Structure via PubChem · Public domain (PubChem)
chelerythrine
Sign in to saveAlso known as broussonpapyrine, cheleritrine, chelerythrine hydroxide, toddalin, 1,2-Dimethoxy-12-methyl(1,3)benzodioxolo(5,6-c)phenanthridinium
Chelerythrine is a benzophenanthridine alkaloid present in the plant Chelidonium majus (greater celandine). It is a potent, selective, and cell-permeable protein kinase C inhibitor in vitro. And an efficacious antagonist of G-protein-coupled CB1 receptors. This molecule also exhibits anticancer qualities and it has served as a base for many potential novel drugs against cancer. Structurally, this molecule has two distinct conformations, one being a positively charged iminium form, and the other being an uncharged form, a pseudo-base.
Chemical data
- Formula
- C21H18NO4+
- Molecular weight
- 348.4 g/mol
- IUPAC name
- 1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium
- SMILES
- C[N+]1=C2C(=C3C=CC(=C(C3=C1)OC)OC)C=CC4=CC5=C(C=C42)OCO5
- InChIKey
- LLEJIEBFSOEYIV-UHFFFAOYSA-N
- XLogP
- 4.6
- Polar surface area
- 40.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 1
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
2,768 papers- Chelerythrine inhibits esophageal squamous cell carcinoma progression via PINK1-Parkin-mediated mitophagy.Journal of translational medicine · 2025
- Therapeutic potential of chelerythrine as a multi-purpose adjuvant for the treatment of COVID-19.Cell cycle (Georgetown, Tex.) · 2021
- Chelerythrine inhibits NR2B NMDA receptor independent of PKC activity.Biochemical and biophysical research communications · 2024
- Chelerythrine Chloride Alleviated Lipopolysaccharide-Induced Acute Lung Injury by Inhibiting Glycolytic Pathway Through Targeting Glyceraldehyde-3-Phosphate Dehydrogenase.Molecules (Basel, Switzerland) · 2025
- Chelerythrine chloride inhibits Zika virus infection by targeting the viral NS4B protein.Antiviral research · 2023
via PubMed
Wikidata facts
- Subclass of
- quaternary ammonium cation
- Mass
- 348.124
Show 5 more facts
- found in taxon
- Macleaya cordata
- canonical SMILES
- C[N+]1=C2C(=C3C=CC(=C(C3=C1)OC)OC)C=CC4=CC5=C(C=C42)OCO5
- subject has role
- antineoplastic
- Commons category
- Chelerythrine
- chemical formula
- C₂₁H₁₈NO₄⁺
via Wikidata · CC0
~4 min read
Encyclopedic overview
7 sectionsContents
- Research
- Antibacterial agent
- Cellular apoptosis
- Other
- Anti-cancer mechanisms
- Role as a protein kinase C inhibitor
- References
Chelerythrine is a benzophenanthridine alkaloid present in the plant Chelidonium majus (greater celandine). It is a potent, selective, and cell-permeable protein kinase C inhibitor in vitro. And an efficacious antagonist of G-protein-coupled CB1 receptors. This molecule also exhibits anticancer qualities and it has served as a base for many potential novel drugs against cancer. Structurally, this molecule has two distinct conformations, one being a positively charged iminium form, and the other being an uncharged form, a pseudo-base.
It is also found in the plants Zanthoxylum clava-herculis and Zanthoxylum rhoifolium, exhibiting antibacterial activity against Staphylococcus aureus and other human pathogens.
Excerpted from Wikipedia’s “chelerythrine” article, available under the CC BY-SA 4.0 licence.
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via Wikidata sitelinks · CC0