compound 16 [PMID: 26794040]   Click here for help

GtoPdb Ligand ID: 9223

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 16 is a novel, potent and selective sphingosine-1-phosphate receptor 2 (S1P2 receptor) antagonist [1]. The series of compounds including 16 is claimed in patent WO2013047701 [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 108.33
Molecular weight 550.25
XLogP 5.86
No. Lipinski's rules broken 1
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Canonical SMILES Fc1ccc(cc1)Oc1cc(Oc2ccc(cc2)C(C(=O)O)(C)C)cc(c1)NC(=O)N1CCC(C1)(O)CC(C)C
Isomeric SMILES Fc1ccc(cc1)Oc1cc(Oc2ccc(cc2)C(C(=O)O)(C)C)cc(c1)NC(=O)N1CCC(C1)(O)CC(C)C
InChI InChI=1S/C31H35FN2O6/c1-20(2)18-31(38)13-14-34(19-31)29(37)33-23-15-26(17-27(16-23)40-25-11-7-22(32)8-12-25)39-24-9-5-21(6-10-24)30(3,4)28(35)36/h5-12,15-17,20,38H,13-14,18-19H2,1-4H3,(H,33,37)(H,35,36)
1. Kusumi K, Shinozaki K, Yamaura Y, Hashimoto A, Kurata H, Naganawa A, Otsuki K, Matsushita T, Sekiguchi T, Kakuuchi A et al.. (2016)
Discovery of novel S1P2 antagonists, part 3: Improving the oral bioavailability of a series of 1,3-bis(aryloxy)benzene derivatives.
Bioorg Med Chem Lett, 26 (4): 1209-13. [PMID:26794040]
2. Naganawa A, Kusumi K, Sekiguchi T, Kakuuchi A, Shinozaki K, Yamamoto H, Nonaka S. (2013)
Phenyl derivative.
Patent number: WO2013047701. Assignee: Ono Pharmaceutical Co., Ltd.. Priority date: 29/09/2011. Publication date: 04/04/2013.
3. Roviezzo F, Brancaleone V, De Gruttola L, Vellecco V, Bucci M, D'Agostino B, Cooper D, Sorrentino R, Perretti M, Cirino G. (2011)
Sphingosine-1-phosphate modulates vascular permeability and cell recruitment in acute inflammation in vivo.
J Pharmacol Exp Ther, 337 (3): 830-7. [PMID:21421740]