RWJ-56423   

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
SMILES / InChI / InChIKey
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
InChI Key VXDAVYUFYPFGDX-SNPRPXQTSA-N
Bioactivity Comments
Apart from tryptase and trypsin, RWJ-56423 is selective vs. other serine proteases tested (e.g. kallikrein, plasmin, and thrombin) [1]. In vivo, RWJ-56423 blocks early and late antigen-induced asthmatic responses in allergic sheep, and ablates airway hyperresponsiveness.
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
serine protease 1 Bt Inhibitor Inhibition 8.1 pKi - 1
pKi 8.1 (Ki 8.09x10-9 M) [1]
tryptase alpha/beta 1 Hs Inhibitor Inhibition 8.0 pKi - 1
pKi 8.0 (Ki 1x10-8 M) [1]