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Identification
NameQuercetin
Accession NumberDB04216  (EXPT02732)
Typesmall molecule
Groupsexperimental
Description

A flavonol widely distributed in plants. It is an antioxidant, like many other phenolic heterocyclic compounds. Glycosylated forms include RUTIN and quercetrin. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
3,5,7,3',4'-PentahydroxyflavoneNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number117-39-5
WeightAverage: 302.2357
Monoisotopic: 302.042652674
Chemical FormulaC15H10O7
InChI KeyInChIKey=REFJWTPEDVJJIY-UHFFFAOYSA-N
InChI
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
IUPAC Name
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
SMILES
OC1=CC2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C(O)=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassPhenylpropanoids and Polyketides
ClassFlavonoids
SubclassFlavones
Direct parentFlavonols
Alternative parentsChromones; Catechols; Pyranones and Derivatives; Polyols; Enols; Polyamines
Substituentschromone; benzopyran; 1,2-diphenol; pyranone; phenol derivative; benzene; pyran; polyol; enol; polyamine
Classification descriptionThis compound belongs to the flavonols. These are compounds that has the 3-hydroxyflavone backbone.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionQuercetin is a specific quinone reductase 2 (QR2) inhibitor, an enzyme (along with the human QR1 homolog) which catalyzes metabolism of toxic quinolines. Inhibition of QR2 in plasmodium may potentially cause lethal oxidative stress. The inhibition of antioxidant activity in plasmodium may contribute to killing the malaria causing parasites.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.965
Blood Brain Barrier - 0.5711
Caco-2 permeable - 0.8957
P-glycoprotein substrate Substrate 0.5629
P-glycoprotein inhibitor I Non-inhibitor 0.9297
P-glycoprotein inhibitor II Non-inhibitor 0.8382
Renal organic cation transporter Non-inhibitor 0.931
CYP450 2C9 substrate Non-substrate 0.7898
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Non-substrate 0.653
CYP450 1A2 substrate Inhibitor 0.9106
CYP450 2C9 substrate Non-inhibitor 0.5823
CYP450 2D6 substrate Non-inhibitor 0.9287
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Inhibitor 0.6951
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5822
Ames test Non AMES toxic 0.722
Carcinogenicity Non-carcinogens 0.945
Biodegradation Not ready biodegradable 0.8672
Rat acute toxicity 3.0200 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9781
hERG inhibition (predictor II) Non-inhibitor 0.8161
Pharmacoeconomics
ManufacturersNot Available
Packagers
  • V Sab Medical Labs Inc.
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point316.5 °CPhysProp
water solubility60 mg/L (at 16 °C)SEIDELL,A (1941)
Predicted Properties
PropertyValueSource
water solubility2.61e-01 g/lALOGPS
logP1.81ALOGPS
logP2.16ChemAxon
logS-3.1ALOGPS
pKa (strongest acidic)6.44ChemAxon
pKa (strongest basic)-4ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count7ChemAxon
hydrogen donor count5ChemAxon
polar surface area127.45ChemAxon
rotatable bond count1ChemAxon
refractivity76.86ChemAxon
polarizability28.54ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
Spectra
References
Synthesis Reference

Miguel M. Taya, Dionisio M. Aedo, Rene Ricard, “Quercetin pentamethyl carbamate and a process for its preparation.” U.S. Patent US4202825, issued October, 1975.

US4202825
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC00389
PubChem Compound5280343
PubChem Substance46506533
ChemSpider4444051
BindingDB7460
ChEBI16243
ChEMBL
Therapeutic Targets DatabaseDAP001419
HETQUE
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Tyrosine-protein kinase HCK

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tyrosine-protein kinase HCK P08631 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

3. UDP-glucuronosyltransferase 3A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 3A1 Q6NUS8 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

4. ATP synthase subunit alpha, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
ATP synthase subunit alpha, mitochondrial P25705 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

5. ATP synthase subunit beta, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
ATP synthase subunit beta, mitochondrial P06576 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

6. ATP synthase subunit gamma, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
ATP synthase subunit gamma, mitochondrial P36542 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

7. Serine/threonine-protein kinase pim-1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serine/threonine-protein kinase pim-1 P11309 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

8. HTH-type transcriptional regulator TtgR

Kind: protein

Organism: Pseudomonas putida (strain DOT-T1E)

Pharmacological action: unknown

Components

Name UniProt ID Details
HTH-type transcriptional regulator TtgR Q9AIU0 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

9. 3-hydroxyisobutyryl-CoA hydrolase, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial Q6NVY1 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

10. 3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZ

Kind: protein

Organism: Helicobacter pylori

Pharmacological action: unknown

Components

Name UniProt ID Details
3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZ Q5G940 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

11. Serine/threonine-protein kinase 17B

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serine/threonine-protein kinase 17B O94768 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

1. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. Pubmed
  2. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

1. Multidrug resistance-associated protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor inducer

Components

Name UniProt ID Details
Multidrug resistance-associated protein 1 P33527 Details

References:

  1. Kauffmann HM, Pfannschmidt S, Zoller H, Benz A, Vorderstemann B, Webster JI, Schrenk D: Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression. Toxicology. 2002 Feb 28;171(2-3):137-46. Pubmed
  2. Leslie EM, Mao Q, Oleschuk CJ, Deeley RG, Cole SP: Modulation of multidrug resistance protein 1 (MRP1/ABCC1) transport and atpase activities by interaction with dietary flavonoids. Mol Pharmacol. 2001 May;59(5):1171-80. Pubmed
  3. Nguyen H, Zhang S, Morris ME: Effect of flavonoids on MRP1-mediated transport in Panc-1 cells. J Pharm Sci. 2003 Feb;92(2):250-7. Pubmed

2. Canalicular multispecific organic anion transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Canalicular multispecific organic anion transporter 1 Q92887 Details

References:

  1. Bock KW, Eckle T, Ouzzine M, Fournel-Gigleux S: Coordinate induction by antioxidants of UDP-glucuronosyltransferase UGT1A6 and the apical conjugate export pump MRP2 (multidrug resistance protein 2) in Caco-2 cells. Biochem Pharmacol. 2000 Mar 1;59(5):467-70. Pubmed

3. Monocarboxylate transporter 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Monocarboxylate transporter 2 O60669 Details

References:

  1. Broer S, Broer A, Schneider HP, Stegen C, Halestrap AP, Deitmer JW: Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes. Biochem J. 1999 Aug 1;341 ( Pt 3):529-35. Pubmed

4. Solute carrier organic anion transporter family member 2B1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 2B1 O94956 Details

References:

  1. Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y: Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B. Drug Metab Dispos. 2005 Apr;33(4):518-23. Epub 2005 Jan 7. Pubmed

5. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Shapiro AB, Ling V: Effect of quercetin on Hoechst 33342 transport by purified and reconstituted P-glycoprotein. Biochem Pharmacol. 1997 Feb 21;53(4):587-96. Pubmed
  2. Eagling VA, Profit L, Back DJ: Inhibition of the CYP3A4-mediated metabolism and P-glycoprotein-mediated transport of the HIV-1 protease inhibitor saquinavir by grapefruit juice components. Br J Clin Pharmacol. 1999 Oct;48(4):543-52. Pubmed
  3. Choi CH, Kim JH, Kim SH: Reversal of P-glycoprotein-mediated MDR by 5,7,3’,4’,5’-pentamethoxyflavone and SAR. Biochem Biophys Res Commun. 2004 Jul 30;320(3):672-9. Pubmed
  4. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. Pubmed
  5. Youdim KA, Qaiser MZ, Begley DJ, Rice-Evans CA, Abbott NJ: Flavonoid permeability across an in situ model of the blood-brain barrier. Free Radic Biol Med. 2004 Mar 1;36(5):592-604. Pubmed
  6. Borska S, Sopel M, Chmielewska M, Zabel M, Dziegiel P: Quercetin as a potential modulator of P-glycoprotein expression and function in cells of human pancreatic carcinoma line resistant to daunorubicin. Molecules. 2010 Feb 9;15(2):857-70. Pubmed

6. Monocarboxylate transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Monocarboxylate transporter 1 P53985 Details

References:

  1. Broer S, Broer A, Schneider HP, Stegen C, Halestrap AP, Deitmer JW: Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes. Biochem J. 1999 Aug 1;341 ( Pt 3):529-35. Pubmed

7. ATP-binding cassette sub-family G member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
ATP-binding cassette sub-family G member 2 Q9UNQ0 Details

References:

  1. Zhang S, Yang X, Morris ME: Flavonoids are inhibitors of breast cancer resistance protein (ABCG2)-mediated transport. Mol Pharmacol. 2004 May;65(5):1208-16. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:23