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9000-38-8 molecular structure
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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 and InChIs

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

Cite this record

CBID:1157 http://www.chembase.cn/molecule-1157.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
9000-38-8
PubChem SID
46505711
160964620
PubChem CID
5281052

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 16.548529  H Acceptors
H Donor LogD (pH = 5.5) 2.0502744 
LogD (pH = 7.4) 2.0502744  Log P 2.0502744 
Molar Refractivity 70.3797 cm3 Polarizability 25.54749 Å3
Polar Surface Area 35.53 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.74  LOG S -3.57 
Solubility (Water) 6.32e-02 g/l 

PROPERTIES

PROPERTIES

Bioassay(PubChem)

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB01322 external link
Item Information
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

REFERENCES

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  • • 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
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PATENTS

PATENTS

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