Record Information |
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Version | 2.0 |
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Created at | 2022-09-11 23:52:03 UTC |
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Updated at | 2022-09-11 23:52:03 UTC |
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NP-MRD ID | NP0321587 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,3s,7r,8r,9z)-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl (3r)-3-hydroxy-2-methylidenebutanoate |
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Description | (1R,3S,7R,8R)-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]Tetradeca-9,11-dien-8-yl (3R)-3-hydroxy-2-methylidenebutanoate 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. (1r,3s,7r,8r,9z)-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl (3r)-3-hydroxy-2-methylidenebutanoate is found in Eremanthus glomerulatus. Based on a literature review very few articles have been published on (1R,3S,7R,8R)-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]Tetradeca-9,11-dien-8-yl (3R)-3-hydroxy-2-methylidenebutanoate. |
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Structure | C[C@@H](O)C(=C)C(=O)O[C@@H]1\C=C(C)/C2=CC(=O)[C@@](C)(C[C@@H]3OC(=O)C(=C)[C@@H]13)O2 InChI=1S/C20H22O7/c1-9-6-14(25-18(23)10(2)12(4)21)17-11(3)19(24)26-15(17)8-20(5)16(22)7-13(9)27-20/h6-7,12,14-15,17,21H,2-3,8H2,1,4-5H3/b9-6-/t12-,14-,15+,17+,20-/m1/s1 |
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Synonyms | Value | Source |
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(1R,3S,7R,8R)-1,10-Dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0,]tetradeca-9,11-dien-8-yl (3R)-3-hydroxy-2-methylidenebutanoic acid | Generator |
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Chemical Formula | C20H22O7 |
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Average Mass | 374.3890 Da |
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Monoisotopic Mass | 374.13655 Da |
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IUPAC Name | (1R,3S,7R,8R,9Z)-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-9,11-dien-8-yl (3R)-3-hydroxy-2-methylidenebutanoate |
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Traditional Name | (1R,3S,7R,8R,9Z)-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-9,11-dien-8-yl (3R)-3-hydroxy-2-methylidenebutanoate |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H](O)C(=C)C(=O)O[C@@H]1\C=C(C)/C2=CC(=O)[C@@](C)(C[C@@H]3OC(=O)C(=C)[C@@H]13)O2 |
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InChI Identifier | InChI=1S/C20H22O7/c1-9-6-14(25-18(23)10(2)12(4)21)17-11(3)19(24)26-15(17)8-20(5)16(22)7-13(9)27-20/h6-7,12,14-15,17,21H,2-3,8H2,1,4-5H3/b9-6-/t12-,14-,15+,17+,20-/m1/s1 |
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InChI Key | IIUNTHCAPVZAJW-YKJCPWKQSA-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 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
- Beta-hydroxy acid
- Fatty acid ester
- Dicarboxylic acid or derivatives
- 3-furanone
- Fatty acyl
- Gamma butyrolactone
- Hydroxy acid
- Dihydrofuran
- Vinylogous ester
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Ketone
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Organic oxygen compound
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Organooxygen compound
- Carbonyl group
- 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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