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Literature summary for 1.13.11.34 extracted from

  • Khayrullina, V.R.; Taipov, I.A.; Veselovsky, A.V.; Shcherbinin, D.S.; Gerchikov, A.Y.
    New inhibitors of 5-lipoxygenase catalytic activity based on 2-(3-methylphenyl)propanoic acid and 4-substituted morpholine derivatives (2014), Biochemistry (Moscow), 79, 376-384 .
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(2,4-dihydroxyphenyl)[3-(1-[hydroxy[(3,4,5-trihydroxyphenyl)methyl]amino]ethyl)phenyl]methanone
-
Homo sapiens
(2,4-dihydroxyphenyl)[3-(1-[hydroxy[(4-hydroxyphenyl)methyl]amino]ethyl)phenyl]methanone
-
Homo sapiens
2-(3-acetylphenyl)propanoic acid
-
Homo sapiens
2-(3-benzoylphenyl)propanoic acid
-
Homo sapiens
2-(3-phenoxyphenyl)propanoic acid
-
Homo sapiens
2-methyl-3-[(morpholine-4-carbonyl)amino]-3-oxopropanoic acid
-
Homo sapiens
2-[3-(2-methylpropanoyl)phenyl]propanoic acid
-
Homo sapiens
2-[3-(morpholine-4-carbonyl)phenyl]propanoic acid
-
Homo sapiens
2-[3-[(4-hydroxyphenyl)carbamoyl]phenyl]propanoic acid
-
Homo sapiens
2-[3-[hydroxy(phenyl)amino]phenyl]propanoic acid
-
Homo sapiens
2-[4'-[(morpholin-4-yl)sulfanyl][1,1'-biphenyl]-3-yl]propanoic acid
-
Homo sapiens
2-[4-(morpholine-4-carbonyl)phenyl]propanoic acid
-
Homo sapiens
3-(1-carboxyethyl)benzoic acid
-
Homo sapiens
4-[(hydroxy[1-[3'-(morpholin-4-yl)[1,1'-biphenyl]-3-yl]ethyl]amino)methyl]phenol
-
Homo sapiens
4-[[hydroxy(2-methyl-1-[3-[(morpholin-4-yl)oxy]phenyl]propyl)amino]methyl]phenol
-
Homo sapiens
5-[[hydroxy(2-methyl-1-[3-[(morpholin-4-yl)oxy]phenyl]propyl)amino]methyl]benzene-1,2,3-triol
-
Homo sapiens
arachidonate substrate inhibition Homo sapiens
additional information synthesis and evaluation of inhibitors of 5-lipoxygenase catalytic activity based on 2-(3-methylphenyl)propanoic acid and 4-substituted morpholine derivatives, inhibitor molecular docking in the active site of 5-LOX, overview. 2-(3-benzoylphenyl)propanoic acid is an active component of the nonsteroidal antiinflammatory drug ketoprofen Homo sapiens
[3-(1-[hydroxy[(3,4,5-trihydroxyphenyl)methyl]amino]ethyl)phenyl](morpholin-4-yl)methanone
-
Homo sapiens
[3-(1-[hydroxy[(4-hydroxyphenyl)methyl]amino]ethyl)phenyl](morpholin-4-yl)methanone
-
Homo sapiens
[3-(bromocarbonyl)phenyl](morpholin-4-yl)acetic acid
-
Homo sapiens

Metals/Ions

Metals/Ions Comment Organism Structure
Fe2+ a nonheme Fe2+ ion coordinated by three polar histidines H372, H550, and H367, the carbonyl group of N554, the carboxylic group of the C-terminal I673, and a water moleculein the active site, overview. On interaction with the active site, the ligands replaces the H2O molecule Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
arachidonate + O2 Homo sapiens
-
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens P09917
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
arachidonate + O2
-
Homo sapiens (5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
?

Synonyms

Synonyms Comment Organism
5-lipoxygenase
-
Homo sapiens
5-LOX
-
Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00011
-
4-[[hydroxy(2-methyl-1-[3-[(morpholin-4-yl)oxy]phenyl]propyl)amino]methyl]phenol pH and temperature not specified in the publication Homo sapiens
0.00013
-
2-[4'-[(morpholin-4-yl)sulfanyl][1,1'-biphenyl]-3-yl]propanoic acid pH and temperature not specified in the publication Homo sapiens
0.00018
-
[3-(1-[hydroxy[(4-hydroxyphenyl)methyl]amino]ethyl)phenyl](morpholin-4-yl)methanone pH and temperature not specified in the publication Homo sapiens
0.00032
-
5-[[hydroxy(2-methyl-1-[3-[(morpholin-4-yl)oxy]phenyl]propyl)amino]methyl]benzene-1,2,3-triol pH and temperature not specified in the publication Homo sapiens
0.00042
-
2-[3-[(4-hydroxyphenyl)carbamoyl]phenyl]propanoic acid pH and temperature not specified in the publication Homo sapiens
0.00059
-
[3-(1-[hydroxy[(3,4,5-trihydroxyphenyl)methyl]amino]ethyl)phenyl](morpholin-4-yl)methanone pH and temperature not specified in the publication Homo sapiens
0.00071
-
(2,4-dihydroxyphenyl)[3-(1-[hydroxy[(3,4,5-trihydroxyphenyl)methyl]amino]ethyl)phenyl]methanone pH and temperature not specified in the publication Homo sapiens
0.0009
-
(2,4-dihydroxyphenyl)[3-(1-[hydroxy[(4-hydroxyphenyl)methyl]amino]ethyl)phenyl]methanone pH and temperature not specified in the publication Homo sapiens
0.00136
-
2-(3-benzoylphenyl)propanoic acid pH and temperature not specified in the publication Homo sapiens
0.00267
-
2-(3-phenoxyphenyl)propanoic acid pH and temperature not specified in the publication Homo sapiens
0.00515
-
4-[(hydroxy[1-[3'-(morpholin-4-yl)[1,1'-biphenyl]-3-yl]ethyl]amino)methyl]phenol pH and temperature not specified in the publication Homo sapiens
0.0057
-
2-[3-[hydroxy(phenyl)amino]phenyl]propanoic acid pH and temperature not specified in the publication Homo sapiens
0.00734
-
2-[3-(2-methylpropanoyl)phenyl]propanoic acid pH and temperature not specified in the publication Homo sapiens
0.00734
-
2-[3-(morpholine-4-carbonyl)phenyl]propanoic acid pH and temperature not specified in the publication Homo sapiens
0.0112
-
2-[4-(morpholine-4-carbonyl)phenyl]propanoic acid pH and temperature not specified in the publication Homo sapiens
0.016
-
2-(3-acetylphenyl)propanoic acid pH and temperature not specified in the publication Homo sapiens
0.0398
-
arachidonate pH and temperature not specified in the publication Homo sapiens
0.0398
-
[3-(bromocarbonyl)phenyl](morpholin-4-yl)acetic acid pH and temperature not specified in the publication Homo sapiens
0.0455
-
2-methyl-3-[(morpholine-4-carbonyl)amino]-3-oxopropanoic acid pH and temperature not specified in the publication Homo sapiens
0.17
-
3-(1-carboxyethyl)benzoic acid pH and temperature not specified in the publication Homo sapiens

General Information

General Information Comment Organism
additional information the active site of 5-LOX contains a nonheme Fe2+ ion coordinated by three polar histidines H372, H550, and H367, the carbonyl group of N554, the carboxylic group of the C-terminal I673, and a water molecule, modeling of the active site of 5-LOX. A hydrophobic cleft formed by nonpolar amino acids L414, I415, L368, L607, L420, F421, F177, A424, A410, A603, V604, and P569 can also play an important role in orientation of ligands in the active site of 5-LOX Homo sapiens