Record Information |
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Version | 2.0 |
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Created at | 2022-09-12 04:33:18 UTC |
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Updated at | 2022-09-12 04:33:18 UTC |
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NP-MRD ID | NP0324461 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 5-[(1s,4r,5s,8r,9r,11r,12s,13r,14r,16r,18s)-5,11-dihydroxy-13-(hydroxymethyl)-9,16-dimethyl-15,17,20-trioxahexacyclo[14.3.1.1¹⁴,¹⁸.0¹,¹³.0⁴,¹².0⁵,⁹]henicosan-8-yl]pyran-2-one |
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Description | Bryophyllin C belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. 5-[(1s,4r,5s,8r,9r,11r,12s,13r,14r,16r,18s)-5,11-dihydroxy-13-(hydroxymethyl)-9,16-dimethyl-15,17,20-trioxahexacyclo[14.3.1.1¹⁴,¹⁸.0¹,¹³.0⁴,¹².0⁵,⁹]henicosan-8-yl]pyran-2-one is found in Kalanchoe pinnata. Based on a literature review very few articles have been published on Bryophyllin C. |
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Structure | C[C@]12C[C@@H](O)[C@H]3[C@@H](CC[C@@]45C[C@@H]6C[C@@H](O[C@@](C)(O6)O4)[C@]35CO)[C@@]1(O)CC[C@@H]2C1=COC(=O)C=C1 InChI=1S/C26H34O8/c1-22-11-18(28)21-17(26(22,30)8-6-16(22)14-3-4-20(29)31-12-14)5-7-24-10-15-9-19(25(21,24)13-27)33-23(2,32-15)34-24/h3-4,12,15-19,21,27-28,30H,5-11,13H2,1-2H3/t15-,16+,17+,18+,19+,21+,22+,23+,24-,25+,26-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C26H34O8 |
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Average Mass | 474.5500 Da |
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Monoisotopic Mass | 474.22537 Da |
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IUPAC Name | 5-[(1S,4R,5S,8S,9R,11R,12S,13R,14R,16R,18S)-5,11-dihydroxy-13-(hydroxymethyl)-9,16-dimethyl-15,17,20-trioxahexacyclo[14.3.1.1^{14,18}.0^{1,13}.0^{4,12}.0^{5,9}]henicosan-8-yl]-2H-pyran-2-one |
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Traditional Name | 5-[(1S,4R,5S,8S,9R,11R,12S,13R,14R,16R,18S)-5,11-dihydroxy-13-(hydroxymethyl)-9,16-dimethyl-15,17,20-trioxahexacyclo[14.3.1.1^{14,18}.0^{1,13}.0^{4,12}.0^{5,9}]henicosan-8-yl]pyran-2-one |
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CAS Registry Number | Not Available |
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SMILES | C[C@]12C[C@@H](O)[C@H]3[C@@H](CC[C@@]45C[C@@H]6C[C@@H](O[C@@](C)(O6)O4)[C@]35CO)[C@@]1(O)CC[C@@H]2C1=COC(=O)C=C1 |
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InChI Identifier | InChI=1S/C26H34O8/c1-22-11-18(28)21-17(26(22,30)8-6-16(22)14-3-4-20(29)31-12-14)5-7-24-10-15-9-19(25(21,24)13-27)33-23(2,32-15)34-24/h3-4,12,15-19,21,27-28,30H,5-11,13H2,1-2H3/t15-,16+,17+,18+,19+,21+,22+,23+,24-,25+,26-/m0/s1 |
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InChI Key | IROGPDLPDYVVFG-BGJAGFQLSA-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 bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Steroid lactones |
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Direct Parent | Bufanolides and derivatives |
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Alternative Parents | |
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Substituents | - Bufanolide-skeleton
- Carboxylic acid orthoester
- Pyranone
- Ortho ester
- Meta-dioxane
- Pyran
- Heteroaromatic compound
- Cyclic alcohol
- Tertiary alcohol
- Lactone
- Secondary alcohol
- Orthocarboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Primary alcohol
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic 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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