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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:19:30 UTC
Update Date2021-10-13 08:35:39 UTC
HMDB IDHMDB0041631
Secondary Accession Numbers
  • HMDB41631
Metabolite Identification
Common Name3-Thujanone
Description3-Thujanone 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?1563863685
Synonyms
ValueSource
4-Methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-oneChEBI
(+)-ThujoneMeSH
(-)-ThujoneMeSH
3-IsothujoneMeSH
alpha, beta-ThujoneMeSH
alpha-ThujoneMeSH
beta-ThujoneMeSH
beta-Thujone, (1S-(1alpha,4alpha,5alpha))-isomerMeSH
beta-Thujone, (1alpha,4alpha,5alpha)-isomerMeSH
beta-Thujone, 1S-(1alpha,4beta,5alpha)-isomerMeSH
cis-ThujoneMeSH
ThujoneMeSH
3-ThujanoneChEBI
(+-)-IsothujoneHMDB
(+-)-ThujoneHMDB
1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-oneHMDB
3-SabinanoneHMDB
4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one, 9ciHMDB
AbsinthoneHMDB
ChrysanthoneHMDB
SalvoneHMDB
TanacetoneHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.237
Monoisotopic Molecular Weight152.120115135
IUPAC Name4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
Traditional Name3-isothujone
CAS Registry Number1125-12-8
SMILES
CC(C)C12CC1C(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
InChI KeyUSMNOWBWPHYOEA-UHFFFAOYSA-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

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point200.00 to 201.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility407.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.044 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.44 g/LALOGPS
logP10(1.74) g/LALOGPS
logP10(2.28) g/LChemAxon
logS10(-2.5) g/LALOGPS
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
Polarizability17.98 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]+135.87731661259
DarkChem[M-H]-129.62531661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-ThujanoneCC(C)C12CC1C(C)C(=O)C21516.6Standard polar33892256
3-ThujanoneCC(C)C12CC1C(C)C(=O)C21117.3Standard non polar33892256
3-ThujanoneCC(C)C12CC1C(C)C(=O)C21104.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Thujanone,1TMS,isomer #1CC1=C(O[Si](C)(C)C)CC2(C(C)C)CC121297.9Semi standard non polar33892256
3-Thujanone,1TMS,isomer #1CC1=C(O[Si](C)(C)C)CC2(C(C)C)CC121311.5Standard non polar33892256
3-Thujanone,1TMS,isomer #2CC1C(O[Si](C)(C)C)=CC2(C(C)C)CC121229.0Semi standard non polar33892256
3-Thujanone,1TMS,isomer #2CC1C(O[Si](C)(C)C)=CC2(C(C)C)CC121286.8Standard non polar33892256
3-Thujanone,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)CC2(C(C)C)CC121547.8Semi standard non polar33892256
3-Thujanone,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)CC2(C(C)C)CC121522.3Standard non polar33892256
3-Thujanone,1TBDMS,isomer #2CC1C(O[Si](C)(C)C(C)(C)C)=CC2(C(C)C)CC121446.4Semi standard non polar33892256
3-Thujanone,1TBDMS,isomer #2CC1C(O[Si](C)(C)C(C)(C)C)=CC2(C(C)C)CC121487.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Thujanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9300000000-eec889eda42ade9a448b2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Thujanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Thujanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Thujanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Thujanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Thujanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Thujanone 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-Thujanone 10V, Positive-QTOFsplash10-0udi-0900000000-e5a1ab6ee8fcd2e7222d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Thujanone 20V, Positive-QTOFsplash10-0udi-7900000000-6bfa698b489e2584c2e82015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Thujanone 40V, Positive-QTOFsplash10-0pe9-9000000000-c1faae6eaa2d099fe95f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Thujanone 10V, Negative-QTOFsplash10-0udi-0900000000-07a82b9f8d15764ed9042015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Thujanone 20V, Negative-QTOFsplash10-0udi-0900000000-65761ceb0d88aa809b6a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Thujanone 40V, Negative-QTOFsplash10-0006-9500000000-4023ebf09d9995d371112015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Thujanone 10V, Positive-QTOFsplash10-0006-8900000000-a32be7e7fd99fd0b8b232021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Thujanone 20V, Positive-QTOFsplash10-000x-9300000000-eac02498908e1d67934a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Thujanone 40V, Positive-QTOFsplash10-0006-9400000000-22a79a891aa2c60d074e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Thujanone 10V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Thujanone 20V, Negative-QTOFsplash10-0udi-0900000000-e8b89c21a7958e1852782021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Thujanone 40V, Negative-QTOFsplash10-0pdl-7900000000-5c5ad8968d995b2431ac2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB021854
KNApSAcK IDC00024784
Chemspider ID10561
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThujone
METLIN IDNot Available
PubChem Compound11027
PDB IDNot Available
ChEBI ID50040
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1137041
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.