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=CC(O)=CC=C3C2

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

Molecular Formula	C15H14O3
Molecular Weight	242.2699
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 2752	1.5 µM [IC50]
Estrogen-related receptor beta 8 Target ID: CHEMBL3751 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28587197	Agonist 2752	0.2 µM [IC50]
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22798715	Inhibitor 8504
Apoptosis 156 Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24487643	Inhibitor 8504

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 186 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
Resveratrol, 4' Acetoxy Resveratrol, R-equol, Racemic Equol or S-equol as Cosmeceuticals to Improve Dermal Health.	2017-06-03	28587197
HIV-1 Tat and cocaine mediated synaptopathy in cortical and midbrain neurons is prevented by the isoflavone Equol.	2015	26441850
Equol induces apoptosis in human hepatocellular carcinoma SMMC-7721 cells through the intrinsic pathway and the endoplasmic reticulum stress pathway.	2014-07	24487643
Potentiation of brain mitochondrial function by S-equol and R/S-equol estrogen receptor β-selective phytoSERM treatments.	2013-06-13	23428542
Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor alpha (ERalpha) and ERbeta in human cells.	2004-07	15084758

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:41:04 GMT 2025` Edited by `admin` on `Mon Mar 31 20:41:04 GMT 2025`
Record UNII	2RZ8A7D0E8
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

EQUOL, (±)-

Common Name

English

(±)-EQUOL

Preferred Name

English

7,4'-HOMOISOFLAVANE

Common Name

English

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

Systematic Name

English

Code System Code Type Description

FDA UNII

2RZ8A7D0E8