Record Information |
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Version | 1.0 |
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Created at | 2022-09-11 03:33:32 UTC |
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Updated at | 2022-09-11 03:33:32 UTC |
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NP-MRD ID | NP0309167 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,2s,3r,5s,6r,8r,9s,10s,11s,12r)-8,10-dihydroxy-13,13-dimethyl-7-methylidene-4,18-dioxahexacyclo[8.6.2.1⁶,⁹.0¹,¹².0²,⁹.0³,⁵]nonadecan-11-yl acetate |
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Description | Oreskaurin B belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. (1r,2s,3r,5s,6r,8r,9s,10s,11s,12r)-8,10-dihydroxy-13,13-dimethyl-7-methylidene-4,18-dioxahexacyclo[8.6.2.1⁶,⁹.0¹,¹².0²,⁹.0³,⁵]nonadecan-11-yl acetate is found in Isodon oresbius. It was first documented in 2021 (PMID: 36122136). Based on a literature review a significant number of articles have been published on Oreskaurin B (PMID: 36122131) (PMID: 36122153) (PMID: 36122119) (PMID: 36122116). |
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Structure | CC(=O)O[C@H]1[C@@H]2C(C)(C)CCC[C@]22CO[C@@]1(O)[C@@]13C[C@@H]([C@@H]4O[C@@H]4[C@@H]21)C(=C)[C@H]3O InChI=1S/C22H30O6/c1-10-12-8-21(17(10)24)15(14-13(12)28-14)20-7-5-6-19(3,4)16(20)18(27-11(2)23)22(21,25)26-9-20/h12-18,24-25H,1,5-9H2,2-4H3/t12-,13+,14+,15+,16-,17-,18+,20-,21+,22-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C22H30O6 |
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Average Mass | 390.4760 Da |
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Monoisotopic Mass | 390.20424 Da |
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IUPAC Name | (1R,2S,3R,5S,6R,8R,9S,10S,11S,12R)-8,10-dihydroxy-13,13-dimethyl-7-methylidene-4,18-dioxahexacyclo[8.6.2.1^{6,9}.0^{1,12}.0^{2,9}.0^{3,5}]nonadecan-11-yl acetate |
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Traditional Name | (1R,2S,3R,5S,6R,8R,9S,10S,11S,12R)-8,10-dihydroxy-13,13-dimethyl-7-methylidene-4,18-dioxahexacyclo[8.6.2.1^{6,9}.0^{1,12}.0^{2,9}.0^{3,5}]nonadecan-11-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)O[C@H]1[C@@H]2C(C)(C)CCC[C@]22CO[C@@]1(O)[C@@]13C[C@@H]([C@@H]4O[C@@H]4[C@@H]21)C(=C)[C@H]3O |
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InChI Identifier | InChI=1S/C22H30O6/c1-10-12-8-21(17(10)24)15(14-13(12)28-14)20-7-5-6-19(3,4)16(20)18(27-11(2)23)22(21,25)26-9-20/h12-18,24-25H,1,5-9H2,2-4H3/t12-,13+,14+,15+,16-,17-,18+,20-,21+,22-/m1/s1 |
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InChI Key | ZRKVMXWMNDIJCN-RDGJSPTHSA-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 kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. |
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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 | Diterpenoids |
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Direct Parent | Kaurane diterpenoids |
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Alternative Parents | |
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Substituents | - Kaurane diterpenoid
- Oxepane
- Oxane
- Cyclic alcohol
- Carboxylic acid ester
- Hemiacetal
- Secondary alcohol
- Oxacycle
- Carboxylic acid derivative
- Organoheterocyclic compound
- Dialkyl ether
- Oxirane
- Ether
- Monocarboxylic acid or derivatives
- Carbonyl group
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxygen compound
- Organic oxide
- 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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