Record Information |
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Version | 1.0 |
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Created at | 2021-06-21 00:42:29 UTC |
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Updated at | 2021-06-30 00:18:49 UTC |
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NP-MRD ID | NP0043243 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | tenuifolin G |
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Provided By | JEOL Database![JEOL Logo](/attributions/jeol_logo.png) |
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Description | Tenuifolin G 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 G is found in Isodon tenuifolius. It was first documented in 2007 (PMID: 18027658). Based on a literature review very few articles have been published on Tenuifolin G (PMID: 18289838) (PMID: 33496139) (PMID: 20645780). |
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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(=O)[C@]3([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])[C@]([H])(O[H])[C@@]3(C([H])([H])[H])[C@]1([H])[C@@]([H])(OC(=O)C([H])([H])[H])C2([H])[H] InChI=1S/C22H32O6/c1-10-12-6-14(28-11(2)23)18-21(5)16(26)7-15(25)20(3,4)17(21)13(24)9-22(18,8-12)19(10)27/h12,14-19,25-27H,1,6-9H2,2-5H3/t12-,14+,15+,16+,17-,18+,19-,21-,22+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C22H32O6 |
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Average Mass | 392.4920 Da |
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Monoisotopic Mass | 392.21989 Da |
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IUPAC Name | (1S,4R,6S,8S,9S,10R,11S,13S,15R)-6,8,15-trihydroxy-5,5,9-trimethyl-14-methylidene-3-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-11-yl acetate |
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Traditional Name | (1S,4R,6S,8S,9S,10R,11S,13S,15R)-6,8,15-trihydroxy-5,5,9-trimethyl-14-methylidene-3-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-11-yl acetate |
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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(=O)[C@]3([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])[C@]([H])(O[H])[C@@]3(C([H])([H])[H])[C@]1([H])[C@@]([H])(OC(=O)C([H])([H])[H])C2([H])[H] |
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InChI Identifier | InChI=1S/C22H32O6/c1-10-12-6-14(28-11(2)23)18-21(5)16(26)7-15(25)20(3,4)17(21)13(24)9-22(18,8-12)19(10)27/h12,14-19,25-27H,1,6-9H2,2-5H3/t12-,14+,15+,16+,17-,18+,19-,21-,22+/m1/s1 |
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InChI Key | UEMIAJOZGWYQEB-GRZRUJNUSA-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 | Species Name | Source | Reference |
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Isodon tenuifolius | JEOL database | - Yang, J. -H., et al, J. Nat. Prod. 76, 256 (2013)
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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
- Ketone
- Carboxylic acid ester
- Polyol
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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 | - Zhang H, Han T, Zhang L, Yu CH, Wan DG, Rahman K, Qin LP, Peng C: Effects of tenuifolin extracted from radix polygalae on learning and memory: a behavioral and biochemical study on aged and amnesic mice. Phytomedicine. 2008 Aug;15(8):587-94. doi: 10.1016/j.phymed.2007.12.004. Epub 2008 Mar 4. [PubMed:18289838 ]
- Zhang T, Wang J, Shen BD, Zhu JJ, Wang LQ, Yuan HL: [Preparation and in vitro quality evaluation of self-microemulsion co-loaded with tenuifolin and beta-asarone]. Zhongguo Zhong Yao Za Zhi. 2020 Dec;45(24):5988-5995. doi: 10.19540/j.cnki.cjcmm.20200922.301. [PubMed:33496139 ]
- Yao Y, Jia M, Wu JG, Zhang H, Sun LN, Chen WS, Rahman K: Anxiolytic and sedative-hypnotic activities of polygalasaponins from Polygala tenuifolia in mice. Pharm Biol. 2010 Jul;48(7):801-7. doi: 10.3109/13880200903280042. [PubMed:20645780 ]
- Dong XB, Li J, Jiang Y, Zheng Y, Dong TX, Tu PF, Tsim WK: [Determination of tenuifolin in Tianwang Buxinwan and Guipiwan by HPLC]. Zhongguo Zhong Yao Za Zhi. 2007 Aug;32(16):1647-9. [PubMed:18027658 ]
- Yang, J. -H., et al. (2013). Yang, J. -H., et al, J. Nat. Prod. 76, 256 (2013). J. Nat. Prod..
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