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napabucasin   Click here for help

GtoPdb Ligand ID: 11358

Synonyms: BBI-608 | BBI608
PDB Ligand
Compound class: Synthetic organic
Comment: Napabucasin (BBI608) is a small molecule naphthoquinone that blocks cancer stemness properties [3,6], It does this by targeting the signal transducer and activator of transcription 3 (STAT3) pathway [4]. Napabucasin is orally administered, and is bioactivated by the intracellular antioxidant NAD(P)H:quinone oxidoreductase 1 (NQO1), to produce reactive oxygen species (ROS), principally NO. The high level of NO generation causes cell death, and positively correlates with the compound's anti-proliferative activity in cancer cells [1].

COVID-19: Napabucasin has been proposed as a potential repurposing candidate for the treatment of COVID-19, based on a virtual screening analysis of the interaction of existing approved and experimental compounds with the SARS-CoV-2 main protease (Mpro) [2]. Extensive in vitro and in vivo studies would be required to validate napabucasin's antiviral activity.

napabucasin 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 3
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 64.35
Molecular weight 240.04
XLogP 1.93
No. Lipinski's rules broken 0

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(=O)c1cc2c(o1)C(=O)c1c(C2=O)cccc1
Isomeric SMILES CC(=O)c1cc2c(o1)C(=O)c1c(C2=O)cccc1
InChI InChI=1S/C14H8O4/c1-7(15)11-6-10-12(16)8-4-2-3-5-9(8)13(17)14(10)18-11/h2-6H,1H3
InChI Key DPHUWDIXHNQOSY-UHFFFAOYSA-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
IUPAC Name Click here for help
2-acetylbenzo[f][1]benzofuran-4,9-dione
International Nonproprietary Names Click here for help
INN number INN
9848 napabucasin
Synonyms Click here for help
BBI-608 | BBI608
Database Links Click here for help
BindingDB Ligand 50366597
CAS Registry No. 83280-65-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL64130
GtoPdb PubChem SID 440816727
PubChem CID 10331844
RCSB PDB Ligand A1D65
Search Google for chemical match using the InChIKey DPHUWDIXHNQOSY-UHFFFAOYSA-N
Search Google for chemicals with the same backbone DPHUWDIXHNQOSY
Search PubMed clinical trials napabucasin
Search PubMed titles napabucasin
Search PubMed titles/abstracts napabucasin
UniChem Compound Search for chemical match using the InChIKey DPHUWDIXHNQOSY-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey DPHUWDIXHNQOSY-UHFFFAOYSA-N

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MedChemExpress
Napabucasin (links to external site)
Cat. No. HY-13919