Structure Database (LMSD)

Common Name
Quercetin 3-methyl ether
Systematic Name
Synonyms
LM ID
LMPK12112729
Formula
Exact Mass
Calculate m/z
316.058305
Status
Curated


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

KEGG ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID

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