2.0 2012-08-03 14:57:54 -0600 2015-09-13 15:15:32 -0600 ECMDB21400 M2MDB001795 Pterin Pterin is a chemical compound composed of a pyrazine ring and a pyrimidine ring; the pyrimidine ring has a carbonyl oxygen and an amino group. Several tautomers of pterin exist and are shown below. Pterin belongs to the pteridine family of heterocycles. -- Wikipedia 2-amino-1H-pteridin-4-one 2-amino-3H-pteridin-4-one 2-Amino-4(1H)-pteridinone 2-Amino-4(3H)-pteridinone 2-Amino-4-hydroxypteridine 2-Amino-4-oxopteridine 2-amino-4-pteridinol 2-Amino-4-pteridone 2-amino-Quinonoid dihydropterin 2-Aminopteridin-4-one 4-Oxo-2-aminopteridine 4-Oxopterin Pteridoxamine Pterin Pterine C6H5N5O 163.1368 163.049409807 2-amino-3,4-dihydropteridin-4-one 2-amino-4-oxopteridine 2236-60-4 NC1=NC2=NC=CN=C2C(=O)N1 InChI=1S/C6H5N5O/c7-6-10-4-3(5(12)11-6)8-1-2-9-4/h1-2H,(H3,7,9,10,11,12) HNXQXTQTPAJEJL-UHFFFAOYSA-N Solid Cytoplasm logp -0.86 ALOGPS logs -2.04 ALOGPS solubility 1.49e+00 g/l ALOGPS logp -0.96 ChemAxon pka_strongest_acidic 10 ChemAxon pka_strongest_basic -1.8 ChemAxon iupac 2-amino-3,4-dihydropteridin-4-one ChemAxon average_mass 163.1368 ChemAxon mono_mass 163.049409807 ChemAxon smiles NC1=NC2=NC=CN=C2C(=O)N1 ChemAxon formula C6H5N5O ChemAxon inchi InChI=1S/C6H5N5O/c7-6-10-4-3(5(12)11-6)8-1-2-9-4/h1-2H,(H3,7,9,10,11,12) ChemAxon inchikey HNXQXTQTPAJEJL-UHFFFAOYSA-N ChemAxon polar_surface_area 93.26 ChemAxon refractivity 41.82 ChemAxon polarizability 14.46 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 19631 Specdb::CMs 130955 Specdb::CMs 138689 Specdb::NmrOneD 1546 Specdb::NmrOneD 145410 Specdb::NmrOneD 145411 Specdb::NmrOneD 145412 Specdb::NmrOneD 145413 Specdb::NmrOneD 145414 Specdb::NmrOneD 145415 Specdb::NmrOneD 145416 Specdb::NmrOneD 145417 Specdb::NmrOneD 145418 Specdb::NmrOneD 145419 Specdb::NmrOneD 145420 Specdb::NmrOneD 145421 Specdb::NmrOneD 145422 Specdb::NmrOneD 145423 Specdb::NmrOneD 145424 Specdb::NmrOneD 145425 Specdb::NmrOneD 145426 Specdb::NmrOneD 145427 Specdb::NmrOneD 145428 Specdb::NmrOneD 145429 Specdb::MsMs 1141 Specdb::MsMs 1142 Specdb::MsMs 1143 Specdb::MsMs 309670 Specdb::MsMs 309671 Specdb::MsMs 309672 Specdb::MsMs 354175 Specdb::MsMs 354176 Specdb::MsMs 354177 Specdb::MsMs 451982 Specdb::MsMs 2226903 Specdb::MsMs 2227829 Specdb::MsMs 2229225 Specdb::MsMs 2230210 Specdb::MsMs 2231528 Specdb::MsMs 2232686 Specdb::MsMs 2233944 Specdb::MsMs 2234973 Specdb::MsMs 2322934 Specdb::MsMs 2322935 Specdb::MsMs 2322936 Specdb::MsMs 2616471 Specdb::MsMs 2616472 Specdb::MsMs 2616473 Specdb::NmrTwoD 1490 HMDB00802 73000 65806 C00715 18265 PE0 Pterin Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776 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 Bonafe L, Thony B, Penzien JM, Czarnecki B, Blau N: Mutations in the sepiapterin reductase gene cause a novel tetrahydrobiopterin-dependent monoamine-neurotransmitter deficiency without hyperphenylalaninemia. Am J Hum Genet. 2001 Aug;69(2):269-77. Epub 2001 Jul 6. 11443547 Dhondt JL, Cotton RG, Danks DM: Liver enzyme activities in hyperphenylalaninaemia due to a defective synthesis of tetrahydrobiopterin. J Inherit Metab Dis. 1985;8(2):47-8. 3939528 Kaufman S, Kapatos G, Rizzo WB, Schulman JD, Tamarkin L, Van Loon GR: Tetrahydropterin therapy for hyperphenylalaninemia caused by defective synthesis of tetrahydrobiopterin. Ann Neurol. 1983 Sep;14(3):308-15. 6139056 Katoh S, Sueoka T, Matsuura S, Sugimoto T: Biopterin and neopterin in human saliva. Life Sci. 1989;45(26):2561-8. 2615555 Dhondt JL, Tilmont P, Ringel J, Farriaux JP: Pterins analysis in amniotic fluid for the prenatal diagnosis of GTP cyclohydrolase deficiency. J Inherit Metab Dis. 1990;13(6):879-82. 2079836 Krumdieck CL, Fukushima K, Fukushima T, Shiota T, Butterworth CE Jr: A long-term study of the excretion of folate and pterins in a human subject after ingestion of 14C folic acid, with observations on the effect of diphenylhydantoin administration. Am J Clin Nutr. 1978 Jan;31(1):88-93. 413430 Han F, Huynh BH, Shi H, Lin B, Ma Y: Pteridine analysis in urine by capillary electrophoresis using laser-induced fluorescence detection. Anal Chem. 1999 Apr 1;71(7):1265-9. 10204031 Yamamoto T, Moriwaki Y, Takahashi S, Tsutsumi Z, Yamakita J, Nasako Y, Hiroishi K, Higashino K: Determination of human plasma xanthine oxidase activity by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Jun 7;681(2):395-400. 8811453 Beckman JS, Parks DA, Pearson JD, Marshall PA, Freeman BA: A sensitive fluorometric assay for measuring xanthine dehydrogenase and oxidase in tissues. Free Radic Biol Med. 1989;6(6):607-15. 2753392 Gordon JH, Perry KO: Pre- and postsynaptic neurochemical alterations following estrogen-induced striatal dopamine hypo- and hypersensitivity. Brain Res Bull. 1983 Apr;10(4):425-8. 6134572 Stupperich E: Recent advances in elucidation of biological corrinoid functions. FEMS Microbiol Rev. 1993 Nov;12(4):349-65. 8268006 Niederwieser A, Blau N, Wang M, Joller P, Atares M, Cardesa-Garcia J: GTP cyclohydrolase I deficiency, a new enzyme defect causing hyperphenylalaninemia with neopterin, biopterin, dopamine, and serotonin deficiencies and muscular hypotonia. Eur J Pediatr. 1984 Feb;141(4):208-14. 6734669 Blau N, Kierat L, Matasovic A, Leimbacher W, Heizmann CW, Guardamagna O, Ponzone A: Antenatal diagnosis of tetrahydrobiopterin deficiency by quantification of pterins in amniotic fluid and enzyme activity in fetal and extrafetal tissue. Clin Chim Acta. 1994 May;226(2):159-69. 7923811 Rokos H, Beazley WD, Schallreuter KU: Oxidative stress in vitiligo: photo-oxidation of pterins produces H(2)O(2) and pterin-6-carboxylic acid. Biochem Biophys Res Commun. 2002 Apr 12;292(4):805-11. 11944885 Taylor, Edward C.; Kobylecki, Ryszard. Pteridines. 43. A facile synthesis of 6-chloropterin and 2,4-diamino-6-chloropteridine. Journal of Organic Chemistry (1978), 43(4), 680-3. http://hmdb.ca/system/metabolites/msds/000/000/720/original/HMDB00802.pdf?1358461693 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 24.1 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 96400 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776