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Compound Detail

CHEMBL1258904

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CCC(=O)N1CCC(NC(=O)Nc2ccc(OC(F)(F)F)cc2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1258904
Phase Preclinical
Structure Type MOL
InChI Key AAJMQTLFRTZCJK-UHFFFAOYSA-N
4
Targets
20
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

359.4
MW (Da)
3.11
ALogP
3
HBA
2
HBD
70.7
PSA (Ų)
0.87
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H20F3N3O3
MW 359.35
Aromatic Rings 1
Heavy Atoms 25
NP-Likeness -1.79

Activity Summary

IC50 15 meas. best 8.55
Ki 5 meas. best 9.04

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional epoxide hydrolase 2
CHEMBL2409
 Ki 9.04 8.628 0.9 5
Bifunctional epoxide hydrolase 2
CHEMBL4140
 IC50 8.55 7.955 2.8 4
Bifunctional epoxide hydrolase 2
CHEMBL2409
 IC50 8.43 8.16 3.7 6
Bifunctional epoxide hydrolase 2
CHEMBL5669
 IC50 7.54 7.54 29.1 1
Unchecked
CHEMBL612545
 IC50 7.36 6.875 44.0 4

Pharmacokinetic Data

Parameter Value Units Species
AUC 3827.08 ng.hr.mL-1 Mus musculus
Cmax 495.0 nM Mus musculus
T1/2 12.1 hr Mus musculus
T1/2 0.1833 hr Homo sapiens
T1/2 0.2267 hr Rattus norvegicus
Tmax 8.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional epoxide hydrolase 2 Ki = 0.91 nM 9.04 Assays for Epoxide Hydrolase Activity: Any of a number of standard assays for de... -
Bifunctional epoxide hydrolase 2 Ki = 0.91 nM 9.04 FRET-displacement assay: FRET assays to determine Ki for the compounds of Table ... -
Bifunctional epoxide hydrolase 2 Ki = 0.91 nM 9.04 Binding affinity to purified recombinant human sEH by FRET-displacement assay 33550801
Bifunctional epoxide hydrolase 2 Ki = 0.91 nM 9.04 Inhibition of human recombinant soluble epoxide hydrolase by FRET-based ACPU dis... 25079952
Bifunctional epoxide hydrolase 2 IC50 = 2.8 nM 8.55 Fluorescent Based Assay: IC50 values were determined using a sensitive fluoresce... -
Bifunctional epoxide hydrolase 2 IC50 = 2.8 nM 8.55 Inhibition of mouse recombinant soluble epoxide hydrolase by fluorescence assay 20812725
Bifunctional epoxide hydrolase 2 IC50 = 3.7 nM 8.43 Inhibition of human recombinant soluble epoxide hydrolase by fluorescence assay 20812725
Bifunctional epoxide hydrolase 2 IC50 = 3.7 nM 8.43 Inhibition of human recombinant soluble epoxide hydrolase assessed as cyano(6-me... 23726028
Bifunctional epoxide hydrolase 2 IC50 = 3.7 nM 8.43 Fluorescent Based Assay: IC50 values were determined using a sensitive fluoresce... -
Bifunctional epoxide hydrolase 2 IC50 = 12.8 nM 7.89 Inhibition of recombinant human full length sEH (1 to 555 residues) expressed in... 32551007
Bifunctional epoxide hydrolase 2 IC50 = 13.0 nM 7.89 Inhibition of recombinant human C-terminal sEH (222 to 555 residues) expressed i... 33620196
Bifunctional epoxide hydrolase 2 IC50 = 12.8 nM 7.89 Inhibition of C-terminal domain of human sEH-H assessed as reduction in fluoresc... 35859883
Bifunctional epoxide hydrolase 2 IC50 = 29.1 nM 7.54 Inhibition of rat soluble epoxide hydrolase using [3H]-t-DPPO as a substrate by ... 25079952
Bifunctional epoxide hydrolase 2 IC50 = 43.77 nM 7.36 Inhibition of sEH in C57BL/6J mouse brain homogenate using 14, 15-EET as substra... 39361006
Unchecked IC50 = 44.0 nM 7.36 Inhibition Assay: The enzyme also can be detected based on the binding of specif... -
Bifunctional epoxide hydrolase 2 IC50 = 43.77 nM 7.36 Inhibition of C57BL/6J mouse brain sEH using 14,15-EET as substrate preincubated... 38215588
Unchecked IC50 = 68.0 nM 7.17 Inhibition Assay: The enzyme also can be detected based on the binding of specif... -
Bifunctional epoxide hydrolase 2 Ki = 104.0 nM 6.98 Displacement of (1R,3S)-N-(4-methoxy-2-(trifluoromethyl)benzyl)-3-((7-nitrobenzo... 35859883
Unchecked IC50 = 270.0 nM 6.57 Inhibition of human P38 MAPK by ADP-Glo kinase assay 37722288
Unchecked IC50 = 400.0 nM 6.4 Inhibition Assay: The enzyme also can be detected based on the binding of specif... -

Literature References

PubMed DOI Target Context # Activities
39361006 10.1021/acs.jmedchem.4c01766 Mus musculus 6
25079952 10.1021/jm500694p Bifunctional epoxide hydrolase 2 4
25079952 10.1021/jm500694p Mus musculus 4
35859883 10.1021/acsmedchemlett.2c00073 Bifunctional epoxide hydrolase 2 3
25079952 10.1021/jm500694p No relevant target 2
33550801 10.1021/acs.jmedchem.0c01886 Bifunctional epoxide hydrolase 2 2
33550801 10.1021/acs.jmedchem.0c01886 No relevant target 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
38215588 10.1016/j.ejmech.2023.116113 Bifunctional epoxide hydrolase 2 2
39361006 10.1021/acs.jmedchem.4c01766 Bifunctional epoxide hydrolase 2 2
20812725 10.1021/jm100691c Bifunctional epoxide hydrolase 2 2
23726028 10.1016/j.bmcl.2013.05.011 Bifunctional epoxide hydrolase 2 1
20812725 10.1021/jm100691c No relevant target 1
25079952 10.1021/jm500694p Voltage-gated inwardly rectifying potassium channel KCNH2 1
25079952 10.1021/jm500694p Plasma 1
25079952 10.1021/jm500694p Cytochrome P450 2J2 1
25079952 10.1021/jm500694p ADMET 1
23726028 10.1016/j.bmcl.2013.05.011 HepG2 1
23726028 10.1016/j.bmcl.2013.05.011 Huh-7 1
23726028 10.1016/j.bmcl.2013.05.011 HUVEC 1

Data from ChEMBL 36 via Core Engine