Ligand prostaglandin E2

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Basic Ligand Information

Molecular Structure
Picture of prostaglandin E2 (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C20H32O5
prostaglandin E2
XEYBRNLFEZDVAW-ARSRFYASSA-N
Synonyms:
(5Z,13E)-(15S)-11,15-dihydroxy-9-oxoprosta-5,13-dienoate, (5Z,13E)-(15S)-11a,15-dihydroxyprosta-5,13-dienoate, (5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate, (5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate, (5Z,13E)-(15S)-11alpha,15-dihydroxyprosta-5,13-dienoate, (5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate, (5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate, prostaglandin E2[side 1], prostaglandin E2[side 2], prostaglandin PGE2


Show all pahtways known for Show all BRENDA pathways known for prostaglandin E2

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
prostaglandin E2 + NADPH = prostaglandin F2alpha + NADP+
show the reaction diagram
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prostaglandin E2 + NADP+ = 15-oxoprostaglandin E2 + NADPH + H+
show the reaction diagram
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prostaglandin E2 + NADP+ = 15-ketoprostaglandin E2 + NADPH + H+
show the reaction diagram
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ATP + H2O + prostaglandin E2/in = ADP + phosphate + prostaglandin E2/out
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In Vivo Product in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADH = (5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD+
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ATP + H2O + prostaglandin E2/in = ADP + phosphate + prostaglandin E2/out
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (24 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
prostaglandin E2 + NADPH = ?
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prostaglandin E2 + NADPH = NADP+ + ?
show the reaction diagram
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prostaglandin E2 + NADP+ = 15-ketoprostaglandin E2 + NADPH + H+
show the reaction diagram
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prostaglandin E2 + NADP+ = 15-ketoprostaglandin E2 + NADPH + H+
show the reaction diagram
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prostaglandin E2 + [reduced NADPH-hemoprotein reductase] + O2 = 20-hydroxy-prostaglandin E2 + [oxidized NADPH-hemoprotein reductase] + H2O
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prostaglandin E2 + NADP+ = 15-ketoprostaglandin E2 + NADPH + H+
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prostaglandin E2 = thromboxane A2 + ?
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Product in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(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
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Activator in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
stimulation of progesterone production and of 11beta-hydroxysteroid dehydrogenase activity via the prostaglandin E receptor 2-cAMP signalling pathway in luteinizing granulosa cells
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0.05 mM induce activity by elevation of cAMP levels
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1.5fold stimulation at 0.1 mM, half maximal stimulation at 0.05 mM
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PGE2, significantly increases MMP-2 activity as well as tube formation in endothelial cells. The PGE2-mediated elevation of MMP-2 activity is associated with the pro-angiogenic responses
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Inhibitor in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibits the reduction of 20alpha-hydroxy-pregn-4-en-3-one to progesterone competitively
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inhibits IKK
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dose-dependent inhibition with maximal effect at 1 nM. The addition of 0.001 mM prostaglandin E2 decreases Na+-ATPase activity by 41%. The inhibitory effect of prostaglandin E2 on proximal tubule Na+-ATPase activity involves G protein and the activation of protein kinase A. The protein A-mediated inhibitory effect of prostaglandin E2 on Na+-ATPase activity requires previous activation of protein kinase C
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (19 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE

KM Value (48 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0152
-
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0.35
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Ki Value (3 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0109
-
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0.025
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competitive inhibitor for the reduction of 20alpha-hydroxy-pregn-4-en-3-one to progesterone
0.128
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at pH 7.6 and 25°C

IC50 Value (3 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.1
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pH 7.4, 37°C, recombinant CES1

References & Links

Links to other databases for prostaglandin E2

ChEBI
PubChem
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PubChem