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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 of EQUOL

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.73 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4953 nM
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
25299 ng × h/mL
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.2 h
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
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

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

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

Sample Use Guides

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
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 UTC 2023
Edited
by admin
on Fri Dec 15 17:19:57 UTC 2023
Record UNII
2T6D2HPX7Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EQUOL
INCI   MI  
INCI  
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
Created by admin on Fri Dec 15 17:19:57 UTC 2023 , Edited by admin on Fri Dec 15 17:19:57 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID0022309
Created by admin on Fri Dec 15 17:19:57 UTC 2023 , Edited by admin on Fri Dec 15 17:19:57 UTC 2023
PRIMARY
FDA UNII
2T6D2HPX7Q
Created by admin on Fri Dec 15 17:19:57 UTC 2023 , Edited by admin on Fri Dec 15 17:19:57 UTC 2023
PRIMARY
DAILYMED
2T6D2HPX7Q
Created by admin on Fri Dec 15 17:19:57 UTC 2023 , Edited by admin on Fri Dec 15 17:19:57 UTC 2023
PRIMARY
SMS_ID
300000025997
Created by admin on Fri Dec 15 17:19:57 UTC 2023 , Edited by admin on Fri Dec 15 17:19:57 UTC 2023
PRIMARY
CAS
531-95-3
Created by admin on Fri Dec 15 17:19:57 UTC 2023 , Edited by admin on Fri Dec 15 17:19:57 UTC 2023
PRIMARY
RXCUI
1803717
Created by admin on Fri Dec 15 17:19:57 UTC 2023 , Edited by admin on Fri Dec 15 17:19:57 UTC 2023
PRIMARY
MERCK INDEX
m4971
Created by admin on Fri Dec 15 17:19:57 UTC 2023 , Edited by admin on Fri Dec 15 17:19:57 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL198877
Created by admin on Fri Dec 15 17:19:57 UTC 2023 , Edited by admin on Fri Dec 15 17:19:57 UTC 2023
PRIMARY
DRUG BANK
DB11674
Created by admin on Fri Dec 15 17:19:57 UTC 2023 , Edited by admin on Fri Dec 15 17:19:57 UTC 2023
PRIMARY
NCI_THESAURUS
C120313
Created by admin on Fri Dec 15 17:19:57 UTC 2023 , Edited by admin on Fri Dec 15 17:19:57 UTC 2023
PRIMARY
WIKIPEDIA
Equol
Created by admin on Fri Dec 15 17:19:57 UTC 2023 , Edited by admin on Fri Dec 15 17:19:57 UTC 2023
PRIMARY
PUBCHEM
91469
Created by admin on Fri Dec 15 17:19:57 UTC 2023 , Edited by admin on Fri Dec 15 17:19:57 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-522-2
Created by admin on Fri Dec 15 17:19:57 UTC 2023 , Edited by admin on Fri Dec 15 17:19:57 UTC 2023
PRIMARY
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TARGET -> AGONIST
BINDING
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PARENT -> METABOLITE ACTIVE
Produced by intestinal microbiota. Similar activity as estrodiol
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ACTIVE MOIETY