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Compound Detail

CHEMBL4783581

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C[C@](O)(Cn1cc(F)cn1)C(=O)Nc1ccc(C#N)c(C(F)(F)F)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4783581
Phase Preclinical
Structure Type MOL
InChI Key YDRMSDHDYRAUBR-AWEZNQCLSA-N
4
Targets
11
Activities
1
Assay Types
4
PK Parameters
16
Publications
0
Known Names

Molecular Properties

356.3
MW (Da)
2.30
ALogP
5
HBA
2
HBD
90.9
PSA (Ų)
0.82
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H12F4N4O2
MW 356.28
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -1.70

Activity Summary

IC50 11 meas. best 7.04

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Androgen receptor
CHEMBL1871
 IC50 7.04 6.4875 92.2 8
Progesterone receptor
CHEMBL208
 IC50 6.39 6.39 403.0 1
Unchecked
CHEMBL612545
 IC50 5.7 5.7 2000.0 1
CWR22R
CHEMBL612657
 IC50 4.89 4.89 12900.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.89 mL.min-1.kg-1 Mus musculus
T1/2 1.299 hr Mus musculus
T1/2 1.299 hr Mus musculus
T1/2 4.567 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Androgen receptor IC50 = 92.2 nM 7.04 Human Androgen Receptor (hAR) Ligand Binding Domain (LBD) Affinity Assay: Method... -
Androgen receptor IC50 = 199.0 nM 6.7 Antagonist activity at recombinant human AR expressed in HEK293 cells assessed a... 33095584
Androgen receptor IC50 = 199.0 nM 6.7 Antagonist activity at human androgen receptor expressed in HEK-293 cells harbor... 34269581
Androgen receptor IC50 = 199.0 nM 6.7 Human Androgen Receptor (hAR) Ligand Binding Domain (LBD) Affinity Assay: Method... -
Androgen receptor IC50 = 199.0 nM 6.7 Human Androgen Receptor (hAR) Ligand Binding Domain (LBD) Affinity Assay: Method... -
Androgen receptor IC50 = 219.0 nM 6.66 Antagonist activity at recombinant human AR F876L mutant expressed in COS cells ... 33095584
Progesterone receptor IC50 = 403.0 nM 6.39 Antagonist activity at recombinant human PR expressed in COS cells assessed as i... 33095584
Unchecked IC50 = 2000.0 nM 5.7 SARD activity at AR-LBD W741L mutant (unknown origin) after 4 hrs by luciferase ... 32546299
Androgen receptor IC50 = 2000.0 nM 5.7 SARD activity at AR-LBD T877A mutant (unknown origin) after 4 hrs by luciferase ... 32546299
Androgen receptor IC50 = 2000.0 nM 5.7 SARD activity at AR-LBD F876L mutant (unknown origin) after 4 hrs by luciferase ... 32546299
CWR22R IC50 = 12900.0 nM 4.89 Antiproliferative activity against AR/AR-V7 positive human 22Rv1 cells assessed ... 38512060

Literature References

PubMed DOI Target Context # Activities
33095584 10.1021/acs.jmedchem.0c00943 Androgen receptor 7
34269581 10.1021/acs.jmedchem.1c00439 Androgen receptor 5
33095584 10.1021/acs.jmedchem.0c00943 ADMET 2
32546299 10.1016/j.bmc.2020.115554 Androgen receptor 2
34269581 10.1021/acs.jmedchem.1c00439 ADMET 2
33095584 10.1021/acs.jmedchem.0c00943 Mineralocorticoid receptor 1
33095584 10.1021/acs.jmedchem.0c00943 Estrogen receptor 1
33095584 10.1021/acs.jmedchem.0c00943 Glucocorticoid receptor 1
33095584 10.1021/acs.jmedchem.0c00943 Unchecked 1
33095584 10.1021/acs.jmedchem.0c00943 Progesterone receptor 1
32546299 10.1016/j.bmc.2020.115554 Unchecked 1
35786895 10.1021/acs.jmedchem.2c00716 Androgen receptor 1
35786895 10.1021/acs.jmedchem.2c00716 MR49F 1
36459083 10.1021/acs.jmedchem.2c01487 LNCaP 1
36459083 10.1021/acs.jmedchem.2c01487 ADMET 1
38512060 10.1021/acs.jmedchem.3c02177 CWR22R 1

Data from ChEMBL 36 via Core Engine