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Information on EC 1.3.1.48 - 13,14-dehydro-15-oxoprostaglandin 13-reductase
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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 expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
prostaglandin reductase 1, ltbdh/pgr, prostaglandin delta13-reductase, leukotriene b4 dehydrogenase, 15-oxoprostaglandin 13-reductase, pgr-2, pg reductase, 15-keto-pg reductase, 15-oxoprostaglandin-delta13-reductase, delta13-15-ketoprostaglandin reductase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
15-ketoprostaglandin DELTA-13-reductase
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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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bifunctional leukotriene B4 12-hydroxydehydrogenase/15-oxo-prostaglandin 13-reductase
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bifunctional LTB4 12-hydroxydehydrogenase/15-oxo-prostaglandin 13-reductase
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a beta-NADPH-dependent alkenal/one oxidoreductase which has a role for leukotriene B4 12-hydroxydehydrogenase/15-ketoprostaglandinDELTA13-reductase
DELTA13-15-ketoprostaglandin reductase
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leukotriene B4 12-hydroxydehydrogenase/15-ketoprostaglandin 13-reductase
PGR
prostaglandin 13-reductase
prostaglandin DELTA13-reductase
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reductase, 15-oxo-DELTA13-prostaglandin
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prostaglandin 13-reductase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
11alpha-hydroxy-9,15-dioxoprostanoate + NAD(P)+ = (13E)-11alpha-hydroxy-9,15-dioxoprost-13-enoate + NAD(P)H + H+
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
reduction
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redox reaction
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PATHWAY SOURCE
PATHWAYS
BRENDA
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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+.
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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+
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?
(5S,6R)-dihydroxy-15-oxo-(7E,9E,11Z,13E)-eicosatetraenoic acid + NADH
13,14-dihydro-(5S,6R)-dihydroxy-15-oxo-(7E,9E,11Z)-eicosatetraenoic acid + NAD+
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trivial name 15-oxo-lipoxin A4
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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)+
(Z)-3-[(5-methoxy-3-oxo-2(3H)-benzofuranylidene)-methyl]benzoic acid + NAD(P)H
3-[(5-methoxy-3-oxo-2,3-dihydro-1-benzofuran-2-yl)methyl]benzoic acid + NAD(P)+
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?
1-(p-carboxyphenyl)-5-cyano-3-oxo-1-pentene + NAD(P)H
1-(p-carboxyphenyl)-5-cyano-3-oxo-pentane + NAD(P)+
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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)+
11-hydroxy-9,15-dioxoprosta-5,13-dien-1-oic acid + NADPH
11-hydroxy-9,15-dioxoprosta-5-en-1-oic acid + NADP+
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?
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 E1 + NADH + H+
13,14-dihydro-15-ketoprostaglandin E1 + NAD+
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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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r
15-ketoprostaglandin E2 + NADPH + H+
13,14-dihydro-15-keto-prostaglandin E2 + NADP+
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?
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
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)+
trans-2-(o-hydroxybenzylidene)acetophenone + NAD(P)H
(o-hydroxybenzyl)acetophenone + NAD(P)+
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?
trans-2-benzylidenecyclohexan-2-one + NAD(P)H
benzylcyclohexan-2-one + NAD(P)+
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?
trans-3-(2-furyl)acrolein + NAD(P)H
2-furylpropanal + NAD(P)+
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?
trans-4-furyl-3-buten-2-one + NAD(P)H
4-furyl-butane-2-one + NAD(P)+
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?
trans-benzylideneacetophenone + NAD(P)H
benzylacetophenone + NAD(P)+
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?
trans-phenyl-1-propenyl ketone + NAD(P)H
phenylpropane-1-one + NAD+
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?
(5S,12R)-dihydroxy-(6E,8Z,10Z,14E)-eicosatetraenoic acid + NADH
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15-keto-prostaglandin-13-reductase activity is 200fold higher than leukotrien B4-12hydroxydehydrogenase activity
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?
(5S,12R)-dihydroxy-(6E,8Z,10Z,14E)-eicosatetraenoic acid + NADH
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trivial name leukotriene B4, enzyme exhibits a 15-ketoprostaglandin-13-reductase and a very low leukotriene B4 12-hydroxydehydrogenase activity
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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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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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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 substrate: prostaglandin E1
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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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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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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
(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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?
(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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?
(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
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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?
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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?
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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?
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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?
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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?
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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?
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 E + NAD(P)H
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second step in metabolism of E- and Falpha-type prostaglandins
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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-ketoprostaglandin E + NAD(P)H
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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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r
15-ketoprostaglandin E1 + NADH + H+
13,14-dihydro-15-keto-prostaglandin E1 + NAD+
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r
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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r
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
15-oxoprostaglandin F1alpha + 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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?
15-oxoprostaglandin F1alpha + NAD(P)H
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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)+
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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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essential enzyme for eicosanoid inactivation
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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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?
additional information
?
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not active towards 6-keto-prostaglandin F1alpha, prostaglandin F2beta, 11beta-prostaglandin F2alpha, 13,14-dihydro-15-keto-prostaglandin D2, 13,14-dihydro-15-keto-prostaglandin E2, 13,14-dihydro-15-keto-PGF2alpha, and leukotriene B4
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?
additional information
?
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bifunctional enzyme capable of inactivating leukotriene B4 and 15-oxo-prostaglandins, enzyme plays a role in growth suppressive functions in lung cancer
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?
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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+
-
-
-
?
15-ketoprostaglandin E + NAD(P)H
?
-
second step in metabolism of E- and Falpha-type prostaglandins
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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-ketoprostaglandin E + NAD(P)H
?
-
second step in metabolism of E- and Falpha-type prostaglandins
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-
?
15-oxoprostaglandin F1alpha + NAD(P)H
?
-
second step in metabolism of E- and Falpha-type prostaglandins
-
-
?
15-oxoprostaglandin F1alpha + NAD(P)H
?
-
second step in metabolism of E- and Falpha-type prostaglandins
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-
?
15-oxoprostaglandin F1alpha + NAD(P)H
?
-
second step in metabolism of E- and Falpha-type prostaglandins
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-
?
additional information
?
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essential enzyme for eicosanoid inactivation
-
-
?
additional information
?
-
bifunctional enzyme capable of inactivating leukotriene B4 and 15-oxo-prostaglandins, enzyme plays a role in growth suppressive functions in lung cancer
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NAD(P)H
-
in crude extracts: NADH is 30% as effective as NADPH, in purified enzyme: NADH is 10% as effectic as NADPH
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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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
-
-
5-(2-chloro-3-(2-(4-methyl-1,3-thiazolidin-5-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
5-(2-chloro-3-(2-(cyclohexyloxy)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
5-(2-chloro-3-(2-(propan-2-yloxy)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
5-(2-chloro-3-(2-(pyridin-2-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
5-(2-chloro-3-(3-phenylpropoxy)benzylidene)thiazolidine-2,4-dione
-
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
-
-
Disulfiram
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0.1 mM, 61% inhibition, cofactor NADPH, substrate 15-ketoprostaglandin E2
Cibacron blue 3 G-A
-
competitive inhibition vs. NADH, noncompetitive vs. 15-keto-prostaglandin E2
dicoumarol
-
0.1 mM, 86% inhibition, cofactor NADPH, substrate 15-ketoprostaglandin E2
indomethacin
-
0.1 mM, 97% inhibition, cofactor NADPH, substrate 15-ketoprostaglandin E2
NADPH
-
competitive inhibition vs. NADH, noncompetitive vs. 15-keto-prostaglandin E2
quercitrin
-
0.1 mM, 76% inhibition, cofactor NADPH, substrate 15-ketoprostaglandin E2
additional information
evaluation of non-steroidal anti-inflammatory drugs (NSAIDs) as enzyme potential inhibitors
-
additional information
-
evaluation of non-steroidal anti-inflammatory drugs (NSAIDs) as enzyme potential inhibitors
-
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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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Adenoviridae Infections
Restoration of leukotriene B(4)-12-hydroxydehydrogenase/15- oxo-prostaglandin 13-reductase (LTBDH/PGR) expression inhibits lung cancer growth in vitro and in vivo.
Breast Neoplasms
Auranofin/Vitamin C: A Novel Drug Combination Targeting Triple-Negative Breast Cancer.
Carcinoma
Effect of prostaglandin reductase 1 (PTGR1) on gastric carcinoma using lentivirus-mediated system [Retraction].
Carcinoma
Effect of prostaglandin reductase 1 (PTGR1) on gastric carcinoma using lentivirus-mediated system.
Carcinoma, Hepatocellular
Increased expression of prostaglandin reductase 1 in hepatocellular carcinomas from clinical cases and experimental tumors in rats.