Record Information |
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Version | 1.0 |
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Created at | 2022-06-29 19:18:37 UTC |
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Updated at | 2022-06-29 19:18:38 UTC |
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NP-MRD ID | NP0138821 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Lirinidine |
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Description | Lirinidine belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Lirinidine is found in Annona purpurea, Liriodendron tulipifera, Magnolia obovata, Nelumbo nucifera, Neostenanthera gabonensis and Ocotea macrophylla. It was first documented in 2013 (PMID: 23270663). Based on a literature review a small amount of articles have been published on Lirinidine (PMID: 31707550) (PMID: 24705566) (PMID: 34664390) (PMID: 34019754). |
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Structure | COC1=C(O)C2=C3[C@H](CC4=CC=CC=C24)N(C)CCC3=C1 InChI=1S/C18H19NO2/c1-19-8-7-12-10-15(21-2)18(20)17-13-6-4-3-5-11(13)9-14(19)16(12)17/h3-6,10,14,20H,7-9H2,1-2H3/t14-/m0/s1 |
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Synonyms | Value | Source |
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Lirinidine, (+-)-isomer | MeSH | Lirinidine, (R)-isomer | MeSH |
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Chemical Formula | C18H19NO2 |
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Average Mass | 281.3550 Da |
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Monoisotopic Mass | 281.14158 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 54383-28-7 |
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SMILES | COC1=C(O)C2=C3[C@H](CC4=CC=CC=C24)N(C)CCC3=C1 |
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InChI Identifier | InChI=1S/C18H19NO2/c1-19-8-7-12-10-15(21-2)18(20)17-13-6-4-3-5-11(13)9-14(19)16(12)17/h3-6,10,14,20H,7-9H2,1-2H3/t14-/m0/s1 |
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InChI Key | YXVXMURDCBMPRH-AWEZNQCLSA-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, 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 aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Aporphines |
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Sub Class | Not Available |
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Direct Parent | Aporphines |
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Alternative Parents | |
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Substituents | - Aporphine
- Benzoquinoline
- Phenanthrene
- 1-naphthol
- Naphthalene
- Quinoline
- Tetrahydroisoquinoline
- Anisole
- Alkyl aryl ether
- Aralkylamine
- Benzenoid
- Tertiary amine
- Tertiary aliphatic amine
- Organoheterocyclic compound
- Azacycle
- Ether
- Amine
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen 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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General References | - Yano M, Nakashima S, Oda Y, Nakamura S, Matsuda H: BBB-permeable aporphine-type alkaloids in Nelumbo nucifera flowers with accelerative effects on neurite outgrowth in PC-12 cells. J Nat Med. 2020 Jan;74(1):212-218. doi: 10.1007/s11418-019-01368-7. Epub 2019 Nov 9. [PubMed:31707550 ]
- Kang YF, Liu CM, Kao CL, Chen CY: Antioxidant and anticancer constituents from the leaves of Liriodendron tulipifera. Molecules. 2014 Apr 3;19(4):4234-45. doi: 10.3390/molecules19044234. [PubMed:24705566 ]
- Cao TW, Xie CL, Chen CQ, He ZH, Yan QX, Xu G, Yang XW: Anti-Food Allergic Alkaloids from the Lotus Seed Pot. Chem Biodivers. 2021 Dec;18(12):e2100770. doi: 10.1002/cbdv.202100770. Epub 2021 Nov 10. [PubMed:34664390 ]
- Maneenet J, Omar AM, Sun S, Kim MJ, Daodee S, Monthakantirat O, Boonyarat C, Chulikhit Y, Awale S: Benzylisoquinoline alkaloids from Nelumbo nucifera Gaertn. petals with antiausterity activities against the HeLa human cervical cancer cell line. Z Naturforsch C J Biosci. 2021 May 24;76(9-10):401-406. doi: 10.1515/znc-2020-0304. Print 2021 Sep 27. [PubMed:34019754 ]
- Nakamura S, Nakashima S, Tanabe G, Oda Y, Yokota N, Fujimoto K, Matsumoto T, Sakuma R, Ohta T, Ogawa K, Nishida S, Miki H, Matsuda H, Muraoka O, Yoshikawa M: Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells. Bioorg Med Chem. 2013 Feb 1;21(3):779-87. doi: 10.1016/j.bmc.2012.11.038. Epub 2012 Dec 5. [PubMed:23270663 ]
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