golcadomide   Click here for help

GtoPdb Ligand ID: 13021

Synonyms: CC-99282 | CC99282 | compound 1 [US20220324855]
Compound class: Synthetic organic
Comment: Golcadomide (CC-99282) is an oral molecular glue that promotes degradation of IKZF1/3 transcription factors (Ikaros/Aiolos) by engaging the cereblon E3 ubiquitin ligase complex. Structurally golcadomide is a novel thalidomide analogue (known as a CELMoD/cereblon E3 ligase modulator). It has immunomodulatory actions, with enhanced antiproliferative and proapoptotic activities compared to lenalidomide. The chemical structure for golcadomide is claimed in several Celgene patents (e.g. US20220324855A1 [1]).
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 10
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 111.29
Molecular weight 535.57
XLogP -1.58
No. Lipinski's rules broken 1
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 C1=CC(=C2C(=C1)C(=O)N([C@H]3CCC(=O)NC3=O)C2=O)NCC4=CC=C(C=C4F)CN5CC(C5)N6CCOCC6
Isomeric SMILES C1CC(=O)NC(=O)[C@H]1N2C(=O)C3=C(C2=O)C(=CC=C3)NCC4=C(C=C(C=C4)CN5CC(C5)N6CCOCC6)F
InChI InChI=1S/C28H30FN5O5/c29-21-12-17(14-32-15-19(16-32)33-8-10-39-11-9-33)4-5-18(21)13-30-22-3-1-2-20-25(22)28(38)34(27(20)37)23-6-7-24(35)31-26(23)36/h1-5,12,19,23,30H,6-11,13-16H2,(H,31,35,36)/t23-/m0/s1
InChI Key NZYDBVQXOGPDDU-QHCPKHFHSA-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
2-[(3S)-2,6-dioxopiperidin-3-yl]-4-[[2-fluoro-4-[(3-morpholin-4-ylazetidin-1-yl)methyl]phenyl]methylamino]isoindole-1,3-dione
International Nonproprietary Names Click here for help
INN number INN
12305 golcadomide
Synonyms Click here for help
CC-99282 | CC99282 | compound 1 [US20220324855]
Database Links Click here for help
ChEMBL Ligand CHEMBL5095226
GtoPdb PubChem SID 485206142
PubChem CID 146195299
Search Google for chemical match using the InChIKey NZYDBVQXOGPDDU-QHCPKHFHSA-N
Search Google for chemicals with the same backbone NZYDBVQXOGPDDU
Search PubMed clinical trials golcadomide
Search PubMed titles golcadomide
Search PubMed titles/abstracts golcadomide
UniChem Compound Search for chemical match using the InChIKey NZYDBVQXOGPDDU-QHCPKHFHSA-N
UniChem Connectivity Search for chemical match using the InChIKey NZYDBVQXOGPDDU-QHCPKHFHSA-N