Showing Compound Card for alpha-Thujene (CDB000206)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-18 23:28:42 UTC
Updated at2020-11-18 16:34:55 UTC
CannabisDB IDCDB000206
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-Thujene
Description(-)-3-Thujene, also known as alpha-Thujene, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (-)-3-Thujene is possibly neutral. It has a green, herb, and woody taste and contributes pungency to the flavor of some herbs such as summer savory. (-)-3-Thujene is found in highest concentrations in cardamoms, sweet bay, and common sages and in lower concentrations in allspices, dills, and cumins. (-)-3-Thujene has also been detected in caraway, corianders, cornmints, spearmints, and pepper (c. annuum). This could make (-)-3-thujene a potential biomarker for the consumption of these foods. (-)-3-Thujene was isolated from Indian olibanum tree (Boswellia serrata), Eucalyptus species, juniper, and cannabis plants (PMID:6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1R,5S)-5-Isopropyl-2-methylbicyclo[3.1.0]hex-2-eneChEBI
(-)-a-ThujeneGenerator
(-)-Α-thujeneGenerator
(1R,5R)-(-)-3-ThujenePhytoBank
(-)-alpha-ThujenePhytoBank
3-ThujenePhytoBank
2-Methyl-5-(1-methylethyl)bicyclo[3.1.0]hex-2-enePhytoBank
(±)-alpha-ThujenePhytoBank
(±)-α-ThujenePhytoBank
alpha-ThujenePhytoBank
2-Methyl-5-isopropylbicyclo[3.1.0]-2-hexenePhytoBank
OriganenePhytoBank
Chemical FormulaC10H16
Average Molecular Weight136.24
Monoisotopic Molecular Weight136.1252
IUPAC Name(1R)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hex-2-ene
Traditional Name(-)-α-thujene
CAS Registry Number3917-48-4
SMILES
CC(C)[C@@]12C[C@@H]1C(C)=CC2
InChI Identifier
InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h4,7,9H,5-6H2,1-3H3/t9-,10-/m1/s1
InChI KeyKQAZVFVOEIRWHN-NXEZZACHSA-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
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.07ALOGPS
logP2.8ChemAxon
logS-2.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.72 m³·mol⁻¹ChemAxon
Polarizability17.32 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSalpha-Thujene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9200000000-774bc6fbebab26aedc23Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900000000-e173719ed4c85f788fe72017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5900000000-1e5d8a47ad13b92d81fb2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7i-9100000000-6e95b4220eff7761b7de2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-b9baf692878a51dd015b2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-3ce9abf1e237066f26522017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-5900000000-6d7bb48e804a65f8fa432017-06-28View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Sensi Star (Pure Indica)Detected and Quantified0.16 +/- 0.00 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound637518
PDB IDNot Available
ChEBI ID50033
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]