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Compound Detail

CHEMBL242459

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O=C(NC12CC3CC(CC(C3)C1)C2)N[C@H]1CC[C@H](Oc2ccc(C(=O)O)cc2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL242459
Phase Preclinical
Structure Type MOL
InChI Key KNBWKJBQDAQARU-KSSCSKLYSA-N
4
Targets
26
Activities
2
Assay Types
5
PK Parameters
20
Publications
0
Known Names

Molecular Properties

412.5
MW (Da)
4.34
ALogP
3
HBA
3
HBD
87.7
PSA (Ų)
0.67
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H32N2O4
MW 412.53
Aromatic Rings 1
Heavy Atoms 30
NP-Likeness -0.52

Activity Summary

IC50 24 meas. best 9.3
Ki 2 meas. best 9.88

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 9.88 9.88 0.1 1
Bifunctional epoxide hydrolase 2
CHEMBL2409
 IC50 9.3 8.9588 0.5 16
Unchecked
CHEMBL612545
 IC50 9.0 8.5475 1.0 4
Bifunctional epoxide hydrolase 2
CHEMBL2409
 Ki 8.82 8.82 1.5 1
Bifunctional epoxide hydrolase 2
CHEMBL4140
 IC50 8.77 8.435 1.7 2
Bifunctional epoxide hydrolase 2
CHEMBL5669
 IC50 8.1 8.1 8.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 14.2 10^4nM.min Canis lupus familiaris
F 98.0 % Canis lupus familiaris
F 98.0 % Canis lupus familiaris
T1/2 19.0 hr Canis lupus familiaris
Tmax 8.0 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.132 nM 9.88 Inhibition of recombinant purified chicken soluble epoxide hydrolase by FRET-bas... 25479771
Bifunctional epoxide hydrolase 2 IC50 = 0.5 nM 9.3 Inhibition of soluble epoxide hydrolase (unknown origin) 31009912
Bifunctional epoxide hydrolase 2 IC50 = 0.5 nM 9.3 Inhibition of recombinant human liver soluble epoxide hydrolase expressed in bac... 31488357
Bifunctional epoxide hydrolase 2 IC50 = 0.5 nM 9.3 Inhibition of recombinant human soluble epoxide hydrolase using CMNPC as substra... 32787085
Bifunctional epoxide hydrolase 2 IC50 = 0.5 nM 9.3 Inhibition of human recombinant sEH using CMNPC as substrate incubated for 5 min... 33945278
Bifunctional epoxide hydrolase 2 IC50 = 0.5 nM 9.3 Inhibition of human recombinant sEH 36222708
Bifunctional epoxide hydrolase 2 IC50 = 0.5 nM 9.3 Inhibition of human recombinant soluble epoxide hydrolase after 10 mins by fluor... 21434686
Bifunctional epoxide hydrolase 2 IC50 = 0.8 nM 9.1 Inhibition of sEH (unknown origin) 35598794
Unchecked IC50 = 1.0 nM 9.0 Inhibition of dog soluble epoxide hydrolase by radioactive assay 17616115
Bifunctional epoxide hydrolase 2 IC50 = 1.0 nM 9.0 Inhibition of human sEH using cyano(6-methoxynaphthalen-2-yl)methyl((3-phenyloxi... 34794001
Bifunctional epoxide hydrolase 2 IC50 = 1.3 nM 8.89 Inhibition of human recombinant soluble epoxide hydrolase 17616115
Bifunctional epoxide hydrolase 2 Ki = 1.5 nM 8.82 Competitive inhibition of human recombinant soluble epoxide hydrolase using [3H]... 23684894
Bifunctional epoxide hydrolase 2 IC50 = 1.5 nM 8.82 sEH Assay: See reference (Jones, P. D.; Wolf, N. M.; Morisseau, C.; Whetstone, P... -
Bifunctional epoxide hydrolase 2 IC50 = 1.5 nM 8.82 Inhibition of human recombinant soluble epoxide hydrolase assessed as cyano(6-me... 23726028
Bifunctional epoxide hydrolase 2 IC50 = 1.5 nM 8.82 Inhibition of human recombinant soluble epoxide hydrolase using CMNPC as substra... 22522007
Bifunctional epoxide hydrolase 2 IC50 = 1.7 nM 8.77 Inhibition of mouse recombinant sEH using CMNPC as substrate incubated for 5 min... 33945278
Unchecked IC50 = 2.0 nM 8.7 Inhibition of hamster soluble epoxide hydrolase by radioactive assay 17616115
Bifunctional epoxide hydrolase 2 IC50 = 2.0 nM 8.7 Inhibition of human sEH by fluorescent assay 17616115
Bifunctional epoxide hydrolase 2 IC50 = 2.0 nM 8.7 Inhibition of human recombinant sEH 32485533
Bifunctional epoxide hydrolase 2 IC50 = 3.0 nM 8.52 Inhibition of human recombinant soluble epoxide hydrolase expressed in baculovir... 29366648

Literature References

PubMed DOI Target Context # Activities
33248848 10.1016/j.ejmech.2020.113028 Mus musculus 8
33945278 10.1021/acs.jmedchem.0c01601 ADMET 6
17616115 10.1021/jm070270t Canis familiaris 5
31488357 10.1016/j.bmc.2019.115078 ADMET 4
17616115 10.1021/jm070270t Bifunctional epoxide hydrolase 2 4
23684894 10.1016/j.bmcl.2013.04.083 Bifunctional epoxide hydrolase 2 3
17616115 10.1021/jm070270t Unchecked 3
32787085 10.1021/acs.jmedchem.0c00310 ADMET 3
33945278 10.1021/acs.jmedchem.0c01601 Bifunctional epoxide hydrolase 2 3
22522007 10.1016/j.bmc.2012.03.058 Mycobacterium tuberculosis 2
25479771 10.1016/j.bmcl.2014.11.053 Unchecked 2
25479771 10.1016/j.bmcl.2014.11.053 Liver microsome 2
33248848 10.1016/j.ejmech.2020.113028 Bifunctional epoxide hydrolase 2 2
33620196 10.1021/acs.jmedchem.0c02063 Heart 2
25479771 10.1016/j.bmcl.2014.11.053 ADMET 2
31488357 10.1016/j.bmc.2019.115078 Bifunctional epoxide hydrolase 2 2
17616115 10.1021/jm070270t Mus musculus 2
35598794 10.1016/j.bmcl.2022.128805 Bifunctional epoxide hydrolase 2 2
32485533 10.1016/j.ejmech.2020.112438 Bifunctional epoxide hydrolase 2 1
22522007 10.1016/j.bmc.2012.03.058 Bifunctional epoxide hydrolase 2 1

Data from ChEMBL 36 via Core Engine