avadomide   Click here for help

GtoPdb Ligand ID: 10522

Synonyms: CC-122 | CC122 | Compound A [WO2014039960A1]
Immunopharmacology Ligand
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].
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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 1
Topological polar surface area 107.08
Molecular weight 286.11
XLogP -0.04
No. Lipinski's rules broken 0
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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)
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
10599 avadomide
Synonyms Click here for help
CC-122 | CC122 | Compound A [WO2014039960A1]
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9681161
Reactome Reaction Reactome logo R-HSA-9681169
Other databases
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
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UniChem Compound Search for chemical match using the InChIKey RSNPAKAFCAAMBH-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey RSNPAKAFCAAMBH-UHFFFAOYSA-N