dual sEH/FAAH inhibitor 11   Click here for help

GtoPdb Ligand ID: 10124

Synonyms: compound B-11 [WO2017160861] | example 28 [WO2017160861]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Inhibitor 11 was designed as a dual inhibitor of fatty acid amide hydrolase (FAAH) and soluble epoxide hydrolase (sEH), two enzymes that independently down-modulate inflammatory and neuropathic pain [2]. The structure-activity relationship exploration was initiated using the potent FAAH inhibitor PF750 (which is a weak sEH inhibitor). Inhibitor 11 is one of the chemical structures claimed in patent WO2017160861A1, specifically example 28 (B-11) [1]. Inhibitor 11 exhibits favourable target selectivity, pharmacokinetic properties and in vivo target engagement [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 63.69
Molecular weight 539.16
XLogP 6.92
No. Lipinski's rules broken 1
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Canonical SMILES O=C(N1CCC(CC1)Cc1cccc(c1)Oc1ccc(cn1)C(F)(F)F)Nc1ccc(cc1)OC(F)(F)F
Isomeric SMILES O=C(N1CCC(CC1)Cc1cccc(c1)Oc1ccc(cn1)C(F)(F)F)Nc1ccc(cc1)OC(F)(F)F
InChI InChI=1S/C26H23F6N3O3/c27-25(28,29)19-4-9-23(33-16-19)37-22-3-1-2-18(15-22)14-17-10-12-35(13-11-17)24(36)34-20-5-7-21(8-6-20)38-26(30,31)32/h1-9,15-17H,10-14H2,(H,34,36)
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Fatty acid amide hydrolase Primary target of this compound Hs Inhibitor Inhibition 7.4 pKi - 2
pKi 7.4 (Ki 3.7x10-8 M) [2]
epoxide hydrolase 2 Primary target of this compound Hs Inhibitor Inhibition 8.3 pIC50 - 1
pIC50 8.3 (IC50 5x10-9 M) [1]
Fatty acid amide hydrolase Primary target of this compound Hs Inhibitor Inhibition 8.1 pIC50 - 1
pIC50 8.1 (IC50 8x10-9 M) [1]
epoxide hydrolase 2 Rn Inhibitor Inhibition 7.7 pIC50 - 2
pIC50 7.7 (IC50 1.8x10-8 M) [2]
epoxide hydrolase 2 Mm Inhibitor Inhibition 7.6 pIC50 - 2
pIC50 7.6 (IC50 2.7x10-8 M) [2]
Fatty acid amide hydrolase Rn Inhibitor Inhibition 6.5 pIC50 - 2
pIC50 6.5 (IC50 3x10-7 M) [2]
Description: Following a 60 min preincubation with inhibitor.
Fatty acid amide hydrolase Mm Inhibitor Inhibition 5.8 pIC50 - 2
pIC50 5.8 (IC50 1.4x10-6 M) [2]