Structure Database (LMSD)
Common Name
Isosinensetin
Systematic Name
5,7,8,3',4'-Pentamethoxyflavone
Synonyms
- 6-Demethoxynobiletin
3D model of Isosinensetin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Isosinensetin is a polymethoxylated flavone that has been found in C. reticulata and has anticancer and anti-inflammatory activities.1,2,3 It inhibits P-glycoprotein (P-gp; IC50 = 4.2 µM) and increases the cytotoxicity of paraquat in MDR1-MDCKII cells and paclitaxel in MX-1 breast and paclitaxel-resistant MX-1/T cancer cells.1 Isosinensetin inhibits the proliferation of A549 lung, HL-60 leukemia, MCF-7 breast, and HO-8910 ovarian cancer cells (IC50s = 23.6, 23.8, 15.1, and 12.5 µM, respectively).2 It prevents decreases in cell viability and inhibits increases in IL-1β, TNF-α, and IL-6 levels and the production of reactive oxygen species (ROS) induced by fine particulate matter less than or equal to 2.5 µm (PM2.5) in 16HBE bronchial epithelial cells when used at a concentration of 80 µg/ml.3
This information has been provided by Cayman Chemical
References
2. Du, Q., and Chen, H. The methoxyflavones in Citrus reticulata Blanco cv. ponkan and their antiproliferative activity against cancer cells. Food Chem. 119(2), 567-572 (2010).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
UYCWETIUOAGWIL-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C20H20O7/c1-22-13-7-6-11(8-15(13)23-2)14-9-12(21)18-16(24-3)10-17(25-4)19(26-5)20(18)27-14/h6-10H,1-5H3
SMILES (Click to copy)
C1(OC)=C(OC)C2OC(C3C=C(OC)C(OC)=CC=3)=CC(=O)C=2C(OC)=C1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
27
Rings
3
Aromatic Rings
3
Rotatable Bonds
6
Van der Waals Molecular Volume
325.19
Topological Polar Surface Area
76.36
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
7
logP
4.40
Molar Refractivity
100.79
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Created at
-
Updated at
9th Jun 2022