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Compound Detail

CHEMBL563495

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Clc1cccc(OC(c2ccccn2)[C@H]2CCNC2)c1Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL563495
Phase Preclinical
Structure Type MOL
InChI Key KWWVMVUZZJMGRZ-CHPOKUKFSA-N
5
Targets
9
Activities
1
Assay Types
2
PK Parameters
9
Publications
0
Known Names

Molecular Properties

323.2
MW (Da)
4.12
ALogP
3
HBA
1
HBD
34.1
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 C16H16Cl2N2O
MW 323.22
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.86

Activity Summary

IC50 9 meas. best 7.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 7.89 7.665 13.0 2
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 7.85 7.61 14.0 2
Cytochrome P450 2D6
CHEMBL289
 IC50 6.22 5.75 600.0 2
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 5.97 5.895 1060.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.0 5.0 10000.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 2.0 hr Homo sapiens
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 IC50 = 13.0 nM 7.89 Inhibition of [3H]5-HT uptake at human 5HTT expressed in HEK293 cells 19359175
Sodium-dependent noradrenaline transporter IC50 = 14.0 nM 7.85 Inhibition of [3H]NA uptake at human NET expressed in HEK293 cells 19359175
Sodium-dependent serotonin transporter IC50 = 36.0 nM 7.44 Inhibition of [3H]5-HT uptake at human 5HTT expressed in HEK293 cells 19359175
Sodium-dependent noradrenaline transporter IC50 = 43.0 nM 7.37 Inhibition of [3H]NA uptake at human NET expressed in HEK293 cells 19359175
Cytochrome P450 2D6 IC50 = 600.0 nM 6.22 Inhibition of CYP2D6 19359175
Sodium-dependent dopamine transporter IC50 = 1060.0 nM 5.97 Inhibition of [3H]DA uptake at human DAT expressed in HEK293 cells 19359175
Sodium-dependent dopamine transporter IC50 = 1530.0 nM 5.82 Inhibition of [3H]DA uptake at human DAT expressed in HEK293 cells 19359175
Cytochrome P450 2D6 IC50 = 5300.0 nM 5.28 Inhibition of CYP2D6 19359175
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 10000.0 nM 5.0 Inhibition of human ERG channel 19359175

Literature References

PubMed DOI Target Context # Activities
19359175 10.1016/j.bmcl.2009.03.090 Sodium-dependent serotonin transporter 2
19359175 10.1016/j.bmcl.2009.03.090 Sodium-dependent noradrenaline transporter 2
19359175 10.1016/j.bmcl.2009.03.090 Sodium-dependent dopamine transporter 2
19359175 10.1016/j.bmcl.2009.03.090 Liver microsomes 2
19359175 10.1016/j.bmcl.2009.03.090 Voltage-gated inwardly rectifying potassium channel KCNH2 2
19359175 10.1016/j.bmcl.2009.03.090 Cytochrome P450 2D6 2
19359175 10.1016/j.bmcl.2009.03.090 Unchecked 2
19359175 10.1016/j.bmcl.2009.03.090 ADMET 1
19359175 10.1016/j.bmcl.2009.03.090 No relevant target 1

Data from ChEMBL 36 via Core Engine