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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:10:46 UTC
Update Date2019-01-11 19:51:20 UTC
HMDB IDHMDB0036113
Secondary Accession Numbers
  • HMDB36113
Metabolite Identification
Common Name(+)-3-Thujone
Description(+)-3-Thujone is found in common sage. Thujone is a ketone and a monoterpene that occurs naturally in two diastereomeric forms: (-)-alpha-thujone and (+)-beta-thujone. It has a menthol odor. In addition to (-)-alpha-thujone and (+)-beta-thujone, there are their enantiomeric forms, (+)-alpha-thujone and (-)-beta-thujone. (Wikipedia
Structure
Data?1547236280
Synonyms
ValueSource
(+)-IsothujoneChEBI
(1S,4S,5R)-(+)-3-ThujanoneChEBI
(1S,4S,5R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-oneChEBI
[1S-(1alpha,4beta,5alpha)]-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-oneChEBI
beta-ThujoneChEBI
D-beta-ThujoneChEBI
D-IsothujoneChEBI
trans-ThujoneChEBI
(+)-b-ThujoneHMDB
(+)-beta-ThujoneHMDB
(+)-cis-ThujoneHMDB
(+)-ThujoneHMDB
-ThujoneHMDB
D-betaHMDB
IsothujoneHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name(1S,4S,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
Traditional Name(+)-β-thujone
CAS Registry Number471-15-8
SMILES
CC(C)[C@@]12C[C@@H]1[C@H](C)C(=O)C2
InChI Identifier
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-/m0/s1
InChI KeyUSMNOWBWPHYOEA-XKSSXDPKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
  • Thujane monoterpenoid
  • Cyclohexanone
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.44 g/LALOGPS
logP1.74ALOGPS
logP2.28ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.54 m³·mol⁻¹ChemAxon
Polarizability18.02 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ou-9300000000-5ac67463cc6dff4e26c5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e5a1ab6ee8fcd2e7222dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-7900000000-e4ab468ffb3afaf16129JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pe9-9000000000-960a6c7d4901afec9233JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-07a82b9f8d15764ed904JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-65761ceb0d88aa809b6aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-4023ebf09d9995d37111JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014960
KNApSAcK IDC00000836
Chemspider ID82583
KEGG Compound IDC20260
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91456
PDB IDNot Available
ChEBI ID50045
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jug-Dujakovic M, Ristic M, Pljevljakusic D, Dajic-Stevanovic Z, Liber Z, Hancevic K, Radic T, Satovic Z: High diversity of indigenous populations of dalmatian sage (Salvia officinalis L.) in essential-oil composition. Chem Biodivers. 2012 Oct;9(10):2309-23. doi: 10.1002/cbdv.201200131. [PubMed:23081929 ]
  2. Walch SG, Lachenmeier DW, Kuballa T, Stuhlinger W, Monakhova YB: Holistic Control of Herbal Teas and Tinctures Based on Sage (Salvia officinalis L.) for Compounds with Beneficial and Adverse Effects using NMR Spectroscopy. Anal Chem Insights. 2012;7:1-12. doi: 10.4137/ACI.S8946. Epub 2012 Mar 21. [PubMed:22493561 ]
  3. Satyal P, Paudel P, Kafle A, Pokharel SK, Lamichhane B, Dosoky NS, Moriarity DM, Setzer WN: Bioactivities of volatile components from Nepalese Artemisia species. Nat Prod Commun. 2012 Dec;7(12):1651-8. [PubMed:23413575 ]
  4. Rice KC, Wilson RS: (-)-3-Isothujone, a small nonnitrogenous molecule with antinociceptive activity in mice. J Med Chem. 1976 Aug;19(8):1054-7. [PubMed:966252 ]
  5. Wise ML, Savage TJ, Katahira E, Croteau R: Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase. J Biol Chem. 1998 Jun 12;273(24):14891-9. [PubMed:9614092 ]
  6. Haider SZ, Andola HC, Mohan M: Constituents of Artemisia gmelinii Weber ex Stechm. from Uttarakhand Himalaya: A Source of Artemisia Ketone. Indian J Pharm Sci. 2012 May;74(3):265-7. doi: 10.4103/0250-474X.106074. [PubMed:23439844 ]
  7. Santos-Gomes PC, Fernandes-Ferreira M: Essential oils produced by in vitro shoots of sage (Salvia officinalis L.). J Agric Food Chem. 2003 Apr 9;51(8):2260-6. [PubMed:12670167 ]
  8. Dehal SS, Croteau R: Metabolism of monoterpenes: specificity of the dehydrogenases responsible for the biosynthesis of camphor, 3-thujone, and 3-isothujone. Arch Biochem Biophys. 1987 Oct;258(1):287-91. [PubMed:3310901 ]
  9. Kolassa N: Menthol differs from other terpenic essential oil constituents. Regul Toxicol Pharmacol. 2013 Feb;65(1):115-8. doi: 10.1016/j.yrtph.2012.11.009. Epub 2012 Dec 1. [PubMed:23207345 ]
  10. Tayade AB, Dhar P, Kumar J, Sharma M, Chauhan RS, Chaurasia OP, Srivastava RB: Chemometric profile of root extracts of Rhodiola imbricata Edgew. with hyphenated gas chromatography mass spectrometric technique. PLoS One. 2013;8(1):e52797. doi: 10.1371/journal.pone.0052797. Epub 2013 Jan 10. [PubMed:23326358 ]
  11. Raut JS, Shinde RB, Chauhan NM, Karuppayil SM: Terpenoids of plant origin inhibit morphogenesis, adhesion, and biofilm formation by Candida albicans. Biofouling. 2013;29(1):87-96. doi: 10.1080/08927014.2012.749398. [PubMed:23216018 ]
  12. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  13. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  14. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  15. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  16. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  17. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.