Myricetin [529-44-2]

Cat# HY-15097-1ml

Size : 10mM/1mL

Brand : MedChemExpress

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Myricetin is a common plant-derived flavonoid with a wide range of activities including strong anti-oxidant, anticancer, antidiabetic and anti-inflammatory activities.

For research use only. We do not sell to patients.

Myricetin Chemical Structure

Myricetin Chemical Structure

CAS No. : 529-44-2

This product is a controlled substance and not for sale in your territory.

Based on 14 publication(s) in Google Scholar

Other Forms of Myricetin:

  • Dihydromyricetin In-stock
  • Myricetin-13C3 Get quote
  • Myricetin (Standard) Get quote

    Myricetin purchased from MedChemExpress. Usage Cited in: Int Immunopharmacol. 2019 Oct;75:105742.   [Abstract]

    Myricetin suppresses the generation of inflammatory mediators in IL-1β induced human chondrocytes. The protein expression of iNOS and COX-2 in chondrocytes is determined by western blots.

    View All PI3K Isoform Specific Products:

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    PI3Kα PI3Kβ PI3Kγ PI3Kδ PI3KC2α PI3KC2β PI3KC2γ Vps34 PI3K PI3KC3 p120γ
    Description

    Myricetin is a common plant-derived flavonoid with a wide range of activities including strong anti-oxidant, anticancer, antidiabetic and anti-inflammatory activities.

    Cellular Effect
    Cell Line Type Value Description References
    A549 IC50
    14.8 mg/mL
    Compound: 23
    Cytotoxicity against human A549 cells after 3 days by SRB assay
    Cytotoxicity against human A549 cells after 3 days by SRB assay
    [PMID: 15568778]
    BV-2 IC50
    > 100 μM
    Compound: 2
    Antineuroinflammatory activity in human BV2 cells assessed as inhibition of LPS-induced NO production after 24 hrs in presence of LPS by Griess reaction
    Antineuroinflammatory activity in human BV2 cells assessed as inhibition of LPS-induced NO production after 24 hrs in presence of LPS by Griess reaction
    [PMID: 27623545]
    CWR22R IC50
    13.1 μM
    Compound: 13
    Antiproliferative activity against human 22Rv1 cells incubated up to 144 hrs by Coulter particle count and size analyzer
    Antiproliferative activity against human 22Rv1 cells incubated up to 144 hrs by Coulter particle count and size analyzer
    [PMID: 22789812]
    H9 EC50
    35 μM
    Compound: 16
    Antiviral activity against HIV1 3B infected in human H9 cells assessed as inhibition of viral replication after 3 days by p24 antigen capture assay
    Antiviral activity against HIV1 3B infected in human H9 cells assessed as inhibition of viral replication after 3 days by p24 antigen capture assay
    [PMID: 8158164]
    H9 IC50
    69 μM
    Compound: 16
    Cytotoxicity against human H9 cells after 3 days
    Cytotoxicity against human H9 cells after 3 days
    [PMID: 8158164]
    HCT-116 IC50
    > 20 μM
    Compound: Myricetin
    Antiproliferative activity against human HCT-116 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay
    Antiproliferative activity against human HCT-116 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay
    [PMID: 32886510]
    HCT-116 IC50
    23 μM
    Compound: 3
    Growth inhibition of human HCT116 cells overexpressing PI3Kalpha after 48 hrs by MTT assay
    Growth inhibition of human HCT116 cells overexpressing PI3Kalpha after 48 hrs by MTT assay
    [PMID: 22212721]
    HCT-116 IC50
    24 μM
    Compound: 3
    Growth inhibition of human HCT116 cells after 48 hrs by MTT assay
    Growth inhibition of human HCT116 cells after 48 hrs by MTT assay
    [PMID: 22212721]
    HCT-116 IC50
    28.2 μM
    Compound: 206b
    Cytotoxicity against human HCT116 cells assessed as reduction in cell growth by WST-1 assay
    Cytotoxicity against human HCT116 cells assessed as reduction in cell growth by WST-1 assay
    [PMID: 30917303]
    HCT-116 IC50
    4.1 μM
    Compound: 3
    Growth inhibition of human HCT116 cells overexpressing PI3Kalpha H1047R mutant after 48 hrs by MTT assay
    Growth inhibition of human HCT116 cells overexpressing PI3Kalpha H1047R mutant after 48 hrs by MTT assay
    [PMID: 22212721]
    HEK293 IC50
    > 10 μM
    Compound: 23
    Inhibition of human TRPC5 expressed in HEK293 cells assessed as reduction in gadolinium-induced calcium entry after 30 mins by fluo-4 dye based fluorescence assay
    Inhibition of human TRPC5 expressed in HEK293 cells assessed as reduction in gadolinium-induced calcium entry after 30 mins by fluo-4 dye based fluorescence assay
    [PMID: 30943030]
    HepG2 IC50
    > 20 μM
    Compound: Myricetin
    Antiproliferative activity against human HepG2 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay
    Antiproliferative activity against human HepG2 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay
    [PMID: 32886510]
    HK-2 IC50
    > 20 μM
    Compound: Myricetin
    Cytotoxicity against human HK2 cells assessed as cell viability incubated for 24 hrs by MTT assay
    Cytotoxicity against human HK2 cells assessed as cell viability incubated for 24 hrs by MTT assay
    [PMID: 32886510]
    HT-29 IC50
    > 20 μM
    Compound: Myricetin
    Antiproliferative activity against human HT-29 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay
    Antiproliferative activity against human HT-29 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay
    [PMID: 32886510]
    HT-29 IC50
    2.12 μM
    Compound: Myricetin
    Desensitization of GPR35 receptor in human HT-29 cells assessed as inhibition of zaprinast-induced dynamic mass redistribution after 10 mins
    Desensitization of GPR35 receptor in human HT-29 cells assessed as inhibition of zaprinast-induced dynamic mass redistribution after 10 mins
    [PMID: 24900447]
    HT-29 EC50
    3.02 μM
    Compound: Myricetin
    Agonist activity at GPR35 receptor in human HT-29 cells after 10 mins by dynamic mass redistribution assay
    Agonist activity at GPR35 receptor in human HT-29 cells after 10 mins by dynamic mass redistribution assay
    [PMID: 24900447]
    Huh-7 CC50
    > 50 μM
    Compound: 28
    Cytotoxicity against human Huh7.5.1 cells by MTT assay
    Cytotoxicity against human Huh7.5.1 cells by MTT assay
    [PMID: 22445328]
    Huh-7 EC50
    46.9 μM
    Compound: 28
    Antiviral activity against HCV JFH-1 J399EM infected in Human Huh7.5.1 cells assessed as suppression of viral replication after 72 hrs by EGFP assay
    Antiviral activity against HCV JFH-1 J399EM infected in Human Huh7.5.1 cells assessed as suppression of viral replication after 72 hrs by EGFP assay
    [PMID: 22445328]
    Jurkat IC50
    10 μM
    Compound: Myricetin
    Inhibition of chymotrypsin-like activity of purified human 20S proteasome expressed in human Jurkat cells assessed as decrease in AMC hydrolysis using Suc-Leu-Leu-Val-Tyr-AMC as substrate incubated for 2 hrs by fluorescence based method
    Inhibition of chymotrypsin-like activity of purified human 20S proteasome expressed in human Jurkat cells assessed as decrease in AMC hydrolysis using Suc-Leu-Leu-Val-Tyr-AMC as substrate incubated for 2 hrs by fluorescence based method
    [PMID: 30776692]
    Jurkat IC50
    12 μM
    Compound: Myricetin
    Inhibition of chymotrypsin-like activity of human 26S proteasome in human Jurkat cells assessed as decrease in AMC hydrolysis using Z-Gly-Gly-Leu-AMC as substrate after 24 hrs by fluorescence based method
    Inhibition of chymotrypsin-like activity of human 26S proteasome in human Jurkat cells assessed as decrease in AMC hydrolysis using Z-Gly-Gly-Leu-AMC as substrate after 24 hrs by fluorescence based method
    [PMID: 30776692]
    L02 IC50
    > 20 μM
    Compound: Myricetin
    Cytotoxicity against human L02 cells assessed as cell viability incubated for 24 hrs by MTT assay
    Cytotoxicity against human L02 cells assessed as cell viability incubated for 24 hrs by MTT assay
    [PMID: 32886510]
    L929 EC50
    55 μM
    Compound: myricetin
    Inhibition of recombinant human TNF-alpha-induced cytotoxicity of mouse L929 cells assessed as survivality preincubated for 15 mins before TNFalpha addition measured after 24 hrs by crystal violet staining
    Inhibition of recombinant human TNF-alpha-induced cytotoxicity of mouse L929 cells assessed as survivality preincubated for 15 mins before TNFalpha addition measured after 24 hrs by crystal violet staining
    [PMID: 9287415]
    L929 EC50
    59 μM
    Compound: myricetin
    Inhibition of recombinant human TNF-alpha-induced cytotoxicity of mouse L929 cells assessed as survivality preincubated for 15 mins before TNFalpha addition measured after 24 hrs by [methyl-3H]thymidine incorporation assay
    Inhibition of recombinant human TNF-alpha-induced cytotoxicity of mouse L929 cells assessed as survivality preincubated for 15 mins before TNFalpha addition measured after 24 hrs by [methyl-3H]thymidine incorporation assay
    [PMID: 9287415]
    MCF7 IC50
    > 20 μM
    Compound: Myricetin
    Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay
    Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay
    [PMID: 32886510]
    MCF7 IC50
    4.7 mg/mL
    Compound: 23
    Cytotoxicity against human MCF7 cells after 3 days by SRB assay
    Cytotoxicity against human MCF7 cells after 3 days by SRB assay
    [PMID: 15568778]
    MV4-11 GI50
    > 50 μM
    Compound: 7
    Cytotoxicity against human MV4-11 cells harboring FLT3 mutation after 72 hrs by tetrazolium based Ez CyTox cell viability assay
    Cytotoxicity against human MV4-11 cells harboring FLT3 mutation after 72 hrs by tetrazolium based Ez CyTox cell viability assay
    [PMID: 23411073]
    Peritoneal macrophage IC50
    99 μM
    Compound: kp22
    Inhibition of LPS-stimulated nitric oxide production in ddy mouse peritoneal macrophages measured after 20 hrs by Greiss method
    Inhibition of LPS-stimulated nitric oxide production in ddy mouse peritoneal macrophages measured after 20 hrs by Greiss method
    [PMID: 27955927]
    RS4-11 GI50
    > 50 μM
    Compound: 7
    Cytotoxicity against human RS4:11 cells harboring wild type FLT3 after 72 hrs by tetrazolium based Ez CyTox cell viability assay
    Cytotoxicity against human RS4:11 cells harboring wild type FLT3 after 72 hrs by tetrazolium based Ez CyTox cell viability assay
    [PMID: 23411073]
    SK-BR-3 IC50
    > 100 μM
    Compound: 4
    Induction of apoptosis in human SKBR3 cells assessed as PARP cleavage by Western blotting analysis
    Induction of apoptosis in human SKBR3 cells assessed as PARP cleavage by Western blotting analysis
    [PMID: 24548207]
    SK-BR-3 IC50
    > 100 μM
    Compound: 4
    Inhibition of Hsp70 in human SKBR3 cells assessed as RAF1 protein degradation by Western blotting analysis
    Inhibition of Hsp70 in human SKBR3 cells assessed as RAF1 protein degradation by Western blotting analysis
    [PMID: 24548207]
    SK-BR-3 IC50
    > 100 μM
    Compound: 4
    Inhibition of Hsp70 in human SKBR3 cells assessed as HER2 protein degradation by Western blotting analysis
    Inhibition of Hsp70 in human SKBR3 cells assessed as HER2 protein degradation by Western blotting analysis
    [PMID: 24548207]
    SK-BR-3 IC50
    13.5 μM
    Compound: 4
    Displacement of GM-cy3B from Hsp90 in human SKBR3 cells after 24 hrs by fluorescence polarization assay
    Displacement of GM-cy3B from Hsp90 in human SKBR3 cells after 24 hrs by fluorescence polarization assay
    [PMID: 24548207]
    U2OS EC50
    14.7 μM
    Compound: Myricetin
    Agonist activity at GPR35 receptor in human U2OS cells coexpressing Gal4-VP16-TEV assessed as beta arrestin translocation after 5 hrs by beta lactamase reporter gene assay
    Agonist activity at GPR35 receptor in human U2OS cells coexpressing Gal4-VP16-TEV assessed as beta arrestin translocation after 5 hrs by beta lactamase reporter gene assay
    [PMID: 24900447]
    In Vitro

    Myricetin exhibits the scavenging activity towards a number of radicals and ions. It displays poor activity (IC50 value=1.4 mg/mL) in a superoxide dismutase (SOD)-like activity assay[1]. It prevents cancer cell death via apoptosis via regulation of PI3K/Akt and MAPK signalling pathways[2].
    Myricetin exhibits antiphotoaging effects by quenching causative free radicals in the skin. Myricetin is able to suppress UVB-induced COX-2 expression in mouse skin epidermal JB6 P+ cells. It inhibits UVB-induced initiation of activator protein-1 and NF-κβ, as well as Fyn kinase activity[1].
    Myricetin inhibits viability of SKOV3 ovarian cancer cells in a dose-dependent manner. It induces DNA DSBs and ER stress, which leads to apoptosis in SKOV3 cells[3].
    Myricetin inhibits human Hsp70 by more than 80% with IC50 values of 83, 11 and 12 μM, respectively[4].

    MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

    In Vivo

    Treatment of orthotopic pancreatic tumors with myricetin results in tumor regression and decreases metastatic spread[2]. Exposure to 150 μM myricetin causes 14%, 26%, 5% and 49% inhibition of rabbit platelet aggregation, induced by ADP, arachidonic acid, collagen and PAF, respectively[5].

    MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

    Molecular Weight

    318.24

    Formula

    C15H10O8

    CAS No.

    529-44-2

    Appearance

    Solid

    Color

    Light yellow to yellow

    SMILES

    OC1=CC(O)=C(C(C(O)=C(C2=CC(O)=C(O)C(O)=C2)O3)=O)C3=C1

    Structure Classification
    • Flavonoids
    • Flavonols
    Initial Source
    • Plants
    • Myricaceae
    • Myrica nagi
    • Endogenous metabolite
    • Human Gut Microbiota Metabolites
    • Microorganisms
    Shipping

    Room temperature in continental US; may vary elsewhere.

    Storage
    Powder -20°C 3 years
    4°C 2 years
    In solvent -80°C 1 year
    -20°C 6 months
    Solvent & Solubility
    In Vitro: 

    DMSO : ≥ 31 mg/mL (97.41 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

    Ethanol : 28.57 mg/mL (89.78 mM; Need ultrasonic)

    *"≥" means soluble, but saturation unknown.

    Preparing
    Stock Solutions
    Concentration Solvent Mass 1 mg 5 mg 10 mg
    1 mM 3.1423 mL 15.7114 mL 31.4228 mL
    5 mM 0.6285 mL 3.1423 mL 6.2846 mL
    View the Complete Stock Solution Preparation Table

    * Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
    Storage method and period of stock solution: -80°C, 1 year; -20°C, 6 months. When stored at -80°C, please use it within 1 year. When stored at -20°C, please use it within 6 months.

    • Molarity Calculator

    • Dilution Calculator

    Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

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    Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

    This equation is commonly abbreviated as: C1V1 = C2V2

    Concentration (start)

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    In Vivo:

    Select the appropriate dissolution method based on your experimental animal and administration route.

    For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
    To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
    The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

    • Protocol 1

      Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% Saline

      Solubility: ≥ 2.08 mg/mL (6.54 mM); Clear solution

      This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).

      Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

      Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
    • Protocol 2

      Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in Saline)

      Solubility: ≥ 2.08 mg/mL (6.54 mM); Clear solution

      This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).

      Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

      Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
    In Vivo Dissolution Calculator
    Please enter the basic information of animal experiments:

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    Number of animals

    Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
    Please enter your animal formula composition:
    %
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    Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
    The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
    Calculation results:
    Working solution concentration: mg/mL
    Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).
    The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
    Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
     If the continuous dosing period exceeds half a month, please choose this protocol carefully.
    Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
    Purity & Documentation

    Purity: 98.42%

    References
    • [1]. Semwal DK, et al. Myricetin: A Dietary Molecule with Diverse Biological Activities. Nutrients. 2016 Feb 16;8(2):90.  [Content Brief]

      [2]. Phillips PA, et al. Myricetin induces pancreatic cancer cell death via the induction of apoptosis and inhibition of thephosphatidylinositol 3-kinase (PI3K) signaling pathway. Cancer Lett. 2011 Sep 28;308(2):181-8.  [Content Brief]

      [3]. Xu Y, et al. Myricetin induces apoptosis via endoplasmic reticulum stress and DNA double-strand breaks in human ovarian cancer cells. Mol Med Rep. 2016 Mar;13(3):2094-100.  [Content Brief]

      [4]. Jinwal UK, et al. Chemical Manipulation of Hsp70 ATPase Activity Regulates Tau Stability. J Neurosci. 2009 Sep 30;29(39):12079-88.  [Content Brief]

      [5]. Tzeng SH, et al. Inhibition of platelet aggregation by some flavonoids. Thromb Res. 1991 Oct 1;64(1):91-100.  [Content Brief]

    Cell Assay
    [2]

    Pancreatic cancer cells (MIA PaCa-2, Panc-1 or S2-013) or normal pancreatic ductal cells (PDCs) are treated with myricetin (12.5–200 μM). Cell viability is determined using the Dojindo Cell Counting Kit-8. Cells are seeded onto a 96-well plate at 1×104 cells per well and allowed to adhere overnight. After treatment with myricetin at various concentrations for 24 hours, 10 μL of the tetrazolium substrate is added to each well of the plate. Plates are incubated at 37°C for 1 hour, after which the absorbance at 450 nm is measured[2].

    MCE has not independently confirmed the accuracy of these methods. They are for reference only.

    Animal Administration
    [2]

    Mice: Mice are given daily intraperitoneal injections of myricetin (30mg/kg in the MIA PaCa-2 model and 50mg/kg in the S2-013 model) or vehicle (DMSO) for 35 days (MIA PaCa-2 model) or 18 days (S2-013 model). Ultrasound measurements are performed at regular intervals to monitor tumor growth. At the end of the in vivo experiment, tumor size is measured using calipers and tumor volume is calculated[2].

    MCE has not independently confirmed the accuracy of these methods. They are for reference only.

    References
    • [1]. Semwal DK, et al. Myricetin: A Dietary Molecule with Diverse Biological Activities. Nutrients. 2016 Feb 16;8(2):90.  [Content Brief]

      [2]. Phillips PA, et al. Myricetin induces pancreatic cancer cell death via the induction of apoptosis and inhibition of thephosphatidylinositol 3-kinase (PI3K) signaling pathway. Cancer Lett. 2011 Sep 28;308(2):181-8.  [Content Brief]

      [3]. Xu Y, et al. Myricetin induces apoptosis via endoplasmic reticulum stress and DNA double-strand breaks in human ovarian cancer cells. Mol Med Rep. 2016 Mar;13(3):2094-100.  [Content Brief]

      [4]. Jinwal UK, et al. Chemical Manipulation of Hsp70 ATPase Activity Regulates Tau Stability. J Neurosci. 2009 Sep 30;29(39):12079-88.  [Content Brief]

      [5]. Tzeng SH, et al. Inhibition of platelet aggregation by some flavonoids. Thromb Res. 1991 Oct 1;64(1):91-100.  [Content Brief]

    Complete Stock Solution Preparation Table

    * Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
    Storage method and period of stock solution: -80°C, 1 year; -20°C, 6 months. When stored at -80°C, please use it within 1 year. When stored at -20°C, please use it within 6 months.

    Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
    Ethanol / DMSO 1 mM 3.1423 mL 15.7114 mL 31.4228 mL 78.5571 mL
    5 mM 0.6285 mL 3.1423 mL 6.2846 mL 15.7114 mL
    10 mM 0.3142 mL 1.5711 mL 3.1423 mL 7.8557 mL
    15 mM 0.2095 mL 1.0474 mL 2.0949 mL 5.2371 mL
    20 mM 0.1571 mL 0.7856 mL 1.5711 mL 3.9279 mL
    25 mM 0.1257 mL 0.6285 mL 1.2569 mL 3.1423 mL
    30 mM 0.1047 mL 0.5237 mL 1.0474 mL 2.6186 mL
    40 mM 0.0786 mL 0.3928 mL 0.7856 mL 1.9639 mL
    50 mM 0.0628 mL 0.3142 mL 0.6285 mL 1.5711 mL
    60 mM 0.0524 mL 0.2619 mL 0.5237 mL 1.3093 mL
    80 mM 0.0393 mL 0.1964 mL 0.3928 mL 0.9820 mL
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    Myricetin Related Classifications

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    Keywords:

    Myricetin529-44-2CannabiscetinPI3KApoptosisAutophagyEndogenous MetabolitePhosphoinositide 3-kinaseInhibitorinhibitorinhibit

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