SLM6071469   Click here for help

GtoPdb Ligand ID: 10641

Synonyms: compound 10 [PMID: 31895563] [1]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 10 is an inhibitor of sphingosine kinase 2 [1]. This compound exploits a novel side cavity on the kinase to provide enhanced potency and selectivity. The PubChem entry for this compound originated via SureChEMBL patent extraction, and is derived from patent WO2017172989A1 from researchers at Virginia Tech [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 101.26
Molecular weight 499.14
XLogP 6.43
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES NC(=N)N1CCC[C@H]1c1onc(n1)c1ccc(c(c1)C(F)(F)F)OCc1ccc(cc1)C(F)(F)F
Isomeric SMILES NC(=N)N1CCC[C@H]1c1onc(n1)c1ccc(c(c1)C(F)(F)F)OCc1ccc(cc1)C(F)(F)F
InChI InChI=1S/C22H19F6N5O2/c23-21(24,25)14-6-3-12(4-7-14)11-34-17-8-5-13(10-15(17)22(26,27)28)18-31-19(35-32-18)16-2-1-9-33(16)20(29)30/h3-8,10,16H,1-2,9,11H2,(H3,29,30)/t16-/m0/s1
InChI Key QOYVZPSXPWIXAV-INIZCTEOSA-N
Immunopharmacology Comments
Blockade of SphK2 activity in vivo causes an elevation of blood S1P levels. S1P signalling and synthesis (via sphingosine kinases) are actively pursued therapeutic modalities, with potential applications across a broad range of cellular processes, including modulating fibrosis, inhibiting tumour growth, angiogenesis, and endothelial cell chemotaxis, and for treating inflammatory and autoimmune diseases and disorders. Compound 10 provides a pharmacological tool to help explore the outcomes of selective SphK2 inhibition in normal and pathological settings, that is suitable for both in vitro and in vivo studies.