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
Bioactivity Comments
In contrast to potent inhibition action via BIR3 domain, LCL161 (compound 3 in [1]) inhibits XIAP BIR2 with an IC50 of 1050 nM, and cIAP1 BIR2 with an IC50 of 2720 nM [1].
Selectivity at other protein targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
X-linked inhibitor of apoptosis Primary target of this compound Hs Inhibitor Inhibition 7.5 pIC50 - 1
pIC50 7.5 (IC50 3x10-8 M) [1]
Description: Assay uses recombinantly expressed BIR3 domain of XIAP
baculoviral IAP repeat containing 2 Primary target of this compound Hs Inhibitor Inhibition 7.2 pIC50 - 1
pIC50 7.2 (IC50 5.8x10-8 M) [1]
Description: Assay uses recombinantly expressed BIR3 domain of cIAP1