2.0 2015-09-08 17:48:55 -0600 2015-09-08 17:48:55 -0600 ECMDB24067 M2MDB006184 5,10-Methenyltetrahydrofolic acid 5,10-Methenyltetrahydrofolate C20H21N7O6 455.424 455.155331439 (6aR)-8-(4-{[(1S)-1,3-dicarboxypropyl]-C-hydroxycarbonimidoyl}phenyl)-1-hydroxy-3-imino-3H,4H,5H,6H,6aH,7H-8lambda5-imidazo[1,5-f]pteridin-8-ylium (6aR)-8-(4-{[(1S)-1,3-dicarboxypropyl]-C-hydroxycarbonimidoyl}phenyl)-1-hydroxy-3-imino-4H,5H,6H,6aH,7H-8lambda5-imidazo[1,5-f]pteridin-8-ylium [H][C@@]12CN(C=[N+]1C1=C(NC2)NC(N)=NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C([O-])=O InChI=1S/C20H21N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/t12-,13+/m1/s1 MEANFMOQMXYMCT-OLZOCXBDSA-N logp -0.68 ALOGPS logs -3.39 ALOGPS solubility 2.07e-01 g/l ALOGPS logp -3.3 ChemAxon pka_strongest_acidic 2.99 ChemAxon pka_strongest_basic 2.04 ChemAxon iupac (6aR)-8-(4-{[(1S)-1,3-dicarboxypropyl]-C-hydroxycarbonimidoyl}phenyl)-1-hydroxy-3-imino-3H,4H,5H,6H,6aH,7H-8lambda5-imidazo[1,5-f]pteridin-8-ylium ChemAxon average_mass 455.424 ChemAxon mono_mass 455.155331439 ChemAxon smiles [H][C@@]12CN(C=[N+]1C1=C(NC2)NC(N)=NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C([O-])=O ChemAxon formula C20H21N7O6 ChemAxon inchi InChI=1S/C20H21N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/t12-,13+/m1/s1 ChemAxon inchikey MEANFMOQMXYMCT-OLZOCXBDSA-N ChemAxon polar_surface_area 196.77 ChemAxon refractivity 155.82 ChemAxon polarizability 45.38 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 12 ChemAxon donor_count 6 ChemAxon physiological_charge 0 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 24104 Specdb::CMs 38038 Specdb::CMs 136159 Specdb::CMs 143893 Specdb::NmrOneD 295715 Specdb::NmrOneD 295716 Specdb::NmrOneD 295717 Specdb::NmrOneD 295718 Specdb::NmrOneD 295719 Specdb::NmrOneD 295720 Specdb::NmrOneD 295721 Specdb::NmrOneD 295722 Specdb::NmrOneD 295723 Specdb::NmrOneD 295724 Specdb::NmrOneD 295725 Specdb::NmrOneD 295726 Specdb::NmrOneD 295727 Specdb::NmrOneD 295728 Specdb::NmrOneD 295729 Specdb::NmrOneD 295730 Specdb::NmrOneD 295731 Specdb::NmrOneD 295732 Specdb::NmrOneD 295733 Specdb::NmrOneD 295734 Specdb::MsMs 24410 Specdb::MsMs 24411 Specdb::MsMs 24412 Specdb::MsMs 30968 Specdb::MsMs 30969 Specdb::MsMs 30970 Specdb::MsMs 2454694 Specdb::MsMs 2454695 Specdb::MsMs 2454696 Specdb::MsMs 2484237 Specdb::MsMs 2484238 Specdb::MsMs 2484239 Aminomethyltransferase P27248 GCST_ECOLI gcvT http://ecmdb.ca/proteins/P27248.xml Phosphoribosylglycinamide formyltransferase 2 P33221 PURT_ECOLI purT http://ecmdb.ca/proteins/P33221.xml Water + 5,10-Methenyltetrahydrofolic acid > N5-Formyl-THF + N5-Formyl-H4F PW_R002552 Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide > Water + 5,10-Methenyltetrahydrofolic acid + Glycineamideribotide + Glycineamideribotide PW_R002546 5'-phosphoribosyl-a-N-formylglycineamidine + Tetrahydrofolic acid + Tetrahydrofolic acid > Water + Glycineamideribotide + 5,10-Methenyltetrahydrofolic acid + Glycineamideribotide PW_R002550