Structure Database (LMSD)

Common Name
Licoflavone C
Systematic Name
8-Prenylapigenin
Synonyms
  • 5,7,4'-Trihydroxy-8-prenylflavone
LM ID
LMPK12110422
Formula
C20H18O5
Exact Mass
Calculate m/z
338.115425
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Flavones and Flavonols [PK1211]

Biological Context

Licoflavone C is a prenylated flavone that has been found in G. ephedroides and has diverse biological activities.1,2,3 It induces estrogen receptor-dependent gene expression in S. cerevisiae expressing human estrogen receptor α (ERα) in a reporter assay when used at a concentration of 0.1 µM.1 Licoflavone C inhibits LPS-induced production of nitric oxide (NO) in RAW 264.7 macrophages (IC50 = 20.4 µM).2 It is active against E. coli, P. aeruginosa, and various strains of Candida (MICs = 7.81-15.62 µg/ml) and is cytotoxic to HepG2 cells (IC50 = 9 µg/ml).3

This information has been provided by Cayman Chemical

References

1. Garritano, S., Pinto, B., Giachi, I., et al. Assessment of estrogenic activity of flavonoids from Mediterranean plants using an in vitro short-term test. Phytomedicine 12(1-2), 143-147 (2005).
2. Han, A.-R., Kang, Y.-J., Windono, T., et al. Prenylated flavonoids from the heartwood of Artocarpus communis with inhibitory activity on lipopolysaccharide-induced nitric oxide production. J. Nat. Prod. 69(4), 719-721 (2006).
3. Edziri, H., Mastouri, M., Mahjoub, M.A., et al. Antibacterial, antifungal and cytotoxic activities of two flavonoids from Retama raetam flowers. Molecules 17(6), 7284-7293 (2012).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
MEHHCBRCXIDGKZ-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C20H18O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9-10,21-23H,8H2,1-2H3
SMILES (Click to copy)
C1(O)=C(C/C=C(/C)\C)C2OC(C3C=CC(O)=CC=3)=CC(=O)C=2C(O)=C1

Other Databases

METABOLOMICS ID
FL3FAANP0003
PubChem CID
10246505
Cayman ID
35031

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 3
Aromatic Rings 3
Rotatable Bonds 3
Van der Waals Molecular Volume 304.97
Topological Polar Surface Area 90.90
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 4.99
Molar Refractivity 96.16

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Created at
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Updated at
9th Jun 2022