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Compound Detail

CHEMBL393576

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CC(C)C[C@H](NCCN)c1cccc(F)c1N1CCN(C(=O)[C@@H](Cc2ccc(Cl)cc2Cl)N2CCCC2=O)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL393576
Phase Preclinical
Structure Type MOL
InChI Key CGANDSYNDFLFKG-RRPNLBNLSA-N
9
Targets
17
Activities
3
Assay Types
15
PK Parameters
20
Publications
0
Known Names

Molecular Properties

592.6
MW (Da)
4.65
ALogP
5
HBA
2
HBD
81.9
PSA (Ų)
0.40
QED
1
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C30H40Cl2FN5O2
MW 592.59
Aromatic Rings 2
Heavy Atoms 40
NP-Likeness -1.11

Activity Summary

Ki 12 meas. best 9.15
IC50 3 meas. best 7.68
EC50 2 meas. best 7.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Melanocortin receptor 4
CHEMBL3719
 Ki 9.15 9.15 0.7 2
Melanocortin receptor 4
CHEMBL259
 Ki 9.05 9.04 0.9 2
Melanocortin receptor 4
CHEMBL2700
 Ki 9.0 9.0 1.0 1
Melanocortin receptor 4
CHEMBL259
 IC50 7.68 7.68 21.0 2
Growth hormone secretagogue receptor type 1
CHEMBL4616
 EC50 7.1 7.1 79.0 2
Melanocortin receptor 3
CHEMBL4774
 Ki 6.75 6.75 180.0 1
Melanocortin receptor 3
CHEMBL4023
 Ki 6.62 6.62 240.0 1
Growth hormone secretagogue receptor type 1
CHEMBL4616
 Ki 6.14 6.14 720.0 1
Melanocortin receptor 3
CHEMBL4644
 Ki 6.12 6.12 750.0 2
Melanocortin receptor 5
CHEMBL4608
 Ki 6.07 6.07 850.0 2
Cytochrome P450 3A4
CHEMBL340
 IC50 5.31 5.31 4900.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 9976.0 ng.hr.mL-1 Mus musculus
AUC 1950.0 ng.hr.mL-1 Mus musculus
AUC 1950.0 ng.hr.mL-1 Mus musculus
CL 15.0 mL.min-1.kg-1 Mus musculus
CL 15.0 mL.min-1.kg-1 Mus musculus
Cmax 931.5 nM Mus musculus
Cmax 931.5 nM Mus musculus
F 19.5 % Mus musculus
F 19.5 % Mus musculus
T1/2 10.0 hr Mus musculus
T1/2 10.0 hr Mus musculus
Tmax 2.0 hr Mus musculus
Tmax 2.0 hr Mus musculus
Vd 13.0 L.kg-1 Mus musculus
Vd 13.0 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 = 0.71 nM 9.15 Binding affinity at mouse MC4R 17822895
Melanocortin receptor 4 Ki = 0.71 nM 9.15 Binding affinity to mouse MC4R 17994683
Melanocortin receptor 4 Ki = 0.9 nM 9.05 Displacement of [125I]NDPMSH from human MC4R expressed in HEK293 cells 17994683
Melanocortin receptor 4 Ki = 0.94 nM 9.03 Binding affinity at human MC4R 17822895
Melanocortin receptor 4 Ki = 1.0 nM 9.0 Binding affinity at rat MC4R 17822895
Melanocortin receptor 4 IC50 = 21.0 nM 7.68 Antagonist activity at human MC4R expressed in HEK293 cells by cAMP accumulation... 17822895
Melanocortin receptor 4 IC50 = 21.0 nM 7.68 Antagonist activity at human MC4R expressed in HEK293 cells assessed as inhibiti... 17994683
Growth hormone secretagogue receptor type 1 EC50 = 79.0 nM 7.1 Agonist activity at GHSR 17994683
Growth hormone secretagogue receptor type 1 EC50 = 79.0 nM 7.1 Agonist activity at ghrelin receptor 17822895
Melanocortin receptor 3 Ki = 180.0 nM 6.75 Binding affinity at mouse MC3R 17822895
Melanocortin receptor 3 Ki = 240.0 nM 6.62 Binding affinity at rat MC3R 17822895
Growth hormone secretagogue receptor type 1 Ki = 720.0 nM 6.14 Binding affinity to GHSR 17994683
Melanocortin receptor 3 Ki = 750.0 nM 6.12 Binding affinity at human MC3R 17822895
Melanocortin receptor 3 Ki = 750.0 nM 6.12 Displacement of [125I]NDPMSH from human MC3R expressed in HEK293 cells 17994683
Melanocortin receptor 5 Ki = 850.0 nM 6.07 Binding affinity at human MC5R 17822895
Melanocortin receptor 5 Ki = 850.0 nM 6.07 Displacement of [125I]NDPMSH from human MC5R expressed in HEK293 cells 17994683
Cytochrome P450 3A4 IC50 = 4900.0 nM 5.31 Inhibition of microsomal CYP3A4 17822895

Literature References

PubMed DOI Target Context # Activities
17822895 10.1016/j.bmcl.2007.07.097 Mus musculus 10
17994683 10.1021/jm701137s Mus musculus 7
17822895 10.1016/j.bmcl.2007.07.097 Melanocortin receptor 4 4
17994683 10.1021/jm701137s Growth hormone secretagogue receptor type 1 3
17822895 10.1016/j.bmcl.2007.07.097 Melanocortin receptor 3 3
17822895 10.1016/j.bmcl.2007.07.097 Brain 3
17994683 10.1021/jm701137s Melanocortin receptor 4 3
17994683 10.1021/jm701137s Caco-2 2
17822895 10.1016/j.bmcl.2007.07.097 Caco-2 2
17994683 10.1021/jm701137s Nucleic Acid 2
17994683 10.1021/jm701137s Brain 2
17822895 10.1016/j.bmcl.2007.07.097 Nucleic Acid 2
17822895 10.1016/j.bmcl.2007.07.097 Growth hormone secretagogue receptor type 1 1
17994683 10.1021/jm701137s No relevant target 1
17994683 10.1021/jm701137s Melanocortin receptor 5 1
17994683 10.1021/jm701137s Melanocortin receptor 3 1
17994683 10.1021/jm701137s Melanocyte-stimulating hormone receptor 1
17822895 10.1016/j.bmcl.2007.07.097 Melanocortin receptor 5 1
17822895 10.1016/j.bmcl.2007.07.097 Melanocyte-stimulating hormone receptor 1
17822895 10.1016/j.bmcl.2007.07.097 No relevant target 1

Data from ChEMBL 36 via Core Engine