STING agonist 2   Click here for help

GtoPdb Ligand ID: 10127

PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: This compound is a potent agonist of the stimulator of interferon genes (STING) protein, which is an intracellular detector/receptor of pathogen-derived and self DNA in the cytosol [2]. It was designed to be a systemically active immune-modifying anti-cancer therapeutic, with the potential to outperfom existing modified cyclic dinucleotide-based cGAMP (the endogenous STING agonist) development compounds, which are generally active by intratumoral delivery in a restricted range of accessible tumours. It is one of the chemical structures claimed in GlaxoSmithKline's patent WO2017175147A1 [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 4
Rotatable bonds 15
Topological polar surface area 215.66
Molecular weight 678.31
XLogP 2.83
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCn1nc(cc1C(=O)Nc1nc2c(n1CCCCn1c(NC(=O)c3cc(nn3CC)C)nc3c1ccc(c3)C(=O)N)ccc(c2)C(=O)N)C
Isomeric SMILES CCn1nc(cc1C(=O)Nc1nc2c(n1CCCCn1c(NC(=O)c3cc(nn3CC)C)nc3c1ccc(c3)C(=O)N)ccc(c2)C(=O)N)C
InChI InChI=1S/C34H38N12O4/c1-5-45-27(15-19(3)41-45)31(49)39-33-37-23-17-21(29(35)47)9-11-25(23)43(33)13-7-8-14-44-26-12-10-22(30(36)48)18-24(26)38-34(44)40-32(50)28-16-20(4)42-46(28)6-2/h9-12,15-18H,5-8,13-14H2,1-4H3,(H2,35,47)(H2,36,48)(H,37,39,49)(H,38,40,50)
InChI Key ICZSAXDKFXTSGL-UHFFFAOYSA-N
References
1. Charnley AK, Darcy MG, Dodson JW, Dong X, Hughes TV, Kang J, Leister LK, Lian Y, Li Y, Mehlmann JF et al.. (2017)
Heterocyclic amides useful as protein modulators.
Patent number: WO2017175147A1. Assignee: Glaxosmithkline Intellectual Property Development Limited. Priority date: 07/04/2016. Publication date: 12/10/2017.
2. Ramanjulu JM, Pesiridis GS, Yang J, Concha N, Singhaus R, Zhang SY, Tran JL, Moore P, Lehmann S, Eberl HC et al.. (2018)
Design of amidobenzimidazole STING receptor agonists with systemic activity.
Nature, 564 (7736): 439-443. [PMID:30405246]