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Compound Detail

CHEMBL244403

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CCCCCOc1ccc(C(=O)c2cccc3ccccc23)c2ccccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL244403
Phase Preclinical
Structure Type MOL
InChI Key RSUMDJRTAFBISX-UHFFFAOYSA-N
4
Targets
14
Activities
3
Assay Types
10
PK Parameters
20
Publications
0
Known Names

Molecular Properties

368.5
MW (Da)
6.79
ALogP
2
HBA
0
HBD
26.3
PSA (Ų)
0.26
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C26H24O2
MW 368.48
Aromatic Rings 4
Heavy Atoms 28
NP-Likeness -0.35

Activity Summary

IC50 6 meas. best 7.82
EC50 4 meas. best 8.21
Ki 4 meas. best 7.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cannabinoid receptor 1
CHEMBL218
 EC50 8.21 7.4967 6.1 3
Cannabinoid receptor 1
CHEMBL218
 IC50 7.82 6.81 15.0 2
Cannabinoid receptor 2
CHEMBL253
 Ki 7.72 7.72 19.0 2
Cannabinoid receptor 1
CHEMBL3571
 IC50 7.66 7.66 22.0 1
Cannabinoid receptor 2
CHEMBL253
 EC50 7.55 7.55 27.9 1
Cannabinoid receptor 1
CHEMBL218
 Ki 7.46 7.46 35.0 2
Cannabinoid receptor 2
CHEMBL253
 IC50 7.01 6.145 98.0 2
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.09 4.09 80800.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2106.97 ng.hr.mL-1 Rattus norvegicus
AUC 3092.28 ng.hr.mL-1 Rattus norvegicus
CL 8.0 mL.min-1.kg-1 Rattus norvegicus
CL 5.0 uL/min Homo sapiens
CL 5.0 uL/min Rattus norvegicus
Cmax 1600.0 nM Rattus norvegicus
Cmax 1130.0 nM Rattus norvegicus
F 43.0 % Rattus norvegicus
T1/2 64.6 hr Rattus norvegicus
Tmax 1.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cannabinoid receptor 1 EC50 = 6.1 nM 8.21 Agonist activity at human CB1 receptor expressed in HEK293 cells assessed as rev... 17630726
Cannabinoid receptor 1 IC50 = 15.0 nM 7.82 Displacement of [3H]CP-55940 from human CB1 receptor expressed in HEK293 cells 17630726
Cannabinoid receptor 2 Ki = 19.0 nM 7.72 Binding affinity to human CB2 receptor 22284817
Cannabinoid receptor 2 Ki = 19.0 nM 7.72 Binding affinity to human CB2 receptor 22607668
Cannabinoid receptor 1 IC50 = 22.0 nM 7.66 Inhibition of rat CB1 receptor 17630726
Cannabinoid receptor 2 EC50 = 27.9 nM 7.55 Agonist activity at human CB2 receptor expressed in CHOK1 cells assessed as reve... 17630726
Cannabinoid receptor 1 Ki = 35.0 nM 7.46 Displacement of [3H]-CP55,940 from human CB1 receptor expressed in HEK293 cells 22284817
Cannabinoid receptor 1 Ki = 35.0 nM 7.46 Displacement of [3H]CP55940 from human CB1 receptor expressed in HEK293 cells 22607668
Cannabinoid receptor 1 EC50 = 72.0 nM 7.14 Agonist activity at human CB1 receptor expressed in HEK293 EBNA cells by [35S]GT... 22284817
Cannabinoid receptor 1 EC50 = 73.0 nM 7.14 Agonist activity at human CB1 receptor expressed in HEK293 cells assessed as [35... 22607668
Cannabinoid receptor 2 IC50 = 98.0 nM 7.01 Displacement of [3H]CP-55940 human CB2 receptor expressed in CHOK1 cells 17630726
Cannabinoid receptor 1 IC50 = 1580.0 nM 5.8 Displacement of [3H]SR141716A from membrane bound human CB1 receptor after 1 hr ... 30217464
Cannabinoid receptor 2 IC50 = 5300.0 nM 5.28 Displacement of [3H]CP55940 from membrane bound human CB2 receptor after 1 hr by... 30217464
Cytochrome P450 2C9 IC50 = 80800.0 nM 4.09 Inhibition of CYP2C9 in human liver microsomes 17630726

Literature References

PubMed DOI Target Context # Activities
17630726 10.1021/jm070317a Rattus norvegicus 11
17630726 10.1021/jm070317a Cannabinoid receptor 1 4
17630726 10.1021/jm070317a Cannabinoid receptor 2 3
30217464 10.1016/j.bmc.2018.09.007 Cannabinoid receptor 2 3
22607668 10.1016/j.bmcl.2012.04.128 Cannabinoid receptor 1 3
30217464 10.1016/j.bmc.2018.09.007 Cannabinoid receptor 1 3
22284817 10.1016/j.bmcl.2011.12.124 Cannabinoid receptor 1 3
30217464 10.1016/j.bmc.2018.09.007 Unchecked 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
17630726 10.1021/jm070317a Liver microsomes 2
17630726 10.1021/jm070317a Cytochrome P450 2D6 1
17630726 10.1021/jm070317a Cytochrome P450 3A4 1
17630726 10.1021/jm070317a Plasma 1
17630726 10.1021/jm070317a No relevant target 1
17630726 10.1021/jm070317a Brain 1
17630726 10.1021/jm070317a Cytochrome P450 2C19 1
17630726 10.1021/jm070317a Cytochrome P450 2C9 1
22284817 10.1016/j.bmcl.2011.12.124 No relevant target 1
22284817 10.1016/j.bmcl.2011.12.124 Nucleic Acid 1
17630726 10.1021/jm070317a Cytochrome P450 2C8 1

Data from ChEMBL 36 via Core Engine