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Information on EC 3.1.1.8 - cholinesterase and Organism(s) Rattus norvegicus and UniProt Accession Q9JKC1

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EC Tree
     3 Hydrolases
         3.1 Acting on ester bonds
             3.1.1 Carboxylic-ester hydrolases
                3.1.1.8 cholinesterase
IUBMB Comments
Acts on a variety of choline esters and a few other compounds.
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This record set is specific for:
Rattus norvegicus
UNIPROT: Q9JKC1
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Word Map
The taxonomic range for the selected organisms is: Rattus norvegicus
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
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
butyrylcholinesterase
-
Acylcholine acylhydrolase
-
-
-
-
benzoylcholinesterase
-
-
-
-
butyrylcholine esterase
-
-
-
-
butyrylcholinesterase
-
-
choline esterase II (unspecific)
-
-
-
-
EQ-BCHE
-
-
-
-
esterase, butyrylcholine
-
-
-
-
esterase, choline
-
-
-
-
non-specific cholinesterase
-
-
-
-
plasmatic cholinesterase
-
-
propionylcholinesterase
-
-
-
-
pseudocholinesterase
-
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an acylcholine + H2O = choline + a carboxylate
show the reaction diagram
mechanism
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of carboxylic ester
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
acylcholine acylhydrolase
Acts on a variety of choline esters and a few other compounds.
CAS REGISTRY NUMBER
COMMENTARY hide
9001-08-5
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
butyrylcholine + H2O
choline + butyrate
show the reaction diagram
-
-
-
?
butyrylthiocholine + H2O
thiocholine + butyrate
show the reaction diagram
-
-
-
?
acetyl choline + H2O
acetate + choline
show the reaction diagram
-
enzyme also acts on acetyl choline to a lesser extent
-
?
acetyl-beta-methylcholine + H2O
acetate + beta-methylcholine
show the reaction diagram
-
poor substrate
-
-
?
acetylthiocholine + H2O
acetate + thiocholine
show the reaction diagram
-
-
-
-
?
acetylthiocholine + H2O
thiocholine + acetate
show the reaction diagram
benzoylcholine + H2O
benzoate + choline
show the reaction diagram
benzoylcholine + H2O
choline + benzoate
show the reaction diagram
butyryl choline + H2O
butyrate + choline
show the reaction diagram
-
preferred substrate
-
?
butyrylcholine + H2O
butyrate + choline
show the reaction diagram
-
-
-
-
?
butyrylthiocholine + H2O
butanoate + thiocholine
show the reaction diagram
-
-
-
-
?
butyrylthiocholine + H2O
thiocholine + butyrate
show the reaction diagram
butyrylthiocholine iodide + H2O
butyrate + thiocholine iodide
show the reaction diagram
bytyrylhiocholine + H2O
thiocholine + butyrate
show the reaction diagram
-
-
-
?
choline esters + H2O
?
show the reaction diagram
-
-
-
-
?
cocaine + H2O
?
show the reaction diagram
-
-
-
?
propionyl choline + H2O
propionate + choline
show the reaction diagram
-
preferred substrate
-
?
propionylthiocholine + H2O
thiocholine + propionate
show the reaction diagram
additional information
?
-
-
hydrolysis of benzoylcholine and its N-alkyl derivatives shows hysteretic pre-steady-state phase of induction. Hysteresis is complex and consists of lag phase superimposed on damped oscillations
-
-
?
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
butyrylcholine + H2O
choline + butyrate
show the reaction diagram
-
-
-
?
butyrylcholine + H2O
butyrate + choline
show the reaction diagram
-
-
-
-
?
butyrylthiocholine + H2O
thiocholine + butyrate
show the reaction diagram
-
-
-
-
?
choline esters + H2O
?
show the reaction diagram
-
-
-
-
?
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+/-)-N-((1-(2,3-dihydro-1H-inden-2-yl)piperidin-3-yl)methyl)-N-(2-(dimethylamino)ethyl)-2-naphthamide
inhibition of BChE in rat brain slices, low cytotoxicity, favorable in vitro pharmacokinetics, and proven penetration into the brain. The brain-to-blood plasma ratio of (+/-)-N-((1-(2,3-dihydro-1H-inden-2-yl)piperidin-3-yl)methyl)-N-(2-(dimethylamino)ethyl)-2-naphthamide is 1.47
10-N-demethyl-10-N-(10-(4-(piperidin-1-ylmethyl)-phenoxy)decan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(12-(4-(piperidin-1-ylmethyl)-phenoxy)dodecan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(2-(4-(piperidin-1-ylmethyl)phenoxy)ethan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(3-(4-(piperidin-1-ylmethyl)phenoxy)propan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(4-(1-benzylpiperidin-4-yloxy)-butan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(4-(3-(1-morpholinoethyl)phenoxy)butan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(4-(4-((diethylamino)methyl)-phenoxy)butan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(4-(4-(morpholinomethyl)phenoxy)butan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(4-(4-(piperidin-1-ylmethyl)phenoxy)butan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(4-(4-(pyrrolidine-1-carbonyl)-phenoxy)butan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(5-(4-(piperidin-1-ylmethyl)phenoxy)pentan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(6-(1-benzylpiperidin-4-yloxy)-hexan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(6-(3-(1-morpholinoethyl)phenoxy)hexan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(6-(4-((diethylamino)methyl)-phenoxy)hexan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(6-(4-(morpholinomethyl)phenoxy)hexan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(6-(4-(piperidin-1-ylmethyl)phenoxy)hexan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(6-(4-(pyrrolidine-1-carbonyl)-phenoxy)hexan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(8-(4-(piperidin-1-ylmethyl)phenoxy)octan-1-yl)-galanthamine
-
-
10-N-demethyl-10-N-(9-(4-(piperidin-1-ylmethyl)phenoxy)nonan-1-yl)-galanthamine
-
-
benzoylthiocholine
-
substrate inhibition
Echothiophate
-
enzyme spontaneously reactivates with a half-life of 4.3 h
ethopropazine hydrochloride
-
-
galanthamine
-
-
lysivane
physostigmine
-
i.e. eserine
pralidoxime
-
significally decreases organophosphate induced mortality of a LD75 dose of paraoxon
pyridostigmine
-
significally decreases organophosphate induced mortality of a LD75 dose of paraoxon
Triton X-100
additional information
-
design, synthesis and evaluation of galanthamine derivatives as acetylcholinesterase inhibitors, overview
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
rat plasma BuChE is increased when pretreated with horse BuChE
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.037 - 0.087
acetylthiocholine
0.047
Benzoylcholine
-
pH 7.4, 37°C
0.094 - 0.134
butyrylthiocholine
0.03 - 2.38
butyrylthiocholine iodide
0.112 - 0.189
propionylthiocholine
additional information
additional information
-
Km-values and kcat-values for benzoylcholine and its N-alkyl derivatives decrease as the length of the alkyl chain increases
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.005 - 23.5
acetylthiocholine
16.8
Benzoylcholine
-
pH 7.4, 37°C
49.2 - 3350
propionylthiocholine
additional information
additional information
-
Km-values and kcat-values for benzoylcholine and its N-alkyl derivatives decrease as the length of the alkyl chain increases
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
additional information
inhibition kinetics, thermodynamic analysis of binding, overview
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.093
10-N-demethyl-10-N-(10-(4-(piperidin-1-ylmethyl)-phenoxy)decan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.0012
10-N-demethyl-10-N-(12-(4-(piperidin-1-ylmethyl)-phenoxy)dodecan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.021
10-N-demethyl-10-N-(2-(4-(piperidin-1-ylmethyl)phenoxy)ethan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.024
10-N-demethyl-10-N-(3-(4-(piperidin-1-ylmethyl)phenoxy)propan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.0043
10-N-demethyl-10-N-(4-(1-benzylpiperidin-4-yloxy)-butan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.0071
10-N-demethyl-10-N-(4-(3-(1-morpholinoethyl)phenoxy)butan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.034
10-N-demethyl-10-N-(4-(4-((diethylamino)methyl)-phenoxy)butan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.0033
10-N-demethyl-10-N-(4-(4-(morpholinomethyl)phenoxy)butan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.028
10-N-demethyl-10-N-(4-(4-(piperidin-1-ylmethyl)phenoxy)butan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.0056
10-N-demethyl-10-N-(4-(4-(pyrrolidine-1-carbonyl)-phenoxy)butan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.029
10-N-demethyl-10-N-(5-(4-(piperidin-1-ylmethyl)phenoxy)pentan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.0055
10-N-demethyl-10-N-(6-(1-benzylpiperidin-4-yloxy)-hexan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.0058
10-N-demethyl-10-N-(6-(3-(1-morpholinoethyl)phenoxy)hexan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.041
10-N-demethyl-10-N-(6-(4-((diethylamino)methyl)-phenoxy)hexan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.0039
10-N-demethyl-10-N-(6-(4-(morpholinomethyl)phenoxy)hexan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.033
10-N-demethyl-10-N-(6-(4-(piperidin-1-ylmethyl)phenoxy)hexan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.0094
10-N-demethyl-10-N-(6-(4-(pyrrolidine-1-carbonyl)-phenoxy)hexan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.053
10-N-demethyl-10-N-(8-(4-(piperidin-1-ylmethyl)phenoxy)octan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.064
10-N-demethyl-10-N-(9-(4-(piperidin-1-ylmethyl)phenoxy)nonan-1-yl)-galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
0.0059
galanthamine
Rattus norvegicus
-
pH 7.4, 37°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
plasma BuChE before and after sarin inhalation exposure of untreated rats and animals pretreated with horse BuChE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
Q9JKC1_RAT
597
0
67777
TrEMBL
Mitochondrion (Reliability: 2)
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
tetramer
-
nonreducing PAGE
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
R286L
-
Km values similar to wild-type enzyme
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in CHO cells
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
hypoxanthine, at 0.01 mM reduces enzyme activity in the serum of 60-day-old rats while trolox and allopurinol, but not ascorbic acid, are able to prevent this reduction in activity
-
reductions in the activity of cholinesterase occur in acute infection by Trypanosoma evansi in rats
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
-
both pyridostigmine and pralidoxime significally decrease organophosphate induced mortality of a LD75 dose of paraoxon by inhibition of enzyme. Decrease in mortality when using both pyridostigmine and pralidoxime together is less than that achieved with their single use
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Wheeler, G.E.; Coleman, R.; Finean, J.B.
Cholinesterase activities in subcellular fractions of rat liver. Association of acetylcholinesterase with the surface membrane and other properties of the enzyme
Biochim. Biophys. Acta
255
917-930
1972
Rattus norvegicus
Manually annotated by BRENDA team
Vigny, M.; Gisiger, V.; Massoulie, J.
Nonspecific cholinesterase and acetylcholinesterase in rat tissues: molecular forms, structural and catalytic properties, and significance of the two enzymes
Proc. Natl. Acad. Sci. USA
75
2588-2592
1978
Rattus norvegicus
Manually annotated by BRENDA team
Brown, S.S.; Kalow, W.; Pilz, W.; Whittaker, M.; Woronick, C.L.
The plasma cholinesterase: a new perspective
Adv. Clin. Chem.
22
1-123
1981
Canis lupus familiaris, Equus caballus, Homo sapiens, Mus musculus, Pleuronectes platessa, Pseudomonas aeruginosa, Rattus norvegicus, Sus scrofa
Manually annotated by BRENDA team
Boeck, A.T.; Schopfer, L.M.; Lockridge, O.
DNA sequence of butyrylcholinesterase from the rat: expression of the protein and characterization of the properties of rat butyrylcholinesterase
Biochem. Pharmacol.
63
2101-2110
2002
Rattus norvegicus
Manually annotated by BRENDA team
Yildiz, O.; Bodur, E.; Cokugras, A.N.; Ozer, N.
Partial purification and characterization of soluble isoform of butyrylcholinesterase from rat intestine
Protein J.
23
143-151
2004
Rattus norvegicus
Manually annotated by BRENDA team
Dave, K.R.; Syal, A.R.; Katyare, S.S.
Tissue cholinesterases. A comparative study of their kinetic properties
Z. Naturforsch. C
55
100-108
2000
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Petroianu, G.A.; Nurulain, S.M.; Arafat, K.; Rajan, S.; Hasan, M.Y.
Effect of pyridostigmine, pralidoxime and their combination on survival and cholinesterase activity in rats exposed to the organophosphate paraoxon
Arch. Toxicol.
80
777-84
2006
Rattus norvegicus
Manually annotated by BRENDA team
Hrabovska, A.; Debouzy, J.C.; Froment, M.T.; Devinsky, F.; Paulikova, I.; Masson, P.
Rat butyrylcholinesterase-catalysed hydrolysis of N-alkyl homologues of benzoylcholine
FEBS J.
273
1185-1197
2006
Rattus norvegicus
Manually annotated by BRENDA team
Bajgar, J.; Bartosova, L.; Kuca, K.; Jun, D.; Fusek, J.
Changes of cholinesterase activities in the rat blood and brain after sarin intoxication pretreated with butyrylcholinesterase
Drug Chem. Toxicol.
30
351-359
2007
Equus caballus, Rattus norvegicus
Manually annotated by BRENDA team
Jia, P.; Sheng, R.; Zhang, J.; Fang, L.; He, Q.; Yang, B.; Hu, Y.
Design, synthesis and evaluation of galanthamine derivatives as acetylcholinesterase inhibitors
Eur. J. Med. Chem.
44
772-784
2008
Rattus norvegicus
Manually annotated by BRENDA team
Wolkmer, P.; Lopes, S.T.; Franciscato, C.; da Silva, A.S.; Traesel, C.K.; Siqueira, L.C.; Pereira, M.E.; Monteiro, S.G.; Mazzanti, C.M.
Trypanosoma evansi: cholinesterase activity in acutely infected Wistar rats
Exp. Parasitol.
125
251-255
2010
Rattus norvegicus
Manually annotated by BRENDA team
Wamser, M.N.; Leite, E.F.; Ferreira, V.V.; Delwing-de Lima, D.; da Cruz, J.G.; Wyse, A.T.; Delwing-Dal Magro, D.
Effect of hypoxanthine, antioxidants and allopurinol on cholinesterase activities in rats
J. Neural Transm.
120
1359-1367
2013
Rattus norvegicus
Manually annotated by BRENDA team
Kosak, U.; Brus, B.; Knez, D.; Zakelj, S.; Trontelj, J.; Pislar, A.; Sink, R.; Jukic, M.; Zivin, M.; Podkowa, A.; Nachon, F.; Brazzolotto, X.; Stojan, J.; Kos, J.; Coquelle, N.; Salat, K.; Colletier, J.P.; Gobec, S.
The magic of crystal structure-based inhibitor optimization development of a butyrylcholinesterase inhibitor with picomolar affinity and in vivo activity
J. Med. Chem.
61
119-139
2018
Homo sapiens (P06276), Homo sapiens, Rattus norvegicus (Q9JKC1)
Manually annotated by BRENDA team