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Compound Detail

CHEMBL4278465

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

Basic Information

ChEMBL ID CHEMBL4278465
Phase Preclinical
Structure Type MOL
InChI Key CVRMQFHSOSVJET-UHFFFAOYSA-N
22
Targets
28
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

539.0
MW (Da)
7.54
ALogP
3
HBA
1
HBD
26.7
PSA (Ų)
0.24
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 C28H28ClF5N2O
MW 538.99
Aromatic Rings 3
Heavy Atoms 37
NP-Likeness -0.95

Activity Summary

Ki 19 meas. best 6.34
IC50 9 meas. best 5.19

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 6.34 6.34 458.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 6.29 6.29 509.0 1
D(2) dopamine receptor
CHEMBL217
Ki 6.26 6.26 550.0 1
D(1B) dopamine receptor
CHEMBL1850
Ki 6.13 6.13 744.0 1
D(3) dopamine receptor
CHEMBL234
Ki 6.11 6.11 782.0 1
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 6.09 6.09 812.0 1
5-hydroxytryptamine receptor 1D
CHEMBL1983
Ki 5.97 5.97 1074.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 5.96 5.96 1094.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 5.95 5.95 1126.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 5.78 5.78 1670.0 1
5-hydroxytryptamine receptor 5A
CHEMBL3426
Ki 5.38 5.38 4152.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 5.22 5.22 6059.0 1
NIH3T3
CHEMBL614822
IC50 5.19 5.0167 6400.0 3
Lewis lung carcinoma cell line
CHEMBL614088
IC50 5.09 5.01 8200.0 3
MDA-MB-231
CHEMBL400
IC50 5.04 4.9767 9200.0 3
Delta-type opioid receptor
CHEMBL236
Ki 5.0 5.0 10000.0 1
Kappa-type opioid receptor
CHEMBL237
Ki 5.0 5.0 10000.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 5.0 5.0 10000.0 1
Mu-type opioid receptor
CHEMBL233
Ki 5.0 5.0 10000.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 5.0 5.0 10000.0 1
D(4) dopamine receptor
CHEMBL219
Ki 5.0 5.0 10000.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 5.0 5.0 10000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent noradrenaline transporter Ki = 458.0 nM 6.34 Displacement of [3H]Nisoxetine from human NET expressed in HEK cells by radiolig... 30389290
5-hydroxytryptamine receptor 2B Ki = 509.0 nM 6.29 Displacement of [3H]LSD from human 5-HT2B receptor expressed in HEK cells by rad... 30389290
D(2) dopamine receptor Ki = 550.0 nM 6.26 Displacement of [3H]N-methylspiperone from human dopamine D2 receptor expressed ... 30389290
D(1B) dopamine receptor Ki = 744.0 nM 6.13 Displacement of [3H]SCH23390 from human dopamine D5 receptor expressed in HEK293... 30389290
D(3) dopamine receptor Ki = 782.0 nM 6.11 Displacement of [3H]N-methylspiperone from human dopamine D3 receptor expressed ... 30389290
5-hydroxytryptamine receptor 7 Ki = 812.0 nM 6.09 Displacement of [3H]LSD from human 5-HT7A receptor expressed in HEK cells by rad... 30389290
5-hydroxytryptamine receptor 1D Ki = 1074.0 nM 5.97 Displacement of [3H]5-CT from human 5-HT1D receptor expressed in HEK293T cells b... 30389290
5-hydroxytryptamine receptor 1A Ki = 1094.0 nM 5.96 Displacement of [3H]-Way100635 from human 5HT1A receptor expressed in stable CHO... 30389290
5-hydroxytryptamine receptor 2C Ki = 1126.0 nM 5.95 Displacement of [3H]Mesulergine from human 5-HT2C receptor expressed in HEK293Fl... 30389290
5-hydroxytryptamine receptor 6 Ki = 1670.0 nM 5.78 Displacement of [3H]LSD from human 5-HT6 receptor expressed in HEK cells by radi... 30389290
5-hydroxytryptamine receptor 5A Ki = 4152.0 nM 5.38 Displacement of [3H]LSD from human 5-HT5A receptor expressed in Flp-In CHO cells... 30389290
5-hydroxytryptamine receptor 2A Ki = 6059.0 nM 5.22 Displacement of [3H]Ketanserin from 5-HT2A receptor (unknown origin) by radiolig... 30389290
NIH3T3 IC50 = 6400.0 nM 5.19 Cytotoxicity against mouse NIH/3T3 cells assessed as reduction in cell viability... 30389290
Lewis lung carcinoma cell line IC50 = 8200.0 nM 5.09 Cytotoxicity against mouse LLC cells harboring luciferin assessed as reduction i... 30389290
MDA-MB-231 IC50 = 9200.0 nM 5.04 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 30389290
D(1A) dopamine receptor Ki = 10000.0 nM 5.0 Displacement of [3H]SCH23390 from human dopamine D1 receptor expressed in HEK293... 30389290
D(4) dopamine receptor Ki = 10000.0 nM 5.0 Displacement of [3H]N-methylspiperone from human dopamine D4 receptor by radioli... 30389290
Kappa-type opioid receptor Ki = 10000.0 nM 5.0 Displacement of [3H]U69593 from KOR (unknown origin) expressed in HEK cells by r... 30389290
Mu-type opioid receptor Ki = 10000.0 nM 5.0 Displacement of [3H]DAMGO from human MOR expressed in HEK cells by radioligand b... 30389290
Delta-type opioid receptor Ki = 10000.0 nM 5.0 Displacement of [3H]DADLE from human DOR expressed in HEK cells by radioligand b... 30389290

Literature References

PubMed DOI Target Context # Activities
30389290 10.1016/j.bmcl.2018.10.036 Lewis lung carcinoma cell line 3
30389290 10.1016/j.bmcl.2018.10.036 NIH3T3 3
30389290 10.1016/j.bmcl.2018.10.036 MDA-MB-231 3
30389290 10.1016/j.bmcl.2018.10.036 Sodium-dependent dopamine transporter 2
30389290 10.1016/j.bmcl.2018.10.036 Histamine H1 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 D(1A) 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