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Information on EC 3.1.1.7 - acetylcholinesterase and Organism(s) Homo sapiens

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EC Tree
     3 Hydrolases
         3.1 Acting on ester bonds
             3.1.1 Carboxylic-ester hydrolases
                3.1.1.7 acetylcholinesterase
IUBMB Comments
Acts on a variety of acetic esters; also catalyses transacetylations.
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Homo sapiens
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Word Map
The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
ache, acetylcholinesterase, acetylcholine esterase, acetyl cholinesterase, hache, eeache, ache1, huache, tcache, membrane-bound acetylcholinesterase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
AcCholE
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acetyl beta-methylcholinesterase
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acetylcholine esterase
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acetylcholine hydrolase
acetylcholinesterase
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acetylthiocholinesterase
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choline esterase I
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cholinesterase
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esterase, acetyl choline
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membrane-bound acetylcholinesterase
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true cholinesterase
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additional information
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the enzyme belongs to the superfamily of alpha/beta-hydrolase fold proteins
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of carboxylic ester
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transacetylation
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PATHWAY SOURCE
PATHWAYS
SYSTEMATIC NAME
IUBMB Comments
acetylcholine acetylhydrolase
Acts on a variety of acetic esters; also catalyses transacetylations.
CAS REGISTRY NUMBER
COMMENTARY hide
9000-81-1
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,1-dimethyl-4-acetylthiomethylpiperidinium + H2O
?
show the reaction diagram
i.e. MATP+, paper spray mass spectrometry is used to monitor the activity of acetylcholinesterase, both in-solution and on modified hydrophobic paper surface. Hydrophobic paper surfaces are prepared using vaporized trichloro(3,3,3-trifluoropropyl)silane. In both approaches, mixtures of diluted human whole blood with and without inhibitor ethyl ((2-[bis(propan-2-yl)amino]ethyl)sulfanyl)(methyl)phosphonate (VX) are mixed with a non-endogenous AChE specific substrate, 1,1-dimethyl-4-acetylthiomethylpiperidinium (MATP+). Formation of the cleaved MATP+ product is monitored over time and compared to MATP+ to determine relative AChE activity. This on-substrate assay is effective at determining AChE activity and identifying the toxicant, while determination of AChE activity in-solution proceeds at a slower rate. Method evaluation, overview
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1-naphthyl acetate + H2O
1-naphthol + acetate
show the reaction diagram
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a chromogenic substrate for detection of erythrocyte acetylcholinesterase activity
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?
2,6-dichloro-3'-methylindophenylacetate + H2O
2,6-dichloro-3'-methylindophenol + acetate
show the reaction diagram
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weak substrate
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?
2,6-dichlorophenolindophenol acetate + H2O
2,6-dichlorophenolindophenol + acetate
show the reaction diagram
2,6-dichlorophenolindophenol acetate computational molecular docking study using the enzyme's crystal structure, PDB ID 4YE7
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?
2,6-dichlorophenolindophenylacetate + H2O
2,6-dichlorophenolindophenol + acetate
show the reaction diagram
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?
2-methoxyacetylthiocholine + H2O
thiocholine + 2-methoxyacetate
show the reaction diagram
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recombinant enzyme shows about 12% activity compared to acetylthiocholine
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?
3',5'-dichloro-2'-methylindophenylacetate + H2O
3',5'-dichloro-2'-methylindophenol + acetate
show the reaction diagram
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weak substrate
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?
3',5'-dichlorophenolindophenylacetate + H2O
3',5'-dichlorophenolindophenol + acetate
show the reaction diagram
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weak substrate
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?
3-(acetamido)-N,N,N-trimethylanilinium + H2O
?
show the reaction diagram
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slow hydrolysis
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?
3-(acetamido)-N,N,N-trimethylanilinum + H2O
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show the reaction diagram
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ATMA
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?
3-methylbutyrylthiocholine + H2O
thiocholine + 3-methylbutyrate
show the reaction diagram
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recombinant enzyme shows about 1% activity compared to acetylthiocholine
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?
6-monoacetylmorphine + H2O
morphine + acetate
show the reaction diagram
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?
acetyl-beta-methylcholine + H2O
methylcholine + acetate
show the reaction diagram
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?
acetyl-beta-methylthiocholine + H2O
beta-methylthiocholine + acetate
show the reaction diagram
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?
acetyl-homo-thiocholine + H2O
?
show the reaction diagram
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recombinant enzyme shows less than 10% activity compared to acetylthiocholine
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?
acetylcholine + H2O
acetate + choline
show the reaction diagram
acetylcholine + H2O
choline + acetate
show the reaction diagram
acetylthiocholine + H2O
acetate + thiocholine
show the reaction diagram
acetylthiocholine + H2O
thiocholine + acetate
show the reaction diagram
acetylthiocholine chloride + H2O
acetate + thiocholine chloride
show the reaction diagram
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?
acetylthiocholine iodide + H2O
acetate + thiocholine iodide
show the reaction diagram
acetylthiocholine iodide + H2O
thiocholine + acetate
show the reaction diagram
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?
acetylthiocholine iodide + H2O
thiocholine iodide + acetate
show the reaction diagram
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?
alpha-naphthyl acetate + H2O
alpha-naphthol + acetate
show the reaction diagram
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?
benzoylthiocholine + H2O
thiocholine + benzoate
show the reaction diagram
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recombinant enzyme shows about 1% activity compared to acetylthiocholine
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?
butyrylthiocholine + H2O
thiocholine + butyrate
show the reaction diagram
carbachol + H2O
?
show the reaction diagram
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slow hydrolysis
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?
cyclopentylcarbonylthiocholine + H2O
thiocholine + cyclopentanecarboxylate
show the reaction diagram
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recombinant enzyme shows about 4% activity compared to acetylthiocholine
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?
cyclopropylcarbonylthiocholine + H2O
thiocholine + cyclopropanecarboxylate
show the reaction diagram
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recombinant enzyme shows about 4% activity compared to acetylthiocholine
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?
diisopropyl phosphofluoridate + H2O
?
show the reaction diagram
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mutant G117H, no activity with the wild-type enzyme
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echothiophate + H2O
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show the reaction diagram
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mutant G117H, no activity with the wild-type enzyme
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heroin + H2O
6-monoacetylmorphine + acetate
show the reaction diagram
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?
hexanoylthiocholine + H2O
thiocholine + hexanoate
show the reaction diagram
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recombinant enzyme shows about 6% activity compared to acetylthiocholine
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?
indophenylacetate + H2O
indophenol + acetate
show the reaction diagram
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isobutyrylthiocholine + H2O
thiocholine + isobutyrate
show the reaction diagram
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recombinant enzyme shows about 2% activity compared to acetylthiocholine
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?
paraoxon + H2O
diethylphosphate + 4-nitrophenol
show the reaction diagram
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mutant G117H, no activity with the wild-type enzyme
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?
pentanoylthiocholine + H2O
thiocholine + pentanoate
show the reaction diagram
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recombinant enzyme shows about 5% activity compared to acetylthiocholine
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phenylacetylthiocholine + H2O
thiocholine + phenylacetate
show the reaction diagram
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recombinant enzyme shows about 7% activity compared to acetylthiocholine
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?
pivaloylthiocholine + H2O
thiocholine + pivalate
show the reaction diagram
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recombinant enzyme shows about 5% activity compared to acetylthiocholine
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?
propionylthiocholine + H2O
thiocholine + propionate
show the reaction diagram
S-acetylthiocholine + H2O
acetate + thiocholine
show the reaction diagram
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detection with 5,5'-dithio-bis-2-nitrobenzoic acid, i.e. DTNB
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?
S-acetylthiocholine iodide + H2O
acetate + thiocholine iodide
show the reaction diagram
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detection with 5,5'-dithio-bis-2-nitrobenzoic acid, i.e. DTNB
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?
additional information
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
acetylcholine + H2O
acetate + choline
show the reaction diagram
acetylcholine + H2O
choline + acetate
show the reaction diagram
acetylthiocholine + H2O
acetate + thiocholine
show the reaction diagram
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?
acetylthiocholine + H2O
thiocholine + acetate
show the reaction diagram
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additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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AchE is not affected by Ca2+
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-haemanthamine
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(+)-tabun
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(-)-huperzine A
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(-)-tabun
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(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-5-nitro-N'-[(R)-1-phenylethyl]isophthalamide
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(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-5-[methyl(methylsulfonyl)-amino]-N'-[(R)-1-(4-fluorophenyl)ethyl]isophthalamide
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(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-5-[methyl(methylsulfonyl)amino]-N-[(R)-1-phenylethyl]isophthalamide
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shows inhibitory effects on beta amyloid production of amyloid precursor protein-transfected HEK293 cells and mild protective effect against hydrogen peroxide-induced cell injury
(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-N',N'-dipropyl-5-nitroisophthalamide
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(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-N',N'-dipropyl-5-[methyl(methylsulfonyl)amino]isophthalamide
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(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-N',N'-dipropylisophthalamide
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(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-N'-[(R)-1-(4-fluorophenyl)ethyl]-5-nitroisophthalamide
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(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-N'-[(R)-1-(4-fluorophenyl)ethyl]-isophthalamide
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(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-N'-[(R)-1-phenylethyl]isophthalamide
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(3,4-dimethoxyphenyl)-(4-([(2-dimethylaminoethyl)-methylamino]methyl)phenyl)-methanone
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(3,4-dimethoxyphenyl)-(4-([(2-methoxybenzyl)methylamino]methyl)phenyl)-methanone
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(3,4-dimethoxyphenyl)-(4-([methyl-(3-methylbenzyl)amino]methyl)phenyl)methanone
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(3,4-dimethoxyphenyl)-(4-([methyl-(3-nitrobenzyl)amino]methyl)phenyl)methanone
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(3,4-dimethoxyphenyl)-(4-morpholin-4-ylmethylphenyl)methanone
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(3,4-dimethoxyphenyl)-(4-[(methylprop-2-ynylamino)-methyl]phenyl)methanone
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(3,4-dimethoxyphenyl)-{4-[(ethylpropylamino)methyl]phenyl}methanone
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(3aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo(2,3-b)indol-5-yl (2-methylphenyl)carbamate
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50% inhibition at 10 nM
(3aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo(2,3-b)indol-5-yl (4-isopropylphenyl)carbamate
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50% inhibition at 760 nM
(3aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo(2,3-b)indol-5-yl ethylcarbamate
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50% inhibition at 94 nM
(3aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo(2,3-b)indol-5-yl methylcarbamate