-beta-2 nACHR in rat cerebral cortex 16722642
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.026 nM 10.59 Displacement of [3H]epibatidine from alpha-4-beta-2 nAChR 17994682
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.026 nM 10.59 Displacement of [3H]epibatidine from alpha4beta2 nAChR in rat cerebral cortex af... 20038125
Unchecked Ki = 0.043 nM 10.37 Binding affinity to alpha4beta2* nAChR in Sprague-Dawley rat cortical membranes ... 26383127
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.045 nM 10.35 Binding affinity to alpha4beta2 nAChR (unknown origin) 26383127
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.045 nM 10.35 Inhibition of [3H]nicotine binding to alpha4-beta2 nACh receptor from rat membra... 15050621
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.045 nM 10.35 Non-specific binding in presence of 300 uM nicotine at nicotinic acetylcholine r... 11405659
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.05 nM 10.3 Displacement of [3H]-cytisine from Alpha4-beta2 Nicotinic acetylcholine receptor... 16078832
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.055 nM 10.26 Inhibition of [3H]nicotine binding to alpha4-beta2 nACh receptor from rat membra... 15050621
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.16 nM 9.8 in vitro binding affinity by inhibiting [3H]cytisine binding in rat brain tissue... 12086489
Neuronal acetylcholine receptor; alpha3/beta4 Ki = 0.38 nM 9.42 Displacement of [3H]epibatidine from Alpha3 Beta4 Nicotinic acetylcholine recept... 16078832
Neuronal acetylcholine receptor; alpha4/beta2 EC50 = 1.3 nM 8.89 In vitro binding affinity by inhibiting [3H]dopamine release in rat brain tissue... 12086489
Neuronal acetylcholine receptor subunit alpha-7 Ki = 4.9 nM 8.31 Displacement of [125I-alpha]-Bungarotoxin from alpha-7 nAChR in rat hippocampal ... 16934977
Neuronal acetylcholine receptor subunit alpha-7 EC50 = 39.81 nM 7.4 Agonist activity at human recombinant alpha7 nAChR expressed in rat GH3 cells by... 19208472

Literature References

PubMed DOI Target Context # Activities
20038125 10.1021/np9006124 Mus musculus 5
15050621 10.1016/j.bmcl.2004.02.007 Mus musculus 4
16722642 10.1021/jm060122n Mus musculus 4
15050621 10.1016/j.bmcl.2004.02.007 Neuronal acetylcholine receptor; alpha4/beta2 3
17994682 10.1021/jm0704696 Mus musculus 3
11405659 10.1021/jm0100178 Neuronal acetylcholine receptor; alpha4/beta2 2
20038125 10.1021/np9006124 Neuronal acetylcholine receptor; alpha4/beta2 2
19208472 10.1016/j.bmcl.2009.01.073 Neuronal acetylcholine receptor subunit alpha-7 2
16078832 10.1021/jm040881a Neuronal acetylcholine receptor; alpha3/beta4 2
12086489 10.1021/jm0103561 Neuronal acetylcholine receptor; alpha4/beta2 2
16078832 10.1021/jm040881a Neuronal acetylcholine receptor; alpha4/beta2 1
16078832 10.1021/jm040881a ADMET 1
16722642 10.1021/jm060122n Neuronal acetylcholine receptor; alpha4/beta2 1
15317468 10.1021/jm040078g Neuronal acetylcholine receptor; alpha4/beta2 1
16934977 10.1016/j.bmcl.2006.08.049 Neuronal acetylcholine receptor subunit alpha-7 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
26383127 10.1016/j.ejmech.2015.09.006 Neuronal acetylcholine receptor; alpha4/beta2 1
11405659 10.1021/jm0100178 Mus musculus 1
11405659 10.1021/jm0100178 Unchecked 1

Data from ChEMBL 36 via Core Engine