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Compound Detail

CHEMBL509075

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COc1cccc(-c2cn(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@H](NCCCC(=O)O)c3ccccc3)c2=O)c1F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL509075
Phase Preclinical
Structure Type MOL
InChI Key FWSQRSDDLDNXGE-VWLOTQADSA-N
2
Targets
10
Activities
2
Assay Types
18
PK Parameters
11
Publications
0
Known Names

Molecular Properties

617.6
MW (Da)
5.23
ALogP
7
HBA
2
HBD
102.6
PSA (Ų)
0.17
QED
2
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C31H28F5N3O5
MW 617.57
Aromatic Rings 4
Heavy Atoms 44
NP-Likeness -0.83

Activity Summary

IC50 6 meas. best 8.31
Ki 4 meas. best 8.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Gonadotropin-releasing hormone receptor
CHEMBL1855
 Ki 8.92 8.8 1.2 4
Gonadotropin-releasing hormone receptor
CHEMBL1855
 IC50 8.31 7.82 4.9 2
Cytochrome P450 3A4
CHEMBL340
 IC50 4.44 4.43 36000.0 4

Pharmacokinetic Data

Parameter Value Units Species
AUC 63.3 ng.hr.mL-1 Rattus norvegicus
AUC 1904.0 ng.hr.mL-1 Macaca fascicularis
CL 64.0 mL.min-1.kg-1 Rattus norvegicus
CL 64.1 mL.min-1.kg-1 Rattus norvegicus
CL 20.9 mL.min-1.kg-1 Macaca fascicularis
CL 10.0 mL.min-1.kg-1 Homo sapiens
Cmax 124.68 nM Rattus norvegicus
Cmax 3301.65 nM Macaca fascicularis
F 2.4 % Rattus norvegicus
F 2.4 % Rattus norvegicus
F 22.6 % Macaca fascicularis
T1/2 0.3 hr Rattus norvegicus
T1/2 0.3 hr Rattus norvegicus
T1/2 1.0 hr Macaca fascicularis
Tmax 0.25 hr Rattus norvegicus
Tmax 0.5 hr Macaca fascicularis
Vd 1.7 L.kg-1 Rattus norvegicus
Vd 1.8 L.kg-1 Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Gonadotropin-releasing hormone receptor Ki = 1.2 nM 8.92 Displacement of [125I]Pro-N-Et-GnRH from human cloned GnRH receptor expressed in... 18667310
Gonadotropin-releasing hormone receptor Ki = 1.2 nM 8.92 Displacement of [125I-Tyr5,DLeu6,NMeLeu7,Pro9-NEt-]GnRH from human GnRH receptor... 19006286
Gonadotropin-releasing hormone receptor Ki = 1.995 nM 8.7 Binding affinity to human GnRHR 18442910
Gonadotropin-releasing hormone receptor Ki = 2.2 nM 8.66 Binding affinity to human GnRHR 18442910
Gonadotropin-releasing hormone receptor IC50 = 4.9 nM 8.31 Antagonist activity at human GnRHR expressed in RBL cells assessed as inhibition... 18442910
Gonadotropin-releasing hormone receptor IC50 = 47.0 nM 7.33 Antagonist activity at human GnRH receptor expressed in RBL1 cells assessed as i... 19006286
Cytochrome P450 3A4 IC50 = 36000.0 nM 4.44 Inhibition of recombinant CYP3A4 by microtiter plate-based fluorimetric assay 18667310
Cytochrome P450 3A4 IC50 = 36000.0 nM 4.44 Inhibition of CYP3A4 18442910
Cytochrome P450 3A4 IC50 = 36000.0 nM 4.44 Inhibition of CYP3A4 19006286
Cytochrome P450 3A4 IC50 = 39810.72 nM 4.4 Inhibition of CYP3A4 18442910

Literature References

PubMed DOI Target Context # Activities
18442910 10.1016/j.bmcl.2008.04.036 Rattus norvegicus 7
18442910 10.1016/j.bmcl.2008.04.036 Cynomolgus monkey 7
18442910 10.1016/j.bmcl.2008.04.036 Gonadotropin-releasing hormone receptor 5
18667310 10.1016/j.bmcl.2008.07.059 Rattus norvegicus 3
18442910 10.1016/j.bmcl.2008.04.036 Cytochrome P450 3A4 2
18442910 10.1016/j.bmcl.2008.04.036 No relevant target 2
19006286 10.1021/jm8006454 Gonadotropin-releasing hormone receptor 2
18667310 10.1016/j.bmcl.2008.07.059 Cytochrome P450 3A4 1
18667310 10.1016/j.bmcl.2008.07.059 Gonadotropin-releasing hormone receptor 1
18442910 10.1016/j.bmcl.2008.04.036 Liver microsomes 1
19006286 10.1021/jm8006454 Cytochrome P450 3A4 1

Data from ChEMBL 36 via Core Engine