Record Information |
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Version | 2.0 |
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Created at | 2022-09-12 00:01:27 UTC |
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Updated at | 2022-09-12 00:01:28 UTC |
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NP-MRD ID | NP0321685 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2s,3r,9s,10s)-9-hydroxy-4-methyl-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),7,13,15(19)-tetraen-12-one |
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Description | (2S,3R,9S,10S)-9-hydroxy-4-methyl-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]Icosa-1(20),7,13,15(19)-tetraen-12-one belongs to the class of organic compounds known as homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids. (2s,3r,9s,10s)-9-hydroxy-4-methyl-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),7,13,15(19)-tetraen-12-one is found in Hippeastrum puniceum. Based on a literature review very few articles have been published on (2S,3R,9S,10S)-9-hydroxy-4-methyl-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]Icosa-1(20),7,13,15(19)-tetraen-12-one. |
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Structure | CN1CCC2=C[C@H](O)[C@H]3OC(=O)C4=CC5=C(OCO5)C=C4[C@H]3[C@@H]12 InChI=1S/C17H17NO5/c1-18-3-2-8-4-11(19)16-14(15(8)18)9-5-12-13(22-7-21-12)6-10(9)17(20)23-16/h4-6,11,14-16,19H,2-3,7H2,1H3/t11-,14-,15-,16+/m0/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 | (2S,3R,9S,10S)-9-hydroxy-4-methyl-11,16,18-trioxa-4-azapentacyclo[11.7.0.0^{2,10}.0^{3,7}.0^{15,19}]icosa-1(20),7,13,15(19)-tetraen-12-one |
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Traditional Name | (2S,3R,9S,10S)-9-hydroxy-4-methyl-11,16,18-trioxa-4-azapentacyclo[11.7.0.0^{2,10}.0^{3,7}.0^{15,19}]icosa-1(20),7,13,15(19)-tetraen-12-one |
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CAS Registry Number | Not Available |
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SMILES | CN1CCC2=C[C@H](O)[C@H]3OC(=O)C4=CC5=C(OCO5)C=C4[C@H]3[C@@H]12 |
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InChI Identifier | InChI=1S/C17H17NO5/c1-18-3-2-8-4-11(19)16-14(15(8)18)9-5-12-13(22-7-21-12)6-10(9)17(20)23-16/h4-6,11,14-16,19H,2-3,7H2,1H3/t11-,14-,15-,16+/m0/s1 |
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InChI Key | DGQPIOQRPAGNGB-VCOSZWKGSA-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 homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids. |
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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 | Homolycorine-type amaryllidaceae alkaloids |
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Direct Parent | Homolycorine-type amaryllidaceae alkaloids |
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Alternative Parents | |
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Substituents | - Homolycorine 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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