esuberaprost   

GtoPdb Ligand ID: 8314

Synonyms: APS-314D free acid | BPS-314d
Compound class: Synthetic organic
Comment: Esuberaprost is a defined enantiomer of the racemate beraprost and represents the active enantiomer [1]. Like beraprost, the compound is a prostacyclin IP1 receptor agonist.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 86.99
Molecular weight 398.21
XLogP 2.82
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CC#CCC(C(C=CC1C(O)CC2C1c1cccc(c1O2)CCCC(=O)O)O)C
Isomeric SMILES CC#CC[C@@H]([C@@H](/C=C/[C@H]1[C@H](O)C[C@H]2[C@@H]1c1cccc(c1O2)CCCC(=O)O)O)C
InChI InChI=1S/C24H30O5/c1-3-4-7-15(2)19(25)13-12-17-20(26)14-21-23(17)18-10-5-8-16(24(18)29-21)9-6-11-22(27)28/h5,8,10,12-13,15,17,19-21,23,25-26H,6-7,9,11,14H2,1-2H3,(H,27,28)/b13-12+/t15-,17-,19+,20+,21-,23-/m0/s1
InChI Key CTPOHARTNNSRSR-NOQAJONNSA-N
Bioactivity Comments
The binding affinity (Kd) of beraprost for a single binding site on human platelets is reported in [2] as 133nM, with the affinity of the active enantiomer APS-314d (= esuberaprost) being 100-fold higher, i.e. approximately 13nM.
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
IP receptor Hs Agonist Agonist 7.9 pKd - 2
pKd 7.9 (Kd 1.3x10-8 M) [2]