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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:10:50 UTC
Update Date2022-03-07 02:54:47 UTC
HMDB IDHMDB0036114
Secondary Accession Numbers
  • HMDB36114
Metabolite Identification
Common Name(-)-3-Thujone
Description(-)-3-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 small amount of articles have been published on (-)-3-Thujone.
Structure
Data?1563862823
Synonyms
ValueSource
(1R,4R,5S)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-oneChEBI
(-)-beta-ThujoneHMDB
(-)-cis-ThujoneHMDB
(-)-IsothujoneHMDB
L-IsothujoneHMDB
(-)-b-ThujoneGenerator
(-)-Β-thujoneGenerator
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name(1R,4R,5S)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
Traditional Name(-)-β-thujone
CAS Registry NumberNot Available
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-/m1/s1
InChI KeyUSMNOWBWPHYOEA-KHQFGBGNSA-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

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
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]+137.34431661259
DarkChem[M-H]-135.95331661259
DeepCCS[M-2H]-172.99630932474
DeepCCS[M+Na]+147.99630932474
AllCCS[M+H]+132.132859911
AllCCS[M+H-H2O]+127.732859911
AllCCS[M+NH4]+136.132859911
AllCCS[M+Na]+137.232859911
AllCCS[M-H]-137.932859911
AllCCS[M+Na-2H]-139.132859911
AllCCS[M+HCOO]-140.532859911

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
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, 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
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
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 IDFDB014961
KNApSAcK IDNot Available
Chemspider ID5026861
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6553876
PDB IDNot Available
ChEBI ID50046
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.