(6R)-6-[2-(2H-1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one

• ChemBase ID: 128389
• Molecular Formular: C15H14O5
• Molecular Mass: 274.26866
• Monoisotopic Mass: 274.08412355
• SMILES: COC1=CC(=O)O[C@H](C1)/C=C/c1cc2c(cc1)OCO2
• Canonical SMILES: COC1=CC(=O)O[C@H](C1)/C=C/c1ccc2c(c1)OCO2
• InChI: InChI=1S/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/t11-/m0/s1
• InChIKey: GTEXBOVBADJOQH-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R)-6-[2-(2H-1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one; (6R)-6-[(E)-2-(2H-1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
• IUPAC Traditional name: (6R)-6-[2-(2H-1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-5,6-dihydropyran-2-one; methysticin
• Synonyms: Methysticin; (6R)-6-[(1E)-2-(1,3-Benzodioxol-5-yl)ethenyl]-5,6-dihydro-4-methoxy-2H-pyran-2-one; (+)-Methysticin; Kavahin; Methysticin; NSC 112158; d-Methysticin; Kavatin

Database IDs

• CAS Number: 495-85-2
• PubChem SID: 162222696
• PubChem CID: 5281567
• Wikipedia Title: Methysticin

CALCULATED PROPERTIES

• Acid pKa: 16.540186
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.0559452
• LogD (pH = 7.4): 2.0559452
• Log P: 2.0559452
• Molar Refractivity: 73.1246 cm^3
• Polarizability: 27.870499 Å^3
• Polar Surface Area: 53.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K145500

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. One of the active components of the intoxicating beverage Kava from t

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)