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Literature summary for 2.3.1.26 extracted from

  • Benfatti, F.; Cardillo, G.; Gentilucci, L.; Tolomelli, A.
    Synthesis and biological evaluation of unprecedented classes of spiro-beta-lactams and azido-beta-lactams as acyl-CoA:cholesterol acyltransferase inhibitors (2007), Bioorg. Med. Chem. Lett., 17, 1946-1950.
    View publication on PubMed

Application

Application Comment Organism
medicine ACAT is a key enzyme in controlling cholesterol metabolism and represents a promising target for the development of therapeutic agents and inhibitors to control hypercholesterolemia, atherosclerosis and Alzheimer's disease Mammalia

Inhibitors

Inhibitors Comment Organism Structure
(1R,3R,7R)-1-[(1S)-1-hydroxypropyl]-3,7-diphenyl-6-[(1S)-1-phenylethyl]-2-oxa-6-azaspiro[3.3]heptan-5-one 45% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia
(1R,3R,7S)-1-[(1S)-1-hydroxypropyl]-3,7-diphenyl-6-[(1S)-1-phenylethyl]-2-oxa-6-azaspiro[3.3]heptan-5-one 66% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia
(1R,3R,7S)-1-[(1S)-1-hydroxypropyl]-3,7-diphenyl-6-[(1S)-1-phenylethyl]-2-oxa-6-azaspiro[3.3]heptan-5-one 0.01 mM, 66% inhibition Oryctolagus cuniculus
(1S)-1-[(1R,3R,5R)-3,5-diphenyl-6-[(1S)-1-phenylethyl]-2-oxa-6-azaspiro[3.3]hept-1-yl]propan-1-ol 0.01 mM, 45% inhibition Oryctolagus cuniculus
(3R,5R,7R,8S)-7-ethyl-8-hydroxy-3,5-diphenyl-2-[(1S)-1-phenylethyl]-6-oxa-2-azaspiro[3.4]octan-1-one 0.01 mM, 23% inhibition Oryctolagus cuniculus
(3R,5S,7S,8R)-7-ethyl-8-hydroxy-3,5-diphenyl-2-[(1R)-1-phenylethyl]-6-oxa-2-azaspiro[3.4]octan-1-one 27% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia
(3S,4S)-3-[(1R,2R)-2-azido-1-hydroxybutyl]-3-bromo-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one 65% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia
(3S,4S)-3-[(1S,2S)-2-azido-1-hydroxybutyl]-3-bromo-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one 60% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia
(3S,5R,7R,8S)-7-ethyl-8-hydroxy-3,5-diphenyl-2-[(1S)-1-phenylethyl]-6-oxa-2-azaspiro[3.4]octan-1-one 0.01 mM, 27% inhibition Oryctolagus cuniculus
(3S,5S,7S,8R)-7-ethyl-8-hydroxy-3,5-diphenyl-2-[(1R)-1-phenylethyl]-6-oxa-2-azaspiro[3.4]octan-1-one 23% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia
(4S)-3-[(1R,2S)-2-azido-1-hydroxybutyl]-3-[(R)-hydroxy(phenyl)methyl]-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one 0.01 mM, 87% inhibition Oryctolagus cuniculus
(4S)-3-[(1R,2S)-2-azido-1-hydroxybutyl]-3-[(S)-hydroxy(phenyl)methyl]-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one 87% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia
(4S)-3-[(1S,2R)-2-azido-1-hydroxybutyl]-3-[(R)-hydroxy(phenyl)methyl]-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one 79% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia
(4S)-3-[(1S,2R)-2-azido-1-hydroxybutyl]-3-[(S)-hydroxy(phenyl)methyl]-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one 0.01 mM, 79% inhibition Oryctolagus cuniculus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
acyl-CoA + cholesterol Mammalia
-
CoA + cholesterol ester
-
?

Organism

Organism UniProt Comment Textmining
Mammalia
-
-
-
Oryctolagus cuniculus
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
acyl-CoA + cholesterol
-
Mammalia CoA + cholesterol ester
-
?
palmitoyl-CoA + cholesterol
-
Oryctolagus cuniculus CoA + cholesteryl palmitate
-
?

Synonyms

Synonyms Comment Organism
ACAT two isoforms, ACAT1 and ACAT2 Mammalia
acyl-CoA cholesterol O-acyltransferase
-
Mammalia
acyl-CoA:cholesterol acyltransferase
-
Mammalia

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
additional information
-
23% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia (3S,5S,7S,8R)-7-ethyl-8-hydroxy-3,5-diphenyl-2-[(1R)-1-phenylethyl]-6-oxa-2-azaspiro[3.4]octan-1-one
additional information
-
27% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia (3R,5S,7S,8R)-7-ethyl-8-hydroxy-3,5-diphenyl-2-[(1R)-1-phenylethyl]-6-oxa-2-azaspiro[3.4]octan-1-one
additional information
-
45% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia (1R,3R,7R)-1-[(1S)-1-hydroxypropyl]-3,7-diphenyl-6-[(1S)-1-phenylethyl]-2-oxa-6-azaspiro[3.3]heptan-5-one
additional information
-
60% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia (3S,4S)-3-[(1S,2S)-2-azido-1-hydroxybutyl]-3-bromo-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one
additional information
-
65% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia (3S,4S)-3-[(1R,2R)-2-azido-1-hydroxybutyl]-3-bromo-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one
additional information
-
66% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia (1R,3R,7S)-1-[(1S)-1-hydroxypropyl]-3,7-diphenyl-6-[(1S)-1-phenylethyl]-2-oxa-6-azaspiro[3.3]heptan-5-one
additional information
-
79% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia (4S)-3-[(1S,2R)-2-azido-1-hydroxybutyl]-3-[(R)-hydroxy(phenyl)methyl]-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one
additional information
-
87% inhibition, reference standard lovastatin, literature data reference IC50 = 0.012 mM, 0.0168 mM when concurrently tested Mammalia (4S)-3-[(1R,2S)-2-azido-1-hydroxybutyl]-3-[(S)-hydroxy(phenyl)methyl]-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one