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
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
| Molecular Formula | C16H12O4 |
| Molecular Weight | 268.2641 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P03372 Gene ID: 2099.0 Gene Symbol: ESR1 Target Organism: Homo sapiens (Human) |
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Target ID: P37231|||Q15179 Gene ID: 5468.0 Gene Symbol: PPARG Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Disposition of flavonoids via recycling: comparison of intestinal versus hepatic disposition. | 2005-12 |
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| Isoflavones modulate the glucuronidation of estradiol in human liver microsomes. | 2005-12 |
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| Regiospecific methylation of naringenin to ponciretin by soybean O-methyltransferase expressed in Escherichia coli. | 2005-09-23 |
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| Simultaneous determination of 10 major flavonoids in Dalbergia odorifera by high performance liquid chromatography. | 2005-09-15 |
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| Formononetin, a phyto-oestrogen, and its metabolites up-regulate interleukin-4 production in activated T cells via increased AP-1 DNA binding activity. | 2005-09 |
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| Determination of isoflavones in soy bits by fast column high-performance liquid chromatography coupled with UV-visible diode-array detection. | 2005-08-19 |
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| Effects of the environment, cultivar, maturity, and preservation method on red clover isoflavone concentration. | 2005-08-10 |
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| Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense). | 2005-08-10 |
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| Disposition of formononetin via enteric recycling: metabolism and excretion in mouse intestinal perfusion and Caco-2 cell models. | 2005-08-02 |
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| Metabolic engineering of isoflavonoid biosynthesis in alfalfa. | 2005-08 |
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| Evaluation of isoflavone aglycon and glycoside distribution in soy plants and soybeans by fast column high-performance liquid chromatography coupled with a diode-array detector. | 2005-07-27 |
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| Separation of compounds interacting with liposome membrane in combined prescription of traditional Chinese medicines with immobilized liposome chromatography. | 2005-06-15 |
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| [Hepatoprotector properties of polyphenolic complexes from wood and cell culture of Maackia amurensis]. | 2005-06-07 |
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| [Preparative isolation and purification of calycosin and formononetin from Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao by high-speed counter-current chromatography]. | 2005-05 |
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| In vitro free radical and ONOO- scavengers from Sophora flavescens. | 2005-05 |
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| Isoflavonoids from Astragalus mongholicus protect PC12 cells from toxicity induced by L-glutamate. | 2005-04-08 |
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| Phytoestrogens derived from red clover: an alternative to estrogen replacement therapy? | 2005-04 |
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| Flavonoids from Millettia nitida var. hirsutissima. | 2005-04 |
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| In vitro search for synergy between flavonoids and epirubicin on multidrug-resistant cancer cells. | 2005-03-31 |
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| Capillary liquid chromatography-microcoil 1H nuclear magnetic resonance spectroscopy and liquid chromatography-ion trap mass spectrometry for on-line structure elucidation of isoflavones in Radix astragali. | 2005-03-04 |
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| Simultaneous determination of six isoflavonoids in commercial Radix Astragali by HPLC-UV. | 2005-03 |
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| One year soy protein supplementation has positive effects on bone formation markers but not bone density in postmenopausal women. | 2005-02-23 |
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| Some flavonoids and DHEA-S prevent the cis-effect of expanded CTG repeats in a stable PC12 cell transformant. | 2005-02-01 |
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| Monoamine oxidase inhibitory components from the roots of Sophora flavescens. | 2005-02 |
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| The soy isoflavone genistein induces a late but sustained activation of the endothelial nitric oxide-synthase system in vitro. | 2005-02 |
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| Absorption and metabolism of genistein and its five isoflavone analogs in the human intestinal Caco-2 model. | 2005-02 |
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| Metabolic O-demethylation does not alter the influence of isoflavones on the biophysical properties of membranes and MRP1-like protein transport activity. | 2005-01-15 |
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| Chemical and biological assessment of a traditional chinese herbal decoction prepared from Radix Astragali and Radix Angelicae Sinensis: orthogonal array design to optimize the extraction of chemical constituents. | 2004-12 |
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| Identification of urinary metabolites of the red clover isoflavones formononetin and biochanin A in human subjects. | 2004-11-03 |
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| [Studies on chromatography fingerprint of huangqi by HPLC]. | 2004-11 |
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| Immunoassay for biochanin A. | 2004-11 |
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| Potential beneficial metabolic interactions between tamoxifen and isoflavones via cytochrome P450-mediated pathways in female rat liver microsomes. | 2004-11 |
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| Isoflavonoids in the Rutaceae family: 1. Fortunella obovata, Murraya paniculata and four Citrus species. | 2004-10-29 |
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| Inhibition of extrahepatic human cytochromes P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pratense (red clover). | 2004-10-20 |
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| Survey of estrogenic activity in fish feed by yeast estrogen-screen assay. | 2004-10 |
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| Liquid chromatography coupled to nuclear magnetic resonance spectroscopy for the identification of isoflavone glucoside malonates in T. pratense L. leaves. | 2004-09 |
|
| Disposition of flavonoids via enteric recycling: enzyme-transporter coupling affects metabolism of biochanin A and formononetin and excretion of their phase II conjugates. | 2004-09 |
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| Assessment of the reactivity of selected isoflavones against proteins in comparison to quercetin. | 2004-08-11 |
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| LC/UV/ESI-MS analysis of isoflavones in Edamame and Tofu soybeans. | 2004-05-19 |
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| Methods of phytochemical standardisation of rhizoma Cimicifugae racemosae. | 2004-05-01 |
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| [Studies on chemical constituents of sini tang]. | 2004-05 |
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| Antimicrobial and antioxidant flavonoids from the root wood of Bolusanthus speciosus. | 2004-04 |
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| The effects of dietary supplementation with isoflavones from red clover on cognitive function in postmenopausal women. | 2004-03 |
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| Flavonoid inhibition of overexpressed human 3beta-hydroxysteroid dehydrogenase type II. | 2004-02 |
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| Isoflavones in several clover species and in milk from goats fed clovers. | 2004 |
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| Effect of red clover isoflavones on cox-2 activity in murine and human monocyte/macrophage cells. | 2004 |
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| Regulation of low-density lipoprotein receptor activity by estrogens and phytoestrogens in a HepG2 cell model. | 2004 |
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| Red-clover-derived isoflavones and mammographic breast density: a double-blind, randomized, placebo-controlled trial [ISRCTN42940165]. | 2004 |
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| Isoflavones and women's health. | 2004 |
|
| [Study of the methods of determining the isoflavones in herbs of Trifolium pratense extractive]. | 2003-11 |
Sample Use Guides
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
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 19:17:46 GMT 2025
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admin
on
Mon Mar 31 19:17:46 GMT 2025
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| Record UNII |
295DQC67BJ
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| Record Status |
Validated (UNII)
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| Record Version |
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C599
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1400 (Number of products:1)
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FORMONONETIN
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m5541
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93360
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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FORMONONETIN was tested for antimicrobial activity against methicillin sensitive Staphylococcus aureus, methicillin resistant S. aureus, Micrococcus luteus, Bacillus subtilis, Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa and found to be inactive.
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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Showed no inhibition at 100 mcg/ml for Staphylococcus aureus (ATCC 13709) and Mycobacterium smegmatis (ATCC 6371). Extracts of G. glabra var. typica (Spanish licorice)-but not var. grandulifera (Russian licorice) were repeatedly active in the screen.
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