| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 08:01:30 UTC |
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| Updated at | 2022-04-28 08:01:30 UTC |
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| NP-MRD ID | NP0063644 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 8beta-Hydroxyzaluzanin D |
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| Description | (3AR,4R,6aR,8S,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl acetate 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. 8beta-Hydroxyzaluzanin D is found in Centaurea kandavanensis and Centaurea nicolai. Based on a literature review very few articles have been published on (3aR,4R,6aR,8S,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl acetate. |
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| Structure | CC(=O)O[C@H]1C[C@@H]2[C@@H]([C@H]3OC(=O)C(=C)[C@@H]3[C@H](O)CC2=C)C1=C InChI=1S/C17H20O5/c1-7-5-12(19)15-9(3)17(20)22-16(15)14-8(2)13(6-11(7)14)21-10(4)18/h11-16,19H,1-3,5-6H2,4H3/t11-,12+,13-,14-,15+,16+/m0/s1 |
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| Synonyms | | Value | Source |
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| (3AR,4R,6ar,8S,9ar,9BR)-4-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl acetic acid | Generator |
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| Chemical Formula | C17H20O5 |
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| Average Mass | 304.3420 Da |
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| Monoisotopic Mass | 304.13107 Da |
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| IUPAC Name | (3aR,4R,6aR,8S,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl acetate |
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| Traditional Name | (3aR,4R,6aR,8S,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl acetate |
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| CAS Registry Number | Not Available |
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| SMILES | CC(=O)O[C@H]1C[C@@H]2[C@@H]([C@H]3OC(=O)C(=C)[C@@H]3[C@H](O)CC2=C)C1=C |
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| InChI Identifier | InChI=1S/C17H20O5/c1-7-5-12(19)15-9(3)17(20)22-16(15)14-8(2)13(6-11(7)14)21-10(4)18/h11-16,19H,1-3,5-6H2,4H3/t11-,12+,13-,14-,15+,16+/m0/s1 |
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| InChI Key | ZOQZWYXGJUDJFV-VNAATALASA-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
- Guaiane sesquiterpenoid
- Sesquiterpenoid
- Dicarboxylic acid or derivatives
- Gamma butyrolactone
- Cyclic alcohol
- Tetrahydrofuran
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- 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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