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Showing Compound (+)-3-Thujone (FDB014960)

Record Information
Version1.0
Creation date2010-04-08 22:11:34 UTC
Update date2019-11-26 03:11:02 UTC
Primary IDFDB014960
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number471-15-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(+)-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
(+)-β-Thujonebiospider
[1S-(1α,4β,5α)]-4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-oneGenerator
β-Thujonebiospider
3-Thujanone, (1S,4S,5R)-(+)-biospider
D-β-Thujonebiospider
D-β-thujoneGenerator
Thujone, (+)-biospider
β-thujoneGenerator
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
Chemical FormulaC10H16O
IUPAC name(1S,4S,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
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
Isomeric SMILESCC(C)[C@@]12C[C@@H]1[C@H](C)C(=O)C2
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
Classification
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

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting PointNot Available
Boiling PointBp 201-202°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +72.46 (neat)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(+)-3-Thujone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ou-9300000000-5ac67463cc6dff4e26c5Spectrum
Predicted GC-MS(+)-3-Thujone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e5a1ab6ee8fcd2e7222d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-7900000000-e4ab468ffb3afaf161292016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pe9-9000000000-960a6c7d4901afec92332016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-07a82b9f8d15764ed9042016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-65761ceb0d88aa809b6a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-4023ebf09d9995d371112016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-e8b89c21a7958e1852782021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdl-7900000000-5c5ad8968d995b2431ac2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-8900000000-a32be7e7fd99fd0b8b232021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-9300000000-eac02498908e1d67934a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-22a79a891aa2c60d074e2021-09-22View Spectrum
NMRNot Available
ChemSpider ID82583
ChEMBL IDCHEMBL3277898
KEGG Compound IDC20260
Pubchem Compound ID91456
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36113
CRC / DFC (Dictionary of Food Compounds) IDJXM68-F:JXM64-B
EAFUS IDNot Available
Dr. Duke IDBETA-THUJONE|3-ISOTHUJONE
BIGG IDNot Available
KNApSAcK IDC00000836
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDThujone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Abortifacient50691 An agent that induces abortion, disrupting pregnancy by blocking progesterone or causing uterine contractions. Therapeutically, it's used to terminate early pregnancies, manage ectopic pregnancies, or treat miscarriages. Key medical uses include medical abortion, pregnancy termination, and menstrual regulation.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti feedantA substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.DUKE
EmmenagogueAn agent that stimulates blood flow in the pelvic area and uterus, often used to induce or regulate menstruation, treating conditions like amenorrhea and dysmenorrhea.DUKE
Insectifuge24852 A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.