2.0 2012-07-30 14:54:46 -0600 2015-06-03 17:20:48 -0600 ECMDB21176 M2MDB001585 5,10-Methenyltetrahydrofolate 5,10-Methenyltetrahydrofolate (5,10-CH=THF) is a form of tetrahydrofolate that is an intermediate in metabolism. 5,10-CH=THF is a coenzyme that accepts and donates methenyl (CH=) groups.;Methylene tetrahydrofolate (CH2FH4) is formed from tetrahydrofolate by the addition of methylene groups from one of three carbon donors: formaldehyde, serine, or glycine. Methyl tetrahydrofolate(CH3FH4) can be made from methylene tetrahydrofolate by reduction of the methylene group, and formyl tetrahydrofolate (CHOFH4, folinic acid) is made by oxidation of methylene tetrahydrofolate.; In the form of a series of tetrahydrofolate compounds, folate derivatives are substrates in a number of single-carbon-transfer reactions, and also are involved in the synthesis of dTMP (2'-deoxythymidine-5'-phosphate) from dUMP (2'-deoxyuridine-5'-phosphate). (6R)-5,10-CH+-H4folate (6R)-5,10-CH+-H4folic acid (6R)-5,10-methenyltetrahydrofolate (6R)-5,10-methenyltetrahydrofolic acid 5,10-Methenyl-THF 5,10-Methenyltetrahydrofolate 5,10-Methenyltetrahydrofolic acid 5,10-Methenyltetrahydropteroylglutamate 5,10-Methenyltetrahydropteroylglutamic acid 5,10Me-THF Anhydro-leucovorin Anhydro-leucovorin a Anhydroleucovorin Anhydroleucovorin a Ch-thf Methenyl-H4F Methenyl-H₄F Methenyl-tetrahydrofolate Methenyl-tetrahydrofolic acid Methenyl-thf Methenyltetrahydrofolate Methenyltetrahydrofolic acid N-{4-[(6aR)-3-amino-1-oxo-1,2,5,6,6a,7-hexahydro-8H-imidazo[1,5-f]pteridin-10-ium-8-yl]benzoyl}-L-glutamate N-{4-[(6aR)-3-amino-1-oxo-1,2,5,6,6a,7-hexahydro-8H-imidazo[1,5-f]pteridin-10-ium-8-yl]benzoyl}-L-glutamic acid N5,n10-methenyl-5,6,7,8-tetrahydrofolate N5,n10-methenyl-5,6,7,8-tetrahydrofolic acid N5,n10-methenyl-tetrahydrofolate N5,n10-methenyl-tetrahydrofolic acid N5-n10-ch-thf N5-n10-methenyltetrahydrofolate N5-n10-methenyltetrahydrofolic acid C20H22N7O6 456.432 456.163156471 (6aR)-3-amino-8-(4-{[(1S)-1,3-dicarboxypropyl]carbamoyl}phenyl)-1-oxo-1H,2H,5H,6H,6aH,7H,8H-10λ⁵-imidazo[1,5-f]pteridin-10-ylium anhydroleucovorin 7444-29-3 [H][C@@]12CN(C=[N+]1C1=C(NC2)N=C(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)/p+1/t12-,13+/m1/s1 MEANFMOQMXYMCT-OLZOCXBDSA-O Solid Cytosol logp -1.25 ALOGPS logs -3.64 ALOGPS solubility 1.13e-01 g/l ALOGPS logp -4.6 ChemAxon pka_strongest_acidic 3.22 ChemAxon pka_strongest_basic 1.31 ChemAxon iupac (6aR)-3-amino-8-(4-{[(1S)-1,3-dicarboxypropyl]carbamoyl}phenyl)-1-oxo-1H,2H,5H,6H,6aH,7H,8H-10λ⁵-imidazo[1,5-f]pteridin-10-ylium ChemAxon average_mass 456.432 ChemAxon mono_mass 456.163156471 ChemAxon smiles [H][C@@]12CN(C=[N+]1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C(O)=O ChemAxon formula C20H22N7O6 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)/p+1/t12-,13+/m1/s1 ChemAxon inchikey MEANFMOQMXYMCT-OLZOCXBDSA-O ChemAxon polar_surface_area 189.46 ChemAxon refractivity 134.37 ChemAxon polarizability 45.83 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 10 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge 1 ChemAxon Reductive carboxylate cycle (CO2 fixation) ec00720 Glyoxylate and dicarboxylate metabolism ec00630 One carbon pool by folate 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. PW000773 ec00670 Metabolic Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 formylTHF biosynthesis I 1CMET2-PWY tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate PWY-6613 Specdb::NmrOneD 290295 Specdb::NmrOneD 290296 Specdb::NmrOneD 290297 Specdb::NmrOneD 290298 Specdb::NmrOneD 290299 Specdb::NmrOneD 290300 Specdb::NmrOneD 290301 Specdb::NmrOneD 290302 Specdb::NmrOneD 290303 Specdb::NmrOneD 290304 Specdb::NmrOneD 290305 Specdb::NmrOneD 290306 Specdb::NmrOneD 290307 Specdb::NmrOneD 290308 Specdb::NmrOneD 290309 Specdb::NmrOneD 290310 Specdb::NmrOneD 290311 Specdb::NmrOneD 290312 Specdb::NmrOneD 290313 Specdb::NmrOneD 290314 Specdb::MsMs 26870 Specdb::MsMs 26871 Specdb::MsMs 26872 Specdb::MsMs 33428 Specdb::MsMs 33429 Specdb::MsMs 33430 HMDB01354 644350 388374 C00445 15638 5-10-METHENYL-THF 5,10-Methenyltetrahydrofolate 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Phosphoribosylglycinamide formyltransferase P08179 PUR3_ECOLI purN http://ecmdb.ca/proteins/P08179.xml Serine hydroxymethyltransferase P0A825 GLYA_ECOLI glyA http://ecmdb.ca/proteins/P0A825.xml Bifunctional protein folD P24186 FOLD_ECOLI folD http://ecmdb.ca/proteins/P24186.xml Aminomethyltransferase P27248 GCST_ECOLI gcvT http://ecmdb.ca/proteins/P27248.xml Phosphoribosylglycinamide formyltransferase 2 P33221 PURT_ECOLI purT http://ecmdb.ca/proteins/P33221.xml Uncharacterized protein ygfA P0AC28 YGFA_ECOLI ygfA http://ecmdb.ca/proteins/P0AC28.xml Water + 5,10-Methenyltetrahydrofolate <> N10-Formyl-THF + Hydrogen ion R01655 METHENYLTHFCYCLOHYDRO-RXN 5,10-Methylene-THF + NADP <> 5,10-Methenyltetrahydrofolate + NADPH + Hydrogen ion R01220 METHYLENETHFDEHYDROG-NADP-RXN Water + 5,10-Methenyltetrahydrofolate > N5-Formyl-H4F + Hydrogen ion N5-Formyl-H4F + Hydrogen ion > Water + 5,10-Methenyltetrahydrofolate R02300 RXN-6321 5,10-Methylene-THF + NADP <> 5,10-Methenyltetrahydrofolate + NADPH R01220 N5-Formyl-H4F <> 5,10-Methenyltetrahydrofolate + Water R02300 Glycineamideribotide + 5,10-Methenyltetrahydrofolate + Water <> 5'-Phosphoribosyl-N-formylglycineamide + Tetrahydrofolic acid R04326 5,10-Methenyltetrahydrofolate + Water Hydrogen ion + N5-Formyl-H4F RXN-6321 N5-Formyl-H4F + Adenosine triphosphate > 5,10-Methenyltetrahydrofolate + ADP + Phosphate 5-FORMYL-THF-CYCLO-LIGASE-RXN 5,10-Methylene-THF + NADP > 5,10-Methenyltetrahydrofolate + NADPH 5,10-Methenyltetrahydrofolate + Water > N10-Formyl-THF Adenosine triphosphate + N5-Formyl-H4F <> ADP + Phosphate + 5,10-Methenyltetrahydrofolate R02301 Water + 5 5,10-Methenyltetrahydrofolate <> N10-Formyl-THF + Hydrogen ion N5-Formyl-H4F + Hydrogen ion > Water +5 5,10-Methenyltetrahydrofolate Water + 5 5,10-Methenyltetrahydrofolate <> N10-Formyl-THF + Hydrogen ion N5-Formyl-H4F + Hydrogen ion > Water +5 5,10-Methenyltetrahydrofolate