Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 08:03:18 UTC |
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Updated at | 2022-04-28 08:03:18 UTC |
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NP-MRD ID | NP0063685 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 3alpha,4alpha-Epoxy-9-oxo-8beta-(5-acetoxy-tiglinoyloxy)-3,4-dihydro-lasiolaenin |
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Description | (1S,2R,6S,7S,10R,12R,14S)-14-methyl-5,9-dimethylidene-4,8-dioxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]Tetradecan-7-yl (2E)-2-[(acetyloxy)methyl]but-2-enoate belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. 3alpha,4alpha-Epoxy-9-oxo-8beta-(5-acetoxy-tiglinoyloxy)-3,4-dihydro-lasiolaenin is found in Lasiolaena santosii. Based on a literature review very few articles have been published on (1S,2R,6S,7S,10R,12R,14S)-14-methyl-5,9-dimethylidene-4,8-dioxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]Tetradecan-7-yl (2E)-2-[(acetyloxy)methyl]but-2-enoate. |
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Structure | C\C=C(/COC(C)=O)C(=O)O[C@H]1[C@@H]2[C@@H](OC(=O)C2=C)[C@@H]2[C@@H](C[C@H]3O[C@@]23C)C(=C)C1=O InChI=1S/C22H24O8/c1-6-12(8-27-11(4)23)21(26)29-19-15-10(3)20(25)28-18(15)16-13(9(2)17(19)24)7-14-22(16,5)30-14/h6,13-16,18-19H,2-3,7-8H2,1,4-5H3/b12-6+/t13-,14+,15-,16-,18+,19-,22+/m0/s1 |
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Synonyms | Value | Source |
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(1S,2R,6S,7S,10R,12R,14S)-14-Methyl-5,9-dimethylidene-4,8-dioxo-3,13-dioxatetracyclo[8.4.0.0,.0,]tetradecan-7-yl (2E)-2-[(acetyloxy)methyl]but-2-enoic acid | Generator |
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Chemical Formula | C22H24O8 |
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Average Mass | 416.4260 Da |
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Monoisotopic Mass | 416.14712 Da |
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IUPAC Name | (1S,2R,6S,7S,10R,12R,14S)-14-methyl-5,9-dimethylidene-4,8-dioxo-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradecan-7-yl (2E)-2-[(acetyloxy)methyl]but-2-enoate |
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Traditional Name | (1S,2R,6S,7S,10R,12R,14S)-14-methyl-5,9-dimethylidene-4,8-dioxo-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradecan-7-yl (2E)-2-[(acetyloxy)methyl]but-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | C\C=C(/COC(C)=O)C(=O)O[C@H]1[C@@H]2[C@@H](OC(=O)C2=C)[C@@H]2[C@@H](C[C@H]3O[C@@]23C)C(=C)C1=O |
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InChI Identifier | InChI=1S/C22H24O8/c1-6-12(8-27-11(4)23)21(26)29-19-15-10(3)20(25)28-18(15)16-13(9(2)17(19)24)7-14-22(16,5)30-14/h6,13-16,18-19H,2-3,7-8H2,1,4-5H3/b12-6+/t13-,14+,15-,16-,18+,19-,22+/m0/s1 |
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InChI Key | LWZIBQYIQKTBQF-DIJNLBKNSA-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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. |
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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 | Guaianolides and derivatives |
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Alternative Parents | |
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Substituents | - Guaianolide-skeleton
- Sesquiterpenoid
- Guaiane sesquiterpenoid
- Tricarboxylic acid or derivatives
- Alpha-acyloxy ketone
- Fatty acid ester
- Fatty acyl
- Oxane
- Gamma butyrolactone
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Cyclic ketone
- Lactone
- Ketone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Ether
- Oxirane
- Dialkyl ether
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- 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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