Record Information
Creation date2010-04-08 22:05:27 UTC
Update date2018-05-28 22:14:06 UTC
Primary IDFDB002608
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDaidzein
DescriptionWidespread isoflavone in the Leguminosae, especies Phaseolus subspecies (broad beans, lima beans); also found in soy and soy products (tofu, miso), chick peas (Cicer arietinum) and peanuts (Arachis hypogaea). Nutriceutical with anticancer and bone protective props. Daidzein 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, Curr Med Chem. 2007;14(26):2824-30., Mol Nutr Food Res. 2007 Jul;51(7):765-81.) Daidzein is a biomarker for the consumption of soy beans and other soy products. .
CAS Number486-66-8
7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9CIdb_source
Dimethylbiochanin Bdb_source
K 251-6db_source
Predicted Properties
Water Solubility0.085 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H10O4
IUPAC name7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=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
Isomeric SMILESOC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O
Average Molecular Weight254.241
Monoisotopic Molecular Weight254.057908802
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
Sub ClassIsoflav-2-enes
Direct ParentIsoflavones
Alternative Parents
  • 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 70.86%; H 3.96%; O 25.17%DFC
Melting PointMp 330° (323°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 252 (e 25400) (MeOH) (Derep)DFC
DensityNot Available
Refractive IndexNot Available
Spectrum TypeDescriptionSplash Key
ChemSpider ID4445025
KEGG Compound IDC10208
Pubchem Compound ID5281708
Pubchem Substance IDNot Available
ChEBI ID28197
Phenol-Explorer ID394
DrugBank IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCMR01-H:CMR01-H
EAFUS IDNot Available
BIGG IDNot Available
KNApSAcK IDC00009380
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDaidzein
Phenol-Explorer Metabolite ID394
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Biological Effects and Interactions
Health Effects / Bioactivities
anti alcoholic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti arrhythmic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti cephalagic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti dipsomanicDUKE
anti estrogenic35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti hemolytic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti microbial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti mutagenicDUKE
anti osteoporotic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 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 proliferativeDUKE
anti radicularDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
aromatase inhibitor50790 An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC and so reduces production of estrogenic steroid hormones.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
estrogen agonist63951 An agonist at the estrogen receptor.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
lipase inhibitor23924 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
quinone-reductase inducerDUKE
topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
topoisomerase-I inhibitor50276 A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.DUKE
utero trophic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
VEGF inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
  1. 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
Synthesis ReferenceNot Available
General ReferenceNot Available
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.
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).