Record Information |
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Version | 1.0 |
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Created at | 2020-03-19 00:38:33 UTC |
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Updated at | 2020-11-18 16:35:11 UTC |
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CannabisDB ID | CDB000468 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | alpha-Ylangene |
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Description | Alpha-Ylangene also known as Ylangene, belongs to the class of organic compounds known as sesquiterpenoids. 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. Alpha-Ylangene is a pale-yellow clear liquid. Alpha-Ylangene is a naturally occurring sesquiterpene found in the leaves of cashew tree (DOI:10.12691/wjac-3-1-2), in grapes (PMID: 17580875 ), and in Cannabis sativa (PMID: 30596146 ). |
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Structure | |
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Synonyms | Not Available |
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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,2R,6R,7R,8S)-1,3-dimethyl-8-(propan-2-yl)tricyclo[4.4.0.0^{2,7}]dec-3-ene |
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Traditional Name | (1S,2R,6R,7R,8S)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0^{2,7}]dec-3-ene |
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CAS Registry Number | 14912-44-8 |
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SMILES | CC(C)[C@@H]1CC[C@@]2(C)[C@@H]3CC=C(C)[C@H]2[C@H]13 |
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InChI Identifier | InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3/t11-,12+,13+,14-,15-/m0/s1 |
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InChI Key | VLXDPFLIRFYIME-QRTUWBSPSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
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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 | Sesquiterpenoids |
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Direct Parent | Sesquiterpenoids |
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Alternative Parents | |
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Substituents | - Copaane sesquiterpenoid
- Sesquiterpenoid
- 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 | Not Available |
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Ontology |
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Not Available | 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 | 0.07 mg/g dry wt | | details | Gabriola | Detected and Quantified | 0.06 mg/g dry wt | | details | Quadra | Detected and Quantified | 0.06 mg/g dry wt | | details | Tangerine Dream | Detected and Quantified | 0.05 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 | 20055075 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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References |
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General References | - 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 ]
- 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 ]
- Parker M, Pollnitz AP, Cozzolino D, Francis IL, Herderich MJ: Identification and quantification of a marker compound for 'pepper' aroma and flavor in shiraz grape berries by combination of chemometrics and gas chromatography-mass spectrometry. J Agric Food Chem. 2007 Jul 25;55(15):5948-55. doi: 10.1021/jf0705320. Epub 2007 Jun 20. [PubMed:17580875 ]
- Gallily R, Yekhtin Z, Hanus LO: The Anti-Inflammatory Properties of Terpenoids from Cannabis. Cannabis Cannabinoid Res. 2018 Dec 26;3(1):282-290. doi: 10.1089/can.2018.0014. eCollection 2018. [PubMed:30596146 ]
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