2.0 2012-05-31 13:46:20 -0600 2015-06-03 15:53:47 -0600 ECMDB01144 M2MDB000274 Dihydroneopterin triphosphate 7,8-Dihydroneopterin triphosphate (DHNTP) is an intermediate in folate biosynthesis. It is converted from 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine by dihydroneopterin triphosphate synthase (EC:3.5.4.16) (KEGG) 2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphate 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl) dihydropteridine triphosphate 2-amino-4-Hydroxy-6-(erythro-1,2,3-trihydroxypropyl) dihydropteridine triphosphoric acid 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphate 2-amino-4-Hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphoric acid 6-(D-erythro-1',2',3'-trihydroxypropyl)-7,8-dihydropterin-3'-triphosphate 6-(D-Erythro-1',2',3'-trihydroxypropyl)-7,8-dihydropterin-3'-triphosphate 6-(D-Erythro-1',2',3'-trihydroxypropyl)-7,8-dihydropterin-3'-triphosphoric acid 6-(D-erythro-1',2',3'-Trihydroxypropyl)-7,8-dihydropterin-3'-triphosphoric acid 6-(L-Erythro-1,2-Dihydroxypropyl 3-triphosphate)-7,8-dihydropterin 6-(L-erythro-1,2-Dihydroxypropyl 3-triphosphoric acid)-7,8-dihydropterin 6-[(1S,2R)-1,2-Dihydroxy-3-triphosphooxypropyl]-7,8-dihydropterin 7,8-Dihydroneopterin 3'-triphosphate 7,8-Dihydroneopterin 3'-triphosphoric acid 7,8-Dihydroneopterin triphosphate 7,8-Dihydroneopterin triphosphoric acid D-Erythro-7,8-dihydroneopterin triphosphate D-erythro-7,8-Dihydroneopterin triphosphoric acid DHNPTP Dihydroneopterin triphosphate Dihydroneopterin triphosphoric acid H2NTP H2NTP C9H16N5O13P3 495.1703 494.995745159 {[({[(2R,3S)-3-(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)-2,3-dihydroxypropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}phosphonic acid {[(2R,3S)-3-(2-amino-4-oxo-7,8-dihydro-1H-pteridin-6-yl)-2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxyphosphonic acid 20574-65-6 NC1=NC2=C(N=C(CN2)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(=O)N1 InChI=1S/C9H16N5O13P3/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,(H,21,22)(H,23,24)(H2,18,19,20)(H4,10,11,13,14,17)/t4-,6+/m1/s1 DGGUVLXVLHAAGT-XINAWCOVSA-N Solid Cytosol logp -0.71 ALOGPS logs -1.89 ALOGPS solubility 6.43e+00 g/l ALOGPS logp -4.3 ChemAxon pka_strongest_acidic 0.9 ChemAxon pka_strongest_basic -1.5 ChemAxon iupac {[({[(2R,3S)-3-(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)-2,3-dihydroxypropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}phosphonic acid ChemAxon average_mass 495.1703 ChemAxon mono_mass 494.995745159 ChemAxon smiles NC1=NC2=C(N=C(CN2)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(=O)N1 ChemAxon formula C9H16N5O13P3 ChemAxon inchi InChI=1S/C9H16N5O13P3/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,(H,21,22)(H,23,24)(H2,18,19,20)(H4,10,11,13,14,17)/t4-,6+/m1/s1 ChemAxon inchikey DGGUVLXVLHAAGT-XINAWCOVSA-N ChemAxon polar_surface_area 292.15 ChemAxon refractivity 102.28 ChemAxon polarizability 37.74 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 15 ChemAxon donor_count 9 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Folate biosynthesis The biosynthesis of folic acid begins with a product of purine nucleotides de novo biosynthesis pathway, GTP. This compound is involved in a reaction with water through a GTP cyclohydrolase 1 protein complex, resulting in a hydrogen ion, formic acid and 7,8-dihydroneopterin 3-triphosphate. The latter compound is dephosphatased through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, hydrogen ion and 7,8-dihydroneopterin 3-phosphate. The latter compound reacts with water spontaneously resulting in the release of a phosphate and a 7,8 -dihydroneopterin. This compound reacts with a dihydroneopterin aldolase, releasing a glycoaldehyde and 6-hydroxymethyl-7,9-dihydropterin. The latter compound is phosphorylated with a ATP-driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in a (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate. Chorismate is metabolized by reacting with L-glutamine through a 4-amino-4-deoxychorismate synthase resulting in L-glutamic acid and 4-amino-4-deoxychorismate. The latter compound then reacts through an aminodeoxychorismate lyase resulting in pyruvic acid,hydrogen ion and p-aminobenzoic acid. (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate and p-aminobenzoic acid react through a dihydropteroate synthase resulting in pyrophosphate and 7,8-dihydropteroic acid. This compound reacts with L-glutamic acid through an ATP driven bifunctional folylpolyglutamate synthetase / dihydrofolate synthetase resulting in a 7,8-dihydrofolate monoglutamate. This compound is reduced through an NADPH mediated dihydrofolate reductase resulting in a tetrahydrofate. This product goes on to a one carbon pool by folate pathway. PW000908 ec00790 Metabolic Metabolic pathways eco01100 6-hydroxymethyl-dihydropterin diphosphate biosynthesis I PWY-6147 preQ0 biosynthesis PWY-6703 tetrahydromonapterin biosynthesis PWY0-1433 Specdb::CMs 19919 Specdb::CMs 37875 Specdb::CMs 158699 Specdb::CMs 1082981 Specdb::CMs 1082982 Specdb::CMs 1082983 Specdb::CMs 1082984 Specdb::CMs 1082985 Specdb::CMs 1082986 Specdb::CMs 1082987 Specdb::CMs 1082988 Specdb::CMs 1082989 Specdb::CMs 1082990 Specdb::CMs 1082991 Specdb::CMs 1082992 Specdb::CMs 1082993 Specdb::CMs 1082994 Specdb::CMs 1082995 Specdb::CMs 1082996 Specdb::CMs 1082997 Specdb::CMs 1082998 Specdb::CMs 1082999 Specdb::CMs 1083000 Specdb::CMs 1083001 Specdb::CMs 1083002 Specdb::NmrOneD 145930 Specdb::NmrOneD 145931 Specdb::NmrOneD 145932 Specdb::NmrOneD 145933 Specdb::NmrOneD 145934 Specdb::NmrOneD 145935 Specdb::NmrOneD 145936 Specdb::NmrOneD 145937 Specdb::NmrOneD 145938 Specdb::NmrOneD 145939 Specdb::NmrOneD 145940 Specdb::NmrOneD 145941 Specdb::NmrOneD 145942 Specdb::NmrOneD 145943 Specdb::NmrOneD 145944 Specdb::NmrOneD 145945 Specdb::NmrOneD 145946 Specdb::NmrOneD 145947 Specdb::NmrOneD 145948 Specdb::NmrOneD 145949 Specdb::MsMs 25073 Specdb::MsMs 25074 Specdb::MsMs 25075 Specdb::MsMs 31631 Specdb::MsMs 31632 Specdb::MsMs 31633 Specdb::MsMs 2747035 Specdb::MsMs 2747036 Specdb::MsMs 2747037 Specdb::MsMs 2931120 Specdb::MsMs 2931121 Specdb::MsMs 2931122 HMDB00980 121885 108735 C04895 DIHYDRONEOPTERIN-P3 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 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 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 Curtius HC, Heintel D, Ghisla S, Kuster T, Leimbacher W, Niederwieser A: Biosynthesis of tetrahydrobiopterin in man. J Inherit Metab Dis. 1985;8 Suppl 1:28-33. 3930838 Ferre, Juan; Naylor, Edwin W.; Jacobson, K. Bruce. Repetitive recycling of guanosine triphosphate cyclohydrolase I for synthesis of dihydroneopterin triphosphate. Analytical Biochemistry (1989), 176(1), 15-18. Alkaline phosphatase P00634 PPB_ECOLI phoA http://ecmdb.ca/proteins/P00634.xml GTP cyclohydrolase 1 P0A6T5 GCH1_ECOLI folE http://ecmdb.ca/proteins/P0A6T5.xml D-erythro-7,8-dihydroneopterin triphosphate epimerase P0AC19 FOLX_ECOLI folX http://ecmdb.ca/proteins/P0AC19.xml Dihydroneopterin triphosphate pyrophosphatase P0AFC0 NUDB_ECOLI nudB http://ecmdb.ca/proteins/P0AFC0.xml 6-carboxy-5,6,7,8-tetrahydropterin synthase P65870 QUED_ECOLI queD http://ecmdb.ca/proteins/P65870.xml Mutator mutT protein P08337 MUTT_ECOLI mutT http://ecmdb.ca/proteins/P08337.xml Dihydroneopterin triphosphate + Water > Dihydroneopterin monophosphate + Hydrogen ion + Pyrophosphate H2NEOPTERINP3PYROPHOSPHOHYDRO-RXN Guanosine triphosphate + Water > Dihydroneopterin triphosphate + Formic acid + Hydrogen ion GTP-CYCLOHYDRO-I-RXN Dihydroneopterin triphosphate <> Dihydromonapterin-triphosphate H2NTPEPIM-RXN Dihydroneopterin triphosphate + Water > Acetaldehyde + 6-Carboxy-5,6,7,8-tetrahydropterin + Hydrogen ion + Triphosphate RXN0-5507 Dihydroneopterin triphosphate <> Dyspropterin + Triphosphate R04286 Dihydroneopterin triphosphate + 3 Water <> 7,8-Dihydroneopterin +3 Phosphate R04620 Dihydroneopterin triphosphate + Water <> 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine R04639 Dihydroneopterin triphosphate > D-erythro-7,8-dihydroneopterin triphosphate Dihydroneopterin triphosphate + Water > 6-Carboxy-5,6,7,8-tetrahydropterin + Acetaldehyde + Triphosphate Guanosine triphosphate + Water <> Formic acid + Dihydroneopterin triphosphate R00424 Dihydroneopterin triphosphate <> Dyspropterin + Triphosphate Dihydroneopterin triphosphate + 3 Water <>7 7,8-Dihydroneopterin +3 Phosphate Dihydroneopterin triphosphate <> Dyspropterin + Triphosphate