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Literature summary extracted from

  • Huard, K.; Ahn, K.; Amor, P.; Beebe, D.A.; Borzilleri, K.A.; Chrunyk, B.A.; Coffey, S.B.; Cong, Y.; Conn, E.L.; Culp, J.S.; Dowling, M.S.; Gorgoglione, M.F.; Gutierrez, J.A.; Knafels, J.D.; Lachapelle, E.A.; Pandit, J.; Parris, K.D.; Perez, S.; Pfefferkorn, J.A.; Price, D.A.; Raymer, B.; Ross, T.T.; Shavnya, A.
    Discovery of fragment-derived small molecules for in vivo inhibition of ketohexokinase (KHK) (2017), J. Med. Chem., 60, 7835-7849 .
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.7.1.3 expression in Escherichia coli Homo sapiens
2.7.1.3 expression in Escherichia coli Rattus norvegicus

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
2.7.1.3
-
 Homo sapiens
2.7.1.3
-
 Rattus norvegicus

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.7.1.3 2-ethyl-7-(3-hydroxy-3-methylpyrrolidin-1-yl)-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile
-
 Homo sapiens
2.7.1.3 3-(trifluoromethyl)quinoxalin-2(1H)-one
-
 Homo sapiens
2.7.1.3 4,6-dimethyl-2-(morpholin-4-yl)pyridine-3-carbonitrile
-
 Homo sapiens
2.7.1.3 6-[(3S,4S)-3,4-dihydroxypyrrolidin-1-yl]-2-[(3S)-3-hydroxy-3-methylpyrrolidin-1-yl]-4-(trifluoromethyl)pyridine-3-carbonitrile nonbasic moderately potent and highly selective ketohexokinase inhibitor Homo sapiens
2.7.1.3 6-[(3S,4S)-3,4-dihydroxypyrrolidin-1-yl]-2-[(3S)-3-hydroxy-3-methylpyrrolidin-1-yl]-4-(trifluoromethyl)pyridine-3-carbonitrile nonbasic moderately potent and highly selective ketohexokinase inhibitor with favorable ADME and safety profiles and good exposure in rats Rattus norvegicus
2.7.1.3 6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-[(3S)-3-hydroxy-3-methylpyrrolidin-1-yl]-4-(trifluoromethyl)pyridine-3-carbonitrile
-
 Homo sapiens
2.7.1.3 6-[4-(2-hydroxyethyl)piperazin-1-yl]-4-[3-(hydroxymethyl)piperidin-1-yl]-2-(trifluoromethyl)pyridine-3-carbonitrile
-
 Homo sapiens
2.7.1.3 7-[(3R)-3-hydroxy-3-methylpyrrolidin-1-yl]-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile
-
 Homo sapiens
2.7.1.3 7-[(3S)-3-hydroxy-3-methylpyrrolidin-1-yl]-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile
-
 Homo sapiens
2.7.1.3 7-[(3S)-3-hydroxy-3-methylpyrrolidin-1-yl]-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile
-
 Rattus norvegicus
2.7.1.3 [(3R)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-yl]methanol
-
 Homo sapiens

Organism

EC Number Organism UniProt Comment Textmining
2.7.1.3 Homo sapiens P50053
-
-
2.7.1.3 Rattus norvegicus Q02974
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.7.1.3
-
 Homo sapiens
2.7.1.3
-
 Rattus norvegicus

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.7.1.3 ATP + D-fructose
-
 Homo sapiens ADP + D-fructose 1-phosphate
-
 ?
2.7.1.3 ATP + D-fructose
-
 Rattus norvegicus ADP + D-fructose 1-phosphate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.7.1.3 KHK
-
 Homo sapiens
2.7.1.3 KHK
-
 Rattus norvegicus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.7.1.3 0.00039
-
 23°C, pH 7.4, splice variant KHK-A Homo sapiens 6-[(3S,4S)-3,4-dihydroxypyrrolidin-1-yl]-2-[(3S)-3-hydroxy-3-methylpyrrolidin-1-yl]-4-(trifluoromethyl)pyridine-3-carbonitrile
2.7.1.3 0.00045
-
 23°C, pH 7.4, splice variant KHK-C Homo sapiens 6-[(3S,4S)-3,4-dihydroxypyrrolidin-1-yl]-2-[(3S)-3-hydroxy-3-methylpyrrolidin-1-yl]-4-(trifluoromethyl)pyridine-3-carbonitrile
2.7.1.3 0.00064
-
 23°C, pH 7.4 Rattus norvegicus 7-[(3S)-3-hydroxy-3-methylpyrrolidin-1-yl]-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile
2.7.1.3 0.00067
-
 23°C, pH 7.4 Homo sapiens 7-[(3S)-3-hydroxy-3-methylpyrrolidin-1-yl]-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile
2.7.1.3 0.00103
-
 23°C, pH 7.4 Homo sapiens 6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-[(3S)-3-hydroxy-3-methylpyrrolidin-1-yl]-4-(trifluoromethyl)pyridine-3-carbonitrile
2.7.1.3 0.00148
-
 23°C, pH 7.4 Homo sapiens 2-ethyl-7-(3-hydroxy-3-methylpyrrolidin-1-yl)-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile
2.7.1.3 0.01679
-
 23°C, pH 7.4 Homo sapiens 6-[4-(2-hydroxyethyl)piperazin-1-yl]-4-[3-(hydroxymethyl)piperidin-1-yl]-2-(trifluoromethyl)pyridine-3-carbonitrile
2.7.1.3 0.02421
-
 23°C, pH 7.4 Homo sapiens 7-[(3R)-3-hydroxy-3-methylpyrrolidin-1-yl]-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile
2.7.1.3 0.1
-
 23°C, pH 7.4 Homo sapiens 3-(trifluoromethyl)quinoxalin-2(1H)-one
2.7.1.3 0.118
-
 23°C, pH 7.4 Homo sapiens [(3R)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-yl]methanol
2.7.1.3 0.319
-
 23°C, pH 7.4 Homo sapiens 4,6-dimethyl-2-(morpholin-4-yl)pyridine-3-carbonitrile

General Information

EC Number General Information Comment Organism
2.7.1.3 metabolism increased fructose consumption and its subsequent metabolism are implicated in hepatic steatosis, dyslipidemia, obesity, and insulin resistance Homo sapiens
2.7.1.3 metabolism increased fructose consumption and its subsequent metabolism are implicated in hepatic steatosis, dyslipidemia, obesity, and insulin resistance Rattus norvegicus