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Compound Detail

CHEMBL4080667

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O=C(CC1(c2ccccc2)C2CC3CC1CC(C2)C3O)N1CC(O)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4080667
Phase Preclinical
Structure Type MOL
InChI Key OAAZMUGLOXGVNH-QKVOFEMESA-N
8
Targets
16
Activities
3
Assay Types
27
PK Parameters
20
Publications
0
Known Names

Molecular Properties

341.4
MW (Da)
1.94
ALogP
3
HBA
2
HBD
60.8
PSA (Ų)
0.88
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H27NO3
MW 341.45
Aromatic Rings 1
Heavy Atoms 25
NP-Likeness 0.40

Activity Summary

IC50 12 meas. best 8.52
EC50 2 meas. best 7.12
Ki 2 meas. best 8.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL4235
 IC50 8.52 7.93 3.0 3
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL4235
 Ki 8.42 8.42 3.8 1
Unchecked
CHEMBL612545
 IC50 8.42 6.8467 3.8 3
Unchecked
CHEMBL612545
 Ki 8.15 8.15 7.0 1
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL3910
 IC50 7.54 7.4 28.6 3
Cynomolgus monkey
CHEMBL613847
 EC50 7.12 7.12 75.0 1
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL2391
 IC50 6.3 6.3 500.0 1
Mus musculus
CHEMBL375
 EC50 6.07 6.07 850.0 1
11-beta-hydroxysteroid dehydrogenase type 2
CHEMBL2908
 IC50 5.46 5.46 3500.0 1
11-beta-hydroxysteroid dehydrogenase type 2
CHEMBL3490
 IC50 5.1 5.1 7900.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 221942.5 ng.hr.mL-1 Rattus norvegicus
AUC 1707.25 ng.hr.mL-1 Mus musculus
AUC 2048.7 ng.hr.mL-1 Rattus norvegicus
AUC 1570.67 ng.hr.mL-1 Canis lupus familiaris
AUC 785.33 ng.hr.mL-1 Macaca fascicularis
CL 50.0 mL.min-1.kg-1 Mus musculus
CL 41.0 mL.min-1.kg-1 Rattus norvegicus
CL 11.0 mL.min-1.kg-1 Canis lupus familiaris
CL 21.2 mL.min-1.kg-1 Macaca fascicularis
F 56.0 % Mus musculus
F 20.0 % Rattus norvegicus
F 72.0 % Canis lupus familiaris
F 57.0 % Macaca fascicularis
MRT 1.3 hr Rattus norvegicus
MRT 3.5 hr Canis lupus familiaris
MRT 3.3 hr Macaca fascicularis
T1/2 3.333 hr Homo sapiens
T1/2 3.333 hr Mus musculus
T1/2 2.017 hr Homo sapiens
T1/2 3.333 hr Macaca fascicularis
T1/2 3.333 hr Canis lupus familiaris
T1/2 0.7833 hr Rattus norvegicus
T1/2 2.0 hr Mus musculus
T1/2 6.0 hr Rattus norvegicus
T1/2 7.4 hr Canis lupus familiaris
T1/2 6.0 hr Macaca fascicularis
Tmax 0.5 hr Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 3.0 nM 8.52 Inhibition of 11beta-HSD1 in human microsomes using [3H]cortisone as substrate p... 28537398
Unchecked IC50 = 3.8 nM 8.42 Inhibition of cynomolgus monkey 11beta-HSD1 28537398
11-beta-hydroxysteroid dehydrogenase 1 Ki = 3.8 nM 8.42 Inhibition of 11beta-HSD1 in human microsomes using [3H]cortisone as substrate p... 28537398
Unchecked Ki = 7.0 nM 8.15 Inhibition of cynomolgus monkey 11beta-HSD1 28537398
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 14.5 nM 7.84 Inhibition of 11beta-HSD1 in human microsomes using [3H]cortisone as substrate p... 28537398
Unchecked IC50 = 16.0 nM 7.8 Inhibition of cynomolgus monkey 11beta-HSD1 28537398
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 28.6 nM 7.54 Inhibition of 11beta-HSD1 in mouse 3T3L1 cells 28537398
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 37.3 nM 7.43 Inhibition of human 11beta-HSD1 expressed in HEK cells 28537398
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 43.5 nM 7.36 Inhibition of mouse 11beta-HSD1 28537398
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 50.3 nM 7.3 Inhibition of mouse 11beta-HSD1 28537398
Cynomolgus monkey EC50 = 75.0 nM 7.12 In vivo inhibition of 11beta-HSD1 in non-fasting diet-induced obese cynomolgus m... 28537398
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 500.0 nM 6.3 Inhibition of rat 11beta-HSD1 28537398
Mus musculus EC50 = 850.0 nM 6.07 In vivo inhibition of 11beta-HSD1 in po dosed non-fasting diet-induced obese mou... 28537398
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 3500.0 nM 5.46 Inhibition of rat 11beta-HSD2 28537398
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 7900.0 nM 5.1 Inhibition of mouse 11beta-HSD2 28537398
Unchecked IC50 = 48000.0 nM 4.32 Inhibition of cynomolgus monkey 11beta-HSD2 28537398

Literature References

PubMed DOI Target Context # Activities
28537398 10.1021/acs.jmedchem.7b00211 Plasma 14
28537398 10.1021/acs.jmedchem.7b00211 Unchecked 13
28537398 10.1021/acs.jmedchem.7b00211 Cynomolgus monkey 13
28537398 10.1021/acs.jmedchem.7b00211 Rattus norvegicus 11
28537398 10.1021/acs.jmedchem.7b00211 Liver 11
28537398 10.1021/acs.jmedchem.7b00211 11-beta-hydroxysteroid dehydrogenase 1 9
28537398 10.1021/acs.jmedchem.7b00211 Mus musculus 8
28537398 10.1021/acs.jmedchem.7b00211 ADMET 7
28537398 10.1021/acs.jmedchem.7b00211 Canis familiaris 6
28537398 10.1021/acs.jmedchem.7b00211 11-beta-hydroxysteroid dehydrogenase type 2 3
28537398 10.1021/acs.jmedchem.7b00211 Cytochrome P450 2A6 1
28537398 10.1021/acs.jmedchem.7b00211 Cytochrome P450 2B6 1
28537398 10.1021/acs.jmedchem.7b00211 Cytochrome P450 2C8 1
28537398 10.1021/acs.jmedchem.7b00211 Cytochrome P450 2C9 1
28537398 10.1021/acs.jmedchem.7b00211 Cytochrome P450 2C19 1
28537398 10.1021/acs.jmedchem.7b00211 Cytochrome P450 2D6 1
28537398 10.1021/acs.jmedchem.7b00211 Cytochrome P450 2E1 1
28537398 10.1021/acs.jmedchem.7b00211 Cytochrome P450 3A4 1
28537398 10.1021/acs.jmedchem.7b00211 HepG2 1
28537398 10.1021/acs.jmedchem.7b00211 Voltage-gated inwardly rectifying potassium channel KCNH2 1

Data from ChEMBL 36 via Core Engine