| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:36:08 UTC |
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| Updated at | 2020-11-18 16:35:10 UTC |
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| CannabisDB ID | CDB000026 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Cannabicyclol |
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| Description | Cannabicyclol (CBL) belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that include a 1-benzopyran moiety, a bicyclic compound made up of a benzene ring fused to a pyran ring, so that the oxygen atom is at the 1-position. Cannabicyclol is a neutral compound . It is a non-psychoactive oxidation product of cannabichromene, produced mainly during long term storage of cannabis (PMID: 31202146 ). CBL has been proposed as a good candidate for a chemical marker to identify cannabis samples from different storage conditions (PMID: 31202146 ). |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C21H30O2 |
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| Average Molecular Weight | 314.47 |
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| Monoisotopic Molecular Weight | 314.2246 |
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| IUPAC Name | (1R,9R,12S,14R)-9,13,13-trimethyl-5-pentyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2,4,6-trien-3-ol |
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| Traditional Name | (1R,9R,12S,14R)-9,13,13-trimethyl-5-pentyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2,4,6-trien-3-ol |
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| CAS Registry Number | 21366-63-2 |
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| SMILES | CCCCCC1=CC(O)=C2[C@@H]3[C@H]4[C@H](CC[C@@]4(C)OC2=C1)C3(C)C |
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| InChI Identifier | InChI=1S/C21H30O2/c1-5-6-7-8-13-11-15(22)17-16(12-13)23-21(4)10-9-14-18(21)19(17)20(14,2)3/h11-12,14,18-19,22H,5-10H2,1-4H3/t14-,18+,19+,21+/m0/s1 |
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| InChI Key | IGHTZQUIFGUJTG-QSMXQIJUSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Benzopyrans |
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| Sub Class | 1-benzopyrans |
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| Direct Parent | 1-benzopyrans |
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| Alternative Parents | |
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| Substituents | - 1-benzopyran
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Alkyl aryl ether
- Benzenoid
- Oxacycle
- Ether
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic 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 | | Type | Description | Splash Key | View |
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| Predicted GC-MS | Cannabicyclol, 1 TMS, 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 | 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 | 0.275 mg/g dry wt | | details | | Gabriola | Detected and Quantified | 0.208 mg/g dry wt | | details | | Island Honey | Detected and Quantified | 0.117 mg/g dry wt | | details | | Quadra | Detected and Quantified | 0.303 mg/g dry wt | | details | | Sensi Star | Detected and Quantified | 0.358 mg/g dry wt | | details | | Tangerine Dream | Detected and Quantified | 0.218 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 | 59444380 |
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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 | - 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 ]
- Grafstrom K, Andersson K, Pettersson N, Dalgaard J, Dunne SJ: Effects of long term storage on secondary metabolite profiles of cannabis resin. Forensic Sci Int. 2019 Aug;301:331-340. doi: 10.1016/j.forsciint.2019.05.035. Epub 2019 May 25. [PubMed:31202146 ]
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