ARV-393   Click here for help

GtoPdb Ligand ID: 13460

Synonyms: ARV393 | compound 81 [WO2022221673A1]
Compound class: Synthetic organic
Comment: ARV-393 is an orally active PROTAC that promotes degradation of the BCL6 transcription repressor protein. A lenalidomide derived moiety promotes formation of a ternary complex of the PROTAC, target protein and the E3 ligase cereblon to induce ubiquitination and degradation. The structure shown here has (1r,3r) configuration around the cyclobutoxy group, as indicated for compound 81 in Arvinas' patent WO2022221673A [1]. We will update this entry whenever ARV-393's chemical structure is formally disclosed.
BCL6 is a transcriptional repressor and major driver of B-cell lymphomas. Reducing BCL6 activity or abundance are proposed as mechanisms to treat advanced B-cell malignancies such as non-Hodgkin's lymphoma.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 16
Hydrogen bond donors 3
Rotatable bonds 13
Topological polar surface area 177.58
Molecular weight 898.42
XLogP 1.33
No. Lipinski's rules broken 3

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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Canonical SMILES CC(C)N1C2=C(C=C(C=C2)NC3=C(C=NC(=N3)N4CCC(CC4)O[C@H]5C[C@@H](C5)N6CCC(CC6)C7=CC=C8C(=C7F)CN(C9CCC(=O)NC9=O)C8=O)Cl)C=C(C1=O)OCC(=O)NC
Isomeric SMILES CNC(=O)COC1=CC2=C(C=CC(NC3=C(Cl)C=NC(=N3)N4CCC(CC4)O[C@H]5C[C@@H](C5)N6CCC(CC6)C7=CC=C8C(=O)N(CC8=C7F)C9CCC(=O)NC9=O)=C2)N(C(C)C)C1=O
InChI InChI=1S/C46H53ClFN9O7/c1-25(2)57-36-7-4-28(18-27(36)19-38(45(57)62)63-24-40(59)49-3)51-42-35(47)22-50-46(53-42)55-16-12-30(13-17-55)64-31-20-29(21-31)54-14-10-26(11-15-54)32-5-6-33-34(41(32)48)23-56(44(33)61)37-8-9-39(58)52-43(37)60/h4-7,18-19,22,25-26,29-31,37H,8-17,20-21,23-24H2,1-3H3,(H,49,59)(H,50,51,53)(H,52,58,60)/t29-,31-,37?
InChI Key ZOGOEUHUEFKKTD-VVDHFOCHSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
Synonyms Click here for help
ARV393 | compound 81 [WO2022221673A1]
Database Links Click here for help
GtoPdb PubChem SID 500839870
PubChem CID 166077922
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UniChem Connectivity Search for chemical match using the InChIKey ZOGOEUHUEFKKTD-VVDHFOCHSA-N