Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 07:59:57 UTC |
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Updated at | 2022-04-28 07:59:57 UTC |
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NP-MRD ID | NP0063614 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 9,10-Dihydroxy-3,11(13)-guaiadien-12,6-olide |
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Description | (3AS)-3a,4,5,6,6abeta,7,9abeta,9balpha-Octahydro-6alpha,9-dimethyl-5beta,6beta-dihydroxy-3-methyleneazuleno[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. 9,10-Dihydroxy-3,11(13)-guaiadien-12,6-olide is found in Ajania achilleoides. Based on a literature review very few articles have been published on (3aS)-3a,4,5,6,6abeta,7,9abeta,9balpha-Octahydro-6alpha,9-dimethyl-5beta,6beta-dihydroxy-3-methyleneazuleno[4,5-b]furan-2(3H)-one. |
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Structure | CC1=CC[C@@H]2[C@H]1[C@H]1OC(=O)C(=C)[C@@H]1C[C@@H](O)[C@@]2(C)O InChI=1S/C15H20O4/c1-7-4-5-10-12(7)13-9(8(2)14(17)19-13)6-11(16)15(10,3)18/h4,9-13,16,18H,2,5-6H2,1,3H3/t9-,10+,11+,12-,13-,15-/m0/s1 |
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Synonyms | Value | Source |
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(3AS)-3a,4,5,6,6abeta,7,9abeta,9balpha-octahydro-6a,9-dimethyl-5b,6b-dihydroxy-3-methyleneazuleno[4,5-b]furan-2(3H)-one | Generator | (3AS)-3a,4,5,6,6abeta,7,9abeta,9balpha-octahydro-6α,9-dimethyl-5β,6β-dihydroxy-3-methyleneazuleno[4,5-b]furan-2(3H)-one | Generator |
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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 | (3aS,5R,6S,6aR,9aR,9bS)-5,6-dihydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one |
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Traditional Name | (3aS,5R,6S,6aR,9aR,9bS)-5,6-dihydroxy-6,9-dimethyl-3-methylidene-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one |
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CAS Registry Number | Not Available |
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SMILES | CC1=CC[C@@H]2[C@H]1[C@H]1OC(=O)C(=C)[C@@H]1C[C@@H](O)[C@@]2(C)O |
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InChI Identifier | InChI=1S/C15H20O4/c1-7-4-5-10-12(7)13-9(8(2)14(17)19-13)6-11(16)15(10,3)18/h4,9-13,16,18H,2,5-6H2,1,3H3/t9-,10+,11+,12-,13-,15-/m0/s1 |
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InChI Key | DCVONVXPVPZIGR-WJLGXSQGSA-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
- Gamma butyrolactone
- Cyclic alcohol
- Tertiary alcohol
- Tetrahydrofuran
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Secondary alcohol
- Lactone
- 1,2-diol
- Carboxylic acid ester
- Oxacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organoheterocyclic compound
- 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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