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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:49 UTC
Update Date2019-07-23 05:45:44 UTC
HMDB IDHMDB0003312
Secondary Accession Numbers
  • HMDB03312
Metabolite 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 , 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.
Structure
Data?1563860744
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 Molecular Weight254.241
Monoisotopic Molecular Weight254.057908802
IUPAC Name7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Namedaidzein
CAS Registry Number486-66-8
SMILES
OC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=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
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point323 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001j-1928000000-f956e5fd0e616ef96161JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-000t-1619000000-eb2f87cd7d535b4d0446JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001j-1928000000-f956e5fd0e616ef96161JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000t-1619000000-eb2f87cd7d535b4d0446JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001j-1927000000-87f11afa0cde5b353147JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1390000000-0ff8f0de4d2d339f9357JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00gi-4229000000-71c73470904ad7b680eeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0090000000-20d2c8ade6aac1f46e8aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0970000000-a2349152106bd9da1257JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-691c394958fd19d47510JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0f7x-4900000000-5acb56232432597c00e5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0pej-1930000000-89bedfb39603a12f3c75JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0a4i-0490000000-c633d3449d8bb0206fc2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0a4i-0190000000-3a5de741e814e47d5cbeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0a4i-0090000000-fb84819005f7f65b4fc8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0a4i-0090000000-b3ae695d217c756a5f8fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-0a4i-0090000000-d25bba2f5a1ac12e3d86JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0190000000-a9b6c8c416cb482a5dc1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0089-1970000000-f6070acf0fd663c4ae6fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0uem-1900000000-fa199caebb806e9eb0f9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-0490000000-3defe1cbaf29e0cd2d1fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-1790000000-2502633932fc66220039JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0290000000-56b4c039a64ab57d3e70JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0089-2970000000-f32e85ba94cb6621d4f1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-7dcbed418d38de120895JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-c522d590074eabe8c4c4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-6950000000-7b85969731514bf2d0bcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-388d21c85a84d4e0988aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-cc8371583b5ba50a4f0dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbi-3950000000-cb120c48a579b9363f74JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-7dcbed418d38de120895JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-c522d590074eabe8c4c4JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0426 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0969 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0069 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.00805 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0237 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0942 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.178 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0088 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.218 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.120 +/- 0.136 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0021 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.00367 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.00405 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.00787 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.00780 +/- 0.0110 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.112 +/- 0.188 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.018 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0035 (0.0031 - 0.0040) uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0031 (0.0028 - 0.0035) uMAdult (>18 years old)FemaleNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.86 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified1.633 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified0.0373 +/- 0.0573 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0373 +/- 0.0400 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.587 +/- 0.833 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified633.249 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.139 +/- 0.275 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified0.187 +/- 0.394 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified0.00157 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0272 umol/mmol creatinineChildren (1 - 13 years old)BothNormal details
UrineDetected and Quantified0.459 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified314.533 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.112 +/- 0.291 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.133 +/- 1.0200 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.026 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0441 umol/mmol creatinineChildren (1 - 13 years old)FemaleNormal details
UrineDetected and Quantified0.0629 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.564 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.577 umol/mmol creatinineChildren (1-13 years old)FemaleNormal details
UrineDetected and Quantified1.843 umol/mmol creatinineChildren (1-13 years old)FemaleNormal details
UrineDetected and Quantified0.0672 +/- 0.104 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0704 +/- 0.106 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.026 (0.002-0.064) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.126 +/- 0.251 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.286 +/- 0.685 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.299 +/- 0.488 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.707 +/- 1.0576 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified1.553 +/- 1.360 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.036 +/- 0.008 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.13 +/- 0.021 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineDetected and Quantified0.0787 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineDetected and Quantified0.195 +/- 0.420 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394 details
UrineDetected and Quantified4.11 +/- 0.54 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0284 (0.0249-0.0324) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.0569 (0.0449-0.0729) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified2.43 +/- 0.65 umol/mmol creatinineAdult (>18 years old)BothSoy consumption (ileostomies) details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Ileostomy
  1. Walsh KR, Haak SJ, Bohn T, Tian Q, Schwartz SJ, Failla ML: Isoflavonoid glucosides are deconjugated and absorbed in the small intestine of human subjects with ileostomies. Am J Clin Nutr. 2007 Apr;85(4):1050-6. [PubMed:17413104 ]
Associated OMIM IDs
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
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceBaker, Wilson; Robinson, Robert; Simpson, N. M. Synthetical experiments in the isoflavone group. VII. Synthesis of daidzein. Journal of the Chemical Society (1933), 274-5.
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]