Structure Database (LMSD)
Common Name
Quercetin 3-methyl ether
Systematic Name
Synonyms
3D model of Quercetin 3-methyl ether
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
3-O-methyl Quercetin is a flavone that has been found in C. balchaschensis and has diverse biological activities.1,2,3,4 It is an inhibitor of β-secretase (IC50 = 6.5 µM).1 It scavenges DPPH radicals and superoxide anions in cell-free assays (IC50s = 14.17 and 17.39 µM, respectively), as well as inhibits lipid peroxidation and hydrogen peroxide-induced neuronal cell death in primary rat cortical cells (IC50s = 19 and 3.5 µM, respectively).2 3-O-methyl Quercetin inhibits poliovirus RNA synthesis in infected HeLa cells when used at concentrations of 2 and 20 µg/ml.3 It also inhibits LPS-induced nitric oxide (NO) production in BV-2 microglia (IC50 = 3.8 µM) and reduces LPS-induced increases in the levels of inducible nitric oxide synthase (iNOS) in BV-2 microglia.4
This information has been provided by Cayman Chemical
References
3. Castrillo, J.L., and Carrasco, L. Action of 3-methylquercetin on poliovirus RNA replication. J. Virol. 61(10), 3319-3321 (1987).
4. Kim, J.Y., Lim, H.J., and Ryu, J.-H. In vitro anti-inflammatory activity of 3-O-methyl-flavones isolated from Siegesbeckia glabrescens. Bioorg. Med. Chem. Lett. 18(4), 1511-1514 (2008).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
WEPBGSIAWZTEJR-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H12O7/c1-22-16-14(21)13-11(20)5-8(17)6-12(13)23-15(16)7-2-3-9(18)10(19)4-7/h2-6,17-20H,1H3
SMILES (Click to copy)
C1(O)=CC2OC(C3C=C(O)C(O)=CC=3)=C(OC)C(=O)C=2C(O)=C1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
23
Rings
3
Aromatic Rings
3
Rotatable Bonds
2
Van der Waals Molecular Volume
255.99
Topological Polar Surface Area
120.36
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
7
logP
3.19
Molar Refractivity
81.24
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Created at
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Updated at
9th Jun 2022