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Compound Detail

CHEMBL285932

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Cc1c(C(=O)NN2CCCCC2)nn(-c2ccc(Cl)cc2Cl)c1-c1ccc(I)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL285932
Phase Preclinical
Structure Type MOL
InChI Key BUZAJRPLUGXRAB-UHFFFAOYSA-N
9
Targets
37
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

555.2
MW (Da)
5.89
ALogP
4
HBA
1
HBD
50.2
PSA (Ų)
0.41
QED
2
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 C22H21Cl2IN4O
MW 555.25
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -1.62

Activity Summary

Ki 22 meas. best 9.22
IC50 7 meas. best 9.49
EC50 6 meas. best 7.24
Kd 2 meas. best 9.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cavia porcellus
CHEMBL369
 Kd 9.66 9.66 0.2 1
Cannabinoid receptor 1
CHEMBL218
 IC50 9.49 7.8729 0.3 7
Mus musculus
CHEMBL375
 Kd 9.3 9.3 0.5 1
Cannabinoid receptor 1
CHEMBL3571
 Ki 9.22 7.868 0.6 5
Cannabinoid receptor 1
CHEMBL218
 Ki 8.64 8.4325 2.3 8
Unchecked
CHEMBL612545
 Ki 7.31 7.31 48.7 1
Cannabinoid receptor 1
CHEMBL218
 EC50 7.24 7.19 57.5 3
Cannabinoid receptor
CHEMBL2111385
 Ki 7.16 7.16 69.0 1
Cannabinoid receptor 2
CHEMBL253
 Ki 6.96 6.7333 110.0 6
G-protein coupled receptor 55
CHEMBL1075322
 EC50 6.2 6.2 630.0 1
Cannabinoid receptor 2
CHEMBL5373
 Ki 5.64 5.64 2290.0 1
Unchecked
CHEMBL612545
 EC50 4.95 4.93 11330.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cavia porcellus Kd = 0.22 nM 9.66 Dissociation constant [100(nM)] in myenteric plexus-longitudinal muscle of guine... 10052983
Cannabinoid receptor 1 IC50 = 0.32 nM 9.49 Displacement of [3H]SR-141716 from human wild type CB1R expressed in CHO cells 18333607
Mus musculus Kd = 0.5 nM 9.3 Dissociation constant [31.6(nM)] in mouse isolated vas deferens using the cannab... 10052983
Cannabinoid receptor 1 IC50 = 0.59 nM 9.23 Displacement of [3H]SR-141716 from human CBR1 S383A mutant expressed in CHO cell... 18333607
Cannabinoid receptor 1 Ki = 0.6 nM 9.22 Binding affinity was determined by using a competition assay with [125 I]- AM251... 12570386
Cannabinoid receptor 1 Ki = 2.3 nM 8.64 Displacement of [3H]CP-55,940 from recombinant human CB1 receptor transfected in... 20943290
Cannabinoid receptor 1 Ki = 2.3 nM 8.64 Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in HE... 19595596
Cannabinoid receptor 1 Ki = 2.3 nM 8.64 Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in HE... 18579386
Cannabinoid receptor 1 Ki = 2.3 nM 8.64 Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in HE... 18293908
Cannabinoid receptor 1 Ki = 3.0 nM 8.52 Binding affinity to human CB1 receptor 17513109
Cannabinoid receptor 1 IC50 = 3.5 nM 8.46 Displacement of [3H]CP-55940 from human wild type CB1R expressed in CHO cells 18333607
Cannabinoid receptor 1 Ki = 6.0 nM 8.22 Inhibition of [3H]CP-55940 binding to cannabinoid receptor 1 in rat brain membra... 11906286
Cannabinoid receptor 1 Ki = 7.49 nM 8.13 Binding affinity to cannabinoid CB1 receptor 20218623
Cannabinoid receptor 1 Ki = 7.49 nM 8.13 Binding affinity against Cannabinoid receptor 1 in rat forebrain 10052983
Cannabinoid receptor 1 Ki = 7.482 nM 8.13 Antagonist activity at CB1 receptor (unknown origin) -
Cannabinoid receptor 1 Ki = 7.49 nM 8.13 Antagonist activity at rat forebrain CB1R assessed as inhibition constant 35694688
Cannabinoid receptor 1 Ki = 7.5 nM 8.12 Antagonist activity at CB1 receptor (unknown origin) -
Cannabinoid receptor 1 IC50 = 30.0 nM 7.52 Displacement of [3H]CP-55940 from human CB1R F200L mutant expressed in CHO cells 18333607
Unchecked Ki = 48.7 nM 7.31 Selectivity index ratio of Ki for recombinant human CB2 to Ki for recombinant hu... 20943290
Cannabinoid receptor 1 EC50 = 57.54 nM 7.24 Inverse agonist activity at human CB1 receptor expressed in Sf9 cells coexpressi... 24984935

Literature References

PubMed DOI Target Context # Activities
18333607 10.1021/jm7014974 Cannabinoid receptor 1 7
30685536 10.1016/j.ejmech.2019.01.030 Cannabinoid receptor 6
18333607 10.1021/jm7014974 Unchecked 5
24984935 10.1016/j.bmc.2014.06.008 Cannabinoid receptor 1 3
25096297 10.1016/j.bmcl.2014.07.038 Cannabinoid receptor 1 3
21661758 10.1021/jm200319u Mus musculus 2
- 10.1007/s00044-012-0418-y Cannabinoid receptor 1 2
32912440 10.1016/j.bmc.2020.115672 Unchecked 2
35694688 10.1039/d2md00006g Cannabinoid receptor 1 2
12570386 10.1021/jm020157x No relevant target 2
38493727 10.1016/j.ejmech.2024.116298 Mus musculus 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
17513109 10.1016/j.bmcl.2007.04.087 Cannabinoid receptor 1 1
18293908 10.1021/jm070566z Cannabinoid receptor 2 1
18293908 10.1021/jm070566z Cannabinoid receptor 1 1
18027904 10.1021/jm070678q Fatty-acid amide hydrolase 1 1
11906286 10.1021/jm010267o Cannabinoid receptor 1 1
10052983 10.1021/jm980363y Cannabinoid receptor 1
10052983 10.1021/jm980363y Cavia porcellus 1

Data from ChEMBL 36 via Core Engine