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Compound Detail

CHEMBL471980

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CCOc1ccc(Cc2nc3cc(C(=O)N(CC)CC)ccc3n2CCC(C)C)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL471980
Phase Preclinical
Structure Type MOL
InChI Key RLLSCGRLMPJHDQ-UHFFFAOYSA-N
4
Targets
19
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

421.6
MW (Da)
5.55
ALogP
4
HBA
0
HBD
47.4
PSA (Ų)
0.43
QED
1
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C26H35N3O2
MW 421.59
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -1.67

Activity Summary

Ki 9 meas. best 8.35
EC50 5 meas. best 9.2
IC50 5 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cannabinoid receptor 2
CHEMBL253
 EC50 9.2 7.8475 0.6 4
Cannabinoid receptor 2
CHEMBL253
 Ki 8.35 7.8243 4.5 7
Cannabinoid receptor 2
CHEMBL253
 IC50 7.7 7.5667 20.0 3
Cannabinoid receptor 1
CHEMBL218
 EC50 5.49 5.49 3235.9 1
Mu-type opioid receptor
CHEMBL233
 Ki 5.2 5.185 6309.6 2
Cholinesterase
CHEMBL5763
 IC50 5.01 5.01 9700.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cannabinoid receptor 2 EC50 = 0.63 nM 9.2 Agonist activity at human CB2 receptor stably expressed in HEK293 cells assessed... 37127287
Cannabinoid receptor 2 EC50 = 2.9 nM 8.54 Agonist activity at cloned human CB2 receptor in Sf9 cells assessed as stimulati... 18522867
Cannabinoid receptor 2 Ki = 4.5 nM 8.35 Displacement of [3H]CP-55940 from human CB2 receptor 18522867
Cannabinoid receptor 2 Ki = 4.5 nM 8.35 Binding affinity to human CB2 receptor stably expressing HEK cells assessed as i... 33094613
Cannabinoid receptor 2 Ki = 4.5 nM 8.35 Displacement of [3H]CP55940 from human CB2 receptor stably expressed in HEK293 c... 37127287
Cannabinoid receptor 2 IC50 = 20.0 nM 7.7 Displacement of [3H]CP55940 from human CB2 receptor expressed in HEK293 cell mem... 37127287
Cannabinoid receptor 2 IC50 = 25.12 nM 7.6 Displacement of [3H]CP55940 from human CB2 receptor expressed in HEK293 cell mem... 37127287
Cannabinoid receptor 2 Ki = 36.7 nM 7.43 Displacement of [3H]-CP55950 from human CB2 receptor expressed in HEK cell membr... 29400965
Cannabinoid receptor 2 Ki = 36.7 nM 7.43 Binding affinity in human CB2R expressed in human HEK cells incubated for 3 hrs ... 31609608
Cannabinoid receptor 2 Ki = 36.7 nM 7.43 Displacement of [3H]-CP55940 from human recombinant cannabinoid CB2 receptor exp... 31609608
Cannabinoid receptor 2 Ki = 36.7 nM 7.43 Binding affinity to human CB2 receptor stably expressed in HEK cells assessed as... 33094613
Cannabinoid receptor 2 IC50 = 39.81 nM 7.4 Displacement of [3H]-CP55950 from human CB2 receptor expressed in HEK cell membr... 29400965
Cannabinoid receptor 2 EC50 = 141.25 nM 6.85 Agonist activity at human CB2 receptor expressed in Sf9 cells coexpressing Galph... 24984935
Cannabinoid receptor 2 EC50 = 158.0 nM 6.8 Agonist activity at human CB2 receptor stably expressed in CHO-K1 cells co-expre... 37127287
Cannabinoid receptor 1 EC50 = 3235.94 nM 5.49 Agonist activity at human CB1 receptor expressed in Sf9 cells coexpressing Galph... 24984935
Mu-type opioid receptor Ki = 6309.57 nM 5.2 Displacement of [3H]-Diprenorphine from human mu opioid receptor expressed in HE... 29400965
Mu-type opioid receptor Ki = 6700.0 nM 5.17 Displacement of [3H]-Diprenorphine from human mu opioid receptor expressed in HE... 29400965
Cholinesterase IC50 = 9700.0 nM 5.01 Inhibition of equine serum BChE 33094613
Cholinesterase IC50 = 9700.0 nM 5.01 Inhibition of equine BChE using BTC iodide as substrate preincubated for 4.5 min... 29400965

Literature References

PubMed DOI Target Context # Activities
29400965 10.1021/acs.jmedchem.7b01760 Cannabinoid receptor 2 8
37127287 10.1021/acs.jmedchem.3c00541 Cannabinoid receptor 2 6
31609608 10.1021/acs.jmedchem.9b00623 Cannabinoid receptor 2 6
31609608 10.1021/acs.jmedchem.9b00623 N9 5
29400965 10.1021/acs.jmedchem.7b01760 Mus musculus 5
18522867 10.1016/j.bmcl.2008.05.073 Cannabinoid receptor 2 3
24984935 10.1016/j.bmc.2014.06.008 Cannabinoid receptor 2 3
29400965 10.1021/acs.jmedchem.7b01760 Acetylcholinesterase 2
29400965 10.1021/acs.jmedchem.7b01760 Cholinesterase 2
29400965 10.1021/acs.jmedchem.7b01760 Mu-type opioid receptor 2
31609608 10.1021/acs.jmedchem.9b00623 Cannabinoid receptor 1 2
24984935 10.1016/j.bmc.2014.06.008 Cannabinoid receptor 1 2
33094613 10.1021/acs.jmedchem.0c01357 Cannabinoid receptor 1 2
33094613 10.1021/acs.jmedchem.0c01357 Cannabinoid receptor 2 2
33094613 10.1021/acs.jmedchem.0c01357 Cholinesterase 2
29400965 10.1021/acs.jmedchem.7b01760 Cannabinoid receptor 1 1
29400965 10.1021/acs.jmedchem.7b01760 U-266 1
24984935 10.1016/j.bmc.2014.06.008 Unchecked 1
31609608 10.1021/acs.jmedchem.9b00623 Acetylcholinesterase 1
37127287 10.1021/acs.jmedchem.3c00541 Cannabinoid receptor 1 1

Data from ChEMBL 36 via Core Engine