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Literature summary for 3.4.14.5 extracted from

  • Madar, D.J.; Kopecka, H.; Pireh, D.; Yong, H.; Pei, Z.; Li, X.; Wiedeman, P.E.; Djuric, S.W.; Von Geldern, T.W.; Fickes, M.G.; Bhagavatula, L.; McDermott, T.; Wittenberger, S.; Richards, S.J.; Longenecker, K.L.; Stewart, K.D.; Lubben, T.H.; Ballaron, S.J.; Stashko, M.A.; Long, M.A.; Wells, H.; Zinker, B.A.
    Discovery of (2-(4-((2-(2S,5R)-2-cyano-5-ethynyl-1-pyrrolidinyl)-2-oxoethyl)amino)-4-methyl-1-piperidinyl)-4-pyridinecarboxylic acid (ABT-279): a very potent, selective, effective, and well-tolerated inhibitor of dipeptidyl peptidase-IV, useful for the treatment of diabetes (2006), J. Med. Chem., 49, 6416-6420.
    View publication on PubMed

Application

Application Comment Organism
medicine (2-(4-((2-(2S,5R)-2-cyano-5-ethynyl-1-pyrrolidinyl)-2-oxoethyl)amino)-4-methyl-1-piperidinyl)-4-pyridinecarboxylic acid (i. e. ABT-279) is a very potent, selective, effective, and well-tolerated inhibitor useful for the treatment of diabetes Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
(2-(4-((2-(2S,5R)-2-cyano-5-ethynyl-1-pyrrolidinyl)-2-oxoethyl)amino)-4-methyl-1-piperidinyl)-4-pyridine carboxylic acid i. e. ABT-279, a very potent, selective, effective, and well-tolerated inhibitor useful for the treatment of diabetes Homo sapiens
(2-(4-((2-(2S,5R)-2-cyano-5-ethynyl-1-pyrrolidinyl)-2-oxoethyl)amino)-4-methyl-1-piperidinyl)-4-pyridinecarboxylic acid i. e. ABT-279, a very potent, selective, effective, and well-tolerated inhibitor useful for the treatment of diabetes Canis lupus familiaris
(2-(4-((2-(2S,5R)-2-cyano-5-ethynyl-1-pyrrolidinyl)-2-oxoethyl)amino)-4-methyl-1-piperidinyl)-4-pyridinecarboxylic acid i. e. ABT-279, a very potent, selective, effective, and well-tolerated inhibitor useful for the treatment of diabetes Rattus norvegicus
(2R,5S)-1-[N-[1-(5-cyanopyridin-2-yl)-4-methylpiperidin-4-yl]glycyl]pyrrolidine-2,5-dicarbonitrile
-
Homo sapiens
(2S)-1-[(1-adamantylamino)acetyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-[(2R)-2-amino-2-cyclopentylacetyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-[(cyclopentylamino)acetyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-[(tert-butylamino)acetyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,5R)-1-[(2R)-2-amino-2-cyclohexylacetyl]-5-ethynylpyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,5R)-1-[(2R)-2-amino-2-cyclopentylacetyl]-5-ethynylpyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,5R)-1-[(2R)-2-amino-2-cyclopentylacetyl]-5-methylpyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,5R)-1-[(2R)-2-amino-2-cyclopentylacetyl]-5-prop-1-yn-1-ylpyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,5R)-1-[(2R)-2-amino-2-cyclopentylacetyl]-5-vinylpyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,5R)-1-[(2R)-2-amino-4-methylpentanoyl]-5-ethynylpyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,5R)-1-[(2R)-2-amino-4-methylpentanoyl]-5-methylpyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,5R)-1-[(cyclohexylamino)acetyl]-5-ethynylpyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,5R)-1-[(cyclopentylamino)acetyl]-5-ethynylpyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,5R)-1-[(cyclopentylamino)acetyl]-5-prop-1-yn-1-ylpyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,5R)-1-[(tert-butylamino)acetyl]-5-ethynylpyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,5R)-1-[N-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)glycyl]-5-prop-1-yn-1-ylpyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,5R)-1-[[(cis-1-ethyl-4-hydroxycyclohexyl)amino]acetyl]-5-ethynylpyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,5S)-1-[(cyclopentylamino)acetyl]-5-methylpyrrolidine-2-carbonitrile
-
Homo sapiens
6-[4-([2-[(2R,5S)-2,5-dicyanopyrrolidin-1-yl]-2-oxoethyl]amino)-4-methylpiperidin-1-yl]pyridine-3-carboxylic acid
-
Homo sapiens
6-[[4-([2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl]amino)cyclohexyl]oxy]nicotinonitrile
-
Homo sapiens
6-[[4-([2-[(2S,5R)-2-cyano-5-ethynylpyrrolidin-1-yl]-2-oxoethyl]amino)cyclohexyl]oxy]pyridine-3-carbonitrile
-
Homo sapiens

Organism

Organism UniProt Comment Textmining
Canis lupus familiaris
-
-
-
Homo sapiens P27487
-
-
Rattus norvegicus
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
Caco-2 cell
-
Homo sapiens
-

Synonyms

Synonyms Comment Organism
dipeptidyl peptidase-IV
-
Rattus norvegicus
dipeptidyl peptidase-IV
-
Canis lupus familiaris
dipeptidyl peptidase-IV
-
Homo sapiens
DPP-IV
-
Rattus norvegicus
DPP-IV
-
Canis lupus familiaris
DPP-IV
-
Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000001
-
(2-(4-((2-(2S,5R)-2-cyano-5-ethynyl-1-pyrrolidinyl)-2-oxoethyl)amino)-4-methyl-1-piperidinyl)-4-pyridinecarboxylic acid
-
Rattus norvegicus
0.000001
-
(2-(4-((2-(2S,5R)-2-cyano-5-ethynyl-1-pyrrolidinyl)-2-oxoethyl)amino)-4-methyl-1-piperidinyl)-4-pyridinecarboxylic acid
-
Canis lupus familiaris
0.000001
-
(2-(4-((2-(2S,5R)-2-cyano-5-ethynyl-1-pyrrolidinyl)-2-oxoethyl)amino)-4-methyl-1-piperidinyl)-4-pyridinecarboxylic acid
-
Homo sapiens
0.000001
-
(2S)-1-[(2R)-2-amino-2-cyclopentylacetyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
0.000001
-
6-[4-([2-[(2R,5S)-2,5-dicyanopyrrolidin-1-yl]-2-oxoethyl]amino)-4-methylpiperidin-1-yl]pyridine-3-carboxylic acid
-
Homo sapiens
0.000003
-
(2R,5S)-1-[N-[1-(5-cyanopyridin-2-yl)-4-methylpiperidin-4-yl]glycyl]pyrrolidine-2,5-dicarbonitrile
-
Homo sapiens
0.000004
-
(2S)-1-[(1-adamantylamino)acetyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
0.000004
-
6-[[4-([2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl]amino)cyclohexyl]oxy]nicotinonitrile
-
Homo sapiens
0.000005
-
6-[[4-([2-[(2S,5R)-2-cyano-5-ethynylpyrrolidin-1-yl]-2-oxoethyl]amino)cyclohexyl]oxy]pyridine-3-carbonitrile
-
Homo sapiens
0.000008
-
(2S,5R)-1-[(2R)-2-amino-2-cyclopentylacetyl]-5-ethynylpyrrolidine-2-carbonitrile
-
Homo sapiens
0.000008
-
(2S,5R)-1-[(2R)-2-amino-4-methylpentanoyl]-5-ethynylpyrrolidine-2-carbonitrile
-
Homo sapiens
0.00001
-
(2S)-1-[(tert-butylamino)acetyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
0.000011
-
(2S)-1-[(cyclopentylamino)acetyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
0.000022
-
(2S,5R)-1-[(cyclopentylamino)acetyl]-5-ethynylpyrrolidine-2-carbonitrile
-
Homo sapiens
0.000024
-
(2S,5R)-1-[(2R)-2-amino-2-cyclopentylacetyl]-5-prop-1-yn-1-ylpyrrolidine-2-carbonitrile
-
Homo sapiens
0.000025
-
(2S,5R)-1-[(tert-butylamino)acetyl]-5-ethynylpyrrolidine-2-carbonitrile
-
Homo sapiens
0.000049
-
(2S,5R)-1-[(2R)-2-amino-4-methylpentanoyl]-5-methylpyrrolidine-2-carbonitrile
-
Homo sapiens
0.000062
-
(2S,5R)-1-[N-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)glycyl]-5-prop-1-yn-1-ylpyrrolidine-2-carbonitrile
-
Homo sapiens
0.000079
-
(2S,5R)-1-[(cyclohexylamino)acetyl]-5-ethynylpyrrolidine-2-carbonitrile
-
Homo sapiens
0.00009
-
(2S,5R)-1-[[(cis-1-ethyl-4-hydroxycyclohexyl)amino]acetyl]-5-ethynylpyrrolidine-2-carbonitrile
-
Homo sapiens
0.000096
-
(2S,5R)-1-[(2R)-2-amino-2-cyclohexylacetyl]-5-ethynylpyrrolidine-2-carbonitrile
-
Homo sapiens
0.000097
-
(2S,5R)-1-[(2R)-2-amino-2-cyclopentylacetyl]-5-methylpyrrolidine-2-carbonitrile
-
Homo sapiens
0.000811
-
(2S,5S)-1-[(cyclopentylamino)acetyl]-5-methylpyrrolidine-2-carbonitrile
-
Homo sapiens
0.000959
-
(2S,5R)-1-[(cyclopentylamino)acetyl]-5-prop-1-yn-1-ylpyrrolidine-2-carbonitrile
-
Homo sapiens
0.0038
-
(2S,5R)-1-[(2R)-2-amino-2-cyclopentylacetyl]-5-vinylpyrrolidine-2-carbonitrile
-
Homo sapiens