PGE2   Click here for help

GtoPdb Ligand ID: 1883

Synonyms: Cervidil® | minprositin E2 | minprostin E2 | Propess® | prostaglandin E2
Approved drug PDB Ligand Immunopharmacology Ligand
PGE2 is an approved drug (FDA (1977))
Compound class: Metabolite or derivative
Comment: PGE2 is a the major endogenous prostaglandin. Synthetic PGE2 is known as dinoprostone. PGE2 activates prostanoid family GPCRs.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: prostaglandin e2

PGE2 is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 12
Topological polar surface area 94.83
Molecular weight 352.22
XLogP 2.79
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCCCCC(C=CC1C(O)CC(=O)C1CC=CCCCC(=O)O)O
Isomeric SMILES CCCCC[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O
InChI 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
References
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Molecular cloning and characterization of the human prostanoid DP receptor.
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Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes.
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Pharmacological characterization of [(3)H]-prostaglandin E(2) binding to the cloned human EP(4) prostanoid receptor.
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Progesterone activates the principal Ca2+ channel of human sperm.
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11. Neuschäfer-Rube F, DeVries C, Hänecke K, Jungermann K, Püschel GP. (1994)
Molecular cloning and expression of a prostaglandin E2 receptor of the EP3 beta subtype from rat hepatocytes.
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12. Neuschäfer-Rube F, Engemaier E, Koch S, Böer U, Püschel GP. (2003)
Identification by site-directed mutagenesis of amino acids contributing to ligand-binding specificity or signal transduction properties of the human FP prostanoid receptor.
Biochem J, 371 (Pt 2): 443-9. [PMID:12519077]
13. Neuschäfer-Rube F, Hermosilla R, Kuna M, Pathe-Neuschäfer-Rube A, Schülein R, Püschel GP. (2005)
A Ser/Thr cluster within the C-terminal domain of the rat prostaglandin receptor EP3alpha is essential for agonist-induced phosphorylation, desensitization and internalization.
Br J Pharmacol, 145 (8): 1132-42. [PMID:15937517]
14. Sawyer N, Cauchon E, Chateauneuf A, Cruz RP, Nicholson DW, Metters KM, O'Neill GP, Gervais FG. (2002)
Molecular pharmacology of the human prostaglandin D2 receptor, CRTH2.
Br J Pharmacol, 137 (8): 1163-72. [PMID:12466225]
15. Sharif NA, Davis TL. (2002)
Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques.
J Pharm Pharmacol, 54 (4): 539-47. [PMID:11999132]
16. Stillman BA, Breyer MD, Breyer RM. (1999)
Importance of the extracellular domain for prostaglandin EP(2) receptor function.
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17. Su X, Leon LA, Wu CW, Morrow DM, Jaworski JP, Hieble JP, Lashinger ES, Jin J, Edwards RM, Laping NJ. (2008)
Modulation of bladder function by prostaglandin EP3 receptors in the central nervous system.
Am J Physiol Renal Physiol, 295 (4): F984-94. [PMID:18632791]
18. Sugimoto Y, Nakato T, Kita A, Hatae N, Tabata H, Tanaka S, Ichikawa A. (2003)
Functional domains essential for Gs activity in prostaglandin EP2 and EP3 receptors.
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19. Suzawa T, Miyaura C, Inada M, Maruyama T, Sugimoto Y, Ushikubi F, Ichikawa A, Narumiya S, Suda T. (2000)
The role of prostaglandin E receptor subtypes (EP1, EP2, EP3, and EP4) in bone resorption: an analysis using specific agonists for the respective EPs.
Endocrinology, 141 (4): 1554-9. [PMID:10746663]
20. Whittle BJ, Silverstein AM, Mottola DM, Clapp LH. (2012)
Binding and activity of the prostacyclin receptor (IP) agonists, treprostinil and iloprost, at human prostanoid receptors: treprostinil is a potent DP1 and EP2 agonist.
Biochem Pharmacol, 84 (1): 68-75. [PMID:22480736]
21. Wilson RJ, Giblin GM, Roomans S, Rhodes SA, Cartwright KA, Shield VJ, Brown J, Wise A, Chowdhury J, Pritchard S et al.. (2006)
GW627368X ((N-{2-[4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetyl} benzene sulphonamide): a novel, potent and selective prostanoid EP4 receptor antagonist.
Br J Pharmacol, 148 (3): 326-39. [PMID:16604093]
22. Wright DH, Metters KM, Abramovitz M, Ford-Hutchinson AW. (1998)
Characterization of the recombinant human prostanoid DP receptor and identification of L-644,698, a novel selective DP agonist.
Br J Pharmacol, 123 (7): 1317-24. [PMID:9579725]