Record Information |
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Version | 1.0 |
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Created at | 2021-11-12 23:55:03 UTC |
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Updated at | 2021-11-26 17:46:24 UTC |
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NP-MRD ID | NP0044187 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Eupalinin C |
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Description | Eupalinin C belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Eupalinin C is found in Eupatorium chinense, Eupatorium glehnii and Eupatorium lindleyanum. It was first documented in 1979 (Kazuo, et al.). Based on a literature review very few articles have been published on eupalinin C. |
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Structure | C\C=C(/CO)C(=O)O[C@@H]1C[C@@]2(C)O[C@@H]2C[C@@H](OC(C)=O)\C(C)=C/[C@H]2OC(=O)C(=C)[C@H]12 InChI=1S/C22H28O8/c1-6-14(10-23)21(26)29-17-9-22(5)18(30-22)8-15(27-13(4)24)11(2)7-16-19(17)12(3)20(25)28-16/h6-7,15-19,23H,3,8-10H2,1-2,4-5H3/b11-7-,14-6+/t15-,16-,17-,18-,19+,22-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C22H28O8 |
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Average Mass | 420.4580 Da |
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Monoisotopic Mass | 420.17842 Da |
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IUPAC Name | (1R,2R,4R,6R,8R,9Z,11R)-8-(acetyloxy)-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2E)-2-(hydroxymethyl)but-2-enoate |
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Traditional Name | (1R,2R,4R,6R,8R,9Z,11R)-8-(acetyloxy)-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2E)-2-(hydroxymethyl)but-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | C\C=C(/CO)C(=O)O[C@@H]1C[C@@]2(C)O[C@@H]2C[C@@H](OC(C)=O)\C(C)=C/[C@H]2OC(=O)C(=C)[C@H]12 |
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InChI Identifier | InChI=1S/C22H28O8/c1-6-14(10-23)21(26)29-17-9-22(5)18(30-22)8-15(27-13(4)24)11(2)7-16-19(17)12(3)20(25)28-16/h6-7,15-19,23H,3,8-10H2,1-2,4-5H3/b11-7-,14-6+/t15-,16-,17-,18-,19+,22-/m1/s1 |
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InChI Key | RDZDKJXIRQNZFT-JARGAAGTSA-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 germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. |
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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 lactones |
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Direct Parent | Germacranolides and derivatives |
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Alternative Parents | |
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Substituents | - Germacranolide
- Sesquiterpenoid
- Tricarboxylic acid or derivatives
- Beta-hydroxy acid
- Fatty acid ester
- Gamma butyrolactone
- Fatty acyl
- Hydroxy acid
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Carboxylic acid ester
- Lactone
- Organoheterocyclic compound
- Oxacycle
- Ether
- Oxirane
- Dialkyl ether
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- Primary 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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