Human Metabolome Database Version 3.5

Showing metabocard for Prostaglandin E2 (HMDB01220)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:30:50 -0600
HMDB ID HMDB01220
Secondary Accession Numbers None
Metabolite Identification
Common Name Prostaglandin E2
Description The 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 Link_out). 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 Link_out). 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C20H32O5
Average Molecular Weight 352.4651
Monoisotopic Molecular Weight 352.224974134
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 Name dinoprostone
CAS Registry Number 363-24-6
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 Key XEYBRNLFEZDVAW-ARSRFYASSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Prostaglandins 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 Parent Prostaglandins and related compounds
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 67 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 2.82 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.044 g/L ALOGPS
LogP 3.31 ALOGPS
LogP 3.23 ChemAxon
LogS -3.90 ALOGPS
pKa (strongest acidic) 4.3 ChemAxon
pKa (strongest basic) -1.6 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 94.83 A2 ChemAxon
Rotatable Bond Count 12 ChemAxon
Refractivity 99.44 ChemAxon
Polarizability 40.03 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 25
MS/MS Spectrum LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 35
MS/MS Spectrum LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 45
MS/MS Spectrum LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 55
MS/MS Spectrum LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 60
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Fibroblasts
  • Placenta
  • Brain
  • Skin
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 map00590 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
3.7E-5 +/- 1.2E-5 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.0967 +/- 0.012 uM Adult (>18 years old) Not Specified Comment Normal
Blood Detected and Quantified
0.172 +/- 0.13 uM Adult (>18 years old) Not Specified Comment Normal
Blood Detected and Quantified
0.00218 +/- 0.00287 uM Adult (>18 years old) Both Comment Normal
Blood Detected and Quantified
0.001 +/- 0.000053 uM Adult (>18 years old) Male Normal
Blood Detected and Quantified
0.0009 +/- 0.000060 uM Adult (>18 years old) Female Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.0013 +/- 0.0020 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
<5.110e-05 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0 - 0.02 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.000057 +/- 0.000020 umol/mmol creatinine Adult (>18 years old) Female Normal
  • Geigy Scient...
Urine Detected and Quantified
0.00012 +/- 0.000025 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Geigy Scient...
Urine Detected and Quantified
0.0098 +/- 0.0011 umol/mmol creatinine Adult (>18 years old) Female Normal
Urine Detected and Quantified
0.015 +/- 0.002 umol/mmol creatinine Adult (>18 years old) Female Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 5.650e-05 +/- 3.975e-06 uM Adult (>18 years old) Female In pregnant women(nonlabor pain)
Cerebrospinal Fluid (CSF) Detected and Quantified 5.724e-05 +/- 5.337e-06 uM Adult (>18 years old) Female In pregnant women(labor pain)
Cerebrospinal Fluid (CSF) Detected and Quantified 4.543e-05 uM Not Specified Not Specified closed head
Cerebrospinal Fluid (CSF) Detected and Quantified 9.937e-05 uM Not Specified Not Specified gunshot wound
Cerebrospinal Fluid (CSF) Detected and Quantified 5.962e-06 +/- 4.259e-07 uM Not Specified Not Specified HIV-seronegative, noninflammatory neurological disease
Cerebrospinal Fluid (CSF) Detected and Quantified 4.826e-06 +/- 6.246e-07 uM Not Specified Not Specified HIV-Seropositive
Cerebrospinal Fluid (CSF) Detected and Quantified 6.246e-05 +/- 0.000165 uM Not Specified Not Specified hydrocephalus
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00716 (0.000116-0.0142) uM Not Specified Not Specified meningitis
Cerebrospinal Fluid (CSF) Detected and Quantified 35.0 +/- 10.0 uM Adult (>18 years old) Not Specified Amyotrophic 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 Link_out
      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 Link_out
          Associated OMIM IDs
          • 105400 Link_out (Amyotrophic lateral sclerosis)
          DrugBank ID Not Available
          DrugBank Metabolite ID Not Available
          Phenol Explorer Compound ID Not Available
          Phenol Explorer Metabolite ID Not Available
          FoodDB ID FDB022498
          KNApSAcK ID Not Available
          Chemspider ID 4444059 Link_out
          KEGG Compound ID C00584 Link_out
          BioCyc ID 5Z13E-15S-1115-DIHYDROXY-9-OXOPROS Link_out
          BiGG ID 35424 Link_out
          Wikipedia Link Dinoprostone Link_out
          NuGOwiki Link HMDB01220 Link_out
          Metagene Link HMDB01220 Link_out
          METLIN ID 6089 Link_out
          PubChem Compound 5280360 Link_out
          PDB ID Not Available
          ChEBI ID 15551 Link_out
          References
          Synthesis Reference Corey, 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) Download (PDF)
          General References
          1. Ilzecka J: Prostaglandin E2 is increased in amyotrophic lateral sclerosis patients. Acta Neurol Scand. 2003 Aug;108(2):125-9. Pubmed: 12859290 Link_out
          2. 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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          13. Greaves MW: Does ultraviolet-evoked prostaglandin formation protect skin from actinic cancer? Lancet. 1978 Jan 28;1(8057):189. Pubmed: 74611 Link_out
          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 Link_out

          Enzymes
          Name: Carbonyl reductase [NADPH] 1
          Reactions:
          Prostaglandin F2a + NADP unknown Prostaglandin E2 + NADPH + Hydrogen Ion details
          Gene Name: CBR1
          Uniprot ID: P16152 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Carbonyl reductase [NADPH] 3
          Reactions:
          Prostaglandin F2a + NADP unknown Prostaglandin E2 + NADPH + Hydrogen Ion details
          Gene Name: CBR3
          Uniprot ID: O75828 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: 15-hydroxyprostaglandin dehydrogenase [NAD(+)]
          Reactions: Not Available
          Gene Name: HPGD
          Uniprot ID: P15428 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Prostaglandin E synthase
          Reactions:
          Prostaglandin H2 unknown Prostaglandin E2 details
          Gene Name: PTGES
          Uniprot ID: O14684 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Prostaglandin E2 receptor EP1 subtype
          Reactions: Not Available
          Gene Name: PTGER1
          Uniprot ID: P34995 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Prostaglandin E2 receptor EP4 subtype
          Reactions: Not Available
          Gene Name: PTGER4
          Uniprot ID: P35408 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Prostaglandin E synthase 2
          Reactions:
          Prostaglandin H2 unknown Prostaglandin E2 details
          Gene Name: PTGES2
          Uniprot ID: Q9H7Z7 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Prostaglandin E2 receptor EP3 subtype
          Reactions: Not Available
          Gene Name: PTGER3
          Uniprot ID: P43115 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Prostaglandin E2 receptor EP2 subtype
          Reactions: Not Available
          Gene Name: PTGER2
          Uniprot ID: P43116 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Prostaglandin E synthase 3
          Reactions:
          Prostaglandin H2 unknown Prostaglandin E2 details
          Gene Name: PTGES3
          Uniprot ID: Q15185 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: CUGBP Elav-like family member 2
          Reactions: Not Available
          Gene Name: CELF2
          Uniprot ID: O95319 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Transporters
          Name: Solute carrier organic anion transporter family member 1B1
          Reactions: Not Available
          Gene Name: SLCO1B1
          Uniprot ID: Q9Y6L6 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Solute carrier family 22 member 7
          Reactions: Not Available
          Gene Name: SLC22A7
          Uniprot ID: Q9Y694 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA