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Compound Detail

CHEMBL158784

RAC-IBIPINABANT
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CN/C(=N\S(=O)(=O)c1ccc(Cl)cc1)N1CC(c2ccccc2)C(c2ccc(Cl)cc2)=N1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL158784
Name RAC-IBIPINABANT
Phase Preclinical
Structure Type MOL
InChI Key AXJQVVLKUYCICH-UHFFFAOYSA-N
3
Targets
14
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

487.4
MW (Da)
4.76
ALogP
3
HBA
1
HBD
74.1
PSA (Ų)
0.43
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 C23H20Cl2N4O2S
MW 487.41
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.88

Activity Summary

Ki 6 meas. best 8.09
IC50 4 meas. best 8.72
Kd 4 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cannabinoid receptor 1
CHEMBL218
 IC50 8.72 7.7467 1.9 3
Cannabinoid receptor 1
CHEMBL218
 Kd 8.7 8.7 2.0 4
Cannabinoid receptor 1
CHEMBL3037
 Ki 8.09 8.09 8.1 1
Cannabinoid receptor 1
CHEMBL218
 Ki 7.6 7.6 25.0 4
Cannabinoid receptor 1
CHEMBL3037
 IC50 7.12 7.12 76.0 1
Cannabinoid receptor 2
CHEMBL253
 Ki 5.1 5.1 7943.3 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cannabinoid receptor 1 IC50 = 1.905 nM 8.72 Antagonist activity against human recombinant cannabinoid-1 receptor 19406638
Cannabinoid receptor 1 Kd = 1.995 nM 8.7 Antagonistic activity towards cannabinoid receptor 1 expressed as [3H]Arachidoni... 14736243
Cannabinoid receptor 1 Kd = 1.995 nM 8.7 Antagonist activity at human CB1 receptor expressed in CHO cells assessed as inh... 19699640
Cannabinoid receptor 1 Kd = 1.995 nM 8.7 Antagonist activity at human CB1 receptor expressed in CHO cells assessed as inh... 20047331
Cannabinoid receptor 1 Kd = 1.995 nM 8.7 Antagonist activity at human cannabinoid CB1 receptor expressed in CHO cells ass... 20137935
Cannabinoid receptor 1 Ki = 8.1 nM 8.09 Displacement of [3H]CP55940 from mouse brain CB1R expressed in CHOK1 cell membra... 28085283
Cannabinoid receptor 1 IC50 = 22.0 nM 7.66 Displacement of 3[H]ligand from recombinant human CB1 receptor 22959249
Cannabinoid receptor 1 Ki = 25.2 nM 7.6 Displacement of CP-55940 binding from recombinant human cannabinoid receptor 1 e... 14736243
Cannabinoid receptor 1 Ki = 25.0 nM 7.6 Displacement of [3H]CP-55940 from human CB1 receptor expressed in CHO cells 19699640
Cannabinoid receptor 1 Ki = 25.0 nM 7.6 Displacement of [3H]CP-55940 from human CB1 receptor expressed in CHO cells 20047331
Cannabinoid receptor 1 Ki = 25.2 nM 7.6 Displacement of [3H]CP-55940 from human cannabinoid CB1 receptor expressed in CH... 20137935
Cannabinoid receptor 1 IC50 = 76.0 nM 7.12 Inverse agonist at mouse brain CB1R expressed in CHOK1 cell membranes assessed a... 28085283
Cannabinoid receptor 1 IC50 = 139.0 nM 6.86 Inverse agonist activity against CB1 receptor expressed in human CHO cells asses... 22959249
Cannabinoid receptor 2 Ki = 7943.28 nM 5.1 Displacement of [3H]CP 55940 from human CB2 receptor in cell free system 21183257

Literature References

PubMed DOI Target Context # Activities
22959249 10.1016/j.bmcl.2012.08.004 Mus musculus 7
22959249 10.1016/j.bmcl.2012.08.004 MDCK 3
22959249 10.1016/j.bmcl.2012.08.004 Cannabinoid receptor 1 3
14736243 10.1021/jm031019q Cannabinoid receptor 1 3
20137935 10.1016/j.bmcl.2010.01.049 Cannabinoid receptor 1 2
28085283 10.1021/acs.jmedchem.6b01504 Cannabinoid receptor 1 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
20047331 10.1021/jm901614b No relevant target 2
20047331 10.1021/jm901614b Cannabinoid receptor 1 2
19699640 10.1016/j.bmcl.2009.08.007 Cannabinoid receptor 1 2
14736243 10.1021/jm031019q Cannabinoid receptor 2 2
20047331 10.1021/jm901614b Acetylcholinesterase 1
20047331 10.1021/jm901614b Cannabinoid receptor 2 1
20137935 10.1016/j.bmcl.2010.01.049 Cannabinoid receptor 2 1
20137935 10.1016/j.bmcl.2010.01.049 Unchecked 1
20137935 10.1016/j.bmcl.2010.01.049 Rattus norvegicus 1
19699640 10.1016/j.bmcl.2009.08.007 Unchecked 1
22959249 10.1016/j.bmcl.2012.08.004 Cannabinoid receptor 2 1
19699640 10.1016/j.bmcl.2009.08.007 Cannabinoid receptor 2 1

Data from ChEMBL 36 via Core Engine