1.0 2016-09-30 22:20:00 UTC 2020-06-04 20:45:00 UTC BMDB0000133 BMDB00133 Guanosine Guanosine, also known as G or 2-amino-inosine, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Guanosine exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Guanosine exists in all living species, ranging from bacteria to humans. In cattle, guanosine is involved in a couple of metabolic pathways, which include the intracellular signalling through adenosine receptor A2A and adenosine pathway and the intracellular signalling through adenosine receptor A2B and adenosine pathway. Guanosine is a potentially toxic compound. 2(3H)-Imino-9-beta-D-ribofuranosyl-9H-purin-6(1H)-one 2-Amino-1,9-dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one 2-Amino-9-beta-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one 9-beta-D-Ribofuranosyl-guanine G Guanine riboside Guanine-9-beta-D-ribofuranoside Guanosin Guo 2(3H)-Imino-9-b-D-ribofuranosyl-9H-purin-6(1H)-one 2(3H)-Imino-9-β-D-ribofuranosyl-9H-purin-6(1H)-one 2-Amino-1,9-dihydro-9-b-D-ribofuranosyl-6H-purin-6-one 2-Amino-1,9-dihydro-9-β-D-ribofuranosyl-6H-purin-6-one 2-Amino-9-b-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one 2-Amino-9-β-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one 9-b-D-Ribofuranosyl-guanine 9-Β-D-ribofuranosyl-guanine Guanine-9-b-D-ribofuranoside Guanine-9-β-D-ribofuranoside 2-Amino-1,9-dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one 2-Amino-inosine 9-beta-delta-Ribofuranosyl-guanine b-D-Ribofuranoside guanine-9 beta-delta-Ribofuranoside guanine-9 Ribonucleoside Vernine C10H13N5O5 283.2407 283.091668551 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one guanosine 118-00-3 NC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1 InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1 NYHBQMYGNKIUIF-UUOKFMHZSA-N belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Organic compounds Nucleosides, nucleotides, and analogues Purine nucleosides Purine nucleosides Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hydroxypyrimidines N-substituted imidazoles Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Pentoses Primary alcohols Purines and purine derivatives Secondary alcohols Tetrahydrofurans Alcohol Aromatic heteropolycyclic compound Azacycle Azole Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydroxypyrimidine Imidazole Imidazopyrimidine Monosaccharide N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose monosaccharide Primary alcohol Purine Purine nucleoside Pyrimidine Secondary alcohol Tetrahydrofuran Aromatic heteropolycyclic compounds Ribonucleosides guanosines Solid melting_point 239 °C water_solubility 0.7 mg/mL at 18 °C logp -1.9 SANGSTER (1993) logp -2.06 ALOGPS logs -1.27 ALOGPS logp -2.7 ChemAxon pka_strongest_acidic 10.16 ChemAxon pka_strongest_basic 0.45 ChemAxon iupac 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one ChemAxon average_mass 283.2407 ChemAxon mono_mass 283.091668551 ChemAxon smiles NC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1 ChemAxon formula C10H13N5O5 ChemAxon inchi InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1 ChemAxon inchikey NYHBQMYGNKIUIF-UUOKFMHZSA-N ChemAxon polar_surface_area 155.22 ChemAxon refractivity 64.62 ChemAxon polarizability 26.03 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 8 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Purine Metabolism SMP0087239 Specdb::EiMs 1973 Specdb::NmrTwoD 965 Specdb::NmrTwoD 1161 Specdb::MsMs 203 Specdb::MsMs 204 Specdb::MsMs 205 Specdb::MsMs 3006 Specdb::MsMs 3007 Specdb::MsMs 3008 Specdb::MsMs 3009 Specdb::MsMs 3010 Specdb::MsMs 3011 Specdb::MsMs 3012 Specdb::MsMs 3013 Specdb::MsMs 3014 Specdb::MsMs 3015 Specdb::MsMs 3016 Specdb::MsMs 3017 Specdb::MsMs 3018 Specdb::MsMs 3019 Specdb::MsMs 3020 Specdb::MsMs 3021 Specdb::MsMs 3022 Specdb::MsMs 3023 Specdb::MsMs 3024 Specdb::MsMs 3025 Specdb::MsMs 3026 Specdb::MsMs 3027 Specdb::NmrOneD 1103 Specdb::NmrOneD 1161 Specdb::NmrOneD 142450 Specdb::NmrOneD 142451 Specdb::NmrOneD 142452 Specdb::NmrOneD 142453 Specdb::NmrOneD 142454 Specdb::NmrOneD 142455 Specdb::NmrOneD 142456 Specdb::NmrOneD 142457 Specdb::NmrOneD 142458 Specdb::NmrOneD 142459 Specdb::NmrOneD 142460 Specdb::NmrOneD 142461 Specdb::NmrOneD 142462 Specdb::NmrOneD 142463 Specdb::NmrOneD 142464 Specdb::NmrOneD 142465 Specdb::NmrOneD 142466 Specdb::NmrOneD 142467 Specdb::NmrOneD 142468 Specdb::NmrOneD 142469 Specdb::NmrOneD 166526 Specdb::NmrOneD 166605 Specdb::CMs 356 Specdb::CMs 357 Specdb::CMs 358 Specdb::CMs 359 Specdb::CMs 2710 Specdb::CMs 30191 Specdb::CMs 30564 Specdb::CMs 30873 Specdb::CMs 30874 Specdb::CMs 37313 Specdb::CMs 131331 Specdb::CMs 139065 Specdb::CMs 1051195 Specdb::CMs 1051196 Specdb::CMs 1051197 Specdb::CMs 1051199 Specdb::CMs 1051201 Specdb::CMs 1051203 Specdb::CMs 1051205 Specdb::CMs 1051207 Specdb::CMs 1051209 Specdb::CMs 1051211 Specdb::CMs 1051213 Specdb::CMs 1051215 Specdb::CMs 1051217 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Milk 0.830 +/- 0.320 uM Raw milk Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52. 1897275 Milk 0.8 uM Raw milk Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68. 11242448 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 6802 C00387 6544 DB02857 16750 C00019679 GUANOSINE Guanosine FDB003632 51567 87 Tang, Shengrong; Huang, Weihong; Hou, Zuorong. Process of guanosine production by fermentation. Gongye Weishengwu (1998), 28(4), 11-16. Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52. 1897275 Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68. 11242448 Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241 BMDBP00149 Cytosolic purine 5'-nucleotidase O46411 NT5C2 Enzyme BMDBP00159 5'-nucleotidase Q05927 NT5E Enzyme BMDBP00698 Purine nucleoside phosphorylase P55859 PNP Enzyme BMDBP01085 DNA-directed RNA polymerase subunit beta A6QLS0 POLR1B Enzyme BMDBP01086 Ribonucleoside-diphosphate reductase Q32LP1 RRM1 Enzyme BMDBP01087 DNA-directed RNA polymerase subunit beta A5PJW8 POLR2B Enzyme BMDBP02547 RpB2 B2WTN5 rpB2 Enzyme