Structure Database (LMSD)

Systematic Name
7-Methoxyflavone
Synonyms
LM ID
LMPK12110021
Formula
C16H12O3
Exact Mass
Calculate m/z
252.078645
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

7-Methoxyflavone is a flavone that has been found in Z. brasiliensis and has diverse biological activities.1,2,3,4 It inhibits aromatase (IC50 = 1.9 µM in a cell-free assay) and LPS-induced nitric oxide (NO) production by 17.74% in RAW 264.7 macrophages when used at a concentration of 20 µM.1,2 7-Methoxyflavone activates androgen and/or glucocorticoid receptor transcriptional activity in a reporter assay and has antinociceptive effects in the acetic acid-induced writhing test in mice (ED50 = 82.5 µmol/kg).3,4

This information has been provided by Cayman Chemical

References

1. Nishizaki, Y., Ishimoto, Y., Hotta, Y., et al. Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assay. Bioorg. Med. Chem. Lett. 19(16), 4706-4710 (2009).
2. An, J.-Y., Lee, H.-H., Shin, J.-S., et al. Identification and structure activity relationship of novel flavone derivatives that inhibit the production of nitric oxide and PGE2 in LPS-induced RAW 264.7 cells. Bioorg. Med. Chem. Lett. 27(11), 2613-2616 (2017).
3. da Silva, A.D.S., Cavalcante-Silva, L.H.A., da Matta, C.B.B., et al. Antinociceptive effect of 7-methoxyflavone isolated from Zornia brasiliensis. Nat. Prod. Res. 27(18), 1695-1699 (2013).
4. Ta, N., and Walle, T. Aromatase inhibition by bioavailable methylated flavones. J. Steroid. Biochem. Mol. Biol. 107(1-2), 127-129 (2007).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
QKNDCRMJDZLFEG-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H12O3/c1-18-12-7-8-13-14(17)10-15(19-16(13)9-12)11-5-3-2-4-6-11/h2-10H,1H3
SMILES (Click to copy)
C1(OC)=CC2OC(C3C=CC=CC=3)=CC(=O)C=2C=C1

Other Databases

CHEBI ID
192603
METABOLOMICS ID
FL3F19NS0001
PubChem CID
466268
Cayman ID
33497

Calculated Physicochemical Properties

Heavy Atoms 19
Rings 3
Aromatic Rings 3
Rotatable Bonds 2
Van der Waals Molecular Volume 220.83
Topological Polar Surface Area 39.44
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 3
logP 4.37
Molar Refractivity 74.58

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Updated at
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