| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:56:04 UTC |
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| Updated at | 2020-12-07 19:07:45 UTC |
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| CannabisDB ID | CDB000770 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Cannabisin E |
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| Description | Cannabisin E is a lignanamide that belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9√Ǭ¥ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. Cannabisin E has been isolated from the roots, fruits and seeds of cannabis plants (PMID: 28799497 ). It is a neutral, hydrophobic molecule that is largely insoluble in water (PMID: 26585089 ). Cannabisins and other lignanamides exhibit interesting and diverse biological activities, including feeding deterrent activity and insecticidal effects (that protect the plant) as well as anti-inflammatory, antioxidant and anti-acetylcholinesterase activity, which may have beneficial health effects (PMID: 26585089 ). Cannibasins have been found to suppress the production and lower the levels of mRNA of pro-inflammatory mediators such as interleukin 6 (IL-6) and tumor necrosis factor α (TNF-α) in a concentration-dependent manner in LPS-stimulated BV2 microglia cells (PMID: 30691004 ). |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C36H38N2O9 |
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| Average Molecular Weight | 642.71 |
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| Monoisotopic Molecular Weight | 642.2577 |
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| IUPAC Name | (E,2E)-3-{4-[(1R,2R)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-{[2-(4-hydroxyphenyl)ethyl]-C-hydroxycarbonimidoyl}ethoxy]-3-methoxyphenyl}-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid |
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| Traditional Name | (E,2E)-3-{4-[(1R,2R)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-{[2-(4-hydroxyphenyl)ethyl]-C-hydroxycarbonimidoyl}ethoxy]-3-methoxyphenyl}-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=C(O)C=CC(=C1)[C@@H](O)[C@@H](OC1=C(OC)C=C(\C=C\C(\O)=N/CCC2=CC=C(O)C=C2)C=C1)C(O)=NCCC1=CC=C(O)C=C1 |
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| InChI Identifier | InChI=1S/C36H38N2O9/c1-45-31-22-26(9-14-29(31)41)34(43)35(36(44)38-20-18-24-5-12-28(40)13-6-24)47-30-15-7-25(21-32(30)46-2)8-16-33(42)37-19-17-23-3-10-27(39)11-4-23/h3-16,21-22,34-35,39-41,43H,17-20H2,1-2H3,(H,37,42)(H,38,44)/b16-8+/t34-,35-/m1/s1 |
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| InChI Key | RMSITXIMTOOGNZ-IYFCKDFNSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. |
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| Kingdom | Organic compounds |
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| Super Class | Lignans, neolignans and related compounds |
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| Class | Not Available |
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| Sub Class | Not Available |
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| Direct Parent | Lignans, neolignans and related compounds |
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| Alternative Parents | |
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| Substituents | - Neolignan skeleton
- Cinnamic acid amide
- Cinnamic acid or derivatives
- Methoxyphenol
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- Styrene
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Fatty amide
- Fatty acyl
- Benzenoid
- Monosaccharide
- Carboxamide group
- Secondary carboxylic acid amide
- Secondary alcohol
- Ether
- Carboxylic acid derivative
- Alcohol
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organonitrogen compound
- Organooxygen compound
- Aromatic alcohol
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Role | Industrial application: 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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| General References | - Pollastro F, Minassi A, Fresu LG: Cannabis Phenolics and their Bioactivities. Curr Med Chem. 2018;25(10):1160-1185. doi: 10.2174/0929867324666170810164636. [PubMed:28799497 ]
- Yan X, Tang J, dos Santos Passos C, Nurisso A, Simoes-Pires CA, Ji M, Lou H, Fan P: Characterization of Lignanamides from Hemp (Cannabis sativa L.) Seed and Their Antioxidant and Acetylcholinesterase Inhibitory Activities. J Agric Food Chem. 2015 Dec 16;63(49):10611-9. doi: 10.1021/acs.jafc.5b05282. Epub 2015 Dec 2. [PubMed:26585089 ]
- Wang S, Luo Q, Fan P: Cannabisin F from Hemp (Cannabis sativa) Seed Suppresses Lipopolysaccharide-Induced Inflammatory Responses in BV2 Microglia as SIRT1 Modulator. Int J Mol Sci. 2019 Jan 25;20(3). pii: ijms20030507. doi: 10.3390/ijms20030507. [PubMed:30691004 ]
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