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Compound Detail

CHEMBL1080787

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CC(C)CN(C(=O)c1cccc(Cl)c1Cl)[C@H]1CCNC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1080787
Phase Preclinical
Structure Type MOL
InChI Key PIKCALBGLDBAKK-NSHDSACASA-N
6
Targets
12
Activities
2
Assay Types
4
PK Parameters
20
Publications
0
Known Names

Molecular Properties

315.2
MW (Da)
3.45
ALogP
2
HBA
1
HBD
32.3
PSA (Ų)
0.92
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H20Cl2N2O
MW 315.24
Aromatic Rings 1
Heavy Atoms 20
NP-Likeness -1.42

Activity Summary

IC50 6 meas. best 5.44
Ki 6 meas. best 8.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 8.22 8.22 6.0 2
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 7.68 7.68 21.0 2
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 6.26 6.26 544.0 2
Unchecked
CHEMBL612545
 IC50 5.44 5.2667 3600.0 3
Kappa-type opioid receptor
CHEMBL237
 IC50 5.24 5.24 5800.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.7 4.7 20000.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 11.0 mL.min-1.g-1 Homo sapiens
CL 3.0 uL.min-1.(10^6cells)-1 Homo sapiens
Fu 4.0 nM Canis lupus familiaris
T1/2 2.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent serotonin transporter Ki = 6.0 nM 8.22 Displacement of [3H]5HT from human 5HT transporter expressed in HEK293 cells by ... 19647430
Sodium-dependent serotonin transporter Ki = 6.0 nM 8.22 Displacement of [3H]citalopram from human SERT expressed in HEK293 cells by scin... 20471260
Sodium-dependent noradrenaline transporter Ki = 21.0 nM 7.68 Displacement of [3H]noradrenaline from human NET receptor expressed in HEK293 ce... 19647430
Sodium-dependent noradrenaline transporter Ki = 21.0 nM 7.68 Displacement of [3H]nisoxetine from human NET expressed in HEK293 cells by scint... 20471260
Sodium-dependent dopamine transporter Ki = 544.0 nM 6.26 Displacement of [3H]dopamine from human DAT receptor expressed in HEK293 cells b... 19647430
Sodium-dependent dopamine transporter Ki = 544.0 nM 6.26 Displacement of [3H]dopamine from human DAT expressed in HEK293 cells by scintil... 20471260
Unchecked IC50 = 3600.0 nM 5.44 Binding affinity to sodium channel 19647430
Unchecked IC50 = 5100.0 nM 5.29 Binding affinity to sigma opioid receptor 19647430
Kappa-type opioid receptor IC50 = 5800.0 nM 5.24 Binding affinity to kappa opioid receptor 19647430
Unchecked IC50 = 8550.0 nM 5.07 Inhibition of tetrodotoxin-sensitive sodium channel 20471260
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 20000.0 nM 4.7 Inhibition of human ERG 19647430
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 20000.0 nM 4.7 Displacement of [3H]dofetilide from human ERG 20471260

Literature References

PubMed DOI Target Context # Activities
19647430 10.1016/j.bmcl.2009.07.049 MDCK 3
19647430 10.1016/j.bmcl.2009.07.049 Cytochrome P450 3A4 3
19647430 10.1016/j.bmcl.2009.07.049 Rattus norvegicus 2
19647430 10.1016/j.bmcl.2009.07.049 Canis familiaris 2
19647430 10.1016/j.bmcl.2009.07.049 No relevant target 2
19647430 10.1016/j.bmcl.2009.07.049 Plasma 2
19647430 10.1016/j.bmcl.2009.07.049 Unchecked 2
19647430 10.1016/j.bmcl.2009.07.049 Caco-2 2
19647430 10.1016/j.bmcl.2009.07.049 Cytochrome P450 2C9 1
20471260 10.1016/j.bmcl.2010.04.052 Unchecked 1
20471260 10.1016/j.bmcl.2010.04.052 Sodium-dependent serotonin transporter 1
19647430 10.1016/j.bmcl.2009.07.049 Kappa-type opioid receptor 1
19647430 10.1016/j.bmcl.2009.07.049 Cytochrome P450 2C19 1
19647430 10.1016/j.bmcl.2009.07.049 Sodium-dependent serotonin transporter 1
19647430 10.1016/j.bmcl.2009.07.049 Cytochrome P450 1A2 1
19647430 10.1016/j.bmcl.2009.07.049 Cytochrome P450 2D6 1
19647430 10.1016/j.bmcl.2009.07.049 Hepatocyte 1
19647430 10.1016/j.bmcl.2009.07.049 Voltage-gated inwardly rectifying potassium channel KCNH2 1
19647430 10.1016/j.bmcl.2009.07.049 Liver microsomes 1
19647430 10.1016/j.bmcl.2009.07.049 Sodium-dependent dopamine transporter 1

Data from ChEMBL 36 via Core Engine