Record Information |
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Version | 1.0 |
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Created at | 2022-05-31 16:40:12 UTC |
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Updated at | 2022-05-31 16:40:13 UTC |
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NP-MRD ID | NP0137944 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 5,8-Epidioxyergosta-6,9(11),22-trien-3-ol |
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Description | 9,11-Dehydroergosterol peroxide, also known as 5,8-edeto, belongs to the class of organic compounds known as ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position. Thus, 9,11-dehydroergosterol peroxide is considered to be a sterol. 5,8-Epidioxyergosta-6,9(11),22-trien-3-ol is found in Duranta erecta, Ganoderma applanatum, Ganoderma tsugae, Grifola frondosa, Haloxylon salicornicum, Ophiocordyceps sinensis, Pellia epiphylla, Sinularia flexibilis, Stereum hirsutum, Mallotus nudiflorus and Typha capensis. It was first documented in 2017 (PMID: 28315853). Based on a literature review a significant number of articles have been published on 9,11-dehydroergosterol peroxide (PMID: 30149516) (PMID: 30092384) (PMID: 30560887) (PMID: 29845223). |
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Structure | [H]\C(=C(\[H])[C@@]([H])(C)[C@@]1([H])CC[C@]2([H])[C@]1(C)CC=C1[C@@]3(C)CC[C@]([H])(O)C[C@@]33OO[C@@]21C=C3)[C@]([H])(C)C(C)C InChI=1S/C28H42O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,12,15-16,18-23,29H,9-11,13-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,25+,26+,27+,28-/m0/s1 |
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Synonyms | |
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Chemical Formula | C28H42O3 |
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Average Mass | 426.6410 Da |
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Monoisotopic Mass | 426.31340 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 86363-50-0 |
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SMILES | [H]\C(=C(\[H])[C@@]([H])(C)[C@@]1([H])CC[C@]2([H])[C@]1(C)CC=C1[C@@]3(C)CC[C@]([H])(O)C[C@@]33OO[C@@]21C=C3)[C@]([H])(C)C(C)C |
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InChI Identifier | InChI=1S/C28H42O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,12,15-16,18-23,29H,9-11,13-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,25+,26+,27+,28-/m0/s1 |
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InChI Key | FWPYIYVSYQRISA-LEOBWYFPSA-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 ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position. |
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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 | Ergostane steroids |
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Direct Parent | Ergostane steroids |
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Alternative Parents | |
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Substituents | - Ergostane-skeleton
- Ortho-dioxane
- Cyclic alcohol
- Dialkyl peroxide
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- 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 | - Lee S, Lee S, Roh HS, Song SS, Ryoo R, Pang C, Baek KH, Kim KH: Cytotoxic Constituents from the Sclerotia of Poria cocos against Human Lung Adenocarcinoma Cells by Inducing Mitochondrial Apoptosis. Cells. 2018 Aug 24;7(9). pii: cells7090116. doi: 10.3390/cells7090116. [PubMed:30149516 ]
- Lee S, Choi E, Yang SM, Ryoo R, Moon E, Kim SH, Kim KH: Bioactive compounds from sclerotia extract of Poria cocos that control adipocyte and osteoblast differentiation. Bioorg Chem. 2018 Dec;81:27-34. doi: 10.1016/j.bioorg.2018.07.031. Epub 2018 Jul 31. [PubMed:30092384 ]
- Wu HY, Yang FL, Li LH, Rao YK, Ju TC, Wong WT, Hsieh CY, Pivkin MV, Hua KF, Wu SH: Ergosterol peroxide from marine fungus Phoma sp. induces ROS-dependent apoptosis and autophagy in human lung adenocarcinoma cells. Sci Rep. 2018 Dec 18;8(1):17956. doi: 10.1038/s41598-018-36411-2. [PubMed:30560887 ]
- Zheng L, Wong YS, Shao M, Huang S, Wang F, Chen J: Apoptosis induced by 9,11dehydroergosterol peroxide from Ganoderma Lucidum mycelium in human malignant melanoma cells is Mcl1 dependent. Mol Med Rep. 2018 Jul;18(1):938-944. doi: 10.3892/mmr.2018.9035. Epub 2018 May 17. [PubMed:29845223 ]
- Merdivan S, Jenett-Siems K, Siems K, Niedermeyer THJ, Schultze N, Steinborn C, Grundemann C, Lindequist U: Effects of extracts and compounds from Tricholoma populinum Lange on degranulation and IL-2/IL-8 secretion of immune cells. Z Naturforsch C J Biosci. 2017 Jul 14;72(7-8):277-283. doi: 10.1515/znc-2016-0247. [PubMed:28315853 ]
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