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Literature summary extracted from

  • Seyedi, S.M.; Jafari, Z.; Attaran, N.; Sadeghian, H.; Saberi, M.R.; Riazi, M.M.
    Design, synthesis and SAR studies of 4-allyoxyaniline amides as potent 15-lipoxygenase inhibitors (2009), Bioorg. Med. Chem., 17, 1614-1622.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.13.11.12 4-(allyloxy)phenyl benzoate
-
 Glycine max
1.13.11.12 4-allylphenyl benzoate
-
 Glycine max
1.13.11.12 estragol
-
 Glycine max
1.13.11.12 eugenol
-
 Glycine max
1.13.11.12 eugenyl benzoate
-
 Glycine max
1.13.11.12 methyleugenol
-
 Glycine max
1.13.11.12 additional information 4-allyloxyaniline amides designed as inhibitors on the basis of eugenol and esteragol structures. Compounds are docked in SLO active site and fixed by hydrogen bonding with two conserved His513 and Gln716. Molecular volume of the amide moiety is a major factor in inhibitory potency variation of the synthetic amides, where the hydrogen bonding of the amide group can involve in the activity of the inhibitors Glycine max
1.13.11.12 N1-(4-(allyloxy) phenyl)-1-admantancarboxamide best inhibitor Glycine max
1.13.11.12 N1-(4-(allyloxy) phenyl)-1-cyclobutanecarboxamide
-
 Glycine max
1.13.11.12 N1-(4-(allyloxy) phenyl)-1-cyclohexanecarboxamide
-
 Glycine max
1.13.11.12 N1-(4-(allyloxy) phenyl)-1-cyclopantanecarboxamide
-
 Glycine max
1.13.11.12 N1-(4-(allyloxy) phenyl)-1-cyclopropanecarboxamide
-
 Glycine max
1.13.11.12 N1-(4-(allyloxy) phenyl)-2-methylpropanamide
-
 Glycine max
1.13.11.12 N1-(4-(allyloxy) phenyl)-3-chlorobenzamide
-
 Glycine max
1.13.11.12 N1-(4-(allyloxy) phenyl)-3-fluorobenzamide
-
 Glycine max
1.13.11.12 N1-(4-(allyloxy) phenyl)-3-methoxybenzamide
-
 Glycine max
1.13.11.12 N1-(4-(allyloxy) phenyl)-3-methylbenzamide
-
 Glycine max
1.13.11.12 N1-(4-(allyloxy) phenyl)-4-chlorobenzamide
-
 Glycine max
1.13.11.12 N1-(4-(allyloxy) phenyl)-4-fluorobenzamide
-
 Glycine max
1.13.11.12 N1-(4-(allyloxy) phenyl)-4-methoxybenzamide
-
 Glycine max
1.13.11.12 N1-(4-(allyloxy) phenyl)-4-methylbenzamide
-
 Glycine max
1.13.11.12 N1-(4-(allyloxy) phenyl)benzamide
-
 Glycine max

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.13.11.12 Fe3+ the allyloxy group of compounds is oriented towards the Fe(3+)-OH moiety in the active site of the enzyme Glycine max

Organism

EC Number Organism UniProt Comment Textmining
1.13.11.12 Glycine max
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.13.11.12 linoleic acid + O2
-
 Glycine max ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.13.11.12 SLO
-
 Glycine max

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.13.11.12 0.00067
-
 pH 9.0, 20°C Glycine max N1-(4-(allyloxy) phenyl)-1-admantancarboxamide
1.13.11.12 0.0022
-
 pH 9.0, 20°C Glycine max N1-(4-(allyloxy) phenyl)-1-cyclobutanecarboxamide
1.13.11.12 0.0033
-
 pH 9.0, 20°C Glycine max N1-(4-(allyloxy) phenyl)benzamide
1.13.11.12 0.0038
-
 pH 9.0, 20°C Glycine max N1-(4-(allyloxy) phenyl)-4-fluorobenzamide
1.13.11.12 0.0041
-
 pH 9.0, 20°C Glycine max N1-(4-(allyloxy) phenyl)-1-cyclopantanecarboxamide
1.13.11.12 0.0056
-
 pH 9.0, 20°C Glycine max N1-(4-(allyloxy) phenyl)-3-fluorobenzamide
1.13.11.12 0.0061
-
 pH 9.0, 20°C Glycine max N1-(4-(allyloxy) phenyl)-1-cyclopropanecarboxamide
1.13.11.12 0.0062
-
 pH 9.0, 20°C Glycine max 4-(allyloxy)phenyl benzoate
1.13.11.12 0.0064
-
 pH 9.0, 20°C Glycine max N1-(4-(allyloxy) phenyl)-1-cyclohexanecarboxamide
1.13.11.12 0.0067
-
 pH 9.0, 20°C Glycine max 4-allylphenyl benzoate
1.13.11.12 0.0067
-
 pH 9.0, 20°C Glycine max N1-(4-(allyloxy) phenyl)-3-methylbenzamide
1.13.11.12 0.007
-
 pH 9.0, 20°C Glycine max eugenyl benzoate
1.13.11.12 0.0081
-
 pH 9.0, 20°C Glycine max N1-(4-(allyloxy) phenyl)-3-chlorobenzamide
1.13.11.12 0.0088
-
 pH 9.0, 20°C Glycine max N1-(4-(allyloxy) phenyl)-4-chlorobenzamide
1.13.11.12 0.0101
-
 pH 9.0, 20°C Glycine max N1-(4-(allyloxy) phenyl)-4-methylbenzamide
1.13.11.12 0.0129
-
 pH 9.0, 20°C Glycine max N1-(4-(allyloxy) phenyl)-2-methylpropanamide
1.13.11.12 0.0138
-
 pH 9.0, 20°C Glycine max N1-(4-(allyloxy) phenyl)-4-methoxybenzamide
1.13.11.12 0.017
-
 pH 9.0, 20°C Glycine max N1-(4-(allyloxy) phenyl)-3-methoxybenzamide
1.13.11.12 0.0382
-
 pH 9.0, 20°C Glycine max eugenol
1.13.11.12 0.0641
-
 pH 9.0, 20°C Glycine max estragol
1.13.11.12 0.0961
-
 pH 9.0, 20°C Glycine max methyleugenol