Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 11:49:55 UTC |
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Updated at | 2022-04-28 11:49:55 UTC |
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NP-MRD ID | NP0067274 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (-)-Spiramine R |
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Description | (1S,5R,8R,10S,11R,12R,14S,16S,17R)-3-(2-hydroxyethyl)-5-methyl-13-methylidene-4-oxo-9-oxa-3-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]Icosan-12-yl acetate belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. (-)-Spiramine R is found in Spiraea japonica and Spiraea japonica var.incisa. Based on a literature review very few articles have been published on (1S,5R,8R,10S,11R,12R,14S,16S,17R)-3-(2-hydroxyethyl)-5-methyl-13-methylidene-4-oxo-9-oxa-3-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]Icosan-12-yl acetate. |
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Structure | CC(=O)O[C@@H]1C(=C)[C@H]2CC[C@@]11[C@@H]3C[C@H]4[C@@]5(C)CC[C@@H](O3)[C@@]4(CN(CCO)C5=O)[C@@H]1C2 InChI=1S/C24H33NO5/c1-13-15-4-7-23(20(13)29-14(2)27)17(10-15)24-12-25(8-9-26)21(28)22(3)6-5-18(24)30-19(23)11-16(22)24/h15-20,26H,1,4-12H2,2-3H3/t15-,16-,17+,18+,19-,20+,22+,23+,24+/m0/s1 |
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Synonyms | Value | Source |
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(1S,5R,8R,10S,11R,12R,14S,16S,17R)-3-(2-Hydroxyethyl)-5-methyl-13-methylidene-4-oxo-9-oxa-3-azahexacyclo[8.6.2.2,.0,.0,.0,]icosan-12-yl acetic acid | Generator |
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Chemical Formula | C24H33NO5 |
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Average Mass | 415.5300 Da |
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Monoisotopic Mass | 415.23587 Da |
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IUPAC Name | (1S,5R,8R,10S,11R,12R,14S,16S,17R)-3-(2-hydroxyethyl)-5-methyl-13-methylidene-4-oxo-9-oxa-3-azahexacyclo[8.6.2.2^{11,14}.0^{1,8}.0^{5,17}.0^{11,16}]icosan-12-yl acetate |
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Traditional Name | (1S,5R,8R,10S,11R,12R,14S,16S,17R)-3-(2-hydroxyethyl)-5-methyl-13-methylidene-4-oxo-9-oxa-3-azahexacyclo[8.6.2.2^{11,14}.0^{1,8}.0^{5,17}.0^{11,16}]icosan-12-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]2CC[C@@]11[C@@H]3C[C@H]4[C@@]5(C)CC[C@@H](O3)[C@@]4(CN(CCO)C5=O)[C@@H]1C2 |
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InChI Identifier | InChI=1S/C24H33NO5/c1-13-15-4-7-23(20(13)29-14(2)27)17(10-15)24-12-25(8-9-26)21(28)22(3)6-5-18(24)30-19(23)11-16(22)24/h15-20,26H,1,4-12H2,2-3H3/t15-,16-,17+,18+,19-,20+,22+,23+,24+/m0/s1 |
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InChI Key | FMOXTYQIUUYGOB-OUXJVHRMSA-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 atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. |
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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 | Atisane diterpenoids |
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Alternative Parents | |
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Substituents | - Atisane diterpenoid
- Isoquinolone
- Azaspirodecane
- Alkaloid or derivatives
- Piperidinone
- Delta-lactam
- Piperidine
- Oxane
- Tertiary carboxylic acid amide
- Lactam
- Carboxylic acid ester
- Carboxamide group
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Alkanolamine
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Alcohol
- 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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