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
References
1. Demolis JL, Robert A, Mouren M, Funck-Brentano C, Jaillon P. (1993)
Pharmacokinetics and platelet antiaggregating effects of beraprost, an oral stable prostacyclin analogue, in healthy volunteers.
J. Cardiovasc. Pharmacol., 22 (5): 711-6. [PMID:7506323]
2. Kajikawa N, Nogimori K, Murata T, Nishio S, Uchiyama S. (1989)
Specific binding of the new stable epoprostenol analogue beraprost sodium to prostacyclin receptors on human and rat platelets.
Arzneimittelforschung, 39 (4): 495-9. [PMID:2665758]