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Details

Stereochemistry ACHIRAL
Molecular Formula C16H12O4
Molecular Weight 268.2641
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FORMONONETIN

SMILES

COC1=CC=C(C=C1)C2=COC3=C(C=CC(O)=C3)C2=O

InChI

InChIKey=HKQYGTCOTHHOMP-UHFFFAOYSA-N
InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3

HIDE SMILES / InChI

Molecular Formula C16H12O4
Molecular Weight 268.2641
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

Formononetin, an isoflavone, derived from Astragalus membranaceus, possesses the potential to reduce obesity and associated metabolic disorders. Formononetin displays estrogenic properties and induces angiogenesis activities. It regulates adipocyte thermogenesis as a partial PPARγ agonist and produces proangiogenesis effects through estrogen receptor alpha (ERα)-enhanced ROCK-II signaling pathways, by direct binding to the ligand-binding domain (LBD) of ERα. Besides, was shown, that formononetin inhibits HMGB1 release by decreasing HMGB1 acetylation via upregulating SIRT1 in a PPARδ-dependent manner and the identification of this process may help to treat inflammation-related disorders.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
The mice were fed on a high fat diet (D12492, Research Diets) for 8 weeks to become obese, and then randomly divided into two groups and gavaged for the following 8 weeks with either Astragalus membranaceus water extract (3.3g/kg) or formononetin (50mg/kg) and vehicle (control) on a high fat diet.
Route of Administration: Oral
In Vitro Use Guide
Formononetin activated expression of the estrogen-responsive reporter gene in human breast cell line MCF-7 in a concentration-dependent manner (0.5-500 microM), and this activation was inhibited by estrogen antagonist (ICI 182780 at 100 nM).
Substance Class Chemical
Record UNII
295DQC67BJ
Record Status Validated (UNII)
Record Version