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 lipid molecule. Prunetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Prunetin is a bitter tasting compound. Prunetin has been detected, but not quantified in, several different foods, such as herbs and spices, prunus (cherry, plum), sour cherries, and tea. This could make prunetin a potential biomarker for the consumption of these foods. |
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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 | 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 |
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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 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0udi-0190000000-b6ecb3ccb54bdeacbe00 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-001i-0090000000-11b97ad586d2e24e7115 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-014r-0090000000-fb797f4684174e26b1d0 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-014i-0090000000-6db4d2441911d696b121 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-001i-0090000000-306c2baf58cc6c40c407 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0159-0090000000-a85c6c3392aa2541b48c | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-001i-0090000000-11b97ad586d2e24e7115 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-014r-0090000000-fb797f4684174e26b1d0 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-014i-0090000000-6db4d2441911d696b121 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-001i-0090000000-306c2baf58cc6c40c407 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-0159-0090000000-a85c6c3392aa2541b48c | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-014r-0090000000-fb797f4684174e26b1d0 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-014i-0090000000-6db4d2441911d696b121 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT 19V, positive | splash10-002r-0290000000-e0d4e56550195007ab89 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT 19V, positive | splash10-0690-0690000000-292dcb6a0c7801e87353 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0090000000-280a25523108ad3de6f1 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0090000000-8512eb234e9b55c8fabc | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gbi-2790000000-911d7dc4d9e528af001b | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0090000000-3539a40fa0eaf6326969 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0090000000-bb3562f94d2cef4ead46 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0gb9-3980000000-4d720fa6bb02944fb579 | 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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