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Information on EC 3.5.1.13 - aryl-acylamidase
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3.5.1.13 aryl-acylamidaseIUBMB Comments
Also acts on 4-substituted anilides.
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Word Map
- 3.5.1.13
- acetylcholinesterase
- aaa
- cholinesterases
- o-nitroacetanilide
- buche
-
acetanilid
- eserine
-
serotonin-sensitive
- propanil
-
3.1.1.8
- neostigmine
- pharmacology
-
acylanilide
- diagnostics
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
aryl acylamidase, aryl-acylamidase, polyamidase, azl13, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
AAA
aryl acylamidase
Azl13
EC 3.5.1.13 AAA-2
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-
-
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EC 3.5.1.13, AAA-1
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-
-
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polyamidase
pseudocholinesterase
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-
-
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additional information
the enzyme belongs to the amidase signature, AS, enzyme family
aryl acylamidase
-
aryl acylamidase activity of fatty acid-free human serum albumin
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
an anilide + H2O = a carboxylate + aniline
-
-
-
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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
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an anilide + H2O = a carboxylate + aniline
mechanism of substrate specificity and reactivity change of the enzyme, acetylcholinesterase, EC 3.1.1.7, and butyrylcholinesterase, EC 3.1.1.8, are known to exhibit aryl acylamidase activities, overview
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
carboxylic acid amide hydrolysis
carboxylic acid amide hydrolysis
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SYSTEMATIC NAME
IUBMB Comments
aryl-acylamide amidohydrolase
Also acts on 4-substituted anilides.
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CAS REGISTRY NUMBER
COMMENTARY
9025-18-7
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2',3'-dichloropropionanilide + H2O
2,3-dichloroaniline + propionate
-
14% of the activity with 3',4'-dichloropropionanilide
-
-
?
2',4'-dichloropropionanilide + H2O
2,4-dichloroaniline + propionate
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49% of the activity with 3',4'-dichloropropionanilide
-
-
?
2'-chloropropionanilide + H2O
2-chloroaniline + propionate
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37% of the activity with 3',4'-dichloropropionanilide
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-
?
2-nitrotrifluoroacetanilide + H2O
2-nitroaniline + trifluoroacetic acid
acetylcholinesterase exhibits two different activities: esterase and aryl acylamidase
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-
?
3',4'-dichloro-2-methacrylanilide + H2O
3,4-dichloroaniline + 2-methyl-2-propenoate
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8% of the activity with 3',4'-dichloropropionanilide
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-
?
3',4'-dichloroacetanilide + H2O
3,4-dichloroaniline + acetate
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49% of the activity with 3',4'-dichloropropionanilide
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-
?
3',4'-dichlorobutyranilide + H2O
3,4-dichloroaniline + butyrate
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37% of the activity with 3',4'-dichloropropionanilide
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-
?
3',4'-dichlorovaleranilide + H2O
3,4-dichloroaniline + pentanoate
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12% of the activity with 3',4'-dichloropropionanilide
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-
?
3'-chloropropionanilide + H2O
3-chloroaniline + propionate
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51% of the activity with 3',4'-dichloropropionanilide
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?
3,4-dichloropropionanilide + H2O
?
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plants with significant amounts of aryl acylamidase are able to hydrolyze acylanilide herbicides quickly and thereby avoid the toxic effects of these compounds
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-
?
3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea + H2O
3,4-dichloroaniline + ?
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i.e. linuron
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?
3-(acetamido)N,N,N-trimethylanilinium + H2O
3-amino-N,N,N-trimethylanilinium + acetic acid
-
-
-
-
?
4'-chloropropionanilide + H2O
4-chloroaniline + propionate
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54% of the activity with 3',4'-dichloropropionanilide
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-
?
4-acetylaminobenzaldehyde thiosemicarbazone + H2O
4-aminobenzaldehyde thiosemicarbazone + acetic acid
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i.e. thiacetazone
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?
acetaminophen + H2O
4-aminophenol + acetate
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i.e. paracetamol
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?
N-(2,4-dinitrophenyl)acetamide + H2O
N-(2,4-dinitrophenyl)aniline + acetate
-
-
-
-
?
N-(2-nitrophenyl)benzamide + H2O
N-(2-nitrophenyl)aniline + benzoic acid
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no activity with acetylcholinesterase
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-
?
N-(2-nitrophenyl)heptanamide + H2O
N-(2-nitrophenyl)aniline + heptanoate
-
-
-
-
?
N-(2-nitrophenyl)octanamide + H2O
N-(2-nitrophenyl)aniline + octanoate
-
-
-
-
?
N-(2-nitrophenyl)phenylacetamide + H2O
N-(2-nitrophenyl)aniline + phenylacetate
-
-
-
-
?
N-(3,4-dichlorophenyl) propanamide + H2O
3,4-dichloroaniline + propanoic acid
i.e. propanil
-
-
?
N-(3,4-dichlorophenyl)propanamide + H2O
3,4-dichloraniline + propanoate
no activity with butachlor, acetochlor, 4-nitroacetanilide, p-chloracetanilide
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-
?
N-(3-nitrophenyl)acetamide + H2O
N-(3-nitrophenyl)aniline + acetate
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-
-
-
?
N-(4-nitrophenyl)acetamide + H2O
N-(4-nitrophenyl)aniline + acetate
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-
-
-
?
N-(o-nitrophenyl)trifluoroacetamide + ?
2-nitroaniline + trifluoracetic acid
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aryl acylamidase activity of fatty acid-free human serum albumin
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?
Nalpha-benzoyl-DL-Arg beta-naphthylamide + H2O
Nalpha-benzoyl-DL-Arg + beta-naphthylamine
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-
-
-
?
o-nitrotrifluoroacetanilide + H2O
o-nitroaniline + trifluoroacetic acid
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reaction is performed by human serum albumin, substrate is more reactive than o-nitroacetanilide
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-
?
2-nitroacetanilide + H2O
2-nitroaniline + acetate
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the reaction in human erythrocytes and plasma is performed by the butyrylcholinesterase, EC 3.1.1.8, which is inactive with butyrylthiocholine, also fatty acid free human albumin has aryl acylacylamidase activity, which accounts for 10% of total human enzyme activity
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-
?
2-nitroacetanilide + H2O
2-nitroaniline + acetate
acetylcholinesterase exhibits two different activities: esterase and aryl acylamidase
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-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
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-
-
-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
-
-
-
-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
-
-
-
-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
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-
-
-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
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-
-
-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
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-
-
-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
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-
-
-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
-
-
-
-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
Oryza malabarensis
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-
-
-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
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-
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-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
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-
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-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
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-
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-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
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i.e. propanil
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?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
i.e. propanil
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-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
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-
-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
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-
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?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
i.e. propanil
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-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
i.e. propanil
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-
?
3',4'-dichloropropionanilide + H2O
3,4-dichloroaniline + propionate
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-
-
-
?
4-acetamidophenol + H2O
acetate + 4-aminophenol
i.e. Tylenol
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-
r
4-acetamidophenol + H2O
acetate + 4-aminophenol
i.e. Tylenol. The enzyme contains a revealed a conserved amidase signature region with a canonical catalytic triad
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r
N-(2-nitrophenyl)-trifluoroacetamide + H2O
2-nitroaniline + trifluoroacetic acid
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-
-
-
?
N-(2-nitrophenyl)-trifluoroacetamide + H2O
2-nitroaniline + trifluoroacetic acid
-
-
-
-
?
N-(2-nitrophenyl)acetamide + H2O
N-(2-nitrophenyl)aniline + acetate
-
-
-
-
?
N-(2-nitrophenyl)butanamide + H2O
N-(2-nitrophenyl)aniline + butyrate
-
no activity with acetylcholinesterase
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-
?
N-(2-nitrophenyl)butanamide + H2O
N-(2-nitrophenyl)aniline + butyrate
-
-
-
-
?
N-(2-nitrophenyl)hexanacetamide + H2O
N-(2-nitrophenyl)aniline + hexanoate
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no activity with acetylcholinesterase
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?
N-(2-nitrophenyl)hexanacetamide + H2O
N-(2-nitrophenyl)aniline + hexanoate
-
-
-
-
?
N-(2-nitrophenyl)pentanacetamide + H2O
N-(2-nitrophenyl)aniline + pentanoate
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-
-
-
?
N-(2-nitrophenyl)pentanacetamide + H2O
N-(2-nitrophenyl)aniline + pentanoate
-
-
-
-
?
N-(2-nitrophenyl)propanamide + H2O
N-(2-nitrophenyl)aniline + propionate
-
-
-
-
?
N-(2-nitrophenyl)propanamide + H2O
N-(2-nitrophenyl)aniline + propionate
-
-
-
-
?
N-(2-nitrophenyl)trifluoroacetamide + H2O
N-(2-nitrophenyl)aniline + trifluoroacetate
-
best substrate of acetylcholinesterase and butyrylcholinesterase
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-
?
N-(2-nitrophenyl)trifluoroacetamide + H2O
N-(2-nitrophenyl)aniline + trifluoroacetate
-
-
-
-
?
N-(3-methoxy-2-nitrophenyl)acetamide + H2O
N-(3-methoxy-2-nitrophenyl)aniline + acetate
-
no activity with acetylcholinesterase
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-
?
N-(3-methoxy-2-nitrophenyl)acetamide + H2O
N-(3-methoxy-2-nitrophenyl)aniline + acetate
-
-
-
-
?
N-(5-methoxy-2-nitrophenyl)acetamide + H2O
N-(5-methoxy-2-nitrophenyl)aniline + acetate
-
-
-
-
?
N-(5-methoxy-2-nitrophenyl)acetamide + H2O
N-(5-methoxy-2-nitrophenyl)aniline + acetate
-
-
-
-
?
o-nitroacetanilide + H2O
2-nitroaniline + acetate
-
-
-
-
?
o-nitroacetanilide + H2O
2-nitroaniline + acetate
-
-
-
-
?
o-nitroacetanilide + H2O
2-nitroaniline + acetate
-
i.e. 2-nitroacetanilide
-
-
?
o-nitroacetanilide + H2O
2-nitroaniline + acetate
-
i.e. 2-nitroacetanilide
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-
?
p-nitroacetanilide + H2O
4-nitroaniline + acetate
-
i.e. 4-nitroacetanilide
-
-
?
p-nitroacetanilide + H2O
4-nitroaniline + acetate
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i.e. 4-nitroacetanilide
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-
?
p-nitroacetanilide + H2O
p-nitroaniline + acetate
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studies on the mechanism of the reaction
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-
r
p-nitroacetanilide + H2O
p-nitroaniline + acetate
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enzymatic activity measured by absorbance spectroscopy at 382 nm
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-
?
phenacetin + H2O
acetate + 4-ethoxyaniline
i.e. N-(4-ethoxyphenyl)acetamide
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-
r
additional information
?
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induction by acetanilide, 2'-methylacetanilide, 3'-methylacetanilide, 4'-methylacetanilide
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?
additional information
?
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induction by 2',6'-dimethylacetanilide
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-
?
additional information
?
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induction by acetanilide, 2'-methylacetanilide, 3'-methylacetanilide, 4'-methylacetanilide
-
-
?
additional information
?
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induction by acetanilide, 2'-methylacetanilide, 3'-methylacetanilide, 4'-methylacetanilide
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-
?
additional information
?
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induction by 2',6'-dimethylacetanilide
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?
additional information
?
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induction by acetanilide, 2'-methylacetanilide, 3'-methylacetanilide, 4'-methylacetanilide
-
-
?
additional information
?
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induction by 2',6'-dimethylacetanilide
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-
?
additional information
?
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induction by acetanilide, 2'-methylacetanilide, 3'-methylacetanilide, 4'-methylacetanilide
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?
additional information
?
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the aryl amide activity of the acetylcholinesterase has a distinct role in embryogenesis
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-
?
additional information
?
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acetylcholinesterase, EC 3.1.1.7, exhibits aryl acylamidase activity
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-
?
additional information
?
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amino acid sequence around the reactive serine residue is Gly-Ser-Ile
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-
?
additional information
?
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serotonin-sensitive aryl acylamidase is identical with acetylcholinesterase
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?
additional information
?
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serotonin-sensitive aryl acylamidase is identical with acetylcholinesterase
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?
additional information
?
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serotonin-sensitive aryl acylamidase is identical with acetylcholinesterase
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?
additional information
?
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enzyme also has acetylcholinesterase activity
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?
additional information
?
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enzyme also has butyrylcholinesterase activity
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?
additional information
?
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enzyme also has butyrylcholinesterase activity
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?
additional information
?
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serotonin-sensitive aryl acylamidase is identical with acetylcholinesterase
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-
?
additional information
?
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enzyme also has butyrylcholinesterase activity
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?
additional information
?
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acetylcholinesterase, EC 3.1.1.7, and butyrylcholinesterase, EC 3.1.1.8, exhibit also aryl acylamidase activity
-
-
?
additional information
?
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serotonin-sensitive aryl acylamidase is identical with acetylcholinesterase
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?
additional information
?
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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
-
-
?
additional information
?
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the reaction in human erythrocytes and plasma is performed by the butyrylcholinesterase, EC 3.1.1.8, which is inactive with butyrylthiocholine, also fatty acid free human albumin has aryl acylacylamidase activity, which accounts for 10% of total human enzyme activity
-
-
?
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
-
-
?
additional information
?
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inducible by various phenylamides of the acylanilide, phenylcarbamate, and methoxysubstituted phenylurea type
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?
additional information
?
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serotonin-sensitive aryl acylamidase is identical with acetylcholinesterase
-
-
?
additional information
?
-
substrate specificity, overview. PamH is highly active on aromatic and short-chain aliphatic amides, e.g. benzamide and propionamide, moderately active on amino acid amides, and possesses weak urease activity. Of the anilides examined, only propanil is a good substrate for PamH. PamH is also able to catalyze the acyl transfer reaction to hydroxylamine for both amide and anilide substrates, including acetamide, propanil, and 4-nitroacetanilide, it shows the highest reaction rate with isobutyramide
-
-
?
additional information
?
-
the PamH enzyme exhibits amidase activity, aryl acylamidase activity (EC 3.5.1.13), and acyl transferase activity. It shows excellent activity toward the majority of the aromatic and aliphatic amides, such as acetamide, propionamide, phenylacetamide, and benzamide. The aromatic amides, with substitutions of one or two carbons in the ring by a nitrogen, have a negative influence on amidase activity, leading to low specific activity values for pyrazinamide and nicotinamide. No activity is detectable on long-chain aliphatic amide hexanoamides. Amino acid amides are also hydrolyzed by the enzyme. The enzyme possesses urease activity, but N-methyl substituted is not hydrolyzed by the enzyme. The amidase shows low activity on asparagines (9%), L-glutamine (17%), and D-glutamine (13%) corresponding to benzamide (100%). The anilide substrate range of the enzyme is very narrow and cannot hydrolyze butachlor, acetochlor, 4-nitroacetanilide, p-chloroacetanilide, or other structurally analogous compounds
-
-
?
additional information
?
-
-
serotonin-sensitive aryl acylamidase is associated with acetylcholinesterase, serotonin-insensitive aryl acylamidase is not associated with acetylcholinesterase
-
-
?
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
-
-
?