2.0 2015-09-08 17:49:01 -0600 2015-09-08 17:49:01 -0600 ECMDB24078 M2MDB006195 5'-phosphoribosyl-a-N-formylglycineamidine C8H16N3O8P 313.2017 313.067501015 ({5-[(Z)-(1-amino-2-formamidoethylidene)amino]-3,4-dihydroxyoxolan-2-yl}methoxy)phosphonic acid {5-[(Z)-(1-amino-2-formamidoethylidene)amino]-3,4-dihydroxyoxolan-2-yl}methoxyphosphonic acid N\C(CNC=O)=N/C1OC(COP(O)(O)=O)C(O)C1O InChI=1S/C8H16N3O8P/c9-5(1-10-3-12)11-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H2,9,11)(H,10,12)(H2,15,16,17) PMCOGCVKOAOZQM-UHFFFAOYSA-N logp -2.35 ALOGPS logs -1.75 ALOGPS solubility 5.58e+00 g/l ALOGPS logp -4.2 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic 6.6 ChemAxon iupac ({5-[(Z)-(1-amino-2-formamidoethylidene)amino]-3,4-dihydroxyoxolan-2-yl}methoxy)phosphonic acid ChemAxon average_mass 313.2017 ChemAxon mono_mass 313.067501015 ChemAxon smiles N\C(CNC=O)=N/C1OC(COP(O)(O)=O)C(O)C1O ChemAxon formula C8H16N3O8P ChemAxon inchi InChI=1S/C8H16N3O8P/c9-5(1-10-3-12)11-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H2,9,11)(H,10,12)(H2,15,16,17) ChemAxon inchikey PMCOGCVKOAOZQM-UHFFFAOYSA-N ChemAxon polar_surface_area 183.93 ChemAxon refractivity 62.43 ChemAxon polarizability 27.07 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon One Carbon Pool by Folate I Dihydrofolic acid, a product of the folate biosynthesis pathway, can be metabolized by multiple enzymes. Dihydrofolic acid can be reduced by a NADP-driven dihydrofolate reductase resulting in a NADPH, hydrogen ion and folic acid. Dihydrofolic acid can also be reduced by an NADPH-driven dihydrofolate reductase resulting in a NADP and a tetrahydrofolic acid. Folic acid can also produce a tetrahydrofolic acid through a NADPH-driven dihydrofolate reductase. Dihydrofolic acid also interacts with 5-thymidylic acid through a thymidylate synthase resulting in the release of dUMP and 5,10-methylene-THF Tetrahydrofolic acid can be converted into 5,10-methylene-THF through two different reversible reactions. Tetrahydrofolic acid interacts with a S-Aminomethyldihydrolipoylprotein through a aminomethyltransferase resulting in the release of ammonia, a dihydrolipoylprotein and 5,10-Methylene-THF Tetrahydrofolic acid interacts with L-serine through a glycine hydroxymethyltransferase resulting in a glycine, water and 5,10-Methylene-THF. The compound 5,10-methylene-THF reacts with an NADPH dependent methylenetetrahydrofolate reductase [NAD(P)H] resulting in NADP and 5-Methyltetrahydrofolic acid. This compound interacts with homocysteine through a methionine synthase resulting in L-methionine and tetrahydrofolic acid. Tetrahydrofolic acid can be metabolized into 10-formyltetrahydrofolate through 4 different enzymes: 1.- Tetrahydrofolic acid interacts with FAICAR through a phosphoribosylaminoimidazolecarboxamide formyltransferase resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide and a 10-formyltetrahydrofolate 2.-Tetrahydrofolic acid interacts with 5'-Phosphoribosyl-N-formylglycinamide through a phosphoribosylglycinamide formyltransferase 2 resulting in a Glycineamideribotide and a 10-formyltetrahydrofolate 3.-Tetrahydrofolic acid interacts with Formic acid through a formyltetrahydrofolate hydrolase resulting in water and a 10-formyltetrahydrofolate 4.-Tetrahydrofolic acid interacts with N-formylmethionyl-tRNA(fMet) through a 10-formyltetrahydrofolate:L-methionyl-tRNA(fMet) N-formyltransferase resulting in a L-methionyl-tRNA(Met) and a 10-formyltetrahydrofolate 10-formyltetrahydrofolate can interact with a hydrogen ion through a bifunctional 5,10-methylene-tetrahydrofolate dehydrogenase resulting in water and 5,10-methenyltetrahydrofolic acid. Tetrahydrofolic acid can be metabolized into 5,10-methenyltetrahydrofolic acid by reacting with a 5'-phosphoribosyl-a-N-formylglycineamidine through a phosphoribosylglycinamide formyltransferase 2 resulting in water, glycineamideribotide and 5,10-methenyltetrahydrofolic acid. The latter compound can either interact with water through an aminomethyltransferase resulting in a N5-Formyl-THF, or it can interact with a NADPH driven bifunctional 5,10-methylene-tetrahydrofolate dehydrogenase resulting in a NADP and 5,10-Methylene THF. PW001735 Metabolic Specdb::CMs 2768 Specdb::CMs 38361 Specdb::MsMs 27653 Specdb::MsMs 27654 Specdb::MsMs 27655 Specdb::MsMs 34211 Specdb::MsMs 34212 Specdb::MsMs 34213 Phosphoribosylglycinamide formyltransferase 2 P33221 PURT_ECOLI purT http://ecmdb.ca/proteins/P33221.xml 5'-phosphoribosyl-a-N-formylglycineamidine + Tetrahydrofolic acid + Tetrahydrofolic acid > Water + Glycineamideribotide + 5,10-Methenyltetrahydrofolic acid + Glycineamideribotide PW_R002550