Ligand prostaglandin H2

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Basic Ligand Information

Molecular Structure
Picture of prostaglandin H2 (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C20H32O5
prostaglandin H2
YIBNHAJFJUQSRA-YNNPMVKQSA-N
Synonyms:
(5Z)-7-{(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}hept-5-enoic acid, (5Z,9alpha,11alpha,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoate, (5Z,13E)-(15S)-9a,11a-epidioxy-15-hydroxyprosta-5,13-dienoate, (5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate, (5Z,13E)-(15S)-9alpha, 11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate, (5Z,13E,15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate, prostaglandin PGH2


Show all pahtways known for Show all BRENDA pathways known for prostaglandin H2

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (28 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
NADPH + H+ + prostaglandin H2 = NADP+ + prostaglandin F2alpha
-

In Vivo Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE

Substrate in Enzyme-catalyzed Reactions (39 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
prostaglandin H2 + [reduced NADPH-hemoprotein reductase] + O2 = 19-hydroxy-prostaglandin H2 + [oxidized NADPH-hemoprotein reductase] + H2O
-
show the reaction diagram
NADPH + H+ + prostaglandin H2 = NADP+ + prostaglandin F2alpha
-

Product in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (5 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
9,11-azoprosta-5,13-dienoic acid prevents inactivation; inactivation originates primarily from a transition-state intermediate, not from malondialdehyde formed by hydrolysis of prostaglandin endoperoxides; rapid inactivation of purified enzyme during incubation with prostaglandin H2
-
9,11-azoprosta-5,13-dienoic acid prevents inactivation; rapid inactivation of purified enzyme during incubation with prostaglandin H2
-
rapid inactivation of purified enzyme during incubation with prostaglandin H2
-
suicide inactivation
-

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (27 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
pH 7.0, 24°C
0.2467
-
-
0.2467
-
pH 7.0, 24°C, i.e. prostaglandin H2
0.25
-
in 0.1 M KPB (pH 7.0), at 24°C
0.25
-
mutant enzyme K59A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
5.84
-
wild type enzyme, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
2.64
-
mutant enzyme Y149A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
5.73
-
mutant enzyme W54A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
2.4
-
mutant enzyme T147A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
3.67
-
mutant enzyme S81A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
2.91
-
mutant enzyme S45A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
2.23
-
mutant enzyme M94A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
2.24
-
mutant enzyme M64A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.63
-
mutant enzyme L79A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.06
-
mutant enzyme L131A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.81
-
mutant enzyme F83A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.87
-
in the presence of 500 mM guanidinium hydrochloride
0.95
-
in the presence of 1 M urea
0.5
-
dodecylmaltoside activated
7
-
recombinant TXAS
0.017
-

KM Value (93 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
-
0.0019
-
expressed lung enzyme
0.008
-
AKR1B7
0.0038
-
AKR1B3
0.0093
-
37°C, liver-type isozyme
0.025
-
native and expressed liver prostaglandin F synthase
0.025
-
native lung prostaglandin F synthase
0.01
-
pH 5.0, 37°C
0.033
-
pH 5.5, 37°C
0.029
-
pH 7.0, 24°C
0.0069
-
-
0.0013
-
recombinant liver-type isozyme, mutant K225S, 37°C
0.028
-
recombinant liver-type isozyme, mutant H170C, 37°C
0.003
-
recombinant liver-type isozyme, mutant R27E, 37°C
0.014
-
recombinant liver-type isozyme, mutant S301R, 37°C
0.03
-
recombinant liver-type isozyme, mutants R91Q, R223L and N306Y, 37°C
0.01
-
recombinant wild-type liver-type isozyme, 37°C
0.025
-
i.e. prostaglandin H2, pH 7.0, 24°C
0.007
-
in 0.1 M KPB (pH 7.0), at 24°C
0.0069
-
pH 7.0, 24°C, i.e. prostaglandin H2
0.0069
-
mutant DELTA1-24_L-PGDS+T67A
0.0028
-
mutant DELTA1-24_L-PGDS+S81A
0.0015
-
mutant DELTA1-24_L-PGDS+S45A/T67A/S81A
0.0012
-
mutant DELTA1-24_L-PGDS+S45A/T67A
0.0021
-
mutant DELTA1-24_L-PGDS+T67A/S81A
0.0021
-
mutant DELTA1-24_L-PGDS+S45A/S81A
0.0012
-
mutant DELTA1-24_L-PGDS+W45A
0.0013
-
mutant DELTA1-24_L-PGDS+W54A/H111A
0.0008
-
mutant DELTA1-24_L-PGDS+S45A
0.0005
-
mutant enzyme F83A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.0245
-
mutant enzyme K59A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.0123
-
mutant enzyme L131A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.0252
-
mutant enzyme L79A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.0328
-
mutant enzyme M64A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.0325
-
mutant enzyme M94A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.0202
-
mutant enzyme S45A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.0204
-
mutant enzyme S81A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.0102
-
mutant enzyme T147A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.0154
-
mutant enzyme W54A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.0161
-
mutant enzyme Y149A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.0127
-
pH 8.0
0.014
-
wild type enzyme, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25°C
0.0138
-
mutant DELTA1-24_L-PGDS+H116A
0.0014
-
mutant DELTA1-24_L-PGDS+P110A
0.0016
-
in the presence of 1 M urea
0.0023
-
in the presence of 500 mM guanidinium hydrochloride
0.0083
-
mutant DELTA1-24_L-PGDS
0.0008
-
mutant DELTA1-24_L-PGDS+H111A
0.0014
-
wild type enzyme
0.215
-
wild-type, 0°C, pH 7.2
0.13
-
mutant Q36E, 0°C, pH 7.2
1.61
-
mutant Q134E, 0°C, pH 7.2
0.734
-
mutant enzyme Y117S
0.2832
-
mutant enzyme Y117A
0.5345
-
mutant enzyme R122A
0.372
-
in the presence of 0.3 mM dodecylmaltoside
0.1
-
IgG1(hei-7)-reactive protein
0.04
-
IgG1(hei-26)-reactive protein
0.15
-
GSH-independent enzyme from heart
0.0826
-
GSH-dependent enzyme from deferent duct
0.0257
-
cPGES plus casein kinase II plus Hsp90
0.0149
-
cPGES plus casein kinase II
0.0357
-
cPGES alone
0.0666
-
mutant enzyme N74A
0.4643
-
mutant enzyme R70A
0.296
-
mutant enzyme R70A/R122A
0.4737
-
mutant enzyme T129V
0.3842
-
at 24°C
0.03
-
-
0.022
-
native TXAS
0.022
-
recombinant TXAS
0.021
-
23°C, pH 7.5
0.02
-
soluble enzyme
0.0053
-
immobilized enzyme
0.002
-
-
0.0207
-

IC50 Value (2 results)

COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
pH not specified in the publication, 37°C, inhibition of human monocytes
0.0096
-
pH not specified in the publication, 37°C, inhibition of human THP-1 cells
0.0072
-

References & Links

Links to other databases for prostaglandin H2

ChEBI
PubChem
-
PubChem