Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-11 17:45:53 UTC |
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Update Date | 2022-09-22 18:34:24 UTC |
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HMDB ID | HMDB0031842 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Rhapontigenin |
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Description | Rhapontigenin is found in garden rhubarb. Rhapontigenin is isolated from rhizomes of Rheum undulatum (rhubarb) 4-Guanidinobutanoate is a normal metabolite present in low concentrations. Patients with hyperargininemia have an arginase deficiency which leads to blockade of the urea cycle in the last step with several clinical symptoms. Owing to the arginase deficiency this patients accumulate arginine which leads eventually to epileptogenic guanidino compounds (PMID 7752905 |
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Structure | COC1=C(O)C=C(\C=C/C2=CC(O)=CC(O)=C2)C=C1 InChI=1S/C15H14O4/c1-19-15-5-4-10(8-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2- |
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Synonyms | Value | Source |
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1-(3,5-Dihydroxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethylene | HMDB | 3,3',5-Trihydroxy-4'-methoxystilbene | HMDB | 4'-Methoxy-3,3',5-trihydroxystilbene | HMDB | 4-Guanidinobutanoic acid | HMDB | Pontigenin | HMDB |
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Chemical Formula | C15H14O4 |
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Average Molecular Weight | 258.2693 |
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Monoisotopic Molecular Weight | 258.089208936 |
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IUPAC Name | 5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol |
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Traditional Name | 5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol |
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CAS Registry Number | 500-65-2 |
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SMILES | COC1=C(O)C=C(\C=C/C2=CC(O)=CC(O)=C2)C=C1 |
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InChI Identifier | InChI=1S/C15H14O4/c1-19-15-5-4-10(8-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2- |
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InChI Key | PHMHDRYYFAYWEG-IHWYPQMZSA-N |
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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 | |
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Substituents | - Stilbene
- Methoxyphenol
- Anisole
- Phenoxy compound
- Phenol ether
- Resorcinol
- Styrene
- Methoxybenzene
- 1-hydroxy-4-unsubstituted benzenoid
- Phenol
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Benzenoid
- Ether
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 186 - 187 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Rhapontigenin,1TMS,isomer #1 | COC1=CC=C(/C=C\C2=CC(O)=CC(O)=C2)C=C1O[Si](C)(C)C | 2766.9 | Semi standard non polar | 33892256 | Rhapontigenin,1TMS,isomer #2 | COC1=CC=C(/C=C\C2=CC(O)=CC(O[Si](C)(C)C)=C2)C=C1O | 2781.3 | Semi standard non polar | 33892256 | Rhapontigenin,2TMS,isomer #1 | COC1=CC=C(/C=C\C2=CC(O)=CC(O[Si](C)(C)C)=C2)C=C1O[Si](C)(C)C | 2724.0 | Semi standard non polar | 33892256 | Rhapontigenin,2TMS,isomer #2 | COC1=CC=C(/C=C\C2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2)C=C1O | 2739.5 | Semi standard non polar | 33892256 | Rhapontigenin,3TMS,isomer #1 | COC1=CC=C(/C=C\C2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2)C=C1O[Si](C)(C)C | 2756.7 | Semi standard non polar | 33892256 | Rhapontigenin,1TBDMS,isomer #1 | COC1=CC=C(/C=C\C2=CC(O)=CC(O)=C2)C=C1O[Si](C)(C)C(C)(C)C | 3074.9 | Semi standard non polar | 33892256 | Rhapontigenin,1TBDMS,isomer #2 | COC1=CC=C(/C=C\C2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1O | 3074.9 | Semi standard non polar | 33892256 | Rhapontigenin,2TBDMS,isomer #1 | COC1=CC=C(/C=C\C2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1O[Si](C)(C)C(C)(C)C | 3287.1 | Semi standard non polar | 33892256 | Rhapontigenin,2TBDMS,isomer #2 | COC1=CC=C(/C=C\C2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1O | 3299.0 | Semi standard non polar | 33892256 | Rhapontigenin,3TBDMS,isomer #1 | COC1=CC=C(/C=C\C2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1O[Si](C)(C)C(C)(C)C | 3538.0 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Rhapontigenin GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4l-0490000000-0c7e3c1cc1544fd01557 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Rhapontigenin GC-MS (3 TMS) - 70eV, Positive | splash10-0bt9-1001900000-036b5d08a976c1505736 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Rhapontigenin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rhapontigenin 10V, Positive-QTOF | splash10-0a4i-0190000000-cc3e35bd8d646ecf9ddd | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rhapontigenin 20V, Positive-QTOF | splash10-0a4i-0590000000-fb36ae977a4e36814287 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rhapontigenin 40V, Positive-QTOF | splash10-0fkl-3920000000-c70ef1d9e39f8d23d409 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rhapontigenin 10V, Negative-QTOF | splash10-0a4i-0090000000-326dbc7596b8abc29f7c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rhapontigenin 20V, Negative-QTOF | splash10-0a4i-0090000000-2c9ea4e757e72cb68c00 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rhapontigenin 40V, Negative-QTOF | splash10-0006-2890000000-e1781ac257911d64c7ac | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rhapontigenin 10V, Negative-QTOF | splash10-0a4i-0090000000-c2a50a42dfada53572a9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rhapontigenin 20V, Negative-QTOF | splash10-0a4i-0190000000-96cc8797cb39e482f4e4 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rhapontigenin 40V, Negative-QTOF | splash10-0ab9-0950000000-a841efaa4f3f27296400 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rhapontigenin 10V, Positive-QTOF | splash10-0a4i-0090000000-5436edd338e0c37ed496 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rhapontigenin 20V, Positive-QTOF | splash10-052r-0960000000-b790cc1b715a020f8232 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rhapontigenin 40V, Positive-QTOF | splash10-05g0-0910000000-d0d4c5ff03d7f0ca5185 | 2021-09-22 | Wishart Lab | View Spectrum |
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General References | - Marescau B, De Deyn PP, Holvoet J, Possemiers I, Nagels G, Saxena V, Mahler C: Guanidino compounds in serum and urine of cirrhotic patients. Metabolism. 1995 May;44(5):584-8. [PubMed:7752905 ]
- Jung DB, Lee HJ, Jeong SJ, Lee HJ, Lee EO, Kim YC, Ahn KS, Chen CY, Kim SH: Rhapontigenin inhibited hypoxia inducible factor 1 alpha accumulation and angiogenesis in hypoxic PC-3 prostate cancer cells. Biol Pharm Bull. 2011;34(6):850-5. [PubMed:21628883 ]
- Kim JK, Kim N, Lim YH: Evaluation of the antibacterial activity of rhapontigenin produced from rhapontin by biotransformation against Propionibacterium acnes. J Microbiol Biotechnol. 2010 Jan;20(1):82-7. [PubMed:20134237 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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