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Compound Detail

CHEMBL436774

AR9281
🧪 Phase II
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🧪 Phase II
CC(=O)N1CCC(NC(=O)NC23CC4CC(CC(C4)C2)C3)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL436774
Name AR9281
Phase Phase II
Structure Type MOL
InChI Key HUDQLWBKJOMXSZ-UHFFFAOYSA-N

Known Names

Ar9281
5
Targets
29
Activities
2
Assay Types
13
PK Parameters
20
Publications
1
Known Names
1
Mechanisms

Molecular Properties

319.4
MW (Da)
2.27
ALogP
2
HBA
2
HBD
61.4
PSA (Ų)
0.82
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Extended Properties

Molecular Formula C18H29N3O2
MW 319.45
Aromatic Rings 0
Heavy Atoms 23
NP-Likeness -1.19

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Epoxide hydratase inhibitor INHIBITOR Bifunctional epoxide hydrolase 2 ✓ ✓

Activity Summary

IC50 26 meas. best 8.77
Ki 3 meas. best 7.71

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional epoxide hydrolase 2
CHEMBL4140
 IC50 8.77 8.465 1.7 4
Unchecked
CHEMBL612545
 IC50 8.7 7.0244 2.0 9
Bifunctional epoxide hydrolase 2
CHEMBL5669
 IC50 8.22 8.22 6.0 1
Bifunctional epoxide hydrolase 2
CHEMBL2409
 IC50 8.15 7.9836 7.0 11
Epoxide hydrolase 1
CHEMBL1968
 IC50 7.84 7.84 14.5 1
Bifunctional epoxide hydrolase 2
CHEMBL2409
 Ki 7.71 7.71 19.5 3

Pharmacokinetic Data

Parameter Value Units Species
AUC 197.0 ng.hr.mL-1 Canis lupus familiaris
AUC 3.7 10^4nM.min Canis lupus familiaris
AUC 720.0 ng.hr.mL-1 Rattus norvegicus
AUC 58.46 ng.hr.mL-1 Mus musculus
Cmax 30.0 nM Mus musculus
F 25.0 % Macaca fascicularis
F 100.0 % Rattus norvegicus
F 25.0 % Macaca fascicularis
F 100.0 % Rattus norvegicus
T1/2 3.0 hr Homo sapiens
T1/2 0.1005 hr Homo sapiens
T1/2 3.0 hr Mus musculus
Tmax 1.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional epoxide hydrolase 2 IC50 = 1.7 nM 8.77 Inhibition of mouse recombinant sEH using PHOME as substrate measured after 10 m... 34218083
Unchecked IC50 = 2.0 nM 8.7 Inhibition of hamster soluble epoxide hydrolase by radioactive assay 17616115
Bifunctional epoxide hydrolase 2 IC50 = 3.0 nM 8.52 Inhibition of mouse soluble epoxide hydrolase 21211973
Bifunctional epoxide hydrolase 2 IC50 = 3.0 nM 8.52 Inhibition of murine soluble epoxide hydrolase expressed in baculovirus infected... 31488357
Bifunctional epoxide hydrolase 2 IC50 = 6.0 nM 8.22 Inhibition of rat recombinant soluble epoxide hydrolase by fluorescent assay 17616115
Bifunctional epoxide hydrolase 2 IC50 = 7.0 nM 8.15 Inhibition of soluble epoxide hydroxylase by kinetic fluorescent assay 16870439
Bifunctional epoxide hydrolase 2 IC50 = 7.0 nM 8.15 Inhibition of human soluble epoxide hydrolase using CMNPC as substrate after 5 m... 22079754
Bifunctional epoxide hydrolase 2 IC50 = 8.0 nM 8.1 Inhibition of human soluble epoxide hydrolase 21211973
Bifunctional epoxide hydrolase 2 IC50 = 8.0 nM 8.1 Inhibition of recombinant human liver soluble epoxide hydrolase expressed in bac... 31488357
Bifunctional epoxide hydrolase 2 IC50 = 8.0 nM 8.1 Inhibition of recombinant human soluble epoxide hydrolase using CMNPC as substra... 32787085
Bifunctional epoxide hydrolase 2 IC50 = 8.0 nM 8.1 Inhibition of human recombinant sEH using CMNPC as substrate incubated for 5 min... 33945278
Bifunctional epoxide hydrolase 2 IC50 = 8.0 nM 8.1 Inhibition of human recombinant sEH 36222708
Bifunctional epoxide hydrolase 2 IC50 = 8.0 nM 8.1 Inhibition of sEH (unknown origin) 37334504
Bifunctional epoxide hydrolase 2 IC50 = 9.0 nM 8.05 Inhibition of mouse recombinant soluble epoxide hydrolase by fluorescent assay 17616115
Unchecked IC50 = 13.0 nM 7.89 Inhibition Assay: The enzyme also can be detected based on the binding of specif... -
Bifunctional epoxide hydrolase 2 IC50 = 13.8 nM 7.86 Inhibition of human recombinant sEH using PHOME as substrate measured after 10 m... 34218083
Epoxide hydrolase 1 IC50 = 14.5 nM 7.84 Inhibition Assay: Inhibition assay of human soluble epoxide hydrolases. -
Bifunctional epoxide hydrolase 2 IC50 = 15.0 nM 7.82 Inhibition of human sEH by fluorescent assay 17616115
Bifunctional epoxide hydrolase 2 Ki = 19.5 nM 7.71 Binding affinity to purified recombinant human sEH by FRET-displacement assay 33550801
Bifunctional epoxide hydrolase 2 Ki = 19.5 nM 7.71 FRET-displacement assay: FRET assays to determine Ki for the compounds of Table ... -

Literature References

PubMed DOI Target Context # Activities
21211973 10.1016/j.bmcl.2010.12.042 Rattus norvegicus 6
22168898 10.1021/jm201468j Homo sapiens 4
25079952 10.1021/jm500694p Mus musculus 4
32787085 10.1021/acs.jmedchem.0c00310 ADMET 3
33945278 10.1021/acs.jmedchem.0c01601 ADMET 3
21211973 10.1016/j.bmcl.2010.12.042 Mus musculus 3
21211973 10.1016/j.bmcl.2010.12.042 Bifunctional epoxide hydrolase 2 3
17616115 10.1021/jm070270t Unchecked 3
17616115 10.1021/jm070270t Bifunctional epoxide hydrolase 2 3
38470246 10.1021/acs.jmedchem.3c02245 Bifunctional epoxide hydrolase 2 2
33550801 10.1021/acs.jmedchem.0c01886 Bifunctional epoxide hydrolase 2 2
34218083 10.1016/j.ejmech.2021.113678 Bifunctional epoxide hydrolase 2 2
33550801 10.1021/acs.jmedchem.0c01886 No relevant target 2
31488357 10.1016/j.bmc.2019.115078 Bifunctional epoxide hydrolase 2 2
22168898 10.1021/jm201468j Mus musculus 2
17616115 10.1021/jm070270t Canis familiaris 1
21211973 10.1016/j.bmcl.2010.12.042 Cytochrome P450 1A2 1
21211973 10.1016/j.bmcl.2010.12.042 Cytochrome P450 2B6 1
21211973 10.1016/j.bmcl.2010.12.042 Cytochrome P450 2C9 1
21211973 10.1016/j.bmcl.2010.12.042 Cytochrome P450 2C19 1

Data from ChEMBL 36 via Core Engine