2.0 2012-05-31 14:25:19 -0600 2015-06-03 17:19:13 -0600 ECMDB20059 M2MDB000908 2,5-Diaminopyrimidine nucleoside triphosphate 2,5-diaminopyrimidine nucleoside triphosphate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. (2R,3S,4R,5R)-5-(2,5-diamino-4-oxo-1H-pyrimidin-6-yl)amino-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl phosphono hydrogen phosphate (2R,3S,4R,5R)-5-(2,5-diamino-4-oxo-1H-Pyrimidin-6-yl)amino-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl phosphono hydrogen phosphoric acid 2,5-diamino-3,4-dihydro-4-oxo-6-(5-triphosphoribosylamino)pyrimidine 2,5-Diaminopyrimidine nucleoside triphosphoric acid N-(2,5-diamino-6-oxo-3,6-dihydro-4-Pyrimidinyl)-5-O-(hydroxy{hydroxy(phosphonooxy)phosphoryloxy}phosphoryl)-b-D-ribofuranosylamine N-(2,5-Diamino-6-oxo-3,6-dihydro-4-pyrimidinyl)-5-O-(hydroxy{hydroxy(phosphonooxy)phosphoryloxy}phosphoryl)-beta-D-ribofuranosylamine N-(2,5-diamino-6-oxo-3,6-dihydro-4-Pyrimidinyl)-5-O-(hydroxy{hydroxy(phosphonooxy)phosphoryloxy}phosphoryl)-β-D-ribofuranosylamine C9H18N5O14P3 513.1856 513.006309845 ({[({[(2R,3S,4R,5R)-5-[(2,5-diamino-6-oxo-1,6-dihydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid ({[(2R,3S,4R,5R)-5-[(2,5-diamino-6-oxo-1H-pyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid NC1=NC(N[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)=C(N)C(=O)N1 InChI=1S/C9H18N5O14P3/c10-3-6(13-9(11)14-7(3)17)12-8-5(16)4(15)2(26-8)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2,4-5,8,15-16H,1,10H2,(H,21,22)(H,23,24)(H2,18,19,20)(H4,11,12,13,14,17)/t2-,4-,5-,8-/m1/s1 CRXOALRUOMUPMC-UMMCILCDSA-N Cytoplasm Periplasm logp -1.00 ALOGPS logs -1.83 ALOGPS solubility 7.65e+00 g/l ALOGPS logp -5.1 ChemAxon pka_strongest_acidic 0.81 ChemAxon pka_strongest_basic 1.58 ChemAxon iupac ({[({[(2R,3S,4R,5R)-5-[(2,5-diamino-6-oxo-1,6-dihydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid ChemAxon average_mass 513.1856 ChemAxon mono_mass 513.006309845 ChemAxon smiles NC1=NC(N[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)=C(N)C(=O)N1 ChemAxon formula C9H18N5O14P3 ChemAxon inchi InChI=1S/C9H18N5O14P3/c10-3-6(13-9(11)14-7(3)17)12-8-5(16)4(15)2(26-8)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2,4-5,8,15-16H,1,10H2,(H,21,22)(H,23,24)(H2,18,19,20)(H4,11,12,13,14,17)/t2-,4-,5-,8-/m1/s1 ChemAxon inchikey CRXOALRUOMUPMC-UMMCILCDSA-N ChemAxon polar_surface_area 315.04 ChemAxon refractivity 103.8 ChemAxon polarizability 38.57 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 15 ChemAxon donor_count 10 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Folate biosynthesis The biosynthesis of folic acid begins with a product of purine nucleotides de novo biosynthesis pathway, GTP. This compound is involved in a reaction with water through a GTP cyclohydrolase 1 protein complex, resulting in a hydrogen ion, formic acid and 7,8-dihydroneopterin 3-triphosphate. The latter compound is dephosphatased through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, hydrogen ion and 7,8-dihydroneopterin 3-phosphate. The latter compound reacts with water spontaneously resulting in the release of a phosphate and a 7,8 -dihydroneopterin. This compound reacts with a dihydroneopterin aldolase, releasing a glycoaldehyde and 6-hydroxymethyl-7,9-dihydropterin. The latter compound is phosphorylated with a ATP-driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in a (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate. Chorismate is metabolized by reacting with L-glutamine through a 4-amino-4-deoxychorismate synthase resulting in L-glutamic acid and 4-amino-4-deoxychorismate. The latter compound then reacts through an aminodeoxychorismate lyase resulting in pyruvic acid,hydrogen ion and p-aminobenzoic acid. (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate and p-aminobenzoic acid react through a dihydropteroate synthase resulting in pyrophosphate and 7,8-dihydropteroic acid. This compound reacts with L-glutamic acid through an ATP driven bifunctional folylpolyglutamate synthetase / dihydrofolate synthetase resulting in a 7,8-dihydrofolate monoglutamate. This compound is reduced through an NADPH mediated dihydrofolate reductase resulting in a tetrahydrofate. This product goes on to a one carbon pool by folate pathway. PW000908 ec00790 Metabolic Specdb::CMs 13225 Specdb::CMs 39102 Specdb::NmrOneD 91712 Specdb::NmrOneD 91713 Specdb::NmrOneD 91714 Specdb::NmrOneD 91715 Specdb::NmrOneD 91716 Specdb::NmrOneD 91717 Specdb::NmrOneD 91718 Specdb::NmrOneD 91719 Specdb::NmrOneD 91720 Specdb::NmrOneD 91721 Specdb::NmrOneD 91722 Specdb::NmrOneD 91723 Specdb::NmrOneD 91724 Specdb::NmrOneD 91725 Specdb::NmrOneD 91726 Specdb::NmrOneD 91727 Specdb::NmrOneD 91728 Specdb::NmrOneD 91729 Specdb::NmrOneD 91730 Specdb::NmrOneD 91731 Specdb::MsMs 29549 Specdb::MsMs 29550 Specdb::MsMs 29551 Specdb::MsMs 36107 Specdb::MsMs 36108 Specdb::MsMs 36109 Specdb::MsMs 2704676 Specdb::MsMs 2704677 Specdb::MsMs 2704678 Specdb::MsMs 3004395 Specdb::MsMs 3004396 Specdb::MsMs 3004397 HMDB06821 440841 389683 C05923 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 Formamidopyrimidine nucleoside triphosphate + Water <> 2,5-Diaminopyrimidine nucleoside triphosphate + Formic acid R05046 2,5-Diaminopyrimidine nucleoside triphosphate <> 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine R05048