Structure Database (LMSD)

Common Name
Sinensetin
Systematic Name
5,6,7,3',4'-Pentamethoxyflavone
Synonyms
  • Pedalitin permethyl ether
LM ID
LMPK12111250
Formula
C20H20O7
Exact Mass
Calculate m/z
372.120905
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Flavones and Flavonols [PK1211]

Biological Context

Sinensetin is a polymethoxylated flavone that is present in the Southeast Asian medical plant O. stamineus, as well as in orange oil. It has been shown to enhance adipogenesis and lipolysis by increasing cAMP levels in 3T3-L1 cells.1 Sinensetin is also reported to inhibit α-glucosidase and α-amylase activity in vitro, indicating its potential usefulness in the control of glucose absorption.2 Additionally, sinensetin has been shown to suppress the expression of genes associated with inflammation by regulating IκBα protein levels in LPS-activated macrophages.3

This information has been provided by Cayman Chemical

References

1. Kang, S.-I., Shin, H.-S., and Kim, S.-J. Sinensetin enhances adipogenesis and lipolysis by increasing cyclic adenosine monophosphate levels in 3T3-L1 adipocytes. Bio. Pharm. Bull. 38(4), 552-558 (2015).
2. Mohamed, E.A., Ahmad, M., Ang, L.F., et al. Evaluation of α-glucosidase inhibitory effect of 50% ethanolic standardized extract of Orthosiphon stamineus benth in normal and streptozotocin-induced diabetic rats. Evid-Based Compl. Alt. 2015:754931, (2015).
3. Shin, H.-S., Kang, S.-I., Yoon, S.-A., et al. Sinensetin attenuates LPS-induced inflammation by regulating the protein level of IκB-α. Biosci. Biotechnol. Biochem. 76(4), 847-849 (2012).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Viridiplantae (#33090)
Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)
LKMNXYDUQXAUCZ-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(27-14)10-17(24-3)19(25-4)20(18)26-5/h6-10H,1-5H3
SMILES (Click to copy)
C1(OC)=CC2OC(C3C=CC(OC)=C(OC)C=3)=CC(=O)C=2C(OC)=C1OC

Other Databases

KEGG ID
C10186
HMDB ID
HMDB0036633
CHEBI ID
9159
METABOLOMICS ID
FL3FECNS0024
PubChem CID
145659
Cayman ID
19751

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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Updated at
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