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 |
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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 | An agent that reduces alcohol cravings and withdrawal symptoms, commonly used in managing alcohol dependence and addiction, aiding in the treatment of alcohol use disorder by blocking the rewarding aspects of alcohol consumption. | DUKE | Anti dipsomanic | | An agent that reduces the compulsion to drink alcoholic beverages, aiding in the management of alcohol use disorder. Its biological role involves modulating neurotransmitters that regulate craving and reward. Therapeutically, it helps decrease alcohol consumption and withdrawal symptoms, making it a key medical use in the treatment of alcohol dependence and addiction. | DUKE | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | DUKE | Anti-spasmodic | 52217 | An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort. | DUKE | Cancer preventive | 35610 | An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence. | DUKE | Estrogenic | | An agent that mimics the effects of estrogen, regulating female reproductive processes and development. Therapeutically, estrogenic agents are used in hormone replacement therapy, contraception, and treating menopausal symptoms, as well as certain cases of osteoporosis and infertility. | DUKE | Fungicide | 24127 | An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage. | DUKE | Hypotensive | | An agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications. | DUKE | Lipase inhibitor | 23924 | An agent that blocks the activity of lipase, an enzyme that breaks down fats. It reduces fat absorption, commonly used in managing obesity and weight loss, particularly in combination with a low-calorie diet. | DUKE | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | 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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