LHVS   Click here for help

GtoPdb Ligand ID: 9298

Synonyms: morpholinurea-leucine-homophenylalanine-vinylsulfone-phenyl | morpholinurea-leucine-homophenylalaninevinyl phenyl sulfone
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: LHVS is a small molecule, vinyl sulfone type, tool compound, which inhibits cathepsins L and S with low nanomolar potency [1].
Cathepsin S inhibitors are being investigated for clinical utility in inflammatory conditions. LHVS is reported to have neuroprotective action in models of traumatic brain injury [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 14
Topological polar surface area 113.19
Molecular weight 527.25
XLogP 4.23
No. Lipinski's rules broken 1
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Canonical SMILES CC(CC(C(=O)NC(C=CS(=O)(=O)c1ccccc1)CCc1ccccc1)NC(=O)N1CCOCC1)C
Isomeric SMILES CC(C[C@H](C(=O)N[C@@H](/C=C/S(=O)(=O)c1ccccc1)CCc1ccccc1)NC(=O)N1CCOCC1)C
InChI InChI=1S/C28H37N3O5S/c1-22(2)21-26(30-28(33)31-16-18-36-19-17-31)27(32)29-24(14-13-23-9-5-3-6-10-23)15-20-37(34,35)25-11-7-4-8-12-25/h3-12,15,20,22,24,26H,13-14,16-19,21H2,1-2H3,(H,29,32)(H,30,33)/b20-15+/t24-,26-/m1/s1
1. Méthot N, Rubin J, Guay D, Beaulieu C, Ethier D, Reddy TJ, Riendeau D, Percival MD. (2007)
Inhibition of the activation of multiple serine proteases with a cathepsin C inhibitor requires sustained exposure to prevent pro-enzyme processing.
J Biol Chem, 282 (29): 20836-46. [PMID:17535802]
2. Xu J, Wang H, Ding K, Lu X, Li T, Wang J, Wang C, Wang J. (2013)
Inhibition of cathepsin S produces neuroprotective effects after traumatic brain injury in mice.
Mediators Inflamm, 2013: 187873. [PMID:24282339]