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Structure Database (LMSD)

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Common Name

Diosmetin

Systematic Name

5,7,3'-Trihydroxy-4'-methoxyflavone

Synonyms

4'-Methylluteolin

LM ID

LMPK12110824

Formula

C₁₆H₁₂O₆

Exact Mass

Calculate m/z

300.06339

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category

Main Class

Sub Class

Polyketides [PK]

Flavonoids [PK12]

Flavones and Flavonols [PK1211]

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).

2. Choi, J., Lee, D.H., Park, S.Y., et al. Diosmetin inhibits tumor development and block tumor angiogenesis in skin cancer. Biomed. Pharmacother. 117, 109091 (2019).

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).

4. Androutsopoulos, V.P., Papakyriakou, A., Vourloumis, D., et al. Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids. Bioorg. Med. Chem. 19(9), 2842-2849 (2011).

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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