iloprost   

GtoPdb Ligand ID: 1895

Synonyms: Ventavis®
iloprost is an approved drug (EMA (2003), FDA (2004))
Compound class: Synthetic organic
Comment: Iloprost is a synthetic analogue of PGI2.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 77.76
Molecular weight 360.23
XLogP 3.19
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CC#CCC(C(C=CC1C(O)CC2C1CC(=CCCCC(=O)O)C2)O)C
Isomeric SMILES CC#CCC([C@@H](/C=C/C1[C@H](O)C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/C2)O)C
InChI InChI=1S/C22H32O4/c1-3-4-7-15(2)20(23)11-10-18-19-13-16(8-5-6-9-22(25)26)12-17(19)14-21(18)24/h8,10-11,15,17-21,23-24H,5-7,9,12-14H2,1-2H3,(H,25,26)/b11-10+,16-8+/t15?,17-,18?,19-,20+,21+/m0/s1
InChI Key HIFJCPQKFCZDDL-SGSAMSKHSA-N
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 Mm Agonist Full agonist 8.0 pKi - 4
pKi 8.0 [4]
EP1 receptor Rn Agonist Partial agonist 7.9 pKi - 2
pKi 7.9 [2]
IP receptor Hs Agonist Full agonist 7.5 – 8.0 pKi - 1,7
pKi 7.5 – 8.0 [1,7]
EP1 receptor Mm Agonist Full agonist 7.7 pKi - 4
pKi 7.7 [4]
EP3 receptor Mm Agonist Full agonist 7.7 pKi - 4
pKi 7.7 (Ki 2.2x10-8 M) [4]
EP3 receptor Rn Agonist Full agonist 7.3 pKi - 2
pKi 7.3 (Ki 4.7x10-8 M) EP3α isoform [2]
EP3 receptor Hs Agonist Full agonist 6.7 – 7.3 pKi - 1,6
pKi 7.3 (Ki 5.6x10-8 M) EP3-III isoform [1]
pKi 6.7 (Ki 2.08x10-7 M) EP3-I isoform [6]
EP1 receptor Hs Agonist Full agonist 5.6 – 8.0 pKi - 1,5
pKi 5.6 – 8.0 [1,5]
DP1 receptor Hs Agonist Full agonist 6.0 – 6.6 pKi - 1,6,8
pKi 6.0 – 6.6 [1,6,8]
FP receptor Hs Agonist Full agonist 6.2 pKi - 1
pKi 6.2 [1]
EP2 receptor Rn Agonist Full agonist 5.9 pKi - 2
pKi 5.9 [2]
EP2 receptor Mm Agonist Full agonist 5.8 pKi - 4
pKi 5.8 [4]
EP2 receptor Hs Agonist Full agonist 5.7 pKi - 1
pKi 5.7 [1]
EP4 receptor Hs Agonist Full agonist 4.6 – 6.7 pKi - 1,3,6
pKi 4.6 – 6.7 (Ki 2.3x10-5 – 2.1x10-7 M) [1,3,6]
EP4 receptor Mm Agonist Full agonist 5.6 pKi - 4
pKi 5.6 [4]
TP receptor Hs Agonist Full agonist 5.2 pKi - 1
pKi 5.2 [1]
EP3 receptor Rn Agonist Full agonist 9.2 pEC50 - 2
pEC50 9.2 (EC50 6.3x10-10 M) EP3α isoform [2]
EP4 receptor Hs Agonist Full agonist 6.4 pEC50 - 6
pEC50 6.4 (EC50 4x10-7 M) [6]
Ligand mentioned in the following text fields