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Compound Detail

CHEMBL267615

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CCc1[nH]c2ccc(OC)cc2c1CCN(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL267615
Phase Preclinical
Structure Type MOL
InChI Key ZEYRDXUWJDGTLD-UHFFFAOYSA-N
11
Targets
24
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

246.3
MW (Da)
2.84
ALogP
2
HBA
1
HBD
28.3
PSA (Ų)
0.88
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H22N2O
MW 246.35
Aromatic Rings 2
Heavy Atoms 18
NP-Likeness -0.18

Activity Summary

Ki 16 meas. best 7.8
IC50 7 meas. best 7.36
EC50 1 meas. best 6.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 6
CHEMBL3371
 Ki 7.8 7.748 16.0 10
5-hydroxytryptamine receptor 4
CHEMBL5017
 IC50 7.36 7.36 44.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
 IC50 7.07 7.07 85.0 2
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 6.77 6.77 170.0 1
5-hydroxytryptamine receptor 1D
CHEMBL1983
 Ki 6.54 6.54 290.0 1
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 6.52 6.52 300.0 1
5-hydroxytryptamine receptor 1E
CHEMBL2182
 Ki 6.28 6.28 520.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 IC50 6.21 6.21 620.0 1
ADMET
CHEMBL612558
 EC50 6.15 6.15 710.0 1
5-hydroxytryptamine receptor 1D
CHEMBL1983
 IC50 5.85 5.85 1400.0 1
5-hydroxytryptamine receptor 7
CHEMBL3155
 IC50 5.82 5.82 1500.0 1
5-hydroxytryptamine receptor 2C
CHEMBL324
 Ki 5.74 5.74 1810.0 1
5-hydroxytryptamine receptor 5A
CHEMBL3426
 Ki 5.33 5.33 4620.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 IC50 5.26 5.26 5500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 6 Ki = 16.0 nM 7.8 Displacement of [3H]lysergic acid diethylamide from human 5-HT6 receptor transfe... 26099069
5-hydroxytryptamine receptor 6 Ki = 16.0 nM 7.8 Binding affinity to 5-HT6 receptor (unknown origin) -
5-hydroxytryptamine receptor 6 Ki = 16.0 nM 7.8 Binding affinity to 5HT6 receptor 19758807
5-hydroxytryptamine receptor 6 Ki = 16.0 nM 7.8 Displacement of [3H]LSD from human 5HT6 receptor expressed in HEK293 cells by li... 19159187
5-hydroxytryptamine receptor 6 Ki = 16.0 nM 7.8 Displacement of [3H]LSD from human 5HT6 receptor expressed in HEK293 cells 18201064
5-hydroxytryptamine receptor 6 Ki = 16.0 nM 7.8 Binding affinity against 5-hydroxytryptamine 6 receptor 15357994
5-hydroxytryptamine receptor 6 Ki = 16.0 nM 7.8 Binding affinity against 5 Hydroxy tryptamine 6 receptor 15745826
5-hydroxytryptamine receptor 6 Ki = 16.0 nM 7.8 Binding affinity towards human 5-hydroxytryptamine 6 receptor 12825922
5-hydroxytryptamine receptor 6 Ki = 16.0 nM 7.8 Compound was evaluated for its binding affinity towards human 5-hydroxytryptamin... 10715164
5-hydroxytryptamine receptor 4 IC50 = 44.0 nM 7.36 Inhibitory activity against 5-hydroxytryptamine 4 receptor in guinea pig 16055331
5-hydroxytryptamine receptor 6 Ki = 52.0 nM 7.28 Binding affinity for human 5-hydroxytryptamine 6 receptor expressed in HEK 293 h... 10715164
5-hydroxytryptamine receptor 6 IC50 = 85.0 nM 7.07 Inhibitory activity against 5-hydroxytryptamine 6 receptor in human 16055331
5-hydroxytryptamine receptor 6 IC50 = 85.0 nM 7.07 Displacement of [3H]LSD binding to cloned human 5-hydroxytryptamine 6 receptor s... 16055331
5-hydroxytryptamine receptor 1A Ki = 170.0 nM 6.77 Compound was evaluated for its binding affinity towards human 5-hydroxytryptamin... 10715164
5-hydroxytryptamine receptor 1D Ki = 290.0 nM 6.54 Compound was evaluated for its binding affinity towards human 5-hydroxytryptamin... 10715164
5-hydroxytryptamine receptor 7 Ki = 300.0 nM 6.52 Compound was evaluated for its binding affinity towards human 5-hydroxytryptamin... 10715164
5-hydroxytryptamine receptor 1E Ki = 520.0 nM 6.28 Compound was evaluated for its binding affinity towards human 5-hydroxytryptamin... 10715164
5-hydroxytryptamine receptor 2A IC50 = 620.0 nM 6.21 Inhibitory activity against 5-hydroxytryptamine 2A receptor in human 16055331
ADMET EC50 = 710.0 nM 6.15 Concentration to stimulate the cAMP production in BHK cells 16055331
5-hydroxytryptamine receptor 1D IC50 = 1400.0 nM 5.85 Inhibitory activity against 5-hydroxytryptamine 1D receptor in calf 16055331

Literature References

PubMed DOI Target Context # Activities
26099069 10.1021/acs.jmedchem.5b00179 Unchecked 3
16055331 10.1016/j.bmcl.2005.06.067 5-hydroxytryptamine receptor 6 3
10715164 10.1021/jm990550b 5-hydroxytryptamine receptor 6 2
15745826 10.1016/j.bmcl.2005.01.031 5-hydroxytryptamine receptor 6 1
12825922 10.1021/jm030030n 5-hydroxytryptamine receptor 6 1
26099069 10.1021/acs.jmedchem.5b00179 5-hydroxytryptamine receptor 6 1
16055331 10.1016/j.bmcl.2005.06.067 5-hydroxytryptamine receptor 1A 1
16055331 10.1016/j.bmcl.2005.06.067 ADMET 1
16055331 10.1016/j.bmcl.2005.06.067 5-hydroxytryptamine receptor 7 1
16055331 10.1016/j.bmcl.2005.06.067 5-hydroxytryptamine receptor 4 1
10715164 10.1021/jm990550b Sodium-dependent noradrenaline transporter 1
15357994 10.1016/j.bmcl.2004.05.076 5-hydroxytryptamine receptor 6 1
10715164 10.1021/jm990550b Sodium-dependent serotonin transporter 1
15771424 10.1021/jm049615n 5-hydroxytryptamine receptor 6 1
10715164 10.1021/jm990550b 5-hydroxytryptamine receptor 7 1
10715164 10.1021/jm990550b 5-hydroxytryptamine receptor 5A 1
10715164 10.1021/jm990550b 5-hydroxytryptamine receptor 2C 1
10715164 10.1021/jm990550b 5-hydroxytryptamine receptor 2A 1
10715164 10.1021/jm990550b 5-hydroxytryptamine receptor 1E 1
10715164 10.1021/jm990550b 5-hydroxytryptamine receptor 1D 1

Data from ChEMBL 36 via Core Engine