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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:10:53 UTC
Update Date2019-01-11 19:51:20 UTC
HMDB IDHMDB0036115
Secondary Accession Numbers
  • HMDB36115
Metabolite Identification
Common Name(-)-3-Isothujone
Description(-)-3-Isothujone is found in alcoholic beverages. Ingredient of absinthe. Presence in food and beverages regulated by legislation.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
(-)-3-ThujanoneChEBI
(1S,4R,5R)-(-)-3-ThujanoneChEBI
(1S,4R,5R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-oneChEBI
[1S-(1alpha,4alpha,5alpha)]-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-oneChEBI
alpha-ThujoneChEBI
L-ThujoneChEBI
ThujonChEBI
ThujoneChEBI
[1S-(1a,4a,5a)]-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-oneGenerator
[1S-(1α,4α,5α)]-4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-oneGenerator
a-ThujoneGenerator
α-thujoneGenerator
(-)-a-ThujoneHMDB
(-)-alpha-ThujoneHMDB
(-)-IsothujoneHMDB
(-)-ThujoneHMDB
(-)-trans-ThujoneHMDB
(1S,4R,5R)-Thujan-3-oneHMDB
alpha-(-)-ThujoneHMDB
L-alpha-ThujoneHMDB
3-IsothujoneMeSH
3-ThujanoneMeSH
beta-Thujone, 1S-(1alpha,4beta,5alpha)-isomerMeSH
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,4R,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
Traditional Namethujone
CAS Registry Number546-80-5
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-MRTMQBJTSA-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
  • 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

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot 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
Polarizability18.01 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0159-9100000000-9e3f8c13550e0c33d603JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0159-9100000000-9e3f8c13550e0c33d603JSpectraViewer | MoNA
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 IDFDB014962
KNApSAcK IDC00003064
Chemspider ID229574
KEGG Compound IDC09906
BioCyc IDCPD-14067
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound261491
PDB IDNot Available
ChEBI ID9577
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.