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Record Information
Version1.0
Created at2006-05-22 15:12:49 UTC
Updated at2021-08-19 20:22:30 UTC
NP-MRD IDNP0000025
Secondary Accession NumbersNone
Natural Product Identification
Common NameDaidzein
DescriptionDaidzein is one of several known isoflavones. Isoflavones compounds are found in a number of plants, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Up until recently, daidzein was considered to be one of the most important and most studied isoflavones, however more recently attention has shifted to isoflavone metabolites. Equol represents the main active product of daidzein metabolism, produced via specific microflora in the gut. The clinical effectiveness of soy isoflavones may be a function of the ability to biotransform soy isoflavones to the more potent estrogenic metabolite, equol, which may enhance the actions of soy isoflavones, owing to its greater affinity for estrogen receptors, unique antiandrogenic properties, and superior antioxidant activity. However, not all individuals consuming daidzein produce equol. Only approximately one-third to one-half of the population is able to metabolize daidzein to equol. This high variability in equol production is presumably attributable to interindividual differences in the composition of the intestinal microflora, which may play an important role in the mechanisms of action of isoflavones. But, the specific bacterial species in the colon involved in the production of equol are yet to be discovered. (PMID: 18045128 , 17579894 ). Daidzein is a biomarker for the consumption of soy beans and other soy products.
Structure
Data?1628564076
Synonyms
ValueSource
4',7-DihydroxyisoflavoneChEBI
7,4'-DihydroxyisoflavoneChEBI
7-Hydroxy-3-(4-hydroxyphenyl)-4-benzopyroneChEBI
7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
DaidzeolChEBI
IsoaurostatinChEBI
4',7-Dihydroxy-isoflavoneHMDB
DiadzeinHMDB
Chemical FormulaC15H10O4
Average Mass254.2410 Da
Monoisotopic Mass254.05791 Da
IUPAC Name7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Namedaidzein
CAS Registry Number486-66-8
SMILES
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])OC2=C([H])C(O[H])=C([H])C([H])=C2C1=O
InChI Identifier
InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H
InChI KeyZQSIJRDFPHDXIC-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, simulated)V.dorna832021-07-19View Spectrum
Species
Species of Origin
Species NameSourceReference
Acca sellowianaKNApSAcK Database
Albizia proceraKNApSAcK Database
Aloe veraKNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaKNApSAcK Database
Brassica oleraceaKNApSAcK Database
Bupleurum scorzonerifoliumKNApSAcK Database
Cajanus cajanKNApSAcK Database
Cicer arietinumKNApSAcK Database
Crotalaria assamicaKNApSAcK Database
Crotalaria pallidaKNApSAcK Database
Dalbergia ecastaphyllumKNApSAcK Database
Dalbergia odoriferaKNApSAcK Database
Dalbergia stevensoniiKNApSAcK Database
Derris oblongaKNApSAcK Database
Erycibe expansaKNApSAcK Database
Erythrina crista-galliKNApSAcK Database
Erythrina indicaKNApSAcK Database
Erythrina latissimaKNApSAcK Database
Erythrina orientalisKNApSAcK Database
Erythroxylum uleiKNApSAcK Database
Euchresta formosanaKNApSAcK Database
Genista corsicaKNApSAcK Database
Genista tinctoriaKNApSAcK Database
Glycine maxKNApSAcK Database
Glycyrrhiza glabraKNApSAcK Database
Glycyrrhiza inflataKNApSAcK Database
Glycyrrhiza uralensisKNApSAcK Database
Lespedeza bicolorKNApSAcK Database
Maackia amurensisKNApSAcK Database
Medicago arabicaKNApSAcK Database
Medicago sativaKNApSAcK Database
Medicago truncatulaKNApSAcK Database
Pericopsis angolensis Baker.KNApSAcK Database
Pericopsis eletaKNApSAcK Database
Pericopsis laxiflora Benth.KNApSAcK Database
Pericopsis moonianaKNApSAcK Database
Phaseolus coccineusKNApSAcK Database
Phaseolus spp.KNApSAcK Database
Phaseolus vulgarisKNApSAcK Database
Piptanthus nepalensisKNApSAcK Database
Pisum sativumKNApSAcK Database
Podocarpus amarusKNApSAcK Database
Psoralea corylifoliaKNApSAcK Database
Pterocarpus marsupiumKNApSAcK Database
Pueraria calycinaKNApSAcK Database
Pueraria candollei var. mirificaKNApSAcK Database
Pueraria edulisKNApSAcK Database
Pueraria lobataKNApSAcK Database
Pueraria mirificaKNApSAcK Database
Pueraria peduncularisKNApSAcK Database
Pueraria PhaseoloidesKNApSAcK Database
Pueraria thunbergianaKNApSAcK Database
Pueraria tuberosaKNApSAcK Database
Punica granatumKNApSAcK Database
Retama raetamKNApSAcK Database
Sophora flavescensKNApSAcK Database
Sophora japonicaKNApSAcK Database
Sophora subprostrataKNApSAcK Database
Taxus fuanaKNApSAcK Database
Taxus yunnanensisKNApSAcK Database
Trifolium pratenseKNApSAcK Database
Trifolium repensKNApSAcK Database
Tripterygium wilfordiiKNApSAcK Database
Ulex europaeusKNApSAcK Database
Vigna radiataKNApSAcK Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Streptomyces xanthophaeus MD865-C3KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflav-2-enes
Direct ParentIsoflavones
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point323 °CNot Available
Boiling Point512.00 to 513.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility568.4 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.632 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility0.085 g/LALOGPS
logP3.3ALOGPS
logP2.73ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)6.48ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.7 m³·mol⁻¹ChemAxon
Polarizability25.75 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0003312
DrugBank IDDB13182
Phenol Explorer Compound ID394
FoodDB IDFDB002608
KNApSAcK IDC00009380
Chemspider ID4445025
KEGG Compound IDC10208
BioCyc IDDAIDZEIN
BiGG IDNot Available
Wikipedia LinkDaidzein
METLIN IDNot Available
PubChem Compound5281708
PDB IDNot Available
ChEBI ID28197
Good Scents IDrw1504461
References
General References
  1. Jackman KA, Woodman OL, Sobey CG: Isoflavones, equol and cardiovascular disease: pharmacological and therapeutic insights. Curr Med Chem. 2007;14(26):2824-30. [PubMed:18045128 ]
  2. Yuan JP, Wang JH, Liu X: Metabolism of dietary soy isoflavones to equol by human intestinal microflora--implications for health. Mol Nutr Food Res. 2007 Jul;51(7):765-81. [PubMed:17579894 ]
  3. Antignac JP, Cariou R, Le Bizec B, Cravedi JP, Andre F: Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2003;17(12):1256-1264. doi: 10.1002/rcm.1052. [PubMed:12811748 ]
  4. Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. [PubMed:18565930 ]
  5. Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. [PubMed:19679050 ]