cicaprost   

GtoPdb Ligand ID: 1917

Synonyms: ZK 96480 | ZK-96480
Compound class: Synthetic organic
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 86.99
Molecular weight 374.21
XLogP 1.89
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCC#CCC(C(C#CC1C(O)CC2C1CC(=CCOCC(=O)O)C2)O)C
Isomeric SMILES CCC#CC[C@@H]([C@@H](C#C[C@H]1[C@H](O)C[C@H]2[C@@H]1C/C(=C/COCC(=O)O)/C2)O)C
InChI InChI=1S/C22H30O5/c1-3-4-5-6-15(2)20(23)8-7-18-19-12-16(9-10-27-14-22(25)26)11-17(19)13-21(18)24/h9,15,17-21,23-24H,3,6,10-14H2,1-2H3,(H,25,26)/b16-9+/t15-,17-,18+,19-,20+,21+/m0/s1
InChI Key ARUGKOZUKWAXDS-SEWALLKFSA-N
References
1. Abramovitz M, Adam M, Boie Y, Carrière M, Denis D, Godbout C, Lamontagne S, Rochette C, Sawyer N, Tremblay NM et al.. (2000)
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
Biochim. Biophys. Acta, 1483 (2): 285-93. [PMID:10634944]
2. Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S. (1997)
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.
Br. J. Pharmacol., 122 (2): 217-24. [PMID:9313928]
3. Wang JW, Vu C, Poloso NJ. (2017)
A Prostacyclin Analog, Cicaprost, Exhibits Potent Anti-Inflammatory Activity in Human Primary Immune Cells and a Uveitis Model.
J Ocul Pharmacol Ther, 33 (3): 186-192. [PMID:28072560]