CC-90009   Click here for help

GtoPdb Ligand ID: 11424

Synonyms: Cereblon modulator 1 | Compound 1 [WO2019006299A1] [1] | compound 16 [PMID: 33591756]
Compound class: Synthetic organic
Comment: CC-90009 is a clinical stage cereblon E3 ligase modulating drug (CELMoD), that targets the G1 to S phase transition 1 (GSPT1, a.k.a. eRF3A) protein for degradation via the CUL4-DDB1-CRBN-RBX1 (CRL4CRBN) E3 ubiquitin ligase complex [2]. Binding of CC-90009 to cereblon alters its conformation, and promotes a change in substrate selectivity away from the transcription factors IKZF1/3 and towards to GSPT1. CC-90009-induced depletion of GSPT1 promotes apoptosis of acute myeloid leukemia (AML) cells via activation of the GCN1/GCN2/ATF4 pathway [3-4].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 95.58
Molecular weight 461.1
XLogP 2.68
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C1CCC(C(=O)N1)N1Cc2c(C1=O)ccc(c2)CNC(=O)C(c1ccc(cc1)Cl)(F)F
Isomeric SMILES O=C1CCC(C(=O)N1)N1Cc2c(C1=O)ccc(c2)CNC(=O)C(c1ccc(cc1)Cl)(F)F
InChI InChI=1S/C22H18ClF2N3O4/c23-15-4-2-14(3-5-15)22(24,25)21(32)26-10-12-1-6-16-13(9-12)11-28(20(16)31)17-7-8-18(29)27-19(17)30/h1-6,9,17H,7-8,10-11H2,(H,26,32)(H,27,29,30)
InChI Key PWBHUSLMHZLGRN-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
2-(4-chlorophenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide
Synonyms Click here for help
Cereblon modulator 1 | Compound 1 [WO2019006299A1] [1] | compound 16 [PMID: 33591756]
Database Links Click here for help
CAS Registry No. 1860875-51-9 (source: PubChem)
GtoPdb PubChem SID 440816793
PubChem CID 118647211
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