compound 8a [PMID: 23713581]   Click here for help

GtoPdb Ligand ID: 8856

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 8a was designed as a small-molecule inhibitor of the lymphoid-specific non-receptor tyrosine phosphatase, LYP (PTPN22) [1]. PTPN22 directly dephosphorylates several kinase enzymes, effecting negative regulation of T-cell receptor (TCR) signaling [3], and is implicated in autoimmune diseases [4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 109
Molecular weight 503.11
XLogP 6.66
No. Lipinski's rules broken 1
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Canonical SMILES CCCNC(=O)COc1ccc(cc1)c1oc2c(c1C#Cc1cccc(c1)Cl)cc(c(c2)O)C(=O)O
Isomeric SMILES CCCNC(=O)COc1ccc(cc1)c1oc2c(c1C#Cc1cccc(c1)Cl)cc(c(c2)O)C(=O)O
InChI InChI=1S/C28H22ClNO6/c1-2-12-30-26(32)16-35-20-9-7-18(8-10-20)27-21(11-6-17-4-3-5-19(29)13-17)22-14-23(28(33)34)24(31)15-25(22)36-27/h3-5,7-10,13-15,31H,2,12,16H2,1H3,(H,30,32)(H,33,34)
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Molecular structure representations generated using Open Babel