2.02012-10-10 12:14:04 -06002015-08-05 16:22:03 -0600ECMDB23049M2MDB003439(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphateTrianion 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-)C7H8N5O8P2352.1146351.9848102816-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-2-imino-1,2,7,8-tetrahydropteridin-4-olate6-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-2-imino-7,8-dihydro-1H-pteridin-4-olateOP(=O)(OCC1=NC2=C(NC1)NC(=N)N=C2[O-])OP([O-])([O-])=OInChI=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-3FCQGJGLSOWZZON-UHFFFAOYSA-Klogp-1.10logs-1.83solubility5.96e+00 g/llogp-2.6pka_strongest_acidic2.07pka_strongest_basic1.48iupac6-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-2-imino-1,2,7,8-tetrahydropteridin-4-olateaverage_mass352.1146mono_mass351.984810281smilesOP(=O)(OCC1=NC2=C(NC1)NC(=N)N=C2[O-])OP([O-])([O-])=OformulaC7H8N5O8P2inchiInChI=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-3inchikeyFCQGJGLSOWZZON-UHFFFAOYSA-Kpolar_surface_area214.64refractivity98.72polarizability26.84rotatable_bond_count5acceptor_count11donor_count4physiological_charge-2formal_charge-3Folate 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.
PW000908ec00790MetabolicMetabolic pathwayseco01100Specdb::MsMs27800Specdb::MsMs27801Specdb::MsMs27802Specdb::MsMs34358Specdb::MsMs34359Specdb::MsMs34360Adenosine 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 diphosphateR035032-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 acidR03067