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Compound Detail

CHEMBL229861

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CC[C@H]1[C@@H]2[C@@H](O)CCN2C(=O)N1c1ccc(C#N)c(Cl)c1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL229861
Phase Preclinical
Structure Type MOL
InChI Key GHMFVPOVQMEIHB-CORIIIEPSA-N
3
Targets
8
Activities
3
Assay Types
9
PK Parameters
20
Publications
0
Known Names

Molecular Properties

319.8
MW (Da)
2.67
ALogP
3
HBA
1
HBD
67.6
PSA (Ų)
0.91
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H18ClN3O2
MW 319.79
Aromatic Rings 1
Heavy Atoms 22
NP-Likeness -0.17

Activity Summary

Ki 4 meas. best 9.05
EC50 3 meas. best 8.74
IC50 1 meas. best 5.12

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Androgen receptor
CHEMBL1871
 Ki 9.05 9.05 0.9 4
Androgen receptor
CHEMBL1871
 EC50 8.74 8.74 1.8 2
Androgen receptor
CHEMBL3072
 EC50 8.74 8.74 1.8 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 5.12 5.12 7600.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1943.68 ng.hr.mL-1 Rattus norvegicus
CL 58.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 3096.0 nM Rattus norvegicus
Cmax 2100.0 nM Rattus norvegicus
F 65.0 % Rattus norvegicus
F 65.0 % Rattus norvegicus
T1/2 5.5 hr Rattus norvegicus
T1/2 5.5 hr Rattus norvegicus
Tmax 0.8 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Androgen receptor Ki = 0.9 nM 9.05 Displacement of [3H]DHT from androgen receptor expressed in MDA-MB-453 cells 17552509
Androgen receptor Ki = 0.9 nM 9.05 Displacement of [3H[DHT from androgen receptor endogenously expressed in human M... 19351168
Androgen receptor Ki = 0.9 nM 9.05 Agonist activity at androgen receptor 19432422
Androgen receptor Ki = 0.9 nM 9.05 Binding affinity to Androgen receptor (unknown origin) 35786895
Androgen receptor EC50 = 1.8 nM 8.74 Agonist activity at androgen receptor expressed in C2C12 mouse cells by lucifera... 17552509
Androgen receptor EC50 = 1.8 nM 8.74 Agonist activity at rat androgen receptor expressed in mouse skeletal muscle C2C... 19351168
Androgen receptor EC50 = 1.8 nM 8.74 Agonist activity at Androgen receptor (unknown origin) 35786895
Cytochrome P450 2C19 IC50 = 7600.0 nM 5.12 Inhibition of CYP2C19 17552509

Literature References

PubMed DOI Target Context # Activities
17552509 10.1021/jm070312d Rattus norvegicus 9
19432422 10.1021/jm900280m Rattus norvegicus 4
17552509 10.1021/jm070312d Androgen receptor 3
35786895 10.1021/acs.jmedchem.2c00716 Androgen receptor 2
35786895 10.1021/acs.jmedchem.2c00716 ADMET 2
19351168 10.1021/jm801583j Androgen receptor 2
17552509 10.1021/jm070312d Cytochrome P450 2C19 1
19351168 10.1021/jm801583j No relevant target 1
17552509 10.1021/jm070312d Voltage-gated inwardly rectifying potassium channel KCNH2 1
17552509 10.1021/jm070312d Cytochrome P450 3A4 1
17552509 10.1021/jm070312d Cytochrome P450 2D6 1
17552509 10.1021/jm070312d Cytochrome P450 2C9 1
17552509 10.1021/jm070312d Cytochrome P450 1A2 1
17552509 10.1021/jm070312d Hepatocyte 1
17552509 10.1021/jm070312d Aromatase 1
17552509 10.1021/jm070312d Sex hormone-binding globulin 1
17552509 10.1021/jm070312d Glucocorticoid receptor 1
17552509 10.1021/jm070312d Steroid hormone receptor ERR2 1
17552509 10.1021/jm070312d Steroid hormone receptor ERR1 1
17552509 10.1021/jm070312d Unchecked 1

Data from ChEMBL 36 via Core Engine