Record Information |
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Version | 1.0 |
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Created at | 2021-11-12 23:56:49 UTC |
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Updated at | 2021-11-26 17:46:35 UTC |
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NP-MRD ID | NP0044203 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Plantamajoside |
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Description | (2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Plantamajoside is found in Digitalis lanata, Digitalis purpurea , Lagotis stolonifera, Picrorhiza scrophulariiflora , Plantago arborescens, Plantago asiatica , Plantago lagopus, Plantago lanceolata, Plantago major , Plantago media , Plantago ovata , Plantago webbii, Rehmannia glutinosa , Veronica beccabunga , Veronica fuhsii, Wulfenia baldaccii Degen and Wulfenia carinthiaca. It was first documented in 2020 (PMID: 34756847). Based on a literature review a significant number of articles have been published on (2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate (PMID: 34758548) (PMID: 34758547) (PMID: 34758546) (PMID: 34758545). |
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Structure | OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](OCCC3=CC=C(O)C(O)=C3)O[C@H](CO)[C@H]2OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C29H36O16/c30-11-19-22(37)23(38)24(39)29(42-19)45-27-25(40)28(41-8-7-14-2-5-16(33)18(35)10-14)43-20(12-31)26(27)44-21(36)6-3-13-1-4-15(32)17(34)9-13/h1-6,9-10,19-20,22-35,37-40H,7-8,11-12H2/b6-3+/t19-,20-,22-,23+,24-,25-,26-,27-,28-,29+/m1/s1 |
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Synonyms | Value | Source |
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(2R,3R,4R,5R,6R)-6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoic acid | Generator |
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Chemical Formula | C29H36O16 |
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Average Mass | 640.5910 Da |
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Monoisotopic Mass | 640.20034 Da |
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IUPAC Name | (2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate |
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Traditional Name | plantamajoside |
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CAS Registry Number | Not Available |
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SMILES | OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](OCCC3=CC=C(O)C(O)=C3)O[C@H](CO)[C@H]2OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C29H36O16/c30-11-19-22(37)23(38)24(39)29(42-19)45-27-25(40)28(41-8-7-14-2-5-16(33)18(35)10-14)43-20(12-31)26(27)44-21(36)6-3-13-1-4-15(32)17(34)9-13/h1-6,9-10,19-20,22-35,37-40H,7-8,11-12H2/b6-3+/t19-,20-,22-,23+,24-,25-,26-,27-,28-,29+/m1/s1 |
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InChI Key | KFEFLPDKISUVNR-QJEHNBJNSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | 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 coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Cinnamic acids and derivatives |
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Sub Class | Hydroxycinnamic acids and derivatives |
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Direct Parent | Coumaric acids and derivatives |
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Alternative Parents | |
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Substituents | - Coumaric acid or derivatives
- Cinnamic acid ester
- Disaccharide
- Glycosyl compound
- O-glycosyl compound
- Tyrosol derivative
- Catechol
- Styrene
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Fatty acid ester
- Phenol
- Monocyclic benzene moiety
- Fatty acyl
- Oxane
- Benzenoid
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Secondary alcohol
- Carboxylic acid ester
- Polyol
- Acetal
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Oxacycle
- Carboxylic acid derivative
- Organooxygen compound
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Primary alcohol
- Alcohol
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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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 | - McDonagh MS, Wagner J, Ahmed AY, Morasco B, Kansagara D, Chou R: Living Systematic Review on Cannabis and Other Plant-Based Treatments for Chronic Pain - Quarterly Progress Report/Addendum: September 2021. 2020 Dec. [PubMed:34756847 ]
- Zhang WB, Yang QB, Wu SF, Lu SH, Cheng M, Sheng Y, Zhang QC, Yang LF, Yu L, Yan SX: [Application of diffusion-weighted magnetic resonance imaging in evaluating the efficacy of radiotherapy and chemotherapy for esophageal cancer]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3427-3430. doi: 10.3760/cma.j.cn112137-20210709-01544. [PubMed:34758548 ]
- Sun Y, Wang DM, Yu H, Liu C, Ji TY, Wang S, Wu Y, Liu XY, Jiang YW, Cai LX, Liu QZ: [The screening of potential biological markers of seizure onset zone in focal cortical dysplasia based on bioinformatics analysis]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3422-3426. doi: 10.3760/cma.j.cn112137-20210331-00779. [PubMed:34758547 ]
- Dong HH, Cai YS, Liang XN, Miao JB, Chen QS, Gao YD, Li H: [Analysis of incidence and risk factors for postoperative venous thromboembolism in patients with stage a non-small-cell lung cancer]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3417-3421. doi: 10.3760/cma.j.cn112137-20210418-00929. [PubMed:34758546 ]
- Chai YR, Gao JB, Lyu PJ, Liang P, Xing JJ, Liu J: [Comparative study of CT relative enhancement value and subjective visual evaluation for intestinal ischemia in patients with closed loop obstruction]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3411-3416. doi: 10.3760/cma.j.cn112137-20210328-00756. [PubMed:34758545 ]
- Lian-Chun Zou et al. (2008). New secoiridoid Glycosides from the Roots of Picrorhiza Scrophulariiflora. Molecules 2008, 13(9), 2049-2057; DOI: 10.3390/molecules13092049. Molecules.
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