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Structure Database (LMSD)

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Common Name

Chrysin

Systematic Name

5,7-Dihydroxyflavone

Synonyms

LM ID

LMPK12110189

Formula

C₁₅H₁₀O₄

Exact Mass

Calculate m/z

254.05791

Status

Curated

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Classification

Category

Main Class

Sub Class

Polyketides [PK]

Flavonoids [PK12]

Flavones and Flavonols [PK1211]

Biological Context

Chrysin is a natural flavonoid with antioxidant, anti-inflammatory, and anticancer properties. It blocks COX-2 gene expression, PGE2 production, and hydroxyl radical formation in LPS-induced RAW 264.7 cells.^1,2 Chrysin inhibits insulin-induced HIF-1α expression (~50% at 10 µM) in human prostate cancer DU145 cells and blocks DU145 xenograft-induced angiogenesis in vivo.³ In a mouse model of ischemia/reperfusion injury, chrysin decreased pro-inflammatory gene expression and oxidative stress, resulting in a reduction of infarct volume and neurological defects.⁴

This information has been provided by Cayman Chemical

References

1. Yao, Y., Chen, L., Xiao, J., et al. Chrysin protects against focal cerebral ischemia/reperfusion injury in mice through attenuation of oxidative stress and inflammation. Int. J. Mol. Sci. 15(11), 20913-20926 (2014).

2. Fu, B., Xue, J., Li, Z., et al. Chrysin inhibits expression of hypoxia-inducible factor-1α through reducing hypoxia-inducible factor-1α stability and inhibiting its protein synthesis. Mol. Cancer Ther. 6(1), 220-226 (2007).

3. Harris, G.K., Qian, Y., Leonard, S.S., et al. Luteolin and chrysin differentially inhibit cyclooxygenase-2 expression and scavenge reactive oxygen species but similarly inhibit prostaglandin-E2 formation in RAW 264.7 cells. J. Nutr. 136(6), 1517-1521 (2006).

4. Woo, K.J., Jeong, Y.J., Inoue, H., et al. Chrysin suppresses lipopolysaccharide-induced cyclooxygenase-2 expression through the inhibition of nuclear factor for IL-6 (NF-IL6) DNA-binding activity. FEBS Lett. 579(3), 705-711 (2005).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Viridiplantae (#33090)

Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)

RTIXKCRFFJGDFG-UHFFFAOYSA-N

InChi (Click to copy)

InChI=1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H

SMILES (Click to copy)

C1(O)=CC2OC(C3C=CC=CC=3)=CC(=O)C=2C(O)=C1

Other Databases

Wikipedia

KEGG ID

HMDB ID

CHEBI ID

METABOLOMICS ID

PubChem CID

Cayman ID

PDB ID

GuidePharm ID

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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