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Details

Stereochemistry ACHIRAL
Molecular Formula C15H8O5
Molecular Weight 268.221
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COUMESTROL

SMILES

OC1=CC=C2C(OC3=C2C(=O)OC4=C3C=CC(O)=C4)=C1

InChI

InChIKey=ZZIALNLLNHEQPJ-UHFFFAOYSA-N
InChI=1S/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H

HIDE SMILES / InChI

Molecular Formula C15H8O5
Molecular Weight 268.221
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Coumestrol is one of the major phytoestrogens, which is abundant in soybeans, legumes, and spinach. It competitively binds the estrogen receptors ERα and ERβ. Besides coumestrol is an endogenous antagonist of the human pregnane X receptor. It is known, that antagonizing the action of the human nuclear xenobiotic receptor pregnane X receptor (PXR) may have important clinical implications in preventing drug-drug interactions and improving therapeutic efficacy. Coumestrol epigenetically suppresses cancer cell proliferation, due to its inhibition of natural haspin kinase. Coumestrol exhibits broad anti-cancer effects against skin melanoma, lung cancer, breast cancer and some others cancer cell growth. Besides, was also shown the beneficial effects of coumestrol in various biological processes including, neuroprotective effects on the nervous system, and the function of the female reproductive system. However, the experiments for male rodents have strongly suggested a deleterious effect of oral, low concentration phytoestrogen content in adult male diets.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.14 nM [Ki]
0.07 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
in mice: 10, 20 or 40 μg/Kg body weight for two weeks
Route of Administration: Oral
In Vitro Use Guide
Coumestrol, is an antagonist of the nuclear receptor PXR (NR1I2). Coumestrol at concentrations above 1.0 microm competed in scintillation proximity assays with a labeled PXR agonist for binding to the ligand-binding cavity. Mammalian two-hybrid assays and transient transcription data using ligand-binding-cavity mutant forms of PXR show that coumestrol also antagonizes coregulator recruitment. This effect is likely by binding to a surface outside the ligand-binding pocket.
Substance Class Chemical
Record UNII
V7NW98OB34
Record Status Validated (UNII)
Record Version