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Literature summary for 3.1.1.7 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

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

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
acetylcholine + H2O Electrophorus electricus
-
acetate + choline
-
?

Organism

Organism UniProt Comment Textmining
Electrophorus electricus
-
-
-

Substrates and Products (Substrate)

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

Synonyms

Synonyms Comment Organism
AChE
-
Electrophorus electricus

Temperature Optimum [°C]

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

pH Optimum

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

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0000008
-
cyclophostin pH 7.5, 25°C Electrophorus electricus
0.006
-
diisopropylfluorophosphate pH 7.5, 25°C Electrophorus electricus
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
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
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
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

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00012
-
pH 7.5, 25°C Electrophorus electricus diisopropylfluorophosphate
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
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
0.005
-
pH 7.5, 25°C Electrophorus electricus methyl 1-methoxy-5-methyl-1,2,3,6-tetrahydrophosphinine-4-carboxylate 1-oxide
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
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
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
0.07
-
pH 7.5, 25°C Electrophorus electricus (E)-dimethyl 1-(2-oxodihydrofuran-3(2H)-ylidene)ethyl phosphate
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
1
-
above, pH 7.5, 25°C Electrophorus electricus (Z)-dimethyl 1-(2-oxodihydrofuran-3(2H)-ylidene)ethyl phosphate