Record Information |
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Version | 1.0 |
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Created at | 2021-06-21 00:42:17 UTC |
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Updated at | 2021-06-30 00:18:48 UTC |
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NP-MRD ID | NP0043238 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | tenuifolin B |
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Provided By | JEOL Database![JEOL Logo](/attributions/jeol_logo.png) |
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Description | Tenuifolin B belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. tenuifolin B is found in Isodon tenuifolius and Maackia tenuifolia. It was first documented in 2009 (PMID: 19754130). Based on a literature review a significant number of articles have been published on Tenuifolin B (PMID: 32168102) (PMID: 29017076) (PMID: 28342292) (PMID: 27888133) (PMID: 25705699) (PMID: 21042868). |
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Structure | [H]O[C@]1([H])C(=C([H])[H])[C@@]2([H])C([H])([H])[C@@]11C([H])([H])C([H])([H])[C@]3([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]1([H])[C@@]([H])(O[H])C2([H])[H] InChI=1S/C20H32O3/c1-11-12-9-13(21)16-19(4)7-6-15(22)18(2,3)14(19)5-8-20(16,10-12)17(11)23/h12-17,21-23H,1,5-10H2,2-4H3/t12-,13+,14-,15+,16+,17-,19-,20-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C20H32O3 |
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Average Mass | 320.4730 Da |
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Monoisotopic Mass | 320.23514 Da |
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IUPAC Name | (1R,4S,6S,9R,10S,11S,13S,15R)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-6,11,15-triol |
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Traditional Name | (1R,4S,6S,9R,10S,11S,13S,15R)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-6,11,15-triol |
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CAS Registry Number | Not Available |
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SMILES | [H]O[C@]1([H])C(=C([H])[H])[C@@]2([H])C([H])([H])[C@@]11C([H])([H])C([H])([H])[C@]3([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]1([H])[C@@]([H])(O[H])C2([H])[H] |
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InChI Identifier | InChI=1S/C20H32O3/c1-11-12-9-13(21)16-19(4)7-6-15(22)18(2,3)14(19)5-8-20(16,10-12)17(11)23/h12-17,21-23H,1,5-10H2,2-4H3/t12-,13+,14-,15+,16+,17-,19-,20-/m1/s1 |
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InChI Key | MQWPDQKLLPDSQK-MJWYYFFNSA-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, 600 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, C5D5N, 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 kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Diterpenoids |
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Direct Parent | Kaurane diterpenoids |
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Alternative Parents | |
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Substituents | - Kaurane diterpenoid
- Cyclic alcohol
- Secondary alcohol
- Polyol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic 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 | - Peng F, Lu L, Wei F, Wu D, Wang K, Tang J: The onjisaponin B metabolite tenuifolin ameliorates dopaminergic neurodegeneration in a mouse model of Parkinson's disease. Neuroreport. 2020 Apr 8;31(6):456-465. doi: 10.1097/WNR.0000000000001428. [PubMed:32168102 ]
- Yang C, Yin X, Dong X, Zhang X, You L, Wang W, Wang J, Chen Q, Ni J: Determination of the phytochemical composition of Jingning fang and the in vivo pharmacokinetics of its metabolites in rat plasma by UPLC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Nov 1;1067:71-88. doi: 10.1016/j.jchromb.2017.09.019. Epub 2017 Sep 21. [PubMed:29017076 ]
- Wang X, Zhang Y, Niu H, Geng Y, Wang B, Yang X, Yan P, Li Q, Bi K: Ultra-fast liquid chromatography with tandem mass spectrometry determination of eight bioactive components of Kai-Xin-San in rat plasma and its application to a comparative pharmacokinetic study in normal and Alzheimer's disease rats. J Sep Sci. 2017 May;40(10):2131-2140. doi: 10.1002/jssc.201601343. Epub 2017 Apr 19. [PubMed:28342292 ]
- Fang J, Wang L, Wu T, Yang C, Gao L, Cai H, Liu J, Fang S, Chen Y, Tan W, Wang Q: Network pharmacology-based study on the mechanism of action for herbal medicines in Alzheimer treatment. J Ethnopharmacol. 2017 Jan 20;196:281-292. doi: 10.1016/j.jep.2016.11.034. Epub 2016 Nov 23. [PubMed:27888133 ]
- Wen L, Xia N, Tang P, Hong Y, Wang Z, Liu Y, Liu Y, Liu J, Li X: The gastrointestinal irritation of polygala saponins and its potential mechanism in vitro and in vivo. Biomed Res Int. 2015;2015:918048. doi: 10.1155/2015/918048. Epub 2015 Feb 1. [PubMed:25705699 ]
- Arai M, Hayashi A, Sobou M, Ishida S, Kawachi T, Kotoku N, Kobayashi M: Anti-angiogenic effect of triterpenoidal saponins from Polygala senega. J Nat Med. 2011 Jan;65(1):149-56. doi: 10.1007/s11418-010-0477-7. Epub 2010 Nov 2. [PubMed:21042868 ]
- Lin RJ, Cheng MJ, Huang JC, Lo WL, Yeh YT, Yen CM, Lu CM, Chen CY: Cytotoxic compounds from the stems of Cinnamomum tenuifolium. J Nat Prod. 2009 Oct;72(10):1816-24. doi: 10.1021/np900225p. [PubMed:19754130 ]
- Yang, J. -H., et al. (2013). Yang, J. -H., et al, J. Nat. Prod. 76, 256 (2013). J. Nat. Prod..
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