PGI2   Click here for help

GtoPdb Ligand ID: 1915

Synonyms: prostacyclin | prostacyclin I2 | prostaglandin I2 | vasocyclin
Approved drug
PGI2 is an approved drug (FDA (1995))
Compound class: Metabolite
Comment: PGI2 is an endogenous prostaglandin. Synthetic PGI2 is known as epoprostenol. PG12 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: pgi2

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 10
Topological polar surface area 86.99
Molecular weight 352.22
XLogP 2.98
No. Lipinski's rules broken 0
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)CC2C1CC(=CCCCC(=O)O)O2)O
Isomeric SMILES CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/O2)O
InChI InChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8-/t14-,16+,17+,18+,19-/m0/s1
InChI Key KAQKFAOMNZTLHT-OZUDYXHBSA-N
Natural/Endogenous Targets
Target
DP1 receptor
DP2 receptor
EP1 receptor
EP2 receptor
EP3 receptor
EP4 receptor
FP receptor
IP receptor
TP receptor
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
IP receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.8 pKi - 3
⤷ pKi 7.8 (Ki 1.585x10-8 M) [3]
EP4 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 5.1 pKi - 1
⤷ pKi 5.1 [1]
EP1 receptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 4.8 pKi - 2
⤷ pKi 4.8 [2]
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
Potency order of endogenous ligands at IP receptor PGI2 >> PGE1 > PGD2, PGF2α > thromboxane A2
Ligand mentioned in the following text fields
1C. Peroxisome proliferator-activated receptors overview
Prostaglandin synthases overview
Prostanoid receptors overview