Record Information |
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Version | 1.0 |
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Created at | 2021-06-19 21:58:18 UTC |
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Updated at | 2021-06-29 23:58:48 UTC |
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NP-MRD ID | NP0030682 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (+-)-3',3''-bisdemethylpinoresinol |
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Provided By | JEOL Database |
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Description | (+)-Sesamin dicatechol is also known as SC-2 (+)-sesamin dicatechol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (+-)-3',3''-bisdemethylpinoresinol is found in Joannesia princeps and Morinda citrifolia. It was first documented in 2003 (PMID: 12617602). Based on a literature review a small amount of articles have been published on (+)-sesamin dicatechol (PMID: 24224843) (PMID: 16597711) (PMID: 27444012) (PMID: 31911267). |
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Structure | [H]OC1=C(O[H])C([H])=C(C([H])=C1[H])[C@@]1([H])OC([H])([H])[C@]2([H])[C@]([H])(OC([H])([H])[C@]12[H])C1=C([H])C(O[H])=C(O[H])C([H])=C1[H] InChI=1S/C18H18O6/c19-13-3-1-9(5-15(13)21)17-11-7-24-18(12(11)8-23-17)10-2-4-14(20)16(22)6-10/h1-6,11-12,17-22H,7-8H2/t11-,12-,17+,18+/m0/s1 |
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Synonyms | |
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Chemical Formula | C18H18O6 |
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Average Mass | 330.3360 Da |
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Monoisotopic Mass | 330.11034 Da |
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IUPAC Name | 4-[(1S,3aR,4S,6aR)-4-(3,4-dihydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]benzene-1,2-diol |
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Traditional Name | 4-[(1S,3aR,4S,6aR)-4-(3,4-dihydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]benzene-1,2-diol |
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CAS Registry Number | Not Available |
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SMILES | [H]OC1=C(O[H])C([H])=C(C([H])=C1[H])[C@@]1([H])OC([H])([H])[C@]2([H])[C@]([H])(OC([H])([H])[C@]12[H])C1=C([H])C(O[H])=C(O[H])C([H])=C1[H] |
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InChI Identifier | InChI=1S/C18H18O6/c19-13-3-1-9(5-15(13)21)17-11-7-24-18(12(11)8-23-17)10-2-4-14(20)16(22)6-10/h1-6,11-12,17-22H,7-8H2/t11-,12-,17+,18+/m0/s1 |
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InChI Key | OQSOTSIYXPYTRE-YDOWWZDFSA-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, 360 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 360 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CD3OD, 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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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 | - Nguyen PH, Yang JL, Uddin MN, Park SL, Lim SI, Jung DW, Williams DR, Oh WK: Protein tyrosine phosphatase 1B (PTP1B) inhibitors from Morinda citrifolia (Noni) and their insulin mimetic activity. J Nat Prod. 2013 Nov 22;76(11):2080-7. doi: 10.1021/np400533h. Epub 2013 Nov 13. [PubMed:24224843 ]
- Nakai M, Harada M, Nakahara K, Akimoto K, Shibata H, Miki W, Kiso Y: Novel antioxidative metabolites in rat liver with ingested sesamin. J Agric Food Chem. 2003 Mar 12;51(6):1666-70. doi: 10.1021/jf0258961. [PubMed:12617602 ]
- Nakano D, Kwak CJ, Fujii K, Ikemura K, Satake A, Ohkita M, Takaoka M, Ono Y, Nakai M, Tomimori N, Kiso Y, Matsumura Y: Sesamin metabolites induce an endothelial nitric oxide-dependent vasorelaxation through their antioxidative property-independent mechanisms: possible involvement of the metabolites in the antihypertensive effect of sesamin. J Pharmacol Exp Ther. 2006 Jul;318(1):328-35. doi: 10.1124/jpet.105.100149. Epub 2006 Apr 5. [PubMed:16597711 ]
- Kumano T, Fujiki E, Hashimoto Y, Kobayashi M: Discovery of a sesamin-metabolizing microorganism and a new enzyme. Proc Natl Acad Sci U S A. 2016 Aug 9;113(32):9087-92. doi: 10.1073/pnas.1605050113. Epub 2016 Jul 21. [PubMed:27444012 ]
- Chen G, Zhao W, Li Y, Zhou D, Ding J, Lin B, Li W, Yang Y, Liu J, Hou Y, Li N: Bioactive chemical constituents from the seed testa of Vernicia fordii as potential neuroinflammatory inhibitors. Phytochemistry. 2020 Mar;171:112233. doi: 10.1016/j.phytochem.2019.112233. Epub 2020 Jan 3. [PubMed:31911267 ]
- Waibel, R., et al. (2003). Waibel, R., et al., Phytochemistry 62, 805 (2003). Phytochem..
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