compound 20 [PMID:12127536]   Click here for help

GtoPdb Ligand ID: 8650

Compound class: Synthetic organic
Comment: Compound 20 is reported as an inhibitor of the serine protease, granzyme B (GZMB) [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 13
Hydrogen bond donors 3
Rotatable bonds 15
Topological polar surface area 192.11
Molecular weight 658.28
XLogP 3.4
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCC(C(N(C(=O)C)C)C(=O)NC1CCc2c3N(C1=O)C(Cc3ccc2)C(=O)NC(C(=O)c1nnc(o1)c1ccccc1)CC(=O)O)C
Isomeric SMILES CC[C@@H]([C@H](N(C(=O)C)C)C(=O)N[C@H]1CCc2c3N(C1=O)[C@@H](Cc3ccc2)C(=O)N[C@H](C(=O)c1nnc(o1)c1ccccc1)CC(=O)O)C
InChI InChI=1S/C34H38N6O8/c1-5-18(2)27(39(4)19(3)41)31(46)35-23-15-14-20-12-9-13-22-16-25(40(28(20)22)34(23)47)30(45)36-24(17-26(42)43)29(44)33-38-37-32(48-33)21-10-7-6-8-11-21/h6-13,18,23-25,27H,5,14-17H2,1-4H3,(H,35,46)(H,36,45)(H,42,43)/t18-,23-,24-,25-,27-/m0/s1
InChI Key UCXMBOHIKJZNMQ-GIYJSHOWSA-N
References
1. Willoughby CA, Bull HG, Garcia-Calvo M, Jiang J, Chapman KT, Thornberry NA. (2002)
Discovery of potent, selective human granzyme B inhibitors that inhibit CTL mediated apoptosis.
Bioorg Med Chem Lett, 12 (16): 2197-200. [PMID:12127536]