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Information on EC 1.3.1.48 - 13,14-dehydro-15-oxoprostaglandin 13-reductase and Organism(s) Homo sapiens and UniProt Accession P15428
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1.3.1.48 13,14-dehydro-15-oxoprostaglandin 13-reductaseIUBMB Comments
Reduces 13,14-dehydro-15-oxoprostaglandins to 13,14-dihydro derivatives. The enzyme from placenta is specific for NAD+.
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The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
prostaglandin reductase 1, leukotriene b4 dehydrogenase, ltbdh/pgr, prostaglandin delta13-reductase, 15-oxoprostaglandin 13-reductase, pgr-2, pg reductase, 15-keto-pg reductase, 15-oxoprostaglandin-delta13-reductase, delta13-15-ketoprostaglandin reductase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
15-ketoprostaglandin DELTA-13-reductase
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-
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15-ketoprostaglandin DELTA13-reductase
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15-oxoprostaglandin 13-oxidase
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15-oxoprostaglandin 13-reductase
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15-oxoprostaglandin DELTA13-reductase
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DELTA13-15-ketoprostaglandin reductase
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prostaglandin 13-reductase
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prostaglandin DELTA13-reductase
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reductase, 15-oxo-DELTA13-prostaglandin
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
redox reaction
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oxidation
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reduction
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SYSTEMATIC NAME
IUBMB Comments
11alpha-hydroxy-9,15-dioxoprostanoate:NAD(P)+ Delta13-oxidoreductase
Reduces 13,14-dehydro-15-oxoprostaglandins to 13,14-dihydro derivatives. The enzyme from placenta is specific for NAD+.
CAS REGISTRY NUMBER
COMMENTARY
57406-74-3
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(13E)-11alpha-hydroxy-9,15-dioxoprost-13-enoate + NADPH + H+
11alpha-hydroxy-9,15-dioxoprostanoate + NADP+
-
-
-
?
11alpha-hydroxy-9,15-dioxoprostanoate + NAD(P)+
(13E)-11alpha-hydroxy-9,15-dioxoprost-13-enoate + NAD(P)H + H+
-
-
-
?
(5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NAD(P)H
(5Z)-11alpha-hydroxy-9,15-dioxoprost-5-enoate + NAD(P)+
11-hydroxy-9,15-dioxoprosta-5,13-dien-1-oic acid + NAD(P)H
11-hydroxy-9,15-dioxoprosta-5-en-1-oic acid + NAD(P)+
15-ketoprostaglandin E + NAD(P)H
?
-
second step in metabolism of E- and Falpha-type prostaglandins
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-
?
15-ketoprostaglandin E1 + NADH + H+
13,14-dihydro-15-keto-prostaglandin E1 + NAD+
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-
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-
r
15-ketoprostaglandin E1 + reduced nicotinamide hypoxanthine dinucleotide + H+
13,14-dihydro-15-keto-prostaglandin E1 + nicotinamide hypoxanthine dinucleotide
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-
-
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r
15-ketoprostaglandin E2 + reduced nicotinamide hypoxanthine dinucleotide + H+
13,14-dihydro-15-ketoprostaglandin E2 + nicotinamide hypoxanthine dinucleotide
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93% activity compared to NADH
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-
r
15-oxoprostaglandin F1alpha + NAD(P)H
?
-
second step in metabolism of E- and Falpha-type prostaglandins
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-
?
9,11-dihydroxy-15-oxoprosta-5,13-dien-1-oic acid + NAD(P)H
9,11-dihydroxy-15-oxoprosta-5-en-1-oic aicd + NAD(P)+
(5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NAD(P)H
(5Z)-11alpha-hydroxy-9,15-dioxoprost-5-enoate + NAD(P)+
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-
-
ir
(5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NAD(P)H
(5Z)-11alpha-hydroxy-9,15-dioxoprost-5-enoate + NAD(P)+
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no substrates: 15-hydroxyprostaglandins, progesterone, cortisone, orotic acid, fumaric acid
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?
(5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NAD(P)H
(5Z)-11alpha-hydroxy-9,15-dioxoprost-5-enoate + NAD(P)+
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no substrates: 15-hydroxyprostaglandins, progesterone, cortisone, orotic acid, fumaric acid
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ir
(5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NAD(P)H
(5Z)-11alpha-hydroxy-9,15-dioxoprost-5-enoate + NAD(P)+
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55% of activity with 15-keto-prostaglandin E2
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ir
11-hydroxy-9,15-dioxoprosta-5,13-dien-1-oic acid + NAD(P)H
11-hydroxy-9,15-dioxoprosta-5-en-1-oic acid + NAD(P)+
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i.e. 15-ketoprostaglandin E2
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?
11-hydroxy-9,15-dioxoprosta-5,13-dien-1-oic acid + NAD(P)H
11-hydroxy-9,15-dioxoprosta-5-en-1-oic acid + NAD(P)+
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i.e. 15-ketoprostaglandin E2
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?
11-hydroxy-9,15-dioxoprosta-5,13-dien-1-oic acid + NAD(P)H
11-hydroxy-9,15-dioxoprosta-5-en-1-oic acid + NAD(P)+
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i.e. 15-ketoprostaglandin E2
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?
11-hydroxy-9,15-dioxoprosta-5,13-dien-1-oic acid + NAD(P)H
11-hydroxy-9,15-dioxoprosta-5-en-1-oic acid + NAD(P)+
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i.e. 15-ketoprostaglandin E2
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?
15-ketoprostaglandin A1 + NAD(P)H
?
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108% of activity with 15-keto-prostaglandin E2
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?
15-ketoprostaglandin B1 + NAD(P)H
?
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79% of activity with 15-keto-prostaglandin E2
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?
15-ketoprostaglandin E2 + NADH + H+
13,14-dihydro-15-ketoprostaglandin E2 + NAD+
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r
15-ketoprostaglandin E2 + NADH + H+
13,14-dihydro-15-ketoprostaglandin E2 + NAD+
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100% activity
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r
9,11-dihydroxy-15-oxoprosta-5,13-dien-1-oic acid + NAD(P)H
9,11-dihydroxy-15-oxoprosta-5-en-1-oic aicd + NAD(P)+
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56% of activity with 15-keto-prostaglandin E2
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?
9,11-dihydroxy-15-oxoprosta-5,13-dien-1-oic acid + NAD(P)H
9,11-dihydroxy-15-oxoprosta-5-en-1-oic aicd + NAD(P)+
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i.e. 15-ketoprostaglandin F2alpha
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?
9,11-dihydroxy-15-oxoprosta-5,13-dien-1-oic acid + NAD(P)H
9,11-dihydroxy-15-oxoprosta-5-en-1-oic aicd + NAD(P)+
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i.e. 15-ketoprostaglandin F2alpha
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?
9,11-dihydroxy-15-oxoprosta-5,13-dien-1-oic acid + NAD(P)H
9,11-dihydroxy-15-oxoprosta-5-en-1-oic aicd + NAD(P)+
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i.e. 15-ketoprostaglandin F2alpha
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?
additional information
?
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PGR1, which catalyzes the NADPH-dependent reduction of the alpha,beta-double bond of aliphatic and aromatic aldehydes and ketones, and 15-keto-prostaglandins. PGR1 also shows low activity in the oxidation of leukotriene B4. The best substrates in terms of kcat/Km are 15-keto-prostaglandins, trans-3-nonen-2-one, and trans-2-decenal. Molecular docking simulations, role of Arg56 and Tyr245 in 15-keto-prostaglandin binding, overview
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?
additional information
?
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PGR1, which catalyzes the NADPH-dependent reduction of the alpha,beta-double bond of aliphatic and aromatic aldehydes and ketones, and 15-keto-prostaglandins. PGR1 also shows low activity in the oxidation of leukotriene B4. The best substrates in terms of kcat/Km are 15-keto-prostaglandins, trans-3-nonen-2-one, and trans-2-decenal. Molecular docking simulations, role of Arg56 and Tyr245 in 15-keto-prostaglandin binding, overview
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-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
11alpha-hydroxy-9,15-dioxoprostanoate + NAD(P)+
(13E)-11alpha-hydroxy-9,15-dioxoprost-13-enoate + NAD(P)H + H+
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?
15-ketoprostaglandin E + NAD(P)H
?
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second step in metabolism of E- and Falpha-type prostaglandins
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?
15-oxoprostaglandin F1alpha + NAD(P)H
?
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second step in metabolism of E- and Falpha-type prostaglandins
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
5-(2-chloro-3-((4-methylcyclohexyl)methoxy)benzylidene)-1,3-thiazolidine-2,4-dione
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5-(2-chloro-3-((5-oxo-5,6,7,8-tetrahydronaphthalen-1-yl)oxy)benzylidene)-1,3-thiazolidine-2,4-dione
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5-(2-chloro-3-(2-(4-methyl-1,3-thiazolidin-5-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
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5-(2-chloro-3-(2-(cyclohexyloxy)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
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-
5-(2-chloro-3-(2-(propan-2-yloxy)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
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-
5-(2-chloro-3-(2-(pyridin-2-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
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5-(2-chloro-3-(3-phenylpropoxy)benzylidene)thiazolidine-2,4-dione
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the compound significantly increases the level of PGE2 in skin defects
5-(3-(bicyclo[2.2.1]hept-2-ylmethoxy)-2-chlorobenzylidene)-1,3-thiazolidine-2,4-dione
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-
Cibacron blue 3 G-A
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competitive inhibition vs. NADH, noncompetitive vs. 15-keto-prostaglandin E2
NADPH
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competitive inhibition vs. NADH, noncompetitive vs. 15-keto-prostaglandin E2
additional information
evaluation of non-steroidal anti-inflammatory drugs (NSAIDs) as enzyme potential inhibitors
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additional information
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evaluation of non-steroidal anti-inflammatory drugs (NSAIDs) as enzyme potential inhibitors
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additional information
-
thiazolidinediones as enzyme inhibitors. No inhibition by 5-(2-chloro-3-(1-cyclopropylethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00014
5-(2-chloro-3-((4-methylcyclohexyl)methoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.00013
5-(2-chloro-3-((5-oxo-5,6,7,8-tetrahydronaphthalen-1-yl)oxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.00109
5-(2-chloro-3-(2-(4-methyl-1,3-thiazolidin-5-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.00023
5-(2-chloro-3-(2-(cyclohexyloxy)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.00017
5-(2-chloro-3-(2-(propan-2-yloxy)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.0103
5-(2-chloro-3-(2-(pyridin-2-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.000029
5-(2-chloro-3-(2-cyclohexylethoxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.00015
5-(2-chloro-3-(2-cyclopentylethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.000059
5-(2-chloro-3-(3-cyclohexylpropoxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.00014
5-(2-chloro-3-(3-nitrophenoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.000045
5-(2-chloro-3-(3-phenylpropoxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.000095
5-(2-chloro-3-(4-cyclohexylbutoxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.0117
5-(2-chloro-3-(4-nitrobenzyloxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.000054
5-(2-chloro-3-(4-phenylbutoxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.00036
5-(2-chloro-3-(cyclobutylmethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.000058
5-(2-chloro-3-(cyclohexylmethoxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.000212
5-(2-chloro-3-(cyclohexyloxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.00002
5-(2-chloro-3-(cyclopentylmethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.00258
5-(2-chloro-3-(cyclopentyloxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.000122
5-(2-chloro-3-phenethoxybenzylidene)thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.000257
5-(3-(benzyloxy)-2-chlorobenzylidene)thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
0.00862
5-(3-(bicyclo[2.2.1]hept-2-ylmethoxy)-2-chlorobenzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH 75, 37°C, recombinant GST-tagged enzyme
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
the three human PG reductases are zinc-independent members of the medium-chain dehydrogenase/reductase (MDR) superfamily
metabolism
prostaglandins are lipid compounds derived from arachidonic acid by the action of cyclooxygenases, acting locally as messenger molecules in a wide variety of physiological processes, such as inflammation, cell survival, apoptosis, smooth muscle contraction, adipocyte differentiation, vasodilation and platelet aggregation inhibition. In the inactivating pathway of prostaglandins, the first metabolic intermediates are 15-keto-prostaglandins, which are further converted into 13,14-dihydro-15-keto-prostaglandins by different enzymes having 15-keto-prostaglandin reductase activity
physiological function
-
prostaglandin E2, PGE2, has a short half-life in vivo because is rapidly oxidized to 15-ketoprostaglandins by the cytosolic enzyme 15-PGDH. PGE2 acts through EP2 and EP4 receptors to mediate regeneration and hematopoietic stem cell development via the Wnt signaling pathway. Wnt activation in stem cells requires PGE2, and the PGE2/Wnt interaction is a master regulator of vertebrate regeneration and recovery. PGE2 regulates vertebrate hematopoietic stem cell induction and engraftment
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 50% glycerol v/v, 5 mM potassium phosphate, 1 mM EDTA, pH 7.0, stable for at least 6 months
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant expression as GST-tagged enzyme in Escherichiacoli strain BL-21LysS
-
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hansen, H.S.
Purification and assay of 15-ketoprostaglandin delta 13-reductase from bovine lung
Methods Enzymol.
86
156-167
1982
Bos taurus, Gallus gallus, Homo sapiens
Jarabak, J.
Isolation and properties of a 15-ketoprostaglandin delta 13-reductase from human placenta
Methods Enzymol.
86
163-167
1982
Homo sapiens
Westbrook, C.; Jarabak, J.
Purification and partial characterization of an NADH-linked delta13-15-ketoprostaglandin reductase from human placenta
Biochem. Biophys. Res. Commun.
66
541-546
1975
Homo sapiens
Westbrook, C.; Jarabak, J.
15-Ketoprostaglandin delta13 reductase from human placenta: purification, kinetics, and inhibitor binding
Arch. Biochem. Biophys.
185
429-442
1978
Homo sapiens
Mesa, J.; Alsina, C.; Oppermann, U.; Pares, X.; Farres, J.; Porte, S.
Human prostaglandin reductase 1 (PGR1) Substrate specificity, inhibitor analysis and site-directed mutagenesis
Chem. Biol. Interact.
234
105-113
2015
Homo sapiens (P15428), Homo sapiens
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