2.0 2012-05-31 14:03:35 -0600 2015-06-03 15:54:41 -0600 ECMDB04052 M2MDB000584 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine 2,5-Diamino-6-hydroxy-4-(5-phospho-D-ribosylamino)pyrimidine or DARP, is an intermediate in flavin biosynthesis. It is a substrate for diaminohydroxyphosphoribosylaminopyrimidine deaminase, which catalyzes the reaction 2,5-diamino-6-hydroxy-4-(5-phospho-D-ribosylamino)pyrimidine + H2O = 5-amino-6-(5-phospho-D-ribosylamino)uracil + NH3 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-(5'-phosphoribosylamino)-4-pyrimidineone 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 2,5DA6RA4P5P DARP C9H16N5O8P 353.2258 353.073649025 {[(2S,3S,4R)-5-[(5-amino-6-hydroxy-2-imino-2,3-dihydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl](hydroxy)methyl}phosphonic acid [(2S,3S,4R)-5-[(5-amino-6-hydroxy-2-imino-3H-pyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl](hydroxy)methylphosphonic acid [H]C(O)([C@@]1([H])OC([H])(NC2=C(N)C(O)=NC(=N)N2)[C@]([H])(O)[C@]1([H])O)P(O)(O)=O InChI=1S/C9H16N5O8P/c10-1-5(13-9(11)14-6(1)17)12-7-3(16)2(15)4(22-7)8(18)23(19,20)21/h2-4,7-8,15-16,18H,10H2,(H2,19,20,21)(H4,11,12,13,14,17)/t2-,3+,4-,7?,8?/m0/s1 CIEXRWBOBYOQGW-DOAYSINJSA-N Cytosol logp -2.57 ALOGPS logs -1.74 ALOGPS solubility 6.36e+00 g/l ALOGPS logp -4.4 ChemAxon pka_strongest_acidic 1.25 ChemAxon pka_strongest_basic 21.89 ChemAxon iupac {[(2S,3S,4R)-5-[(5-amino-6-hydroxy-2-imino-2,3-dihydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl](hydroxy)methyl}phosphonic acid ChemAxon average_mass 353.2258 ChemAxon mono_mass 353.073649025 ChemAxon smiles [H]C(O)([C@@]1([H])OC([H])(NC2=C(N)C(O)=NC(=N)N2)[C@]([H])(O)[C@]1([H])O)P(O)(O)=O ChemAxon formula C9H16N5O8P ChemAxon inchi InChI=1S/C9H16N5O8P/c10-1-5(13-9(11)14-6(1)17)12-7-3(16)2(15)4(22-7)8(18)23(19,20)21/h2-4,7-8,15-16,18H,10H2,(H2,19,20,21)(H4,11,12,13,14,17)/t2-,3+,4-,7?,8?/m0/s1 ChemAxon inchikey CIEXRWBOBYOQGW-DOAYSINJSA-N ChemAxon polar_surface_area 233.97 ChemAxon refractivity 92.41 ChemAxon polarizability 30.01 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 13 ChemAxon donor_count 10 ChemAxon physiological_charge 0 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 1083522 Specdb::NmrOneD 262568 Specdb::NmrOneD 262569 Specdb::NmrOneD 262570 Specdb::NmrOneD 262571 Specdb::NmrOneD 262572 Specdb::NmrOneD 262573 Specdb::NmrOneD 262574 Specdb::NmrOneD 262575 Specdb::NmrOneD 262576 Specdb::NmrOneD 262577 Specdb::NmrOneD 262578 Specdb::NmrOneD 262579 Specdb::NmrOneD 262580 Specdb::NmrOneD 262581 Specdb::NmrOneD 262582 Specdb::NmrOneD 262583 Specdb::NmrOneD 262584 Specdb::NmrOneD 262585 Specdb::NmrOneD 262586 Specdb::NmrOneD 262587 Specdb::MsMs 25043 Specdb::MsMs 25044 Specdb::MsMs 25045 Specdb::MsMs 31601 Specdb::MsMs 31602 Specdb::MsMs 31603 25244331 26331269 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 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 GTP cyclohydrolase 1 P0A6T5 GCH1_ECOLI folE http://ecmdb.ca/proteins/P0A6T5.xml GTP cyclohydrolase-2 P0A7I7 RIBA_ECOLI ribA http://ecmdb.ca/proteins/P0A7I7.xml 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 Guanosine triphosphate + 3 Water <> 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Formic acid +2 Hydrogen ion + Pyrophosphate + 2,5-diamino-6-hydroxy-4-(5-phospho-D-ribosylamino)pyrimidine R00425 GTP-CYCLOHYDRO-II-RXN Guanosine triphosphate + 3 Water <> Formic acid + 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Pyrophosphate R00425 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 + Guanosine triphosphate > Hydrogen ion + Pyrophosphate + 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Formic acid GTP-CYCLOHYDRO-II-RXN Water + 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine > 5-Amino-6-(5'-phosphoribosylamino)uracil + Ammonia RIBOFLAVINSYNDEAM-RXN Guanosine triphosphate + 3 Water > Formic acid + 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Pyrophosphate Guanosine triphosphate + Water > 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Hydrogen ion + Formic acid + Pyrophosphate PW_R005545 Guanosine triphosphate + 3 Water <>2 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Formic acid +2 Hydrogen ion + Pyrophosphate +2 2,5-diamino-6-hydroxy-4-(5-phospho-D-ribosylamino)pyrimidine