2.02012-05-31 14:06:25 -06002015-06-03 15:54:47 -0600ECMDB04145M2MDB0006355-Amino-6-ribitylamino uracil5-Amino-6-ribitylamino uracil is an intermediate in riboflavin metabolism. It is converted from 5-Amino-6-(5'-phosphoribitylamino)uracil via dephosphorylation by the enzyme phosphohistidine phosphatase 1 (EC 3.1.3.-). (HMDB, KEGG) 1-[(5-Amino-2,6-dihydroxypyrimidin-4-yl)amino]-1-deoxy-D-ribitol1-[(5-Amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-1-deoxy-D-ribitol4-(1-D-Ribitylamino)-5-amino-2,6 dihydroxypyrimidine4-(1-D-Ribitylamino)-5-amino-2,6-dihydroxypyrimidine4-(1-D-Ribitylamino)-5-aminouracil5-Amino-6-(2,3,4,5-tetrahydroxypentylamino)-1H-pyrimidine-2,4-dione5A6RbA2,4PD6-Ribitylamino-5-aminouracilC9H16N4O6276.2465276.1069842645-amino-6-[(2,3,4,5-tetrahydroxypentyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dione5-amino-6-[(2,3,4,5-tetrahydroxypentyl)amino]-1,3-dihydropyrimidine-2,4-dioneNC1=C(NCC(O)C(O)C(O)CO)NC(=O)NC1=OInChI=1S/C9H16N4O6/c10-5-7(12-9(19)13-8(5)18)11-1-3(15)6(17)4(16)2-14/h3-4,6,14-17H,1-2,10H2,(H3,11,12,13,18,19)XKQZIXVJVUPORE-UHFFFAOYSA-NSolidCytosollogp-2.44logs-1.29solubility1.43e+01 g/llogp-4.4pka_strongest_acidic9.41pka_strongest_basic4.36iupac5-amino-6-[(2,3,4,5-tetrahydroxypentyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dioneaverage_mass276.2465mono_mass276.106984264smilesNC1=C(NCC(O)C(O)C(O)CO)NC(=O)NC1=OformulaC9H16N4O6inchiInChI=1S/C9H16N4O6/c10-5-7(12-9(19)13-8(5)18)11-1-3(15)6(17)4(16)2-14/h3-4,6,14-17H,1-2,10H2,(H3,11,12,13,18,19)inchikeyXKQZIXVJVUPORE-UHFFFAOYSA-Npolar_surface_area177.17refractivity71.48polarizability25.92rotatable_bond_count6acceptor_count8donor_count8physiological_charge0formal_charge0Methane metabolismec00680Riboflavin metabolismec00740Microbial metabolism in diverse environmentsec01120Flavin 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.
PW001971MetabolicSpecdb::CMs2464Specdb::CMs39546Specdb::NmrOneD279538Specdb::NmrOneD279539Specdb::NmrOneD279540Specdb::NmrOneD279541Specdb::NmrOneD279542Specdb::NmrOneD279543Specdb::NmrOneD279544Specdb::NmrOneD279545Specdb::NmrOneD279546Specdb::NmrOneD279547Specdb::NmrOneD279548Specdb::NmrOneD279549Specdb::NmrOneD279550Specdb::NmrOneD279551Specdb::NmrOneD279552Specdb::NmrOneD279553Specdb::NmrOneD279554Specdb::NmrOneD279555Specdb::NmrOneD279556Specdb::NmrOneD279557Specdb::MsMs24389Specdb::MsMs24390Specdb::MsMs24391Specdb::MsMs30947Specdb::MsMs30948Specdb::MsMs30949HMDB11106221216C0473215934Kanehisa, 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-D114.22080510WACKER H, HARVEY RA, WINESTOCK CH, PLAUT GW: 4-(1'-D-RIBITYLAMINO)-5-AMINO-2,6-DIHYDROXYPYRIMIDINE, THE SECOND PRODUCT OF THE RIBOFLAVIN SYNTHETASE REACTION. J Biol Chem. 1964 Oct;239:3493-7.14245407Riboflavin synthase alpha chainP0AFU8RISA_ECOLIribEhttp://ecmdb.ca/proteins/P0AFU8.xml6,7-dimethyl-8-ribityllumazine synthaseP61714RISB_ECOLIribHhttp://ecmdb.ca/proteins/P61714.xmlPhosphatase ybjIP75809YBJI_ECOLIybjIhttp://ecmdb.ca/proteins/P75809.xml5-amino-6-(5-phospho-D-ribitylamino)uracil phosphatase YigBP0ADP0YIGB_ECOLIyigBhttp://ecmdb.ca/proteins/P0ADP0.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-(5'-phosphoribitylamino)uracil + Water + 5-Amino-6-(5'-phosphoribitylamino)uracil > Phosphate + 5-Amino-6-ribitylamino uracilPW_R0055525-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