2.02012-05-31 14:30:00 -06002015-06-03 17:19:24 -0600ECMDB20148M2MDB000995Formamidopyrimidine nucleoside triphosphateFormamidopyrimidine 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 acidFormamidopyrimidine nucleoside triphosphoric acidN-(2-amino-5-formamido-6-oxo-3,6-dihydro-4-Pyrimidinyl)-5-O-(hydroxy{hydroxy(phosphonooxy)phosphoryloxy}phosphoryl)-b-D-ribofuranosylamineN-(2-Amino-5-formamido-6-oxo-3,6-dihydro-4-pyrimidinyl)-5-O-(hydroxy{hydroxy(phosphonooxy)phosphoryloxy}phosphoryl)-beta-D-ribofuranosylamineN-(2-amino-5-formamido-6-oxo-3,6-dihydro-4-Pyrimidinyl)-5-O-(hydroxy{hydroxy(phosphonooxy)phosphoryloxy}phosphoryl)-β-D-ribofuranosylamineC10H18N5O15P3541.1957541.001224467({[({[(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 acidNC1=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)N1InChI=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/s1NDXMRXXKCCKQQV-UUOKFMHZSA-NCytoplasmPeriplasmlogp-0.82logs-1.95solubility6.05e+00 g/llogp-4.7pka_strongest_acidic0.9pka_strongest_basic-3.7iupac({[({[(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 acidaverage_mass541.1957mono_mass541.001224467smilesNC1=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)N1formulaC10H18N5O15P3inchiInChI=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/s1inchikeyNDXMRXXKCCKQQV-UUOKFMHZSA-Npolar_surface_area318.12refractivity108.76polarizability40.47rotatable_bond_count10acceptor_count15donor_count10physiological_charge-4formal_charge0Folate biosynthesisThe 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.
PW000908ec00790MetabolicSpecdb::CMs22622Specdb::CMs39103Specdb::CMs265377Specdb::CMs265378Specdb::CMs265379Specdb::CMs265380Specdb::CMs265381Specdb::CMs265382Specdb::CMs265383Specdb::CMs265384Specdb::CMs265385Specdb::CMs265386Specdb::CMs265387Specdb::CMs265388Specdb::CMs265389Specdb::CMs265390Specdb::CMs265391Specdb::CMs265392Specdb::CMs265393Specdb::CMs265394Specdb::CMs265395Specdb::CMs265396Specdb::CMs265397Specdb::CMs265398Specdb::CMs265399Specdb::NmrOneD91732Specdb::NmrOneD91733Specdb::NmrOneD91734Specdb::NmrOneD91735Specdb::NmrOneD91736Specdb::NmrOneD91737Specdb::NmrOneD91738Specdb::NmrOneD91739Specdb::NmrOneD91740Specdb::NmrOneD91741Specdb::NmrOneD91742Specdb::NmrOneD91743Specdb::NmrOneD91744Specdb::NmrOneD91745Specdb::NmrOneD91746Specdb::NmrOneD91747Specdb::NmrOneD91748Specdb::NmrOneD91749Specdb::NmrOneD91750Specdb::NmrOneD91751Specdb::MsMs31913Specdb::MsMs31914Specdb::MsMs31915Specdb::MsMs2268490Specdb::MsMs2268491Specdb::MsMs2268492Specdb::MsMs25355Specdb::MsMs25356Specdb::MsMs25357Specdb::MsMs3071076Specdb::MsMs3071077Specdb::MsMs3071078HMDB06822440840389682C05922Kanehisa, 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-D114.22080510GTP cyclohydrolase 1P0A6T5GCH1_ECOLIfolEhttp://ecmdb.ca/proteins/P0A6T5.xmlGuanosine triphosphate + Water <> Formamidopyrimidine nucleoside triphosphateR00428Formamidopyrimidine nucleoside triphosphate + Water <> 2,5-Diaminopyrimidine nucleoside triphosphate + Formic acidR05046