GtoPdb Ligand ID: 6623

Synonyms: compound 22a [PMID: 22397330] | PF 543 | sphingosine kinase 1 Inhibitor II
Compound class: Synthetic organic
Comment: PF-543 is a selective inhibitor of sphingosine kinase-1 [2]. It is >100-fold selective for SphK1 over the SphK2 isoform.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 75.22
Molecular weight 465.2
XLogP 4.63
No. Lipinski's rules broken 0
Canonical SMILES OCC1CCCN1Cc1ccc(cc1)COc1cc(C)cc(c1)CS(=O)(=O)c1ccccc1
Isomeric SMILES OC[C@H]1CCCN1Cc1ccc(cc1)COc1cc(C)cc(c1)CS(=O)(=O)c1ccccc1
InChI InChI=1S/C27H31NO4S/c1-21-14-24(20-33(30,31)27-7-3-2-4-8-27)16-26(15-21)32-19-23-11-9-22(10-12-23)17-28-13-5-6-25(28)18-29/h2-4,7-12,14-16,25,29H,5-6,13,17-20H2,1H3/t25-/m1/s1
1. Schnute ME, McReynolds MD, Carroll J, Chrencik J, Highkin MK, Iyanar K, Jerome G, Rains JW, Saabye M, Scholten JA et al.. (2017)
Discovery of a Potent and Selective Sphingosine Kinase 1 Inhibitor through the Molecular Combination of Chemotype-Distinct Screening Hits.
J. Med. Chem., 60 (6): 2562-2572. [PMID:28231433]
2. Schnute ME, McReynolds MD, Kasten T, Yates M, Jerome G, Rains JW, Hall T, Chrencik J, Kraus M, Cronin CN et al.. (2012)
Modulation of cellular S1P levels with a novel, potent and specific inhibitor of sphingosine kinase-1.
Biochem. J., 444 (1): 79-88. [PMID:22397330]