UFM24   Click here for help

GtoPdb Ligand ID: 9878

Immunopharmacology Ligand
Comment: UFM24 is a flavone extracted from the Annonaceae Uvaria flexuosa [2]. It exhibits anti-inflammatory effects that are mediated by inhibition of PDE4 cAMP phosphodiesterases in neutrophils. The anti-inflammatory activities (inhibition of superoxide anion generation and elastase release from human neutrophils in response to fMLP) of seco-cyclohexenes and cyclohexenes isolated from Uvaria flexuosa leaves are reported by Hsu et al. (2016) [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 68.9
Molecular weight 298.08
XLogP 4.04
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1cc2oc(cc(=O)c2c(c1O)OC)c1ccccc1
Isomeric SMILES COc1cc2oc(cc(=O)c2c(c1O)OC)c1ccccc1
InChI InChI=1S/C17H14O5/c1-20-14-9-13-15(17(21-2)16(14)19)11(18)8-12(22-13)10-6-4-3-5-7-10/h3-9,19H,1-2H3
InChI Key YLSUKCVZCXUJBF-UHFFFAOYSA-N
References
1. Hsu YM, Wu TY, Du YC, El-Shazly M, Beerhues L, Thang TD, Van Luu H, Hwang TL, Chang FR, Wu YC. (2016)
3-Methyl-4,5-dihydro-oxepine, polyoxygenated seco-cyclohexenes and cyclohexenes from Uvaria flexuosa and their anti-inflammatory activity.
Phytochemistry, 122: 184-192. [PMID:26732672]
2. Tsai YF, Chu TC, Chang WY, Wu YC, Chang FR, Yang SC, Wu TY, Hsu YM, Chen CY, Chang SH et al.. (2017)
6-Hydroxy-5,7-dimethoxy-flavone suppresses the neutrophil respiratory burst via selective PDE4 inhibition to ameliorate acute lung injury.
Free Radic Biol Med, 106: 379-392. [PMID:28263828]