Compound Detail

CHEMBL543876

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Cl.Cl.Fc1ccc(C(OCCN2CCN(CCCc3ccccc3)CC2)c2ccc(F)cc2)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL543876
Phase	Preclinical
Structure Type	MOL
InChI Key	MIBSKSYCRFWIRU-UHFFFAOYSA-N
Parent Compound	CHEMBL281594
Active Moiety	CHEMBL281594

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

450.6

MW (Da)

5.32

ALogP

HBA

HBD

15.7

PSA (Å²)

0.42

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C28H34Cl2F2N2O
MW	523.50
Aromatic Rings	3
Heavy Atoms	33
NP-Likeness	-0.81

Activity Summary

IC50 33 meas. best 9.0

Ki 6 meas. best 8.62

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Sodium-dependent dopamine transporter CHEMBL238	IC50	9.0	7.565	1.0	6
Sodium-dependent dopamine transporter CHEMBL238	Ki	8.62	8.62	2.4	1
Sodium-dependent dopamine transporter CHEMBL338	Ki	8.43	8.11	3.7	2
Sodium-dependent dopamine transporter CHEMBL338	IC50	8.18	8.04	6.6	3
Unchecked CHEMBL612545	Ki	7.31	7.31	48.5	1
Unchecked CHEMBL612545	IC50	6.95	5.8643	113.0	7
Sodium-dependent serotonin transporter CHEMBL313	IC50	6.88	6.88	132.0	2
Sodium-dependent serotonin transporter CHEMBL313	Ki	6.7	6.7	198.0	1
Norepinephrine transporter CHEMBL304	IC50	6.3	6.3	496.0	1
Transporter CHEMBL6184	Ki	6.3	6.3	496.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	5.84	5.84	1460.0	2
Kappa-type opioid receptor CHEMBL237	IC50	5.67	5.67	2140.0	1
Plasmodium falciparum CHEMBL364	IC50	5.6	5.2714	2511.9	7
Mu-type opioid receptor CHEMBL233	IC50	5.45	5.45	3530.0	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	5.42	5.42	3840.0	2
Danio rerio CHEMBL613963	IC50	5.24	5.24	5730.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Sodium-dependent dopamine transporter	IC50	=	1.0	nM	9.0	Affinity On-target Cellular interaction: (Inhibition of radiolabelled [3H]dopami...	-
Sodium-dependent dopamine transporter	Ki	=	2.42	nM	8.62	Displacement of [125I]IPT from DAT overexpressed in LLC-PK1 cell membrane by com...	22658558
Sodium-dependent dopamine transporter	Ki	=	3.7	nM	8.43	Binding affinity at dopamine transporter in rat brain by [3H]WIN-35428 displacem...	15189035
Sodium-dependent dopamine transporter	IC50	=	4.0	nM	8.4	Affinity On-target Cellular interaction: (Competitive radioligand binding assay,...	-
Sodium-dependent dopamine transporter	IC50	=	6.63	nM	8.18	Concentration required to inhibit [3H]DA (dopamine) uptake into rat striatal syn...	15456254
Sodium-dependent dopamine transporter	IC50	=	10.6	nM	7.97	Displacement of [3H]WIN35428 from DAT in Sprague-Dawley rat brain homogenates af...	22055716
Sodium-dependent dopamine transporter	IC50	=	10.6	nM	7.97	Inhibition of [3H]WIN-35428 binding to dopamine transporter of rat striatum	15456254
Sodium-dependent dopamine transporter	IC50	=	14.0	nM	7.85	Displacement of [3H]Win35428 from human recombinant DAT over-expressed in CHOK1 ...	24012181
Sodium-dependent dopamine transporter	Ki	=	16.2	nM	7.79	Inhibition of DAT in rat striatum assessed as [3H]dopamine accumulation	21446715
Unchecked	Ki	=	48.5	nM	7.31	Inhibition of NET in rat cerebral cortex assessed as [3H]norepinephrine accumula...	21446715
Unchecked	IC50	=	113.0	nM	6.95	PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf...	-
Sodium-dependent serotonin transporter	IC50	=	132.0	nM	6.88	Inhibition of [3H]citalopram binding to serotonin transporter of rat cerebral co...	15456254
Sodium-dependent serotonin transporter	IC50	=	132.0	nM	6.88	Displacement of [3H]citalopram from SERT in Sprague-Dawley rat brain homogenates...	22055716
Sodium-dependent dopamine transporter	IC50	=	190.0	nM	6.72	Inhibition of human DAT expressed in HEK293 cells assessed as inhibition of dopa...	22938049
Sodium-dependent dopamine transporter	IC50	=	190.0	nM	6.72	Inhibition of DA reuptake at human DAT expressed in HEK293 cells after 15 mins b...	24974340
Sodium-dependent dopamine transporter	IC50	=	200.0	nM	6.7	Inhibition of the Dopamine transporter (DAT, SLC6A3) as assessed by GPCR-mediate...	33446713
Sodium-dependent serotonin transporter	Ki	=	198.0	nM	6.7	Inhibition of SERT in rat cerebral cortex assessed as [3H]serotonin accumulation	21446715
Transporter	Ki	=	496.0	nM	6.3	Displacement of [3H]nisoxetine from NET in Sprague-Dawley rat brain cortex membr...	22055716
Norepinephrine transporter	IC50	=	496.0	nM	6.3	Inhibition of [3H]nisoxetine binding to norepinephrine transporter of rat cerebr...	15456254
Unchecked	IC50	=	903.2	nM	6.04	PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co...	-

Literature References

PubMed	DOI	Target Context	# Activities
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
24974340	10.1016/j.bmcl.2014.06.026	Sodium-dependent dopamine transporter	4
24974340	10.1016/j.bmcl.2014.06.026	Sodium-dependent serotonin transporter	4
24974340	10.1016/j.bmcl.2014.06.026	Sodium-dependent noradrenaline transporter	4
15456254	10.1021/jm049796t	Sodium-dependent dopamine transporter	3
22938049	10.1021/jm3008294	Sodium-dependent dopamine transporter	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
22938049	10.1021/jm3008294	Sodium-dependent noradrenaline transporter	2
22055716	10.1016/j.bmc.2011.10.028	Unchecked	2
22938049	10.1021/jm3008294	Sodium-dependent serotonin transporter	2
-	10.6019/CHEMBL5723379	Sodium-dependent dopamine transporter	2
24012181	10.1016/j.bmcl.2013.08.062	Sodium-dependent dopamine transporter	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
17417631	10.1038/nchembio873	Unchecked	1
21446715	10.1021/jm200020a	Sodium-dependent serotonin transporter	1
21446715	10.1021/jm200020a	Sodium-dependent dopamine transporter	1
-	10.6019/CHEMBL5724796	Bromodomain-containing protein 4	1
15456254	10.1021/jm049796t	No relevant target	1
15456254	10.1021/jm049796t	Sodium-dependent serotonin transporter	1
15189035	10.1021/jm030646c	Sodium-dependent dopamine transporter	1

Data from ChEMBL 36 via Core Engine