Record Information |
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Version | 1.0 |
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Created at | 2022-09-11 03:16:58 UTC |
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Updated at | 2022-09-11 03:16:59 UTC |
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NP-MRD ID | NP0309022 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2s,3r,4s,5s,6r)-2-{[(1r,3r,4ar,6r,7s,7as)-3-chloro-6,7-dihydroxy-7-(hydroxymethyl)-hexahydro-1h-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol |
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Description | Kankanoside C belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. (2s,3r,4s,5s,6r)-2-{[(1r,3r,4ar,6r,7s,7as)-3-chloro-6,7-dihydroxy-7-(hydroxymethyl)-hexahydro-1h-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Cistanche tubulosa. It was first documented in 2006 (PMID: 16651763). Based on a literature review a small amount of articles have been published on Kankanoside C (PMID: 24748124) (PMID: 31257323). |
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Structure | OC[C@H]1O[C@@H](O[C@@H]2O[C@H](Cl)C[C@H]3C[C@@H](O)[C@@](O)(CO)[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C15H25ClO10/c16-8-2-5-1-7(19)15(23,4-18)9(5)13(25-8)26-14-12(22)11(21)10(20)6(3-17)24-14/h5-14,17-23H,1-4H2/t5-,6-,7-,8+,9-,10-,11+,12-,13+,14+,15+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C15H25ClO10 |
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Average Mass | 400.8100 Da |
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Monoisotopic Mass | 400.11362 Da |
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IUPAC Name | (2S,3R,4S,5S,6R)-2-{[(1R,3R,4aR,6R,7S,7aS)-3-chloro-6,7-dihydroxy-7-(hydroxymethyl)-octahydrocyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol |
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Traditional Name | (2S,3R,4S,5S,6R)-2-{[(1R,3R,4aR,6R,7S,7aS)-3-chloro-6,7-dihydroxy-7-(hydroxymethyl)-hexahydro-1H-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol |
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CAS Registry Number | Not Available |
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SMILES | OC[C@H]1O[C@@H](O[C@@H]2O[C@H](Cl)C[C@H]3C[C@@H](O)[C@@](O)(CO)[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C15H25ClO10/c16-8-2-5-1-7(19)15(23,4-18)9(5)13(25-8)26-14-12(22)11(21)10(20)6(3-17)24-14/h5-14,17-23H,1-4H2/t5-,6-,7-,8+,9-,10-,11+,12-,13+,14+,15+/m1/s1 |
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InChI Key | PUHFWRUOXJAPDN-AGVMVRSDSA-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 iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Terpene glycosides |
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Direct Parent | Iridoid O-glycosides |
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Alternative Parents | |
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Substituents | - Iridoid o-glycoside
- Hexose monosaccharide
- Glycosyl compound
- Iridoid-skeleton
- O-glycosyl compound
- Bicyclic monoterpenoid
- Monoterpenoid
- Monosaccharide
- Oxane
- Cyclic alcohol
- Tertiary alcohol
- Secondary alcohol
- Polyol
- Acetal
- Organoheterocyclic compound
- Oxacycle
- Organohalogen compound
- Organooxygen compound
- Primary alcohol
- Hydrocarbon derivative
- Organic oxygen compound
- Alkyl halide
- Alkyl chloride
- Alcohol
- Organochloride
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic 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, Ninomiya K, Imamura M, Akaki J, Fujikura S, Pan Y, Yuan D, Yoshikawa M, Jia X, Li Z, Muraoka O: Acylated phenylethanoid glycosides, echinacoside and acteoside from Cistanche tubulosa, improve glucose tolerance in mice. J Nat Med. 2014 Jul;68(3):561-6. doi: 10.1007/s11418-014-0837-9. Epub 2014 Apr 19. [PubMed:24748124 ]
- Morikawa T, Xie H, Pan Y, Ninomiya K, Yuan D, Jia X, Yoshikawa M, Nakamura S, Matsuda H, Muraoka O: A Review of Biologically Active Natural Products from a Desert Plant Cistanche tubulosa. Chem Pharm Bull (Tokyo). 2019;67(7):675-689. doi: 10.1248/cpb.c19-00008. [PubMed:31257323 ]
- Xie H, Morikawa T, Matsuda H, Nakamura S, Muraoka O, Yoshikawa M: Monoterpene constituents from Cistanche tubulosa--chemical structures of kankanosides A-E and kankanol-. Chem Pharm Bull (Tokyo). 2006 May;54(5):669-75. doi: 10.1248/cpb.54.669. [PubMed:16651763 ]
- LOTUS database [Link]
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