1.0 2016-09-30 22:18:58 UTC 2020-06-04 20:45:19 UTC BMDB0000050 BMDB00050 Adenosine Adenosine, also known as adenocard or ade-rib, 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. Adenosine is a drug which is used as an initial treatment for the termination of paroxysmal supraventricular tachycardia (pvst), including that associated with accessory bypass tracts, and is a drug of choice for terminating stable, narrow-complex supraventricular tachycardias (svt). also used as an adjunct to thallous chloride ti 201 myocardial perfusion scintigraphy (thallium stress test) in patients who are unable to exercise adequately, as well as an adjunct to vagal maneuvers and clinical assessment to establish a specific diagnosis of undefined, stable, narrow-complex svt. Adenosine exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Adenosine exists in all living species, ranging from bacteria to humans. Adenosine is a potentially toxic compound. (2R,3R,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol 6-Amino-9-beta-D-ribofuranosyl-9H-purine 9-beta-D-Ribofuranosidoadenine 9-beta-D-Ribofuranosyl-9H-purin-6-amine Ade-rib Adenine deoxyribonucleoside Adenocard Adenocor Adenoscan Adenosin Adenyldeoxyriboside Ado beta-D-Adenosine Deoxyadenosine Desoxyadenosine 6-Amino-9-b-D-ribofuranosyl-9H-purine 6-Amino-9-β-D-ribofuranosyl-9H-purine 9-b-D-Ribofuranosidoadenine 9-Β-D-ribofuranosidoadenine 9-b-D-Ribofuranosyl-9H-purin-6-amine 9-Β-D-ribofuranosyl-9H-purin-6-amine b-D-Adenosine Β-D-adenosine 1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-D-ribofuranose 1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-delta-ribofuranose 6-Amino-9beta-D-ribofuranosyl-9H-purine 6-Amino-9beta-delta-ribofuranosyl-9H-purine 9-beta-D-Arabinofuranosyladenine 9-beta-D-Ribofuranosyladenine 9-beta-delta-Arabinofuranosyladenine 9-beta-delta-Ribofuranosidoadenine 9-beta-delta-Ribofuranosyl-9H-purin-6-amine 9-beta-delta-Ribofuranosyladenine 9beta-D-Ribofuranosyl-9H-purin-6-amine 9beta-D-Ribofuranosyladenine 9beta-delta-Ribofuranosyl-9H-purin-6-amine 9beta-delta-Ribofuranosyladenine Adenine nucleoside Adenine riboside Adenine-9beta-D-ribofuranoside Adenine-9beta-delta-ribofuranoside beta-Adenosine beta-delta-Adenosine Boniton Myocol Nucleocardyl Sandesin C10H13N5O4 267.2413 267.096753929 (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol adenosine 58-61-7 NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1 InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1 OIRDTQYFTABQOQ-KQYNXXCUSA-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 6-aminopurines Aminopyrimidines and derivatives Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Imidolactams N-substituted imidazoles Organopnictogen compounds Oxacyclic compounds Pentoses Primary alcohols Primary amines Secondary alcohols Tetrahydrofurans 6-aminopurine Alcohol Amine Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Imidazole Imidazopyrimidine Imidolactam 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 Primary amine Purine Purine nucleoside Pyrimidine Secondary alcohol Tetrahydrofuran Aromatic heteropolycyclic compounds Ribonucleosides adenosines Solid melting_point 235.5 °C water_solubility 37 mg/mL Human Metabolome Project logp -1.05 HANSCH,C ET AL. (1995) logp -1.21 ALOGPS logs -1.28 ALOGPS logp -2.1 ChemAxon pka_strongest_acidic 12.45 ChemAxon pka_strongest_basic 3.92 ChemAxon iupac (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol ChemAxon average_mass 267.2413 ChemAxon mono_mass 267.096753929 ChemAxon smiles NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1 ChemAxon formula C10H13N5O4 ChemAxon inchi InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1 ChemAxon inchikey OIRDTQYFTABQOQ-KQYNXXCUSA-N ChemAxon polar_surface_area 139.54 ChemAxon refractivity 63.2 ChemAxon polarizability 25.28 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 8 ChemAxon donor_count 4 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 Betaine Metabolism SMP0087182 Intracellular Signalling Through Adenosine Receptor A2a and Adenosine SMP0108174 Intracellular Signalling Through Adenosine Receptor A2b and Adenosine SMP0108178 Methionine Metabolism SMP0087249 Purine Metabolism SMP0087239 Selenoamino Acid Metabolism SMP0087161 Specdb::MsMs 81 Specdb::MsMs 82 Specdb::MsMs 83 Specdb::MsMs 2654 Specdb::MsMs 2655 Specdb::MsMs 2656 Specdb::MsMs 2657 Specdb::MsMs 2658 Specdb::MsMs 2659 Specdb::MsMs 2660 Specdb::MsMs 2661 Specdb::MsMs 2662 Specdb::MsMs 2663 Specdb::MsMs 2664 Specdb::MsMs 2665 Specdb::MsMs 2666 Specdb::MsMs 2667 Specdb::MsMs 2668 Specdb::MsMs 2669 Specdb::MsMs 2674 Specdb::MsMs 2675 Specdb::MsMs 2676 Specdb::MsMs 2677 Specdb::MsMs 179655 Specdb::MsMs 179656 Specdb::NmrTwoD 943 Specdb::NmrTwoD 1111 Specdb::NmrOneD 1053 Specdb::NmrOneD 1131 Specdb::NmrOneD 141970 Specdb::NmrOneD 141971 Specdb::NmrOneD 141972 Specdb::NmrOneD 141973 Specdb::NmrOneD 141974 Specdb::NmrOneD 141975 Specdb::NmrOneD 141976 Specdb::NmrOneD 141977 Specdb::NmrOneD 141978 Specdb::NmrOneD 141979 Specdb::NmrOneD 141980 Specdb::NmrOneD 141981 Specdb::NmrOneD 141982 Specdb::NmrOneD 141983 Specdb::NmrOneD 141984 Specdb::NmrOneD 141985 Specdb::NmrOneD 141986 Specdb::NmrOneD 141987 Specdb::NmrOneD 141988 Specdb::NmrOneD 141989 Specdb::NmrOneD 166516 Specdb::CMs 297 Specdb::CMs 298 Specdb::CMs 299 Specdb::CMs 300 Specdb::CMs 2034 Specdb::CMs 2087 Specdb::CMs 3195 Specdb::CMs 30173 Specdb::CMs 30263 Specdb::CMs 30473 Specdb::CMs 30822 Specdb::CMs 30969 Specdb::CMs 30970 Specdb::CMs 37266 Specdb::CMs 164828 Specdb::CMs 1048288 Specdb::CMs 1048290 Specdb::CMs 1048291 Specdb::CMs 1048293 Specdb::CMs 1048295 Specdb::CMs 1048297 Specdb::CMs 1048299 Specdb::CMs 1048301 Specdb::CMs 1048302 Specdb::CMs 1048304 All Tissues 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 Colostrum Detected by NMR Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15. 25637742 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 Mammary Gland 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 Mammary Gland 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 Milk Commercial, conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 Milk Detected but not quantified in conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 Milk 1.4 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 Muscle Detected by NMR Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15. 25637742 Muscle Detected by NMR in beef muscle (longissimus dorsi). S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404 doi: 10.1007/s11306-010-0206-y 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 Testis 150 +/- 114 nmol/g of tissue By NMR Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 54923 DB00640 60961 FDB003554 C00212 16335 C00007444 ADENOSINE 34273 Adenosine 86 Liao, Ben-ren; Yuan, Zhen-wen. Synthesis of adenosine from inosine. Huaxue Shiji (2006), 28(10), 633-634. 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 Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 BMDBP00698 Purine nucleoside phosphorylase P55859 PNP Enzyme BMDBP00837 Adenosylhomocysteinase A5PKK6 AHCYL1 Enzyme BMDBP00838 Adenosylhomocysteinase 3 A6QLP2 AHCYL2 Enzyme BMDBP00839 Adenosine deaminase P56658 ADA Enzyme BMDBP01293 Adenosylhomocysteinase Q3MHL4 AHCY Enzyme BMDBP02088 Adenosine receptor A3 Q0VC81 ADORA3 Enzyme BMDBP02089 Adenosine receptor A2b Q1LZD0 ADORA2B Enzyme BMDBP02090 Cleavage and polyadenylation specificity factor subunit 5 Q3ZCA2 NUDT21 Enzyme BMDBP02091 Adenosine receptor A1 P28190 ADORA1 Enzyme