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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
SpectraGC-MSLC-MS1D NMR2D NMR
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
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.7E-5 +/- 1.2E-5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0967 +/- 0.012 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.172 +/- 0.13 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.00218 +/- 0.00287 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.001 +/- 0.000053 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0009 +/- 0.000060 uMAdult (>18 years old)FemaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0013 +/- 0.0020 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified<5.110e-05 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0 - 0.02 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.000057 +/- 0.000020 umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.00012 +/- 0.000025 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.0098 +/- 0.0011 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.015 +/- 0.002 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified5.650e-05 +/- 3.975e-06 uMAdult (>18 years old)FemalePregnant women(nonlabor pain) details
Cerebrospinal Fluid (CSF)Detected and Quantified5.724e-05 +/- 5.337e-06 uMAdult (>18 years old)FemalePregnant women(labor pain) details
Cerebrospinal Fluid (CSF)Detected and Quantified4.543e-05 uMNot SpecifiedNot Specifiedclosed head injury details
Cerebrospinal Fluid (CSF)Detected and Quantified9.937e-05 uMNot SpecifiedNot Specifiedgunshot wound details
Cerebrospinal Fluid (CSF)Detected and Quantified5.962e-06 +/- 4.259e-07 uMNot SpecifiedNot SpecifiedHIV-seronegative, noninflammatory neurological disease details
Cerebrospinal Fluid (CSF)Detected and Quantified4.826e-06 +/- 6.246e-07 uMNot SpecifiedNot SpecifiedHIV-Seropositive details
Cerebrospinal Fluid (CSF)Detected and Quantified6.246e-05 +/- 0.000165 uMNot SpecifiedNot Specifiedhydrocephalus details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00716 (0.000116-0.0142) uMNot SpecifiedNot Specifiedmeningitis details
Cerebrospinal Fluid (CSF)Detected and Quantified35.0 +/- 10.0 uMAdult (>18 years old)Not SpecifiedAmyotrophic lateral sclerosis details
Associated Disorders and Diseases
Disease References
Amyotrophic lateral sclerosis
  1. 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
  1. 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)Download (PDF)
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

General function:
Involved in oxidoreductase activity
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:
CBR1
Uniprot ID:
P16152
Molecular weight:
30374.73
Reactions
Prostaglandin F2a + NADP → Prostaglandin E2 + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Has low NADPH-dependent oxidoreductase activity towards 4-benzoylpyridine and menadione (in vitro).
Gene Name:
CBR3
Uniprot ID:
O75828
Molecular weight:
30849.97
Reactions
Prostaglandin F2a + NADP → Prostaglandin E2 + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Prostaglandin inactivation. Contributes to the regulation of events that are under the control of prostaglandin levels. Catalyzes the NAD-dependent dehydrogenation of lipoxin A4 to form 15-oxo-lipoxin A4. Inhibits in vivo proliferation of colon cancer cells.
Gene Name:
HPGD
Uniprot ID:
P15428
Molecular weight:
28977.105
General function:
Involved in prostaglandin-E synthase activity
Specific function:
Catalyzes the oxidoreduction of prostaglandin endoperoxide H2 (PGH2) to prostaglandin E2 (PGE2).
Gene Name:
PTGES
Uniprot ID:
O14684
Molecular weight:
17102.135
Reactions
Prostaglandin H2 → Prostaglandin E2details
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(q) proteins which activate a phosphatidylinositol-calcium second messenger system. May play a role as an important modulator of renal function. Implicated the smooth muscle contractile response to PGE2 in various tissues
Gene Name:
PTGER1
Uniprot ID:
P34995
Molecular weight:
41800.7
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. Has a relaxing effect on smooth muscle. May play an important role in regulating renal hemodynamics, intestinal epithelial transport, adrenal aldosterone secretion, and uterine function
Gene Name:
PTGER4
Uniprot ID:
P35408
Molecular weight:
53118.8
General function:
Involved in electron carrier activity
Specific function:
Isomerase that catalyzes the conversion of unstable intermediate of prostaglandin E2 H2 (PGH2) into the more stable prostaglandin E2 (PGE2) form. May also have transactivation activity toward IFN-gamma (IFNG), possibly via an interaction with CEBPB; however, the relevance of transcription activation activity remains unclear.
Gene Name:
PTGES2
Uniprot ID:
Q9H7Z7
Molecular weight:
21337.205
Reactions
Prostaglandin H2 → Prostaglandin E2details
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for prostaglandin E2 (PGE2); the EP3 receptor may be involved in inhibition of gastric acid secretion, modulation of neurotransmitter release in central and peripheral neurons, inhibition of sodium and water reabsorption in kidney tubulus and contraction in uterine smooth muscle. The activity of this receptor can couple to both the inhibition of adenylate cyclase mediated by G-I proteins, and to an elevation of intracellular calcium. The various isoforms have identical ligand binding properties but can interact with different second messenger systems
Gene Name:
PTGER3
Uniprot ID:
P43115
Molecular weight:
43309.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. The subsequent raise in intracellular cAMP is responsible for the relaxing effect of this receptor on smooth muscle
Gene Name:
PTGER2
Uniprot ID:
P43116
Molecular weight:
39759.9
General function:
Involved in prostaglandin-E synthase activity
Specific function:
Molecular chaperone that localizes to genomic response elements in a hormone-dependent manner and disrupts receptor-mediated transcriptional activation, by promoting disassembly of transcriptional regulatory complexes.
Gene Name:
PTGES3
Uniprot ID:
Q15185
Molecular weight:
18697.195
Reactions
Prostaglandin H2 → Prostaglandin E2details
General function:
Involved in nucleotide binding
Specific function:
RNA-binding protein implicated in the regulation of several post-transcriptional events. Involved in pre-mRNA alternative splicing, mRNA translation and stability. Mediates exon inclusion and/or exclusion in pre-mRNA that are subject to tissue-specific and developmentally regulated alternative splicing. Specifically activates exon 5 inclusion of TNNT2 in embryonic, but not adult, skeletal muscle. Activates TNNT2 exon 5 inclusion by antagonizing the repressive effect of PTB. Acts as both an activator and repressor of a pair of coregulated exons:promotes inclusion of the smooth muscle (SM) exon but exclusion of the non-muscle (NM) exon in actinin pre-mRNAs. Promotes inclusion of exonS 21 and exclusion of exon 5 of the NMDA receptor R1 pre- mRNA. Involved in the apoB RNA editing activity. Increases COX2 mRNA stability and inhibits COX2 mRNA translation in epithelial cells after radiation injury. Modulates the cellular apoptosis program by regulating COX2-mediated prostaglandin E2 (PGE2) expression. Binds to (CUG)n triplet repeats in the 3'-UTR of transcripts such as DMPK. Binds to the muscle-specific splicing enhancer (MSE) intronic sites flanking the TNNT2 alternative exon 5. Binds preferentially to UG-rich sequences, in particular UG repeat and UGUU motifs. Binds to apoB mRNA, specifically to AU-rich sequences located immediatly upstream of the edited cytidine. Binds AU-rich sequences in the 3'-UTR of COX2 mRNA. Binds to an intronic RNA element responsible for the silencing of exon 21 splicing. Binds to (CUG)n repeats
Gene Name:
CELF2
Uniprot ID:
O95319
Molecular weight:
54284.4

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular weight:
76448.0
General function:
Involved in transmembrane transport
Specific function:
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
Molecular weight:
60025.0