2.0 2012-05-31 14:00:20 -0600 2015-06-03 15:54:32 -0600 ECMDB03826 M2MDB000524 6,7-Dimethyl-8-(1-D-ribityl)lumazine 6,7-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)-ribitol 1-Deoxy-1-[6,7-dimethyl-2,4-dioxo-3,4-dihydropteridin-8(2H)-yl]-D-ribitol 6,7-Dimethyl-8-(1'-D-ribityl)lumazine 6,7-Dimethyl-8-(1-D-ribityl)lumazine 6,7-Dimethyl-8-ribityllumazine 6,7-Dimethyl-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]pteridine-2,4-dione 6,7D81RbL DMDRL C13H18N4O6 326.3052 326.122634328 6,7-dimethyl-8-(2,3,4,5-tetrahydroxypentyl)-2,3,4,8-tetrahydropteridine-2,4-dione 6,7-dimethyl-8-(2,3,4,5-tetrahydroxypentyl)-3H-pteridine-2,4-dione 5118-16-1 CC1=C(C)N(CC(O)C(O)C(O)CO)C2=NC(=O)NC(=O)C2=N1 InChI=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-N Solid Cytosol logp -1.84 ALOGPS logs -2.42 ALOGPS solubility 1.23e+00 g/l ALOGPS logp -2.7 ChemAxon pka_strongest_acidic 6.97 ChemAxon pka_strongest_basic -1.2 ChemAxon iupac 6,7-dimethyl-8-(2,3,4,5-tetrahydroxypentyl)-2,3,4,8-tetrahydropteridine-2,4-dione ChemAxon average_mass 326.3052 ChemAxon mono_mass 326.122634328 ChemAxon smiles CC1=C(C)N(CC(O)C(O)C(O)CO)C2=NC(=O)NC(=O)C2=N1 ChemAxon formula C13H18N4O6 ChemAxon inchi InChI=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) ChemAxon inchikey SXDXRJZUAJBNFL-UHFFFAOYSA-N ChemAxon polar_surface_area 155.05 ChemAxon refractivity 79 ChemAxon polarizability 31.53 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Riboflavin metabolism ec00740 Flavin biosynthesis The 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. PW001971 Metabolic flavin biosynthesis I (bacteria and plants) RIBOSYN2-PWY Specdb::CMs 10009 Specdb::CMs 38657 Specdb::NmrOneD 271638 Specdb::NmrOneD 271639 Specdb::NmrOneD 271640 Specdb::NmrOneD 271641 Specdb::NmrOneD 271642 Specdb::NmrOneD 271643 Specdb::NmrOneD 271644 Specdb::NmrOneD 271645 Specdb::NmrOneD 271646 Specdb::NmrOneD 271647 Specdb::NmrOneD 271648 Specdb::NmrOneD 271649 Specdb::NmrOneD 271650 Specdb::NmrOneD 271651 Specdb::NmrOneD 271652 Specdb::NmrOneD 271653 Specdb::NmrOneD 271654 Specdb::NmrOneD 271655 Specdb::NmrOneD 271656 Specdb::NmrOneD 271657 Specdb::MsMs 24431 Specdb::MsMs 24432 Specdb::MsMs 24433 Specdb::MsMs 30989 Specdb::MsMs 30990 Specdb::MsMs 30991 HMDB03826 168989 652 C04332 17601 DIMETHYL-D-RIBITYL-LUMAZINE Keseler, 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. 21097882 Kanehisa, 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. 22080510 van 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. 17765195 Winder, 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. 18331064 Riboflavin synthase alpha chain P0AFU8 RISA_ECOLI ribE http://ecmdb.ca/proteins/P0AFU8.xml 6,7-dimethyl-8-ribityllumazine synthase P61714 RISB_ECOLI ribH http://ecmdb.ca/proteins/P61714.xml 2 6,7-Dimethyl-8-(1-D-ribityl)lumazine > 5-Amino-6-ribitylamino uracil + Riboflavin R00066 5-Amino-6-ribitylamino uracil + 3,4-Dihydroxy-2-butanone-4-P > 6,7-Dimethyl-8-(1-D-ribityl)lumazine +2 Water + Phosphate R04457 2 6,7-Dimethyl-8-(1-D-ribityl)lumazine <> Riboflavin + 5-Amino-6-ribitylamino uracil R00066 5-Amino-6-ribitylamino uracil + 3,4-Dihydroxy-2-butanone-4-P <> 6,7-Dimethyl-8-(1-D-ribityl)lumazine +2 Water + Phosphate R04457 5-amino-6-(D-ribitylamino)uracil + 3,4-Dihydroxy-2-butanone-4-P > Hydrogen ion + 6,7-Dimethyl-8-(1-D-ribityl)lumazine + Phosphate + Water LUMAZINESYN-RXN Hydrogen ion + 6,7-Dimethyl-8-(1-D-ribityl)lumazine > 5-amino-6-(D-ribitylamino)uracil + Riboflavin RIBOFLAVIN-SYN-RXN 5-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)lumazine PW_R005556 6,7-Dimethyl-8-(1-D-ribityl)lumazine + Hydrogen ion + 6,7-Dimethyl-8-(1-D-ribityl)lumazine > Riboflavin + 5-Amino-6-ribitylamino uracil + Riboflavin PW_R005563 2 6,7-Dimethyl-8-(1-D-ribityl)lumazine >5 5-Amino-6-ribitylamino uracil + Riboflavin