Information on EC 1.1.1.141 - 15-hydroxyprostaglandin dehydrogenase (NAD+)

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The expected taxonomic range for this enzyme is: Amniota

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
-
-
-
-
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
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
rhesus monkey, inducible isozyme
-
-
Manually annotated by BRENDA team
Mus musculus C57BL/6J
C57BL/6J mice
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
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,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-hydroxyeicosatetraenoic acid + NAD+
15-ketoeicosatetraenoic acid + NADH
show the reaction diagram
-
-
-
?
15-hydroxyprostaglandin + NAD+
15-oxoprostaglandin + NADH + H+
show the reaction diagram
19-hydroxyprostaglandin E1 + NAD+
19-hydroxy-15-oxoprostaglandin E1 + NADH
show the reaction diagram
-
-
-
?
20-hydroxyprostaglandin E1 + NAD+
20-hydroxy-15-ketoprostaglandin E1 + NADH
show the reaction diagram
-
-
-
?
5,6-chrysenequinone + NADH
?
show the reaction diagram
-
-
-
-
?
5,6-chrysenequinone + NADH
? + H2O2
show the reaction diagram
-
formation of potentially hazardous semiquinones, reaction mechanism, overview
-
-
?
6-keto-prostaglandin E1 + NAD+
? + NADH
show the reaction diagram
-
-
-
-
?
6-keto-prostaglandin F1alpha + NAD+
? + NADH
show the reaction diagram
-
-
-
-
?
6-ketoprostaglandin E1 + NAD+
6,15-diketoprostaglandin E1
show the reaction diagram
-
-
-
?
6-ketoprostaglandin F1alpha + NAD+
6,15-diketoprostaglandin F1alpha
show the reaction diagram
-
-
-
?
6-ketoprostaglandin F1alpha + NAD+
6,15-diketoprostaglandin F1alpha + NADH + H+
show the reaction diagram
-
-
-
?
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 A1 + NAD+
? + NADH
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 D2 + NAD+
15-ketoprostaglandin D2 + NADH + H+
show the reaction diagram
prostaglandin D2 + NAD+
? + NADH
show the reaction diagram
-
-
-
-
?
prostaglandin E1 + NAD+
15-ketoprostaglandin E1 + NADH + H+
show the reaction diagram
prostaglandin E1 + NAD+
? + NADH
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 E3 + NAD+
15-keto-prostaglandin E3 + 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
-
-
-
-
?
prostaglandin F2alpha + NAD+
? + NADH
show the reaction diagram
-
-
-
-
?
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
15-hydroxyprostaglandin + NAD+
15-oxoprostaglandin + NADH + H+
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-Azido-NAD+
-
2.4% of activity with NAD+
NADP+
-
more efficient than NAD+
thio-NAD+
-
5-33% of activity with NAD+ depending on substrate
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(4-([(4-chlorophenyl)sulfanyl]methyl)phenyl)(4-methylpiperidin-1-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
-
-
(9Z,12E)-13-hydroxyoctadeca-9,12-dienoic acid
-
0.01 mM, 45% inhibition
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
13-cis-Prostaglandin F2alpha
-
; 0.124 mM, 50% inhibition
13-hydroxyperoxyoctadecadienoic acid
-
0.001 mM to 0.01 mM, 50% inhibition with 0.003 mM, uncompetitive inhibition vs. NAD+, noncompetitive vs. prostaglandin E2
15-deoxy-DELTA12,14-prostaglandin J2
-
0.024 mM, 50% inhibition
15-epi-prostaglandin E1
-
-
15-Epiprostaglandin E1
-
0.17 mM, 50% inhibition
15-ketoprostaglandin E1
-
-
15-Ketoprostaglandin E2
-
-
2,4,6-Trinitrobenzenesulfonic acid
-
-
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
2-methyl-1,4-naphthoquinone
-
0.02 mM, time dependent inactivation
3,3',5-triiodothyronine
-
-
3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
-
4,5-benzo[a]pyrenequinone
-
0.0002 mM, time dependent inactivation
4-chloromercuriphenylsulfonic acid
-
-
4-methoxybenzyl-2,4-thiazolidinedione
-
-
4-methoxybenzylidene-2,4-thiazolidinedione
-
-
5-(4-((4-methylcyclohexyl)methoxy)benzylidene) 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-(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
5-[[4-(ethoxycarbonyl)phenyl]azo]2-hydroxy-benzene acetic acid
CAY-10397
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
-
-
Acetylsalicylate
-
-
acrolein
-
irreversible inhibition
adenosine-5'-diphosphoribose
-
-
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
Cu2+
-
0.05 mM to 0.5 mM, 50% inhibition with 0.1 mM, uncompetitive vs. NAD+, non-competitive vs. prostaglandin E2
curcumin
-
0.01 mM, 50% inhibition
diethyldicarbonate
-
-
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
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
linoleic acid
-
0.01 mM, 30% 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-(2-phenylethyl)-indomethacin amide
-
0.098 mM, 50% inhibition
N-(3-pyridyl)-indomethacin amide
-
0.1 mM, 50% inhibition
N-Chlorosuccinimide
-
-
N-ethylmaleimide
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
p-Chloromercuriphenylsulfonic acid
-
-
papaverine
PD 98059
-
an ERK kinase inhibitor
Phenylglyoxal
-
-
Prostaglandin B1
prostaglandin E1
-
-
prostaglandin E2
prostaglandin F2alpha
-
-
Prostanoic acid
pyridoxal 5'-phosphate
-
-
resveratrol
-
0.054 mM, 50% inhibition
rosiglitazone
sulfaphasalazine
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
Tetraiodothyroacetic acid
-
-
Tetranitromethane
-
-
thyroxine
troglitazone
Zn2+
-
0.05 mM to 0.5 mM, 50% inhibition with 0.15 mM, uncompetitive vs. NAD+, non-competitive vs. prostaglandin E2
[1-(3-methylphenyl)-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 - 0.012
(5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid
0.016
15-hydroxyeicosatetraenoic acid
-
-
0.0521
15-ketoprostaglandin E1
-
at pH 7.0
0.0266 - 0.0528
15-Ketoprostaglandin E2
0.077
19-hydroxyprostaglandin E1
-
-
0.283
20-hydroxyprostaglandin E1
-
-
0.066
6-ketoprostaglandin E1
-
-
0.111
6-ketoprostaglandin F1alpha
-
-
0.063
6-oxo-prostaglandin F1alpha
-
recombinant enzyme expressed in E. coli
0.022 - 0.72
NAD+
0.0156 - 0.0594
NADH
0.0045 - 0.038
prostaglandin A1
0.003 - 0.022
Prostaglandin A2
0.741
Prostaglandin D2
-
-
0.0013 - 0.033
prostaglandin E1
0.00158 - 0.059
prostaglandin E2
0.077
prostaglandin E3
-
-
0.0213 - 0.133
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
0.02 - 0.031
15-Ketoprostaglandin E2
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
0.02 - 0.225
adenosine-5'-diphosphoribose
0.14
indomethacin
-
-
0.117 - 0.168
NAD+
0.0135 - 0.015
NADH
0.026 - 0.4
papaverine
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
0.000631
(4-([(4-chlorophenyl)sulfanyl]methyl)phenyl)(4-methylpiperidin-1-yl)methanone
Homo sapiens
-
pH 8, 25C
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
0.000141
2-([(6-bromo-4H-imidazo[4,5-b]pyridin-2-yl)sulfanyl]methyl)benzonitrile
Homo sapiens
-
pH 8, 25C
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
0.000052
5-(4-((4-methylcyclohexyl)methoxy)benzylidene) thiazolidine-2,4-dione
Homo sapiens
-
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
0.000045
5-(4-(cyclopentylmethoxy)benzylidene)thiazolidine-2,4-dione
Homo sapiens
-
pH 7.5, temperature not specified in the publication
0.000056
[1-(3-methylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
Homo sapiens
-
pH 8, 25C
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
0.000077
-
enzyme activity in kidney cortex
0.00083
-
recombinant 15-PGDH
0.0014
-
enzyme from lung
0.0098
-
enzyme from kidney cortex
0.025
-
enzyme from heart, substrate prostaglandin E2
0.136
-
enzyme from brain, substrate prostaglandin E2
1.75
-
-
1.765
-
-
1.791
-
-
7.79
-
purified native enzyme
12.15
-
enzyme from placenta
13.2
-
assay at 37C
19.8
-
recombinant enzyme
24
-
enzyme from placenta
25
-
; purified enzyme
70
-
enzyme from lung
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 9
-
assay at
7
-
assay at
7.2 - 8.5
7.5 - 8.8
-
sharp optimum
7.5
-
assay at
8
-
assay at
9
assay at
10 - 10.4
-
; prostaglandin E1, 3-(cyclohexylamine)propanesulfonic acid buffer
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
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
-
both 15-hydroxyprostaglandin dehydrogenase mRNA and protein levels are significantly higher in kidney cortex than in papilla. Enzyme is mainly localized to the tubular epithelial cells in kidney cortex and outer medulla
Manually annotated by BRENDA team
-
55000 Da form of enzyme, level increases with preterm premature rupture of membrane
Manually annotated by BRENDA team
-
low expression
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
-
intense immunofluorescent staining for 15-hydroxyprostaglandin dehydrogenase in macula densa and glomerulus of cyclooxygenase-2 knock-out mice
Manually annotated by BRENDA team
-
high enzyme expression level
Manually annotated by BRENDA team
-
low 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
-
macula densa cell line, significantly lower enzyme levels than in a proximal tubule cell line. Treatment with an inhibitor of cyclooxygenase-2 increases enzyme level
Manually annotated by BRENDA team
-
enzyme activity is reduced in inflamed mucosa
Manually annotated by BRENDA team
-
intense immunofluorescent staining for 15-hydroxyprostaglandin dehydrogenase in macula densa and glomerulus of cyclooxygenase-2 knock-out mice
Manually annotated by BRENDA team
-
enzyme is mainly localized to the tubular epithelial cells in kidney cortex and outer medulla
Manually annotated by BRENDA team
-
low expression level of 15-PGDH
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
very low enzyme expression level
Manually annotated by BRENDA team
-
low enzyme expression level
Manually annotated by BRENDA team
the enzyme is expressed mainly in the glandular epithelium, enzyme activity during the oestrous cycle and early pregnancy, overview
Manually annotated by BRENDA team
-
PGDH messenger RNA (mRNA) abundance decreases significantly in the visceral yolk sac membrane and the amnion throughout the last third of pregnancy
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information
-
subcellular localization, overview
-
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
24500
-
gel filtration
28000
-
gel filtration, MALDI-MS
29000
-
recombinant enzyme expressed in E. coli, western-blot
31000
-
wild type recombinant protein, SDS-PAGE
32000
-
gel filtration in the presence of mercaptoethanol
40000
-
gel filtration
51500
-
gel filtration
54000
-
gel filtration
55000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
-
-80C, 3-4 weeks
-
4C, 20% glycerol, 4 weeks, 25% loss of activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
; native enzyme 2600fold from lung cytosol of pregnant rabbits, by cation and anion exchange chromatography, gel filtration, hydrophobic interaction and hydroxylapatite chromatography to homogeneity
-
; native enzyme from lung by ammonium sulfate fractionation and acetone precipitation
-
CM-Sepharose, DEAE-Sepharose, Blue Sepharose, Mono-Q
-
native enzyme partially from heart; native soluble enzyme partially from lung by ultracentrifugation, ammonium sulfate fractionation and anion exchange chromatography; partial
-
native enzyme partially from kidney; partial
-
native soluble enzyme partially from heart ventricular tissue by ultracentrifugation, ammonium sulfate fractionation, gel filtration, and anion exchange chromatography; partial
-
native soluble enzyme partially from lung; partial
-
nickel-Sepharose column chromatography
-
partial
recombinant 15-PGDH
-
recombinant His-tagged lung enzyme from Escherichia coli by nickel affinity chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
15-PGDH, DNA and amino acid sequence determination and analysis, functional overexpression of His-tagged lung enzyme in Escherichia coli
cloning of cDNA
-
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 strain JM109(DE3); expression in Escherichia coli
-
expressed in Mus musculus RAW macrophages (R15L cells)
-
expression in 293-T cell, together with mouse peroxisome proliferator-activated receptor gamma
-
expression in Escherichia coli
-
expression in IEC-18 cell
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-PGDH is overexpressed in malignant ovarian tissue
-
interleukin 4 induces up-regulation of 15-PGDH expression in A549 cells as well as in other lung cancer cell lines
-
PDGH shows little expression in the myometrium; PGDH messenger RNA (mRNA) abundance decreases significantly in the visceral yolk sac membrane and the amnion throughout the last third of pregnancy
-
PGDH protein is highly expressed in the endometrial epithelium
-
PGDH protein is robustly expressed in the visceral yolk sac epithelium and mesoderm, correlating strongly with PGDH mRNA levels
-
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