2.0 2012-05-31 14:30:00 -0600 2015-06-03 17:19:24 -0600 ECMDB20148 M2MDB000995 Formamidopyrimidine nucleoside triphosphate Formamidopyrimidine 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-amino-5-formamido-4-oxo-1H-pyrimidin-6-yl)amino-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl phosphono hydrogen phosphate (2R,3S,4R,5R)-5-(2-amino-5-formamido-4-oxo-1H-Pyrimidin-6-yl)amino-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl phosphono hydrogen phosphoric acid Formamidopyrimidine nucleoside triphosphoric acid N-(2-amino-5-formamido-6-oxo-3,6-dihydro-4-Pyrimidinyl)-5-O-(hydroxy{hydroxy(phosphonooxy)phosphoryloxy}phosphoryl)-b-D-ribofuranosylamine N-(2-Amino-5-formamido-6-oxo-3,6-dihydro-4-pyrimidinyl)-5-O-(hydroxy{hydroxy(phosphonooxy)phosphoryloxy}phosphoryl)-beta-D-ribofuranosylamine N-(2-amino-5-formamido-6-oxo-3,6-dihydro-4-Pyrimidinyl)-5-O-(hydroxy{hydroxy(phosphonooxy)phosphoryloxy}phosphoryl)-β-D-ribofuranosylamine C10H18N5O15P3 541.1957 541.001224467 ({[({[(2R,3S,4R,5R)-5-[(2-amino-5-formamido-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-amino-5-formamido-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(NC=O)C(=O)N1 InChI=1S/C10H18N5O15P3/c11-10-14-7(4(12-2-16)8(19)15-10)13-9-6(18)5(17)3(28-9)1-27-32(23,24)30-33(25,26)29-31(20,21)22/h2-3,5-6,9,17-18H,1H2,(H,12,16)(H,23,24)(H,25,26)(H2,20,21,22)(H4,11,13,14,15,19)/t3-,5-,6-,9-/m1/s1 NDXMRXXKCCKQQV-UUOKFMHZSA-N Cytoplasm Periplasm logp -0.82 ALOGPS logs -1.95 ALOGPS solubility 6.05e+00 g/l ALOGPS logp -4.7 ChemAxon pka_strongest_acidic 0.9 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac ({[({[(2R,3S,4R,5R)-5-[(2-amino-5-formamido-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 541.1957 ChemAxon mono_mass 541.001224467 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(NC=O)C(=O)N1 ChemAxon formula C10H18N5O15P3 ChemAxon inchi InChI=1S/C10H18N5O15P3/c11-10-14-7(4(12-2-16)8(19)15-10)13-9-6(18)5(17)3(28-9)1-27-32(23,24)30-33(25,26)29-31(20,21)22/h2-3,5-6,9,17-18H,1H2,(H,12,16)(H,23,24)(H,25,26)(H2,20,21,22)(H4,11,13,14,15,19)/t3-,5-,6-,9-/m1/s1 ChemAxon inchikey NDXMRXXKCCKQQV-UUOKFMHZSA-N ChemAxon polar_surface_area 318.12 ChemAxon refractivity 108.76 ChemAxon polarizability 40.47 ChemAxon rotatable_bond_count 10 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 22622 Specdb::CMs 39103 Specdb::CMs 265377 Specdb::CMs 265378 Specdb::CMs 265379 Specdb::CMs 265380 Specdb::CMs 265381 Specdb::CMs 265382 Specdb::CMs 265383 Specdb::CMs 265384 Specdb::CMs 265385 Specdb::CMs 265386 Specdb::CMs 265387 Specdb::CMs 265388 Specdb::CMs 265389 Specdb::CMs 265390 Specdb::CMs 265391 Specdb::CMs 265392 Specdb::CMs 265393 Specdb::CMs 265394 Specdb::CMs 265395 Specdb::CMs 265396 Specdb::CMs 265397 Specdb::CMs 265398 Specdb::CMs 265399 Specdb::NmrOneD 91732 Specdb::NmrOneD 91733 Specdb::NmrOneD 91734 Specdb::NmrOneD 91735 Specdb::NmrOneD 91736 Specdb::NmrOneD 91737 Specdb::NmrOneD 91738 Specdb::NmrOneD 91739 Specdb::NmrOneD 91740 Specdb::NmrOneD 91741 Specdb::NmrOneD 91742 Specdb::NmrOneD 91743 Specdb::NmrOneD 91744 Specdb::NmrOneD 91745 Specdb::NmrOneD 91746 Specdb::NmrOneD 91747 Specdb::NmrOneD 91748 Specdb::NmrOneD 91749 Specdb::NmrOneD 91750 Specdb::NmrOneD 91751 Specdb::MsMs 25355 Specdb::MsMs 25356 Specdb::MsMs 25357 Specdb::MsMs 31913 Specdb::MsMs 31914 Specdb::MsMs 31915 Specdb::MsMs 2268490 Specdb::MsMs 2268491 Specdb::MsMs 2268492 Specdb::MsMs 3071076 Specdb::MsMs 3071077 Specdb::MsMs 3071078 HMDB06822 440840 389682 C05922 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 Guanosine triphosphate + Water <> Formamidopyrimidine nucleoside triphosphate R00428 Formamidopyrimidine nucleoside triphosphate + Water <> 2,5-Diaminopyrimidine nucleoside triphosphate + Formic acid R05046