Record Information |
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Version | 1.0 |
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Created at | 2021-06-21 00:57:07 UTC |
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Updated at | 2021-06-30 00:19:21 UTC |
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NP-MRD ID | NP0043586 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | huperzine D |
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Provided By | JEOL Database![JEOL Logo](/attributions/jeol_logo.png) |
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Description | Huperzine D belongs to the class of organic compounds known as quinolones and derivatives. Quinolones and derivatives are compounds containing a quinoline moiety which bears a ketone group. huperzine D is found in Huperzia serrata and Lycopodiastrum casuarinoides. It was first documented in 2020 (PMID: 32970179). Based on a literature review a significant number of articles have been published on Huperzine D (PMID: 34072855) (PMID: 33930191) (PMID: 32590113) (PMID: 31826414). |
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Structure | [H]OC([H])([H])C1=C([H])[C@@]2([H])C([H])([H])C3=C(C([H])=C([H])C(=O)N3[H])[C@@](N(C([H])([H])[H])C([H])([H])[H])(C1([H])[H])[C@]2([H])C([H])=C([H])[H] InChI=1S/C17H22N2O2/c1-4-13-12-7-11(10-20)9-17(13,19(2)3)14-5-6-16(21)18-15(14)8-12/h4-7,12-13,20H,1,8-10H2,2-3H3,(H,18,21)/t12-,13+,17+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C17H22N2O2 |
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Average Mass | 286.3750 Da |
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Monoisotopic Mass | 286.16813 Da |
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IUPAC Name | (1R,9R,13R)-1-(dimethylamino)-13-ethenyl-11-(hydroxymethyl)-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,10-trien-5-one |
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Traditional Name | (1R,9R,13R)-1-(dimethylamino)-13-ethenyl-11-(hydroxymethyl)-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,10-trien-5-one |
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CAS Registry Number | Not Available |
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SMILES | [H]OC([H])([H])C1=C([H])[C@@]2([H])C([H])([H])C3=C(C([H])=C([H])C(=O)N3[H])[C@@](N(C([H])([H])[H])C([H])([H])[H])(C1([H])[H])[C@]2([H])C([H])=C([H])[H] |
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InChI Identifier | InChI=1S/C17H22N2O2/c1-4-13-12-7-11(10-20)9-17(13,19(2)3)14-5-6-16(21)18-15(14)8-12/h4-7,12-13,20H,1,8-10H2,2-3H3,(H,18,21)/t12-,13+,17+/m0/s1 |
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InChI Key | NWIQTODXBDJEAN-OGHNNQOOSA-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, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | 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 quinolones and derivatives. Quinolones and derivatives are compounds containing a quinoline moiety which bears a ketone group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Quinolines and derivatives |
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Sub Class | Quinolones and derivatives |
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Direct Parent | Quinolones and derivatives |
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Alternative Parents | |
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Substituents | - Quinolone
- Pyridinone
- Aralkylamine
- Pyridine
- Heteroaromatic compound
- Lactam
- Tertiary amine
- Tertiary aliphatic amine
- Azacycle
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Amine
- Alcohol
- 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 | - Yang Y, Dai L, Wu D, Dong L, Tu Y, Xie J, Luo X: In Vitro Propagation, Huperzine A Content and Antioxidant Activity of Three Genotypic Huperzia serrata. Plants (Basel). 2021 May 31;10(6). pii: plants10061112. doi: 10.3390/plants10061112. [PubMed:34072855 ]
- Mak S, Li W, Fu H, Luo J, Cui W, Hu S, Pang Y, Carlier PR, Tsim KW, Pi R, Han Y: Promising tacrine/huperzine A-based dimeric acetylcholinesterase inhibitors for neurodegenerative disorders: From relieving symptoms to modifying diseases through multitarget. J Neurochem. 2021 Apr 30. doi: 10.1111/jnc.15379. [PubMed:33930191 ]
- Wen-Xia H, Zhong-Wen H, Min J, Han Z, Wei-Ze L, Li-Bin Y, Fei L, Lu H, Ning Z, Xiao-Feng L: Five novel and highly efficient endophytic fungi isolated from Huperzia serrata expressing huperzine A for the treatment of Alzheimer's disease. Appl Microbiol Biotechnol. 2020 Nov;104(21):9159-9177. doi: 10.1007/s00253-020-10894-4. Epub 2020 Sep 24. [PubMed:32970179 ]
- Xu W, Liu X, He X, Jiang Y, Zhang J, Zhang Q, Wang N, Qin L, Xin H: Bajitianwan attenuates D-galactose-induced memory impairment and bone loss through suppression of oxidative stress in aging rat model. J Ethnopharmacol. 2020 Oct 28;261:112992. doi: 10.1016/j.jep.2020.112992. Epub 2020 Jun 23. [PubMed:32590113 ]
- Shi W, Zhong J, Zhang Q, Yan C: Structural characterization and antineuroinflammatory activity of a novel heteropolysaccharide obtained from the fruits of Alpinia oxyphylla. Carbohydr Polym. 2020 Feb 1;229:115405. doi: 10.1016/j.carbpol.2019.115405. Epub 2019 Oct 1. [PubMed:31826414 ]
- Tang, Y., et al. (2013). Tang, Y., et al, J. Nat. Prod. 76, 1475 (2013). J. Nat. Prod..
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