Information on EC 1.1.1.188 - prostaglandin-F synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.1.1.188
-
RECOMMENDED NAME
GeneOntology No.
prostaglandin-F synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+ = (5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
arachidonic acid metabolism
-
-
Arachidonic acid metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate:NADP+ 11-oxidoreductase
Reduces prostaglandin D2 and prostaglandin H2 to prostaglandin F2; prostaglandin D2 is not an intermediate in the reduction of prostaglandin H2. Also catalyses the reduction of a number of carbonyl compounds, such as 9,10-phenanthroquinone and 4-nitroacetophenone.
CAS REGISTRY NUMBER
COMMENTARY hide
55976-95-9
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
AKR1C3
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
AKR1C3
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
the result of amino acid analysis and sequence comparison suggest that epsilon-crystallin of the lens and prostaglandin F synthase are identical enzymes
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
metabolism
physiological function
additional information
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)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
show the reaction diagram
(5Z,13E)-(15S)-9alpha,11beta,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
show the reaction diagram
-
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11beta,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
4-nitroacetophenone + NADPH
?
show the reaction diagram
-
high activity
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzalcohol + NADP+
show the reaction diagram
-
high activity
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
show the reaction diagram
4-nitrobenzaldehyde + NADPH + H+
(4-nitrophenyl)methanol + NADP+
show the reaction diagram
5beta-androstane-3,17-dione + NADPH
5beta-androstan-3alpha-ol-17-one + NADP+
show the reaction diagram
-
-
-
-
r
5beta-dihydrotestosterone + NADPH
?
show the reaction diagram
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
show the reaction diagram
9,10-phenanthrenequinone + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
9,10-phenanthrenequinone + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
androst-4-ene-3,17-dione + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
cyclohexanone + NADPH
cyclohexanol + NADP+
show the reaction diagram
D-xylose + NADPH
?
show the reaction diagram
-
-
-
-
?
daunorubicin + NADPH
?
show the reaction diagram
-
high activity
-
-
?
DL-glyceraldehyde + NADPH
DL-glycerol + NADP+
show the reaction diagram
-
-
-
-
?
DL-glyceraldehyde + NADPH
glyceral + NADP+
show the reaction diagram
-
-
-
-
?
duroquinone + NADPH
?
show the reaction diagram
-
-
-
-
?
hydrindantin + NADPH
?
show the reaction diagram
menadione + NADPH
?
show the reaction diagram
n-butyraldehyde + NADPH
n-butanol + NADP+
show the reaction diagram
-
-
-
-
?
p-nitroacetophenone + NADPH
?
show the reaction diagram
-
-
-
-
?
phenylglyoxal + NADPH
?
show the reaction diagram
prostaglandin A2 + NADPH
?
show the reaction diagram
-
-
-
-
?
prostaglandin D1 + NADPH
?
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADP+
9alpha,11beta-prostaglandin F2 + NADPH
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADP+
9alpha11beta-prostaglandin F2 + NADPH
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH
9alpha,11alpha-prostaglandin F2alpha + NADP+
show the reaction diagram
prostaglandin D2 + NADPH
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
prostaglandin D2 + NADPH
9alpha,11beta-prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
r
prostaglandin D2 + NADPH
9alpha,11beta-prostaglandin F2alphabeta + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
?
prostaglandin D2 + NADPH + H+
9-alpha,11-beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
show the reaction diagram
prostaglandin D2 ethanolamide + NADPH
prostaglandin 9alpha,11beta-F2 ethanolamide + NADP+
show the reaction diagram
i.e. prostamide D2
i.e. 91lpha,11beta-prostamide F2
-
?
prostaglandin D3 + NADPH
?
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADP+
prostaglandin F2alpha + NADPH + H+
show the reaction diagram
prostaglandin H2 + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
prostaglandin H2 + NADPH
9alpha,11alpha-prostaglandin F2alpha + NADP+
show the reaction diagram
prostaglandin H2 + NADPH
prostaglandin 9alpha,11beta-F2 + NADP+
show the reaction diagram
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin D2 + NADP+
show the reaction diagram
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
prostaglandin H2 + NADPH + H+
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
aldo-keto reductase has prostaglandin F2alpha synthase activity. AKR1B1 is a more efficient prostaglandin F2alpha synthase than AKR1C3
-
-
?
prostaglandin H2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
show the reaction diagram
prostaglandin I2 + NADPH
?
show the reaction diagram
-
-
-
-
?
prostamide D2 + NADPH + H+
9alpha,11beta-prostamide F2 + NADP+
show the reaction diagram
-
-
-
?
prostamide H2 + NADPH + H+
prostamide F2alpha + NADP+
show the reaction diagram
-
about 70% of prostamide H2 is converted to prostamide F2alpha after 2 min at 37C
-
-
?
retinal + NADPH
retinol + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH
?
show the reaction diagram
-
-
-
-
?
ubiquinone-10 + NADPH
?
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
show the reaction diagram
(5Z,13E)-(15S)-9alpha,11beta,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
show the reaction diagram
-
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
show the reaction diagram
prostaglandin D2 + NADP+
9alpha,11beta-prostaglandin F2 + NADPH
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH
9alpha,11alpha-prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH
9alpha,11beta-prostaglandin F2alphabeta + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH + H+
9-alpha,11-beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
show the reaction diagram
prostaglandin H2 + NADP+
prostaglandin F2alpha + NADPH + H+
show the reaction diagram
prostaglandin H2 + NADPH
9alpha,11alpha-prostaglandin F2alpha + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin H2 + NADPH
prostaglandin D2 + NADP+
show the reaction diagram
prostaglandin H2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
prostaglandin H2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
CaCl2
-
activation
Cl-
-
the liver-type isozyme is 3fold more activated than the lung-type isozyme
MgCl2
-
activation
NaBr
-
activation
NaCl
-
activation
NaI
-
activation
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
-
bimatoprost
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
-
ONO1370
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
-
ONO1349
(5Z)-7-[(1S,4S,5S,6R)-2-methyl-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
-
ONO1373
(Z)-7-[(1R,4S,5S,6R)-((E)-6-oct-1-enyl)-2-aza-bicyclo[2.2.1]hept-5-yl]-hept-5-enoic acid
-
inhibition of PGH2 9,11-endoperoxide reductase activity, slight inhibition of prostamide D2 11-ketoreductase and PGD2 11-ketoreductase activity
(Z)-7-[(1R,4S,5S,6R)-2-methyl-6-((E)-oct-1-enyl)-2-aza-bicyclo[2.2.1]hept-5-yl]-hept-5-enoic acid
-
inhibition of PGH2 9,11-endoperoxide reductase activity, slight inhibition of prostamide D2 11-ketoreductase and PGD2 11-ketoreductase activity, competitive, binds to the active site
(Z)-7-[(1R,4S,5S,6R)-6-((E)-(S)-3-hydroxy-oct-1-enyl)-2-aza-bicyclo[2.2.1]hept-5-yl]-hept-5-enoic acid
-
inhibition of PGH2 9,11-endoperoxide reductase activity, slight inhibition of prostamide D2 11-ketoreductase and PGD2 11-ketoreductase activity
1-(4-aminobenzyl)-5-methoxy-2-methylindoleacetic acid
-
-
15-deoxy-DELTA12,14-prostaglandin J2
-
15d-PGJ2, the enzyme inhibitor attenuates proliferation, inhibits collagen gel contraction and induces activation of the apoptotic marker, caspase-3, in CRL1762 keloid fibroblasts
2-(1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)-N-((trifluoromethyl)sulfonyl)acetamide
257fold selectivity for isoform AKR1C3 over isoform AKR1C2
-
3-(1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl)-propanoic acid
540fold selectivity for isoform AKR1C3 over isoform AKR1C2
3-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-propanoic acid
257fold selectivity for isoform AKR1C3 over isoform AKR1C2
4-benzoyl-benzoic acid
-
;
4-carboxy-2',4'-dinitrodiphenylamine
-
;
4-carboxy-2-aminodiphenylamine
-
;
4-chloro-N-(4-tolyl)-anthranilic acid
-
;
4-chloro-N-phenylanthranilic acid
-
;
4-nitro-N-phenylanthranilic acid
-
;
4-Nitrobenzaldehyde
-
competitive inhibition of PGD2 but not of PGH2 reduction
5-methyl-N-phenylanthranilic acid
-
;
9,10-phenanthrenequinone
acetate
-
occupies the oxyanion hole of the active site, 2 complex structures
Ag+
-
IC50 = 0.005 mM
AgNO3
-
at 0.05 mM 87-100% inhibition, depending on the substrate
aspirin
-
;
bimatoprost
Cd2+
-
IC50 = 0.95 mM
CdSO4
-
at 5 mM 91-100% inhibition, depending on the substrate
Cu2+
-
IC50 = 0.4 mM
CuSO4
-
at 5 mM 93-96% inhibition, depending on the substrate; the liver-type isozyme is 2fold less sensitive than the lung-type isozyme
FeCl2
-
-
Flufenamic acid
-
nonsteroidal anti-inflammatory drug, binds to both the active site and the beta-hairpin loop at the opposite end of the central beta-barrel, complex structure
flurbiprofen
HgCl2
-
at 1 mM 94-100% inhibition, depending on the substrate; IC50 = 0.3 mM, the liver-type isozyme is 2fold less sensitive than the lung-type isozyme
Ibuprofen
indomethacin
indomethacin methyl ester
-
specific inhibition of isoform AKR1C3 versus AKR1C1 and AKR1C3
interferon tau
-
Meclofenamic acid
Mefenamic acid
-
;
methylglyoxal
N-(4-chlorobenzoyl)-melatonin
NaF
-
-
naproxen
ONO1349
-
-
ONO1370
-
-
ONO1373
-
-
ponalrestat
-
specific inhibitor developed to block AKR1B1 activity. Application reduces prostaglandin F2alpha production in response to interleukin IL-1beta in both cultured endometrial cells and endometrial explants
rutin
-
binding structure at the substrate binding site
salicylic acid
-
;
sorbinil
sulindac
tert-butyl hydroperoxide
-
-
Tolrestat
Zn2+
-
IC50 = 1.4 mM
ZnSO4
-
at 5 mM 71-100% inhibition, depending on the substrate
Zomepirac
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ammonium sulfate
activity of the purified recombinant enzyme is stimulated about 4fold by 1.5 M
chloride
-
stimulates the reduction of prostaglandin D2 and carbonyl compounds, but had no effect on prostaglandin H2 reduction
Gonadotropin
-
prostaglandin F synthase mRNA and protein levels are low before treatment with gonadotropin and peak 24-36 h after gonadotropin administration to granulosa cells
-
imidazole
-
in vitro stimulation of prostaglandin F2alpha and D2 production
Interleukin-1beta
-
membrane-associated, not soluble, isozyme in WI-38 cells
-
lipopolysaccharide
-
induces the membrane-associated isozyme
lipopolysaccharides
-
strong induction of the membrane-bound lung isozyme, slight induction in spleen, kidney, testis, and pancreas, overview
-
NaBr
-
stimulates prostaglandin D2 11-ketoreductase activity
NaCl
-
stimulates prostaglandin D2 11-ketoreductase activity
NaI
-
stimulates prostaglandin D2 11-ketoreductase activity
Oxytocin
-
increases prostaglandin F synthase mRNA synthesis
Oxytoxin
-
stimulates enzyme expression and PGD2 11-ketoreductase activity in myometrial tissue of cyclic, but not significantly of early-pregnant, sows, at 0.0001 mM
phorbol 12-myristate 13-acetate
-
stimulates prostaglandin synthesis
piroxicam
-
-
warfarin
-
-
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.134
(5Z,13E)-(15S)-9alpha,11beta,15-trihydroxyprosta-5,13-dienoate
-
-
0.0119 - 0.013
4-Nitroacetophenone
0.0008 - 0.125
4-Nitrobenzaldehyde
0.0031
5beta-androstan-3,17-dione
-
-
0.001
5beta-Androstan-3alpha-ol-17-one
-
-
0.0175
5beta-dihydrotestosterone
-
; 37C, liver-type isozyme
0.0001 - 0.002
9,10-phenanthrenequinone
0.0066
androst-4-ene-3,17-dione
-
pH 7.0, 37C
0.053
cyclohexanone
-
; 37C, liver-type isozyme
135
D-xylose
-
-
0.143
DL-glyceraldehyde
-
; 37C, liver-type isozyme
0.0031 - 0.018
Hydrindantin
0.013 - 0.1
menadione
0.0034 - 0.067
NADPH
0.0119
p-nitroacetophenone
-
-
0.02 - 0.08
Phenylglyoxal
0.25
Prostaglandin A2
-
lung enzyme
0.007
prostaglandin D1
-
; 37C, liver-type isozyme
0.0034 - 2
Prostaglandin D2
0.0056
Prostaglandin D3
-
; 37C, liver-type isozyme
0.0013 - 0.033
prostaglandin H2
0.015 - 0.18
prostaglandin PGD2
0.003 - 0.03
prostaglandin PGH2
0.02
retinal
-
-
0.0057
testosterone
-
-
additional information
additional information
-
kinetics of 3alpha-hydroxysteroid dehydrogenase type II activity
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.4
9,10-phenanthrenequinone
-
pH 7.0, 37C
0.0027
androst-4-ene-3,17-dione
-
pH 7.0, 37C
0.2467
prostaglandin H2
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
35.85
prostaglandin H2
-
pH 7.0, 24C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0019
4-benzoyl-benzoic acid
-
;
0.00038
4-carboxy-2',4'-dinitrodiphenylamine
-
;
0.01
4-carboxy-2-aminodiphenylamine
-
;
0.0014
4-chloro-N-(4-tolyl)-anthranilic acid
-
;
0.0029
4-chloro-N-phenylanthranilic acid
-
;
0.0019
4-nitro-N-phenylanthranilic acid
-
;
0.023
4-Nitrobenzaldehyde
-
37C, liver-type isozyme, versus prostaglandin D2
0.0073
5-methyl-N-phenylanthranilic acid
-
;
0.0009
9,10-phenanthrenequinone
-
37C, liver-type isozyme, versus prostaglandin D2
0.005
AgNO3
-
prostaglandin D2 11-ketoreductase activity
0.95
CdSO4
-
prostaglandin D2 11-ketoreductase activity
0.4
CuSO4
-
prostaglandin D2 11-ketoreductase activity
0.3
HgCl2
-
prostaglandin D2 11-ketoreductase activity
0.0003
Mefenamic acid
-
;
0.0034
N-(4-chlorobenzoyl)-melatonin
-
-
0.00089 - 0.0217
sorbinil
0.00026 - 0.0036
Tolrestat
1.4
ZnSO4
-
prostaglandin D2 11-ketoreductase activity
additional information
additional information
-
Ki values for the nonsteroidal anti-inflammatory drug inhibitors with 3alpha-androstanediol as a substrate
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.005 - 0.06
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
0.3 - 1
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
0.13 - 1
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
0.06 - 1
(5Z)-7-[(1S,4S,5S,6R)-2-methyl-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
0.052
1-(4-aminobenzyl)-5-methoxy-2-methylindoleacetic acid
Homo sapiens
-
pH 7.0, 37C
0.00021
2-(1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl )-N-((trifluoromethyl)sulfonyl)acetamide
Homo sapiens
P42330
pH not specified in the publication, temperature not specified in the publication
-
0.00009
3-(1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl)-propanoic acid
Homo sapiens
P42330
pH not specified in the publication, temperature not specified in the publication
0.00022
3-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-propanoic acid
Homo sapiens
P42330
pH not specified in the publication, temperature not specified in the publication
0.002
4-benzoyl-benzoic acid
Homo sapiens
-
;
0.0004
4-carboxy-2',4'-dinitrodiphenylamine
Homo sapiens
-
;
0.011
4-carboxy-2-aminodiphenylamine
Homo sapiens
-
;
0.0015
4-chloro-N-(4-tolyl)-anthranilic acid
Homo sapiens
-
;
0.003
4-chloro-N-phenylanthranilic acid
Homo sapiens
-
;
0.002
4-nitro-N-phenylanthranilic acid
Homo sapiens
-
;
0.011
5-methyl-N-phenylanthranilic acid
Homo sapiens
-
;
0.005
Ag+
Bos taurus
-
IC50 = 0.005 mM
1.2
aspirin
Homo sapiens
-
;
0.005 - 0.06
bimatoprost
0.95
Cd2+
Bos taurus
-
IC50 = 0.95 mM
0.4
Cu2+
Bos taurus
-
IC50 = 0.4 mM
0.0078
flurbiprofen
0.3
HgCl2
Bos taurus
-
IC50 = 0.3 mM, the liver-type isozyme is 2fold less sensitive than the lung-type isozyme
0.0099
Ibuprofen
0.0023
indomethacin
0.0023
indomethacin methyl ester
Homo sapiens
-
pH 7.0, 37C
0.0007
Meclofenamic acid
0.00039
Mefenamic acid
Homo sapiens
-
;
0.0078
N-(4-chlorobenzoyl)-melatonin
Homo sapiens
-
pH 7.0, 37C
0.0014
naproxen
0.13 - 1
ONO1349
0.3 - 1
ONO1370
0.06 - 1
ONO1373
0.77
salicylic acid
Homo sapiens
-
;
0.0034
sulindac
0.1 - 0.45
Tolrestat
1.4
Zn2+
Bos taurus
-
IC50 = 1.4 mM
0.04
Zomepirac
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0015
-
prostaglandin D2 as substrate
0.003
-
prostaglandin H2 as substrate; purified liver-type isozyme, substrate prostaglandin H2
0.008
-
purified liver-type isozyme, substrate prostaglandin I2
0.034
-
-
0.041
purified recombinant enzyme, pH 7.0, 25C, in presence of 0.05 mM 9,10-phenanthrenequinone
0.046
-
prostaglandin D1 as substrate; purified liver-type isozyme, substrate prostaglandin D1
0.062
PGF synthase activity of the purified enzyme
0.065
-
xylose as substrate
0.078
-
purified recombinant enzyme, pH 7.0, 25C, in presence of 0.05 mM 9,10-phenanthrenequinone
0.089
-
prostaglandin D3 as substrate; purified liver-type isozyme, substrate prostaglandin D3
0.095
-
prostaglandin D2 as substrate; purified liver-type isozyme, substrate prostaglandin D2
0.115
-
4-nitrobenzaldehyde reductase activity
0.13
-
5beta-dihydrotestosterone as substrate
0.15
-
prostaglandin F2alpha as product
0.159
-
cyclohexanone as substrate
0.167
-
menadione and hydrindantin as substrate
0.174
-
4-nitroacetophenone as substrate
0.2
-
about, purified recombinant enzyme, pH 7.0, 25C
0.206
-
DL-glyceraldehyde as substrate
0.207
-
phenylglyoxal as substrate
0.31
-
4-nitrobenzaldehyde as substrate; purified liver-type isozyme, substrate 4-nitrobenzaldehyde
0.339
-
9,10-phenanthrenequinone as substrate; purified liver-type isozyme, substrate 9,10-phenanthrenequinone
0.41
about, purified recombinant enzyme, pH 7.0, 25C
0.69
-
PGF synthase activity of the purified enzyme
2.4
-
pH 5.5, 37C
3.6
-
pH 5.0, 37C
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8 - 9
-
reduction of prostaglandin D2
9 - 10
-
oxidation of 9alpha,11beta-prostaglandin F2
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
assay at, PGH2 9,11-endoperoxide reductase activity
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25 - 37
-
the activity increases gradually as the temperature increases from 25 to 37C, and then decreases significantly at 45C compared with that at 37C
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
AKR1B3 mRNA 9 is expressed in preadipocytes, and its level increases about 4fold at day 1 after initiation of adipocyte differentiation, and then quickly decreases the following day to a level lower than that in the preadipocytes
Manually annotated by BRENDA team
-
expression of genes for PGE2 synthesis, with low levels of prostaglandin transporters and dehydrogenase
Manually annotated by BRENDA team
-
endothel, isozymes PGF synthase I and II
Manually annotated by BRENDA team
-
normal breast expresses very high levels of AKR1C3 relative to other tissues
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
production of PGE2, PGF2 and PGD2 and high prostaglandin turnover
Manually annotated by BRENDA team
-
peri- and postimplantation conceptus. Prostaglandin H synthase and prostaglandin E synthase are down-regulated, and prostaglandin G synthase, prostaglandin F synthase and carbonyl reductase/prostaglandin 9-reductase are down-regulated in conceptuses during trophoblasic elongation. After initiation of implantation, expression of prostaglandin G synthase, prostaglandin F synthase and carbonyl reductase/prostaglandin 9-reductase in conceptuses increases and remains higher until days 24-25 of pregnancy
Manually annotated by BRENDA team
-
keloid fibroblasts
Manually annotated by BRENDA team
-
isoform AKR1B1 is expressed at a high level during the menstrual cycle during the secretory phase and in both epithelial and stromal cells
Manually annotated by BRENDA team
-
isozyme PGF synthase II
Manually annotated by BRENDA team
-
isoform AKR1B1 is expressed at a high level during the menstrual cycle during the secretory phase and in both epithelial and stromal cells
Manually annotated by BRENDA team
-
glioblastoma cell
Manually annotated by BRENDA team
-
embryonic kidney cell, isozyme PGFS-I
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
co-localization of cyclooxygenase-1, prostaglandin F receptor and prostaglandin F synthase
Manually annotated by BRENDA team
-
peritoneal
Manually annotated by BRENDA team
-
high expression level
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
enzyme co-localizes with myelin basic protein in myelin sheaths but not in axons
Manually annotated by BRENDA team
-
dendrites and somata, isozyme PGF synthase I
Manually annotated by BRENDA team
-
cultured oligodendrocytes at 7 days in vitro express the enzyme in cytoplasmic processes where the enzyme is co-localized with myelin basic protein
Manually annotated by BRENDA team
-
the enzyme is associated with the cyclooxygenase-II, COX-II
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
AKR1C3 is overexpressed in skin squamous cell carcinoma (SCC) and affects SCC growth via prostaglandin metabolism
Manually annotated by BRENDA team
-
high expression level
Manually annotated by BRENDA team
-
isozyme PGF synthase II
Manually annotated by BRENDA team
-
glioblastoma cell
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
lung fibroblast cell
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
16000
-
1 * 16000
17000
-
-
20000
immunoprecipitation, Western blot analysis
23000
-
by zinc staining
23230
-
expressed protein
30500
-
SDS-PAGE, sedimentation equilibrium and gel filtration
36700
-
Western blot with antibody staining
36742
-
1 * 36666, lung-type isozyme, sequence calculation, 1 * 36742, liver-type isozyme, sequence calculation
36800
x * 36800, approximately, sequence calculation
36840
-
amino acid analysis
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
additional information
-
enzyme has a (alpha/beta)8 barrel structure, from crystal structure determination
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
16 mg/ml purified enzyme complexed with inhibitors acetate, flufenamic acid or indomethacin, hanging drop vapour diffusion method in 0.006 ml drops, 1:1 mixture of protein solution containing 10 mM potassium phosphate, pH 7.0, 1 mM DTT, 1 mM EDTA, 2 mM NADP+, with reservoir solution containing 25% w/v PEG 4000, 100 mM sodium citrate, pH 6.0, 2.5% v/v 2-methyl-2,4-pentanediol, and 800 mM ammonium acetate, 6 days to maximum size, X-ray diffraction structure determination of the complexes and analysis at 1.2-2.1 A resolution
-
20 mg/ml purified recombinant enzyme in a solution containing 1.4 mM PGD2 or inhibitor rutin, 1.2 mM NADP+ and NADPH, 50 mM MES, pH 6.0, and 25% w/v PEG 8000, hanging drop vapour diffusion method, 2-3 days, thick plate-shaped crystals of enzyme with NADP+ and PGD2 and of enzyme with NADPH and rutin, X-ray diffraction structure determination and analysis at 1.69 A resolution
-
AKR1C3 in complex with NADP+ and indomethacin
-
homology modeling of enzyme in complex with inhibitor indomethacin
-
in complex with bimatoprost and NADPH, hanging drop vapor diffusion method, using 1.0 mM BMP, 1.0 mM NADPH, 0.14 M NaCl, 50 mM MES buffer (pH 7.0), and 26% (w/v) PEG 8000; purified recombinant enzyme in complex with NADPH and bimatoprost BMP, an ocular hypotensive agent bound near the PGD2 binding site located on the alpha- and omega-chains, hanging drop vapour diffusion method, from 50 mM MES, pH 7.0, containing 7 mg/ml protein, 0.14 M NaCl, 26% w/v PEG 8000, 1.0 mM NADPH, and 1.0 mM BMP, added in a 95% ethanol solution, 4C, 14 days, thick plate-shaped crystals, X-ray diffraction structure determination and analysis at 2.0 A resolution
-
purified recombinant apoenzyme or enzyme with bound cofactor NADPH, mixing of 20 mg/ml protein in 25 mM Tris, pH 8.0, 200 mM NaCl, 1% v/v glycerol, 1 mM TCEP with the reservoir solution containing 0.1 M sodium citrate pH 5.50, 20% PEG 3000 200 mM magnesium chloride, 100 mM Tris, pH 7.0, 10% PEG 8000 for apo- and complexed enzyme, 16C, 2-4 weeks, X-ray diffraction structure determination and analysis at 1.8 A and 1.6 A resolution, respectively, molecular replacement
10 mg/ml purified recombinant enzyme from 0.1 M HEPES/NaOH, pH 7.5, 2.0 M ammonium sulfate, 5% w/v PEG 400, and 0.5 M NADPH by hanging drop vapour diffusion method, 20C, 3 weeks, X-ray diffraction structure determination at room temperature and analysis at 2.6 A resolution
-
purified recombinant apoenzyme or enzyme with bound cofactor NADP+, mixing of 20 mg/ml protein in 25 mM Tris pH 8.0, 200 mM NaCl, 1% v/v glycerol, 1 mM TCEP with reservoir solution. For the apoenzyme, the reservoir solution contains 0.1 M MES-imidazole, pH 6.5, 10% PEG 20 000, 20% PEG 550 MME, 0.02 M glutamic acid, glycine, serine, alanine, and lysine, and for the cofactor complexed enzyme, it contains 0.2 M ammonium acetate, 0.1 M Bis-Tris pH 5.5, 25% PEG 3350, cryoprotectant is 15% ethylene glycol, 16C, 2-4 weeks, X-ray diffraction structure determination and analysis at 1.25 A and 2.6 A resolution, respectively, molecular replacement