Information on EC 2.5.1.78 - 6,7-dimethyl-8-ribityllumazine synthase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea

EC NUMBER
COMMENTARY hide
2.5.1.78
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RECOMMENDED NAME
GeneOntology No.
6,7-dimethyl-8-ribityllumazine synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
1-deoxy-L-glycero-tetrulose 4-phosphate + 5-amino-6-(D-ribitylamino)uracil = 6,7-dimethyl-8-(D-ribityl)lumazine + 2 H2O + phosphate
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
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flavin biosynthesis
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flavin biosynthesis I (bacteria and plants)
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flavin biosynthesis II (archaea)
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flavin biosynthesis III (fungi)
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Metabolic pathways
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Riboflavin metabolism
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SYSTEMATIC NAME
IUBMB Comments
5-amino-6-(D-ribitylamino)uracil butanedionetransferase
Involved in riboflavin biosynthesis.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain C58, ATCC 33970
SwissProt
Manually annotated by BRENDA team
strain C58, ATCC 33970
SwissProt
Manually annotated by BRENDA team
strain PCC 7120
SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
isoform RibH1
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-
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
subsp. nucleatum
SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
Methanothermobacter thermautotrophicum
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SwissProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
strain PCC 6803
SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
pv. campestris
SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
disruption mutants of either isform RibH1 or RibH2 obtained without any major difficulty, are not auxotrophic for riboflavin and grow at wild-type rates in both rich and minimal media. A double mutant lacking both RibH1 and RibH2 activity is not viable; disruption mutants of either isform RibH1 or RibH2 obtained without any major difficulty, are not auxotrophic for riboflavin and grow at wild-type rates in both rich and minimal media. A double mutant lacking both RibH1 and RibH2 activity is not viable. For virulence, at least one isoform must be present for Brucella abortus survival and RibH2 and not RibH1 is essential for intracellular survival due to its luminazine synthase activity in vivo.
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione + (3R)-3,4-dihydroxy-2-butanone 4-phosphate
6,7-dimethyl-8-(1-D-ribityl)lumazine + 2 H2O + phosphate
show the reaction diagram
5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione + (3S)-3,4-dihydroxy-2-butanone
?
show the reaction diagram
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-
-
-
?
5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione + (S)-2-hydroxy-3-oxobutyl dihydrogen phosphate
6,7-dimethyl-8-(1-D-ribityl)lumazine + phosphate
show the reaction diagram
5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione + (S)-2-hydroxy-3-oxobutyl dihydrogen phosphate
6,7-dimethyl-8-(1-D-ribityl)lumazine + phosphate + 2 H2O
show the reaction diagram
5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione + 5-nitro-6-ribitylamino-2,4(1H,3H)-pyrimidinedione
?
show the reaction diagram
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-
?
5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione + L-3,4-dihydroxybutan-2-one 4-phosphate
6,7-dimethyl-8-(1-D-ribityl)lumazine + 2 H2O + phosphate
show the reaction diagram
5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione + 3,4-dihydroxy-2-butanone 4-phosphate
6,7-dimethyl-8-ribityllumazine + 2 H2O + phosphate
show the reaction diagram
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?
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione + (S)-2-hydroxy-3-oxobutyl dihydrogen phosphate
6,7-dimethyl-8-(1-D-ribityl)lumazine + phosphate
show the reaction diagram
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penultimate step of riboflavin biosynthesis
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?
5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione + (S)-2-hydroxy-3-oxobutyl dihydrogen phosphate
6,7-dimethyl-8-(1-D-ribityl)lumazine + phosphate + 2 H2O
show the reaction diagram
5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione + L-3,4-dihydroxybutan-2-one 4-phosphate
6,7-dimethyl-8-(1-D-ribityl)lumazine + 2 H2O + phosphate
show the reaction diagram
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?
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(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
-
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
-
mixed inhibition
4-(6,7(5H,8H)-dioxo-8-D-ribityllumazine-5-yl)butane 1-phosphate
-
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
-
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
-
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
-
competitive
4-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-yl)butyl 1-phosphate
-
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
-
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
-
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
-
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
-
association constants and thermodynamic parameters of binding
5-(1,3,7-trihydro-9-D-ribityl-2,4,8-purinetrione-7-yl)pentane1-phosphate
-
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
-
comparison with inhibition of Escherichia coli riboflavin synthase
5-(5-phosphonopentyl)amino-6-D-ribitylaminouracil
-
comparison with inhibition of Escherichia coli riboflavin synthase
5-(5-phosphonoxyvaleryl)amino-6-D-ribitylaminouracil
-
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
-
competitive
5-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-yl)-n-pentyl 1-phosphonate
-
competitive
5-(6-D-ribitylamino-2,4(1H,3H)pyrimidinedione-5-yl)-1-pentyl-phosphonic acid
-
-
5-(hexyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione
-
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
-
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-styryluracil
5-nitro-6-[(D-ribityl)methyl]pyrimidine-2,4-dione
-
-
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
-
-
5-nitroso-6-ribityl-amino-2,4(1H,3H)pyrimidinedione
-
-
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
-
-
6-(1,3,7-trihydro-9-d-ribityl-2,4,8-purinetrione-7-yl)hexane 1-phosphate
-
association constants and thermodynamic parameters of binding
6-carboxyethyl-7-oxo-8-ribityllumazine
-
-
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
-
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
-
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
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.13
(3S)-3,4-dihydroxy-2-butanone
-
native enzyme complex, pH 7.0, 37C
0.0025 - 0.72
5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione
0.005
5-nitro-6-ribitylamino-2,4(1H,3H)-pyrimidinedione
-
native enzyme complex, pH 7.0, 37C
0.0052 - 3.14
L-3,4-dihydroxybutan-2-one 4-phosphate
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0003 - 0.0557
5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione
0.056 - 0.076
5-nitro-6-ribitylamino-2,4(1H,3H)-pyrimidinedione
0.0022 - 0.076
L-3,4-dihydroxybutan-2-one 4-phosphate
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.113
(1R)-1,2-dideoxy-1-fluoro-1-(5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-D-ribo-hexitol
-
pH 7.0, 37C, variable concentration of 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione
0.074 - 0.221
(1S)-1,2-dideoxy-1-fluoro-1-(5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-D-ribo-hexitol
0.13 - 0.197
(E)-3-hydroxy-4-(2-(5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-yl)vinyl)benzoic acid
0.041
(E)-4-(2-(5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-yl)vinyl)benzoate
-
pH 7.0, 27C
0.035
(E)-4-(2-(5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-yl)vinyl)benzoic acid
-
pH 7.0, 27C
0.095 - 0.21
(E)-5-nitro-6-(2-hydroxystyryl)pyrimidine-2,4(1H,3H)-dione
0.026
(E)-5-nitro-6-(3-(pyridin-3-yl)vinyl)pyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27C
0.011 - 0.042
(E)-5-nitro-6-(3-nitrostyryl)pyrimidine-2,4(1H,3H)-dione
0.026
(E)-5-nitro-6-(4-bromostyryl)pyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27C
0.0037 - 0.013
(E)-5-nitro-6-(4-nitrostyryl)pyrimidine-2,4(1H,3H)-dione
0.013 - 0.03
(E)-5-nitro-6-[2-(1H-pyrrol-2-yl)vinyl]pyrimidine-2,4(1H,3H)-dione
0.048
(E)-6-(2,3,4-trimethoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27C
0.0049 - 0.012
(E)-6-(2,3-dihydroxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
0.0096 - 0.243
(E)-6-(2,3-dimethoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
0.07 - 0.141
(E)-6-(2-(3H-indol-3-yl)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione
0.011 - 0.094
(E)-6-(2-(naphthalen-2-yl)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione
0.024 - 0.151
(E)-6-(2-fluoro-3-methoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
0.0078
(E)-6-(2-fluorostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27C
0.042
(E)-6-(2-hydroxy-3-nitrostyryl)-3-nitropyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27C
0.031
(E)-6-(2-hydroxy-5-nitrostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27C
0.023 - 0.085
(E)-6-(2-methoxy-5-nitrostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
0.028 - 0.205
(E)-6-(2-methoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
0.016
(E)-6-(2-nitrostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27C
0.017
(E)-6-(3,4,5-trimethoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27C
0.032
(E)-6-(3,4-dimethoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27C
0.052
(E)-6-(3-hydroxy-4-methoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27C
0.012 - 0.094
(E)-6-(3-hydroxy-4-nitrostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
0.0071
(E)-6-(3-hydroxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27C
0.045
(E)-6-(4-chlorostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27C
0.086
(E)-6-(4-fluorostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27C
0.087
(E)-6-(4-hydroxy-3-nitrostyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27C
0.012
(E)-6-(4-hydroxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27C
0.35
1,3,6,8-tetrahydroxynaphthyridine
-
pH 7.0, 37C
0.0014 - 0.0078
1-deoxy-1-(2,4,6,7-tetraoxo-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl)-D-ribitol
0.0091 - 0.046
1-deoxy-1-(2,6,8-trioxo-1,2,3,6,7,8-hexahydro-9H-purin-9-yl)-D-ribitol
0.83
1-deoxy-1-[(2,6-dioxo-5-[[5-(phosphonooxy)pentanoyl]amino]-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-D-ribitol
-
pH 7.0, 37C, variable concentration of L-3,4-dihydroxybutan-2-one 4-phosphate
0.000036
1-deoxy-1-[2,4,6,7-tetraoxo-5-[4-(phosphonooxy)butyl]-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl]-D-ribitol
-
pH 7.0, 37C
0.000012
1-deoxy-1-[2,4,6,7-tetraoxo-5-[5-(phosphonooxy)pentyl]-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl]-D-ribitol
-
pH 7.0, 37C
0.0000041 - 0.17
1-deoxy-1-[2,6,8-trioxo-7-[4-(phosphonooxy)butyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
0.0000047 - 0.852
1-deoxy-1-[2,6,8-trioxo-7-[5-(phosphonooxy)pentyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
0.0783 - 0.175
1-deoxy-1-[2,6,8-trioxo-7-[6-(phosphonooxy)hexyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
0.44
1-deoxy-1-[[2,6-dioxo-5-(4-phosphonobutyl)-1,2,3,6-tetrahydropyrimidin-4-yl]amino]-D-ribitol
-
pH 7.0, 37C, variable concentration of L-3,4-dihydroxybutan-2-one 4-phosphate
0.18
1-deoxy-1-[[2,6-dioxo-5-(5-phosphonopentyl)-1,2,3,6-tetrahydropyrimidin-4-yl]amino]-D-ribitol
-
pH 7.0, 37C, variable concentration of L-3,4-dihydroxybutan-2-one 4-phosphate
0.13
1-deoxy-1-[[2,6-dioxo-5-(6-phosphonohexyl)-1,2,3,6-tetrahydropyrimidin-4-yl]amino]-D-ribitol
-
pH 7.0, 37C, variable concentration of L-3,4-dihydroxybutan-2-one 4-phosphate
0.18 - 0.492
1-[(5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)(methyl)amino]-1-deoxy-D-ribitol hydrochloride
0.00016 - 0.031
2,4-dioxo-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
0.022 - 0.066
2,5,8,11-tetraaza-5,11-dihydro-4,10-dihydroxyperylene-1,3,6,7,9,12-hexaone
0.07
2-(2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamido)acetic acid
-
pH 7.0, 27C
0.0026
3-(1,3,7,9-tetrahydro-9-D-ribityl-2,6,8-trioxopurin-7-yl)-1-propanol
-
pH 7.0, 37C, variable concentration of 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione
0.0045 - 0.0414
3-(1,3,7,9-tetrahydro-9-D-ribityl-2,6,8-trioxopurin-7-yl)propane 1-phosphate
0.000002 - 0.000015
3-(1,3,7-trihydro-9-D-ribityl-2,6,8-purinetrione-7-yl)butane 1-phosphate
0.0000008 - 0.00003
3-(1,3,7-trihydro-9-D-ribityl-2,6,8-purinetrione-7-yl)pentane 1-phosphate
0.0000037 - 0.000101
3-[4,6-dioxo-4,5,6,7-tetrahydro-1-D-ribityl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]propyl 1-phosphate
0.0041 - 0.168
4-(1,3,7,9-tetrahydro-9-D-ribityl-2,6,8-trioxopurin-7-yl)butane 1-phosphate
0.000036 - 0.15
4-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)butane 1-phosphate
0.038
4-(2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamido)butyl dihydrogen phosphate
-
pH 7.0, 27C
0.000023
4-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-yl)-n-butyl 1-phosphate
-
pH 7.0, temperature not specified in the publication
0.084
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
-
pH 7.5, 37C, recombinant beta60 capsid
0.16
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
-
pH 7.5, 37C, recombinant beta60 capsid
0.12
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
-
pH 7.5, 37C, recombinant beta60 capsid
0.0000013 - 0.0000041
4-[4,6-dioxo-4,5,6,7-tetrahydro1-D-ribityl-1H-pyrazolo[3,4-d]-pyrimidin-3-yl]butyl 1-phosphate
0.06 - 0.132
5-(1,3,7,9-tetrahydro-9-D-ribityl-2,6,8-trioxopurin-7-yl)-1,1-difluoropentane 1-phosphonate
0.000012 - 0.027
5-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)pentane 1-phosphate
0.86
5-(4-phosphonobutyryl)amino-6-D-ribitylaminouracil
-
pH 7.5, 37C, recombinant beta60 capsid
1
5-(5-phosphonopentyl)amino-6-D-ribitylaminouracil
-
pH 7.5, 37C, recombinant beta60 capsid
0.83
5-(5-phosphonoxyvaleryl)amino-6-D-ribitylaminouracil
-
pH 7.5, 37C, recombinant beta60 capsid
0.00014
5-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-5-oxopentyl phosphate
-
pH 7.0, temperature not specified in the publication
0.00043
5-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-yl)-n-pentyl 1-phosphonate
-
pH 7.0, temperature not specified in the publication
0.13
5-(hexyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione
-
pH 7.5, 37C, recombinant beta60 capsid
0.18
5-(pentyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione
-
pH 7.5, 37C, recombinant beta60 capsid
0.015 - 0.143
5-nitro-6-styryluracil
0.264
5-nitro-6-[(D-ribityl)methyl]pyrimidine-2,4-dione
-
pH 7.0, 37C, variable concentration of 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione
0.002 - 0.026
5-nitro-6-[[(2R,3R,4R)-2,3,4,5 tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
0.0000047 - 0.0000077
5-[4,6-dioxo-4,5,6,7-tetrahydro-1-D-ribityl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]pentyl 1-phosphate
0.094
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
-
pH 7.5, 37C, recombinant beta60 capsid
0.0014 - 0.0078
8-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]tetrahydropteridine-2,4,6,7(1H,3H)-tetrone
0.046
9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,9-dihydro-1H-purine-2,6,8(3H)-trione
-
pH 7.5, 37C, recombinant beta60 capsid
0.0011 - 0.607
ethyl [(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)amino](oxo)acetate
0.017
riboflavin
pH 7.0, 37C, wild-type enzyme
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.011 - 0.11
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dion-5-ylpropionamide
0.0079 - 0.095
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dione-5-ylisobutyramide
0.00101 - 0.607
N-[2,4-dioxo-6-(ribitylamino)-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid ethyl ester
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.018
-
-
0.031
-
37C, pH 7.0
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.6
-
calculated from sequence
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
high expression
Manually annotated by BRENDA team
high expression in young leaf
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
constitutes less than 0.02% of the total chloroplast protein. The enzyme is exclusivelylocated in the chloroplast stroma
Manually annotated by BRENDA team
sequence contains an N-terminal extension representing a plastid-targeting sequence
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
Aquifex aeolicus (strain VF5)
Aquifex aeolicus (strain VF5)
Aquifex aeolicus (strain VF5)
Aquifex aeolicus (strain VF5)
Aquifex aeolicus (strain VF5)
Bacillus subtilis (strain 168)
Bacillus subtilis (strain 168)
Brucella abortus biovar 1 (strain 9-941)
Brucella abortus biovar 1 (strain 9-941)
Brucella abortus biovar 1 (strain 9-941)
Brucella abortus biovar 1 (strain 9-941)
Brucella abortus biovar 1 (strain 9-941)
Brucella melitensis biotype 1 (strain 16M / ATCC 23456 / NCTC 10094)
Candida glabrata (strain ATCC 2001 / CBS 138 / JCM 3761 / NBRC 0622 / NRRL Y-65)
Magnaporthe oryzae (strain 70-15 / ATCC MYA-4617 / FGSC 8958)
Mycobacterium leprae (strain Br4923)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Rhizobium loti (strain MAFF303099)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Schizosaccharomyces pombe (strain 972 / ATCC 24843)
Schizosaccharomyces pombe (strain 972 / ATCC 24843)
Schizosaccharomyces pombe (strain 972 / ATCC 24843)
Schizosaccharomyces pombe (strain 972 / ATCC 24843)
Schizosaccharomyces pombe (strain 972 / ATCC 24843)
Schizosaccharomyces pombe (strain 972 / ATCC 24843)
Schizosaccharomyces pombe (strain 972 / ATCC 24843)
Schizosaccharomyces pombe (strain 972 / ATCC 24843)
Schizosaccharomyces pombe (strain 972 / ATCC 24843)
Schizosaccharomyces pombe (strain 972 / ATCC 24843)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
75300
-
isoform RibH1, light scattering experiments
80100
-
light scattering experiments, isoform RibH1
85500
-
isoform RibH1, light scattering experiments
87000
sedimentation equilibrium centrifugation
88000
-
sedimentation equilibrium experiments
158500
-
isoform RinH2, light scattering experiments
850000
-
gel filtration
973000 - 991000
-
sedimentaion equilibrium studies
977000
-
sedimentation equilibrium analysis
additional information
-
the protein is an icosahedral capsid of 60 subunits with a mass of about 1 MDa as shown by hydrodynamic studies and by electron microscopy. The lumazine synthase of Escherichia coli is not physically associated with another enzyme of the riboflavin pathway, and the core of the icosahedral capsid is empty
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60-mer
decamer
pentamer
additional information