| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 11:00:26 UTC |
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| Updated at | 2022-04-28 11:00:26 UTC |
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| NP-MRD ID | NP0066769 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 1,2-Dihydrogalanthamine |
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| Description | Lycoramine, also known as (+-)-lycoramine, belongs to the class of organic compounds known as galanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids with a structure characterized a tetracyclic skeleton with two ortho aromatic protons in ring A. 1,2-Dihydrogalanthamine is found in Brunsvigia gregaria, Hymenocallis littoralis, Hymenocallis rotata, Lycoris aurea , Lycoris guangxiensis, Lycoris incarnata, Lycoris longituba, Lycoris radiata, Lycoris radiata Herb. , Lycoris sanguinea, Lycoris sanguinea Maxim, Lycoris squamigera, Lycoris traubii, Narcissus papyraceus Kerl-Gawl, Narcissus pseudonarcissus subsp.pseudonarcissus, Narcissus tazetta L. and Pancratium maritimum. 1,2-Dihydrogalanthamine was first documented in 2021 (PMID: 33434626). Based on a literature review a small amount of articles have been published on Lycoramine (PMID: 35483192) (PMID: 34874174) (PMID: 34659286) (PMID: 33200692). |
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| Structure | COC1=C2O[C@H]3C[C@@H](O)CC[C@]33CCN(C)CC(C=C1)=C23 InChI=1S/C17H23NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-4,12,14,19H,5-10H2,1-2H3/t12-,14-,17-/m0/s1 |
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| Synonyms | | Value | Source |
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| 1,2-Dihydrogalanthamine | Kegg | | (+-)-Lycoramine | MeSH |
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| Chemical Formula | C17H23NO3 |
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| Average Mass | 289.3750 Da |
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| Monoisotopic Mass | 289.16779 Da |
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| IUPAC Name | (1R,12S,14S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6(17),7,9-trien-14-ol |
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| Traditional Name | (1R,12S,14S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6(17),7,9-trien-14-ol |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=C2O[C@H]3C[C@@H](O)CC[C@]33CCN(C)CC(C=C1)=C23 |
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| InChI Identifier | InChI=1S/C17H23NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-4,12,14,19H,5-10H2,1-2H3/t12-,14-,17-/m0/s1 |
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| InChI Key | GJRMHIXYLGOZSE-JDFRZJQESA-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 galanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids with a structure characterized a tetracyclic skeleton with two ortho aromatic protons in ring A. |
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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 | Galanthamine-type amaryllidaceae alkaloids |
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| Direct Parent | Galanthamine-type amaryllidaceae alkaloids |
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| Alternative Parents | |
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| Substituents | - Galanthamine-type amaryllidaceae alkaloid
- Benzazepine
- Coumaran
- Anisole
- Alkyl aryl ether
- Azepine
- Aralkylamine
- Benzenoid
- Cyclic alcohol
- Secondary alcohol
- Tertiary amine
- Tertiary aliphatic amine
- Ether
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organic nitrogen compound
- Alcohol
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxygen compound
- Amine
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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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 | - Aleya F, Xianmin C, Anthony H, Meriel J: Relative expression of putative genes involved in galanthamine and other Amaryllidaceae alkaloids biosynthesis in Narcissus field and in vitro tissues. Gene. 2021 Mar 30;774:145424. doi: 10.1016/j.gene.2021.145424. Epub 2021 Jan 9. [PubMed:33434626 ]
- 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 ]
- Chang YP, Ma X, Shao H, Zhao YM: Total Syntheses of Galanthamine and Lycoramine via a Palladium-Catalyzed Cascade Cyclization and Late-Stage Reorganization of the Cyclized Skeleton. Org Lett. 2021 Dec 17;23(24):9659-9663. doi: 10.1021/acs.orglett.1c03943. Epub 2021 Dec 7. [PubMed:34874174 ]
- Li Q, Xu J, Zheng Y, Zhang Y, Cai Y: Transcriptomic and Metabolomic Analyses Reveals That Exogenous Methyl Jasmonate Regulates Galanthamine Biosynthesis in Lycoris longituba Seedlings. Front Plant Sci. 2021 Sep 30;12:713795. doi: 10.3389/fpls.2021.713795. eCollection 2021. [PubMed:34659286 ]
- Kiris I, Basar MK, Sahin B, Gurel B, Coskun J, Mroczek T, Baykal AT: Evaluation of the Therapeutic Effect of Lycoramine on Alzheimer's Disease in Mouse Model. Curr Med Chem. 2021;28(17):3449-3473. doi: 10.2174/0929867327999201116193126. [PubMed:33200692 ]
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