| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 01:17:41 UTC |
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| Updated at | 2022-04-28 01:17:41 UTC |
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| NP-MRD ID | NP0055159 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (-)-Sophocarpine |
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| Description | Sophocarpine belongs to the class of organic compounds known as matrine alkaloids. These are lupin alkaloids with a structure based on the matrine skeleton, a four-ring skeleton that based on a saturated dipyrido[2,1-f:3',2',1'-Ij][1,6]naphthyridin-10-one skeleton. (-)-Sophocarpine is found in Ammodendron bifolium, Ammothamnus lehmanni Bge., Corydalis yanhusuo , Daphniphyllum oldhami, Leontice smirnovii, Sophora alopecuroides, Sophora davidii, Sophora flavescens , Sophora flavescens var. angustifolia , Sophora japonica L. , Sophora jaubertii, Sophora moorcroftiana Benth. , Sophora pachycarpa, Sophora subprostrata, Sophora tonkinensis, Sophora viciifolia, Styphnolobium japonicum and Vexibia pachycarpa. (-)-Sophocarpine was first documented in 2021 (PMID: 35002280). Based on a literature review a small amount of articles have been published on Sophocarpine (PMID: 35468537) (PMID: 35185568) (PMID: 35126158) (PMID: 34830730). |
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| Structure | O=C1C=CC[C@@H]2[C@H]3CCCN4CCC[C@@H](CN12)[C@@H]34 InChI=1S/C15H22N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h1,7,11-13,15H,2-6,8-10H2/t11-,12+,13+,15-/m0/s1 |
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| Synonyms | | Value | Source |
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| 13,14-Didehydro-matridin-15-one | MeSH | | Sophocarpine hydrobromide | MeSH |
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| Chemical Formula | C15H22N2O |
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| Average Mass | 246.3540 Da |
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| Monoisotopic Mass | 246.17321 Da |
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| IUPAC Name | (1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-6-one |
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| Traditional Name | (1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-6-one |
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| CAS Registry Number | Not Available |
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| SMILES | O=C1C=CC[C@@H]2[C@H]3CCCN4CCC[C@@H](CN12)[C@@H]34 |
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| InChI Identifier | InChI=1S/C15H22N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h1,7,11-13,15H,2-6,8-10H2/t11-,12+,13+,15-/m0/s1 |
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| InChI Key | AAGFPTSOPGCENQ-JLNYLFASSA-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 matrine alkaloids. These are lupin alkaloids with a structure based on the matrine skeleton, a four-ring skeleton that based on a saturated dipyrido[2,1-f:3',2',1'-Ij][1,6]naphthyridin-10-one skeleton. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Lupin alkaloids |
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| Sub Class | Matrine alkaloids |
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| Direct Parent | Matrine alkaloids |
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| Alternative Parents | |
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| Substituents | - Matrine
- Diazanaphthalene
- Naphthyridine
- Quinolizidine
- Piperidine
- Tertiary carboxylic acid amide
- Amino acid or derivatives
- Carboxamide group
- Lactam
- Tertiary amine
- Tertiary aliphatic amine
- Carboxylic acid derivative
- Organoheterocyclic compound
- Azacycle
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Hydrocarbon derivative
- Amine
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic 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 | - Chen S, Ma S, Wang H, Shao X, Ding B, Guo Z, Chen X, Wang Y: Unraveling the mechanism of alkaloids from Sophora alopecuroides Linn combined with immune checkpoint blockade in the treatment of non-small cell lung cancer based on systems pharmacology. Bioorg Med Chem. 2022 Jun 15;64:116724. doi: 10.1016/j.bmc.2022.116724. Epub 2022 Mar 26. [PubMed:35468537 ]
- Zhang Z, Xie Z, Lv S, Shi Y, Zhai C, Li X, Qiao B, Gao X: Integrated Metabolomics and Network Pharmacology Study on the Mechanism of Kangfuxiaoyan Suppository for Treating Chronic Pelvic Inflammatory Disease. Front Pharmacol. 2022 Feb 4;13:812587. doi: 10.3389/fphar.2022.812587. eCollection 2022. [PubMed:35185568 ]
- Weng Q, Lan X, Wang Y, Fan C, Xu RA, Zhang P: Effect of Sophocarpine on the Pharmacokinetics of Umbralisib in Rat Plasma Using a Novel UPLC-MS/MS Method. Front Pharmacol. 2022 Jan 20;13:749095. doi: 10.3389/fphar.2022.749095. eCollection 2022. [PubMed:35126158 ]
- Wang DD, Wu XY, Dong JY, Cheng XP, Gu SF, Olatunji OJ, Li Y, Zuo J: Qing-Luo-Yin Alleviated Experimental Arthritis in Rats by Disrupting Immune Feedback Between Inflammatory T Cells and Monocytes: Key Evidences from Its Effects on Immune Cell Phenotypes. J Inflamm Res. 2021 Dec 30;14:7467-7486. doi: 10.2147/JIR.S346365. eCollection 2021. [PubMed:35002280 ]
- Yang G, Zeng R, Song X, Liu C, Ni L: Sophocarpine Alleviates Injury-Induced Intima Hyperplasia of Carotid Arteries by Suppressing Inflammation in a Rat Model. J Clin Med. 2021 Nov 22;10(22). pii: jcm10225449. doi: 10.3390/jcm10225449. [PubMed:34830730 ]
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