2.0 2012-07-30 14:54:47 -0600 2015-06-03 17:20:49 -0600 ECMDB21182 M2MDB001591 6-Hydroxymethyl-dihydropterin pyrophosphate 6-hydroxymethyl-dihydropterin pyrophosphate is a member of the chemical class known as Pterins and Derivatives. These are polycyclic aromatic compounds containing a pterin moeity, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one. (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate (2-amino-4-Hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphoric acid 2-Amino-7,8-dihydro-4-hydroxy-6-(diphosphooxymethyl)-pteridine 6-hydroxymethyl-dihydropterin pyrophosphate 6-Hydroxymethyl-dihydropterin pyrophosphoric acid AHHMeDHPDP Dihydropterin-CH2OH-diphosphate Dihydropterin-CH2OH-diphosphoric acid Dihydropterin-CH2OH-pp 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 Cytosol 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 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 6-hydroxymethyl-dihydropterin diphosphate biosynthesis I PWY-6147 tetrahydrofolate biosynthesis PWY-6614 Specdb::MsMs 27800 Specdb::MsMs 27801 Specdb::MsMs 27802 Specdb::MsMs 34358 Specdb::MsMs 34359 Specdb::MsMs 34360 25244074 24784870 C04807 57602 DIHYDROPTERIN-CH2OH-PP Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Dihydropteroate synthase P0AC13 DHPS_ECOLI folP http://ecmdb.ca/proteins/P0AC13.xml 2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinase P26281 HPPK_ECOLI folK http://ecmdb.ca/proteins/P26281.xml 6-Hydroxymethyl dihydropterin + Adenosine triphosphate > 6-Hydroxymethyl-dihydropterin pyrophosphate + Adenosine monophosphate + Hydrogen ion H2PTERIDINEPYROPHOSPHOKIN-RXN p-Aminobenzoic acid + 6-Hydroxymethyl-dihydropterin pyrophosphate > 7,8-Dihydropteroic acid + Pyrophosphate H2PTEROATESYNTH-RXN 6-Hydroxymethyl-dihydropterin pyrophosphate + p-Aminobenzoic acid > Pyrophosphate + 7,8-Dihydropteroic acid PW_R003401