Record Information |
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Version | 1.0 |
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Created at | 2020-03-19 00:33:19 UTC |
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Updated at | 2020-12-07 19:07:23 UTC |
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CannabisDB ID | CDB000368 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Quebrachitol |
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Description | Quebrachitol or L-Quebrachitol or QCT, belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Quebrachitol can also be classified as a cyclitol (a cyclic polyol). L-Quebrachitol is an optically active, hydrophilic, neutral molecule that is very water soluble. It exists as a white powder. It was first isolated in 1887 from the bark of Aspidosperma quebracho (a South American rubber tree species), from whence it received its name. Quebrachitol along with sucrose is one of the main sugars in the latex of rubber trees. Quebrachitol is a natural product that is found in a number of plants and plant foods, with the highest concentration being found in sea-buckthorn berries. L-Quebrachitol has also been detected, but not quantified in litchi, mugworts and in Cannabis sativa (PMID: 6991645 ). It shows a sweetening property half of that of sucrose but induces colic or diarrhea at concentration used to render the food palatable. Quebrachito has been shown to have gastroprotective effects against acute gastric lesions caused by NSAIDs (PMID: 28132388 ). It also acts as a platelet activating factor (PAF) inhibitor and binds to the platelet activating factor receptor (PAFR) at micromolar concentrations (PMID: 21060292 ). Quebrachito also appears to bind to a number of other proteins or protein targets including the IP3 receptor, β-glucosidase, PAFR, COX2, nitric oxide synthase, and K+ATP channels (PMID: 28132388 ). |
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Structure | |
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Synonyms | Not Available |
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Chemical Formula | C7H14O6 |
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Average Molecular Weight | 194.18 |
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Monoisotopic Molecular Weight | 194.079 |
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IUPAC Name | (1S,2R,3S,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol |
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Traditional Name | (1S,2R,3S,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol |
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CAS Registry Number | 642-38-6 |
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SMILES | CO[C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3+,4-,5-,6-,7-/m0/s1 |
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InChI Key | DSCFFEYYQKSRSV-OUIVRQFQSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Alcohols and polyols |
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Direct Parent | Cyclohexanols |
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Alternative Parents | |
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Substituents | - Cyclohexanol
- Cyclitol or derivatives
- Cyclic alcohol
- Polyol
- Ether
- Dialkyl ether
- Hydrocarbon derivative
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | Not Available |
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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 | 190 to 198 °C | Wikipedia | 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 | |
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Transporters | |
Nitric oxide synthase, inducible | NOS2 | 17q11.2-q12 | P35228 | details | ATP-sensitive inward rectifier potassium channel 1 | KCNJ1 | 11q24 | P48048 | details | Inositol 1,4,5-trisphosphate receptor type 1 | ITPR1 | 3p26.1 | Q14643 | details | Inositol 1,4,5-trisphosphate receptor type 2 | ITPR2 | 12p11 | Q14571 | details | Inositol 1,4,5-trisphosphate receptor type 3 | ITPR3 | 6p21 | Q14573 | details |
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Metal Bindings | |
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Receptors | |
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Transcriptional Factors | |
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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 | - 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 ]
- Wang D, Zhang S, Chang Z, Kong DX, Zuo Z: Quebrachitol: Global Status and Basic Research. Nat Prod Bioprospect. 2017 Feb;7(1):113-122. doi: 10.1007/s13659-017-0120-3. Epub 2017 Jan 28. [PubMed:28132388 ]
- Moharam BA, Jantan I, Jalil J, Shaari K: Inhibitory effects of phylligenin and quebrachitol isolated from Mitrephora vulpina on platelet activating factor receptor binding and platelet aggregation. Molecules. 2010 Nov 3;15(11):7840-8. doi: 10.3390/molecules15117840. [PubMed:21060292 ]
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