2.0 2012-05-31 14:09:40 -0600 2015-06-03 15:54:55 -0600 ECMDB06823 M2MDB000695 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine is involved in folate biosynthesis. 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine is created from 2,5-Diaminopyrimidine nucleoside triphosphate by GTP cyclohydrolase I [EC:3.5.4.16]. 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine can be converted into 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine 1-Deoxy-1-(2,5-diamino-6-oxo-3,6-dihydro-4-pyrimidinyl)amino-5-O-(hydroxy{hydroxy(phosphonooxy)phosphoryloxy}phosphoryl)pent-2-ulose 5-(2,5-diamino-4-oxo-1H-pyrimidin-6-yl)amino-2,3-dihydroxy-4-oxopentoxy-hydroxyphosphoryl phosphono hydrogen phosphate 5-(2,5-diamino-4-oxo-1H-Pyrimidin-6-yl)amino-2,3-dihydroxy-4-oxopentoxy-hydroxyphosphoryl phosphono hydrogen phosphoric acid C9H18N5O14P3 513.1856 513.006309845 [({[({5-[(2,5-diamino-6-oxo-3,6-dihydropyrimidin-4-yl)amino]-2,3-dihydroxy-4-oxopentyl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid [({5-[(2,5-diamino-6-oxo-3H-pyrimidin-4-yl)amino]-2,3-dihydroxy-4-oxopentyl}oxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxyphosphonic acid NC1=NC(=O)C(N)=C(NCC(=O)C(O)C(O)COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1 InChI=1S/C9H18N5O14P3/c10-5-7(13-9(11)14-8(5)18)12-1-3(15)6(17)4(16)2-26-30(22,23)28-31(24,25)27-29(19,20)21/h4,6,16-17H,1-2,10H2,(H,22,23)(H,24,25)(H2,19,20,21)(H4,11,12,13,14,18) ZJYBJXKSWQPKFW-UHFFFAOYSA-N Solid Cytoplasm Periplasm logp -0.86 ALOGPS logs -1.90 ALOGPS solubility 6.42e+00 g/l ALOGPS logp -6.2 ChemAxon pka_strongest_acidic 0.89 ChemAxon pka_strongest_basic 3.72 ChemAxon iupac [({[({5-[(2,5-diamino-6-oxo-3,6-dihydropyrimidin-4-yl)amino]-2,3-dihydroxy-4-oxopentyl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid ChemAxon average_mass 513.1856 ChemAxon mono_mass 513.006309845 ChemAxon smiles NC1=NC(=O)C(N)=C(NCC(=O)C(O)C(O)COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1 ChemAxon formula C9H18N5O14P3 ChemAxon inchi InChI=1S/C9H18N5O14P3/c10-5-7(13-9(11)14-8(5)18)12-1-3(15)6(17)4(16)2-26-30(22,23)28-31(24,25)27-29(19,20)21/h4,6,16-17H,1-2,10H2,(H,22,23)(H,24,25)(H2,19,20,21)(H4,11,12,13,14,18) ChemAxon inchikey ZJYBJXKSWQPKFW-UHFFFAOYSA-N ChemAxon polar_surface_area 322.88 ChemAxon refractivity 105.24 ChemAxon polarizability 38.94 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 16 ChemAxon donor_count 10 ChemAxon physiological_charge -3 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 9692 Specdb::CMs 39104 Specdb::NmrOneD 91752 Specdb::NmrOneD 91753 Specdb::NmrOneD 91754 Specdb::NmrOneD 91755 Specdb::NmrOneD 91756 Specdb::NmrOneD 91757 Specdb::NmrOneD 91758 Specdb::NmrOneD 91759 Specdb::NmrOneD 91760 Specdb::NmrOneD 91761 Specdb::NmrOneD 91762 Specdb::NmrOneD 91763 Specdb::NmrOneD 91764 Specdb::NmrOneD 91765 Specdb::NmrOneD 91766 Specdb::NmrOneD 91767 Specdb::NmrOneD 91768 Specdb::NmrOneD 91769 Specdb::NmrOneD 91770 Specdb::NmrOneD 91771 Specdb::MsMs 23150 Specdb::MsMs 23151 Specdb::MsMs 23152 Specdb::MsMs 29948 Specdb::MsMs 29949 Specdb::MsMs 29950 Specdb::MsMs 2759792 Specdb::MsMs 2759793 Specdb::MsMs 2759794 Specdb::MsMs 2945532 Specdb::MsMs 2945533 Specdb::MsMs 2945534 HMDB06823 440923 389753 C06148 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 Dihydroneopterin triphosphate + Water <> 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine R04639 2,5-Diaminopyrimidine nucleoside triphosphate <> 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine R05048