4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one

• ChemBase ID: 130222
• Molecular Formular: C15H14O4
• Molecular Mass: 258.26926
• Monoisotopic Mass: 258.08920893
• SMILES: COc1ccc(cc1)/C=C/c1cc(cc(=O)o1)OC
• Canonical SMILES: COc1ccc(cc1)/C=C/c1cc(OC)cc(=O)o1
• InChI: 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
• InChIKey: XLHIYUYCSMZCCC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one; 4-methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one
• IUPAC Traditional name: yangonin; 4-methoxy-6-[2-(4-methoxyphenyl)ethenyl]pyran-2-one
• Synonyms: 4-Methoxy-6-[(1E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one; 4-Methoxy-6-[β-(p-anisyl)vinyl]-α-pyrone; 6-(p-Methoxystyryl)-4-methoxy-α-pyrone; Yangonin

Database IDs

• CAS Number: 500-62-9
• PubChem SID: 162224502
• PubChem CID: 5281575
• CHEMBL: 1098658
• Chemspider ID: 4444896
• Wikipedia Title: Yangonin

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.4818187
• LogD (pH = 7.4): 2.4818187
• Log P: 2.4818187
• Molar Refractivity: 75.2039 cm^3
• Polarizability: 27.653633 Å^3
• Polar Surface Area: 44.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - Y100550

A lactone isolated from the Kava plant (Piper methysticum). The active constituents of Kava are a group of approx. 18 compounds collectively referred to as kavalactones or kava pyrones. Kawain, dihydrokawain, methysticin, dihydromethysticin, yangonin, and

REFERENCES

• Keledjian, J., et al.: J. Pharm. Sci., 77, 1003 (1988)
• Clouatre, D., et al.: Toxicol. Lett., 150, 85 (1988)
• Mathews, J., et al.: Drug Metab. Dispos., 33, 1555 (1988)
• Clayton, N., et al.: Exp. Toxicol. Pathol., 58, 223 (1988)