MPPA   Click here for help

GtoPdb Ligand ID: 9897

Synonyms: inhibitor 23 [PMID: 29614224]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: MMPA is an orally bioavailable dual inhibitor of soluble epoxide hydrolase (sEH) and phosphodiesterase 4 (PDE4) [1]. It was designed to provide enhanced analgesia for the treatment of inflammatory pain. MMPA can be described as a polypharmacological agent, i.e. a single molecule with at least two pharmacophores in a novel molecular design.
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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 8
Topological polar surface area 58.64
Molecular weight 372.17
XLogP 2.36
No. Lipinski's rules broken 0
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Canonical SMILES CCC(=O)N1CCC(CC1)C(=O)NCc1ccc(cc1C(F)(F)F)OC
Isomeric SMILES CCC(=O)N1CCC(CC1)C(=O)NCc1ccc(cc1C(F)(F)F)OC
InChI InChI=1S/C18H23F3N2O3/c1-3-16(24)23-8-6-12(7-9-23)17(25)22-11-13-4-5-14(26-2)10-15(13)18(19,20)21/h4-5,10,12H,3,6-9,11H2,1-2H3,(H,22,25)
Bioactivity Comments
MMPA inhibits general PDE4 activity in a cell based system, but has not been shown to inhibit any of the 20 individual PDE4 isoforms [1]. PDE4 was assessed in vitro by inhibitor-induced increase in cAMP in HEK cells as deterimned using a PKA biosensor. MMPA increased cAMP signals with an EC50 of 8.1nM [1].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
epoxide hydrolase 2 Hs Inhibitor Inhibition 8.7 pIC50 - 1
pIC50 8.7 (IC50 2.1x10-9 M) [1]
Description: In vitro assay measuring inhibition of recombinant human sEH enzymatic activity.
epoxide hydrolase 2 Rn Inhibitor Inhibition 6.8 pIC50 - 1
pIC50 6.8 (IC50 1.5x10-7 M) [1]
Description: In vitro assay measuring inhibition of recombinant rat sEH enzymatic activity.