Record Information |
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Version | 1.0 |
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Created at | 2021-01-06 01:48:54 UTC |
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Updated at | 2021-07-15 17:24:12 UTC |
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NP-MRD ID | NP0016970 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Antroquinonol S |
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Provided By | NPAtlas![NPAtlas Logo](/attributions/npatlas_logo_square_small.png) |
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Description | Antroquinonol S is found in Antrodia and Taiwanofungus camphoratus. It was first documented in 2017 (PMID: 28898082). Based on a literature review a small amount of articles have been published on Antroquinonol S (PMID: 32378228) (PMID: 31392378) (PMID: 33556840) (PMID: 31933057). |
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Structure | [H]O[C@@]1([H])C([H])=C(OC([H])([H])[H])C(=O)[C@]([H])(C([H])([H])[H])[C@@]1([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])[C@@]1([H])OC(=O)[C@]([H])(C([H])([H])[H])C1([H])[H] InChI=1S/C23H34O5/c1-14(7-6-8-15(2)11-18-12-16(3)23(26)28-18)9-10-19-17(4)22(25)21(27-5)13-20(19)24/h8-9,13,16-20,24H,6-7,10-12H2,1-5H3/b14-9+,15-8+/t16-,17-,18-,19-,20+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C23H34O5 |
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Average Mass | 390.5200 Da |
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Monoisotopic Mass | 390.24062 Da |
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IUPAC Name | (3R,5S)-5-[(2E,6E)-8-[(1R,2R,6R)-2-hydroxy-4-methoxy-6-methyl-5-oxocyclohex-3-en-1-yl]-2,6-dimethylocta-2,6-dien-1-yl]-3-methyloxolan-2-one |
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Traditional Name | (3R,5S)-5-[(2E,6E)-8-[(1R,2R,6R)-2-hydroxy-4-methoxy-6-methyl-5-oxocyclohex-3-en-1-yl]-2,6-dimethylocta-2,6-dien-1-yl]-3-methyloxolan-2-one |
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CAS Registry Number | Not Available |
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SMILES | COC1=C[C@H](O)[C@H](C\C=C(/C)CC\C=C(/C)C[C@@H]2C[C@@H](C)C(=O)O2)[C@@H](C)C1=O |
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InChI Identifier | InChI=1S/C23H34O5/c1-14(7-6-8-15(2)11-18-12-16(3)23(26)28-18)9-10-19-17(4)22(25)21(27-5)13-20(19)24/h8-9,13,16-20,24H,6-7,10-12H2,1-5H3/b14-9+,15-8+/t16-,17-,18-,19-,20+/m1/s1 |
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InChI Key | FHZXTBYGLVPEAT-VAXJKGLHSA-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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Classification | Not classified |
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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 MC, Cho TY, Kuo YH, Lee TH: Meroterpenoids from a Medicinal Fungus Antrodia cinnamomea. J Nat Prod. 2017 Sep 22;80(9):2439-2446. doi: 10.1021/acs.jnatprod.7b00223. Epub 2017 Sep 12. [PubMed:28898082 ]
- Liu X, Xia Y, Zhang Y, Sang K, Xiong Z, Wang G, Liu X, Ai L: RNA-Seq transcriptomic analyses of Antrodia camphorata to determine antroquinonol and antrodin C biosynthetic mechanisms in the in situ extractive fermentation. J Sci Food Agric. 2020 Aug 30;100(11):4252-4262. doi: 10.1002/jsfa.10467. Epub 2020 May 21. [PubMed:32378228 ]
- Liu X, Xia Y, Zhang Y, Yi Z, Meng P, Wang G, Ai L: Enhancement of antroquinonol and antrodin C productions via in situ extractive fermentation of Antrodia camphorata S-29. Appl Microbiol Biotechnol. 2019 Oct;103(20):8351-8361. doi: 10.1007/s00253-019-10034-7. Epub 2019 Aug 8. [PubMed:31392378 ]
- Liu X, Xia Y, Zhang Y, Liang L, Xiong Z, Wang G, Song X, Ai L: Enhancement of antroquinonol production via the overexpression of 4-hydroxybenzoate polyprenyltransferase biosynthesis-related genes in Antrodia cinnamomea. Phytochemistry. 2021 Apr;184:112677. doi: 10.1016/j.phytochem.2021.112677. Epub 2021 Feb 5. [PubMed:33556840 ]
- Liu XF, Xia YJ, Lai PF, Zhang Y, Yi ZW, Xie CL, Hong YQ, Ai LZ: An increase in cell membrane permeability in the in situ extractive fermentation improves the production of antroquinonol from Antrodia camphorata S-29. J Ind Microbiol Biotechnol. 2020 Feb;47(2):197-207. doi: 10.1007/s10295-020-02258-8. Epub 2020 Jan 14. [PubMed:31933057 ]
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