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butyrylcholine + H2O
choline + butyrate
-
-
-
?
butyrylthiocholine + H2O
thiocholine + butyrate
-
-
-
?
acetyl choline + H2O
acetate + choline
-
enzyme also acts on acetyl choline to a lesser extent
-
?
acetyl-beta-methylcholine + H2O
acetate + beta-methylcholine
-
poor substrate
-
-
?
acetylthiocholine + H2O
acetate + thiocholine
-
-
-
-
?
acetylthiocholine + H2O
thiocholine + acetate
benzoylcholine + H2O
benzoate + choline
benzoylcholine + H2O
choline + benzoate
butyryl choline + H2O
butyrate + choline
-
preferred substrate
-
?
butyrylcholine + H2O
butyrate + choline
-
-
-
-
?
butyrylthiocholine + H2O
butanoate + thiocholine
-
-
-
-
?
butyrylthiocholine + H2O
thiocholine + butyrate
butyrylthiocholine iodide + H2O
butyrate + thiocholine iodide
bytyrylhiocholine + H2O
thiocholine + butyrate
-
-
-
?
choline esters + H2O
?
-
-
-
-
?
propionyl choline + H2O
propionate + choline
-
preferred substrate
-
?
propionylthiocholine + H2O
thiocholine + propionate
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
-
-
?
acetylthiocholine + H2O
thiocholine + acetate
-
-
-
?
acetylthiocholine + H2O
thiocholine + acetate
-
increasing activity with substrates in the following order: acetylthiocholine, propionylthiocholine, butyrylthiocholine
-
?
benzoylcholine + H2O
benzoate + choline
-
-
-
-
?
benzoylcholine + H2O
benzoate + choline
-
most specific substrate
-
-
?
benzoylcholine + H2O
choline + benzoate
-
-
-
?
benzoylcholine + H2O
choline + benzoate
-
-
-
?
benzoylcholine + H2O
choline + benzoate
-
-
-
-
?
butyrylthiocholine + H2O
thiocholine + butyrate
-
-
-
-
?
butyrylthiocholine + H2O
thiocholine + butyrate
-
increasing activity with substrates in the following order: acetylthiocholine, propionylthiocholine, butyrylthiocholine
-
?
butyrylthiocholine iodide + H2O
butyrate + thiocholine iodide
-
-
-
-
?
butyrylthiocholine iodide + H2O
butyrate + thiocholine iodide
-
detection with 5,5'-dithio-bis-2-nitrobenzoic acid, i.e. DTNB
-
-
?
propionylthiocholine + H2O
thiocholine + propionate
-
best substrate
-
?
propionylthiocholine + H2O
thiocholine + propionate
-
increasing activity with substrates in the following order: acetylthiocholine, propionylthiocholine, butyrylthiocholine
-
?
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(+/-)-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
-
-
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
additional information
-
design, synthesis and evaluation of galanthamine derivatives as acetylcholinesterase inhibitors, overview
-
lysivane
-
0.1 mM, complete inhibition
Triton X-100
-
competitive inhibition
Triton X-100
-
inhibition above 0.01 mM
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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
-
0.037
acetylthiocholine
-
pH 7.0, 25°C, R286L mutant
0.06
acetylthiocholine
-
pH 7.4, 37°C
0.061
acetylthiocholine
-
pH 7.0, 25°C, wild-type
0.087
acetylthiocholine
-
pH 7.4, 37°C
0.094
butyrylthiocholine
-
pH 7.0, 25°C, R286L mutant
0.134
butyrylthiocholine
-
pH 7.0, 25°C, wild-type
0.03
butyrylthiocholine iodide
-
pH 8, 37°C, liver, soluble form, component I
0.068
butyrylthiocholine iodide
-
pH 8, 37°C, liver, membrane-bound form, component I
0.18
butyrylthiocholine iodide
-
pH 8, 37°C, heart, soluble form, component I
0.24
butyrylthiocholine iodide
-
pH 8, 37°C, heart, membrane-bound form, component I
0.53
butyrylthiocholine iodide
-
pH 8, 37°C, erythrocyte, membrane-bound form, component II
0.86
butyrylthiocholine iodide
-
pH 8, 37°C, liver, membrane-bound form, component II
0.92
butyrylthiocholine iodide
-
pH 8, 37°C, heart, membrane-bound form, component II
1.46
butyrylthiocholine iodide
-
pH 8, 37°C, liver, soluble form, component II
1.49
butyrylthiocholine iodide
-
pH 8, 37°C, heart, soluble form, component II
2.38
butyrylthiocholine iodide
-
pH 8, 37°C, erythrocyte, membrane-bound form, component III
0.112
propionylthiocholine
-
pH 7.0, 25°C, R286L mutant
0.115
propionylthiocholine
-
pH 7.4, 37°C
0.189
propionylthiocholine
-
pH 7.0, 25°C, wild-type
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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
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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
brenda
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
brenda
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
brenda
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
brenda
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
brenda
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
brenda
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
brenda
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
brenda
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
brenda
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
brenda
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
brenda
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
brenda
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)
brenda