CAS 9000-38-8|6-[(E)-2-(cyclohexa-1,5-dien-1-yl)ethenyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one|Kava|kavapyrone

General Information

Structure

Molecular Formula

C₁₄H₁₆O₃

Molecular Mass

232.27504

Exact Mass

232.10994437

Charge

0

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

Canonic Smiles

COC1=CC(=O)OC(C1)/C=C/C1=CCCC=C1

Isomeric Smiles

O1C(CC(=CC1=O)OC)/C=C/C1=CCCC=C1

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

Polarizability

25.54749

Polar Surface Area

35.53

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

Data Source

Academic Data

Data Source

Names and Identifiers

IUPAC name

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

Synonyms

Kava

IUPAC Traditional name

kavapyrone

Names and Identifiers

Registration numbers

PubChem SID

16096462046505711

PubChem CID

5281052

CAS Number

9000-38-8

Registration numbers

Properties

No Data Available

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Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:1157