Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H14O4 |
Molecular Weight | 258.2693 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(\C=C\C2=CC(OC)=CC(=O)O2)C=C1
InChI
InChIKey=XLHIYUYCSMZCCC-VMPITWQZSA-N
InChI=1S/C15H14O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-10H,1-2H3/b8-5+
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20734326Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28959001 | https://www.ncbi.nlm.nih.gov/pubmed/22525682 | https://www.ncbi.nlm.nih.gov/pubmed/22510965 | https://www.ncbi.nlm.nih.gov/pubmed/17059882
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20734326
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28959001 | https://www.ncbi.nlm.nih.gov/pubmed/22525682 | https://www.ncbi.nlm.nih.gov/pubmed/22510965 | https://www.ncbi.nlm.nih.gov/pubmed/17059882
Yangonin is a natural kavalactone found in the kava plant. Yangonin has been shown to possess binding affinity for the cannabinoid receptor CB1, where it behaves as an agonist. Yangonin also inhibits anchorage-dependent and independent growth of bladder cancer cell lines through induction of autophagic cell death. Yangonin displays marked in vitro toxicity on human hepatocytes with approximately 40% reduction in viability based on an ethidium bromide assay and FDA advises against the use of kava in food due to the potential risk of severe liver damage.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL218 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22525682 |
0.72 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17059882
Groups of 10 male and 10 female rats were administered kava extract (Yangonin: 42.76%) by gavage at 0, 0.125, 0.25, 0.5, 1.0, and 2.0 g/kg/day for 90 days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28959001
RT4, T24, UMUC3, HT1376, and HT 1197 cells, as well as TSC1+/+/p53+/+, TSC1–/–/p53+/+, TSC2+/+/ p53–/–, TSC2–/–/p53–/– MEFs, LKB knockout and wildtype MEFs were plated at a density of 2 x 10^5 per well in 24-well culture plates in medium containing 10% FBS. After 24 hours, the medium was refreshed and then was either left untreated or was treated with yangonin (1.25-100mg/ml), docetaxel or flavokawain A After treatment, MTT was added to the wells at a final concentration of 1 mg/mL and incubated at 37°C for 3 hours. The absorbance was determined at 570 nm. Cell sensitivity to drug treatment was expressed as the drug concentration that yielded 50% cell growth inhibition
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2592 (Number of products:13)
Created by
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C110481
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R970U49V3C
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500-62-9
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m11561
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212502
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5281575
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DTXSID4034102
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YANGONIN
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SUBSTANCE RECORD