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Literature summary for 1.1.1.188 extracted from

  • Koda, N.; Tsutsui, Y.; Niwa, H.; Ito, S.; Woodward, D.F.; Watanabe, K.
    Synthesis of prostaglandin F ethanolamide by prostaglandin F synthase and identification of Bimatoprost as a potent inhibitor of the enzyme: new enzyme assay method using LC/ESI/MS (2004), Arch. Biochem. Biophys., 424, 128-136.
    View publication on PubMed
Search for more literature for 1.1.1.188

Cloned(Commentary)

Cloned (Comment) Organism
expressed in Escherichia coli HB101 cells Homo sapiens
expression Escherichia coli HB101 Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide bimatoprost Homo sapiens
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid ONO1370 Homo sapiens
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid ONO1349 Homo sapiens
(5Z)-7-[(1S,4S,5S,6R)-2-methyl-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid ONO1373 Homo sapiens
(Z)-7-[(1R,4S,5S,6R)-((E)-6-oct-1-enyl)-2-aza-bicyclo[2.2.1]hept-5-yl]-hept-5-enoic acid inhibition of PGH2 9,11-endoperoxide reductase activity, slight inhibition of prostamide D2 11-ketoreductase and PGD2 11-ketoreductase activity Homo sapiens
(Z)-7-[(1R,4S,5S,6R)-2-methyl-6-((E)-oct-1-enyl)-2-aza-bicyclo[2.2.1]hept-5-yl]-hept-5-enoic acid inhibition of PGH2 9,11-endoperoxide reductase activity, slight inhibition of prostamide D2 11-ketoreductase and PGD2 11-ketoreductase activity, competitive, binds to the active site Homo sapiens
(Z)-7-[(1R,4S,5S,6R)-6-((E)-(S)-3-hydroxy-oct-1-enyl)-2-aza-bicyclo[2.2.1]hept-5-yl]-hept-5-enoic acid inhibition of PGH2 9,11-endoperoxide reductase activity, slight inhibition of prostamide D2 11-ketoreductase and PGD2 11-ketoreductase activity Homo sapiens
bimatoprost ethyl amide analogue of 17-phenyl-trinor PGF2alpha, inhibits all enzyme activities noncompetitively at low concentration, binds to a site different from the active site; potent inhibitor Homo sapiens
ONO1349
-
 Homo sapiens
ONO1370
-
 Homo sapiens
ONO1373
-
 Homo sapiens
Tolrestat inhibition of all 3 enzyme activities, most effective inhibiting the PGD2 11-ketoreductase activity Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-
Homo sapiens P42330
-
-

Purification (Commentary)

Purification (Comment) Organism
-
 Homo sapiens
recombinant enzyme from Escherichia coli, to homogeneity Homo sapiens

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information substrate and product detection by liquid chromatographic-electrospray ionization-mass spectrometry Homo sapiens ?
-
 ?
prostaglandin D2 + NADPH + H+
-
 Homo sapiens prostaglandin 9alpha,11beta-F2 + NADP+
-
 ?
prostaglandin D2 + NADPH + H+
-
 Homo sapiens prostaglandin F2alpha + NADP+
-
 ?
prostaglandin D2 + NADPH + H+
-
 Homo sapiens 9alpha,11beta-prostaglandin F2 + NADP+
-
 ?
prostaglandin D2 ethanolamide + NADPH i.e. prostamide D2 Homo sapiens prostaglandin 9alpha,11beta-F2 ethanolamide + NADP+ i.e. 91lpha,11beta-prostamide F2 ?
prostaglandin H2 + NADPH + H+
-
 Homo sapiens prostaglandin F2alpha + NADP+
-
 ?
prostaglandin H2 + NADPH + H+
-
 Homo sapiens prostaglandin 9alpha,11beta-F2 + NADP+
-
 ?
prostamide D2 + NADPH + H+
-
 Homo sapiens 9alpha,11beta-prostamide F2 + NADP+
-
 ?

Synonyms

Synonyms Comment Organism
PGD2 11-ketoreductase
-
 Homo sapiens
PGF synthase
-
 Homo sapiens
PGH2 9,11-endoperoxide reductase
-
 Homo sapiens
prostaglandin F synthase
-
 Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 PGD2 11-ketoreductase activity assay at Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6.5
-
 PGD2 11-ketoreductase activity assay at Homo sapiens

Cofactor

Cofactor Comment Organism Structure
NADPH
-
 Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.005
-
 recombinant enzyme, using prostaglandin D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
0.005
-
 recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens bimatoprost
0.006
-
 recombinant enzyme, using prostaglandin H2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
0.006
-
 recombinant enzyme, using prostaglandin H2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens bimatoprost
0.06
-
 recombinant enzyme, using prostaglandin H2 2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens ONO1373
0.06
-
 recombinant enzyme, using prostaglandin H2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens (5Z)-7-[(1S,4S,5S,6R)-2-methyl-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
0.06
-
 recombinant enzyme, using prostamide D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
0.06
-
 recombinant enzyme, using prostamide D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens bimatoprost
0.1
-
 recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens Tolrestat
0.13
-
 recombinant enzyme, using prostaglandin H2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens (5Z)-7-[(1R,4S,5S,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
0.13
-
 recombinant enzyme, using prostaglandin H2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens ONO1349
0.3
-
 recombinant enzyme, using prostaglandin H2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens (5Z)-7-[(1R,4S,5S,6R)-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
0.3
-
 recombinant enzyme, using prostaglandin H2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens Tolrestat
0.3
-
 recombinant enzyme, using prostaglandin H2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens ONO1370
0.45
-
 recombinant enzyme, using prostamide D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens Tolrestat
1
-
 IC50 about 1 mM, recombinant enzyme, using prostaglandin D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens (5Z)-7-[(1S,4S,5S,6R)-2-methyl-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
1
-
 IC50 about 1 mM, recombinant enzyme, using prostaglandin D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens (5Z)-7-[(1R,4S,5S,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
1
-
 IC50 about 1 mM, recombinant enzyme, using prostaglandin D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens (5Z)-7-[(1R,4S,5S,6R)-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
1
-
 IC50 about 1 mM, recombinant enzyme, using prostamide D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens (5Z)-7-[(1S,4S,5S,6R)-2-methyl-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
1
-
 IC50 about 1 mM, recombinant enzyme, using prostamide D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens (5Z)-7-[(1R,4S,5S,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
1
-
 IC50 about 1 mM, recombinant enzyme, using prostamide D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens (5Z)-7-[(1R,4S,5S,6R)-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
1
-
 recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens ONO1373
1
-
 recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens ONO1349
1
-
 recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens ONO1370
1
-
 recombinant enzyme, using prostamide D2 2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens ONO1373
1
-
 recombinant enzyme, using prostamide D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens ONO1349
1
-
 recombinant enzyme, using prostamide D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C Homo sapiens ONO1370