Record Information |
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Version | 2.0 |
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Created at | 2022-09-12 00:53:27 UTC |
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Updated at | 2022-09-12 00:53:27 UTC |
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NP-MRD ID | NP0322231 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate |
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Description | (3AR)-3abeta,4,5,6,6abeta,7,8,9,9abeta,9balpha-Decahydro-3,6,9-trismethylene-4beta-hydroxy-8alpha-(benzoyloxy)azuleno[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. (3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate is found in Centaurea scoparia. Based on a literature review very few articles have been published on (3aR)-3abeta,4,5,6,6abeta,7,8,9,9abeta,9balpha-Decahydro-3,6,9-trismethylene-4beta-hydroxy-8alpha-(benzoyloxy)azuleno[4,5-b]furan-2(3H)-one. |
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Structure | O[C@H]1CC(=C)[C@@H]2C[C@H](OC(=O)C3=CC=CC=C3)C(=C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12 InChI=1S/C22H22O5/c1-11-9-16(23)19-13(3)21(24)27-20(19)18-12(2)17(10-15(11)18)26-22(25)14-7-5-4-6-8-14/h4-8,15-20,23H,1-3,9-10H2/t15-,16-,17-,18-,19+,20+/m0/s1 |
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Synonyms | Value | Source |
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(3AR)-3abeta,4,5,6,6abeta,7,8,9,9abeta,9balpha-decahydro-3,6,9-trismethylene-4b-hydroxy-8a-(benzoyloxy)azuleno[4,5-b]furan-2(3H)-one | Generator | (3AR)-3abeta,4,5,6,6abeta,7,8,9,9abeta,9balpha-decahydro-3,6,9-trismethylene-4β-hydroxy-8α-(benzoyloxy)azuleno[4,5-b]furan-2(3H)-one | Generator |
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Chemical Formula | C22H22O5 |
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Average Mass | 366.4130 Da |
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Monoisotopic Mass | 366.14672 Da |
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IUPAC Name | (3aR,4S,6aR,8S,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl benzoate |
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Traditional Name | (3aR,4S,6aR,8S,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate |
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CAS Registry Number | Not Available |
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SMILES | O[C@H]1CC(=C)[C@@H]2C[C@H](OC(=O)C3=CC=CC=C3)C(=C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12 |
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InChI Identifier | InChI=1S/C22H22O5/c1-11-9-16(23)19-13(3)21(24)27-20(19)18-12(2)17(10-15(11)18)26-22(25)14-7-5-4-6-8-14/h4-8,15-20,23H,1-3,9-10H2/t15-,16-,17-,18-,19+,20+/m0/s1 |
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InChI Key | UIIZHPJVPKARSE-GFLQDLJJSA-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
- Sesquiterpenoid
- Guaiane sesquiterpenoid
- Benzoate ester
- Benzoic acid or derivatives
- Benzoyl
- Benzenoid
- Gamma butyrolactone
- Dicarboxylic acid or derivatives
- Monocyclic benzene moiety
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Cyclic alcohol
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic 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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