Information on EC 1.1.1.189 - prostaglandin-E2 9-reductase

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The expected taxonomic range for this enzyme is: Tetrapoda

EC NUMBER
COMMENTARY hide
1.1.1.189
-
RECOMMENDED NAME
GeneOntology No.
prostaglandin-E2 9-reductase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+ = (5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
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reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Arachidonic acid metabolism
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-
Metabolic pathways
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arachidonic acid metabolism
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SYSTEMATIC NAME
IUBMB Comments
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate:NADP+ 9-oxidoreductase
Reduces prostaglandin E2 to prostaglandin F2alpha. A number of other 9-oxo- and 15-oxo-prostaglandin derivatives can also be reduced to the corresponding hydroxy compounds. May be identical with EC 1.1.1.197 15-hydroxyprostaglandin dehydrogenase (NADP+).
CAS REGISTRY NUMBER
COMMENTARY hide
42613-35-4
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate + NAD(P)+
(5Z,13E)-11alpha-hydroxy-9,15-dioxoprosta-5,13-dienoate + NAD(P)H
show the reaction diagram
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate + NADPH
show the reaction diagram
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-9alpha,11alpha-dihydroxy-15-oxoprosta-5,13-dienoate + NADPH
show the reaction diagram
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADP+
(5Z,13E)-9alpha-hydroxy-11,15-dioxoprosta-5,13-dienoate + NADPH
show the reaction diagram
17alpha-hydroxyprogesterone + NADPH
?
show the reaction diagram
-
-
-
-
?
2,6-dichloroindophenol + NADPH
?
show the reaction diagram
-
-
-
-
?
20alpha-hydroxy-pregn-4-en-3-one + NADP+
progesterone + NADPH
show the reaction diagram
4-nitrobenzaldehyde + NADPH
?
show the reaction diagram
-
-
-
-
?
5alpha-dihydrotestosterone + NADPH
?
show the reaction diagram
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
show the reaction diagram
alpha-tocopherolquinone + NADPH
?
show the reaction diagram
-
-
-
-
?
corticosterone + NADPH
?
show the reaction diagram
-
-
-
-
?
cortisole + NADPH
?
show the reaction diagram
-
-
-
-
?
menadione + NADPH
?
show the reaction diagram
-
-
-
-
?
phenylglyoxal + NADPH
?
show the reaction diagram
-
-
-
-
?
prostaglandin E2 + NAD(P)H
prostaglandin F2alpha + NAD(P)+
show the reaction diagram
prostaglandin E2 + NAD(P)H + H+
prostaglandin F2alpha + NAD(P)+
show the reaction diagram
-
-
-
-
?
prostaglandin E2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
prostaglandin E2 + NADPH + H+
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NAD(P)H
prostaglandin E2 + NAD(P)+
show the reaction diagram
prostaglandin H2 + NAD(P)H
prostaglandin F2alpha + NAD(P)+
show the reaction diagram
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate + NADPH
show the reaction diagram
prostaglandin E2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
key enzyme responsible for the control of prostaglandin levels in placental tissues
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-
r
prostaglandin E2 + NADPH + H+
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NAD(P)H
prostaglandin E2 + NAD(P)+
show the reaction diagram
prostaglandin H2 + NAD(P)H
prostaglandin F2alpha + NAD(P)+
show the reaction diagram
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
NADPH
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Zn2+
-
1.9 g-atoms per mol enzyme
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
17beta-estradiol
5,5'-dithiobis(2-nitrobenzoate)
-
complete inhibition at 1 mM concentration
aspirin
-
equimolar to substrate inhibits 65% of enzyme activity
cortisol
Cu2+
-
5 mM concentration
FAD
-
5 mM concentration
Fentiazac
-
non competitive
indomethacin
interferon tau
-
recombinant ovine interferon tau inhibits 25% prostaglandin E2 and prostaglandin F2alpha production at a concentration of 1 ng per ml
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lonazolac
-
equimolar to substrate inhibits 78% of enzyme activity
NAD+
-
5 mM concentration 60% inhibition, competitive
NADP+
-
5 mM concentration 60% inhibition, non-competitive
nitric oxide
-
inhibition e.g. by NOC-18, a NO donor
p-chloromercuribenzoate
-
complete inhibition at 1 mM concentration
palmitic acid
-
inhibits enzyme in dose-dependent manner
progesterone
prostaglandin E2
-
inhibits the reduction of 20alpha-hydroxy-pregn-4-en-3-one to progesterone competitively
Substance P
-
-
vitamin D3
-
equimolar to substrate inhibits 38% of enzyme activity
additional information
-
no effect: Mg2+, Ca2+, EDTA, EGTA, cAMP and cGMP
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
angiotensin I
-
at 0.1 mM concentration
ATP
-
at 1mM concentration slight stimulation
CTP
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at 1mM concentration slight stimulation
gonadotropin-releasing hormone
-
-
GTP
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at 1mM concentration slight stimulation
interferon tau
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recombinant ovine interferon tau stimulates significantly prostaglandin E2 and prostaglandin F2alpha production at a concentration of 0.01 mg per ml
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lipopolysaccharides
-
strong induction of the membrane-bound lung isozyme, significant induction in stomach, intestine, spleen, kidney, testis, and pancreas, overview
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Oxytocin
Sodium diphosphate
-
-
additional information
-
aminoguanidine, an inducible nitric oxide synthase inhibitor, does not affect the enzyme, but activates L-NAME, a non-selective nitric oxide synthase inhibitor, thereby increasing prostaglandin F2alpha synthesis
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.022 - 0.028
20alpha-hydroxy-pregn-4-en-3-one
0.45
4-Nitrobenzaldehyde
-
-
0.0023 - 0.006
9,10-phenanthrenequinone
0.83
DL-glyceraldehyde
-
-
0.31
menadione
-
-
1.1
methylglyoxal
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-
0.0016 - 0.0164
NADPH
0.08 - 0.32
prostaglandin E2
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.45
Fentiazac
-
non competitive
0.85
indomethacin
-
non competitive
1.5
progesterone
-
non competitive
0.025
prostaglandin E2
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competitive inhibitor for the reduction of 20alpha-hydroxy-pregn-4-en-3-one to progesterone
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00036
-
-
0.00038
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-
0.00052
-
-
0.02
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0.034
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-
additional information
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activities in retained and not retained placenta samples from different animal groups
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4
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assay at
7.4 - 8.8
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-
7.4
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assay at
7.4 - 9
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-
7.8 - 9
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8.3
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forward reaction
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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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
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endometrial
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
28000
-
gel filtration, 4 isoforms
29000
-
gel filtration
31000
-
alpha, 1 * 31000, SDS-PAGE
33000
-
gel filtration
35000
-
alpha, 1 * 35000, SDS-PAGE
45000 - 55000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45
-
25% activity after incubation at 45°C for 10 min
100
-
no activity after heating at 100°C for 3 min
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
partial purification
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
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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
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