2.0 2012-05-31 14:27:26 -0600 2015-06-03 17:19:18 -0600 ECMDB20099 M2MDB000947 5-Amino-6-(5'-phosphoribosylamino)uracil 5-amino-6-(5'-phosphoribosylamino)uracil is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. 5-amino-6-(5'-phosphoribosylamino)uracil 5-Amino-6-(5-phosphoribosylamino)uracil 5-Amino-6-(ribosylamino)-2,4-(1H,3H)-pyrimidinedione 5'-phosphate 5-amino-6-(ribosylamino)-2,4-(1H,3H)-Pyrimidinedione 5'-phosphoric acid 5A6-5'PRAU C9H15N4O9P 354.2106 354.05766461 {[(2R,3S,4R,5R)-5-[(5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid [(2R,3S,4R,5R)-5-[(5-amino-2,6-dioxo-1,3-dihydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid NC1=C(N[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)NC(=O)NC1=O InChI=1S/C9H15N4O9P/c10-3-6(12-9(17)13-7(3)16)11-8-5(15)4(14)2(22-8)1-21-23(18,19)20/h2,4-5,8,14-15H,1,10H2,(H2,18,19,20)(H3,11,12,13,16,17)/t2-,4-,5-,8-/m1/s1 LZEXYCAGPMYXLX-UMMCILCDSA-N Cytosol logp -1.84 ALOGPS logs -1.99 ALOGPS solubility 3.64e+00 g/l ALOGPS logp -3.7 ChemAxon pka_strongest_acidic 1.23 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac {[(2R,3S,4R,5R)-5-[(5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 354.2106 ChemAxon mono_mass 354.05766461 ChemAxon smiles NC1=C(N[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)NC(=O)NC1=O ChemAxon formula C9H15N4O9P ChemAxon inchi InChI=1S/C9H15N4O9P/c10-3-6(12-9(17)13-7(3)16)11-8-5(15)4(14)2(22-8)1-21-23(18,19)20/h2,4-5,8,14-15H,1,10H2,(H2,18,19,20)(H3,11,12,13,16,17)/t2-,4-,5-,8-/m1/s1 ChemAxon inchikey LZEXYCAGPMYXLX-UMMCILCDSA-N ChemAxon polar_surface_area 212.7 ChemAxon refractivity 79.88 ChemAxon polarizability 29.55 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 10 ChemAxon donor_count 8 ChemAxon physiological_charge -2 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 1083609 Specdb::NmrOneD 260428 Specdb::NmrOneD 260429 Specdb::NmrOneD 260430 Specdb::NmrOneD 260431 Specdb::NmrOneD 260432 Specdb::NmrOneD 260433 Specdb::NmrOneD 260434 Specdb::NmrOneD 260435 Specdb::NmrOneD 260436 Specdb::NmrOneD 260437 Specdb::NmrOneD 260438 Specdb::NmrOneD 260439 Specdb::NmrOneD 260440 Specdb::NmrOneD 260441 Specdb::NmrOneD 260442 Specdb::NmrOneD 260443 Specdb::NmrOneD 260444 Specdb::NmrOneD 260445 Specdb::NmrOneD 260446 Specdb::NmrOneD 260447 Specdb::MsMs 26933 Specdb::MsMs 26934 Specdb::MsMs 26935 Specdb::MsMs 33491 Specdb::MsMs 33492 Specdb::MsMs 33493 439462 388566 C01268 18337 CPD-602 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 biosynthesis protein ribD P25539 RIBD_ECOLI ribD http://ecmdb.ca/proteins/P25539.xml 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Hydrogen ion + Water > 5-Amino-6-(5'-phosphoribosylamino)uracil + Ammonium 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 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Water + 2,5-diamino-6-hydroxy-4-(5-phospho-D-ribosylamino)pyrimidine <> 5-Amino-6-(5'-phosphoribosylamino)uracil + Ammonia R03459 RIBOFLAVINSYNDEAM-RXN Water + 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine > 5-Amino-6-(5'-phosphoribosylamino)uracil + Ammonia RIBOFLAVINSYNDEAM-RXN 5-Amino-6-(5'-phosphoribitylamino)uracil + NADP < 5-Amino-6-(5'-phosphoribosylamino)uracil + NADPH + Hydrogen ion RIBOFLAVINSYNREDUC-RXN 2,5-Diamino-6-(5'-phosphoribosylamino)-4-pyrimidineone + Water + Hydrogen ion > Ammonium + 5-Amino-6-(5'-phosphoribosylamino)uracil PW_R005547 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 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