SM-337   Click here for help

GtoPdb Ligand ID: 7732

Compound class: Synthetic organic
Comment: SM-377 is compound 6 in [1]. SM-337 is a potent, orally bioavailable Smac mimetic which acts as an antagonist of caspase binding to IAP family members, XIAP, cIAP1 and cIAP2 [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 12
Topological polar surface area 110.85
Molecular weight 595.32
XLogP 3.79
No. Lipinski's rules broken 0
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Canonical SMILES CNC(C(=O)NC1CN(CCC2N(C1=O)C(CC2)C(=O)NC(c1ccccc1)c1ccccc1)C(=O)Cc1ccccc1)C
Isomeric SMILES CN[C@H](C(=O)N[C@H]1CN(CC[C@@H]2N(C1=O)[C@@H](CC2)C(=O)NC(c1ccccc1)c1ccccc1)C(=O)Cc1ccccc1)C
InChI InChI=1S/C35H41N5O4/c1-24(36-2)33(42)37-29-23-39(31(41)22-25-12-6-3-7-13-25)21-20-28-18-19-30(40(28)35(29)44)34(43)38-32(26-14-8-4-9-15-26)27-16-10-5-11-17-27/h3-17,24,28-30,32,36H,18-23H2,1-2H3,(H,37,42)(H,38,43)/t24-,28+,29-,30-/m0/s1
1. Peng Y, Sun H, Nikolovska-Coleska Z, Qiu S, Yang CY, Lu J, Cai Q, Yi H, Kang S, Yang D et al.. (2008)
Potent, orally bioavailable diazabicyclic small-molecule mimetics of second mitochondria-derived activator of caspases.
J Med Chem, 51 (24): 8158-62. [PMID:19049347]