| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-10 00:22:56 UTC |
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| Updated at | 2022-09-10 00:22:56 UTC |
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| NP-MRD ID | NP0292715 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 4a,6-dihydroxy-3,5-dimethylidene-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-2-one |
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| Description | 4A,6-dihydroxy-3,5-dimethylidene-decahydro-2H-spiro[azuleno[6,5-b]furan-8,2'-oxirane]-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. 4a,6-dihydroxy-3,5-dimethylidene-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-2-one is found in Arctotis stoechadifolia. 4A,6-dihydroxy-3,5-dimethylidene-decahydro-2H-spiro[azuleno[6,5-b]furan-8,2'-oxirane]-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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| Structure | OC1CC2C3(CO3)CC3OC(=O)C(=C)C3CC2(O)C1=C InChI=1S/C15H18O5/c1-7-9-4-15(18)8(2)10(16)3-12(15)14(6-19-14)5-11(9)20-13(7)17/h9-12,16,18H,1-6H2 |
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| Synonyms | Not Available |
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| Chemical Formula | C15H18O5 |
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| Average Mass | 278.3040 Da |
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| Monoisotopic Mass | 278.11542 Da |
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| IUPAC Name | 4a,6-dihydroxy-3,5-dimethylidene-decahydro-2H-spiro[azuleno[6,5-b]furan-8,2'-oxirane]-2-one |
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| Traditional Name | 4a,6-dihydroxy-3,5-dimethylidene-hexahydro-3aH-spiro[azuleno[6,5-b]furan-8,2'-oxirane]-2-one |
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| CAS Registry Number | Not Available |
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| SMILES | OC1CC2C3(CO3)CC3OC(=O)C(=C)C3CC2(O)C1=C |
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| InChI Identifier | InChI=1S/C15H18O5/c1-7-9-4-15(18)8(2)10(16)3-12(15)14(6-19-14)5-11(9)20-13(7)17/h9-12,16,18H,1-6H2 |
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| InChI Key | NRQMQZXLJOVXEZ-UHFFFAOYSA-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
- Gamma butyrolactone
- Cyclic alcohol
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Tertiary alcohol
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Carboxylic acid derivative
- Dialkyl ether
- Oxirane
- Ether
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Carbonyl group
- Alcohol
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- Organooxygen compound
- 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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