Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:38:39 UTC |
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Update Date | 2022-03-07 02:52:40 UTC |
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HMDB ID | HMDB0030724 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Euxanthone |
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Description | Euxanthone, also known as purrenone, belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Euxanthone has been detected, but not quantified in, fruits and mammee apples (Mammea americana). This could make euxanthone a potential biomarker for the consumption of these foods. Euxanthone 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. Based on a literature review a significant number of articles have been published on Euxanthone. |
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Structure | OC1=CC2=C(OC3=CC=CC(O)=C3C2=O)C=C1 InChI=1S/C13H8O4/c14-7-4-5-10-8(6-7)13(16)12-9(15)2-1-3-11(12)17-10/h1-6,14-15H |
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Synonyms | Value | Source |
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1,7-Dihydroxyxanthone | ChEBI | Eyxanthone | ChEBI | Purrenone | ChEBI | 1,7-Dihydroxy-9H-xanthen-9-one | HMDB | 1,7-Dihydroxy-9H-xanthen-9-one, 9ci | HMDB |
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Chemical Formula | C13H8O4 |
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Average Molecular Weight | 228.2002 |
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Monoisotopic Molecular Weight | 228.042258744 |
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IUPAC Name | 1,7-dihydroxy-9H-xanthen-9-one |
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Traditional Name | euxanthone |
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CAS Registry Number | 529-61-3 |
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SMILES | OC1=CC2=C(OC3=CC=CC(O)=C3C2=O)C=C1 |
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InChI Identifier | InChI=1S/C13H8O4/c14-7-4-5-10-8(6-7)13(16)12-9(15)2-1-3-11(12)17-10/h1-6,14-15H |
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InChI Key | KDXFPEKLLFWHMN-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzopyrans |
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Sub Class | 1-benzopyrans |
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Direct Parent | Xanthones |
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Alternative Parents | |
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Substituents | - Xanthone
- Chromone
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- Benzenoid
- Pyran
- Heteroaromatic compound
- Vinylogous acid
- Oxacycle
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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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 | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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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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Euxanthone,1TMS,isomer #1 | C[Si](C)(C)OC1=CC=C2OC3=CC=CC(O)=C3C(=O)C2=C1 | 2637.3 | Semi standard non polar | 33892256 | Euxanthone,1TMS,isomer #2 | C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=CC(O)=CC=C1O2 | 2567.8 | Semi standard non polar | 33892256 | Euxanthone,2TMS,isomer #1 | C[Si](C)(C)OC1=CC=C2OC3=CC=CC(O[Si](C)(C)C)=C3C(=O)C2=C1 | 2702.9 | Semi standard non polar | 33892256 | Euxanthone,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2OC3=CC=CC(O)=C3C(=O)C2=C1 | 2828.8 | Semi standard non polar | 33892256 | Euxanthone,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=CC(O)=CC=C1O2 | 2815.9 | Semi standard non polar | 33892256 | Euxanthone,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2OC3=CC=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2=C1 | 3130.2 | Semi standard non polar | 33892256 |
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Spectra |
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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 - Euxanthone GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fb9-2790000000-af1524aa23d87b7665fa | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Euxanthone GC-MS (2 TMS) - 70eV, Positive | splash10-05fr-7396000000-9b6f035c8eba5b144bf3 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Euxanthone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Euxanthone 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - Euxanthone , positive-QTOF | splash10-056r-0970000000-cf4db3179bd9a6325f78 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Euxanthone 10V, Positive-QTOF | splash10-004i-0090000000-a08f275bc45444bec166 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Euxanthone 20V, Positive-QTOF | splash10-004i-0090000000-3cbc1086267323b74841 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Euxanthone 40V, Positive-QTOF | splash10-000i-4920000000-26bf1905ebade1e277ab | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Euxanthone 10V, Negative-QTOF | splash10-004i-0090000000-a52ce41d5a789009ff70 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Euxanthone 20V, Negative-QTOF | splash10-004i-0090000000-b2fa0915a7aef67969e3 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Euxanthone 40V, Negative-QTOF | splash10-000f-9720000000-d6c24bdf3bfeb5017c77 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Euxanthone 10V, Positive-QTOF | splash10-004i-0090000000-02cbe499adea44a39627 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Euxanthone 20V, Positive-QTOF | splash10-004i-0090000000-02cbe499adea44a39627 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Euxanthone 40V, Positive-QTOF | splash10-0udj-9620000000-9b9454f1242b9bdf94a9 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Euxanthone 10V, Negative-QTOF | splash10-004i-0090000000-d8e725b6742766a16bb5 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Euxanthone 20V, Negative-QTOF | splash10-004i-0090000000-d8e725b6742766a16bb5 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Euxanthone 40V, Negative-QTOF | splash10-0002-1900000000-3369c888fefdc216e03e | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB002648 |
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KNApSAcK ID | C00002949 |
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Chemspider ID | 4444950 |
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KEGG Compound ID | C10061 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Indian yellow |
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METLIN ID | Not Available |
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PubChem Compound | 5281631 |
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PDB ID | Not Available |
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ChEBI ID | 4946 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1822271 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Camara DV, Lemos VS, Santos MH, Nagem TJ, Cortes SF: Mechanism of the vasodilator effect of Euxanthone in rat small mesenteric arteries. Phytomedicine. 2010 Jul;17(8-9):690-2. doi: 10.1016/j.phymed.2009.12.003. Epub 2010 Jan 22. [PubMed:20097048 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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