Record Information |
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Version | 1.0 |
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Created at | 2022-09-11 03:18:36 UTC |
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Updated at | 2022-09-11 03:18:37 UTC |
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NP-MRD ID | NP0309035 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (3r,3ar,4s,6r,6as,9s,9as,9bs)-6a-hydroperoxy-4,6,9-trihydroxy-3-(hydroxymethyl)-6,9-dimethyl-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2-one |
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Description | (3R)-3abeta,4,5,6,6a,9,9abeta,9balpha-Octahydro-6abeta-(hydroperoxy)-3beta-(hydroxymethyl)-4beta,6beta,9alpha-trihydroxy-6,9-dimethylazuleno[4,5-b]furan-2(3H)-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. (3r,3ar,4s,6r,6as,9s,9as,9bs)-6a-hydroperoxy-4,6,9-trihydroxy-3-(hydroxymethyl)-6,9-dimethyl-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2-one is found in Ajania fruticulosa. Based on a literature review very few articles have been published on (3R)-3abeta,4,5,6,6a,9,9abeta,9balpha-Octahydro-6abeta-(hydroperoxy)-3beta-(hydroxymethyl)-4beta,6beta,9alpha-trihydroxy-6,9-dimethylazuleno[4,5-b]furan-2(3H)-one. |
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Structure | C[C@]1(O)C=C[C@]2(OO)[C@H]1[C@H]1OC(=O)[C@@H](CO)[C@@H]1[C@@H](O)C[C@@]2(C)O InChI=1S/C15H22O8/c1-13(19)3-4-15(23-21)11(13)10-9(7(6-16)12(18)22-10)8(17)5-14(15,2)20/h3-4,7-11,16-17,19-21H,5-6H2,1-2H3/t7-,8-,9+,10-,11-,13-,14+,15-/m0/s1 |
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Synonyms | Value | Source |
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(3R)-3Abeta,4,5,6,6a,9,9abeta,9balpha-octahydro-6abeta-(hydroperoxy)-3b-(hydroxymethyl)-4b,6b,9a-trihydroxy-6,9-dimethylazuleno[4,5-b]furan-2(3H)-one | Generator | (3R)-3Abeta,4,5,6,6a,9,9abeta,9balpha-octahydro-6abeta-(hydroperoxy)-3β-(hydroxymethyl)-4β,6β,9α-trihydroxy-6,9-dimethylazuleno[4,5-b]furan-2(3H)-one | Generator |
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Chemical Formula | C15H22O8 |
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Average Mass | 330.3330 Da |
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Monoisotopic Mass | 330.13147 Da |
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IUPAC Name | (3R,3aR,4S,6R,6aS,9S,9aS,9bS)-6a-hydroperoxy-4,6,9-trihydroxy-3-(hydroxymethyl)-6,9-dimethyl-2H,3H,3aH,4H,5H,6H,6aH,9H,9aH,9bH-azuleno[4,5-b]furan-2-one |
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Traditional Name | (3R,3aR,4S,6R,6aS,9S,9aS,9bS)-6a-hydroperoxy-4,6,9-trihydroxy-3-(hydroxymethyl)-6,9-dimethyl-3H,3aH,4H,5H,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@]2(OO)[C@H]1[C@H]1OC(=O)[C@@H](CO)[C@@H]1[C@@H](O)C[C@@]2(C)O |
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InChI Identifier | InChI=1S/C15H22O8/c1-13(19)3-4-15(23-21)11(13)10-9(7(6-16)12(18)22-10)8(17)5-14(15,2)20/h3-4,7-11,16-17,19-21H,5-6H2,1-2H3/t7-,8-,9+,10-,11-,13-,14+,15-/m0/s1 |
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InChI Key | FAEGAUFRSWMWGU-LSSUBMIMSA-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 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
- Guaiane sesquiterpenoid
- Sesquiterpenoid
- Gamma butyrolactone
- Cyclic alcohol
- Tertiary alcohol
- Tetrahydrofuran
- Carboxylic acid ester
- Lactone
- Hydroperoxide
- Secondary alcohol
- Polyol
- Peroxol
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Alkyl hydroperoxide
- Oxacycle
- Carboxylic acid derivative
- Organooxygen compound
- Carbonyl group
- Organic oxide
- Organic oxygen compound
- Alcohol
- Primary alcohol
- Hydrocarbon derivative
- 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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