2.0 2012-05-31 14:25:15 -0600 2015-06-03 17:19:13 -0600 ECMDB20058 M2MDB000907 2,5-Diamino-6-(5'-phosphoribosylamino)-4-pyrimidineone 2,5-diamino-6-(5'-phosphoribosylamino)-4-pyrimidineone is a nucleotide analog. It is involved in cofactor biosynthesis and riboflavin biosynthesis 2,5-Diamino-4-hydroxy-6-(5-phosphoribosylamino)pyrimidine 2,5-Diamino-6-(1-D-ribosylamino)pyrimidin-4(3H)-one 5'-phosphate 2,5-diamino-6-(1-D-ribosylamino)Pyrimidin-4(3H)-one 5'-phosphoric acid 2,5-Diamino-6-(D-ribosylamino)pyrimidin-4(3H)-one 5'-phosphate 2,5-diamino-6-(D-ribosylamino)Pyrimidin-4(3H)-one 5'-phosphoric acid 2,5-Diamino-6-(ribosylamino)-4-(3H)-pyrimidinone 5'-phosphate 2,5-diamino-6-(ribosylamino)-4-(3H)-Pyrimidinone 5'-phosphoric acid 2,5-Diamino-6-hydroxy-4-(5'-phosphoribosylamino)-pyrimidine 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)-pyrimidine 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine DARP C9H16N5O8P 353.2258 353.073649025 {[(2R,3S,4R,5R)-5-[(2,5-diamino-6-oxo-1,6-dihydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid APy NC1=NC(N[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)=C(N)C(O)=N1 InChI=1S/C9H16N5O8P/c10-3-6(13-9(11)14-7(3)17)12-8-5(16)4(15)2(22-8)1-21-23(18,19)20/h2,4-5,8,15-16H,1,10H2,(H2,18,19,20)(H4,11,12,13,14,17)/t2-,4-,5-,8-/m1/s1 OCLCLRXKNJCOJD-UMMCILCDSA-N Cytoplasm Periplasm logp -2.25 ALOGPS logs -1.79 ALOGPS solubility 5.70e+00 g/l ALOGPS logp -4.2 ChemAxon pka_strongest_acidic 1.05 ChemAxon pka_strongest_basic 1.71 ChemAxon iupac {[(2R,3S,4R,5R)-5-[(2,5-diamino-6-oxo-1,6-dihydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 353.2258 ChemAxon mono_mass 353.073649025 ChemAxon smiles NC1=NC(N[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)=C(N)C(O)=N1 ChemAxon formula C9H16N5O8P ChemAxon inchi InChI=1S/C9H16N5O8P/c10-3-6(13-9(11)14-7(3)17)12-8-5(16)4(15)2(22-8)1-21-23(18,19)20/h2,4-5,8,15-16H,1,10H2,(H2,18,19,20)(H4,11,12,13,14,17)/t2-,4-,5-,8-/m1/s1 ChemAxon inchikey OCLCLRXKNJCOJD-UMMCILCDSA-N ChemAxon polar_surface_area 221.98 ChemAxon refractivity 82.06 ChemAxon polarizability 29.99 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 11 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 1083382 Specdb::EiMs 4462 Specdb::NmrOneD 283629 Specdb::NmrOneD 283630 Specdb::NmrOneD 283631 Specdb::NmrOneD 283632 Specdb::NmrOneD 283633 Specdb::NmrOneD 283634 Specdb::NmrOneD 283635 Specdb::NmrOneD 283636 Specdb::NmrOneD 283637 Specdb::NmrOneD 283638 Specdb::NmrOneD 283639 Specdb::NmrOneD 283640 Specdb::NmrOneD 283641 Specdb::NmrOneD 283642 Specdb::NmrOneD 283643 Specdb::NmrOneD 283644 Specdb::NmrOneD 283645 Specdb::NmrOneD 283646 Specdb::NmrOneD 283647 Specdb::NmrOneD 283648 Specdb::MsMs 28973 Specdb::MsMs 28974 Specdb::MsMs 28975 Specdb::MsMs 35531 Specdb::MsMs 35532 Specdb::MsMs 35533 Specdb::MsMs 3607885 Specdb::MsMs 3607886 Specdb::MsMs 3607887 Specdb::MsMs 3607888 Specdb::MsMs 3607889 Specdb::MsMs 3607890 439480 388579 C01304 29114 DIAMINO-OH-PHOSPHORIBOSYLAMINO-PYR 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 GTP cyclohydrolase 1 P0A6T5 GCH1_ECOLI folE http://ecmdb.ca/proteins/P0A6T5.xml Riboflavin biosynthesis protein ribD P25539 RIBD_ECOLI ribD http://ecmdb.ca/proteins/P25539.xml Guanosine triphosphate + 3 Water > Formic acid + Pyrophosphate +2 Hydrogen ion + 2,5-Diamino-6-(5'-phosphoribosylamino)-4-pyrimidineone PW_R005542 2,5-Diamino-6-(5'-phosphoribosylamino)-4-pyrimidineone + Water + Hydrogen ion > Ammonium + 5-Amino-6-(5'-phosphoribosylamino)uracil PW_R005547