xevinapant   Click here for help

GtoPdb Ligand ID: 7729

Synonyms: AT 406 | AT406 | Debio-1143 | Debio1143 | QCR-136 | SM 406
Compound class: Synthetic organic
Comment: Xevinapant (formerly AT-406, Debio 1143) is an orally available inhibitor of IAPs (inhibitor of apoptosis proteins), that is in development for anticancer potential. It was initially developed by Ascenta Therapeutics, and was originally progressed by Debiopharm. Merck in-licensed the asset when it was in late stage development. Structurally, xevinapant is a small molecule SMAC mimetic; SMAC being an endogenous IAP antagonist. Inhibition of IAPs which are often overexpressed in cancer cells (blocking apoptosis) leads to cancer cell death. SMAC mimetic-induced cancer cell death appears to involve multiple pathways, including re-activation of the apoptotic pathway, and/or ubiquitin-directed degradation of IAPs, which promotes TNFα/caspase-8-induced cell death [2-3].
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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 561.33
XLogP 3.59
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CNC(C(=O)NC1CN(CCC2N(C1=O)C(CC2)C(=O)NC(c1ccccc1)c1ccccc1)C(=O)CC(C)C)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)CC(C)C)C
InChI InChI=1S/C32H43N5O4/c1-21(2)19-28(38)36-18-17-25-15-16-27(37(25)32(41)26(20-36)34-30(39)22(3)33-4)31(40)35-29(23-11-7-5-8-12-23)24-13-9-6-10-14-24/h5-14,21-22,25-27,29,33H,15-20H2,1-4H3,(H,34,39)(H,35,40)/t22-,25+,26-,27-/m0/s1
InChI Key LSXUTRRVVSPWDZ-MKKUMYSQSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(5S,8S,10aR)-N-benzhydryl-5-[[(2S)-2-(methylamino)propanoyl]amino]-3-(3-methylbutanoyl)-6-oxo-1,2,4,5,8,9,10,10a-octahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide
International Nonproprietary Names Click here for help
INN number INN
11228 xevinapant
Synonyms Click here for help
AT 406 | AT406 | Debio-1143 | Debio1143 | QCR-136 | SM 406
Database Links Click here for help
CAS Registry No. 1071992-99-8
ChEMBL Ligand CHEMBL2158051
GtoPdb PubChem SID 223366062
PubChem CID 25022340
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