Showing metabocard for Equol (BMDB0002209)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:52:41 UTC
Update Date2020-06-04 21:10:23 UTC
MCDB ID BMDB0002209
Secondary Accession Numbers
  • BMDB02209
Metabolite Identification
Common NameEquol
DescriptionEquol, also known as aus-131(S)-equol or 3'-hydroxy-equol, belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton. Equol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Equol is a potentially toxic compound.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(+-)-Isomer OF equolMeSH
3' Hydroxy equolMeSH
3'-Hydroxy-equolMeSH
4' O Methyl equolMeSH
4' Methoxy 7 isoflavanolMeSH
4'-O-Methyl equolMeSH
4'-Methoxy-7-isoflavanolMeSH
6' Hydroxy equolMeSH
6'-Hydroxy-equolMeSH
Equol, 4'-O-methylMeSH
AUS-131(S)-equolChEMBL, HMDB
(-)-(S)-EquolHMDB
(-)-EquolHMDB
(S)-(-)-4',7-IsoflavandiolHMDB
(S)-3,4-dihydro-3-(4-Hydroxyphenyl)-2H-1-benzopyran-7-olHMDB
(S)-EquolHMDB
4',7-DihydroxyisoflavanHMDB
4',7-IsoflavandiolHMDB
Chemical FormulaC15H14O3
Average Molecular Weight242.2699
Monoisotopic Molecular Weight242.094294314
IUPAC Name(3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol
Traditional Name(-)-equol
CAS Registry Number531-95-3
SMILES
OC1=CC=C(C=C1)[C@H]1COC2=CC(O)=CC=C2C1
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 KeyADFCQWZHKCXPAJ-GFCCVEGCSA-N
Chemical Taxonomy
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-2590000000-de6943a0e29cb74d29c42017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-6439000000-bd3446db9a81b442105b2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0890000000-7e7596ef550328bb2d8b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0950000000-eb2fba880af94e2ffaa42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adi-5910000000-ae99af1d6277808c807a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0390000000-9e81ff09baf0494659552016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0390000000-23c63d12aef21bc1a2fe2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0603-4930000000-18ce0b21dd8e144014a52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0005-0960000000-9edad7cf7d51f7a71fee2021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0590000000-19e7c74a42b427564aac2021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-4930000000-a7500058dae2b15f912b2021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006x-0970000000-7b598fa2edd4a41a1f9b2021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-1970000000-4a2a37c7a8d430f4f1642021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3910000000-5790b5708e0e13e02c982021-09-25View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.186 - 1.209 uM details
Detected and Quantified0.0206 - 0.124 uM details
Detected and Quantified0.256 uM details
Detected and Quantified1.696 uM details
Detected and Quantified1125 uM details
Detected and Quantified1503 uM details
Detected and Quantified214 uM details
Detected and Quantified400 uM details
Detected and Quantified0.237 - 4.14 uM details
Detected and Quantified0.194 +/- 0.0144 uM
  • Shin Tsen, Jinyi ...
 details
Detected and Quantified0.1 +/- 0.0103 uM
  • Shin Tsen, Jinyi ...
 details
Detected and Quantified0.01 +/- 0.004 uM
  • Shin Tsen, Jinyi ...
 details
Detected and Quantified0.0024 +/- 0.00008 uM
  • Shin Tsen, Jinyi ...
 details
HMDB IDHMDB0002209
DrugBank IDDB11674
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021824
KNApSAcK IDC00009707
Chemspider ID82594
KEGG Compound IDC14131
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEquol
METLIN IDNot Available
PubChem Compound91469
PDB IDNot Available
ChEBI ID428126
References
Synthesis ReferenceWang, 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
  1. King RA, Mano MM, Head RJ: Assessment of isoflavonoid concentrations in Australian bovine milk samples. J Dairy Res. 1998 Aug;65(3):479-89. [PubMed:9718497 ]
  2. Antignac JP, Cariou R, Le Bizec B, Cravedi JP, Andre F: Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2003;17(12):1256-64. doi: 10.1002/rcm.1052. [PubMed:12811748 ]
  3. Hoikkala A, Mustonen E, Saastamoinen I, Jokela T, Taponen J, Saloniemi H, Wahala K: High levels of equol in organic skimmed Finnish cow milk. Mol Nutr Food Res. 2007 Jul;51(7):782-6. doi: 10.1002/mnfr.200600222. [PubMed:17576638 ]
  4. Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. [PubMed:18565930 ]
  5. Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. [PubMed:19679050 ]
  6. Shin Tsen, Jinyi Siew, Eunice Lau, Farzana A qah Bte Roslee, Hui Chan, Wai Loke (2014). Shin Tsen, Jinyi Siew, Eunice Lau, Farzana A qah Bte Roslee, Hui Chan, Wai Loke Cow’s milk as a dietary source of equol and phenolic antioxidants: di erential distribution in the milk aqueous and lipid fractions. Dairy Sci. & Technol. (2014) 94:625–632. DOI 10.1007/s13594-014-0183-4. Dairy Science & Technology.