Record Information |
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Version | 1.0 |
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Created at | 2021-06-21 00:04:00 UTC |
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Updated at | 2021-06-30 00:17:26 UTC |
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NP-MRD ID | NP0042389 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | lycopodine |
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Provided By | JEOL Database![JEOL Logo](/attributions/jeol_logo.png) |
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Description | lycopodine is found in Austrolycopodium magellanicum, Dendrolycopodium obscurum, Diphasiastrum alpinum, Diphasiastrum thyoides, Diphasiastrum tristachyum, Huperzia lucidula, Palhinhaea cernua, Phlegmariurus filiformis, Phlegmariurus phlegmaria, Phlegmariurus varius and Pseudodiphasium volubile. It was first documented in 2019 (PMID: 30928888). Based on a literature review a significant number of articles have been published on lycopodine (PMID: 33804083) (PMID: 32941036) (PMID: 32914364) (PMID: 32009077). |
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Structure | [H]C([H])([H])[C@]1([H])C([H])([H])[C@@]2([H])C([H])([H])C(=O)[C@@]3([H])C([H])([H])C([H])([H])C([H])([H])N4C([H])([H])C([H])([H])C([H])([H])[C@@]2([H])[C@]34C1([H])[H] InChI=1S/C16H25NO/c1-11-8-12-9-15(18)14-5-3-7-17-6-2-4-13(12)16(14,17)10-11/h11-14H,2-10H2,1H3/t11-,12+,13-,14-,16-/m1/s1 |
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Synonyms | Value | Source |
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(16R)-Methyllycopodan-5-one | MeSH |
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Chemical Formula | C16H25NO |
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Average Mass | 247.3820 Da |
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Monoisotopic Mass | 247.19361 Da |
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IUPAC Name | (1R,2R,10S,13S,15R)-15-methyl-6-azatetracyclo[8.6.0.0^{1,6}.0^{2,13}]hexadecan-11-one |
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Traditional Name | (1R,2R,10S,13S,15R)-15-methyl-6-azatetracyclo[8.6.0.0^{1,6}.0^{2,13}]hexadecan-11-one |
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CAS Registry Number | Not Available |
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SMILES | [H]C([H])([H])[C@]1([H])C([H])([H])[C@@]2([H])C([H])([H])C(=O)[C@@]3([H])C([H])([H])C([H])([H])C([H])([H])N4C([H])([H])C([H])([H])C([H])([H])[C@@]2([H])[C@]34C1([H])[H] |
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InChI Identifier | InChI=1S/C16H25NO/c1-11-8-12-9-15(18)14-5-3-7-17-6-2-4-13(12)16(14,17)10-11/h11-14H,2-10H2,1H3/t11-,12+,13-,14-,16-/m1/s1 |
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InChI Key | BCZFSDNVXODRAJ-JTTNIQEDSA-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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1D NMR | 13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | 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, 100 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, chcl3, 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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Classification | Not classified |
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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 | - Dymek A, Widelski J, Wojtanowski KK, Ploszaj P, Zhuravchak R, Mroczek T: Optimization of Pressurized Liquid Extraction of Lycopodiaceae Alkaloids Obtained from Two Lycopodium Species. Molecules. 2021 Mar 15;26(6). pii: molecules26061626. doi: 10.3390/molecules26061626. [PubMed:33804083 ]
- Zhu X, Xia D, Zhou Z, Xie S, Shi Z, Chen G, Wang L, Pan K: Lycosquarrines A-R, Lycopodium Alkaloids from Phlegmariurus squarrosus. J Nat Prod. 2020 Oct 23;83(10):2831-2843. doi: 10.1021/acs.jnatprod.9b00815. Epub 2020 Sep 17. [PubMed:32941036 ]
- Yang Z, Yin Q, Ma J, Yang C, Sheng Y, Song L, Pang T, Zhuang P, Guo H, Zhang Y: Screen the Effective Components of Lycopodii herba on Rheumatoid Arthritis with the Aid of Spectrum-Effect Relationship and Uncover its Potential Mechanism. Inflammation. 2020 Dec;43(6):2087-2097. doi: 10.1007/s10753-020-01276-z. [PubMed:32914364 ]
- Takayama H: Total Syntheses of Lycopodium and Monoterpenoid Indole Alkaloids Based on Biosynthesis-Inspired Strategies. Chem Pharm Bull (Tokyo). 2020;68(2):103-116. doi: 10.1248/cpb.c19-00872. [PubMed:32009077 ]
- Xiong J, Meng WJ, Zhang HY, Zou Y, Wang WX, Wang XY, Yang QL, Osman EEA, Hu JF: Lycofargesiines A-F, further Lycopodium alkaloids from the club moss Huperzia fargesii. Phytochemistry. 2019 Jun;162:183-192. doi: 10.1016/j.phytochem.2019.03.015. Epub 2019 Mar 29. [PubMed:30928888 ]
- Halldorsdottir, E. S., et al. (2013). Halldorsdottir, E. S., et al, Phytochem. Lett. 6, 355 (2013). Phytochem..
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