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Record Information
Version2.0
Created at2006-05-22 15:12:49 UTC
Updated at2025-02-11 15:40:14 UTC
NP-MRD IDNP0000025
Natural Product DOIhttps://doi.org/10.57994/0927
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
Experimental Spectra
Predicted Spectra
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-07-19View Spectrum
Species
Species of Origin
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 Parents
Substituents
  • Isoflavone
  • Hydroxyisoflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Pyranone
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
HMDB IDHMDB0003312
DrugBank IDDB13182
Phenol Explorer Compound ID394
FoodDB IDFDB093497
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 ]