6-[(E)-2-(cyclohexa-1,5-dien-1-yl)ethenyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one

• ChemBase ID: 1157
• Molecular Formular: C14H16O3
• Molecular Mass: 232.27504
• Monoisotopic Mass: 232.10994437
• SMILES: O1C(CC(=CC1=O)OC)/C=C/C1=CCCC=C1
• Canonical SMILES: COC1=CC(=O)OC(C1)/C=C/C1=CCCC=C1
• InChI: InChI=1S/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h3,5-8,10,12H,2,4,9H2,1H3/b8-7+
• InChIKey: OMNGEVNATYFZGG-BQYQJAHWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[(E)-2-(cyclohexa-1,5-dien-1-yl)ethenyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
• IUPAC Traditional name: kavapyrone
• Synonyms: Kava

Database IDs

• CAS Number: 9000-38-8
• PubChem SID: 46505711; 160964620
• PubChem CID: 5281052

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.548529
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.0502744
• LogD (pH = 7.4): 2.0502744
• Log P: 2.0502744
• Molar Refractivity: 70.3797 cm^3
• Polarizability: 25.54749 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.74
• LOG S: -3.57
• Solubility (Water): 6.32e-02 g/l

DETAILS

DrugBank - DB01322

• Drug Groups: nutraceutical
• References: Uebelhack R, Franke L, Schewe HJ: Inhibition of platelet MAO-B by kava pyrone-enriched extract from Piper methysticum Forster (kava-kava). Pharmacopsychiatry. 1998 Sep;31(5):187-92. [Pubmed] ; Baum SS, Hill R, Rommelspacher H: Effect of kava extract and individual kavapyrones on neurotransmitter levels in the nucleus accumbens of rats. Prog Neuropsychopharmacol Biol Psychiatry. 1998 Oct;22(7):1105-20. [Pubmed] ; Seitz U, Schule A, Gleitz J: [3H]-monoamine uptake inhibition properties of kava pyrones. Planta Med. 1997 Dec;63(6):548-9. [Pubmed] ; Lim ST, Dragull K, Tang CS, Bittenbender HC, Efird JT, Nerurkar PV: Effects of kava alkaloid, pipermethystine, and kavalactones on oxidative stress and cytochrome P450 in F-344 rats. Toxicol Sci. 2007 May;97(1):214-21. Epub 2007 Feb 27. [Pubmed] ; Sorrentino L, Capasso A, Schmidt M: Safety of ethanolic kava extract: Results of a study of chronic toxicity in rats. Phytomedicine. 2006 Sep;13(8):542-9. Epub 2006 Aug 14. [Pubmed]
• External Links: Wikipedia; Drugs.com

REFERENCES

• Sorrentino L, Capasso A, Schmidt M: Safety of ethanolic kava extract: Results of a study of chronic toxicity in rats. Phytomedicine. 2006 Sep;13(8):542-9. Epub 2006 Aug 14. Pubmed
• Uebelhack R, Franke L, Schewe HJ: Inhibition of platelet MAO-B by kava pyrone-enriched extract from Piper methysticum Forster (kava-kava). Pharmacopsychiatry. 1998 Sep;31(5):187-92. Pubmed
• Baum SS, Hill R, Rommelspacher H: Effect of kava extract and individual kavapyrones on neurotransmitter levels in the nucleus accumbens of rats. Prog Neuropsychopharmacol Biol Psychiatry. 1998 Oct;22(7):1105-20. Pubmed
• Seitz U, Schule A, Gleitz J: [3H]-monoamine uptake inhibition properties of kava pyrones. Planta Med. 1997 Dec;63(6):548-9. Pubmed
• Lim ST, Dragull K, Tang CS, Bittenbender HC, Efird JT, Nerurkar PV: Effects of kava alkaloid, pipermethystine, and kavalactones on oxidative stress and cytochrome P450 in F-344 rats. Toxicol Sci. 2007 May;97(1):214-21. Epub 2007 Feb 27. Pubmed