Compound Detail

CHEMBL2391541

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C=CCN(CC=C)CCc1c[nH]c2ccc(OC)cc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL2391541
Phase	Preclinical
Structure Type	MOL
InChI Key	HGRHWEAUHXYNNP-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

270.4

MW (Da)

3.39

ALogP

HBA

HBD

28.3

PSA (Å²)

0.74

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C17H22N2O
MW	270.38
Aromatic Rings	2
Heavy Atoms	20
NP-Likeness	-0.62

Activity Summary

Ki 58 meas. best 7.77

EC50 6 meas. best 8.55

IC50 3 meas. best 5.06

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 2A CHEMBL224	EC50	8.55	8.055	2.8	2
5-hydroxytryptamine receptor 2B CHEMBL1833	EC50	8.26	8.26	5.5	2
5-hydroxytryptamine receptor 2C CHEMBL225	EC50	8.03	8.03	9.3	2
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	7.77	7.53	17.0	3
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	7.72	7.235	19.0	4
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	7.5	7.4	31.6	3
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	7.08	6.9867	84.0	3
5-hydroxytryptamine receptor 1D CHEMBL1983	Ki	7.0	6.8625	100.0	4
5-hydroxytryptamine receptor 1B CHEMBL1898	Ki	6.89	6.6367	128.8	3
Alpha-2A adrenergic receptor CHEMBL1867	Ki	6.67	6.67	213.8	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.66	6.46	218.0	4
Unchecked CHEMBL612545	Ki	6.6	6.4067	251.2	3
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	6.52	6.52	302.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL4153	Ki	6.4	6.4	398.1	2
5-hydroxytryptamine receptor 1E CHEMBL2182	Ki	6.38	6.3533	413.0	3
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.34	5.9533	457.1	3
D(3) dopamine receptor CHEMBL234	Ki	6.31	6.305	489.8	2
Alpha-2C adrenergic receptor CHEMBL1916	Ki	6.3	6.1433	501.2	3
Histamine H1 receptor CHEMBL231	Ki	6.3	6.0767	501.2	3
Sodium-dependent serotonin transporter CHEMBL228	Ki	6.3	6.0625	501.2	4
Alpha-2B adrenergic receptor CHEMBL1942	Ki	6.14	6.14	724.4	1
Kappa-type opioid receptor CHEMBL237	Ki	5.95	5.95	1122.0	1
Histamine H3 receptor CHEMBL264	Ki	5.77	5.77	1698.2	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	5.5	5.135	3162.3	2
5-hydroxytryptamine receptor 5A CHEMBL3426	Ki	5.48	5.48	3311.3	1
Histamine H2 receptor CHEMBL1941	Ki	5.37	5.37	4247.0	2
Sodium-dependent serotonin transporter CHEMBL228	IC50	5.06	5.06	8709.6	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	4.92	4.92	12008.0	1
Sodium-dependent dopamine transporter CHEMBL238	IC50	4.49	4.49	32359.4	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	4.37	4.37	42657.9	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 2A	EC50	=	2.8	nM	8.55	Agonist activity at human 5-HT2A receptor expressed in HEK293 cells assessed as ...	23602445
5-hydroxytryptamine receptor 2B	EC50	=	5.5	nM	8.26	Agonist activity at human 5-HT2B receptor expressed in HEK293 cells assessed as ...	23602445
5-hydroxytryptamine receptor 2B	EC50	=	5.495	nM	8.26	Agonist activity at human 5-HT2B receptor expressed in HEK293 cells assessed as ...	23602445
5-hydroxytryptamine receptor 2C	EC50	=	9.4	nM	8.03	Agonist activity at human 5-HT2C receptor expressed in HEK293 cells assessed as ...	23602445
5-hydroxytryptamine receptor 2C	EC50	=	9.333	nM	8.03	Agonist activity at human 5-HT2C receptor expressed in HEK293 cells assessed as ...	23602445
5-hydroxytryptamine receptor 7	Ki	=	16.98	nM	7.77	Displacement of [3H]LSD from human recombinant 5-HT7 receptor expressed in HEK29...	23602445
5-hydroxytryptamine receptor 7	Ki	=	17.0	nM	7.77	Displacement of [3H]LSD from human recombinant 5-HT7 receptor expressed in HEK29...	23602445
5-hydroxytryptamine receptor 1A	Ki	=	19.0	nM	7.72	Binding affinity to 5-HT 1A (unknown origin) by competition binding assay	26739781
5-hydroxytryptamine receptor 1A	Ki	=	19.95	nM	7.7	Binding affinity to 5-HT 1A (unknown origin) by competition binding assay	26739781
5-hydroxytryptamine receptor 2A	EC50	=	27.54	nM	7.56	Agonist activity at human 5-HT2A receptor expressed in HEK293 cells assessed as ...	23602445
5-hydroxytryptamine receptor 2B	Ki	=	31.62	nM	7.5	Displacement of [3H]LSD from human recombinant 5-HT2B receptor expressed in HEK2...	23602445
5-hydroxytryptamine receptor 2B	Ki	=	34.0	nM	7.47	Displacement of [3H]LSD from human recombinant 5-HT2B receptor expressed in HEK2...	23602445
5-hydroxytryptamine receptor 2B	Ki	=	58.88	nM	7.23	Binding affinity to 5-HT 2B (unknown origin) by competition binding assay	26739781
5-hydroxytryptamine receptor 6	Ki	=	84.0	nM	7.08	Displacement of [3H]LSD from human recombinant 5-HT6 receptor expressed in HEK29...	23602445
5-hydroxytryptamine receptor 6	Ki	=	85.11	nM	7.07	Displacement of [3H]LSD from human recombinant 5-HT6 receptor expressed in HEK29...	23602445
5-hydroxytryptamine receptor 7	Ki	=	89.13	nM	7.05	Binding affinity to 5-HT 7 (unknown origin) by competition binding assay	26739781
5-hydroxytryptamine receptor 1D	Ki	=	100.0	nM	7.0	Binding affinity to 5-HT 1D (unknown origin) by competition binding assay	26739781
5-hydroxytryptamine receptor 1B	Ki	=	129.0	nM	6.89	Displacement of [3H]GR127543 from human recombinant 5-HT1B receptor expressed in...	23602445
5-hydroxytryptamine receptor 1B	Ki	=	128.82	nM	6.89	Displacement of [3H]GR127543 from human recombinant 5-HT1B receptor expressed in...	23602445
5-hydroxytryptamine receptor 1D	Ki	=	149.0	nM	6.83	Displacement of [3H]GR127543 from human recombinant 5-HT1D receptor expressed in...	23602445

Literature References

PubMed	DOI	Target Context	# Activities
23602445	10.1016/j.bmcl.2013.03.066	5-hydroxytryptamine receptor 2B	5
23602445	10.1016/j.bmcl.2013.03.066	5-hydroxytryptamine receptor 2A	5
23602445	10.1016/j.bmcl.2013.03.066	Unchecked	5
23602445	10.1016/j.bmcl.2013.03.066	5-hydroxytryptamine receptor 2C	5
23602445	10.1016/j.bmcl.2013.03.066	Sodium-dependent serotonin transporter	4
23602445	10.1016/j.bmcl.2013.03.066	Sodium-dependent dopamine transporter	3
26739781	10.1016/j.bmcl.2015.12.053	5-hydroxytryptamine receptor 1A	3
26739781	10.1016/j.bmcl.2015.12.053	5-hydroxytryptamine receptor 2A	3
23602445	10.1016/j.bmcl.2013.03.066	Sodium-dependent noradrenaline transporter	3
26739781	10.1016/j.bmcl.2015.12.053	5-hydroxytryptamine receptor 1D	3
23602445	10.1016/j.bmcl.2013.03.066	Neuronal acetylcholine receptor; alpha4/beta2	2
23602445	10.1016/j.bmcl.2013.03.066	5-hydroxytryptamine receptor 1A	2
26739781	10.1016/j.bmcl.2015.12.053	Sigma non-opioid intracellular receptor 1	2
23602445	10.1016/j.bmcl.2013.03.066	5-hydroxytryptamine receptor 1B	2
23602445	10.1016/j.bmcl.2013.03.066	5-hydroxytryptamine receptor 7	2
23602445	10.1016/j.bmcl.2013.03.066	5-hydroxytryptamine receptor 1D	2
23602445	10.1016/j.bmcl.2013.03.066	5-hydroxytryptamine receptor 6	2
23602445	10.1016/j.bmcl.2013.03.066	D(3) dopamine receptor	2
23602445	10.1016/j.bmcl.2013.03.066	Histamine H2 receptor	2
23602445	10.1016/j.bmcl.2013.03.066	Histamine H1 receptor	2

Data from ChEMBL 36 via Core Engine