SWE101   

GtoPdb Ligand ID: 10494

Synonyms: compound 22b [PMID: 31436984]
Compound class: Synthetic organic
Comment: SWE101 is a soluble epoxide hydrolase (sEH; EPHX2) inhibitor that selectively, and competitively targets the enzyme's phosphatase activity [2]. Its structure was developed from the scaffold of the NSAID oxaprozin which exhibits weak sEH-phosphatase inhibitory activity [1]. SWE101 is a tool compound that was designed to aid investigations of the physiological and pathophysiological role of sEH phosphatase activity in vivo.
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 63.33
Molecular weight 375.04
XLogP 5.28
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES OC(=O)CCCc1oc(c(n1)c1ccc(c(c1)Cl)Cl)c1ccccc1
Isomeric SMILES OC(=O)CCCc1oc(c(n1)c1ccc(c(c1)Cl)Cl)c1ccccc1
InChI InChI=1S/C19H15Cl2NO3/c20-14-10-9-13(11-15(14)21)18-19(12-5-2-1-3-6-12)25-16(22-18)7-4-8-17(23)24/h1-3,5-6,9-11H,4,7-8H2,(H,23,24)
InChI Key UIADWSXPNFQQCZ-UHFFFAOYSA-N
References
1. Klingler FM, Wolf M, Wittmann S, Gribbon P, Proschak E. (2016)
Bacterial Expression and HTS Assessment of Soluble Epoxide Hydrolase Phosphatase.
J Biomol Screen, 21 (7): 689-94. [PMID:27009944]
2. Kramer JS, Woltersdorf S, Duflot T, Hiesinger K, Lillich FF, Knöll F, Wittmann SK, Klingler FM, Brunst S, Chaikuad A et al.. (2019)
Discovery of the First in Vivo Active Inhibitors of the Soluble Epoxide Hydrolase Phosphatase Domain.
J. Med. Chem., 62 (18): 8443-8460. [PMID:31436984]