2.0 2015-09-08 17:50:23 -0600 2015-09-14 16:46:03 -0600 ECMDB24245 M2MDB006362 7,8-dihydroneopterin 3'-triphosphate 7,8-dihydroneopterin 3'-triphosphate (DHNTP) is an intermediate in folate biosynthesis. It is converted from 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine by dihydroneopterin triphosphate synthase (EC:3.5.4.16) (KEGG) 7,8-Dihydroneopterin 3'-triphosphoric acid C9H12N5O13P3 491.14 490.96664078 {[3-(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)-2,3-dihydroxypropyl phosphonato]oxy}(phosphonatooxy)phosphinate [3-(2-amino-4-oxo-7,8-dihydro-1H-pteridin-6-yl)-2,3-dihydroxypropyl phosphonato]oxy(phosphonatooxy)phosphinate NC1=NC(=O)C2=C(NCC(=N2)C(O)C(O)COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)N1 InChI=1S/C9H16N5O13P3/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-25-29(21,22)27-30(23,24)26-28(18,19)20/h4,6,15-16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H4,10,11,13,14,17)/p-4 DGGUVLXVLHAAGT-UHFFFAOYSA-J logp -0.91 ALOGPS logs -1.45 ALOGPS solubility 2.02e+01 g/l ALOGPS logp -4.3 ChemAxon pka_strongest_acidic 0.9 ChemAxon pka_strongest_basic -1.5 ChemAxon iupac {[3-(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)-2,3-dihydroxypropyl phosphonato]oxy}(phosphonatooxy)phosphinate ChemAxon average_mass 491.14 ChemAxon mono_mass 490.96664078 ChemAxon smiles NC1=NC(=O)C2=C(NCC(=N2)C(O)C(O)COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)N1 ChemAxon formula C9H12N5O13P3 ChemAxon inchi InChI=1S/C9H16N5O13P3/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-25-29(21,22)27-30(23,24)26-28(18,19)20/h4,6,15-16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H4,10,11,13,14,17)/p-4 ChemAxon inchikey DGGUVLXVLHAAGT-UHFFFAOYSA-J ChemAxon polar_surface_area 303.47 ChemAxon refractivity 97.79 ChemAxon polarizability 36.25 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 15 ChemAxon donor_count 5 ChemAxon physiological_charge -3 ChemAxon formal_charge -4 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 GTP degradation GTP, produced in the nucleotide de novo biosyntheis pathway, interacts with a water molecule through a GTP cyclohydrolase resulting in a formate, hydrogen ion and a 7,8-dihydroneopterin 3'-triphosphate. The latter compound interacts with a water molecule through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, a hydrogen ion and a 7,8-dihydroneopterin 3'-phosphate. The latter compound interacts with water spontaneously resulting in the release of a phosphate and a 7,8 dihydroneopterin. The latter compound interacts with a dihydroneopterin aldolase resulting in the release of a glycolaldehyde and a 6-hydroxymethyl-7,8-dihydropterin. This compound then is then diphosphorylated by reacting with a ATP driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in the release of a hydrogen ion, an AMP and 6-hydroxymethyl-7,8-dihydropterin diphosphate. GTP interacts with a cyclic pyranopterin monophosphate synthase resulting in the release of a diphosphate and a cyclic pyranopterin phosphate. The latter compound interacts with a thiocarboxylated small subunit of molybdopterin synthase (a protein) and a water molecule through a molybdopterin synthase resulting in the release of 4 hydrogen ions, 2 small subunits of molybdopterin synthase and a molybdopterin. The molybdopterin interacts with an ATP and a hydrogen ion through a molybdopterin adenylyltransferase resulting in the release of a diphosphate and a molybdopterin adenine dinucleotide. PW001888 Metabolic preQ0 metabolism PreQ0 or 7-cyano-7-carbaguanine is biosynthesized by degrading GTP. GTP first interacts with water through a GTP cyclohydrolase resulting in the release of a formate, a hydrogen ion and a 7,8-dihydroneopterin 3'-triphosphate. The latter compound then interacts with water through a 6-carboxy-5,6,7,8-tetrahydropterin synthase resulting in a acetaldehyde, triphosphate, 2 hydrogen ion and 6-carboxy-5,6,7,8-tetrahydropterin. The latter compound then reacts spontaneously with a hydrogen ion resulting in the release of a ammonium molecule and a 7-carboxy-7-deazaguanine. This compound then interacts with ATP and ammonium through 7-cyano-7-deazaguanine synthase resulting in the release of water, phosphate, ADP, hydrogen ion and a 7-cyano-7-carbaguanine. The degradation of 7-cyano-7-deazaguanine can lead to produce a preQ1 or a queuine by reacting with 3 hydrogen ions and 2 NADPH through a 7-cyano-7-deazaguanine reductase. PreQ1 then interacts with a guanine 34 in tRNA through a tRNA-guanine transglycosylase resulting in a release of a guanine and a 7-aminomethyl-7-deazaguanosine 34 in tRNA. This nucleic acid then interacts with SAM through a S-adenosylmethionine tRNA ribosyltransferase-isomerase resulting in a release of a hydrogen ion, L-methionine, adenine and an epoxyqueuosine PW001893 Metabolic Tetrahydromonapterin Biosynthesis 5,6,7,8-tetrahydromonapterin is the major tetrahydropterin in E. coli, although the biological role of tetrahydromonapterin in E. coli is currently unknown. It was shown to be a cofactor for the phenylalanine hydroxylase PhhA of Pseudomonas aeruginosa, but no enzyme requiring tetrahydromonapterin as a cofactor has yet been discovered in E. coli. Production of tetrahydromonapterin far exceeds production of folate, indicating that the majority of 7,8-dihydroneopterin 3'-triphosphate, the product of the first committed step of the superpathway of tetrahydrofolate biosynthesis and salvage pathway, is diverted from folate biosynthesis to this pathway. High levels of monapterin are found in the growth medium. PW002043 Metabolic Specdb::MsMs 28133 Specdb::MsMs 28134 Specdb::MsMs 28135 Specdb::MsMs 34691 Specdb::MsMs 34692 Specdb::MsMs 34693 GTP cyclohydrolase 1 P0A6T5 GCH1_ECOLI folE http://ecmdb.ca/proteins/P0A6T5.xml D-erythro-7,8-dihydroneopterin triphosphate epimerase P0AC19 FOLX_ECOLI folX http://ecmdb.ca/proteins/P0AC19.xml Dihydroneopterin triphosphate pyrophosphatase P0AFC0 NUDB_ECOLI nudB http://ecmdb.ca/proteins/P0AFC0.xml 6-carboxy-5,6,7,8-tetrahydropterin synthase P65870 QUED_ECOLI queD http://ecmdb.ca/proteins/P65870.xml Guanosine triphosphate + Water > Formic acid + Hydrogen ion + 7,8-dihydroneopterin 3'-triphosphate PW_R003396 7,8-dihydroneopterin 3'-triphosphate + Water > Pyrophosphate + Hydrogen ion + Dihydroneopterin monophosphate PW_R003397 7,8-dihydroneopterin 3'-triphosphate + Water > Acetaldehyde + Triphosphate +2 Hydrogen ion + 6-Carboxy-5,6,7,8-tetrahydropterin + Triphosphate PW_R005178 7,8-dihydroneopterin 3'-triphosphate <> Dihydromonapterin-triphosphate PW_R005965