LCL161   Click here for help

GtoPdb Ligand ID: 7912

Synonyms: LCL-161 | NVP-LCL161
Compound class: Synthetic organic
Comment: LCL161 is a SMAC mimetic which acts as an inhibitor of IAPs (inhibitor of apoptosis proteins), binding predominantly to their BIR3 domain [1]. Use the following hyperlinks to view protein sequences for XIAP BIR3 and cIAP1 BIR3 provided by UniProt.org.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 119.64
Molecular weight 500.23
XLogP 3.95
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CNC(C(=O)NC(C(=O)N1CCCC1c1scc(n1)C(=O)c1ccc(cc1)F)C1CCCCC1)C
Isomeric SMILES CN[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1c1scc(n1)C(=O)c1ccc(cc1)F)C1CCCCC1)C
InChI InChI=1S/C26H33FN4O3S/c1-16(28-2)24(33)30-22(17-7-4-3-5-8-17)26(34)31-14-6-9-21(31)25-29-20(15-35-25)23(32)18-10-12-19(27)13-11-18/h10-13,15-17,21-22,28H,3-9,14H2,1-2H3,(H,30,33)/t16-,21-,22-/m0/s1
InChI Key UFPFGVNKHCLJJO-SSKFGXFMSA-N
References
1. Donnell AF, Michoud C, Rupert KC, Han X, Aguilar D, Frank KB, Fretland AJ, Gao L, Goggin B, Hogg JH et al.. (2013)
Benzazepinones and benzoxazepinones as antagonists of inhibitor of apoptosis proteins (IAPs) selective for the second baculovirus IAP repeat (BIR2) domain.
J Med Chem, 56 (20): 7772-87. [PMID:24083782]