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Structure via PubChem · Public domain (PubChem)
yangonin
Sign in to saveAlso 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
~4 min read
Encyclopedic overview
4 sectionsContents
- Pharmacology
- Toxicity
- Biosynthesis
- References
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 vitro.
==Pharmacology==
Excerpted from Wikipedia’s “yangonin” article, available under the CC BY-SA 4.0 licence.