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

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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.
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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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
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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
-
top print hide
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 22°C
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 22°C
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 22°C
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 25°C
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 25°C
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 25°C
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 25°C
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 22°C
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 30°C
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 30°C
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 30°C
-
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 25°C
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 22°C
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 22°C
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 22°C
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 22°C
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 22°C
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 22°C
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 22°C
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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)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
44000
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x * 44000, SDS-PAGE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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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
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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
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
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LINKS TO OTHER DATABASES (specific for EC-Number 1.1.98.3)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)