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Compound Detail

CHEMBL4293307

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COc1ccc(N(CCCCN2CCC(O)(c3ccc(Cl)c(C(F)(F)F)c3)CC2)c2ccc(OC)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4293307
Phase Preclinical
Structure Type MOL
InChI Key DYLSSJRMONSQGQ-UHFFFAOYSA-N
23
Targets
29
Activities
2
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

563.1
MW (Da)
7.28
ALogP
5
HBA
1
HBD
45.2
PSA (Ų)
0.26
QED
2
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C30H34ClF3N2O3
MW 563.06
Aromatic Rings 3
Heavy Atoms 39
NP-Likeness -0.75

Activity Summary

Ki 20 meas. best 6.38
IC50 9 meas. best 5.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(2) dopamine receptor
CHEMBL217
 Ki 6.38 6.38 417.0 1
D(3) dopamine receptor
CHEMBL234
 Ki 6.36 6.36 437.0 1
D(4) dopamine receptor
CHEMBL219
 Ki 6.34 6.34 459.0 1
D(1B) dopamine receptor
CHEMBL1850
 Ki 6.21 6.21 623.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 6.21 6.21 622.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 6.14 6.14 729.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 6.13 6.13 740.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 6.05 6.05 900.0 1
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 6.02 6.02 949.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 5.88 5.88 1314.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
 Ki 5.85 5.85 1400.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 5.84 5.84 1438.0 1
Lewis lung carcinoma cell line
CHEMBL614088
 IC50 5.57 5.39 2700.0 3
5-hydroxytryptamine receptor 5A
CHEMBL3426
 Ki 5.3 5.3 4973.0 1
MDA-MB-231
CHEMBL400
 IC50 5.27 5.17 5400.0 3
Histamine H1 receptor
CHEMBL231
 Ki 5.15 5.15 7031.0 1
Mu-type opioid receptor
CHEMBL233
 Ki 5.08 5.08 8253.0 1
NIH3T3
CHEMBL614822
 IC50 5.06 4.99 8700.0 3
Kappa-type opioid receptor
CHEMBL237
 Ki 5.0 5.0 10000.0 1
Delta-type opioid receptor
CHEMBL236
 Ki 5.0 5.0 10000.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 5.0 5.0 10000.0 1
D(1A) dopamine receptor
CHEMBL2056
 Ki 5.0 5.0 10000.0 1
5-hydroxytryptamine receptor 1D
CHEMBL1983
 Ki 5.0 5.0 10000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Tmax 6.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(2) dopamine receptor Ki = 417.0 nM 6.38 Displacement of [3H]N-methylspiperone from human dopamine D2 receptor expressed ... 30389290
D(3) dopamine receptor Ki = 437.0 nM 6.36 Displacement of [3H]N-methylspiperone from human dopamine D3 receptor expressed ... 30389290
D(4) dopamine receptor Ki = 459.0 nM 6.34 Displacement of [3H]N-methylspiperone from human dopamine D4 receptor by radioli... 30389290
D(1B) dopamine receptor Ki = 623.0 nM 6.21 Displacement of [3H]SCH23390 from human dopamine D5 receptor expressed in HEK293... 30389290
Sodium-dependent dopamine transporter Ki = 622.0 nM 6.21 Displacement of [3H]WIN35428 from human DAT expressed in HEK cells by radioligan... 30389290
5-hydroxytryptamine receptor 2B Ki = 729.0 nM 6.14 Displacement of [3H]LSD from human 5-HT2B receptor expressed in HEK cells by rad... 30389290
5-hydroxytryptamine receptor 2C Ki = 740.0 nM 6.13 Displacement of [3H]Mesulergine from human 5-HT2C receptor expressed in HEK293Fl... 30389290
5-hydroxytryptamine receptor 2A Ki = 900.0 nM 6.05 Displacement of [3H]Ketanserin from 5-HT2A receptor (unknown origin) by radiolig... 30389290
5-hydroxytryptamine receptor 7 Ki = 949.0 nM 6.02 Displacement of [3H]LSD from human 5-HT7A receptor expressed in HEK cells by rad... 30389290
Sodium-dependent serotonin transporter Ki = 1314.0 nM 5.88 Displacement of [3H]Citalopram from human SERT expressed in HEK cells by radioli... 30389290
5-hydroxytryptamine receptor 6 Ki = 1400.0 nM 5.85 Displacement of [3H]LSD from human 5-HT6 receptor expressed in HEK cells by radi... 30389290
Sodium-dependent noradrenaline transporter Ki = 1438.0 nM 5.84 Displacement of [3H]Nisoxetine from human NET expressed in HEK cells by radiolig... 30389290
Lewis lung carcinoma cell line IC50 = 2700.0 nM 5.57 Cytotoxicity against mouse LLC cells harboring luciferin assessed as reduction i... 30389290
Lewis lung carcinoma cell line IC50 = 4000.0 nM 5.4 Cytotoxicity against mouse LLC cells harboring luciferin assessed as reduction i... 30389290
5-hydroxytryptamine receptor 5A Ki = 4973.0 nM 5.3 Displacement of [3H]LSD from human 5-HT5A receptor expressed in Flp-In CHO cells... 30389290
MDA-MB-231 IC50 = 5400.0 nM 5.27 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 30389290
Lewis lung carcinoma cell line IC50 = 6300.0 nM 5.2 Cytotoxicity against mouse LLC cells harboring luciferin assessed as reduction i... 30389290
MDA-MB-231 IC50 = 7100.0 nM 5.15 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 30389290
Histamine H1 receptor Ki = 7031.0 nM 5.15 Displacement of [3H]Pyrilamine from human H1 receptor expressed in HEK cells by ... 30389290
MDA-MB-231 IC50 = 8100.0 nM 5.09 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 Mus musculus 21
30389290 10.1016/j.bmcl.2018.10.036 ADMET 4
30389290 10.1016/j.bmcl.2018.10.036 Lewis lung carcinoma cell line 3
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 D(2) 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 5-hydroxytryptamine receptor 1A 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

Data from ChEMBL 36 via Core Engine