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Compound Detail

CHEMBL381791

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Cc1ccc(Cn2nc(C(=O)N[C@@H]3C(C)(C)[C@@H]4CC[C@@]3(C)C4)cc2-c2ccc(Cl)c(C)c2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL381791
Phase Preclinical
Structure Type MOL
InChI Key SUGVYNSRNKFXQM-XRHWURSXSA-N
2
Targets
42
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

476.1
MW (Da)
6.81
ALogP
3
HBA
1
HBD
46.9
PSA (Ų)
0.44
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C29H34ClN3O
MW 476.06
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -0.71

Activity Summary

Ki 31 meas. best 9.51
IC50 6 meas. best 7.7
EC50 5 meas. best 7.63

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cannabinoid receptor 2
CHEMBL253
 Ki 9.51 8.3781 0.3 16
Cannabinoid receptor 1
CHEMBL218
 Ki 8.7 6.5323 2.0 13
Cannabinoid receptor 2
CHEMBL253
 IC50 7.7 6.495 19.9 4
Cannabinoid receptor 2
CHEMBL253
 EC50 7.63 6.278 23.3 5
Cannabinoid receptor 1
CHEMBL218
 IC50 6.1 6.1 794.3 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cannabinoid receptor 2 Ki = 0.31 nM 9.51 Displacement of [3H]-CP55940 from human CB2 receptor transfected in HEK293EBNA c... 26209834
Cannabinoid receptor 2 Ki = 0.6 nM 9.22 Displacement of [3H]-CP 55,940 from human CB2 receptor expressed in CHO cells by... -
Cannabinoid receptor 2 Ki = 0.6 nM 9.22 Displacement of [3H]-CP55940 from human CB2 receptor transfected in CHO cell mem... 26209834
Cannabinoid receptor 2 Ki = 0.6 nM 9.22 Binding affinity to human CB2 receptor expressed in CHO cells 23855811
Cannabinoid receptor 2 Ki = 1.8 nM 8.74 Displacement of [3H]-CP-55,940 from recombinant human CB2R expressed in HEK293 c... 32515588
Cannabinoid receptor 2 Ki = 1.8 nM 8.74 Displacement of [3H]CP55940 from recombinant human CB2R expressed in HEK293 cell... 30359820
Cannabinoid receptor 2 Ki = 1.82 nM 8.74 Displacement of [3H]-CP-55940 from human CB2 receptor expressed in HEK293 cell m... 27448919
Cannabinoid receptor 1 Ki = 2.0 nM 8.7 Displacement of [3H]CP55940 from recombinant human CB1R expressed in HEK293 cell... 31302448
Cannabinoid receptor 2 Ki = 2.23 nM 8.65 Displacement of [3H]CP-55,940 from human CB2 receptor after 1 hr by competitive ... 23855811
Cannabinoid receptor 2 Ki = 4.35 nM 8.36 Displacement of [3H]CP55940 from recombinant human CB2 receptor expressed in hum... 22483967
Cannabinoid receptor 2 Ki = 5.6 nM 8.25 Displacement of [3H]-CP55950 from human CB2 receptor expressed in HEK cell membr... 29400965
Cannabinoid receptor 2 Ki = 13.2 nM 7.88 Displacement of [3H]CP55,940 from human CB2 receptor 29407590
Cannabinoid receptor 2 Ki = 13.18 nM 7.88 Displacement of [3H]CP55,940 from human CB2 receptor 29407590
Cannabinoid receptor 2 Ki = 19.7 nM 7.71 Displacement of [3H]-CP55950 from human CB2 receptor expressed in HEK cell membr... 29400965
Cannabinoid receptor 2 Ki = 19.7 nM 7.71 Displacement of [3H]-CP55940 from human recombinant cannabinoid CB2 receptor exp... 31609608
Cannabinoid receptor 2 IC50 = 19.95 nM 7.7 Displacement of [3H]-CP55950 from human CB2 receptor expressed in HEK cell membr... 29400965
Cannabinoid receptor 2 EC50 = 23.31 nM 7.63 Antagonist activity at CB2 receptor in HEK293 cells assessed as increase in CP-5... 23855811
Cannabinoid receptor 2 EC50 = 41.0 nM 7.39 Antagonist activity at N-terminal Flag epitope tagged CB2 (unknown origin) expre... 31302448
Cannabinoid receptor 2 Ki = 51.0 nM 7.29 Displacement of [3H]CP55,940 from N-terminal HA-tagged human CB2 receptor expres... 29407590
Cannabinoid receptor 2 IC50 = 96.2 nM 7.02 Inverse agonist activity at human CB2 receptor expressed in HEK293 EBNA cell mem... 28088085

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5058564 U2OS 8
29407590 10.1016/j.ejmech.2017.11.076 Cannabinoid receptor 2 7
29407590 10.1016/j.ejmech.2017.11.076 Cannabinoid receptor 1 6
- 10.6019/CHEMBL5058564 Fibroblast 6
31302448 10.1016/j.ejmech.2019.07.002 Cannabinoid receptor 2 4
- 10.6019/CHEMBL5058564 HEK-293T 4
23855811 10.1021/jm400070u Cannabinoid receptor 2 4
26209834 10.1016/j.ejmech.2015.06.057 Cannabinoid receptor 2 3
27448919 10.1016/j.ejmech.2016.07.012 Cannabinoid receptor 2 3
29400965 10.1021/acs.jmedchem.7b01760 Cannabinoid receptor 2 3
29400965 10.1021/acs.jmedchem.7b01760 Cannabinoid receptor 1 3
31185414 10.1016/j.ejmech.2019.05.080 Cannabinoid receptor 2 2
32515588 10.1021/acs.jmedchem.0c00595 Cannabinoid receptor 2 2
29407590 10.1016/j.ejmech.2017.11.076 HEK293 2
33550084 10.1016/j.bmc.2021.116035 Cannabinoid receptor 2 2
33550084 10.1016/j.bmc.2021.116035 Cannabinoid receptor 1 2
31302448 10.1016/j.ejmech.2019.07.002 Cannabinoid receptor 1 2
30359820 10.1016/j.ejmech.2018.09.070 Cannabinoid receptor 2 2
22483967 10.1016/j.ejmech.2012.03.031 DU-145 2
30359820 10.1016/j.ejmech.2018.09.070 Cannabinoid receptor 1 2

Data from ChEMBL 36 via Core Engine