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Literature summary extracted from

  • Sadeghian, H.; Attaran, N.; Jafari, Z.; Saberi, M.R.; Pordel, M.; Riazi, M.M.
    Design and synthesis of 4-methoxyphenylacetic acid esters as 15-lipoxygenase inhibitors and SAR comparative studies of them (2009), Bioorg. Med. Chem., 17, 2327-2335.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.13.11.12 1-(4-methoxyphenyl)-2-butanone
-
 Glycine max
1.13.11.12 1-(4-methoxyphenyl)acetone
-
 Glycine max
1.13.11.12 1-methoxy-4-(2-ethylallyl)benzene
-
 Glycine max
1.13.11.12 1-methoxy-4-(2-methylallyl)benzene
-
 Glycine max
1.13.11.12 4-Methoxyphenylacetic acid
-
 Glycine max
1.13.11.12 butyl 2-(4-methoxyphenyl)acetate
-
 Glycine max
1.13.11.12 cyclohexyl 2-(4-methoxyphenyl)acetate
-
 Glycine max
1.13.11.12 cyclopentyl 2-(4-methoxyphenyl)acetate
-
 Glycine max
1.13.11.12 esteragol
-
 Glycine max
1.13.11.12 ethyl 2-(4-methoxyphenyl)acetate
-
 Glycine max
1.13.11.12 eugenol
-
 Glycine max
1.13.11.12 hexyl 2-(4-methoxyphenyl)acetate
-
 Glycine max
1.13.11.12 isobutyl 2-(4-methoxyphenyl)acetate
-
 Glycine max
1.13.11.12 isopropyl 2-(4-methoxyphenyl)acetate
-
 Glycine max
1.13.11.12 methyleugenol
-
 Glycine max
1.13.11.12 additional information 4-methoxyphenylacetic acid esters designed as inhibitors on the basis of eugenol and esteragol structures are docked in SLO active site and show that carbonyl group of compounds is oriented toward the FeIII-OH moiety in the active site of enzyme and fixed by hydrogen bonding with hydroxyl group. Lipophilic interaction of ligand-enzyme is in charge of inhibiting the enzyme activity. Is not inhibited by 6-methoxy-2-methylene-1,2,3,4-tetrahydronaphthalene Glycine max
1.13.11.12 pentyl 2-(4-methoxyphenyl)acetate long chain and lipophile 4-methoxyphenylacetic acid ester, behaves as the best SLO inhibitor Glycine max
1.13.11.12 propyl 2-(4-methoxyphenyl)acetate
-
 Glycine max
1.13.11.12 sec-butyl 2-(4-methoxyphenyl)acetate
-
 Glycine max
1.13.11.12 tert-butyl 2-(4-methoxyphenyl)acetate
-
 Glycine max

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.13.11.12 Fe3+ the carbonyl group of inhibitors is oriented towards the Fe(III)-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 0.0019
-
 pH 9.0, 20°C Glycine max pentyl 2-(4-methoxyphenyl)acetate
1.13.11.12 0.0038
-
 pH 9.0, 20°C Glycine max butyl 2-(4-methoxyphenyl)acetate
1.13.11.12 0.0116
-
 pH 9.0, 20°C Glycine max propyl 2-(4-methoxyphenyl)acetate
1.13.11.12 0.032
-
-
 Glycine max ethyl 2-(4-methoxyphenyl)acetate
1.13.11.12 0.033
-
 pH 9.0, 20°C Glycine max 1-(4-methoxyphenyl)-2-butanone
1.13.11.12 0.0344
-
 pH 9.0, 20°C Glycine max isopropyl 2-(4-methoxyphenyl)acetate
1.13.11.12 0.035
-
 pH 9.0, 20°C Glycine max hexyl 2-(4-methoxyphenyl)acetate
1.13.11.12 0.0357
-
 pH 9.0, 20°C Glycine max sec-butyl 2-(4-methoxyphenyl)acetate
1.13.11.12 0.0382
-
 pH 9.0, 20°C Glycine max eugenol
1.13.11.12 0.0387
-
 pH 9.0, 20°C Glycine max tert-butyl 2-(4-methoxyphenyl)acetate
1.13.11.12 0.043
-
 pH 9.0, 20°C Glycine max 1-(4-methoxyphenyl)acetone
1.13.11.12 0.0562
-
 pH 9.0, 20°C Glycine max 4-Methoxyphenylacetic acid
1.13.11.12 0.0565
-
 pH 9.0, 20°C Glycine max cyclopentyl 2-(4-methoxyphenyl)acetate
1.13.11.12 0.064
-
 pH 9.0, 20°C Glycine max cyclohexyl 2-(4-methoxyphenyl)acetate
1.13.11.12 0.0641
-
 pH 9.0, 20°C Glycine max esteragol
1.13.11.12 0.0881
-
 pH 9.0, 20°C Glycine max isobutyl 2-(4-methoxyphenyl)acetate
1.13.11.12 0.0961
-
 pH 9.0, 20°C Glycine max methyleugenol
1.13.11.12 0.137
-
 pH 9.0, 20°C Glycine max 1-methoxy-4-(2-methylallyl)benzene
1.13.11.12 0.145
-
 pH 9.0, 20°C Glycine max 1-methoxy-4-(2-ethylallyl)benzene