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Compound Detail

CHEMBL460480

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CCn1cc(CN2CCN(c3cccc4[nH]c(-c5ccc(C(C)(C)C)cc5)nc34)CC2)c(=O)[nH]c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL460480
Phase Preclinical
Structure Type MOL
InChI Key YJBAGQATRBRFBC-UHFFFAOYSA-N
4
Targets
11
Activities
2
Assay Types
10
PK Parameters
12
Publications
0
Known Names

Molecular Properties

486.6
MW (Da)
3.72
ALogP
6
HBA
2
HBD
90.0
PSA (Ų)
0.45
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C28H34N6O2
MW 486.62
Aromatic Rings 4
Heavy Atoms 36
NP-Likeness -1.41

Activity Summary

IC50 10 meas. best 8.8
Ki 1 meas. best 6.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Gonadotropin-releasing hormone receptor
CHEMBL1855
 IC50 8.8 8.628 1.6 5
Gonadotropin-releasing hormone receptor
CHEMBL3066
 IC50 7.76 7.6225 17.5 4
Unchecked
CHEMBL612545
 IC50 7.23 7.23 59.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 6.64 6.64 230.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2717.0 ng.hr.mL-1 Rattus norvegicus
AUC 190.0 ng.hr.mL-1 Rattus norvegicus
CL 95.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 986.4 nM Rattus norvegicus
F 72.0 % Rattus norvegicus
F 74.0 % Rattus norvegicus
T1/2 0.08333 hr Rattus norvegicus
T1/2 3.1 hr Rattus norvegicus
T1/2 1.1 hr Rattus norvegicus
Tmax 0.67 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Gonadotropin-releasing hormone receptor IC50 = 1.6 nM 8.8 Binding affinity at human GnRH receptor by competition binding assay 18419112
Gonadotropin-releasing hormone receptor IC50 = 1.7 nM 8.77 Displacement of [125I]-(D-Trp6)-GnRH from human GnRH receptor 19251413
Gonadotropin-releasing hormone receptor IC50 = 1.7 nM 8.77 Displacement of [125I]-(D-Trp6)LHRH from human recombinant GnRH receptor 18511284
Gonadotropin-releasing hormone receptor IC50 = 4.0 nM 8.4 Antagonist activity at human recombinant GnRH receptor expressed in HEK293 cells... 19251413
Gonadotropin-releasing hormone receptor IC50 = 4.0 nM 8.4 Antagonist activity at human recombinant GnRH receptor assessed as reduction in ... 18511284
Gonadotropin-releasing hormone receptor IC50 = 17.5 nM 7.76 Displacement of [125I]-(D-Trp6)LHRH from rat recombinant GnRH receptor 18511284
Gonadotropin-releasing hormone receptor IC50 = 18.0 nM 7.75 Displacement of [125I]-(D-Trp6)-GnRH from rat GnRH receptor 19251413
Gonadotropin-releasing hormone receptor IC50 = 18.0 nM 7.75 Binding affinity at rat GnRH receptor by competition binding assay 18419112
Unchecked IC50 = 59.0 nM 7.23 Reduction in leutinizing hormone release in (D-Trp6)-GnRH-stimulated rat primary... 19251413
Gonadotropin-releasing hormone receptor IC50 = 59.0 nM 7.23 Antagonist activity at recombinant GnRH receptor in CO2 asphyxiated rat primary ... 18511284
5-hydroxytryptamine receptor 2A Ki = 230.0 nM 6.64 Binding affinity to 5HT2A receptor 18511284

Literature References

PubMed DOI Target Context # Activities
18511284 10.1016/j.bmc.2008.05.024 Rattus norvegicus 10
18511284 10.1016/j.bmc.2008.05.024 Gonadotropin-releasing hormone receptor 4
19251413 10.1016/j.bmcl.2009.02.043 Gonadotropin-releasing hormone receptor 3
19251413 10.1016/j.bmcl.2009.02.043 Liver microsomes 2
18419112 10.1021/jm701249f Gonadotropin-releasing hormone receptor 2
19251413 10.1016/j.bmcl.2009.02.043 Cytochrome P450 2C9 1
19251413 10.1016/j.bmcl.2009.02.043 Cytochrome P450 2D6 1
19251413 10.1016/j.bmcl.2009.02.043 Cytochrome P450 3A4 1
19251413 10.1016/j.bmcl.2009.02.043 No relevant target 1
19251413 10.1016/j.bmcl.2009.02.043 Unchecked 1
18419112 10.1021/jm701249f Rattus norvegicus 1
18511284 10.1016/j.bmc.2008.05.024 5-hydroxytryptamine receptor 2A 1

Data from ChEMBL 36 via Core Engine