Record Information |
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Version | 1.0 |
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Created at | 2022-09-06 03:37:21 UTC |
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Updated at | 2022-09-06 03:37:21 UTC |
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NP-MRD ID | NP0225024 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,2r)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]-3-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}-6-methoxy-1,2-dihydronaphthalene-2-carboximidic acid |
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Description | (?)-Cannabisin D belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. (1r,2r)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]-3-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}-6-methoxy-1,2-dihydronaphthalene-2-carboximidic acid is found in Mesembryanthemum cordifolium and Xylopia aethiopica. It was first documented in 2013 (PMID: 24354193). Based on a literature review a small amount of articles have been published on (?)-Cannabisin D (PMID: 29751713) (PMID: 33076708) (PMID: 25068200). |
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Structure | COC1=CC(=CC=C1O)[C@H]1[C@@H](C(O)=NCCC2=CC=C(O)C=C2)C(=CC2=CC(OC)=C(O)C=C12)C(=O)NCCC1=CC=C(O)C=C1 InChI=1S/C36H36N2O8/c1-45-31-18-23(7-12-29(31)41)33-27-20-30(42)32(46-2)19-24(27)17-28(35(43)37-15-13-21-3-8-25(39)9-4-21)34(33)36(44)38-16-14-22-5-10-26(40)11-6-22/h3-12,17-20,33-34,39-42H,13-16H2,1-2H3,(H,37,43)(H,38,44)/t33-,34+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C36H36N2O8 |
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Average Mass | 624.6900 Da |
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Monoisotopic Mass | 624.24717 Da |
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IUPAC Name | (1R,2R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-3-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}-6-methoxy-1,2-dihydronaphthalene-2-carboximidic acid |
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Traditional Name | (1R,2R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-3-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}-6-methoxy-1,2-dihydronaphthalene-2-carboximidic acid |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC(=CC=C1O)[C@H]1[C@@H](C(O)=NCCC2=CC=C(O)C=C2)C(=CC2=CC(OC)=C(O)C=C12)C(=O)NCCC1=CC=C(O)C=C1 |
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InChI Identifier | InChI=1S/C36H36N2O8/c1-45-31-18-23(7-12-29(31)41)33-27-20-30(42)32(46-2)19-24(27)17-28(35(43)37-15-13-21-3-8-25(39)9-4-21)34(33)36(44)38-16-14-22-5-10-26(40)11-6-22/h3-12,17-20,33-34,39-42H,13-16H2,1-2H3,(H,37,43)(H,38,44)/t33-,34+/m1/s1 |
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InChI Key | XYTYRVFKBJENPE-NOCHOARKSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. |
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Kingdom | Organic compounds |
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Super Class | Lignans, neolignans and related compounds |
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Class | Aryltetralin lignans |
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Sub Class | Not Available |
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Direct Parent | Aryltetralin lignans |
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Alternative Parents | |
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Substituents | - 1-aryltetralin lignan
- 2-naphthalenecarboxylic acid or derivatives
- Methoxyphenol
- Naphthalene
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Carboxamide group
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Ether
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic homopolycyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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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 | - Yang BY, Yang CL, Liu Y, Kuang HX: [Chemical constituents from roots of Datura metel]. Zhongguo Zhong Yao Za Zhi. 2018 Apr;43(8):1654-1661. doi: 10.19540/j.cnki.cjcmm.20180115.008. [PubMed:29751713 ]
- Zhang D, Li C, Zhang L, Li B, Wang Y, Wang R, Chen Z, Xu L, Liu T: Cannabisin D from Sinomenium Acutum Inhibits Proliferation and Migration of Glioblastoma Cells through MAPKs Signaling. Nutr Cancer. 2021;73(11-12):2491-2501. doi: 10.1080/01635581.2020.1836240. Epub 2020 Oct 19. [PubMed:33076708 ]
- Sun J, Gu YF, Su XQ, Li MM, Huo HX, Zhang J, Zeng KW, Zhang Q, Zhao YF, Li J, Tu PF: Anti-inflammatory lignanamides from the roots of Solanum melongena L. Fitoterapia. 2014 Oct;98:110-6. doi: 10.1016/j.fitote.2014.07.012. Epub 2014 Jul 25. [PubMed:25068200 ]
- Wang TS, Luo YP, Wang J, He MX, Zhong MG, Li Y, Song XP: (+)-rumphiin and polyalthurea, new compounds from the stems of Polyalthia rumphii. Nat Prod Commun. 2013 Oct;8(10):1427-9. [PubMed:24354193 ]
- LOTUS database [Link]
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