Showing Compound Card for alpha-cis-Bergamotene (CDB000470)

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Record Information
Version1.0
Created at2020-03-19 00:38:40 UTC
Updated at2020-12-07 19:07:27 UTC
CannabisDB IDCDB000470
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-cis-Bergamotene
Descriptionα-cis-bergamotene belongs to the class of organic compounds known as bicyclic sesquiterpenoids. These are sesquiterpenoids containing exactly two rings, which are fused together. It is a naturally occurring sesquiterpene found in the essential oils of plants such as tobacco (PMID:28434859 ) and cannabis (PMID:6991645 ). It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpene as it is synthesized via 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-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. There are four known Bergamotene isomers including α-cis-, α-trans-, β-cis- and β-trans-bergamotene. α-cis-Bergamotene is found in the oils of carrot, bergamot, lime, citron, cottonseed, and kumquat. Isomers of bergamotene have a function as pheromones for some insect species. Evidence suggests that plants under attack by herbivore insects are able to release specific amounts of bergamotene to attract natural enemies of the herbivores, using these sesquiterpenes as a defense mechanism (PMID: 16418295 ). α-Bergamotene has also been detected in the volatile fraction of Cannabis sativa samples (PMID: 26657499 ). It is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(e)-a-BergamoteneGenerator
(e)-Α-bergamoteneGenerator
Chemical FormulaC15H24
Average Molecular Weight204.35
Monoisotopic Molecular Weight204.1878
IUPAC Name(1R,5R,6S)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene
Traditional Name(1R,5R,6S)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene
CAS Registry NumberNot Available
SMILES
CC(C)=CCC[C@@]1(C)[C@H]2C[C@@H]1C(C)=CC2
InChI Identifier
InChI=1S/C15H24/c1-11(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6-7,13-14H,5,8-10H2,1-4H3/t13-,14-,15+/m1/s1
InChI KeyYMBFCQPIMVLNIU-KFWWJZLASA-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
  • Pinane monoterpenoid
  • Bicyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.91ALOGPS
logP4.46ChemAxon
logS-4.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.52 m³·mol⁻¹ChemAxon
Polarizability26.58 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1390000000-d6a0ba11c5a26587cd862016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-4940000000-9dc882467486d9fdf0612016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-5900000000-ea9024d4d9b8c46f77562016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-1d073790940a713722d22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-de5ae459f3052d9744b72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fy9-3910000000-729cba2ca70dcf19f20f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-0790000000-5f2697dd150bf0825ae52021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-060r-2920000000-b37f23a73e76ccb776332021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3900000000-bdedd611b0ff9d6258632021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-069r-9000000000-b2a695a52a29c98c42602021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0302249
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003887
KNApSAcK IDNot Available
Chemspider ID10250932
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13889654
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Zhou W, Kugler A, McGale E, Haverkamp A, Knaden M, Guo H, Beran F, Yon F, Li R, Lackus N, Kollner TG, Bing J, Schuman MC, Hansson BS, Kessler D, Baldwin IT, Xu S: Tissue-Specific Emission of (E)-alpha-Bergamotene Helps Resolve the Dilemma When Pollinators Are Also Herbivores. Curr Biol. 2017 May 8;27(9):1336-1341. doi: 10.1016/j.cub.2017.03.017. Epub 2017 Apr 20. [PubMed:28434859 ]
  2. 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 ]
  3. Schnee C, Kollner TG, Held M, Turlings TC, Gershenzon J, Degenhardt J: The products of a single maize sesquiterpene synthase form a volatile defense signal that attracts natural enemies of maize herbivores. Proc Natl Acad Sci U S A. 2006 Jan 24;103(4):1129-34. doi: 10.1073/pnas.0508027103. Epub 2006 Jan 17. [PubMed:16418295 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]