Structure Database (LMSD)
Common Name
Syringetin
Systematic Name
Synonyms
3D model of Syringetin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Syringetin is a methylated flavonol that has been found in G. biloba and has diverse biological activities.1,2,3 It inhibits α-glucosidase and scavenges radicals in a Trolox equivalent antioxidant capacity (TEAC) assay (IC50s = 36.8 and 12.3 µM, respectively).1,3 Syringetin (50 µM) reduces the proliferation of, induces cell cycle arrest at the G2/M phase in, and decreases cyclin D1 and COX-2 levels in, Caco-2 colorectal adenocarcinoma cells.2 It increases the lifespan of C. elegans when used at a concentration of 100 µM.3
This information has been provided by Cayman Chemical
References
2. Gómez-Alonso, S., Collins, V.J., Vauzour, D., et al. Inhibition of colon adenocarcinoma cell proliferation by flavonols is linked to a G2/M cell cycle block and reduction in cyclin D1 expression. Food Chem. 130(3), 493-500 (2012).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
UZMAPBJVXOGOFT-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C17H14O8/c1-23-11-3-7(4-12(24-2)14(11)20)17-16(22)15(21)13-9(19)5-8(18)6-10(13)25-17/h3-6,18-20,22H,1-2H3
SMILES (Click to copy)
C1(O)=CC2OC(C3C=C(OC)C(O)=C(OC)C=3)=C(O)C(=O)C=2C(O)=C1
Other Databases
Wikipedia
KEGG ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
25
Rings
3
Aromatic Rings
3
Rotatable Bonds
3
Van der Waals Molecular Volume
282.08
Topological Polar Surface Area
129.59
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
8
logP
3.20
Molar Refractivity
87.79
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Updated at
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