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Literature summary for 1.1.1.145 extracted from

  • Thomas, S.T.; Yang, X.; Sampson, N.S.
    Inhibition of the M. tuberculosis 3beta-hydroxysteroid dehydrogenase by azasteroids (2011), Bioorg. Med. Chem. Lett., 21, 2216-2219.
    View publication on PubMedView publication on EuropePMC

Inhibitors

Inhibitors Comment Organism Structure
(12S,12aS,14bR)-N,N,12a,14b-tetramethyl-3-oxo-1,2,3,4,5,6,7,9,9a,9b,10,11,12,12a,13,14,14a,14b-octadecahydroazepino[3,2,1-de]cyclopenta[i]phenanthridine-12-carboxamide
-
Mycobacterium tuberculosis
(1R,4S,9aR,11aR)-4,9a,11a-trimethyl-1-((R)-6-methylheptan-2-yl)-3,3a,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridin-7(2H)-one
-
Mycobacterium tuberculosis
(1R,9aR,11aR)-9a,11a-dimethyl-1-((R)-6-methylheptan-2-yl)-3,3a,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridin-7(2H)-one
-
Mycobacterium tuberculosis
(1S,8bS,10aS)-N,N-diethyl-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,7,7a,8,8a,8b,8c,9,10,10a-hexadecahydrocyclopenta[i]cyclopropa[a]phenanthridine-1-carboxamide
-
Mycobacterium tuberculosis
(1S,8bS,10aS)-N-tert-butyl-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,7,7a,8,8a,8b,8c,9,10,10a-hexadecahydrocyclopenta[i]cyclopropa[a]phenanthridine-1-carboxamide
-
Mycobacterium tuberculosis
(1S,9aR,11aS)-1-(4,5-diphenyl-4,5-dihydro-1,3-oxazol-2-yl)-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[i]phenanthridin-7-one
-
Mycobacterium tuberculosis
(1S,9aR,11aS)-5-butyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
Mycobacterium tuberculosis
(1S,9aR,11aS)-5-hexyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
Mycobacterium tuberculosis
(1S,9aR,11aS)-6-ethyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
Mycobacterium tuberculosis
(1S,9aR,11aS)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxylic acid
-
Mycobacterium tuberculosis
(1S,9aR,11aS)-9a,11a-dimethyl-N-[4-(morpholin-4-yl)phenyl]-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
Mycobacterium tuberculosis
(1S,9aR,11aS)-N,N,5,9a,11a-pentamethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
Mycobacterium tuberculosis
(1S,9aR,11aS)-N,N,6,9a,11a-pentamethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
Mycobacterium tuberculosis
(1S,9aR,11aS)-N,N,9a,11a-tetramethyl-7-oxo-5-propyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
Mycobacterium tuberculosis
(1S,9aR,11aS)-N-(2,5-di-tert-butylphenyl)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
Mycobacterium tuberculosis
(1S,9aR,11aS)-N-(2-benzoylphenyl)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
Mycobacterium tuberculosis
(1S,9aR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
Mycobacterium tuberculosis
(1S,9aR,11aS)-N-[2-tert-butyl-5-(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
Mycobacterium tuberculosis
(4aR,6aS,7S)-7-[2,5-bis(trifluoromethyl)benzoyl]-4a,6a-dimethyl-1,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-2H-indeno[5,4-f]quinolin-2-one
-
Mycobacterium tuberculosis
(4aR,6aS,7S)-N-tert-butyl-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
Mycobacterium tuberculosis

Organism

Organism UniProt Comment Textmining
Mycobacterium tuberculosis P9WQP7
-
-
Mycobacterium tuberculosis H37Rv P9WQP7
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
dehydroepiandrosterone + NAD+
-
Mycobacterium tuberculosis androst-5-en-3,17-dione + NADH + H+
-
?
dehydroepiandrosterone + NAD+
-
Mycobacterium tuberculosis H37Rv androst-5-en-3,17-dione + NADH + H+
-
?

Synonyms

Synonyms Comment Organism
3beta-hydroxysteroid dehydrogenase
-
Mycobacterium tuberculosis

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
assay at Mycobacterium tuberculosis

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8.5
-
assay at Mycobacterium tuberculosis

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0005
-
pH 8.5, 30°C Mycobacterium tuberculosis (1R,9aR,11aR)-9a,11a-dimethyl-1-((R)-6-methylheptan-2-yl)-3,3a,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridin-7(2H)-one
0.0008
-
pH 8.5, 30°C Mycobacterium tuberculosis (1R,4S,9aR,11aR)-4,9a,11a-trimethyl-1-((R)-6-methylheptan-2-yl)-3,3a,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridin-7(2H)-one
0.009
-
pH 8.5, 30°C Mycobacterium tuberculosis (1S,9aR,11aS)-1-(4,5-diphenyl-4,5-dihydro-1,3-oxazol-2-yl)-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[i]phenanthridin-7-one
0.023
-
pH 8.5, 30°C Mycobacterium tuberculosis (1S,9aR,11aS)-N-(2,5-di-tert-butylphenyl)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
0.027
-
pH 8.5, 30°C Mycobacterium tuberculosis (1S,9aR,11aS)-N-[2-tert-butyl-5-(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
0.027
-
pH 8.5, 30°C Mycobacterium tuberculosis (1S,9aR,11aS)-N-(2-benzoylphenyl)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
0.043
-
pH 8.5, 30°C Mycobacterium tuberculosis (12S,12aS,14bR)-N,N,12a,14b-tetramethyl-3-oxo-1,2,3,4,5,6,7,9,9a,9b,10,11,12,12a,13,14,14a,14b-octadecahydroazepino[3,2,1-de]cyclopenta[i]phenanthridine-12-carboxamide
0.05
-
value above, pH 8.5, 30°C Mycobacterium tuberculosis (1S,9aR,11aS)-N,N,9a,11a-tetramethyl-7-oxo-5-propyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
0.05
-
value above, pH 8.5, 30°C Mycobacterium tuberculosis (1S,9aR,11aS)-5-butyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
0.1
-
value above, pH 8.5, 30°C Mycobacterium tuberculosis (1S,9aR,11aS)-9a,11a-dimethyl-N-[4-(morpholin-4-yl)phenyl]-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
0.14
-
pH 8.5, 30°C Mycobacterium tuberculosis (1S,9aR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
0.15
-
value above, pH 8.5, 30°C Mycobacterium tuberculosis (4aR,6aS,7S)-7-[2,5-bis(trifluoromethyl)benzoyl]-4a,6a-dimethyl-1,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-2H-indeno[5,4-f]quinolin-2-one
0.156
-
pH 8.5, 30°C Mycobacterium tuberculosis (1S,9aR,11aS)-5-hexyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
0.2
-
value above, pH 8.5, 30°C Mycobacterium tuberculosis (1S,9aR,11aS)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxylic acid
0.2
-
value above, pH 8.5, 30°C Mycobacterium tuberculosis (1S,8bS,10aS)-N-tert-butyl-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,7,7a,8,8a,8b,8c,9,10,10a-hexadecahydrocyclopenta[i]cyclopropa[a]phenanthridine-1-carboxamide
0.26
-
value above, pH 8.5, 30°C Mycobacterium tuberculosis (1S,9aR,11aS)-6-ethyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
0.312
-
pH 8.5, 30°C Mycobacterium tuberculosis (4aR,6aS,7S)-N-tert-butyl-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
0.4
-
value above, pH 8.5, 30°C Mycobacterium tuberculosis (1S,9aR,11aS)-N,N,6,9a,11a-pentamethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
0.4
-
value above, pH 8.5, 30°C Mycobacterium tuberculosis (1S,9aR,11aS)-N,N,5,9a,11a-pentamethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
0.54
-
pH 8.5, 30°C Mycobacterium tuberculosis (1S,8bS,10aS)-N,N-diethyl-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,7,7a,8,8a,8b,8c,9,10,10a-hexadecahydrocyclopenta[i]cyclopropa[a]phenanthridine-1-carboxamide