Structure Database (LMSD)
Common Name
Diosmetin
Systematic Name
5,7,3'-Trihydroxy-4'-methoxyflavone
Synonyms
- 4'-Methylluteolin
3D model of Diosmetin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Diosmetin is a flavonoid that has been found in citrus fruits and has diverse biological activities.1,2,3,4 It inhibits the cytochrome P450 (CYP) isoforms CYP1A1 and CYP1B1 (Kis = 89 and 16 nM, respectively).1 Diosmetin prevents increases in erythrocyte reactive oxygen species (ROS) and malondialdehyde (MDA) levels induced by AAPH in a concentration-dependent manner.2 It reduces tumor growth and tumor blood vessel density in a B16/F10 murine melanoma model when administered at a dose of 1 mg/kg twice per day.3 Diosmetin (0.5 mg/kg) inhibits lung goblet cell hyperplasia and collagen deposition and decreases the number of eosinophils and neutrophils in bronchoalveolar lavage fluid (BALF) in a mouse model of chronic asthma induced by ovalbumin.4
This information has been provided by Cayman Chemical
References
1. Ge, A., Liu, Y., Zeng, X., et al. Effect of diosmetin on airway remodeling in a murine model of chronic asthma. Acta Biochim. Biophys. Sin. (Shanghai) 47(8), 604-611 (2015).
3. Liao, W., Ning, Z., Chen, L., et al. Intracellular antioxidant detoxifying effects of diosmetin on 2,2-azobis(2-amidinopropane) dihydrochloride (AAPH)-induced oxidative stress through inhibition of reactive oxygen species generation. J. Agric. Food Chem. 62(34), 8648-8654 (2014).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
MBNGWHIJMBWFHU-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3
SMILES (Click to copy)
C1(O)=CC2OC(C3C=CC(OC)=C(O)C=3)=CC(=O)C=2C(O)=C1
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID
PDB ID
Calculated Physicochemical Properties
Heavy Atoms
22
Rings
3
Aromatic Rings
3
Rotatable Bonds
2
Van der Waals Molecular Volume
247.20
Topological Polar Surface Area
100.13
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
6
logP
3.49
Molar Refractivity
79.57
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