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Literature summary extracted from

  • Chen, L.Y.; Watanabe, K.; Hayaishi, O.
    Purification and characterization of prostaglandin F synthase from bovine liver (1992), Arch. Biochem. Biophys., 296, 17-26.
    View publication on PubMed

Activating Compound

EC Number Activating Compound Comment Organism Structure
1.1.1.188 chloride stimulates the reduction of prostaglandin D2 and carbonyl compounds, but had no effect on prostaglandin H2 reduction Bos taurus
1.1.1.188 NaBr stimulates prostaglandin D2 11-ketoreductase activity Bos taurus
1.1.1.188 NaCl stimulates prostaglandin D2 11-ketoreductase activity Bos taurus
1.1.1.188 NaI stimulates prostaglandin D2 11-ketoreductase activity Bos taurus
1.1.1.188 piroxicam
-
 Bos taurus
1.1.1.188 warfarin
-
 Bos taurus

General Stability

EC Number General Stability Organism
1.1.1.188 activity is reduced less than 20% after freezing and thawing several times Bos taurus
1.1.1.188 several freezing and thawing cycles reduce the activity of stored purified liver-type isozyme by 50% Bos taurus

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.188 4-nitrobenzaldehyde competitive inhibition of PGD2 but not of PGH2 reduction Bos taurus
1.1.1.188 9,10-phenanthrenequinone competitive inhibition of PGD2 but not of PGH2 reduction; competitive inhibitor of the reduction of prostaglandin D2, not of prostaglandin H2 Bos taurus
1.1.1.188 Ag+ IC50 = 0.005 mM Bos taurus
1.1.1.188 AgNO3 at 0.05 mM 87-100% inhibition, depending on the substrate Bos taurus
1.1.1.188 Cd2+ IC50 = 0.95 mM Bos taurus
1.1.1.188 CdSO4 at 5 mM 91-100% inhibition, depending on the substrate Bos taurus
1.1.1.188 Cu2+ IC50 = 0.4 mM Bos taurus
1.1.1.188 CuSO4 at 5 mM 93-96% inhibition, depending on the substrate; the liver-type isozyme is 2fold less sensitive than the lung-type isozyme Bos taurus
1.1.1.188 HgCl2 at 1 mM 94-100% inhibition, depending on the substrate; IC50 = 0.3 mM, the liver-type isozyme is 2fold less sensitive than the lung-type isozyme Bos taurus
1.1.1.188 NaF
-
 Bos taurus
1.1.1.188 Zn2+ IC50 = 1.4 mM Bos taurus
1.1.1.188 ZnSO4 at 5 mM 71-100% inhibition, depending on the substrate Bos taurus

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.1.1.188 0.002
-
 9,10-phenanthrenequinone
-
 Bos taurus
1.1.1.188 0.002
-
 9,10-phenanthrenequinone 37°C, liver-type isozyme Bos taurus
1.1.1.188 0.0031
-
 Hydrindantin
-
 Bos taurus
1.1.1.188 0.0031
-
 Hydrindantin 37°C, liver-type isozyme Bos taurus
1.1.1.188 0.0056
-
 Prostaglandin D3
-
 Bos taurus
1.1.1.188 0.0056
-
 Prostaglandin D3 37°C, liver-type isozyme Bos taurus
1.1.1.188 0.007
-
 prostaglandin D1
-
 Bos taurus
1.1.1.188 0.007
-
 prostaglandin D1 37°C, liver-type isozyme Bos taurus
1.1.1.188 0.01
-
 Prostaglandin D2
-
 Bos taurus
1.1.1.188 0.01
-
 Prostaglandin D2 37°C, liver-type isozyme Bos taurus
1.1.1.188 0.0119
-
 p-nitroacetophenone
-
 Bos taurus
1.1.1.188 0.0119
-
 4-Nitroacetophenone 37°C, liver-type isozyme Bos taurus
1.1.1.188 0.0143
-
 4-nitrobenzaldehyde
-
 Bos taurus
1.1.1.188 0.0143
-
 4-nitrobenzaldehyde 37°C, liver-type isozyme Bos taurus
1.1.1.188 0.0167
-
 menadione
-
 Bos taurus
1.1.1.188 0.0167
-
 menadione 37°C, liver-type isozyme Bos taurus
1.1.1.188 0.0175
-
 5beta-dihydrotestosterone
-
 Bos taurus
1.1.1.188 0.0175
-
 5beta-dihydrotestosterone 37°C, liver-type isozyme Bos taurus
1.1.1.188 0.02
-
 Phenylglyoxal
-
 Bos taurus
1.1.1.188 0.02
-
 Phenylglyoxal 37°C, liver-type isozyme Bos taurus
1.1.1.188 0.025
-
 prostaglandin H2
-
 Bos taurus
1.1.1.188 0.025
-
 prostaglandin H2 37°C, liver-type isozyme Bos taurus
1.1.1.188 0.053
-
 cyclohexanone
-
 Bos taurus
1.1.1.188 0.053
-
 cyclohexanone 37°C, liver-type isozyme Bos taurus
1.1.1.188 0.12
-
 Prostaglandin D2 37°C, lung-type isozyme Bos taurus
1.1.1.188 0.143
-
 DL-glyceraldehyde
-
 Bos taurus
1.1.1.188 0.143
-
 DL-glyceraldehyde 37°C, liver-type isozyme Bos taurus
1.1.1.188 135
-
 D-xylose
-
 Bos taurus

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.1.1.188 cytosol liver-type isozyme Bos taurus 5829
-

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.1.1.188 CaCl2 activation Bos taurus
1.1.1.188 Cl- the liver-type isozyme is 3fold more activated than the lung-type isozyme Bos taurus
1.1.1.188 MgCl2 activation Bos taurus
1.1.1.188 NaBr activation Bos taurus
1.1.1.188 NaCl activation Bos taurus
1.1.1.188 NaI activation Bos taurus

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
1.1.1.188 36000
-
 SDS-PAGE Bos taurus
1.1.1.188 36000
-
 liver-type isozyme, gel filtration Bos taurus

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.188 Bos taurus
-
-
-
1.1.1.188 Bos taurus
-
 liver-type and lung-type isozymes
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.1.1.188 native liver-type isozyme from liver, 342fold to homogeneity by ammonium sulfate fractionation, anion exchange and adsorption chromatography Bos taurus

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.1.1.188 liver two different active sites Bos taurus
-
1.1.1.188 liver liver-type isozyme Bos taurus
-
1.1.1.188 lung lung-type isozyme Bos taurus
-

Specific Activity [micromol/min/mg]

EC Number Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
1.1.1.188 additional information
-
-
 Bos taurus
1.1.1.188 0.003
-
 prostaglandin H2 as substrate Bos taurus
1.1.1.188 0.003
-
 purified liver-type isozyme, substrate prostaglandin H2 Bos taurus
1.1.1.188 0.008
-
 purified liver-type isozyme, substrate prostaglandin I2 Bos taurus
1.1.1.188 0.046
-
 prostaglandin D1 as substrate Bos taurus
1.1.1.188 0.046
-
 purified liver-type isozyme, substrate prostaglandin D1 Bos taurus
1.1.1.188 0.065
-
 xylose as substrate Bos taurus
1.1.1.188 0.089
-
 prostaglandin D3 as substrate Bos taurus
1.1.1.188 0.089
-
 purified liver-type isozyme, substrate prostaglandin D3 Bos taurus
1.1.1.188 0.095
-
 prostaglandin D2 as substrate Bos taurus
1.1.1.188 0.095
-
 purified liver-type isozyme, substrate prostaglandin D2 Bos taurus
1.1.1.188 0.13
-
 5beta-dihydrotestosterone as substrate Bos taurus
1.1.1.188 0.159
-
 cyclohexanone as substrate Bos taurus
1.1.1.188 0.167
-
 menadione and hydrindantin as substrate Bos taurus
1.1.1.188 0.174
-
 4-nitroacetophenone as substrate Bos taurus
1.1.1.188 0.206
-
 DL-glyceraldehyde as substrate Bos taurus
1.1.1.188 0.207
-
 phenylglyoxal as substrate Bos taurus
1.1.1.188 0.31
-
 4-nitrobenzaldehyde as substrate Bos taurus
1.1.1.188 0.31
-
 purified liver-type isozyme, substrate 4-nitrobenzaldehyde Bos taurus
1.1.1.188 0.339
-
 9,10-phenanthrenequinone as substrate Bos taurus
1.1.1.188 0.339
-
 purified liver-type isozyme, substrate 9,10-phenanthrenequinone Bos taurus

Storage Stability

EC Number Storage Stability Organism
1.1.1.188 -80°C, concentration 1.5 mg per ml 10 mM potassium phosphate buffer pH 7.0, stable for several months Bos taurus
1.1.1.188 -80°C, purified liver-type isozyme at 1.5 mg/ml in 10 mM potassium phosphate, pH 7.0, stable for several months, several freezing and thawing cycles reduce the activity by 50% Bos taurus
1.1.1.188 25°C, concentration 1.5 mg per ml 10 mM potassium phosphate buffer pH 7.0, 80-90% activity, 1 month Bos taurus
1.1.1.188 4-23°C, purified liver-type isozyme, 1 month, 80-90% remaining activity Bos taurus
1.1.1.188 4°C, concentration 1.5 mg per ml 10 mM potassium phosphate buffer pH 7.0, 80-90% activity, 1 month Bos taurus

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.188 (5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
-
 Bos taurus (5Z,13E)-(15S)-9alpha,11beta,15-trihydroxyprosta-5,13-dienoate + NADP+
-
 ?
1.1.1.188 4-nitroacetophenone + NADPH high activity Bos taurus ?
-
 ?
1.1.1.188 4-nitrobenzaldehyde + NADPH
-
 Bos taurus 4-nitrobenzyl alcohol + NADP+
-
 ?
1.1.1.188 4-nitrobenzaldehyde + NADPH high activity Bos taurus 4-nitrobenzalcohol + NADP+
-
 ?
1.1.1.188 5beta-dihydrotestosterone + NADPH
-
 Bos taurus ?
-
 ?
1.1.1.188 9,10-phenanthrenequinone + NADPH
-
 Bos taurus ?
-
 ?
1.1.1.188 9,10-phenanthrenequinone + NADPH best substrate Bos taurus ?
-
 ?
1.1.1.188 cyclohexanone + NADPH
-
 Bos taurus cyclohexanol + NADP+
-
 ?
1.1.1.188 cyclohexanone + NADPH high activity Bos taurus cyclohexanol + NADP+
-
 ?
1.1.1.188 D-xylose + NADPH
-
 Bos taurus ?
-
 ?
1.1.1.188 daunorubicin + NADPH high activity Bos taurus ?
-
 ?
1.1.1.188 DL-glyceraldehyde + NADPH
-
 Bos taurus DL-glycerol + NADP+
-
 ?
1.1.1.188 duroquinone + NADPH
-
 Bos taurus ?
-
 ?
1.1.1.188 hydrindantin + NADPH
-
 Bos taurus ?
-
 ?
1.1.1.188 hydrindantin + NADPH high activity Bos taurus ?
-
 ?
1.1.1.188 menadione + NADPH
-
 Bos taurus ?
-
 ?
1.1.1.188 menadione + NADPH high activity Bos taurus ?
-
 ?
1.1.1.188 additional information two different active sites, one for the endoperoxide group of prostaglandin H2 and the other one for the keto group of prostaglandin D2 and other carbonyl compounds Bos taurus ?
-
 ?
1.1.1.188 additional information the liver-type isozyme possesses two catalytic centres and a broad substrate specificity, D-xylose is a poor substrate, no activity with prostaglandin A1, prostaglandin B2, prostaglandin E2, 4-carboxybenzaldehyde, testosterone, 2,6-dichloroindophenol, D-glucose, D-glucuronic acid, and potassium ferricyanide, overview, the enzyme also exhibits aldose reductase, EC 1.1.1.21, and alcohol dehydrogenase, EC 1.1.1.1, activities, respectively Bos taurus ?
-
 ?
1.1.1.188 n-butyraldehyde + NADPH
-
 Bos taurus n-butanol + NADP+
-
 ?
1.1.1.188 p-nitroacetophenone + NADPH
-
 Bos taurus ?
-
 ?
1.1.1.188 phenylglyoxal + NADPH
-
 Bos taurus ?
-
 ?
1.1.1.188 phenylglyoxal + NADPH high activity Bos taurus ?
-
 ?
1.1.1.188 prostaglandin D1 + NADPH
-
 Bos taurus ?
-
 ?
1.1.1.188 prostaglandin D2 + NADPH + H+
-
 Bos taurus 9alpha,11beta-prostaglandin F2 + NADP+
-
 ?
1.1.1.188 prostaglandin D3 + NADPH
-
 Bos taurus ?
-
 ?
1.1.1.188 prostaglandin H2 + NADPH + H+
-
 Bos taurus (5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
-
 ?
1.1.1.188 prostaglandin H2 + NADPH + H+
-
 Bos taurus 9alpha,11alpha-prostaglandin F2alpha + NADP+
-
 ?
1.1.1.188 prostaglandin I2 + NADPH
-
 Bos taurus ?
-
 ?
1.1.1.188 ubiquinone-10 + NADPH
-
 Bos taurus ?
-
 ?

Subunits

EC Number Subunits Comment Organism
1.1.1.188 monomer 1 * 36000, SDS-PAGE Bos taurus
1.1.1.188 monomer 1 x 36000, liver-type isozyme, SDS-PAGE Bos taurus

Synonyms

EC Number Synonyms Comment Organism
1.1.1.188 prostaglandin D2 11-ketoreductase
-
 Bos taurus
1.1.1.188 prostaglandin F synthase
-
 Bos taurus

Temperature Stability [°C]

EC Number Temperature Stability Minimum [°C] Temperature Stability Maximum [°C] Comment Organism
1.1.1.188 100
-
 5 min, inactivation Bos taurus
1.1.1.188 100
-
 no reduction of prostaglandin D2 11-reductase after 5 min Bos taurus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.1.1.188 6 7
-
 Bos taurus

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.188 NADPH
-
 Bos taurus
1.1.1.188 NADPH highly preferred cofactor Bos taurus

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.1.1.188 0.0009
-
 9,10-phenanthrenequinone 37°C, liver-type isozyme, versus prostaglandin D2 Bos taurus
1.1.1.188 0.005
-
 AgNO3 prostaglandin D2 11-ketoreductase activity Bos taurus
1.1.1.188 0.023
-
 4-nitrobenzaldehyde 37°C, liver-type isozyme, versus prostaglandin D2 Bos taurus
1.1.1.188 0.3
-
 HgCl2 prostaglandin D2 11-ketoreductase activity Bos taurus
1.1.1.188 0.4
-
 CuSO4 prostaglandin D2 11-ketoreductase activity Bos taurus
1.1.1.188 0.95
-
 CdSO4 prostaglandin D2 11-ketoreductase activity Bos taurus
1.1.1.188 1.4
-
 ZnSO4 prostaglandin D2 11-ketoreductase activity Bos taurus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.1.1.188 0.005
-
 IC50 = 0.005 mM Bos taurus Ag+
1.1.1.188 0.3
-
 IC50 = 0.3 mM, the liver-type isozyme is 2fold less sensitive than the lung-type isozyme Bos taurus HgCl2
1.1.1.188 0.4
-
 IC50 = 0.4 mM Bos taurus Cu2+
1.1.1.188 0.95
-
 IC50 = 0.95 mM Bos taurus Cd2+
1.1.1.188 1.4
-
 IC50 = 1.4 mM Bos taurus Zn2+