Compound Detail

CHEMBL476108

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O=C(CCCN1CCCN(c2ccc(Cl)cc2)CC1)c1ccc(F)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL476108
Phase	Preclinical
Structure Type	MOL
InChI Key	MVKKLGNVARQKRP-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

374.9

MW (Da)

4.65

ALogP

HBA

HBD

23.6

PSA (Å²)

0.69

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C21H24ClFN2O
MW	374.89
Aromatic Rings	2
Heavy Atoms	26
NP-Likeness	-1.78

Activity Summary

Ki 18 meas. best 8.29

IC50 9 meas. best 6.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Sigma intracellular receptor 2 CHEMBL4105907	Ki	8.29	8.27	5.1	2
D(4) dopamine receptor CHEMBL219	Ki	8.18	8.18	6.6	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	7.63	7.63	23.6	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	7.63	7.625	23.4	2
D(2) dopamine receptor CHEMBL217	Ki	7.36	7.36	43.3	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	7.25	7.25	56.6	1
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	6.93	6.93	117.4	1
D(3) dopamine receptor CHEMBL234	Ki	6.8	6.8	158.8	1
D(1A) dopamine receptor CHEMBL2056	Ki	6.79	6.79	162.7	1
Histamine H1 receptor CHEMBL231	Ki	6.72	6.72	188.6	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	6.53	6.53	295.9	1
PANC-1 CHEMBL614139	IC50	6.4	6.4	400.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	6.3	6.3	495.2	1
Transporter CHEMBL6184	Ki	6.07	6.07	850.7	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	6.06	6.06	871.6	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	5.94	5.94	1150.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	5.85	5.85	1425.0	1
MIA PaCa-2 CHEMBL614725	IC50	5.7	5.7	2000.0	1
MDA-MB-468 CHEMBL614335	IC50	5.3	5.3	5000.0	1
A549 CHEMBL392	IC50	5.21	5.21	6200.0	1
PC-3 CHEMBL390	IC50	5.09	5.09	8200.0	1
MDA-MB-231 CHEMBL400	IC50	4.82	4.67	15000.0	3
MCF-10A CHEMBL614321	IC50	4.66	4.66	22000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Sigma intracellular receptor 2	Ki	=	5.129	nM	8.29	Displacement [3H]-DTG from sigma 2 receptor (unknown origin) expressed in HEK ce...	30737135
Sigma intracellular receptor 2	Ki	=	5.6	nM	8.25	Displacement [3H]-DTG from sigma 2 receptor (unknown origin) expressed in HEK ce...	30737135
D(4) dopamine receptor	Ki	=	6.6	nM	8.18	Binding affinity to human cloned dopamine D4 receptor	18595716
Sigma non-opioid intracellular receptor 1	Ki	=	23.44	nM	7.63	Displacement [3H]-Pentazocine from sigma 1 receptor (unknown origin) expressed i...	30737135
5-hydroxytryptamine receptor 2A	Ki	=	23.6	nM	7.63	Binding affinity to human cloned 5HT2A receptor	18595716
Sigma non-opioid intracellular receptor 1	Ki	=	24.0	nM	7.62	Displacement [3H]-Pentazocine from sigma 1 receptor (unknown origin) expressed i...	30737135
D(2) dopamine receptor	Ki	=	43.3	nM	7.36	Binding affinity to human cloned dopamine D2 receptor	18595716
Sodium-dependent serotonin transporter	Ki	=	56.6	nM	7.25	Binding affinity to human SERT	18595716
5-hydroxytryptamine receptor 1A	Ki	=	117.4	nM	6.93	Binding affinity to human cloned 5HT1A receptor	18595716
D(3) dopamine receptor	Ki	=	158.8	nM	6.8	Binding affinity to human cloned dopamine D3 receptor	18595716
D(1A) dopamine receptor	Ki	=	162.7	nM	6.79	Binding affinity to human cloned dopamine D1 receptor	18595716
Histamine H1 receptor	Ki	=	188.6	nM	6.72	Binding affinity to human cloned histamine H1 receptor	18595716
5-hydroxytryptamine receptor 6	Ki	=	295.9	nM	6.53	Binding affinity to human cloned 5HT6 receptor	18595716
PANC-1	IC50	=	400.0	nM	6.4	Cytotoxicity against human PANC1 cells assessed as reduction in cell viability r...	30987780
5-hydroxytryptamine receptor 2B	Ki	=	495.2	nM	6.3	Binding affinity to human cloned 5HT2B receptor	18595716
Transporter	Ki	=	850.7	nM	6.07	Binding affinity to rat NET	18595716
Muscarinic acetylcholine receptor M1	Ki	=	871.6	nM	6.06	Binding affinity to human cloned muscarinic M1 receptor	18595716
Sodium-dependent dopamine transporter	Ki	=	1150.0	nM	5.94	Binding affinity to human DAT	18595716
5-hydroxytryptamine receptor 2C	Ki	=	1425.0	nM	5.85	Binding affinity to human cloned 5HT2C receptor	18595716
MIA PaCa-2	IC50	=	2000.0	nM	5.7	Cytotoxicity against human MIAPaCa2 cells assessed as reduction in cell viabilit...	30987780

Literature References

PubMed	DOI	Target Context	# Activities
30987780	10.1016/j.bmc.2019.04.012	MDA-MB-231	3
36202063	10.1016/j.bmc.2022.117032	MDA-MB-231	2
30737135	10.1016/j.bmc.2019.01.035	Sigma non-opioid intracellular receptor 1	2
30737135	10.1016/j.bmc.2019.01.035	Sigma intracellular receptor 2	2
18595716	10.1016/j.bmc.2008.06.030	Mus musculus	1
30737135	10.1016/j.bmc.2019.01.035	Unchecked	1
18595716	10.1016/j.bmc.2008.06.030	5-hydroxytryptamine receptor 2C	1
18595716	10.1016/j.bmc.2008.06.030	5-hydroxytryptamine receptor 2A	1
18595716	10.1016/j.bmc.2008.06.030	5-hydroxytryptamine receptor 1A	1
18595716	10.1016/j.bmc.2008.06.030	D(4) dopamine receptor	1
18595716	10.1016/j.bmc.2008.06.030	D(2) dopamine receptor	1
18595716	10.1016/j.bmc.2008.06.030	Histamine H1 receptor	1
18595716	10.1016/j.bmc.2008.06.030	Rattus norvegicus	1
18595716	10.1016/j.bmc.2008.06.030	Sodium-dependent serotonin transporter	1
18595716	10.1016/j.bmc.2008.06.030	Transporter	1
18595716	10.1016/j.bmc.2008.06.030	Sodium-dependent dopamine transporter	1
18595716	10.1016/j.bmc.2008.06.030	Muscarinic acetylcholine receptor M1	1
18595716	10.1016/j.bmc.2008.06.030	5-hydroxytryptamine receptor 6	1
18595716	10.1016/j.bmc.2008.06.030	5-hydroxytryptamine receptor 2B	1
18595716	10.1016/j.bmc.2008.06.030	D(1A) dopamine receptor	1

Data from ChEMBL 36 via Core Engine