| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-30 16:47:32 UTC |
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| Updated at | 2024-09-03 04:20:09 UTC |
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| NP-MRD ID | NP0137279 |
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| Natural Product DOI | https://doi.org/10.57994/2001 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Lycorine |
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| Description | 5,7-Dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]Nonadeca-2,4(8),9,15-tetraene-17,18-diol belongs to the class of organic compounds known as lycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the lycorine skeleton, made up of a pyrrolo[d,e]phenanthridine ring system. Lycorine is found in Crinum amabile, Crinum asiaticum, Crinum bulbispermum, Crinum kirkii, Crinum latifolium, Crinum yemense, Hippeastrum vittatum, Hymenocallis rotata, Imperata cylindrica, Leucojum vernum, Lycoris sanguinea and Zephyranthes candida. 5,7-Dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]Nonadeca-2,4(8),9,15-tetraene-17,18-diol is a very strong basic compound (based on its pKa). |
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| Structure | OC1C=C2CCN3CC4=CC5=C(OCO5)C=C4C(C23)C1O InChI=1S/C16H17NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h3-5,11,14-16,18-19H,1-2,6-7H2 |
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| Synonyms | Not Available |
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| Chemical Formula | C16H17NO4 |
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| Average Mass | 287.3150 Da |
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| Monoisotopic Mass | 287.11576 Da |
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| IUPAC Name | 5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9,15-tetraene-17,18-diol |
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| Traditional Name | lycorine |
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| CAS Registry Number | Not Available |
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| SMILES | OC1C=C2CCN3CC4=CC5=C(OCO5)C=C4C(C23)C1O |
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| InChI Identifier | InChI=1S/C16H17NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h3-5,11,14-16,18-19H,1-2,6-7H2 |
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| InChI Key | XGVJWXAYKUHDOO-UHFFFAOYSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| COSY NMR | [1H, 1H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental) | luis.guerrero@unige.ch | University of Geneva | Luis Quiros-Guerrero, PhD | 2024-03-28 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | luis.guerrero@unige.ch | University of Geneva | Luis Quiros-Guerrero, PhD | 2024-03-28 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, CDCl3, experimental) | luis.guerrero@unige.ch | University of Geneva | Luis Quiros-Guerrero, PhD | 2024-03-28 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | luis.guerrero@unige.ch | University of Geneva | Luis Quiros-Guerrero, PhD | 2024-03-28 | View Spectrum |
| | 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 lycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the lycorine skeleton, made up of a pyrrolo[d,e]phenanthridine ring system. |
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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 | Lycorine-type amaryllidaceae alkaloids |
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| Direct Parent | Lycorine-type amaryllidaceae alkaloids |
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| Alternative Parents | |
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| Substituents | - Lycorine skeleton
- Benzoquinoline
- Phenanthridine
- Quinoline
- Tetrahydroisoquinoline
- Benzodioxole
- Indole or derivatives
- Aralkylamine
- Benzenoid
- N-alkylpyrrolidine
- Pyrrolidine
- Tertiary aliphatic amine
- Tertiary amine
- Secondary alcohol
- 1,2-diol
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Acetal
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Organic nitrogen compound
- Organic oxygen compound
- Amine
- Alcohol
- Organopnictogen 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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