compound 7f [PMID: 31251063]   Click here for help

GtoPdb Ligand ID: 10523

Compound class: Synthetic organic
Comment: Compound 7f is a cereblon-targeting compound with immunomodulatory potential [2]. It promotes proteasomal degradation of the lymphoid transcription factor neo-substrate Aiolos (IKZF3), but utilises a recognition mode that is distinct from that of the classical thalidomide-based immunomodulatory drugs (IMiDs). 7f contains a cinnamamide group in place of the glutarimide moeity found in thalidomide IMiDs [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 75.27
Molecular weight 244.08
XLogP 0.89
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C(NC1CC(=O)NC1=O)C=Cc1ccccc1
Isomeric SMILES O=C(NC1CC(=O)NC1=O)/C=C/c1ccccc1
InChI InChI=1S/C13H12N2O3/c16-11(7-6-9-4-2-1-3-5-9)14-10-8-12(17)15-13(10)18/h1-7,10H,8H2,(H,14,16)(H,15,17,18)/b7-6+
InChI Key NSEUGMATEWSNTO-VOTSOKGWSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
IUPAC Name Click here for help
N-(2,5-Dioxopyrrolidin-3-yl)cinnamamide
Database Links Click here for help
GtoPdb PubChem SID 387065605
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