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Compound Detail

CHEMBL377231

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COc1cc(Cl)ccc1CC(C)C(=O)N1CCN(c2ccc(C(F)(F)F)cc2[C@@H](N)CC(C)C)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL377231
Phase Preclinical
Structure Type MOL
InChI Key HQACQGVVMYJUAG-IMMUGOHXSA-N
3
Targets
8
Activities
2
Assay Types
14
PK Parameters
15
Publications
0
Known Names

Molecular Properties

526.0
MW (Da)
5.94
ALogP
4
HBA
1
HBD
58.8
PSA (Ų)
0.46
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H35ClF3N3O2
MW 526.04
Aromatic Rings 2
Heavy Atoms 36
NP-Likeness -0.98

Activity Summary

Ki 6 meas. best 7.85
IC50 2 meas. best 5.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Melanocortin receptor 4
CHEMBL259
 Ki 7.85 7.85 14.0 2
Melanocortin receptor 5
CHEMBL4608
 Ki 7.07 7.07 86.0 2
Melanocortin receptor 3
CHEMBL4644
 Ki 6.5 6.5 320.0 2
Melanocortin receptor 4
CHEMBL259
 IC50 5.77 5.77 1700.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 1452.0 ng.hr.mL-1 Mus musculus
AUC 249.0 ng.hr.mL-1 Mus musculus
AUC 249.0 ng.hr.mL-1 Mus musculus
CL 62.3 mL.min-1.kg-1 Mus musculus
CL 62.3 mL.min-1.kg-1 Mus musculus
Cmax 188.2 nM Mus musculus
Cmax 188.2 nM Mus musculus
F 8.6 % Mus musculus
F 8.6 % Mus musculus
T1/2 1.9 hr Mus musculus
T1/2 1.9 hr Mus musculus
Tmax 0.25 hr Mus musculus
Tmax 0.25 hr Mus musculus
Vd 10.3 L.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Melanocortin receptor 4 Ki = 14.0 nM 7.85 Displacement of [125I]NDP-MSH from human MC4R stably expressed in HEK293 cells 16824757
Melanocortin receptor 4 Ki = 14.0 nM 7.85 Displacement of [125I]NDPMSH from human MC4R expressed in HEK293 cells 17994683
Melanocortin receptor 5 Ki = 86.0 nM 7.07 Displacement of [125I]NDP-MSH from human MC5R stably expressed in HEK293 cells 16824757
Melanocortin receptor 5 Ki = 86.0 nM 7.07 Displacement of [125I]NDPMSH from human MC5R expressed in HEK293 cells 17994683
Melanocortin receptor 3 Ki = 320.0 nM 6.5 Displacement of [125I]NDP-MSH from human MC3R stably expressed in HEK293 cells 16824757
Melanocortin receptor 3 Ki = 320.0 nM 6.5 Displacement of [125I]NDPMSH from human MC3R expressed in HEK293 cells 17994683
Melanocortin receptor 4 IC50 = 1700.0 nM 5.77 Activity at MC4R assessed as inhibition of alpha MSH-stimulated cAMP production ... 16824757
Melanocortin receptor 4 IC50 = 1700.0 nM 5.77 Antagonist activity at human MC4R expressed in HEK293 cells assessed as inhibiti... 17994683

Literature References

PubMed DOI Target Context # Activities
16824757 10.1016/j.bmcl.2006.06.075 Mus musculus 12
17994683 10.1021/jm701137s Mus musculus 7
16824757 10.1016/j.bmcl.2006.06.075 Melanocortin receptor 4 2
17994683 10.1021/jm701137s Melanocortin receptor 4 2
17994683 10.1021/jm701137s Brain 2
17994683 10.1021/jm701137s Nucleic Acid 2
16824757 10.1016/j.bmcl.2006.06.075 Melanocyte-stimulating hormone receptor 1
16824757 10.1016/j.bmcl.2006.06.075 Melanocortin receptor 3 1
16824757 10.1016/j.bmcl.2006.06.075 Melanocortin receptor 5 1
16824757 10.1016/j.bmcl.2006.06.075 No relevant target 1
17994683 10.1021/jm701137s Melanocyte-stimulating hormone receptor 1
17994683 10.1021/jm701137s Melanocortin receptor 5 1
17994683 10.1021/jm701137s No relevant target 1
17994683 10.1021/jm701137s Melanocortin receptor 3 1
17994683 10.1021/jm701137s Unchecked 1

Data from ChEMBL 36 via Core Engine