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Information on EC 1.1.98.3 - decaprenylphospho-beta-D-ribofuranose 2-dehydrogenase
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1.1.98.3 decaprenylphospho-beta-D-ribofuranose 2-dehydrogenaseIUBMB Comments
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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Word Map
- 1.1.98.3
- tuberculosis
- mycobacterium
-
antitubercular
-
benzothiazinones
-
antimycobacterial
- pbtz169
-
antituberculosis
- arabinogalactan
- arabinans
-
anti-tb
-
nitroso
-
dinitrobenzamides
-
1,2,3-triazole
-
drug-susceptible
- d-arabinose
- corynebacterineae
-
xdr-tb
- analysis
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
decaprenylphospho-beta-D-ribofuranose 2-oxidase, decaprenylphosphoryl-beta-D-ribofuranose 2'-epimerase, decaprenylphosphoryl-beta-D-ribose 2'-epimerase, decaprenylphosphoryl-beta-D-ribose 2'-oxidase, decaprenylphosphoryl-beta-D-ribose 2-epimerase, decaprenylphosphoryl-beta-D-ribose oxidase, decaprenylphosphoryl-beta-D-ribose-2'-epimerase, decaprenylphosphoryl-D-ribose oxidase, DprE1, DprE2, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
decaprenylphosphoryl-beta-D-ribose 2'-epimerase
decaprenylphosphoryl-beta-D-ribose 2'-oxidase
decaprenylphosphoryl-beta-D-ribose oxidase
decaprenylphosphoryl-beta-D-ribose-2'-epimerase
DprE1
Rv3790
decaprenylphosphoryl-beta-D-ribose oxidase
-
DprE1
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD = trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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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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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2Z,6E)-farnesylphosphoryl-beta-D-ribofuranose + FAD
(2Z,6E)-farnesylphosphoryl-D-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
oxidation reaction calyzed by decaprenylphospho-beta-D-ribofuranose 2-oxidase DprE1
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
trans,octacis-decaprenylphospho-beta-D-ribofuranose + O2 + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + H2O2 + FADH2
trans,octacis-decaprenylphospho-beta-D-ribofuranose + resazurin + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + resorufin + FADH2
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
oxidation reaction catalyzed by decaprenylphospho-beta-D-ribofuranose 2-oxidase DprE1
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + O2 + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + H2O2 + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + O2 + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + H2O2 + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + resazurin + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + resorufin + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + resazurin + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + resorufin + FADH2
-
-
-
?
additional information
?
-
decaprenylphospho-beta-D-ribofuranose 2-oxidase DprE1 and decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose 2-reductase DprE2 together catalyze the epimerization of decaprenylphosphoryl-beta-D-ribofuranose to decaprenylphosphoryl-beta-D-arabinofuranose. Neither protein individually is sufficient to support the activity
-
-
?
additional information
?
-
-
the enzyme can use synthetic electron acceptors such as 2,6-dichlorophenolindophenol with good efficiency
-
-
?
additional information
?
-
decaprenylphospho-beta-D-ribofuranose 2-oxidase DprE1 and decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose 2-reductase DprE2 together catalyze the epimerization of decaprenylphosphoryl-beta-D-ribofuranose to decaprenylphosphoryl-beta-D-arabinofuranose. Neither protein individually is sufficient to support the activity
-
-
?
additional information
?
-
decaprenylphosphoryl-beta-D-ribofuranose 2'-epimerase is constituted of decaprenylphospho-beta-D-ribofuranose 2-oxidase DprE1 and decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose 2-reductase DprE2 that together catalyze the epimerization of decaprenylphosphoryl-beta-D-ribofuranose to decaprenylphosphoryl-beta-D-arabinofuranose
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
trans,octacis-decaprenylphospho-beta-D-ribofuranose + O2 + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + H2O2 + FADH2
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + O2 + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + H2O2 + FADH2
-
-
-
?
trans,octacis-decaprenylphospho-beta-D-ribofuranose + O2 + FAD
trans,octacis-decaprenylphospho-beta-D-erythro-pentofuranosid-2-ulose + H2O2 + FADH2
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(3,4-dihydroisoquinolin-2(1H)-yl)[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
-
(4-(2-methoxyethyl)piperazin-1-yl)(6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)methanone
-
(4-benzylpiperazin-1-yl)[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
-
(4-methylpiperidin-1-yl)[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidin-4-yl]methanone
-
(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
-
(5-chloro-1-methyl-1H-pyrazol-4-yl)(4-((2-methoxyquinolin-4-yl)amino)piperidin-1-yl)methanone
-
(5-chloro-1-methyl-1H-pyrazol-4-yl)(4-((5-fluoro-1H-indazol-3-yl)amino)piperidin-1-yl)methanone
-
(5-chloro-1-methyl-1H-pyrazol-4-yl)(4-(cinnolin-4-ylamino)-piperidin-1-yl)methanone
-
(6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)(piperidin-1-yl)methanone
-
(S)-(2-(6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)-4,5-dihydrooxazol-4-yl)(pyrrolidin-1-yl)methanone
-
(S)-(2-(7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)-4,5-dihydrooxazol-4-yl)(pyrrolidin-1-yl)methanone
-
(S)-7-nitro-2-(1-oxo-1-(pyrrolidin-1-yl)propan-2-ylcarbamoyl)-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
-
(S)-N-(3-hydroxy-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)-6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazole-2-carboxamide
-
(S)-N-(4-hydroxy-1-oxo-1-(piperidin-1-yl)butan-2-yl)-6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazole-2-carboxamide
-
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
mutations C387S and C387G confer resistance to 1-methyl-2,4,7-trinitroxanthone
1-[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidine-4-carbonyl]piperidine-4-carboxylic acid
-
2-(4,5-dihydrooxazol-2-yl)-7-nitro-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
-
2-(4-(2-methoxyethyl)piperazine-1-carbonyl)-7-nitro-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
-
2-(4-butylpiperazin-1-yl)-8-(1H-pyrrol-1-yl)-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
PyrBTZ03
2-(6-methyl-7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)-4,5-dihydrooxazole
-
2-(7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)-4,5-dihydrooxazole
-
2-(methoxymethyl)-7-nitro-5-(trifluoromethyl)benzo[d]thiazole
-
2-(piperidine-1-carbonyl)-5-(trifluoromethyl)benzo[d]thiazol-7-ylboronic acid
-
2-(piperidine-1-carbonyl)-5-(trifluoromethyl)benzo[d]thiazole-7-carbonitrile
-
2-(piperidine-1-carbonyl)-5-(trifluoromethyl)benzo[d]thiazole-7-carboxylic acid
-
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
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
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
PyrBTZ02
2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-(2,5-dimethyl-1H-pyrrol-1-yl)-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
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
-
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-((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-nitroso-N-[(1R)-1-phenylethyl]-5-(trifluoromethyl)benzamide
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
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
-
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
-
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
-
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
-
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
-
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
-
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
-
4-(((2S,4R)-1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-2-methylpiperidin-4-yl)amino)-6,7-difluoroquinolin-2(1H)-one
-
4-(((2S,4R)-1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-2-methylpiperidin-4-yl)amino)quinolin-2(1H)-one
-
4-(((2S,4S)-1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)-2-methylpiperidin-4-yl)amino)quinolin-2(1H)-one
-
4-((1-((1,5-dimethyl-1H-1,2,3-triazol-4-yl)carbonyl)piperidin-4-yl)amino)-6-fluoroquinolin-2(1H)-one
-
4-((1-((1,5-dimethyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)-amino)quinolin-2(1H)-one
-
4-((1-((1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-quinolin-2(1H)-one
-
4-((1-((4,5-dimethyl-1,2-oxazol-3-yl)carbonyl)piperidin-4-yl)-amino)-6,7-difluoroquinolin-2(1H)-one
-
4-((1-((4,5-dimethylisoxazol-3-yl)carbonyl)piperidin-4-yl)amino)-6,7-difluoro-1-methylquinolin-2(1H)-one
-
4-((1-((4,5-dimethylisoxazol-3-yl)carbonyl)piperidin-4-yl)amino)-6-fluoroquinolin-2(1H)-one
-
4-((1-((5-chloro-1-ethyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)-amino)-6-fluoroquinolin-2(1H)-one
-
4-((1-((5-chloro-1-isopropyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)quinolin-2(1H)-one
-
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)azetidin-3-yl)amino)quinolin-2(1H)-one
-
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-1-ethylquinolin-2(1H)-one
-
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-1-methylquinolin-2(1H)-one
-
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-6,7-difluoro-1-methylquinolin-2(1H)-one
-
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-6,7-difluoroquinolin-2(1H)-one
-
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-6-fluoroquinolin-2(1H)-one
-
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-6-phenylpyridin-2(1H)-one
-
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-7,8-difluoroquinolin-2(1H)-one
-
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-7-fluoroquinolin-2(1H)-one
-
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)-8-fluoroquinolin-2(1H)-one
-
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)amino)quinolin-2(1H)-one
-
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)methylamino)quinolin-2(1H)-one
-
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)piperidin-4-yl)oxy)quinolin-2(1H)-one
-
4-((1-((5-chloro-1-methyl-1H-pyrazol-4-yl)carbonyl)pyrrolidin-3-yl)amino)quinolin-2(1H)-one
-
4-((2-methoxyethyl)piperazin-1-yl)(7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)methanone
-
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
-
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
-
4-((7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)methyl)morpholine
-
6-fluoro-4-((1-((1-methyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-carbonyl)piperidin-4-yl)amino)quinolin-2(1H)-one
-
6-methyl-7-nitro-N-(pyridin-2-ylmethyl)-5-(trifluoromethyl)benzo[d]thiazole-2-carboxamide
-
7-nitro-2-(piperidine-1-carbonyl)-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
-
7-nitro-2-(piperidine-1-carbonyl)benzo[d]thiazole-5-carbonitrile
-
7-nitro-2-(pyridin-2-ylmethylcarbamoyl)-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
-
7-nitro-2-(pyridin-3-ylmethylcarbamoyl)-5-(trifluoromethyl)benzo[d]thiazole 3-oxide
-
7-nitro-5-((trifluoromethyl)-1,3-benzothiazol-2-yl)-piperidin-1-ylmethanone
-
7-nitro-N-(pyridin-2-ylmethyl)-5-(trifluoromethyl)benzo[d]thiazole-2-carboxamide
-
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
-
ethyl 1-[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidine-4-carbonyl]piperidine-4-carboxylate
-
morpholino(7-nitro-5-(trifluoromethyl)benzo[d]thiazol-2-yl)methanone
-
N,N-dimethyl-1-[1-[5-(1H-pyrrol-1-yl)-1,3,4-thiadiazol-2-yl]piperidine-4-carbonyl]piperidine-4-carboxamide
-
N-(2-(4-methoxyphenoxy)ethyl)-3,5-dinitrobenzamide
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
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-(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
-
N-methyl-7-nitro-2-(piperidine-1-carbonyl)benzo[d]thiazole-5-carboxamide
-
N-[(2S)-3-hydroxy-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]-7-nitro-5-(trifluoromethyl)-1,3-benzothiazole-2-carboxamide
-
[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
-
[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
-
1,3-dimethyl-5-((3-(trifluoromethyl)benzylamino)methyl)-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
-
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-(6-methoxy-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-N-(3-(trifluoromethyl)benzyl)methanamine
-
2-[(2S)-2-methyl-1,4-dioxa-8-azaspiro[4.5]dec-8-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
tuberculosis drug candidate with high activity against Mycobacterium tuberculosis in vitro and in vivo. Compound is activated in the bacterium by reduction of an essential nitro group to a nitroso derivative, which then specifically reacts with a cysteine residue in the active site of DprE1
2-[(2S)-2-methyl-1,4-dioxa-8-azaspiro[4.5]dec-8-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
i.e. BTZ043, inhibits enzyme by formation of a semimercaptal
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-[(2S)-2-methyl-1,4-dioxa-8-azaspiro[4.5]decan-8-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
BTZ043
2-[(2S)-2-methyl-1,4-dioxa-8-azaspiro[4.5]decan-8-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
BTZ043
2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
PBTZ169
2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
complete inhibition at 0.04 mM
2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
PBTZ169
2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
PBTZ169
3,7-dimethyl-1-phenyl-5-((3-(trifluoromethyl)benzylamino)-methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-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-(((3-methyl-6-oxo-1-phenyl-6,7-dihydro-1H-pyrazolo[3,4-b]-pyridin-5-yl)methylamino)methyl)benzonitrile
-
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-(((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-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-(((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-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-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-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-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-(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-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-((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-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-((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-((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-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-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
high activity against Mycobacterium smegmatis and Mycobacterium tuberculosis H37Rv but no significant activity against benzothiazinone-resistant strains with the mutations Cys387Ser or Cys387Gly in DprE1
3-nitro-N-[(1R)-1-phenylethyl]-5-(trifluoromethyl)benzamide
forms a noncovalent complex with the enzyme
5-((3,4-dimethylbenzylamino)methyl)-3-methyl-1-phenyl-1Hpyrazolo[3,4-b]pyridin-6(7H)-one
-
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-((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
-
5-((benzylamino)methyl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]-pyridin-6(7H)-one
-
ethyl {2-[(1,3-benzothiazole-2-carbonyl)amino]thiophene-3-carbonyl}carbamate
-
-
ethyl {2-[(1,3-benzothiazole-2-carbonyl)amino]thiophene-3-carbonyl}carbamate
TCA1
ethyl {2-[(1,3-benzothiazole-2-carbonyl)amino]thiophene-3-carbonyl}carbamate
TCA1
N-(2-fluoroethyl)-1-[(6-methoxy-5-methylpyrimidin-4-yl)methyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide
-
N-(2-fluoroethyl)-1-[(6-methoxy-5-methylpyrimidin-4-yl)methyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide
-
additional information
benzothiazinone and dinitrobenzamide inhibitors target decaprenylphospho-beta-D-ribofuranose 2-oxidase DprE1. Several mutants showing high levels of dinitrobenzamide resistance, exhibit a mutation in residue Cys394 of DprE1
-
additional information
-
benzothiazinone and dinitrobenzamide inhibitors target decaprenylphospho-beta-D-ribofuranose 2-oxidase DprE1. Several mutants showing high levels of dinitrobenzamide resistance, exhibit a mutation in residue Cys394 of DprE1
-
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Infections
In Vivo Activity of the Benzothiazinones PBTZ169 and BTZ043 against Nocardia brasiliensis.
Infections
Optimization of Hydantoins as Potent Antimycobacterial Decaprenylphosphoryl-?-d-Ribose Oxidase (DprE1) Inhibitors.
Mycetoma
In Vivo Activity of the Benzothiazinones PBTZ169 and BTZ043 against Nocardia brasiliensis.
Tuberculosis
2-Carboxyquinoxalines Kill Mycobacterium tuberculosis through Noncovalent Inhibition of DprE1.
Tuberculosis
A Simple Work-Up-free, Solvent-free Approach to Novel Amino Acid Linked 1,4-Disubstituted 1,2,3-Triazoles as Potent Antituberculosis Agents.
Tuberculosis
Azaindoles: noncovalent DprE1 inhibitors from scaffold morphing efforts, kill Mycobacterium tuberculosis and are efficacious in vivo.
Tuberculosis
Benzothiazinones mediate killing of Corynebacterineae by blocking decaprenyl phosphate recycling involved in cell wall biosynthesis.
Tuberculosis
Benzothiazinones: prodrugs that covalently modify the decaprenylphosphoryl-?-D-ribose 2'-epimerase DprE1 of Mycobacterium tuberculosis.
Tuberculosis
Characterization of DprE1-mediated benzothiazinone resistance in Mycobacterium tuberculosis.
Tuberculosis
Clinical isolates of Mycobacterium tuberculosis in four European hospitals are uniformly susceptible to benzothiazinones.
Tuberculosis
Crystal structure of decaprenylphosphoryl-?- D-ribose 2'-epimerase from Mycobacterium smegmatis.
Tuberculosis
Determinants of the Inhibition of DprE1 and CYP2C9 by Antitubercular Thiophenes.
Tuberculosis
DprE1 Is a Vulnerable Tuberculosis Drug Target Due to Its Cell Wall Localization.
Tuberculosis
Exploring the Potential Inhibition of Candidate Drug Molecules for Clinical Investigation based on their Docking or Crystallographic Analyses against M. tuberculosis Enzyme Targets.
Tuberculosis
Fluorescent Benzothiazinone Analogues Efficiently and Selectively Label Dpre1 in Mycobacteria and Actinobacteria.
Tuberculosis
Identification of a pyrimidinetrione derivative as the potent DprE1 inhibitor by structure-based virtual ligand screening.
Tuberculosis
In vitro combination studies of benzothiazinone lead compound BTZ043 against Mycobacterium tuberculosis.
Tuberculosis
Novel insight into the reaction of nitro, nitroso and hydroxylamino benzothiazinones and of benzoxacinones with Mycobacterium tuberculosis DprE1.
Tuberculosis
Overview of the Development of DprE1 Inhibitors for Combating the Menace of Tuberculosis.
Tuberculosis
Pseudomonas aeruginosa D-Arabinofuranose Biosynthetic Pathway and Its Role in Type IV Pilus Assembly.
Tuberculosis
Scaffold Morphing To Identify Novel DprE1 Inhibitors with Antimycobacterial Activity.
Tuberculosis
Structural and inhibition analysis of novel sulfur-rich 2-mercaptobenzothiazole and 1,2,3-triazole ligands against Mycobacterium tuberculosis DprE1 enzyme.
Tuberculosis
Structural basis of inhibition of Mycobacterium tuberculosis DprE1 by benzothiazinone inhibitors.
Tuberculosis
Structural studies of Mycobacterium tuberculosis DprE1 interacting with its inhibitors.
Tuberculosis
Structure based pharmacophore modelling approach for the design of azaindole derivatives as DprE1 inhibitors for tuberculosis.
Tuberculosis
Structure, dynamics, and interaction of Mycobacterium tuberculosis (Mtb) DprE1 and DprE2 examined by molecular modeling, simulation, and electrostatic studies.
Tuberculosis
Structure-Based Drug Design and Characterization of Sulfonyl-Piperazine Benzothiazinone Inhibitors of DprE1 from Mycobacterium tuberculosis.
Tuberculosis
The 8-Pyrrole-Benzothiazinones Are Noncovalent Inhibitors of DprE1 from Mycobacterium tuberculosis.
Tuberculosis
The DprE1 enzyme, one of the most vulnerable targets of Mycobacterium tuberculosis.
Tuberculosis
The frequently occurring components of essential oils beta elemene and R-limonene alter expression of dprE1 and clgR genes of Mycobacterium tuberculosis H37Ra.
Tuberculosis
Towards a new combination therapy for tuberculosis with next generation benzothiazinones.
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
Mycolicibacterium smegmatis
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
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ORGANISM
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GENERAL INFORMATION
ORGANISM
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COMMENTARY
LITERATURE
physiological function
physiological function
construction of a conditional gene knockout strain targeting the gene encoding subunit dprE1 of decaprenylphosphoribose 2' epimerase. The gene is essential for viability, results suggests that decaprenylphosphoryl arabinose synthesis is essential in mycobacteria, indicate a lack of redundancy in decaprenylphosphoryl arabinose synthesis and suggest that no alternative arabinose donors for cell wall biosynthesis exist
physiological function
decaprenylphosphoryl-beta-D-ribofuranose 2'-epimerase is constituted of DprE1 and DprE2 that together catalyze the epimerization of decaprenylphosphoryl-beta-D-ribofuranose to decaprenylphosphoryl-beta-D-arabinofuranose
physiological function
decaprenylphosphoryl-D-arabinofuranose is synthesized by the following sequence of events: 5-phosphoribose 1-diphosphate is transferred to a decaprenyl-phosphate molecule to form decaprenylphosphoryl-beta-D-5-phosphoribose. Decaprenylphosphoryl-beta-D-5-phosphoribose is dephosphorylated to form decaprenylphosphoryl-beta-D-ribose. The hydroxyl group at the 2 position of the ribose is oxidized and is likely to form decaprenylphosphoryl-2-keto-beta-D-erythro-pentofuranose. Decaprenylphosphoryl-2-keto-beta-D-erythro-pentofuranose is reduced to form decaprenylphosphoryl-beta-D-arabinofuranose. Thus, the epimerization of the ribosyl to an arabinosyl residue occurs at the lipid-linked level
physiological function
-
decaprenylphosphoryl-D-arabinofuranose is synthesized by the following sequence of events: 5-phosphoribose 1-diphosphate is transferred to a decaprenyl-phosphate molecule to form decaprenylphosphoryl-beta-D-5-phosphoribose. Decaprenylphosphoryl-beta-D-5-phosphoribose is dephosphorylated to form decaprenylphosphoryl-beta-D-ribose. The hydroxyl group at the 2 position of the ribose is oxidized and is likely to form decaprenylphosphoryl-2-keto-beta-D-erythro-pentofuranose. Decaprenylphosphoryl-2-keto-beta-D-erythro-pentofuranose is reduced to form decaprenylphosphoryl-beta-D-arabinofuranose. Thus, the epimerization of the ribosyl to an arabinosyl residue occurs at the lipid-linked level
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PDB
SCOP
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MOLECULAR WEIGHT
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LITERATURE
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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
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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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C387G
C387N
the mutation confers resistance to benzothiazinones and reduces the overall catalytic efficiency by about 4fold compared to the wild type enzyme
C387S
C387G
C387N
-
the mutation confers resistance to benzothiazinones and reduces the overall catalytic efficiency by about 4fold compared to the wild type enzyme
C387S
C394G
benzothiazinone-resistant mutant, reduces benzothiazinones to inert metabolites while avoiding covalent inactivation
C394S
benzothiazinone-resistant mutant, reduces benzothiazinones to inert metabolites while avoiding covalent inactivation
additional information
C387G
mutation confers resistance to 1-methyl-2,4,7-trinitroxanthone and to 3-nitro-N-[(1R)-1-phenylethyl]-5-(trifluoromethyl)benzamide
C387G
the mutation confers resistance to benzothiazinones and reduces the overall catalytic efficiency by about 4fold compared to the wild type enzyme
C387S
mutation confers resistance to 1-methyl-2,4,7-trinitroxanthone and to 3-nitro-N-[(1R)-1-phenylethyl]-5-(trifluoromethyl)benzamide
C387G
-
mutation confers resistance to 1-methyl-2,4,7-trinitroxanthone and to 3-nitro-N-[(1R)-1-phenylethyl]-5-(trifluoromethyl)benzamide
C387G
-
the mutation confers resistance to benzothiazinones and reduces the overall catalytic efficiency by about 4fold compared to the wild type enzyme
C387S
-
mutation confers resistance to 1-methyl-2,4,7-trinitroxanthone and to 3-nitro-N-[(1R)-1-phenylethyl]-5-(trifluoromethyl)benzamide
additional information
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
additional information
-
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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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
analysis
analysis
developed of an assay method based on the visualization of mycobacterium replication within host cells and application for the search of compounds that are able to chase the pathogen from its hideout
analysis
-
developed of an assay method based on the visualization of mycobacterium replication within host cells and application for the search of compounds that are able to chase the pathogen from its hideout
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Trefzer, C.; Rengifo-Gonzalez, M.; Hinner, M.J.; Schneider, P.; Makarov, V.; Cole, S.T.; Johnsson, K.
Benzothiazinones: prodrugs that covalently modify the decaprenylphosphoryl-beta-D-ribose 2-epimerase DprE1 of Mycobacterium tuberculosis
J. Am. Chem. Soc.
132
13663-13665
2010
Mycobacterium tuberculosis (P9WJF1), Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv (P9WJF1)
brenda
Trefzer, C.; Skovierova, H.; Buroni, S.; Bobovska, A.; Nenci, S.; Molteni, E.; Pojer, F.; Pasca, M.; Makarov, V.; Cole, S.; Riccardi, G.; Mikusova, K.; Johnsson, K.
Benzothiazinones are suicide inhibitors of mycobacterial decaprenylphosphoryl-beta-D-ribofuranose 2'-oxidase DprE1
J. Am. Chem. Soc.
134
912-915
2012
Mycolicibacterium smegmatis (A0R607)
brenda
Mikusova, K.; Huang, H.; Yagi, T.; Holsters, M.; Vereecke, D.; DHaeze, W.; Scherman, M.S.; Brennan, P.J.; McNeil, M.R.; Crick, D.C.
Decaprenylphosphoryl arabinofuranose, the donor of the D-arabinofuranosyl residues of mycobacterial arabinan, is formed via a two-step epimerization of decaprenylphosphoryl ribose
J. Bacteriol.
187
8020-8025
2005
Mycobacterium tuberculosis (P9WJF1), Mycobacterium tuberculosis H37Rv (P9WJF1)
brenda
Crellin, P.K.; Brammananth, R.; Coppel, R.L.
Decaprenylphosphoryl-beta-D-ribose 2-epimerase, the target of benzothiazinones and dinitrobenzamides, is an essential enzyme in Mycobacterium smegmatis
PLoS ONE
6
e16869
2011
Mycolicibacterium smegmatis (A0R607), Mycolicibacterium smegmatis
brenda
Ribeiro, A.L.; Degiacomi, G.; Ewann, F.; Buroni, S.; Incandela, M.L.; Chiarelli, L.R.; Mori, G.; Kim, J.; Contreras-Dominguez, M.; Park, Y.S.; Han, S.J.; Brodin, P.; Valentini, G.; Rizzi, M.; Riccardi, G.; Pasca, M.R.
Analogous mechanisms of resistance to benzothiazinones and dinitrobenzamides in Mycobacterium smegmatis
PLoS ONE
6
e26675
2011
Mycolicibacterium smegmatis (A0R607), Mycolicibacterium smegmatis
brenda
Christophe, T.; Jackson, M.; Hee, K.; Fenistein, D.; Contreras-Dominguez, M.; Kim, J.; Genovesio, A.; Carralot, J.; Ewann, F.; Kim, E.; Lee, S.; Kang, S.; Seo, M.; Eun, J.; Skovierova, H.; Pham, H.; Riccardi, G.; Youn, N.; Marsollier, L.; Kempf, M.; Jol
High content screening identifies decaprenyl-phosphoribose 2'-epimerase as a target for intracellular antimycobacterial inhibitors
PLoS Pathog.
5
e1000645
2009
Mycobacterium tuberculosis (P9WJF1), Mycobacterium tuberculosis H37Rv (P9WJF1)
brenda
Batt, S.M.; Jabeen, T.; Bhowruth, V.; Quill, L.; Lund, P.A.; Eggeling, L.; Alderwick, L.J.; Fuetterer, K.; Besra, G.S.
Structural basis of inhibition of Mycobacterium tuberculosis DprE1 by benzothiazinone inhibitors
Proc. Natl. Acad. Sci. USA
109
11354-11359
2012
Mycobacterium tuberculosis (P9WJF1), Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv (P9WJF1)
brenda
Batt, S.M.; Cacho Izquierdo, M.; Castro Pichel, J.; Stubbs, C.J.; Vela-Glez Del Peral, L.; Perez-Herran, E.; Dhar, N.; Mouzon, B.; Rees, M.; Hutchinson, J.P.; Young, R.J.; McKinney, J.D.; Barros Aguirre, D.; Ballell, L.; Besra, G.S.; Argyrou, A.
Whole cell target engagement identifies novel inhibitors of Mycobacterium tuberculosis decaprenylphosphoryl-beta-D-ribose oxidase
ACS Infect. Dis.
1
615-626
2015
Mycobacterium tuberculosis (P9WJF1), Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv (P9WJF1)
brenda
Makarov, V.; Neres, J.; Hartkoorn, R.C.; Ryabova, O.B.; Kazakova, E.; Sarkan, M.; Huszar, S.; Piton, J.; Kolly, G.S.; Vocat, A.; Conroy, T.M.; Mikusova, K.; Cole, S.T.
The 8-pyrrole-benzothiazinones are noncovalent inhibitors of DprE1 from Mycobacterium tuberculosis
Antimicrob. Agents Chemother.
59
4446-4452
2015
Mycobacterium tuberculosis (P9WJF1), Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv (P9WJF1)
brenda
Foo, C.S.; Lechartier, B.; Kolly, G.S.; Boy-Roettger, S.; Neres, J.; Rybniker, J.; Lupien, A.; Sala, C.; Piton, J.; Cole, S.T.
Characterization of DprE1-mediated benzothiazinone resistance in Mycobacterium tuberculosis
Antimicrob. Agents Chemother.
60
6451-6459
2016
Mycobacterium tuberculosis (P9WJF1), Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv (P9WJF1)
brenda
Riccardi, G.; Pasca, M.R.; Chiarelli, L.R.; Manina, G.; Mattevi, A.; Binda, C.
The DprE1 enzyme, one of the most vulnerable targets of Mycobacterium tuberculosis
Appl. Microbiol. Biotechnol.
97
8841-8848
2013
Mycobacterium tuberculosis
brenda
Landge, S.; Mullick, A.B.; Nagalapur, K.; Neres, J.; Subbulakshmi, V.; Murugan, K.; Ghosh, A.; Sadler, C.; Fellows, M.D.; Humnabadkar, V.; Mahadevaswamy, J.; Vachaspati, P.; Sharma, S.; Kaur, P.; Mallya, M.; Rudrapatna, S.; Awasthy, D.; Sambandamurthy, V.K.; Pojer, F.; Cole, S.T.; Balganesh, T.S.; Ug, U.g.a.
Discovery of benzothiazoles as antimycobacterial agents: Synthesis, structure-activity relationships and binding studies with Mycobacterium tuberculosis decaprenylphosphoryl-beta-D-ribose 2'-oxidase
Bioorg. Med. Chem.
23
7694-7710
2015
Mycobacterium tuberculosis (P9WJF1)
brenda
Panda, M.; Ramachandran, S.; Ramachandran, V.; Shirude, P.S.; Humnabadkar, V.; Nagalapur, K.; Sharma, S.; Kaur, P.; Guptha, S.; Narayan, A.; Mahadevaswamy, J.; Ambady, A.; Hegde, N.; Rudrapatna, S.S.; Hosagrahara, V.P.; Sambandamurthy, V.K.; Raichurkar, A.
Discovery of pyrazolopyridones as a novel class of noncovalent DprE1 inhibitor with potent anti-mycobacterial activity
J. Med. Chem.
57
4761-4771
2014
Mycobacterium tuberculosis (P9WJF1), Mycobacterium tuberculosis, Mycolicibacterium smegmatis (P9WJF1), Mycobacterium tuberculosis H37Rv (P9WJF1)
brenda
Naik, M.; Humnabadkar, V.; Tantry, S.J.; Panda, M.; Narayan, A.; Guptha, S.; Panduga, V.; Manjrekar, P.; Jena, L.K.; Koushik, K.; Shanbhag, G.; Jatheendranath, S.; Manjunatha, M.R.; Gorai, G.; Bathula, C.; Rudrapatna, S.; Achar, V.; Sharma, S.; Ambady, A.; Hegde, N.; Mahadevaswamy, J.; Kaur, P.; Samb, S.a.m.b.a.
4-aminoquinolone piperidine amides: noncovalent inhibitors of DprE1 with long residence time and potent antimycobacterial activity
J. Med. Chem.
57
5419-5434
2014
Mycobacterium tuberculosis (P9WJF1), Mycobacterium tuberculosis
brenda
Bhutani, I.; Loharch, S.; Gupta, P.; Madathil, R.; Parkesh, R.
Structure, dynamics, and interaction of Mycobacterium tuberculosis (Mtb) DprE1 and DprE2 examined by molecular modeling, simulation, and electrostatic studies
PLoS ONE
10
e0119771
2015
Mycobacterium tuberculosis (P9WJF0), Mycobacterium tuberculosis (P9WJF1), Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv (P9WJF1), Mycobacterium tuberculosis CDC 1551 (P9WJF0)
brenda
Li, H.; Jogl, G.
Crystal structure of decaprenylphosphoryl-beta-D-ribose 2'-epimerase from Mycobacterium smegmatis
Proteins
81
538-543
2013
Mycolicibacterium smegmatis (A0R607), Mycolicibacterium smegmatis, Mycolicibacterium smegmatis ATCC 700084 (A0R607)
brenda
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