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 17:30:33 UTC |
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Update Date | 2022-03-07 02:52:10 UTC |
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HMDB ID | HMDB0029463 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Gentisein |
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Description | Gentisein, also known as xanthone deriv, 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. Gentisein 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 Gentisein. |
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Structure | OC1=CC=C2OC3=CC(O)=CC(O)=C3C(=O)C2=C1 InChI=1S/C13H8O5/c14-6-1-2-10-8(3-6)13(17)12-9(16)4-7(15)5-11(12)18-10/h1-5,14-16H |
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Synonyms | Value | Source |
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1,3,7-Trihydroxyxanthone | ChEBI | 1,3,7-Trihydroxy-9H-xanthen-9-one | HMDB | 1,3,7-Trihydroxy-9H-xanthen-9-one, 9ci | HMDB | 1,3,7-Trihydroxy-xanthen-9-one | HMDB | Xanthone deriv | HMDB | 1,3,7-Trihydroxy-xanthone | HMDB |
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Chemical Formula | C13H8O5 |
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Average Molecular Weight | 244.1996 |
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Monoisotopic Molecular Weight | 244.037173366 |
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IUPAC Name | 1,3,7-trihydroxy-9H-xanthen-9-one |
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Traditional Name | gentisein |
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CAS Registry Number | 529-49-7 |
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SMILES | OC1=CC=C2OC3=CC(O)=CC(O)=C3C(=O)C2=C1 |
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InChI Identifier | InChI=1S/C13H8O5/c14-6-1-2-10-8(3-6)13(17)12-9(16)4-7(15)5-11(12)18-10/h1-5,14-16H |
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InChI Key | JJUNZBRHHGLJQW-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
- Pyran
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Polyol
- Oxacycle
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organic oxygen 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 | Property | Value | Reference |
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Melting Point | 321 - 323 °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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Gentisein,1TMS,isomer #1 | C[Si](C)(C)OC1=CC=C2OC3=CC(O)=CC(O)=C3C(=O)C2=C1 | 2809.4 | Semi standard non polar | 33892256 | Gentisein,1TMS,isomer #2 | C[Si](C)(C)OC1=CC(O)=C2C(=O)C3=CC(O)=CC=C3OC2=C1 | 2788.5 | Semi standard non polar | 33892256 | Gentisein,1TMS,isomer #3 | C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C1=CC(O)=CC=C1O2 | 2755.8 | Semi standard non polar | 33892256 | Gentisein,2TMS,isomer #1 | C[Si](C)(C)OC1=CC(O)=C2C(=O)C3=CC(O[Si](C)(C)C)=CC=C3OC2=C1 | 2842.1 | Semi standard non polar | 33892256 | Gentisein,2TMS,isomer #2 | C[Si](C)(C)OC1=CC=C2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C(=O)C2=C1 | 2795.8 | Semi standard non polar | 33892256 | Gentisein,2TMS,isomer #3 | C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC(O)=CC=C3OC2=C1 | 2813.2 | Semi standard non polar | 33892256 | Gentisein,3TMS,isomer #1 | C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC(O[Si](C)(C)C)=CC=C3OC2=C1 | 2857.3 | Semi standard non polar | 33892256 | Gentisein,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2OC3=CC(O)=CC(O)=C3C(=O)C2=C1 | 3036.5 | Semi standard non polar | 33892256 | Gentisein,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C3=CC(O)=CC=C3OC2=C1 | 3041.6 | Semi standard non polar | 33892256 | Gentisein,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C1=CC(O)=CC=C1O2 | 3015.1 | Semi standard non polar | 33892256 | Gentisein,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3OC2=C1 | 3292.4 | Semi standard non polar | 33892256 | Gentisein,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2=C1 | 3247.7 | Semi standard non polar | 33892256 | Gentisein,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC(O)=CC=C3OC2=C1 | 3284.7 | Semi standard non polar | 33892256 | Gentisein,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3OC2=C1 | 3541.4 | 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 - Gentisein GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fr6-0390000000-b08cd65092c7da190655 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Gentisein GC-MS (3 TMS) - 70eV, Positive | splash10-00ds-6209400000-15b97fd8747668fc1538 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Gentisein 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 - Gentisein 10V, Positive-QTOF | splash10-0002-0090000000-c0438723fffbec08dc29 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gentisein 20V, Positive-QTOF | splash10-0002-0090000000-eadef615280a124da677 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gentisein 40V, Positive-QTOF | splash10-004i-2490000000-7249d7b2ec50b9e7de69 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gentisein 10V, Negative-QTOF | splash10-0006-0090000000-32e1f65672dbbc366f46 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gentisein 20V, Negative-QTOF | splash10-0006-0090000000-bfc86c5529e7480203af | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gentisein 40V, Negative-QTOF | splash10-0frf-3590000000-21fea4ab2dc19a33c18f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gentisein 10V, Negative-QTOF | splash10-0006-0090000000-9b916dc13378b5552663 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gentisein 20V, Negative-QTOF | splash10-0006-0090000000-9b916dc13378b5552663 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gentisein 40V, Negative-QTOF | splash10-0zfr-4890000000-f33161dcb8704bab6515 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gentisein 10V, Positive-QTOF | splash10-0002-0090000000-375ead9ffd42ab31b405 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gentisein 20V, Positive-QTOF | splash10-0002-0090000000-375ead9ffd42ab31b405 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gentisein 40V, Positive-QTOF | splash10-014i-3980000000-37e149a1e400513096be | 2021-09-25 | Wishart Lab | View Spectrum |
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