EQUOL

Investigational

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-GFCCVEGCSA-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-/m1/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: http://www.ausiopharma.com/TechPages/TechOverview.html
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15883431

EQUOL, (-)- is the (S)-enantiomer of the naturally-occurring isoflavandiol estrogen, equol. EQUOL, (-)- (US-131), is a first-in-class, nonsteroidal, nonhormonal, small molecule (S-equol) that has higher selectivity toward estrogen receptor β (ERβ) than to estrogen receptor α (ERα). S-equol is the exclusive product of human intestinal bacterial synthesis from soy isoflavones. Two-Phase 1 studies have seen completed and published; AUS-131 was safe and well-tolerated in humans. A Phase 2a trial in menopausal women with vasomotor symptoms (VMS) has recently been completed (169 patients). A second Phase 2a trial in men with benign prostatic hyperplasia (BPH) is on track.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor beta 110 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15883431	Agonist 2678		0.73 nM [Ki]
PC-3 15 Target ID: CHEMBL390 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26638886	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vasomotor symptoms due to menopause 4 Sources: https://clinicaltrials.gov/ct2/show/NCT00962585	Primary		Phase II 1132	Unknown Approved Use Unknown
Benign prostatic hyperplasia 28 Sources: https://clinicaltrials.gov/ct2/show/NCT00962390	Primary		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
4953 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19776178	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		EQUOL, (-)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
1907 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19776178	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		EQUOL, (-)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
25299 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19776178	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		EQUOL, (-)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
8584 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19776178	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		EQUOL, (-)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19776178	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		EQUOL, (-)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
7.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19776178	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		EQUOL, (-)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	NO16359	https://www.001chemical.com/chem/search?q=NO16359
1PlusChem LLC	1P005VLD	https://www.1pchem.com/search?query=1P005VLD
1PlusChem LLC	1P00I9Y2	https://www.1pchem.com/search?query=1P00I9Y2
A2B Chem	AC73425	http://a2bchem.com/prod/AC73425
AK Scientific	2127AH	https://aksci.com/item_detail.php?cat=2127AH
AK Scientific	W6768	https://aksci.com/item_detail.php?cat=W6768
AOBIOUS INC	AOB5550	http://aobious.com/aobious/search?search_query=AOB5550
Achemo Scientific Limited	AC-77361	http://www.achemo.com/search/?Keyword=AC-77361
Ambeed	A168315	http://www.ambeed.com/search/Search.html?keyword=A168315
Angene	AGN-PC-07A1Y7	http://www.angenechemical.com/productshow/AGN-PC-07A1Y7.html
Angene	AGN-PC-0OBU98	http://www.angenechemical.com/productshow/AGN-PC-0OBU98.html
Apollo Scientific	BIE531	http://www.apolloscientific.co.uk/chemical_results.php?qstext=BIE531&product_group=%25&search_fieldname=header_search
Apollo Scientific	OR60026	http://www.apolloscientific.co.uk/chemical_results.php?qstext=OR60026&product_group=%25&search_fieldname=header_search
AstaTech	25531	http://astatechinc.com/CPSResult.php?CRNO=25531
AstaTech	F17393	http://astatechinc.com/CPSResult.php?CRNO=F17393
BOC Sciences	531-95-3	http://www.bocsci.com/description.asp?cas=531-95-3
BOC Sciences	66036-38-2	http://www.bocsci.com/description.asp?cas=66036-38-2
BOC Sciences	94105-90-5	http://www.bocsci.com/description.asp?cas=94105-90-5
Cayman Chemical	10010172	http://www.caymanchem.com/app/template/Product.vm/catalog/10010172
Cayman Chemical	10010173	http://www.caymanchem.com/app/template/Product.vm/catalog/10010173
Cayman Chemical	13184	http://www.caymanchem.com/app/template/Product.vm/catalog/13184
Chem Scene	CS-6870	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-6870
Chem Scene	CS-7937	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-7937
ChemShuttle	102638	https://www.chemshuttle.com/catalogsearch/result/?q=102638
Combi-Blocks	QA-5873	http://www.combi-blocks.com/cgi-bin/find.cgi?QA-5873
Combi-Blocks	QC-1372	http://www.combi-blocks.com/cgi-bin/find.cgi?QC-1372
Fluorochem	223335	http://www.fluorochem.co.uk/Products/Product?code=223335
Fluorochem	306415	http://www.fluorochem.co.uk/Products/Product?code=306415
Hairui	HR129156	http://www.hairuichem.com/en/product/search.do?q=HR129156
Indofine	21268	https://indofinechemical.com/details.aspx?Sku=021268
KeyOrganics	AS-71147	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-71147
KeyOrganics	DS-2344	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=DS-2344
Lab Network	LN00176749	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00176749
Lab Network	LN00224158	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00224158
Lab Seeker	SC-19277	http://www.labseeker.com/search.php?keywords=SC-19277&category=0
Lab Seeker	SC-94870	http://www.labseeker.com/search.php?keywords=SC-94870&category=0
LabSeeker	SC-19277	http://www.labseeker.com/search.php?keywords=SC-19277&category=0
LabSeeker	SC-94870	http://www.labseeker.com/search.php?keywords=SC-94870&category=0
Matrix Scientific	76049	http://www.matrixscientific.com/076049.html
Matrix Scientific	126267	http://www.matrixscientific.com/126267.html
MedChem Express	HY-100583	https://www.medchemexpress.com/search.html?q=HY-100583A&ft=&fa=&fp=
MedChem Express	HY-100583A	https://www.medchemexpress.com/search.html?q=HY-100583A&ft=&fa=&fp=
MolPort	MolPort-003-847-077	https://www.molport.com/shop/molecule-link/MolPort-003-847-077
MolPort	MolPort-003-847-078	https://www.molport.com/shop/molecule-link/MolPort-003-847-078
Molcore	CS16359	http://www.molcore.com/CatCS16359.html
Molnova	M14893	https://www.molnova.com/en/serch-list.html?keywords=M14893
Molnova	M19273	https://www.molnova.com/en/serch-list.html?keywords=M19273
MuseChem	R004033	https://www.musechem.com/product/R004033.html
MuseChem	R005377	https://www.musechem.com/product/R005377.html
PI Chemicals	PI-41481	http://www.pipharm.com/catalog_products/PI-41481.html
Selleck Chemicals	S2450	http://www.selleckchem.com/search.html?searchDTO.searchParam=S2450
Selleck Chemicals	S6601	http://www.selleckchem.com/search.html?searchDTO.searchParam=S6601
ShangHai Biochempartner	BCP13598	http://www.biochempartner.com/search_BCP13598
Sigma Aldrich	SML2147	http://www.sigmaaldrich.com/catalog/search?term=SML2147&interface=All&N=0&mode=match%20partialmax&lang=en®ion=US&focus=product
SynQuest	239	http://www.synquestlabs.com/search-result.html?q=239
SynQuest	2H04-1-47	http://www.synquestlabs.com/search-result.html?q=2H04-1-47
Synchem UG and Co KG	a160fp1	https://www.synchem.de/?s=a160fp1&post_type=product
TargetMol	T4000	https://www.targetmol.com/search?keyword=T4000
TargetMol	T6491	https://www.targetmol.com/search?keyword=T6491
Tetrahedron	TS08468	http://www.thsci.com/search.do?q=TS08468
TimTec	ST50331725	http://www.echemstore.com/catalogsearch/result/?q=ST50331725
Toronto Research Chemicals	E593000	https://www.trc-canada.com/product-detail/?CatNum=E593000
Toronto Research Chemicals	E593001	https://www.trc-canada.com/product-detail/?CatNum=E593001
Toronto Research Chemicals	T790705	https://www.trc-canada.com/product-detail/?CatNum=T790705
Vesino Industrial Co Ltd	VA10827	http://www.vsnchem.com/search.do?a=s&psize=20&q=VA10827
Wonderchem	WD04EVO	http://www.wonder-chem.com/search.html?text=WD04EVO
eMolecules	299986807	https://orderbb.emolecules.com/search/#?query=299986807
eMolecules	4368726	https://orderbb.emolecules.com/search/#?query=4368726
eMolecules	509672	https://orderbb.emolecules.com/search/#?query=509672
eNovation Chemicals	D508623	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D508623&searchbtn.x=0&searchbtn.y=0
eNovation Chemicals	D711198	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D711198&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-1231583021	https://mcule.com/MCULE-1231583021/
mcule	MCULE-1358694468	https://mcule.com/MCULE-1358694468/
mcule	MCULE-5874318771	https://mcule.com/MCULE-5874318771/

PubMed

Title	Date	PubMed
The production of S-equol from daidzein is associated with a cluster of three genes in Eggerthella sp. YY7918.	2016	27508112
Phytoestrogen Metabolism by Adult Human Gut Microbiota.	2016 Aug 9	27517891
Tyrosine phosphorylation regulates ERβ ubiquitination, protein turnover, and inhibition of breast cancer.	2016 Jul 5	27323858

Patents

Sample Use Guides

In Vivo Use Guide

The following doses have been studied in scientific research: BY MOUTH: For menopausal symptoms such as hot flashes: 10-40 mg per day in divided doses. For preventing weak bones (osteoporosis): 10 mg per day. For reducing skin wrinkles: 5 or 15 mg two times per day. For metabolic syndrome: 10 mg per day.

Route of Administration: Oral

In Vitro Use Guide

S-equol (EQUOL, (-)-) inhibited the growth of the breast cancer cell line MDA-MB-231 (> or = 10 uM) and the prostate cancer cell lines LNCaP (> or = 5 uM) and LAPC-4 (> or = 2.5 uM).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:19:57 GMT 2023` Edited by `admin` on `Fri Dec 15 17:19:57 GMT 2023`
Record UNII	2T6D2HPX7Q
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

EQUOL

Official Name

English

EQUOL [MI]

Common Name

English

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

Systematic Name

English

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

Systematic Name

English

EQUOL [INCI]

Common Name

English

S-EQUOL

Common Name

English

EQUOL (S)-FORM

Common Name

English

EQUOL, (S)-

Common Name

English

EQUOL, (-)-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2182