Structure Database (LMSD)

Common Name
Flavone
Systematic Name
Synonyms
LM ID
LMPK12110097
Formula
C15H10O2
Exact Mass
Calculate m/z
222.06808
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View BMRB ID(NMR) spectrum
View NP-MRD ID(NMR) spectrum
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

Flavone is a polyketide synthase-derived polyphenolic flavonoid that has been found in various edible plants.1 It is the backbone scaffold of many pharmacologically active flavonoids, including luteolin , apigenin , and wogonin .1,2 Flavone reduces proliferation of (EC50 = 54.8 µM), and induces apoptosis in, HT-29 colon cancer cells.1 It enhances dengue virus type 2 (DENV-2) infectivity in Vero cells when used at a concentration of 100 µg/ml.2

This information has been provided by Cayman Chemical

References

1. Wenzel, U., Kuntz, S., Brendel, M.D., et al. Dietary flavone is a potent apoptosis inducer in human colon carcinoma cells. Cancer Res. 60(14), 3823-3831 (2000).
2. Zandi, K., Lani, R., Wong, P.-F., et al. Flavone enhances dengue virus type-2 (NGC strain) infectivity and replication in Vero cells. Molecules 17(3), 2437-2445 (2012).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
VHBFFQKBGNRLFZ-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C15H10O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10H
SMILES (Click to copy)
C1=CC2OC(C3C=CC=CC=3)=CC(=O)C=2C=C1

Other Databases

Wikipedia
Flavone
KEGG ID
C10043
HMDB ID
HMDB0003075
CHEBI ID
42491
METABOLOMICS ID
FL3F99NS0001
PubChem CID
10680
Cayman ID
34028
PDB ID
FLN
GuidePharm ID
409

Calculated Physicochemical Properties

Heavy Atoms 17
Rings 3
Aromatic Rings 3
Rotatable Bonds 1
Van der Waals Molecular Volume 194.74
Topological Polar Surface Area 30.21
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 2
logP 4.36
Molar Refractivity 68.03

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Created at
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Updated at
9th Jun 2022