2.0 2012-07-30 14:54:47 -0600 2015-06-03 17:20:49 -0600 ECMDB21181 M2MDB001590 6-Hydroxymethyl dihydropterin 6-hydroxymethyl dihydropterin 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-6-hydroxymethyl dihydropteridin Dihydropterin-CH2OH C7H9N5O2 195.1787 195.075624557 2-amino-6-(hydroxymethyl)-3,4,7,8-tetrahydropteridin-4-one 2-amino-6-(hydroxymethyl)-7,8-dihydro-3H-pteridin-4-one NC1=NC2=C(N=C(CO)CN2)C(=O)N1 InChI=1S/C7H9N5O2/c8-7-11-5-4(6(14)12-7)10-3(2-13)1-9-5/h13H,1-2H2,(H4,8,9,11,12,14) CQQNNQTXUGLUEV-UHFFFAOYSA-N Cytosol logp -1.69 ALOGPS logs -1.90 ALOGPS solubility 2.47e+00 g/l ALOGPS logp -1.9 ChemAxon pka_strongest_acidic 7.62 ChemAxon pka_strongest_basic 0.76 ChemAxon iupac 2-amino-6-(hydroxymethyl)-3,4,7,8-tetrahydropteridin-4-one ChemAxon average_mass 195.1787 ChemAxon mono_mass 195.075624557 ChemAxon smiles NC1=NC2=C(N=C(CO)CN2)C(=O)N1 ChemAxon formula C7H9N5O2 ChemAxon inchi InChI=1S/C7H9N5O2/c8-7-11-5-4(6(14)12-7)10-3(2-13)1-9-5/h13H,1-2H2,(H4,8,9,11,12,14) ChemAxon inchikey CQQNNQTXUGLUEV-UHFFFAOYSA-N ChemAxon polar_surface_area 112.1 ChemAxon refractivity 57.86 ChemAxon polarizability 18.4 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 0 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 Metabolic pathways eco01100 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 Specdb::CMs 2430 Specdb::NmrOneD 318611 Specdb::NmrOneD 318612 Specdb::NmrOneD 318613 Specdb::NmrOneD 318614 Specdb::NmrOneD 318615 Specdb::NmrOneD 318616 Specdb::NmrOneD 318617 Specdb::NmrOneD 318618 Specdb::NmrOneD 318619 Specdb::NmrOneD 318620 Specdb::NmrOneD 318621 Specdb::NmrOneD 318622 Specdb::NmrOneD 318623 Specdb::NmrOneD 318624 Specdb::NmrOneD 318625 Specdb::NmrOneD 318626 Specdb::NmrOneD 318627 Specdb::NmrOneD 318628 Specdb::NmrOneD 318629 Specdb::NmrOneD 318630 Specdb::MsMs 20069 Specdb::MsMs 20070 Specdb::MsMs 20071 Specdb::MsMs 21620 Specdb::MsMs 21621 Specdb::MsMs 21622 Specdb::MsMs 3608275 Specdb::MsMs 3608276 Specdb::MsMs 3608277 Specdb::MsMs 3608278 Specdb::MsMs 3608279 Specdb::MsMs 3608280 218 213 C01300 17083 AMINO-OH-HYDROXYMETHYL-DIHYDROPTERIDINE PH2 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 Dihydroneopterin aldolase P0AC16 FOLB_ECOLI folB http://ecmdb.ca/proteins/P0AC16.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 7,8-Dihydroneopterin <> 6-Hydroxymethyl dihydropterin + Glycolaldehyde R03504 H2NEOPTERINALDOL-RXN 6-Hydroxymethyl dihydropterin + p-Aminobenzoic acid <> 7,8-Dihydropteroic acid + Water R03066 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 7,8-Dihydroneopterin > Glycolaldehyde + 6-Hydroxymethyl dihydropterin H2NEOPTERINALDOL-RXN 2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine > 6-Hydroxymethyl dihydropterin + Glycolaldehyde Adenosine triphosphate + 6-Hydroxymethyl dihydropterin > Adenosine monophosphate + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate 7,8-Dihydroneopterin + 7,8-Dihydroneopterin > Glycolaldehyde + 6-Hydroxymethyl dihydropterin PW_R003399 7 7,8-Dihydroneopterin <>6 6-Hydroxymethyl dihydropterin + Glycolaldehyde 6 6-Hydroxymethyl dihydropterin + p-Aminobenzoic acid <>7 7,8-Dihydropteroic acid + Water 7 7,8-Dihydroneopterin <>6 6-Hydroxymethyl dihydropterin + Glycolaldehyde 6 6-Hydroxymethyl dihydropterin + p-Aminobenzoic acid <>7 7,8-Dihydropteroic acid + Water