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Compound Detail

CHEMBL188

WIN-552122
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Cc1c(C(=O)c2cccc3ccccc23)c2cccc3c2n1[C@H](CN1CCOCC1)CO3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL188
Name WIN-552122
Phase Preclinical
Structure Type MOL
InChI Key HQVHOQAKMCMIIM-HXUWFJFHSA-N
13
Targets
220
Activities
3
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

426.5
MW (Da)
4.60
ALogP
5
HBA
0
HBD
43.7
PSA (Ų)
0.45
QED
0
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 C27H26N2O3
MW 426.52
Aromatic Rings 4
Heavy Atoms 32
NP-Likeness -0.43

Activity Summary

Ki 154 meas. best 9.55
EC50 41 meas. best 9.41
IC50 25 meas. best 9.37

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cannabinoid receptor 2
CHEMBL253
 Ki 9.55 8.6343 0.3 68
Cannabinoid receptor 2
CHEMBL253
 EC50 9.41 8.0147 0.4 17
Mus musculus
CHEMBL375
 IC50 9.37 6.935 0.4 4
Cannabinoid receptor 2
CHEMBL253
 IC50 8.96 8.37 1.1 5
Cannabinoid receptor 2
CHEMBL2470
 EC50 8.82 8.82 1.5 1
Cannabinoid receptor 1
CHEMBL3037
 Ki 8.8 8.2167 1.6 3
Unchecked
CHEMBL612545
 Ki 8.74 8.74 1.8 1
Cannabinoid receptor 1
CHEMBL218
 Ki 8.72 7.6658 1.9 69
Cannabinoid receptor 1
CHEMBL3571
 Ki 8.72 8.0425 1.9 8
Cannabinoid receptor 1
CHEMBL218
 IC50 8.7 7.4643 2.0 7
Cannabinoid receptor
CHEMBL2111385
 IC50 8.56 8.41 2.8 2
Cavia porcellus
CHEMBL369
 EC50 8.31 8.31 4.9 1
Cannabinoid receptor 2
CHEMBL5373
 Ki 8.22 8.22 6.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.15 6.426 7.0 5
Cannabinoid receptor 1
CHEMBL218
 EC50 8.14 7.2747 7.2 15
Cannabinoid receptor 2
CHEMBL2470
 Ki 8.12 8.115 7.6 2
Cannabinoid receptor 1
CHEMBL3571
 EC50 8.0 7.42 10.0 2
Cannabinoid receptor
CHEMBL2096981
 Ki 7.62 7.62 24.0 1
Unchecked
CHEMBL612545
 EC50 7.33 7.33 47.0 1
Rattus norvegicus
CHEMBL376
 EC50 6.75 6.75 180.0 1
Cannabinoid receptor 1
CHEMBL3037
 EC50 6.69 6.265 204.0 2
Cannabinoid receptor 1
CHEMBL3571
 IC50 6.37 6.37 430.0 1
Cannabinoid receptor 2
CHEMBL2470
 IC50 5.66 5.66 2200.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC - - Rattus norvegicus
F - % Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cannabinoid receptor 2 Ki = 0.28 nM 9.55 Compound was evaluated for its binding affinity against Cannabinoid receptor 2 i... 9857088
Cannabinoid receptor 2 Ki = 0.28 nM 9.55 Binding affinity to displace [3H]CP-55940 from cloned human CB2 receptor 16005223
Cannabinoid receptor 2 Ki = 0.28 nM 9.55 Binding affinity to human CB2 receptor by filtration assay 22341572
Cannabinoid receptor 2 Ki = 0.28 nM 9.55 Agonist activity at CB2 receptor (unknown origin) 27560280
Cannabinoid receptor 2 Ki = 0.3 nM 9.52 Binding affinity of compound was determined against to human cannabinoid recepto... 12747783
Cannabinoid receptor 2 Ki = 0.3 nM 9.52 Binding affinity to CB2 receptor 18680277
Cannabinoid receptor 2 Ki = 0.3 nM 9.52 Binding affinity to CB2 receptor (unknown origin) 23466226
Cannabinoid receptor 2 Ki = 0.3 nM 9.52 Binding affinity to CB2 receptor (unknown origin) 23672690
Cannabinoid receptor 2 Ki = 0.3 nM 9.52 Binding affinity to CB2 receptor (unknown origin) 23865723
Cannabinoid receptor 2 EC50 = 0.39 nM 9.41 Agonist activity at human recombinant CB2 receptor expressed in HEK293 cells ass... 19921781
Mus musculus IC50 = 0.43 nM 9.37 In vitro inhibition of electrically stimulated contractions of isolated mouse va... 1732519
Cannabinoid receptor 2 Ki = 0.45 nM 9.35 Displacement of [3H]CP55940 from human cannabinoid CB2 receptor expressed in CHO... 25072877
Cannabinoid receptor 2 EC50 = 0.47 nM 9.33 Agonist activity at human CB2 receptor expressed in CHOK1 cells assessed as reve... 17630726
Cannabinoid receptor 2 Ki = 0.9 nM 9.05 Displacement of [3H]-CP55940 from human recombinant CB2 receptor expressed in HE... 26149623
Cannabinoid receptor 2 IC50 = 1.1 nM 8.96 Agonist activity at human CB2 in CHO cells assessed as inhibition of cAMP produc... 17521907
Cannabinoid receptor 2 Ki = 1.2 nM 8.92 Displacement of [3H]CP-55940 from human recombinant cannabinoid CB2 receptor exp... 19278853
Cannabinoid receptor 2 Ki = 1.3 nM 8.89 Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HE... 18311894
Cannabinoid receptor 2 Ki = 1.288 nM 8.89 Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HE... 18311894
Cannabinoid receptor 2 Ki = 1.3 nM 8.89 Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HE... 19921781
Cannabinoid receptor 2 Ki = 1.3 nM 8.89 Displacement of [3H]CP 55940 from human CB2 receptor in cell free system 21183257

Literature References

PubMed DOI Target Context # Activities
30685536 10.1016/j.ejmech.2019.01.030 Cannabinoid receptor 18
19921781 10.1021/jm901214q Cannabinoid receptor 2 8
17027269 10.1016/j.bmcl.2006.09.049 Cannabinoid receptor 1 7
14613317 10.1021/jm0302647 Cannabinoid receptor 1 6
19921781 10.1021/jm901214q Cannabinoid receptor 1 6
1732519 10.1021/jm00079a016 Mus musculus 6
21885167 10.1016/j.ejmech.2011.08.021 No relevant target 6
27560280 10.1016/j.ejmech.2016.08.005 NON-PROTEIN TARGET 5
17870539 10.1016/j.bmc.2007.07.056 Mus musculus 5
29939744 10.1021/acs.jmedchem.8b00435 Cannabinoid receptor 1 5
22341572 10.1016/j.bmc.2012.01.038 Mus musculus 4
16392793 10.1021/jm050467q Cannabinoid receptor 2 4
26922225 10.1016/j.ejmech.2016.02.032 Cannabinoid receptor 2 4
22421020 10.1016/j.bmcl.2012.02.048 Rattus norvegicus 4
23849204 10.1016/j.bmc.2013.06.010 Cannabinoid receptor 2 4
21505060 10.1124/jpet.111.180257 Mus musculus 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
23017078 10.1021/jm3008568 Cannabinoid receptor 2 4
23227781 10.1021/jm301511h Canis familiaris 4
15139773 10.1021/jm031099y Unchecked 4

Data from ChEMBL 36 via Core Engine