2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one

• ChemBase ID: 3829
• Molecular Formular: C15H10O7
• Molecular Mass: 302.2357
• Monoisotopic Mass: 302.04265266
• SMILES: c1c(c2c(cc1O)oc(c(c2=O)O)c1ccc(c(c1)O)O)O
• Canonical SMILES: Oc1cc(O)c2c(c1)oc(c(c2=O)O)c1ccc(c(c1)O)O
• 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
• InChIKey: REFJWTPEDVJJIY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
• IUPAC Traditional name: quercetin
• Synonyms: Xanthaurine; Quercetol; Quercitin; Quertine; Flavin meletin; Sophoretin; Meletin; Quercetine; Quercetin(Sophoretin); 3,5,7,3',4'-Pentahydroxyflavone; Quercetin; 3,3',4',5,7-Pentahydroxyflavone; Quercetin

Database IDs

• CAS Number: 117-39-5
• PubChem SID: 46506533; 160967266
• PubChem CID: 5280343
• CHEBI ID: 16243
• CHEMBL: 50
• Chemspider ID: 4444051
• DrugBank ID: DB04216
• KEGG ID: C00389
• Unique Ingredient Identifier: 9IKM0I5T1E
• Wikipedia Title: Quercetin

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.3790317
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 2.1026077
• LogD (pH = 7.4): 1.000175
• Log P: 2.1562994
• Molar Refractivity: 76.8622 cm^3
• Polarizability: 28.418238 Å^3
• Polar Surface Area: 127.45 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.81
• LOG S: -3.06
• Solubility (Water): 2.61e-01 g/l

PROPERTIES

Physical Property

• Solubility: Practically insoluble in water; soluble in aqueous alkaline solutions
• Apperance: yellow crystalline powder; Yellow powder
• Melting Point: 316 °C
• Density: 1.799 g/cm^3

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: PI3K / PKC / Src-bcr

Product Information

• Purity: 99.0
• Salt Data: Free Base

DETAILS

DrugBank - DB04216

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

Selleck Chemicals - S2391

Research Area: Cancer
Biological Activity:
Quercetin (Sophoretin) is a PI3K and PKC inhibitor with IC50 of 3.8 μM and 15µg/ml. It strongly abrogated PI3K and Src kinases, mildly inhibited Akt1/2, and slightly affected PKC, p38 and ERK1/2. [1][2] Quercetin is a naturally-occurring polar auxin transport inhibitor with IC50 of 0.8, 16.7, 6.1, 11.36 µM for the inhibition of LDH% release, the inhibition of TNF-induced PMN-EC adhesion, TNF-induced inhibition of DNA synthesis and proliferation. It is a type of plant-based chemical, or phytochemical, known as a flavonol and a plant-derived flavonoid found in fruits, vegetables, leaves and grains. It also may be used as an ingredient in supplements, beverages or foods. In several studies, it may have anti-inflammatory and antioxidant properties, and it is being investigated for a wide range of potential health benefits. [3]References on Quercetin (Sophoretin)[1] Mol Pharmacol, 2001, 59:1138–1146[2] Fitoterapia, 2010, 81:75–80

REFERENCES

• Sidhu JS et al. Mol Pharmacol. 2001 May; 59(5):1138-46.