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Compound Detail

CHEMBL1644978

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OC1(c2ccc(Cl)c(C(F)(F)F)c2)CCN(CCCCC(c2ccc(F)cc2)c2ccc(F)cc2)CC1

Basic Information

ChEMBL ID CHEMBL1644978
Phase Preclinical
Structure Type MOL
InChI Key QBWLTDPVSJCLIE-UHFFFAOYSA-N
24
Targets
30
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

538.0
MW (Da)
7.92
ALogP
2
HBA
1
HBD
23.5
PSA (Ų)
0.23
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C29H29ClF5NO
MW 538.00
Aromatic Rings 3
Heavy Atoms 37
NP-Likeness -0.70

Activity Summary

Ki 20 meas. best 7.11
IC50 9 meas. best 5.39
EC50 1 meas. best 5.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 7.11 7.11 77.0 1
D(2) dopamine receptor
CHEMBL217
Ki 6.71 6.71 194.0 1
D(3) dopamine receptor
CHEMBL234
Ki 6.68 6.68 209.0 1
Mu-type opioid receptor
CHEMBL233
Ki 6.45 6.45 356.0 1
D(4) dopamine receptor
CHEMBL219
Ki 6.42 6.42 385.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 6.37 6.37 423.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 6.37 6.37 428.0 1
D(1B) dopamine receptor
CHEMBL1850
Ki 6.28 6.28 529.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 6.28 6.28 529.0 1
Histamine H2 receptor
CHEMBL1941
Ki 6.26 6.26 546.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 6.1 6.1 798.0 1
5-hydroxytryptamine receptor 1D
CHEMBL1983
Ki 6.07 6.07 844.0 1
5-hydroxytryptamine receptor 5A
CHEMBL3426
Ki 6.05 6.05 894.0 1
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 6.01 6.01 969.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 6.0 6.0 1000.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 5.86 5.86 1395.0 1
Delta-type opioid receptor
CHEMBL236
Ki 5.85 5.85 1413.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 5.78 5.78 1671.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 5.77 5.77 1712.0 1
Kappa-type opioid receptor
CHEMBL237
Ki 5.57 5.57 2669.0 1
H4
CHEMBL1075452
EC50 5.57 5.57 2700.0 1
Lewis lung carcinoma cell line
CHEMBL614088
IC50 5.39 5.34 4100.0 3
NIH3T3
CHEMBL614822
IC50 5.39 5.2867 4100.0 3
MDA-MB-231
CHEMBL400
IC50 5.32 5.28 4800.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent noradrenaline transporter Ki = 77.0 nM 7.11 Displacement of [3H]Nisoxetine from human NET expressed in HEK cells by radiolig... 30389290
D(2) dopamine receptor Ki = 194.0 nM 6.71 Displacement of [3H]N-methylspiperone from human dopamine D2 receptor expressed ... 30389290
D(3) dopamine receptor Ki = 209.0 nM 6.68 Displacement of [3H]N-methylspiperone from human dopamine D3 receptor expressed ... 30389290
Mu-type opioid receptor Ki = 356.0 nM 6.45 Displacement of [3H]DAMGO from human MOR expressed in HEK cells by radioligand b... 30389290
D(4) dopamine receptor Ki = 385.0 nM 6.42 Displacement of [3H]N-methylspiperone from human dopamine D4 receptor by radioli... 30389290
Sodium-dependent serotonin transporter Ki = 428.0 nM 6.37 Displacement of [3H]Citalopram from human SERT expressed in HEK cells by radioli... 30389290
5-hydroxytryptamine receptor 2B Ki = 423.0 nM 6.37 Displacement of [3H]LSD from human 5-HT2B receptor expressed in HEK cells by rad... 30389290
Sodium-dependent dopamine transporter Ki = 529.0 nM 6.28 Displacement of [3H]WIN35428 from human DAT expressed in HEK cells by radioligan... 30389290
D(1B) dopamine receptor Ki = 529.0 nM 6.28 Displacement of [3H]SCH23390 from human dopamine D5 receptor expressed in HEK293... 30389290
Histamine H2 receptor Ki = 546.0 nM 6.26 Displacement of [3H]Cimetidine from human H2 receptor expressed in HEK cells by ... 30389290
D(1A) dopamine receptor Ki = 798.0 nM 6.1 Displacement of [3H]SCH23390 from human dopamine D1 receptor expressed in HEK293... 30389290
5-hydroxytryptamine receptor 1D Ki = 844.0 nM 6.07 Displacement of [3H]5-CT from human 5-HT1D receptor expressed in HEK293T cells b... 30389290
5-hydroxytryptamine receptor 5A Ki = 894.0 nM 6.05 Displacement of [3H]LSD from human 5-HT5A receptor expressed in Flp-In CHO cells... 30389290
5-hydroxytryptamine receptor 7 Ki = 969.0 nM 6.01 Displacement of [3H]LSD from human 5-HT7A receptor expressed in HEK cells by rad... 30389290
5-hydroxytryptamine receptor 2A Ki = 1000.0 nM 6.0 Displacement of [3H]Ketanserin from 5-HT2A receptor (unknown origin) by radiolig... 30389290
5-hydroxytryptamine receptor 1A Ki = 1395.0 nM 5.86 Displacement of [3H]-Way100635 from human 5HT1A receptor expressed in stable CHO... 30389290
Delta-type opioid receptor Ki = 1413.0 nM 5.85 Displacement of [3H]DADLE from human DOR expressed in HEK cells by radioligand b... 30389290
5-hydroxytryptamine receptor 6 Ki = 1671.0 nM 5.78 Displacement of [3H]LSD from human 5-HT6 receptor expressed in HEK cells by radi... 30389290
5-hydroxytryptamine receptor 2C Ki = 1712.0 nM 5.77 Displacement of [3H]Mesulergine from human 5-HT2C receptor expressed in HEK293Fl... 30389290
H4 EC50 = 2700.0 nM 5.57 Induction of autophagy in human H4 cells expressing LC3 using DAPI staining afte... 21126871

Literature References

PubMed DOI Target Context # Activities
30389290 10.1016/j.bmcl.2018.10.036 Mus musculus 21
30389290 10.1016/j.bmcl.2018.10.036 MDA-MB-231 3
30389290 10.1016/j.bmcl.2018.10.036 NIH3T3 3
30389290 10.1016/j.bmcl.2018.10.036 ADMET 3
30389290 10.1016/j.bmcl.2018.10.036 Lewis lung carcinoma cell line 3
30389290 10.1016/j.bmcl.2018.10.036 D(1A) dopamine receptor 2
30389290 10.1016/j.bmcl.2018.10.036 Delta-type opioid receptor 2
30389290 10.1016/j.bmcl.2018.10.036 Mu-type opioid receptor 2
30389290 10.1016/j.bmcl.2018.10.036 Kappa-type opioid receptor 2
30389290 10.1016/j.bmcl.2018.10.036 D(1B) dopamine receptor 2
30389290 10.1016/j.bmcl.2018.10.036 D(4) dopamine receptor 2
30389290 10.1016/j.bmcl.2018.10.036 D(3) dopamine receptor 2
30389290 10.1016/j.bmcl.2018.10.036 D(2) dopamine receptor 2
30389290 10.1016/j.bmcl.2018.10.036 5-hydroxytryptamine receptor 7 2
30389290 10.1016/j.bmcl.2018.10.036 5-hydroxytryptamine receptor 6 2
30389290 10.1016/j.bmcl.2018.10.036 5-hydroxytryptamine receptor 5A 2
30389290 10.1016/j.bmcl.2018.10.036 5-hydroxytryptamine receptor 2C 2
30389290 10.1016/j.bmcl.2018.10.036 5-hydroxytryptamine receptor 2B 2
30389290 10.1016/j.bmcl.2018.10.036 5-hydroxytryptamine receptor 2A 2
30389290 10.1016/j.bmcl.2018.10.036 5-hydroxytryptamine receptor 1D 2

Data from ChEMBL 36 via Core Engine