Showing Compound Card for trans-gamma-Bisabolene (CDB000449)

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Record Information
Version1.0
Created at2020-03-19 00:37:32 UTC
Updated at2020-11-18 16:35:10 UTC
CannabisDB IDCDB000449
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nametrans-gamma-Bisabolene
DescriptionTrans-gamma-Bisabolene or (E)-gamma-bisabolene is biochemically a sesquiterpenoid. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Beta-Bisabolene is considered to be an isoprenoid lipid molecule, as such, Beta-Bisabolene is a very hydrophobic molecule, practically insoluble in water and relatively neutral. Bisabolene has three isomers (α-, β-, and γ-bisabolene) which differ by the positions of the double bonds. Bisabolenes are naturally occurring sesquiterpenoid found in the essential oils of bisabol, and of a wide variety of other plants including cubeb, lemon, oregano and found in trace amounts in cannabis plants (PMID: 6991645 ). Trans-gamma-Bisabolene is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). Bisabolenes are also produced in different insects such as stink bugs, fruit flies and by several fungi (PMID: 11673844 ; PMID: 25957494 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(Z)-g-BisaboleneGenerator
(Z)-Γ-bisaboleneGenerator
gamma-BisaboleneMeSH
(4Z)-4-(1,5-Dimethyl-4-hexen-1-ylidene)-1-methylcyclohexenePhytoBank
(Z)-gamma-BisabolenePhytoBank
cis-gamma-BisabolenePhytoBank
cis-γ-BisabolenePhytoBank
4-(1,5-Dimethyl-4-hexen-1-ylidene)-1-methylcyclohexenePhytoBank
γ-BisabolenePhytoBank
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(4Z)-1-methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene
Traditional Name(Z)-gamma-bisabolene
CAS Registry Number11003-31-9
SMILES
CC(C)=CCC\C(C)=C1\CCC(C)=CC1
InChI Identifier
InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8H,5,7,9-11H2,1-4H3/b15-14+
InChI KeyXBGUIVFBMBVUEG-CCEZHUSRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Bisabolane sesquiterpenoid
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Cycloalkene
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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
logP5.88ALOGPS
logP4.78ChemAxon
logS-3.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.09 m³·mol⁻¹ChemAxon
Polarizability26.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)Not Available2022-08-06View Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00035441
Chemspider ID2298446
KEGG Compound IDC16814
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBisabolene
METLIN IDNot Available
PubChem Compound3033866
PDB IDNot Available
ChEBI ID49238
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 ]
  2. Lu F, Teal PE: Sex pheromone components in oral secretions and crop of male Caribbean fruit flies, Anastrepha suspensa (Loew). Arch Insect Biochem Physiol. 2001 Nov;48(3):144-54. doi: 10.1002/arch.1067. [PubMed:11673844 ]
  3. Spakowicz DJ, Strobel SA: Biosynthesis of hydrocarbons and volatile organic compounds by fungi: bioengineering potential. Appl Microbiol Biotechnol. 2015 Jun;99(12):4943-51. doi: 10.1007/s00253-015-6641-y. Epub 2015 May 10. [PubMed:25957494 ]