Literature summary for 2.7.1.3 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 .

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Cloned(Commentary)

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

Crystallization (Commentary)

Crystallization (Comment)	Organism
-	Homo sapiens
-	Rattus norvegicus

Inhibitors

Inhibitors	Comment	Organism	Structure
2-ethyl-7-(3-hydroxy-3-methylpyrrolidin-1-yl)-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile	-	Homo sapiens
3-(trifluoromethyl)quinoxalin-2(1H)-one	-	Homo sapiens
4,6-dimethyl-2-(morpholin-4-yl)pyridine-3-carbonitrile	-	Homo sapiens
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
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
6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-[(3S)-3-hydroxy-3-methylpyrrolidin-1-yl]-4-(trifluoromethyl)pyridine-3-carbonitrile	-	Homo sapiens
6-[4-(2-hydroxyethyl)piperazin-1-yl]-4-[3-(hydroxymethyl)piperidin-1-yl]-2-(trifluoromethyl)pyridine-3-carbonitrile	-	Homo sapiens
7-[(3R)-3-hydroxy-3-methylpyrrolidin-1-yl]-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile	-	Homo sapiens
7-[(3S)-3-hydroxy-3-methylpyrrolidin-1-yl]-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile	-	Homo sapiens
7-[(3S)-3-hydroxy-3-methylpyrrolidin-1-yl]-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile	-	Rattus norvegicus
[(3R)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-yl]methanol	-	Homo sapiens

Organism

Organism	UniProt	Comment	Textmining
Homo sapiens	P50053	-	-
Rattus norvegicus	Q02974	-	-

Purification (Commentary)

Purification (Comment)	Organism
-	Homo sapiens
-	Rattus norvegicus

Substrates and Products (Substrate)

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

Synonyms

Synonyms	Comment	Organism
KHK	-	Homo sapiens
KHK	-	Rattus norvegicus

IC50 Value

IC50 Value	IC50 Value Maximum	Comment	Organism	Inhibitor	Structure
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
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
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
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
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
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
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
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
0.1	-	23°C, pH 7.4	Homo sapiens	3-(trifluoromethyl)quinoxalin-2(1H)-one
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
0.319	-	23°C, pH 7.4	Homo sapiens	4,6-dimethyl-2-(morpholin-4-yl)pyridine-3-carbonitrile

General Information

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

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Release 2023.1 (January 2023)