Record Information |
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Version | 1.0 |
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Created at | 2022-09-06 09:19:48 UTC |
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Updated at | 2022-09-06 09:19:48 UTC |
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NP-MRD ID | NP0229323 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,5r,8r,9s,11s,13r,14r,16r,17r,18s,19r)-11,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-13-yl 2-methylpropanoate |
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Description | (1R,5R,8R,9S,11S,13R,14R,16R,17R,18S,19R)-11,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-13-yl 2-methylpropanoate belongs to the class of organic compounds known as hetisine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hetisine skeleton, which is a heptacyclic compound with an additional N-C-6 bond as compared with the hetidine-type, and thus, is one of most complex entries in the atisane-class. (1r,5r,8r,9s,11s,13r,14r,16r,17r,18s,19r)-11,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-13-yl 2-methylpropanoate is found in Delphinium verdunense. It was first documented in 2022 (PMID: 36088123). Based on a literature review a significant number of articles have been published on (1R,5R,8R,9S,11S,13R,14R,16R,17R,18S,19R)-11,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-13-yl 2-methylpropanoate (PMID: 36088122) (PMID: 36088121) (PMID: 36088120) (PMID: 36088119). |
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Structure | CC(C)C(=O)O[C@H]1C(=C)[C@@]2(O)C[C@@H]3[C@H]4N5C[C@]6(C)CCC[C@]44[C@H]([C@H]2O)[C@]13C[C@@]5(O)[C@H]64 InChI=1S/C24H33NO5/c1-11(2)18(27)30-17-12(3)23(28)8-13-15-21-7-5-6-20(4)10-25(15)24(29,19(20)21)9-22(13,17)14(21)16(23)26/h11,13-17,19,26,28-29H,3,5-10H2,1-2,4H3/t13-,14+,15-,16-,17+,19-,20+,21+,22-,23+,24-/m1/s1 |
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Synonyms | Value | Source |
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(1R,5R,8R,9S,11S,13R,14R,16R,17R,18S,19R)-11,16,19-Trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0,.0,.0,.0,.0,]nonadecan-13-yl 2-methylpropanoic 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 | (1R,5R,8R,9S,11S,13R,14R,16R,17R,18S,19R)-11,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-13-yl 2-methylpropanoate |
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Traditional Name | (1R,5R,8R,9S,11S,13R,14R,16R,17R,18S,19R)-11,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-13-yl 2-methylpropanoate |
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CAS Registry Number | Not Available |
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SMILES | CC(C)C(=O)O[C@H]1C(=C)[C@@]2(O)C[C@@H]3[C@H]4N5C[C@]6(C)CCC[C@]44[C@H]([C@H]2O)[C@]13C[C@@]5(O)[C@H]64 |
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InChI Identifier | InChI=1S/C24H33NO5/c1-11(2)18(27)30-17-12(3)23(28)8-13-15-21-7-5-6-20(4)10-25(15)24(29,19(20)21)9-22(13,17)14(21)16(23)26/h11,13-17,19,26,28-29H,3,5-10H2,1-2,4H3/t13-,14+,15-,16-,17+,19-,20+,21+,22-,23+,24-/m1/s1 |
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InChI Key | XSDJVVZNKHIOBC-PRVJHFKZSA-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 hetisine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hetisine skeleton, which is a heptacyclic compound with an additional N-C-6 bond as compared with the hetidine-type, and thus, is one of most complex entries in the atisane-class. |
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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 | Hetisine-type diterpenoid alkaloids |
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Alternative Parents | |
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Substituents | - Hetisine-type diterpenoid alkaloid
- Azaspirodecane
- Quinolizidine
- Indole or derivatives
- Indolizidine
- Isoindoline
- Alkaloid or derivatives
- Isoindole or derivatives
- Azepane
- N-alkylpyrrolidine
- Piperidine
- Cyclic alcohol
- Tertiary alcohol
- Pyrrolidine
- 1,2-diol
- Carboxylic acid ester
- Hemiaminal
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Azacycle
- Carboxylic acid derivative
- Alkanolamine
- Polyol
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Alcohol
- Carbonyl group
- Organic oxygen compound
- Organic nitrogen compound
- Organonitrogen compound
- 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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