2.0 2012-10-10 12:14:04 -0600 2015-08-05 16:22:03 -0600 ECMDB23049 M2MDB003439 (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate Trianion of (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate arising from deprotonation of the three diphosphate OH groups (2-amino-4-Hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate trianion (2-amino-4-Hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate(3-) (2-amino-4-Hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphoric acid (2-amino-4-Hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphoric acid trianion (2-amino-4-Hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphoric acid(3-) C7H8N5O8P2 352.1146 351.984810281 6-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-2-imino-1,2,7,8-tetrahydropteridin-4-olate 6-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-2-imino-7,8-dihydro-1H-pteridin-4-olate OP(=O)(OCC1=NC2=C(NC1)NC(=N)N=C2[O-])OP([O-])([O-])=O InChI=1S/C7H11N5O8P2/c8-7-11-5-4(6(13)12-7)10-3(1-9-5)2-19-22(17,18)20-21(14,15)16/h1-2H2,(H,17,18)(H2,14,15,16)(H4,8,9,11,12,13)/p-3 FCQGJGLSOWZZON-UHFFFAOYSA-K logp -1.10 ALOGPS logs -1.83 ALOGPS solubility 5.96e+00 g/l ALOGPS logp -2.6 ChemAxon pka_strongest_acidic 2.07 ChemAxon pka_strongest_basic 1.48 ChemAxon iupac 6-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-2-imino-1,2,7,8-tetrahydropteridin-4-olate ChemAxon average_mass 352.1146 ChemAxon mono_mass 351.984810281 ChemAxon smiles OP(=O)(OCC1=NC2=C(NC1)NC(=N)N=C2[O-])OP([O-])([O-])=O ChemAxon formula C7H8N5O8P2 ChemAxon inchi InChI=1S/C7H11N5O8P2/c8-7-11-5-4(6(13)12-7)10-3(1-9-5)2-19-22(17,18)20-21(14,15)16/h1-2H2,(H,17,18)(H2,14,15,16)(H4,8,9,11,12,13)/p-3 ChemAxon inchikey FCQGJGLSOWZZON-UHFFFAOYSA-K ChemAxon polar_surface_area 214.64 ChemAxon refractivity 98.72 ChemAxon polarizability 26.84 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 11 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge -3 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 Metabolic pathways eco01100 Specdb::MsMs 27800 Specdb::MsMs 27801 Specdb::MsMs 27802 Specdb::MsMs 34358 Specdb::MsMs 34359 Specdb::MsMs 34360 Adenosine triphosphate + 6-Hydroxymethyl dihydropterin <> Adenosine monophosphate + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate R03503 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + p-Aminobenzoic acid + (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate <> Pyrophosphate + 7,8-Dihydropteroic acid R03067