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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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)
InChI Key RSNPAKAFCAAMBH-UHFFFAOYSA-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
3-(5-amino-2-methyl-4-oxoquinazolin-3-yl)piperidine-2,6-dione
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
Search Google for chemicals with the same backbone RSNPAKAFCAAMBH
Search PubMed clinical trials avadomide
Search PubMed titles avadomide
Search PubMed titles/abstracts avadomide
UniChem Compound Search for chemical match using the InChIKey RSNPAKAFCAAMBH-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey RSNPAKAFCAAMBH-UHFFFAOYSA-N