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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Dietary flavonoids: bioavailability, metabolic effects, and safety. | 2002 |
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[Studies on the chemical constituents from Ampelopsis grossedentata]. | 2002 Apr |
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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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Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies. | 2002 Dec |
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Pinostrobin from honey and Thai ginger (Boesenbergia pandurata): a potent flavonoid inducer of mammalian phase 2 chemoprotective and antioxidant enzymes. | 2002 Dec 4 |
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Flavonoids as DNA topoisomerase I poisons. | 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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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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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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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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Polyphenols and red wine as peroxynitrite scavengers: a chemiluminescent assay. | 2002 May |
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Molecular modeling of flavonoids that inhibits xanthine oxidase. | 2002 May 31 |
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Antioxidant and free-radical scavenging activity of constituents of the leaves of Tachigalia paniculata. | 2002 Nov |
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Ardisiphenols and other antioxidant principles from the fruits of Ardisia colorata. | 2002 Nov |
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Nitric oxide formation and corresponding relaxation of porcine coronary arteries induced by plant phenols: essential structural features. | 2002 Nov |
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Rat kidney antioxidant response to long-term exposure to flavonol rich red wine. | 2002 Nov 1 |
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Flavonol and flavone intakes in US health professionals. | 2002 Oct |
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Flavonoids and antioxidant capacity of Georgia-grown Vidalia onions. | 2002 Sep 11 |
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The unique occurrence of the flavone aglycone tricetin in Myrtaceae pollen. | 2002 Sep-Oct |
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Antioxidant principles of Nelumbo nucifera stamens. | 2003 Apr |
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Phenolic content and antioxidant capacity of muscadine grapes. | 2003 Aug 27 |
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Flavones inhibit proliferation and increase mediator content in human leukemic mast cells (HMC-1). | 2003 Dec |
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Nonaqueous capillary electrophoretic separation of polyphenolic compounds in wine using coated capillaries at high pH in methanol. | 2003 Dec |
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Neuroprotection by flavonoids. | 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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Inhibition of syk activity and degranulation of human mast cells by flavonoids. | 2003 Dec |
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Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context. | 2003 Dec |
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L-type Ca2+ channels activation and contraction elicited by myricetin on vascular smooth muscles. | 2003 Dec |
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The inhibitory effects of flavonoids and antiestrogens on the Glut1 glucose transporter in human erythrocytes. | 2003 Dec 15 |
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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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Effects of several polyhydroxylated flavonoids on the growth of B16F10 melanoma and Melan-a melanocyte cell lines: influence of the sequential oxidation state of the flavonoid skeleton. | 2003 Feb |
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Malonylated flavonol glycosides from the petals of Clitoria ternatea. | 2003 Jan |
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Anti-complement activity of constituents from the stem-bark of Juglans mandshurica. | 2003 Jul |
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Effect of fraxetin and myricetin on rotenone-induced cytotoxicity in SH-SY5Y cells: comparison with N-acetylcysteine. | 2003 Jul 4 |
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Fisetin, a flavonol, inhibits TH2-type cytokine production by activated human basophils. | 2003 Jun |
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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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Flavonol glycosides of Warburgia ugandensis leaves. | 2003 Oct |
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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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Different antioxidant effects of polyphenols on lipid peroxidation and hydroxyl radicals in the NADPH-, Fe-ascorbate- and Fe-microsomal systems. | 2003 Oct 1 |
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Flavonoid intake and breast cancer risk: a case--control study in Greece. | 2003 Oct 6 |
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Paclitaxel metabolism in rat and human liver microsomes is inhibited by phenolic antioxidants. | 2003 Sep |
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Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102. | 2003 Sep 9 |
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
Fri Dec 15 19:02:39 GMT 2023
by
admin
on
Fri Dec 15 19:02:39 GMT 2023
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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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NCI_THESAURUS |
C792
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DSLD |
1291 (Number of products:23)
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18152
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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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