Information on EC 1.1.1.141 - 15-hydroxyprostaglandin dehydrogenase (NAD+) and Organism(s) Homo sapiens

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The enzyme appears in selected viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.1.1.141
-
RECOMMENDED NAME
GeneOntology No.
15-hydroxyprostaglandin dehydrogenase (NAD+)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD+ = (5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
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-
-
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SYSTEMATIC NAME
IUBMB Comments
(5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate:NAD+ 15-oxidoreductase
Acts on prostaglandin E2, F2alpha and B1, but not on prostaglandin D2. cf. EC 1.1.1.196 15-hydroxyprostaglandin-D dehydrogenase (NADP+) and EC 1.1.1.197 15-hydroxyprostaglandin dehydrogenase (NADP+).
CAS REGISTRY NUMBER
COMMENTARY hide
9030-87-9
-
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
physiological function
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-oxoprost-5,13-dienoate + NAD+
(5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADH + H+
show the reaction diagram
(5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADH
(5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD+
show the reaction diagram
-
-
i.e. 15-hydroxyprostaglandin or (15S)-PGE2
-
r
(5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD+
(5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADH + H+
show the reaction diagram
-
-
-
-
?
(5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid + NAD+
(5Z,8E,10E)-12-oxo-5,8,10-heptadecatrienoic acid + NADH
show the reaction diagram
11alpha,15(S)-dihydroxy-9-ketoprost-5,13-dienoic acid + NAD(P)+
11alpha-hydroxy-9,15-diketoprost-5,13-dienoic acid + NADH
show the reaction diagram
15(S)-hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid + NAD+
15-oxo-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid + NADH
show the reaction diagram
-
-
-
-
?
15-hydroxyprostaglandin + NAD+
15-oxoprostaglandin + NADH + H+
show the reaction diagram
5,6-chrysenequinone + NADH
?
show the reaction diagram
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-
-
-
?
5,6-chrysenequinone + NADH
? + H2O2
show the reaction diagram
-
formation of potentially hazardous semiquinones, reaction mechanism, overview
-
-
?
6-ketoprostaglandin F1alpha + NAD+
6,15-diketoprostaglandin F1alpha
show the reaction diagram
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-
-
?
9,10-phenanthrenequinone + NADH
?
show the reaction diagram
-
-
-
-
?
9,10-phenanthrenequinone + NADH
? + H2O2
show the reaction diagram
-
formation of potentially hazardous semiquinones, reaction mechanism, overview
-
-
?
prostaglandin A1 + NAD+
15-ketoprostaglandin A1 + NADH + H+
show the reaction diagram
prostaglandin A2 + NAD+
15-ketoprostaglandin A2 + NADH + H+
show the reaction diagram
prostaglandin D1 + NAD+
15-ketoprostaglandin D1 + NADH + H+
show the reaction diagram
-
very low activity
-
?
prostaglandin E1 + NAD+
15-ketoprostaglandin E1 + NADH + H+
show the reaction diagram
prostaglandin E2 + NAD+
15-ketoprostaglandin E2 + NADH + H+
show the reaction diagram
prostaglandin E2 + NAD+
15-oxoprostaglandin E2 + NADH + H+
show the reaction diagram
-
-
-
-
?
prostaglandin F2alpha + NAD(P)+
15-ketoprostaglandin F2alpha + NADH + H+
show the reaction diagram
prostaglandin F2alpha + NAD+
15-ketoprostaglandin F2alpha + NADH + H+
show the reaction diagram
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-
-
-
?
prostaglandin I2 + NAD+
15-ketoprostaglandin I2 + NADH + H+
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)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD+
(5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADH + H+
show the reaction diagram
(5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADH
(5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD+
show the reaction diagram
-
-
i.e. 15-hydroxyprostaglandin or (15S)-PGE2
-
r
(5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD+
(5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADH + H+
show the reaction diagram
-
-
-
-
?
15-hydroxyprostaglandin + NAD+
15-oxoprostaglandin + NADH + H+
show the reaction diagram
prostaglandin E2 + NAD+
15-oxoprostaglandin E2 + NADH + H+
show the reaction diagram
-
-
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-Azido-NAD+
-
2.4% of activity with NAD+
thio-NAD+
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5-33% of activity with NAD+ depending on substrate
additional information
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1-butyl-1H-benzimidazol-5-yl)(piperidin-1-yl)methanone
-
-
(1-phenyl-1H-benzimidazol-5-yl)(piperidin-1-yl)methanone
-
-
(1-tert-butyl-1H-benzimidazol-5-yl)(piperidin-1-yl)methanone
-
-
(3,3-dimethylpiperidin-1-yl)[1-(3-methylphenyl)-1H-benzimidazol-5-yl]methanone
-
-
(3,5-dimethylpiperidin-1-yl)[1-(3-methylphenyl)-1H-benzimidazol-5-yl]methanone
-
-
(4-([(4-chlorophenyl)sulfanyl]methyl)phenyl)(4-methylpiperidin-1-yl)methanone
-
-
(4-bromopiperidin-1-yl)[1-(3-methylphenyl)-1H-benzimidazol-5-yl]methanone
-
-
(4-[(2-bromophenoxy)methyl]phenyl)(piperidin-1-yl)methanone
-
-
(5Z)-5-[3-bromo-4-(2-cyclohexylethoxy)benzylidene]-1,3-thiazolidine-2,4-dione
-
-
(5Z)-5-[3-chloro-4-(2-cyclohexylethoxy)benzylidene]-1,3-thiazolidine-2,4-dione
-
-
(5Z)-5-[3-chloro-4-(3-cyclohexylpropoxy)benzylidene]-1,3-thiazolidine-2,4-dione
-
-
(5Z)-5-[3-chloro-4-(4-cyclohexylbutoxy)benzylidene]-1,3-thiazolidine-2,4-dione
-
-
(5Z)-5-[3-chloro-4-(cyclohexylmethoxy)benzylidene]-1,3-thiazolidine-2,4-dione
-
-
(5Z)-5-[3-chloro-4-(cyclohexyloxy)benzylidene]-1,3-thiazolidine-2,4-dione
-
-
(5Z)-5-[4-(2-cyclohexylethoxy)-3-methoxybenzylidene]-1,3-thiazolidine-2,4-dione
-
-
(5Z)-5-[4-(2-cyclohexylethoxy)-3-methoxybenzylidene]-3-methyl-1,3-thiazolidine-2,4-dione
-
-
(5Z)-5-[4-(2-cyclohexylethoxy)benzylidene]-1,3-thiazolidine-2,4-dione
-
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(piperidin-1-yl)[1-[3-(propan-2-yl)phenyl]-1H-benzimidazol-5-yl]methanone
-
-
(piperidin-1-yl)[1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-5-yl]methanone
-
-
(piperidin-1-yl)[1-[4-(trifluoromethyl)phenyl]-1H-benzimidazol-5-yl]methanone
-
-
1,2-naphthoquinone
-
0.0002 mM, time dependent inactivation, 1 mM glutathione or 40% glycerol protect from inactivation; inactivation, glutathione protects
12-O-tetradecanoylphorbol-13-acetate
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10 nM, rapid loss of activity in eryrthroleukemia cells during 40 min, inhibition can be prevented by staurosporin indicating that protein kinase C is involved; induces the synthesis of 15-PGDH but inhibits the enzyme activity a protein kinase C mediated mechanism
13-cis-Prostaglandin F2alpha
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; 0.124 mM, 50% inhibition
15-deoxy-DELTA12,14-prostaglandin J2
-
0.024 mM, 50% inhibition
15-epi-prostaglandin E1
-
-
15-Epiprostaglandin E1
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0.17 mM, 50% inhibition
15-ketoprostaglandin E1
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2-([(6-bromo-4H-imidazo[4,5-b]pyridin-2-yl)sulfanyl]methyl)benzonitrile
-
-
2-azido NAD+
-
photoaffinity analog of NAD+, 0.115 mM, complete inactivation
2-hydroxy-5-(3,5-dimethoxycarbonyl-benzoyl)-benzene acetic acid
-
1000 times more potent inhibitor than sulfaphasalazine
2-methyl-1,4-naphthoquinone
-
0.02 mM, time dependent inactivation
2-[[(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)sulfanyl]methyl]benzonitrile
-
-
3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine
-
-
3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine
-
-
3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7,8,9,10,11-hexahydro-5H-[1,2,4]triazolo[4,3-a]azonine
-
-
3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine
-
-
3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole
-
-
3-[1-(3,4-dichlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-[1-(3-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-[1-(4-bromophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-[1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-[1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-[1-(4-methoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-[1-(4-tert-butylphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-[2,5-dimethyl-1-(4-methylphenyl)-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-[2,5-dimethyl-1-(4-nitrophenyl)-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-[2,5-dimethyl-1-[3-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-[2,5-dimethyl-1-[4-(naphthalen-2-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-[2,5-dimethyl-1-[4-(pyridin-2-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-[2,5-dimethyl-1-[4-(pyridin-3-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-[2,5-dimethyl-1-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-[2,5-dimethyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
3-[2,5-dimethyl-3-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)-1H-pyrrol-1-yl]benzonitrile
-
-
4,5-benzo[a]pyrenequinone
-
0.0002 mM, time dependent inactivation
4-((2,5-dioxopyrrolidin-3-ylidene)methyl)phenylthiophene-2-carboxylate
-
-
-
4-methoxybenzyl-2,4-thiazolidinedione
-
-
4-methoxybenzylidene-2,4-thiazolidinedione
-
-
4-[2,5-dimethyl-3-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)-1H-pyrrol-1-yl]benzonitrile
-
-
5-(2-chloro-3-(2-(pyridin-2-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(2-chloro-4-(2-(cyclohexyloxy)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(2-chloro-4-(2-(propan-2-yloxy)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(2-chloro-4-(2-cyclohexylethoxy)benzylidene)-thiazolidine-2,4-dione
-
-
-
5-(2-chloro-4-(2-cyclopentylethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(2-chloro-4-(4-nitrobenzyloxy)benzylidene)thiazolidine-2,4-dione
-
-
-
5-(2-chloro-4-phenbutoxybenzylidene)thiazolidine-2,4-dione
-
-
-
5-(2-chloro-4-phenethoxybenzylidene)thiazolidine-2,4-dione
-
-
-
5-(2-chloro-4-phenpropoxybenzylidene)thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-((4-(prop-1-en-2-yl)cyclohexyl)methoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-((5-oxo-5,6,7,8-tetrahydronaphthalen-1-yl)oxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(2-(4-methyl-1,3-thiazolidin-5-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(2-(5-nitrofuran-2-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(2-(cyclohexyloxy)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(2-(propan-2-yloxy)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(2-(pyridin-2-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(2-(thiophen-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(2-cyclopentylethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(2-cyclopropylpropyl)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(2-thiomorpholine 1,1-dioxideethoxy)benzylidene)-2,4-thiazolidinedione
-
-
-
5-(3-chloro-4-(3-(2-nitroethenyl)phenoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(3-nitrophenoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(3-phenylpropoxy)benzylidene)thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(4-nitrobenzyloxy)benzylidene)thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(4-phenylbutoxy)benzylidene)thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(cyclobutylmethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-(cyclopentylmethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(3-chloro-4-phenylethoxybenzylidene)thiazolidine-2,4-dione
-
-
-
5-(4-((4-methylcyclohexyl)methoxy)benzylidene) thiazolidine-2,4-dione
-
-
5-(4-(1,3-benzodioxol-5-ylmethoxy)-3-chlorobenzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(4-(2-(thiophen-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione
-
-
5-(4-(2-(thiophen-3-yl)ethoxy)benzylidene)thiazolidine-2,4-dione
-
-
5-(4-(2-cyclopentylethoxy)benzylidene)thiazolidine-2,4-dione
-
-
5-(4-(4-(chloromethyl)benzyloxy)benzylidene) thiazolidine-2,4-dione
-
-
5-(4-(benzyloxy)-2-chlorobenzylidene)thiazolidine-2,4-dione
-
-
-
5-(4-(benzyloxy)-3-chlorobenzylidene)thiazolidine-2,4-dione
-
-
-
5-(4-(bicyclo[2.2.1]hept-2-ylmethoxy)-3-chlorobenzylidene)-1,3-thiazolidine-2,4-dione
-
-
-
5-(4-(cyclopentylmethoxy)benzylidene)thiazolidine-2,4-dione
-
-
5-[4-((1-methyl)-cyclohexylmethoxy)benzylidene]-2,4-thiazolidenedione
-
-
5-[4-((1-methyl)-cyclohexylmethoxy)benzyl]-2,4-thiazolidenedione
-
trivial name ciglitazone
5-[4-(benzoxy)benzylidene]-2,4-thiazolidenedione
-
-
5-[4-(cyclohexylbutoxy)benzylidene]-2,4-thiazolidenedione
-
-
5-[4-(cyclohexylethoxy)benzylidene]-2,4-thiazolidenedione
-
-
5-[4-(cyclohexylmethoxy)benzylidene]-2,4-thiazolidenedione
-
-
5-[4-(cyclohexyloxy)benzylidene]-2,4-thiazolidenedione
-
-
5-[4-(cyclohexylpropoxy)benzylidene]-2,4-thiazolidenedione
-
-
5-[[4-(ethoxycarbonyl)phenyl]azo]-2-hydroxy-benzeneacetic acid
-
CAY-10397, specific 15-PGDH inhibitor
7,8-benzo[a]pyrenequinone
-
0.0002 mM, time dependent inactivation, 40% glycerol protects from inactivation; inactivation, glutathione protects
-
7-Oxa-13-prostynoic acid
-
; 0.0475 mM, 50% inhibition
7-oxa-prostanoic acid
-
-
7-Oxoprostanoic acid
-
-
7-Thia-13-prostynoic acid
-
; 0.0068 mM, 50% inhibition
7-thia-prostanoic acid
-
-
arachidonic acid
Berberine
-
0.023 mM, 50% inhibition
Biochanin A
-
0.031 mM, 50% inhibition
CAY 10397
-
specific inhibitor, completely reverses the stimulating effect of ibuprofen on cell proliferation in TT cells
chalcone
-
0.016 mM, 50% inhibition
chrysin
-
0.021 mM, 50% inhibition
ciglitazone
CT-8
-
-
curcumin
-
0.01 mM, 50% inhibition
DuP 697
-
0.022 mM, 50% inhibition
ent-13-dehydro-15-epi-prostaglandin F2alpha
-
-
Ent-13-dehydro-15-epiprostaglandin F3alpha
-
0.055 mM, 50% inhibition
ent-13-dehydroprostaglandin E2
-
; 0.0068 mM, 50% inhibition
epi-7-thia-prostaglandin F2alpha
-
-
epi-7-thiaprostaglandin F2alpha
-
0.0052 mM, 50% inhibition
epigallocatechin gallate
-
0.012 mM, 50% inhibition
Ethacrynic acid
ethanol
ethyl 4-[2,5-dimethyl-3-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)-1H-pyrrol-1-yl]benzoate
-
-
Flufenamic acid
-
0.041 mM, 50% inhibition
flurbiprofen
-
0.062 mM, 50% inhibition
genistein
-
-
glycerol
-
slight inhibition
hexadecanoic acid
-
0.01 mM
ICI 81008
-
-
indomethacin
ketorolac
-
0.028 mM, 50% inhibition
Meclofenamic acid
-
0.073 mM, 50% inhibition
Mefenamic acid
-
0.076 mM, 50% inhibition
mixture of endogenous fatty acids
-
mixture contains palmitic acid, stearic acid linoleic acid and oleic acid, competitive vs. prostaglandine E2
-
MK 886
-
0.037 mM, 50% inhibition
N,N-diethyl-1-(3-methylphenyl)-1H-benzimidazole-5-carboxamide
-
-
N-(2-phenylethyl)-indomethacin amide
-
0.098 mM, 50% inhibition
N-(3-pyridyl)-indomethacin amide
-
0.1 mM, 50% inhibition
N-butyl-1-(3-methylphenyl)-1H-benzimidazole-5-carboxamide
-
-
N-cyclopentyl-1-(3-methylphenyl)-1H-benzimidazole-5-carboxamide
-
-
NAD+
-
-
NADPH
-
-
nat-13-dehydroprostaglandin E2
-
-
nat-13-dehydroprostaglandin F3alpha
-
-
Nat-13-thiaprostaglandin F2alpha
-
0.0088 mM, 50% inhibition
-
nat-7-thia-prostaglandin F2alpha
-
-
nat-l3-dehydroprostaglandin F2alpha
-
-
niflumic acid
-
0.058 mM, 50% inhibition
nimesulide
-
0.051 mM, 50% inhibition
NS 398
-
0.064 mM, 50% inhibition
octadecanoic acid
-
0.01 mM
PD 98059
-
an ERK kinase inhibitor
Prostaglandin B1
prostaglandin E1
-
-
prostaglandin E2
-
-
prostaglandin F2alpha
-
-
Prostanoic acid
pyridoxal 5'-phosphate
-
-
resveratrol
-
0.054 mM, 50% inhibition
rosiglitazone
sulfaphasalazine
-
anticolitic drug
-
sulindac
-
0.041 mM, 50% inhibition
sulindac sulfide
-
0.018 mM, 50% inhibition
sulindac sulfone
-
0.038 mM, 50% inhibition
tetradecanoic acid
-
0.01 mM
Tetranitromethane
-
-
thyroxine
-
-
troglitazone
[1-(2-methoxyphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
-
[1-(3-chlorophenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
-
[1-(3-methoxyphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
-
[1-(3-methylphenyl)-1H-benzimidazol-5-yl](3-methylpiperidin-1-yl)methanone
-
-
[1-(3-methylphenyl)-1H-benzimidazol-5-yl](3-phenylpiperidin-1-yl)methanone
-
-
[1-(3-methylphenyl)-1H-benzimidazol-5-yl](4-methylpiperazin-1-yl)methanone
-
-
[1-(3-methylphenyl)-1H-benzimidazol-5-yl](morpholin-4-yl)methanone
-
-
[1-(3-methylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
-
[1-(3-methylphenyl)-1H-benzimidazol-5-yl](pyrrolidin-1-yl)methanone
-
-
[1-(3-methylphenyl)-1H-benzimidazol-5-yl][3-(propan-2-yl)piperidin-1-yl]methanone
-
-
[1-(3-methylphenyl)-1H-benzimidazol-5-yl][3-(trifluoromethyl)piperidin-1-yl]methanone
-
-
[1-(3-methylphenyl)-1H-benzimidazol-5-yl][4-(trifluoromethyl)piperidin-1-yl]methanone
-
-
[1-(3-tert-butylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
-
[1-(4-chlorophenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
-
[1-(4-methoxyphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
-
[1-(4-methylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
-
[1-(4-tert-butylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
-
[4-(4-methoxyphenyl)piperazin-1-yl](4-[(phenylsulfanyl)methyl]phenyl)methanone
-
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
17beta-estradiol
-
slight activation
corticosterone
-
4fold activation
cortisone
-
5fold activation
cyclooxygenase-1 inhibitors
-
selective or not
-
dexamethasone
-
10fold activation
dihydrotestosterone
-
-
erlotinib
-
epidermal growth factor receptor tyrosine kinase inhibitor, trreatment of cells increases the expression of the enzyme in a subset of non-small-cell lung cancer lines
estradiol
-
2fold activation
pioglitazone
-
upregulation of expression, involving peroxisome proliferator-activated receptor gamma. Upregulation results in reduced production of prostaglandin E2 and finally inhibition of lung cancer growth
Prednisolone
-
6fold activation
progesterone
rosiglitazone
-
upregulation of expression, involving peroxisome proliferator-activated receptor gamma. Upregulation results in reduced production of prostaglandin E2 and finally inhibition of lung cancer growth
sulindac sulfone
-
-
testosterone
Thionicotinamide adenine dinucleotide
Triamcinolone
-
7fold activation
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0012 - 0.026
(5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate
0.00765
(5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid
-
-
0.0521
15-ketoprostaglandin E1
-
at pH 7.0
0.0266 - 0.0528
15-ketoprostaglandin E2
0.063
6-oxo-prostaglandin F1alpha
-
recombinant enzyme expressed in E. coli
0.022 - 0.72
NAD+
0.0156 - 0.0594
NADH
0.0045 - 0.033
prostaglandin A1
0.003 - 0.022
Prostaglandin A2
0.0013 - 0.027
prostaglandin E1
0.0025 - 0.0135
prostaglandin E2
0.0213 - 0.059
prostaglandin F2alpha
additional information
additional information
-
Michaelis-Menten kinetics, overview
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
37 - 262
(5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate
35 - 247
NAD+
6.1 - 14.1
prostaglandin E2
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
900 - 2800
prostaglandin E2
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.26
15-ketoprostaglandin E1
-
substrate prostaglandin E1
0.62
4-methoxybenzyl-2,4-thiazolidinedione
-
37C, pH 7.5
0.017
4-methoxybenzylidene-2,4-thiazolidinedione
-
37C, pH 7.5
0.0006
5-[4-((1-methyl)-cyclohexylmethoxy)benzylidene]-2,4-thiazolidenedione
-
37C, pH 7.5
0.0022
5-[4-((1-methyl)-cyclohexylmethoxy)benzyl]-2,4-thiazolidenedione
-
37C, pH 7.5
0.0012
5-[4-(benzoxy)benzylidene]-2,4-thiazolidenedione
-
37C, pH 7.5
0.005
5-[4-(cyclohexylbutoxy)benzylidene]-2,4-thiazolidenedione
-
37C, pH 7.5
0.00009
5-[4-(cyclohexylethoxy)benzylidene]-2,4-thiazolidenedione
-
37C, pH 7.5
0.00027
5-[4-(cyclohexylmethoxy)benzylidene]-2,4-thiazolidenedione
-
37C, pH 7.5
0.0009
5-[4-(cyclohexyloxy)benzylidene]-2,4-thiazolidenedione
-
37C, pH 7.5
0.117 - 0.168
NAD+
0.015
NADH
-
substrate prostaglandin E1
0.0139
prostaglandin E1
-
-
0.0109
prostaglandin E2
-
-
0.0873
prostaglandin F2alpha
-
-
additional information
additional information
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000068
(1-butyl-1H-benzimidazol-5-yl)(piperidin-1-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000022
(1-phenyl-1H-benzimidazol-5-yl)(piperidin-1-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000034
(1-tert-butyl-1H-benzimidazol-5-yl)(piperidin-1-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000068
(3,3-dimethylpiperidin-1-yl)[1-(3-methylphenyl)-1H-benzimidazol-5-yl]methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000271
(3,5-dimethylpiperidin-1-yl)[1-(3-methylphenyl)-1H-benzimidazol-5-yl]methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000631
(4-([(4-chlorophenyl)sulfanyl]methyl)phenyl)(4-methylpiperidin-1-yl)methanone
Homo sapiens
-
pH 8, 25C
0.000076
(4-bromopiperidin-1-yl)[1-(3-methylphenyl)-1H-benzimidazol-5-yl]methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000089
(4-[(2-bromophenoxy)methyl]phenyl)(piperidin-1-yl)methanone
Homo sapiens
-
pH 8, 25C
0.000019
(5Z)-5-[3-bromo-4-(2-cyclohexylethoxy)benzylidene]-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH and temperature not specified in the publication
0.000008
(5Z)-5-[3-chloro-4-(2-cyclohexylethoxy)benzylidene]-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH and temperature not specified in the publication
0.00001
(5Z)-5-[3-chloro-4-(3-cyclohexylpropoxy)benzylidene]-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH and temperature not specified in the publication
0.000024
(5Z)-5-[3-chloro-4-(4-cyclohexylbutoxy)benzylidene]-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH and temperature not specified in the publication
0.000028
(5Z)-5-[3-chloro-4-(cyclohexylmethoxy)benzylidene]-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH and temperature not specified in the publication
0.000047
(5Z)-5-[3-chloro-4-(cyclohexyloxy)benzylidene]-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH and temperature not specified in the publication
0.000025
(5Z)-5-[4-(2-cyclohexylethoxy)-3-methoxybenzylidene]-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH and temperature not specified in the publication
0.05
(5Z)-5-[4-(2-cyclohexylethoxy)-3-methoxybenzylidene]-3-methyl-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH and temperature not specified in the publication
0.000051
(5Z)-5-[4-(2-cyclohexylethoxy)benzylidene]-1,3-thiazolidine-2,4-dione
Homo sapiens
-
pH and temperature not specified in the publication
0.000068
(piperidin-1-yl)[1-[3-(propan-2-yl)phenyl]-1H-benzimidazol-5-yl]methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000048
(piperidin-1-yl)[1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-5-yl]methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.00086
(piperidin-1-yl)[1-[4-(trifluoromethyl)phenyl]-1H-benzimidazol-5-yl]methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000141
2-([(6-bromo-4H-imidazo[4,5-b]pyridin-2-yl)sulfanyl]methyl)benzonitrile
Homo sapiens
-
pH 8, 25C
0.000242
3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine
Homo sapiens
-
pH and temperature not specified in the publication
0.000192
3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine
Homo sapiens
-
pH and temperature not specified in the publication
0.000383
3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7,8,9,10,11-hexahydro-5H-[1,2,4]triazolo[4,3-a]azonine
Homo sapiens
-
pH and temperature not specified in the publication
0.000054
3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.00089
3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH 8, 25C
0.00304
3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole
Homo sapiens
-
pH and temperature not specified in the publication
0.000022
3-[1-(3,4-dichlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.000034
3-[1-(3-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.000048
3-[1-(4-bromophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.000038
3-[1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.000121
3-[1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.000086
3-[1-(4-methoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.000136
3-[1-(4-tert-butylphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.000034
3-[2,5-dimethyl-1-(4-methylphenyl)-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.000108
3-[2,5-dimethyl-1-(4-nitrophenyl)-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.000048
3-[2,5-dimethyl-1-[3-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.000108
3-[2,5-dimethyl-1-[4-(naphthalen-2-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.001078
3-[2,5-dimethyl-1-[4-(pyridin-2-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.000271
3-[2,5-dimethyl-1-[4-(pyridin-3-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.000383
3-[2,5-dimethyl-1-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.000068
3-[2,5-dimethyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
Homo sapiens
-
pH and temperature not specified in the publication
0.000076
3-[2,5-dimethyl-3-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)-1H-pyrrol-1-yl]benzonitrile
Homo sapiens
-
pH and temperature not specified in the publication
0.000264
4-((2,5-dioxopyrrolidin-3-ylidene)methyl)phenylthiophene-2-carboxylate
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000096
4-[2,5-dimethyl-3-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)-1H-pyrrol-1-yl]benzonitrile
Homo sapiens
-
pH and temperature not specified in the publication
0.008915
5-(2-chloro-3-(2-(pyridin-2-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000211
5-(2-chloro-4-(2-(cyclohexyloxy)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.00105
5-(2-chloro-4-(2-(propan-2-yloxy)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000013
5-(2-chloro-4-(2-cyclohexylethoxy)benzylidene)-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000042
5-(2-chloro-4-(2-cyclopentylethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.00454
5-(2-chloro-4-(4-nitrobenzyloxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000081
5-(2-chloro-4-phenbutoxybenzylidene)thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000178
5-(2-chloro-4-phenethoxybenzylidene)thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000052
5-(2-chloro-4-phenpropoxybenzylidene)thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000075
5-(3-chloro-4-((4-(prop-1-en-2-yl)cyclohexyl)methoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000071
5-(3-chloro-4-((5-oxo-5,6,7,8-tetrahydronaphthalen-1-yl)oxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.005165
5-(3-chloro-4-(2-(4-methyl-1,3-thiazolidin-5-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.002077
5-(3-chloro-4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000123
5-(3-chloro-4-(2-(5-nitrofuran-2-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.00002
5-(3-chloro-4-(2-(cyclohexyloxy)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.002738
5-(3-chloro-4-(2-(propan-2-yloxy)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.00444
5-(3-chloro-4-(2-(pyridin-2-yl)ethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000084
5-(3-chloro-4-(2-(thiophen-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000099
5-(3-chloro-4-(2-cyclopentylethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000132
5-(3-chloro-4-(2-cyclopropylpropyl)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000223
5-(3-chloro-4-(2-thiomorpholine 1,1-dioxideethoxy)benzylidene)-2,4-thiazolidinedione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000059
5-(3-chloro-4-(3-(2-nitroethenyl)phenoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.0001
5-(3-chloro-4-(3-nitrophenoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000038
5-(3-chloro-4-(3-phenylpropoxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.00093
5-(3-chloro-4-(4-nitrobenzyloxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000048
5-(3-chloro-4-(4-phenylbutoxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000009
5-(3-chloro-4-(cyclobutylmethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000011
5-(3-chloro-4-(cyclopentylmethoxy)benzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.00002
5-(3-chloro-4-phenylethoxybenzylidene)thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000052
5-(4-((4-methylcyclohexyl)methoxy)benzylidene) thiazolidine-2,4-dione
Homo sapiens
-
pH 7.5, temperature not specified in the publication
0.000193
5-(4-(1,3-benzodioxol-5-ylmethoxy)-3-chlorobenzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000031
5-(4-(2-(thiophen-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
pH 7.5, temperature not specified in the publication
0.00006
5-(4-(2-(thiophen-3-yl)ethoxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
pH 7.5, temperature not specified in the publication
0.000116
5-(4-(2-cyclopentylethoxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
pH 7.5, temperature not specified in the publication
0.000124
5-(4-(4-(chloromethyl)benzyloxy)benzylidene) thiazolidine-2,4-dione
Homo sapiens
-
pH 7.5, temperature not specified in the publication
0.000487
5-(4-(benzyloxy)-2-chlorobenzylidene)thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000048
5-(4-(benzyloxy)-3-chlorobenzylidene)thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000165
5-(4-(bicyclo[2.2.1]hept-2-ylmethoxy)-3-chlorobenzylidene)-1,3-thiazolidine-2,4-dione
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
-
0.000045
5-(4-(cyclopentylmethoxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
pH 7.5, temperature not specified in the publication
0.000051
CT-8
Homo sapiens
-
at pH 7.5, temperature not specified in the publication
0.000038
ethyl 4-[2,5-dimethyl-3-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)-1H-pyrrol-1-yl]benzoate
Homo sapiens
-
pH and temperature not specified in the publication
0.000383
N,N-diethyl-1-(3-methylphenyl)-1H-benzimidazole-5-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.001358
N-butyl-1-(3-methylphenyl)-1H-benzimidazole-5-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.000961
N-cyclopentyl-1-(3-methylphenyl)-1H-benzimidazole-5-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.000027
[1-(2-methoxyphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000012
[1-(3-chlorophenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000019
[1-(3-methoxyphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000022
[1-(3-methylphenyl)-1H-benzimidazol-5-yl](3-methylpiperidin-1-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000429
[1-(3-methylphenyl)-1H-benzimidazol-5-yl](3-phenylpiperidin-1-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.00271
[1-(3-methylphenyl)-1H-benzimidazol-5-yl](4-methylpiperazin-1-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.00304
[1-(3-methylphenyl)-1H-benzimidazol-5-yl](morpholin-4-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000019 - 0.000056
[1-(3-methylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
0.000383
[1-(3-methylphenyl)-1H-benzimidazol-5-yl](pyrrolidin-1-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000048
[1-(3-methylphenyl)-1H-benzimidazol-5-yl][3-(propan-2-yl)piperidin-1-yl]methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000068
[1-(3-methylphenyl)-1H-benzimidazol-5-yl][3-(trifluoromethyl)piperidin-1-yl]methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.001524
[1-(3-methylphenyl)-1H-benzimidazol-5-yl][4-(trifluoromethyl)piperidin-1-yl]methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000171
[1-(3-tert-butylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.00022
[1-(4-chlorophenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.00019
[1-(4-methoxyphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.00019
[1-(4-methylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.000054
[1-(4-tert-butylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.01
[4-(4-methoxyphenyl)piperazin-1-yl](4-[(phenylsulfanyl)methyl]phenyl)methanone
Homo sapiens
-
value above, pH 8, 25C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00083
-
recombinant 15-PGDH
1.75
-
-
1.765
-
-
1.791
-
-
7.79
-
purified native enzyme
12.15
-
enzyme from placenta
19.8
-
recombinant enzyme
24
-
enzyme from placenta
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 9
-
assay at
7
-
assay at
7.5 - 8.8
-
sharp optimum
7.5
-
assay at
8
-
assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 10
-
strong increase in activity between pH 8.0 and 9.5, sharp decrease above
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
non-small cell lung carcinoma cell line A549, expression of 15-PGDH is induced by dexamethason, prednisolone, betamethasone and triamcinolone
Manually annotated by BRENDA team
-
55000 Da form of enzyme, level increases with preterm premature rupture of membrane
Manually annotated by BRENDA team
-
in preterm chorion, levles of 15-hydroxyprostaglandin dehydrogenase protein and activity are lower when compared to term, and are further reduced with the presence of infection. Preterm premature rapture of membranes and subclinical inflammation do not affect the levels of 29000 Da 15-hydroxyprostaglandin dehydrogenase protein in the fetal membranes
Manually annotated by BRENDA team
-
low enzyme expression level
Manually annotated by BRENDA team
-
lung adenocarcinoma cell line
Manually annotated by BRENDA team
-
15-hydroxyprostaglandin dehydrogenase is expressed mainly in keratinocytes and melanocytes
Manually annotated by BRENDA team
-
erythroleukemia cell line
Manually annotated by BRENDA team
-
invasiveapocrine carcinoma cells correspond to a distinct molecular subtype of breast carcinomas characterized by the expression of 15-prostaglandin dehydrogenase alone or in combination with a novel form of acyl-CoA synthetase medium-chain family member 1, 15-prostaglandin dehydrogenase is not expressed by other breast cancer types
Manually annotated by BRENDA team
-
in hair follicle, 15-hydroxyprostaglandin dehydrogenase is expressed mainly in keratinocytes and melanocytes
Manually annotated by BRENDA team
-
high enzyme expression level
Manually annotated by BRENDA team
-
in hair follicle, 15-hydroxyprostaglandin dehydrogenase is expressed mainly in keratinocytes and melanocytes
Manually annotated by BRENDA team
-
high expression level of 15-PGDH
Manually annotated by BRENDA team
-
enzyme activity is reduced in inflamed mucosa
Manually annotated by BRENDA team
-
low expression level of 15-PGDH
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
UNIPROT
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
24000
-
1 * 24000, SDS-PAGE
24500
-
gel filtration
25000
-
x * 25000, SDS-PAGE
28000
-
gel filtration, MALDI-MS
31000
-
wild type recombinant protein, SDS-PAGE
32000
-
gel filtration in the presence of mercaptoethanol
42000
-
1 * 42000, SDS-PAGE
51500
-
gel filtration
54000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
2 * 29000, SDS-PAGE
monomer
additional information
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
modeling of structure for mutant A140P. Mutation disrupts binding of the substrate prostaglandin E2 both because the pyrrolidine ring of Pro140 fills a space that in the wildtype complex is occupied by the prostaglandin E2 target side-chain 15-OH and because there is a resulting loss of catalytically important hydrogen bonding of the 15-OH to the nearby serine at residue 138
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
when expression is induced at 37C, almost all wild type recombinant HPGD protein is soluble
41.2
-
melting point at pH 8.0, ligand free
45.9
-
melting point at pH 8.0, in the presence of NAD+
52.5
-
melting point at pH 8.0, in the presence of NADH
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
glycerol, 50%, stabilizes
-
NAD+ stabilizes
-
no stabilization by addition of prostaglandins
-
the assay mix containing 50 mM Tris HCl, pH 7.5, 1 mM dithiothreitol, 100 mM prostaglandin E2 and 1 mM NAD+ at 22C is not optimal for HPGD activity, but avoids a sharp, unphysiological pH optimum around pH 9
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, 20% glycerol, 4 weeks, no loss of activity
-
-20C, 5 mM potassium phosphate, pH 7.0, 50% glycerol, 1 mM EDTA, 7 months, 10% loss of activity
-
-20C, 50% glycerol, 10 mM 2-mercaptoethanol, stable for at least 1 year
-
-20C, 50% glycerol, 2 months, 8% loss of activity
-
-20C, purified enzyme in a buffer containing 50% glycerol, 5 mM potassium phosphate, pH 7.0, and 1 mM EDTA, loss less than 10% of its initial activity in 2 months
-
4C, 20% glycerol, 4 weeks, 25% loss of activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
CM-Sepharose, DEAE-Sepharose, Blue Sepharose, Mono-Q
-
glutathione Sepharose column chromatography
-
nickel-Sepharose column chromatography
-
recombinant 15-PGDH
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence, expression analysis and transcriptional regulation, overview
-
enzyme expression analysis
-
expressed in Escherichia coli
-
expressed in Escherichia coli as a His-tagged fusion protein
-
expressed in Escherichia coli BL-21 LysS cells
-
expressed in Escherichia coli strain JM109(DE3); expression in Escherichia coli
-
expressed in Mus musculus RAW macrophages (R15L cells)
-
expression in Escherichia coli
-
expression of 15-PGDH as GST-fusion in Escherichia coli
-
stable expression of wild-type and mutant enzymes in AD-293 cells using an adenovirus shuttle vector
-
transient expression in HT29 cells
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
15-deoxy-DELTA(12,14)-prostaglandin J2 upregulates the expression and the activity of the enzyme through reactive oxygen species-mediated activation of extracellular-signal related kinase1/2 and subsequently Elk-1 in human breast cancer MDA-MB-231 cells
-
15-hydroxyprostaglandin dehydrogenase is upregulated by hydroxychloroquine in rheumatoid arthritis fibroblast-like synoviocytes
-
15-PGDH is overexpressed in malignant ovarian tissue
-
enzyme mRNA levels are significantly higher in aorta samples from patients undergoing abdominal aortic aneurysm repair than in those from healthy multiorgan donors
-
interleukin 4 induces up-regulation of 15-PGDH expression in A549 cells as well as in other lung cancer cell lines
-
the enzyme is downregulated in human hepatoma cells with a high cyclooxygenase-2 expression
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A13G/A14S/Q15K/D36S/W37R
-
no activity
A140P
-
naturally occuring mutation in patients with pulmonary hypertropic osteoarthropathy. Homozygous individuals develop pulmonary hypertrophic osteoarthropathy secondary to chronically elevated prostaglandin E2 levels. Heterozygous relatives also show milder biochemical and clinical manifestations. After expression in Escherichia coli, the mutations renders the protein largely insoluble at 37C, but mostly souble at 20C. Mutant exhibits less than 1.5% of wild-type activity; the mutant shows no detectable activity, the A140P substitution renders the enzyme largely insoluble at 37C, at 27C, the mutant protein is partially soluble, and at 20C it is mostly soluble
A14S/Q15K/D36S/W37R
-
no activity
C152A
-
similar activity as wild-type
C152F
-
no activity
C182A
-
no activity
C182F
-
no activity
C42A
-
similar activity as wild-type
C45F
-
similar activity as wild-type
C63A
-
similar activity as wild-type
C63F
-
10% of wild-type activity
D64E
-
no activity
D64K
-
low activity
D64N
-
similar activity as wild type
D86E
-
similar activity as wild type
D86N
-
similar activity as wild type
I17A
-
270% of wild-type activity
I17E
-
no activity
I17K
-
no activity
I17L
-
364% of wild-type activity
I17V
-
300% of wild-type activity
K155L
-
inactive enzyme
K155Q
-
inactive enzyme
L155L
-
no activity
L155Q
-
no activity
N91A
-
136% of wild-type activity
N91D
-
86% of wild-type activity
N91K
-
no activity
N91L
-
no activity
Q15K
-
approx. 200% of wild-type activity
Q15K/D36A/W37R
-
no activity with NAD+ as cofactor, low activity with NADP+ as cofactor
Q15K/D36S/W37R
-
no activity with NAD+ as cofactor, low activity with NADP+ as cofactor
Q15K/W37K
-
approx. 350% of wild-type activity
Q15K/W37R
-
approx. 350% of wild-type activity, strong activity with NADP+ as cofactor
Q15R
-
approx. 100% of wild-type activity
Q15R/W37K
-
approx. 200% of wild-type activity
Q15R/W37R
-
approx. 200% of wild-type activity, strong activity with NADP+ as cofactor
S138A
-
no activity
S193P
-
the missense mutation in exon 6 of the human HPGD gene encoding NAD+ dependent 15-hydroxyprostaglandin dehydrogenase is involved in the pathogenesis of isolated congenital nail clubbing
T11A
-
no activity
T11C
-
no activity
T11S
-
110% of wild-type activity
T188A
-
no activity
T188S
-
substantial activity, lower than wild-type
T188Y
-
no activity
V186A
-
143% of wild-type activity
V186D
-
no activity
V186I
-
468% of wild-type activity
V186K
-
71% of wild-type activity
W37K
-
approx. 100% of wild-type activity
W37R
-
approx. 100% of wild-type activity
Y151L/K155E
-
inactive
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine