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

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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
Bioactivity Comments
Although PGE2 has potent affinity across the EP receptor family we have tagged the EP1 and EP2 receptors as primary drug targets.
Natural/Endogenous Targets
Target
DP1 receptor
DP2 receptor
EP1 receptor
EP2 receptor
EP3 receptor
EP4 receptor
FP receptor
IP receptor
TP receptor
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
mPGES2 5.3.99.3 PGH2 = PGE2
mPGES1 5.3.99.3 PGH2 = PGE2
CBR1 1.1.1.189 PGE2 + NADP+ = PGF2α + NADPH + H+
cPGES 5.3.99.3 PGH2 = PGE2
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Organic cation transporter 1
Organic cation transporter 2 8
Organic anion transporter 2
OATP1A2
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
EP3 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 8.9 pKd - 9
⤷ pKd 8.9 (Kd 1.4x10-9 M) [9]
EP3 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 8.2 – 9.1 pKd - 21,25-26
⤷ pKd 8.7 (Kd 2.1x10-9 M) EP3-II & -III isoforms [21]
pKd 8.2 – 9.1 (Kd 6x10-9 – 8x10-10 M) EP3-I isoform [21,25-26]
EP4 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 8.6 pKd - 9
⤷ pKd 8.6 (Kd 2.5x10-9 M) [9]
EP3 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 7.8 – 9.1 pKd - 3,13,15,21
⤷ pKd 9.0 (Kd 1.1x10-9 M) EP3γ isoform [21]
pKd 8.3 – 9.1 (Kd 5x10-9 – 8x10-10 M) EP3α isoform [3,15,21]
pKd 7.8 – 8.4 (Kd 1.5x10-8 – 3.9x10-9 M) EP3β isoform [13,15]
EP3 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 9.5 pKi - 1
⤷ pKi 9.5 (Ki 3.3x10-10 M) EP3-III isoform [1]
EP3 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 9.1 pKi - 9
⤷ pKi 9.1 (Ki 8.5x10-10 M) [9]
EP3 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 9.0 pKi - 3
⤷ pKi 9.0 [3]
EP4 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 9.0 pKi - 3
⤷ pKi 9.0 [3]
EP4 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 8.5 – 8.7 pKi - 9,23
⤷ pKi 8.5 – 8.7 (Ki 3x10-9 – 2x10-9 M) [9,23]
EP4 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 8.1 – 9.1 pKi - 1,5,12,20,26
⤷ pKi 8.1 – 9.1 (Ki 7.94x10-9 – 7.94x10-10 M) [1,5,12,20,26]
EP2 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 8.2 pKi - 3
⤷ pKi 8.2 [3]
EP2 receptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 7.5 – 8.3 pKi - 1,20,26
⤷ pKi 7.5 – 8.3 (Ki 3.16x10-8 – 5.01x10-9 M) [1,20,26]
EP1 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 7.7 pKi - 9,23
⤷ pKi 7.7 [9,23]
EP1 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 7.7 pKi - 3
⤷ pKi 7.7 [3]
EP1 receptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 7.3 – 8.0 pKi - 1,19,26
⤷ pKi 7.3 – 8.0 [1,19,26]
EP2 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 7.4 – 7.9 pKi - 9,22-23
⤷ pKi 7.4 – 7.9 [9,22-23]
FP receptor Ligand is endogenous in the given species Mm Agonist Full agonist 7.0 pKi - 9
⤷ pKi 7.0 [9]
DP1 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 6.5 – 7.0 pKi - 1-2,27
⤷ pKi 6.5 – 7.0 [1-2,27]
FP receptor Ligand is endogenous in the given species Hs Agonist Full agonist 6.4 – 6.9 pKi - 1,14
⤷ pKi 6.4 – 6.9 [1,14]
DP2 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 5.5 pKi - 7
⤷ pKi 5.5 [7]
DP2 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 5.3 pKi - 18
⤷ pKi 5.3 [18]
TP receptor Ligand is endogenous in the given species Hs Agonist Full agonist 4.5 pKi - 1
⤷ pKi 4.5 [1]
EP3 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 9.4 pEC50 - 3
⤷ pEC50 9.4 (EC50 4.1x10-10 M) EP3α isoform [3]
EP4 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 6.1 pEC50 - 10
⤷ pEC50 6.1 (EC50 9x10-7 M) [10]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CatSper1 Ligand is endogenous in the given species Hs Activator Full agonist 6.3 pEC50 - 11
⤷ pEC50 6.3 (EC50 5x10-7 M) [11]
Voltage: -80.0 mV
Description: Patch clamp electrophysiology
CatSper2 Ligand is endogenous in the given species Hs Activator Full agonist 6.3 pEC50 - 11
⤷ pEC50 6.3 (EC50 5x10-7 M) [11]
Voltage: -80.0 mV
Description: Patch clamp electrophysiology.
CatSper3 Ligand is endogenous in the given species Hs Activator Full agonist 6.3 pEC50 - 11
⤷ pEC50 6.3 (EC50 5x10-7 M) [11]
Voltage: -80.0 mV
Description: Patch clamp electrophysiology.
CatSper4 Ligand is endogenous in the given species Hs Activator Full agonist 6.3 pEC50 - 11
⤷ pEC50 6.3 (EC50 5x10-7 M) [11]
Voltage: -80.0 mV
Description: Patch clamp electrophysiology.
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Potency order of endogenous ligands at DP1 receptor PGD2 > PGE1 >> PGE2 > PGF2α > PGI2, thromboxane A2
Potency order of endogenous ligands at FP receptor PGF2α > PGD2 > PGE2 > PGI2, thromboxane A2
Potency order of endogenous ligands at EP4 receptor PGE2 = PGE1 > PGF2α, PGI2 > PGD2, thromboxane A2
Potency order of endogenous ligands at DP2 receptor PGD2 >> PGF2α, PGE2 > PGI2, thromboxane A2
Potency order of endogenous ligands at TP receptor thromboxane A2 = PGH2 >> PGD2, PGE2, PGF2α, PGI2
Potency order of endogenous ligands at EP2 receptor PGE2 = PGE1 > PGF2α, PGI2 > PGD2, thromboxane A2
Potency order of endogenous ligands at EP1 receptor PGE2 > PGE1 > PGF2α, PGI2 > PGD2, thromboxane A2
Potency order of endogenous ligands at EP3 receptor PGE2, PGE1 > PGF2α, PGI2 > PGD2, thromboxane A2
Targets where the ligand is described in the comment field
Target Comment
ABCC4 Although reported to facilitate cellular cyclic nucleotide export, this role has been questioned [4]; reported to export prostaglandins in a manner sensitive to NSAIDS [17]. A common binding site accommodates substrates including PGE1, PGE2 and dehydroepiandrosterone sulphate (DHEAS) [16].
mPGES2 Heme-free mPGES2 catalyses the isomerisation of prostaglandin H2 (PGE2) to prostaglandin E2 (PGE2) in the presence of glutathione (GSH); in contrast heme-bound mPGES2 catalyses the degradation of PGH2 to 12-hydroxyheptadecatrienoic acid (HHT) and malondialdehyde (MDA) [24,28-29]. In colon cancer cells artemisinin has been reported to bind reversibly to mPGES2 (occupying the PGH2 site), with the effect of blocking PGE2 biosynthesis and inhibiting cell proliferation [6].
Ligand mentioned in the following text fields
Prostaglandin synthases overview
Prostanoid receptors overview