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Compound Detail

CHEMBL306764

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CCCn1c(C)c(C(=O)c2cccc3ccccc23)c2ccccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL306764
Phase Preclinical
Structure Type MOL
InChI Key LJSBBBWQTLXQEN-UHFFFAOYSA-N
9
Targets
33
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

327.4
MW (Da)
5.74
ALogP
2
HBA
0
HBD
22.0
PSA (Ų)
0.44
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C23H21NO
MW 327.43
Aromatic Rings 4
Heavy Atoms 25
NP-Likeness -0.76

Activity Summary

Ki 20 meas. best 7.88
IC50 8 meas. best 5.49
EC50 5 meas. best 7.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cannabinoid receptor 2
CHEMBL253
 Ki 7.88 7.656 13.3 10
Cannabinoid receptor 2
CHEMBL5373
 EC50 7.52 7.16 30.0 2
Cannabinoid receptor
CHEMBL2096981
 Ki 6.79 6.79 164.0 1
Cannabinoid receptor 1
CHEMBL3571
 Ki 6.79 6.79 164.1 1
Cannabinoid receptor 1
CHEMBL218
 Ki 6.42 6.17 383.0 8
Cannabinoid receptor 2
CHEMBL253
 EC50 6.2 6.2 634.0 2
Nuclear receptor subfamily 1 group I member 2
CHEMBL3401
 EC50 5.58 5.58 2640.0 1
Bile acid receptor
CHEMBL2047
 IC50 5.49 5.49 3220.0 1
Jurkat
CHEMBL397
 IC50 5.02 5.02 9600.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.0 4.9667 10000.0 6

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cannabinoid receptor 2 Ki = 13.3 nM 7.88 Displacement of [3H]CP 55940 from human CB2 receptor in cell free system 21183257
Cannabinoid receptor 2 Ki = 13.8 nM 7.86 Binding affinity to human Cannabinoid receptor 2 assessed as inhibition constant 37478557
Cannabinoid receptor 2 Ki = 13.8 nM 7.86 Displacement of [3H]CP-55940 from human cloned CB2 receptor by filtration assay 19249138
Cannabinoid receptor 2 Ki = 14.0 nM 7.85 Binding affinity to CB2 receptor (unknown origin) 23865723
Cannabinoid receptor 2 Ki = 14.0 nM 7.85 Binding affinity to CB2 receptor (unknown origin) 23672690
Cannabinoid receptor 2 EC50 = 30.0 nM 7.52 Inverse agonist activity at mouse CB2 receptor expressed in HEK293 cells assesse... 29939744
Cannabinoid receptor 2 Ki = 35.0 nM 7.46 Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HE... 19921781
Cannabinoid receptor 2 Ki = 35.0 nM 7.46 Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HE... 18311894
Cannabinoid receptor 2 Ki = 35.48 nM 7.45 Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HE... 19921781
Cannabinoid receptor 2 Ki = 35.48 nM 7.45 Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HE... 18311894
Cannabinoid receptor 2 Ki = 36.0 nM 7.44 In vitro inhibitory activity towards human cannabinoid receptors 2 using fluores... 15993070
Cannabinoid receptor 2 EC50 = 160.0 nM 6.8 Inverse agonist activity at C-terminally prolink-tagged mouse CB2 receptor expre... 29939744
Cannabinoid receptor 1 Ki = 164.06 nM 6.79 Displacement of [3H]CP-55940 from CB1 receptor in rat brain by filtration assay 19249138
Cannabinoid receptor Ki = 164.0 nM 6.79 Binding affinity was determined in vitro against cannabinoid receptor by ability... -
Cannabinoid receptor 1 Ki = 383.0 nM 6.42 Binding affinity to human Cannabinoid receptor 1 assessed as inhibition constant 37478557
Cannabinoid receptor 1 Ki = 383.0 nM 6.42 Binding affinity to CB1 receptor (unknown origin) 23865723
Cannabinoid receptor 1 Ki = 383.0 nM 6.42 Binding affinity to CB1 receptor (unknown origin) 23672690
Cannabinoid receptor 1 Ki = 383.0 nM 6.42 Displacement of [3H]CP 55940 from human CB1 receptor in cell free system 21183257
Cannabinoid receptor 2 EC50 = 634.0 nM 6.2 Agonist activity at human recombinant CB2 receptor expressed in HEK293 cells coe... 19921781
Cannabinoid receptor 2 EC50 = 634.0 nM 6.2 Agonist activity at human recombinant CB2 receptor expressed in HEK cells assess... 18311894

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
29939744 10.1021/acs.jmedchem.8b00435 Cannabinoid receptor 2 5
22341572 10.1016/j.bmc.2012.01.038 Mus musculus 4
19921781 10.1021/jm901214q Cannabinoid receptor 2 4
18311894 10.1021/jm7011613 Cannabinoid receptor 2 4
37478557 10.1016/j.ejmech.2023.115647 BT-549 3
15993070 10.1016/j.bmcl.2005.05.049 Cannabinoid receptor 2 2
18311894 10.1021/jm7011613 Cannabinoid receptor 1 2
19435366 10.1021/jm801563d NON-PROTEIN TARGET 2
37478557 10.1016/j.ejmech.2023.115647 Cannabinoid receptor 2 2
19249138 10.1016/j.ejmech.2009.01.026 Unchecked 2
19921781 10.1021/jm901214q Cannabinoid receptor 1 2
23688559 10.1016/j.bmc.2013.04.069 Bile acid receptor 2
23688559 10.1016/j.bmc.2013.04.069 Nuclear receptor subfamily 1 group I member 2 2
21183257 10.1016/j.ejmech.2010.11.034 Cannabinoid receptor 1 1
17417631 10.1038/nchembio873 Unchecked 1
19249138 10.1016/j.ejmech.2009.01.026 Cannabinoid receptor 1 1
37478557 10.1016/j.ejmech.2023.115647 Cannabinoid receptor 1 1
18311894 10.1021/jm7011613 Unchecked 1
10882356 10.1021/jm991074s Cannabinoid receptor 2 1

Data from ChEMBL 36 via Core Engine