Record Information |
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Version | 2.0 |
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Created at | 2022-09-12 03:10:49 UTC |
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Updated at | 2022-09-12 03:10:49 UTC |
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NP-MRD ID | NP0323629 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1s,2r,4s,6s,9s,10s,11s,13s,15r)-2,6,11-tris(acetyloxy)-5,5,9-trimethyl-14-methylidene-3-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate |
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Description | (1S,2R,4S,6S,9S,10S,11S,13S,15R)-2,6,11-tris(acetyloxy)-5,5,9-trimethyl-14-methylidene-3-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-15-yl acetate 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. (1s,2r,4s,6s,9s,10s,11s,13s,15r)-2,6,11-tris(acetyloxy)-5,5,9-trimethyl-14-methylidene-3-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate is found in Isodon gesneroides. Based on a literature review very few articles have been published on (1S,2R,4S,6S,9S,10S,11S,13S,15R)-2,6,11-tris(acetyloxy)-5,5,9-trimethyl-14-methylidene-3-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-15-yl acetate. |
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Structure | CC(=O)O[C@@H]1C(=C)[C@H]2C[C@@]11[C@@H](OC(C)=O)C(=O)[C@@H]3C(C)(C)[C@H](CC[C@@]3(C)[C@@H]1[C@H](C2)OC(C)=O)OC(C)=O InChI=1S/C28H38O9/c1-13-18-11-19(34-14(2)29)22-27(8)10-9-20(35-15(3)30)26(6,7)23(27)21(33)25(37-17(5)32)28(22,12-18)24(13)36-16(4)31/h18-20,22-25H,1,9-12H2,2-8H3/t18-,19+,20+,22+,23-,24-,25+,27+,28+/m1/s1 |
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Synonyms | Value | Source |
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(1S,2R,4S,6S,9S,10S,11S,13S,15R)-2,6,11-Tris(acetyloxy)-5,5,9-trimethyl-14-methylidene-3-oxotetracyclo[11.2.1.0,.0,]hexadecan-15-yl acetic acid | Generator |
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Chemical Formula | C28H38O9 |
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Average Mass | 518.6030 Da |
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Monoisotopic Mass | 518.25158 Da |
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IUPAC Name | (1S,2R,4S,6S,9S,10S,11S,13S,15R)-2,6,11-tris(acetyloxy)-5,5,9-trimethyl-14-methylidene-3-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-yl acetate |
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Traditional Name | (1S,2R,4S,6S,9S,10S,11S,13S,15R)-2,6,11-tris(acetyloxy)-5,5,9-trimethyl-14-methylidene-3-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)O[C@@H]1C(=C)[C@H]2C[C@@]11[C@@H](OC(C)=O)C(=O)[C@@H]3C(C)(C)[C@H](CC[C@@]3(C)[C@@H]1[C@H](C2)OC(C)=O)OC(C)=O |
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InChI Identifier | InChI=1S/C28H38O9/c1-13-18-11-19(34-14(2)29)22-27(8)10-9-20(35-15(3)30)26(6,7)23(27)21(33)25(37-17(5)32)28(22,12-18)24(13)36-16(4)31/h18-20,22-25H,1,9-12H2,2-8H3/t18-,19+,20+,22+,23-,24-,25+,27+,28+/m1/s1 |
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InChI Key | FOVABTAYMLCRNI-CNEKVFIFSA-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
- Tetracarboxylic acid or derivatives
- Alpha-acyloxy ketone
- Ketone
- Carboxylic acid ester
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic 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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