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
Classification Click here for help
Compound class Metabolite or derivative
Approved drug? Yes (FDA (1977))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
International Nonproprietary Names Click here for help
INN number INN
3075 dinoprostone
Synonyms Click here for help
Cervidil® | minprositin E2 | minprostin E2 | Propess® | prostaglandin E2
Database Links Click here for help
Specialist databases
GPCRdb Ligand PGE2
Other databases
CAS Registry No. 363-24-6
ChEBI CHEBI:116390
ChEMBL Ligand CHEMBL548
DrugBank Ligand DB00917
DrugCentral Ligand 913
GtoPdb PubChem SID 135651539
PubChem CID 5280360
RCSB PDB Ligand P2E
Search Google for chemical match using the InChIKey XEYBRNLFEZDVAW-ARSRFYASSA-N
Search Google for chemicals with the same backbone XEYBRNLFEZDVAW
Search PubMed clinical trials dinoprostone
Search PubMed titles dinoprostone
Search PubMed titles/abstracts dinoprostone
UniChem Compound Search for chemical match using the InChIKey XEYBRNLFEZDVAW-ARSRFYASSA-N
UniChem Connectivity Search for chemical match using the InChIKey XEYBRNLFEZDVAW-ARSRFYASSA-N
Wikipedia Prostaglandin_E2

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Tocris
Prostaglandin E2 (links to external site)
Cat. No. 2296