| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:56:19 UTC |
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| Updated at | 2020-12-07 19:07:45 UTC |
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| CannabisDB ID | CDB000774 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Cannabisin O |
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| Description | Cannabisin O is a lignanamide. It belongs to the class of organic compounds known as lignans, neolignans and related compounds and is the first reported case of trimeric feruloyltyramine identified in cannabis seed extracts. Lignanamides 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 O has been isolated from the 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, anti-oxidant 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 | | Value | Source |
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| (2S,3S)-5-[(1Z)-2-{4-[(1Z)-2-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]-C-hydroxycarbonimidoyl}eth-1-en-1-yl]-2-methoxyphenoxy}-2-{[2-(4-hydroxyphenyl)ethyl]-C-hydroxycarbonimidoyl}eth-1-en-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboximidate | Generator |
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| Chemical Formula | C54H53N3O13 |
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| Average Molecular Weight | 952.03 |
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| Monoisotopic Molecular Weight | 951.3578 |
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| IUPAC Name | (2S,3S)-5-[(1Z)-2-{4-[(1Z)-2-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}eth-1-en-1-yl]-2-methoxyphenoxy}-2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}eth-1-en-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxamide |
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| Traditional Name | (2S,3S)-5-[(1Z)-2-{4-[(1Z)-2-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}eth-1-en-1-yl]-2-methoxyphenoxy}-2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}eth-1-en-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxamide |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=C2O[C@@H]([C@@H](C(=O)NCCC3=CC=C(O)C=C3)C2=CC(\C=C(/OC2=C(OC)C=C(\C=C(/O)C(=O)NCCC3=CC=C(O)C=C3)C=C2)C(=O)NCCC2=CC=C(O)C=C2)=C1)C1=CC=C(O)C(OC)=C1 |
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| InChI Identifier | InChI=1S/C54H53N3O13/c1-66-45-31-37(11-18-42(45)61)50-49(54(65)57-25-22-34-8-16-40(60)17-9-34)41-26-36(29-47(68-3)51(41)70-50)30-48(53(64)56-24-21-33-6-14-39(59)15-7-33)69-44-19-10-35(28-46(44)67-2)27-43(62)52(63)55-23-20-32-4-12-38(58)13-5-32/h4-19,26-31,49-50,58-62H,20-25H2,1-3H3,(H,55,63)(H,56,64)(H,57,65)/b43-27-,48-30-/t49-,50+/m0/s1 |
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| InChI Key | CSQQEMKVBJNOGU-RXPWIXMXSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | 2-arylbenzofuran flavonoids |
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| Sub Class | Not Available |
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| Direct Parent | 2-arylbenzofuran flavonoids |
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| Alternative Parents | |
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| Substituents | - 2-arylbenzofuran flavonoid
- Neolignan skeleton
- Cinnamic acid or derivatives
- Cinnamic acid amide
- Methoxyphenol
- Coumaran
- Benzofuran
- Phenoxy compound
- Methoxybenzene
- Phenol ether
- Anisole
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Alkyl aryl ether
- Benzenoid
- Monocyclic benzene moiety
- Secondary carboxylic acid amide
- Carboxamide group
- Oxacycle
- Organoheterocyclic compound
- Ether
- Enol
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- 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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| 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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