GtoPdb Ligand ID: 9333

Synonyms: (2S)-6 [1]
Compound class: Synthetic organic
Comment: RWJ-56423 is an inhibitor of human mast cell tryptase (TPSAB1) [1]. Such compounds have therapeutic potential for treating allergic or inflammatory disorders.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 10
Hydrogen bond donors 5
Rotatable bonds 11
Topological polar surface area 189.74
Molecular weight 446.17
XLogP -0.07
No. Lipinski's rules broken 0
Canonical SMILES NC(=N)NCCCC(C(=O)c1nc2c(s1)cccc2)NC(=O)C1CC(CN1C(=O)C)O
Isomeric SMILES NC(=N)NCCC[C@@H](C(=O)c1nc2c(s1)cccc2)NC(=O)[C@@H]1C[C@H](CN1C(=O)C)O
InChI InChI=1S/C20H26N6O4S/c1-11(27)26-10-12(28)9-15(26)18(30)24-14(6-4-8-23-20(21)22)17(29)19-25-13-5-2-3-7-16(13)31-19/h2-3,5,7,12,14-15,28H,4,6,8-10H2,1H3,(H,24,30)(H4,21,22,23)/t12-,14+,15+/m1/s1
1. Costanzo MJ, Yabut SC, Almond Jr HR, Andrade-Gordon P, Corcoran TW, De Garavilla L, Kauffman JA, Abraham WM, Recacha R, Chattopadhyay D et al.. (2003)
Potent, small-molecule inhibitors of human mast cell tryptase. Antiasthmatic action of a dipeptide-based transition-state analogue containing a benzothiazole ketone.
J. Med. Chem., 46 (18): 3865-76. [PMID:12930148]
2. Erin EM, Leaker BR, Zacharasiewicz A, Higgins LA, Nicholson GC, Boyce MJ, de Boer P, Jones RC, Durham SR, Barnes PJ et al.. (2006)
Effects of a reversible beta-tryptase and trypsin inhibitor (RWJ-58643) on nasal allergic responses.
Clin. Exp. Allergy, 36 (4): 458-64. [PMID:16630150]