compound 27 [WO2019226977A1]   Click here for help

GtoPdb Ligand ID: 11977

Compound class: Synthetic organic
Comment: This compound is predicted to be the active version of the TLR7 agonist prodrug polvitolimod. It is claimed as compound 27 in Primmune Therapeutics' patent WO2019226977A1 [3]. TLR7 agonists are predicted to offer clinical benefit in patients with severe COVID-19 [2], since some loss-of-function variants in TLR7 are associated with increased COVID-19 disease severity (likely via blunted type I IFN production) [1]. We can make a provisional link between compound 27 and the active TLR7 agonist PRX034.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 4
Rotatable bonds 3
Topological polar surface area 148.39
Molecular weight 339.1
XLogP -1.66
No. Lipinski's rules broken 0
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Canonical SMILES C#CCn1c(=O)n(c2c1c(=O)[nH]c(n2)N)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO
Isomeric SMILES Nc1[nH]c(=O)c2n(c(=O)n(c2n1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)CC#C
InChI InChI=1S/C13H14FN5O5/c1-2-3-18-7-9(16-12(15)17-10(7)22)19(13(18)23)11-8(21)6(14)5(4-20)24-11/h1,5-6,8,11,20-21H,3-4H2,(H3,15,16,17,22)/t5-,6-,8-,11-/m1/s1
Classification Click here for help
Compound class Synthetic organic
Prodrug polvitolimod
IUPAC Name Click here for help
Database Links Click here for help
GtoPdb PubChem SID 464244118
PubChem CID 153282971
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