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Information on EC 3.1.1.8 - cholinesterase and Organism(s) Homo sapiens
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3.1.1.8 cholinesteraseIUBMB Comments
Acts on a variety of choline esters and a few other compounds.
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Word Map
- 3.1.1.8
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ache
- alzheimer
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cholinergic
- acetylcholine
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organophosphate
- nerve
- dementia
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pesticide
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poison
- donepezil
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organophosphorus
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insecticide
- erythrocyte
- physostigmine
- deficit
- atropine
- neuromuscular
- carbamate
- rivastigmine
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muscarinic
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intoxication
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neurotoxicity
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amyloid
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nicotinic
- galantamine
- tacrine
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neuroprotective
- oxime
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placebo
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innervation
- carboxylesterase
- chlorpyrifos
- soman
- memantine
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caregiver
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mini-mental
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antipsychotic
- esterases
- parathion
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placebo-controlled
- myasthenia
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anticholinergic
- paraoxon
- dfp
- scopolamine
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antidote
- gravis
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subscale
- delirium
- medicine
- pharmacology
- environmental protection
- drug development
- diagnostics
- analysis
- hallucinations
- biotechnology
The taxonomic range for the selected organisms is: Homo sapiens
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Synonyms
cholinesterase, butyrylcholinesterase, buche, plasma cholinesterase, serum cholinesterase, pseudocholinesterase, choline esterase, hubche, hbche, plasma esterase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Acylcholine acylhydrolase
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BChE
benzoylcholinesterase
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BuChE
butyrylcholine esterase
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butyrylcholinesterase
choline esterase II (unspecific)
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EQ-BCHE
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esterase, butyrylcholine
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esterase, choline
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hBChE
non-specific cholinesterase
propionylcholinesterase
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BChE
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BChE
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BuChE
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butyrylcholinesterase
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35207, 94449, 94450, 94453, 94461, 667928, 678430, 678453, 678541, 678608, 679287, 682017, 682120, 691103, 691741, 691744, 691745, 691746, 691747, 691748, 691853, 691944, 692330, 693395, 693553, 693565, 694365, 694383, 694563, 694972, 695282, 695283, 702617, 702676, 703470, 706041, 706828, 713701, 714416, 714702, 716278, 728949, 729273, 729366, 729566, 729571, 750298, 750901
butyrylcholinesterase
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non-specific cholinesterase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
an acylcholine + H2O = choline + a carboxylate
enzyme is able to stabilize covalent tetrahedral intermediate adduct with substrate
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an acylcholine + H2O = choline + a carboxylate
molecular dynamics simulation in aqueous solution, nucleophilic S198 and the various binding subsites in the catalytic cavitiy are readily accessible from the exterior of the protein, the catalytic triad E325/H438/S198 is stablized by presence of a sodium ion
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an acylcholine + H2O = choline + a carboxylate
the catalytic residue is Ser198
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of carboxylic ester
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SYSTEMATIC NAME
IUBMB Comments
acylcholine acylhydrolase
Acts on a variety of choline esters and a few other compounds.
CAS REGISTRY NUMBER
COMMENTARY
9001-08-5
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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
2,2,2-trifluoro-N-(2-nitrophenyl)acetamide + H2O
2-nitroaniline + trifluoroacetate
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a neutral amide
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?
3-(acetamido) N,N,N-trimethylanilinium + H2O
3-amino-N,N,N-trimethylanilinium + acetate
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a positively charged amide, hydrolysis by the wild-type enzyme and the mutant D70G shows a long transient phase preceeding the steady state, hysteretic burst induction phase, overview
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?
acetylthiocholine + H2O
?
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detection with 5,5-dithiobis(2-nitrobenzoic acid)
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?
adipyldicholine + H2O
adipic acid + choline
lower activity, monitoring the dicholine substrates, the monocholine intermediates, the dicarboxylic acid and choline products by mass spectrometry,
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?
BChE-FP + H2O
?
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structure-based design and application of a fluorogenic molecular probe, BChE-FP, specific to butyrylcholinesterase (BChE). This compound is rationally designed by mimicking the native substrate and optimized stepwise by manipulating the steric feature and the reactivity of the designed probe targeting the structural difference of the active pockets of BChE and acetylcholinesterase (AChE). The refined probe, BChE-FP, exhibits high specificity toward BChE compared to AChE, producing about 275fold greater fluorescence enhancement upon the catalysis by BChE, molecular docking simulation, overview. The proximity of Ser198 to the carbonyl group of BChE-FP is about 4.3 A in the BChE active site, whereas the proximity of Ser203 to the carbonyl group of BChE-FP is about 7.4 A in the AChE active site. The binding affinity of BChE-FP with BChE is B100fold greater than that of acetylthiocholine, while the catalytic constant for BChE-FP is 190fold lower than that of acetylthiocholine
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?
butyrylthiocholine iodide + H2O
butyrate + thiocholine iodide
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detection with 5,5'-dithio-bis-2-nitrobenzoic acid, i.e. DTNB
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?
ethyl ([2-[bis(propan-2-yl)amino]ethyl]-sulfanyl)(methyl)phosphinate + H2O
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substrate for mutant enzyme G117H
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?
N-methyl-(7-dimethylcarbamoxy)quinolinium iodide + H2O
?
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atypical and usual enzyme
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?
o-nitrophenylbutyrate + H2O
o-nitrophenol + butanoate
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atypical and usual enzyme
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?
sebacyldicholine + H2O
sebacic acid + choline
high activity, monitoring the dicholine substrates, the monocholine intermediates, the dicarboxylic acid and choline products by mass spectrometry, sebacyldicholine is hydrolyzed at both choline ester sites, though hydrolysis of dicholine is faster than hydrolysis of monocholine, overview
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?
(-)-cocaine + H2O
?
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unique role of the oxyanion hole G116/G117/A199 in hydrolysis of cocaine, molecular dynamics simulation
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?
acetylthiocholine + H2O
acetate + thiocholine
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?
acetylthiocholine + H2O
acetate + thiocholine
detection using 5,5'-dithiobis(2-nitrobenzoic acid)
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?
acetylthiocholine + H2O
thiocholine + acetate
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100fold lower binding activity compared to butyrylthiocholine
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?
benzoylcholine + H2O
choline + benzoate
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rate-limiting step for hydrolysis is deacylation, k3
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?
benzoylthiocholine + H2O
thiocholine + benzoate
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rate-limiting step for hydrolysis is acylation, k2
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?
butyrylthiocholine + H2O
butyrate + thiocholine
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?
butyrylthiocholine + H2O
butyrate + thiocholine
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BuChE activity is decreased in Alzehimer's disease patients compared to healthy persons, overview
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?
butyrylthiocholine + H2O
butyrate + thiocholine
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detection by 5,5-dithiobis(2-nitrobenzoic acid)
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?
butyrylthiocholine + H2O
butyrate + thiocholine
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detection using 5,5'-dithiobis(2-nitrobenzoic acid)
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?
butyrylthiocholine + H2O
butyrate + thiocholine
detection using 5,5'-dithiobis(2-nitrobenzoic acid)
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?
butyrylthiocholine + H2O
thiocholine + butyrate
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?
butyrylthiocholine + H2O
thiocholine + butyrate
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BuChE catalyses the hydrolysis of numerous endogenous substances, including choline esters and the growth hormone secretagogue, octanoyl ghrelin and has an important role in Alzheimerâs disease
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?
butyrylthiocholine + H2O
thiocholine + butyrate
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the enzyme might be involved in slowing of neurodegeneration in Alzheimerâs and Parkinsonâs diseases, overview
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?
butyrylthiocholine + H2O
thiocholine + butyrate
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substrate as butyrylthiocholine iodide
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?
butyrylthiocholine + H2O
thiocholine + butyrate
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best enzyme for the wild type enzyme
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?
butyrylthiocholine + H2O
thiocholine + butyrate
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histochemic activity detection
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?
butyrylthiocholine + H2O
thiocholine + butyrate
substrate is butyrylthiocholine iodide, activity detection using 5,5'-dithio-bis(2-nitrobenzoic acid) colorimetric assay and measurement of the absorbance at 412 nm
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?
propionylthiocholine + H2O
?
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detection by 5,5-dithiobis(2-nitrobenzoic acid)
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?
additional information
?
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atypical and usual enzymes differ only in the structure of their anionic site
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?
additional information
?
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limited alpha-chymotrypsin digestion of purified enzyme exhibits cholinesterase, acryl acylamidase, and peptidase activities
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?
additional information
?
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human atypical butyrylcholinesterase is a variant with an aspartic acid to glycine substitution at position 70
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?
additional information
?
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butyrylcholine is not a physiological substrate, enzyme may replace acetylcholine esterase in hydrolysing brain acetylcholine in patients with advanced stages of Alzheimer's disease
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?
additional information
?
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causes a concentration-dependent enhancement of the catalytic activity of trypsin, may assume a regulatory role by interacting with other proteins
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?
additional information
?
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the oxoanion hole of enzyme can lower the energy barrier for the acetylcholine hydrolysis significantly more than that for cocaine hydrolysis
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?
additional information
?
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the oxoanion hole of enzyme can lower the energy barrier for the acetylcholine hydrolysis significantly more than that for cocaine hydrolysis
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?
additional information
?
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calcium-activated butyrylcholinesterase as a major protective mechanism against suicide inhibition of acetylcholinesterase by organophosphates in this non-neuronal tissue
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?
additional information
?
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the enzyme is assessed as a marker for liver pathologies, patients with diminished BChE activity do not have increased BChE aryl acylamidase activity, but the overall aryl acylamidase activity is increased, overview
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?
additional information
?
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BChE also shows aryl acylamidase activity, i.e. AAA activity, the rate-determining step of which is the acylation, overview
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?
additional information
?
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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
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?
additional information
?
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BChE tetramers from human plasma are associated with proline-rich peptides derived froma cytoplasmic protein, lamellipodin or RAPH1. BChE does exert a toxic effect on cultured neurons
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?
additional information
?
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butyrylcholinesterase is important in human cocaine metabolism despite its limited ability to hydrolyze this drug, it is a major contributor to cocaine metabolism and detoxification
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?
additional information
?
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hBChE is primarily involved in neuronal transmission and is a potential bioscavenger of toxic organophosphates to protect acetylcholinesterase
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