Record Information |
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Version | 1.0 |
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Created at | 2020-03-19 00:32:19 UTC |
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Updated at | 2020-12-07 19:07:22 UTC |
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CannabisDB ID | CDB000349 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Viridiflorene |
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Description | Viridiflorene also known as leden, belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Sesquiterpenoids 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 (PMID: 7640522 ). 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. Viridiflorene is a hydrophobic, neutral molecule that is insoluble in water. It exists as a clear, colorless oil. Viridiflorene can be found in a number of plant foods and spices such as allspice, sweet basil, sweet marjoram, eucalyptus, common oregano, sage, thyme and rosemary, which makes viridiflorene a potential biomarker for the consumption of these food products. Viridiflorene is one of more than 140 terpenoids found in cannabis plants (PMID: 6991645 ). |
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Structure | |
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Synonyms | Value | Source |
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Leden | ChEBI | Ledene | ChEBI | (+)-Ledene | PhytoBank | (+)-Viridiflorene | PhytoBank |
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Chemical Formula | C15H24 |
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Average Molecular Weight | 204.35 |
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Monoisotopic Molecular Weight | 204.1878 |
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IUPAC Name | (1aR,7R,7aS,7bR)-1,1,4,7-tetramethyl-1H,1aH,2H,3H,5H,6H,7H,7aH,7bH-cyclopropa[e]azulene |
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Traditional Name | leden |
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CAS Registry Number | 21747-46-6 |
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SMILES | C[C@@H]1CCC2=C(C)CC[C@@H]3[C@H]([C@H]12)C3(C)C |
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InChI Identifier | InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h10,12-14H,5-8H2,1-4H3/t10-,12-,13-,14-/m1/s1 |
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InChI Key | WGTRJVCFDUCKCM-FMKGYKFTSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. |
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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 | 5,10-cycloaromadendrane sesquiterpenoids |
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Alternative Parents | |
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Substituents | - 5,10-cycloaromadendrane 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 | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Biological role: |
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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 | Type | Description | Splash Key | View |
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Predicted GC-MS | Viridiflorene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03g0-2900000000-63472047d599d586b269 | Spectrum | Predicted GC-MS | Viridiflorene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Viridiflorene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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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 | splash10-0a4i-0190000000-e64f631cf60f6a1f7a05 | 2017-10-06 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-0590000000-9f28e598a4bda5410442 | 2017-10-06 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0j70-4900000000-466b15f55197d449e74e | 2017-10-06 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0090000000-6589dee75f8602eecab5 | 2017-10-06 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0190000000-4952e3011b37d390d501 | 2017-10-06 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-009i-1910000000-dc6219dfb1223f764f77 | 2017-10-06 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0090000000-7ccf03fa1149a1e9f55f | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0090000000-7ccf03fa1149a1e9f55f | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-0290000000-aa81f6087aa508ac1dbd | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0090000000-4a9d324bd2752a856f35 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ab9-9710000000-791d4a4cf8c97d62cd5a | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-009y-9400000000-8af31644afd13bb682f0 | 2021-09-25 | 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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External Links |
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HMDB ID | HMDB0061849 |
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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 | C00021220 |
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Chemspider ID | Not Available |
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KEGG Compound ID | C20162 |
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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 | 10910653 |
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PDB ID | Not Available |
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ChEBI ID | 63444 |
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References |
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General References | - 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 ]
- McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
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