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Literature summary extracted from

  • Dutta, S.; Malla, R.K.; Bandyopadhyay, S.; Spilling, C.D.; Dupureur, C.M.
    Synthesis and kinetic analysis of some phosphonate analogs of cyclophostin as inhibitors of human acetylcholinesterase (2010), Bioorg. Med. Chem., 18, 2265-2274.
    View publication on PubMedView publication on EuropePMC

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.1.1.7 (2-methoxy-7-methyl-2-oxido-2,3,4,5-tetrahydro-1,2-oxaphosphepin-6-yl)methanol
-
 Electrophorus electricus
3.1.1.7 (3R,5aR)-3-methoxy-1-methyl-4,5,5a,6-tetrahydro-3H,8H-furo[3,4-e][1,2]oxaphosphepin-8-one 3-oxide a diastereoisomeric bicyclic phosphonate analogue Electrophorus electricus
3.1.1.7 (3S,5aR)-3-methoxy-1-methyl-4,5,5a,6-tetrahydro-3H,8H-furo[3,4-e][1,2]oxaphosphepin-8-one 3-oxide a diastereoisomeric bicyclic phosphonate analogue Electrophorus electricus
3.1.1.7 (E)-dimethyl 1-(2-oxodihydrofuran-3(2H)-ylidene)ethyl phosphate
-
 Electrophorus electricus
3.1.1.7 (Z)-dimethyl 1-(2-oxodihydrofuran-3(2H)-ylidene)ethyl phosphate
-
 Electrophorus electricus
3.1.1.7 cyclophostin a natural AChE inhibitor Electrophorus electricus
3.1.1.7 diethylfluorophosphate
-
 Electrophorus electricus
3.1.1.7 diisopropylfluorophosphate
-
 Electrophorus electricus
3.1.1.7 methyl (2R,5R)-5-[(benzyloxy)methyl]-2-methoxy-7-methyl-2,3,4,5-tetrahydro-1,2-oxaphosphepine-6-carboxylate 2-oxide
-
 Electrophorus electricus
3.1.1.7 methyl (2S,5R)-5-[(benzyloxy)methyl]-2-methoxy-7-methyl-2,3,4,5-tetrahydro-1,2-oxaphosphepine-6-carboxylate 2-oxide
-
 Electrophorus electricus
3.1.1.7 methyl 1-methoxy-5-methyl-1,2,3,6-tetrahydrophosphinine-4-carboxylate 1-oxide
-
 Electrophorus electricus
3.1.1.7 methyl 2-acetyl-4-(dimethoxyphosphoryl)butanoate
-
 Electrophorus electricus
3.1.1.7 methyl 2-acetyl-5-(dimethoxyphosphoryl)pent-4-enoate
-
 Electrophorus electricus
3.1.1.7 methyl 2-acetyl-5-(dimethoxyphosphoryl)pentanoate
-
 Electrophorus electricus
3.1.1.7 methyl 2-methoxy-7-methyl-2,3,4,5-tetrahydro-1,2-oxaphosphepine-6-carboxylate 2-oxide
-
 Electrophorus electricus
3.1.1.7 additional information synthesis and kinetic analysis of some phosphonate analogs of cyclophostin as inhibitors of acetylcholinesterase, mechanism of inhibition, overview Electrophorus electricus
3.1.1.7 paraoxon
-
 Electrophorus electricus
3.1.1.7 soman
-
 Electrophorus electricus
3.1.1.7 Tabun
-
 Electrophorus electricus
3.1.1.7 VX (nerve agent)
-
 Electrophorus electricus

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 Electrophorus electricus
-
 acetate + choline
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.1.1.7 Electrophorus electricus
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.1.1.7 acetylcholine + H2O
-
 Electrophorus electricus acetate + choline
-
 ?
3.1.1.7 acetylthiocholine + H2O
-
 Electrophorus electricus acetate + thiocholine
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.1.1.7 AChE
-
 Electrophorus electricus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.1.1.7 25
-
 irreversible inhibition assay at Electrophorus electricus
3.1.1.7 37
-
 assay at Electrophorus electricus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.1.1.7 7.5
-
 irreversible inhibition assay at Electrophorus electricus
3.1.1.7 8
-
 enzyme assay at Electrophorus electricus

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
3.1.1.7 0.0000008
-
 cyclophostin pH 7.5, 25°C Electrophorus electricus
3.1.1.7 0.006
-
 diisopropylfluorophosphate pH 7.5, 25°C Electrophorus electricus
3.1.1.7 0.024
-
 (3S,5aR)-3-methoxy-1-methyl-4,5,5a,6-tetrahydro-3H,8H-furo[3,4-e][1,2]oxaphosphepin-8-one 3-oxide pH 7.5, 25°C Electrophorus electricus
3.1.1.7 0.076
-
 methyl 2-methoxy-7-methyl-2,3,4,5-tetrahydro-1,2-oxaphosphepine-6-carboxylate 2-oxide pH 7.5, 25°C Electrophorus electricus
3.1.1.7 0.14
-
 (3R,5aR)-3-methoxy-1-methyl-4,5,5a,6-tetrahydro-3H,8H-furo[3,4-e][1,2]oxaphosphepin-8-one 3-oxide pH 7.5, 25°C Electrophorus electricus
3.1.1.7 0.31
-
 methyl 1-methoxy-5-methyl-1,2,3,6-tetrahydrophosphinine-4-carboxylate 1-oxide pH 7.5, 25°C Electrophorus electricus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.1.1.7 0.00012
-
 pH 7.5, 25°C Electrophorus electricus diisopropylfluorophosphate
3.1.1.7 0.0003
-
 pH 7.5, 25°C Electrophorus electricus (3S,5aR)-3-methoxy-1-methyl-4,5,5a,6-tetrahydro-3H,8H-furo[3,4-e][1,2]oxaphosphepin-8-one 3-oxide
3.1.1.7 0.003
-
 pH 7.5, 25°C Electrophorus electricus (3R,5aR)-3-methoxy-1-methyl-4,5,5a,6-tetrahydro-3H,8H-furo[3,4-e][1,2]oxaphosphepin-8-one 3-oxide
3.1.1.7 0.005
-
 pH 7.5, 25°C Electrophorus electricus methyl 1-methoxy-5-methyl-1,2,3,6-tetrahydrophosphinine-4-carboxylate 1-oxide
3.1.1.7 0.006
-
 pH 7.5, 25°C Electrophorus electricus methyl (2R,5R)-5-[(benzyloxy)methyl]-2-methoxy-7-methyl-2,3,4,5-tetrahydro-1,2-oxaphosphepine-6-carboxylate 2-oxide
3.1.1.7 0.007
-
 pH 7.5, 25°C Electrophorus electricus methyl 2-methoxy-7-methyl-2,3,4,5-tetrahydro-1,2-oxaphosphepine-6-carboxylate 2-oxide
3.1.1.7 0.035
-
 pH 7.5, 25°C Electrophorus electricus methyl (2S,5R)-5-[(benzyloxy)methyl]-2-methoxy-7-methyl-2,3,4,5-tetrahydro-1,2-oxaphosphepine-6-carboxylate 2-oxide
3.1.1.7 0.07
-
 pH 7.5, 25°C Electrophorus electricus (E)-dimethyl 1-(2-oxodihydrofuran-3(2H)-ylidene)ethyl phosphate
3.1.1.7 0.6
-
 pH 7.5, 25°C Electrophorus electricus (2-methoxy-7-methyl-2-oxido-2,3,4,5-tetrahydro-1,2-oxaphosphepin-6-yl)methanol
3.1.1.7 1
-
 above, pH 7.5, 25°C Electrophorus electricus (Z)-dimethyl 1-(2-oxodihydrofuran-3(2H)-ylidene)ethyl phosphate