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Human Metabolome Database Version 3.5

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Showing metabocard for Equol (HMDB02209)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:42 -0600
Update Date 2013-02-08 17:11:34 -0700
HMDB ID HMDB02209
Secondary Accession Numbers None
Metabolite Identification
Common Name Equol
Description Equol is a metabolite of daidzein, a phytoestrogen common in the human diet and abundant in soy. Intestinal bacteria in humans can reduce daidzein to equol, and can be found in normal human urine. 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. (PMID: 17579895 Link_out, 17579894 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (-)-(S)-Equol
  2. (-)-Equol
  3. (S)-(-)-4',7-Isoflavandiol
  4. (S)-3,4-dihydro-3-(4-hydroxyphenyl)-2H-1-Benzopyran-7-ol
  5. (S)-Equol
  6. 4',7-Dihydroxyisoflavan
  7. 4',7-Isoflavandiol
Chemical Formula C15H14O3
Average Molecular Weight 242.2699
Monoisotopic Molecular Weight 242.094294314
IUPAC Name (3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol
Traditional IUPAC Name (3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol
CAS Registry Number 531-95-3
SMILES OC1=CC=C(C=C1)[C@H]1COC2=C(C1)C=CC(O)=C2
InChI Identifier InChI=1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2/t12-/m1/s1
InChI Key ADFCQWZHKCXPAJ-GFCCVEGCSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Flavonoids
Sub Class Isoflavans
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Isoflavanes(KEGG)
  • Isoflavans
  • Isoflavans(KEGG)
Substituents
  • Alkyl Aryl Ether
  • Benzopyran
  • Chromane
  • Phenol
  • Phenol Derivative
  • Pyran
Direct Parent Isoflavanols
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 189.5 °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 0.044 g/L ALOGPS
LogP 2.91 ALOGPS
LogP 3.19 ChemAxon
LogS -3.74 ALOGPS
pKa (strongest acidic) 9.63 ChemAxon
pKa (strongest basic) -4.9 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 49.69 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 68.96 ChemAxon
Polarizability 25.81 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
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
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0.0006 (0.00057 - 0.00066) uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
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0.0006 (0.00057 - 0.0007) uM Adult (>18 years old) Female Normal Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 866 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 866 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 866 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 866 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 866 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 866 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 866 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 866 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 866 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 866 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 866 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 866 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 866 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 866 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 866 Not Available
Urine Detected and Quantified
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0.06 (0.01-0.10) umol/mmol creatinine Adult (>18 years old) Both Normal by HPLC-UV
Urine Detected and Quantified
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0.13 +/- 0.12 (0.0061-0.623) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
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0 - 36.7 umol/mmol creatinine Adult (>18 years old) Both Soy consumption ( ileostomies) Not Available
Associated Disorders and Diseases
Disease References
Ileostomy
  • 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 Link_out
    Associated OMIM IDs None
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID 866 Link_out
    FoodDB ID FDB021824
    KNApSAcK ID C00009707 Link_out
    Chemspider ID 82594 Link_out
    KEGG Compound ID C14131 Link_out
    BioCyc ID Not Available
    BiGG ID Not Available
    Wikipedia Link Equol Link_out
    NuGOwiki Link HMDB02209 Link_out
    Metagene Link HMDB02209 Link_out
    METLIN ID Not Available
    PubChem Compound 91469 Link_out
    PDB ID Not Available
    ChEBI ID 428126 Link_out
    References
    Synthesis Reference Wang, Xiu-Ling; Hur, Hor-Gil; Lee, Je Hyeon; Kim, Ki Tae; Kim, Su-Il. Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium. Applied and Environmental Microbiology (2005), 71(1), 214-219
    Material Safety Data Sheet (MSDS) Download (PDF)
    General References Not Available