BRENDA - Enzyme Database

9-Methylidine-2,3-oxidosqualene derivatives as stereospecific mechanism-based inhibitors of liver and yeast oxidosqualene cyclase

Ceruti, M.; Rocco, F.; Viola, F.; Balliano, G.; Milla, P.; Arpicco, S.; Cattel, L.; J. Med. Chem. 41, 540-554 (1998)

Data extracted from this reference:

Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
5.4.99.7
(18E)-29-Methylidene-2,3-oxidohexanorsqualene
IC50: 0.0015 mM, irreversible; potent, irreversible
Saccharomyces cerevisiae
5.4.99.7
(18E)-29-Methylidene-2,3-oxidohexanorsqualene
IC50: 0.0035 mM, irreversible; potent, irreversible
Sus scrofa
5.4.99.7
(18Z)-29-Methylidene-2,3-oxidohexanorsqualene
IC50: 0.015 mM; potent, irreversible
Saccharomyces cerevisiae
5.4.99.7
(18Z)-29-Methylidene-2,3-oxidohexanorsqualene
IC50: 0.02 mM; potent, irreversible
Sus scrofa
5.4.99.7
(5E,9E,13E,17E)-21,22-epoxy-2,9,14,18,22-pentamethyl-5-vinyl-2,5,9,13,17-tricosapentaene
IC50: 0.018 mM
Saccharomyces cerevisiae
5.4.99.7
(5E,9E,13E,17E)-21,22-epoxy-2,9,14,18,22-pentamethyl-5-vinyl-2,5,9,13,17-tricosapentaene
IC50: 0.032 mM
Sus scrofa
5.4.99.7
(6E,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
IC50: 0.005 mM
Saccharomyces cerevisiae
5.4.99.7
(6E,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
IC50: 0.004 mM
Sus scrofa
5.4.99.7
(6Z,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
IC50: 0.001 mM
Saccharomyces cerevisiae
5.4.99.7
(6Z,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
IC50: 0.0004 mM
Sus scrofa
5.4.99.7
18,19-dihydro-29-methylidene-2,3-oxidosqualene
IC50: 0.1 mM
Sus scrofa
5.4.99.7
18-heptanor-2,3-oxidosqualene
IC50: 0.07 mM
Saccharomyces cerevisiae
5.4.99.7
18-heptanor-2,3-oxidosqualene
IC50: 0.015 mM
Sus scrofa
Organism
EC Number
Organism
UniProt
Commentary
Textmining
5.4.99.7
Saccharomyces cerevisiae
-
-
-
5.4.99.7
Sus scrofa
-
-
-
Source Tissue
EC Number
Source Tissue
Commentary
Organism
Textmining
5.4.99.7
liver
-
Sus scrofa
-
Substrates and Products (Substrate)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
5.4.99.7
(S)-squalene-2,3-epoxide
-
3615
Sus scrofa
Lanosterol
-
3615
Sus scrofa
-
5.4.99.7
(S)-squalene-2,3-epoxide
-
3615
Saccharomyces cerevisiae
Lanosterol
-
3615
Saccharomyces cerevisiae
-
IC50 Value
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
5.4.99.7
0.0004
-
IC50: 0.0004 mM
Sus scrofa
(6Z,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
5.4.99.7
0.001
-
IC50: 0.001 mM
Saccharomyces cerevisiae
(6Z,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
5.4.99.7
0.0015
-
IC50: 0.0015 mM, irreversible
Saccharomyces cerevisiae
(18E)-29-Methylidene-2,3-oxidohexanorsqualene
5.4.99.7
0.0035
-
IC50: 0.0035 mM, irreversible
Sus scrofa
(18E)-29-Methylidene-2,3-oxidohexanorsqualene
5.4.99.7
0.004
-
IC50: 0.004 mM
Sus scrofa
(6E,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
5.4.99.7
0.005
-
IC50: 0.005 mM
Saccharomyces cerevisiae
(6E,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
5.4.99.7
0.015
-
IC50: 0.015 mM
Sus scrofa
18-heptanor-2,3-oxidosqualene
5.4.99.7
0.015
-
IC50: 0.015 mM
Saccharomyces cerevisiae
(18Z)-29-Methylidene-2,3-oxidohexanorsqualene
5.4.99.7
0.018
-
IC50: 0.018 mM
Saccharomyces cerevisiae
(5E,9E,13E,17E)-21,22-epoxy-2,9,14,18,22-pentamethyl-5-vinyl-2,5,9,13,17-tricosapentaene
5.4.99.7
0.02
-
IC50: 0.02 mM
Sus scrofa
(18Z)-29-Methylidene-2,3-oxidohexanorsqualene
5.4.99.7
0.032
-
IC50: 0.032 mM
Sus scrofa
(5E,9E,13E,17E)-21,22-epoxy-2,9,14,18,22-pentamethyl-5-vinyl-2,5,9,13,17-tricosapentaene
5.4.99.7
0.07
-
IC50: 0.07 mM
Saccharomyces cerevisiae
18-heptanor-2,3-oxidosqualene
5.4.99.7
0.1
-
IC50: 0.1 mM
Sus scrofa
18,19-dihydro-29-methylidene-2,3-oxidosqualene
IC50 Value (protein specific)
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
5.4.99.7
0.0004
-
IC50: 0.0004 mM
Sus scrofa
(6Z,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
5.4.99.7
0.001
-
IC50: 0.001 mM
Saccharomyces cerevisiae
(6Z,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
5.4.99.7
0.0015
-
IC50: 0.0015 mM, irreversible
Saccharomyces cerevisiae
(18E)-29-Methylidene-2,3-oxidohexanorsqualene
5.4.99.7
0.0035
-
IC50: 0.0035 mM, irreversible
Sus scrofa
(18E)-29-Methylidene-2,3-oxidohexanorsqualene
5.4.99.7
0.004
-
IC50: 0.004 mM
Sus scrofa
(6E,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
5.4.99.7
0.005
-
IC50: 0.005 mM
Saccharomyces cerevisiae
(6E,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
5.4.99.7
0.015
-
IC50: 0.015 mM
Sus scrofa
18-heptanor-2,3-oxidosqualene
5.4.99.7
0.015
-
IC50: 0.015 mM
Saccharomyces cerevisiae
(18Z)-29-Methylidene-2,3-oxidohexanorsqualene
5.4.99.7
0.018
-
IC50: 0.018 mM
Saccharomyces cerevisiae
(5E,9E,13E,17E)-21,22-epoxy-2,9,14,18,22-pentamethyl-5-vinyl-2,5,9,13,17-tricosapentaene
5.4.99.7
0.02
-
IC50: 0.02 mM
Sus scrofa
(18Z)-29-Methylidene-2,3-oxidohexanorsqualene
5.4.99.7
0.032
-
IC50: 0.032 mM
Sus scrofa
(5E,9E,13E,17E)-21,22-epoxy-2,9,14,18,22-pentamethyl-5-vinyl-2,5,9,13,17-tricosapentaene
5.4.99.7
0.07
-
IC50: 0.07 mM
Saccharomyces cerevisiae
18-heptanor-2,3-oxidosqualene
5.4.99.7
0.1
-
IC50: 0.1 mM
Sus scrofa
18,19-dihydro-29-methylidene-2,3-oxidosqualene
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
5.4.99.7
(18E)-29-Methylidene-2,3-oxidohexanorsqualene
IC50: 0.0015 mM, irreversible; potent, irreversible
Saccharomyces cerevisiae
5.4.99.7
(18E)-29-Methylidene-2,3-oxidohexanorsqualene
IC50: 0.0035 mM, irreversible; potent, irreversible
Sus scrofa
5.4.99.7
(18Z)-29-Methylidene-2,3-oxidohexanorsqualene
IC50: 0.015 mM; potent, irreversible
Saccharomyces cerevisiae
5.4.99.7
(18Z)-29-Methylidene-2,3-oxidohexanorsqualene
IC50: 0.02 mM; potent, irreversible
Sus scrofa
5.4.99.7
(5E,9E,13E,17E)-21,22-epoxy-2,9,14,18,22-pentamethyl-5-vinyl-2,5,9,13,17-tricosapentaene
IC50: 0.018 mM
Saccharomyces cerevisiae
5.4.99.7
(5E,9E,13E,17E)-21,22-epoxy-2,9,14,18,22-pentamethyl-5-vinyl-2,5,9,13,17-tricosapentaene
IC50: 0.032 mM
Sus scrofa
5.4.99.7
(6E,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
IC50: 0.005 mM
Saccharomyces cerevisiae
5.4.99.7
(6E,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
IC50: 0.004 mM
Sus scrofa
5.4.99.7
(6Z,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
IC50: 0.001 mM
Saccharomyces cerevisiae
5.4.99.7
(6Z,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene
IC50: 0.0004 mM
Sus scrofa
5.4.99.7
18,19-dihydro-29-methylidene-2,3-oxidosqualene
IC50: 0.1 mM
Sus scrofa
5.4.99.7
18-heptanor-2,3-oxidosqualene
IC50: 0.07 mM
Saccharomyces cerevisiae
5.4.99.7
18-heptanor-2,3-oxidosqualene
IC50: 0.015 mM
Sus scrofa
Source Tissue (protein specific)
EC Number
Source Tissue
Commentary
Organism
Textmining
5.4.99.7
liver
-
Sus scrofa
-
Substrates and Products (Substrate) (protein specific)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
5.4.99.7
(S)-squalene-2,3-epoxide
-
3615
Sus scrofa
Lanosterol
-
3615
Sus scrofa
-
5.4.99.7
(S)-squalene-2,3-epoxide
-
3615
Saccharomyces cerevisiae
Lanosterol
-
3615
Saccharomyces cerevisiae
-