| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 15:50:54 UTC |
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| Updated at | 2022-04-28 15:50:54 UTC |
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| NP-MRD ID | NP0070443 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Siwanine D |
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| Description | (1S,2S,3S,4S,5R,6R,8R,12R,13R,16S,19S,20S,21S)-2,6-dihydroxy-4,19-dimethoxy-14,16-dimethyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]Docos-17-en-21-yl acetate belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom. Siwanine D is found in Delphinium siwanense var. leptogen. Based on a literature review very few articles have been published on (1S,2S,3S,4S,5R,6R,8R,12R,13R,16S,19S,20S,21S)-2,6-dihydroxy-4,19-dimethoxy-14,16-dimethyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]Docos-17-en-21-yl acetate. |
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| Structure | CO[C@H]1[C@@H]2C[C@]3(O)[C@H]1[C@@]1(C[C@H]2O)OCO[C@]11[C@@H](OC(C)=O)[C@@H]2[C@@]33[C@H]1N(C)C[C@@]2(C)C=C[C@@H]3OC InChI=1S/C25H35NO8/c1-12(27)34-19-18-21(2)7-6-15(30-4)24(18)20(26(3)10-21)25(19)23(32-11-33-25)9-14(28)13-8-22(24,29)17(23)16(13)31-5/h6-7,13-20,28-29H,8-11H2,1-5H3/t13-,14-,15+,16+,17+,18+,19+,20-,21-,22+,23-,24+,25+/m1/s1 |
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| Synonyms | | Value | Source |
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| (1S,2S,3S,4S,5R,6R,8R,12R,13R,16S,19S,20S,21S)-2,6-Dihydroxy-4,19-dimethoxy-14,16-dimethyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1,.0,.0,.0,.0,]docos-17-en-21-yl acetic acid | Generator |
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| Chemical Formula | C25H35NO8 |
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| Average Mass | 477.5540 Da |
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| Monoisotopic Mass | 477.23627 Da |
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| IUPAC Name | (1S,2S,3S,4S,5R,6R,8R,12R,13R,16S,19S,20S,21S)-2,6-dihydroxy-4,19-dimethoxy-14,16-dimethyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1^{2,5}.0^{1,13}.0^{3,8}.0^{8,12}.0^{16,20}]docos-17-en-21-yl acetate |
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| Traditional Name | (1S,2S,3S,4S,5R,6R,8R,12R,13R,16S,19S,20S,21S)-2,6-dihydroxy-4,19-dimethoxy-14,16-dimethyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1^{2,5}.0^{1,13}.0^{3,8}.0^{8,12}.0^{16,20}]docos-17-en-21-yl acetate |
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| CAS Registry Number | Not Available |
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| SMILES | CO[C@H]1[C@@H]2C[C@]3(O)[C@H]1[C@@]1(C[C@H]2O)OCO[C@]11[C@@H](OC(C)=O)[C@@H]2[C@@]33[C@H]1N(C)C[C@@]2(C)C=C[C@@H]3OC |
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| InChI Identifier | InChI=1S/C25H35NO8/c1-12(27)34-19-18-21(2)7-6-15(30-4)24(18)20(26(3)10-21)25(19)23(32-11-33-25)9-14(28)13-8-22(24,29)17(23)16(13)31-5/h6-7,13-20,28-29H,8-11H2,1-5H3/t13-,14-,15+,16+,17+,18+,19+,20-,21-,22+,23-,24+,25+/m1/s1 |
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| InChI Key | YIRIOYAORYKQRE-BXSHUTGGSA-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 | | Species Name | Source | Reference |
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| Delphinium siwanense var. leptogen | Plant | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom. |
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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 | Aconitane-type diterpenoid alkaloids |
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| Alternative Parents | |
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| Substituents | - Aconitane-type diterpenoid alkaloid
- Quinolidine
- Alkaloid or derivatives
- Azepane
- Piperidine
- Tertiary alcohol
- Cyclic alcohol
- Meta-dioxolane
- Tertiary aliphatic amine
- Tertiary amine
- Secondary alcohol
- Carboxylic acid ester
- Amino acid or derivatives
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Acetal
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Amine
- 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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