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یانگونین

Structure via PubChem · Public domain (PubChem)

EntityQ8048635· pop 8· linked from 1,001 articles

یانگونین

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Also known as 4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one

Yangonin is one of the six major kavalactones found in the kava plant. It acts as a selective agonist at the CB1 cannabinoid receptor, inhibits monoamine oxidase (particularly MAO-B), and modulates GABAA receptor activity. Yangonin significantly reduces nociception and inflammatory hyperalgesia via spinal CB1 receptors in rats, highlighting its potential as a promising treatment for pain. It is the strongest COX-II inhibitor among the six major kavalactones. Yangonin also exhibits neuroprotective, antifungal, and antimicrobial properties, though it has shown toxicity to human hepatocytes in vi

Chemical data

Formula
C15H14O4
Molecular weight
258.27 g/mol
IUPAC name
4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one
SMILES
COC1=CC=C(C=C1)/C=C/C2=CC(=CC(=O)O2)OC
InChIKey
XLHIYUYCSMZCCC-VMPITWQZSA-N
XLogP
2.7
Polar surface area
44.8 Ų
H-bond donors
0
H-bond acceptors
4
Formal charge
0

via PubChem

Drug data · ChEMBL

Molecule type
Small molecule

via ChEMBL · EBI

Wikidata facts

Subclass of
kavalactone
Mass
258.089209
Show 5 more facts
canonical SMILES
COC1=CC=C(C=C1)C=CC2=CC(=CC(=O)O2)OC
chemical formula
C₁₅H₁₄O₄
isomeric SMILES
COC1=CC=C(C=C1)/C=C/C2=CC(=CC(=O)O2)OC
found in taxon
Piper majusculum
Commons category
Yangonin
Sources (2)

via Wikidata · CC0

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via Wikidata sitelinks · CC0