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Literature summary extracted from
- 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 .
Inhibitors
| EC Number | Inhibitors | Comment | Organism | Structure |
|---|---|---|---|---|
| 3.1.1.7 | 1-(1-benzyl-7-chloro-4-methoxy-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | - |
Homo sapiens |  |
| 3.1.1.7 | 1-(1-benzyl-7-chloro-4-methoxy-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | - |
Tetronarce californica | |
| 3.1.1.7 | 1-(1-benzylindol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 1-(1-benzylindol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | - |
Tetronarce californica | |
| 3.1.1.7 | 1-(4-amino-3-chloro-5-iodo-phenyl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 1-(4-amino-3-iodo-phenyl)-3-(1-benzyl-4-piperidyl)propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 1-(4-amino-3-iodo-phenyl)-3-(1-butyl-4-piperidyl)propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 1-(4-amino-3-iodo-phenyl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 1-(4-amino-3-iodo-phenyl)-3-[1-(cyclopentylmethyl)-4-piperidyl]propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 1-(4-amino-5-chloro-2-methoxyphenyl)-3-(1-butyl-4-piperidinyl)-1-propanone | i.e. RS67333 | Homo sapiens | |
| 3.1.1.7 | 1-(4-amino-5-chloro-2-methoxyphenyl)-3-(1-butyl-4-piperidinyl)-1-propanone | i.e. RS67333 | Tetronarce californica | |
| 3.1.1.7 | 1-(4-amino-5-chloro-3-iodo-2-methoxy-phenyl)-3-(1-benzyl-4-piperidyl)propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 1-(4-amino-5-chloro-3-iodo-2-methoxy-phenyl)-3-[1-(cyclohexylmethyl)-4-piperidyl] propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 1-(7-chloro-1H-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 1-(7-chloro-1H-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | - |
Tetronarce californica | |
| 3.1.1.7 | 1-(7-chloro-4-methoxy-1-methyl-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 1-(7-chloro-4-methoxy-1-methyl-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | - |
Tetronarce californica | |
| 3.1.1.7 | 1-(7-chloro-4-methoxy-1H-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 1-(7-chloro-4-methoxy-1H-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | - |
Tetronarce californica | |
| 3.1.1.7 | 1-[1-(benzenesulfonyl)-7-chloro-4-methoxy-indol-5-yl]-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 1-[1-(benzenesulfonyl)-7-chloro-4-methoxy-indol-5-yl]-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | - |
Tetronarce californica | |
| 3.1.1.7 | 1-[7-chloro-2-(trimethylsilyl)-1H-inden-5-yl]-3-[1-(cyclohexylmethyl)piperidin-4-yl]propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 1-[7-chloro-4-methoxy-2-(trimethylsilyl)-1H-inden-5-yl]-3-[1-(cyclohexylmethyl)piperidin-4-yl]propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 3-(1-benzyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 3-(1-benzyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one | - |
Tetronarce californica | |
| 3.1.1.7 | 3-(1-benzyl-4-piperidyl)-1-(7-chloro-4-methoxy-1H-indol-5-yl)propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 3-(1-benzyl-4-piperidyl)-1-(7-chloro-4-methoxy-1H-indol-5-yl)propan-1-one | - |
Tetronarce californica | |
| 3.1.1.7 | 3-(1-benzyl-4-piperidyl)-1-(7-chloro-4-methoxy-2-trimethylsilyl-1H-indol-5-yl)propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 3-(1-benzyl-4-piperidyl)-1-(7-chloro-4-methoxy-2-trimethylsilyl-1H-indol-5-yl)propan-1-one | - |
Tetronarce californica | |
| 3.1.1.7 | 3-(1-butyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 3-(1-butyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one | - |
Tetronarce californica | |
| 3.1.1.7 | 3-(1-butylpiperidin-4-yl)-1-[2-(trimethylsilyl)-1H-inden-5-yl]propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 3-(1-phenoxypiperidin-4-yl)-1-[2-(trimethylsilyl)-1H-inden-5-yl]propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one | - |
Tetronarce californica | |
| 3.1.1.7 | 3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(4-methoxy-1Hindol-5-yl)propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(4-methoxy-1Hindol-5-yl)propan-1-one | - |
Tetronarce californica | |
| 3.1.1.7 | 3-[1-(cyclohexylmethyl)piperidin-4-yl]-1-[2-(trimethylsilyl)-1H-inden-5-yl]propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 3-[1-(cyclopentylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 3-[1-(cyclopentylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one | - |
Tetronarce californica | |
| 3.1.1.7 | 3-[1-(cyclopentylmethyl)piperidin-4-yl]-1-[2-(trimethylsilyl)-1H-inden-5-yl]propan-1-one | - |
Homo sapiens | |
| 3.1.1.7 | 4-amino-3-chloro-5-iodobenzoic acid | - |
Homo sapiens | |
| 3.1.1.7 | 4-amino-3-iodobenzoic acid | - |
Homo sapiens | |
| 3.1.1.7 | 4-amino-5-chloro-3-iodo-2-methoxybenzoic acid | - |
Homo sapiens | |
| 3.1.1.7 | 4-methoxy-1H-indole-5-carboxylic acid | - |
Homo sapiens | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | donepezil | - |
Homo sapiens | |
| 3.1.1.7 | donepezil | - |
Tetronarce californica | |
| 3.1.1.7 | ethyl 3-(4-amino-3-chloro-5-iodo-phenyl)-3-oxo-propanoate | - |
Homo sapiens | |
| 3.1.1.7 | ethyl 3-(4-amino-3-iodo-phenyl)-3-oxo-propanoate | - |
Homo sapiens | |
| 3.1.1.7 | ethyl 3-(4-amino-5-chloro-3-iodo-2-methoxy-phenyl)-3-oxo-propanoate | - |
Homo sapiens | |
| 3.1.1.7 | ethyl 3-(4-methoxy-1H-indol-5-yl)-3-oxo-propanoate | - |
Homo sapiens | |
| 3.1.1.7 | galantamine | - |
Homo sapiens | |
| 3.1.1.7 | galantamine | - |
Tetronarce californica | |
| 3.1.1.7 | methyl 4-amino-5-chloro-3-iodo-2-methoxybenzoate | - |
Homo sapiens | |
| 3.1.1.7 | methyl 4-methoxy-1H-indole-5-carboxylate | - |
Homo sapiens | |
| 3.1.1.7 | methyl 7-chloro-4-methoxy-1H-indole-5-carboxylate | - |
Homo sapiens | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | rivastigmine | - |
Homo sapiens | |
| 3.1.1.7 | rivastigmine | - |
Tetronarce californica | |
| 3.1.1.7 | tert-butyl 4-[3-(4-amino-3-chloro-5-iodo-phenyl)-3-oxopropyl]piperidine-1-carboxylate | - |
Homo sapiens | |
| 3.1.1.7 | tert-butyl 4-[3-(4-amino-3-iodo-phenyl)-3-oxo-propyl]piperidine-1-carboxylate | - |
Homo sapiens | |
| 3.1.1.7 | tert-butyl 4-[3-(4-amino-5-chloro-3-iodo-2-methoxyphenyl)-3-oxo-propyl]piperidine-1-carboxylate | - |
Homo sapiens | |
| 3.1.1.7 | tert-butyl 4-[3-(4-methoxy-1H-indol-5-yl)-3-oxo-propyl]piperidine-1-carboxylate | - |
Homo sapiens | |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 3.1.1.7 | acetylcholine + H2O | Tetronarce californica | - |
choline + acetate | - |
? | |
| 3.1.1.7 | acetylcholine + H2O | Homo sapiens | - |
choline + acetate | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 3.1.1.7 | Homo sapiens | P22303 | - |
- |
| 3.1.1.7 | Tetronarce californica | P04058 | i.e. Tetronarce californica | - |
Source Tissue
| EC Number | Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|---|
| 3.1.1.7 | erythrocyte | - |
Homo sapiens | - |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 3.1.1.7 | acetylcholine + H2O | - |
Tetronarce californica | choline + acetate | - |
? | |
| 3.1.1.7 | acetylcholine + H2O | - |
Homo sapiens | choline + acetate | - |
? | |
| 3.1.1.7 | 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 | - |
? | |
| 3.1.1.7 | 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
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 3.1.1.7 | AChE | - |
Tetronarce californica |
| 3.1.1.7 | AChE | - |
Homo sapiens |
Temperature Optimum [°C]
| EC Number | Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|---|
| 3.1.1.7 | 25 | - |
assay at | Tetronarce californica |
| 3.1.1.7 | 25 | - |
assay at | Homo sapiens |
pH Optimum
| EC Number | pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|---|
| 3.1.1.7 | 8 | - |
assay at | Tetronarce californica |
| 3.1.1.7 | 8 | - |
assay at | Homo sapiens |
IC50 Value
| EC Number | IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|---|
| 3.1.1.7 | 0.0000133 | - |
pH 8.0, 25°C | Tetronarce californica | 3-(1-benzyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one | |
| 3.1.1.7 | 0.0000133 | - |
pH 8.0, 25°C | Homo sapiens | 3-(1-benzyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one | |
| 3.1.1.7 | 0.000016 | - |
pH 8.0, 25°C | Homo sapiens | donecopride | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | 0.0000288 | - |
pH 8.0, 25°C | Tetronarce californica | 1-(7-chloro-1H-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | |
| 3.1.1.7 | 0.0000288 | - |
pH 8.0, 25°C | Homo sapiens | 1-(7-chloro-1H-indol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | |
| 3.1.1.7 | 0.00004 | - |
pH 8.0, 25°C | Tetronarce californica | 3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(4-methoxy-1Hindol-5-yl)propan-1-one | |
| 3.1.1.7 | 0.00004 | - |
pH 8.0, 25°C | Homo sapiens | 3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(4-methoxy-1Hindol-5-yl)propan-1-one | |
| 3.1.1.7 | 0.000051 | - |
pH 8.0, 25°C | Tetronarce californica | 3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one | |
| 3.1.1.7 | 0.000051 | - |
pH 8.0, 25°C | Homo sapiens | 3-[1-(cyclohexylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one | |
| 3.1.1.7 | 0.00006 | - |
pH 8.0, 25°C | Homo sapiens | donepezil | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | 0.000094 | - |
pH 8.0, 25°C | Tetronarce californica | 3-[1-(cyclopentylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one | |
| 3.1.1.7 | 0.000094 | - |
pH 8.0, 25°C | Homo sapiens | 3-[1-(cyclopentylmethyl)-4-piperidyl]-1-(1H-indol-5-yl)propan-1-one | |
| 3.1.1.7 | 0.000133 | - |
pH 8.0, 25°C | Tetronarce californica | 1-(1-benzylindol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | |
| 3.1.1.7 | 0.000133 | - |
pH 8.0, 25°C | Homo sapiens | 1-(1-benzylindol-5-yl)-3-[1-(cyclohexylmethyl)-4-piperidyl]propan-1-one | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | 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 | |
| 3.1.1.7 | 0.000716 | - |
pH 8.0, 25°C | Tetronarce californica | 3-(1-butyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one | |
| 3.1.1.7 | 0.000716 | - |
pH 8.0, 25°C | Homo sapiens | 3-(1-butyl-4-piperidyl)-1-(1H-indol-5-yl)propan-1-one | |
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