BI-1935   Click here for help

GtoPdb Ligand ID: 9717

Synonyms: BI 1935 | example 3 [WO2007067836]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: BI-1935 is a potent and selective small molecule inhibitor of epoxide hydrolase 2 (a.k.a. soluble epoxide hydrolase, sEH). It is claimed as Example 3 in Boehringer Ingelheim's patent WO2007067836 [1].
This ligand is one of the compounds available from Boehringer Ingelheim's opnMe molecular library.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 103.41
Molecular weight 498.16
XLogP 3.81
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCOCCn1cc(ccc1=O)C(=O)Nc1ccc(cn1)n1nc(cc1C(F)(F)F)c1cccnc1
Isomeric SMILES CCOCCn1cc(ccc1=O)C(=O)Nc1ccc(cn1)n1nc(cc1C(F)(F)F)c1cccnc1
InChI InChI=1S/C24H21F3N6O3/c1-2-36-11-10-32-15-17(5-8-22(32)34)23(35)30-21-7-6-18(14-29-21)33-20(24(25,26)27)12-19(31-33)16-4-3-9-28-13-16/h3-9,12-15H,2,10-11H2,1H3,(H,29,30,35)
InChI Key KMESAVNRPDKZCQ-UHFFFAOYSA-N
References
1. Fleck RW, Guo X, Lo HY, Man CC. (2007)
Substituted pyrazole compounds useful as soluble epoxide hyrolase inhibitors.
Patent number: WO2007067836. Assignee: Boehringer Ingelheim Int, Fleck RW, Guo X, Lo HY, Man CC. Priority date: 05/12/2005. Publication date: 15/11/2007.
2. Taylor SJ, Soleymanzadeh F, Eldrup AB, Farrow NA, Muegge I, Kukulka A, Kabcenell AK, De Lombaert S. (2009)
Design and synthesis of substituted nicotinamides as inhibitors of soluble epoxide hydrolase.
Bioorg Med Chem Lett, 19 (20): 5864-8. [PMID:19758802]
3. Yu Z, Xu F, Huse LM, Morisseau C, Draper AJ, Newman JW, Parker C, Graham L, Engler MM, Hammock BD et al.. (2000)
Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids.
Circ Res, 87 (11): 992-8. [PMID:11090543]