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Compound Detail

CHEMBL1644759

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Cc1cc(-c2cccc3cc[nH]c23)c(Cl)c2c1NC(C)(C)[C@H](O)[C@H]2C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1644759
Phase Preclinical
Structure Type MOL
InChI Key YFJZCMOHVUUOJJ-FKIZINRSSA-N
4
Targets
11
Activities
3
Assay Types
2
PK Parameters
7
Publications
0
Known Names

Molecular Properties

354.9
MW (Da)
5.47
ALogP
2
HBA
3
HBD
48.0
PSA (Ų)
0.54
QED
1
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H23ClN2O
MW 354.88
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness 0.32

Activity Summary

Ki 5 meas. best 8.77
IC50 4 meas. best 8.96
EC50 2 meas. best 8.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glucocorticoid receptor
CHEMBL2034
 IC50 8.96 8.4575 1.1 4
Glucocorticoid receptor
CHEMBL2034
 Ki 8.77 8.77 1.7 2
Glucocorticoid receptor
CHEMBL2034
 EC50 8.15 8.15 7.1 2
Mineralocorticoid receptor
CHEMBL1994
 Ki 6.1 6.1 800.0 1
Androgen receptor
CHEMBL1871
 Ki 6.05 6.05 900.0 1
Progesterone receptor
CHEMBL208
 Ki 5.92 5.92 1200.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.055 hr Rattus norvegicus
T1/2 0.07833 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glucocorticoid receptor IC50 = 1.1 nM 8.96 Transrepression activity at glucocorticoid receptor in TNFalpha/IL1beta-stimulat... 21115247
Glucocorticoid receptor IC50 = 1.1 nM 8.96 Agonist activity at GR expressed in IL-1beta- and TNFalpha-stimulated HepG2 cell... 21316964
Glucocorticoid receptor Ki = 1.7 nM 8.77 Displacement of radiolabeled Dexamethasone from glucocorticoid receptor expresse... 21115247
Glucocorticoid receptor Ki = 1.7 nM 8.77 Displacement of radiolabeled Dexamethasone from GR 21316964
Glucocorticoid receptor EC50 = 7.1 nM 8.15 Agonist activity at glucocorticoid receptor in human HepG2 cells co-transfected ... 21115247
Glucocorticoid receptor EC50 = 7.1 nM 8.15 Agonist activity at GR expressed in african green monkey CV1 cells transfected w... 21316964
Glucocorticoid receptor IC50 = 7.8 nM 8.11 Agonist activity at human GR expressed in NHDF cells assessed as inhibition of I... 21316964
Glucocorticoid receptor IC50 = 16.0 nM 7.8 Transrepression activity at glucocorticoid receptor in IL-1beta-stimulated human... 21115247
Mineralocorticoid receptor Ki = 800.0 nM 6.1 Binding affinity to mineralocorticoid receptor 21115247
Androgen receptor Ki = 900.0 nM 6.05 Binding affinity to androgen receptor 21115247
Progesterone receptor Ki = 1200.0 nM 5.92 Binding affinity to progesterone receptor 21115247

Literature References

PubMed DOI Target Context # Activities
21115247 10.1016/j.bmcl.2010.11.047 Glucocorticoid receptor 7
21316964 10.1016/j.bmcl.2011.01.093 Glucocorticoid receptor 7
21115247 10.1016/j.bmcl.2010.11.047 Unchecked 3
21316964 10.1016/j.bmcl.2011.01.093 Liver microsomes 2
21115247 10.1016/j.bmcl.2010.11.047 Progesterone receptor 1
21115247 10.1016/j.bmcl.2010.11.047 Mineralocorticoid receptor 1
21115247 10.1016/j.bmcl.2010.11.047 Androgen receptor 1

Data from ChEMBL 36 via Core Engine