EQUOL, (+)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H14O3
Molecular Weight	242.2699
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(C=C1)[C@@H]2COC3=CC(O)=CC=C3C2

InChI

InChIKey=ADFCQWZHKCXPAJ-LBPRGKRZSA-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/t12-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C15H14O3
Molecular Weight	242.2699
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20110282 | https://www.ncbi.nlm.nih.gov/pubmed/20519411 | https://www.ncbi.nlm.nih.gov/pubmed/24487643

(R)-Equol is a non-steroidal estrogen produced from the metabolism of the isoflavonoid phytoestrogen daidzein. R-(+)equol binds dihydrotestosterone and inhibit the in vivo stimulatory effect of this potent androgen on prostate growth. R-(+)equol was found in the model of the growth of mammary tumors induced by the chemical carcinogen dimethylbenz[a]anthracene to be a potently chemopreventive. R-(+)-equol can induce apoptosis of human hepatocellular carcinoma SMMC-7721 cells through the intrinsic pathway and the endoplasmic reticulum stress pathway.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Estrogen-related receptor beta 8 Target ID: CHEMBL3751 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28587197	Agonist 2752	15.4 nM [Ki]
Estrogen-related receptor alpha 12 Target ID: CHEMBL3429 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28587197	Agonist 2752	27.4 nM [Ki]
Apoptosis 156 Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24487643	Activator 1447

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
HIV-1 infection + drug abuse synaptopathy 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26441850	Preventing	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
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20691242 https://www.ncbi.nlm.nih.gov/pubmed/20110282	Preventing	Preclinical	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
S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora.	2005-05	15883431

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 250 mg/kg

Route of Administration: Oral

In Vitro Use Guide

Midbrain neurons were pre-treated with either EQUOL, (+)- (33 or 50 nM) for 24 h prior to 50 nM HIV-1 Tat. There was a significant main effect of treatment F(1,22) = 9.4, p ≤ 0.001, with 50 nM HIV-1 Tat producing a significant reduction in F-actin puncta (p ≤ 0.001). Pretreatment with 50 nM EQUOL, (+)- (p ≤ 0.01), but not 33 nM EQUOL, (+)-, prevented significant loss of F-actin puncta following 50 nM HIV-1 Tat.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:40:29 GMT 2025` Edited by `admin` on `Mon Mar 31 20:40:29 GMT 2025`
Record UNII	2V8RAP1HXA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EQUOL, (+)-

Common Name

English

EQUOL (R)-FORM

Preferred Name

English

(+)-EQUOL

Common Name

English

(R)-EQUOL

Common Name

English

EQUOL (R)-FORM [MI]

Common Name

English

ISOEQUOL

Common Name

English

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

Systematic Name

English

Code System Code Type Description

MERCK INDEX

m4971