2.02012-05-31 14:27:26 -06002015-06-03 17:19:18 -0600ECMDB20099M2MDB0009475-Amino-6-(5'-phosphoribosylamino)uracil5-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)uracil5-Amino-6-(5-phosphoribosylamino)uracil5-Amino-6-(ribosylamino)-2,4-(1H,3H)-pyrimidinedione 5'-phosphate5-amino-6-(ribosylamino)-2,4-(1H,3H)-Pyrimidinedione 5'-phosphoric acid5A6-5'PRAUC9H15N4O9P354.2106354.05766461{[(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 acidNC1=C(N[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)NC(=O)NC1=OInChI=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/s1LZEXYCAGPMYXLX-UMMCILCDSA-NCytosollogp-1.84logs-1.99solubility3.64e+00 g/llogp-3.7pka_strongest_acidic1.23pka_strongest_basic-3.7iupac{[(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 acidaverage_mass354.2106mono_mass354.05766461smilesNC1=C(N[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)NC(=O)NC1=OformulaC9H15N4O9PinchiInChI=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/s1inchikeyLZEXYCAGPMYXLX-UMMCILCDSA-Npolar_surface_area212.7refractivity79.88polarizability29.55rotatable_bond_count5acceptor_count10donor_count8physiological_charge-2formal_charge0Riboflavin metabolismec00740Flavin 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.
PW001971Metabolicflavin biosynthesis I (bacteria and plants)RIBOSYN2-PWYSpecdb::CMs1083609Specdb::NmrOneD260428Specdb::NmrOneD260429Specdb::NmrOneD260430Specdb::NmrOneD260431Specdb::NmrOneD260432Specdb::NmrOneD260433Specdb::NmrOneD260434Specdb::NmrOneD260435Specdb::NmrOneD260436Specdb::NmrOneD260437Specdb::NmrOneD260438Specdb::NmrOneD260439Specdb::NmrOneD260440Specdb::NmrOneD260441Specdb::NmrOneD260442Specdb::NmrOneD260443Specdb::NmrOneD260444Specdb::NmrOneD260445Specdb::NmrOneD260446Specdb::NmrOneD260447Specdb::MsMs26933Specdb::MsMs26934Specdb::MsMs26935Specdb::MsMs33491Specdb::MsMs33492Specdb::MsMs33493439462388566C0126818337CPD-602Keseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Riboflavin biosynthesis protein ribDP25539RIBD_ECOLIribDhttp://ecmdb.ca/proteins/P25539.xml2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Hydrogen ion + Water > 5-Amino-6-(5'-phosphoribosylamino)uracil + Ammonium5-Amino-6-(5'-phosphoribosylamino)uracil + Hydrogen ion + NADPH > 5-Amino-6-(5'-phosphoribitylamino)uracil + NADPR03458RIBOFLAVINSYNREDUC-RXN5-Amino-6-(5'-phosphoribitylamino)uracil + NADP <> 5-Amino-6-(5'-phosphoribosylamino)uracil + NADPH + Hydrogen ionR03458RIBOFLAVINSYNREDUC-RXN2,5-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 + AmmoniaR03459RIBOFLAVINSYNDEAM-RXNWater + 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine > 5-Amino-6-(5'-phosphoribosylamino)uracil + AmmoniaRIBOFLAVINSYNDEAM-RXN5-Amino-6-(5'-phosphoribitylamino)uracil + NADP < 5-Amino-6-(5'-phosphoribosylamino)uracil + NADPH + Hydrogen ionRIBOFLAVINSYNREDUC-RXN2,5-Diamino-6-(5'-phosphoribosylamino)-4-pyrimidineone + Water + Hydrogen ion > Ammonium + 5-Amino-6-(5'-phosphoribosylamino)uracilPW_R0055475-Amino-6-(5'-phosphoribosylamino)uracil + Hydrogen ion + NADPH + NADPH > NADP + 5-Amino-6-(5'-phosphoribitylamino)uracil + 5-Amino-6-(5'-phosphoribitylamino)uracilPW_R0055485 5-Amino-6-(5'-phosphoribosylamino)uracil + Hydrogen ion + NADPH >5 5-Amino-6-(5'-phosphoribitylamino)uracil + NADP5 5-Amino-6-(5'-phosphoribosylamino)uracil + Hydrogen ion + NADPH >5 5-Amino-6-(5'-phosphoribitylamino)uracil + NADP