GSK2256294   

GtoPdb Ligand ID: 9718

Synonyms: GSK-2256294 | GSK-2256294A | GSK2256294A
Compound class: Synthetic organic
Comment: GSK2256294 is an epoxide hydrolase 2 (sEH) inhibitor.
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 115.62
Molecular weight 447.2
XLogP 2.78
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CNc1nc(NC2CCCC(C2)C(=O)NCc2ccc(cc2C(F)(F)F)C#N)nc(n1)C
Isomeric SMILES CNc1nc(N[C@H]2CCC[C@H](C2)C(=O)NCc2ccc(cc2C(F)(F)F)C#N)nc(n1)C
InChI InChI=1S/C21H24F3N7O/c1-12-28-19(26-2)31-20(29-12)30-16-5-3-4-14(9-16)18(32)27-11-15-7-6-13(10-25)8-17(15)21(22,23)24/h6-8,14,16H,3-5,9,11H2,1-2H3,(H,27,32)(H2,26,28,29,30,31)/t14-,16+/m1/s1
InChI Key LQHDJQIMETZMPH-ZBFHGGJFSA-N
References
1. Blocher R, Lamers C, Wittmann SK, Diehl O, Hanke T, Merk D, Steinhilber D, Schubert-Zsilavecz M, Kahnt AS, Proschak E. (2016)
Design and synthesis of fused soluble epoxide hydrolase/peroxisome proliferator-activated receptor modulators.
Medchemcomm, 7: 1209-1216. DOI: 10.1039/C6MD00042H
2. Lazaar AL, Yang L, Boardley RL, Goyal NS, Robertson J, Baldwin SJ, Newby DE, Wilkinson IB, Tal-Singer R, Mayer RJ et al.. (2016)
Pharmacokinetics, pharmacodynamics and adverse event profile of GSK2256294, a novel soluble epoxide hydrolase inhibitor.
Br J Clin Pharmacol, 81 (5): 971-9. [PMID:26620151]
3. Spector AA, Fang X, Snyder GD, Weintraub NL. (2004)
Epoxyeicosatrienoic acids (EETs): metabolism and biochemical function.
Prog. Lipid Res., 43 (1): 55-90. [PMID:14636671]
4. Spector AA, Norris AW. (2007)
Action of epoxyeicosatrienoic acids on cellular function.
Am. J. Physiol., Cell Physiol., 292 (3): C996-1012. [PMID:16987999]