Information on EC 1.1.98.3 - decaprenylphospho-beta-D-ribofuranose 2-dehydrogenase

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The expected taxonomic range for this enzyme is: Mycobacterium

EC NUMBER
COMMENTARY hide
1.1.98.3
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RECOMMENDED NAME
GeneOntology No.
decaprenylphospho-beta-D-ribofuranose 2-dehydrogenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD = trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
mycolyl-arabinogalactan-peptidoglycan complex biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
trans,octacis-decaprenylphospho-beta-D-ribofuranose:FAD 2-oxidoreductase
The enzyme, isolated from the bacterium Mycobacterium smegmatis, is involved, along with EC 1.1.1.333, decaprenylphospho-D-erythro-pentofuranosid-2-ulose 2-reductase, in the epimerization of trans,octacis-decaprenylphospho-beta-D-ribofuranose to trans,octacis-decaprenylphospho-beta-D-arabinofuranose, the arabinosyl donor for the biosynthesis of mycobacterial cell wall arabinan polymers.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2Z,6E)-farnesylphosphoryl-beta-D-ribofuranose + FAD
(2Z,6E)-farnesylphosphoryl-D-beta-D-erythro-pentofuranosid-2-ulose + FADH2
show the reaction diagram
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oxidation reaction calyzed by decaprenylphospho-beta-D-ribofuranose 2-oxidase DprE1
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?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
show the reaction diagram
trans,octacis-decaprenylphospho-beta-D-ribofuranose + O2 + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + H2O2 + FADH2
show the reaction diagram
trans,octacis-decaprenylphospho-beta-D-ribofuranose + resazurin + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + resorufin + FADH2
show the reaction diagram
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
show the reaction diagram
trans,octacis-decaprenylphospho-beta-D-ribofuranose + O2 + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + H2O2 + FADH2
show the reaction diagram
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(3,4-dihydroisoquinolin-2(1H)-yl)[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
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(4-(2-methoxyethyl)piperazin-1-yl)(6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)methanone
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(4-benzylpiperazin-1-yl)[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
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(4-methylpiperidin-1-yl)[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
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(5-chloro-1-methyl-1H-pyrazol-4-yl)(3-endo-3-((5-fluoro-1H-indazol-3-yl)amino)-8-azabicyclo[3.2.1]oct-8-yl)methanone
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(5-chloro-1-methyl-1H-pyrazol-4-yl)(4-((2-methoxyquinolin-4-yl)amino)piperidin-1-yl)methanone
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(5-chloro-1-methyl-1H-pyrazol-4-yl)(4-((5-fluoro-1H-indazol-3-yl)amino)piperidin-1-yl)methanone
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(5-chloro-1-methyl-1H-pyrazol-4-yl)(4-(cinnolin-4-ylamino)-piperidin-1-yl)methanone
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(6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)(piperidin-1-yl)methanone
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(S)-(2-(6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)-4,5-dihydrooxazol-4-yl)(pyrrolidin-1-yl)methanone
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(S)-(2-(7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)-4,5-dihydrooxazol-4-yl)(pyrrolidin-1-yl)methanone
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(S)-7-nitro-2-(1-oxo-1-(pyrrolidin-1-yl)propan-2-ylcarbamoyl)-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
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(S)-N-(3-hydroxy-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)-6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazole-2-carboxamide
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(S)-N-(4-hydroxy-1-oxo-1-(piperidin-1-yl)butan-2-yl)-6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazole-2-carboxamide
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1,3-dimethyl-5-((3-(trifluoromethyl)benzylamino)methyl)-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
1-(6-methoxy-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-N-(3-(trifluoromethyl)benzyl)methanamine
1-methyl-2,4,7-trinitroxanthone
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mutations C387S and C387G confer resistance to 1-methyl-2,4,7-trinitroxanthone
1-[(4-tert-butylphenyl)methyl]-3-nitro-1H-1,2,4-triazole
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1-[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidine-4-carbonyl]piperidine-4-carboxylic acid
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2-(4,5-dihydrooxazol-2-yl)-7-nitro-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
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2-(4-(2-methoxyethyl)piperazine-1-carbonyl)-7-nitro-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
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2-(4-butylpiperazin-1-yl)-8-(1H-pyrrol-1-yl)-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
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PyrBTZ03
2-(6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)-4,5-dihydrooxazole
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2-(7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)-4,5-dihydrooxazole
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2-(methoxymethyl)-7-nitro-5-(trifluoromethyl)benzo[d]thiazole
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2-(piperidine-1-carbonyl)-5-(trifluoromethyl)benzo[d]thiazol-7-ylboronic acid
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2-(piperidine-1-carbonyl)-5-(trifluoromethyl)benzo[d]thiazole-7-carbonitrile
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2-(piperidine-1-carbonyl)-5-(trifluoromethyl)benzo[d]thiazole-7-carboxylic acid
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2-[(2S)-2-methyl-1,4-dioxa-8-azaspiro[4,5]dec-8-yl]-8-(1H-pyrrol-1-yl)-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
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PyrBTZ01
2-[(2S)-2-methyl-1,4-dioxa-8-azaspiro[4,5]dec-8-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
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BTZ043
2-[(2S)-2-methyl-1,4-dioxa-8-azaspiro[4.5]dec-8-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
2-[(2S)-2-methyl-1,4-dioxa-8-azaspiro[4.5]decan-8-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-(1H-pyrrol-1-yl)-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
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PyrBTZ02
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2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-(2,5-dimethyl-1H-pyrrol-1-yl)-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
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PyrBTZ04
2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
3,7-dimethyl-1-phenyl-5-((3-(trifluoromethyl)benzylamino)-methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
3-(((3-methyl-6-oxo-1-phenyl-6,7-dihydro-1H-pyrazolo[3,4-b]-pyridin-5-yl)methylamino)methyl)benzonitrile
3-(2-(piperidine-1-carbonyl)-5-(trifluoromethyl)benzo[d]thiazol-7-yl)-1,2,3-oxadiazol-3-ium-5-olate
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3-cyclopropyl-1-phenyl-5-(((6-(trifluoromethyl)pyridin-2-yl)-methylamino)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
3-cyclopropyl-1-phenyl-5-((3-(trifluoromethyl)benzylamino)-methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
3-cyclopropyl-5-(((3-methyl-6-(trifluoromethyl)pyridin-2-yl)-methylamino)methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
3-cyclopropyl-5-((2-fluoro-3-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
3-cyclopropyl-5-((2-fluoro-5-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
3-cyclopropyl-5-((2-methyl-5-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
3-isopropyl-5-((2-methyl-5-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
3-methyl-1-(pyridin-2-yl)-5-((3-(trifluoromethyl)benzylamino)-methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
3-methyl-1-p-tolyl-5-((3-(trifluoromethyl)benzylamino)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
3-methyl-1-phenyl-5-((3-(trifluoromethyl)benzylamino)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
3-methyl-1-phenyl-5-((7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
3-methyl-5-((2-methyl-5-(trifluoromethyl)benzylamino)methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
3-methyl-5-((3-methylbenzylamino)methyl)-1-phenyl-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
3-methyl-5-((methyl(3-(trifluoromethyl)benzyl)amino)methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
3-methyl-6-oxo-1-phenyl-N-(3-(trifluoromethyl)benzyl)-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
3-nitro-N-[(1R)-1-phenylethyl]-5-(trifluoromethyl)benzamide
3-nitroso-N-[(1R)-1-phenylethyl]-5-(trifluoromethyl)benzamide
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benzothiazinone-derived inhibitor, binding includes a covalent link to conserved Cys387, and trifluoromethyl group is a second key determinant of interaction with the enzyme
3-{[(4-methoxyphenyl)methyl]amino}-6-(trifluoromethyl)quinoxaline-2-carboxylic acid
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97% inhibition at 0.04 mM
4-(((1R,3R,5S)-8-((4,5-dimethylisoxazol-3-yl)carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)amino)-6,7-difluoroquinolin-2(1H)-one
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4-(((1R,3R,5S)-8-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)amino)-1-methyl-1,8-naphthyridin-2(1H)-one
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4-(((1R,3R,5S)-8-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)amino)-6,7-difluoro-1-methylquinolin-2(1H)-one
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4-(((1R,3R,5S)-8-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)amino)-6-fluoro-1-methylquinolin-2(1H)-one
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4-(((1R,3R,5S)-8-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)amino)-6-fluoroquinolin-2(1H)-one
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4-(((1R,3R,5S)-8-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)amino)-6-phenylpyridin-2(1H)-one
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4-(((1R,3S,5S)-8-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)amino)-6-fluoroquinolin-2(1H)-one
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4-(((2S,4R)-1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-2-methylpiperidin-4-yl)amino)-6,7-difluoroquinolin-2(1H)-one
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4-(((2S,4R)-1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-2-methylpiperidin-4-yl)amino)quinolin-2(1H)-one
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4-(((2S,4S)-1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-2-methylpiperidin-4-yl)amino)quinolin-2(1H)-one
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4-((1-((1,5-dimethyl-1H-1,2,3-triazol-4-yl)carbonyl)piperidin-4-yl)amino)-6-fluoroquinolin-2(1H)-one
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4-((1-((1,5-dimethyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)-amino)quinolin-2(1H)-one
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4-((1-((1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-quinolin-2(1H)-one
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4-((1-((4,5-dimethyl-1,2-oxazol-3-yl)carbonyl)piperidin-4-yl)-amino)-6,7-difluoroquinolin-2(1H)-one
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4-((1-((4,5-dimethylisoxazol-3-yl)carbonyl)piperidin-4-yl)amino)-6,7-difluoro-1-methylquinolin-2(1H)-one
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4-((1-((4,5-dimethylisoxazol-3-yl)carbonyl)piperidin-4-yl)amino)-6-fluoroquinolin-2(1H)-one
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4-((1-((5-chloro-1-ethyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)-amino)-6-fluoroquinolin-2(1H)-one
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4-((1-((5-chloro-1-isopropyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)quinolin-2(1H)-one
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4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)azetidin-3-yl)amino)quinolin-2(1H)-one
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4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-1-ethylquinolin-2(1H)-one
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4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-1-methylquinolin-2(1H)-one
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4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-6,7-difluoro-1-methylquinolin-2(1H)-one
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4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-6,7-difluoroquinolin-2(1H)-one
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4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-6-fluoroquinolin-2(1H)-one
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4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-6-phenylpyridin-2(1H)-one
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4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-7,8-difluoroquinolin-2(1H)-one
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4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-7-fluoroquinolin-2(1H)-one
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4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-8-fluoroquinolin-2(1H)-one
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4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)quinolin-2(1H)-one
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4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)methylamino)quinolin-2(1H)-one
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4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)oxy)quinolin-2(1H)-one
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4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)pyrrolidin-3-yl)amino)quinolin-2(1H)-one
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4-((2-methoxyethyl)piperazin-1-yl)(7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)methanone
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4-((3-endo-8-((4,5-Dimethyl-1,2-oxazol-3-yl)carbonyl)-8-azabicyclo[3.2.1]oct-3-yl)amino)-6,7-difluoro-1-methylquinolin-2(1H)-one
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4-((3-endo-8-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-8-azabicyclo[3.2.1]oct-3-yl)amino)-6,7-difluoroquinolin-2(1H)-one
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4-((7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)methyl)morpholine
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5-((3,4-dimethylbenzylamino)methyl)-3-methyl-1-phenyl-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
5-((3-fluorobenzylamino)methyl)-3-methyl-1-phenyl-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
5-((benzylamino)methyl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]-pyridin-6(7H)-one
6-bromo-3-methyl-8-nitro-2-phenylquinoline
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6-fluoro-4-((1-((1-methyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-carbonyl)piperidin-4-yl)amino)quinolin-2(1H)-one
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6-methyl-7-nitro-N-(pyridin-2-ylmethyl)-5-(trifluoromethyl)benzo[d]thiazole-2-carboxamide
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7-nitro-2-(piperidine-1-carbonyl)-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
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7-nitro-2-(piperidine-1-carbonyl)benzo[d]thiazole-5-carbonitrile
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7-nitro-2-(pyridin-2-ylmethylcarbamoyl)-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
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7-nitro-2-(pyridin-3-ylmethylcarbamoyl)-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
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7-nitro-5-((trifluoromethyl)-1,3-benzothiazol-2-yl)-piperidin-1-ylmethanone
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7-nitro-N-(pyridin-2-ylmethyl)-5-(trifluoromethyl)benzo[d]thiazole-2-carboxamide
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8-((3-endo-8-((4,5-dimethyl-1,2-oxazol-3-yl)carbonyl)-8-azabicyclo[3.2.1]oct-3-yl)amino)-5-methylpyrido[2,3-b]pyrazin-6(5H)-one
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BTZ043
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ethyl 1-[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidine-4-carbonyl]piperidine-4-carboxylate
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ethyl {2-[(1,3-benzothiazole-2-carbonyl)amino]thiophene-3-carbonyl}carbamate
morpholino(7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)methanone
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N,N-dimethyl-1-[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidine-4-carbonyl]piperidine-4-carboxamide
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N-(2-(4-methoxyphenoxy)ethyl)-3,5-dinitrobenzamide
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more than a ten-fold decrease in the number of colony-forming units is observed with both human and mouse primary cells at a N-(2-(4-methoxyphenoxy) ethyl)-3,5-dinitrobenzamide concentrations above 5 microM, compound is also highly active against multidrug-resistant and extensively drug-resistant clinical isolates. N-(2-(4-methoxyphenoxy)ethyl)-3,5-dinitrobenzamide shows a clear-cut effect on the synthesis of the arabinan domains of arabinogalactan and lipoarabinomannan, and inhibition of decaprenyl-phospho-arabinose formation in the treated extracts concurrent with the accumulation of decaprenylphospho-ribose. Target of the inhibitors is probably the heteromeric decaprenylphospho-ribose 29 epimerase encoded by the dprE1/dprE2 genes
N-(2-(benzyloxy)ethyl)-3,5-dinitrobenzamide
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more than a ten-fold decrease in the number of colony-forming units is observed with both human and mouse primary cells at a N-(2-(benzyloxy)ethyl)-3,5-dinitrobenzamide concentrations above 5 microM, compound is also highly active against multidrug-resistant and extensively drug-resistant clinical isolates. N-(2-(benzyloxy)ethyl)-3,5-dinitrobenzamide shows a clear-cut effect on the synthesis of the arabinan domains of arabinogalactan and lipoarabinomannan, and inhibition of decaprenyl-phospho-arabinose formation in the treated extracts concurrent with the accumulation of decaprenylphospho-ribose. Target of the inhibitors is probably the heteromeric decaprenylphospho-ribose 29 epimerase encoded by the dprE1/dprE2 genes
N-(2-fluoroethyl)-1-[(6-methoxy-5-methylpyrimidin-4-yl)methyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide
N-(pyridin-2-ylmethyl)-5-(trifluoromethyl)benzo[d]thiazole-2-carboxamide
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N-methyl-7-nitro-2-(piperidine-1-carbonyl)benzo[d]thiazole-5-carboxamide
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N-[(2S)-3-hydroxy-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]-7-nitro-5-(trifluoromethyl)-1,3-benzothiazole-2-carboxamide
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N-[2-(4-methoxyphenoxy)ethyl]-3,5-dinitrobenzamide
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[4-[(2H-1,3-benzodioxol-5-yl)methyl]piperazin-1-yl][1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
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[4-[(4-fluorophenyl)methyl]piperidin-1-yl][1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
-
-
[4-[(methylamino)methyl]piperidin-1-yl][1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
-
-
[4-[(pyridin-2-yl)methyl]piperidin-1-yl][1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
-
-
[4-[(pyridin-3-yl)methyl]piperidin-1-yl][1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
-
-
additional information
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00026
(3,4-dihydroisoquinolin-2(1H)-yl)[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
Mycobacterium tuberculosis
-
at pH 7.5 and 22C
0.0017
(4-(2-methoxyethyl)piperazin-1-yl)(6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)methanone
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.0012
(4-benzylpiperazin-1-yl)[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
Mycobacterium tuberculosis
-
at pH 7.5 and 22C
0.0017
(4-methylpiperidin-1-yl)[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
Mycobacterium tuberculosis
-
at pH 7.5 and 22C
0.00012
(5-chloro-1-methyl-1H-pyrazol-4-yl)(3-endo-3-((5-fluoro-1H-indazol-3-yl)amino)-8-azabicyclo[3.2.1]oct-8-yl)methanone
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.078
(5-chloro-1-methyl-1H-pyrazol-4-yl)(4-((2-methoxyquinolin-4-yl)amino)piperidin-1-yl)methanone
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.00013
(5-chloro-1-methyl-1H-pyrazol-4-yl)(4-((5-fluoro-1H-indazol-3-yl)amino)piperidin-1-yl)methanone
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.01
(5-chloro-1-methyl-1H-pyrazol-4-yl)(4-(cinnolin-4-ylamino)-piperidin-1-yl)methanone
Mycobacterium tuberculosis
-
IC50 above 0.01 mM, at pH 8.5 and 25C
0.0022
(6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)(piperidin-1-yl)methanone
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.0012
(S)-(2-(6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)-4,5-dihydrooxazol-4-yl)(pyrrolidin-1-yl)methanone
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.000654
(S)-(2-(7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)-4,5-dihydrooxazol-4-yl)(pyrrolidin-1-yl)methanone
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.00006
(S)-7-nitro-2-(1-oxo-1-(pyrrolidin-1-yl)propan-2-ylcarbamoyl)-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.0012
(S)-N-(3-hydroxy-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)-6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazole-2-carboxamide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.0012
(S)-N-(4-hydroxy-1-oxo-1-(piperidin-1-yl)butan-2-yl)-6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazole-2-carboxamide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.1
1,3-dimethyl-5-((3-(trifluoromethyl)benzylamino)methyl)-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
IC50 above 0.1 mM, pH and temperature not specified in the publication
0.01
1-(6-methoxy-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-N-(3-(trifluoromethyl)benzyl)methanamine
Mycobacterium smegmatis
P9WJF1
IC50 above 0.01 mM, pH and temperature not specified in the publication
0.1
1-[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidine-4-carbonyl]piperidine-4-carboxylic acid
Mycobacterium tuberculosis
-
IC50 above 0.1 mM, at pH 7.5 and 22C
0.000276
2-(4,5-dihydrooxazol-2-yl)-7-nitro-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.000027
2-(4-(2-methoxyethyl)piperazine-1-carbonyl)-7-nitro-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.0039
2-(6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)-4,5-dihydrooxazole
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.0059
2-(methoxymethyl)-7-nitro-5-(trifluoromethyl)benzo[d]thiazole
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.1
2-(piperidine-1-carbonyl)-5-(trifluoromethyl)benzo[d]thiazole-7-carboxylic acid
Mycobacterium tuberculosis
-
IC50 above 0.1 mM, pH and temperature not specified in the publication
0.00161
2-[(2S)-2-methyl-1,4-dioxa-8-azaspiro[4,5]dec-8-yl]-8-(1H-pyrrol-1-yl)-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
Mycobacterium tuberculosis
-
at pH 7.5 and 30C
0.00000425
2-[(2S)-2-methyl-1,4-dioxa-8-azaspiro[4,5]dec-8-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
Mycobacterium tuberculosis
-
at pH 7.5 and 30C
0.00734
2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-(1H-pyrrol-1-yl)-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
Mycobacterium tuberculosis
-
at pH 7.5 and 30C
-
0.01
3,7-dimethyl-1-phenyl-5-((3-(trifluoromethyl)benzylamino)-methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
IC50 above 0.01 mM, pH and temperature not specified in the publication
0.0026
3-(((3-methyl-6-oxo-1-phenyl-6,7-dihydro-1H-pyrazolo[3,4-b]-pyridin-5-yl)methylamino)methyl)benzonitrile
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.0282
3-(2-(piperidine-1-carbonyl)-5-(trifluoromethyl)benzo[d]thiazol-7-yl)-1,2,3-oxadiazol-3-ium-5-olate
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.0005
3-cyclopropyl-1-phenyl-5-(((6-(trifluoromethyl)pyridin-2-yl)-methylamino)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.00004
3-cyclopropyl-1-phenyl-5-((3-(trifluoromethyl)benzylamino)-methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.00001
3-cyclopropyl-5-(((3-methyl-6-(trifluoromethyl)pyridin-2-yl)-methylamino)methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.000005
3-cyclopropyl-5-((2-fluoro-3-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.00007
3-cyclopropyl-5-((2-fluoro-5-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.00001
3-cyclopropyl-5-((2-methyl-5-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.000005
3-isopropyl-5-((2-methyl-5-(trifluoromethyl)benzylamino)-methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.0006
3-methyl-1-p-tolyl-5-((3-(trifluoromethyl)benzylamino)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.0004
3-methyl-1-phenyl-5-((3-(trifluoromethyl)benzylamino)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.0062
3-methyl-1-phenyl-5-((7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.000007
3-methyl-5-((2-methyl-5-(trifluoromethyl)benzylamino)methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.0028
3-methyl-5-((3-methylbenzylamino)methyl)-1-phenyl-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.00006
3-methyl-5-((methyl(3-(trifluoromethyl)benzyl)amino)methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.001
3-methyl-6-oxo-1-phenyl-N-(3-(trifluoromethyl)benzyl)-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.000007
4-(((1R,3R,5S)-8-((4,5-dimethylisoxazol-3-yl)carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)amino)-6,7-difluoroquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000026
4-(((1R,3R,5S)-8-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)amino)-1-methyl-1,8-naphthyridin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000008
4-(((1R,3R,5S)-8-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)amino)-6,7-difluoro-1-methylquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000012
4-(((1R,3R,5S)-8-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)amino)-6-fluoro-1-methylquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.00003
4-(((1R,3R,5S)-8-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)amino)-6-fluoroquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000053
4-(((1R,3R,5S)-8-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)amino)-6-phenylpyridin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.043
4-(((1R,3S,5S)-8-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)amino)-6-fluoroquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000021
4-(((2S,4R)-1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-2-methylpiperidin-4-yl)amino)-6,7-difluoroquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000026
4-(((2S,4R)-1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-2-methylpiperidin-4-yl)amino)quinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.01
4-(((2S,4S)-1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-2-methylpiperidin-4-yl)amino)quinolin-2(1H)-one
Mycobacterium tuberculosis
-
IC50 above 0.01 mM, at pH 8.5 and 25C
0.000011
4-((1-((1,5-dimethyl-1H-1,2,3-triazol-4-yl)carbonyl)piperidin-4-yl)amino)-6-fluoroquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.00021
4-((1-((1,5-dimethyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)-amino)quinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.0022
4-((1-((1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-quinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000018
4-((1-((4,5-dimethyl-1,2-oxazol-3-yl)carbonyl)piperidin-4-yl)-amino)-6,7-difluoroquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000038
4-((1-((4,5-dimethylisoxazol-3-yl)carbonyl)piperidin-4-yl)amino)-6,7-difluoro-1-methylquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000006
4-((1-((4,5-dimethylisoxazol-3-yl)carbonyl)piperidin-4-yl)amino)-6-fluoroquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000045
4-((1-((5-chloro-1-ethyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)-amino)-6-fluoroquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.007
4-((1-((5-chloro-1-isopropyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)quinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.0018
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)azetidin-3-yl)amino)quinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.1
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-1-ethylquinolin-2(1H)-one
Mycobacterium tuberculosis
-
IC50 above 0.1 mM, at pH 8.5 and 25C
0.00014
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-1-methylquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.00002
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-6,7-difluoro-1-methylquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000006
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-6,7-difluoroquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000005
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-6-fluoroquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.003
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-6-phenylpyridin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000009
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-7,8-difluoroquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000007
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-7-fluoroquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000011
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-8-fluoroquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.018
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)methylamino)quinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.008
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)oxy)quinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.0047
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)pyrrolidin-3-yl)amino)quinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000247
4-((2-methoxyethyl)piperazin-1-yl)(7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)methanone
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.000017
4-((3-endo-8-((4,5-Dimethyl-1,2-oxazol-3-yl)carbonyl)-8-azabicyclo[3.2.1]oct-3-yl)amino)-6,7-difluoro-1-methylquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.000009
4-((3-endo-8-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-8-azabicyclo[3.2.1]oct-3-yl)amino)-6,7-difluoroquinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.0052
4-((7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)methyl)morpholine
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.0012
5-((3,4-dimethylbenzylamino)methyl)-3-methyl-1-phenyl-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.002
5-((3-fluorobenzylamino)methyl)-3-methyl-1-phenyl-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.0014
5-((benzylamino)methyl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]-pyridin-6(7H)-one
Mycobacterium smegmatis
P9WJF1
pH and temperature not specified in the publication
0.000021
6-fluoro-4-((1-((1-methyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-carbonyl)piperidin-4-yl)amino)quinolin-2(1H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.0012
6-methyl-7-nitro-N-(pyridin-2-ylmethyl)-5-(trifluoromethyl)benzo[d]thiazole-2-carboxamide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.000095
7-nitro-2-(piperidine-1-carbonyl)-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.0018
7-nitro-2-(piperidine-1-carbonyl)benzo[d]thiazole-5-carbonitrile
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.000026
7-nitro-2-(pyridin-2-ylmethylcarbamoyl)-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.000213
7-nitro-5-((trifluoromethyl)-1,3-benzothiazol-2-yl)-piperidin-1-ylmethanone
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.000452
7-nitro-N-(pyridin-2-ylmethyl)-5-(trifluoromethyl)benzo[d]thiazole-2-carboxamide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.000183
8-((3-endo-8-((4,5-dimethyl-1,2-oxazol-3-yl)carbonyl)-8-azabicyclo[3.2.1]oct-3-yl)amino)-5-methylpyrido[2,3-b]pyrazin-6(5H)-one
Mycobacterium tuberculosis
-
at pH 8.5 and 25C
0.0036
ethyl 1-[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidine-4-carbonyl]piperidine-4-carboxylate
Mycobacterium tuberculosis
-
at pH 7.5 and 22C
0.0003
morpholino(7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)methanone
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.021
N,N-dimethyl-1-[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidine-4-carbonyl]piperidine-4-carboxamide
Mycobacterium tuberculosis
-
at pH 7.5 and 22C
0.1
N-(pyridin-2-ylmethyl)-5-(trifluoromethyl)benzo[d]thiazole-2-carboxamide
Mycobacterium tuberculosis
-
IC50 above 0.1 mM, pH and temperature not specified in the publication
0.053
N-methyl-7-nitro-2-(piperidine-1-carbonyl)benzo[d]thiazole-5-carboxamide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.000349
N-[(2S)-3-hydroxy-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]-7-nitro-5-(trifluoromethyl)-1,3-benzothiazole-2-carboxamide
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.0004
[4-[(2H-1,3-benzodioxol-5-yl)methyl]piperazin-1-yl][1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
Mycobacterium tuberculosis
-
at pH 7.5 and 22C
0.000054
[4-[(4-fluorophenyl)methyl]piperidin-1-yl][1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
Mycobacterium tuberculosis
-
at pH 7.5 and 22C
0.1
[4-[(methylamino)methyl]piperidin-1-yl][1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
Mycobacterium tuberculosis
-
IC50 above 0.1 mM, at pH 7.5 and 22C
0.0026
[4-[(pyridin-2-yl)methyl]piperidin-1-yl][1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
Mycobacterium tuberculosis
-
at pH 7.5 and 22C
0.00044
[4-[(pyridin-3-yl)methyl]piperidin-1-yl][1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
Mycobacterium tuberculosis
-
at pH 7.5 and 22C
PDB
SCOP
CATH
ORGANISM
UNIPROT
Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155)
Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155)
Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155)
Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)
Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)
Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)
Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)
Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)
Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)
Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)
Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
44000
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x * 44000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
sitting drop vapor diffusion method, using 15-20% (v/v) isopropanol, 0.2 M sodium citrate pH 6.8, and 0.5% (w/v) N,N-dimethyldodecylamine-N-oxide
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different crystal forms of ligand-free enzyme reveal considerable levels of structural flexibility of two surface loops that seem to govern accessibility of the active site. Structures of complexes with the benzothiazinone-derived nitroso derivative 3-nitroso-N-[(1R)-1-phenylethyl]-5-(trifluoromethyl)benzamide reveal that inhibitor binding includes a covalent link to conserved Cys387, and reveal a trifluoromethyl group as a second key determinant of interaction with the enzyme. A noncovalent complex is formed between the enzyme and 3-nitro-N-[(1R)-1-phenylethyl]-5-(trifluoromethyl)benzamide, which is structurally identical to 3-nitroso-N-[(1R)-1-phenylethyl]-5-(trifluoromethyl)benzamide except for an inert nitro group replacing the reactive nitroso group. Binding of benzothiazinone-class inhibitors to the enzyme is not strictly dependent on formation of the covalent link to Cys387
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
nickel-agarose affinity resin column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
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expressed in Escherichia coli BL21star cells
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expressed in Mycobacterium bovis strain BCG
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expression in Escherichia coli
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C394G
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benzothiazinone-resistant mutant, reduces benzothiazinones to inert metabolites while avoiding covalent inactivation
C394S
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benzothiazinone-resistant mutant, reduces benzothiazinones to inert metabolites while avoiding covalent inactivation
C387A
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the mutation confers resistance to benzothiazinones
C387N
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the mutation confers resistance to benzothiazinones and reduces the overall catalytic efficiency by about 4fold compared to the wild type enzyme
C387T
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the mutation confers resistance to benzothiazinones
C387A
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the mutation confers resistance to benzothiazinones
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C387G
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mutation confers resistance to 1-methyl-2,4,7-trinitroxanthone and to 3-nitro-N-[(1R)-1-phenylethyl]-5-(trifluoromethyl)benzamide; the mutation confers resistance to benzothiazinones and reduces the overall catalytic efficiency by about 4fold compared to the wild type enzyme
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C387N
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the mutation confers resistance to benzothiazinones and reduces the overall catalytic efficiency by about 4fold compared to the wild type enzyme
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C387S
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mutation confers resistance to 1-methyl-2,4,7-trinitroxanthone and to 3-nitro-N-[(1R)-1-phenylethyl]-5-(trifluoromethyl)benzamide; the mutation confers resistance to benzothiazinones
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C387T
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the mutation confers resistance to benzothiazinones
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additional information
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isolation of mutant strains resistant to dinitrobenzamides. All mutants show cross-resistance to benzothiazinones and dinitrobenzamides, and all the mutant strains with a higher level of resistance to dinitrobenzamides have a substitution C394G of MSMEG_6382 gene encoding decaprenylphospho-?-D-ribofuranose 2-oxidase
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis