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 |
|---|---|---|
| [Study of the methods of determining the isoflavones in herbs of Trifolium pratense extractive]. | 2003 Nov |
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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 |
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| Antimicrobial and antioxidant flavonoids from the root wood of Bolusanthus speciosus. | 2004 Apr |
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| Assessment of the reactivity of selected isoflavones against proteins in comparison to quercetin. | 2004 Aug 11 |
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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 Dec |
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| Flavonoid inhibition of overexpressed human 3beta-hydroxysteroid dehydrogenase type II. | 2004 Feb |
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| The effects of dietary supplementation with isoflavones from red clover on cognitive function in postmenopausal women. | 2004 Mar |
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| Methods of phytochemical standardisation of rhizoma Cimicifugae racemosae. | 2004 Mar-Apr |
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| [Studies on chemical constituents of sini tang]. | 2004 May |
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| LC/UV/ESI-MS analysis of isoflavones in Edamame and Tofu soybeans. | 2004 May 19 |
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| [Studies on chromatography fingerprint of huangqi by HPLC]. | 2004 Nov |
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| Immunoassay for biochanin A. | 2004 Nov |
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| Potential beneficial metabolic interactions between tamoxifen and isoflavones via cytochrome P450-mediated pathways in female rat liver microsomes. | 2004 Nov |
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| Identification of urinary metabolites of the red clover isoflavones formononetin and biochanin A in human subjects. | 2004 Nov 3 |
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| Survey of estrogenic activity in fish feed by yeast estrogen-screen assay. | 2004 Oct |
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| Inhibition of extrahepatic human cytochromes P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pratense (red clover). | 2004 Oct 20 |
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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 Sep |
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| Disposition of flavonoids via enteric recycling: enzyme-transporter coupling affects metabolism of biochanin A and formononetin and excretion of their phase II conjugates. | 2004 Sep |
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| Isoflavonoids in the Rutaceae family: 1. Fortunella obovata, Murraya paniculata and four Citrus species. | 2004 Sep-Oct |
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| Phytoestrogens derived from red clover: an alternative to estrogen replacement therapy? | 2005 Apr |
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| Flavonoids from Millettia nitida var. hirsutissima. | 2005 Apr |
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| Isoflavonoids from Astragalus mongholicus protect PC12 cells from toxicity induced by L-glutamate. | 2005 Apr 8 |
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| Metabolic engineering of isoflavonoid biosynthesis in alfalfa. | 2005 Aug |
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| Effects of the environment, cultivar, maturity, and preservation method on red clover isoflavone concentration. | 2005 Aug 10 |
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| Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense). | 2005 Aug 10 |
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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 Aug 19 |
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| Disposition of flavonoids via recycling: comparison of intestinal versus hepatic disposition. | 2005 Dec |
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| Isoflavones modulate the glucuronidation of estradiol in human liver microsomes. | 2005 Dec |
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| Monoamine oxidase inhibitory components from the roots of Sophora flavescens. | 2005 Feb |
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| The soy isoflavone genistein induces a late but sustained activation of the endothelial nitric oxide-synthase system in vitro. | 2005 Feb |
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| Absorption and metabolism of genistein and its five isoflavone analogs in the human intestinal Caco-2 model. | 2005 Feb |
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| Some flavonoids and DHEA-S prevent the cis-effect of expanded CTG repeats in a stable PC12 cell transformant. | 2005 Feb 1 |
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| One year soy protein supplementation has positive effects on bone formation markers but not bone density in postmenopausal women. | 2005 Feb 23 |
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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 Jan 15 |
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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 Jul 27 |
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| Disposition of formononetin via enteric recycling: metabolism and excretion in mouse intestinal perfusion and Caco-2 cell models. | 2005 Jul-Aug |
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| Separation of compounds interacting with liposome membrane in combined prescription of traditional Chinese medicines with immobilized liposome chromatography. | 2005 Jun 15 |
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| Simultaneous determination of six isoflavonoids in commercial Radix Astragali by HPLC-UV. | 2005 Mar |
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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 Mar 4 |
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| [Hepatoprotector properties of polyphenolic complexes from wood and cell culture of Maackia amurensis]. | 2005 Mar-Apr |
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| In vitro search for synergy between flavonoids and epirubicin on multidrug-resistant cancer cells. | 2005 Mar-Apr |
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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 May |
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| In vitro free radical and ONOO- scavengers from Sophora flavescens. | 2005 May |
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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 Sep |
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| Simultaneous determination of 10 major flavonoids in Dalbergia odorifera by high performance liquid chromatography. | 2005 Sep 15 |
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| Regiospecific methylation of naringenin to ponciretin by soybean O-methyltransferase expressed in Escherichia coli. | 2005 Sep 23 |
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
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on
Fri Dec 15 18:38:32 GMT 2023
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| Record UNII |
295DQC67BJ
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| Record Status |
Validated (UNII)
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C599
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1400 (Number of products:1)
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FORMONONETIN
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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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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