Showing Compound Card for Bisabolene (CDB005829)

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Record Information
Version1.0
Created at2020-04-27 17:00:43 UTC
Updated at2021-01-04 18:49:23 UTC
CannabisDB IDCDB005829
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBisabolene
Description2,7,10-Bisabolatriene, also known as cis-alpha-bisabolene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenes 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. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway 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. 2,7,10-Bisabolatriene is also classified as a bisabolene. Bisabolenes are a group of closely related natural chemical compounds found in the essential oils of bisabol, and of many other plants including cubeb, lemon, and oregano. Three isomers of bisabolene are known, α-, β-and γ-bisabolene, which differ by the positions of the double bonds. Bisabolenes are used as intermediates in the biosynthesis of many other natural chemical compounds, including hernandulcin, a natural sweetener. 2,7,10-Bisabolatriene is a neutral, hydrophobic molecule that is practically insoluble in water. Some bisabolene derivatives also act as pheromones in different insects, such as stink bugs and fruit flies (PMID: 11673844 ). Bisabolenes are also produced by several fungi, though their biological role in that group of organisms remains unclear (PMID: 25957494 ). Bisabolenes are found in cannabis smoke. Cis-alpha-Bisabolene is formed during the combustion of cannabis ( Ref:DOI ). 
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
cis-alpha-BisaboleneChEBI
cis-a-BisaboleneGenerator
cis-Α-bisaboleneGenerator
1,8,12-BisabolatrieneHMDB
4-(1,5-Dimethyl-1,4-hexadien-1-yl)-1-methyl-cyclohexeneHMDB
4-(1,5-Dimethyl-1,4-hexadienyl)-1-methyl-cyclohexeneHMDB
4-(1,5-Dimethyl-1,4-hexadienyl)-1-methylcyclohexene, 9ciHMDB
4-(1,5-Dimethylhexa-1,4-dien-1-yl)-1-methylcyclohexeneHMDB
6-Methyl-2-(4-methylcyclohex-3-enyl)hept-2,5-dieneHMDB
a-Bisabolene?HMDB
a-LimeneHMDB
alpha-BisaboleneHMDB
Bisabola-4,7(11),9-trieneHMDB
FEMA 3331HMDB
(Z)-a-BisaboleneGenerator
(Z)-Α-bisaboleneGenerator
Chemical FormulaC15H24
Average Molecular Weight204.35
Monoisotopic Molecular Weight204.1878
IUPAC Name1-methyl-4-[(2Z)-6-methylhepta-2,5-dien-2-yl]cyclohex-1-ene
Traditional Name(Z)-α-bisabolene
CAS Registry Number17627-44-0
SMILES
CC(C)=CC\C=C(\C)C1CCC(C)=CC1
InChI Identifier
InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6-8,15H,5,9-11H2,1-4H3/b14-7-
InChI KeyYHBUQBJHSRGZNF-AUWJEWJLSA-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
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.95ALOGPS
logP4.82ChemAxon
logS-3.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.36 m³·mol⁻¹ChemAxon
Polarizability26.24 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSBisabolene, non-derivatized, GC-MS Spectrumsplash10-0006-9400000000-576519ffe2ba01b6c4c3Spectrum
GC-MSBisabolene, non-derivatized, GC-MS Spectrumsplash10-0006-9400000000-576519ffe2ba01b6c4c3Spectrum
Predicted GC-MSBisabolene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052r-5900000000-a812889865879cbf4026Spectrum
Predicted GC-MSBisabolene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2690000000-1854756b571fb37095022016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0awa-6910000000-1e87e31d3933669b57092016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9400000000-061d6056005f5a65828f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-81dda3745c41269261fc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-5727e5b0323d38ca0d8e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-4900000000-aaf3a5a5f258fb429ece2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-6132f923f45ce08bf3102021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fr7-5930000000-547fa0da9e0ebceba8e82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053s-9210000000-04f4b8e8c9ac5369e9102021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kg-9200000000-abe260239558b7dcf1502021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9100000000-ee852b066c969b19b1a42021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0035161
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014953
KNApSAcK IDC00052803
Chemspider ID4509521
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5352653
PDB IDNot Available
ChEBI ID49241
References
General References
  1. 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 ]
  2. 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 ]