Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:09 UTC |
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Update date | 2019-11-26 03:06:42 UTC |
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Primary ID | FDB012400 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Prunetin |
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Description | Prunetin, also known as padmakastein, belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone. Thus, prunetin is considered to be a flavonoid. Prunetin is a bitter tasting compound. Prunetin has been detected, but not quantified in, several different foods, such as herbal tea, red clovers (Trifolium pratense), black tea, herbs and spices, and teas (Camellia sinensis). This could make prunetin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Prunetin. |
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CAS Number | 552-59-0 |
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Structure | |
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Synonyms | Synonym | Source |
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4',5-Dihydroxy-7-methoxygenistein | ChEBI | 4',5-Dihydroxy-7-methoxyisoflavone | ChEBI | 5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4-benzopyrone | ChEBI | 5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one | ChEBI | 7-O-Methyl-genistein | ChEBI | Padmakastein | ChEBI | Prunusetin | ChEBI | 5,4'-Dihydroxy-7-methoxyisoflavone | HMDB, MeSH | 5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one, 9ci | HMDB | 5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one | HMDB | Isoflavone, 4',5-dihydroxy-7-methoxy- (7ci,8ci) | HMDB | 5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one, 9CI | db_source | 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one | biospider | 5,4'-dihydroxy-7-methoxyisoflavone | biospider | Isoflavone, 4',5-dihydroxy-7-methoxy- (7CI,8CI) | biospider | Prunetin | db_source |
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Predicted Properties | |
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Chemical Formula | C16H12O5 |
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IUPAC name | 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one |
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InChI Identifier | InChI=1S/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3 |
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InChI Key | KQMVAGISDHMXJJ-UHFFFAOYSA-N |
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Isomeric SMILES | COC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C=C1 |
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Average Molecular Weight | 284.267 |
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Monoisotopic Molecular Weight | 284.068473486 |
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Classification |
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Description | Belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Isoflavonoids |
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Sub Class | O-methylated isoflavonoids |
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Direct Parent | 7-O-methylisoflavones |
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Alternative Parents | |
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Substituents | - 7-o-methylisoflavone
- Hydroxyisoflavonoid
- Isoflavone
- Chromone
- Benzopyran
- 1-benzopyran
- Anisole
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Pyranone
- Monocyclic benzene moiety
- Benzenoid
- Pyran
- Heteroaromatic compound
- Vinylogous acid
- Organoheterocyclic compound
- Ether
- Oxacycle
- Organooxygen compound
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- 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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Disposition | Route of exposure: Source: Biological location: |
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Role | Biological role: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 67.60%; H 4.25%; O 28.14% | DFC |
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Melting Point | Mp 246-248° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | Prunetin, non-derivatized, GC-MS Spectrum | splash10-03di-1932800000-7ba8925a2b1306b10b50 | Spectrum | GC-MS | Prunetin, non-derivatized, GC-MS Spectrum | splash10-03di-1932800000-7ba8925a2b1306b10b50 | Spectrum | Predicted GC-MS | Prunetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4i-0490000000-568458ba8831c097f5c5 | Spectrum | Predicted GC-MS | Prunetin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-08ml-3439700000-90e7b4e47d986f3bfb5f | Spectrum | Predicted GC-MS | Prunetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Prunetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0udi-0190000000-b6ecb3ccb54bdeacbe00 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0udi-0190000000-b6ecb3ccb54bdeacbe00 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-001i-0090000000-11b97ad586d2e24e7115 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-014r-0090000000-fb797f4684174e26b1d0 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-014i-0090000000-6db4d2441911d696b121 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-001i-0090000000-306c2baf58cc6c40c407 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0159-0090000000-a85c6c3392aa2541b48c | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-001i-0090000000-11b97ad586d2e24e7115 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-014r-0090000000-fb797f4684174e26b1d0 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-014i-0090000000-6db4d2441911d696b121 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-001i-0090000000-306c2baf58cc6c40c407 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-0159-0090000000-a85c6c3392aa2541b48c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-014r-0090000000-fb797f4684174e26b1d0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-014i-0090000000-6db4d2441911d696b121 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT 19V, positive | splash10-002r-0290000000-e0d4e56550195007ab89 | 2020-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT 19V, positive | splash10-0690-0690000000-292dcb6a0c7801e87353 | 2020-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0090000000-306c2baf58cc6c40c407 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0159-0090000000-a85c6c3392aa2541b48c | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-014i-0090000000-6db4d2441911d696b121 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0090000000-280a25523108ad3de6f1 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0090000000-8512eb234e9b55c8fabc | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gbi-2790000000-911d7dc4d9e528af001b | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0090000000-3539a40fa0eaf6326969 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0090000000-bb3562f94d2cef4ead46 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0gb9-3980000000-4d720fa6bb02944fb579 | 2015-04-25 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 4445116 |
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ChEMBL ID | CHEMBL491174 |
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KEGG Compound ID | C10521 |
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Pubchem Compound ID | 5281804 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 8600 |
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Phenol-Explorer ID | 881 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB34127 |
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CRC / DFC (Dictionary of Food Compounds) ID | HGS77-A:HGS77-A |
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EAFUS ID | Not Available |
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Dr. Duke ID | PRUNETIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002564 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Prunetin |
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Phenol-Explorer Metabolite ID | 881 |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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