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Literature summary for 3.1.1.7 extracted from

  • Lalut, J.; Santoni, G.; Karila, D.; Lecoutey, C.; Davis, A.; Nachon, F.; Silman, I.; Sussman, J.; Weik, M.; Maurice, T.; Dallemagne, P.; Rochais, C.
    Novel multitarget-directed ligands targeting acetylcholinesterase and sigma1 receptors as lead compounds for treatment of Alzheimers disease synthesis, evaluation, and structural characterization of their complexes with acetylcholinesterase (2018), Eur. J. Med. Chem., 162, 234-248 .
    View publication on PubMed
Search for more literature for 3.1.1.7

Inhibitors

Inhibitors Comment Organism Structure
1-(1-benzyl-7-chloro-4-methoxy-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
-
 Homo sapiens
1-(1-benzyl-7-chloro-4-methoxy-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
-
 Tetronarce californica
1-(1-benzylindol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
-
 Homo sapiens
1-(1-benzylindol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
-
 Tetronarce californica
1-(4-amino-3-chloro-5-iodo-phenyl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
-
 Homo sapiens
1-(4-amino-3-iodo-phenyl)-3-(1-benzyl-4-piperidyl)propan-1-one
-
 Homo sapiens
1-(4-amino-3-iodo-phenyl)-3-(1-butyl-4-piperidyl)propan-1-one
-
 Homo sapiens
1-(4-amino-3-iodo-phenyl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
-
 Homo sapiens
1-(4-amino-3-iodo-phenyl)-3-[1-(cyclopentylmethyl)-4-piperidyl]propan-1-one
-
 Homo sapiens
1-(4-amino-5-chloro-2-methoxyphenyl)-3-(1-butyl-4-piperidinyl)-1-propanone i.e. RS67333 Homo sapiens
1-(4-amino-5-chloro-2-methoxyphenyl)-3-(1-butyl-4-piperidinyl)-1-propanone i.e. RS67333 Tetronarce californica
1-(4-amino-5-chloro-3-iodo-2-methoxy-phenyl)-3-(1-benzyl-4-piperidyl)propan-1-one
-
 Homo sapiens
1-(4-amino-5-chloro-3-iodo-2-methoxy-phenyl)-3-[1-(cyclohexylmethyl)-4-piperidyl] propan-1-one
-
 Homo sapiens
1-(7-chloro-1H-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
-
 Homo sapiens
1-(7-chloro-1H-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
-
 Tetronarce californica
1-(7-chloro-4-methoxy-1-methyl-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
-
 Homo sapiens
1-(7-chloro-4-methoxy-1-methyl-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
-
 Tetronarce californica
1-(7-chloro-4-methoxy-1H-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
-
 Homo sapiens
1-(7-chloro-4-methoxy-1H-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
-
 Tetronarce californica
1-[1-(benzenesulfonyl)-7-chloro-4-methoxy-indol-5-yl]-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
-
 Homo sapiens
1-[1-(benzenesulfonyl)-7-chloro-4-methoxy-indol-5-yl]-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
-
 Tetronarce californica
1-[7-chloro-2-(trimethylsilyl)-1H-inden-5-yl]-3-[1-(cyclohexylmethyl)piperidin-4-yl]propan-1-one
-
 Homo sapiens
1-[7-chloro-4-methoxy-2-(trimethylsilyl)-1H-inden-5-yl]-3-[1-(cyclohexylmethyl)piperidin-4-yl]propan-1-one
-
 Homo sapiens
3-(1-benzyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one
-
 Homo sapiens
3-(1-benzyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one
-
 Tetronarce californica
3-(1-benzyl-4-piperidyl)-1-(7-chloro-4-methoxy-1H-indol-5-yl)propan-1-one
-
 Homo sapiens
3-(1-benzyl-4-piperidyl)-1-(7-chloro-4-methoxy-1H-indol-5-yl)propan-1-one
-
 Tetronarce californica
3-(1-benzyl-4-piperidyl)-1-(7-chloro-4-methoxy-2-trimethylsilyl-1H-indol-5-yl)propan-1-one
-
 Homo sapiens
3-(1-benzyl-4-piperidyl)-1-(7-chloro-4-methoxy-2-trimethylsilyl-1H-indol-5-yl)propan-1-one
-
 Tetronarce californica
3-(1-butyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one
-
 Homo sapiens
3-(1-butyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one
-
 Tetronarce californica
3-(1-butylpiperidin-4-yl)-1-[2-(trimethylsilyl)-1H-inden-5-yl]propan-1-one
-
 Homo sapiens
3-(1-phenoxypiperidin-4-yl)-1-[2-(trimethylsilyl)-1H-inden-5-yl]propan-1-one
-
 Homo sapiens
3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one
-
 Homo sapiens
3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one
-
 Tetronarce californica
3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(4-methoxy-1Hindol-5-yl)propan-1-one
-
 Homo sapiens
3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(4-methoxy-1Hindol-5-yl)propan-1-one
-
 Tetronarce californica
3-[1-(cyclohexylmethyl)piperidin-4-yl]-1-[2-(trimethylsilyl)-1H-inden-5-yl]propan-1-one
-
 Homo sapiens
3-[1-(cyclopentylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one
-
 Homo sapiens
3-[1-(cyclopentylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one
-
 Tetronarce californica
3-[1-(cyclopentylmethyl)piperidin-4-yl]-1-[2-(trimethylsilyl)-1H-inden-5-yl]propan-1-one
-
 Homo sapiens
4-amino-3-chloro-5-iodobenzoic acid
-
 Homo sapiens
4-amino-3-iodobenzoic acid
-
 Homo sapiens
4-amino-5-chloro-3-iodo-2-methoxybenzoic acid
-
 Homo sapiens
4-methoxy-1H-indole-5-carboxylic acid
-
 Homo sapiens
donecopride synthesized from donepezil and RS67333, shows a double mechanism of action and good bioavailability, docking into the active-site gorge of hAChE. Replacement of the benzene ring of the compound by an indole residue should increase the interaction of the ligand with the peripheral anionic site (PAS), thus resulting in increased inhibition of beta-amyloid aggregation Homo sapiens
donecopride synthesized from donepezil and RS67333, shows a double mechanism of action and good bioavailability. Replacement of the benzene ring of the compound by an indole residue should increase the interaction of the ligand with the peripheral anionic site (PAS), thus resulting in increased inhibition of beta-amyloid aggregation Tetronarce californica
donepezil
-
 Homo sapiens
donepezil
-
 Tetronarce californica
ethyl 3-(4-amino-3-chloro-5-iodo-phenyl)-3-oxo-propanoate
-
 Homo sapiens
ethyl 3-(4-amino-3-iodo-phenyl)-3-oxo-propanoate
-
 Homo sapiens
ethyl 3-(4-amino-5-chloro-3-iodo-2-methoxy-phenyl)-3-oxo-propanoate
-
 Homo sapiens
ethyl 3-(4-methoxy-1H-indol-5-yl)-3-oxo-propanoate
-
 Homo sapiens
galantamine
-
 Homo sapiens
galantamine
-
 Tetronarce californica
methyl 4-amino-5-chloro-3-iodo-2-methoxybenzoate
-
 Homo sapiens
methyl 4-methoxy-1H-indole-5-carboxylate
-
 Homo sapiens
methyl 7-chloro-4-methoxy-1H-indole-5-carboxylate
-
 Homo sapiens
additional information development, synthesis, and evaluation of a series of indole derivatives possessing in vitro inhibitory activities against AChE, structure-function analysis, overview Homo sapiens
additional information development, synthesis, and evaluation of a series of indole derivatives possessing in vitro inhibitory activities against AChE, structure-function analysis, overview. Crystal structures of complexes of the most promising compounds with Torpedo californica AChE are solved in order to further understand their mode of inhibition Tetronarce californica
rivastigmine
-
 Homo sapiens
rivastigmine
-
 Tetronarce californica
tert-butyl 4-[3-(4-amino-3-chloro-5-iodo-phenyl)-3-oxopropyl]piperidine-1-carboxylate
-
 Homo sapiens
tert-butyl 4-[3-(4-amino-3-iodo-phenyl)-3-oxo-propyl]piperidine-1-carboxylate
-
 Homo sapiens
tert-butyl 4-[3-(4-amino-5-chloro-3-iodo-2-methoxyphenyl)-3-oxo-propyl]piperidine-1-carboxylate
-
 Homo sapiens
tert-butyl 4-[3-(4-methoxy-1H-indol-5-yl)-3-oxo-propyl]piperidine-1-carboxylate
-
 Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
acetylcholine + H2O Tetronarce californica
-
 choline + acetate
-
 ?
acetylcholine + H2O Homo sapiens
-
 choline + acetate
-
 ?

Organism

Organism UniProt Comment Textmining
Homo sapiens P22303
-
-
Tetronarce californica P04058 i.e. Tetronarce californica
-

Source Tissue

Source Tissue Comment Organism Textmining
erythrocyte
-
 Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
acetylcholine + H2O
-
 Tetronarce californica choline + acetate
-
 ?
acetylcholine + H2O
-
 Homo sapiens choline + acetate
-
 ?
acetylthiocholine + H2O substrate is acetylthiocholine iodide, activity detection using 5,5'-dithio-bis(2-nitrobenzoic acid) colorimetric assay and measurement of the absorbance at 412 nm Tetronarce californica thiocholine + acetate
-
 ?
acetylthiocholine + H2O substrate is acetylthiocholine iodide, activity detection using 5,5'-dithio-bis(2-nitrobenzoic acid) colorimetric assay and measurement of the absorbance at 412 nm Homo sapiens thiocholine + acetate
-
 ?

Synonyms

Synonyms Comment Organism
AChE
-
 Tetronarce californica
AChE
-
 Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Tetronarce californica
25
-
 assay at Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8
-
 assay at Tetronarce californica
8
-
 assay at Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0000133
-
 pH 8.0, 25°C Tetronarce californica 3-(1-benzyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one
0.0000133
-
 pH 8.0, 25°C Homo sapiens 3-(1-benzyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one
0.000016
-
 pH 8.0, 25°C Homo sapiens donecopride
0.0000204
-
 pH 8.0, 25°C Tetronarce californica 3-(1-benzyl-4-piperidyl)-1-(7-chloro-4-methoxy-1H-indol-5-yl)propan-1-one
0.0000204
-
 pH 8.0, 25°C Homo sapiens 3-(1-benzyl-4-piperidyl)-1-(7-chloro-4-methoxy-1H-indol-5-yl)propan-1-one
0.0000288
-
 pH 8.0, 25°C Tetronarce californica 1-(7-chloro-1H-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
0.0000288
-
 pH 8.0, 25°C Homo sapiens 1-(7-chloro-1H-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
0.00004
-
 pH 8.0, 25°C Tetronarce californica 3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(4-methoxy-1Hindol-5-yl)propan-1-one
0.00004
-
 pH 8.0, 25°C Homo sapiens 3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(4-methoxy-1Hindol-5-yl)propan-1-one
0.000051
-
 pH 8.0, 25°C Tetronarce californica 3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one
0.000051
-
 pH 8.0, 25°C Homo sapiens 3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one
0.00006
-
 pH 8.0, 25°C Homo sapiens donepezil
0.0000844
-
 pH 8.0, 25°C Tetronarce californica 1-(7-chloro-4-methoxy-1-methyl-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
0.0000844
-
 pH 8.0, 25°C Homo sapiens 1-(7-chloro-4-methoxy-1-methyl-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
0.0000914
-
 pH 8.0, 25°C Tetronarce californica 1-(7-chloro-4-methoxy-1H-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
0.0000914
-
 pH 8.0, 25°C Homo sapiens 1-(7-chloro-4-methoxy-1H-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
0.000094
-
 pH 8.0, 25°C Tetronarce californica 3-[1-(cyclopentylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one
0.000094
-
 pH 8.0, 25°C Homo sapiens 3-[1-(cyclopentylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one
0.000133
-
 pH 8.0, 25°C Tetronarce californica 1-(1-benzylindol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
0.000133
-
 pH 8.0, 25°C Homo sapiens 1-(1-benzylindol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
0.0002606
-
 pH 8.0, 25°C Tetronarce californica 1-(1-benzyl-7-chloro-4-methoxy-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
0.0002606
-
 pH 8.0, 25°C Homo sapiens 1-(1-benzyl-7-chloro-4-methoxy-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
0.000275
-
 pH 8.0, 25°C Tetronarce californica 3-(1-benzyl-4-piperidyl)-1-(7-chloro-4-methoxy-2-trimethylsilyl-1H-indol-5-yl)propan-1-one
0.000275
-
 pH 8.0, 25°C Homo sapiens 3-(1-benzyl-4-piperidyl)-1-(7-chloro-4-methoxy-2-trimethylsilyl-1H-indol-5-yl)propan-1-one
0.000559
-
 pH 8.0, 25°C Tetronarce californica 1-[1-(benzenesulfonyl)-7-chloro-4-methoxy-indol-5-yl]-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
0.000559
-
 pH 8.0, 25°C Homo sapiens 1-[1-(benzenesulfonyl)-7-chloro-4-methoxy-indol-5-yl]-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one
0.000716
-
 pH 8.0, 25°C Tetronarce californica 3-(1-butyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one
0.000716
-
 pH 8.0, 25°C Homo sapiens 3-(1-butyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one