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Literature summary extracted from

  • Pizzirani, D.; Pagliuca, C.; Realini, N.; Branduardi, D.; Bottegoni, G.; Mor, M.; Bertozzi, F.; Scarpelli, R.; Piomelli, D.; Bandiera, T.
    Discovery of a new class of highly potent inhibitors of acid ceramidase: synthesis and structure-activity relationship (SAR) (2013), J. Med. Chem., 56, 3518-3530.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
3.5.1.23 recombinant expression of V5/His-tagged enzyme using vector pEF6-V5/His in HEK-293 cells Rattus norvegicus

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.5.1.23 (1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol
-
 Rattus norvegicus
3.5.1.23 (1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
-
 Rattus norvegicus
3.5.1.23 3-(cyclopropylmethyl)-5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 3-benzoyl-5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 3-ethyl-5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 5-(benzyl(methyl)amino)-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 5-chloro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
 Rattus norvegicus
3.5.1.23 5-cyano-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
 Rattus norvegicus
3.5.1.23 5-ethyl-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 5-fluoro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
 Rattus norvegicus
3.5.1.23 5-fluoro-N-hexyl-3-(2-methylpropanoyl)-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 5-fluoro-N-hexyl-3-methyl-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 5-fluoro-N-octyl-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 6-chloro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
 Rattus norvegicus
3.5.1.23 carmofur
-
 Rattus norvegicus
3.5.1.23 ethyl 5-fluoro-3-(hexylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
-
 Rattus norvegicus
3.5.1.23 isobutyl 5-fluoro-3-(hexylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
-
 Rattus norvegicus
3.5.1.23 methyl 5-fluoro-3-(hexylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
-
 Rattus norvegicus
3.5.1.23 methyl 5-fluoro-3-(octylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
-
 Rattus norvegicus
3.5.1.23 additional information synthesis and evaluation of a series of 2,4-dioxopyrimidine-1-carboxamides as acid ceramidase enzyme inhibitors, structural features of uracil derivatives that are critical for inhibition, overview. No inhibition by 7 and 27b, while 4o, 26 and 30 are unstable Rattus norvegicus
3.5.1.23 N-butyl-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-heptyl-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-hexyl-2,4-dioxo-5-(trifluoromethyl)-3,4-dihydropyrimidine-1(2H)-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-hexyl-2,4-dioxo-5-phenylpyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-hexyl-2,4-dioxohexahydropyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-hexyl-3-methyl-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-hexyl-5,6-dimethyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-hexyl-5-(4-methylpiperazin-1-yl)-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-hexyl-5-(hydroxymethyl)-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-hexyl-5-bromo-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-hexyl-5-iodo-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-hexyl-5-methoxy-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-hexyl-5-methyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-hexyl-5-methylamino-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-hexyl-5-morpholino-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-hexyl-N-methyl-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-nonyl-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-octyl-2,4-dioxo-5-(trifluoromethyl)pyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-octyl-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 N-pentyl-2,4-dioxopyrimidine-1-carboxamide
-
 Rattus norvegicus
3.5.1.23 oleoylethanolamide
-
 Rattus norvegicus

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
3.5.1.23 intracellular
-
 Rattus norvegicus 5622
-

Organism

EC Number Organism UniProt Comment Textmining
3.5.1.23 Rattus norvegicus Q6P7S1
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.5.1.23 N-lauroylceramide + H2O
-
 Rattus norvegicus laureate + sphingosine
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.5.1.23 acid ceramidase
-
 Rattus norvegicus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.5.1.23 37
-
 assay at Rattus norvegicus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.5.1.23 4.5
-
 assay at Rattus norvegicus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.5.1.23 0.000004
-
 pH 4.5, 37°C Rattus norvegicus methyl 5-fluoro-3-(octylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
3.5.1.23 0.0000046
-
 pH 4.5, 37°C Rattus norvegicus 5-fluoro-N-octyl-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.000007
-
 pH 4.5, 37°C Rattus norvegicus methyl 5-fluoro-3-(hexylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
3.5.1.23 0.000007
-
 pH 4.5, 37°C Rattus norvegicus N-octyl-2,4-dioxo-5-(trifluoromethyl)pyrimidine-1-carboxamide
3.5.1.23 0.000012
-
 pH 4.5, 37°C Rattus norvegicus ethyl 5-fluoro-3-(hexylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
3.5.1.23 0.000012
-
 pH 4.5, 37°C Rattus norvegicus N-hexyl-2,4-dioxo-5-(trifluoromethyl)-3,4-dihydropyrimidine-1(2H)-carboxamide
3.5.1.23 0.000013
-
 pH 4.5, 37°C Rattus norvegicus 5-fluoro-N-hexyl-3-methyl-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.000016
-
 pH 4.5, 37°C Rattus norvegicus isobutyl 5-fluoro-3-(hexylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
3.5.1.23 0.000018
-
 pH 4.5, 37°C Rattus norvegicus 3-ethyl-5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.00002
-
 pH 4.5, 37°C Rattus norvegicus 3-benzoyl-5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.000021
-
 pH 4.5, 37°C Rattus norvegicus 5-fluoro-N-hexyl-3-(2-methylpropanoyl)-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.000029
-
 pH 4.5, 37°C Rattus norvegicus 5-fluoro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
3.5.1.23 0.000029
-
 pH and temperature not specified in the publication Rattus norvegicus carmofur
3.5.1.23 0.0000325
-
 pH 4.5, 37°C Rattus norvegicus N-heptyl-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.000051
-
 pH 4.5, 37°C Rattus norvegicus N-hexyl-5-bromo-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.000053
-
 pH 4.5, 37°C Rattus norvegicus N-hexyl-3-methyl-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.000061
-
 pH 4.5, 37°C Rattus norvegicus 3-(cyclopropylmethyl)-5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.000067
-
 pH 4.5, 37°C Rattus norvegicus 5-chloro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
3.5.1.23 0.000147
-
 pH 4.5, 37°C Rattus norvegicus N-hexyl-5-iodo-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.000177
-
 pH 4.5, 37°C Rattus norvegicus N-hexyl-2,4-dioxo-5-phenylpyrimidine-1-carboxamide
3.5.1.23 0.000283
-
 pH 4.5, 37°C Rattus norvegicus N-octyl-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.000417
-
 pH 4.5, 37°C Rattus norvegicus N-hexyl-5-(hydroxymethyl)-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.000426
-
 pH 4.5, 37°C Rattus norvegicus N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
3.5.1.23 0.000464
-
 pH 4.5, 37°C Rattus norvegicus N-nonyl-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.000733
-
 pH 4.5, 37°C Rattus norvegicus 5-ethyl-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.000875
-
 pH 4.5, 37°C Rattus norvegicus N-hexyl-5-morpholino-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.0011
-
 pH 4.5, 37°C Rattus norvegicus N-hexyl-5-methoxy-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.0014
-
 pH 4.5, 37°C Rattus norvegicus N-hexyl-5-(4-methylpiperazin-1-yl)-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.00146
-
 pH 4.5, 37°C Rattus norvegicus N-hexyl-5-methyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
3.5.1.23 0.0021
-
 pH 4.5, 37°C Rattus norvegicus N-pentyl-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.0034
-
 pH 4.5, 37°C Rattus norvegicus N-hexyl-5-methylamino-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.0055
-
 pH 4.5, 37°C Rattus norvegicus 5-(benzyl(methyl)amino)-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
3.5.1.23 0.0085
-
 pH 4.5, 37°C Rattus norvegicus N-butyl-2,4-dioxopyrimidine-1-carboxamide