| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 13:07:00 UTC |
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| Updated at | 2022-04-28 13:07:00 UTC |
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| NP-MRD ID | NP0068112 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | D-(-)-Nuciferine |
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| Description | Nuciferine 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. D-(-)-Nuciferine is found in Annona cherimola, Annona cherimolia, Artabotrys venustus, Cissampelos pareira , Hexalobus monopetalus, Liriodendron tulipifera, Nelumbo caerulea, Nelumbo nucifera , Paliurus hemsleyanus, Papaver caucasicum, Plumula nelumbensis, Ziziphus jujuba and Zizyphus vulgaris. D-(-)-Nuciferine was first documented in 2021 (PMID: 35003297). Based on a literature review a small amount of articles have been published on Nuciferine (PMID: 35350700) (PMID: 35298888) (PMID: 35167658) (PMID: 35098593). |
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| Structure | COC1=C(OC)C2=C3[C@@H](CC4=CC=CC=C24)N(C)CCC3=C1 InChI=1S/C19H21NO2/c1-20-9-8-13-11-16(21-2)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,11,15H,8-10H2,1-3H3/t15-/m1/s1 |
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| Synonyms | | Value | Source |
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| L-5,6-Dimethoxyaporphine | MeSH | | Nuciferine, (+-)-isomer | MeSH | | Nuciferine, (S)-isomer | MeSH |
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| Chemical Formula | C19H21NO2 |
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| Average Mass | 295.3820 Da |
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| Monoisotopic Mass | 295.15723 Da |
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| IUPAC Name | (9R)-15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,13,15-hexaene |
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| Traditional Name | (9R)-15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,13,15-hexaene |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=C(OC)C2=C3[C@@H](CC4=CC=CC=C24)N(C)CCC3=C1 |
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| InChI Identifier | InChI=1S/C19H21NO2/c1-20-9-8-13-11-16(21-2)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,11,15H,8-10H2,1-3H3/t15-/m1/s1 |
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| InChI Key | ORJVQPIHKOARKV-OAHLLOKOSA-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 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
- Naphthalene
- Quinoline
- Tetrahydroisoquinoline
- Anisole
- Aralkylamine
- Alkyl aryl ether
- Benzenoid
- Tertiary aliphatic amine
- Tertiary amine
- Organoheterocyclic compound
- Azacycle
- Ether
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Organic oxygen compound
- Organic nitrogen compound
- Organopnictogen 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 | - Xu X, Wang W, Chen Y, Zhang Q, Li B, Zhong Y, Tu Y, Zhang W, Xu G, Jiang L: Simultaneous Determination of Ten Bioactive Components from Shenling Baizhu San in Rat Plasma by UHPLC-MS/MS: Application to a Comparative Pharmacokinetic Study in Normal and Two Models of Ulcerative Colitis Rats. Evid Based Complement Alternat Med. 2021 Dec 29;2021:3518241. doi: 10.1155/2021/3518241. eCollection 2021. [PubMed:35003297 ]
- Zheng L, Jiang H, Li R, Song L, Chen R, Dong H: The Pharmacological Mechanisms of Xiaochaihutang in Treating Breast Cancer Based on Network Pharmacology. Contrast Media Mol Imaging. 2022 Mar 9;2022:3900636. doi: 10.1155/2022/3900636. eCollection 2022. [PubMed:35350700 ]
- Bai X, Liu X, Li S, An H, Kang X, Guo S: Nuciferine Inhibits TMEM16A in Dietary Adjuvant Therapy for Lung Cancer. J Agric Food Chem. 2022 Mar 30;70(12):3687-3696. doi: 10.1021/acs.jafc.1c08375. Epub 2022 Mar 17. [PubMed:35298888 ]
- Wu M, Qi F, Qiu R, Feng J, Ren X, Rong S, Ma H, Pan H, Chang D: Electrochemical Detection of Nuciferine in the Lotus Leaf Based on Efficient Catalysis by Zirconium-MOFs. J AOAC Int. 2022 Jun 29;105(4):1175-1182. doi: 10.1093/jaoacint/qsac024. [PubMed:35167658 ]
- Yu X, Chen ML, Liu Y, Li CH, Qiu XL, Ren XL, Wang M, Zhang DQ: An eco-friendly extraction and purification method of nuciferine from Folium nelumbinis with p-sulfonatocalix[6]arenes. Phytochem Anal. 2022 Jun;33(4):543-553. doi: 10.1002/pca.3108. Epub 2022 Jan 31. [PubMed:35098593 ]
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