CC-885   Click here for help

GtoPdb Ligand ID: 9224

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Structural studies have shown that thalidomide class immunomodulatory drugs bind in a shallow hydrophobic pocket on the surface of cereblon, that is mediated by a glutarimide ring of the ligand. Binding of small molecules to cereblon can alter its substrate specificity [1]. Thalidomide and its related drugs enhance recruitment of Ikaros and Aiolos to the E3 ubiquitin ligase complex. CC-885 has a different mechanism of action compared to thalidomide, lenalidomide and pomalidomide. The anti-tumour activity of CC-885 is mediated through the cereblon-dependent ubiquitination and degradation of the translation termination factor GSPT1. Patient-derived acute myeloid leukaemia tumour cells exhibit high sensitivity to CC-885, indicating the clinical potential of this mechanism [2].
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 8
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 107.61
Molecular weight 440.13
XLogP 1.83
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=C(Nc1ccc(c(c1)Cl)C)NCc1ccc2c(c1)CN(C2=O)C1CCC(=O)NC1=O
Isomeric SMILES O=C(Nc1ccc(c(c1)Cl)C)NCc1ccc2c(c1)CN(C2=O)C1CCC(=O)NC1=O
InChI InChI=1S/C22H21ClN4O4/c1-12-2-4-15(9-17(12)23)25-22(31)24-10-13-3-5-16-14(8-13)11-27(21(16)30)18-6-7-19(28)26-20(18)29/h2-5,8-9,18H,6-7,10-11H2,1H3,(H2,24,25,31)(H,26,28,29)
InChI Key DOEVCIHTTTYVCC-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
3-(3-chloro-4-methylphenyl)-1-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]urea
Database Links Click here for help
GtoPdb PubChem SID 340590211
PubChem CID 24788636
Search Google for chemical match using the InChIKey DOEVCIHTTTYVCC-UHFFFAOYSA-N
Search Google for chemicals with the same backbone DOEVCIHTTTYVCC
UniChem Compound Search for chemical match using the InChIKey DOEVCIHTTTYVCC-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey DOEVCIHTTTYVCC-UHFFFAOYSA-N