Compound Detail

CHEMBL122270

LOBELINE

🧪 Phase II

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🧪 Phase II

CN1[C@@H](CC(=O)c2ccccc2)CCC[C@H]1C[C@H](O)c1ccccc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL122270
Name	LOBELINE
Phase	Phase II
Structure Type	MOL
InChI Key	MXYUKLILVYORSK-HBMCJLEFSA-N

Known Names

(-)-lobeline .alpha.-lobeline Alpha-lobeline Inflatine Lobelina Lobeline Lobelinum NSC-757421

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

337.5

MW (Da)

4.24

ALogP

HBA

HBD

40.5

PSA (Å²)

0.80

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula	C22H27NO2
MW	337.46
Aromatic Rings	2
Heavy Atoms	25
NP-Likeness	0.51

Indications

Attention Deficit Disorder with Hyperactivity Amphetamine-Related Disorders

Activity Summary

Ki 43 meas. best 8.7

IC50 10 meas. best 7.06

Kd 4 meas. best 7.9

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907596	Ki	8.7	8.312	2.0	5
Soluble acetylcholine receptor CHEMBL1944497	Ki	8.6	8.6	2.5	1
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907589	Ki	8.4	8.325	4.0	4
Neuronal acetylcholine receptor CHEMBL2094110	Ki	8.4	8.4	4.0	1
Synaptic vesicular amine transporter CHEMBL4828	Ki	8.4	5.8982	4.0	11
Unchecked CHEMBL612545	Kd	7.9	7.895	12.6	2
Neuronal acetylcholine receptor CHEMBL2094110	IC50	7.06	5.9	87.0	2
Neuronal acetylcholine receptor; alpha4/beta4 CHEMBL1907595	Ki	6.92	6.91	120.0	2
Cytochrome P450 2D6 CHEMBL289	Ki	6.92	6.92	120.0	1
Synaptic vesicular amine transporter CHEMBL4295886	IC50	6.42	6.42	381.0	1
Neuronal acetylcholine receptor; alpha3/beta4 CHEMBL1907593	Ki	6.32	6.31	480.0	2
Acetylcholine-binding protein CHEMBL6084	Ki	6.2	6.2	631.0	1
Acetylcholine-binding protein CHEMBL6084	Kd	6.2	6.2	630.0	2
Acetylcholine receptor subunit alpha CHEMBL3097	IC50	6.0	5.415	1010.0	2
Synaptic vesicular amine transporter CHEMBL1893	Ki	5.74	5.67	1840.0	3
Synaptic vesicular amine transporter CHEMBL1893	IC50	5.38	5.38	4200.0	1
Unchecked CHEMBL612545	IC50	5.34	5.34	4600.0	1
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL4980	Ki	5.2	5.1933	6260.0	3
Unchecked CHEMBL612545	Ki	5.2	5.12	6260.0	2
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	5.13	5.13	7400.0	1
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL2492	Ki	5.1	5.1	7943.3	1
Histamine H1 receptor CHEMBL4701	IC50	4.95	4.95	11220.2	1
Nicotinic acetylcholine receptor alpha 5 subunit CHEMBL2366408	Ki	4.89	4.89	12800.0	1
Sodium-dependent dopamine transporter CHEMBL338	Ki	4.55	4.55	28200.0	2
Histamine H1 receptor CHEMBL231	IC50	4.35	4.35	44668.4	1
Sodium-dependent serotonin transporter CHEMBL313	Ki	4.33	4.33	46800.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	0.8333	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	1.995	nM	8.7	Displacement of [3H]epibatidine from rat alpha4beta2 nAChR expressed in HEK293 c...	26301559
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	2.2	nM	8.66	Displacement of [3H]epibatidine from rat alpha4beta2 nAChR expressed in HEK293 c...	26301559
Soluble acetylcholine receptor	Ki	=	2.512	nM	8.6	Displacement of [3H]epibatidine from Aplysia californica acetylcholine binding p...	22243960
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	4.0	nM	8.4	Displacement of [3H]-nicotine from alpha4beta2 nicotine acetylcholine receptor (...	26142318
Neuronal acetylcholine receptor	Ki	=	4.0	nM	8.4	Evaluated for its binding affinity towards Nicotinic acetylcholine receptor in r...	10479304
Synaptic vesicular amine transporter	Ki	=	4.0	nM	8.4	Inhibition constant against [3H]nicotine binding to vesicular monoamine transpor...	16112864
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	4.0	nM	8.4	Inhibition of [3H]NIC binding to alpha-4-beta-2 nAChR in rat brain membrane	16905316
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	4.0	nM	8.4	Displacement of [3H]nicotine from alpha4beta2 nAChR in rat brain homogenate by l...	20036131
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	5.012	nM	8.3	Binding affinity to alpha4beta2 (unknown origin)	26301559
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	5.0	nM	8.3	Binding affinity to alpha4beta2 (unknown origin)	26301559
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	5.012	nM	8.3	Displacement of [3H]epibatidine from human nAChR alpha4beta2 receptor expressed ...	22243960
Unchecked	Kd	=	12.59	nM	7.9	Binding affinity to Aplysia californica AChBP after 300 seconds by SPR biosensor...	26301559
Unchecked	Kd	=	13.0	nM	7.89	Binding affinity to Aplysia californica AChBP after 300 seconds by SPR biosensor...	26301559
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	40.0	nM	7.4	Inhibition of 3 nM [3H]NIC binding to Nicotinic acetylcholine receptor alpha4-be...	16107155
Neuronal acetylcholine receptor	IC50	=	87.0	nM	7.06	Binding affinity towards nicotinic acetylcholine receptor using [3H]-cytisine as...	14552793
Cytochrome P450 2D6	Ki	=	120.0	nM	6.92	Inhibitory constant for cytochrome P450 2D6	8487254
Neuronal acetylcholine receptor; alpha4/beta4	Ki	=	120.0	nM	6.92	Displacement of [3H]epibatidine from rat alpha4beta4 nACHR expressed in HEK293 c...	26301559
Neuronal acetylcholine receptor; alpha4/beta4	Ki	=	125.89	nM	6.9	Displacement of [3H]epibatidine from rat alpha4beta4 nACHR expressed in HEK293 c...	26301559
Synaptic vesicular amine transporter	IC50	=	381.0	nM	6.42	Inhibition of VMAT2 in C57Bl/6J mouse striatal membranes assessed as reduction i...	30240563
Synaptic vesicular amine transporter	Ki	=	470.0	nM	6.33	Inhibition of [3H]dopamine uptake at VMAT2 in rat brain synaptic vesicle by liqu...	19691331

Literature References

PubMed	DOI	Target Context	# Activities
39136667	10.1021/acs.jnatprod.4c00406	N6-adenosine-methyltransferase catalytic subunit	24
39136667	10.1021/acs.jnatprod.4c00406	Lenvatinib-resistant Huh7/Len	19
39136667	10.1021/acs.jnatprod.4c00406	ADMET	8
39136667	10.1021/acs.jnatprod.4c00406	Lenvatinib-resistant Hep3B/Len	6
30240563	10.1021/acs.jmedchem.8b00542	Synaptic vesicular amine transporter	5
39136667	10.1021/acs.jnatprod.4c00406	Lenvatinib-resistant HCC/Len	5
26301559	10.1016/j.ejmech.2015.07.024	Neuronal acetylcholine receptor; alpha4/beta2	4
-	10.1584/jpestics.20.49	Acetylcholine receptor subunit alpha	4
16112864	10.1016/j.bmcl.2005.07.032	Synaptic vesicular amine transporter	3
19691331	10.1021/jm900770h	Synaptic vesicular amine transporter	3
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
14552793	10.1016/s0960-894x(03)00728-5	Neuronal acetylcholine receptor	2
-	10.1584/jpestics.20.57	Unchecked	2
26301559	10.1016/j.ejmech.2015.07.024	Neuronal acetylcholine receptor; alpha4/beta4	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
26301559	10.1016/j.ejmech.2015.07.024	Unchecked	2
16905316	10.1016/j.bmcl.2006.07.070	Unchecked	2
23527317	10.1039/c3md20374c	Synaptic vesicular amine transporter	2
20036131	10.1016/j.bmc.2009.12.002	Synaptic vesicular amine transporter	2
20036131	10.1016/j.bmc.2009.12.002	Unchecked	2

Data from ChEMBL 36 via Core Engine