| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 11:02:00 UTC |
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| Updated at | 2022-04-28 11:02:00 UTC |
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| NP-MRD ID | NP0066803 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Vittatine |
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| Description | Vittatine belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other. Vittatine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Vittatine is found in Amaryllis belladonna, Crinum asiaticum, Crinum bulbispermum, Crinum bulbispermum Milne, Crinum yemense, Eucharis amazonica, Hippeastrum papilio, Hippeastrum puniceum, Hippeastrum vittatum, Hippeastrum vittatum L.'Herr., Hymenocallis littoralis, Hymenocallis rotata, Ismene narcissiflora, Lycoris radiata, Narcissus pseudonarcissus subsp.pseudonarcissus, Nerine sarniensis, Pancratium canariense, Pancratium maritimum, Pancratium sickenbergeri and Zephyranthes citrina. Vittatine was first documented in 2020 (PMID: 30636443). Based on a literature review a small amount of articles have been published on vittatine (PMID: 35483192) (PMID: 35448871) (PMID: 34641567) (PMID: 33801149). |
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| Structure | O[C@H]1C[C@@H]2N3CC[C@@]2(C=C1)C1=CC2=C(OCO2)C=C1C3 InChI=1S/C16H17NO3/c18-11-1-2-16-3-4-17(15(16)6-11)8-10-5-13-14(7-12(10)16)20-9-19-13/h1-2,5,7,11,15,18H,3-4,6,8-9H2/t11-,15+,16+/m1/s1 |
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| Synonyms | | Value | Source |
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| (3beta,5alpha,13beta,19alpha)-1,2-Didehydro-crinan-3-ol | Kegg | | (3b,5a,13b,19a)-1,2-Didehydro-crinan-3-ol | Generator | | (3Β,5α,13β,19α)-1,2-didehydro-crinan-3-ol | Generator |
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| Chemical Formula | C16H17NO3 |
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| Average Mass | 271.3160 Da |
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| Monoisotopic Mass | 271.12084 Da |
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| IUPAC Name | (1R,13S,15S)-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraen-15-ol |
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| Traditional Name | (1R,13S,15S)-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraen-15-ol |
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| CAS Registry Number | Not Available |
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| SMILES | O[C@H]1C[C@@H]2N3CC[C@@]2(C=C1)C1=CC2=C(OCO2)C=C1C3 |
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| InChI Identifier | InChI=1S/C16H17NO3/c18-11-1-2-16-3-4-17(15(16)6-11)8-10-5-13-14(7-12(10)16)20-9-19-13/h1-2,5,7,11,15,18H,3-4,6,8-9H2/t11-,15+,16+/m1/s1 |
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| InChI Key | RPAORVSEYNOMBR-RLCCDNCMSA-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 crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other. |
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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 | Crinine- and Haemanthamine-type amaryllidaceae alkaloids |
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| Direct Parent | Crinine- and Haemanthamine-type amaryllidaceae alkaloids |
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| Alternative Parents | |
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| Substituents | - Hemanthamine/crinine alkaloid skeleton
- Benzoquinoline
- Phenanthridine
- Benzazepine
- Quinoline
- Tetrahydroisoquinoline
- Benzodioxole
- Indole or derivatives
- Azepine
- Aralkylamine
- N-alkylpyrrolidine
- Benzenoid
- Pyrrolidine
- Tertiary aliphatic amine
- Tertiary amine
- Secondary alcohol
- Organoheterocyclic compound
- Acetal
- Oxacycle
- Azacycle
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Alcohol
- Organonitrogen compound
- Organooxygen compound
- Amine
- 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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| General References | - Sierra K, de Andrade JP, R Tallini L, Osorio EH, Yanez O, Osorio MI, Oleas NH, Garcia-Beltran O, de S Borges W, Bastida J, Osorio E, Cortes N: In vitro and in silico analysis of galanthine from Zephyranthes carinata as an inhibitor of acetylcholinesterase. Biomed Pharmacother. 2022 Jun;150:113016. doi: 10.1016/j.biopha.2022.113016. Epub 2022 Apr 25. [PubMed:35483192 ]
- Masi M, Di Lecce R, Merindol N, Girard MP, Berthoux L, Desgagne-Penix I, Calabro V, Evidente A: Cytotoxicity and Antiviral Properties of Alkaloids Isolated from Pancratium maritimum. Toxins (Basel). 2022 Apr 7;14(4). pii: toxins14040262. doi: 10.3390/toxins14040262. [PubMed:35448871 ]
- Maafi N, Mamun AA, Jandourek O, Marikova J, Breiterova K, Diepoltova A, Konecna K, Hostalkova A, Hulcova D, Kunes J, Kohelova E, Koutova D, Safratova M, Novakova L, Cahlikova L: Semisynthetic Derivatives of Selected Amaryllidaceae Alkaloids as a New Class of Antimycobacterial Agents. Molecules. 2021 Oct 4;26(19). pii: molecules26196023. doi: 10.3390/molecules26196023. [PubMed:34641567 ]
- Atrahimovich D, Harris R, Eitan R, Cohen M, Khatib S: Galantamine Quantity and Alkaloid Profile in the Bulbs of Narcissus tazetta and daffodil cultivars (Amaryllidaceae) Grown in Israel. Metabolites. 2021 Mar 21;11(3). pii: metabo11030185. doi: 10.3390/metabo11030185. [PubMed:33801149 ]
- Katoch D, Kumar D, Padwad YS, Singh B, Sharma U: Narciclasine-4-O-beta-D-xylopyranoside, a new narciclasine glycoside from Zephyranthes minuta. Nat Prod Res. 2020 Jan;34(2):233-240. doi: 10.1080/14786419.2018.1527836. Epub 2019 Jan 12. [PubMed:30636443 ]
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