Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:03 UTC |
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Update date | 2019-11-26 03:06:26 UTC |
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Primary ID | FDB012225 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Daidzin |
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Description | Daidzin, also known as daidzoside, belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Thus, daidzin is considered to be a flavonoid. Daidzin is a bitter tasting compound. Daidzin is found, on average, in the highest concentration within a few different foods, such as soy beans (Glycine max), yogurt, and soy yogurt and in a lower concentration in miso, other soy product, and soy milk. Daidzin has also been detected, but not quantified in, several different foods, such as fox grapes (Vitis labrusca), green zucchinis (Cucurbita pepo var. cylindrica), fruits, globe artichokes (Cynara scolymus), and canola. This could make daidzin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Daidzin. |
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CAS Number | 552-66-9 |
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Structure | |
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Synonyms | Synonym | Source |
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Daidzein 7-glucoside | ChEBI | Daidzein 7-O-glucoside | ChEBI | Daidzoside | ChEBI | 7-O-Glucosyl-4'-hydroxyisoflavone | MeSH | 4',7-Dihydroxyisoflavone 7-O-b-D-glucopyranoside | HMDB | Daidzein 7-O-beta-D-glucopyranoside | HMDB | Daidzein 7-O-beta-D-glucoside | HMDB | DZN | HMDB | Daidzin | ChEBI | Daidzein 7-O-b-D-glucoside | Generator, HMDB | Daidzein 7-O-β-D-glucoside | Generator, HMDB |
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Predicted Properties | |
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Chemical Formula | C21H20O9 |
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IUPAC name | 3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one |
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InChI Identifier | InChI=1S/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16-,18-,19+,20-,21-/m1/s1 |
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InChI Key | KYQZWONCHDNPDP-QNDFHXLGSA-N |
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Isomeric SMILES | OC[C@H]1O[C@@H](OC2=CC3=C(C=C2)C(=O)C(=CO3)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O |
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Average Molecular Weight | 416.382 |
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Monoisotopic Molecular Weight | 416.110732224 |
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Classification |
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Description | Belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. |
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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 | Isoflavonoid O-glycosides |
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Direct Parent | Isoflavonoid O-glycosides |
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Alternative Parents | |
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Substituents | - Isoflavonoid o-glycoside
- Isoflavonoid-7-o-glycoside
- Isoflavone
- Phenolic glycoside
- Hexose monosaccharide
- Chromone
- Glycosyl compound
- O-glycosyl compound
- Benzopyran
- 1-benzopyran
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Pyran
- Monocyclic benzene moiety
- Oxane
- Benzenoid
- Monosaccharide
- Heteroaromatic compound
- Secondary alcohol
- Polyol
- Acetal
- Oxacycle
- Organoheterocyclic compound
- Organic oxide
- Organic oxygen compound
- Primary alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- 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 | Industrial application: 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 60.58%; H 4.84%; O 34.58% | DFC |
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Melting Point | Mp 233-235° | 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]20D -36.4 (0.02M KOH) | DFC |
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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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Predicted GC-MS | Daidzin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0f72-5619000000-9a00dd3afb417b948c0d | Spectrum | Predicted GC-MS | Daidzin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-014i-3614129000-e673b080216b7c841658 | Spectrum | Predicted GC-MS | Daidzin, 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 30V, Negative | splash10-03di-0000092000-84a513c4afef1602030f | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-03di-0000092000-84a513c4afef1602030f | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-03di-0000900000-a8a90b48831795fcef5b | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-03di-0000900000-a8a90b48831795fcef5b | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0w29-0090800000-71336b3ac56112e89965 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-0w29-0090800000-71336b3ac56112e89965 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-0udi-0090100000-a3ff46535f112a06438e | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-0udi-0090000000-806672a9fe6ab0e8821b | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-03di-0000900000-a8a90b48831795fcef5b | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0udi-0090300000-0e1086947a1b1fb0fc9c | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0w29-0090800000-71336b3ac56112e89965 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-0udi-0090000000-3c95cabcacf790fe32be | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0uxr-0190300000-7c009a9b8fd016988c20 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0090300000-87d938e172f23b8f9266 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0090101010-00cce9f1d03944bfc839 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0090000000-f372e3204e88dfa0fac6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0089-2970000000-19bb9d5854402bda7386 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0190200000-21f48ac2697d0d52ecd2 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0udi-0090000000-65cde820e99b7330181c | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0aor-0194400000-29efa8833365732bd0d9 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-0090000000-c52f4b92c3ebc772069d | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a6r-2290000000-8c00534d044e8a4e8e17 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0gb9-1173900000-06545d43f6fa1210591a | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-1091000000-d49a71a5c4f62e485da7 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-3390000000-2d121e77ef35344d0179 | 2016-08-03 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 97088 |
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ChEMBL ID | CHEMBL486422 |
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KEGG Compound ID | C10216 |
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Pubchem Compound ID | 107971 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 4307 |
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Phenol-Explorer ID | 403 |
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DrugBank ID | DB02115 |
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HMDB ID | HMDB33991 |
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CRC / DFC (Dictionary of Food Compounds) ID | CMR01-H:HFG13-P |
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EAFUS ID | Not Available |
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Dr. Duke ID | DAIDZIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002518 |
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HET ID | DZN |
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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 | Daidzin |
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Phenol-Explorer Metabolite ID | 403 |
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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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anti alcoholic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti dipsomanic | | | DUKE | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | estrogenic | | | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | hypotensive | | | DUKE | lipase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | 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 | — 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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