PGE1   Click here for help

GtoPdb Ligand ID: 1882

Synonyms: Alprostadil® | MR-256 | prostaglandin E1
Approved drug PDB Ligand
PGE1 is an approved drug (FDA (1981))
Compound class: Metabolite
Comment: PGE1 is an endogenous prostaglandin. Synthetic PGE1 is known as alprostadil. PGE1 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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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 13
Topological polar surface area 94.83
Molecular weight 354.24
XLogP 3.31
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCCCC(C=CC1C(O)CC(=O)C1CCCCCCC(=O)O)O
Isomeric SMILES CCCCC[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O)O
InChI InChI=1S/C20H34O5/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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1
InChI Key GMVPRGQOIOIIMI-DWKJAMRDSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Bioactivity Comments
Although PGE1 has potent affinity across the EP receptor family we have tagged the EP1 and EP2 receptors as primary drug targets as it is believed that its clinical efficacy is manifest primarily through agonism at these receptors.
Natural/Endogenous Targets
Target
DP1 receptor
EP1 receptor
EP2 receptor
EP3 receptor
EP4 receptor
IP receptor
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
EP4 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 9.2 pKi - 2
⤷ pKi 9.2 [2]
EP3 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 9.0 pKi - 5
⤷ pKi 9.0 (Ki 1x10-9 M) [5]
EP3 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 9.0 pKi - 2
⤷ pKi 9.0 (Ki 1x10-9 M) [2]
EP4 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 8.8 pKi - 4
⤷ pKi 8.8 (Ki 1.58x10-9 M) [4]
EP4 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 8.7 pKi - 5
⤷ pKi 8.7 [5]
EP2 receptor Primary target of this compound Hs Agonist Full agonist 8.0 pKi - 1
⤷ pKi 8.0 (Ki 9.1x10-9 M) [1]
EP2 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 8.0 pKi - 5
⤷ pKi 8.0 [5]
EP2 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 8.0 pKi - 2
⤷ pKi 8.0 [2]
IP receptor Ligand is endogenous in the given species Mm Agonist Full agonist 7.5 pKi - 5
⤷ pKi 7.5 [5]
EP1 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 7.4 pKi - 5
⤷ pKi 7.4 [5]
DP1 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 7.3 pKi - 13
⤷ pKi 7.3 [13]
EP1 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 7.0 pKi - 2
⤷ pKi 7.0 [2]
EP1 receptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 6.8 pKi - 11
⤷ pKi 6.8 [11]
IP receptor Ligand is endogenous in the given species Hs Agonist Full agonist 6.5 – 6.8 pKi - 8,12
⤷ pKi 6.5 – 6.8 (Ki 3.18x10-7 – 1.5x10-7 M) [8,12]
EP4 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 9.5 pEC50 - 6
⤷ pEC50 9.5 (EC50 3.1x10-10 M) [6]
EP3 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 9.4 pEC50 - 2
⤷ pEC50 9.4 (EC50 4.5x10-10 M) EP3α isoform [2]
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 - 7
⤷ pEC50 6.3 (EC50 5x10-7 M) [7]
Voltage: -80.0 mV
Description: Patch clamp electrophysiology
CatSper2 Ligand is endogenous in the given species Hs Activator Full agonist 6.3 pEC50 - 7
⤷ pEC50 6.3 (EC50 5x10-7 M) [7]
Voltage: -80.0 mV
Description: Patch clamp electrophysiology.
CatSper3 Ligand is endogenous in the given species Hs Activator Full agonist 6.3 pEC50 - 7
⤷ pEC50 6.3 (EC50 5x10-7 M) [7]
Voltage: -80.0 mV
Description: Patch clamp electrophysiology.
CatSper4 Ligand is endogenous in the given species Hs Activator Full agonist 6.3 pEC50 - 7
⤷ pEC50 6.3 (EC50 5x10-7 M) [7]
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 EP4 receptor PGE2 = PGE1 > PGF2α, PGI2 > PGD2, thromboxane A2
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
Potency order of endogenous ligands at IP receptor PGI2 >> PGE1 > PGD2, PGF2α > 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 [3]; reported to export prostaglandins in a manner sensitive to NSAIDS [10]. A common binding site accommodates substrates including PGE1, PGE2 and dehydroepiandrosterone sulphate (DHEAS) [9].
Ligand mentioned in the following text fields
Prostanoid receptors overview
CatSper and Two-Pore channels (TPC) comments