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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
Structure of MYRICETIN

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

HIDE SMILES / InChI
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

Curator's Comment: referenced study was conducted on rats

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P33527|||Q9UQ99
Gene ID: 4363.0
Gene Symbol: ABCC1
Target Organism: Homo sapiens (Human)
Target ID: P52332
Gene ID: NA
Gene Symbol: Jak1
Target Organism: Mus musculus (Mouse)
Target ID: P04746
Gene ID: 279.0
Gene Symbol: AMY2A
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A novel cytotoxic flavonoid glycoside from Physalis angulata.
2001 Aug
Acylated flavonol glycosides from Eugenia jambolana leaves.
2001 Dec
[Comparison of photometric, electrochemical and post-column fluorescence detection for the determination of flavonoids by HPLC].
2001 Jun
Effects of flavonols on the generation of superoxide anion radicals by xanthine oxidase and stimulated neutrophils.
2001 Nov 1
Antioxidant ability of various flavonoids against DPPH radicals and LDL oxidation.
2001 Oct
Determination of flavonoids and stilbenes in red wine and related biological products by HPLC and HPLC-ESI-MS-MS.
2001 Sep
Polyphenolic compounds: interactions with the gut and implications for human health.
2001 Sep
Dietary flavonoids: bioavailability, metabolic effects, and safety.
2002
[Studies on the chemical constituents from Ampelopsis grossedentata].
2002 Apr
Prevention of cellular ROS damage by isovitexin and related flavonoids.
2002 Apr
A new flavonol from leaves of Eugenia jambolana.
2002 Apr
Phenolic compounds and antioxidant capacity of Georgia-grown blueberries and blackberries.
2002 Apr 10
Pinostrobin from honey and Thai ginger (Boesenbergia pandurata): a potent flavonoid inducer of mammalian phase 2 chemoprotective and antioxidant enzymes.
2002 Dec 4
Flavonoids as DNA topoisomerase I poisons.
2002 Feb
Involvement of protein kinase C and Na+/K+-ATPase in the contractile response induced by myricetin in rat isolated aorta.
2002 Feb
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
Inhibitory effects of anthocyanins and other phenolic compounds on nitric oxide production in LPS/IFN-gamma-activated RAW 264.7 macrophages.
2002 Feb 13
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
The contribution of the pyrogallol moiety to the superoxide radical scavenging activity of flavonoids.
2002 Jan
A pharmacophore for human pregnane X receptor ligands.
2002 Jan
Intracellular flavonoids as electron donors for extracellular ferricyanide reduction in human erythrocytes.
2002 Jan 1
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
QSAR aspects of flavonoids as a plentiful source of new drugs.
2002 Jul
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
Interactions of different phenolic acids and flavonoids with soy proteins.
2002 Jun 18
Nicotinamide is not a substrate of the facilitative hexose transporter GLUT1.
2002 Jun 25
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
Main constituents of a commercial Drosera fluid extract and their antagonist activity at muscarinic M3 receptors in guinea-pig ileum.
2002 Mar
Flavonoids increase the intracellular glutathione level by transactivation of the gamma-glutamylcysteine synthetase catalytical subunit promoter.
2002 Mar 1
Structure-activity relationships for inhibition of human 5alpha-reductases by polyphenols.
2002 Mar 15
Identification and quantification of galloyl derivatives, flavonoid glycosides and anthocyanins in leaves of Pistacia lentiscus L.
2002 Mar-Apr
Rutin-enhanced antibacterial activities of flavonoids against Bacillus cereus and Salmonella enteritidis.
2002 May
Polyphenols and red wine as peroxynitrite scavengers: a chemiluminescent assay.
2002 May
Inhibition by wine polyphenols of peroxynitrite-initiated chemiluminescence and NADH oxidation.
2002 May
Molecular modeling of flavonoids that inhibits xanthine oxidase.
2002 May 31
Interactions of flavonoids with iron and copper ions: a mechanism for their antioxidant activity.
2002 Nov
Polyphenols from the heartwood of Cercidiphyllum japonicum and their effects on proliferation of mouse hair epithelial cells.
2002 Nov
Antioxidant and free-radical scavenging activity of constituents of the leaves of Tachigalia paniculata.
2002 Nov
Rat kidney antioxidant response to long-term exposure to flavonol rich red wine.
2002 Nov 1
Antioxidant activities and antitumor screening of extracts from cranberry fruit (Vaccinium macrocarpon).
2002 Oct 9
Antitumor-promoting constituents from Dioscorea bulbifera L. in JB6 mouse epidermal cells.
2002 Sep
Flavonoids and antioxidant capacity of Georgia-grown Vidalia onions.
2002 Sep 11
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
Bioflavonoids attenuate renal proximal tubular cell injury during cold preservation in Euro-Collins and University of Wisconsin solutions.
2003 Feb
Effect of flavone derivatives on interleukin-1beta (IL-1beta) mRNA expression and IL-1beta protein synthesis in stimulated RAW 264.7 macrophages.
2003 Feb
Effect of fraxetin and myricetin on rotenone-induced cytotoxicity in SH-SY5Y cells: comparison with N-acetylcysteine.
2003 Jul 4
Fisetin, a flavonol, inhibits TH2-type cytokine production by activated human basophils.
2003 Jun
Separation of polyphenolic compounds extracted from plant matrices using capillary electrophoresis.
2003 Mar 21
Flavonol glycosides of Warburgia ugandensis leaves.
2003 Oct
Different antioxidant effects of polyphenols on lipid peroxidation and hydroxyl radicals in the NADPH-, Fe-ascorbate- and Fe-microsomal systems.
2003 Oct 1
Patents

Sample Use Guides

In Vivo Use Guide
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
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.
Name Type Language
MYRICETIN
HSDB   INCI   MI  
INCI  
Official Name English
NSC-407290
Preferred Name English
DELPHIDENOLON 1575
Common Name English
MYRICETIN [MI]
Common Name English
3,3',4',5,5',7-HEXAHYDROXYFLAVONE
Systematic Name English
CANNABISCETIN
Common Name English
MYRICETIN [HSDB]
Common Name English
3,5,7-TRIHYDROXY-2-(3,4,5-TRIHYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C792
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
DSLD 1291 (Number of products:23)
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
Code System Code Type Description
CHEBI
18152
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY
CHEBI
58395
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY
NCI_THESAURUS
C68458
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY
DRUG BANK
DB02375
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-463-2
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY
FDA UNII
76XC01FTOJ
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY
MESH
C040015
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY
DAILYMED
76XC01FTOJ
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY
PUBCHEM
5281672
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY
WIKIPEDIA
MYRICETIN
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY
EPA CompTox
DTXSID8022400
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY
RXCUI
1368374
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY RxNorm
MERCK INDEX
m7687
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY Merck Index
CAS
529-44-2
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY
NSC
407290
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY
HSDB
7682
Created by admin on Mon Mar 31 19:31:23 GMT 2025 , Edited by admin on Mon Mar 31 19:31:23 GMT 2025
PRIMARY