2.5.1.9: riboflavin synthase
This is an abbreviated version!
For detailed information about riboflavin synthase, go to the full flat file.
Word Map on EC 2.5.1.9
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2.5.1.9
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6,7-dimethyl-8-ribityllumazine
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cyclohydrolase
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5-amino-6-ribitylamino-2,41h,3h-pyrimidinedione
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dismutation
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guilliermondii
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3,4-dihydroxy-2-butanone
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icosahedral
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bartonellae
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photobacterium
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flavinogenic
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flavinogenesis
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ashbyii
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eremothecium
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ribitylated
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leiognathi
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henselae
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famata
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drug development
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pharmacology
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medicine
- 2.5.1.9
- 6,7-dimethyl-8-ribityllumazine
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cyclohydrolase
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5-amino-6-ribitylamino-2,41h,3h-pyrimidinedione
-
dismutation
- guilliermondii
- 3,4-dihydroxy-2-butanone
-
icosahedral
-
bartonellae
- photobacterium
-
flavinogenic
-
flavinogenesis
-
ashbyii
- eremothecium
-
ribitylated
- leiognathi
- henselae
- famata
- drug development
- pharmacology
- medicine
Reaction
2 6,7-dimethyl-8-(1-D-ribityl)lumazine = +
Synonyms
heavy riboflavin synthase, light riboflavin synthase, lumazine synthase/riboflavin synthase complex, RibD, RibE1, riboflavin synthase, riboflavin synthetase, riboflavine synthase, riboflavine synthetase, synthase, riboflavin
ECTree
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Inhibitors
Inhibitors on EC 2.5.1.9 - riboflavin synthase
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(2-ethyl-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)methyl 3,4,5-triethoxybenzoate
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(2E)-3-(2,3-dimethoxyphenyl)-N-[4-methyl-2-(4-methylpiperazin-1-yl)quinolin-6-yl]prop-2-enamide
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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
2,4-dioxo-6-[(3S,4S,5R)-3,4,5,6-tetrahydroxyhexyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
2,4-dioxo-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
2-(4-ethoxyphenyl)-N-[3-(piperidin-1-yl)propyl]imidazo[2,1-b][1,3]benzothiazole-7-carboxamide
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2-(4-methoxyphenyl)-N-[3-(piperidin-1-yl)propyl]imidazo[2,1-b][1,3]benzothiazole-7-carboxamide
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2-chloro-N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide
2-chloro-N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
2-[ethyl(methyl)amino]ethyl 4-[(5-ethyl-4-oxo-4,5-dihydrothieno[3,2-c]quinoline-2-carbonyl)amino]benzoate
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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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comparison with inhibition of Bacillus subtilis lumazine 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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comparison with inhibition of Bacillus subtilis lumazine 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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competitive, comparison with inhibition of Bacillus subtilis lumazine synthase
5-(4-phosphonobutyryl)amino-6-D-ribitylaminouracil
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comparison with inhibition of Bacillus subtilis luminazine synthase/riboflavin synthase
5-(4-phosphonopentyryl)amino-6-D-ribitylaminouracil
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comparison with inhibition of Bacillus subtilis luminazine synthase/riboflavin synthase
5-(5-phosphonoxyvaleryl)amino-6-D-ribitylaminouracil
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mixed inhibition, comparison with inhibition of Bacillus subtilis luminazine synthase/riboflavin synthase
5-(hexyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione
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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comparison with inhibition of Bacillus subtilis lumazine synthase
5-[3-(propan-2-yl)-1H-pyrazol-5-yl]-3-(3,4,5-trimethoxyphenyl)-1,2,4-oxadiazole
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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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competitive, comparison with inhibition of Bacillus subtilis lumazine synthase
7-Hydroxy-6-(L-1,2-dihydroxyethyl)-8-(1-D-ribityl)lumazine
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i.e. photolumazine A
7-hydroxy-7-methyl-8-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)-7,8-dihydropteridin-2,4,6(1H,3H,5H)-trione
ethyl 2-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-ylamino)-2-oxoacetate
ethyl 5-(diethylcarbamoyl)-2-[2-(4-methoxyphenoxy)acetamido]-4-methylthiophene-3-carboxylate
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ethyl [(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)amino](oxo)acetate
methyl 2-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-ylamino)-2-oxoacetate
N-(2,4-dioxo-6-((2R,3R,4R)-2,3,4,5-tetrahydroxypentylthio)-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
N-(2,4-dioxo-6-((2R,3R,4R)-2,3,4,5-tetrahydroxypentylthio)-1,2,3,4-tetrahydropyrimidin-5-yl)propionamide
N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)isobutyramide
N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)propionamide
N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)-3,3,3-trifluoropropanamide
N-(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)-2-methylpropanamide
N-(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dion-5-ylpropionamide
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uncompetitive
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dione-5-ylisobutyramide
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uncompetitive
N-[2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino]-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
N-[2,4-dioxo-6-(ribitylamino)-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid ethyl ester
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mixed type inhibition
N-[3-(azepan-1-yl)propyl]-2-(4-methoxyphenyl)imidazo[2,1-b][1,3]benzothiazole-7-carboxamide
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N-[3-(diethylamino)propyl]-2-(4-ethoxyphenyl)imidazo[2,1-b][1,3]benzothiazole-7-carboxamide
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N-[3-(diethylamino)propyl]-2-(4-methylphenyl)imidazo[2,1-b][1,3]benzothiazole-7-carboxamide
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p-chloromercuribenzenesulfonate
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reversible by cysteine or 2-mercaptoethanol
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
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competitive inhibition
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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competitive inhibition
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uncompetitive inhibition
2,4-dioxo-6-[(3S,4S,5R)-3,4,5,6-tetrahydroxyhexyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
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uncompetitive inhibition
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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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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2-chloro-N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide
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2-chloro-N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide
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uncompetitive inhibition
2-chloro-N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
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2-chloro-N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
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competitive inhibition
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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comparison with inhibition of Bacillus subtilis lumazine synthase
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 Bacillus subtilis luminazine synthase/riboflavin synthase
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uncompetitive inhibition
5-amino-6-((2R,3R,4S)-2,3,4,5-tetrahydroxypentyloxy)-pyrimidine-2,4(1H,3H)-dione
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uncompetitive inhibition
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partial inhibition
5-amino-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
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competitive inhibition
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partial inhibition
5-nitro-6-[(3S,4S,5R)-3,4,5,6-tetrahydroxyhexyl]pyrimidine-2,4(1H,3H)-dione
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competitive inhibition
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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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partial inhibition
5-nitro-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
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partial inhibition
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competitive inhibition
5-nitro-6-[[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy]pyrimidine-2,4(1H,3H)-dione
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partial inhibition
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mixed-type inhibition
5-nitro-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]pyrimidine-2,4(1H,3H)-dione
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competitive inhibition
7-hydroxy-7-methyl-8-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)-7,8-dihydropteridin-2,4,6(1H,3H,5H)-trione
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7-hydroxy-7-methyl-8-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)-7,8-dihydropteridin-2,4,6(1H,3H,5H)-trione
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competitive inhibition
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competitive inhibition
8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-5,8-dihydropteridine-2,4,6,7(1H,3H)-tetrone
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competitive, comparison with inhibition of Bacillus subtilis lumazine synthase
9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,9-dihydro-1H-purine-2,6,8(3H)-trione
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competitive inhibition
9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,9-dihydro-1H-purine-2,6,8(3H)-trione
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ethyl 2-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-ylamino)-2-oxoacetate
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uncompetitive inhibition
ethyl 2-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-ylamino)-2-oxoacetate
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uncompetitive 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
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mixed-type 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
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ethyl [(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)amino](oxo)acetate
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uncompetitive inhibition
methyl 2-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-ylamino)-2-oxoacetate
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uncompetitive inhibition
methyl 2-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-ylamino)-2-oxoacetate
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uncompetitive inhibition
N-(2,4-dioxo-6-((2R,3R,4R)-2,3,4,5-tetrahydroxypentylthio)-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
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N-(2,4-dioxo-6-((2R,3R,4R)-2,3,4,5-tetrahydroxypentylthio)-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
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uncompetitive inhibition
N-(2,4-dioxo-6-((2R,3R,4R)-2,3,4,5-tetrahydroxypentylthio)-1,2,3,4-tetrahydropyrimidin-5-yl)propionamide
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N-(2,4-dioxo-6-((2R,3R,4R)-2,3,4,5-tetrahydroxypentylthio)-1,2,3,4-tetrahydropyrimidin-5-yl)propionamide
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uncompetitive inhibition
N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)isobutyramide
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N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)isobutyramide
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uncompetitive inhibition
N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
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N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
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uncompetitive inhibition
N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)propionamide
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N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)propionamide
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uncompetitive inhibition
N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)-3,3,3-trifluoropropanamide
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N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)-3,3,3-trifluoropropanamide
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uncompetitive inhibition
N-(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)-2-methylpropanamide
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uncompetitive inhibition
N-(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)-2-methylpropanamide
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N-(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
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uncompetitive inhibition
N-(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
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N-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-methacrylamide
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uncompetitive inhibition
N-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
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uncompetitive inhibition
N-[2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino]-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
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N-[2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino]-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
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partial inhibition
covalent hydrate of trifluoromethylated pyrazole
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
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covalent hydrate of trifluoromethylated pyrazole
covalent hydrate of trifluoromethylated pyrazole
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
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covalent hydrate of trifluoromethylated pyrazole
covalent hydrate of trifluoromethylated pyrazole
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
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covalent hydrate of trifluoromethylated pyrazole
covalent hydrate of trifluoromethylated pyrazole
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
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covalent hydrate of trifluoromethylated pyrazole
covalent hydrate of trifluoromethylated pyrazole
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
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covalent hydrate of trifluoromethylated pyrazole
covalent hydrate of trifluoromethylated pyrazole
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
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covalent hydrate of trifluoromethylated pyrazole
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a high-throughput screening for inhibitors of riboflavin synthase identifies antimicrobial compounds to treat brucellosis
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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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