berberine

Also 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 Å²
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

Mass: 336.1230344760899

Show 4 more facts

canonical SMILES: O1c2c(OC1)cc5c(c2)c4cc3ccc(OC)c(OC)c3c[n+]4CC5
NCI Thesaurus ID: C83551
chemical formula: C₂₀H₁₈NO₄⁺
Commons category: Berberine

Sources (3)

via Wikidata · CC0

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Article

8 sections

Contents

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).