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Showing Compound (-)-3-Isothujone (FDB014962)

Record Information
Version1.0
Creation date2010-04-08 22:11:34 UTC
Update date2019-11-26 03:11:02 UTC
Primary IDFDB014962
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-3-Isothujone
DescriptionIngredient 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. (-)-3-Isothujone is found in many foods, some of which are mugwort, pepper (c. frutescens), common oregano, and cornmint.
CAS Number546-80-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-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, MeSH
(-)-trans-ThujoneHMDB
(1S,4R,5R)-Thujan-3-oneHMDB
alpha-(-)-ThujoneHMDB
L-alpha-ThujoneHMDB
3-IsothujoneMeSH, HMDB
3-ThujanoneMeSH, HMDB
beta-Thujone, 1S-(1alpha,4beta,5alpha)-isomerMeSH, HMDB
beta-ThujoneMeSH, HMDB
beta-Thujone, (1S-(1alpha,4alpha,5alpha))-isomerMeSH, HMDB
beta-Thujone, (1alpha,4alpha,5alpha)-isomerMeSH, HMDB
(-)-3-IsothujoneKEGG
(+)-ThujoneMeSH
cis-ThujoneMeSH
alpha, beta-ThujoneMeSH
(1S,4R,5R)-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-onePhytoBank
(-)-α-ThujonePhytoBank
AbsintholPhytoBank
[1S-(1α,4α,5α)]-4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-oneGenerator
α-Thujonebiospider
3-Thujanone, (-)-biospider
3-Thujanone, (1S,4R,5R)-(-)-biospider
Isothujone, (-)-biospider
α-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
Polarizability17.94 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16O
IUPAC name(1S,4R,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+/m1/s1
InChI KeyUSMNOWBWPHYOEA-MRTMQBJTSA-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 Point< 25 oC
Boiling PointBp12 78°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D -20.5 (c, 2 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(-)-3-Isothujone, non-derivatized, GC-MS Spectrumsplash10-0159-9100000000-9e3f8c13550e0c33d603Spectrum
GC-MS(-)-3-Isothujone, non-derivatized, GC-MS Spectrumsplash10-0159-9100000000-9e3f8c13550e0c33d603Spectrum
Predicted GC-MS(-)-3-Isothujone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ou-9300000000-5ac67463cc6dff4e26c5Spectrum
Predicted GC-MS(-)-3-Isothujone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e5a1ab6ee8fcd2e7222d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-7900000000-e4ab468ffb3afaf161292016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pe9-9000000000-960a6c7d4901afec92332016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-07a82b9f8d15764ed9042016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-65761ceb0d88aa809b6a2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-4023ebf09d9995d371112016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-e8b89c21a7958e1852782021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdl-7900000000-5c5ad8968d995b2431ac2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-8900000000-a32be7e7fd99fd0b8b232021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-9300000000-eac02498908e1d67934a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-22a79a891aa2c60d074e2021-09-25View Spectrum
NMRNot Available
ChemSpider ID229574
ChEMBL IDCHEMBL1444078
KEGG Compound IDC09906
Pubchem Compound ID261491
Pubchem Substance IDNot Available
ChEBI ID9577
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36115
CRC / DFC (Dictionary of Food Compounds) IDJXM68-F:JXM66-D
EAFUS IDNot Available
Dr. Duke IDALPHA-THUJONE|(-)-THUJONE|THUJONE
BIGG IDNot Available
KNApSAcK IDC00034795
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1048021
SuperScent IDNot Available
Wikipedia IDThujone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
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-helmintic33281 An agent that kills or expels parasitic worms, treating helminthic infections. Therapeutically, it targets intestinal parasites, reducing infection symptoms. Key medical uses include treating roundworm, hookworm, and tapeworm infections.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 septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
CerebrodepressantAn agent that depresses brain activity, reducing alertness and sedating the central nervous system, used therapeutically to manage insomnia, anxiety, and seizures, and medically to induce anesthesia or coma in critical care situations.DUKE
ConvulsantAn agent that induces convulsions and/or epileptic seizures, acting as a stimulant at low doses. It has no therapeutic applications due to its high risk of causing seizures and excitotoxicity, and is the opposite of an anticonvulsant.DUKE
CounterirritantAn agent that induces mild irritation or inflammation in one area to reduce discomfort and/or inflammation in another, often used to relieve pain, reduce swelling, and promote healing in conditions like arthritis, sprains, and strains.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
EpileptigenicAn agent that induces or exacerbates epileptic seizures, playing a role in neurological disorders. Therapeutically, it is used to model and study epilepsy in research. Medically, understanding epileptigenic agents helps in developing treatments for epilepsy and seizure management.DUKE
HallucinogenicAn agent that alters perception, thought, and mood, causing hallucinations and subjective changes. It has a biological role in serotonin receptor modulation. Therapeutically, it's explored for treating mental health disorders, such as depression and anxiety. Key medical uses include research in psychiatric treatment and potential applications in palliative care.DUKE
Herbicide24527 A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.DUKE
Insecticide24852 An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.DUKE
LarvicideAn insecticide that targets the larval life stage of insects, preventing their development into adults. Its biological role is to control insect populations, and its therapeutic applications include managing mosquito-borne diseases such as malaria and dengue fever, as well as controlling pest infestations in agriculture and public health.DUKE
Neurotoxic50910 A substance that damages or destroys nerve cells, disrupting normal brain function. It has no therapeutic applications, but is used in research to study neurodegenerative diseases. Key medical uses include understanding and developing treatments for conditions like Alzheimer's and Parkinson's diseases, where neurotoxicity plays a role.DUKE
Perfumery48318 The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.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
Respira inhibitor35222 An agent that blocks excessive respiratory drive, reducing breathing rate. Therapeutically, it's used to manage respiratory distress, alleviate symptoms of chronic obstructive pulmonary disease (COPD), and facilitate mechanical ventilation in critically ill patients.DUKE
Toxic52209 A substance that can harm or poison living organisms. Biologically, it can disrupt cellular functions and cause damage. Therapeutically, toxins are used in small, controlled doses for applications such as cancer treatment and immunosuppression. Key medical uses include chemotherapy and immunotherapy, where toxins are used to target and destroy diseased cells.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
cedarleaf
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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.