2.0 2012-05-31 13:47:20 -0600 2015-06-03 15:53:50 -0600 ECMDB01195 M2MDB000292 Dyspropterin Dyspropterin, an intermediate formed from dihydroneopterin triphosphate in the biosynthetic pathway of tetrahydrobiopterin. 6-(1,2-Dioxopropyl)-5,6,7,8-tetrahydropterin 6-Pyruvoyl-5,6,7,8-tetrahydropterin 6-Pyruvoyl-tetrahydropterin 6-Pyruvoyltetrahydropterin Dyspropterin PPH4 Pyruvoyl-H4-pterin Pyruvoyl-H<SUB>4</SUB>-pterin C9H11N5O3 237.2153 237.086189243 1-(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)propane-1,2-dione 1-(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)propane-1,2-dione 89687-39-8 CC(=O)C(=O)C1CNC2=C(N1)C(=O)NC(N)=N2 InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h4,12H,2H2,1H3,(H4,10,11,13,14,17) WBJZXBUVECZHCE-UHFFFAOYSA-N Solid Cytoplasm Periplasm logp -1.01 ALOGPS logs -2.56 ALOGPS solubility 6.47e-01 g/l ALOGPS logp -1.2 ChemAxon pka_strongest_acidic 7.81 ChemAxon pka_strongest_basic 1.82 ChemAxon iupac 1-(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)propane-1,2-dione ChemAxon average_mass 237.2153 ChemAxon mono_mass 237.086189243 ChemAxon smiles CC(=O)C(=O)C1CNC2=C(N1)C(=O)NC(N)=N2 ChemAxon formula C9H11N5O3 ChemAxon inchi InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h4,12H,2H2,1H3,(H4,10,11,13,14,17) ChemAxon inchikey WBJZXBUVECZHCE-UHFFFAOYSA-N ChemAxon polar_surface_area 125.68 ChemAxon refractivity 67.02 ChemAxon polarizability 21.98 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge 0 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 Specdb::CMs 23259 Specdb::CMs 119218 Specdb::CMs 137213 Specdb::CMs 144947 Specdb::NmrOneD 8902 Specdb::NmrOneD 8903 Specdb::NmrOneD 8904 Specdb::NmrOneD 8905 Specdb::NmrOneD 8906 Specdb::NmrOneD 8907 Specdb::NmrOneD 8908 Specdb::NmrOneD 8909 Specdb::NmrOneD 8910 Specdb::NmrOneD 8911 Specdb::NmrOneD 8912 Specdb::NmrOneD 8913 Specdb::NmrOneD 8914 Specdb::NmrOneD 8915 Specdb::NmrOneD 8916 Specdb::NmrOneD 8917 Specdb::NmrOneD 8918 Specdb::NmrOneD 8919 Specdb::NmrOneD 8920 Specdb::NmrOneD 8921 Specdb::MsMs 27689 Specdb::MsMs 27690 Specdb::MsMs 27691 Specdb::MsMs 34247 Specdb::MsMs 34248 Specdb::MsMs 34249 Specdb::MsMs 2385221 Specdb::MsMs 2385222 Specdb::MsMs 2385223 Specdb::MsMs 2577687 Specdb::MsMs 2577688 Specdb::MsMs 2577689 HMDB01195 128973 114280 C03684 17804 6-PYRUVOYL-5678-TETRAHYDROPTERIN 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 Bonafe L, Thony B, Leimbacher W, Kierat L, Blau N: Diagnosis of dopa-responsive dystonia and other tetrahydrobiopterin disorders by the study of biopterin metabolism in fibroblasts. Clin Chem. 2001 Mar;47(3):477-85. 11238300 Niederwieser A, Curtius HC: Tetrahydrobiopterin biosynthetic pathway and deficiency. Enzyme. 1987;38(1-4):302-11. 3326735 Dhondt JL, Hayte JM: [Screening of tetrahydrobiopterin deficiency among hyperphenylalaninemic patients] Ann Biol Clin (Paris). 2002 Mar-Apr;60(2):165-71. 11937441 Iwanaga N, Yamamasu S, Tachibana D, Nishio J, Nakai Y, Shintaku H, Ishiko O: Activity of synthetic enzymes of tetrahydrobiopterin in the human placenta. Int J Mol Med. 2004 Jan;13(1):117-20. 14654981 6-carboxy-5,6,7,8-tetrahydropterin synthase P65870 QUED_ECOLI queD http://ecmdb.ca/proteins/P65870.xml Dihydroneopterin triphosphate <> Dyspropterin + Triphosphate R04286 Dihydroneopterin triphosphate <> Dyspropterin + Triphosphate Dihydroneopterin triphosphate <> Dyspropterin + Triphosphate