Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 07:59:24 UTC |
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Updated at | 2022-04-28 07:59:24 UTC |
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NP-MRD ID | NP0063609 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Pyrethroidin |
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Description | (3AR,6S,6aR,9S,9aR,9bS)-6,9-dihydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,9H,9aH,9bH-azuleno[4,5-b]furan-2-one 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. Pyrethroidin is found in Pyrethrum pyrethroides. Based on a literature review very few articles have been published on (3aR,6S,6aR,9S,9aR,9bS)-6,9-dihydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,9H,9aH,9bH-azuleno[4,5-b]furan-2-one. |
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Structure | C[C@]1(O)C=C[C@@H]2[C@@H]1[C@H]1OC(=O)C(=C)[C@H]1CC[C@]2(C)O InChI=1S/C15H20O4/c1-8-9-4-6-14(2,17)10-5-7-15(3,18)11(10)12(9)19-13(8)16/h5,7,9-12,17-18H,1,4,6H2,2-3H3/t9-,10-,11-,12+,14+,15+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C15H20O4 |
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Average Mass | 264.3210 Da |
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Monoisotopic Mass | 264.13616 Da |
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IUPAC Name | (3aR,6S,6aR,9S,9aR,9bS)-6,9-dihydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,9H,9aH,9bH-azuleno[4,5-b]furan-2-one |
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Traditional Name | (3aR,6S,6aR,9S,9aR,9bS)-6,9-dihydroxy-6,9-dimethyl-3-methylidene-3aH,4H,5H,6aH,9aH,9bH-azuleno[4,5-b]furan-2-one |
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CAS Registry Number | Not Available |
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SMILES | C[C@]1(O)C=C[C@@H]2[C@@H]1[C@H]1OC(=O)C(=C)[C@H]1CC[C@]2(C)O |
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InChI Identifier | InChI=1S/C15H20O4/c1-8-9-4-6-14(2,17)10-5-7-15(3,18)11(10)12(9)19-13(8)16/h5,7,9-12,17-18H,1,4,6H2,2-3H3/t9-,10-,11-,12+,14+,15+/m1/s1 |
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InChI Key | SZCYFRYSKNGMRA-ACBLYQCWSA-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
- Gamma butyrolactone
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Tertiary alcohol
- Cyclic alcohol
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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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