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Literature summary extracted from

  • Nicholas, G.M.; Eckman, L.L.; Ray, S.; Hughes, R.O.; Pfefferkorn, J.A.; Barluenga, S.; Nicolaou, K.C.; Bewley, C.A.
    Bromotyrosine-derived natural and synthetic products as inhibitors of mycothiol-S-conjugate amidase (2002), Bioorg. Med. Chem. Lett., 12, 2487-2490.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.5.1.115 (2E)-3-(3,5-difluorophenyl)-N-[2-[(4-fluorophenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide
-
 Mycobacterium tuberculosis
3.5.1.115 (2E)-3-(3-bromophenyl)-N-[2-[(2,6-dimethylphenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide
-
 Mycobacterium tuberculosis
3.5.1.115 (2E)-3-(3-bromophenyl)-N-[2-[(4-fluorophenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide
-
 Mycobacterium tuberculosis
3.5.1.115 (2E)-3-(3-chloro-4-hydroxyphenyl)-N-[2-[(4-fluorophenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide
-
 Mycobacterium tuberculosis
3.5.1.115 (2E)-N-(5-amino-5-iminopentyl)-3-[4-(3-aminopropoxy)-3,5-dibromophenyl]-2-(hydroxyimino)propanamide
-
 Mycobacterium tuberculosis
3.5.1.115 (2E)-N-[2-(2-amino-1H-imidazol-5-yl)ethyl]-3-[4-(3-aminopropoxy)-3,5-dibromophenyl]-2-(hydroxyimino)propanamide
-
 Mycobacterium tuberculosis
3.5.1.115 (2E)-N-[2-[(4-aminophenyl)disulfanyl]ethyl]-3-(3,5-difluorophenyl)-2-(hydroxyimino)propanamide
-
 Mycobacterium tuberculosis
3.5.1.115 (2E)-N-[2-[(4-aminophenyl)disulfanyl]ethyl]-3-(3-bromophenyl)-2-(hydroxyimino)propanamide
-
 Mycobacterium tuberculosis
3.5.1.115 (2E)-N-[2-[(4-aminophenyl)disulfanyl]ethyl]-3-(3-chloro-4-hydroxyphenyl)-2-(hydroxyimino)propanamide
-
 Mycobacterium tuberculosis
3.5.1.115 (5R,10S)-N-[2-[2-amino-4-(3,5,8-trihydroxy-4-oxo-1,4-dihydroquinolin-6-yl)-1H-imidazol-5-yl]ethyl]-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide
-
 Mycobacterium tuberculosis
3.5.1.115 psammaplin A
-
 Mycobacterium tuberculosis
3.5.1.115 psammaplysin A
-
 Mycobacterium tuberculosis
3.5.1.115 psammaplysin B
-
 Mycobacterium tuberculosis
3.5.1.115 pseudoceratine
-
 Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.5.1.115 a mycothiol S-conjugate + H2O Mycobacterium tuberculosis
-
 an N-acetyl L-cysteine-S-conjugate + 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.5.1.115 Mycobacterium tuberculosis
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.5.1.115 a mycothiol S-conjugate + H2O
-
 Mycobacterium tuberculosis an N-acetyl L-cysteine-S-conjugate + 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol
-
 ?
3.5.1.115 mycothiol bimane + H2O
-
 Mycobacterium tuberculosis ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.5.1.115 MCA
-
 Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.5.1.115 0.002
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis (5R,10S)-N-[2-[2-amino-4-(3,5,8-trihydroxy-4-oxo-1,4-dihydroquinolin-6-yl)-1H-imidazol-5-yl]ethyl]-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide
3.5.1.115 0.0028
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis psammaplin A
3.5.1.115 0.0028
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis (2E)-N-(5-amino-5-iminopentyl)-3-[4-(3-aminopropoxy)-3,5-dibromophenyl]-2-(hydroxyimino)propanamide
3.5.1.115 0.02
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis psammaplysin A
3.5.1.115 0.026
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis psammaplysin B
3.5.1.115 0.035
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis (2E)-N-[2-[(4-aminophenyl)disulfanyl]ethyl]-3-(3-chloro-4-hydroxyphenyl)-2-(hydroxyimino)propanamide
3.5.1.115 0.036
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis (2E)-N-[2-(2-amino-1H-imidazol-5-yl)ethyl]-3-[4-(3-aminopropoxy)-3,5-dibromophenyl]-2-(hydroxyimino)propanamide
3.5.1.115 0.037
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis (2E)-3-(3-chloro-4-hydroxyphenyl)-N-[2-[(4-fluorophenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide
3.5.1.115 0.065
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis (2E)-3-(3-bromophenyl)-N-[2-[(2,6-dimethylphenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide
3.5.1.115 0.09
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis (2E)-3-(3-bromophenyl)-N-[2-[(4-fluorophenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide
3.5.1.115 0.1
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis pseudoceratine
3.5.1.115 0.185
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis (2E)-N-[2-[(4-aminophenyl)disulfanyl]ethyl]-3-(3-bromophenyl)-2-(hydroxyimino)propanamide
3.5.1.115 0.45
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis (2E)-N-[2-[(4-aminophenyl)disulfanyl]ethyl]-3-(3,5-difluorophenyl)-2-(hydroxyimino)propanamide
3.5.1.115 2.72
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis (2E)-3-(3,5-difluorophenyl)-N-[2-[(4-fluorophenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide