avadomide   

GtoPdb Ligand ID: 10522

Synonyms: CC-122 | CC122 | Compound A [WO2014039960A1]
Compound class: Synthetic organic
Comment: Avadomide (CC-122) is a cereblon (CRBN)-targeting compound [2] that exhibits potent single-agent clinical antitumour and immunomodulatory activities [3]. It retains the glutarimide moiety that is shared by all thalidomide family drugs, and which is known to directly interact with CRBN. The INN record specifies avadomide as a racemic mixture of enantiomers. We show the structure without specified stereochemistry to represent the mixture. It is claimed as Compound A in Celgene's patent WO2014039960A1 [1].
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 107.08
Molecular weight 286.11
XLogP -0.04
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES O=C1CCC(C(=O)N1)n1c(C)nc2c(c1=O)c(N)ccc2
Isomeric SMILES O=C1CCC(C(=O)N1)n1c(C)nc2c(c1=O)c(N)ccc2
InChI InChI=1S/C14H14N4O3/c1-7-16-9-4-2-3-8(15)12(9)14(21)18(7)10-5-6-11(19)17-13(10)20/h2-4,10H,5-6,15H2,1H3,(H,17,19,20)
InChI Key RSNPAKAFCAAMBH-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Ligand families/groups PROTACs and molecular glues
IUPAC Name
3-(5-amino-2-methyl-4-oxoquinazolin-3-yl)piperidine-2,6-dione
International Nonproprietary Names
INN number INN
10599 avadomide
Synonyms
CC-122 | CC122 | Compound A [WO2014039960A1]
Database Links
BindingDB Ligand 76986
CAS Registry No. 1015474-32-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL3989934
GtoPdb PubChem SID 387065604
PubChem CID 24967599
Search Google for chemical match using the InChIKey RSNPAKAFCAAMBH-UHFFFAOYSA-N
Search Google for chemicals with the same backbone RSNPAKAFCAAMBH
Search PubMed clinical trials avadomide
Search PubMed titles avadomide
Search PubMed titles/abstracts avadomide
Search UniChem for chemical match using the InChIKey RSNPAKAFCAAMBH-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone RSNPAKAFCAAMBH