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Literature summary extracted from

  • Darvesh, S.; McDonald, R.S.; Darvesh, K.V.; Mataija, D.; Mothana, S.; Cook, H.; Carneiro, K.M.; Richard, N.; Walsh, R.; Martin, E.
    On the active site for hydrolysis of aryl amides and choline esters by human cholinesterases (2006), Bioorg. Med. Chem., 14, 4586-4599.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.1.1.8 Butyrylcholine competitive to butyrylthiocholine Homo sapiens
3.1.1.8 butyrylthiocholine competitive to butyrylcholine Homo sapiens

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.1.1.8 additional information
-
 additional information structure-activity relationships and kinetic studies, overview Homo sapiens
3.5.1.13 0.14
-
 N-(2-nitrophenyl)octanamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 0.36
-
 N-(2-nitrophenyl)butanamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 0.38
-
 N-(2-nitrophenyl)heptanamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 0.49
-
 N-(2-nitrophenyl)hexanamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 0.56
-
 N-(2-nitrophenyl)pentanamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 0.6
-
 N-(2-nitrophenyl)acetamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 1.78
-
 N-(2-nitrophenyl)propanamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 141
-
 N-(2-nitrophenyl)trifluoroacetamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.5.1.13 additional information Homo sapiens the aryl acylamidase activity, especially of butyrylcholinesterase, is involved in the development of the nervous system and in pathological processes such as the formation of neuritic plaques in Alzheimer's disease ?
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.1.1.8 Homo sapiens
-
-
-
3.5.1.13 Homo sapiens
-
-
-
3.5.1.13 Pseudomonas fluorescens
-
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
3.5.1.13 an anilide + H2O = a carboxylate + aniline acetylcholinesterase, EC 3.1.1.7, and butyrylcholinesterase, EC 3.1.1.8, also show aryl acylamidase activity using the same active site for both reactions, overview Homo sapiens
a

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.5.1.13 commercial preparation acetylcholinesterase Homo sapiens
-

Specific Activity [micromol/min/mg]

EC Number Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
3.5.1.13 additional information
-
 substrate specificity, initial reaction rates, overview Homo sapiens
3.5.1.13 additional information
-
 substrate specificity, initial reaction rates, overview Pseudomonas fluorescens

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.1.1.8 butyrylcholine + H2O
-
 Homo sapiens choline + butyrate
-
 ?
3.1.1.8 butyrylthiocholine + H2O
-
 Homo sapiens thiocholine + butyrate
-
 ?
3.1.1.8 additional information structure-activity relationships and kinetic studies, overview, the enzyme also shows an aryl acylamidase activity, EC 3.5.1.13, whereby it catalyzes the hydrolysis of amides of certain aromatic amines, BuChE shows high activity with larger N-(2-nitrophenyl)alkylamides, the ester and anilide substrates compete for the some catalytic site, no significant hydrolysis of the anilide takes place until the preferred choline ester hydrolysis is completed, overview Homo sapiens ?
-
 ?
3.5.1.13 additional information the aryl acylamidase activity, especially of butyrylcholinesterase, is involved in the development of the nervous system and in pathological processes such as the formation of neuritic plaques in Alzheimer's disease Homo sapiens ?
-
 ?
3.5.1.13 additional information acetylcholinesterase, EC 3.1.1.7, and butyrylcholinesterase, EC 3.1.1.8, also show aryl acylamidase activity using the same active site for both reactions, structure-activity relationship analysis, overview, substrate specificity of the aryl amidase activity, overview, no activity with N-(2,4-dinitrophenyl)acetamide, N-(4-nitrophenyl)aniline, N-(3-nitrophenyl)aniline, N-phenylacetamide, N-phenylbenzamide, N-(2-nitrophenyl)-3,3-dimethylbutanamide, N-methyl-N-(2-nitrophenyl)acetamide, N-methyl-N-(2-nitrophenyl)butanamide, N-phenyltrifluoroacetamide, and N-(2,6-dinitrophenyl)acetamide Homo sapiens ?
-
 ?
3.5.1.13 additional information structure-activity relationship analysis, overview, substrate specificity, overview, no activity with N-(2-nitrophenyl)benzamide, N-(2-nitrophenyl)phenylacetamide, N-(2-nitrophenyl)octanacetamide, N-(2-nitrophenyl)heptanacetamide, N-phenylbenzamide, N-(2-nitrophenyl)-3,3-dimethylbutanamide, N-methyl-N-(2-nitrophenyl)acetamide, N-methyl-N-(2-nitrophenyl)butanamide, N-phenyltrifluoroacetamide, and N-(2,6-dinitrophenyl)acetamide Pseudomonas fluorescens ?
-
 ?
3.5.1.13 N-(2,4-dinitrophenyl)acetamide + H2O
-
 Pseudomonas fluorescens N-(2,4-dinitrophenyl)aniline + acetate
-
 ?
3.5.1.13 N-(2-nitrophenyl)acetamide + H2O
-
 Homo sapiens N-(2-nitrophenyl)aniline + acetate
-
 ?
3.5.1.13 N-(2-nitrophenyl)acetamide + H2O
-
 Pseudomonas fluorescens N-(2-nitrophenyl)aniline + acetate
-
 ?
3.5.1.13 N-(2-nitrophenyl)benzamide + H2O no activity with acetylcholinesterase Homo sapiens N-(2-nitrophenyl)aniline + benzoic acid
-
 ?
3.5.1.13 N-(2-nitrophenyl)butanamide + H2O
-
 Pseudomonas fluorescens N-(2-nitrophenyl)aniline + butyrate
-
 ?
3.5.1.13 N-(2-nitrophenyl)butanamide + H2O no activity with acetylcholinesterase Homo sapiens N-(2-nitrophenyl)aniline + butyrate
-
 ?
3.5.1.13 N-(2-nitrophenyl)heptanamide + H2O
-
 Homo sapiens N-(2-nitrophenyl)aniline + heptanoate
-
 ?
3.5.1.13 N-(2-nitrophenyl)hexanacetamide + H2O
-
 Pseudomonas fluorescens N-(2-nitrophenyl)aniline + hexanoate
-
 ?
3.5.1.13 N-(2-nitrophenyl)hexanacetamide + H2O no activity with acetylcholinesterase Homo sapiens N-(2-nitrophenyl)aniline + hexanoate
-
 ?
3.5.1.13 N-(2-nitrophenyl)octanamide + H2O
-
 Homo sapiens N-(2-nitrophenyl)aniline + octanoate
-
 ?
3.5.1.13 N-(2-nitrophenyl)pentanacetamide + H2O
-
 Homo sapiens N-(2-nitrophenyl)aniline + pentanoate
-
 ?
3.5.1.13 N-(2-nitrophenyl)pentanacetamide + H2O
-
 Pseudomonas fluorescens N-(2-nitrophenyl)aniline + pentanoate
-
 ?
3.5.1.13 N-(2-nitrophenyl)phenylacetamide + H2O
-
 Homo sapiens N-(2-nitrophenyl)aniline + phenylacetate
-
 ?
3.5.1.13 N-(2-nitrophenyl)propanamide + H2O
-
 Homo sapiens N-(2-nitrophenyl)aniline + propionate
-
 ?
3.5.1.13 N-(2-nitrophenyl)propanamide + H2O
-
 Pseudomonas fluorescens N-(2-nitrophenyl)aniline + propionate
-
 ?
3.5.1.13 N-(2-nitrophenyl)trifluoroacetamide + H2O
-
 Pseudomonas fluorescens N-(2-nitrophenyl)aniline + trifluoroacetate
-
 ?
3.5.1.13 N-(2-nitrophenyl)trifluoroacetamide + H2O best substrate of acetylcholinesterase and butyrylcholinesterase Homo sapiens N-(2-nitrophenyl)aniline + trifluoroacetate
-
 ?
3.5.1.13 N-(3-methoxy-2-nitrophenyl)acetamide + H2O
-
 Pseudomonas fluorescens N-(3-methoxy-2-nitrophenyl)aniline + acetate
-
 ?
3.5.1.13 N-(3-methoxy-2-nitrophenyl)acetamide + H2O no activity with acetylcholinesterase Homo sapiens N-(3-methoxy-2-nitrophenyl)aniline + acetate
-
 ?
3.5.1.13 N-(3-nitrophenyl)acetamide + H2O
-
 Pseudomonas fluorescens N-(3-nitrophenyl)aniline + acetate
-
 ?
3.5.1.13 N-(4-nitrophenyl)acetamide + H2O
-
 Pseudomonas fluorescens N-(4-nitrophenyl)aniline + acetate
-
 ?
3.5.1.13 N-(5-methoxy-2-nitrophenyl)acetamide + H2O
-
 Homo sapiens N-(5-methoxy-2-nitrophenyl)aniline + acetate
-
 ?
3.5.1.13 N-(5-methoxy-2-nitrophenyl)acetamide + H2O
-
 Pseudomonas fluorescens N-(5-methoxy-2-nitrophenyl)aniline + acetate
-
 ?
3.5.1.13 N-phenylacetamide + H2O
-
 Pseudomonas fluorescens N-phenylaniline + acetate
-
 ?

Subunits

EC Number Subunits Comment Organism
3.5.1.13 More structure-activity relationship analysis, overview Homo sapiens

Synonyms

EC Number Synonyms Comment Organism
3.1.1.8 BuChE
-
 Homo sapiens
3.1.1.8 butyrylcholinesterase
-
 Homo sapiens
3.1.1.8 ChE
-
 Homo sapiens
3.1.1.8 cholinesterase
-
 Homo sapiens
3.1.1.8 More cf. EC 3.5.1.13 Homo sapiens

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.5.1.13 23
-
 assay at Homo sapiens
3.5.1.13 23
-
 assay at Pseudomonas fluorescens

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
3.5.1.13 0.05
-
 N-(2-nitrophenyl)acetamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 0.58
-
 N-(2-nitrophenyl)butanamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 0.77
-
 N-(2-nitrophenyl)propanamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 2.87
-
 N-(2-nitrophenyl)pentanamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 3 6 N-(2-nitrophenyl)pentanamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 3.3
-
 N-(2-nitrophenyl)heptanamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 3.3
-
 N-(2-nitrophenyl)octanamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 3.83
-
 N-(2-nitrophenyl)hexanamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 4.98
-
 N-(2-nitrophenyl)heptanamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 5.43
-
 N-(2-nitrophenyl)octanamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens
3.5.1.13 1672
-
 N-(2-nitrophenyl)trifluoroacetamide pH 8.0, 23°C, butyrylcholinesterase Homo sapiens

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.5.1.13 8
-
 assay at Homo sapiens
3.5.1.13 8
-
 assay at Pseudomonas fluorescens