2.0 2012-05-31 14:06:25 -0600 2015-06-03 15:54:47 -0600 ECMDB04145 M2MDB000635 5-Amino-6-ribitylamino uracil 5-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-ribitol 1-[(5-Amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-1-deoxy-D-ribitol 4-(1-D-Ribitylamino)-5-amino-2,6 dihydroxypyrimidine 4-(1-D-Ribitylamino)-5-amino-2,6-dihydroxypyrimidine 4-(1-D-Ribitylamino)-5-aminouracil 5-Amino-6-(2,3,4,5-tetrahydroxypentylamino)-1H-pyrimidine-2,4-dione 5A6RbA2,4PD 6-Ribitylamino-5-aminouracil C9H16N4O6 276.2465 276.106984264 5-amino-6-[(2,3,4,5-tetrahydroxypentyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dione 5-amino-6-[(2,3,4,5-tetrahydroxypentyl)amino]-1,3-dihydropyrimidine-2,4-dione NC1=C(NCC(O)C(O)C(O)CO)NC(=O)NC1=O InChI=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-N Solid Cytosol logp -2.44 ALOGPS logs -1.29 ALOGPS solubility 1.43e+01 g/l ALOGPS logp -4.4 ChemAxon pka_strongest_acidic 9.41 ChemAxon pka_strongest_basic 4.36 ChemAxon iupac 5-amino-6-[(2,3,4,5-tetrahydroxypentyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dione ChemAxon average_mass 276.2465 ChemAxon mono_mass 276.106984264 ChemAxon smiles NC1=C(NCC(O)C(O)C(O)CO)NC(=O)NC1=O ChemAxon formula C9H16N4O6 ChemAxon inchi InChI=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) ChemAxon inchikey XKQZIXVJVUPORE-UHFFFAOYSA-N ChemAxon polar_surface_area 177.17 ChemAxon refractivity 71.48 ChemAxon polarizability 25.92 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 8 ChemAxon donor_count 8 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Methane metabolism ec00680 Riboflavin metabolism ec00740 Microbial metabolism in diverse environments ec01120 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 Specdb::CMs 2464 Specdb::CMs 39546 Specdb::NmrOneD 279538 Specdb::NmrOneD 279539 Specdb::NmrOneD 279540 Specdb::NmrOneD 279541 Specdb::NmrOneD 279542 Specdb::NmrOneD 279543 Specdb::NmrOneD 279544 Specdb::NmrOneD 279545 Specdb::NmrOneD 279546 Specdb::NmrOneD 279547 Specdb::NmrOneD 279548 Specdb::NmrOneD 279549 Specdb::NmrOneD 279550 Specdb::NmrOneD 279551 Specdb::NmrOneD 279552 Specdb::NmrOneD 279553 Specdb::NmrOneD 279554 Specdb::NmrOneD 279555 Specdb::NmrOneD 279556 Specdb::NmrOneD 279557 Specdb::MsMs 24389 Specdb::MsMs 24390 Specdb::MsMs 24391 Specdb::MsMs 30947 Specdb::MsMs 30948 Specdb::MsMs 30949 HMDB11106 221 216 C04732 15934 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 WACKER 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. 14245407 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 Phosphatase ybjI P75809 YBJI_ECOLI ybjI http://ecmdb.ca/proteins/P75809.xml 5-amino-6-(5-phospho-D-ribitylamino)uracil phosphatase YigB P0ADP0 YIGB_ECOLI yigB http://ecmdb.ca/proteins/P0ADP0.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-(5'-phosphoribitylamino)uracil + Water + 5-Amino-6-(5'-phosphoribitylamino)uracil > Phosphate + 5-Amino-6-ribitylamino uracil PW_R005552 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