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Literature summary for 3.4.22.28 extracted from

  • Zeng, D.; Ma, Y.; Zhang, R.; Nie, Q.; Cui, Z.; Wang, Y.; Shang, L.; Yin, Z.
    Synthesis and structure-activity relationship of alpha-keto amides as enterovirus 71 3C protease inhibitors (2016), Bioorg. Med. Chem. Lett., 26, 1762-1766 .
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
additional information inhibitor synthesis and assay for their biochemical and antiviral activities, structure-activity relationship (SAR) study, ligand docking, overview. The small moieties are primarily tolerated at P1' and the introduction of para-fluoro benzyl at P2 notably improves the inhibitor's potency Enterovirus A71
N-[(2S)-1-oxo-3-[(3S)-2-oxopiperidin-3-yl]propan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]-4-(pentylamino)butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]-4-(phenylamino)butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]-4-(propan-2-ylamino)butan-2-yl]-4-fluoro-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide docking modeling Enterovirus A71
N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]-4-(propan-2-ylamino)butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]-4-(propylamino)butan-2-yl]-4-fluoro-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]-4-(propylamino)butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]-4-(phenylamino)butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]-4-(propan-2-ylamino)butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-(benzylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-(benzylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-(butylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-(butylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-(cyclohexylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-4-fluoro-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-(cyclohexylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-(cyclohexylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-4-fluoro-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-(dodecylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-(hexylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-(methylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-(tert-butylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-[(2-methylpropyl)amino]-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-[(4-methylphenyl)amino]-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-[(4-nitrophenyl)amino]-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
N-[(2S)-4-[(furan-2-ylmethyl)amino]-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
Enterovirus A71
Nalpha-(tert-butoxycarbonyl)-N-[(2S)-4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-4-fluoro-L-phenylalaninamide
-
Enterovirus A71
Nalpha-[(benzyloxy)carbonyl]-N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]-4-(propan-2-ylamino)butan-2-yl]-4-fluoro-L-phenylalaninamide
-
Enterovirus A71
rupintrivir
-
Enterovirus A71

Organism

Organism UniProt Comment Textmining
Enterovirus A71
-
EV71
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information usage of a fluorescence resonance energy transfer (FRET)-based enzyme assay for activity determination Enterovirus A71 ?
-
?

Synonyms

Synonyms Comment Organism
3C protease
-
Enterovirus A71
3Cpro
-
Enterovirus A71
EV71 3Cpro
-
Enterovirus A71

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00054
-
51 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-1-oxo-3-[(3S)-2-oxopiperidin-3-yl]propan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.00132
-
73 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]-4-(propan-2-ylamino)butan-2-yl]-4-fluoro-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.00134
-
57 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]-4-(propan-2-ylamino)butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.00142
-
77 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 Nalpha-[(benzyloxy)carbonyl]-N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]-4-(propan-2-ylamino)butan-2-yl]-4-fluoro-L-phenylalaninamide
0.00152
-
75 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-4-fluoro-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.00178
-
78 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 Nalpha-(tert-butoxycarbonyl)-N-[(2S)-4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-4-fluoro-L-phenylalaninamide
0.00188
-
74 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]-4-(propylamino)butan-2-yl]-4-fluoro-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.0023
-
pH and temperature not specified in the publication Enterovirus A71 rupintrivir
0.00332
-
64 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.00371
-
76 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-(cyclohexylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-4-fluoro-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.00381
-
50 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.00408
-
62 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-(methylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.00486
-
59 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-(cyclohexylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.00507
-
65 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-[(2-methylpropyl)amino]-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.00622
-
63 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]-4-(propylamino)butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.0063
-
72 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-[(furan-2-ylmethyl)amino]-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.00783
-
61 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-(benzylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.00821
-
58 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-(butylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.00875
-
52 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]-4-(propan-2-ylamino)butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.0127
-
54 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-(cyclohexylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.0176
-
53 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-(butylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.02
-
55 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]-4-(phenylamino)butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.02
-
56 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-(benzylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.02
-
60 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]-4-(phenylamino)butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.02
-
66 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-(tert-butylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.02
-
67 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]-4-(pentylamino)butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.02
-
68 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-(hexylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.02
-
69 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-(dodecylamino)-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.02
-
70 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-[(4-methylphenyl)amino]-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
0.02
-
71 mM Tris, pH 7.0, 150 mM NaCl, 1 mM EDTA, 2 mM DTT, 10% glycerol, 30°C, substrate (2-(N-methylamino)benzoyl)-IEALFQGPPK(2,4-dinitrophenyl)-FR Enterovirus A71 N-[(2S)-4-[(4-nitrophenyl)amino]-3,4-dioxo-1-[(3S)-2-oxopiperidin-3-yl]butan-2-yl]-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide