BI-3802   Click here for help

GtoPdb Ligand ID: 11338

Synonyms: BI3802
PDB Ligand
Compound class: Synthetic organic
Comment: BI-3802 is a small molecule that promotes ubiquitin-mediated, proteasomal degradation of the oncogenic transcription factor BCL6 [2,4]. It binds to BCL6's BTB domain and initiates polymerization of BCL6 into structural foci that become targets for ubiquitination by the SIAH1 E3 ubiquitin ligase. BI-3802's mechanism of action is distinct from those of PROTACs and molecular glue type protein degraders [1]. BI-3802-promoted degradation of BCL6 results in significant derepression of BCL6 target genes and anti-proliferative effects in model cancer cell lines. The chemical structure was claimed in a patent granted to Boehringer Ingelheim in 2018 [3].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 101.38
Molecular weight 484.2
XLogP 4.74
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES CNC(=O)COc1cc2cc(ccc2n(c1=O)C)Nc1nc(ncc1Cl)N1C[C@H](C)C[C@@H](C1)C
Isomeric SMILES CNC(=O)COc1cc2cc(ccc2n(c1=O)C)Nc1nc(ncc1Cl)N1C[C@H](C)C[C@@H](C1)C
InChI InChI=1S/C24H29ClN6O3/c1-14-7-15(2)12-31(11-14)24-27-10-18(25)22(29-24)28-17-5-6-19-16(8-17)9-20(23(33)30(19)4)34-13-21(32)26-3/h5-6,8-10,14-15H,7,11-13H2,1-4H3,(H,26,32)(H,27,28,29)/t14-,15+
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
IUPAC Name Click here for help
Synonyms Click here for help
Database Links Click here for help
CAS Registry No. 2166387-65-9 (source: PubChem)
GtoPdb PubChem SID 440816707
PubChem CID 131632978
RCSB PDB Ligand U52
Search Google for chemical match using the InChIKey GXTJETQFYHZHNB-GASCZTMLSA-N
Search Google for chemicals with the same backbone GXTJETQFYHZHNB
UniChem Compound Search for chemical match using the InChIKey GXTJETQFYHZHNB-GASCZTMLSA-N
UniChem Connectivity Search for chemical match using the InChIKey GXTJETQFYHZHNB-GASCZTMLSA-N