2.0 2012-07-30 14:54:47 -0600 2015-09-17 15:41:18 -0600 ECMDB21177 M2MDB001586 5-Amino-6-(5'-phosphoribitylamino)uracil 5-Amino-6-(5'-phosphoribitylamino)uracil is an intermediate in Riboflavin metabolism. 5-Amino-6-(5'-phosphoribitylamino)uracil is the; 3rd to last step in the synthesis of 7-Hydroxy-6-methyl-8-ribityl lumazine and is converted from 5-Amino-6-(5'-phosphoribosylamino)uracil via the enzyme 5-amino-6-(5-phosphoribosylamino)uracil reductase (EC 1.1.1.193). It is then; converted to 4-(1-D-Ribitylamino)-5-amino-2,6-dihydroxypyrimidine via the enzyme Hydrolases (EC 3.1.3.- ). 1-(5-Amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-ylamino)-1-deoxy-5-O-phosphono-D-ribitol 1-(5-Amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-ylamino)-1-deoxy-D-ribitol 5-(dihydrogen phosphate) 1-(5-amino-2,6-dioxo-1,2,3,6-Tetrahydropyrimidin-4-ylamino)-1-deoxy-D-ribitol 5-(dihydrogen phosphoric acid) 1-[(5-Amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-1-deoxy-5-O-phosphono-D-ribitol 5-Amino-2,6-dioxy-4-(5'-phospho-D-ribitylamino)pyrimidine 5-Amino-2,6-dioxy-4-(5'-phosphoribitylamino)pyrimidine 5-Amino-6-(5'-phospho-D-ribitylamino)uracil 5-Amino-6-(5'-phosphoribitylamino)uracil 5-Amino-6-(5-phospho-D-ribitylamino)uracil 5-Amino-6-(5-phosphoribitylamino)uracil 5-Amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione 5'-phosphate 5-amino-6-ribitylamino-2,4(1H,3H)-Pyrimidinedione 5'-phosphoric acid 5A6-5'PRbAU C9H17N4O9P 356.2264 356.073314674 {[(2R,3S,4S)-5-[(5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-2,3,4-trihydroxypentyl]oxy}phosphonic acid [(2R,3S,4S)-5-[(5-amino-2,6-dioxo-1,3-dihydropyrimidin-4-yl)amino]-2,3,4-trihydroxypentyl]oxyphosphonic acid NC1=C(NCC(O)C(O)C(O)COP(O)(O)=O)NC(=O)NC1=O InChI=1S/C9H17N4O9P/c10-5-7(12-9(18)13-8(5)17)11-1-3(14)6(16)4(15)2-22-23(19,20)21/h3-4,6,14-16H,1-2,10H2,(H2,19,20,21)(H3,11,12,13,17,18) RQRINYISXYAZKL-UHFFFAOYSA-N Solid Cytosol logp -2.49 ALOGPS logs -2.09 ALOGPS solubility 2.89e+00 g/l ALOGPS logp -4.5 ChemAxon pka_strongest_acidic 1.49 ChemAxon pka_strongest_basic -2.7 ChemAxon iupac {[(2R,3S,4S)-5-[(5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-2,3,4-trihydroxypentyl]oxy}phosphonic acid ChemAxon average_mass 356.2264 ChemAxon mono_mass 356.073314674 ChemAxon smiles NC1=C(NCC(O)C(O)C(O)COP(O)(O)=O)NC(=O)NC1=O ChemAxon formula C9H17N4O9P ChemAxon inchi InChI=1S/C9H17N4O9P/c10-5-7(12-9(18)13-8(5)17)11-1-3(14)6(16)4(15)2-22-23(19,20)21/h3-4,6,14-16H,1-2,10H2,(H2,19,20,21)(H3,11,12,13,17,18) ChemAxon inchikey RQRINYISXYAZKL-UHFFFAOYSA-N ChemAxon polar_surface_area 223.7 ChemAxon refractivity 82.36 ChemAxon polarizability 30.06 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 10 ChemAxon donor_count 9 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon 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 3461 Specdb::CMs 134619 Specdb::CMs 142353 Specdb::NmrOneD 149640 Specdb::NmrOneD 149641 Specdb::NmrOneD 149642 Specdb::NmrOneD 149643 Specdb::NmrOneD 149644 Specdb::NmrOneD 149645 Specdb::NmrOneD 149646 Specdb::NmrOneD 149647 Specdb::NmrOneD 149648 Specdb::NmrOneD 149649 Specdb::NmrOneD 149650 Specdb::NmrOneD 149651 Specdb::NmrOneD 149652 Specdb::NmrOneD 149653 Specdb::NmrOneD 149654 Specdb::NmrOneD 149655 Specdb::NmrOneD 149656 Specdb::NmrOneD 149657 Specdb::NmrOneD 149658 Specdb::NmrOneD 149659 Specdb::MsMs 26840 Specdb::MsMs 26841 Specdb::MsMs 26842 Specdb::MsMs 33398 Specdb::MsMs 33399 Specdb::MsMs 33400 Specdb::MsMs 2455689 Specdb::MsMs 2455690 Specdb::MsMs 2455691 Specdb::MsMs 2479999 Specdb::MsMs 2480000 Specdb::MsMs 2480001 HMDB03841 333 18921533 C04454 18247 CPD-1086 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 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 biosynthesis protein ribD P25539 RIBD_ECOLI ribD http://ecmdb.ca/proteins/P25539.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 5-Amino-6-(5'-phosphoribosylamino)uracil + Hydrogen ion + NADPH > 5-Amino-6-(5'-phosphoribitylamino)uracil + NADP R03458 RIBOFLAVINSYNREDUC-RXN 5-Amino-6-(5'-phosphoribitylamino)uracil + NADP <> 5-Amino-6-(5'-phosphoribosylamino)uracil + NADPH + Hydrogen ion R03458 RIBOFLAVINSYNREDUC-RXN 5-Amino-6-(5'-phosphoribitylamino)uracil + Water > 5-amino-6-(D-ribitylamino)uracil + Phosphate RIBOPHOSPHAT-RXN 5-Amino-6-(5'-phosphoribitylamino)uracil + NADP < 5-Amino-6-(5'-phosphoribosylamino)uracil + NADPH + Hydrogen ion RIBOFLAVINSYNREDUC-RXN 5-Amino-6-(5'-phosphoribitylamino)uracil + NADP > 5-amino-6-(5-phospho-D-ribosylamino)uracil + NADPH 5-Amino-6-(5'-phosphoribosylamino)uracil + Hydrogen ion + NADPH + NADPH > NADP + 5-Amino-6-(5'-phosphoribitylamino)uracil + 5-Amino-6-(5'-phosphoribitylamino)uracil PW_R005548 5-Amino-6-(5'-phosphoribitylamino)uracil + Water + 5-Amino-6-(5'-phosphoribitylamino)uracil > Phosphate + 5-Amino-6-ribitylamino uracil PW_R005552 5 5-Amino-6-(5'-phosphoribosylamino)uracil + Hydrogen ion + NADPH >5 5-Amino-6-(5'-phosphoribitylamino)uracil + NADP 5 5-Amino-6-(5'-phosphoribosylamino)uracil + Hydrogen ion + NADPH >5 5-Amino-6-(5'-phosphoribitylamino)uracil + NADP