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Natural Product (NP) Details

General Information of the NP (ID: NP1168)
Name
Quercetin
Synonyms
Kvercetin; Meletin; QUE; Quercetine; Quercetol; Quercitin; Quertin; Quertine; Sophoretin; Xanthaurine; Flavin meletin; Kvercetin [Czech]; Quercetin content; Quercetin dihydrate; CI Natural Yellow 10; Cyanidelonon 1522; KUC104418N; KUC107684N; MixCom3_000183; Natural Yellow 10; P0042; Q 0125; TNP00070; TNP00089; LIM-5662; LNS-5662; C.I . natural yellow 10; C.I. 75670; C.I. Natural Yellow 10; C.I. Natural red 1; CU-01000012502-3; KSC-10-126; KSC-23-76; T-Gelb bzw. grun 1; C.I. Natural yellow 10 & 13; 2-(3,4-Dihydroxy-phenyl)-3,5,7-trihydroxy-chromen-4-one; 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one; 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one dihydrate; 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one; 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one; 3',4',5,7-Tetrahydroxyflavan-3-ol; 3',4',5,7-tetrahydroxyflavon-3-ol; 3,3',4',5,7-Pentahydroxyflavone dihydrate; 3,5,7,3',4'-Pentahydroxyflavone; 3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-on; 3,5,7-trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one
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Species Origin Averrhoa carambola ...     Click to Show/Hide
Averrhoa carambola
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Oxalidales
Family: Oxalidaceae
Genus: Averrhoa
Species: Averrhoa carambola
Astragalus sinicus
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Astragalus
Species: Astragalus sinicus
Amorpha fruticosa
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Amorpha
Species: Amorpha fruticosa
Bupleurum chinense
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Apiales
Family: Apiaceae
Genus: Bupleurum
Species: Bupleurum chinense
Kalanchoe pinnata
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Saxifragales
Family: Crassulaceae
Genus: Kalanchoe
Species: Kalanchoe pinnata
Abelmoschus manihot
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Malvales
Family: Malvaceae
Genus: Abelmoschus
Species: Abelmoschus manihot
Annona squamosa
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Magnoliales
Family: Annonaceae
Genus: Annona
Species: Annona squamosa
Apocynum venetum
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Gentianales
Family: Apocynaceae
Genus: Apocynum
Species: Apocynum venetum
Callicarpa cathayana
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Callicarpa
Species: Callicarpa cathayana
Disease Obesity [ICD-11: 5B81] Approved [1]
Structure
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2D MOL

3D MOL

    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C15H10O7
PubChem CID
5280343
Canonical SMILES
C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O
InChI
1S/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H
InChIKey
REFJWTPEDVJJIY-UHFFFAOYSA-N
CAS Number
CAS 117-39-5
ChEBI ID
CHEBI:16243
Herb ID
HBIN041495
ETMC ID
1697
SymMap ID
SMIT00013
TCMSP ID
MOL000098
TTD Drug ID
D0K8KX
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Expression ABCB1  Molecule Info 
Pathway MAP
Down-regulation Expression METTL3  Molecule Info 
Pathway MAP
Down-regulation Expression MMP-2  Molecule Info 
Pathway MAP
                    In-vitro Model HeLa CVCL_0030 Endocervical adenocarcinoma Homo sapiens
SiHa CVCL_0032 Cervical squamous cell carcinoma Homo sapiens
                    Experimental
                    Result(s)
Quercetin and cisplatin had synergistic inhibitory effect on cervical cancer cells. Quercetin might enhance the antitumor effect of cisplatin via inhibiting proliferation, migration and invasion and elevating apoptosis through weakening MMP2, ezrin, METTL3 and P-Gp expression of cancer cells.
          Temozolomide      Brain cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
Up-regulation Phosphorylation TP53  Molecule Info 
Pathway MAP
                    In-vitro Model SK-MEL-28 CVCL_0526 Cutaneous melanoma Homo sapiens
SK-MEL-5 CVCL_0527 Cutaneous melanoma Homo sapiens
DB-1 Melanoma Homo sapiens
                    Experimental
                    Result(s)
Qct can sensitize cells to TMZ and that the mechanisms of sensitization involve modulation of p53 family members.
          2-methoxyestradiol      Pulmonary hypertension     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Expression CASP3  Molecule Info 
Pathway MAP
                    In-vitro Model PC-3 CVCL_0035 Prostate carcinoma Homo sapiens
LNCaP CVCL_0395 Prostate carcinoma Homo sapiens
                    Experimental
                    Result(s)
Combination of quercetin and 2-Methoxyestradiol enhances inhibition of human prostate cancer LNCaP and PC-3 cells xenograft tumor growth.
          5-fluorouracil      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression TP53  Molecule Info 
Pathway MAP
                    In-vitro Model Co-115 CVCL_D102 Colon adenocarcinoma Homo sapiens
HCT 15 CVCL_0292 Colon adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)
Quercetin enhances 5-fluorouracil-induced apoptosis in MSI colorectal cancer cells through p53 modulation.
          Doxorubicin      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Expression ABCB1  Molecule Info 
Pathway MAP
                    In-vitro Model MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
                    Experimental
                    Result(s)
Quercetin potentiates the effect of adriamycin in a multidrug-resistant MCF-7 human breast-cancer cell line by down-regulating P-glycoprotein.
          Chloroquine      Malaria     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [7]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation
Induction Ca(2+) homeostasis disruption
Induction Lysosomal defects
                    In-vitro Model T98G CVCL_0556 Glioblastoma Homo sapiens
U-251MG CVCL_0021 Astrocytoma Homo sapiens
U-373MG ATCC CVCL_2219 Astrocytoma Homo sapiens
                    Experimental
                    Result(s)
Quercetin and chloroquine synergistically kill glioma cells by inducing organelle stress and disrupting Ca2+ homeostasis.
          Dacarbazine      Melanoma     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation
Increase Nuclear localization of deltaNp73
                    In-vitro Model DB1 CVCL_W884 Diffuse large B-cell lymphoma Homo sapiens
SK-MEL-28 CVCL_0526 Cutaneous melanoma Homo sapiens
                    Experimental
                    Result(s)
Quercetin abrogates chemoresistance in melanoma cells by modulating deltaNp73.
          Cis-diamminedichloroplatinum      Ovarian cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [8]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model LXFL 529L CVCL_D085 Lung non-small cell carcinoma Homo sapiens
                    Experimental
                    Result(s)
Quercetin enhances the antiproliferative activity of cis-diamminedichloroplatinum (II) in lung cancer cells.
          Carboxyamidotriazole      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [9]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model MDA-MB-435 CVCL_0417 Breast cancer Homo sapiens
                    Experimental
                    Result(s)
Quercetin and carboxyamidotriazole showed synergistic anticancer effects in breast carcinoma cells.
Target and Pathway
Target(s) Acetyl-CoA:lyso-PAF acetyltransferase (PCAT)  Molecule Info  [10]
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5346).
Reference 2 Effects of Quercetin on the Efficacy of Various Chemotherapeutic Drugs in Cervical Cancer Cells. Drug Des Devel Ther. 2021 Feb 15;15:577-588.
Reference 3 Quercetin abrogates chemoresistance in melanoma cells by modulating deltaNp73. BMC Cancer. 2010 Jun 11;10:282.
Reference 4 Combination of Quercetin and 2-Methoxyestradiol Enhances Inhibition of Human Prostate Cancer LNCaP and PC-3 Cells Xenograft Tumor Growth. PLoS One. 2015 May 26;10(5):e0128277.
Reference 5 Quercetin enhances 5-fluorouracil-induced apoptosis in MSI colorectal cancer cells through p53 modulation. Cancer Chemother Pharmacol. 2011 Dec;68(6):1449-57.
Reference 6 Quercetin potentiates the effect of adriamycin in a multidrug-resistant MCF-7 human breast-cancer cell line: P-glycoprotein as a possible target. Cancer Chemother Pharmacol. 1994;34(6):459-64.
Reference 7 Quercetin and chloroquine synergistically kill glioma cells by inducing organelle stress and disrupting Ca 2+ homeostasis. Biochem Pharmacol. 2020 Aug;178:114098.
Reference 8 Enhancement of the antiproliferative activity of cis-diamminedichloroplatinum(II) by quercetin. Int J Cancer. 1990 Mar 15;45(3):536-9.
Reference 9 Quercetin: synergistic action with carboxyamidotriazole in human breast carcinoma cells. Life Sci. 1995;57(13):1285-92.
Reference 10 Modulation by flavonoids of PAF and related phospholipids in endothelial cells during oxidative stress. J Lipid Res. 2003 Feb;44(2):380-7.
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Cite NPCDR
Visitor Map
Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China