| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-31 16:32:53 UTC |
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| Updated at | 2022-05-31 16:32:54 UTC |
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| NP-MRD ID | NP0137772 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (+)-Sophoranol |
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| Description | Sophoranol, also known as 5-hydroxymatrine, 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. (+)-Sophoranol is found in Cuscuta chilensis, Sophora flavescens, Sophora jaubertii, Sophora macrocarpa and Sophora tonkinensis. (+)-Sophoranol was first documented in 2007 (PMID: 17370298). Based on a literature review a small amount of articles have been published on Sophoranol (PMID: 32924588) (PMID: 28936848) (PMID: 30209906) (PMID: 26132528). |
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| Structure | [H][C@]12CCCC(=O)N1C[C@]1(O)CCCN3CCC[C@@]2([H])[C@]13[H] InChI=1S/C15H24N2O2/c18-13-6-1-5-12-11-4-2-8-16-9-3-7-15(19,14(11)16)10-17(12)13/h11-12,14,19H,1-10H2/t11-,12-,14-,15-/m1/s1 |
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| Synonyms | | Value | Source |
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| 5-Hydroxymatrine | Kegg |
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| Chemical Formula | C15H24N2O2 |
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| Average Mass | 264.3690 Da |
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| Monoisotopic Mass | 264.18378 Da |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | 3411-37-8 |
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| SMILES | [H][C@]12CCCC(=O)N1C[C@]1(O)CCCN3CCC[C@@]2([H])[C@]13[H] |
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| InChI Identifier | InChI=1S/C15H24N2O2/c18-13-6-1-5-12-11-4-2-8-16-9-3-7-15(19,14(11)16)10-17(12)13/h11-12,14,19H,1-10H2/t11-,12-,14-,15-/m1/s1 |
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| InChI Key | VQYBAEAOOJBSTR-QHSBEEBCSA-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 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
- Quinolizidinone
- Diazanaphthalene
- Naphthyridine
- Quinolizidine
- Delta-lactam
- Piperidinone
- Piperidine
- Tertiary carboxylic acid amide
- Tertiary alcohol
- 1,2-aminoalcohol
- Amino acid or derivatives
- Carboxamide group
- Lactam
- Tertiary aliphatic amine
- Tertiary amine
- Carboxylic acid derivative
- Azacycle
- Organoheterocyclic compound
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic nitrogen compound
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Amine
- Organonitrogen compound
- Organooxygen compound
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | |
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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 | - Li JC, Zhang ZJ, Liu D, Jiang MY, Li RT, Li HM: Quinolizidine alkaloids from the roots of Sophora flavescens. Nat Prod Res. 2022 Apr;36(7):1781-1788. doi: 10.1080/14786419.2020.1817011. Epub 2020 Sep 14. [PubMed:32924588 ]
- Han FM, Wang LX, Chen Y, Chen LM, Feng WH, Wang JY, Liu DW, You Y, Tong Y: [Simultaneous determination of seven alkaloids and three flavonoids in Sophorae Tonkinensis Radix et Rhizoma by HPLC]. Zhongguo Zhong Yao Za Zhi. 2016 Dec;41(24):4628-4634. doi: 10.4268/cjcmm20162423. [PubMed:28936848 ]
- Pan L, Zhang M, Chen HR: [Chemical Constituents of Alkaloids from the Bark of Sophora japonica]. Zhong Yao Cai. 2016 Sep;39(9):2027-9. [PubMed:30209906 ]
- Pan QM, Li YH, Hua J, Huang FP, Wang HS, Liang D: Antiviral Matrine-Type Alkaloids from the Rhizomes of Sophora tonkinensis. J Nat Prod. 2015 Jul 24;78(7):1683-8. doi: 10.1021/acs.jnatprod.5b00325. Epub 2015 Jul 1. [PubMed:26132528 ]
- Ye G, Zhu HY, Li ZX, Ma CH, Fan MS, Sun ZL, Huang CG: LC-MS characterization of efficacy substances in serum of experimental animals treated with Sophora flavescens extracts. Biomed Chromatogr. 2007 Jun;21(6):655-60. doi: 10.1002/bmc.805. [PubMed:17370298 ]
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