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Record Information
Version3.6
Creation Date2006-05-22 15:12:49 UTC
Update Date2016-02-11 01:06:09 UTC
HMDB IDHMDB03312
Secondary Accession NumbersNone
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.).
Structure
Thumb
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
Chemical FormulaC15H10O4
Average Molecular Weight254.2375
Monoisotopic Molecular Weight254.057908808
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 KeyInChIKey=ZQSIJRDFPHDXIC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydroxyisoflavonoid
  • Isoflavone
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • Phenol
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Plant
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.7 m3·mol-1ChemAxon
Polarizability25.75 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-001j-1928000000-f956e5fd0e616ef96161View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-000t-1619000000-eb2f87cd7d535b4d0446View 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 Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
UrineDetected and Quantified0.026 (0.002-0.064) umol/mmol creatinineAdult (>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 QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 394
  • Not Applicable
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
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified2.43 +/- 0.65 umol/mmol creatinineAdult (>18 years old)BothSoy consumption (ileostomies) details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID394
Phenol Explorer Metabolite ID394
FoodDB IDFDB002608
KNApSAcK IDC00009380
Chemspider ID4445025
KEGG Compound IDC10208
BioCyc ID2-HYDROXYDAIDZEIN
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03312
Metagene LinkHMDB03312
METLIN IDNot Available
PubChem Compound5281708
PDB IDNot Available
ChEBI ID28197
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. [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. [17579894 ]