Showing Compound Card for Cis-gamma-Bisabolene (CDB000465)

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Record Information
Version1.0
Created at2020-03-19 00:38:21 UTC
Updated at2020-12-07 19:07:26 UTC
CannabisDB IDCDB000465
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCis-gamma-Bisabolene
DescriptionCis-gamma-Bisabolene is an isomer of Bisabolene. Three isomers are known, α-, β-, and γ-bisabolene, which differ by the positions of the double bonds. Bisabolenes are a group of closely related natural chemical compounds which are classified as sesquiterpenes. belongs to the class of organic compounds known as sesquiterpenoids. These 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-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ) 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. Bisabolenes are present in the essential oils of German chamomile (PMID: 22096322 ), and of a wide variety of other plants including cubeb, lemon, oregano, and Cannabis sativa (PMID: 6991645 , 26657499 ). Cis-gamma-Bisabolene is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). Various derivates of bisabolol also function as pheromones in different insects (PMID: 31659569 ). Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear (doi:10.3390/f11030290).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(Z)-laquo gammaraquo -BisaboleneHMDB
(e)-g-BisaboleneGenerator
(e)-Γ-bisaboleneGenerator
Chemical FormulaC15H24
Average Molecular Weight204.35
Monoisotopic Molecular Weight204.1878
IUPAC Name(4E)-1-methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene
Traditional Name(E)-gamma-bisabolene
CAS Registry Number13062-00-5
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-PFONDFGASA-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
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
Polarizability26.87 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCis-gamma-Bisabolene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ku-7900000000-f0996e8952fb933ec1a1Spectrum
Predicted GC-MSCis-gamma-Bisabolene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCis-gamma-Bisabolene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3790000000-d9bfff51a973f095b0f72016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-6910000000-b3ba4af91c15ca820f022016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9400000000-c572c8e71209344306bb2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-b9ec3a3fca68549c9c682016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-c4fd97be688246991a842016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-4900000000-85130b2dad3062d4c6012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a59-9420000000-5092d8f0b03c4273c2ad2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kg-9300000000-f48deeaf43b19cf036f52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-9100000000-6e8c9fc99a0906a174582021-09-24View 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-0190000000-8f291e3c98cfd164ba302021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5900000000-a8d4d6ee48d3fc56bc3f2021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0036154
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015018
KNApSAcK IDC00011631
Chemspider ID4509327
KEGG Compound IDC19748
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5352437
PDB IDNot Available
ChEBI ID49239
References
General References
  1. Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
  2. Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]
  3. Singh O, Khanam Z, Misra N, Srivastava MK: Chamomile (Matricaria chamomilla L.): An overview. Pharmacogn Rev. 2011 Jan;5(9):82-95. doi: 10.4103/0973-7847.79103. [PubMed:22096322 ]
  4. 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 ]
  5. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
  6. Yang CY, Seo MH, Lee SC: Male-Produced Aggregation Pheromone of the Sloe Bug, Dolycoris baccarum L. (Hemiptera: Heteroptera: Pentatomidae). J Chem Ecol. 2019 Oct;45(10):818-822. doi: 10.1007/s10886-019-01110-3. Epub 2019 Oct 28. [PubMed:31659569 ]