Compound Detail

CHEMBL14144

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CN1C2CCC1C(C(=O)Oc1ccccc1)C(c1ccc(Cl)cc1)C2

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL14144
Phase	Preclinical
Structure Type	MOL
InChI Key	AAEKULYONKUBOZ-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

355.9

MW (Da)

4.51

ALogP

HBA

HBD

29.5

PSA (Å²)

0.60

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C21H22ClNO2
MW	355.87
Aromatic Rings	2
Heavy Atoms	25
NP-Likeness	-0.01

Activity Summary

IC50 15 meas. best 8.7

Ki 10 meas. best 8.28

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Sodium-dependent dopamine transporter CHEMBL338	IC50	8.7	8.7	2.0	5
Sodium-dependent dopamine transporter CHEMBL238	Ki	8.28	8.28	5.2	1
Sodium-dependent dopamine transporter CHEMBL338	Ki	8.28	8.28	5.2	1
Norepinephrine transporter CHEMBL304	Ki	6.67	6.3467	213.0	3
Sodium-dependent serotonin transporter CHEMBL313	Ki	6.67	6.2767	214.0	3
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	6.62	6.62	242.3	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	6.41	6.41	390.0	1
Norepinephrine transporter CHEMBL304	IC50	5.63	5.55	2340.0	5
Sodium-dependent serotonin transporter CHEMBL313	IC50	5.63	5.61	2336.0	5

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Sodium-dependent dopamine transporter	IC50	=	1.98	nM	8.7	Inhibitory concentration required to inhibit dopamine transporter DAT was determ...	14711303
Sodium-dependent dopamine transporter	IC50	=	1.99	nM	8.7	Binding affinity towards Dopamine transporter by displacement of [3H]WIN-35428 r...	8411004
Sodium-dependent dopamine transporter	IC50	=	1.98	nM	8.7	Binding affinity towards dopamine transporter was determined using DA[3H]WIN-354...	7658431
Sodium-dependent dopamine transporter	IC50	=	1.98	nM	8.7	Inhibition of [3H]WIN-35428 binding at dopamine transporter was determined	12723940
Sodium-dependent dopamine transporter	IC50	=	1.98	nM	8.7	Binding affinity at the Dopamine transporter in rat striata by inhibition of 0.5...	7830281
Sodium-dependent dopamine transporter	Ki	=	5.25	nM	8.28	In vitro binding affinity against human dopamine transporter in dog kidney cell ...	14971892
Sodium-dependent dopamine transporter	Ki	=	5.25	nM	8.28	Inhibition of [3H]DA uptake by rat striatal dopamine transporter	7830281
Sodium-dependent serotonin transporter	Ki	=	214.0	nM	6.67	Inhibition of [3H]paroxetine binding at serotonin transporter was determined	12723940
Norepinephrine transporter	Ki	=	213.0	nM	6.67	Binding affinity towards norepinephrine transporter was determined using [3H]nis...	14711303
Sodium-dependent noradrenaline transporter	Ki	=	242.29	nM	6.62	In vitro binding affinity against human norepinephrine transporter in human embr...	14971892
Norepinephrine transporter	Ki	=	242.29	nM	6.62	Inhibition of [3H]NE uptake by rat frontal cortex Norepinephrine transporter	7830281
Sodium-dependent serotonin transporter	Ki	=	390.0	nM	6.41	Inhibition of [125I]RTI-55 binding to human serotonin transporter expressed in h...	14971892
Sodium-dependent serotonin transporter	Ki	=	390.68	nM	6.41	Inhibition of [3H]- 5-HT uptake in Serotonin transporter using serotonin uptake ...	7830281
Norepinephrine transporter	Ki	=	1780.0	nM	5.75	Affinity for norepinephrine transporter determined by [3H]nisoxetine displacemen...	12723940
Sodium-dependent serotonin transporter	Ki	=	1780.0	nM	5.75	Binding affinity towards serotonin transporter 5-HTT was determined using [3H]pa...	14711303
Sodium-dependent serotonin transporter	IC50	=	2340.0	nM	5.63	Inhibition of [3H]paroxetine binding at serotonin transporter was determined	12723940
Sodium-dependent serotonin transporter	IC50	=	2340.0	nM	5.63	Binding affinity towards Serotonin transporter was determined using 5-HT [3H]par...	7658431
Sodium-dependent serotonin transporter	IC50	=	2340.0	nM	5.63	Binding affinity towards serotonin transporter by displacement of [3H]- paroxeti...	8411004
Norepinephrine transporter	IC50	=	2340.0	nM	5.63	Inhibition of norepinephrine transporter (NET) determined using [3H]nisoxetine r...	14711303
Sodium-dependent serotonin transporter	IC50	=	2336.0	nM	5.63	Binding affinity at the Serotonin transporter in rat midbrain by inhibition of 0...	7830281

Literature References

PubMed	DOI	Target Context	# Activities
12723940	10.1021/jm030092d	Rattus norvegicus	5
7830281	10.1021/jm00002a020	Norepinephrine transporter	2
12723940	10.1021/jm030092d	Sodium-dependent serotonin transporter	2
12723940	10.1021/jm030092d	Norepinephrine transporter	2
14711303	10.1021/jm030453p	Sodium-dependent serotonin transporter	2
14711303	10.1021/jm030453p	Norepinephrine transporter	2
7830281	10.1021/jm00002a020	Monoamine transporters; serotonin & dopamine	2
7830281	10.1021/jm00002a020	Monoamine transporters; Norepininephrine & dopamine	2
7830281	10.1021/jm00002a020	Sodium-dependent serotonin transporter	2
7830281	10.1021/jm00002a020	Sodium-dependent dopamine transporter	2
14711303	10.1021/jm030453p	Sodium-dependent dopamine transporter	1
14971892	10.1021/jm030384e	Sodium-dependent serotonin transporter	1
14971892	10.1021/jm030384e	Sodium-dependent dopamine transporter	1
14971892	10.1021/jm030384e	Sodium-dependent noradrenaline transporter	1
14971892	10.1021/jm030384e	Monoamine transporters; serotonin & dopamine	1
8411004	10.1021/jm00072a007	Sodium-dependent dopamine transporter	1
8411004	10.1021/jm00072a007	Norepinephrine transporter	1
8411004	10.1021/jm00072a007	Sodium-dependent serotonin transporter	1
8411004	10.1021/jm00072a007	Monoamine transporters; Norepininephrine & dopamine	1
7658431	10.1021/jm00018a004	Sodium-dependent dopamine transporter	1

Data from ChEMBL 36 via Core Engine