Record Information
Version1.0
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
Structure
Thumb
Synonyms
SynonymSource
4',7-Dihydroxy-isoflavoneHMDB
4',7-Dihydroxyisoflavonedb_source
7-Hydroxy-3-(4-hydroxy-phenyl)-chromonebiospider
7-Hydroxy-3-(4-hydroxyphenyl)-4-benzopyronebiospider
7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9CIdb_source
7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-onebiospider
7,4'-Dihydroxyisoflavonebiospider
Daidzeindb_source
Daidzeoldb_source
Daizeoldb_source
Dimethylbiochanin Bdb_source
Isoaurostatinbiospider
K 251-6db_source
Tatoindb_source
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
Bioavailability1ChemAxon
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
InChI KeyZQSIJRDFPHDXIC-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O
Average Molecular Weight254.241
Monoisotopic Molecular Weight254.057908802
Classification
ClassificationNot classified
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001j-1928000000-f956e5fd0e616ef96161View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-000t-1619000000-eb2f87cd7d535b4d0446View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001j-1928000000-f956e5fd0e616ef96161View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000t-1619000000-eb2f87cd7d535b4d0446View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001j-1927000000-87f11afa0cde5b353147View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1390000000-0ff8f0de4d2d339f9357View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00gi-4229000000-71c73470904ad7b680eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0090000000-20d2c8ade6aac1f46e8aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0970000000-a2349152106bd9da1257View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-691c394958fd19d47510View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0f7x-4900000000-5acb56232432597c00e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0pej-1930000000-89bedfb39603a12f3c75View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0a4i-0490000000-c633d3449d8bb0206fc2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0a4i-0190000000-3a5de741e814e47d5cbeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0a4i-0090000000-fb84819005f7f65b4fc8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0a4i-0090000000-b3ae695d217c756a5f8fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-0a4i-0090000000-d25bba2f5a1ac12e3d86View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0190000000-a9b6c8c416cb482a5dc1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0089-1970000000-f6070acf0fd663c4ae6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0uem-1900000000-fa199caebb806e9eb0f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-0490000000-3defe1cbaf29e0cd2d1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-1790000000-2502633932fc66220039View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0290000000-56b4c039a64ab57d3e70View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0089-2970000000-f32e85ba94cb6621d4f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-7dcbed418d38de120895View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-c522d590074eabe8c4c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-6950000000-7b85969731514bf2d0bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-388d21c85a84d4e0988aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-cc8371583b5ba50a4f0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbi-3950000000-cb120c48a579b9363f74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-7dcbed418d38de120895View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-c522d590074eabe8c4c4View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID4445025
ChEMBL IDCHEMBL8145
KEGG Compound IDC10208
Pubchem Compound ID5281708
Pubchem Substance IDNot Available
ChEBI ID28197
Phenol-Explorer ID394
DrugBank IDNot Available
HMDB IDHMDB03312
CRC / DFC (Dictionary of Food Compounds) IDCMR01-H:CMR01-H
EAFUS IDNot Available
Dr. Duke IDTATOIN|DAIDZEIN
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
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 1.14.14.14) and so reduces production of estrogenic steroid hormones.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
coronarydilatorDUKE
estrogen agonist63951 An agonist at the estrogen receptor.DUKE
estrogenicDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hypotensiveDUKE
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 5.99.1.3 (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 5.99.1.2) 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
Flavours
FlavorCitations
bitter
  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
Files
MSDSshow
References
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).