Record Information |
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Version | 1.0 |
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Created at | 2021-11-12 23:48:30 UTC |
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Updated at | 2021-11-26 17:45:07 UTC |
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NP-MRD ID | NP0044072 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Kankanoside I |
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Description | (2R,3R,4R,5R,6R)-5-hydroxy-6-(2-phenylethoxy)-2-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. Kankanoside I is found in Cistanche tubulosa. It was first documented in 2010 (PMID: 20159656). Based on a literature review a significant number of articles have been published on (2R,3R,4R,5R,6R)-5-hydroxy-6-(2-phenylethoxy)-2-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate (PMID: 34756847) (PMID: 34758548) (PMID: 34758547) (PMID: 34758546). |
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Structure | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](OCCC3=CC=CC=C3)O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O InChI=1S/C35H46O18/c1-16-24(40)26(42)29(45)35(49-16)53-32-30(46)34(47-12-11-17-5-3-2-4-6-17)51-22(15-48-33-28(44)27(43)25(41)21(14-36)50-33)31(32)52-23(39)10-8-18-7-9-19(37)20(38)13-18/h2-10,13,16,21-22,24-38,40-46H,11-12,14-15H2,1H3/b10-8+/t16-,21+,22+,24-,25+,26+,27-,28+,29+,30+,31+,32+,33+,34+,35-/m0/s1 |
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Synonyms | Value | Source |
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(2R,3R,4R,5R,6R)-5-Hydroxy-6-(2-phenylethoxy)-2-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoic acid | Generator |
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Chemical Formula | C35H46O18 |
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Average Mass | 754.7350 Da |
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Monoisotopic Mass | 754.26841 Da |
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IUPAC Name | (2R,3R,4R,5R,6R)-5-hydroxy-6-(2-phenylethoxy)-2-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate |
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Traditional Name | (2R,3R,4R,5R,6R)-5-hydroxy-6-(2-phenylethoxy)-2-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](OCCC3=CC=CC=C3)O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C35H46O18/c1-16-24(40)26(42)29(45)35(49-16)53-32-30(46)34(47-12-11-17-5-3-2-4-6-17)51-22(15-48-33-28(44)27(43)25(41)21(14-36)50-33)31(32)52-23(39)10-8-18-7-9-19(37)20(38)13-18/h2-10,13,16,21-22,24-38,40-46H,11-12,14-15H2,1H3/b10-8+/t16-,21+,22+,24-,25+,26+,27-,28+,29+,30+,31+,32+,33+,34+,35-/m0/s1 |
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InChI Key | LXLTWMNTGBZOLH-GGPLKTKBSA-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, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol-d4, 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 oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. |
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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 | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Oligosaccharides |
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Alternative Parents | |
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Substituents | - Oligosaccharide
- Cinnamic acid or derivatives
- Coumaric acid or derivatives
- Hydroxycinnamic acid or derivatives
- Cinnamic acid ester
- Glycosyl compound
- O-glycosyl compound
- Catechol
- Styrene
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Fatty acid ester
- Phenol
- Monocyclic benzene moiety
- Fatty acyl
- Benzenoid
- Oxane
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Carboxylic acid ester
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Acetal
- Polyol
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Primary alcohol
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic 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 | - Morikawa T, Pan Y, Ninomiya K, Imura K, Matsuda H, Yoshikawa M, Yuan D, Muraoka O: Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa. Bioorg Med Chem. 2010 Mar 1;18(5):1882-90. doi: 10.1016/j.bmc.2010.01.047. Epub 2010 Jan 25. [PubMed:20159656 ]
- 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 ]
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