| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:30:03 UTC |
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| Updated at | 2020-12-07 19:07:20 UTC |
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| CannabisDB ID | CDB000306 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | α-trans-bergamotene |
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| Description | α-Trans-bergamotene belongs to the class of organic compounds known as bicyclic sesquiterpenoids. These are sesquiterpenoids containing exactly two rings, which are fused together. α-Trans-bergamotene is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpene as it synthesized via multiple 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. There are four known Bergamotene isomers including α-cis-, α-trans-, β-cis- and β-trans-bergamotene. α-trans-bergamotene is a neutral, hydrophobic molecule that is insoluble in water. It exists as a clear, greenish oil that has a woody or warm tea-like odor. It is found in the fruits and essential oils of anise, basil, cumin, carrot, bergamot, lime, lemon, cottonseed, nutmeg, black pepper and kumquat. α-trans-bergamotene is also found in the essential oils of plants such as tobacco (PMID:28434859 ) and cannabis (PMID:6991645 ). It is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). 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 insect herbivores, using these sesquiterpenes as a defense mechanism (PMID: 16418295 ). More specifically, the tobacco plant emits α-trans-bergamotene from its flowers at night to attract the tobacco hawk moth (Manduca sexta) as a pollinator; however, during the day the leaves produce α-trans-bergamotene to lure predatory insects to feed on any larvae and eggs that the pollinator may have produced (PMID: 28434859 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| (-)-trans-alpha-Bergamotene | ChEBI | | (-)-trans-a-Bergamotene | Generator | | (-)-trans-Α-bergamotene | Generator | | (-)-exo-a-Bergamotene | Generator | | (-)-exo-Α-bergamotene | Generator | | alpha-Bergamotene | MeSH | | cis-alpha-Bergamotene | MeSH |
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| Chemical Formula | C15H24 |
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| Average Molecular Weight | 204.36 |
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| Monoisotopic Molecular Weight | 204.1878 |
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| IUPAC Name | (1S,5S,6R)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene |
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| Traditional Name | (-)-trans-α-bergamotene |
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| CAS Registry Number | 13474-59-4 |
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| SMILES | CC(C)=CCC[C@]1(C)[C@@H]2C[C@H]1C(C)=CC2 |
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| 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+/m0/s1 |
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| InChI Key | YMBFCQPIMVLNIU-SOUVJXGZSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Monoterpenoids |
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| Direct Parent | Bicyclic monoterpenoids |
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| Alternative Parents | |
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| Substituents | - Pinane monoterpenoid
- Bicyclic monoterpenoid
- Branched unsaturated hydrocarbon
- Polycyclic hydrocarbon
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Role | Industrial application: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | logP | Not Available | Not Available |
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| Predicted Properties | [] |
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| Spectra |
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| EI-MS/GC-MS | Not Available |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | Not Available | 2020-06-30 | View Spectrum |
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| NMR | Not Available |
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| Pathways |
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| Pathways | Not Available |
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| Protein Targets |
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| Enzymes | Not Available |
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| Transporters | Not Available |
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| Metal Bindings | Not Available |
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| Receptors | Not Available |
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| Transcriptional Factors | Not Available |
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| Concentrations Data |
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| Alien Dawg | Detected and Quantified | 0.28 mg/g dry wt | | details | | Gabriola | Detected and Quantified | 0.32 mg/g dry wt | | details | | Island Honey | Detected and Quantified | 0.14 mg/g dry wt | | details | | Quadra | Detected and Quantified | 0.19 mg/g dry wt | | details | | Sensi Star | Detected and Quantified | 0.16 mg/g dry wt | | details | | Tangerine Dream | Detected and Quantified | 0.29 mg/g dry wt | | details |
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| External Links |
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| HMDB ID | Not Available |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | Not Available |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | Not Available |
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| KEGG Compound ID | Not Available |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Not Available |
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| METLIN ID | Not Available |
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| PubChem Compound | 6429302 |
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| PDB ID | Not Available |
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| ChEBI ID | 62756 |
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| References |
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| General References | - 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 ]
- 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 ]
- 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 ]
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