Structure via PubChem · Public domain (PubChem)
sanguinarine
Sign in to saveAlso known as sanguinarium
Sanguinarine is a polycyclic quaternary alkaloid. It is extracted from some plants, including the bloodroot plant (Sanguinaria canadensis, from whose scientific name its name is derived), the Mexican prickly poppy (Argemone mexicana), Chelidonium majus, and Macleaya cordata.
Chemical data
- Formula
- C20H14NO4+
- Molecular weight
- 332.3 g/mol
- IUPAC name
- 24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene
- SMILES
- C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6
- InChIKey
- INVGWHRKADIJHF-UHFFFAOYSA-N
- XLogP
- 4.4
- Polar surface area
- 40.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 1
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,188 papers- Sanguinarine.Cardiovascular therapeutics · 2008
- Sanguinarine: A Double-Edged Sword of Anticancer and Carcinogenesis and Its Future Application Prospect.Anti-cancer agents in medicinal chemistry · 2021
- Sanguinarine synergistically potentiates aminoglycoside-mediated bacterial killing.Microbial biotechnology · 2022
- Sanguinarine and Its Role in Chronic Diseases.Advances in experimental medicine and biology · 2016
- Molecular Mechanisms of Sanguinarine in Cancer Prevention and Treatment.Anti-cancer agents in medicinal chemistry · 2023
via PubMed
Wikidata facts
- Mass
- 332.092
Show 5 more facts
- canonical SMILES
- C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6
- found in taxon
- Corydalis livida
- subject has role
- cardiotonic
- Commons category
- Sanguinarine
- chemical formula
- C₂₀H₁₄NO₄⁺
via Wikidata · CC0
~4 min read
Encyclopedic overview
5 sectionsContents
- Toxicity
- Alternative medicine
- Biosynthesis
- See also
- References
Sanguinarine is a polycyclic quaternary alkaloid. It is extracted from some plants, including the bloodroot plant (Sanguinaria canadensis, from whose scientific name its name is derived), the Mexican prickly poppy (Argemone mexicana), Chelidonium majus, and Macleaya cordata.
==Toxicity== Sanguinarine is a toxin that kills animal cells through its action on the Na+/K+-ATPase transmembrane protein. Epidemic dropsy is a disease that results from ingesting sanguinarine.
Excerpted from Wikipedia’s “sanguinarine” article, available under the CC BY-SA 4.0 licence.