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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
0.73 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
4953 nM
30 mg single, oral
EQUOL, (-)- plasma
Homo sapiens
1907 nM
10 mg single, oral
EQUOL, (-)- plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
25299 ng × h/mL
30 mg single, oral
EQUOL, (-)- plasma
Homo sapiens
8584 ng × h/mL
10 mg single, oral
EQUOL, (-)- plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
8.2 h
30 mg single, oral
EQUOL, (-)- plasma
Homo sapiens
7.4 h
10 mg single, oral
EQUOL, (-)- plasma
Homo sapiens

PubMed

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
Record UNII
2T6D2HPX7Q
Record Status Validated (UNII)
Record Version