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(4-Benzenesulfonyl-piperazin-1-yl)-(3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl)-methanone
-
IC50: 326 nM
(4aalpha,5alpha,6alpha,8abeta)-Decahydro-5,8a-dimethyl-2-(1,5,9-trimethyldecyl)-6-isoquinolinol
-
and simplified analogues
(6E)-10-Aza-10,11-dihydrosqualene-2,3-epoxide
(6Z)-10-aza-10,11-dihydrosqualene-2,3-epoxide
-
IC50: above 0.02 mM, at a protein concentration of 5 mg/ml
(Z)-3-[4-(4-bromobenzoyl)phenacylidene]quinuclidine
-
IC50: 124 nM, oral and selective inhibition of cholesterol biosynthesis derived from enzyme inhibition
1-(2-methyl-4-pyrimidinyl)-4-(1-(4-bromophenylsulfonyl)piperazin-4-ylcarbonyl)piperidine
-
76% inhibition at 0.001 mM, IC50: 398 nM
1-(2-oxazolinyl)-4-(1-(4-bromophenylsulfonyl)piperazin-4-ylcarbonyl)piperidine
-
87% inhibition at 0.001 mM
1-(2-pyrimidinyl)-4-(1-(4-bromophenylsulfonyl)piperazin-4-ylcarbonyl)piperidine
-
8% inhibition at 0.001 mM
1-(2-thiazolinyl)-4-(1-(4-bromophenylsulfonyl)piperazin-4-ylcarbonyl)piperidine
-
complete inhibition at 0.001 mM
1-(4-iodophenylsulfonyl)-4-(1-(4-pyridyl)piperidon-4-ylcarbonyl)piperazine
-
IC50: 82 nM
1-(4-pyrimidinyl)-4-(1-(4-bromophenylsulfonyl)piperazin-4-ylcarbonyl)piperidine
-
complete inhibition at 0.001 mM, IC50: 116 nM
19-aza-18,19,22,23-tetrahydrosqualene-2,3-epoxide
-
IC50: 0.0075 mM, protein concentration of 5 mg/ml
19-Aza-18,19,22,3-tetrahydrosqualene-2,3-epoxide
-
-
19-Azasqualene-2,3-epoxide
-
-
2-Aza-2,3-dihydrosqualene
2-aza-2,3-dihydrosqualene alcohol
-
-
2-Aza-2,3-dihydrosqualene N-oxide
22,23-Epoxy-2-aza-2,3-dihydrosqualene
-
slight
22,23-epoxy-2-aza-2,3-dihydrosqualene-N-oxide
-
0.01 mM, 14% inhibition
3-[(4-chlorobenzoyl)-4-phenoxy]quinuclidin-3-ol
-
-
3-[(4-chlorobenzoyl)-4-phenoxy]quinuclidine
3-[2-(4-bromobenzophenone)ethynyl]quinuclidin-3-ol
-
-
3-[Methyl-(4,8,13,17,21-pentamethyl-docosa-4,8,12,16,20-pentaenyl)-amino]-propan-1-ol
-
0.01 mM, 2% inhibition
4-(4-bromobenzoyl)-1-(1-(4-pyridyl)piperidin-4-ylcarbonyl)piperazine
-
96% inhibition at 0.001 mM
4-(4-bromophenylmethyl)-1-(1-(4-pyridyl)piperidin-4-ylcarbonyl)piperazine
-
complete inhibition at 0.001 mM
azasqualene alcohol
-
0.01 mM, 13% inhibition
cholesterol
-
an increased cholesterol level suppresses the expression of 2,3-oxidosqualene cyclase
diethyl-(4,8,13,17,21-pentamethyl-docosa-4,8,12,16,20-pentaenyl)-aminoxide
-
IC50: 1.5 mM
Diethyl-(4,8,13,17,21-pentamethyl-docosa-4,8,12,16,20-pentaenyl)-ammonium
-
IC50: 3.2 mM
KCl
-
0-0.1 M: activity decreases with increasing concentration of KCl in the presence of optimal concentrations of Triton X-100
N-(1-Oxododecyl)-4alpha,10-dimethyl-8-aza-trans-decal-3beta-ol
-
potent, competitive
N-[(1,5,9)-Trimethyl-decyl]-4alpha,10-dimethyl-8-aza-decal-3beta-ol
-
strong
N-[3-(1,1'-biphenyl-4-yloxy)propyl]-N,N-dimethylamine
-
IC50: 2500 nM
Sulfur-substituted squalene oxide analogues
-
mechanism-based inhibition
-
Trimethyl-(4,8,13,17,21-pentamethyl-docosa-4,8,12,16,20-pentaenyl)-ammonium
-
IC50: 5.1 mM
[19-(3,3-Dimethyl-oxiranyl)-4,8,13,17-tetramethyl-nonadeca-4,8,12,16-tetraenyl]-dimethyl-amine
-
0.01 mM, 8% inhibition
[4-(4-Bromo-benzenesulfonyl)-piperazin-1-yl]-(3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl)-methanone
-
IC50: 228 nM
[5-(4-(4-chloro-benzoyl)-3-fluoro-phenoxy)-pentyl]-methyl-propyl-ammonium fumarate
-
IC50: 49 nM
{4-[4-(4,5-Dihydro-oxazol-2-yl)-benzylidene]-piperidin-1-yl}-(4-trifluoromethyl-phenyl)-methanone
-
IC50: 90 nM, complete inhibition at 0.001 nM
(6E)-10-Aza-10,11-dihydrosqualene-2,3-epoxide
-
-
(6E)-10-Aza-10,11-dihydrosqualene-2,3-epoxide
-
IC50: 0.0048 mM, at a protein concentration of 5 mg/ml
2-Aza-2,3-dihydrosqualene
-
-
2-Aza-2,3-dihydrosqualene
-
0.01 mM, 70% inhibition
2-Aza-2,3-dihydrosqualene
-
IC50: 7.5 mM
2-Aza-2,3-dihydrosqualene N-oxide
-
-
2-Aza-2,3-dihydrosqualene N-oxide
-
IC50: 3.7 mM
3-[(4-chlorobenzoyl)-4-phenoxy]quinuclidine
-
-
3-[(4-chlorobenzoyl)-4-phenoxy]quinuclidine
-
IC50: 160 nM
additional information
-
-
-
additional information
-
no inhibition: cholesterol
-
additional information
-
oxidosqualene cyclase inhibitors as antimicrobial agents
-
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0.000326
(4-Benzenesulfonyl-piperazin-1-yl)-(3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl)-methanone
Rattus norvegicus
-
IC50: 326 nM
0.0048
(6E)-10-Aza-10,11-dihydrosqualene-2,3-epoxide
Rattus norvegicus
-
IC50: 0.0048 mM, at a protein concentration of 5 mg/ml
0.02
(6Z)-10-aza-10,11-dihydrosqualene-2,3-epoxide
Rattus norvegicus
-
IC50: above 0.02 mM, at a protein concentration of 5 mg/ml
0.000124
(Z)-3-[4-(4-bromobenzoyl)phenacylidene]quinuclidine
Rattus norvegicus
-
IC50: 124 nM, oral and selective inhibition of cholesterol biosynthesis derived from enzyme inhibition
0.000398
1-(2-methyl-4-pyrimidinyl)-4-(1-(4-bromophenylsulfonyl)piperazin-4-ylcarbonyl)piperidine
Rattus norvegicus
-
76% inhibition at 0.001 mM, IC50: 398 nM
0.000082
1-(4-iodophenylsulfonyl)-4-(1-(4-pyridyl)piperidon-4-ylcarbonyl)piperazine
Rattus norvegicus
-
IC50: 82 nM
0.000116
1-(4-pyrimidinyl)-4-(1-(4-bromophenylsulfonyl)piperazin-4-ylcarbonyl)piperidine
Rattus norvegicus
-
complete inhibition at 0.001 mM, IC50: 116 nM
0.0075
19-aza-18,19,22,23-tetrahydrosqualene-2,3-epoxide
Rattus norvegicus
-
IC50: 0.0075 mM, protein concentration of 5 mg/ml
7.5
2-Aza-2,3-dihydrosqualene
Rattus norvegicus
-
IC50: 7.5 mM
3.7
2-Aza-2,3-dihydrosqualene N-oxide
Rattus norvegicus
-
IC50: 3.7 mM
0.00016
3-[(4-chlorobenzoyl)-4-phenoxy]quinuclidine
Rattus norvegicus
-
IC50: 160 nM
1.5
diethyl-(4,8,13,17,21-pentamethyl-docosa-4,8,12,16,20-pentaenyl)-aminoxide
Rattus norvegicus
-
IC50: 1.5 mM
3.2
Diethyl-(4,8,13,17,21-pentamethyl-docosa-4,8,12,16,20-pentaenyl)-ammonium
Rattus norvegicus
-
IC50: 3.2 mM
0.0025
N-[3-(1,1'-biphenyl-4-yloxy)propyl]-N,N-dimethylamine
Rattus norvegicus
-
IC50: 2500 nM
5.1
Trimethyl-(4,8,13,17,21-pentamethyl-docosa-4,8,12,16,20-pentaenyl)-ammonium
Rattus norvegicus
-
IC50: 5.1 mM
0.000228
[4-(4-Bromo-benzenesulfonyl)-piperazin-1-yl]-(3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl)-methanone
Rattus norvegicus
-
IC50: 228 nM
0.000049
[5-(4-(4-chloro-benzoyl)-3-fluoro-phenoxy)-pentyl]-methyl-propyl-ammonium fumarate
Rattus norvegicus
-
IC50: 49 nM
0.00009
{4-[4-(4,5-Dihydro-oxazol-2-yl)-benzylidene]-piperidin-1-yl}-(4-trifluoromethyl-phenyl)-methanone
Rattus norvegicus
-
IC50: 90 nM, complete inhibition at 0.001 nM
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Willett, J.D.; Sharpless, K.B.; Lord, K.E.; van Tamelen, E.E.; Clayton, R.B.
Squalene-2,3-oxide, an intermediate in the enzymatic conversion of squalene to lanosterol and cholesterol
J. Biol. Chem.
242
4182-4191
1967
Rattus norvegicus
brenda
Saat, Y.A.; Bloch, K.E.
Effect of a supernatant protein on microsomal squalene epoxidase and 2,3-oxidosqualene-lanosterol cyclase
J. Biol. Chem.
251
5155-5160
1976
Rattus norvegicus
brenda
Taton, M.; Benveniste, P.; Rahier, A.
N-[(1,5,9)-Trimethyl-decyl]-4alpha,10-dimethyl-8-aza-trans-decal-3beta-ol a novel potent inhibitor of 2,3-oxidosqualene cycloartenol and lanosterol cyclases
Biochem. Biophys. Res. Commun.
138
764-770
1986
Rattus norvegicus
brenda
Cattel, L.; Ceruti, M.; Balliano, G.; Viola, F.; Grosa, G.; Rocco, F.; Brusa, P.
2,3-Oxidosqualene cyclase: from azasqualenes to new site-directed inhibitors
Lipids
30
235-246
1995
Saccharomyces cerevisiae, Candida albicans, Rattus norvegicus, Sus scrofa
brenda
Viola, F.; Brusa, P.; Balliano, G.; Ceruti, M.; Boutaud, O.; Schuber, F.; Cattel, L.
Inhibition of 2,3-oxidosqualene cyclase and sterol biosynthesis by 10- and 19-azasqualene derivatives
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50
787-796
1995
Saccharomyces cerevisiae, Candida albicans, Homo sapiens, Rattus norvegicus, Sus scrofa
brenda
Jolidon, S.; Polak, A.M.; Guerry, P.; Hartman, P.G.
Inhibitors of 2,3-oxidosqualene lanosterol-cyclase as potential antifungal agents
Biochem. Soc. Trans.
18
47-48
1990
Candida albicans, Rattus norvegicus
brenda
Kusano, M.; Abe, I.; Sankawa, U.; Ebizuka, Y.
Purification and some properties of squalene 2,3-epoxide: lanosterol cyclase from rat liver
Chem. Pharm. Bull.
39
239-241
1991
Rattus norvegicus
brenda
Wannamaker, M.W.; Waid, P.P.; van Sickle, W.A.; McCarthy, J.R.; Wilson, P.K.; Schatzman, G.L.; Moore, W.R.
N-(1-Oxododecyl)-4alpha,10-dimethyl-8-aza-trans-decal-3beta-ol: a potent competitive inhibitor of 2,3-oxidosqualene cyclase
J. Med. Chem.
35
3581-3583
1992
Rattus norvegicus
brenda
Barth, M.M.; Binet, J.L.; Thomas, D.M.; de Fornel, D.C.; Samreth, S.; Schuber, F.J.; Renaut, P.P.
Structural and stereoelectronic requirements for the inhibition of mammalian oxidosqualene cyclase by substituted isoquinoline derivatives
J. Med. Chem.
39
2302-2312
1996
Rattus norvegicus
brenda
Stach, D.; Zheng, Y.F.; Perez, A.L.; Oehlschlager, A.C.; Abe, I.; Prestwich, G.D.; Hartman, P.G.
Synthesis and inhibition studies of sulfur-substituted squalene oxide analogues as mechanism-based inhibitors of 2,3-oxidosqualene-lanosterol cyclase
J. Med. Chem.
40
201-209
1997
Candida albicans, Rattus norvegicus, Sus scrofa
brenda
Moore, W.R.; Schatzman, G.L.
Purification of 2,3-oxidosqualene cyclase from rat liver
J. Biol. Chem.
267
22003-22006
1992
Rattus norvegicus
brenda
Abe, I.; Prestwich, G.D.
Molecular cloning, characterization, and functional expression of rat oxidosqualene cyclase cDNA
Proc. Natl. Acad. Sci. USA
92
9274-9278
1995
Rattus norvegicus
brenda
Astruc, M.; Tabacik, C.; Descomps, B.; Crastes de Paulet, A.
Squalene epoxidase and oxidosqualene lanosterol-cyclase activities in cholesterogenic and non-cholesterogenic tissues
Biochim. Biophys. Acta
487
204-211
1977
Rattus norvegicus
brenda
Cattel, L.; Ceruti, M.
Inhibitors of 2,3-oxidosqualene cyclase as tools for studying the mechanism and function of the enzyme
Crit. Rev. Biochem. Mol. Biol.
33
353-373
1998
Saccharomyces cerevisiae, Candida albicans, Canis lupus familiaris, Rattus norvegicus, Sus scrofa
brenda
Brown, G.R.; Hollinshead, D.M.; Stokes, E.S.; Clarke, D.S.; Eakin, M.A.; Foubister, A.J.; Glossop, S.C.; Griffiths, D.; Johnson, M.C.; McTaggart, F.; Mirrlees, D.J.; Smith, G.J.; Wood, R.
Quinuclidine inhibitors of 2,3-oxidosqualene cyclase-lanosterol synthase: optimization from lipid profiles
J. Med. Chem.
42
1306-1311
1999
Homo sapiens, Rattus norvegicus
brenda
Brown, G.R.; Hollinshead, D.M.; Stokes, E.S.; Waterson, D.; Clarke, D.S.; Foubister, A.J.; Glossop, S.C.; McTaggart, F.; Mirrlees, D.J.; Smith, G.J.; Wood, R.
A novel series of 4-piperidinopyridine and 4-piperidinopyrimidine inhibitors of 2,3-oxidosqualene cyclase-lanosterol synthase
J. Med. Chem.
43
4964-4972
2000
Homo sapiens, Rattus norvegicus
brenda
Hinshaw, J.C.; Suh, D.Y.; Garnier, P.; Buckner, F.S.; Eastman, R.T.; Matsuda, S.P.; Joubert, B.M.; Coppens, I.; Joiner, K.A.; Merali, S.; Nash, T.E.; Prestwich, G.D.
Oxidosqualene cyclase inhibitors as antimicrobial agents
J. Med. Chem.
46
4240-4243
2003
Pneumocystis carinii, Rattus norvegicus, Trypanosoma brucei, Trypanosoma cruzi
brenda
Venteclef, N.; Guillard, R.; Issandou, M.
The imidazoline-like drug S23515 affects lipid metabolism in hepatocyte by inhibiting the oxidosqualene: lanosterol cyclase activity
Biochem. Pharmacol.
69
1041-1048
2005
Macaca fascicularis, Homo sapiens, Rattus norvegicus
brenda
Mori, M.; Li, G.; Abe, I.; Nakayama, J.; Guo, Z.; Sawashita, J.; Ugawa, T.; Nishizono, S.; Serikawa, T.; Higuchi, K.; Shumiya, S.
Lanosterol synthase mutations cause cholesterol deficiency-associated cataracts in the Shumiya cataract rat
J. Clin. Invest.
116
395-404
2006
Rattus norvegicus (P48450)
brenda
Dang, H.; Liu, Y.; Pang, W.; Wang, N.; Shyy, J.Y.; Zhu, Y.
Suppression of 2,3-oxidosqualene cyclase by high-fat diet contributes to liver X receptor-alpha -mediated improvement of hepatic lipid profile
J. Biol. Chem.
284
6218-6226
2009
Mus musculus, Rattus norvegicus
brenda
Kang, L.; Shen, X.; Yang, M.; Zhang, G.; Zhang, J.; Qin, B.; Yang, L.; Hu, N.; Guan, H.
Distribution of lanosterol synthase and lanosterol in cornea, lens and retina tissue of rats
Zhonghua Shiyan Yanke Zazhi
35
201-206
2017
Rattus norvegicus
-
brenda