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Compound Detail

CHEMBL2397148

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O=C(Nc1ccc(OC(F)(F)F)cc1)N[C@H]1CC[C@H](Oc2ccc(C(=O)O)cc2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2397148
Phase Preclinical
Structure Type MOL
InChI Key XDVFKCZZXOGEMN-CZIWCDLHSA-N
6
Targets
21
Activities
2
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

438.4
MW (Da)
4.80
ALogP
4
HBA
3
HBD
96.9
PSA (Ų)
0.60
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H21F3N2O5
MW 438.40
Aromatic Rings 2
Heavy Atoms 31
NP-Likeness -0.93

Activity Summary

IC50 20 meas. best 9.55
Ki 1 meas. best 6.81

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional epoxide hydrolase 2
CHEMBL2409
 IC50 9.55 9.1938 0.3 8
Unchecked
CHEMBL612545
 IC50 8.7 6.9133 2.0 6
Bifunctional epoxide hydrolase 2
CHEMBL4140
 IC50 8.55 8.395 2.8 2
Bifunctional epoxide hydrolase 2
CHEMBL5669
 IC50 7.27 7.27 54.0 1
Fatty-acid amide hydrolase 1
CHEMBL2243
 IC50 6.85 6.715 140.0 2
Bifunctional epoxide hydrolase 2
CHEMBL2409
 Ki 6.81 6.81 156.0 1
Fatty-acid amide hydrolase 1
CHEMBL3455
 IC50 5.2 5.2 6300.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.2683 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional epoxide hydrolase 2 IC50 = 0.28 nM 9.55 Inhibition of recombinant human soluble epoxide hydrolase using PHOME as substra... 36689364
Bifunctional epoxide hydrolase 2 IC50 = 0.4 nM 9.4 Inhibition of soluble epoxide hydrolase (unknown origin) 29366648
Bifunctional epoxide hydrolase 2 IC50 = 0.4 nM 9.4 Inhibition of human recombinant sEH 36222708
Bifunctional epoxide hydrolase 2 IC50 = 0.8 nM 9.1 Inhibition of human recombinant soluble epoxide hydrolase expressed in baculovir... 29366648
Bifunctional epoxide hydrolase 2 IC50 = 0.9 nM 9.05 Inhibition of human recombinant soluble epoxide hydrolase assessed as cyano(6-me... 23726028
Bifunctional epoxide hydrolase 2 IC50 = 0.9 nM 9.05 sEH Assay: See reference (Jones, P. D.; Wolf, N. M.; Morisseau, C.; Whetstone, P... -
Bifunctional epoxide hydrolase 2 IC50 = 1.0 nM 9.0 Inhibition of human soluble epoxide hydrolase using CMNPC as substrate by fluore... 31870649
Bifunctional epoxide hydrolase 2 IC50 = 1.0 nM 9.0 Inhibition of recombinant human soluble epoxide hydrolase using CMNPC as fluores... 32736212
Unchecked IC50 = 2.0 nM 8.7 Inhibition of soluble epoxide in cat brain microsomes using CMNPC substrate by f... 29366648
Bifunctional epoxide hydrolase 2 IC50 = 2.8 nM 8.55 Inhibition of recombinant mouse soluble epoxide hydrolase using PHOME as substra... 36689364
Unchecked IC50 = 5.6 nM 8.25 Inhibition of soluble epoxide in dog brain microsomes using CMNPC substrate by f... 29366648
Bifunctional epoxide hydrolase 2 IC50 = 5.7 nM 8.24 Inhibition of soluble epoxide in mouse brain microsomes using CMNPC substrate by... 29366648
Unchecked IC50 = 19.0 nM 7.72 Inhibition of soluble epoxide in horse brain microsomes using CMNPC substrate by... 29366648
Bifunctional epoxide hydrolase 2 IC50 = 54.0 nM 7.27 Inhibition of soluble epoxide in rat brain microsomes using CMNPC substrate by f... 29366648
Fatty-acid amide hydrolase 1 IC50 = 140.0 nM 6.85 Inhibition of human FAAH expressed in baculovirus-infected High Five cells S9 fr... 29366648
Bifunctional epoxide hydrolase 2 Ki = 156.0 nM 6.81 Competitive inhibition of human recombinant soluble epoxide hydrolase expressed ... 29366648
Fatty-acid amide hydrolase 1 IC50 = 260.0 nM 6.58 Inhibition of human FAAH 29366648
Unchecked IC50 = 1200.0 nM 5.92 Inhibition of FAAH in cat brain microsomes using OMP substrate by fluorescence b... 29366648
Unchecked IC50 = 3300.0 nM 5.48 Inhibition of FAAH in horse brain microsomes using OMP substrate by fluorescence... 29366648
Unchecked IC50 = 3900.0 nM 5.41 Inhibition of FAAH in dog brain microsomes using OMP substrate by fluorescence b... 29366648

Literature References

PubMed DOI Target Context # Activities
29366648 10.1016/j.bmcl.2018.01.003 Bifunctional epoxide hydrolase 2 7
29366648 10.1016/j.bmcl.2018.01.003 Unchecked 6
29366648 10.1016/j.bmcl.2018.01.003 Fatty-acid amide hydrolase 1 4
36689364 10.1021/acs.jmedchem.2c01996 Bifunctional epoxide hydrolase 2 2
23726028 10.1016/j.bmcl.2013.05.011 Receptor-type tyrosine-protein kinase FLT3 1
29366648 10.1016/j.bmcl.2018.01.003 Epoxide hydrolase 1 1
25079952 10.1021/jm500694p Bifunctional epoxide hydrolase 2 1
23726028 10.1016/j.bmcl.2013.05.011 Bifunctional epoxide hydrolase 2 1
23726028 10.1016/j.bmcl.2013.05.011 Tyrosine-protein kinase ABL2 1
23726028 10.1016/j.bmcl.2013.05.011 Fibroblast growth factor receptor 2 1
23726028 10.1016/j.bmcl.2013.05.011 Vascular endothelial growth factor receptor 1 1
23726028 10.1016/j.bmcl.2013.05.011 HUVEC 1
23726028 10.1016/j.bmcl.2013.05.011 Glycogen synthase kinase-3 alpha 1
23726028 10.1016/j.bmcl.2013.05.011 Hepatocyte growth factor receptor 1
23726028 10.1016/j.bmcl.2013.05.011 Platelet-derived growth factor receptor alpha 1
23726028 10.1016/j.bmcl.2013.05.011 Platelet-derived growth factor receptor beta 1
23726028 10.1016/j.bmcl.2013.05.011 3-phosphoinositide-dependent protein kinase 1 1
23726028 10.1016/j.bmcl.2013.05.011 Vascular endothelial growth factor receptor 2 1
23726028 10.1016/j.bmcl.2013.05.011 RAF proto-oncogene serine/threonine-protein kinase 1
23726028 10.1016/j.bmcl.2013.05.011 HepG2 1

Data from ChEMBL 36 via Core Engine