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.

ARV-393 is commercially available from our sponsors

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 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/). 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 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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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.

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/)

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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/)
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Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel