Record Information
Version1.0
Creation date2010-04-08 22:05:27 UTC
Update date2019-11-26 02:57:41 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
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
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
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Foods

Nuts and legumes:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSDaidzein, non-derivatized, GC-MS Spectrumsplash10-001j-1928000000-f956e5fd0e616ef96161Spectrum
GC-MSDaidzein, 2 TMS, GC-MS Spectrumsplash10-000t-1619000000-eb2f87cd7d535b4d0446Spectrum
GC-MSDaidzein, non-derivatized, GC-MS Spectrumsplash10-001j-1928000000-f956e5fd0e616ef96161Spectrum
GC-MSDaidzein, non-derivatized, GC-MS Spectrumsplash10-000t-1619000000-eb2f87cd7d535b4d0446Spectrum
GC-MSDaidzein, non-derivatized, GC-MS Spectrumsplash10-001j-1927000000-87f11afa0cde5b353147Spectrum
Predicted GC-MSDaidzein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-1390000000-0ff8f0de4d2d339f9357Spectrum
Predicted GC-MSDaidzein, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00gi-4229000000-71c73470904ad7b680eeSpectrum
Predicted GC-MSDaidzein, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0090000000-20d2c8ade6aac1f46e8a2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0970000000-a2349152106bd9da12572012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-691c394958fd19d475102012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0f7x-4900000000-5acb56232432597c00e52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0pej-1930000000-89bedfb39603a12f3c752012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0a4i-0490000000-c633d3449d8bb0206fc22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0a4i-0190000000-3a5de741e814e47d5cbe2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0a4i-0090000000-fb84819005f7f65b4fc82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0a4i-0090000000-b3ae695d217c756a5f8f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-0a4i-0090000000-d25bba2f5a1ac12e3d862012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0190000000-a9b6c8c416cb482a5dc12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0089-1970000000-f6070acf0fd663c4ae6f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0uem-1900000000-fa199caebb806e9eb0f92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-0490000000-3defe1cbaf29e0cd2d1f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-1790000000-2502633932fc662200392012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0290000000-56b4c039a64ab57d3e702012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0089-2970000000-f32e85ba94cb6621d4f12012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-7dcbed418d38de1208952015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-c522d590074eabe8c4c42015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-6950000000-7b85969731514bf2d0bc2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-388d21c85a84d4e0988a2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-cc8371583b5ba50a4f0d2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbi-3950000000-cb120c48a579b9363f742015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-7dcbed418d38de1208952015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-c522d590074eabe8c4c42015-05-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
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
Food Biomarker OntologyNot Available
VMH 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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
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).