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a mycothiol S-conjugate + H2O
an N-acetyl L-cysteine-S-conjugate + 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol
mycothiol bimane + H2O
?
-
-
-
-
?
mycothiol disulfide + H2O
?
-
-
-
-
?
mycothiol-3-(N-maleimidopropionyl)biocytin + H2O
?
-
-
-
-
?
mycothiol-7-(diethylamino)-3-(4'-maleimidylphenyl)-4-methylcoumarin + H2O
?
-
-
-
-
?
mycothiol-acetophenone + H2O
?
-
-
-
-
?
mycothiol-cerulenin + H2O
?
-
-
-
-
?
mycothiol-N-ethylmaleimide + H2O
?
-
-
-
-
?
RifS13 + H2O
1-D-myo-inositol-alpha-D-glucopyranoside + N-acetyl-S-[(2R,12Z,14E,16S,18S,19S,20S,21S,22S,23S,24E)-5,6,9,17,19-pentahydroxy-23-methoxy-21-(methoxycarbonyl)-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-8-yl]-L-cysteine
-
-
-
-
?
RifS17 + H2O
1-D-myo-inositol-alpha-D-glucopyranoside + N-acetyl-S-[(2R,12Z,14E,16S,18S,19S,20S,21S,22S,23S,24E)-5,17,19-trihydroxy-23-methoxy-21-(methoxycarbonyl)-2,4,12,16,18,20,22-heptamethyl-1,6,9,11-tetraoxo-1,2,6,9-tetrahydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-8-yl]-L-cysteine
-
-
-
-
?
additional information
?
-
-
the enzyme is highly specific for the mycothiol moiety of mycothiol S-conjugates and relatively nonspecific for the structure of the sulfur-linked conjugate
-
-
?
a mycothiol S-conjugate + H2O
an N-acetyl L-cysteine-S-conjugate + 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol
-
-
-
-
?
a mycothiol S-conjugate + H2O
an N-acetyl L-cysteine-S-conjugate + 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol
-
the enzyme is extremely specific for the mycothiol portion of the mycothiol S-conjugate and relatively nonspecific with respect to the R-moiety
-
-
?
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arenosclerin E
homology model built for Mca protein of Mycobacterium tuberculosis have high reliability and docking analysis show that arenosclerin E is a potent drug candidate for tuberculosis
(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl 2-({[3-chloro-4-(propan-2-ylsulfonyl)thiophen-2-yl]carbonyl}amino)-2-deoxy-alpha-D-glucopyranoside
-
11% inhibition at 0.05 mM
(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl 2-deoxy-2-({[1-(3,5-dichlorophenyl)-5-ethyl-1H-pyrazol-4-yl]carbonyl}amino)-alpha-D-glucopyranoside
-
26% inhibition at 0.05 mM
(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl 2-deoxy-2-[(4-nitrobenzoyl)amino]-alpha-D-glucopyranoside
-
15% inhibition at 0.05 mM
(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl 2-deoxy-2-[(furan-2-ylcarbonyl)amino]-alpha-D-glucopyranoside
-
15% inhibition at 0.05 mM
(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl 2-deoxy-2-[(naphthalen-2-ylcarbonyl)amino]-alpha-D-glucopyranoside
-
13% inhibition at 0.05 mM
(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl 2-deoxy-2-[(pyridin-4-ylcarbonyl)amino]-alpha-D-glucopyranoside
-
46% inhibition at 0.05 mM
(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl 2-deoxy-2-[(thiophen-2-ylcarbonyl)amino]-alpha-D-glucopyranoside
-
13% inhibition at 0.05 mM
(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl 2-deoxy-2-{[3-(propylsulfanyl)benzoyl]amino}-alpha-D-glucopyranoside
-
less than 10% inhibition at 0.05 mM
(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl 2-deoxy-2-{[4-(dimethylamino)benzoyl]amino}-alpha-D-glucopyranoside
-
44% inhibition at 0.05 mM
(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl 2-deoxy-2-{[4-(trifluoromethyl)benzoyl]amino}-alpha-D-glucopyranoside
-
16% inhibition at 0.05 mM
(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl 2-[(1-benzothiophen-6-ylcarbonyl)amino]-2-deoxy-alpha-D-glucopyranoside
-
15% inhibition at 0.05 mM
(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl 2-[(cyclopropylcarbonyl)amino]-2-deoxy-alpha-D-glucopyranoside
-
13% inhibition at 0.05 mM
(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl 2-[({6-[(4-chlorophenyl)sulfanyl]pyridin-2-yl}carbonyl)amino]-2-deoxy-alpha-D-glucopyranoside
-
10% inhibition at 0.05 mM
(2E)-3-(3,5-difluorophenyl)-N-[2-[(4-fluorophenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide
-
-
(2E)-3-(3-bromophenyl)-N-[2-[(2,6-dimethylphenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide
-
-
(2E)-3-(3-bromophenyl)-N-[2-[(4-fluorophenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide
-
-
(2E)-3-(3-chloro-4-hydroxyphenyl)-N-[2-[(4-fluorophenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide
-
-
(2E)-N-(5-amino-5-iminopentyl)-3-[4-(3-aminopropoxy)-3,5-dibromophenyl]-2-(hydroxyimino)propanamide
-
-
(2E)-N-[2-(2-amino-1H-imidazol-5-yl)ethyl]-3-[4-(3-aminopropoxy)-3,5-dibromophenyl]-2-(hydroxyimino)propanamide
-
-
(2E)-N-[2-[(4-aminophenyl)disulfanyl]ethyl]-3-(3,5-difluorophenyl)-2-(hydroxyimino)propanamide
-
-
(2E)-N-[2-[(4-aminophenyl)disulfanyl]ethyl]-3-(3-bromophenyl)-2-(hydroxyimino)propanamide
-
-
(2E)-N-[2-[(4-aminophenyl)disulfanyl]ethyl]-3-(3-chloro-4-hydroxyphenyl)-2-(hydroxyimino)propanamide
-
-
(2S,3R,26S,27S)-2,27-diamino-1,3,26-trihydroxyoctacosan-13-one
-
-
(2Z)-3-[4-(3-aminopropoxy)-3,5-dibromophenyl]-N-(4-carbamimidamidobutyl)-2-(hydroxyimino)propanamide
-
-
(2Z)-N-(4-amino-4-iminobutyl)-3-[4-(3-aminopropoxy)-3,5-dibromophenyl]-2-(hydroxyimino)propanamide
-
-
(2Z)-N-[(2-amino-1H-imidazol-5-yl)methyl]-3-[4-(3-aminopropoxy)-3,5-dibromophenyl]-2-(hydroxyimino)propanamide
-
-
(2Z)-N-[2-(2-amino-1H-imidazol-5-yl)ethyl]-3-[4-(3-aminopropoxy)-3,5-dibromophenyl]-2-(hydroxyimino)propanamide
-
-
(5R,10S)-N-[2-(2-amino-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
-
-
(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
-
-
(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
-
strongest inhibitor
1,10-phenanthroline
-
0.19% residual activity at 1 mM 1,10-phenanthroline
1,7-phenanthroline
-
slightly more than 50% inhibition at 1 mM 1,7-phenanthroline
1-pentyl-2-[10-(3-pentylpyridinium-1-yl)decyl]pyridinium
-
-
3,5,8-trihydroxyquinolin-4(1H)-one
-
-
disodium 3-[(E)-2-carboxylatoethenyl]benzoate
-
-
gliotoxin
-
mixed non-competitive inhibitor
mycothiol
-
about 20% residual activity at 2 mM mycothiol
oceanapiside
-
low micromolar, non-competitive inhibitor
S,S-dimethyl gliotoxin
-
-
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2.72
(2E)-3-(3,5-difluorophenyl)-N-[2-[(4-fluorophenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.065
(2E)-3-(3-bromophenyl)-N-[2-[(2,6-dimethylphenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.09
(2E)-3-(3-bromophenyl)-N-[2-[(4-fluorophenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.037
(2E)-3-(3-chloro-4-hydroxyphenyl)-N-[2-[(4-fluorophenyl)disulfanyl]ethyl]-2-(hydroxyimino)propanamide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.0028
(2E)-N-(5-amino-5-iminopentyl)-3-[4-(3-aminopropoxy)-3,5-dibromophenyl]-2-(hydroxyimino)propanamide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.036
(2E)-N-[2-(2-amino-1H-imidazol-5-yl)ethyl]-3-[4-(3-aminopropoxy)-3,5-dibromophenyl]-2-(hydroxyimino)propanamide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.45
(2E)-N-[2-[(4-aminophenyl)disulfanyl]ethyl]-3-(3,5-difluorophenyl)-2-(hydroxyimino)propanamide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.185
(2E)-N-[2-[(4-aminophenyl)disulfanyl]ethyl]-3-(3-bromophenyl)-2-(hydroxyimino)propanamide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.035
(2E)-N-[2-[(4-aminophenyl)disulfanyl]ethyl]-3-(3-chloro-4-hydroxyphenyl)-2-(hydroxyimino)propanamide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.1
(2S,3R,26S,27S)-2,27-diamino-1,3,26-trihydroxyoctacosan-13-one
Mycobacterium tuberculosis
-
at 31°C, pH not specified in the publication
0.003
(2Z)-N-(4-amino-4-iminobutyl)-3-[4-(3-aminopropoxy)-3,5-dibromophenyl]-2-(hydroxyimino)propanamide
Mycobacterium tuberculosis
-
at 31°C, pH not specified in the publication
0.03
(2Z)-N-[(2-amino-1H-imidazol-5-yl)methyl]-3-[4-(3-aminopropoxy)-3,5-dibromophenyl]-2-(hydroxyimino)propanamide
Mycobacterium tuberculosis
-
at 31°C, pH not specified in the publication
0.1
(5R,10S)-N-[2-(2-amino-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
-
at 31°C, pH not specified in the publication
0.002
(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
-
pH and temperature not specified in the publication
0.0001
1-pentyl-2-[10-(3-pentylpyridinium-1-yl)decyl]pyridinium
Mycobacterium tuberculosis
-
at 31°C, pH not specified in the publication
0.03
bromotyrosine oxime
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.003
disodium 3-[(E)-2-carboxylatoethenyl]benzoate
Mycobacterium tuberculosis
-
at 31°C, pH not specified in the publication
0.05
gliotoxin
Mycobacterium tuberculosis
-
at 31°C, pH not specified in the publication
0.01
oceanapiside
Mycobacterium tuberculosis
-
at 31°C, pH not specified in the publication
0.0028
psammaplin A
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.02 - 0.03
psammaplysin A
0.026 - 0.03
psammaplysin B
0.1
pseudoceratine
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.07
S,S-dimethyl gliotoxin
Mycobacterium tuberculosis
-
at 31°C, pH not specified in the publication
0.02
psammaplysin A
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.03
psammaplysin A
Mycobacterium tuberculosis
-
at 31°C, pH not specified in the publication
0.026
psammaplysin B
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.03
psammaplysin B
Mycobacterium tuberculosis
-
at 31°C, pH not specified in the publication
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Metaferia, B.B.; Ray, S.; Smith, J.A.; Bewley, C.A.
Design and synthesis of substrate-mimic inhibitors of mycothiol-S-conjugate amidase from Mycobacterium tuberculosis
Bioorg. Med. Chem. Lett.
17
444-447
2007
Mycobacterium tuberculosis
brenda
Steffek, M.; Newton, G.L.; Av-Gay, Y.; Fahey, R.C.
Characterization of Mycobacterium tuberculosis mycothiol S-conjugate amidase
Biochemistry
42
12067-12076
2003
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
brenda
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
Bioorg. Med. Chem. Lett.
12
2487-2490
2002
Mycobacterium tuberculosis
brenda
Fetterolf, B.; Bewley, C.A.
Synthesis of a bromotyrosine-derived natural product inhibitor of mycothiol-S-conjugate amidase
Bioorg. Med. Chem. Lett.
14
3785-3788
2004
Mycobacterium tuberculosis
brenda
Nicholas, G.M.; Eckman, L.L.; Newton, G.L.; Fahey, R.C.; Ray, S.; Bewley, C.A.
Inhibition and kinetics of mycobacterium tuberculosis and Mycobacterium smegmatis mycothiol-S-conjugate amidase by natural product inhibitors
Bioorg. Med. Chem.
11
601-608
2003
Mycobacterium tuberculosis, Mycolicibacterium smegmatis
brenda
Nicholas, G.M.; Newton, G.L.; Fahey, R.C.; Bewley, C.A.
Novel bromotyrosine alkaloids: inhibitors of mycothiol S-conjugate amidase
Org. Lett.
3
1543-1545
2001
Mycobacterium tuberculosis
brenda
Saxena, A.; Mishra, S.
Marine sponge derived natural products as inhibitors of mycothiol-S-conjugate amidase
Bioinformation
13
256-260
2017
Mycobacterium tuberculosis (P9WJN1), Mycobacterium tuberculosis ATCC 25618 (P9WJN1)
brenda
Kocabas, E.; Liu, H.; Hernick, M.
Identity of cofactor bound to mycothiol conjugate amidase (Mca) influenced by expression and purification conditions
Biometals
28
755-763
2015
Mycobacterium tuberculosis, Mycolicibacterium smegmatis
brenda