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
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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
1. Sibley CD, Morris EA, Kharel Y, Brown AM, Huang T, Bevan DR, Lynch KR, Santos WL. (2020)
Discovery of a Small Side Cavity in Sphingosine Kinase 2 that Enhances Inhibitor Potency and Selectivity.
J Med Chem, 63 (3): 1178-1198. [PMID:31895563]
2. Thorpe SB, Santos WL, Lynch KR. (2017)
Sphingosine kinase inhibitor amidoxime prodrugs.
Patent number: WO2017172989A1. Assignee: Thorpe SB, Santos WL, Lynch KR. Priority date: 30/03/2016. Publication date: 05/10/2017.