Structure via PubChem · Public domain (PubChem)
berberine
Sign in to saveAlso known as umbellatine
Berberine is an organic compound classified as benzylisoquinoline alkaloid. Chemically, it is a quaternary ammonia compound.
Chemical data
- Formula
- C20H18NO4+
- Molecular weight
- 336.4 g/mol
- IUPAC name
- 16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene
- SMILES
- COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC
- InChIKey
- YBHILYKTIRIUTE-UHFFFAOYSA-N
- XLogP
- 3.6
- Polar surface area
- 40.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 1
via PubChem
Research
10,033 papers- Biological properties and clinical applications of berberine.Frontiers of medicine · 2020
- The metabolism of berberine and its contribution to the pharmacological effects.Drug metabolism reviews · 2017
- Inhibition of inflammation by berberine: Molecular mechanism and network pharmacology analysis.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2024
- Berberine and Its Role in Chronic Disease.Advances in experimental medicine and biology · 2016
- Berberine pharmacology and the gut microbiota: A hidden therapeutic link.Pharmacological research · 2020
via PubMed
Wikidata facts
- Subclass of
- quaternary ammonium cation
- Has part
- carbon
- Mass
- 336.1230344760899
Show 8 more facts
- found in taxon
- Streptomyces
- canonical SMILES
- O1c2c(OC1)cc5c(c2)c4cc3ccc(OC)c(OC)c3c[n+]4CC5
- NCI Thesaurus ID
- C83551
- subject has role
- aromatase inhibitors
- chemical formula
- C₂₀H₁₈NO₄⁺
- has characteristic
- bitterness
- Commons category
- Berberine
- described by source
- Encyclopædia Britannica 11th edition
via Wikidata · CC0
~5 min read
Encyclopedic overview
8 sectionsContents
- Biological sources
- Structure and biosynthesis
- Research
- Supplements, regulation, and safety
- Adverse effects
- Drug interactions
- Use in China
- References
Berberine is an organic compound classified as benzylisoquinoline alkaloid. Chemically, it is a quaternary ammonia compound.
Its name is derived from the genus of plants, Berberis. Berberine occurs in the roots, bark, stems, and leaves of Berberis vulgaris (barberry), Berberis aristata (tree turmeric), Mahonia aquifolium (Oregon grape) and Hydrastis canadensis (goldenseal).
Excerpted from Wikipedia’s “berberine” article, available under the CC BY-SA 4.0 licence.