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Literature summary for 3.1.1.8 extracted from

  • Carolan, C.G.; Dillon, G.P.; Gaynor, J.M.; Reidy, S.; Ryder, S.A.; Khan, D.; Marquez, J.F.; Gilmer, J.F.
    Isosorbide-2-carbamate esters: potent and selective butyrylcholinesterase inhibitors (2008), J. Med. Chem., 51, 6400-6409.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(2x)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-([[(2E)-3-phenylprop-2-enoyl]oxy]carbonyl)-D-arabino-hexitol 96% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-(2-methylbutanoyl)-D-arabino-hexitol 99% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-(biphenyl-4-ylcarbonyl)-D-arabino-hexitol 99% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-(carboxycarbamoyl)-D-arabino-hexitol 92% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-(cyclopentylcarbonyl)-D-arabino-hexitol 99% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-(cyclopropylcarbonyl)-D-arabino-hexitol 97% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-(phenoxycarbonyl)-D-arabino-hexitol 99% inhibition at 0.1 mM, highly selective for BuChE, with about 50000fold selectivity over human erythrocyte acetylcholinesterase. Competitive, and slowly reversible inhibition by active site carbamylation Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-([[(4-methylphenyl)sulfonyl]oxy]carbonyl)-D-arabino-hexitol 25% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-([[(trifluoromethyl)sulfonyl]oxy]carbonyl)-D-arabino-hexitol 85% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[(2H-chromen-2-yloxy)carbonyl]-D-arabino-hexitol 100% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[(3,4-dihydroxyphenyl)carbonyl]-D-arabino-hexitol 38% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[(pentanoyloxy)carbonyl]-D-arabino-hexitol 95% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[(propanoyloxy)carbonyl]-D-arabino-hexitol 97% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[([[4-(heptyloxy)phenyl]carbonyl]oxy)carbonyl]-D-arabino-hexitol 80% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[[(methylsulfonyl)oxy]carbonyl]-D-arabino-hexitol 9.8% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[[(naphthalen-2-ylcarbonyl)oxy]carbonyl]-D-arabino-hexitol 100% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[[(pyridin-3-ylcarbonyl)oxy]carbonyl]-D-arabino-hexitol 99% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[[(pyridin-4-ylcarbonyl)oxy]carbonyl]-D-arabino-hexitol 97% inhibition at 0.1 mM Homo sapiens
(2xi)-1,4:3,6-dianhydro-2-O-([2-[(carbamoyloxy)methyl]-5-hydroxybenzyl]carbamoyl)-D-arabino-hexitol 95% inhibition at 0.1 mM Homo sapiens
(2xi)-5-O-[(acetyloxy)carbonyl]-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-D-arabino-hexitol 97% inhibition at 0.1 mM Homo sapiens
1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-nitro-D-threo-hexitol 96% inhibition at 0.1 mM Homo sapiens
1,4:3,6-dianhydro-2-O-(butylcarbamoyl)-5-O-nitro-D-threo-hexitol 92% inhibition at 0.1 mM Homo sapiens
1,4:3,6-dianhydro-2-O-(cyclohexylcarbamoyl)-5-O-nitro-D-threo-hexitol 99% inhibition at 0.1 mM Homo sapiens
1,4:3,6-dianhydro-2-O-(ethylcarbamoyl)-5-O-nitro-D-threo-hexitol 73% inhibition at 0.1 mM Homo sapiens
1,4:3,6-dianhydro-2-O-(methylcarbamoyl)-5-O-nitro-D-threo-hexitol 82% inhibition at 0.1 mM Homo sapiens
1,4:3,6-dianhydro-2-O-nitro-5-O-(phenylcarbamoyl)-D-threo-hexitol 37% inhibition at 0.1 mM Homo sapiens
1,4:3,6-dianhydro-2-O-nitro-5-O-(propylcarbamoyl)-D-threo-hexitol 93% inhibition at 0.1 mM Homo sapiens
1,4:3,6-dianhydro-2-O-nitro-5-O-[[4-(trifluoromethyl)phenyl]carbamoyl]-D-threo-hexitol 10% inhibition at 0.1 mM Homo sapiens
1,4:3,6-dianhydro-2-O-[(2-chlorophenyl)carbamoyl]-5-O-nitro-D-threo-hexitol 11% inhibition at 0.1 mM Homo sapiens
1,4:3,6-dianhydro-2-O-[(3,4-dichlorophenyl)carbamoyl]-5-O-nitro-D-threo-hexitol 28% inhibition at 0.1 mM Homo sapiens
1,4:3,6-dianhydro-2-O-[(3-chlorophenyl)carbamoyl]-5-O-nitro-D-threo-hexitol 11% inhibition at 0.1 mM Homo sapiens
2-(benzylaminocarbonyloxy-)-5-O-(1-naphthoyl)-1,4:3,6-dianhydro-D-glucitol 99% inhibition at 0.1 mM Homo sapiens
additional information modeling, stability, and binding structure of isosorbide-2-carbamate ester inhibitors, overview Homo sapiens

Localization

Localization Comment Organism GeneOntology No. Textmining
extracellular
-
Homo sapiens
-
-

Organism

Organism UniProt Comment Textmining
Homo sapiens P06276
-
-

Source Tissue

Source Tissue Comment Organism Textmining
plasma
-
Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
butyrylthiocholine + H2O detection using 5,5'-dithiobis(2-nitrobenzoic acid) Homo sapiens butyrate + thiocholine
-
?

Synonyms

Synonyms Comment Organism
BuChE
-
Homo sapiens
butyrylcholinesterase
-
Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
assay at Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
assay at Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0000043
-
pH 7.4, 37°C Homo sapiens (2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-(phenoxycarbonyl)-D-arabino-hexitol
0.000006
-
pH 7.4, 37°C Homo sapiens (2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-(cyclopentylcarbonyl)-D-arabino-hexitol
0.000012
-
pH 7.4, 37°C Homo sapiens (2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-(biphenyl-4-ylcarbonyl)-D-arabino-hexitol
0.000028
-
pH 7.4, 37°C Homo sapiens 2-(benzylaminocarbonyloxy-)-5-O-(1-naphthoyl)-1,4:3,6-dianhydro-D-glucitol
0.000032
-
pH 7.4, 37°C Homo sapiens (2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[[(naphthalen-2-ylcarbonyl)oxy]carbonyl]-D-arabino-hexitol
0.000051
-
pH 7.4, 37°C Homo sapiens 1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-nitro-D-threo-hexitol
0.000072
-
pH 7.4, 37°C Homo sapiens (2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-(2-methylbutanoyl)-D-arabino-hexitol
0.000073
-
pH 7.4, 37°C Homo sapiens (2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[(2H-chromen-2-yloxy)carbonyl]-D-arabino-hexitol
0.000088
-
pH 7.4, 37°C Homo sapiens (2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[[(pyridin-4-ylcarbonyl)oxy]carbonyl]-D-arabino-hexitol
0.000137
-
pH 7.4, 37°C Homo sapiens (2x)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-([[(2E)-3-phenylprop-2-enoyl]oxy]carbonyl)-D-arabino-hexitol
0.000334
-
pH 7.4, 37°C Homo sapiens (2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-(cyclopropylcarbonyl)-D-arabino-hexitol
0.00036
-
pH 7.4, 37°C Homo sapiens (2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-([[(trifluoromethyl)sulfonyl]oxy]carbonyl)-D-arabino-hexitol
0.00057
-
pH 7.4, 37°C Homo sapiens (2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[[(pyridin-3-ylcarbonyl)oxy]carbonyl]-D-arabino-hexitol
0.000639
-
pH 7.4, 37°C Homo sapiens 1,4:3,6-dianhydro-2-O-nitro-5-O-(propylcarbamoyl)-D-threo-hexitol
0.000669
-
pH 7.4, 37°C Homo sapiens (2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[(3,4-dihydroxyphenyl)carbonyl]-D-arabino-hexitol
0.0007
-
pH 7.4, 37°C Homo sapiens (2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[(pentanoyloxy)carbonyl]-D-arabino-hexitol
0.000894
-
pH 7.4, 37°C Homo sapiens 1,4:3,6-dianhydro-2-O-(butylcarbamoyl)-5-O-nitro-D-threo-hexitol
0.00098
-
pH 7.4, 37°C Homo sapiens (2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[(propanoyloxy)carbonyl]-D-arabino-hexitol
0.0025
-
pH 7.4, 37°C Homo sapiens 1,4:3,6-dianhydro-2-O-(cyclohexylcarbamoyl)-5-O-nitro-D-threo-hexitol
0.0028
-
pH 7.4, 37°C Homo sapiens (2xi)-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-5-O-[([[4-(heptyloxy)phenyl]carbonyl]oxy)carbonyl]-D-arabino-hexitol
0.0037
-
pH 7.4, 37°C Homo sapiens (2xi)-1,4:3,6-dianhydro-2-O-([2-[(carbamoyloxy)methyl]-5-hydroxybenzyl]carbamoyl)-D-arabino-hexitol
0.0039
-
pH 7.4, 37°C Homo sapiens 1,4:3,6-dianhydro-2-O-(ethylcarbamoyl)-5-O-nitro-D-threo-hexitol
0.0041
-
pH 7.4, 37°C Homo sapiens (2xi)-5-O-[(acetyloxy)carbonyl]-1,4:3,6-dianhydro-2-O-(benzylcarbamoyl)-D-arabino-hexitol
0.0051
-
pH 7.4, 37°C Homo sapiens 1,4:3,6-dianhydro-2-O-(methylcarbamoyl)-5-O-nitro-D-threo-hexitol