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Literature summary extracted from

  • Johansson, L.; Fotsch, C.; Bartberger, M.D.; Castro, V.M.; Chen, M.; Emery, M.; Gustafsson, S.; Hale, C.; Hickman, D.; Homan, E.; Jordan, S.R.; Komorowski, R.; Li, A.; McRae, K.; Moniz, G.; Matsumoto, G.; Orihuela, C.; Palm, G.; Veniant, M.; Wang, M.; Williams, M.; Zhang, J.
    2-amino-1,3-thiazol-4(5H)-ones as potent and selective 11beta-hydroxysteroid dehydrogenase type 1 inhibitors: enzyme-ligand co-crystal structure and demonstration of pharmacodynamic effects in C57Bl/6 mice (2008), J. Med. Chem., 51, 2933-2943.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.1.1.B40 the 11beta-HSD2 enzyme is produced in HEK-293 cells Homo sapiens
1.1.1.146 the 11beta-HSD1 enzyme is expressed in Escherichia coli Homo sapiens

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
1.1.1.146 11beta-HSD1 (24-292) C272S mutant, hanging drop vapour diffusion method, using 25% (w/v) PEG 3350, 0.2 M ammonium acetate, and 0.1 M sodium citrate buffer (pH 5.6) Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.146 (+/-)-2-((cyclohexylmethyl)amino)-5-ethyl-5-methyl-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-2-((cyclohexylmethyl)amino)-5-methyl-5-propyl-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-2-(1-adamantylamino)-5-ethyl-5-methyl-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-2-(1-adamantylamino)-5-methyl-5-propyl-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-2-(cycloheptylamino)-5-ethyl-5-methyl-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-2-(cycloheptylamino)-5-methyl-5-propyl-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-2-(cyclohexylamino)-5-ethyl-5-methyl-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-2-(cyclohexylamino)-5-methyl-5-propyl-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-2-(cyclooctylamino)-5-ethyl-5-methyl-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-2-(cyclooctylamino)-5-methyl-5-propyl-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-5-ethyl-5-methyl-2-(1-norbornylamino)-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-5-ethyl-5-methyl-2-(3-noradamantylamino)-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-5-ethyl-5-methyl-2-(7-norbornylamino)-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-5-ethyl-5-methyl-2-[(2,2,3,3-tetramethylcyclopropyl)amino]-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-5-methyl-2-(1-norbornylamino)-5-propyl-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-5-methyl-2-(3-noradamantylamino)-5-propyl-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-5-methyl-2-(7-norbornylamino)-5-propyl-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 (+/-)-5-methyl-5-propyl-2-[(2,2,3,3-tetramethylcyclopropyl)amino]-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 2-(1-adamantylamino)-1-thia-3-azaspiro[4.4]non-2-en-4-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 2-(1-adamantylamino)-5,5-diethyl-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 2-(3-noradamantylamino)-1-thia-3-azaspiro[4.4]non-2-en-4-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 2-(cyclooctylamino)-1-thia-3-azaspiro[4.4]non-2-en-4-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 2-(cyclooctylamino)-5,5-diethyl-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens
1.1.1.146 5,5-diethyl-2-(3-noradamantylamino)-1,3-thiazol-4-(5H)-one inhibitor for isozyme 11beta-HSD1, but not for isozyme 11beta-HSD2 Homo sapiens

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.B40 Homo sapiens
-
-
-
1.1.1.146 Homo sapiens P28845
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.B40 cortisol + NAD+
-
Homo sapiens cortisone + NADH
-
ir
1.1.1.146 cortisone + NADPH + H+
-
Homo sapiens cortisol + NADP+
-
r

Synonyms

EC Number Synonyms Comment Organism
1.1.1.B40 11beta-HSD2
-
Homo sapiens
1.1.1.B40 11beta-hydroxysteroid dehydrogenase type 2
-
Homo sapiens
1.1.1.146 11beta-HSD1
-
Homo sapiens
1.1.1.146 11beta-hydroxysteroid dehydrogenase type 1
-
Homo sapiens

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.B40 NAD+
-
Homo sapiens
1.1.1.146 NADP+
-
Homo sapiens

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.1.1.146 0.000003
-
2-(3-noradamantylamino)-1-thia-3-azaspiro[4.4]non-2-en-4-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000012
-
(+/-)-5-methyl-2-(3-noradamantylamino)-5-propyl-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000013
-
(+/-)-5-ethyl-5-methyl-2-(3-noradamantylamino)-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000013
-
5,5-diethyl-2-(3-noradamantylamino)-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000014
-
2-(cyclooctylamino)-1-thia-3-azaspiro[4.4]non-2-en-4-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.00002
-
2-(1-adamantylamino)-5,5-diethyl-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000024
-
(+/-)-2-(1-adamantylamino)-5-ethyl-5-methyl-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000024
-
(+/-)-2-(1-adamantylamino)-5-methyl-5-propyl-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000025
-
(+/-)-5-methyl-2-(1-norbornylamino)-5-propyl-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000026
-
2-(cyclooctylamino)-5,5-diethyl-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000028
-
(+/-)-2-(cyclooctylamino)-5-methyl-5-propyl-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000028
-
2-(1-adamantylamino)-1-thia-3-azaspiro[4.4]non-2-en-4-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000032
-
(+/-)-2-(cycloheptylamino)-5-methyl-5-propyl-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000034
-
(+/-)-2-((cyclohexylmethyl)amino)-5-methyl-5-propyl-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000038
-
(+/-)-5-methyl-5-propyl-2-[(2,2,3,3-tetramethylcyclopropyl)amino]-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000047
-
(+/-)-2-(cyclooctylamino)-5-ethyl-5-methyl-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000055
-
(+/-)-2-(cyclohexylamino)-5-methyl-5-propyl-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000058
-
(+/-)-5-ethyl-5-methyl-2-[(2,2,3,3-tetramethylcyclopropyl)amino]-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000064
-
(+/-)-2-((cyclohexylmethyl)amino)-5-ethyl-5-methyl-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000073
-
(+/-)-5-ethyl-5-methyl-2-(1-norbornylamino)-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000082
-
(+/-)-2-(cycloheptylamino)-5-ethyl-5-methyl-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000126
-
(+/-)-2-(cyclohexylamino)-5-ethyl-5-methyl-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000149
-
(+/-)-5-methyl-2-(7-norbornylamino)-5-propyl-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens
1.1.1.146 0.000372
-
(+/-)-5-ethyl-5-methyl-2-(7-norbornylamino)-1,3-thiazol-4-(5H)-one pH and temperature not specified in the publication Homo sapiens