Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:30:50 UTC
HMDB IDHMDB01220
Secondary Accession NumbersNone
Metabolite Identification
Common NameProstaglandin E2
DescriptionThe naturally occurring prostaglandin E2 (PGE2) is known in medicine as dinoprostone. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bone's mineralized matrix). PGE2 is also the prostaglandin that ultimately induces fever. PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, induction of uterine contractions and of platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1α and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype (PMID: 16978535 ). Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bone's mineralized matrix). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, to induce uterine contractions and to activate platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1alpha and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype (PMID: 16978535 ). Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways.
Structure
Thumb
Synonyms
  1. (-)-Prostaglandin E2
  2. (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate
  3. (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acid
  4. (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoate
  5. (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid
  6. (5Z,13E,15S)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoate
  7. (5Z,13E,15S)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoic acid
  8. 5-trans-PGE2
  9. Dinoprostone
  10. Dinoprostonum
  11. Glandin
  12. L-Prostaglandin E2
  13. Minprositin E2
  14. Minprostin E2
  15. PGE2
  16. Prepidil
  17. Prostaglandin E
  18. Prostaglandin E2
  19. Prostaglandin E2alpha
  20. Prostarmon E
  21. Prostin
  22. Prostin E2
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
Traditional IUPAC Namedinoprostone
CAS Registry Number363-24-6
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1
InChI KeyXEYBRNLFEZDVAW-ARSRFYASSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassEicosanoids
Sub ClassProstaglandins and related compounds
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Carbocyclic Fatty Acids
  • Keto Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Allyl Alcohol
  • Carboxylic Acid
  • Cyclic Alcohol
  • Ketone
  • Secondary Alcohol
Direct ParentProstaglandins and related compounds
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Prostaglandin and leukotriene metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point67 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.82HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility0.044 g/LALOGPS
logP3.31ALOGPS
logP3.23ChemAxon
logS-3.9ALOGPS
pKa (strongest acidic)4.3ChemAxon
pKa (strongest basic)-1.6ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area94.83ChemAxon
rotatable bond count12ChemAxon
refractivity99.44ChemAxon
polarizability40.03ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Brain
  • Fibroblasts
  • Placenta
  • Skin
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075map00590
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified3.7E-5 +/- 1.2E-5 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified0.0967 +/- 0.012 uMAdult (>18 years old)Not SpecifiedCommentNormal
BloodDetected and Quantified0.172 +/- 0.13 uMAdult (>18 years old)Not SpecifiedCommentNormal
BloodDetected and Quantified0.00218 +/- 0.00287 uMAdult (>18 years old)BothCommentNormal
BloodDetected and Quantified0.001 +/- 0.000053 uMAdult (>18 years old)MaleNormal
BloodDetected and Quantified0.0009 +/- 0.000060 uMAdult (>18 years old)FemaleNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.0013 +/- 0.0020 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified<5.110e-05 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0 - 0.02 uMAdult (>18 years old)BothNormal
UrineDetected and Quantified0.000057 +/- 0.000020 umol/mmol creatinineAdult (>18 years old)FemaleNormal
  • Geigy Scient...
UrineDetected and Quantified0.00012 +/- 0.000025 umol/mmol creatinineAdult (>18 years old)MaleNormal
  • Geigy Scient...
UrineDetected and Quantified0.0098 +/- 0.0011 umol/mmol creatinineAdult (>18 years old)FemaleNormal
UrineDetected and Quantified0.015 +/- 0.002 umol/mmol creatinineAdult (>18 years old)FemaleNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
Cerebrospinal Fluid (CSF)Detected and Quantified5.650e-05 +/- 3.975e-06 uMAdult (>18 years old)FemaleIn pregnant women(nonlabor pain)
Cerebrospinal Fluid (CSF)Detected and Quantified5.724e-05 +/- 5.337e-06 uMAdult (>18 years old)FemaleIn pregnant women(labor pain)
Cerebrospinal Fluid (CSF)Detected and Quantified4.543e-05 uMNot SpecifiedNot Specifiedclosed head
Cerebrospinal Fluid (CSF)Detected and Quantified9.937e-05 uMNot SpecifiedNot Specifiedgunshot wound
Cerebrospinal Fluid (CSF)Detected and Quantified5.962e-06 +/- 4.259e-07 uMNot SpecifiedNot SpecifiedHIV-seronegative, noninflammatory neurological disease
Cerebrospinal Fluid (CSF)Detected and Quantified4.826e-06 +/- 6.246e-07 uMNot SpecifiedNot SpecifiedHIV-Seropositive
Cerebrospinal Fluid (CSF)Detected and Quantified6.246e-05 +/- 0.000165 uMNot SpecifiedNot Specifiedhydrocephalus
Cerebrospinal Fluid (CSF)Detected and Quantified0.00716 (0.000116-0.0142) uMNot SpecifiedNot Specifiedmeningitis
Cerebrospinal Fluid (CSF)Detected and Quantified35.0 +/- 10.0 uMAdult (>18 years old)Not SpecifiedAmyotrophic lateral sclerosis
Associated Disorders and Diseases
Disease References
Amyotrophic lateral sclerosis
  • Almer G, Teismann P, Stevic Z, Halaschek-Wiener J, Deecke L, Kostic V, Przedborski S: Increased levels of the pro-inflammatory prostaglandin PGE2 in CSF from ALS patients. Neurology. 2002 Apr 23;58(8):1277-9. Pubmed: 11971099
Normal
  • Farker K, Schweer H, Vollandt R, Nassr N, Nagel U, Seyberth HW, Hoffmann A, Oettel M: Measurements of urinary prostaglandins in young ovulatory women during the menstrual cycle and in postmenopausal women. Prostaglandins. 1997 Sep;54(3):655-64. Pubmed: 9373880
Associated OMIM IDs
    105400 (Amyotrophic lateral sclerosis)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022498
KNApSAcK IDNot Available
Chemspider ID4444059
KEGG Compound IDC00584
BioCyc ID5Z13E-15S-1115-DIHYDROXY-9-OXOPROS
BiGG ID35424
Wikipedia LinkDinoprostone
NuGOwiki LinkHMDB01220
Metagene LinkHMDB01220
METLIN ID6089
PubChem Compound5280360
PDB IDNot Available
ChEBI ID15551
References
Synthesis ReferenceCorey, Elias J.; Weinshenker, Ned M.; Schaaf, Thomas K.; Huber, Willy. Stereo-controlled synthesis of dl-prostaglandins F2a and E2. Journal of the American Chemical Society (1969), 91(20), 5675-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Catanzarite VA: Prophylactic intramyometrial carboprost tromethamine does not substantially reduce blood loss relative to intramyometrial oxytocin at routine cesarean section. Am J Perinatol. 1990 Jan;7(1):39-42. Pubmed: 2403792
  2. Ilzecka J: Prostaglandin E2 is increased in amyotrophic lateral sclerosis patients. Acta Neurol Scand. 2003 Aug;108(2):125-9. Pubmed: 12859290
  3. Waschbisch A, Fiebich BL, Akundi RS, Schmitz ML, Hoozemans JJ, Candelario-Jalil E, Virtainen N, Veerhuis R, Slawik H, Yrjanheikki J, Hull M: Interleukin-1 beta-induced expression of the prostaglandin E-receptor subtype EP3 in U373 astrocytoma cells depends on protein kinase C and nuclear factor-kappaB. J Neurochem. 2006 Feb;96(3):680-93. Epub 2006 Jan 9. Pubmed: 16405508
  4. Seo JY, Kim EK, Lee SH, Park KC, Kim KH, Eun HC, Chung JH: Enhanced expression of cylooxygenase-2 by UV in aged human skin in vivo. Mech Ageing Dev. 2003 Aug-Sep;124(8-9):903-10. Pubmed: 14499495
  5. Amato F, Rizzuto G, Nicoletti A, Senatore M, Roberti R: [Isolated peripheral arterial ischaemia and medullary neurostimulation: case report] G Ital Nefrol. 2003 Mar-Apr;20(2):200-4. Pubmed: 12746806
  6. Laitinen K, Arvola T, Moilanen E, Lampi AM, Ruuska T, Isolauri E: Characterization of breast milk received by infants with gross blood in stools. Biol Neonate. 2005;87(1):66-72. Epub 2004 Nov 9. Pubmed: 15542928
  7. Yamada M, Ogata M, Kawai M, Mashima Y, Nishida T: Substance P in human tears. Cornea. 2003 Oct;22(7 Suppl):S48-54. Pubmed: 14703707
  8. Choi SH, Langenbach R, Bosetti F: Cyclooxygenase-1 and -2 enzymes differentially regulate the brain upstream NF-kappa B pathway and downstream enzymes involved in prostaglandin biosynthesis. J Neurochem. 2006 Aug;98(3):801-11. Epub 2006 Jun 19. Pubmed: 16787416
  9. Schmitz T, Dallot E, Leroy MJ, Breuiller-Fouche M, Ferre F, Cabrol D: EP(4) receptors mediate prostaglandin E(2)-stimulated glycosaminoglycan synthesis in human cervical fibroblasts in culture. Mol Hum Reprod. 2001 Apr;7(4):397-402. Pubmed: 11279302
  10. Christidis N, Kopp S, Ernberg M: The effect on mechanical pain threshold over human muscles by oral administration of granisetron and diclofenac-sodium. Pain. 2005 Feb;113(3):265-70. Pubmed: 15661432
  11. Konopka T, Rutkowska M, Hirnle L, Kopec W, Karolewska E: The secretion of prostaglandin E2 and interleukin 1-beta in women with periodontal diseases and preterm low-birth-weight. Bull Group Int Rech Sci Stomatol Odontol. 2003 Jan-Apr;45(1):18-28. Pubmed: 14535055
  12. Iizuka H, Ohkawara A, Ishibashi Y: Human skin epidermal adenylate cyclase systems: defective beta-adrenergic responsiveness in the involved epidermis of Darier's disease. Curr Probl Dermatol. 1983;11:45-58. Pubmed: 6317292
  13. Greaves MW: Does ultraviolet-evoked prostaglandin formation protect skin from actinic cancer? Lancet. 1978 Jan 28;1(8057):189. Pubmed: 74611
  14. Harizi H, Gualde N: Pivotal role of PGE2 and IL-10 in the cross-regulation of dendritic cell-derived inflammatory mediators. Cell Mol Immunol. 2006 Aug;3(4):271-7. Pubmed: 16978535

Enzymes

Gene Name:
CBR1
Uniprot ID:
P16152
Reactions
Prostaglandin F2a + NADP unknown Prostaglandin E2 + NADPH + Hydrogen Iondetails
Gene Name:
CBR3
Uniprot ID:
O75828
Reactions
Prostaglandin F2a + NADP unknown Prostaglandin E2 + NADPH + Hydrogen Iondetails
Gene Name:
PTGES
Uniprot ID:
O14684
Reactions
Prostaglandin H2 unknown Prostaglandin E2details
Gene Name:
PTGER1
Uniprot ID:
P34995
Gene Name:
PTGER4
Uniprot ID:
P35408
Gene Name:
PTGES2
Uniprot ID:
Q9H7Z7
Reactions
Prostaglandin H2 unknown Prostaglandin E2details
Gene Name:
PTGER3
Uniprot ID:
P43115
Gene Name:
PTGER2
Uniprot ID:
P43116
Gene Name:
PTGES3
Uniprot ID:
Q15185
Reactions
Prostaglandin H2 unknown Prostaglandin E2details
Gene Name:
CELF2
Uniprot ID:
O95319

Transporters

Gene Name:
SLC22A7
Uniprot ID:
Q9Y694