Structure Database (LMSD)

Common Name
chrysin 5,7-dimethyl ether
Systematic Name
5,7-Dimethoxyflavone
Synonyms
LM ID
LMPK12110188
Formula
C17H14O4
Exact Mass
Calculate m/z
282.08921
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

5,7-Dimethoxyflavone (5,7-DMF) is a flavonoid that has been found in B. pandurata and has diverse biological activities.1,2,3 It induces the production of reactive oxygen species (ROS), cell cycle arrest at the G1 phase, and apoptosis in HepG2 liver cancer cells when used at concentrations of 10, 25, and 50 µM.2 In vivo, 5,7-DMF (75-150 mg/kg) reduces exudate volume and inhibits prostaglandin production in a rat model of carrageenan-induced pleurisy.1 It reduces rectal temperature in a rat model of yeast-induced hyperthermia. 5,7-DMF also reduces serum triglyceride, total cholesterol, and LDL levels, as well as increases serum insulin levels and reduces blood glucose levels in a rat model of diabetes induced by streptozotocin (STZ).3

This information has been provided by Cayman Chemical

References

1. Xie, Y., Zhang, Y., and Su, X. Antidiabetic and hypolipidemic effects of 5,7-dimethoxyflavone in streptozotocin-induced diabetic rats. Med. Sci. Monit. 25, 9893-9901 (2019).
2. Panthong, A., Tassaneeyakul, W., Kanjanapothi, D., et al. Anti-inflammatory activity of 5,7-dimethoxyflavone. Planta Med. 55(2), 133-136 (1989).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
JRFZSUMZAUHNSL-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C17H14O4/c1-19-12-8-15(20-2)17-13(18)10-14(21-16(17)9-12)11-6-4-3-5-7-11/h3-10H,1-2H3
SMILES (Click to copy)
C1(OC)=CC2OC(C3C=CC=CC=3)=CC(=O)C=2C(OC)=C1

Other Databases

KEGG ID
C10029
HMDB ID
HMDB0036620
CHEBI ID
3684
METABOLOMICS ID
FL3FA9NS0001
PubChem CID
88881
Cayman ID
37361

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 3
Aromatic Rings 3
Rotatable Bonds 3
Van der Waals Molecular Volume 246.92
Topological Polar Surface Area 48.67
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 4
logP 4.38
Molar Refractivity 81.13

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Updated at
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