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Human Metabolome Database Version 3.5

Showing metabocard for Daidzein (HMDB03312)

• Identification
• Taxonomy
• Ontology
• Physical properties
• Spectra
• Biological properties
• Concentrations
• Links
• References

• Blood
• Urine

Record Information
Version	3.5
Creation Date	2006-05-22 09:12:49 -0600
Update Date	2013-02-08 17:12:25 -0700
HMDB ID	HMDB03312
Secondary Accession Numbers	None
Metabolite Identification
Common Name	Daidzein
Description	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.).
Structure	Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure
Synonyms	4',7-Dihydroxy-Isoflavone 4',7-Dihydroxyisoflavone 7,4'-Dihydroxyisoflavone 7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one Daidzeol Isoaurostatin
Chemical Formula	C15H10O4
Average Molecular Weight	254.2375
Monoisotopic Molecular Weight	254.057908808
IUPAC Name	7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional IUPAC Name	daidzein
CAS Registry Number	486-66-8
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 Key	ZQSIJRDFPHDXIC-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom	Organic Compounds
Super Class	Aromatic Heteropolycyclic Compounds
Class	Flavonoids
Sub Class	Isoflavones
Other Descriptors	Aromatic Heteropolycyclic Compounds Isoflavones(KEGG) Isoflavonoids(KEGG) Isoflavonoids(Lipidmaps) a 4'-hydroxyisoflavone(Cyc) an isoflavone(Cyc) hydroxyisoflavone(ChEBI)
Substituents	Benzopyran Chromone Phenol Phenol Derivative Pyran Pyranone
Direct Parent	Isoflavones
Ontology
Status	Detected and Quantified
Origin	Plant
Biofunction	Not Available
Application	Not Available
Cellular locations	Not Available
Physical Properties
State	Solid
Experimental Properties	Property Value Reference Melting Point 323 °C Not Available Boiling Point Not Available Not Available Water Solubility Not Available Not Available LogP Not Available Not Available
Predicted Properties	Property Value Source Water Solubility 0.085 g/L ALOGPS LogP 3.30 ALOGPS LogP 2.73 ChemAxon LogS -3.48 ALOGPS pKa (strongest acidic) 6.48 ChemAxon pKa (strongest basic) -5.3 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 66.76 A2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 69.7 ChemAxon Polarizability 25.75 ChemAxon Formal Charge 0 ChemAxon Physiological Charge -1 ChemAxon
Spectra
	1H NMR Spectrum MS/MS Spectrum Quattro_QQQ 10 MS/MS Spectrum Quattro_QQQ 25 MS/MS Spectrum Quattro_QQQ 40 MS/MS Spectrum LC-APPI-QQ (API2000) MS/MS Spectrum LC-APPI-QQ (API2000) MS/MS Spectrum LC-APPI-QQ (API2000) MS/MS Spectrum LC-APPI-QQ (API2000) MS/MS Spectrum LC-APPI-QQ (API2000) MS/MS Spectrum LC-APPI-QQ (API2000) MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies ) MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5 MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) [1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations	Not Available
Biofluid Locations	Blood Urine
Tissue Location	Not Available
Pathways	Not Available
Normal Concentrations
	Biofluid Status Value Age Sex Condition Comments Blood Detected and Quantified 0.0035 (0.0031 - 0.0040) uM Adult (>18 years old) Male Normal Not Available Blood Detected and Quantified 0.0031 (0.0028 - 0.0035) uM Adult (>18 years old) Female Normal Not Available Urine Detected and Quantified 0.026 (0.002-0.064) umol/mmol creatinine Adult (>18 years old) Both Normal by HPLC-UV Urine Detected and Quantified 0.036 +/- 0.008 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available Urine Detected and Quantified 0.13 +/- 0.021 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 394 Not Available Urine Detected and Quantified 4.11 +/- 0.54 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
	Biofluid Status Value Age Sex Condition Comments Urine Detected and Quantified 2.43 +/- 0.65 umol/mmol creatinine Adult (>18 years old) Both Soy consumption (ileostomies) Not Available
Associated Disorders and Diseases
Disease References	None
Associated OMIM IDs	None
External Links
DrugBank ID	Not Available
Phenol Explorer Compound ID	394
Phenol Explorer Metabolite ID	394
FoodDB ID	FDB002608
KNApSAcK ID	C00009380
Chemspider ID	4445025
KEGG Compound ID	C10208
BioCyc ID	2-HYDROXYDAIDZEIN
BiGG ID	Not Available
Wikipedia Link	Not Available
NuGOwiki Link	HMDB03312
Metagene Link	HMDB03312
METLIN ID	Not Available
PubChem Compound	5281708
PDB ID	Not Available
ChEBI ID	28197
References
Synthesis Reference	Baker, 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	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 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

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government.