EQUOL, (±)-

Details

Stereochemistry	RACEMIC
Molecular Formula	C15H14O3
Molecular Weight	242.2699
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(C=C1)C2COC3=C(C2)C=CC(O)=C3

InChI

InChIKey=ADFCQWZHKCXPAJ-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28587197 | https://www.ncbi.nlm.nih.gov/pubmed/24487643 | https://www.ncbi.nlm.nih.gov/pubmed/16898868

EQUOL is a chiral compound and can exist in three forms, racemic (±)equol (R/S-equol), R-equol and S-equol. Racemic equol refers to exact equal portions of S-equol and R-equol. EQUOL, (±)- can induce apoptosis of human hepatocellular carcinoma cells through the intrinsic pathway and the endoplasmic reticulum stress pathway. Racemic equol (10, 30 uM) prevented DNA damage in MCF-10A cells following exposure to 2-hydroxy-4-nonenal or menadione. This finding suggest that racemic equol has strong antigenotoxic activity in contrast to the purified S-equol enantiomer implicating the R-, rather than the S-enantiomer as being responsible for the antioxidant effects of racemic equol, a finding that may have implications for the in vivo chemoprotective properties of EQUOL, (±)-.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Estrogen-related receptor alpha 12 Target ID: CHEMBL3429 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28587197	Agonist 2678	1.5 µM [IC50]
Estrogen-related receptor beta 8 Target ID: CHEMBL3751 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28587197	Agonist 2678	0.2 µM [IC50]
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22798715	Inhibitor 8297
Apoptosis 155 Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24487643	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Skin diseases 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28587197	Primary	Basic research	Unknown Approved Use Unknown
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22798715 https://www.ncbi.nlm.nih.gov/pubmed/16898868	Primary	Basic research	Unknown Approved Use Unknown
Hepatocellular carcinoma 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24487643	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor alpha (ERalpha) and ERbeta in human cells.	2004 Jul	15084758
Potentiation of brain mitochondrial function by S-equol and R/S-equol estrogen receptor β-selective phytoSERM treatments.	2013 Jun 13	23428542
Equol induces apoptosis in human hepatocellular carcinoma SMMC-7721 cells through the intrinsic pathway and the endoplasmic reticulum stress pathway.	2014 Jul	24487643
HIV-1 Tat and cocaine mediated synaptopathy in cortical and midbrain neurons is prevented by the isoflavone Equol.	2015	26441850
Resveratrol, 4' Acetoxy Resveratrol, R-equol, Racemic Equol or S-equol as Cosmeceuticals to Improve Dermal Health.	2017 Jun 3	28587197

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 50 or100 or 200 mg/kg 8-wk diet

Route of Administration: Oral

In Vitro Use Guide

Treatment with 5 uM, 10 uM, 50 uM EQUOL, (±)- for 24 h decreased human prostate cancer DU145 cells migration and invasion significantly. EQUOL, (±)- activated phosphatase and tensin homologue deleted on chromosome ten at protein level but not mRNA level, which activated antioxidants, including superoxide dismutase and nuclear factor (erythroid-derived 2)-like 2.

Name

Type

Language

EQUOL, (±)-

Common Name

English

7,4'-HOMOISOFLAVANE

Common Name

English

2H-1-BENZOPYRAN-7-OL, 3,4-DIHYDRO-3-(4-HYDROXYPHENYL)-

Systematic Name

English

(±)-EQUOL

Common Name

English

Code System Code Type Description

FDA UNII

2RZ8A7D0E8