2.0 2012-05-31 14:50:09 -0600 2015-06-03 17:20:12 -0600 ECMDB20549 M2MDB001355 Dihydromonapterin-triphosphate Dihydromonapterin-triphosphate is a member of the chemical class known as Biopterins and Derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. 7,8-Dihydroneopterin triphosphate (DHNTP) is an intermediate in tetrahydrobiopterin and tetrahydromonopterin biosynthesis. Tetrahydromonapterin is the major tetrahydropterin in E. coli, although the biological role of tetrahydromonapterin in E. coli is currently unknown. 6-(L-<I>threo</I>-1',2',3'-trihydroxypropyl)-7,8-dihydropterin-3'-triphosphate 6-(L-Threo-1',2',3'-trihydroxypropyl)-7,8-dihydropterin-3'-triphosphate 6-(L-Threo-1',2',3'-trihydroxypropyl)-7,8-dihydropterin-3'-triphosphoric acid 6-(L-threo-1',2',3'-Trihydroxypropyl)-7,8-dihydropterin-3'-triphosphoric acid Dihydromonapterin-triphosphate Dihydromonapterin-triphosphoric acid H2MTP H<SUB>2</SUB>MTP C9H14N5O13P3 493.1544 492.980095095 6-[(1S,2S)-3-[({[(hydrogen phosphonatooxy)phosphinato]oxy}phosphinato)-λ³-oxidanyliumyl]-1,2-dihydroxypropyl]-4-hydroxy-2-iminiumyl-2,7-dihydro-1H-5λ⁵-pteridin-8-ium-5-ylium 6-[(1S,2S)-3-{[(hydrogen phosphonatooxyphosphinato)oxyphosphinato]-λ³-oxidanyliumyl}-1,2-dihydroxypropyl]-4-hydroxy-2-iminio-1,7-dihydro-5λ⁵-pteridin-8-ium-5-ylium [H][C@](O)(C[O+]P([O-])(=O)OP([O-])(=O)O[P+](O)([O-])[O-])[C@@]([H])(O)C1=[N+]=C2C(O)=NC(=[NH2+])NC2=[NH+]C1 InChI=1S/C9H14N5O13P3/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-25-29(21,22)27-30(23,24)26-28(18,19)20/h4,6,15-16H,1-2H2,(H6-,10,11,13,14,17,18,19,20,21,22,23,24)/q+1/t4-,6-/m0/s1 FXEIKSFXDSWHMF-NJGYIYPDSA-N Cytosol logp 1.29 ALOGPS logs -1.73 ALOGPS solubility 1.29e+01 g/l ALOGPS logp -9.2 ChemAxon pka_strongest_acidic -12 ChemAxon pka_strongest_basic 15.21 ChemAxon iupac 6-[(1S,2S)-3-[({[(hydrogen phosphonatooxy)phosphinato]oxy}phosphinato)-λ³-oxidanyliumyl]-1,2-dihydroxypropyl]-4-hydroxy-2-iminiumyl-2,7-dihydro-1H-5λ⁵-pteridin-8-ium-5-ylium ChemAxon average_mass 493.1544 ChemAxon mono_mass 492.980095095 ChemAxon smiles [H][C@](O)(C[O+]P([O-])(=O)OP([O-])(=O)O[P+](O)([O-])[O-])[C@@]([H])(O)C1=[N+]=C2C(O)=NC(=[NH2+])NC2=[NH+]C1 ChemAxon formula C9H14N5O13P3 ChemAxon inchi InChI=1S/C9H14N5O13P3/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-25-29(21,22)27-30(23,24)26-28(18,19)20/h4,6,15-16H,1-2H2,(H6-,10,11,13,14,17,18,19,20,21,22,23,24)/q+1/t4-,6-/m0/s1 ChemAxon inchikey FXEIKSFXDSWHMF-NJGYIYPDSA-N ChemAxon polar_surface_area 298.94 ChemAxon refractivity 121.55 ChemAxon polarizability 37.69 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 13 ChemAxon donor_count 7 ChemAxon physiological_charge 0 ChemAxon formal_charge 1 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::NmrOneD 254748 Specdb::NmrOneD 254749 Specdb::NmrOneD 254750 Specdb::NmrOneD 254751 Specdb::NmrOneD 254752 Specdb::NmrOneD 254753 Specdb::NmrOneD 254754 Specdb::NmrOneD 254755 Specdb::NmrOneD 254756 Specdb::NmrOneD 254757 Specdb::NmrOneD 254758 Specdb::NmrOneD 254759 Specdb::NmrOneD 254760 Specdb::NmrOneD 254761 Specdb::NmrOneD 254762 Specdb::NmrOneD 254763 Specdb::NmrOneD 254764 Specdb::NmrOneD 254765 Specdb::NmrOneD 254766 Specdb::NmrOneD 254767 25203084 DIHYDROMONAPTERIN-TRIPHOSPHATE 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 D-erythro-7,8-dihydroneopterin triphosphate epimerase P0AC19 FOLX_ECOLI folX http://ecmdb.ca/proteins/P0AC19.xml Dihydroneopterin triphosphate <> Dihydromonapterin-triphosphate H2NTPEPIM-RXN Dihydromonapterin-triphosphate + Water > Hydrogen ion + 7,8-Dihydroneopterin + Phosphate RXN0-6368 7,8-dihydroneopterin 3'-triphosphate <> Dihydromonapterin-triphosphate PW_R005965