sabizabulin   Click here for help

GtoPdb Ligand ID: 11422

Synonyms: VERU-111 | VERU111
PDB Ligand
Compound class: Synthetic organic
Comment: Sabizabulin (VERU-111) is an orally bioavailable βIII/βIV-tubulin inhibitor that was developed for anti-tumour potential [1-2]. It interacts with the tubulin colchicine binding site. VERU-111 induces mitotic arrest and apoptosis in cancer cells in vitro, and inhibits xenograft tumour growth. It is suggested that like colchicine, VERU-111 may have anti-viral and anti-inflammatory actions in addition to its antiproliferative activity.
COVID-19: Sabizabulin has been repositioned as a potential therapeutic for COVID-19; in particular for patients who are hospitalised with moderate to severe COVID-19 and who are at high risk for developing acute respiratory distress syndrome (ARDS).
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 2
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 89.23
Molecular weight 377.14
XLogP 3.03
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 COc1cc(cc(c1OC)OC)C(=O)c1cnc([nH]1)c1c[nH]c2c1cccc2
Isomeric SMILES COc1cc(cc(c1OC)OC)C(=O)c1cnc([nH]1)c1c[nH]c2c1cccc2
InChI InChI=1S/C21H19N3O4/c1-26-17-8-12(9-18(27-2)20(17)28-3)19(25)16-11-23-21(24-16)14-10-22-15-7-5-4-6-13(14)15/h4-11,22H,1-3H3,(H,23,24)
InChI Key WQGVHOVEXMOLOK-UHFFFAOYSA-N
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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