Compound Detail

CHEMBL6623

EPIBATIDINE

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Clc1ccc(C2CC3CCC2N3)cn1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL6623
Name	EPIBATIDINE
Phase	Preclinical
Structure Type	MOL
InChI Key	NLPRAJRHRHZCQQ-UHFFFAOYSA-N

Targets

245

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

208.7

MW (Da)

2.34

ALogP

HBA

HBD

24.9

PSA (Å²)

0.72

QED

Ro5 Violations

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 155 meas. best 11.0

EC50 41 meas. best 10.7

Kd 35 meas. best 10.7

IC50 14 meas. best 10.43

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907589	Ki	11.0	10.3889	0.0	9
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907596	Ki	11.0	10.1154	0.0	37
Neuronal acetylcholine receptor; alpha2/beta2 CHEMBL1907592	Ki	11.0	10.5786	0.0	7
Neuronal acetylcholine receptor subunit alpha-4 CHEMBL5569	Ki	11.0	11.0	0.0	1
Neuronal acetylcholine receptor; alpha3/beta2 CHEMBL1907587	Ki	10.85	10.4389	0.0	9
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907589	EC50	10.7	7.8363	0.0	8
Neuronal acetylcholine receptor; alpha2/beta2 CHEMBL1907592	Kd	10.7	10.7	0.0	1
Unchecked CHEMBL612545	Kd	10.7	8.1933	0.0	24
Neuronal acetylcholine receptor CHEMBL2094110	Ki	10.68	10.2871	0.0	7
Neuronal acetylcholine receptor subunit beta-4 CHEMBL2658	Ki	10.66	10.66	0.0	1
Unchecked CHEMBL612545	Ki	10.6	9.5241	0.0	22
Neuronal acetylcholine receptor subunit alpha-2 CHEMBL2584	Ki	10.6	10.6	0.0	2
Neuronal acetylcholine receptor; alpha3/beta2 CHEMBL1907587	Kd	10.52	10.52	0.0	1
Neuronal acetylcholine receptor; alpha3/beta2 CHEMBL2109234	Kd	10.52	10.52	0.0	1
Neuronal acetylcholine receptor; alpha3/beta2 CHEMBL2109234	Ki	10.46	10.46	0.0	1
Neuronal acetylcholine receptor subunit alpha-4 CHEMBL4457	IC50	10.43	10.43	0.0	1
Neuronal acetylcholine receptor; alpha3/beta4 CHEMBL1907593	EC50	10.43	7.7533	0.0	6
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907596	Kd	10.4	10.4	0.0	2
Neuronal acetylcholine receptor CHEMBL2094110	IC50	10.39	9.36	0.0	4
Acetylcholine receptor; alpha1/beta1/delta/gamma CHEMBL1907588	EC50	10.28	10.28	0.1	1
Unchecked CHEMBL612545	IC50	10.15	8.99	0.1	5
Neuronal acetylcholine receptor; alpha4/beta4 CHEMBL1907591	Ki	10.14	10.14	0.1	1
Neuronal acetylcholine receptor; alpha3/beta4 CHEMBL1907593	Ki	10.11	9.3823	0.1	13
Neuronal acetylcholine receptor; alpha2/beta4 CHEMBL1907590	Kd	10.1	10.1	0.1	1
Neuronal acetylcholine receptor; alpha4/beta4 CHEMBL1907595	Ki	10.07	9.8322	0.1	9
Neuronal acetylcholine receptor; alpha2/beta4 CHEMBL1907590	Ki	10.06	10.03	0.1	7
Neuronal acetylcholine receptor; alpha4/beta4 CHEMBL1907595	Kd	10.05	10.05	0.1	1
Neuronal acetylcholine receptor; alpha2/beta4 CHEMBL2109230	Ki	10.04	10.04	0.1	1
Acetylcholine receptor subunit delta CHEMBL3916	Ki	10.0	10.0	0.1	1
Neuronal acetylcholine receptor; alpha3/beta4 CHEMBL1907594	Ki	9.82	9.636	0.1	5
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907596	EC50	9.7	8.504	0.2	5
Acetylcholine-binding protein CHEMBL6084	Ki	9.52	9.52	0.3	1
Neuronal acetylcholine receptor; alpha3/beta4 CHEMBL1907594	Kd	9.52	9.52	0.3	1
Neuronal acetylcholine receptor; alpha3/beta4 CHEMBL1907593	Kd	9.52	9.52	0.3	1
Striatum CHEMBL613663	EC50	9.08	9.08	0.8	2
Soluble acetylcholine receptor CHEMBL1944497	Ki	9.0	9.0	1.0	1
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL2492	Kd	8.97	8.585	1.1	2
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907589	IC50	8.97	8.97	1.1	1
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL2492	Ki	8.66	8.164	2.2	5
Acetylcholine receptor CHEMBL2096975	Ki	8.57	8.57	2.7	1
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL4980	Ki	8.57	7.669	2.7	10
Neuronal acetylcholine receptor; alpha3/beta4 CHEMBL1907594	EC50	8.15	7.8183	7.0	6
Neuronal acetylcholine receptor subunit alpha-3 CHEMBL3068	EC50	8.15	8.15	7.0	1
IMR-32 CHEMBL614585	EC50	8.15	7.81	7.0	2
K177 cell line CHEMBL614687	EC50	7.77	7.115	17.0	2
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL2492	IC50	7.51	7.51	31.0	1
Rattus norvegicus CHEMBL376	EC50	7.43	7.43	37.0	1
Neuronal acetylcholine receptor CHEMBL2094110	EC50	7.0	7.0	100.0	1
Acetylcholine receptor subunit alpha CHEMBL4808	IC50	6.8	6.8	160.0	1
Acetylcholine receptor CHEMBL2096975	EC50	6.7	6.7	200.0	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	In vitro inhibition of 5-(125I)A-85380 binding to nicotinic acetylcholine recept...	12061886
Neuronal acetylcholine receptor; alpha2/beta2	Ki	=	0.01	nM	11.0	Binding affinity towards rat alpha2-beta2 neuronal nAChR expressed in Xenopus oo...	15050621
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	0.01	nM	11.0	Potency to displace [3H]nicotine binding to Nicotinic acetylcholine receptor alp...	12061885
Neuronal acetylcholine receptor subunit alpha-4	Ki	=	0.01	nM	11.0	Binding affinity to recombinant Gallus gallus (chicken) alpha4beta2 nicotinic ac...	21341671
Neuronal acetylcholine receptor; alpha3/beta2	Ki	=	0.014	nM	10.85	Binding affinity towards rat Nicotinic acetylcholine receptor alpha3-beta2 expre...	15050621
Neuronal acetylcholine receptor; alpha4/beta2	EC50	=	0.02	nM	10.7	Agonist activity at alpha4beta 2 nAChR	22591063
Neuronal acetylcholine receptor; alpha2/beta2	Kd	=	0.02	nM	10.7	Tested for binding affinity against Nicotinic acetylcholine receptor alpha2-beta...	12620069
Unchecked	Kd	=	0.02	nM	10.7	Dissociation constant against Nicotinic acetylcholine receptor alpha2-beta2	15771418
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	0.02	nM	10.7	Inhibition of [3H]nicotine binding to Nicotinic acetylcholine receptor alpha4-be...	-
Neuronal acetylcholine receptor; alpha2/beta2	Ki	=	0.02	nM	10.7	Displacement of [3H]epibatidine from rat alpha-2-beta-2 nACHR expressed in human...	16640326
Neuronal acetylcholine receptor	Ki	=	0.021	nM	10.68	Compound was evaluated for potency towards nicotinic acetylcholine receptor in r...	-
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	0.021	nM	10.68	Binding affinity at rat brain Nicotinic acetylcholine receptor alpha4-beta2	12109907
Neuronal acetylcholine receptor subunit beta-4	Ki	=	0.022	nM	10.66	Binding affinity to Nicotinic acetylcholine receptor alpha3-beta4 using +/-[3H]e...	11855986
Neuronal acetylcholine receptor; alpha2/beta2	Ki	=	0.025	nM	10.6	Tested for binding affinity against Nicotinic acetylcholine receptor alpha2-beta...	12620069
Neuronal acetylcholine receptor subunit alpha-2	Ki	=	0.025	nM	10.6	Displacement of [3H]epibatidine from rat alpha2beta2 nicotinic receptor expresse...	19481945
Neuronal acetylcholine receptor subunit alpha-2	Ki	=	0.025	nM	10.6	Displacement of [3H]epibatidine from rat alpha2beta2 nAChR expressed in HEK293 c...	18605717
Neuronal acetylcholine receptor; alpha2/beta2	Ki	=	0.025	nM	10.6	In vitro binding affinity towards rat Nicotinic acetylcholine receptor alpha2-be...	16039849
Neuronal acetylcholine receptor; alpha2/beta2	Ki	=	0.025	nM	10.6	Binding affinity towards nicotinic acetylcholine receptor alpha2-beta2 using [3H...	15050615
Neuronal acetylcholine receptor; alpha3/beta2	Ki	=	0.025	nM	10.6	Binding affinity towards rat Nicotinic acetylcholine receptor alpha3-beta2 expre...	15050613
Unchecked	Ki	=	0.025	nM	10.6	Inhibition of [3H]epibatidine binding to Nicotinic acetylcholine receptor alpha2...	15771418

Literature References

PubMed	DOI	Target Context	# Activities
19459645	10.1021/jm900153c	Unchecked	55
-	10.1016/S0960-894X(01)80759-9	Mus musculus	22
15050613	10.1016/j.bmcl.2003.09.105	Unchecked	10
33120080	10.1016/j.bmc.2020.115820	Unchecked	9
33120080	10.1016/j.bmc.2020.115820	Muscarinic acetylcholine receptor M1	7
15771418	10.1021/jm0492406	Unchecked	7
9435889	10.1021/jm970377o	Unchecked	5
15050621	10.1016/j.bmcl.2004.02.007	Neuronal acetylcholine receptor; alpha4/beta2	5
33120080	10.1016/j.bmc.2020.115820	Mus musculus	4
24428686	10.1021/jm401602p	Mus musculus	4
-	10.1016/j.bmcl.2004.08.026	Neuronal acetylcholine receptor; alpha4/beta2	4
20337496	10.1021/np900727e	Neuronal acetylcholine receptor; alpha3/beta4	4
9513595	10.1021/jm970427p	Mus musculus	4
29671588	10.1021/acs.jnatprod.8b00062	Neuronal acetylcholine receptor; alpha4/beta2	4
17585748	10.1021/jm070018l	Neuronal acetylcholine receptor; alpha4/beta2	4
29671588	10.1021/acs.jnatprod.8b00062	Neuronal acetylcholine receptor; alpha3/beta4	4
17964169	10.1016/j.bmc.2007.10.027	Mus musculus	4
12086489	10.1021/jm0103561	Neuronal acetylcholine receptor; alpha4/beta2	4
15715488	10.1021/jm040160b	Mus musculus	4
9435889	10.1021/jm970377o	Neuronal acetylcholine receptor; alpha4/beta2	4

Data from ChEMBL 36 via Core Engine