2.0 2012-05-31 10:21:39 -0600 2015-09-13 12:56:06 -0600 ECMDB00132 M2MDB000051 Guanine Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA. Guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with conjugated double bonds. Being unsaturated, the bicyclic molecule is planar. The guanine nucleoside is called guanosine. High affinity binding of guanine nucleotides and the ability to hydrolyze bound GTP to GDP are characteristics of an extended family of intracellular proteins. Hypoxanthine-guanine phosphoribosyltransferase (HPRT, EC 2.4.2.8) is a purine salvage enzyme that catalyses the conversion of hypoxanthine and guanine to their respective mononucleotides. Peroxynitrite induces DNA base damage predominantly at guanine (G) and 8-oxoguanine (8-oxoG) nucleobases via oxidation reactions. G and 8-oxoG are the most reactive bases toward Peroxynitrite and possibly the major contributors to peroxynitrite-derived genotoxic and mutagenic lesions. The neutral G radical, reacts with NO2 to yield 8-nitroguanine and 5-nitro-4-guanidinohydantoin. (PMID: 16352449, 2435586) 2-Amino-1,7-dihydro-6H-Purin-6-one 2-Amino-1,9-dihydro-6H-purin-6-one 2-Amino-1,9-dihydro-purin-6-one 2-Amino-3,7-dihydro-6H-purin-6-one 2-Amino-6-hydroxy-1H-purine 2-Amino-6-hydroxypurine 2-Amino-6-purinol 2-Amino-Hypoxanthine 2-Aminohypoxanthine 6-Hydroxy-2-aminopurine C.I. Natural White 1 CI Natural white 1 Dew Pearl GUA Guanin Guanine Guanine enol GUN Mearlmaid Mearlmaid AA Natural pearl essence Natural White 1 Naturon Pathocidin Pearl Essence Stella Polaris C5H5N5O 151.1261 151.049409807 2-amino-6,7-dihydro-3H-purin-6-one 2-aminohypoxanthine 73-40-5 NC1=NC(=O)C2=C(N1)N=CN2 InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11) UYTPUPDQBNUYGX-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp -0.92 ALOGPS logs -1.82 ALOGPS solubility 2.31e+00 g/l ALOGPS melting_point 360 oC logp -0.59 ChemAxon pka_strongest_acidic 8.95 ChemAxon pka_strongest_basic 2.22 ChemAxon iupac 2-amino-6,7-dihydro-3H-purin-6-one ChemAxon average_mass 151.1261 ChemAxon mono_mass 151.049409807 ChemAxon smiles NC1=NC(=O)C2=C(N1)N=CN2 ChemAxon formula C5H5N5O ChemAxon inchi InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11) ChemAxon inchikey UYTPUPDQBNUYGX-UHFFFAOYSA-N ChemAxon polar_surface_area 96.16 ChemAxon refractivity 38.9 ChemAxon polarizability 13.34 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Metabolic pathways eco01100 preQ0 metabolism PreQ0 or 7-cyano-7-carbaguanine is biosynthesized by degrading GTP. GTP first interacts with water through a GTP cyclohydrolase resulting in the release of a formate, a hydrogen ion and a 7,8-dihydroneopterin 3'-triphosphate. The latter compound then interacts with water through a 6-carboxy-5,6,7,8-tetrahydropterin synthase resulting in a acetaldehyde, triphosphate, 2 hydrogen ion and 6-carboxy-5,6,7,8-tetrahydropterin. The latter compound then reacts spontaneously with a hydrogen ion resulting in the release of a ammonium molecule and a 7-carboxy-7-deazaguanine. This compound then interacts with ATP and ammonium through 7-cyano-7-deazaguanine synthase resulting in the release of water, phosphate, ADP, hydrogen ion and a 7-cyano-7-carbaguanine. The degradation of 7-cyano-7-deazaguanine can lead to produce a preQ1 or a queuine by reacting with 3 hydrogen ions and 2 NADPH through a 7-cyano-7-deazaguanine reductase. PreQ1 then interacts with a guanine 34 in tRNA through a tRNA-guanine transglycosylase resulting in a release of a guanine and a 7-aminomethyl-7-deazaguanosine 34 in tRNA. This nucleic acid then interacts with SAM through a S-adenosylmethionine tRNA ribosyltransferase-isomerase resulting in a release of a hydrogen ion, L-methionine, adenine and an epoxyqueuosine PW001893 Metabolic guanine and guanosine salvage Guanosine can be converted into guanine through a phosphate driven guanosine phosphorylase resulting in the release of an alpha-D-ribose 1 phosphate and a guanine. This compound in turn reacts with a PRPP through a guanine phosphoribosyltransferase resulting in the release of a pyrophosphate and a GMP. Guanosine can also react with and ATP driven guanosine kinase resulting in the release of an ADP, s hydrogen ion and a GMP PW002074 Metabolic purine deoxyribonucleosides degradation PW002077 Metabolic purine ribonucleosides degradation Purine ribonucleoside degradation leads to the production of alpha-D-ribose-1-phosphate. Xanthosine is transported into the cytosol through a xapB. Once in the cytosol xanthosine interacts with phosphate through a xanthosine phosphorylase resulting in the release of a xanthine and a alpha-D-ribose-1-phosphate. Adenosine is transported through a nupC or a nupG transporter, once inside the cytosol it can either react with a phosphate through a adenosine phosphorylase resultin in the release of a adenine and an alpha-D-ribose-1-phosphate. Adenosine reacts with water and hydrogen ion through a adenosine deaminase resulting in the release of ammonium and inosine. Inosine reacts with phosphate through a inosine phosphorylase resulting in the release of a hypoxanthine and an alpha-D-ribose-1-phosphate. Guanosine reacts with a phosphate through a guanosine phosphorylase resulting in the release of a guanine and a alpha-D-ribose-1-phosphate. PW002076 Metabolic purine ribonucleosides degradation to ribose-1-phosphate PWY0-1296 purine deoxyribonucleosides degradation PWY0-1297 queuosine biosynthesis PWY-6700 guanosine nucleotides degradation III PWY-6608 guanine and guanosine salvage I PWY-6620 Specdb::CMs 861 Specdb::CMs 1824 Specdb::CMs 3036 Specdb::CMs 29897 Specdb::CMs 30563 Specdb::CMs 31016 Specdb::CMs 31820 Specdb::CMs 31821 Specdb::CMs 163048 Specdb::EiMs 1803 Specdb::NmrOneD 1102 Specdb::NmrOneD 4947 Specdb::NmrOneD 4948 Specdb::NmrOneD 142430 Specdb::NmrOneD 142431 Specdb::NmrOneD 142432 Specdb::NmrOneD 142433 Specdb::NmrOneD 142434 Specdb::NmrOneD 142435 Specdb::NmrOneD 142436 Specdb::NmrOneD 142437 Specdb::NmrOneD 142438 Specdb::NmrOneD 142439 Specdb::NmrOneD 142440 Specdb::NmrOneD 142441 Specdb::NmrOneD 142442 Specdb::NmrOneD 142443 Specdb::NmrOneD 142444 Specdb::NmrOneD 142445 Specdb::NmrOneD 142446 Specdb::NmrOneD 142447 Specdb::NmrOneD 142448 Specdb::NmrOneD 142449 Specdb::NmrOneD 166581 Specdb::MsMs 6223 Specdb::MsMs 6224 Specdb::MsMs 6225 Specdb::MsMs 6226 Specdb::MsMs 6227 Specdb::MsMs 6228 Specdb::MsMs 6229 Specdb::MsMs 6230 Specdb::MsMs 6231 Specdb::MsMs 6232 Specdb::MsMs 6233 Specdb::MsMs 6234 Specdb::MsMs 6236 Specdb::MsMs 6237 Specdb::MsMs 19967 Specdb::MsMs 19968 Specdb::MsMs 19969 Specdb::MsMs 21518 Specdb::MsMs 21519 Specdb::MsMs 21520 Specdb::MsMs 438628 Specdb::MsMs 438828 Specdb::MsMs 438829 Specdb::MsMs 439072 Specdb::MsMs 440048 Specdb::NmrTwoD 964 Specdb::NmrTwoD 1160 HMDB00132 764 744 C00242 16235 GUANINE GUN Guanine 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 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 Niles, J. C., Wishnok, J. S., Tannenbaum, S. R. (2006). "Peroxynitrite-induced oxidation and nitration products of guanine and 8-oxoguanine: structures and mechanisms of product formation." Nitric Oxide 14:109-121. 16352449 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. 19212411 Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. 12829005 Sculley DG, Dawson PA, Emmerson BT, Gordon RB: A review of the molecular basis of hypoxanthine-guanine phosphoribosyltransferase (HPRT) deficiency. Hum Genet. 1992 Nov;90(3):195-207. 1487231 Boulias C, Moscarello MA: Guanine nucleotides stimulate hydrolysis of phosphatidyl inositol bis phosphate in human myelin membranes. Biochem Biophys Res Commun. 1989 Jul 14;162(1):282-7. 2546548 Harkness RA: Hypoxanthine, xanthine and uridine in body fluids, indicators of ATP depletion. J Chromatogr. 1988 Jul 29;429:255-78. 3062020 Castro-Gago M, Cid E, Trabazo S, Pavon P, Camina F, Rodriguez-Segade S, Einis Punal J, Rodriguez-Nunez A: Cerebrospinal fluid purine metabolites and pyrimidine bases after brief febrile convulsions. Epilepsia. 1995 May;36(5):471-4. 7614924 Steyn LM, Harley EH: Intracellular activity of HPRT Cape Town: purine uptake and growth of cultured cells in selective media. J Inherit Metab Dis. 1985;8(4):198-203. 3939543 Yafe A, Etzioni S, Weisman-Shomer P, Fry M: Formation and properties of hairpin and tetraplex structures of guanine-rich regulatory sequences of muscle-specific genes. Nucleic Acids Res. 2005 May 20;33(9):2887-900. Print 2005. 15908587 Russo TA, Jodush ST, Brown JJ, Johnson JR: Identification of two previously unrecognized genes (guaA and argC) important for uropathogenesis. Mol Microbiol. 1996 Oct;22(2):217-29. 8930907 Liu Z, Li T, Wang E: Simultaneous determination of guanine, uric acid, hypoxanthine and xanthine in human plasma by reversed-phase high-performance liquid chromatography with amperometric detection. Analyst. 1995 Aug;120(8):2181-4. 7677251 Parkinson SJ, Waldman SA: An intracellular adenine nucleotide binding site inhibits guanyly cyclase C by a guanine nucleotide-dependent mechanism. Biochemistry. 1996 Mar 12;35(10):3213-21. 8605156 Rodriguez-Nunez A, Camina F, Lojo S, Rodriguez-Segade S, Castro-Gago M: Concentrations of nucleotides, nucleosides, purine bases and urate in cerebrospinal fluid of children with meningitis. Acta Paediatr. 1993 Oct;82(10):849-52. 8241644 Groopman JD, Zhu JQ, Donahue PR, Pikul A, Zhang LS, Chen JS, Wogan GN: Molecular dosimetry of urinary aflatoxin-DNA adducts in people living in Guangxi Autonomous Region, People's Republic of China. Cancer Res. 1992 Jan 1;52(1):45-52. 1727385 Shioya M, Wakabayashi K, Yamashita K, Nagao M, Sugimura T: Formation of 8-hydroxydeoxyguanosine in DNA treated with fecapentaene-12 and -14. Mutat Res. 1989 Mar;225(3):91-4. 2927433 Allgayer H, Kolb M, Stuber V, Kruis W: Effects of bile acids on base hydroxylation in a model of human colonic mucosal DNA. Cancer Detect Prev. 2002;26(1):85-9. 12088208 Schei MA, Hessen JO, Lund E: House-dust mites and mattresses. Allergy. 2002 Jun;57(6):538-42. 12028120 Weimann A, Belling D, Poulsen HE: Quantification of 8-oxo-guanine and guanine as the nucleobase, nucleoside and deoxynucleoside forms in human urine by high-performance liquid chromatography-electrospray tandem mass spectrometry. Nucleic Acids Res. 2002 Jan 15;30(2):E7. 11788733 Spiegel AM: Signal transduction by guanine nucleotide binding proteins. Mol Cell Endocrinol. 1987 Jan;49(1):1-16. 2435586 Fain JN, Wallace MA, Wojcikiewicz RJ: Evidence for involvement of guanine nucleotide-binding regulatory proteins in the activation of phospholipases by hormones. FASEB J. 1988 Jul;2(10):2569-74. 2838362 Xiao, Xuhua; Ma, Weiyong. One-pot synthesis of guanine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp. http://hmdb.ca/system/metabolites/msds/000/000/092/original/HMDB00132.pdf?1358894467 Queuine tRNA-ribosyltransferase P0A847 TGT_ECOLI tgt http://ecmdb.ca/proteins/P0A847.xml Hypoxanthine phosphoribosyltransferase P0A9M2 HPRT_ECOLI hpt http://ecmdb.ca/proteins/P0A9M2.xml Xanthine phosphoribosyltransferase P0A9M5 XGPT_ECOLI gpt http://ecmdb.ca/proteins/P0A9M5.xml Purine nucleoside phosphorylase deoD-type P0ABP8 DEOD_ECOLI deoD http://ecmdb.ca/proteins/P0ABP8.xml Pyrimidine-specific ribonucleoside hydrolase rihB P33022 RIHB_ECOLI rihB http://ecmdb.ca/proteins/P33022.xml Adenine phosphoribosyltransferase P69503 APT_ECOLI apt http://ecmdb.ca/proteins/P69503.xml Guanine deaminase P76641 GUAD_ECOLI guaD http://ecmdb.ca/proteins/P76641.xml Xanthosine phosphorylase P45563 XAPA_ECOLI xapA http://ecmdb.ca/proteins/P45563.xml Xanthine permease XanP P0AGM9 XANP_ECOLI xanP http://ecmdb.ca/proteins/P0AGM9.xml Nucleoside-specific channel-forming protein tsx P0A927 TSX_ECOLI tsx http://ecmdb.ca/proteins/P0A927.xml Guanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + Pyrophosphate R01229 GUANPRIBOSYLTRAN-RXN Deoxyguanosine + Phosphate <> Deoxyribose 1-phosphate + Guanine R01969 Guanosine + Phosphate <> Guanine + Ribose-1-phosphate RXN0-5199 Guanine + Hydrogen ion + Water > Ammonium + Xanthine Guanosine monophosphate + Pyrophosphate <> Guanine + Phosphoribosyl pyrophosphate R01229 Guanine + Water <> Xanthine + Ammonia R01676 GUANINE-DEAMINASE-RXN Guanosine + Water <> Guanine + Ribose R01677 Guanosine + Phosphate <> Guanine + alpha-D-Ribose 1-phosphate R02147 Deoxyguanosine + Phosphate <> deoxyribose-1-phosphate + Guanine DEOXYGUANPHOSPHOR-RXN Water + Guanine > Ammonia + Xanthine GUANINE-DEAMINASE-RXN Guanine(34) in tRNA + Queuine > queuosine(34) in tRNA + Guanine Guanine(34) in tRNA + 7-Aminomethyl-7-carbaguanine > 7-aminomethyl-7-carbaguanine(34) in tRNA + Guanine Queuine + 7-Aminomethyl-7-carbaguanine <> Guanine R03789 7-Aminomethyl-7-carbaguanine + tRNA guanine > 7-aminomethyl-7-deazaguanosine34 in tRNA + Guanine PW_R005183 Guanosine + Phosphate > Ribose-1-phosphate + Guanine PW_R006058 Guanine + Phosphoribosyl pyrophosphate > Pyrophosphate + Guanosine monophosphate PW_R006059 Guanine + Water <> Xanthine + Ammonia Guanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + Pyrophosphate Queuine + 7 7-Aminomethyl-7-carbaguanine <> Guanine Guanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + Pyrophosphate Queuine + 7 7-Aminomethyl-7-carbaguanine <> Guanine Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 188.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 752000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Shake flask and filter culture 3.13 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 12520 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Shake flask and filter culture 3.13 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 12520 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 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 65.1 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 260400 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