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Details

Stereochemistry ACHIRAL
Molecular Formula C15H10O8
Molecular Weight 318.2357
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MYRICETIN

SMILES

c1c(cc(c(c1O)O)O)-c2c(c(=O)c3c(cc(cc3o2)O)O)O

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

Molecular Formula C15H10O8
Molecular Weight 318.2357
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

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
Flavones are inhibitors of HIV-1 proteinase.
1992 Oct 30
Evaluation of the clastogenic, DNA intercalative, and topoisomerase II-interactive properties of bioflavonoids in Chinese hamster V79 cells.
2002
[Studies on the chemical constituents from Ampelopsis grossedentata].
2002 Apr
Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.
2002 Dec
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
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 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
Ardisiphenols and other antioxidant principles from the fruits of Ardisia colorata.
2002 Nov
Nitric oxide formation and corresponding relaxation of porcine coronary arteries induced by plant phenols: essential structural features.
2002 Nov
Rat kidney antioxidant response to long-term exposure to flavonol rich red wine.
2002 Nov 1
Flavonol and flavone intakes in US health professionals.
2002 Oct
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
The unique occurrence of the flavone aglycone tricetin in Myrtaceae pollen.
2002 Sep-Oct
Antioxidant principles of Nelumbo nucifera stamens.
2003 Apr
Phenolic compounds from Nymphaea odorata.
2003 Apr
Phenolic content and antioxidant capacity of muscadine grapes.
2003 Aug 27
Flavones inhibit proliferation and increase mediator content in human leukemic mast cells (HMC-1).
2003 Dec
Nonaqueous capillary electrophoretic separation of polyphenolic compounds in wine using coated capillaries at high pH in methanol.
2003 Dec
Neuroprotection by flavonoids.
2003 Dec
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
Inhibition of syk activity and degranulation of human mast cells by flavonoids.
2003 Dec
Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context.
2003 Dec
L-type Ca2+ channels activation and contraction elicited by myricetin on vascular smooth muscles.
2003 Dec
The inhibitory effects of flavonoids and antiestrogens on the Glut1 glucose transporter in human erythrocytes.
2003 Dec 15
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
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
Cytotoxic effect of the diterpene lactone dehydrocrotonin from Croton cajucara on human promyelocytic leukemia cells.
2003 Jan
Malonylated flavonol glycosides from the petals of Clitoria ternatea.
2003 Jan
A flavonol O-methyltransferase from Catharanthus roseus performing two sequential methylations.
2003 Jan
Anti-complement activity of constituents from the stem-bark of Juglans mandshurica.
2003 Jul
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
Flavonol and drimane-type sesquiterpene glycosides of Warburgia stuhlmannii leaves.
2003 Jun
Chain-breaking antioxidant activity of natural polyphenols as determined during the chain oxidation of methyl linoleate in Triton X-100 micelles.
2003 Jun 15
Kinetic and stoichiometric assessment of the antioxidant activity of flavonoids by electron spin resonance spectroscopy.
2003 Mar 12
Separation of polyphenolic compounds extracted from plant matrices using capillary electrophoresis.
2003 Mar 21
Flavonol glycosides of Warburgia ugandensis leaves.
2003 Oct
Potent anti-amyloidogenic and fibril-destabilizing effects of polyphenols in vitro: implications for the prevention and therapeutics of Alzheimer's disease.
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
Flavonoid intake and breast cancer risk: a case--control study in Greece.
2003 Oct 6
Paclitaxel metabolism in rat and human liver microsomes is inhibited by phenolic antioxidants.
2003 Sep
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
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:06:55 UTC 2021
Edited
by admin
on Sat Jun 26 11:06:55 UTC 2021
Record UNII
76XC01FTOJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MYRICETIN
HSDB   INCI   MI  
INCI  
Official Name English
DELPHIDENOLON 1575
Common Name English
MYRICETIN [MI]
Common Name English
3,3',4',5,5',7-HEXAHYDROXYFLAVONE
Systematic Name English
NSC-407290
Code English
MYRICETIN [INCI]
Common 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 Sat Jun 26 11:06:55 UTC 2021 , Edited by admin on Sat Jun 26 11:06:55 UTC 2021
DSLD 1291 (Number of products:23)
Created by admin on Sat Jun 26 11:06:55 UTC 2021 , Edited by admin on Sat Jun 26 11:06:55 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C68458
Created by admin on Sat Jun 26 11:06:55 UTC 2021 , Edited by admin on Sat Jun 26 11:06:55 UTC 2021
PRIMARY
DRUG BANK
DB02375
Created by admin on Sat Jun 26 11:06:55 UTC 2021 , Edited by admin on Sat Jun 26 11:06:55 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-463-2
Created by admin on Sat Jun 26 11:06:55 UTC 2021 , Edited by admin on Sat Jun 26 11:06:55 UTC 2021
PRIMARY
FDA UNII
76XC01FTOJ
Created by admin on Sat Jun 26 11:06:55 UTC 2021 , Edited by admin on Sat Jun 26 11:06:55 UTC 2021
PRIMARY
MESH
C040015
Created by admin on Sat Jun 26 11:06:55 UTC 2021 , Edited by admin on Sat Jun 26 11:06:55 UTC 2021
PRIMARY
PUBCHEM
5281672
Created by admin on Sat Jun 26 11:06:55 UTC 2021 , Edited by admin on Sat Jun 26 11:06:55 UTC 2021
PRIMARY
WIKIPEDIA
MYRICETIN
Created by admin on Sat Jun 26 11:06:55 UTC 2021 , Edited by admin on Sat Jun 26 11:06:55 UTC 2021
PRIMARY
EPA CompTox
529-44-2
Created by admin on Sat Jun 26 11:06:55 UTC 2021 , Edited by admin on Sat Jun 26 11:06:55 UTC 2021
PRIMARY
RXCUI
1368374
Created by admin on Sat Jun 26 11:06:55 UTC 2021 , Edited by admin on Sat Jun 26 11:06:55 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M7687
Created by admin on Sat Jun 26 11:06:55 UTC 2021 , Edited by admin on Sat Jun 26 11:06:55 UTC 2021
PRIMARY Merck Index
CAS
529-44-2
Created by admin on Sat Jun 26 11:06:55 UTC 2021 , Edited by admin on Sat Jun 26 11:06:55 UTC 2021
PRIMARY
HSDB
7682
Created by admin on Sat Jun 26 11:06:55 UTC 2021 , Edited by admin on Sat Jun 26 11:06:55 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR