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Ligand prostaglandin E2

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

arachidonic acid metabolism

KEGG

African trypanosomiasis, Amoebiasis, Arachidonic acid metabolism, Bile secretion, C-type lectin receptor signaling pathway, cAMP signaling pathway, Human cytomegalovirus infection, Human papillomavirus infection, Inflammatory mediator regulation of TRP channels, Leishmaniasis, Neuroactive ligand-receptor interaction, Oxytocin signaling pathway, Pathways in cancer, Regulation of lipolysis in adipocytes, Renin secretion, Rheumatoid arthritis, Serotonergic synapse more

MetaCyc

arachidonate metabolites biosynthesis, C20 prostanoid biosynthesis

Show all BRENDA pathways known for prostaglandin E2

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Roles as Enzyme Ligand

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

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Show Natural Substrate (9 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.141

(5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD+ = (5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADH + H+

285931, 654158, 654348, 654361, 654374, 654380, 657209, 667924, 668172, 657210, 285917, 348015, 670868, 668162, 285918, 285932, 285921, 285916, 670691, 670734, 285939, 669380, 668160, 668173, 667558, 668359

-

1.1.1.141

(5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD+ = (5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADH + H+

739837, 741244, 762674, 763614

-

1.1.1.141

prostaglandin E2 + NAD+ = 15-oxoprostaglandin E2 + NADH + H+

740159, 740709, 741014, 741035

-

1.1.1.141

3 entries

1.1.1.184

prostaglandin E2 + NADPH = prostaglandin F2alpha + NADP+

285938

-

1.1.1.189

prostaglandin E2 + NADPH + H+ = prostaglandin F2alpha + NADP+

670733

-

1.1.1.189

prostaglandin E2 + NADPH = prostaglandin F2alpha + NADP+

657212

-

1.1.1.189

2 entries

1.1.1.197

prostaglandin E2 + NADP+ = 15-oxoprostaglandin E2 + NADPH + H+

347828

-

1.3.1.48

prostaglandin E2 + NADP+ = 15-ketoprostaglandin E2 + NADPH + H+

746356

-

7.6.2.2

ATP + H2O + prostaglandin E2/in = ADP + phosphate + prostaglandin E2/out

701356

-

In Vivo Product in Enzyme-catalyzed Reactions (7 results)

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Show Natural Product (7 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.141

(5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADH = (5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD+

0

-

1.1.1.189

(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+ = (5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate + NADPH + H+

0

-

1.1.1.189

prostaglandin H2 + NAD(P)H + H+ = prostaglandin E2 + NAD(P)+

0

-

5.3.99.3

(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate = (5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate

0

-

5.3.99.3

(5Z,13E,15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate = (5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate

0

-

5.3.99.3

Prostaglandin H2 = Prostaglandin E2

0

-

1.1.1.189

2 entries

5.3.99.3

3 entries

7.6.2.2

ATP + H2O + prostaglandin E2/in = ADP + phosphate + prostaglandin E2/out

0

-

Substrate in Enzyme-catalyzed Reactions (24 results)

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Show Substrate (24 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.141

(5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD+ = (5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADH + H+

285919, 285927, 285931, 285938, 654158, 654348, 654361, 654374, 654380, 657209, 667924, 668172, 711448, 657210, 285924, 285917, 285926, 285921, 348015, 670868, 686593, 285923, 285915, 668162, 285918, 285932, 285916, 670691, 285939, 667558, 668160, 668173, 670734, 669380, 668359

-

1.1.1.141

(5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD+ = (5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADH + H+

739837, 741244, 762674, 763614

-

1.1.1.141

prostaglandin E2 + NAD+ = 15-ketoprostaglandin E2 + NADH + H+

285916, 695481, 695883, 697090, 688932, 689129

-

1.1.1.141

prostaglandin E2 + NAD+ = 15-oxoprostaglandin E2 + NADH + H+

285912, 725664, 726267, 740148, 740159, 740536, 740709, 741014, 741035, 741244, 740130

-

1.1.1.141

4 entries

1.1.1.145

prostaglandin E2 + NADPH = ?

389394

-

1.1.1.149

prostaglandin E2 + NADPH = NADP+ + ?

286001

-

1.1.1.184

prostaglandin E2 + NADPH + H+ = prostaglandin F2alpha + NADP+

347776, 762501, 740436

-

1.1.1.184

prostaglandin E2 + NADPH = ?

347770, 347763, 655213

-

1.1.1.184

prostaglandin E2 + NADPH = prostaglandin F2alpha + NADP+

686356, 285938

-

1.1.1.189

(5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate + NAD(P)+ = (5Z,13E)-11alpha-hydroxy-9,15-dioxoprosta-5,13-dienoate + NAD(P)H

347776, 389470, 389476

-

1.1.1.189

prostaglandin E2 + NAD(P)H + H+ = prostaglandin F2alpha + NAD(P)+

697637

-

1.1.1.189

prostaglandin E2 + NAD(P)H = prostaglandin F2alpha + NAD(P)+

657211

-

1.1.1.189

prostaglandin E2 + NADPH + H+ = prostaglandin F2alpha + NADP+

670733

-

1.1.1.189

prostaglandin E2 + NADPH = prostaglandin F2alpha + NADP+

657212

-

1.1.1.184

3 entries

1.1.1.189

5 entries

1.1.1.196

prostaglandin E2 + NADP+ = 15-ketoprostaglandin E2 + NADPH + H+

347826, 347824

-

1.1.1.197

prostaglandin E2 + NADP+ = 15-oxoprostaglandin E2 + NADPH + H+

347828

-

1.1.1.197

prostaglandin E2 + NADPH + H+ = prostaglandin F2 + NADP+

347831, 347830

-

1.1.1.197

prostaglandin E2 + NADPH + H+ = prostaglandin F2alpha + NADP+

347828, 348015, 348018

-

1.1.1.197

3 entries

1.1.1.231

prostaglandin E2 + NADP+ = 15-ketoprostaglandin E2 + NADPH + H+

348015, 348012

-

1.14.14.1

prostaglandin E2 + [reduced NADPH-hemoprotein reductase] + O2 = 20-hydroxy-prostaglandin E2 + [oxidized NADPH-hemoprotein reductase] + H2O

660409

-

1.3.1.48

prostaglandin E2 + NADP+ = 15-ketoprostaglandin E2 + NADPH + H+

746356

-

5.3.99.5

prostaglandin E2 = thromboxane A2 + ?

690411

-

7.6.2.2

ATP + H2O + prostaglandin E2/in = ADP + phosphate + prostaglandin E2/out

701356

-

7.6.2.2

ATP + H2O + prostaglandin E2[side 1] = ADP + phosphate + prostaglandin E2[side 2]

747619

-

7.6.2.2

2 entries

Product in Enzyme-catalyzed Reactions (13 results)

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Show Product (13 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.141

(5Z,13E)-11alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADH = (5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD+

0

-

1.1.1.189

(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+ = (5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate + NADPH + H+

0

-

1.1.1.189

prostaglandin H2 + NAD(P)H + H+ = prostaglandin E2 + NAD(P)+

0

-

1.1.1.189

2 entries

1.14.99.1

arachidonic acid + AH2 + 2 O2 = prostaglandin E2 + A + H2O

438390, 0

-

5.3.99.3

(5Z,13E)-(15S)-9a,11a-epidioxy-15-hydroxyprosta-5,13-dienoate + GSH = (5Z,13E)-(15S)-11a,15-dihydroxyprosta-5,13-dienoate + GSSG

0, 652399

-

5.3.99.3

(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate = (5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate

0

-

5.3.99.3

(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate + GSH = (5Z,13E)-(15S)-11alpha,15-dihydroxyprosta-5,13-dienoate + GSSG

652244, 653633

-

5.3.99.3

(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate + reduced glutathione = (5Z,13E)-(15S)-11alpha,15-dihydroxyprosta-5,13-dienoate + oxidized glutathione

653753

-

5.3.99.3

(5Z,13E,15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate = (5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate

0

-

5.3.99.3

15-hydroperoxy-prostaglandin E2 + GSH = prostaglandin E2 + GSSG

652399

-

5.3.99.3

Prostaglandin H2 = Prostaglandin E2

0, 3134, 3127, 3129, 3126, 3128

-

7.6.2.2

ATP + H2O + prostaglandin E2/in = ADP + phosphate + prostaglandin E2/out

0

-

7.6.2.2

ATP + H2O + prostaglandin E2[side 1] = ADP + phosphate + prostaglandin E2[side 2]

0

-

5.3.99.3

7 entries

7.6.2.2

2 entries

Activator in Enzyme-catalyzed Reactions (5 results)

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Show Activating Compound (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.B40

stimulation of progesterone production and of 11beta-hydroxysteroid dehydrogenase activity via the prostaglandin E receptor 2-cAMP signalling pathway in luteinizing granulosa cells

693380

-

2.4.1.212

-

695183, 691042

-

2.7.11.11

0.05 mM induce activity by elevation of cAMP levels

692212

-

2.8.2.20

1.5fold stimulation at 0.1 mM, half maximal stimulation at 0.05 mM

645821

-

3.4.24.24

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

755131

-

Inhibitor in Enzyme-catalyzed Reactions (16 results)

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Show Inhibitors (16 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.141

-

285920

-

1.1.1.141

product inhibition

285924

-

1.1.1.141

2 entries

1.1.1.189

inhibits the reduction of 20alpha-hydroxy-pregn-4-en-3-one to progesterone competitively

389468

-

1.1.1.50

-

389527

-

1.13.11.52

-

743716

-

2.4.2.4

-

689271

-

2.7.11.10

inhibits IKK

660649

-

3.1.1.1

-

707570

-

3.1.1.4

-

679119

-

3.4.11.3

-

35899

-

3.4.11.3

at pH 6.2, not at pH 6.8 and 7. 4

35897

-

3.4.11.3

pH-dependent inhibition

35898

-

3.4.11.3

3 entries

5.3.99.2

-

748520

-

7.2.2.13

-

751973

-

7.2.2.13

PGE2

673231

-

7.2.2.13

2 entries

7.2.2.3

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

718694

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (19 results)

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Show Turnover Number (19 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.141

6.1

-

pH 8.0, 25°C, 20 nM [1-(3-methylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone

726267

1.1.1.141

7.5

-

pH 8.0, 25°C, 10 nM 3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine

726267

1.1.1.141

10.3

-

pH 8.0, 25°C, 10 nM [1-(3-methylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone

726267

1.1.1.141

11.1

-

pH 8.0, 25°C, 4 nM 3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine

726267

1.1.1.141

12.4

-

pH 8.0, 25°C, 10 nM 2-([(6-bromo-4H-imidazo[4,5-b]pyridin-2-yl)sulfanyl]methyl)benzonitrile

726267

1.1.1.141

13.6

-

pH 8.0, 25°C

726267

1.1.1.141

14.1

-

pH 8.0, 25°C, 10 nM 2-([(6-bromo-4H-imidazo[4,5-b]pyridin-2-yl)sulfanyl]methyl)benzonitrile

726267

1.1.1.141

37

-

37°C, pH 7.5, V186K mutant

654374

1.1.1.141

45

-

37°C, pH 7.5, N91D mutant

654374

1.1.1.141

50

-

37°C, pH 7.5

654374

1.1.1.141

73

-

37°C, pH 7.5, N91A mutant

654374

1.1.1.141

78

-

37°C, pH 7.5, V186A mutant

654374

1.1.1.141

127

-

37°C, pH 7.5, I17A mutant

654374

1.1.1.141

143

-

37°C, pH 7.5, I17V mutant

654374

1.1.1.141

210

-

37°C, pH 7.5, I17L mutant

654374

1.1.1.141

262

-

37°C, pH 7.5, V186I mutant

654374

1.1.1.184

0.68

-

pH 6.5, 25°C

740436

1.1.1.184

18

-

mutant V88I, 37°C, pH 7.4

686356

1.1.1.184

25

-

wild-type, 37°C, pH 7.4

686356

1.1.1.141

16 entries

1.1.1.184

3 entries

K_M Value (48 results)

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Show KM Value (48 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.141

0.0012

-

37°C, pH 7.5, I17L mutant

654374

1.1.1.141

0.00158

-

-

285924

1.1.1.141

0.0025

-

at pH 7.0

285916

1.1.1.141

0.0026

-

37°C, pH 7.5, N91D mutant

654374

1.1.1.141

0.0026

-

-

285920

1.1.1.141

0.0028

-

at pH 9.0

285916

1.1.1.141

0.0028

-

pH 8.0, 25°C, 20 nM [1-(3-methylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone

726267

1.1.1.141

0.0034

-

37°C, pH 7.5

654374

1.1.1.141

0.0035

-

37°C, pH 7.5, V186K mutant

654374

1.1.1.141

0.0037

-

pH 8.0, 25°C, 10 nM [1-(3-methylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone

726267

1.1.1.141

0.0039

-

-

654158

1.1.1.141

0.0039

-

recombinant enzyme expressed in E. coli

285937

1.1.1.141

0.0045

-

37°C, pH 7.5, V186A mutant

654374

1.1.1.141

0.0055

-

pH 8.0, 25°C

726267

1.1.1.141

0.0056

-

pH 8.0, 25°C, 4 nM 3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine

726267

1.1.1.141

0.006

-

37°C, pH 7.5, N91A mutant

654374

1.1.1.141

0.0063

-

37°C, pH 7.5

654361

1.1.1.141

0.0064

-

pH 8.0, 25°C, 10 nM 3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine

726267

1.1.1.141

0.0071

-

37°C, pH 7.5

657209

1.1.1.141

0.0075

-

pH 8.0, 25°C, 10 nM 2-([(6-bromo-4H-imidazo[4,5-b]pyridin-2-yl)sulfanyl]methyl)benzonitrile

726267

1.1.1.141

0.0086

-

37°C, pH 7.5, T11S mutant

657209

1.1.1.141

0.01

-

pH 7.4, 37°C

285918

1.1.1.141

0.01

-

-

285927, 285935

1.1.1.141

0.011

-

37°C, pH 7.5, I17A mutant

654374

1.1.1.141

0.011

-

37°C, pH 7.5, I17V mutant

654374

1.1.1.141

0.0117

-

-

285933

1.1.1.141

0.013

-

37°C, pH 7.5, Q15K/W37K double mutant

654361

1.1.1.141

0.0135

-

pH 8.0, 25°C, 10 nM 2-([(6-bromo-4H-imidazo[4,5-b]pyridin-2-yl)sulfanyl]methyl)benzonitrile

726267

1.1.1.141

0.014

-

-

285912

1.1.1.141

0.022

-

37°C, pH 7.5, V186I mutant

654374

1.1.1.141

0.026

-

37°C, pH 7.5, Q15K mutant

654361

1.1.1.141

0.059

-

-

285921, 285938

1.1.1.141

0.059

-

pH 10.2

285921

1.1.1.141

33 entries

1.1.1.145

0.0152

-

-

389394

1.1.1.184

0.03

-

pH 6.5, 25°C

740436

1.1.1.184

0.1

-

-

347770

1.1.1.184

0.16

-

-

347776

1.1.1.184

0.24

-

form CR2

347763

1.1.1.184

0.309

-

wild-type, 37°C, pH 7.4

686356

1.1.1.184

0.32

-

mutant V88I, 37°C, pH 7.4

686356

1.1.1.189

0.08

-

-

389473

1.1.1.189

0.09

-

-

389476

1.1.1.189

0.092

-

-

389472

1.1.1.189

0.117

-

-

389466

1.1.1.189

0.122

-

-

389468, 389471

1.1.1.189

0.16

-

-

347776

1.1.1.189

0.32

-

-

389478

1.1.1.184

6 entries

1.1.1.189

7 entries

1.1.1.196

0.35

-

-

347826

K_i Value (3 results)

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Show KI Value (3 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.141

0.0109

-

-

285920

1.1.1.189

0.025

-

competitive inhibitor for the reduction of 20alpha-hydroxy-pregn-4-en-3-one to progesterone

389468

5.3.99.2

0.128

-

at pH 7.6 and 25°C

748520

IC₅₀ Value (3 results)

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Show IC50 Value (3 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.13.11.52

0.01

-

pH not specified in the publication, 37°C, inhibition of human THP-1 cells

743716

1.13.11.52

0.0221

-

pH not specified in the publication, 37°C, inhibition of human monocytes

743716

1.13.11.52

2 entries

3.1.1.1

0.1

-

pH 7.4, 37°C, recombinant CES1

707570

References & Links

Literature References (120)

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Show Reference (120 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

3126

3100531

Immunochemical and kinetic evidence for two different prostaglandin H-prostaglandin E isomerases in sheep vesicular gland microsomes

1987

Tanaka, Y.; Ward, S.L.; Smith, W.L.

J. Biol. Chem.

262

1374-1381

3127

6365099

Modulation of prostacyclin synthetase and unmasking of PGE2 isomerase in bovine coronary arterial microsomes

1984

McNamara, D.B.; Hussey, J.L.; Kerstein, M.D.; Rosenson, R.S.; Hyman, A.L.; Kadowitz, P.J.

Biochem. Biophys. Res. Commun.

118

33-39

3128

7132776

Purification of PGH-PGE isomerase from sheep vesicular glands

1982

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Control of the intracellular levels of prostaglandin E2 through inhibition of the 15-hydroxyprostaglandin dehydrogenase for wound healing

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A novel NAD(P)H-dependent carbonyl reductase specifically expressed in the thyroidectomized chicken fatty liver: catalytic properties and crystal structure

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2013

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Lipocalin-type prostaglandin D synthase is a novel phytocannabinoid-binding protein

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Regulation of matrix metalloproteinase-2 activity by COX-2-PGE2-pAKT axis promotes angiogenesis in endometriosis

2016

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Substructural dynamics of the phase-I drug metabolizing enzyme, carbonyl reductase 1, in response to various substrate and inhibitor configurations

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15-Keto prostaglandin E2 induces heme oxygenase-1 expression through activation of Nrf2 in human colon epithelial CCD 841 CoN cells

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Links to other databases for prostaglandin E2

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