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Literature summary for 3.4.22.B14 extracted from

  • Ghosh, A.K.; Takayama, J.; Aubin, Y.; Ratia, K.; Chaudhuri, R.; Baez, Y.; Sleeman, K.; Coughlin, M.; Nichols, D.B.; Mulhearn, D.C.; Prabhakar, B.S.; Baker, S.C.; Johnson, M.E.; Mesecar, A.D.
    Structure-based design, synthesis, and biological evaluation of a series of novel and reversible inhibitors for the severe acute respiratory syndrome-coronavirus papain-like protease (2009), J. Med. Chem., 52, 5228-5240.
    View publication on PubMedView publication on EuropePMC
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Cloned(Commentary)

Cloned (Comment) Organism
expressed in Escherichia coli Severe acute respiratory syndrome-related coronavirus

Inhibitors

Inhibitors Comment Organism Structure
2,6-dimethyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
2,N-dimethyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
2-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
2-methoxymethyl-5-nitrobenzoic acid methyl ester
-
 Severe acute respiratory syndrome-related coronavirus
2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
2-methyl-N-[1-(naphthalen-2-yl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
3-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
3-methyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
4-amino-N-[(R)-1-(1-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
4-amino-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
4-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
4-methyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
5-amino-2-methoxymethyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
5-amino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
5-amino-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
5-cyano-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
5-iodo-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
5-methylamino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
5-N-acetylamino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
5-N-tert-butoxycarbonylmethylamino-2-methyl-N'-[(R)-1-(1-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus
additional information not inhibited by 2-hydroxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide, 4-N'-tert-butoxycarbonylamino-N-[(R)-1-(2-naphthyl)ethyl]-benzamide, 2-methyl-N-[1-(2-naphthyl)propyl]benzamide, and 2-methyl-N-[1-(2-naphthyl)benzyl]benzamide Severe acute respiratory syndrome-related coronavirus
N-methyl-5-methylamino-2-methyl-N'-[(R)-1-(1-naphthyl)ethyl]benzamide
-
 Severe acute respiratory syndrome-related coronavirus

Organism

Organism UniProt Comment Textmining
Severe acute respiratory syndrome-related coronavirus
-
-
-

Purification (Commentary)

Purification (Comment) Organism
-
 Severe acute respiratory syndrome-related coronavirus

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
L-Arg-L-Leu-L-Arg-Gly-Gly-7-amido-4-methylcoumarin + H2O
-
 Severe acute respiratory syndrome-related coronavirus L-Arg-L-Leu-L-Arg-Gly-Gly + 7-amino-4-methylcoumarin
-
 ?

Synonyms

Synonyms Comment Organism
PLpro
-
 Severe acute respiratory syndrome-related coronavirus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00046
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 5-methylamino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
0.00056
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 5-amino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
0.00056
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 5-amino-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
0.0013
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus N-methyl-5-methylamino-2-methyl-N'-[(R)-1-(1-naphthyl)ethyl]benzamide
0.0014
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 2-methoxymethyl-5-nitrobenzoic acid methyl ester
0.0023
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
0.00264
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 5-N-acetylamino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
0.0027
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 5-iodo-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
0.0048
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 5-N-tert-butoxycarbonylmethylamino-2-methyl-N'-[(R)-1-(1-naphthyl)ethyl]benzamide
0.0052
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 5-amino-2-methoxymethyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
0.0087
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 2-methyl-N-[1-(naphthalen-2-yl)ethyl]benzamide
0.0111
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 5-cyano-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
0.0121
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 2,6-dimethyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.0135
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 3-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.0148
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 3-methyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.0226
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 2,N-dimethyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.0248
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 4-amino-N-[(R)-1-(1-naphthyl)ethyl]benzamide
0.0291
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 4-methyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.0461
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 4-amino-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.09
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 2-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.149
-
 in 50 mM HEPES, pH 7.5 Severe acute respiratory syndrome-related coronavirus 4-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide