3-(5-hydroxy-1-oxoisoindolin-2-yl)piperidine-2,6-dione Chemical Properties

Boiling point:

631.5±55.0 °C(Predicted)

Density 

1.498±0.06 g/cm3(Predicted)

storage temp. 

Storage temp. 2-8°C

pka

8.32±0.20(Predicted)

form 

Solid

color 

Off-white to gray

InChI

InChI=1S/C13H12N2O4/c16-8-1-2-9-7(5-8)6-15(13(9)19)10-3-4-11(17)14-12(10)18/h1-2,5,10,16H,3-4,6H2,(H,14,17,18)

InChIKey

JJUMFQGCQAUIFH-UHFFFAOYSA-N

SMILES

N1C(=O)CCC(N2CC3=C(C2=O)C=CC(O)=C3)C1=O

3-(5-hydroxy-1-oxoisoindolin-2-yl)piperidine-2,6-dione Usage And Synthesis

Uses

Lenalidomide-OH is an analog of cereblon (CRBN) ligand Lenalidomide for E3 ubiquitin ligase, and is used in the recruitment of CRBN protein. Lenalidomide-OH can be connected to the ligand for protein by a linker to form PROTACs, such as the PROTAC BTK degrader SJF620 (HY-133137)[1].

IC 50

Cereblon

References

[1] Jaime-Figueroa S, et al. Design, synthesis and biological evaluation of Proteolysis Targeting Chimeras (PROTACs) as a BTK degraders with improved pharmacokinetic properties. 2020 Feb 1;30(3):126877. DOI:10.1016/j.bmcl.2019.126877