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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:10:46 UTC
Update Date2022-03-07 02:54:47 UTC
HMDB IDHMDB0036113
Secondary Accession Numbers
  • HMDB36113
Metabolite Identification
Common Name(+)-3-Thujone
Description(+)-3-Thujone, also known as beta-thujone or β-thujone, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (+)-3-thujone is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on (+)-3-Thujone.
Structure
Data?1563862822
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
[1S-(1a,4b,5a)]-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-oneGenerator
[1S-(1Α,4β,5α)]-4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-oneGenerator
b-ThujoneGenerator
Β-thujoneGenerator
D-b-ThujoneGenerator
D-Β-thujoneGenerator
(+)-b-ThujoneHMDB, Generator
(+)-beta-ThujoneHMDB
(+)-cis-ThujoneHMDB
(+)-ThujoneHMDB
-ThujoneHMDB
D-betaHMDB
IsothujoneHMDB
(+)-3-ThujoneChEBI
(+)-Β-thujoneGenerator
alpha-ThujoneMeSH
cis-ThujoneMeSH
ThujoneMeSH
(-)-ThujoneMeSH
3-IsothujoneMeSH
3-ThujanoneMeSH
beta-Thujone, 1S-(1alpha,4beta,5alpha)-isomerMeSH
alpha, beta-ThujoneMeSH
beta-Thujone, (1S-(1alpha,4alpha,5alpha))-isomerMeSH
beta-Thujone, (1alpha,4alpha,5alpha)-isomerMeSH
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
Description 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
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility407.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.20931661259
DarkChem[M-H]-136.50831661259
DeepCCS[M-2H]-173.930932474
DeepCCS[M+Na]+148.95830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(+)-3-ThujoneCC(C)[C@@]12C[C@@H]1[C@H](C)C(=O)C21519.4Standard polar33892256
(+)-3-ThujoneCC(C)[C@@]12C[C@@H]1[C@H](C)C(=O)C21130.1Standard non polar33892256
(+)-3-ThujoneCC(C)[C@@]12C[C@@H]1[C@H](C)C(=O)C21097.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(+)-3-Thujone,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C[C@]2(C(C)C)C[C@H]121290.3Semi standard non polar33892256
(+)-3-Thujone,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C[C@]2(C(C)C)C[C@H]121341.1Standard non polar33892256
(+)-3-Thujone,1TMS,isomer #2CC(C)[C@]12C=C(O[Si](C)(C)C)[C@@H](C)[C@H]1C21220.7Semi standard non polar33892256
(+)-3-Thujone,1TMS,isomer #2CC(C)[C@]12C=C(O[Si](C)(C)C)[C@@H](C)[C@H]1C21300.1Standard non polar33892256
(+)-3-Thujone,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C[C@]2(C(C)C)C[C@H]121520.9Semi standard non polar33892256
(+)-3-Thujone,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C[C@]2(C(C)C)C[C@H]121549.2Standard non polar33892256
(+)-3-Thujone,1TBDMS,isomer #2CC(C)[C@]12C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@H]1C21436.0Semi standard non polar33892256
(+)-3-Thujone,1TBDMS,isomer #2CC(C)[C@]12C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@H]1C21487.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (+)-3-Thujone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ou-9300000000-5ac67463cc6dff4e26c52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-3-Thujone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-3-Thujone 10V, Positive-QTOFsplash10-0udi-0900000000-e5a1ab6ee8fcd2e7222d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-3-Thujone 20V, Positive-QTOFsplash10-0udi-7900000000-e4ab468ffb3afaf161292016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-3-Thujone 40V, Positive-QTOFsplash10-0pe9-9000000000-960a6c7d4901afec92332016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-3-Thujone 10V, Negative-QTOFsplash10-0udi-0900000000-07a82b9f8d15764ed9042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-3-Thujone 20V, Negative-QTOFsplash10-0udi-0900000000-65761ceb0d88aa809b6a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-3-Thujone 40V, Negative-QTOFsplash10-0006-9500000000-4023ebf09d9995d371112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-3-Thujone 10V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-3-Thujone 20V, Negative-QTOFsplash10-0udi-0900000000-e8b89c21a7958e1852782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-3-Thujone 40V, Negative-QTOFsplash10-0pdl-7900000000-5c5ad8968d995b2431ac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-3-Thujone 10V, Positive-QTOFsplash10-0006-8900000000-a32be7e7fd99fd0b8b232021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-3-Thujone 20V, Positive-QTOFsplash10-000x-9300000000-eac02498908e1d67934a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-3-Thujone 40V, Positive-QTOFsplash10-0006-9400000000-22a79a891aa2c60d074e2021-09-22Wishart LabView Spectrum
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1384741
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
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  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.