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Compound Detail

CHEMBL179691

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COc1cccc(-c2c(C)n(Cc3c(F)cccc3F)c(=O)n(C[C@H](N)c3ccccc3)c2=O)c1F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL179691
Phase Preclinical
Structure Type MOL
InChI Key CJUWBZDJMYYRDG-QFIPXVFZSA-N
4
Targets
89
Activities
2
Assay Types
17
PK Parameters
16
Publications
0
Known Names

Molecular Properties

495.5
MW (Da)
4.16
ALogP
6
HBA
1
HBD
79.2
PSA (Ų)
0.42
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H24F3N3O3
MW 495.50
Aromatic Rings 4
Heavy Atoms 36
NP-Likeness -0.78

Activity Summary

IC50 77 meas. best 9.3
Ki 12 meas. best 9.25

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Gonadotropin-releasing hormone receptor
CHEMBL1855
 IC50 9.3 8.3379 0.5 76
Gonadotropin-releasing hormone receptor
CHEMBL1855
 Ki 9.25 9.1371 0.6 7
Gonadotropin-releasing hormone receptor
CHEMBL5647
 Ki 8.46 8.35 3.5 2
Cytochrome P450 3A4
CHEMBL340
 IC50 6.16 6.16 700.0 1
Gonadotropin-releasing hormone receptor
CHEMBL3066
 Ki 5.52 5.4167 3000.0 3

Pharmacokinetic Data

Parameter Value Units Species
AUC 2392.0 ng/mL.kg Cercopithecidae
AUC 106.0 ng.hr.mL-1 Rattus norvegicus
CL 12.6 mL.min-1.kg-1 Cercopithecidae
CL 64.7 mL.min-1.kg-1 Rattus norvegicus
Cmax 1487.39 nM Cercopithecidae
Cmax 48.84 nM Rattus norvegicus
F 16.0 % Cercopithecidae
F 3.5 % Rattus norvegicus
T1/2 3.1 hr Cercopithecidae
T1/2 2.7 hr Homo sapiens
T1/2 4.3 hr -
T1/2 1.3 hr Rattus norvegicus
Tmax 3.0 hr Cercopithecidae
Tmax 0.4 hr Homo sapiens
Tmax 1.0 hr Rattus norvegicus
Vd 3.4 L.kg-1 Cercopithecidae
Vd 7.1 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Gonadotropin-releasing hormone receptor IC50 = 0.5 nM 9.3 Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR H182A 16420049
Gonadotropin-releasing hormone receptor Ki = 0.56 nM 9.25 Binding affinity for Human gonadotropin-releasing hormone receptor 15715483
Gonadotropin-releasing hormone receptor Ki = 0.56 nM 9.25 Binding affinity for Human gonadotropin-releasing hormone receptor 15715483
Gonadotropin-releasing hormone receptor Ki = 0.56 nM 9.25 Binding affinity towards human gonadotropin-releasing hormone receptor (GNRHR) u... 15863308
Gonadotropin-releasing hormone receptor Ki = 0.56 nM 9.25 Binding affinity to human GnRHR 18442905
Gonadotropin-releasing hormone receptor Ki = 0.56 nM 9.25 Binding affinity at human GnRH receptor 18419112
Gonadotropin-releasing hormone receptor Ki = 0.56 nM 9.25 Displacement of [125I-Tyr5,DLeu6,NMeLeu7,Pro9-NEt-]GnRH from human GnRH receptor... 19006286
Gonadotropin-releasing hormone receptor IC50 = 0.59 nM 9.23 Displacement of [125I]D-Trp6-LHRH from human GnRH receptor expressed in CHO-K1 c... 27608177
Gonadotropin-releasing hormone receptor IC50 = 0.59 nM 9.23 Displacement of [125I]D-Trp6-LHRH from human GnRH receptor expressed in CHO-K1 c... 29335207
Gonadotropin-releasing hormone receptor IC50 = 0.6 nM 9.22 Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR H182E 16420049
Gonadotropin-releasing hormone receptor IC50 = 0.7 nM 9.15 Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR E111K 16420049
Gonadotropin-releasing hormone receptor IC50 = 0.8 nM 9.1 Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR E111A 16420049
Gonadotropin-releasing hormone receptor IC50 = 0.9 nM 9.05 Displacement of [125I]-His5, D-Tyr6]GnRH from human wild type GnRHR 16420049
Gonadotropin-releasing hormone receptor IC50 = 1.0 nM 9.0 Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR S203K 16420049
Gonadotropin-releasing hormone receptor IC50 = 1.0 nM 9.0 Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR N305A 16420049
Gonadotropin-releasing hormone receptor IC50 = 1.1 nM 8.96 Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR S168A 16420049
Gonadotropin-releasing hormone receptor IC50 = 1.1 nM 8.96 Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR Q189K 16420049
Gonadotropin-releasing hormone receptor IC50 = 1.1 nM 8.96 Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR E295A 16420049
Gonadotropin-releasing hormone receptor IC50 = 1.1 nM 8.96 Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR K191E 16420049
Gonadotropin-releasing hormone receptor IC50 = 1.1 nM 8.96 Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR Q189A 16420049

Literature References

PubMed DOI Target Context # Activities
16420049 10.1021/jm0506928 Gonadotropin-releasing hormone receptor 77
15715483 10.1021/jm049218c ADMET 7
19006286 10.1021/jm8006454 Rattus norvegicus 7
15715483 10.1021/jm049218c Gonadotropin-releasing hormone receptor 5
19006286 10.1021/jm8006454 Gonadotropin-releasing hormone receptor 4
18419112 10.1021/jm701249f Gonadotropin-releasing hormone receptor 3
18419112 10.1021/jm701249f Homo sapiens 2
19006286 10.1021/jm8006454 No relevant target 2
19006286 10.1021/jm8006454 Caco-2 2
27608177 10.1021/acs.jmedchem.6b01071 Gonadotropin-releasing hormone receptor 2
15863308 10.1016/j.bmcl.2005.03.057 Gonadotropin-releasing hormone receptor 1
18442905 10.1016/j.bmcl.2008.04.029 Gonadotropin-releasing hormone receptor 1
18419112 10.1021/jm701249f Rhesus monkey 1
19006286 10.1021/jm8006454 Cytochrome P450 3A4 1
19006286 10.1021/jm8006454 Cynomolgus monkey 1
29335207 10.1016/j.ejmech.2017.12.095 Gonadotropin-releasing hormone receptor 1

Data from ChEMBL 36 via Core Engine