| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:29:27 UTC |
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| Updated at | 2020-11-18 16:35:01 UTC |
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| CannabisDB ID | CDB000295 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | m-Mentha-1,8(9)-dien-5-ol |
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| Description | m-Mentha-1,8(9)-dien-5-ol or meta-Mentha-1,8(9)-dien-5-ol belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. M-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 3 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. M-mentha-1,8(9)-dien-5-ol is formally classified as an alcohol although it is biochemically a monocyclic monoterpenoid as it is synthesized via isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. M-mentha-1,8(9)-dien-5-ol is one of 140 terpenes that are found in cannabis plants (PMID: 6991645 ) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. M-mentha-1,8(9)-dien-5-ol is a unique terpenoid found only in Cannabis. |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C10H16O |
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| Average Molecular Weight | 152.24 |
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| Monoisotopic Molecular Weight | 152.1201 |
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| IUPAC Name | (1R,5R)-3-methyl-5-(prop-1-en-2-yl)cyclohex-3-en-1-ol |
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| Traditional Name | (1R,5R)-3-methyl-5-(prop-1-en-2-yl)cyclohex-3-en-1-ol |
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| CAS Registry Number | Not Available |
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| SMILES | CC(=C)[C@@H]1C[C@@H](O)CC(C)=C1 |
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| InChI Identifier | InChI=1S/C10H16O/c1-7(2)9-4-8(3)5-10(11)6-9/h4,9-11H,1,5-6H2,2-3H3/t9-,10-/m0/s1 |
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| InChI Key | SFULVKXOLMZBEC-UWVGGRQHSA-N |
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| Chemical Taxonomy |
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| Classification | Not classified |
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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 | m-Mentha-1,8(9)-dien-5-ol, 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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| Not Available |
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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 | Not Available |
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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 | - McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
- 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 ]
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