Compound Detail

CHEMBL2387229

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Cc1cc(=O)oc2c(Cl)c(OCCCCN3CCC(c4noc5cc(F)ccc45)CC3)ccc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL2387229
Phase	Preclinical
Structure Type	MOL
InChI Key	QBXXUIOGPPBTJN-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

485.0

MW (Da)

6.07

ALogP

HBA

HBD

68.7

PSA (Å²)

0.23

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C26H26ClFN2O4
MW	484.96
Aromatic Rings	4
Heavy Atoms	34
NP-Likeness	-1.03

Activity Summary

Ki 16 meas. best 9.52

IC50 5 meas. best 7.93

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	9.52	9.52	0.3	1
5-hydroxytryptamine receptor 2A CHEMBL322	Ki	9.52	9.52	0.3	1
D(2) dopamine receptor CHEMBL217	Ki	8.59	8.59	2.6	1
D(2) dopamine receptor CHEMBL339	Ki	8.59	8.59	2.6	1
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	8.48	8.48	3.3	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	8.48	8.48	3.3	1
D(3) dopamine receptor CHEMBL234	Ki	8.37	8.37	4.3	1
D(3) dopamine receptor CHEMBL3138	Ki	8.37	8.37	4.3	1
5-hydroxytryptamine receptor 1A CHEMBL214	IC50	7.93	7.93	11.8	1
Adrenergic receptor alpha-2 CHEMBL2093864	Ki	7.81	7.81	15.6	1
D(3) dopamine receptor CHEMBL234	IC50	7.61	7.61	24.8	1
D(2) dopamine receptor CHEMBL217	IC50	7.58	7.58	26.3	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	7.41	7.41	39.2	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	6.64	6.64	228.4	1
Histamine H1 receptor CHEMBL3943	Ki	5.95	5.95	1125.3	1
Histamine H1 receptor CHEMBL231	Ki	5.95	5.95	1125.3	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.8	5.8	1591.0	1
5-hydroxytryptamine receptor 2C CHEMBL324	Ki	5.77	5.77	1700.7	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	5.77	5.77	1700.7	1
Alpha-1A adrenergic receptor CHEMBL229	Ki	5.59	5.59	2569.2	1
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	5.59	5.59	2569.2	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	914.4	ng.hr.mL-1	Rattus norvegicus
AUC	702.7	ng.hr.mL-1	Rattus norvegicus
AUC	822.1	ng.hr.mL-1	Rattus norvegicus
AUC	644.4	ng.hr.mL-1	Rattus norvegicus
Cmax	148.67	nM	Rattus norvegicus
F	32.0	%	Rattus norvegicus
T1/2	5.0	hr	Rattus norvegicus
T1/2	6.7	hr	Rattus norvegicus
Tmax	3.0	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 2A	Ki	=	0.3	nM	9.52	Displacement of [3H]ketanserin from 5HT2A receptor in rat cerebral cortex after ...	23675993
5-hydroxytryptamine receptor 2A	Ki	=	0.3	nM	9.52	Binding affinity to 5-HT2A receptor (unknown origin)	33705900
D(2) dopamine receptor	Ki	=	2.6	nM	8.59	Displacement of [3H]spiperone from dopamine D2 receptor in rat striatum after 15...	23675993
D(2) dopamine receptor	Ki	=	2.6	nM	8.59	Binding affinity to dopamine D2 receptor (unknown origin)	33705900
5-hydroxytryptamine receptor 1A	Ki	=	3.3	nM	8.48	Displacement of [3H]8-OH-DPAT from 5HT1A receptor in rat cerebral cortex after 3...	23675993
5-hydroxytryptamine receptor 1A	Ki	=	3.3	nM	8.48	Binding affinity to 5-HT1A receptor (unknown origin)	33705900
D(3) dopamine receptor	Ki	=	4.3	nM	8.37	Binding affinity to dopamine D3 receptor (unknown origin)	33705900
D(3) dopamine receptor	Ki	=	4.3	nM	8.37	Displacement of [3H]7-OH-DPAT from dopamine D3 receptor in rat olfactory tubercl...	23675993
5-hydroxytryptamine receptor 1A	IC50	=	11.8	nM	7.93	Antagonist activity at 5HT1A receptor (unknown origin) expressed in CHOK1 cells ...	23675993
Adrenergic receptor alpha-2	Ki	=	15.6	nM	7.81	Displacement of [3H]rauwolscine from alpha-2 adrenergic receptor in rat cerebral...	23675993
D(3) dopamine receptor	IC50	=	24.8	nM	7.61	Antagonist activity at dopamine D3 receptor (unknown origin) expressed in CHOK1 ...	23675993
D(2) dopamine receptor	IC50	=	26.3	nM	7.58	Antagonist activity at dopamine D2 receptor (unknown origin) expressed in CHOK1 ...	23675993
5-hydroxytryptamine receptor 2A	IC50	=	39.2	nM	7.41	Antagonist activity at 5HT2A receptor (unknown origin) expressed in CHOK1 cells ...	23675993
5-hydroxytryptamine receptor 6	Ki	=	228.4	nM	6.64	Binding affinity to 5-HT6 receptor (unknown origin)	33705900
Histamine H1 receptor	Ki	=	1125.3	nM	5.95	Displacement of [3H]mepyramine from histamine H1 receptor in guinea pig cerebell...	23675993
Histamine H1 receptor	Ki	=	1125.3	nM	5.95	Binding affinity to histamine H1 receptor (unknown origin)	33705900
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	1591.0	nM	5.8	Inhibition of human ERG expressed in HEK293 cells by electrophysiology assay	23675993
5-hydroxytryptamine receptor 2C	Ki	=	1700.7	nM	5.77	Displacement of [3H]mesulergine from 5HT2C receptor in rat cerebral cortex after...	23675993
5-hydroxytryptamine receptor 2C	Ki	=	1700.7	nM	5.77	Binding affinity to 5-HT2C receptor (unknown origin)	33705900
Adrenergic receptor alpha-1	Ki	=	2569.2	nM	5.59	Displacement of [3H]prazosin from alpha-1 adrenergic receptor in rat cerebral co...	23675993

Literature References

PubMed	DOI	Target Context	# Activities
23675993	10.1021/jm400408r	Rattus norvegicus	12
23675993	10.1021/jm400408r	Mus musculus	8
23675993	10.1021/jm400408r	5-hydroxytryptamine receptor 2A	4
23675993	10.1021/jm400408r	5-hydroxytryptamine receptor 1A	4
23675993	10.1021/jm400408r	D(3) dopamine receptor	4
23675993	10.1021/jm400408r	D(2) dopamine receptor	4
23675993	10.1021/jm400408r	ADMET	2
33705900	10.1016/j.bmcl.2021.127909	Histamine H1 receptor	1
33705900	10.1016/j.bmcl.2021.127909	Alpha-1A adrenergic receptor	1
33705900	10.1016/j.bmcl.2021.127909	5-hydroxytryptamine receptor 6	1
33705900	10.1016/j.bmcl.2021.127909	5-hydroxytryptamine receptor 2C	1
33705900	10.1016/j.bmcl.2021.127909	5-hydroxytryptamine receptor 2A	1
33705900	10.1016/j.bmcl.2021.127909	5-hydroxytryptamine receptor 1A	1
33705900	10.1016/j.bmcl.2021.127909	D(3) dopamine receptor	1
33705900	10.1016/j.bmcl.2021.127909	D(2) dopamine receptor	1
23675993	10.1021/jm400408r	Histamine H1 receptor	1
23675993	10.1021/jm400408r	5-hydroxytryptamine receptor 2C	1
23675993	10.1021/jm400408r	Adrenergic receptor alpha-1	1
23675993	10.1021/jm400408r	Adrenergic receptor alpha-2	1
23675993	10.1021/jm400408r	Voltage-gated inwardly rectifying potassium channel KCNH2	1

Data from ChEMBL 36 via Core Engine