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Literature summary for 3.2.1.18 extracted from

  • Krueger, A.C.; Xu, Y.; Kati, W.M.; Kempf, D.J.; Maring, C.J.; McDaniel, K.F.; Molla, A.; Montgomery, D.; Kohlbrenner, W.E.
    Synthesis of potent pyrrolidine influenza neuraminidase inhibitors (2008), Bioorg. Med. Chem. Lett., 18, 1692-1695.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(2R,4S,5R)-5-[(1R,2R)-1-(acetylamino)-2-ethoxybut-3-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
(2R,4S,5R)-5-[(1R,2R)-1-(acetylamino)-2-ethoxybut-3-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
(2R,4S,5R)-5-[(1R,2R)-1-(acetylamino)-2-methoxybut-3-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
(2R,4S,5R)-5-[(1R,2R)-1-(acetylamino)-2-methoxybut-3-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
(2R,4S,5R)-5-[(1R,2R)-1-(acetylamino)-2-methoxypent-4-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
(2R,4S,5R)-5-[(1R,2R)-1-(acetylamino)-2-methoxypent-4-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
(2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-hydroxy-2-methylpentyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
(2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-hydroxy-2-methylpentyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
(2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid i.e. A-315675 influenza A virus
(2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid i.e. A-315675 influenza B virus
(2R,4S,5R)-5-[(1S,2S)-1-(acetylamino)-2-hydroxybut-3-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
(2R,4S,5R)-5-[(1S,2S)-1-(acetylamino)-2-hydroxybut-3-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
(2R,4S,5R)-5-[(1S,2S)-1-(acetylamino)-2-hydroxybutyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
(2R,4S,5R)-5-[(1S,2S)-1-(acetylamino)-2-hydroxybutyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
(2R,4S,5R)-5-[(2S)-1-(acetylamino)-2-hydroxypent-4-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
(2R,4S,5R)-5-[(2S)-1-(acetylamino)-2-hydroxypent-4-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
(2R,4S,5R)-5-[(2S)-1-(acetylamino)-2-hydroxypentyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
(2R,4S,5R)-5-[(2S)-1-(acetylamino)-2-hydroxypentyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
oseltamivir carboxylate
-
influenza A virus
oseltamivir carboxylate
-
influenza B virus
zanamivir
-
influenza A virus
zanamivir
-
influenza B virus

Organism

Organism UniProt Comment Textmining
influenza A virus
-
-
-
influenza A virus A/N1/PR/8/34
-
-
-
influenza B virus
-
-
-
influenza B virus B/Memphis/3/89
-
-
-

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00000006
-
zanamivir
-
influenza A virus
0.0000001
-
zanamivir
-
influenza B virus
0.0000001
-
oseltamivir carboxylate
-
influenza A virus
0.00000014
-
(2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
0.00000021
-
(2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
0.0000006
-
(2R,4S,5R)-5-[(1R,2R)-1-(acetylamino)-2-methoxybut-3-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
0.00000067
-
(2R,4S,5R)-5-[(1R,2R)-1-(acetylamino)-2-methoxypent-4-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
0.0000011
-
oseltamivir carboxylate
-
influenza B virus
0.0000012
-
(2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-hydroxy-2-methylpentyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
0.0000013
-
(2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-hydroxy-2-methylpentyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
0.0000013
-
(2R,4S,5R)-5-[(2S)-1-(acetylamino)-2-hydroxypentyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
0.0000016
-
(2R,4S,5R)-5-[(2S)-1-(acetylamino)-2-hydroxypent-4-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
0.000002
-
(2R,4S,5R)-5-[(1S,2S)-1-(acetylamino)-2-hydroxybut-3-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
0.0000028
-
(2R,4S,5R)-5-[(1S,2S)-1-(acetylamino)-2-hydroxybutyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
0.0000048
-
(2R,4S,5R)-5-[(1R,2R)-1-(acetylamino)-2-ethoxybut-3-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza B virus
0.0000053
-
(2R,4S,5R)-5-[(2S)-1-(acetylamino)-2-hydroxypentyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
0.00001
-
(2R,4S,5R)-5-[(2S)-1-(acetylamino)-2-hydroxypent-4-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
0.0000115
-
(2R,4S,5R)-5-[(1S,2S)-1-(acetylamino)-2-hydroxybutyl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
0.0000173
-
(2R,4S,5R)-5-[(1R,2R)-1-(acetylamino)-2-methoxypent-4-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
0.0000198
-
(2R,4S,5R)-5-[(1R,2R)-1-(acetylamino)-2-methoxybut-3-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
0.000021
-
(2R,4S,5R)-5-[(1R,2R)-1-(acetylamino)-2-ethoxybut-3-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus
0.000025
-
(2R,4S,5R)-5-[(1S,2S)-1-(acetylamino)-2-hydroxybut-3-en-1-yl]-4-[(1Z)-prop-1-en-1-yl]pyrrolidine-2-carboxylic acid
-
influenza A virus