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(1R)-1,2-dideoxy-1-fluoro-1-(5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-D-ribo-hexitol
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(1S)-1,2-dideoxy-1-fluoro-1-(5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-D-ribo-hexitol
(E)-3-hydroxy-4-(2-(5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-yl)vinyl)benzoic acid
(E)-4-(2-(5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-yl)vinyl)benzoate
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(E)-4-(2-(5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-yl)vinyl)benzoic acid
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-
(E)-5-nitro-6-(2-hydroxystyryl)pyrimidine-2,4(1H,3H)-dione
(E)-5-nitro-6-(3-(pyridin-3-yl)vinyl)pyrimidine-2,4(1H,3H)-dione
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(E)-5-nitro-6-(3-nitrostyryl)pyrimidine-2,4(1H,3H)-dione
(E)-5-nitro-6-(4-bromostyryl)pyrimidine-2,4(1H,3H)-dione
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(E)-5-nitro-6-(4-nitrostyryl)pyrimidine-2,4(1H,3H)-dione
(E)-5-nitro-6-[2-(1H-pyrrol-2-yl)vinyl]pyrimidine-2,4(1H,3H)-dione
(E)-6-(2,3,4-trimethoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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-
(E)-6-(2,3-dihydroxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
(E)-6-(2,3-dimethoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
(E)-6-(2-(3H-indol-3-yl)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione
(E)-6-(2-(naphthalen-2-yl)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione
(E)-6-(2-fluoro-3-methoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
(E)-6-(2-fluorostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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-
(E)-6-(2-hydroxy-3-nitrostyryl)-3-nitropyrimidine-2,4(1H,3H)-dione
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-
(E)-6-(2-hydroxy-5-nitrostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(2-methoxy-5-nitrostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
(E)-6-(2-methoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
(E)-6-(2-nitrostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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-
(E)-6-(3,4,5-trimethoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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-
(E)-6-(3,4-dimethoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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-
(E)-6-(3-hydroxy-4-methoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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-
(E)-6-(3-hydroxy-4-nitrostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
(E)-6-(3-hydroxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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competitive
(E)-6-(4-chlorostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(4-fluorostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(4-hydroxy-3-nitrostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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-
(E)-6-(4-hydroxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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-
1,3,6,8-tetrahydroxynaphthyridine
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-
1,3,7-trihydro-9-D-ribityl-2,4,8-purinetrione
1-deoxy-1-(2,4,6,7-tetraoxo-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl)-D-ribitol
1-deoxy-1-(2,6,8-trioxo-1,2,3,6,7,8-hexahydro-9H-purin-9-yl)-D-ribitol
1-deoxy-1-[(2,6-dioxo-5-[[5-(phosphonooxy)pentanoyl]amino]-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-D-ribitol
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-
1-deoxy-1-[2,4,6,7-tetraoxo-5-[4-(phosphonooxy)butyl]-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl]-D-ribitol
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-
1-deoxy-1-[2,4,6,7-tetraoxo-5-[5-(phosphonooxy)pentyl]-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl]-D-ribitol
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-
1-deoxy-1-[2,6,8-trioxo-7-[4-(phosphonooxy)butyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
1-deoxy-1-[2,6,8-trioxo-7-[5-(phosphonooxy)pentyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
1-deoxy-1-[2,6,8-trioxo-7-[6-(phosphonooxy)hexyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
1-deoxy-1-[[2,6-dioxo-5-(4-phosphonobutyl)-1,2,3,6-tetrahydropyrimidin-4-yl]amino]-D-ribitol
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1-deoxy-1-[[2,6-dioxo-5-(5-phosphonopentyl)-1,2,3,6-tetrahydropyrimidin-4-yl]amino]-D-ribitol
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1-deoxy-1-[[2,6-dioxo-5-(6-phosphonohexyl)-1,2,3,6-tetrahydropyrimidin-4-yl]amino]-D-ribitol
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-
1-[(5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)(methyl)amino]-1-deoxy-D-ribitol hydrochloride
2,4-dioxo-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
2,5,8,11-tetraaza-5,11-dihydro-4,10-dihydroxyperylene-1,3,6,7,9,12-hexaone
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-
2-(2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamido)acetic acid
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possible lead compound for inhibitor screening
3-(1,3,7,9-tetrahydro-9-D-ribityl-2,6,8-trioxopurin-7-yl)-1-propanol
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-
3-(1,3,7,9-tetrahydro-9-D-ribityl-2,6,8-trioxopurin-7-yl)propane 1-phosphate
3-(1,3,7-trihydro-9-D-ribityl-2,6,8-purinetrion-7-yl)butane 1-phosphate
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highly specific binding of the purinetrione inhibitor to the Mycobacterium tuberculosis enzyme with dissociation constants in micromolar range
3-(1,3,7-trihydro-9-D-ribityl-2,6,8-purinetrione-7-yl)butane 1-phosphate
3-(1,3,7-trihydro-9-D-ribityl-2,6,8-purinetrione-7-yl)pentane 1-phosphate
3-(1,3,7-trihydro-9-D-ribityl-2,6,8-purinetrione-7-yl)propane 1-phosphate
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highly specific binding of the purinetrione inhibitor to the Mycobacterium tuberculosis enzyme with dissociation constants in micromolar range
3-(1,3-dihydro-9-D-ribityl-2,4,8-purinetrione-7-yl)propane 1-phosphate
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association constants and thermodynamic parameters of binding of different inhibitors to lumazine synthase
3-(7-hydroxy-8-ribityllumazine-6-yl)propionic acid
3-[4,6-dioxo-4,5,6,7-tetrahydro-1-D-ribityl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]propyl 1-phosphate
4-(1,3,7,9-tetrahydro-9-D-ribityl-2,6,8-trioxopurin-7-yl)butane 1-phosphate
4-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)butane 1-phosphate
4-(2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamido)butyl dihydrogen phosphate
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mixed inhibition
4-(6,7(5H,8H)-dioxo-8-D-ribityllumazine-5-yl)butane 1-phosphate
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association constants and thermodynamic parameters of binding of different inhibitors to lumazine synthase
4-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)butyl dihydrogen phosphate
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molecular modeling of binding to luminazine synthase. The main forces stabilizing the complex with the enzyme involve pi-pi stacking interactions with Trp27 and hydrogen bonding of the phosphates with Arg128, the backbone nitrogens of Gly85 and Gln86, and the side chain hydroxyl of Thr87
4-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-yl)-butyl phosphate
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association constants and thermodynamic parameters of binding of different inhibitors to lumazine synthase
4-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-yl)-n-butyl 1-phosphate
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competitive
4-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-yl)butyl 1-phosphate
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association constants and thermodynamic parameters of binding
4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]butanoic acid
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uncompetitive, comparison with inhibition of Escherichia coli riboflavin synthase
4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]butyl dihydrogen phosphate
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competitive, comparison with inhibition of Escherichia coli riboflavin synthase
4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]propyl dihydrogen phosphate
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uncompetitive, comparison with inhibition of Escherichia coli riboflavin synthase
4-[4,6-dioxo-4,5,6,7-tetrahydro1-D-ribityl-1H-pyrazolo[3,4-d]-pyrimidin-3-yl]butyl 1-phosphate
5-(1,3,7,9-tetrahydro-9-D-ribityl-2,6,8-trioxopurin-7-yl)-1,1-difluoropentane 1-phosphonate
5-(1,3,7-trihydro-9-d-ribityl-2,4,8-purinetrione-7-yl)1,1-difluoropentane-1-phosphate
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association constants and thermodynamic parameters of binding
5-(1,3,7-trihydro-9-D-ribityl-2,4,8-purinetrione-7-yl)pentane1-phosphate
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association constants and thermodynamic parameters of binding
5-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)pentane 1-phosphate
5-(4-phosphonobutyryl)amino-6-D-ribitylaminouracil
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comparison with inhibition of Escherichia coli riboflavin synthase
5-(5-phosphonopentyl)amino-6-D-ribitylaminouracil
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comparison with inhibition of Escherichia coli riboflavin synthase
5-(5-phosphonoxyvaleryl)amino-6-D-ribitylaminouracil
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mixed inhibition, comparison with inhibition of Escherichia coli riboflavin synthase
5-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-5-oxopentyl phosphate
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competitive
5-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-yl)-n-pentyl 1-phosphonate
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competitive
5-(6-D-ribitylamino-2,4(1H,3H)pyrimidinedione-5-yl)-1-pentyl-phosphonic acid
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5-(hexyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione
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mixed inhibition, comparison with inhibition of Escherichia coli riboflavin synthase
5-(pentyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione
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mixed inhibition, comparison with inhibition of Escherichia coli riboflavin synthase
5-nitro-6-(D-ribitylamino)-2,4(1H,3H)-pyrimidinedione
5-nitro-6-ribitylamino-2,4(1H,3H)-pyrimidinedione
5-nitro-6-[(D-ribityl)methyl]pyrimidine-2,4-dione
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5-nitro-6-[[(2R,3R,4R)-2,3,4,5 tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
5-nitroso-6-(D-ribitylamino)-2,4(1H,3H)-pyrimidinedione
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-
5-nitroso-6-ribityl-amino-2,4(1H,3H)pyrimidinedione
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5-[4,6-dioxo-4,5,6,7-tetrahydro-1-D-ribityl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]pentyl 1-phosphate
6,7-dioxo-5H-8-ribitylaminolumazine
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-
6-(1,3,7-trihydro-9-d-ribityl-2,4,8-purinetrione-7-yl)hexane 1-phosphate
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association constants and thermodynamic parameters of binding
6-carboxyethyl-7-oxo-8-ribityllumazine
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-
6-methyl-7-methylidene-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,8-dihydropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione
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mixed inhibition, comparison with inhibition of Escherichia coli riboflavin synthase
8-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]tetrahydropteridine-2,4,6,7(1H,3H)-tetrone
9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,9-dihydro-1H-purine-2,6,8(3H)-trione
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comparison with inhibition of Escherichia coli riboflavin synthase
ethyl [(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)amino](oxo)acetate
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dion-5-ylpropionamide
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dione-5-ylisobutyramide
N-[2,4-dioxo-6-(ribitylamino)-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid ethyl ester
(1S)-1,2-dideoxy-1-fluoro-1-(5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-D-ribo-hexitol
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-
(1S)-1,2-dideoxy-1-fluoro-1-(5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-D-ribo-hexitol
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-
(E)-3-hydroxy-4-(2-(5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-yl)vinyl)benzoic acid
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(E)-3-hydroxy-4-(2-(5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-yl)vinyl)benzoic acid
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-
(E)-5-nitro-6-(2-hydroxystyryl)pyrimidine-2,4(1H,3H)-dione
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competitive
(E)-5-nitro-6-(2-hydroxystyryl)pyrimidine-2,4(1H,3H)-dione
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competitive
(E)-5-nitro-6-(3-nitrostyryl)pyrimidine-2,4(1H,3H)-dione
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(E)-5-nitro-6-(3-nitrostyryl)pyrimidine-2,4(1H,3H)-dione
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(E)-5-nitro-6-(4-nitrostyryl)pyrimidine-2,4(1H,3H)-dione
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(E)-5-nitro-6-(4-nitrostyryl)pyrimidine-2,4(1H,3H)-dione
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(E)-5-nitro-6-[2-(1H-pyrrol-2-yl)vinyl]pyrimidine-2,4(1H,3H)-dione
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(E)-5-nitro-6-[2-(1H-pyrrol-2-yl)vinyl]pyrimidine-2,4(1H,3H)-dione
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(E)-6-(2,3-dihydroxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(2,3-dihydroxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(2,3-dimethoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(2,3-dimethoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(2-(3H-indol-3-yl)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(2-(3H-indol-3-yl)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(2-(naphthalen-2-yl)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(2-(naphthalen-2-yl)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(2-fluoro-3-methoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(2-fluoro-3-methoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(2-methoxy-5-nitrostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(2-methoxy-5-nitrostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(2-methoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(2-methoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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(E)-6-(3-hydroxy-4-nitrostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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-
(E)-6-(3-hydroxy-4-nitrostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
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1,3,7-trihydro-9-D-ribityl-2,4,8-purinetrione
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association constants and thermodynamic parameters of binding of different inhibitors to lumazine synthase
1,3,7-trihydro-9-D-ribityl-2,4,8-purinetrione
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association constants and thermodynamic parameters of binding
1-deoxy-1-(2,4,6,7-tetraoxo-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl)-D-ribitol
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1-deoxy-1-(2,4,6,7-tetraoxo-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl)-D-ribitol
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-
1-deoxy-1-(2,6,8-trioxo-1,2,3,6,7,8-hexahydro-9H-purin-9-yl)-D-ribitol
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-
1-deoxy-1-(2,6,8-trioxo-1,2,3,6,7,8-hexahydro-9H-purin-9-yl)-D-ribitol
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-
1-deoxy-1-[2,6,8-trioxo-7-[4-(phosphonooxy)butyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
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-
1-deoxy-1-[2,6,8-trioxo-7-[4-(phosphonooxy)butyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
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-
1-deoxy-1-[2,6,8-trioxo-7-[5-(phosphonooxy)pentyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
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-
1-deoxy-1-[2,6,8-trioxo-7-[5-(phosphonooxy)pentyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
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-
1-deoxy-1-[2,6,8-trioxo-7-[6-(phosphonooxy)hexyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
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-
1-deoxy-1-[2,6,8-trioxo-7-[6-(phosphonooxy)hexyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
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-
1-[(5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)(methyl)amino]-1-deoxy-D-ribitol hydrochloride
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-
1-[(5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)(methyl)amino]-1-deoxy-D-ribitol hydrochloride
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-
2,4-dioxo-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
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inhibition of both lumazine synthase and riboflavin synthase
2,4-dioxo-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
-
inhibition of both lumazine synthase and riboflavin synthase
2,4-dioxo-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
-
inhibition of both lumazine synthase and riboflavin synthase
3-(1,3,7,9-tetrahydro-9-D-ribityl-2,6,8-trioxopurin-7-yl)propane 1-phosphate
-
-
3-(1,3,7,9-tetrahydro-9-D-ribityl-2,6,8-trioxopurin-7-yl)propane 1-phosphate
-
-
3-(1,3,7-trihydro-9-D-ribityl-2,6,8-purinetrione-7-yl)butane 1-phosphate
-
competitive
3-(1,3,7-trihydro-9-D-ribityl-2,6,8-purinetrione-7-yl)butane 1-phosphate
-
competitive
3-(1,3,7-trihydro-9-D-ribityl-2,6,8-purinetrione-7-yl)butane 1-phosphate
-
competitive
3-(1,3,7-trihydro-9-D-ribityl-2,6,8-purinetrione-7-yl)pentane 1-phosphate
-
competitive
3-(1,3,7-trihydro-9-D-ribityl-2,6,8-purinetrione-7-yl)pentane 1-phosphate
-
competitive
3-(1,3,7-trihydro-9-D-ribityl-2,6,8-purinetrione-7-yl)pentane 1-phosphate
-
competitive
3-(7-hydroxy-8-ribityllumazine-6-yl)propionic acid
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-
3-(7-hydroxy-8-ribityllumazine-6-yl)propionic acid
binding structure, overview
3-[4,6-dioxo-4,5,6,7-tetrahydro-1-D-ribityl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]propyl 1-phosphate
-
competitive
3-[4,6-dioxo-4,5,6,7-tetrahydro-1-D-ribityl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]propyl 1-phosphate
-
competitive
3-[4,6-dioxo-4,5,6,7-tetrahydro-1-D-ribityl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]propyl 1-phosphate
-
mixed type inhibition
4-(1,3,7,9-tetrahydro-9-D-ribityl-2,6,8-trioxopurin-7-yl)butane 1-phosphate
-
-
4-(1,3,7,9-tetrahydro-9-D-ribityl-2,6,8-trioxopurin-7-yl)butane 1-phosphate
-
-
4-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)butane 1-phosphate
-
-
4-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)butane 1-phosphate
-
-
4-[4,6-dioxo-4,5,6,7-tetrahydro1-D-ribityl-1H-pyrazolo[3,4-d]-pyrimidin-3-yl]butyl 1-phosphate
-
competitive
4-[4,6-dioxo-4,5,6,7-tetrahydro1-D-ribityl-1H-pyrazolo[3,4-d]-pyrimidin-3-yl]butyl 1-phosphate
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competitive
5-(1,3,7,9-tetrahydro-9-D-ribityl-2,6,8-trioxopurin-7-yl)-1,1-difluoropentane 1-phosphonate
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-
5-(1,3,7,9-tetrahydro-9-D-ribityl-2,6,8-trioxopurin-7-yl)-1,1-difluoropentane 1-phosphonate
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-
5-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)pentane 1-phosphate
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-
5-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)pentane 1-phosphate
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-
5-nitro-6-(D-ribitylamino)-2,4(1H,3H)-pyrimidinedione
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5-nitro-6-(D-ribitylamino)-2,4(1H,3H)-pyrimidinedione
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5-nitro-6-ribitylamino-2,4(1H,3H)-pyrimidinedione
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crystallization data
5-nitro-6-ribitylamino-2,4(1H,3H)-pyrimidinedione
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crystallization data
5-nitro-6-ribitylamino-2,4(1H,3H)-pyrimidinedione
crystallization data; crystallization data
5-nitro-6-styryluracil
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-
5-nitro-6-styryluracil
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-
5-nitro-6-[[(2R,3R,4R)-2,3,4,5 tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
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inhibition of both lumazine synthase and riboflavin synthase
5-nitro-6-[[(2R,3R,4R)-2,3,4,5 tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
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inhibition of both lumazine synthase and riboflavin synthase
5-nitro-6-[[(2R,3R,4R)-2,3,4,5 tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
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inhibition of both lumazine synthase and riboflavin synthase
5-[4,6-dioxo-4,5,6,7-tetrahydro-1-D-ribityl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]pentyl 1-phosphate
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competitive
5-[4,6-dioxo-4,5,6,7-tetrahydro-1-D-ribityl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]pentyl 1-phosphate
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competitive
8-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]tetrahydropteridine-2,4,6,7(1H,3H)-tetrone
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competitive
8-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]tetrahydropteridine-2,4,6,7(1H,3H)-tetrone
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competitive
ethyl [(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)amino](oxo)acetate
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competitive
ethyl [(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)amino](oxo)acetate
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partial inhibition
ethyl [(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)amino](oxo)acetate
mixed type inhibition
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dion-5-ylpropionamide
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partial inhibition, inhibition of both lumazine synthase and riboflavin synthase
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dion-5-ylpropionamide
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competitive, inhibition of both lumazine synthase and riboflavin synthase (EC 2.5.1.9)
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dion-5-ylpropionamide
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competitive, inhibition of both lumazine synthase and riboflavin synthase
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dione-5-ylisobutyramide
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partial inhibition, inhibition of both lumazine synthase and riboflavin synthase
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dione-5-ylisobutyramide
-
partial inhibition, inhibition of both lumazine synthase and riboflavin synthase (EC 2.5.1.9)
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dione-5-ylisobutyramide
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competitive, inhibition of both lumazine synthase and riboflavin synthase
N-[2,4-dioxo-6-(ribitylamino)-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid ethyl ester
-
competitive, inhibition of both lumazine synthase and riboflavin synthase
N-[2,4-dioxo-6-(ribitylamino)-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid ethyl ester
-
partial inhibition, inhibition of both lumazine synthase and riboflavin synthase (EC 2.5.1.9)
N-[2,4-dioxo-6-(ribitylamino)-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid ethyl ester
-
mixed type inhibition, inhibition of both lumazine synthase and riboflavin synthase
additional information
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incorporation of an amide into 5-phosphonoalkyl-6-D-ribitylaminopyrimidinedione lumazine synthase inhibitors results in an unexpected reversal of selectivity for riboflavin synthase versus lumazine synthase
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additional information
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certain purinetriones bearing phosphate side chains can inhibit both lumazine synthase as well as riboflavin synthase, and molecular modeling with 3-(1,3,7,9-tetrahydro-9-D-ribityl-2,6,8-trioxopurin-7-yl)propane 1-phosphate suggests possible binding modes to each enzyme. Antibiotics that would inhibit both lumazine synthase and riboflavin synthase would be less likely to suffer from the development of antibiotic resistance by the organisms that they are supposed to treat, since pathogenic microorganisms would have to simultaneously select for mutations in both enzymes in order to escape the cytotoxic effects of the antibiotics
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additional information
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no inhibition: 5-amino-6-[(D-ribityl)methyl]pyrimidine-2,4-dione hydrochloride, 5-nitro-6-(N-methyl)ribitylpyrimidine-2,4-dione
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