Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary extracted from

  • Giera, M.; Renard, D.; Ploessl, F.; Bracher, F.
    Lathosterol side chain amides—a new class of human lathosterol oxidase inhibitors (2008), Steroids, 73, 299-308.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.3.1.72 (2S)-2-((3S,5S,10S,13R,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-N-methylpropanamide 1 microM, 58% inhibition of total cholesterol production. Acts both on sterol reductoase and lathosterol oxidase Homo sapiens
1.3.1.72 (2S)-2-((3S,5S,10S,13R,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-N-propylpropanamide 1 microM, 45% inhibition of total cholesterol production. Acts both on sterol reductoase and lathosterol oxidase Homo sapiens
1.3.1.72 (2S)-2-((3S,5S,10S,13R,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)propanamide 1 microM, 75% inhibition of total cholesterol production Homo sapiens
1.3.1.72 (2S)-N-ethyl-2-((3S,5S,10S,13R,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)propanamide 1 microM, 61% inhibition of total cholesterol production Homo sapiens
1.3.1.72 (3S,5S,10S,13R,17R)-10,13-dimethyl-17-((S)-1-(methylamino)-1-oxopropan-2-yl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 1 microM, 84% inhibition of total cholesterol production. Acts both on sterol reductoase and lathosterol oxidase Homo sapiens
1.3.1.72 (3S,5S,10S,13R,17R)-10,13-dimethyl-17-((S)-1-oxo-1-(propylamino)propan-2-yl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 1 microM, 71% inhibition of total cholesterol production. Acts both on sterol reductoase and lathosterol oxidase Homo sapiens
1.3.1.72 (3S,5S,10S,13R,17R)-17-((S)-1-(ethylamino)-1-oxopropan-2-yl)-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 1 microM, 97% inhibition of total cholesterol production Homo sapiens
1.3.1.72 (3S,5S,10S,13R,17R)-17-((S)-1-amino-1-oxopropan-2-yl)-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 1 microM, 94% inhibition of total cholesterol production Homo sapiens
1.14.19.20 (3S,20S)-20-N-(2-methylpropyl)carbamoylpregn-7-en-3beta-ol specific Homo sapiens
1.14.19.20 (3S,20S)-20-N-(2-methylpropyl)carbamoylpregn-7-en-3beta-yl acetate specific for the enzyme. Prodrug, transformed into the 3beta-hydroxy derivative under in vitro conditions Homo sapiens
1.14.19.20 (3S,20S)-20-N-butylcarbamoylpregn-7-en-3beta-ol specific Homo sapiens
1.14.19.20 (3S,20S)-20-N-butylcarbamoylpregn-7-en-3beta-yl acetate specific for the enzyme. Prodrug, transformed into the 3beta-hydroxy derivative under in vitro conditions Homo sapiens
1.14.19.20 (3S,20S)-20-N-ethylcarbamoylpregn-7-en-3beta-ol
-
 Homo sapiens
1.14.19.20 (3S,20S)-20-N-ethylcarbamoylpregn-7-en-3beta-yl acetate
-
 Homo sapiens
1.14.19.20 (3S,20S)-20-N-pentylcarbamoylpregn-7-en-3beta-ol specific Homo sapiens
1.14.19.20 (3S,20S)-20-N-pentylcarbamoylpregn-7-en-3beta-yl acetate specific for the enzyme. Prodrug, transformed into the 3beta-hydroxy derivative under in vitro conditions Homo sapiens
1.14.19.20 (3S,20S)-20-N-propylcarbamoylpregn-7-en-3beta-ol
-
 Homo sapiens
1.14.19.20 (3S,20S)-20-N-propylcarbamoylpregn-7-en-3beta-yl acetate
-
 Homo sapiens
1.14.19.20 (3S,20S)-20-N-tert-butylcarbamoylpregn-7-en-3beta-ol specific Homo sapiens
1.14.19.20 (3S,20S)-20-N-tert-butylcarbamoylpregn-7-en-3beta-yl acetate specific for the enzyme. Prodrug, transformed into the 3beta-hydroxy derivative under in vitro conditions Homo sapiens
1.14.19.20 lathosterol side chain amides synthesis and compound screening, influence of different sterol amides on inhibition of the enzyme, overview, lathosterol-derived amides with larger substituents, e.g. butyl, isobutyl, tert-butyl, pentyl, at the amide nitrogen are selective inhibitors of lathosterol oxidase, overview Homo sapiens
1.14.19.20 additional information cytotoxicity and inhibitor potencies for inhibition of total cholesterol biosynthesis, overview Homo sapiens
1.14.19.20 Triarimol weak inhibition Homo sapiens

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.14.19.20 membrane bound Homo sapiens 16020
-
1.14.19.20 microsome
-
 Homo sapiens
-
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.19.20 additional information Homo sapiens the enzyme is involved in the post-squalene part of cholesterol biosynthesis ?
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.3.1.72 Homo sapiens
-
-
-
1.14.19.20 Homo sapiens
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.3.1.72 HL-60 cell
-
 Homo sapiens
-
1.14.19.20 HL-60 cell
-
 Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.19.20 additional information the enzyme is involved in the post-squalene part of cholesterol biosynthesis Homo sapiens ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.19.20 5-DES
-
 Homo sapiens
1.14.19.20 DELTA7-sterol-C5(6)-desaturase
-
 Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.14.19.20 0.00033
-
 inhibition of total cholesterol production Homo sapiens (3S,20S)-20-N-(2-methylpropyl)carbamoylpregn-7-en-3beta-ol
1.14.19.20 0.00045
-
 inhibition of total cholesterol production Homo sapiens (3S,20S)-20-N-(2-methylpropyl)carbamoylpregn-7-en-3beta-yl acetate
1.14.19.20 0.0007
-
 inhibition of total cholesterol production Homo sapiens (3S,20S)-20-N-butylcarbamoylpregn-7-en-3beta-ol
1.14.19.20 0.00091
-
 inhibition of total cholesterol production Homo sapiens (3S,20S)-20-N-butylcarbamoylpregn-7-en-3beta-yl acetate
1.14.19.20 0.00095
-
 inhibition of total cholesterol production Homo sapiens (3S,20S)-20-N-tert-butylcarbamoylpregn-7-en-3beta-yl acetate
1.14.19.20 0.00105
-
 inhibition of total cholesterol production Homo sapiens (3S,20S)-20-N-tert-butylcarbamoylpregn-7-en-3beta-ol
1.14.19.20 0.0011
-
 inhibition of total cholesterol production Homo sapiens (3S,20S)-20-N-pentylcarbamoylpregn-7-en-3beta-yl acetate
1.14.19.20 0.00116
-
 inhibition of total cholesterol production Homo sapiens (3S,20S)-20-N-pentylcarbamoylpregn-7-en-3beta-ol