Bovine Metabolome Database: Showing metabocard for Equol (BMDB0002209)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:52:41 UTC

Update Date

2020-06-04 21:10:23 UTC

BMDB ID

BMDB0002209

Secondary Accession Numbers

BMDB02209

Metabolite Identification

Common Name

Equol

Description

Equol, 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(+-)-Isomer OF equol	MeSH
3' Hydroxy equol	MeSH
3'-Hydroxy-equol	MeSH
4' O Methyl equol	MeSH
4' Methoxy 7 isoflavanol	MeSH
4'-O-Methyl equol	MeSH
4'-Methoxy-7-isoflavanol	MeSH
6' Hydroxy equol	MeSH
6'-Hydroxy-equol	MeSH
Equol, 4'-O-methyl	MeSH
AUS-131(S)-equol	ChEMBL, HMDB
(-)-(S)-Equol	HMDB
(-)-Equol	HMDB
(S)-(-)-4',7-Isoflavandiol	HMDB
(S)-3,4-dihydro-3-(4-Hydroxyphenyl)-2H-1-benzopyran-7-ol	HMDB
(S)-Equol	HMDB
4',7-Dihydroxyisoflavan	HMDB
4',7-Isoflavandiol	HMDB

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 Name

(-)-equol

CAS Registry Number

531-95-3

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 Key

ADFCQWZHKCXPAJ-GFCCVEGCSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanols

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavans (CHEBI:34741 )
isoflavans (C14131 )
Isoflavanes (C14131 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.91	ALOGPS
logP	3.19	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.63	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.96 m³·mol⁻¹	ChemAxon
Polarizability	25.81 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-2590000000-de6943a0e29cb74d29c4	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-6439000000-bd3446db9a81b442105b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0890000000-7e7596ef550328bb2d8b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0950000000-eb2fba880af94e2ffaa4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0adi-5910000000-ae99af1d6277808c807a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0390000000-9e81ff09baf049465955	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0390000000-23c63d12aef21bc1a2fe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0603-4930000000-18ce0b21dd8e144014a5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0005-0960000000-9edad7cf7d51f7a71fee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0590000000-19e7c74a42b427564aac	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-4930000000-a7500058dae2b15f912b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-006x-0970000000-7b598fa2edd4a41a1f9b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kf-1970000000-4a2a37c7a8d430f4f164	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-3910000000-5790b5708e0e13e02c98	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

Milk

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Milk	Detected and Quantified	0.0206 - 0.124 uM	Not Specified	Not Specified	Normal	PMID: 12811748	details
Milk	Detected and Quantified	0.194 +/- 0.0144 uM	Not Specified	Not Specified	Normal	Shin Tsen, Jinyi ...	details
Milk	Detected and Quantified	0.0778 +/- 0.0103 uM	Not Specified	Not Specified	Normal	Shin Tsen, Jinyi ...	details
Milk	Detected and Quantified	0.00516 +/- 0.00347 uM	Not Specified	Not Specified	Normal	Shin Tsen, Jinyi ...	details
Milk	Detected and Quantified	0.00239 +/- 8.255e-05 uM	Not Specified	Not Specified	Normal	Shin Tsen, Jinyi ...	details
Milk	Detected and Quantified	0.186 - 1.209 uM	Not Specified	Not Specified	Normal	PMID: 9718497	details
Milk	Detected and Quantified	0.256 uM	Not Specified	Not Specified	Normal	PMID: 17576638	details
Milk	Detected and Quantified	1.696 uM	Not Specified	Not Specified	Normal	PMID: 17576638	details
Milk	Detected and Quantified	1125.604 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details
Milk	Detected and Quantified	1502.456 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details
Milk	Detected and Quantified	214.637 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details
Milk	Detected and Quantified	400.793 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details
Milk	Detected and Quantified	0.237 - 4.140 uM	Not Specified	Not Specified	Normal	PMID: 19679050	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0002209

DrugBank ID

DB11674

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Equol

METLIN ID

Not Available

PubChem Compound

91469

PDB ID

Not Available

ChEBI ID

428126

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)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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.

Showing metabocard for Equol (BMDB0002209)

Structure for BMDB0002209 (Equol)