(+)-3-Thujone (CED0033108)

Record Information
Version1.0
Creation Date2016-05-26 01:32:13 UTC
Update Date2026-04-05 16:14:33 UTC
Accession NumberCHEM029946
Identification
Common Name(+)-3-Thujone
ClassSmall Molecule
Description
(+)-3-Thujone is an organic compound with the formula C10H16O and an average molecular weight of 152.23 g/mol. (+)-3-Thujone belongs to the monoterpenoids, a subclass of prenol lipids within the organic compounds. This compound is found in or released from 13 recorded sources across several sectors. Within the electrical and electronic equipment sector, it is associated with cell phones, capacitors, wires and cables, batteries, and printed circuit boards, among one other source. In the textiles, leather and furnishings sector, it is found in synthetic textiles as well as carpets and rugs. It is also present in food packaging within the food, food processing and cookware sector. Additionally, it is linked to medical devices in the healthcare, pharmaceuticals and veterinary products sector. In the energy, oil and gas sector and the industrial manufacturing and chemical processing sector, it is found in lubricants. One other sector is also recorded as a source. Recorded exposure routes for (+)-3-Thujone include inhalation, oral, and touch.
Contaminant Type
  • Human Neurotoxin
  • PFAS
  • Phytotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
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 Mass152.233 g/mol
Monoisotopic Mass152.120 g/mol
CAS Registry Number471-15-8
IUPAC Name(1S,4S,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
Traditional Name(+)-β-thujone
SMILESCC(C)[C@@]12C[C@@H]1[C@H](C)C(=O)C2
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00ou-9300000000-5ac67463cc6dff4e26c5Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-e5a1ab6ee8fcd2e7222dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-7900000000-e4ab468ffb3afaf16129Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pe9-9000000000-960a6c7d4901afec9233Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-07a82b9f8d15764ed904Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-65761ceb0d88aa809b6aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9500000000-4023ebf09d9995d37111Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-c373c9eea3cebf186f53Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-e8b89c21a7958e185278Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pdl-7900000000-5c5ad8968d995b2431acNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-8900000000-a32be7e7fd99fd0b8b23Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000x-9300000000-eac02498908e1d67934aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9400000000-22a79a891aa2c60d074eNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
253.0Log mg/kg[140:450]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
604Pest AttractantsAgriculture & land managementNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
634BucklesTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureSerine/threonine-protein phosphatase 2A 65 kDa regulatory subunit A alpha isoformQ76MZ3Mus musculusPredicted (SEA)2.49118
Click to view 3D structureSynaptic vesicle glycoprotein 2AQ02563Rattus norvegicusPredicted (SEA)82.1309
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)6314.43
Click to view 3D structureHemagglutininP03438Influenza A virus (strain A/X-31 H3N2)Predicted (SEA)74.0346
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)138.338
11-beta-hydroxysteroid dehydrogenase 1 structureClick to view 3D structure11-beta-hydroxysteroid dehydrogenase 1P28845HumansPredicted (SEA)5425.94
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)305.091
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)7748.26
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)2959.2
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)1026.13
Click to view 3D structureDNA damage-inducible transcript 3 proteinP35639Mus musculusPredicted (SEA)7100.24
X-box-binding protein 1 structureClick to view 3D structureX-box-binding protein 1P17861HumansPredicted (SEA)7103.43
Click to view 3D structureGamma-aminobutyric acid receptor subunit alpha-4P28471Rattus norvegicusPredicted (SEA)41.5715
Click to view 3D structureHTH-type quorum-sensing regulator RhlRP54292Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)Predicted (SEA)373.754
Aromatase structureClick to view 3D structureAromataseP11511HumansPredicted (SEA)6205.83
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)7576.83
Click to view 3D structureEcdysone receptorP34021Drosophila melanogasterPredicted (SEA)57.1413
Click to view 3D structureAcetylcholinesteraseP04058Torpedo californicaPredicted (SEA)3740.97
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)7709.49
Click to view 3D structureBeta-lactamase OXA-48Q6XEC0Klebsiella pneumoniaePredicted (SEA)28.0257
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)7689.87
Protein kinase C alpha type structureClick to view 3D structureProtein kinase C alpha typeP17252HumansPredicted (SEA)7509.65
Click to view 3D structureAcetylcholinesteraseO42275Electrophorus electricusPredicted (SEA)7278.98
Click to view 3D structureExtended-spectrum beta-lactamase PER-6D5HSX5Aeromonas allosaccharophilaPredicted (SEA)93.2634
Click to view 3D structureADC-14 proteinQ0VTR6Acinetobacter genomosp. 3Predicted (SEA)93.2634
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0036113
FooDB IDFDB014960
Phenol Explorer IDNot Available
KNApSAcK IDC00000836
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID82583
ChEBI ID50045
PubChem Compound ID91456
Kegg Compound IDC20260
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
12. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
16. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
17. The lipid handbook with CD-ROM