A286982   Click here for help

GtoPdb Ligand ID: 6592

Synonyms: A 286982 | A-286982
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Potent inhibitor of the LFA-1/ICAM-1 interaction [1]. LFA-1 (leukocyte function-associated antigen-1) is a beta2-integrin, and ICAM-1 (CD54) is an endothelial cell adhesion molecule.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 111.74
Molecular weight 453.17
XLogP 4.55
No. Lipinski's rules broken 0
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Canonical SMILES O=C(N1CCN(CC1)C(=O)C)C=Cc1ccc(c(c1)N(=O)=O)Sc1ccccc1C(C)C
Isomeric SMILES O=C(N1CCN(CC1)C(=O)C)/C=C/c1ccc(c(c1)N(=O)=O)Sc1ccccc1C(C)C
InChI InChI=1S/C24H27N3O4S/c1-17(2)20-6-4-5-7-22(20)32-23-10-8-19(16-21(23)27(30)31)9-11-24(29)26-14-12-25(13-15-26)18(3)28/h4-11,16-17H,12-15H2,1-3H3/b11-9+
1. Liu G, Link JT, Pei Z, Reilly EB, Leitza S, Nguyen B, Marsh KC, Okasinski GF, von Geldern TW, Ormes M et al.. (2000)
Discovery of novel p-arylthio cinnamides as antagonists of leukocyte function-associated antigen-1/intracellular adhesion molecule-1 interaction. 1. Identification of an additional binding pocket based on an anilino diaryl sulfide lead.
J Med Chem, 43 (21): 4025-40. [PMID:11052808]