Compound Detail

CHEMBL6200

NORNICOTINE

Phase I

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Phase I

c1cncc([C@@H]2CCCN2)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL6200
Name	NORNICOTINE
Phase	Phase I
Structure Type	MOL
InChI Key	MYKUKUCHPMASKF-VIFPVBQESA-N

Known Names

1'-demethylnicotine 3-(2-pyrrolidinyl)-(s)-pyridine Nicotine related compound f Nornicotine

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

148.2

MW (Da)

1.51

ALogP

HBA

HBD

24.9

PSA (Å²)

0.65

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula	C9H12N2
MW	148.21
Aromatic Rings	1
Heavy Atoms	11
NP-Likeness	-0.09

Activity Summary

Ki 16 meas. best 7.85

IC50 6 meas. best 7.1

EC50 4 meas. best 4.76

Kd 2 meas. best 8.97

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL2492	Kd	8.97	8.97	1.1	1
Unchecked CHEMBL612545	Kd	8.51	8.51	3.1	1
Unchecked CHEMBL612545	Ki	7.85	6.568	14.0	5
Neuronal acetylcholine receptor CHEMBL2094110	Ki	7.66	7.66	22.0	1
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907589	Ki	7.54	7.54	29.0	1
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907596	Ki	7.52	7.5067	30.0	3
Neuronal acetylcholine receptor; alpha3/beta2 CHEMBL1907587	Ki	7.33	7.33	47.0	1
Neuronal acetylcholine receptor CHEMBL2094110	IC50	7.1	7.05	80.0	2
Acetylcholine receptor CHEMBL2096975	IC50	7.0	6.76	100.0	2
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL2492	Ki	6.14	6.14	730.0	1
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL4980	Ki	5.92	5.895	1190.0	2
Nicotinic acetylcholine receptor alpha 5 subunit CHEMBL2366408	Ki	5.06	5.06	8770.0	1
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL4980	EC50	4.76	4.76	17400.0	1
Unchecked CHEMBL612545	EC50	4.59	4.59	25730.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Neuronal acetylcholine receptor subunit alpha-7	Kd	=	1.06	nM	8.97	Dissociation constant for nicotinic acetylcholine receptor alpha 7 from human ne...	15686879
Unchecked	Kd	=	3.08	nM	8.51	Dissociation constant for nicotinic acetylcholine receptor alpha4-beta2 of mouse...	15686879
Unchecked	Ki	=	14.0	nM	7.85	Binding affinity for nicotinic acetylcholine receptor alpha4-beta2 from mouse M1...	15686879
Neuronal acetylcholine receptor	Ki	=	22.0	nM	7.66	In vitro binding affinity to neuronal nAChRs was determined by measuring the dis...	7799396
Unchecked	Ki	=	22.0	nM	7.66	Binding affinity at CCR was determined by displacement of [3H]cytisine from rat ...	7909335
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	29.0	nM	7.54	Binding affinity at heteropentameric Nicotinic acetylcholine receptor alpha4-bet...	10447950
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	30.0	nM	7.52	Binding affinity for rat brain Nicotinic acetylcholine receptor alpha4-beta2 usi...	16039854
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	30.0	nM	7.52	Affinity at alpha4-beta2 nACh receptors in rat brain (minus cerebellum) homogena...	12639569
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	33.0	nM	7.48	Binding affinity towards alpha4-beta2 measured by using the inhibition of [3H]NI...	12467625
Neuronal acetylcholine receptor; alpha3/beta2	Ki	=	47.0	nM	7.33	Affinity for Nicotinic acetylcholine receptor alpha4-beta2 tested by analogue-in...	11354387
Unchecked	Ki	=	56.0	nM	7.25	Binding affinity at CCR was determined by displacement of [3H]nicotine from rat ...	7909335
Neuronal acetylcholine receptor	IC50	=	80.0	nM	7.1	Inhibition of (-)-[3H]nicotine binding to rat brain membranes	3346870
Neuronal acetylcholine receptor	IC50	=	100.0	nM	7.0	Inhibition of [3H]MCC binding to rat brain membranes	3346870
Acetylcholine receptor	IC50	=	100.0	nM	7.0	inhibition of (-)-[3H]nicotine binding to torpedo electroplax membranes	3346870
Acetylcholine receptor	IC50	=	300.0	nM	6.52	Inhibition of [3H]MCC binding to torpedo electroplax membranes	3346870
Neuronal acetylcholine receptor subunit alpha-7	Ki	=	730.0	nM	6.14	Binding affinity at homopentameric Nicotinic acetylcholine receptor alpha-7 subt...	10447950
Neuronal acetylcholine receptor subunit alpha-7	Ki	=	1190.0	nM	5.92	Binding affinity towards alpha-7 neuronal nicotinic acetylcholine receptor (nACh...	12467625
Neuronal acetylcholine receptor subunit alpha-7	Ki	=	1340.0	nM	5.87	Affinity for alpha-7 neuronal nicotinic acetylcholine receptor subtype determine...	11354387
Unchecked	Ki	=	7610.0	nM	5.12	Displacement of [3H]alpha-bungarotoxin from nAChR in honeybee head membrane afte...	-
Nicotinic acetylcholine receptor alpha 5 subunit	Ki	=	8770.0	nM	5.06	Displacement of [3H]alpha-bungarotoxin from nAChR in Musca domestica (house fly)...	-

Literature References

PubMed	DOI	Target Context	# Activities
7909335	10.1021/jm00034a002	Unchecked	5
3346870	10.1021/jm00398a004	Acetylcholine receptor	4
3346870	10.1021/jm00398a004	Neuronal acetylcholine receptor	3
7799396	10.1021/jm00052a005	Neuronal acetylcholine receptor	2
3346870	10.1021/jm00398a004	Rattus norvegicus	2
-	10.1584/jpestics.17.4_231	Acetylcholinesterase	2
-	10.1584/jpestics.17.4_231	No relevant target	2
15686879	10.1016/j.bmcl.2004.12.069	Neuronal acetylcholine receptor subunit alpha-7	2
15686879	10.1016/j.bmcl.2004.12.069	Unchecked	2
33120080	10.1016/j.bmc.2020.115820	Neuronal acetylcholine receptor subunit alpha-7	1
-	10.1584/jpestics.17.4_231	Nicotinic acetylcholine receptor alpha 5 subunit	1
-	10.1584/jpestics.17.4_231	Unchecked	1
16039854	10.1016/j.bmcl.2005.06.053	Neuronal acetylcholine receptor; alpha4/beta2	1
10447950	10.1021/jm990093z	Neuronal acetylcholine receptor subunit alpha-7	1
10447950	10.1021/jm990093z	Neuronal acetylcholine receptor; alpha4/beta2	1
12639569	10.1016/s0960-894x(02)01031-4	Neuronal acetylcholine receptor; alpha4/beta2	1
12467625	10.1016/s0960-894x(02)00849-1	Neuronal acetylcholine receptor subunit alpha-7	1
12467625	10.1016/s0960-894x(02)00849-1	Neuronal acetylcholine receptor; alpha4/beta2	1
11354387	10.1016/s0960-894x(01)00193-7	Neuronal acetylcholine receptor subunit alpha-7	1
11354387	10.1016/s0960-894x(01)00193-7	Neuronal acetylcholine receptor; alpha3/beta2	1

Data from ChEMBL 36 via Core Engine