Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H10O8 |
Molecular Weight | 318.2351 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC2=C(C(O)=C1)C(=O)C(O)=C(O2)C3=CC(O)=C(O)C(O)=C3
InChI
InChIKey=IKMDFBPHZNJCSN-UHFFFAOYSA-N
InChI=1S/C15H10O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,16-20,22H
Molecular Formula | C15H10O8 |
Molecular Weight | 318.2351 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Myricetin is a member of the flavonoid class of polyphenolic compounds with antioxidant properties. It occurs naturally in a wide variety of plants. Myricetin has demonstrated anti-inflammatory, antioxidative, anti-non-enzymatic glycation and anti-hyperlipidemia in a number of cellular and animal models. It has been investigated for potential therapeutic effects against cancers and diabetes.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27171848
Curator's Comment: referenced study was conducted on rats
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P33527|||Q9UQ99 Gene ID: 4363.0 Gene Symbol: ABCC1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11306701 |
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Target ID: P52332 Gene ID: NA Gene Symbol: Jak1 Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18995957 |
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Target ID: P04746 Gene ID: 279.0 Gene Symbol: AMY2A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23050660 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Flavones are inhibitors of HIV-1 proteinase. | 1992 Oct 30 |
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Acylated flavonol glycosides from Eugenia jambolana leaves. | 2001 Dec |
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[Comparison of photometric, electrochemical and post-column fluorescence detection for the determination of flavonoids by HPLC]. | 2001 Jun |
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Effects of flavonols on the generation of superoxide anion radicals by xanthine oxidase and stimulated neutrophils. | 2001 Nov 1 |
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Antioxidant ability of various flavonoids against DPPH radicals and LDL oxidation. | 2001 Oct |
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Determination of flavonoids and stilbenes in red wine and related biological products by HPLC and HPLC-ESI-MS-MS. | 2001 Sep |
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Polyphenolic compounds: interactions with the gut and implications for human health. | 2001 Sep |
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Evaluation of the clastogenic, DNA intercalative, and topoisomerase II-interactive properties of bioflavonoids in Chinese hamster V79 cells. | 2002 |
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Dietary flavonoids: bioavailability, metabolic effects, and safety. | 2002 |
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Prevention of cellular ROS damage by isovitexin and related flavonoids. | 2002 Apr |
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A new flavonol from leaves of Eugenia jambolana. | 2002 Apr |
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Phenolic compounds and antioxidant capacity of Georgia-grown blueberries and blackberries. | 2002 Apr 10 |
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Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies. | 2002 Dec |
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Flavonoids as DNA topoisomerase I poisons. | 2002 Feb |
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Involvement of protein kinase C and Na+/K+-ATPase in the contractile response induced by myricetin in rat isolated aorta. | 2002 Feb |
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Bioactive constituents of Chinese natural medicines. VII. Inhibitors of degranulation in RBL-2H3 cells and absolute stereostructures of three new diarylheptanoid glycosides from the bark of Myrica rubra. | 2002 Feb |
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Inhibitory effects of anthocyanins and other phenolic compounds on nitric oxide production in LPS/IFN-gamma-activated RAW 264.7 macrophages. | 2002 Feb 13 |
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Composition of a chemopreventive proanthocyanidin-rich fraction from cranberry fruits responsible for the inhibition of 12-O-tetradecanoyl phorbol-13-acetate (TPA)-induced ornithine decarboxylase (ODC) activity. | 2002 Feb 27 |
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The contribution of the pyrogallol moiety to the superoxide radical scavenging activity of flavonoids. | 2002 Jan |
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A pharmacophore for human pregnane X receptor ligands. | 2002 Jan |
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Intracellular flavonoids as electron donors for extracellular ferricyanide reduction in human erythrocytes. | 2002 Jan 1 |
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Wogonin and fisetin induce apoptosis in human promyeloleukemic cells, accompanied by a decrease of reactive oxygen species, and activation of caspase 3 and Ca(2+)-dependent endonuclease. | 2002 Jan 15 |
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QSAR aspects of flavonoids as a plentiful source of new drugs. | 2002 Jul |
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Effects of anthocyanins and other phenolic compounds on the production of tumor necrosis factor alpha in LPS/IFN-gamma-activated RAW 264.7 macrophages. | 2002 Jul 17 |
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Interactions of different phenolic acids and flavonoids with soy proteins. | 2002 Jun 18 |
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Nicotinamide is not a substrate of the facilitative hexose transporter GLUT1. | 2002 Jun 25 |
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Functional analysis of the copper-dependent quercetin 2,3-dioxygenase. 2. X-ray absorption studies of native enzyme and anaerobic complexes with the substrates quercetin and myricetin. | 2002 Jun 25 |
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Main constituents of a commercial Drosera fluid extract and their antagonist activity at muscarinic M3 receptors in guinea-pig ileum. | 2002 Mar |
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Flavonoids increase the intracellular glutathione level by transactivation of the gamma-glutamylcysteine synthetase catalytical subunit promoter. | 2002 Mar 1 |
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Structure-activity relationships for inhibition of human 5alpha-reductases by polyphenols. | 2002 Mar 15 |
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Identification and quantification of galloyl derivatives, flavonoid glycosides and anthocyanins in leaves of Pistacia lentiscus L. | 2002 Mar-Apr |
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Rutin-enhanced antibacterial activities of flavonoids against Bacillus cereus and Salmonella enteritidis. | 2002 May |
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Polyphenols and red wine as peroxynitrite scavengers: a chemiluminescent assay. | 2002 May |
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Inhibition by wine polyphenols of peroxynitrite-initiated chemiluminescence and NADH oxidation. | 2002 May |
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Molecular modeling of flavonoids that inhibits xanthine oxidase. | 2002 May 31 |
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Ardisiphenols and other antioxidant principles from the fruits of Ardisia colorata. | 2002 Nov |
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Flavonol and flavone intakes in US health professionals. | 2002 Oct |
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Antioxidant activities and antitumor screening of extracts from cranberry fruit (Vaccinium macrocarpon). | 2002 Oct 9 |
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Antitumor-promoting constituents from Dioscorea bulbifera L. in JB6 mouse epidermal cells. | 2002 Sep |
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Flavonoids and antioxidant capacity of Georgia-grown Vidalia onions. | 2002 Sep 11 |
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Inactivation of the human brain muscarinic acetylcholine receptor by oxidative damage catalyzed by a low molecular weight endogenous inhibitor from Alzheimer's brain is prevented by pyrophosphate analogs, bioflavonoids and other antioxidants. | 2002 Sep 20 |
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Phenolic compounds from Nymphaea odorata. | 2003 Apr |
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Flavones inhibit proliferation and increase mediator content in human leukemic mast cells (HMC-1). | 2003 Dec |
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Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. | 2003 Dec |
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Effect of flavone derivatives on interleukin-1beta (IL-1beta) mRNA expression and IL-1beta protein synthesis in stimulated RAW 264.7 macrophages. | 2003 Feb |
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Malonylated flavonol glycosides from the petals of Clitoria ternatea. | 2003 Jan |
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Flavonol and drimane-type sesquiterpene glycosides of Warburgia stuhlmannii leaves. | 2003 Jun |
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Separation of polyphenolic compounds extracted from plant matrices using capillary electrophoresis. | 2003 Mar 21 |
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Potent anti-amyloidogenic and fibril-destabilizing effects of polyphenols in vitro: implications for the prevention and therapeutics of Alzheimer's disease. | 2003 Oct |
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Paclitaxel metabolism in rat and human liver microsomes is inhibited by phenolic antioxidants. | 2003 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22083509
Curator's Comment: referenced study was conducted on rats
Male Albino Wistar rats were induced to diabetes by intraperitoneal (ip) injection of streptozotocin (50 mg/kg), and rats having fasting blood glucose (FBG) levels greater than 200 mg/dl were included in the study. Treatment of myricetin (6 mg/day ip) was initiated 16 weeks after diabetes was confirmed. Myricetin treatment significantly decreased glomerulosclerosis and reduced BUN, urinary volume and protein excretion, which had been profoundly increased in diabetic rats. Decreased creatinine clearance measured in diabetic rats was significantly increased following myricetin treatment. Myricetin also restored altered renal activities of GPx and XO, which were decreased and increased in diabetic rats, respectively.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11306701
HeLa cell line T5 was transfected with MRP1 transporter gene and maintained in RPMI-1640 medium supplemented with 4 mM L-glutamine and 5% defined bovine calf serum and 400 micro-g/mL geneticin. Transfected Hela cells were homogenized and lysed. The suspension was centrifuged and the supernatant and membranes extracted. The membranes were washed and resuspended in a buffer of 25 mM sucrose, 50 mM Tris pH 7.4. LTC4 transport inhibition assays were carried out by a rapid filtration method. Assays were conducted at 23 deg-C in a 50 micro-L volume containing 2 micro-g of vesicles, 4 mM ATP, 4 mM AMP, 10 mM MgCl2, GSH (0, 1 or 3 mM), 10 mM DTT, 10 mM creatine phosphate, 100 μg/ml creatine kinase, 50 nM [3H]LTC4 (40 nCi), and Myricetin dissolved in DMSO (0.7%). The mixture was incubated for 60 seconds then added to 800 micro-L of an ice-cold Tris-sucrose buffer. The solution was then filtered, washed twice, and radioactivity was quantified by liquid scintillation. Myricetin was examined at 0, 25, 50, 75, and 100 micro-M. And, eight different concentrations of LTC were used between 10 - 500 nM. Myricetin demonstrated a potent inhibitory effect with IC50 values between 7 - 12 micro-M.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:31:23 GMT 2025
by
admin
on
Mon Mar 31 19:31:23 GMT 2025
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Record UNII |
76XC01FTOJ
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Record Status |
Validated (UNII)
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Record Version |
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C792
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DSLD |
1291 (Number of products:23)
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58395
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C68458
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DB02375
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208-463-2
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76XC01FTOJ
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C040015
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76XC01FTOJ
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5281672
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MYRICETIN
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DTXSID8022400
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1368374
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m7687
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529-44-2
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407290
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7682
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