Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H9O5.Na.2H2O |
| Molecular Weight | 328.2493 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.[Na+].OC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C3=CC=C([O-])C=C3
InChI
InChIKey=PHLUGZPQDPVBGQ-UHFFFAOYSA-M
InChI=1S/C15H10O5.Na.2H2O/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19;;;/h1-7,16-18H;;2*1H2/q;+1;;/p-1
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C15H10O5 |
| Molecular Weight | 270.2369 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/15909536 | https://www.ncbi.nlm.nih.gov/pubmed/28265354 | https://www.ncbi.nlm.nih.gov/pubmed/25996650 | https://clinicaltrials.gov/ct2/show/NCT01664650
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/15909536 | https://www.ncbi.nlm.nih.gov/pubmed/28265354 | https://www.ncbi.nlm.nih.gov/pubmed/25996650 | https://clinicaltrials.gov/ct2/show/NCT01664650
GENISTEIN is an isoflavonoid derived from soy products. It inhibits protein-tyrosine kinase and topoisomerase-II (DNA topoisomerases, type II) activity and is used as an antineoplastic and antitumor agent. Experimentally, it has been shown to induce G2 phase arrest in human and murine cell lines. Additionally, genistein has antihelmintic activity. It has been determined to be the active ingredient in Felmingia vestita, which is a plant traditionally used against worms. It has also been demonstrated to be effective against intestinal parasites such as the common liver fluke, pork trematode and poultry cestode. Further, genistein is a phytoestrogen which has selective estrogen receptor modulator properties. It has been investigated in clinical trials as an alternative to classical hormone therapy to help prevent cardiovascular disease in postmenopausal women. Genistein can be found in food sources such as tofu, fava beans, soybeans, kudzu, and lupin. It is also present in certain cell cultures and medicinal plants.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1806 |
0.11 µM [IC50] | ||
Target ID: CHEMBL242 |
6.8 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Differential estrogen receptor binding of estrogenic substances: a species comparison. | 2000 Nov 15 |
|
| Tyrosine kinase inhibitors against EGF receptor-positive malignancies. | 2001 |
|
| FAK induction in keratinocytes in an in vitro model of reepithelialization. | 2001 Apr |
|
| Mitogenic effect of oxidized low-density lipoprotein on vascular smooth muscle cells mediated by activation of Ras/Raf/MEK/MAPK pathway. | 2001 Apr |
|
| Characterization of the serotonin receptor mediating contraction in the mouse thoracic aorta and signal pathway coupling. | 2001 Apr |
|
| PTH stimulates PLCbeta and PLCgamma isoenzymes in rat enterocytes: influence of ageing. | 2001 Feb |
|
| Involvement of ErbB-2 in rheumatoid synovial cell growth. | 2001 Feb |
|
| Effects of genistein on the periovulatory expression of messenger ribonucleic acid for matrix metalloproteinases and tissue inhibitors of metalloproteinases in the rat ovary. | 2001 Feb |
|
| Differences in electromechanical coupling between bradykinin and the nonpeptide kinin B2 receptor agonist, FR 190997, in the circular muscle of guinea-pig colon. | 2001 Feb |
|
| Regulation of MAP kinase by calcium-sensing receptor in bovine parathyroid and CaR-transfected HEK293 cells. | 2001 Feb |
|
| Effect of genistein-enriched diets on the endocrine process of gametogenesis and on reproduction efficiency of the rainbow trout Oncorhynchus mykiss. | 2001 Feb |
|
| Purinoceptor-mediated calcium mobilization and proliferation in HaCaT keratinocytes. | 2001 Feb |
|
| A common mechanism for cystic fibrosis transmembrane conductance regulator protein activation by genistein and benzimidazolone analogs. | 2001 Feb |
|
| Assessment of CFTR chloride channel openers in intact normal and cystic fibrosis murine epithelia. | 2001 Feb |
|
| Detrimental effect of cancer preventive phytochemicals silymarin, genistein and epigallocatechin 3-gallate on epigenetic events in human prostate carcinoma DU145 cells. | 2001 Feb 1 |
|
| Antagonistic and synergistic effects of combined treatment with interleukin-2 and interleukin-4 on mixed retinal cell cultures. | 2001 Feb 1 |
|
| Cytokine regulation of the expression of estrogenic biosynthetic enzymes in cultured rat granulosa cells. | 2001 Feb 14 |
|
| Heparin-binding epidermal-growth-factor-like growth factor gene expression is induced by scrape-wounding epithelial cell monolayers: involvement of mitogen-activated protein kinase cascades. | 2001 Feb 15 |
|
| Regulation of p42/p44 MAPK and p38 MAPK by the adenosine A(1) receptor in DDT(1)MF-2 cells. | 2001 Feb 16 |
|
| Sex steroid receptor regulation by genistein in the prepubertal rat uterus. | 2001 Feb 28 |
|
| Molecular biology of transplant arteriosclerosis and sites of therapeutic intervention. | 2001 Feb-Mar |
|
| Comparative assessment of endocrine modulators with oestrogenic activity: I. Definition of a hygiene-based margin of safety (HBMOS) for xeno-oestrogens against the background of European developments. | 2001 Jan |
|
| Secretory transport of p-aminohippuric acid across intestinal epithelial cells in Caco-2 cells and isolated intestinal tissue. | 2001 Jan |
|
| [In vitro and in vivo study of regulation mechanisms of type I interleukin-1 receptor]. | 2001 Jan |
|
| Modulation of noradrenaline-induced microvascular constriction by protein kinase inhibitors. | 2001 Jan |
|
| Contractile actions of proteinase-activated receptor-derived polypeptides in guinea-pig gastric and lung parenchymal strips: evidence for distinct receptor systems. | 2001 Jan |
|
| Vasoconstrictor actions of isoprostanes via tyrosine kinase and Rho kinase in human and canine pulmonary vascular smooth muscles. | 2001 Jan |
|
| Effects of tyrosine kinase inhibitors on cell death induced by sodium fluoride and pertussis toxin in the pancreatic beta-cell line, RINm5F. | 2001 Jan |
|
| Leukotriene C(4) enhances the contraction of porcine tracheal smooth muscle through the activation of Y-27632, a rho kinase inhibitor, sensitive pathway. | 2001 Jan |
|
| Growth hormone- and prolactin-induced proliferation of insulinoma cells, INS-1, depends on activation of STAT5 (signal transducer and activator of transcription 5). | 2001 Jan |
|
| Activation of human neutrophils by technical toxaphene. | 2001 Jan |
|
| Genistein inhibits nonoxidative ribose synthesis in MIA pancreatic adenocarcinoma cells: a new mechanism of controlling tumor growth. | 2001 Jan |
|
| Differential regulation of protein tyrosine kinase on free radical production, granule enzyme release, and cytokine synthesis by activated murine peritoneal macrophages. | 2001 Jan 1 |
|
| Agents that increase tyrosine phosphorylation activate a non-selective cation current in single rabbit portal vein smooth muscle cells. | 2001 Jan 15 |
|
| The phytoestrogen genistein produces acute nitric oxide-dependent dilation of human forearm vasculature with similar potency to 17beta-estradiol. | 2001 Jan 16 |
|
| Leflunomide inhibits activation of inducible nitric oxide synthase in rat astrocytes. | 2001 Jan 19 |
|
| Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5. | 2001 Jan 22 |
|
| Direct inhibition of the hexose transporter GLUT1 by tyrosine kinase inhibitors. | 2001 Jan 23 |
|
| Effect of intraovarian factors on porcine follicular cells: cumulus expansion, granulosa and cumulus cell progesterone production. | 2001 Jan 31 |
|
| Differential effects of protein tyrosine kinase inhibitors on interferon-gamma-induction of major histocompatibility complex class II and intercellular adhesion molecule-1 expression in human corneal epithelial cells. | 2001 Jan-Feb |
|
| Novel CFTR chloride channel activators identified by screening of combinatorial libraries based on flavone and benzoquinolizinium lead compounds. | 2001 Jun 8 |
|
| Interleukin-6 up-regulates the oxytocin receptor in cultured uterine smooth muscle cells. | 2001 Mar |
|
| Effects of estrogens in vitro and in vivo on cartilage growth in the tilapia (Oreochromis mossambicus). | 2001 Mar |
|
| Protein tyrosine kinase inhibitors alter human dopamine transporter activity in Xenopus oocytes. | 2001 Mar |
|
| Phytoestrogens and gonadotropin-releasing hormone pulse generator activity and pituitary luteinizing hormone release in the rat. | 2001 Mar |
|
| Adenosine-induced late preconditioning in mouse hearts: role of p38 MAP kinase and mitochondrial K(ATP) channels. | 2001 Mar |
|
| Initiation of polyoma virus origin-dependent DNA replication through STAT5 activation by human granulocyte-macrophage colony-stimulating factor. | 2001 Mar 1 |
|
| Paclitaxel sensitization of multidrug-resistant cells to chemotherapy is independent of the cell cycle. | 2001 Mar 1 |
|
| Corticosterone-induced rapid phosphorylation of p38 and JNK mitogen-activated protein kinases in PC12 cells. | 2001 Mar 16 |
|
| Dihydropyridine calcium channel blockers inhibit ascorbic acid accumulation in human intestinal Caco-2 cells. | 2001 Mar 2 |
Sample Use Guides
Cells were cultured in Dulbecco’s modified Eagle’s medium (U2OS, HCT116) media containing fetal calf serum, penicillin, streptomycin, glutamine, nonessential amino acids (Hyclone). The long-term growth curves of both 10 μmol/L genistein-treated U2OS and HCT116 cells were then determined by MTS assay. The experiment was conducted for 60 days with measuring the population doublings (PD) every 2–4 days after each dilution.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 14:59:21 GMT 2023
by
admin
on
Sat Dec 16 14:59:21 GMT 2023
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| Record UNII |
Z6D785B7J3
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| Record Status |
Validated (UNII)
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| Record Version |
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