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))
Comment: PGE1 is an endogenous prostaglandin. Synthetic PGE1 is known as alprostadil. PGE1 activates prostanoid family GPCRs.
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
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 - 4
pKi 9.0 (Ki 1x10-9 M) [4]
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 - 3
pKi 8.8 (Ki 1.58x10-9 M) [3]
EP4 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 8.7 pKi - 4
pKi 8.7 [4]
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 - 4
pKi 8.0 [4]
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 - 4
pKi 7.5 [4]
EP1 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 7.4 pKi - 4
pKi 7.4 [4]
DP1 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 7.3 pKi - 10
pKi 7.3 [10]
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 - 8
pKi 6.8 [8]
IP receptor Ligand is endogenous in the given species Hs Agonist Full agonist 6.5 – 6.8 pKi - 7,9
pKi 6.5 – 6.8 (Ki 3.18x10-7 – 1.5x10-7 M) [7,9]
EP4 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 9.5 pEC50 - 5
pEC50 9.5 (EC50 3.1x10-10 M) [5]
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 - 6
pEC50 6.3 (EC50 5x10-7 M) [6]
Voltage: -80.0 mV
Description: Patch clamp electrophysiology
CatSper2 Ligand is endogenous in the given species Hs Activator Full agonist 6.3 pEC50 - 6
pEC50 6.3 (EC50 5x10-7 M) [6]
Voltage: -80.0 mV
Description: Patch clamp electrophysiology.
CatSper3 Ligand is endogenous in the given species Hs Activator Full agonist 6.3 pEC50 - 6
pEC50 6.3 (EC50 5x10-7 M) [6]
Voltage: -80.0 mV
Description: Patch clamp electrophysiology.
CatSper4 Ligand is endogenous in the given species Hs Activator Full agonist 6.3 pEC50 - 6
pEC50 6.3 (EC50 5x10-7 M) [6]
Voltage: -80.0 mV
Description: Patch clamp electrophysiology.
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Ligand mentioned in the following text fields