Compound Detail

CHEMBL259656

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O=C(c1cc2c(cc1F)OC(c1ccc(F)cc1)(c1ccc(Cl)cc1Cl)O2)N1CCOCC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL259656
Phase	Preclinical
Structure Type	MOL
InChI Key	VUCKSZWMRCSPME-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

492.3

MW (Da)

5.42

ALogP

HBA

HBD

48.0

PSA (Å²)

0.49

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C24H17Cl2F2NO4
MW	492.31
Aromatic Rings	3
Heavy Atoms	33
NP-Likeness	-1.09

Activity Summary

Ki 10 meas. best 8.4

IC50 3 meas. best 5.5

EC50 1 meas. best 7.96

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cannabinoid receptor 1 CHEMBL218	Ki	8.4	8.4	4.0	1
Cannabinoid receptor 1 CHEMBL218	EC50	7.96	7.96	11.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.5	6.5	319.1	1
Kappa-type opioid receptor CHEMBL237	Ki	6.3	6.3	502.8	1
Sigma intracellular receptor 2 CHEMBL4105907	Ki	6.29	6.29	508.9	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	6.22	6.22	607.3	1
D(1B) dopamine receptor CHEMBL1850	Ki	6.15	6.15	708.4	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	5.6	5.6	2537.8	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	5.58	5.58	2657.4	1
Mu-type opioid receptor CHEMBL233	Ki	5.5	5.5	3141.9	1
Glucose-dependent insulinotropic receptor CHEMBL5652	IC50	5.5	5.5	3129.2	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	5.46	5.46	3456.6	1
G-protein coupled receptor 183 CHEMBL3259470	IC50	5.45	5.45	3575.4	1
G-protein coupled receptor 35 CHEMBL1293267	IC50	5.27	5.27	5353.4	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	10.0	mL.min-1.g-1	Homo sapiens
CL	22.0	mL.min-1.g-1	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cannabinoid receptor 1	Ki	=	4.0	nM	8.4	Displacement of [3H]CP-55940 from human CB1R expressed in HEK293 cells	18335976
Cannabinoid receptor 1	EC50	=	11.0	nM	7.96	Activity at human CB1R expressed in HEK293 cells assessed as intracellular cAMP ...	18335976
5-hydroxytryptamine receptor 2C	Ki	=	319.12	nM	6.5	PDSP Secondary Binding target: HTR2C - Compounds are tested at 10 uM concentrati...	-
Kappa-type opioid receptor	Ki	=	502.75	nM	6.3	PDSP Secondary Binding target: OPRK1 - Compounds are tested at 10 uM concentrati...	-
Sigma intracellular receptor 2	Ki	=	508.86	nM	6.29	PDSP Secondary Binding target: TMEM97 - Compounds are tested at 10 uM concentrat...	-
5-hydroxytryptamine receptor 2B	Ki	=	607.3	nM	6.22	PDSP Secondary Binding target: HTR2B - Compounds are tested at 10 uM concentrati...	-
D(1B) dopamine receptor	Ki	=	708.43	nM	6.15	PDSP Secondary Binding target: DRD5 - Compounds are tested at 10 uM concentratio...	-
Sodium-dependent noradrenaline transporter	Ki	=	2537.76	nM	5.6	PDSP Secondary Binding target: SLC6A2 - Compounds are tested at 10 uM concentrat...	-
5-hydroxytryptamine receptor 2A	Ki	=	2657.36	nM	5.58	PDSP Secondary Binding target: HTR2A - Compounds are tested at 10 uM concentrati...	-
Glucose-dependent insulinotropic receptor	IC50	=	3129.2	nM	5.5	GPCR PRESTO-Tango dose-response in antagonist mode with target: GPR119	-
Mu-type opioid receptor	Ki	=	3141.95	nM	5.5	PDSP Secondary Binding target: OPRM1 - Compounds are tested at 10 uM concentrati...	-
Sodium-dependent dopamine transporter	Ki	=	3456.6	nM	5.46	PDSP Secondary Binding target: SLC6A3 - Compounds are tested at 10 uM concentrat...	-
G-protein coupled receptor 183	IC50	=	3575.39	nM	5.45	GPCR PRESTO-Tango dose-response in antagonist mode with target: GPR183	-
G-protein coupled receptor 35	IC50	=	5353.35	nM	5.27	GPCR PRESTO-Tango dose-response in antagonist mode with target: GPR35	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL4689842	HEK-293T	346
-	10.6019/CHEMBL4689842	U2OS	345
-	10.6019/CHEMBL4689842	Fibroblast	343
-	10.6019/CHEMBL5209801	N-formyl peptide receptor 2	5
-	10.6019/CHEMBL5209801	Glucose-dependent insulinotropic receptor	5
-	10.6019/CHEMBL5209801	Glucagon-like peptide 1 receptor	5
-	10.6019/CHEMBL5209801	Apelin receptor	5
-	10.6019/CHEMBL5209801	CX3C chemokine receptor 1	5
-	10.6019/CHEMBL5209801	Beta-2 adrenergic receptor	5
-	10.6019/CHEMBL5209801	C5a anaphylatoxin chemotactic receptor 1	5
-	10.6019/CHEMBL5209801	Adhesion G-protein coupled receptor F1	5
-	10.6019/CHEMBL5209801	Type-1 angiotensin II receptor	5
-	10.6019/CHEMBL5209801	Free fatty acid receptor 4	5
-	10.6019/CHEMBL5209801	Sphingosine 1-phosphate receptor 1	5
-	10.6019/CHEMBL5209801	Alpha-2A adrenergic receptor	5
-	10.6019/CHEMBL5209801	G-protein coupled receptor 35	2
18335976	10.1021/jm701487t	Cannabinoid receptor 1	2
18335976	10.1021/jm701487t	Liver microsomes	2
-	10.6019/CHEMBL5060014	Fibroblast growth factor receptor 3	1
-	10.6019/CHEMBL5060014	Casein kinase I isoform delta	1

Data from ChEMBL 36 via Core Engine