Structure Database (LMSD)

Common Name
(-)-alpha-Thujone
Systematic Name
(1S,4R,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one (1S,4S,5R)-thujan-3-one
Synonyms
  • (1S,4R,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
LM ID
LMPR0102120019
Formula
Exact Mass
Calculate m/z
152.120115
Status
Curated




Classification

Biological Context

(–)-α-Thujone is a monoterpene ketone and a major component of absinthe and has diverse biological activities.1,2,3,4 It inhibits currents induced by acetylcholine (ACh) in Xenopus oocytes expressing human α7 nicotinic acetylcholine receptors (nAChRs; IC50 = 27 µM).1 (–)-α-Thujone (100 and 300 µM) reduces GABA-induced current amplitude in HEK293 cells expressing α1β2δ subunit-containing GABA receptors.2 It reduces levels of the Norovirus surrogates feline calcivirus-F9 (FCV-F9) and murine norovirus 1 (MNV-1) in a plaque formation assay when used at a concentration of 25 mM.3 In vivo, (–)-α-thujone (1.25 mg/kg, i.p.) impairs nicotine-induced enhancement of long-term potentiation in the dentate gyrus, a marker of learning and memory, in rats.1 It also inhibits lung metastasis and increases survival in a B16/F10 murine melanoma model when administered at a dose of 1 mg/kg.4

This information has been provided by Cayman Chemical

References

3. Chung, M.S. Antiviral activities of Artemisia princeps var. orientalis essential oil and its α-thujone against norovirus surrogates. Food Sci. Biotechnol. 26(5), 1457-1461 (2017).
4. Siveen, K.S., and Kuttan, G. Thujone inhibits lung metastasis induced by B16F-10 melanoma cells in C57BL/6 mice. Can. J. Physiol. Pharmacol. 89(10), 89(10) (2011).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Artemisia absinthium (#72332)
Magnoliopsida (#3398)
Alpha-thujone (the active component of absinthe): gamma-aminobutyric acid type A receptor modulation and metabolic detoxification.,
Proc Natl Acad Sci U S A, 2000
Pubmed ID: 10725394

String Representations

InChiKey (Click to copy)
USMNOWBWPHYOEA-MRTMQBJTSA-N
InChi (Click to copy)
InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8-,10+/m1/s1
SMILES (Click to copy)
[C@]12(C(C)C)CC([C@H](C)[C@@]1([H])C2)=O

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 11
Rings 2
Aromatic Rings 0
Rotatable Bonds 1
Van der Waals Molecular Volume 162.99
Topological Polar Surface Area 17.07
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 1
logP 2.26
Molar Refractivity 44.17

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Created at
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Updated at
31st Jul 2024