Structure Database (LMSD)

Common Name
Isosinensetin
Systematic Name
5,7,8,3',4'-Pentamethoxyflavone
Synonyms
  • 6-Demethoxynobiletin
LM ID
LMPK12111403
Formula
Exact Mass
Calculate m/z
372.120905
Status
Curated


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

HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID

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