Structure Database (LMSD)

Systematic Name
7,4'-Dihydroxyflavone
Synonyms
LM ID
LMPK12110035
Formula
C15H10O4
Exact Mass
Calculate m/z
254.05791
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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View NP-MRD ID(NMR) spectrum

Classification

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

Biological Context

7,4’-Dihydroxyflavone (7,4'-DHF) is a flavonoid that has been found in G. uralensis and has diverse biological activities.1,2,3 It inhibits the activity of rat lens aldose reductase (IC50 = 3.8 µM).1 7,4'-DHF is active against L. donovani amastigotes and T. b. rhodesiense, but not T. cruzi, trypomastigotes (IC50s = 11.1, 6.9, and >30 µg/ml, respectively).2 It scavenges DPPH radicals when used at a concentration of 15 µM.3

This information has been provided by Cayman Chemical

References

1. Matsuda, H., Morikawa, T., Toguchida, I., et al. Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity. Chem. Pharm. Bull. (Tokyo) 50(6), 788-795 (2002).
2. Tasdemir, D., Kaiser, M., Brun, R., et al. Antitrypanosomal and antileishmanial activities of flavonoids and their analogues: In vitro, in vivo, structure-activity relationship, and quantitative structure-activity relationship studies. Antimicrob. Agents Chemother. 50(4), 1352-1364 (2006).
3. Cotelle, N., Bernier, J.-L., Catteau, J.-P., et al. Antioxidant properties of hydroxy-flavones. Free Radic. Biol. Med. 20(1), 35-43 (1996).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
LCAWNFIFMLXZPQ-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-8,16-17H
SMILES (Click to copy)
C1(O)=CC2OC(C3C=CC(O)=CC=3)=CC(=O)C=2C=C1

Other Databases

KEGG ID
C12123
CHEBI ID
29503
METABOLOMICS ID
FL3F1ANS0001
PubChem CID
5282073
Cayman ID
35491

Calculated Physicochemical Properties

Heavy Atoms 19
Rings 3
Aromatic Rings 3
Rotatable Bonds 1
Van der Waals Molecular Volume 212.32
Topological Polar Surface Area 70.67
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 3.77
Molar Refractivity 71.36

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Updated at
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