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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
Structure of YANGONIN

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+

HIDE SMILES / InChI

Description
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

Sources: Archiv der Pharmazie (Weinheim, Germany) (1909), 246, 338.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.72 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1.
2011 Dec
Patents

Patents

Sample Use Guides

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
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
Name Type Language
YANGONIN
MI  
Common Name English
YANGONIN [MI]
Common Name English
NSC-212502
Code English
4-METHOXY-6-((E)-2-(4-METHOXYPHENYL)ETHENYL)PYRAN-2-ONE
Systematic Name English
2H-PYRAN-2-ONE, 4-METHOXY-6-((1E)-2-(4-METHOXYPHENYL)ETHENYL)-
Systematic Name English
2H-PYRAN-2-ONE, 4-METHOXY-6-(2-(4-METHOXYPHENYL)ETHENYL)-, (E)-
Systematic Name English
2H-PYRAN-2-ONE, 4-METHOXY-6-(P-METHOXYSTYRYL)-
Systematic Name English
Classification Tree Code System Code
DSLD 2592 (Number of products:13)
Created by admin on Fri Dec 15 19:48:26 GMT 2023 , Edited by admin on Fri Dec 15 19:48:26 GMT 2023
Code System Code Type Description
MESH
C110481
Created by admin on Fri Dec 15 19:48:26 GMT 2023 , Edited by admin on Fri Dec 15 19:48:26 GMT 2023
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FDA UNII
R970U49V3C
Created by admin on Fri Dec 15 19:48:26 GMT 2023 , Edited by admin on Fri Dec 15 19:48:26 GMT 2023
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CAS
500-62-9
Created by admin on Fri Dec 15 19:48:26 GMT 2023 , Edited by admin on Fri Dec 15 19:48:26 GMT 2023
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MERCK INDEX
m11561
Created by admin on Fri Dec 15 19:48:26 GMT 2023 , Edited by admin on Fri Dec 15 19:48:26 GMT 2023
PRIMARY Merck Index
NSC
212502
Created by admin on Fri Dec 15 19:48:26 GMT 2023 , Edited by admin on Fri Dec 15 19:48:26 GMT 2023
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PUBCHEM
5281575
Created by admin on Fri Dec 15 19:48:26 GMT 2023 , Edited by admin on Fri Dec 15 19:48:26 GMT 2023
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EPA CompTox
DTXSID4034102
Created by admin on Fri Dec 15 19:48:26 GMT 2023 , Edited by admin on Fri Dec 15 19:48:26 GMT 2023
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WIKIPEDIA
YANGONIN
Created by admin on Fri Dec 15 19:48:26 GMT 2023 , Edited by admin on Fri Dec 15 19:48:26 GMT 2023
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