2.0 2012-07-30 14:55:14 -0600 2015-06-03 17:21:05 -0600 ECMDB21288 M2MDB001694 Tetrahydromonapterin Tetrahydromonapterin is a member of the chemical class known as Biopterins and Derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. Tetrahydromonapterin is a major pterin in Escherichia coli and is hypothesized to be the cofactor for phenylalanine hydroxylase (PhhA) in Pseudomonas aeruginosa, but neither its biosynthetic origin nor its cofactor role has been clearly demonstrated. Collectively, these data establish that tetrahydromonapterin formation requires both FolX and FolM, that tetrahydromonapterin is the physiological cofactor for PhhA, and that tetrahydromonapterin can outrank folate as an end product of pterin biosynthesis. (PMID 19897652) H4-MPt H₄-MPt C9H15N5O4 257.2465 257.112403993 2-amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one 2-amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-5,6,7,8-tetrahydro-1H-pteridin-4-one [H]OC([H])([H])[C@]([H])(O[H])[C@@]([H])(O[H])C1([H])N([H])C2=C(N([H])C(=NC2=O)N([H])[H])N([H])C1([H])[H] InChI=1S/C9H15N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h3-4,6,12,15-17H,1-2H2,(H4,10,11,13,14,18)/t3?,4-,6-/m0/s1 XHIXPVCTDRNTTC-YQVKZWHSSA-N Cytosol logp -2.19 ALOGPS logs -1.74 ALOGPS solubility 4.68e+00 g/l ALOGPS logp -3.7 ChemAxon pka_strongest_acidic 10.01 ChemAxon pka_strongest_basic 3.58 ChemAxon iupac 2-amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one ChemAxon average_mass 257.2465 ChemAxon mono_mass 257.112403993 ChemAxon smiles [H]OC([H])([H])[C@]([H])(O[H])[C@@]([H])(O[H])C1([H])N([H])C2=C(N([H])C(=NC2=O)N([H])[H])N([H])C1([H])[H] ChemAxon formula C9H15N5O4 ChemAxon inchi InChI=1S/C9H15N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h3-4,6,12,15-17H,1-2H2,(H4,10,11,13,14,18)/t3?,4-,6-/m0/s1 ChemAxon inchikey XHIXPVCTDRNTTC-YQVKZWHSSA-N ChemAxon polar_surface_area 152.23 ChemAxon refractivity 69.98 ChemAxon polarizability 24.59 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 9 ChemAxon donor_count 7 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Tetrahydromonapterin Biosynthesis 5,6,7,8-tetrahydromonapterin is the major tetrahydropterin in E. coli, although the biological role of tetrahydromonapterin in E. coli is currently unknown. It was shown to be a cofactor for the phenylalanine hydroxylase PhhA of Pseudomonas aeruginosa, but no enzyme requiring tetrahydromonapterin as a cofactor has yet been discovered in E. coli. Production of tetrahydromonapterin far exceeds production of folate, indicating that the majority of 7,8-dihydroneopterin 3'-triphosphate, the product of the first committed step of the superpathway of tetrahydrofolate biosynthesis and salvage pathway, is diverted from folate biosynthesis to this pathway. High levels of monapterin are found in the growth medium. PW002043 Metabolic tetrahydromonapterin biosynthesis PWY0-1433 Specdb::CMs 1083346 Specdb::NmrOneD 301165 Specdb::NmrOneD 301166 Specdb::NmrOneD 301167 Specdb::NmrOneD 301168 Specdb::NmrOneD 301169 Specdb::NmrOneD 301170 Specdb::NmrOneD 301171 Specdb::NmrOneD 301172 Specdb::NmrOneD 301173 Specdb::NmrOneD 301174 Specdb::NmrOneD 301175 Specdb::NmrOneD 301176 Specdb::NmrOneD 301177 Specdb::NmrOneD 301178 Specdb::NmrOneD 301179 Specdb::NmrOneD 301180 Specdb::NmrOneD 301181 Specdb::NmrOneD 301182 Specdb::NmrOneD 301183 Specdb::NmrOneD 301184 Specdb::MsMs 27356 Specdb::MsMs 27357 Specdb::MsMs 27358 Specdb::MsMs 33914 Specdb::MsMs 33915 Specdb::MsMs 33916 45479608 CPD0-2101 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 Pribat, A., Blaby, I. K., Lara-Nunez, A., Gregory, J. F. 3rd, de Crecy-Lagard, V., Hanson, A. D. (2010). "FolX and FolM are essential for tetrahydromonapterin synthesis in Escherichia coli and Pseudomonas aeruginosa." J Bacteriol 192:475-482. 19897652 Dihydrofolate reductase folM P0AFS3 FOLM_ECOLI folM http://ecmdb.ca/proteins/P0AFS3.xml 7,8-Dihydroneopterin + Hydrogen ion + NADPH > NADP + Tetrahydromonapterin RXN0-6367 Tetrahydromonapterin + NADP < Hydrogen ion + 7,8-Dihydroneopterin + NADPH RXN0-6367 Dihydromethysticin + NADPH + Hydrogen ion > Tetrahydromonapterin + NADP PW_R005967