Record Information |
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Version | 1.0 |
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Created at | 2020-10-06 22:11:38 UTC |
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Updated at | 2024-04-19 10:08:42 UTC |
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NP-MRD ID | NP0001738 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Resveratrol |
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Description | Resveratrol, also known as trans-resveratrol, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Thus, resveratrol is considered to be an aromatic polyketide. Resveratrol exists in all living species, ranging from bacteria to plants to humans. Resveratrol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Resveratrol is found in Ammopiptanthus mongolicus, Artocarpus chaplasha, Artocarpus gomezianus, Artocarpus lakoocha , Bagassa guianensis, Bolboschoenus fluviatilis, Botrytis cinerea, Caragana tibetica, Cyperus longus, Dracaena cochinchinensis, Elephantorrhiza goetzei, Fagopyrum megacarpum, Fallopia multiflora, Festuca rubra, Gentum parvifolium, Gnetum gnemonoides, Gnetum hainanense, Gnetum klossii, Gnetum latifolium Blume, Gnetum macrostachyum, Gnetum montanum, Gnetum pendulum, Holodiscus discolor, Humulus japonicus, Humulus lupulus, Hydrangea macrophylla, Belamcanda chinensis , Iris halophila, Juniperus polycarpos, Larix gmelinii, Lonchocarpus utilis, Maclura pomifera, Morus alba, Paeonia lactiflora, Paeonia suffruticosa, Pholidota chinensis, Plasmopara viticola, Pleuropterus cilinervis, Pterolobium hexapetalum, Rheum palaestinum, Rheum undulatum, Rumex bucephalophorus, Rumex hastatus, Rumex nepalensis, Salacia lehmbachii, Schizocarphus nervosus, Smilax aspera, Smilax corbularia, Smilax excelsa, Smilax glabra, Smilax perfoliata, Spirotropis longifolia, Streptomyces avermitilis, Streptomyces venezuelae, Syagrus romanzoffiana, Toxylon pomifera, Uncinula necator, Upuna borneensis, Vaccinium alaskaense, Vateria indica, Veratrum taliense, Vitis amurensis, Vitis chunganensis, Vitis davidii, Yucca periculosa and Yucca schidigera. It was first documented in 1999 (PMID: 10824865). Based on a literature review a significant number of articles have been published on Resveratrol (PMID: 16275073) (PMID: 16988123) (PMID: 15517885) (PMID: 15647782). |
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Structure | OC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1 InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1+ |
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Synonyms | Value | Source |
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(e)-5-(2-(4-Hydroxyphenyl)ethenyl)-1,3-benzenediol | ChEBI | (e)-Resveratrol | ChEBI | 3,4',5-Stilbenetriol | ChEBI | 3,4',5-Trihydroxy-trans-stilbene | ChEBI | 3,4',5-Trihydroxystilbene | ChEBI | 3,5,4'-Trihydroxystilbene | ChEBI | 5-[(e)-2-(4-Hydroxyphenyl)vinyl]benzene-1,3-diol | ChEBI | trans-Resveratrol | Kegg | trans-3,4',5 - Trihydroxystilbene | HMDB | SRT 501 | MeSH, HMDB | SRT-501 | MeSH, HMDB | trans Resveratrol | MeSH, HMDB | (E)-2-(3,5-Dihydroxyphenyl)-1-(4-hydroxyphenyl)ethene | HMDB | (E)-3,4',5-Trihydroxystilbene | HMDB | (E)-3,4’,5-Trihydroxystilbene | HMDB | (E)-5-(p-Hydroxystyryl)resorcinol | HMDB | 3,4’,5-Stilbenetriol | HMDB | 3,4’,5-Trihydroxy-trans-stilbene | HMDB | 3,4’,5-Trihydroxystilbene | HMDB | 5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol | HMDB | Resveratrol | HMDB | trans-3,5,4'-Trihydroxystilbene | HMDB | trans-3,5,4’-Trihydroxystilbene | HMDB | (E)-5-[2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol | PhytoBank |
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Chemical Formula | C14H12O3 |
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Average Mass | 228.2470 Da |
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Monoisotopic Mass | 228.07864 Da |
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IUPAC Name | 5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol |
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Traditional Name | resveratrol |
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CAS Registry Number | Not Available |
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SMILES | OC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1 |
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InChI Identifier | InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1+ |
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InChI Key | LUKBXSAWLPMMSZ-OWOJBTEDSA-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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HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-02-02 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-02-02 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-02-02 | View Spectrum | 1D NMR | [13C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-02-02 | View Spectrum | 1D NMR | [1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-02-02 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | john.cort@pnnl.gov | Not Available | Not Available | 2023-06-14 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | john.cort@pnnl.gov | Not Available | Not Available | 2023-06-14 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | john.cort@pnnl.gov | Not Available | Not Available | 2023-06-14 | View Spectrum | 1D NMR | [13C, ] NMR Spectrum (2D, 126 MHz, CD3OD, experimental) | john.cort@pnnl.gov | Not Available | Not Available | 2023-06-14 | View Spectrum | 1D NMR | [1H, ] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | john.cort@pnnl.gov | Not Available | Not Available | 2023-06-14 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400Mz MHz, DMSO, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125.79 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500.2 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600.133705802 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201.216488466 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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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 400Mz, DMSO, simulated) | Rgf8b | | | 2020-10-06 | View Spectrum |
| Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Stilbenes |
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Sub Class | Not Available |
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Direct Parent | Stilbenes |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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Molecular Framework | Aromatic homomonocyclic 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 | |
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Predicted Properties | |
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General References | - Olas B, Zbikowska HM, Wachowicz B, Krajewski T, Buczynski A, Magnuszewska A: Inhibitory effect of resveratrol on free radical generation in blood platelets. Acta Biochim Pol. 1999;46(4):961-6. [PubMed:10824865 ]
- Vilar S, Quezada E, Santana L, Uriarte E, Yanez M, Fraiz N, Alcaide C, Cano E, Orallo F: Design, synthesis, and vasorelaxant and platelet antiaggregatory activities of coumarin-resveratrol hybrids. Bioorg Med Chem Lett. 2006 Jan 15;16(2):257-61. doi: 10.1016/j.bmcl.2005.10.013. Epub 2005 Nov 3. [PubMed:16275073 ]
- Niles RM, Cook CP, Meadows GG, Fu YM, McLaughlin JL, Rankin GO: Resveratrol is rapidly metabolized in athymic (nu/nu) mice and does not inhibit human melanoma xenograft tumor growth. J Nutr. 2006 Oct;136(10):2542-6. doi: 10.1093/jn/136.10.2542. [PubMed:16988123 ]
- Aggarwal BB, Bhardwaj A, Aggarwal RS, Seeram NP, Shishodia S, Takada Y: Role of resveratrol in prevention and therapy of cancer: preclinical and clinical studies. Anticancer Res. 2004 Sep-Oct;24(5A):2783-840. [PubMed:15517885 ]
- Olas B, Nowak P, Wachowicz B: Resveratrol protects against peroxynitrite-induced thiol oxidation in blood platelets. Cell Mol Biol Lett. 2004;9(4A):577-87. [PubMed:15647782 ]
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