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Literature summary extracted from

  • Korhonen, J.; Kuusisto, A.; van Bruchem, J.; Patel, J.Z.; Laitinen, T.; Navia-Paldanius, D.; Laitinen, J.T.; Savinainen, J.R.; Parkkari, T.; Nevalainen, T.J.
    Piperazine and piperidine carboxamides and carbamates as inhibitors of fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL) (2014), Bioorg. Med. Chem., 22, 6694-6705.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
3.5.1.99 transient expression of the enzyme in COS7 cells Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.5.1.99 (1H-benzo[d][1,2,3]triazol-1-yl)(4-(3-phenoxybenzyl)-piperazin-1-yl)-methanone
-
 Homo sapiens
3.5.1.99 (1H-benzo[d][1,2,3]triazol-1-yl)(4-(4-phenoxybenzyl)-piperazin-1-yl)-methanone hydrochloride
-
 Homo sapiens
3.5.1.99 (1H-imidazol-1-yl)(4-(3-phenoxybenzyl)piperazin-1-yl)methanone
-
 Homo sapiens
3.5.1.99 (1H-imidazol-1-yl)(4-(4-phenoxy-benzyl)-piperazin-1-yl)-methanone hydrochloride
-
 Homo sapiens
3.5.1.99 (3H-[1,2,3]triazol[4,5-b]pyridin-3-yl)(4-(3-phenoxybenzyl)-piperazin-1-yl)-methanone
-
 Homo sapiens
3.5.1.99 (4-(bis(benzo[d][1,3]dioxol-5-yl)(hydroxy)methyl)-piperidin-1-yl)(1H-1,2,4-triazol-1-yl)methanone
-
 Homo sapiens
3.5.1.99 (4-benzhydrylpiperazin-1-yl)(4-phenyl-1H-imidazol-1-yl)methanone 62% activity remaining at 0.01 mM Homo sapiens
3.5.1.99 (4-phenylpiperazin-1-yl)(1H-1,2,4-triazol-1-yl)methanone
-
 Homo sapiens
3.5.1.99 1,1,1,3,3,3-hexafluoropropan-2-yl 4-(3-phenoxybenzyl)piperazine-1-carboxylate
-
 Homo sapiens
3.5.1.99 1-[4-[bis(1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidin-1-yl]-3,3,3-trifluoro-2-(trifluoromethyl)propan-1-one
-
 Homo sapiens
3.5.1.99 1H-benzotriazol-1-yl[4-(diphenylmethyl)piperazin-1-yl]methanone
-
 Homo sapiens
3.5.1.99 2,2,2-trichloroethyl 4-(bis(benzo[d][1,3]dioxol-5-yl)(hydroxy)methyl)piperidine-1-carboxylate
-
 Homo sapiens
3.5.1.99 2H-benzotriazol-2-yl(4-phenylpiperazin-1-yl)methanone
-
 Homo sapiens
3.5.1.99 2H-benzotriazol-2-yl[4-(diphenylmethyl)piperazin-1-yl]methanone
-
 Homo sapiens
3.5.1.99 4-(3-phenoxybenzyl)-N-(4-methoxyphenyl)piperazine-1-carboxamide
-
 Homo sapiens
3.5.1.99 4-(3-phenoxybenzyl)-N-(4-nitrophenyl)piperazine-1-carboxamide
-
 Homo sapiens
3.5.1.99 4-(3-phenoxybenzyl)-N-phenylpiperazine-1-carboxamide
-
 Homo sapiens
3.5.1.99 4-benzhydryl-N-(4-(trifluoromethyl)phenyl)piperazine-1-carboxamide 86% activity remaining at 0.01 mM Homo sapiens
3.5.1.99 4-benzhydryl-N-(4-butylphenyl)piperazine-1-carboxamide 84% activity remaining at 0.01 mM Homo sapiens
3.5.1.99 4-benzhydryl-N-(4-methoxyphenyl)piperazine-1-carboxamide 89% activity remaining at 0.01 mM Homo sapiens
3.5.1.99 4-benzhydryl-N-(4-nitrophenyl)piperazine-1-carboxamide 84% activity remaining at 0.01 mM Homo sapiens
3.5.1.99 4-benzhydryl-N-(pyridin-2-yl)piperazine-1-carboxamide 87% activity remaining at 0.01 mM Homo sapiens
3.5.1.99 4-benzhydryl-N-(pyridin-3-yl)piperazine-1-carboxamide 87% activity remaining at 0.01 mM Homo sapiens
3.5.1.99 4-benzhydryl-N-phenylpiperazine-1-carboxamide 88% activity remaining at 0.01 mM Homo sapiens
3.5.1.99 4-nitrophenyl 4-(3-phenoxybenzyl)piperazine-1-carboxylate
-
 Homo sapiens
3.5.1.99 4-nitrophenyl 4-(diphenylmethyl)piperazine-1-carboxylate
-
 Homo sapiens
3.5.1.99 4-nitrophenyl 4-[bis(1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate
-
 Homo sapiens
3.5.1.99 4-nitrophenyl 4-[bis(4-fluorophenyl)methyl]piperazine-1-carboxylate
-
 Homo sapiens
3.5.1.99 4-nitrophenyl-4-(4-phenoxy-benzyl)-piperazine-1-carboxylate
-
 Homo sapiens
3.5.1.99 4-nitrophenyl-4-(bis(benzo[d][1,3]dioxol-5-yl)methyl)piperidine-1-carboxylate
-
 Homo sapiens
3.5.1.99 4-[4-(2,4-difluorophenyl)-1,3-thiazol-2-yl]-N-(3,4-dimethyl-1,2-oxazol-5-yl)piperazine-1-carboxamide
-
 Homo sapiens
3.5.1.99 benzyl 4-(dibenzo[d][1,3]dioxol-5-yl(hydroxy)methyl)-piperidine-1-carboxylate
-
 Homo sapiens
3.5.1.99 ethyl 4-(1H-1,2,4-triazol-1-ylcarbonyl)piperazine-1-carboxylate
-
 Homo sapiens
3.5.1.99 ethyl 4-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-ylcarbonyl)piperazine-1-carboxylate
-
 Homo sapiens
3.5.1.99 additional information piperazine and piperidine carboxamides and carbamates as enzyme inhibitors, molecular modeling, overview. Diverse leaving groups are tolerated for FAAH inhibitors Homo sapiens
3.5.1.99 N-(pyridin-3-yl)-4-(3-[[5-(trifluoromethyl)pyridin-2-yl]oxy]benzyl)piperidine-1-carboxamide
-
 Homo sapiens
3.5.1.99 N-phenyl-4-(3-phenyl-4,5-dihydro-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide
-
 Homo sapiens
3.5.1.99 [4-(3-phenoxybenzyl)piperazin-1-yl](1H-1,2,4-triazol-1-yl)methanone
-
 Homo sapiens
3.5.1.99 [4-(diphenylmethyl)piperazin-1-yl](1H-1,2,4-triazol-1-yl)methanone
-
 Homo sapiens
3.5.1.99 [4-(diphenylmethyl)piperazin-1-yl](1H-imidazol-1-yl)methanone
-
 Homo sapiens
3.5.1.99 [4-[bis(1,3-benzodioxol-5-yl)methyl]piperidin-1-yl](1H-1,2,4-triazol-1-yl)methanone
-
 Homo sapiens
3.5.1.99 [4-[bis(4-fluorophenyl)methyl]piperazin-1-yl](1H-1,2,4-triazol-1-yl)methanone
-
 Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.5.1.99 additional information Homo sapiens FAAH is the primary N-arachidonoylethanolamine-degrading enzyme, but it is also capable of hydrolyzing other bioactive N-acylethanolamines, such as N-palmitoylethanolamine, N-oleoylethanolamine and the sleep-inducing lipid oleamide ?
-
 ?
3.5.1.99 N-arachidonoylethanolamine + H2O Homo sapiens
-
 arachidonic acid + ethanolamine
-
 ?
3.5.1.99 N-oleoylethanolamine + H2O Homo sapiens
-
 oleic acid + ethanolamine
-
 ?
3.5.1.99 N-palmitoylethanolamine + H2O Homo sapiens
-
 palmitic acid + ethanolamine
-
 ?
3.5.1.99 oleamide + H2O Homo sapiens
-
 oleic acid + NH3
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.5.1.99 Homo sapiens O00519
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.5.1.99 additional information FAAH is the primary N-arachidonoylethanolamine-degrading enzyme, but it is also capable of hydrolyzing other bioactive N-acylethanolamines, such as N-palmitoylethanolamine, N-oleoylethanolamine and the sleep-inducing lipid oleamide Homo sapiens ?
-
 ?
3.5.1.99 N-arachidonoylethanolamine + H2O
-
 Homo sapiens arachidonic acid + ethanolamine
-
 ?
3.5.1.99 N-oleoylethanolamine + H2O
-
 Homo sapiens oleic acid + ethanolamine
-
 ?
3.5.1.99 N-palmitoylethanolamine + H2O
-
 Homo sapiens palmitic acid + ethanolamine
-
 ?
3.5.1.99 oleamide + H2O
-
 Homo sapiens oleic acid + NH3
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.5.1.99 FAAH
-
 Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.5.1.99 0.00000163
-
 pH and temperature not specified in the publication Homo sapiens 4-nitrophenyl-4-(4-phenoxy-benzyl)-piperazine-1-carboxylate
3.5.1.99 0.00000175
-
 pH and temperature not specified in the publication Homo sapiens 4-(3-phenoxybenzyl)-N-(4-methoxyphenyl)piperazine-1-carboxamide
3.5.1.99 0.00000188
-
 pH and temperature not specified in the publication Homo sapiens 1,1,1,3,3,3-hexafluoropropan-2-yl 4-(3-phenoxybenzyl)piperazine-1-carboxylate
3.5.1.99 0.00000199
-
 pH and temperature not specified in the publication Homo sapiens 4-(3-phenoxybenzyl)-N-(4-nitrophenyl)piperazine-1-carboxamide
3.5.1.99 0.0000034
-
 pH and temperature not specified in the publication Homo sapiens (1H-imidazol-1-yl)(4-(4-phenoxy-benzyl)-piperazin-1-yl)-methanone hydrochloride
3.5.1.99 0.000015
-
 pH and temperature not specified in the publication Homo sapiens (1H-imidazol-1-yl)(4-(3-phenoxybenzyl)piperazin-1-yl)methanone
3.5.1.99 0.000023
-
 pH and temperature not specified in the publication Homo sapiens (3H-[1,2,3]triazol[4,5-b]pyridin-3-yl)(4-(3-phenoxybenzyl)-piperazin-1-yl)-methanone
3.5.1.99 0.000089
-
 pH and temperature not specified in the publication Homo sapiens (1H-benzo[d][1,2,3]triazol-1-yl)(4-(3-phenoxybenzyl)-piperazin-1-yl)-methanone
3.5.1.99 0.000708
-
 pH and temperature not specified in the publication Homo sapiens (1H-benzo[d][1,2,3]triazol-1-yl)(4-(4-phenoxybenzyl)-piperazin-1-yl)-methanone hydrochloride
3.5.1.99 0.00162
-
 pH and temperature not specified in the publication Homo sapiens (4-(bis(benzo[d][1,3]dioxol-5-yl)(hydroxy)methyl)-piperidin-1-yl)(1H-1,2,4-triazol-1-yl)methanone
3.5.1.99 0.00194
-
 pH and temperature not specified in the publication Homo sapiens 4-nitrophenyl-4-(bis(benzo[d][1,3]dioxol-5-yl)methyl)piperidine-1-carboxylate
3.5.1.99 0.00195
-
 pH and temperature not specified in the publication Homo sapiens benzyl 4-(dibenzo[d][1,3]dioxol-5-yl(hydroxy)methyl)-piperidine-1-carboxylate
3.5.1.99 0.00196
-
 pH and temperature not specified in the publication Homo sapiens 2,2,2-trichloroethyl 4-(bis(benzo[d][1,3]dioxol-5-yl)(hydroxy)methyl)piperidine-1-carboxylate
3.5.1.99 0.00302
-
 pH and temperature not specified in the publication Homo sapiens 4-(3-phenoxybenzyl)-N-phenylpiperazine-1-carboxamide

General Information

EC Number General Information Comment Organism
3.5.1.99 metabolism fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL) are key hydrolytic enzymes of the endocannabinoid system Homo sapiens