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Compound Detail

CHEMBL4287623

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OC1(c2ccc(Cl)c(C(F)(F)F)c2)CCN(CCCC=C(c2ccc(F)cc2)c2ccc(F)cc2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4287623
Phase Preclinical
Structure Type MOL
InChI Key GOFKTWKLJPDQCU-UHFFFAOYSA-N
15
Targets
21
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

536.0
MW (Da)
7.83
ALogP
2
HBA
1
HBD
23.5
PSA (Ų)
0.25
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C29H27ClF5NO
MW 535.98
Aromatic Rings 3
Heavy Atoms 37
NP-Likeness -0.54

Activity Summary

Ki 12 meas. best 6.5
IC50 9 meas. best 5.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(2) dopamine receptor
CHEMBL217
 Ki 6.5 6.5 317.0 1
Mu-type opioid receptor
CHEMBL233
 Ki 6.48 6.48 328.0 1
Histamine H2 receptor
CHEMBL1941
 Ki 6.28 6.28 526.0 1
D(3) dopamine receptor
CHEMBL234
 Ki 6.26 6.26 552.0 1
Histamine H1 receptor
CHEMBL231
 Ki 6.14 6.14 718.0 1
Kappa-type opioid receptor
CHEMBL237
 Ki 5.99 5.99 1021.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 5.96 5.96 1105.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 5.87 5.87 1363.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 5.79 5.79 1603.0 1
D(4) dopamine receptor
CHEMBL219
 Ki 5.78 5.78 1643.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 5.66 5.66 2199.0 1
NIH3T3
CHEMBL614822
 IC50 5.15 4.8033 7100.0 3
MDA-MB-231
CHEMBL400
 IC50 5.02 4.8233 9600.0 3
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 5.0 5.0 10000.0 1
Lewis lung carcinoma cell line
CHEMBL614088
 IC50 4.95 4.8933 11200.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(2) dopamine receptor Ki = 317.0 nM 6.5 Displacement of [3H]N-methylspiperone from human dopamine D2 receptor expressed ... 30389290
Mu-type opioid receptor Ki = 328.0 nM 6.48 Displacement of [3H]DAMGO from human MOR expressed in HEK cells by radioligand b... 30389290
Histamine H2 receptor Ki = 526.0 nM 6.28 Displacement of [3H]Cimetidine from human H2 receptor expressed in HEK cells by ... 30389290
D(3) dopamine receptor Ki = 552.0 nM 6.26 Displacement of [3H]N-methylspiperone from human dopamine D3 receptor expressed ... 30389290
Histamine H1 receptor Ki = 718.0 nM 6.14 Displacement of [3H]Pyrilamine from human H1 receptor expressed in HEK cells by ... 30389290
Kappa-type opioid receptor Ki = 1021.0 nM 5.99 Displacement of [3H]U69593 from KOR (unknown origin) expressed in HEK cells by r... 30389290
5-hydroxytryptamine receptor 2A Ki = 1105.0 nM 5.96 Displacement of [3H]Ketanserin from 5-HT2A receptor (unknown origin) by radiolig... 30389290
5-hydroxytryptamine receptor 1A Ki = 1363.0 nM 5.87 Displacement of [3H]-Way100635 from human 5HT1A receptor expressed in stable CHO... 30389290
5-hydroxytryptamine receptor 2C Ki = 1603.0 nM 5.79 Displacement of [3H]Mesulergine from human 5-HT2C receptor expressed in HEK293Fl... 30389290
D(4) dopamine receptor Ki = 1643.0 nM 5.78 Displacement of [3H]N-methylspiperone from human dopamine D4 receptor by radioli... 30389290
5-hydroxytryptamine receptor 2B Ki = 2199.0 nM 5.66 Displacement of [3H]LSD from human 5-HT2B receptor expressed in HEK cells by rad... 30389290
NIH3T3 IC50 = 7100.0 nM 5.15 Cytotoxicity against mouse NIH/3T3 cells assessed as reduction in cell viability... 30389290
MDA-MB-231 IC50 = 9600.0 nM 5.02 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 30389290
5-hydroxytryptamine receptor 7 Ki = 10000.0 nM 5.0 Displacement of [3H]LSD from human 5-HT7A receptor expressed in HEK cells by rad... 30389290
Lewis lung carcinoma cell line IC50 = 11200.0 nM 4.95 Cytotoxicity against mouse LLC cells harboring luciferin assessed as reduction i... 30389290
Lewis lung carcinoma cell line IC50 = 12000.0 nM 4.92 Cytotoxicity against mouse LLC cells harboring luciferin assessed as reduction i... 30389290
NIH3T3 IC50 = 14800.0 nM 4.83 Cytotoxicity against mouse NIH/3T3 cells assessed as reduction in cell viability... 30389290
MDA-MB-231 IC50 = 14900.0 nM 4.83 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 30389290
Lewis lung carcinoma cell line IC50 = 15600.0 nM 4.81 Cytotoxicity against mouse LLC cells harboring luciferin assessed as reduction i... 30389290
MDA-MB-231 IC50 = 23900.0 nM 4.62 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 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