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Literature summary for 5.4.99.17 extracted from

  • Lenhart, A.; Reinert, D.J.; Aebi, J.D.; Dehmlow, H.; Morand, O.H.; Schulz, G.E.
    Binding structures and potencies of oxidosqualene cyclase inhibitors with the homologous squalene-hopene cyclase (2003), J. Med. Chem., 46, 2083-2092.
    View publication on PubMed
Search for more literature for 5.4.99.17

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli JM 105 Alicyclobacillus acidocaldarius

Crystallization (Commentary)

Crystallization (Comment) Organism
complexes with 11 human oxidosqualene cyclase inhibitors produced by cocrystallization, elucidation of the structures by X-ray diffraction analyses Alicyclobacillus acidocaldarius

Inhibitors

Inhibitors Comment Organism Structure
(4-(2-[(allyl-cyclopropyl-amino)-methyl]-cyclopropylmethoxy)-phenyl)-(4-bromo-phenyl)-methanone IC50 59 nM Alicyclobacillus acidocaldarius
(4-bromo-phenyl)-(4-(2-[(cyclopropyl-methyl-amino)-methyl]-cyclopropylmethoxy)-2-fluoro-phenyl)-methanone IC50 50 nM Alicyclobacillus acidocaldarius
(4-bromo-phenyl)-(4-(2-[(cyclopropyl-methyl-amino)-methyl]-cyclopropylmethoxy)-phenyl)-methanone IC50 62 nM Alicyclobacillus acidocaldarius
(4-bromo-phenyl)-(4-[4-(cyclopropyl-methyl-amino)-but-2-enyloxy]-phenyl)-methanone IC50 18 nM Alicyclobacillus acidocaldarius
(4-bromo-phenyl)-(4-[6-(cyclopropyl-methyl-amino)-hexyloxy]-2-fluoro-phenyl)-methanone IC50 38 nM Alicyclobacillus acidocaldarius
(4-chloro-phenyl)-(4-[4-(4,5-dihydro-oxazol-2-yl)-benzylidene]-piperidin-1-yl)-methanone IC50 2800 nM Alicyclobacillus acidocaldarius
(4-[6-(allyl-methyl-amino)-hexyloxy]-2-fluoro-phenyl)-(4-bromo-phenyl)-methanone IC50 60 nM Alicyclobacillus acidocaldarius
(4-[6-(allyl-methyl-amino)-hexyloxy]-phenyl)-(4-bromo-phenyl)-methanone IC50 96 nM Alicyclobacillus acidocaldarius
1-(4-(4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexyl)-benzyl)-1-hydroxy-piperidinium IC50 123 nM Alicyclobacillus acidocaldarius
4'-[4-(allyl-methyl-amino)-but-2-enyloxy]-biphenyl-4-yl-(4-bromo-phenyl)-methanone IC50 29 nM Alicyclobacillus acidocaldarius
4-[4-(allyl-methyl-amino)-but-2-enyloxy]-phenyl-(4-bromo-phenyl)-methanone IC50 40 nM Alicyclobacillus acidocaldarius
4-[6-(allyl-methyl-amino)-hexyloxy]-piperidin-1-yl-(4-fluoro-phenyl)-methanone IC50 1200 nM Alicyclobacillus acidocaldarius
4-[6-(cyclopropyl-methyl-amino)-hexyloxy]-piperidin-1-yl-(4-fluoro-phenyl)-methanone IC50 760 nM Alicyclobacillus acidocaldarius
allyl-(4-[3-(4-bromo-phenyl)-5-fluoro-1-methyl-1H-indazol-6-yloxy]-but-2-enyl)-methyl-amine IC50 281 nM; IC50 332 nM Alicyclobacillus acidocaldarius
allyl-(4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl)-methyl-amine IC50 23 nM Alicyclobacillus acidocaldarius
allyl-(4-[3-(4-bromo-phenyl)-benzo[b]thiophen-6-yloxy]-butyl)-methyl-amine IC50 75 nM Alicyclobacillus acidocaldarius
allyl-(4-[3-(4-bromo-phenyl)-benzo[d]isoxazol-6-yloxy]-but-2-enyl)-amine IC50 49 nM Alicyclobacillus acidocaldarius
allyl-(4-[4-(6-bromo-benzo[d]isothiazol-3-yl)-phenoxy]-but-2-enyl)-methyl-amine IC50 130 nM Alicyclobacillus acidocaldarius
allyl-(6-[1-(4-bromo-phenyl)-isoquinolin-6-yloxy]-hexyl)-methyl-amine IC50 186 nM Alicyclobacillus acidocaldarius
allyl-(6-[3-(4-bromo-phenyl)-1-methyl-1H-indazol-6-yloxy]-hexyl)-methyl-amine IC50 289 nM Alicyclobacillus acidocaldarius
allyl-(6-[3-(4-bromo-phenyl)-1H-indazol-6-yloxy]-hexyl)-methyl-amine IC50 180 nM Alicyclobacillus acidocaldarius
allyl-(6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl)-methyl-amine IC50 80 nM Alicyclobacillus acidocaldarius
allyl-(6-[3-(4-bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-hexyl)-methyl-amine IC50 306 nM Alicyclobacillus acidocaldarius
allyl-(6-[3-(4-bromo-phenyl)-benzo[d]isoxazol-6-yloxy]-hexyl)-methyl-amine IC50 75 nM Alicyclobacillus acidocaldarius
allyl-(6-[4-(4-bromo-phenyl)-1H-benzo[d][1,2]oxazin-7-yloxy]-hexyl)-methyl-amine IC50 172 nM Alicyclobacillus acidocaldarius
allyl-(6-[4-(6-bromo-benzo[d]isothiazol-3-yl)-phenoxy]-hexyl)-methyl-amine IC50 141 nM Alicyclobacillus acidocaldarius
methyl-[4-(4-piperidin-1-ylmethyl-phenyl)-cyclohexyl]-carbamic acid 4-chloro-phenyl ester IC50 406 nM Alicyclobacillus acidocaldarius
additional information inhibitors designed as cholesterol-lowering agents, for 11 inhibitors the structures of the enzyme-inhibitor complexes were determined by X-ray crystallography Alicyclobacillus acidocaldarius

Organism

Organism UniProt Comment Textmining
Alicyclobacillus acidocaldarius P33247
-
-

Synonyms

Synonyms Comment Organism
SHC
-
 Alicyclobacillus acidocaldarius

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000018
-
 IC50 18 nM Alicyclobacillus acidocaldarius (4-bromo-phenyl)-(4-[4-(cyclopropyl-methyl-amino)-but-2-enyloxy]-phenyl)-methanone
0.000023
-
 IC50 23 nM Alicyclobacillus acidocaldarius allyl-(4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl)-methyl-amine
0.000029
-
 IC50 29 nM Alicyclobacillus acidocaldarius 4'-[4-(allyl-methyl-amino)-but-2-enyloxy]-biphenyl-4-yl-(4-bromo-phenyl)-methanone
0.000038
-
 IC50 38 nM Alicyclobacillus acidocaldarius (4-bromo-phenyl)-(4-[6-(cyclopropyl-methyl-amino)-hexyloxy]-2-fluoro-phenyl)-methanone
0.00004
-
 IC50 40 nM Alicyclobacillus acidocaldarius 4-[4-(allyl-methyl-amino)-but-2-enyloxy]-phenyl-(4-bromo-phenyl)-methanone
0.000049
-
 IC50 49 nM Alicyclobacillus acidocaldarius allyl-(4-[3-(4-bromo-phenyl)-benzo[d]isoxazol-6-yloxy]-but-2-enyl)-amine
0.00005
-
 IC50 50 nM Alicyclobacillus acidocaldarius (4-bromo-phenyl)-(4-(2-[(cyclopropyl-methyl-amino)-methyl]-cyclopropylmethoxy)-2-fluoro-phenyl)-methanone
0.000059
-
 IC50 59 nM Alicyclobacillus acidocaldarius (4-(2-[(allyl-cyclopropyl-amino)-methyl]-cyclopropylmethoxy)-phenyl)-(4-bromo-phenyl)-methanone
0.00006
-
 IC50 60 nM Alicyclobacillus acidocaldarius (4-[6-(allyl-methyl-amino)-hexyloxy]-2-fluoro-phenyl)-(4-bromo-phenyl)-methanone
0.000062
-
 IC50 62 nM Alicyclobacillus acidocaldarius (4-bromo-phenyl)-(4-(2-[(cyclopropyl-methyl-amino)-methyl]-cyclopropylmethoxy)-phenyl)-methanone
0.000075
-
 IC50 75 nM Alicyclobacillus acidocaldarius allyl-(4-[3-(4-bromo-phenyl)-benzo[b]thiophen-6-yloxy]-butyl)-methyl-amine
0.000075
-
 IC50 75 nM Alicyclobacillus acidocaldarius allyl-(6-[3-(4-bromo-phenyl)-benzo[d]isoxazol-6-yloxy]-hexyl)-methyl-amine
0.00008
-
 IC50 80 nM Alicyclobacillus acidocaldarius allyl-(6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl)-methyl-amine
0.000096
-
 IC50 96 nM Alicyclobacillus acidocaldarius (4-[6-(allyl-methyl-amino)-hexyloxy]-phenyl)-(4-bromo-phenyl)-methanone
0.000123
-
 IC50 123 nM Alicyclobacillus acidocaldarius 1-(4-(4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexyl)-benzyl)-1-hydroxy-piperidinium
0.00013
-
 IC50 130 nM Alicyclobacillus acidocaldarius allyl-(4-[4-(6-bromo-benzo[d]isothiazol-3-yl)-phenoxy]-but-2-enyl)-methyl-amine
0.000141
-
 IC50 141 nM Alicyclobacillus acidocaldarius allyl-(6-[4-(6-bromo-benzo[d]isothiazol-3-yl)-phenoxy]-hexyl)-methyl-amine
0.000172
-
 IC50 172 nM Alicyclobacillus acidocaldarius allyl-(6-[4-(4-bromo-phenyl)-1H-benzo[d][1,2]oxazin-7-yloxy]-hexyl)-methyl-amine
0.00018
-
 IC50 180 nM Alicyclobacillus acidocaldarius allyl-(6-[3-(4-bromo-phenyl)-1H-indazol-6-yloxy]-hexyl)-methyl-amine
0.000186
-
 IC50 186 nM Alicyclobacillus acidocaldarius allyl-(6-[1-(4-bromo-phenyl)-isoquinolin-6-yloxy]-hexyl)-methyl-amine
0.000281
-
 IC50 281 nM Alicyclobacillus acidocaldarius allyl-(4-[3-(4-bromo-phenyl)-5-fluoro-1-methyl-1H-indazol-6-yloxy]-but-2-enyl)-methyl-amine
0.000289
-
 IC50 289 nM Alicyclobacillus acidocaldarius allyl-(6-[3-(4-bromo-phenyl)-1-methyl-1H-indazol-6-yloxy]-hexyl)-methyl-amine
0.000306
-
 IC50 306 nM Alicyclobacillus acidocaldarius allyl-(6-[3-(4-bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-hexyl)-methyl-amine
0.000332
-
 IC50 332 nM Alicyclobacillus acidocaldarius allyl-(4-[3-(4-bromo-phenyl)-5-fluoro-1-methyl-1H-indazol-6-yloxy]-but-2-enyl)-methyl-amine
0.000406
-
 IC50 406 nM Alicyclobacillus acidocaldarius methyl-[4-(4-piperidin-1-ylmethyl-phenyl)-cyclohexyl]-carbamic acid 4-chloro-phenyl ester
0.00076
-
 IC50 760 nM Alicyclobacillus acidocaldarius 4-[6-(cyclopropyl-methyl-amino)-hexyloxy]-piperidin-1-yl-(4-fluoro-phenyl)-methanone
0.0012
-
 IC50 1200 nM Alicyclobacillus acidocaldarius 4-[6-(allyl-methyl-amino)-hexyloxy]-piperidin-1-yl-(4-fluoro-phenyl)-methanone
0.0028
-
 IC50 2800 nM Alicyclobacillus acidocaldarius (4-chloro-phenyl)-(4-[4-(4,5-dihydro-oxazol-2-yl)-benzylidene]-piperidin-1-yl)-methanone