B3C   Click here for help

GtoPdb Ligand ID: 7859

Synonyms: compound 23 [PMID: 18752942] [1]
Compound class: Synthetic organic
Comment: This compound was developed by Novartis Institute as an inhibitor of protease, serine, 8 (PRSS8/prostasin), which acts as an activator of the epithelial sodium channel ENa. Inhibition of such activators may target cystic fibrosis [1]. 257 analogues are included in patent WO2007137080, but without inhibition data.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 5
Rotatable bonds 22
Topological polar surface area 189.48
Molecular weight 777.37
XLogP 4.4
No. Lipinski's rules broken 2
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Canonical SMILES NCCCCC(C(c1nc2c(o1)cccc2)(O)O)NC(=O)C1CC(CN1C(=O)C(NC(=O)OCc1ccccc1)CCc1ccccc1)OCc1ccc(cc1)C
Isomeric SMILES NCCCC[C@@H](C(c1nc2c(o1)cccc2)(O)O)NC(=O)[C@@H]1C[C@H](CN1C(=O)[C@H](NC(=O)OCc1ccccc1)CCc1ccccc1)OCc1ccc(cc1)C
InChI InChI=1S/C44H51N5O8/c1-30-19-21-33(22-20-30)28-55-34-26-37(40(50)48-39(18-10-11-25-45)44(53,54)42-46-35-16-8-9-17-38(35)57-42)49(27-34)41(51)36(24-23-31-12-4-2-5-13-31)47-43(52)56-29-32-14-6-3-7-15-32/h2-9,12-17,19-22,34,36-37,39,53-54H,10-11,18,23-29,45H2,1H3,(H,47,52)(H,48,50)/t34-,36-,37+,39+/m1/s1
1. Tully DC, Vidal A, Chatterjee AK, Williams JA, Roberts MJ, Petrassi HM, Spraggon G, Bursulaya B, Pacoma R, Shipway A et al.. (2008)
Discovery of inhibitors of the channel-activating protease prostasin (CAP1/PRSS8) utilizing structure-based design.
Bioorg Med Chem Lett, 18 (22): 5895-9. [PMID:18752942]