Information on EC 1.1.1.188 - prostaglandin-F synthase

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY
1.1.1.188
-
RECOMMENDED NAME
GeneOntology No.
prostaglandin-F synthase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+ = (5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
show the reaction diagram
-
-
-
-
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+ = (5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
show the reaction diagram
active site structure, enzyme also shows 3alpha-hydroxysteroid dehydrogenase type II activity, i.e. 3alpha-HSD
-
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+ = (5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
show the reaction diagram
substrate binding and catalytic mechanism, catalytic site residues are Y55 and H117, enzyme also shows 3alpha-hydroxysteroid dehydrogenase type II activity, i.e. 3alpha-HSD
-
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+ = (5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
show the reaction diagram
Tyr55 is critical for the reaction, the reactions with different substrates might follow different mechanisms
-
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+ = (5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
show the reaction diagram
catalytic mechanisms, the catalytic sites for PGD2 11-ketoreductase and PGH2 9,11-endoperoxide reductase activities are located differently in the active site cavity, residue Y55 is important for the PGD2 11-ketoreductase activity, but not for the PGH2 9,11-endoperoxide reductase activity, involved structural features, overview
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
reduction
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Arachidonic acid metabolism
-
-
arachidonic acid metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate:NADP+ 11-oxidoreductase
Reduces prostaglandin D2 and prostaglandin H2 to prostaglandin F2; prostaglandin D2 is not an intermediate in the reduction of prostaglandin H2. Also catalyses the reduction of a number of carbonyl compounds, such as 9,10-phenanthroquinone and 4-nitroacetophenone.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
20alpha-HSD/PGFS
-
-
20alpha-hydroxysteroid dehydrogenase/prostaglandin F-synthase
-
-
AKR1B1
-
-
AKR1B1
P15121
-
AKR1B3
-
-
AKR1B7
-
-
AKR1C3
P42330
-
aldo-keto reductase
P15121, P42330
-
aldo-keto reductase
-
-
aldo-keto reductase 1C3
P42330
-
ALDR1
P15121
-
ALR2
P15121
-
dihydrodiol dehydrogenase 1
-
-
NADPH-dependent prostaglandin D2 11-keto reductase
-
-
-
-
PG endoperoxide reductase
-
-
PGD 11-ketoreductase
-
-
PGD 11-ketoreductase
-
-
PGD2 11-ketoreductase
-
-
-
-
PGD2 11-ketoreductase
-
-
PGD2 11-ketoreductase
-
-
PGD2 11-ketoreductase
-
-
PGD2 11-ketoreductase
-
-
PGD2 11-ketoreductase activity
-
-
PGF synthase
-
-
-
-
PGF synthase
-
-
PGF synthase I
-
-
PGF synthase II
-
-
PGF2alpha synthase
-
-
-
-
PGF2alpha synthase
-
-
PGF2alpha-synthetic activity
-
-
PGFS
-
-
PGFS
P15121
-
PGFS
P42330
-
PGFS
-
-
PGFS
Q2TJA5
-
PGFS-I
-
-
PGFS-II
-
-
PGFSI
-
-
-
-
PGFSII
-
-
-
-
PGH 9-,11-endoperoxide reductase
-
-
PGH2 9,11-endoperoxidase
-
-
PGH2 9,11-endoperoxide reductase
-
-
PGH2 9-,11-endoperoxide reductase
-
-
PGH2 9-,11-endoperoxide reductase
-
-
PGH2 9-,11-endoperoxide reductase
-
-
prostaglandin 11-keto reductase
-
-
-
-
prostaglandin 11-ketoreductase
-
-
-
-
prostaglandin D2 11-ketoreductase
-
-
prostaglandin D2-ketoreductase
-
-
-
-
prostaglandin F synthase
-
-
-
-
prostaglandin F synthase
-
-
prostaglandin F synthase
-
-
prostaglandin F synthase
P42330
-
prostaglandin F synthase
-
-
prostaglandin F synthase
Q2TJA5
-
prostaglandin F synthase I
-
-
prostaglandin F synthase II
-
-
prostaglandin F synthetase
-
-
-
-
prostaglandin F2alpha synthase
-
-
prostaglandin F2alpha synthase
P15121, P42330
-
prostaglandin F2alpha synthase
-
-
prostaglandin F2alpha-synthase
-
-
prostaglandin-D2 11-reductase
-
-
-
-
prostaglandin-F2alpha synthase
-
-
prostamide/PGF synthase
-
-
prostamide/PGF synthase
A9CQL8
-
prostamide/prostaglandin F synthase
-
-
prostamide/prostaglandin F synthase
A9CQL8
-
reductase, 15-hydroxy-11-oxoprostaglandin
-
-
-
-
synthetase, prostaglandin F2alpha
-
-
-
-
type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase
P42330
-
vas deferens protein
-
-
additional information
-
enzyme belongs to the AKR aldo-keto-reductase superfamily
additional information
-
enzyme also shows 3alpha-hydroxysteroid dehydrogenase type II activity, i.e. 3alpha-HSD
additional information
-
enzyme belongs to the AKR aldo-keto-reductase superfamily
additional information
-
enzyme belongs to the aldo-keto reductase AKR family, enzyme also shows 3alpha-hydroxysteroid dehydrogenase type II activity, i.e. 3alpha-HSD
additional information
-
enzyme belongs to the AKR aldo-keto-reductase superfamily
additional information
-
enzyme belongs to the AKR aldo-keto reductase superfamily
CAS REGISTRY NUMBER
COMMENTARY
55976-95-9
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
liver- and lung-type isozymes
-
-
Manually annotated by BRENDA team
liver-type and lung-type isozymes
-
-
Manually annotated by BRENDA team
to isozymes in lung and liver
-
-
Manually annotated by BRENDA team
two isozymes, lung-type and liver-type
-
-
Manually annotated by BRENDA team
2 isozymes PGFS-I and PGFS-II, soluble and membrane-associated isozymes
-
-
Manually annotated by BRENDA team
AKR1C3
UniProt
Manually annotated by BRENDA team
isoform AKR1C3
UniProt
Manually annotated by BRENDA team
Homo sapiens AKR1C3
AKR1C3
UniProt
Manually annotated by BRENDA team
Macaca fascicularis AKR1C3
AKR1C3
-
-
Manually annotated by BRENDA team
the result of amino acid analysis and sequence comparison suggest that epsilon-crystallin of the lens and prostaglandin F synthase are identical enzymes
-
-
Manually annotated by BRENDA team
isozymes: 1 soluble not-inducible and 1 membraneous inducible by lipopolysaccharides
-
-
Manually annotated by BRENDA team
male and female Wistar rats
-
-
Manually annotated by BRENDA team
male Wistar rats
-
-
Manually annotated by BRENDA team
two isozymes in lung and liver
-
-
Manually annotated by BRENDA team
two isozymes, lung-type and liver-type
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
cyclic and early pregnant sows
-
-
Manually annotated by BRENDA team
several isozymes, e.g. the endometrium-type, the lung-type and the liver-type isozymes
SwissProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
-
prostamide/PGF synthase may play an important functional role in the central nervous system
physiological function
A9CQL8
prostamide/PGF synthase may play an important functional role in the central nervous system. It directly synthesizes prostamide/PGF2alpha from prostamide/PGH2 better than PGF synthase
physiological function
-
knock-down by small interfering RNA for Akr1b3 suppresses PGF2 production and enhances the expression of adipogenic genes such as peroxisome proliferator-activated receptor gamma, fatty acid-binding protein 4, and stearoyl-CoA desaturase
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
-
-
-
-
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
-
-
-
-
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
-
-
-
ir
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
prostaglandin F2alpha exhibits contraction of smooth muscles in the uterus, brochus trachea, luteolysis, the initiation of partutition and pain transmission
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
transformation of endogenous prostaglandin D2 to prostaglandin F2alpha
-
-
-
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
transformation of endogenous prostaglandin D2 to prostaglandin F2alpha
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11beta,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11beta,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
-
-
-
?
4-nitroacetophenone + NADPH
?
show the reaction diagram
-
high activity
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
show the reaction diagram
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
show the reaction diagram
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
show the reaction diagram
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzalcohol + NADP+
show the reaction diagram
-
high activity
-
-
?
4-nitrobenzaldehyde + NADPH + H+
(4-nitrophenyl)methanol + NADP+
show the reaction diagram
-
-
-
-
?
5beta-androstane-3,17-dione + NADPH
5beta-androstan-3alpha-ol-17-one + NADP+
show the reaction diagram
-
-
-
-
r
5beta-dihydrotestosterone + NADPH
?
show the reaction diagram
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
show the reaction diagram
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
show the reaction diagram
-
-
-
-
-
9,10-phenanthrenequinone + NADPH
?
show the reaction diagram
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
show the reaction diagram
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
show the reaction diagram
-
best substrate
-
-
?
9,10-phenanthrenequinone + NADPH
?
show the reaction diagram
-
i.e. PQ
-
-
?
9,10-phenanthrenequinone + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
9,10-phenanthrenequinone + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
androst-4-ene-3,17-dione + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
cyclohexanone + NADPH
cyclohexanol + NADP+
show the reaction diagram
-
-
-
-
?
cyclohexanone + NADPH
cyclohexanol + NADP+
show the reaction diagram
-
high activity
-
-
?
D-xylose + NADPH
?
show the reaction diagram
-
-
-
-
?
daunorubicin + NADPH
?
show the reaction diagram
-
high activity
-
-
?
DL-glyceraldehyde + NADPH
DL-glycerol + NADP+
show the reaction diagram
-
-
-
-
?
DL-glyceraldehyde + NADPH
glyceral + NADP+
show the reaction diagram
-
-
-
-
?
duroquinone + NADPH
?
show the reaction diagram
-
-
-
-
?
hydrindantin + NADPH
?
show the reaction diagram
-
-
-
-
-
hydrindantin + NADPH
?
show the reaction diagram
-
-
-
-
?
hydrindantin + NADPH
?
show the reaction diagram
-
high activity
-
-
?
menadione + NADPH
?
show the reaction diagram
-
-
-
-
?
n-butyraldehyde + NADPH
n-butanol + NADP+
show the reaction diagram
-
-
-
-
?
p-nitroacetophenone + NADPH
?
show the reaction diagram
-
-
-
-
?
phenylglyoxal + NADPH
?
show the reaction diagram
-
-
-
-
-
phenylglyoxal + NADPH
?
show the reaction diagram
-
-
-
-
?
phenylglyoxal + NADPH
?
show the reaction diagram
-
high activity
-
-
?
prostaglandin A2 + NADPH
?
show the reaction diagram
-
-
-
-
?
prostaglandin D + NADPH
9alpha,11alpha-prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D + NADPH
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D1 + NADPH
?
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH
9alpha,11beta-prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
r
prostaglandin D2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
P42330
-
-
-
?
prostaglandin D2 + NADPH
9alpha,11beta-prostaglandin F2alphabeta + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH
9alpha,11alpha-prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH
9alpha,11alpha-prostaglandin F2alpha + NADP+
show the reaction diagram
-
reaction via formation of the endoperoxide ethanolamide intermediate prostaglandin H2
-
-
?
prostaglandin D2 + NADPH
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
show the reaction diagram
P42330
-
-
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
show the reaction diagram
-
-
-
-
-
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
show the reaction diagram
-
-
product is involved in bronchial, vascular, and arterial smooth muscle contraction, product inhibits platelet aggregation and activates urinary excretion
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
show the reaction diagram
-
-
i.e. 11-epi PGF2alpha
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
show the reaction diagram
-
amino acid residues Arg27, Arg91, His170, Arg223, and Asn306 are involved in substrate binding
-
-
?
prostaglandin D2 + NADPH + H+
9-alpha,11-beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
P42330
-
-
-
?
prostaglandin D2 ethanolamide + NADPH
prostaglandin 9alpha,11beta-F2 ethanolamide + NADP+
show the reaction diagram
P42330
i.e. prostamide D2
i.e. 91lpha,11beta-prostamide F2
-
?
prostaglandin D3 + NADPH
?
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
-
-
-
-
prostaglandin H2 + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
aldo-keto reductases AKR1B3 and AKR1B7 have prostaglandin F2alpha synthase activity
-
-
?
prostaglandin H2 + NADPH
prostaglandin D2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
P42330
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
no stereochemic determination/identification of the product
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
enzyme also shows PGH2 9-,11-endoperoxide reductase activity
-
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
His170 is involved in binding, and Asn306 is critical for catalytic activity
-
-
?
prostaglandin H2 + NADPH
prostaglandin 9alpha,11beta-F2 + NADP+
show the reaction diagram
P42330
-
-
-
?
prostaglandin H2 + NADPH
9alpha,11alpha-prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
9alpha,11alpha-prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH + H+
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
P15121
aldo-keto reductase has prostaglandin F2alpha synthase activity. AKR1B1 is a more efficient prostaglandin F2alpha synthase than AKR1C3
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
r
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
show the reaction diagram
A9CQL8
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
show the reaction diagram
P42330
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin I2 + NADPH
?
show the reaction diagram
-
-
-
-
?
prostamide D2 + NADPH + H+
9alpha,11beta-prostamide F2 + NADP+
show the reaction diagram
P42330
-
-
-
?
prostamide H2 + NADPH + H+
prostamide F2alpha + NADP+
show the reaction diagram
-
about 70% of prostamide H2 is converted to prostamide F2alpha after 2 min at 37C
-
-
?
retinal + NADPH
retinol + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH
?
show the reaction diagram
-
-
-
-
?
ubiquinone-10 + NADPH
?
show the reaction diagram
-
-
-
-
?
menadione + NADPH
?
show the reaction diagram
-
high activity
-
-
?
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
-
-
-
additional information
?
-
-
enzyme interacts with cyclooxygenase 1 and 2, isozyme PGFS-I interacts predominantly with cyclooxygenase 2, i.e. COX-2
-
-
-
additional information
?
-
-
the cytosolic enzyme synergistically interacts with cyclooxygenase 1 and 2, coupling, isozyme PGFS-I interacts predominantly with cyclooxygenase 2, i.e. COX-2
-
-
-
additional information
?
-
-
acive site structure, enzyme also shows 3alpha-hydroxysteroid dehydrogenase type II activity
-
-
-
additional information
?
-
-
enzyme does not reduce prostaglandins D2 and E2
-
-
-
additional information
?
-
-
enzyme shows no prostaglandin D2 11-ketoreductase activity, and no glutathione S-transferase activity, although it is similar to the glutathione S-transferase
-
-
-
additional information
?
-
P42330
substrate and product detection by liquid chromatographic-electrospray ionization-mass spectrometry
-
-
-
additional information
?
-
-
Y55 and H117 are involved in catalysis, enzyme also shows 3alpha-hydroxysteroid dehydrogenase type II activity
-
-
-
additional information
?
-
-
coupling ability between cyclooxygenase COX-2 and the prostanoid synthases performing the last stepes in the biosynthesis of prostaglandins PGE2, PGD2, PGF2alpha, and PGI2, regulation, overview, the 20alpha-hydroxysteroid dehydrogenase also shows prostaglandin F synthase activity in the endometrium during luteolysis
-
-
-
additional information
?
-
-
the enzyme has dual activity as PGD2 11-ketoreductase and PGH2 9,11-endoperoxide reductase
-
-
-
additional information
?
-
-
the enzyme is important for the production of lyteolytic prostaglandin F2alpha in the endometrium of cows, regulatory mechanisms, overview
-
-
-
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
-
-
-
additional information
?
-
-
prostaglandin F synthase and prostaglandin F receptor are involved in the control of testosterone release from Leydig cells and in spermatogenesis via the local pathway and the hypothalamo-hypophysial-testis-pathway
-
-
-
additional information
?
-
-
no activity with prostaglandin D2 and prostaglandin E2
-
-
-
additional information
?
-
-
PGFS does not catalyze the reduction of prostaglandin E2
-
-
-
additional information
?
-
-
in the absence of NADPH or NADP+, enzyme catalyzes the isomerization of prostaglandin H2 to prostaglandin D2 with a Km value of 0.018 mM. This activity activity of AKR1B1 increases with increasing pH, with an optimum of pH 8.5. Residue His110 acts as a base in concert with Asp43 and Lys77 and as an acid to generate PGD2 and PGF2a in the absence of NADPH or NADP+ and in the presence of NADPH, respectively
-
-
-
additional information
?
-
-
in the absence of NADPH or NADP+, enzyme catalyzes the isomerization of prostaglandin H2 to prostaglandin D2 with a Km value of 0.023 mM. This activity of AKR1B1 increases with increasing pH, with an optimum of pH 8.5. Residue His110 acts as a base in concert with Asp43 and Lys77 and as an acid to generate PGD2 and PGF2a in the absence of NADPH or NADP+ and in the presence of NADPH, respectively
-
-
-
additional information
?
-
-
no activity with prostaglandin E2
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
prostaglandin F2alpha exhibits contraction of smooth muscles in the uterus, brochus trachea, luteolysis, the initiation of partutition and pain transmission
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
transformation of endogenous prostaglandin D2 to prostaglandin F2alpha
-
-
-
prostaglandin D + NADPH
9alpha,11alpha-prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D + NADPH
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH
9alpha,11beta-prostaglandin F2alphabeta + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
show the reaction diagram
-
-
product is involved in bronchial, vascular, and arterial smooth muscle contraction, product inhibits platelet aggregation and activates urinary excretion
-
?
prostaglandin D2 + NADPH + H+
9-alpha,11-beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin D2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
enzyme also shows PGH2 9-,11-endoperoxide reductase activity
-
-
?
prostaglandin H2 + NADPH
9alpha,11alpha-prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
-
transformation of endogenous prostaglandin D2 to prostaglandin F2alpha
-
-
?
additional information
?
-
-
enzyme interacts with cyclooxygenase 1 and 2, isozyme PGFS-I interacts predominantly with cyclooxygenase 2, i.e. COX-2
-
-
-
additional information
?
-
-
the cytosolic enzyme synergistically interacts with cyclooxygenase 1 and 2, coupling, isozyme PGFS-I interacts predominantly with cyclooxygenase 2, i.e. COX-2
-
-
-
additional information
?
-
-
coupling ability between cyclooxygenase COX-2 and the prostanoid synthases performing the last stepes in the biosynthesis of prostaglandins PGE2, PGD2, PGF2alpha, and PGI2, regulation, overview, the 20alpha-hydroxysteroid dehydrogenase also shows prostaglandin F synthase activity in the endometrium during luteolysis
-
-
-
additional information
?
-
-
the enzyme has dual activity as PGD2 11-ketoreductase and PGH2 9,11-endoperoxide reductase
-
-
-
additional information
?
-
-
the enzyme is important for the production of lyteolytic prostaglandin F2alpha in the endometrium of cows, regulatory mechanisms, overview
-
-
-
additional information
?
-
-
prostaglandin F synthase and prostaglandin F receptor are involved in the control of testosterone release from Leydig cells and in spermatogenesis via the local pathway and the hypothalamo-hypophysial-testis-pathway
-
-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADH
-
less effective than NADPH
NADH
-
less effective than NADPH
NADH
-
with NADH as cofactor no activity observed
NADP+
-
binding structure at the active site
NADP+
Q2TJA5
-
NADP+
-
-
NADPH
-
no NADPH-generating system required
NADPH
-
binding structure at the active site, catalytic structure and mechanism involving the cofactor
NADPH
-
dependent on
NADPH
-
highly preferred cofactor
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
CaCl2
-
activation
Cl-
-
the liver-type isozyme is 3fold more activated than the lung-type isozyme
MgCl2
-
activation
NaBr
-
activation
NaCl
-
activation
NaI
-
activation
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(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
(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
(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
(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
(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
(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
(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
1-(4-aminobenzyl)-5-methoxy-2-methylindoleacetic acid
-
-
2-(1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)-N-((trifluoromethyl)sulfonyl)acetamide
P42330
257fold selectivity for isoform AKR1C3 over isoform AKR1C2
-
3-(1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl)-propanoic acid
P42330
540fold selectivity for isoform AKR1C3 over isoform AKR1C2
3-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-propanoic acid
P42330
257fold selectivity for isoform AKR1C3 over isoform AKR1C2
4-benzoyl-benzoic acid
-
;
4-carboxy-2',4'-dinitrodiphenylamine
-
;
4-carboxy-2-aminodiphenylamine
-
;
4-chloro-N-(4-tolyl)-anthranilic acid
-
;
4-chloro-N-phenylanthranilic acid
-
;
4-nitro-N-phenylanthranilic acid
-
;
4-Nitrobenzaldehyde
-
competitive inhibition of PGD2 but not of PGH2 reduction
5-methyl-N-phenylanthranilic acid
-
;
9,10-phenanthrenequinone
-
competitive inhibitor of the reduction of prostaglandin D2, not of prostaglandin H2
9,10-phenanthrenequinone
-
competitive inhibition of the PGD2 11-ketoreductase activity, not of PGH2 9-,11-endoperoxide reductase activity
9,10-phenanthrenequinone
-
competitive inhibition of PGD2 but not of PGH2 reduction
9,10-phenanthrenequinone
-
the prostaglandin D2 11-ketoreductase activity of PGFS is competitively inhibited by 9,10-phenanthrenequinone
acetate
-
occupies the oxyanion hole of the active site, 2 complex structures
Ag+
-
IC50 = 0.005 mM
AgNO3
-
at 0.05 mM 87-100% inhibition, depending on the substrate
aspirin
-
;
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
bimatoprost
-
inhibits the prostaglandin D2 11-ketoreductase activity as well as the prostaglandin H2 9,11-endoperoxide reductase activity of PGFS
Cd2+
-
IC50 = 0.95 mM
CdSO4
-
at 5 mM 91-100% inhibition, depending on the substrate
Cu2+
-
IC50 = 0.4 mM
CuSO4
-
at 5 mM 93-96% inhibition, depending on the substrate
CuSO4
-
the liver-type isozyme is 2fold less sensitive than the lung-type isozyme
FeCl2
-
-
Flufenamic acid
-
nonsteroidal anti-inflammatory drug, binds to both the active site and the beta-hairpin loop at the opposite end of the central beta-barrel, complex structure
Flurbiprofen
-
-
Flurbiprofen
-
;
HgCl2
-
at 1 mM 94-100% inhibition, depending on the substrate
HgCl2
-
IC50 = 0.3 mM, the liver-type isozyme is 2fold less sensitive than the lung-type isozyme
Ibuprofen
-
-
Ibuprofen
-
;
indomethacin
-
at 0.005 mg/ml in vivo inhibition of prostaglandin formation
indomethacin
-
nonsteroidal anti-inflammatory drug, 1 molecule binds to the active site, complex structure
indomethacin
-
; specific inhibition of isoform AKR1C3 versus AKR1C1 and AKR1C3
indomethacin
-
; inhibits AKR1C3, but does not inhibit highly related AKR1C1 or AKR1C2
indomethacin methyl ester
-
specific inhibition of isoform AKR1C3 versus AKR1C1 and AKR1C3
interferon tau
-
recombinant ovine interferon tau down-regulates mRNA gene expression of the prostaglandin F synthase at a concentration of 0.000001 mg/ml
-
interferon tau
-
recombinant bovine interferon tau down-regulates mRNA gene expression of the prostaglandin F synthase after stimulation with oxytocin
-
Meclofenamic acid
-
-
Meclofenamic acid
-
;
N-(4-chlorobenzoyl)-melatonin
-
specific inhibition of isoform AKR1C3 versus AKR1C1 and AKR1C3, not inhibitory to cyclooxygenases. Uncompetitive versus 9,10-phenynthrenequinone, competitive versus DELTA4-andostene-3,17-dione
N-(4-chlorobenzoyl)-melatonin
-
exhibits uncompetitive inhibition patterns for the reduction of 9,10-phenanthrenequinone but competitive inhibition patterns for the reduction of androstenedione by AKR1C3
NaF
-
-
Naproxen
-
-
Naproxen
-
;
ONO1349
-
-
ONO1370
-
-
ONO1373
-
-
Ponalrestat
-
specific inhibitor developed to block AKR1B1 activity. Application reduces prostaglandin F2alpha production in response to interleukin IL-1beta in both cultured endometrial cells and endometrial explants
rutin
-
binding structure at the substrate binding site
salicylic acid
-
;
Sorbinil
-
;
Sorbinil
-
significantly inhibits the prostaglandin F2alpha synthase activity of AKR1B3 in a non-competitive fashion, whereas AKR1B7 is not sensitive to the inhibitor
stafil
-
-
-
sulindac
-
-
sulindac
-
;
Tolrestat
-
; inhibition of all 3 enzyme activities, most effective inhibiting the PGD2 11-ketoreductase activity
Tolrestat
-
;
Tolrestat
-
significantly inhibits the prostaglandin F2alpha synthase activity of AKR1B3 in a non-competitive fashion, whereas AKR1B7 is not sensitive to the inhibitor
Zn2+
-
IC50 = 1.4 mM
ZnSO4
-
at 5 mM 71-100% inhibition, depending on the substrate
Zomepirac
-
-
Zomepirac
-
;
Mefenamic acid
-
;
additional information
-
no inhibition by 9,10-phenanthrenequinone
-
additional information
-
AKR1C3 is potently inhibited by non-steroidal anti-inflammatory drugs, which are protective against breast cancer
-
additional information
-
heat treatment of AKR1B1 at 100C for 5 min completely inactivates the prostaglandin F2alpha synthase activity, which is strictly dependent on the presence of NADPH
-
additional information
-
heat treatment of AKR1B3 and AKR1B7 at 100C for 5 min completely inactivates the prostaglandin F2alpha synthase activities, which is strictly dependent on the presence of NADPH
-
additional information
-
inhibitors such as alrestatin, ponalrestat, and EBPC exhibit distinct and characteristic inhibition of prostaglandin F2alpha production in different cell models
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
ammonium sulfate
A9CQL8
activity of the purified recombinant enzyme is stimulated about 4fold by 1.5 M
chloride
-
stimulates the reduction of prostaglandin D2 and carbonyl compounds, but had no effect on prostaglandin H2 reduction
Gonadotropin
-
prostaglandin F synthase mRNA and protein levels are low before treatment with gonadotropin and peak 24-36 h after gonadotropin administration to granulosa cells
-
GSH
-
dependent on
imidazole
-
in vitro stimulation of prostaglandin F2alpha and D2 production
Interleukin-1beta
-
membrane-associated, not soluble, isozyme in WI-38 cells
-
lipopolysaccharide
-
induces the membrane-associated isozyme
NaBr
-
stimulates prostaglandin D2 11-ketoreductase activity
NaCl
-
stimulates prostaglandin D2 11-ketoreductase activity
NaI
-
stimulates prostaglandin D2 11-ketoreductase activity
Oxytocin
-
increases prostaglandin F synthase mRNA synthesis
Oxytoxin
-
stimulates enzyme expression and PGD2 11-ketoreductase activity in myometrial tissue of cyclic, but not significantly of early-pregnant, sows, at 0.0001 mM
phorbol 12-myristate 13-acetate
-
stimulates prostaglandin synthesis
piroxicam
-
-
Warfarin
-
-
lipopolysaccharides
-
strong induction of the membrane-bound lung isozyme, slight induction in spleen, kidney, testis, and pancreas, overview
-
additional information
-
no thiol required for activity
-
additional information
-
PGF synthase I activity in HEK 293 cells is unaffected by interleukin-1beta
-
additional information
-
4fold activation by heat treatment
-
additional information
-
oxytoxin does not stimulate PGH2 9,11-endoperoxide reductase expression and activity in myometrial tissue of cyclic and early-pregnant sows
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.134
(5Z,13E)-(15S)-9alpha,11beta,15-trihydroxyprosta-5,13-dienoate
-
-
0.0119
4-Nitroacetophenone
-
37C, liver-type isozyme
0.013
4-Nitroacetophenone
-
lung enzyme
0.0008
4-Nitrobenzaldehyde
-
-
0.0008
4-Nitrobenzaldehyde
-
liver enzyme
0.0083
4-Nitrobenzaldehyde
-
lung enzyme
0.0143
4-Nitrobenzaldehyde
-
-
0.0143
4-Nitrobenzaldehyde
-
37C, liver-type isozyme
0.0774
4-Nitrobenzaldehyde
-
-
0.125
4-Nitrobenzaldehyde
-
lung enzyme
0.0031
5beta-androstan-3,17-dione
-
-
0.001
5beta-Androstan-3alpha-ol-17-one
-
-
0.0175
5beta-dihydrotestosterone
-
-
0.0175
5beta-dihydrotestosterone
-
37C, liver-type isozyme
0.0001
9,10-phenanthrenequinone
-
expressed lung enzyme
0.00013
9,10-phenanthrenequinone
-
lung enzyme
0.00042
9,10-phenanthrenequinone
-
-
0.0007
9,10-phenanthrenequinone
-
native lung prostaglandin F synthase
0.0008
9,10-phenanthrenequinone
-
-
0.001
9,10-phenanthrenequinone
-
liver enzyme
0.0011
9,10-phenanthrenequinone
-
expressed liver prostaglandin F synthase
0.0011
9,10-phenanthrenequinone
-
recombinant wild-type liver-type isozyme, 37C
0.0015
9,10-phenanthrenequinone
-
pH 7.0, 37C
0.002
9,10-phenanthrenequinone
-
native liver prostaglandin F synthase
0.002
9,10-phenanthrenequinone
-
-
0.002
9,10-phenanthrenequinone
-
37C, liver-type isozyme
0.0066
androst-4-ene-3,17-dione
-
pH 7.0, 37C
0.053
cyclohexanone
-
-
0.053
cyclohexanone
-
37C, liver-type isozyme
135
D-xylose
-
-
0.143
DL-glyceraldehyde
-
-
0.143
DL-glyceraldehyde
-
37C, liver-type isozyme
0.0031
Hydrindantin
-
-
0.0031
Hydrindantin
-
37C, liver-type isozyme
0.018
Hydrindantin
-
lung enzyme
0.013
menadione
-
lung enzyme
0.0167
menadione
-
-
0.0167
menadione
-
37C, liver-type isozyme
0.0034
NADPH
-
-
0.0057
NADPH
-
-
0.0074
NADPH
-
AKR1B3
0.0092
NADPH
-
AKR1B7
0.067
NADPH
-
-
0.0119
p-nitroacetophenone
-
-
0.02
Phenylglyoxal
-
-
0.02
Phenylglyoxal
-
37C, liver-type isozyme
0.08
Phenylglyoxal
-
lung enzyme
0.25
Prostaglandin A2
-
lung enzyme
0.007
Prostaglandin D1
-
-
0.007
Prostaglandin D1
-
37C, liver-type isozyme
0.0034
Prostaglandin D2
-
-
0.01
Prostaglandin D2
-
native liver prostaglandin F synthase
0.01
Prostaglandin D2
-
-
0.01
Prostaglandin D2
-
37C, liver-type isozyme
0.015
Prostaglandin D2
-
expressed liver prostaglandin F synthase
0.1
Prostaglandin D2
-
expressed lung enzyme
0.1
Prostaglandin D2
-
lung enzyme
0.12
Prostaglandin D2
-
native lung prostaglandin F synthase
0.12
Prostaglandin D2
-
37C, lung-type isozyme
0.174
Prostaglandin D2
-
-
0.2
Prostaglandin D2
-
liver enzyme
0.2
Prostaglandin D2
-
-
2
Prostaglandin D2
-
-
0.0056
Prostaglandin D3
-
-
0.0056
Prostaglandin D3
-
37C, liver-type isozyme
0.0013
prostaglandin H2
-
-
0.0019
prostaglandin H2
-
-
0.0038
prostaglandin H2
-
AKR1B7
0.0069
prostaglandin H2
-
pH 7.0, 24C
0.007
prostaglandin H2
A9CQL8
-
0.008
prostaglandin H2
-
expressed lung enzyme
0.0093
prostaglandin H2
-
AKR1B3
0.01
prostaglandin H2
-
native lung prostaglandin F synthase
0.018
prostaglandin H2
-
-
0.025
prostaglandin H2
-
native and expressed liver prostaglandin F synthase
0.025
prostaglandin H2
-
-
0.025
prostaglandin H2
-
37C, liver-type isozyme
0.029
prostaglandin H2
-
pH 5.5, 37C
0.033
prostaglandin H2
-
pH 5.0, 37C
0.015
prostaglandin PGD2
-
recombinant wild-type liver-type isozyme, 37C
0.04
prostaglandin PGD2
-
recombinant liver-type isozyme mutant S301R, 37C
0.05
prostaglandin PGD2
-
recombinant liver-type isozyme mutant K225S, 37C
0.075
prostaglandin PGD2
-
recombinant liver-type isozyme mutant H170C, 37C
0.1
prostaglandin PGD2
-
recombinant liver-type isozyme mutant N306Y, 37C
0.11
prostaglandin PGD2
-
recombinant liver-type isozyme mutant R27E, 37C
0.12
prostaglandin PGD2
-
recombinant wild-type lung-type isozyme
0.145
prostaglandin PGD2
-
recombinant liver-type isozyme mutant R91Q, 37C
0.18
prostaglandin PGD2
-
recombinant liver-type isozyme mutant R223L, 37C
0.003
prostaglandin PGH2
-
recombinant liver-type isozyme, mutant H170C, 37C
0.01
prostaglandin PGH2
-
recombinant liver-type isozyme, mutants R91Q, R223L and N306Y, 37C
0.014
prostaglandin PGH2
-
recombinant liver-type isozyme, mutant R27E, 37C
0.025
prostaglandin PGH2
-
recombinant wild-type liver-type isozyme, 37C
0.028
prostaglandin PGH2
-
recombinant liver-type isozyme, mutant K225S, 37C
0.03
prostaglandin PGH2
-
recombinant liver-type isozyme, mutant S301R, 37C
0.02
retinal
-
-
0.0057
testosterone
-
-
0.1
menadione
-
liver enzyme
additional information
additional information
-
kinetics of 3alpha-hydroxysteroid dehydrogenase type II activity
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1.4
9,10-phenanthrenequinone
-
pH 7.0, 37C
0.0027
androst-4-ene-3,17-dione
-
pH 7.0, 37C
0.2467
prostaglandin H2
-
pH 7.0, 24C
0.2467
prostaglandin H2
A9CQL8
-
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
35.85
prostaglandin H2
-
pH 7.0, 24C
612
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0019
4-benzoyl-benzoic acid
-
;
0.00038
4-carboxy-2',4'-dinitrodiphenylamine
-
;
0.01
4-carboxy-2-aminodiphenylamine
-
;
0.0014
4-chloro-N-(4-tolyl)-anthranilic acid
-
;
0.0029
4-chloro-N-phenylanthranilic acid
-
;
0.0019
4-nitro-N-phenylanthranilic acid
-
;
0.023
4-Nitrobenzaldehyde
-
37C, liver-type isozyme, versus prostaglandin D2
0.0073
5-methyl-N-phenylanthranilic acid
-
;
0.0009
9,10-phenanthrenequinone
-
37C, liver-type isozyme, versus prostaglandin D2
0.005
AgNO3
-
prostaglandin D2 11-ketoreductase activity
0.95
CdSO4
-
prostaglandin D2 11-ketoreductase activity
0.4
CuSO4
-
prostaglandin D2 11-ketoreductase activity
0.3
HgCl2
-
prostaglandin D2 11-ketoreductase activity
0.0034
N-(4-chlorobenzoyl)-melatonin
-
-
0.00089
Sorbinil
-
AKR1B3
0.0217
Sorbinil
-
-
0.00026
Tolrestat
-
AKR1B3
0.0036
Tolrestat
-
-
1.4
ZnSO4
-
prostaglandin D2 11-ketoreductase activity
0.0003
Mefenamic acid
-
;
additional information
additional information
-
Ki values for the nonsteroidal anti-inflammatory drug inhibitors with 3alpha-androstanediol as a substrate
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.005
(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
-
recombinant enzyme, using prostaglandin D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
0.006
(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
-
recombinant enzyme, using prostaglandin H2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
0.06
(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
-
recombinant enzyme, using prostamide D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
0.3
(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
-
recombinant enzyme, using prostaglandin H2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
1
(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
-
IC50 about 1 mM, recombinant enzyme, using prostaglandin D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37C; IC50 about 1 mM, recombinant enzyme, using prostamide D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
0.13
(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
-
recombinant enzyme, using prostaglandin H2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
1
(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
-
IC50 about 1 mM, recombinant enzyme, using prostaglandin D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37C; IC50 about 1 mM, recombinant enzyme, using prostamide D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
0.06
(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
-
recombinant enzyme, using prostaglandin H2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
1
(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
-
IC50 about 1 mM, recombinant enzyme, using prostaglandin D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37C; IC50 about 1 mM, recombinant enzyme, using prostamide D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
0.052
1-(4-aminobenzyl)-5-methoxy-2-methylindoleacetic acid
-
pH 7.0, 37C
0.00021
2-(1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl )-N-((trifluoromethyl)sulfonyl)acetamide
P42330
pH not specified in the publication, temperature not specified in the publication
0.00009
3-(1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl)-propanoic acid
P42330
pH not specified in the publication, temperature not specified in the publication
0.00022
3-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-propanoic acid
P42330
pH not specified in the publication, temperature not specified in the publication
0.002
4-benzoyl-benzoic acid
-
;
0.0004
4-carboxy-2',4'-dinitrodiphenylamine
-
;
0.011
4-carboxy-2-aminodiphenylamine
-
;
0.0015
4-chloro-N-(4-tolyl)-anthranilic acid
-
;
0.003
4-chloro-N-phenylanthranilic acid
-
;
0.002
4-nitro-N-phenylanthranilic acid
-
;
0.011
5-methyl-N-phenylanthranilic acid
-
;
0.005
Ag+
-
IC50 = 0.005 mM
1.2
aspirin
-
;
0.005
bimatoprost
-
recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
0.006
bimatoprost
-
recombinant enzyme, using prostaglandin H2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
0.06
bimatoprost
-
recombinant enzyme, using prostamide D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
0.95
Cd2+
-
IC50 = 0.95 mM
0.4
Cu2+
-
IC50 = 0.4 mM
0.0078
Flurbiprofen
-
pH 7.0, 37C
0.0078
Flurbiprofen
-
;
0.3
HgCl2
-
IC50 = 0.3 mM, the liver-type isozyme is 2fold less sensitive than the lung-type isozyme
0.0099
Ibuprofen
-
pH 7.0, 37C
0.0099
Ibuprofen
-
;
0.0023
indomethacin
-
pH 7.0, 37C
0.0023
indomethacin
-
;
0.0023
indomethacin methyl ester
-
pH 7.0, 37C
0.0007
Meclofenamic acid
-
pH 7.0, 37C
0.0007
Meclofenamic acid
-
;
0.00039
Mefenamic acid
-
;
0.0078
N-(4-chlorobenzoyl)-melatonin
-
pH 7.0, 37C
0.0014
Naproxen
-
pH 7.0, 37C
0.0014
Naproxen
-
;
0.13
ONO1349
-
recombinant enzyme, using prostaglandin H2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
1
ONO1349
-
recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C; recombinant enzyme, using prostamide D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
0.3
ONO1370
-
recombinant enzyme, using prostaglandin H2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
1
ONO1370
-
recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C; recombinant enzyme, using prostamide D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
0.06
ONO1373
-
recombinant enzyme, using prostaglandin H2 2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
1
ONO1373
-
recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C; recombinant enzyme, using prostamide D2 2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
0.77
salicylic acid
-
;
0.012
stafil
-
recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
-
0.013
stafil
-
recombinant enzyme, using prostamide D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
-
0.058
stafil
-
recombinant enzyme, using prostaglandin H2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
-
0.0034
sulindac
-
pH 7.0, 37C
0.0034
sulindac
-
;
0.1
Tolrestat
-
recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
0.3
Tolrestat
-
recombinant enzyme, using prostaglandin H2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
0.45
Tolrestat
-
recombinant enzyme, using prostamide D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37C
1.4
Zn2+
-
IC50 = 1.4 mM
0.04
Zomepirac
-
pH 7.0, 37C
0.04
Zomepirac
-
;
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.0015
-
prostaglandin D2 as substrate
0.003
-
prostaglandin H2 as substrate
0.003
-
purified liver-type isozyme, substrate prostaglandin H2
0.008
-
purified liver-type isozyme, substrate prostaglandin I2
0.034
-
-
0.046
-
prostaglandin D1 as substrate
0.046
-
purified liver-type isozyme, substrate prostaglandin D1
0.062
A9CQL8
PGF synthase activity of the purified enzyme
0.065
-
xylose as substrate
0.089
-
prostaglandin D3 as substrate
0.089
-
purified liver-type isozyme, substrate prostaglandin D3
0.095
-
prostaglandin D2 as substrate
0.095
-
purified liver-type isozyme, substrate prostaglandin D2
0.115
-
4-nitrobenzaldehyde reductase activity
0.13
-
5beta-dihydrotestosterone as substrate
0.15
-
prostaglandin F2alpha as product
0.159
-
cyclohexanone as substrate
0.167
-
menadione and hydrindantin as substrate
0.174
-
4-nitroacetophenone as substrate
0.206
-
DL-glyceraldehyde as substrate
0.207
-
phenylglyoxal as substrate
0.31
-
4-nitrobenzaldehyde as substrate
0.31
-
purified liver-type isozyme, substrate 4-nitrobenzaldehyde
0.339
-
9,10-phenanthrenequinone as substrate
0.339
-
purified liver-type isozyme, substrate 9,10-phenanthrenequinone
0.69
-
PGF synthase activity of the purified enzyme
2.4
-
pH 5.5, 37C
3.6
-
pH 5.0, 37C
additional information
-
-
additional information
-
expression levels in the placentome of pregnant cows at different developmental stages
additional information
-
at 37C in 100 mM Tris/HCl (pH 7.0), the reaction product, 9-alpha,11-beta-prostaglandin F2 is detected as well as the substrate prostaglandin D2 in the reaction solution after reaction for 1 h, the amount of the product increases linearly for 1 h and then gradually plateaues
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5
-
assay at
6.5
-
PGD2 11-ketoreductase activity assay at
6.5
-
assay at, PGD2 11-ketoreductase activity and PGH2 9,11-endoperoxide reductase activity
7
-
in 100 mM Tris/HCl
8 - 9
-
reduction of prostaglandin D2
9 - 10
-
oxidation of 9alpha,11beta-prostaglandin F2
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
-
assay at, PGH2 9,11-endoperoxide reductase activity
37
-
assay at
37
-
assay at
37
-
assay at
37
-
PGD2 11-ketoreductase activity assay at
37
-
assay at
37
-
assay at, PGD2 11-ketoreductase activity
37
-
assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25 - 37
-
the activity increases gradually as the temperature increases from 25 to 37C, and then decreases significantly at 45C compared with that at 37C
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
AKR1B3 mRNA 9 is expressed in preadipocytes, and its level increases about 4fold at day 1 after initiation of adipocyte differentiation, and then quickly decreases the following day to a level lower than that in the preadipocytes
Manually annotated by BRENDA team
-
expression of genes for PGE2 synthesis, with low levels of prostaglandin transporters and dehydrogenase
Manually annotated by BRENDA team
-
endothel, isozymes PGF synthase I and II
Manually annotated by BRENDA team
A9CQL8
highest activity
Manually annotated by BRENDA team
-
high activity
Manually annotated by BRENDA team
-
enzyme is expressed preferentially in the white matter bundles of the entire central nervous system of adult mice with less marked expression inneuronal cell bodies. The enzyme co-localizes with myelin basic protein in myelin sheaths but not in axons
Manually annotated by BRENDA team
-
normal breast expresses very high levels of AKR1C3 relative to other tissues
Manually annotated by BRENDA team
-
18fold increase in the median AKR1C3 mRNA levels in breast cancer patients as compared to those without disease
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
production of PGE2, PGF2 and PGD2 and high prostaglandin turnover
Manually annotated by BRENDA team
-
peri- and postimplantation conceptus. Prostaglandin H synthase and prostaglandin E synthase are down-regulated, and prostaglandin G synthase, prostaglandin F synthase and carbonyl reductase/prostaglandin 9-reductase are down-regulated in conceptuses during trophoblasic elongation. After initiation of implantation, expression of prostaglandin G synthase, prostaglandin F synthase and carbonyl reductase/prostaglandin 9-reductase in conceptuses increases and remains higher until days 24-25 of pregnancy
Manually annotated by BRENDA team
Q2TJA5
high expression level of the lung-type and the microsomal endometrium-type isozymes
Manually annotated by BRENDA team
-
at days 12-14 of pregnancy and the estrous cycle, the expression of prostaglandin E2 synthase, prostaglandin F synthase, and carbonyl reductase/prostaglandin 9-ketoreductase genes and prostaglandin E2 synthase/prostaglandin F synthase ratio are significantly higher in corpora lutea of the pregnant gilts compared to the corpora lutea from the parallel ovaries of the cyclic gilts. There is no difference in expression of prostaglandin E2 synthase, prostaglandin F synthase, and carbonyl reductase/prostaglandin 9-ketoreductase genes and prostaglandin E2 synthase/prostaglandin F synthase ratio between corpora lutea ipsi- and contralateral to the uterine horn with the developing embryos
Manually annotated by BRENDA team
Q5FYA7
no or very low expression of prostaglandin F2alpha synthase synthase
Manually annotated by BRENDA team
-
isoform AKR1B1 is expressed at a high level during the menstrual cycle during the secretory phase and in both epithelial and stromal cells
Manually annotated by BRENDA team
-
during luteolysis, activity of 20alpha-hydroxysteroid dehydrogenase synthesizing prostaglandin F2alpha
Manually annotated by BRENDA team
Q2TJA5
from cyclic and pregnant animals, high expression level of the microsomal endometrium-type isozyme, spatiotemporal expression during estrous cycle and early pregnancy
Manually annotated by BRENDA team
-
isozyme PGF synthase I in endothelial cells of the whole area of the spinal cord, and isozyme PGF synthase II in endothelial cells of the blood vessels only
Manually annotated by BRENDA team
-
liver-type isozyme, sinusoidal endothelial cells in the liver
Manually annotated by BRENDA team
-
isozyme PGF synthase II
Manually annotated by BRENDA team
-
isoform AKR1B1 is expressed at a high level during the menstrual cycle during the secretory phase and in both epithelial and stromal cells
Manually annotated by BRENDA team
A9CQL8
-
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
anterior uveal and scleral complex
Manually annotated by BRENDA team
-
glioblastoma cell
Manually annotated by BRENDA team
P42330
both activities of enzymes AKR1C1/AKR1C2 and AKR1C3 are present in the periovuatory granulosa cell
Manually annotated by BRENDA team
-
both activities of enzymes AKR1C1/AKR1C2 and AKR1C3 are present in the periovuatory granulosa cell. Prostaglandin F synthase mRNA and protein levels are low before treatment with gonadotropin and peak 24-36 h after gonadotropin administration
Manually annotated by BRENDA team
Macaca fascicularis AKR1C3
-
both activities of enzymes AKR1C1/AKR1C2 and AKR1C3 are present in the periovuatory granulosa cell. Prostaglandin F synthase mRNA and protein levels are low before treatment with gonadotropin and peak 24-36 h after gonadotropin administration
-
Manually annotated by BRENDA team
-
high activity
Manually annotated by BRENDA team
-
embryonic kidney cell, isozyme PGFS-I
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
proximal tubule, the enzyme is associated with the cyclooxygenase-I, COX-I
Manually annotated by BRENDA team
-
co-localization of cyclooxygenase-1, prostaglandin F receptor and prostaglandin F synthase
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
two different active sites
Manually annotated by BRENDA team
-
liver-type isozyme
Manually annotated by BRENDA team
-
liver-type isozyme
Manually annotated by BRENDA team
-
liver-type isozyme, sinusoidal endothelial cells
Manually annotated by BRENDA team
Q2TJA5
high expression level of the lung-type and the liver-type isozymes
Manually annotated by BRENDA team
-
PGFS-II, liver-type isozyme
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
contractile interstitial cells
Manually annotated by BRENDA team
-
two different active sites
Manually annotated by BRENDA team
-
lung-type isozyme
Manually annotated by BRENDA team
-
lung-type isozyme
Manually annotated by BRENDA team
-
PGH2 9-,11-endoperoxide reductase activity lung-type isozyme
Manually annotated by BRENDA team
-
PGFS-I, lung-type isozyme
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
enzyme co-localizes with myelin basic protein in myelin sheaths but not in axons
Manually annotated by BRENDA team
-
PGH2 9-,11-endoperoxide reductase activity is expressed and active at early pregnant sows, probably also in cyclic sows
Manually annotated by BRENDA team
-
in pregnant myometrium, PGI2, PGD2 and PGF2 synthases are highly expressed while prostaglandin dehydrogenase is underexpressed. Myometrium from non-pregnant women has lower levels of prostaglandin synthases and higher levels of prostaglandin dehydrogenase than pregnant myometrium
Manually annotated by BRENDA team
-
dendrites and somata, isozyme PGF synthase I
Manually annotated by BRENDA team
-
cultured oligodendrocytes at 7 days in vitro express the enzyme in cytoplasmic processes where the enzyme is co-localized with myelin basic protein
Manually annotated by BRENDA team
Macaca fascicularis AKR1C3
-
-
-
Manually annotated by BRENDA team
-
high activity
Manually annotated by BRENDA team
Macaca fascicularis AKR1C3
-
-
-
Manually annotated by BRENDA team
-
expression levels in uninucleated trophoblasts of the placentome of pregnant cows, especially chorionic plate and apical tertiary villi, overview
Manually annotated by BRENDA team
-
the prostaglandin synthase expression profile favours production of PGD2, PGE2 and PGF2, with high levels of prostaglandin transporters and catabolic prostaglandin dehydrogenase suggesting rapid prostaglandin turnover
Manually annotated by BRENDA team
-
utero/placental expression of isoform AKR1C3 is found in the superficial uterine glands throughout gestation and in the trophoblast cells within the feto-maternal contact zone during placentation
Manually annotated by BRENDA team
-
the enzyme is associated with the cyclooxygenase-II, COX-II
Manually annotated by BRENDA team
-
neuronal dendrites and somata of gray matter
Manually annotated by BRENDA team
-
isozymes PGF synthase I and II
Manually annotated by BRENDA team
-
colocalization of prostaglandin F2alpha receptor FP and PGFS I
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
isozyme PGF synthase II
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
expression of both cyclooxygenase-1 and prostaglandin F synthase proteins in wild-type and prostaglandin F-receptor deficient strain
Manually annotated by BRENDA team
-
high activity
Manually annotated by BRENDA team
-
uninucleated cell
Manually annotated by BRENDA team
-
glioblastoma cell
Manually annotated by BRENDA team
-
high activity
Manually annotated by BRENDA team
-
PGFS mRNA and protein expression in the endometrium does not differ between pregnancy and oestrous cycle but PGFS mRNA in the myometrium increases during pregnancy both in the gravid and the non-gravid uterine horns
Manually annotated by BRENDA team
-
uterine tissues at delivery
Manually annotated by BRENDA team
-
uterine expression of isoforms AKR1C3 is up-regulated postimplantation and declines prepartum. Enzyme co-localizes with 15-prostaglandin dehydrogenase
Manually annotated by BRENDA team
-
lung fibroblast cell
Manually annotated by BRENDA team
additional information
-
immunocytochemical localization study
Manually annotated by BRENDA team
additional information
-
enzyme tissue localization analysis
Manually annotated by BRENDA team
additional information
Q2TJA5
isozyme expression levels and tissue distribution, overview
Manually annotated by BRENDA team
additional information
-
low activity in deferent duct and epididymidis
Manually annotated by BRENDA team
additional information
-
isoform AKR1C3 expression is weak or absent in luteal samples
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
liver-type isozyme
Manually annotated by BRENDA team
-
cultured oligodendrocytes at 7 days in vitro express the enzyme in cytoplasmic processes where the enzyme is co-localized with myelin basic protein
Manually annotated by BRENDA team
-
liver-type isozyme
Manually annotated by BRENDA team
-
not-inducible isozyme
Manually annotated by BRENDA team
-
not-inducible isozyme PGFS-I
Manually annotated by BRENDA team
-
inducible isozyme m-PGFS
Manually annotated by BRENDA team
Q2TJA5
microsomal endometrium-type isozyme
-
Manually annotated by BRENDA team
additional information
-
no liver-type isozyme in mitochondrion, nucleus, or Golgi apparatus
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
17000
-
-
657211
20000
A9CQL8
immunoprecipitation, Western blot analysis
687797
23000
-
by zinc staining
687797
23230
-
expressed protein
687797
30500
-
SDS-PAGE, sedimentation equilibrium and gel filtration
389460
33000
-
SDS-PAGE
389446
33000
-
-
657211
36000
-
gel filtration
389453
36000
-
SDS-PAGE
389454
36000
-
gel filtration; SDS-PAGE
389455
36000
-
liver-type isozyme, gel filtration
667297
36670
-
amino acid analysis
389458
36670
-
lung-type isozyme, sequence calculation
654159
36670
-
lung enzyme, sequence calculation
657211
36700
-
Western blot with antibody staining
389445
36740
-
amino acid analysis, SDS-PAGE
389449
36740
-
liver-type isozyme, sequence calculation
654159
36840
-
amino acid analysis
389448
37000
-
lung and liver isozymes
657211
37000
-
lung isozyme
657211
66000
-
SDS-PAGE
389461, 389462
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 35000, SDS-PAGE
?
-
x * 35000, SDS-PAGE
?
-
x * 37000, SDS-PAGE
?
Q2TJA5
x * 36800, approximately, sequence calculation
dimer
A9CQL8
-
dimer
-
2 * 23000, wild-type and mutants, SDS-PAGE
monomer
-
1 * 36000, SDS-PAGE
monomer
-
1 * 36000, gel filtration
monomer
-
1 * 16000
monomer
-
1 * 36666, lung enzyme, sequence calculation
monomer
-
1 * 36666, lung-type isozyme, sequence calculation, 1 * 36742, liver-type isozyme, sequence calculation
monomer
-
1 x 36000, liver-type isozyme, SDS-PAGE
additional information
-
enzyme has a (alpha/beta)8 barrel structure, from crystal structure determination
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
16 mg/ml purified enzyme complexed with inhibitors acetate, flufenamic acid or indomethacin, hanging drop vapour diffusion method in 0.006 ml drops, 1:1 mixture of protein solution containing 10 mM potassium phosphate, pH 7.0, 1 mM DTT, 1 mM EDTA, 2 mM NADP+, with reservoir solution containing 25% w/v PEG 4000, 100 mM sodium citrate, pH 6.0, 2.5% v/v 2-methyl-2,4-pentanediol, and 800 mM ammonium acetate, 6 days to maximum size, X-ray diffraction structure determination of the complexes and analysis at 1.2-2.1 A resolution
-
20 mg/ml purified recombinant enzyme in a solution containing 1.4 mM PGD2 or inhibitor rutin, 1.2 mM NADP+ and NADPH, 50 mM MES, pH 6.0, and 25% w/v PEG 8000, hanging drop vapour diffusion method, 2-3 days, thick plate-shaped crystals of enzyme with NADP+ and PGD2 and of enzyme with NADPH and rutin, X-ray diffraction structure determination and analysis at 1.69 A resolution
-
AKR1C3 in complex with NADP+ and indomethacin
-
homology modeling of enzyme in complex with inhibitor indomethacin
-
in complex with bimatoprost and NADPH, hanging drop vapor diffusion method, using 1.0 mM BMP, 1.0 mM NADPH, 0.14 M NaCl, 50 mM MES buffer (pH 7.0), and 26% (w/v) PEG 8000; purified recombinant enzyme in complex with NADPH and bimatoprost BMP, an ocular hypotensive agent bound near the PGD2 binding site located on the alpha- and omega-chains, hanging drop vapour diffusion method, from 50 mM MES, pH 7.0, containing 7 mg/ml protein, 0.14 M NaCl, 26% w/v PEG 8000, 1.0 mM NADPH, and 1.0 mM BMP, added in a 95% ethanol solution, 4C, 14 days, thick plate-shaped crystals, X-ray diffraction structure determination and analysis at 2.0 A resolution
-
10 mg/ml purified recombinant enzyme from 0.1 M HEPES/NaOH, pH 7.5, 2.0 M ammonium sulfate, 5% w/v PEG 400, and 0.5 M NADPH by hanging drop vapour diffusion method, 20C, 3 weeks, X-ray diffraction structure determination at room temperature and analysis at 2.6 A resolution
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
100
-
no reduction of prostaglandin D2 11-reductase after 5 min
389454
100
-
5 min, inactivation
667297
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
activity is reduced less than 20% after freezing and thawing several times
-
several freezing and thawing cycles reduce the activity of stored purified liver-type isozyme by 50%
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80C, concentration 1.5 mg per ml 10 mM potassium phosphate buffer pH 7.0, stable for several months
-
-80C, 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%
-
25C, concentration 1.5 mg per ml 10 mM potassium phosphate buffer pH 7.0, 80-90% activity, 1 month
-
4-23C, purified liver-type isozyme, 1 month, 80-90% remaining activity
-
4C, concentration 1.5 mg per ml 10 mM potassium phosphate buffer pH 7.0, 80-90% activity, 1 month
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native liver-type isozyme from liver, 342fold to homogeneity by ammonium sulfate fractionation, anion exchange and adsorption chromatography
-
partial
-
recombinant wild-type liver-type isoyzme and mutant enzymes from COS-7 cells, to homogeneity
-
; recombinant enzyme from Escherichia coli strain HB101 to homogeneity
-
; recombinant enzyme from Escherichia coli, to homogeneity
-
recombinant enzyme from Escherichia coli to homogeneity
-
to apparent homogeneity, on Ni-NTA resin and by gel filtration; to apparent homogeneity, on Ni-NTA resin and by gel filtration
-
to apparent homogeneity on Ni2+ column
-
to apparent homogeneity, on Ni-NTA resin and by gel filtration
-
enzyme from lung, to homogeneity
-
on Ni2+ column, 102- and 152fold purification of the prostamide F synthase and PGF synthase activities, respectively, achieved from the swine brain (90 g) with a yield of 1.4 and 2%, respectively. Mutants expressed to homogeneity
A9CQL8
recombinant enzyme from Escherichia coli by GSH affinity chromatography, cleavage of the fusion protein glutathione S-tranferase by thrombin, and DEAE ion exchange chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expession in Escherichia coli MC1061 or HB101
-
expression in COS-7 cells
-
expression in Escherichia coli
-
liver-type isozyme, full length cDNA from cDNA library, DNA and amino acid sequence determination and analysis, transient expression of wild-type and mutant enzymes in COS-7 cells
-
-
P42330
expressed in Escherichia coli HB101 cells; expression Escherichia coli HB101
-
expressed in Escherichia coli HB101 cells; expression in Escherichia coli strain HB101
-
expression in Escherichia coli
-
expression in Escherichia coli BL21(DE3)
-
expression in Escherichia coli HB101
-
into vector pET-28a and expressed in Escherichia coli BL21 (DE3); into vector pET-28a and expressed in Escherichia coli BL21 (DE3)
-
overexpression of AKR1C3 using a pLNCX retroviral vector in MCF-7 cell line
-
recombinant enzyme is expressed in Escherichia coli
-
expression in Escherichia coli
-
into vector pET-28a and expressed in Escherichia coli BL21 (DE3)
-
wild-type and mutants, plasmid pCold II-PM/PGFS expressed in Escherichia coli BL21 cells
-
DNA and amino acid sequence analysis, expression analysis in endometrium of cyclic and pregnant animals
Q2TJA5
expressed in Escherichia coli BL21 cells
A9CQL8
expression in Escherichia coli
-
expression in Escherichia coli strain BL21(DE3) as GST-fusion protein
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
uterine expression of isoforms AKR1C3 is up-regulated post implantation and declines prepartum
-
expression is significantly up-regulated by oestradiol plus progesterone at oestrus and the mid phase of pseudopregnancy and is also up-regulated by a single treatment with progesterone at late pseudopregnancy. Simultaneous incubation with oestradiol and progesterone up-regulates prostaglandin-endoperoxide synthase PTGS2 gene expression at oestrus and mid-luteal phase. Treatment with oestradiol and /or progesterone affects neither prostaglandin F2alpha secretion nor prostaglandin F2alpha synthase expression at any phase after 12 h of culture
E2IGW3
in cultured myometrial cells there is a dose-dependent stimulatory effect of interleukin 1beta and tumor necrosis factor alpha on PTGS2, PTGES and AKR1B1, i.e.PGF synthase expression
-
interleukin IL-1beta is able to upregulate COX-2 and AKR1B1 proteins as well as prostaglandin F2alpha production under normal glucose concentrations. The promoter activity of AKR1B1 gene is increased by IL-1beta particularly around the multiple stress response region
-
AKR1B3 mRNA is expressed in preadipocytes, and its level increases about 4fold at day 1 after initiation of adipocyte differentiation, and then quickly decreases the following day to a level lower than that in the preadipocytes
-
expression of the enzyme increases between P9 and P14 during the postnatal development, presumably in accordance with myelinogenesis
-
PGFS mRNA in the myometrium increases during pregnancy both in the gravid and the non-gravid uterine horns
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
H170C
-
fully active
H170C
-
site-directed mutagenesis, increased Km for prostaglandin PGD2 and 8fold decreased Km for prostaglandin PGH2 compared to the wild-type enzyme
K225S
-
2fold as active as wild-type
K225S
-
site-directed mutagenesis, slightly increased Km for prostaglandin PGD2 and PGH2 compared to the wild-type enzyme
N306Y
-
half as active as wild-type
N306Y
-
site-directed mutagenesis, increased Km for prostaglandin PGD2 and 5fold increased activity with prostaglandin PGH2 compared to the wild-type enzyme
R223L
-
5fold as active as wild-type
R223L
-
site-directed mutagenesis, increased Km for prostaglandin PGD2 compared to the wild-type enzyme
R27E
-
fully active
R27E
-
site-directed mutagenesis, increased Km for prostaglandin PGD2 compared to the wild-type enzyme
R91Q
-
fully active
R91Q
-
site-directed mutagenesis, increased Km for prostaglandin PGD2 compared to the wild-type enzyme
S301R
-
2.5fold as active as wild-type
S301R
-
site-directed mutagenesis, slightly increased Km for prostaglandin PGD2 and PGH2 compared to the wild-type enzyme
D43E
-
only trace activities in presence and absence of NADPH
D43N
-
only trace activities in presence and absence of NADPH
H110A
-
only trace activities in presence and absence of NADPH
H110F
-
only trace activities in presence and absence of NADPH
K77L
-
only trace activities in presence and absence of NADPH
Y48F
-
69% of wild-type activity in presence of NADPH, 138% of wild-type isomerization activity in absence of NADPH, 0.2% of wild-type activity reducing 4-nitrobenzaldehyde
Y55F
-
site-directed mutagenesis, the mutant loses its PGD2 11-ketoreductase activity, but not the PGH2 9,11-endoperoxide reductase, the mutated enzyme loses the prostaglandin D2 11-ketoreductase activity but retains the prostaglandin H2 9,-11-endoperoxide reductase activity
C44S
-
retains 63% of the enzyme activity of the wild-type
C44S/C47S
-
shows values below 1% of the enzyme activity of the wild-type
C47S
-
shows values below 1% of the enzyme activity of the wild-type
Y55F
-
complete elimination of PGD2, and PQ reductase activities, 27fold stimulation of PGH2 reductase activity
K77R
-
only trace activities in presence and absence of NADPH
additional information
-
coexpression of COX-1 and COX-2 increases the endogenous cytosolic PGFS-I activity, but only slightly the membrane-bound activity, overview
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
-
AKR1C3 likely plays important roles in the development of hormone-dependent, and possibly hormone-independent, breast cancer. It is highly expressed in normal breast and upregulated in breast cancer, where its expression is associated with a worse prognosis
pharmacology
-
enzyme is a target for cyclooxygenase-independent antineoplastic actions of nonsteroidal anti-inflammatory drugs
synthesis
-
development of a coupled assay method for enzymatic formation of prostamide F2alpha from anandamide by the cyclooxygenase-II and the prostaglandin synthase F involving the intermediate metabolite, prostamide H2
medicine
-
peri- and postimplantation conceptus. Prostaglandin H synthase and prostaglandin E synthase are down-regulated, and prostaglandin G synthase, prostaglandin F synthase and carbonyl reductase/prostaglandin 9-reductase are down-regulated in conceptuses during trophoblasic elongation. After initiation of implantation, expression of prostaglandin G synthase, prostaglandin F synthase and carbonyl reductase/prostaglandin 9-reductase in conceptuses increases and remains higher until days 24-25 of pregnancy