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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
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.
2000 Jul-Aug
Measurement of copper-binding sites on low density lipoprotein.
2001 Apr
A novel cytotoxic flavonoid glycoside from Physalis angulata.
2001 Aug
Activity of plant flavonoids against antibiotic-resistant bacteria.
2001 Feb
[Comparison of photometric, electrochemical and post-column fluorescence detection for the determination of flavonoids by HPLC].
2001 Jun
Anti-androgenic activity of Myricae Cortex--isolation of active constituents from bark of Myrica rubra.
2001 Mar
Flavonoids and urate antioxidant interplay in plasma oxidative stress.
2001 May
Modulation of multidrug resistance protein 1 (MRP1/ABCC1) transport and atpase activities by interaction with dietary flavonoids.
2001 May
Effects of flavonols on the generation of superoxide anion radicals by xanthine oxidase and stimulated neutrophils.
2001 Nov 1
Evaluation of the clastogenic, DNA intercalative, and topoisomerase II-interactive properties of bioflavonoids in Chinese hamster V79 cells.
2002
Dietary flavonoids: bioavailability, metabolic effects, and safety.
2002
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
Identification and quantification of galloyl derivatives, flavonoid glycosides and anthocyanins in leaves of Pistacia lentiscus L.
2002 Mar-Apr
Polyphenols from the heartwood of Cercidiphyllum japonicum and their effects on proliferation of mouse hair epithelial cells.
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
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
Phenolic compounds from Nymphaea odorata.
2003 Apr
Bioflavonoids attenuate renal proximal tubular cell injury during cold preservation in Euro-Collins and University of Wisconsin solutions.
2003 Feb
Malonylated flavonol glycosides from the petals of Clitoria ternatea.
2003 Jan
Separation of polyphenolic compounds extracted from plant matrices using capillary electrophoresis.
2003 Mar 21
Flavonol glycosides of Warburgia ugandensis leaves.
2003 Oct
Paclitaxel metabolism in rat and human liver microsomes is inhibited by phenolic antioxidants.
2003 Sep
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
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 Fri Dec 15 19:02:39 GMT 2023 , Edited by admin on Fri Dec 15 19:02:39 GMT 2023
DSLD 1291 (Number of products:23)
Created by admin on Fri Dec 15 19:02:39 GMT 2023 , Edited by admin on Fri Dec 15 19:02:39 GMT 2023
Code System Code Type Description
CHEBI
18152
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PRIMARY
CHEBI
58395
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PRIMARY
NCI_THESAURUS
C68458
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PRIMARY
DRUG BANK
DB02375
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PRIMARY
ECHA (EC/EINECS)
208-463-2
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PRIMARY
FDA UNII
76XC01FTOJ
Created by admin on Fri Dec 15 19:02:39 GMT 2023 , Edited by admin on Fri Dec 15 19:02:39 GMT 2023
PRIMARY
MESH
C040015
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PRIMARY
DAILYMED
76XC01FTOJ
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PUBCHEM
5281672
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PRIMARY
WIKIPEDIA
MYRICETIN
Created by admin on Fri Dec 15 19:02:39 GMT 2023 , Edited by admin on Fri Dec 15 19:02:39 GMT 2023
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EPA CompTox
DTXSID8022400
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PRIMARY
RXCUI
1368374
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PRIMARY RxNorm
MERCK INDEX
m7687
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PRIMARY Merck Index
CAS
529-44-2
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PRIMARY
NSC
407290
Created by admin on Fri Dec 15 19:02:39 GMT 2023 , Edited by admin on Fri Dec 15 19:02:39 GMT 2023
PRIMARY
HSDB
7682
Created by admin on Fri Dec 15 19:02:39 GMT 2023 , Edited by admin on Fri Dec 15 19:02:39 GMT 2023
PRIMARY