Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 14:43:50 UTC |
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Updated at | 2022-04-28 14:43:50 UTC |
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NP-MRD ID | NP0069379 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (+)-3-O-demethyl-3-epimacronine |
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Description | (+)-3-O-Demethyl-3-epi-macronine belongs to the class of organic compounds known as tazettine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids derived from the haemanthamine-type alkaloids, which are characterized as a linkage between C6 and C11 by an oxygen atom to form a [3,4-g]benzopyran framework. (+)-3-O-demethyl-3-epimacronine is found in Galanthus byzantinus, Galanthus gracilis and Galanthus plicatus. Based on a literature review very few articles have been published on (+)-3-O-Demethyl-3-epi-macronine. |
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Structure | CN1C[C@@H]2OC(=O)C3=CC4=C(OCO4)C=C3[C@]22C=C[C@@H](O)C[C@H]12 InChI=1S/C17H17NO5/c1-18-7-15-17(3-2-9(19)4-14(17)18)11-6-13-12(21-8-22-13)5-10(11)16(20)23-15/h2-3,5-6,9,14-15,19H,4,7-8H2,1H3/t9-,14+,15+,17+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C17H17NO5 |
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Average Mass | 315.3250 Da |
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Monoisotopic Mass | 315.11067 Da |
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IUPAC Name | (1S,13R,16S,18S)-18-hydroxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0^{1,16}.0^{2,10}.0^{4,8}]icosa-2,4(8),9,19-tetraen-11-one |
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Traditional Name | (1S,13R,16S,18S)-18-hydroxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0^{1,16}.0^{2,10}.0^{4,8}]icosa-2,4(8),9,19-tetraen-11-one |
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CAS Registry Number | Not Available |
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SMILES | CN1C[C@@H]2OC(=O)C3=CC4=C(OCO4)C=C3[C@]22C=C[C@@H](O)C[C@H]12 |
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InChI Identifier | InChI=1S/C17H17NO5/c1-18-7-15-17(3-2-9(19)4-14(17)18)11-6-13-12(21-8-22-13)5-10(11)16(20)23-15/h2-3,5-6,9,14-15,19H,4,7-8H2,1H3/t9-,14+,15+,17+/m1/s1 |
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InChI Key | YMULCYGIAHPJSE-HNOLUEMASA-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 tazettine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids derived from the haemanthamine-type alkaloids, which are characterized as a linkage between C6 and C11 by an oxygen atom to form a [3,4-g]benzopyran framework. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Amaryllidaceae alkaloids |
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Sub Class | Tazettine-type amaryllidaceae alkaloids |
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Direct Parent | Tazettine-type amaryllidaceae alkaloids |
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Alternative Parents | |
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Substituents | - Tazettine alkaloid skeleton
- Benzopyran
- Isochromane
- 2-benzopyran
- Benzodioxole
- Indole or derivatives
- Aralkylamine
- N-alkylpyrrolidine
- Benzenoid
- Pyrrolidine
- Amino acid or derivatives
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Tertiary amine
- Tertiary aliphatic amine
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Acetal
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Amine
- Organic oxide
- Alcohol
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic 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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