Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:32 UTC |
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Update date | 2020-02-24 19:10:39 UTC |
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Primary ID | FDB002820 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Avicularin |
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Description | Avicularin belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Avicularin is found, on average, in the highest concentration within a few different foods, such as highbush blueberries (Vaccinium corymbosum), american cranberries (Vaccinium macrocarpon), and lingonberries (Vaccinium vitis-idaea) and in a lower concentration in grape wine, teas (Camellia sinensis), and beer. Avicularin has also been detected, but not quantified in, several different foods, such as allspices (Pimenta dioica), fennels (Foeniculum vulgare), guavas (Psidium guajava), cocoa powder, and pears (Pyrus communis). This could make avicularin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Avicularin. |
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CAS Number | 572-30-5 |
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Structure | |
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Synonyms | Synonym | Source |
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3-(a-L-Arabinofuranosyloxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one, 9ci | HMDB | Avicularine | HMDB | Avicularoside | HMDB | Fenicularin | HMDB | Quercetin 3-a-L-arabofuranoside | HMDB | Quercetin 3-alpha-L-arabinofuranoside | HMDB | 3-(a-L-Arabinofuranosyloxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one, 9CI | db_source |
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Predicted Properties | |
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Chemical Formula | C20H18O11 |
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IUPAC name | 3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one |
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InChI Identifier | InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2 |
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InChI Key | BDCDNTVZSILEOY-UHFFFAOYSA-N |
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Isomeric SMILES | OCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)C(O)C1O |
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Average Molecular Weight | 434.3503 |
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Monoisotopic Molecular Weight | 434.084911418 |
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Classification |
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Description | Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | Flavonoid glycosides |
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Direct Parent | Flavonoid-3-O-glycosides |
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Alternative Parents | |
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Substituents | - Flavonoid-3-o-glycoside
- 3'-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavone
- Hydroxyflavonoid
- Chromone
- Glycosyl compound
- O-glycosyl compound
- Benzopyran
- 1-benzopyran
- Pentose monosaccharide
- Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Pyran
- Monocyclic benzene moiety
- Benzenoid
- Monosaccharide
- Heteroaromatic compound
- Vinylogous acid
- Tetrahydrofuran
- Secondary alcohol
- Oxacycle
- Acetal
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Organic oxide
- Primary alcohol
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Physico-Chemical Properties |
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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 55.30%; H 4.18%; O 40.52% | DFC |
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Melting Point | Mp 217° (anhyd. 222°) | 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 | [a]D -241 (c, 0.138 in MeOH) -> -116 (24 hr) | DFC |
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Spectroscopic UV Data | 360 (e 17400) (EtOH) (Berdy) | DFC |
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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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Predicted GC-MS | Avicularin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-074l-9002200000-165c1bc22134fd2b13d3 | Spectrum | Predicted GC-MS | Avicularin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000i-6900016000-052fe746be5b26272330 | Spectrum | Predicted GC-MS | Avicularin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Avicularin, 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 - DI-ESI-qTof , Negative | splash10-0udi-0179000000-5a91dfb63e4e3fdb59e8 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Positive | splash10-0udi-0009000000-bc5743bd40f3c7a2a0d5 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udr-1239700000-28b26f9b0787af6359a8 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0269100000-7a94db25e6a9fec0926f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f79-3972000000-fc79be30bd59abcaa268 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0f89-1115900000-e00178a2826bcd705265 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ue9-0649200000-08c4ad36ee9b747c1603 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0zgr-2952000000-5bfe8c304eb8f6a07051 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0000900000-1453f61e7eeaeb92b36b | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0000900000-b96d174742d0ab482807 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udr-1910400000-98cf5ef937c3621d177c | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0000900000-5783c018f9dec347d81f | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0401900000-6d6d89904d44ae2a2c95 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0f80-1911100000-ba0b08fba31dc160222b | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 15727203 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 12308704 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 298 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB30860 |
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CRC / DFC (Dictionary of Food Compounds) ID | CNT75-X:CNT75-X |
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EAFUS ID | Not Available |
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Dr. Duke ID | AVICULARIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00005367 |
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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 | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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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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aldose reductase inhibitor | 48550 | An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). | DUKE | antibiotic | 22582 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | cyclooxygenase activator | | | DUKE | diuretic | 35498 | An agent that promotes the excretion of urine through its effects on kidney function. | 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 | tissue thromboplastin inhibitor | 50427 | A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. | 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 | Not Available |
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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 | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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