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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

Molecular Formula C15H14O4
Molecular Weight 258.2693
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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.
2011-12
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:57:42 GMT 2025
Edited
by admin
on Mon Mar 31 19:57:42 GMT 2025
Record UNII
R970U49V3C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-212502
Preferred Name English
YANGONIN
MI  
Common Name English
YANGONIN [MI]
Common Name 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 Mon Mar 31 19:57:42 GMT 2025 , Edited by admin on Mon Mar 31 19:57:42 GMT 2025
Code System Code Type Description
MESH
C110481
Created by admin on Mon Mar 31 19:57:42 GMT 2025 , Edited by admin on Mon Mar 31 19:57:42 GMT 2025
PRIMARY
FDA UNII
R970U49V3C
Created by admin on Mon Mar 31 19:57:42 GMT 2025 , Edited by admin on Mon Mar 31 19:57:42 GMT 2025
PRIMARY
CAS
500-62-9
Created by admin on Mon Mar 31 19:57:42 GMT 2025 , Edited by admin on Mon Mar 31 19:57:42 GMT 2025
PRIMARY
MERCK INDEX
m11561
Created by admin on Mon Mar 31 19:57:42 GMT 2025 , Edited by admin on Mon Mar 31 19:57:42 GMT 2025
PRIMARY Merck Index
NSC
212502
Created by admin on Mon Mar 31 19:57:42 GMT 2025 , Edited by admin on Mon Mar 31 19:57:42 GMT 2025
PRIMARY
PUBCHEM
5281575
Created by admin on Mon Mar 31 19:57:42 GMT 2025 , Edited by admin on Mon Mar 31 19:57:42 GMT 2025
PRIMARY
EPA CompTox
DTXSID4034102
Created by admin on Mon Mar 31 19:57:42 GMT 2025 , Edited by admin on Mon Mar 31 19:57:42 GMT 2025
PRIMARY
WIKIPEDIA
YANGONIN
Created by admin on Mon Mar 31 19:57:42 GMT 2025 , Edited by admin on Mon Mar 31 19:57:42 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT