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Compound Detail

CHEMBL4752759

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CC[C@H](C)C(=O)N1CCC(NC(=O)Nc2ccc(OC(F)(F)F)c(F)c2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4752759
Phase Preclinical
Structure Type MOL
InChI Key LHRXHTKENPCGSZ-NSHDSACASA-N
2
Targets
5
Activities
1
Assay Types
9
PK Parameters
16
Publications
0
Known Names

Molecular Properties

405.4
MW (Da)
3.88
ALogP
3
HBA
2
HBD
70.7
PSA (Ų)
0.73
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H23F4N3O3
MW 405.39
Aromatic Rings 1
Heavy Atoms 28
NP-Likeness -1.79

Activity Summary

IC50 5 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional epoxide hydrolase 2
CHEMBL2409
 IC50 9.4 9.1867 0.4 3
Bifunctional epoxide hydrolase 2
CHEMBL4140
 IC50 7.72 7.72 19.1 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 879.29 ng.hr.mL-1 Mus musculus
AUC 84.32 ng.hr.mL-1 Rattus norvegicus
Cmax 166.0 nM Mus musculus
Cmax 42.0 nM Rattus norvegicus
T1/2 3.3 hr Mus musculus
T1/2 1.6 hr Rattus norvegicus
T1/2 42.0 hr Homo sapiens
Tmax 5.2 hr Mus musculus
Tmax 1.8 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional epoxide hydrolase 2 IC50 = 0.4 nM 9.4 Inhibition of human recombinant sEH using CMNPC as substrate incubated for 5 min... 33945278
Bifunctional epoxide hydrolase 2 IC50 = 0.4 nM 9.4 Inhibition of human recombinant sEH 36222708
Bifunctional epoxide hydrolase 2 IC50 = 1.73 nM 8.76 Inhibition of full length human sEH (1 to 555 residues) using 14,15-EET as subst... 38215588
Bifunctional epoxide hydrolase 2 IC50 = 19.11 nM 7.72 Inhibition of C57BL/6J mouse brain sEH using 14,15-EET as substrate preincubated... 38215588
Bifunctional epoxide hydrolase 2 IC50 = 19.1 nM 7.72 Inhibition of sEH in C57BL/6J mouse brain homogenate using 14, 15-EET as substra... 39361006

Literature References

PubMed DOI Target Context # Activities
33550801 10.1021/acs.jmedchem.0c01886 ADMET 8
33550801 10.1021/acs.jmedchem.0c01886 Unchecked 6
33007552 10.1016/j.bmc.2020.115735 ADMET 5
39361006 10.1021/acs.jmedchem.4c01766 Mus musculus 4
38236416 10.1021/acs.jmedchem.3c02006 Mus musculus 3
38215588 10.1016/j.ejmech.2023.116113 Bifunctional epoxide hydrolase 2 3
38215588 10.1016/j.ejmech.2023.116113 Mus musculus 3
33007552 10.1016/j.bmc.2020.115735 No relevant target 2
33007552 10.1016/j.bmc.2020.115735 Bifunctional epoxide hydrolase 2 2
33550801 10.1021/acs.jmedchem.0c01886 No relevant target 2
33550801 10.1021/acs.jmedchem.0c01886 Bifunctional epoxide hydrolase 2 2
39361006 10.1021/acs.jmedchem.4c01766 Bifunctional epoxide hydrolase 2 2
33550801 10.1021/acs.jmedchem.0c01886 Cytochrome P450 2C9 1
33550801 10.1021/acs.jmedchem.0c01886 Cytochrome P450 2C19 1
33945278 10.1021/acs.jmedchem.0c01601 Bifunctional epoxide hydrolase 2 1
36222708 10.1021/acs.jmedchem.2c00515 Bifunctional epoxide hydrolase 2 1

Data from ChEMBL 36 via Core Engine