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Literature summary for 3.4.21.26 extracted from

  • Wallen, E.A.; Christiaans, J.A.; Jarho, E.M.; Forsberg, M.M.; Venalainen, J.I.; Mannisto, P.T.; Gynther, J.
    New prolyl oligopeptidase inhibitors developed from dicarboxylic acid bis(l-prolyl-pyrrolidine) amides (2003), J. Med. Chem., 46, 4543-4551.
    View publication on PubMed
Search for more literature for 3.4.21.26

Inhibitors

Inhibitors Comment Organism Structure
isophthalic acid (L-proline methyl ester) L-prolyl-pyrrolidine amide IC50: 54 nM Sus scrofa
isophthalic acid 2(S)-(cyclopentanecarbonyl)pyrrolidine (L-proline methyl ester) amide IC50: 640 nM Sus scrofa
isophthalic acid 2(S)-(cyclopentanecarbonyl)pyrrolidine L-prolyl-2(S)-(hydroxyacetyl)pyrrolidine amide IC50: 0.61 nM, log P: 0.2, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa
isophthalic acid 2(S)-(cyclopentylcarbonyl)pyrrolidine L-prolyl-pyrrolidine amide IC50: 14 nM, log P: 1.1, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa
isophthalic acid 2(S)-(cylcohexanecarbonyl)pyrrolidine L-prolyl-2(S)-cynaopyrrolidine amide IC50: 0.72 nM Sus scrofa
isophthalic acid 2(S)-(cylcopentanecarbonyl)pyrrolidine L-prolyl-2(S)-cynaopyrrolidine amide IC50: 1.1 nM, log P: 0.8, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa
isophthalic acid 2(S)-acetylpyrrolidine L-prolyl-2(S)-(hydroxyacetyl)pyrrolidine amide IC50: 1.2 nM Sus scrofa
isophthalic acid 2(S)-acetylpyrrolidine L-prolyl-2(S)-cynaopyrrolidine amide IC50: 4.2 nM, log P: -0.6, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa
isophthalic acid 2(S)-acetylpyrrolidine L-prolyl-pyrrolidine amide IC50: 65 nM Sus scrofa
isophthalic acid 2(S)-benzoylpyrrolidine L-prolyl-2(S)-cynaopyrrolidine amide IC50: 1.3 nM, log P: 1.1, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa
isophthalic acid 2(S)-benzoylpyrrolidine L-prolyl-pyrrolidine amide IC50: 18 nM Sus scrofa
isophthalic acid 2(S)-isobutanoylpyrrolidine L-prolyl-2(S)-cynaopyrrolidine amide IC50: 1.6 nM, log P: 0.3, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa
isophthalic acid bis(L-prolyl-pyrrolidine) amide IC50: 26 nM, log O = -0.2, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa
isophthalic acid bis-2(S)-(cyclopentanecarbonyl)pyrrolidine amide IC50: 78 nM, log P: 2.7, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa
isophthalic acid bis-2(S)-acetylpyrrolidine amide 54% inhibition at 0.1 nM Sus scrofa
isophthalic acid L-prolyl-2(S)-(hydroxyacetyl)pyrrolidine L-prolyl-pyrrolidine amide IC50: 0.39 nM Sus scrofa
isophthalic acid L-prolyl-2(S)-cyanopyrrolidine L-prolyl-pyrrolidine amide IC50: 1.5 nM Sus scrofa
isophthalic acid L-prolyl-pyrrolidine L-prolyl-L-prolinal amide IC50: 1.3 nM Sus scrofa
isophthalic acid L-prolylbenzylamine L-prolyl-pyrrolidine amide IC50: 31 nM Sus scrofa

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0194
-
 Ala-Pro-p-nitroanilide pH 7.5, 85°C Pyrococcus furiosus
0.0207
-
 Gly-Pro-p-nitroanilide pH 7.5, 85°C Pyrococcus furiosus
0.0229
-
 Arg-Pro-p-nitroanilide pH 7.5, 85°C Pyrococcus furiosus
0.04
-
 Asp-Pro-p-nitroanilide pH 7.5, 85°C Pyrococcus furiosus
0.043
-
 benzyloxycarbonyl-Ala-Ala-p-nitroanilide pH 7.5, 85°C Pyrococcus furiosus
0.0437
-
 benzyloxycarbonyl-Ala-Pro-p-nitroanilide pH 7.5, 85°C Pyrococcus furiosus
0.16
-
 benzyloxycarbonyl-Gly-Pro-p-nitroanilide pH 7.5, 85°C Pyrococcus furiosus

Organism

Organism UniProt Comment Textmining
Pyrococcus furiosus
-
-
-
Sus scrofa
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
brain
-
 Sus scrofa
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
Ala-Pro-p-nitroanilide + H2O
-
 Pyrococcus furiosus Ala-Pro + p-nitroaniline
-
 ?
Arg-Pro-p-nitroanilide + H2O
-
 Pyrococcus furiosus Arg-Pro + p-nitroaniline
-
 ?
Asp-Pro-p-nitroanilide + H2O
-
 Pyrococcus furiosus Asp-Pro + p-nitroaniline
-
 ?
benzyloxycarbonyl-Ala-Ala-p-nitroanilide + H2O
-
 Pyrococcus furiosus benzyloxycarbonyl-Ala-Ala + p-nitroaniline
-
 ?
benzyloxycarbonyl-Ala-Pro-p-nitroanilide + H2O
-
 Pyrococcus furiosus benzyloxycarbonyl-Ala-Pro + p-nitroaniline
-
 ?
benzyloxycarbonyl-Gly-Pro-p-nitroanilide + H2O
-
 Pyrococcus furiosus benzyloxycarbonyl-Gly-Pro + p-nitroaniline
-
 ?
Gly-Pro-p-nitroanilide + H2O
-
 Pyrococcus furiosus Gly-Pro + p-nitroaniline
-
 ?
succinyl-Gly-Pro-4-methylcoumaryl-7-amide + H2O
-
 Sus scrofa succinyl-Gly-Pro + 7-amino-4-methylcoumarin
-
 ?

Synonyms

Synonyms Comment Organism
POP
-
 Pyrococcus furiosus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.03
-
 Arg-Pro-p-nitroanilide pH 7.5, 85°C Pyrococcus furiosus
0.06
-
 Gly-Pro-p-nitroanilide pH 7.5, 85°C Pyrococcus furiosus
0.073
-
 Asp-Pro-p-nitroanilide pH 7.5, 85°C Pyrococcus furiosus
0.079
-
 Ala-Pro-p-nitroanilide pH 7.5, 85°C Pyrococcus furiosus
2.5
-
 benzyloxycarbonyl-Ala-Ala-p-nitroanilide pH 7.5, 85°C Pyrococcus furiosus
16.9
-
 benzyloxycarbonyl-Gly-Pro-p-nitroanilide pH 7.5, 85°C Pyrococcus furiosus
17.9
-
 benzyloxycarbonyl-Ala-Pro-p-nitroanilide pH 7.5, 85°C Pyrococcus furiosus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00000039
-
 IC50: 0.39 nM Sus scrofa isophthalic acid L-prolyl-2(S)-(hydroxyacetyl)pyrrolidine L-prolyl-pyrrolidine amide
0.00000061
-
 IC50: 0.61 nM, log P: 0.2, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa isophthalic acid 2(S)-(cyclopentanecarbonyl)pyrrolidine L-prolyl-2(S)-(hydroxyacetyl)pyrrolidine amide
0.00000072
-
 IC50: 0.72 nM Sus scrofa isophthalic acid 2(S)-(cylcohexanecarbonyl)pyrrolidine L-prolyl-2(S)-cynaopyrrolidine amide
0.0000011
-
 IC50: 1.1 nM, log P: 0.8, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa isophthalic acid 2(S)-(cylcopentanecarbonyl)pyrrolidine L-prolyl-2(S)-cynaopyrrolidine amide
0.0000012
-
 IC50: 1.2 nM Sus scrofa isophthalic acid 2(S)-acetylpyrrolidine L-prolyl-2(S)-(hydroxyacetyl)pyrrolidine amide
0.0000013
-
 IC50: 1.3 nM Sus scrofa isophthalic acid L-prolyl-pyrrolidine L-prolyl-L-prolinal amide
0.0000013
-
 IC50: 1.3 nM, log P: 1.1, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa isophthalic acid 2(S)-benzoylpyrrolidine L-prolyl-2(S)-cynaopyrrolidine amide
0.0000015
-
 IC50: 1.5 nM Sus scrofa isophthalic acid L-prolyl-2(S)-cyanopyrrolidine L-prolyl-pyrrolidine amide
0.0000016
-
 IC50: 1.6 nM, log P: 0.3, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa isophthalic acid 2(S)-isobutanoylpyrrolidine L-prolyl-2(S)-cynaopyrrolidine amide
0.0000042
-
 IC50: 4.2 nM, log P: -0.6, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa isophthalic acid 2(S)-acetylpyrrolidine L-prolyl-2(S)-cynaopyrrolidine amide
0.000014
-
 IC50: 14 nM, log P: 1.1, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa isophthalic acid 2(S)-(cyclopentylcarbonyl)pyrrolidine L-prolyl-pyrrolidine amide
0.000018
-
 IC50: 18 nM Sus scrofa isophthalic acid 2(S)-benzoylpyrrolidine L-prolyl-pyrrolidine amide
0.000026
-
 IC50: 26 nM, log O = -0.2, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa isophthalic acid bis(L-prolyl-pyrrolidine) amide
0.000031
-
 IC50: 31 nM Sus scrofa isophthalic acid L-prolylbenzylamine L-prolyl-pyrrolidine amide
0.000054
-
 IC50: 54 nM Sus scrofa isophthalic acid (L-proline methyl ester) L-prolyl-pyrrolidine amide
0.000065
-
 IC50: 65 nM Sus scrofa isophthalic acid 2(S)-acetylpyrrolidine L-prolyl-pyrrolidine amide
0.000078
-
 IC50: 78 nM, log P: 2.7, the log P value is a first prediction of the blood-brain barrier penetrability Sus scrofa isophthalic acid bis-2(S)-(cyclopentanecarbonyl)pyrrolidine amide
0.00064
-
 IC50: 640 nM Sus scrofa isophthalic acid 2(S)-(cyclopentanecarbonyl)pyrrolidine (L-proline methyl ester) amide