2.02012-05-31 14:00:20 -06002015-06-03 15:54:32 -0600ECMDB03826M2MDB0005246,7-Dimethyl-8-(1-D-ribityl)lumazine6,7-Dimethyl-8-(1-D-ribityl)lumazine is an intermediate in riboflavin metabolism. 6,7-Dimethyl-8-(1-D-ribityl)lumazine is the second to last step in the synthesis of ribitol and is converted from 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine via the enzyme riboflavin synthase beta chain. It is then 1-Deoxy-1-(3,4-dihydro-6,7-dimethyl-2,4-dioxo-8(2H)-pteridinyl)-ribitol1-Deoxy-1-[6,7-dimethyl-2,4-dioxo-3,4-dihydropteridin-8(2H)-yl]-D-ribitol6,7-Dimethyl-8-(1'-D-ribityl)lumazine6,7-Dimethyl-8-(1-D-ribityl)lumazine6,7-Dimethyl-8-ribityllumazine6,7-Dimethyl-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]pteridine-2,4-dione6,7D81RbLDMDRLC13H18N4O6326.3052326.1226343286,7-dimethyl-8-(2,3,4,5-tetrahydroxypentyl)-2,3,4,8-tetrahydropteridine-2,4-dione6,7-dimethyl-8-(2,3,4,5-tetrahydroxypentyl)-3H-pteridine-2,4-dione5118-16-1CC1=C(C)N(CC(O)C(O)C(O)CO)C2=NC(=O)NC(=O)C2=N1InChI=1S/C13H18N4O6/c1-5-6(2)17(3-7(19)10(21)8(20)4-18)11-9(14-5)12(22)16-13(23)15-11/h7-8,10,18-21H,3-4H2,1-2H3,(H,16,22,23)SXDXRJZUAJBNFL-UHFFFAOYSA-NSolidCytosollogp-1.84logs-2.42solubility1.23e+00 g/llogp-2.7pka_strongest_acidic6.97pka_strongest_basic-1.2iupac6,7-dimethyl-8-(2,3,4,5-tetrahydroxypentyl)-2,3,4,8-tetrahydropteridine-2,4-dioneaverage_mass326.3052mono_mass326.122634328smilesCC1=C(C)N(CC(O)C(O)C(O)CO)C2=NC(=O)NC(=O)C2=N1formulaC13H18N4O6inchiInChI=1S/C13H18N4O6/c1-5-6(2)17(3-7(19)10(21)8(20)4-18)11-9(14-5)12(22)16-13(23)15-11/h7-8,10,18-21H,3-4H2,1-2H3,(H,16,22,23)inchikeySXDXRJZUAJBNFL-UHFFFAOYSA-Npolar_surface_area155.05refractivity79polarizability31.53rotatable_bond_count5acceptor_count9donor_count5physiological_charge-1formal_charge0Riboflavin metabolismec00740Flavin biosynthesisThe process of flavin biosynthesis starts with GTP being metabolized by interacting with 3 molecules of water through a GTP cyclohydrolase resulting in a release of formic acid, a pyrophosphate, two hydrog ions and 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one or 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine. Either of these compounds interacts with a water molecule and a hydrogen ion through a fused diaminohydroxyphosphoribosylaminopyrimidine deaminase / 5-amino-6-(5-phosphoribosylamino)uracil reductase resulting in an ammonium and 5-amino-6-(5-phospho-D-ribosylamino)uracil. This compound then interacts with a hydrogen ion through a NADPH dependent fused diaminohydroxyphosphoribosylaminopyrimidine deaminase / 5-amino-6-(5-phosphoribosylamino)uracil reductase resulting in the release of a NADP and a 5-amino-6-(5-phospho-D-ribitylamino)uracil. This compound then interacts with a water molecule through a 5-amino-6-(5-phospho-D-ribitylamino)uracil phosphatase resulting in a release of a phosphate, and a 5-amino-6-(D-ribitylamino)uracil.
D-ribulose 5-phosphate interacts with a3,4-dihydroxy-2-butanone 4-phosphate synthase resulting in the release of formic acid, a hydrogen ion and 1-deoxy-L-glycero-tetrulose 4-phosphate.
A 5-amino-6-(D-ribitylamino)uracil and 1-deoxy-L-glycero-tetrulose 4-phosphate interact through a 6,7-dimethyl-8-ribityllumazine synthase resulting in the release of 2 water molecules, a phosphate, a hydrogen ion and a 6,7-dimethyl-8-(1-D-ribityl)lumazine.
The latter compound then interacts with a hydrogen ion through a riboflavin synthase resulting in the release of a riboflavin and a 5-amino-6-(d-ribitylamino)uracil.
The riboflavin is then phosphorylated through an ATP dependent riboflavin kinase resulting in the release of a ADP, a hydrogen ion and a FLAVIN MONONUCLEOTIDE.
The flavin mononucleotide interad with a hydrogen ion and an ATP through the riboflavin kinase resulting in the release of a pyrophosphate and Flavin Adenine dinucleotide. This compound is then exported into the periplasm through a FMN/FAD exporter.
PW001971Metabolicflavin biosynthesis I (bacteria and plants)RIBOSYN2-PWYSpecdb::CMs10009Specdb::CMs38657Specdb::NmrOneD271638Specdb::NmrOneD271639Specdb::NmrOneD271640Specdb::NmrOneD271641Specdb::NmrOneD271642Specdb::NmrOneD271643Specdb::NmrOneD271644Specdb::NmrOneD271645Specdb::NmrOneD271646Specdb::NmrOneD271647Specdb::NmrOneD271648Specdb::NmrOneD271649Specdb::NmrOneD271650Specdb::NmrOneD271651Specdb::NmrOneD271652Specdb::NmrOneD271653Specdb::NmrOneD271654Specdb::NmrOneD271655Specdb::NmrOneD271656Specdb::NmrOneD271657Specdb::MsMs24431Specdb::MsMs24432Specdb::MsMs24433Specdb::MsMs30989Specdb::MsMs30990Specdb::MsMs30991HMDB03826168989652C0433217601DIMETHYL-D-RIBITYL-LUMAZINEKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Riboflavin synthase alpha chainP0AFU8RISA_ECOLIribEhttp://ecmdb.ca/proteins/P0AFU8.xml6,7-dimethyl-8-ribityllumazine synthaseP61714RISB_ECOLIribHhttp://ecmdb.ca/proteins/P61714.xml2 6,7-Dimethyl-8-(1-D-ribityl)lumazine > 5-Amino-6-ribitylamino uracil + RiboflavinR000665-Amino-6-ribitylamino uracil + 3,4-Dihydroxy-2-butanone-4-P > 6,7-Dimethyl-8-(1-D-ribityl)lumazine +2 Water + PhosphateR044572 6,7-Dimethyl-8-(1-D-ribityl)lumazine <> Riboflavin + 5-Amino-6-ribitylamino uracilR000665-Amino-6-ribitylamino uracil + 3,4-Dihydroxy-2-butanone-4-P <> 6,7-Dimethyl-8-(1-D-ribityl)lumazine +2 Water + PhosphateR044575-amino-6-(D-ribitylamino)uracil + 3,4-Dihydroxy-2-butanone-4-P > Hydrogen ion + 6,7-Dimethyl-8-(1-D-ribityl)lumazine + Phosphate + WaterLUMAZINESYN-RXNHydrogen ion + 6,7-Dimethyl-8-(1-D-ribityl)lumazine > 5-amino-6-(D-ribitylamino)uracil + RiboflavinRIBOFLAVIN-SYN-RXN5-Amino-6-ribitylamino uracil + 1-Deoxy-L-glycero-tetrulose 4-phosphate > Water + Phosphate + Hydrogen ion + 6,7-Dimethyl-8-(1-D-ribityl)lumazine + 6,7-Dimethyl-8-(1-D-ribityl)lumazinePW_R0055566,7-Dimethyl-8-(1-D-ribityl)lumazine + Hydrogen ion + 6,7-Dimethyl-8-(1-D-ribityl)lumazine > Riboflavin + 5-Amino-6-ribitylamino uracil + RiboflavinPW_R0055632 6,7-Dimethyl-8-(1-D-ribityl)lumazine >5 5-Amino-6-ribitylamino uracil + Riboflavin