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Equol (FDB021824)

Record Information
Version1.0
Creation date2011-04-11 17:01:49 UTC
Update date2019-11-26 03:20:55 UTC
Primary IDFDB021824
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEquol
DescriptionEquol 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, 17579894) [HMDB]
CAS Number531-95-3
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP2.91ALOGPS
logP3.19ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.63ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity68.96 m³·mol⁻¹ChemAxon
Polarizability25.81 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H14O3
IUPAC name(3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol
InChI IdentifierInChI=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 KeyADFCQWZHKCXPAJ-GFCCVEGCSA-N
Isomeric SMILESOC1=CC=C(C=C1)[C@H]1COC2=CC(O)=CC=C2C1
Average Molecular Weight242.2699
Monoisotopic Molecular Weight242.094294314
Classification
Description Belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavans
Direct ParentIsoflavanols
Alternative Parents
Substituents
  • Hydroxyisoflavonoid
  • Isoflavanol
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

Foods

Nuts and legumes:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSEquol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dl-2590000000-de6943a0e29cb74d29c4Spectrum
Predicted GC-MSEquol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-6439000000-bd3446db9a81b442105bSpectrum
Predicted GC-MSEquol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0890000000-7e7596ef550328bb2d8b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0950000000-eb2fba880af94e2ffaa42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adi-5910000000-ae99af1d6277808c807a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0390000000-9e81ff09baf0494659552016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0390000000-23c63d12aef21bc1a2fe2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0603-4930000000-18ce0b21dd8e144014a52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0005-0960000000-9edad7cf7d51f7a71fee2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0590000000-19e7c74a42b427564aac2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-4930000000-a7500058dae2b15f912b2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006x-0970000000-7b598fa2edd4a41a1f9b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-1970000000-4a2a37c7a8d430f4f1642021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3910000000-5790b5708e0e13e02c982021-09-25View Spectrum
NMRNot Available
ChemSpider ID82594
ChEMBL IDCHEMBL198877
KEGG Compound IDC14131
Pubchem Compound ID91469
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID866
DrugBank IDNot Available
HMDB IDHMDB02209
CRC / DFC (Dictionary of Food Compounds) IDGZK56-X:FWN69-M
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00009707
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDEquol
Phenol-Explorer Metabolite ID866
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference