1.0 2016-09-30 22:26:35 UTC 2020-06-04 20:45:06 UTC BMDB0000195 BMDB00195 Inosine Inosine, also known as hypoxanthosine or panholic-L, 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. Inosine exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Inosine exists in all living species, ranging from bacteria to humans. Inosine is a potentially toxic compound. 9-beta-D-Ribofuranosyl-9H-purin-6-ol 9-beta-D-Ribofuranosylhypoxanthine Hypoxanthine D-riboside Hypoxanthosine i Inosin Inosina Inosinum Inotin 9-b-D-Ribofuranosyl-9H-purin-6-ol 9-Β-D-ribofuranosyl-9H-purin-6-ol 9-b-D-Ribofuranosylhypoxanthine 9-Β-D-ribofuranosylhypoxanthine (-)-Inosine 1,9-Dihydro-9-b-D-ribofuranosyl-6H-purin-6-one 1,9-Dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one 1,9-Dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one 9-b-D-Ribofuranosyl-hypoxanthine 9-beta-D-Ribofuranosyl-hypoxanthine 9-beta-delta-Ribofuranosyl-hypoxanthine 9-beta-delta-Ribofuranosylhypoxanthine 9beta-D-Ribofuranosylhypoxanthine 9beta-delta-Ribofuranosylhypoxanthine Atorel beta-D-Ribofuranoside hypoxanthine-9 beta-delta-Ribofuranoside hypoxanthine-9 beta-Inosine HXR Hypoxanthine 9-beta-D-ribofuranoside Hypoxanthine 9-beta-delta-ribofuranoside Hypoxanthine nucleoside Hypoxanthine ribonucleoside Hypoxanthine riboside Hypoxanthine-9 beta-D-ribofuranoside Hypoxanthine-9 beta-delta-ribofuranoside Hypoxanthine-9-beta-D-ribofuranoside Hypoxanthine-9-beta-delta-ribofuranoside Hypoxanthine-9-D-ribofuranoside Hypoxanthine-9-delta-ribofuranoside Hypoxanthine-ribose Indole-3-carboxaldehyde Ino Inosie Iso-prinosine Oxiamin Panholic-L Pantholic-L Ribonosine Selfer Trophicardyl C10H12N4O5 268.2261 268.080769514 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one inosine 58-63-9 OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(O)N=CN=C12 InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1 UGQMRVRMYYASKQ-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-oxopurines Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hypoxanthines N-substituted imidazoles Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Pentoses Primary alcohols Pyrimidones Secondary alcohols Tetrahydrofurans Vinylogous amides 6-oxopurine Alcohol Aromatic heteropolycyclic compound Azacycle Azole Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hypoxanthine Imidazole Imidazopyrimidine Monosaccharide N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose monosaccharide Primary alcohol Purine Purine nucleoside Purinone Pyrimidine Pyrimidone Secondary alcohol Tetrahydrofuran Vinylogous amide Aromatic heteropolycyclic compounds inosines Solid melting_point 218 °C water_solubility 15.8 mg/mL YALKOWSKY,SH & DANNENFELSER,RM (1992) logp -2.1 HANSCH,C ET AL. (1995) logp -2 ChemAxon pka_strongest_acidic 6.94 ChemAxon pka_strongest_basic 2.74 ChemAxon iupac 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one ChemAxon average_mass 268.2261 ChemAxon mono_mass 268.080769514 ChemAxon smiles OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(O)N=CN=C12 ChemAxon formula C10H12N4O5 ChemAxon inchi InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1 ChemAxon inchikey UGQMRVRMYYASKQ-KQYNXXCUSA-N ChemAxon polar_surface_area 129.2 ChemAxon refractivity 60.9 ChemAxon polarizability 24.6 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 Purine Metabolism SMP0087239 Specdb::NmrTwoD 992 Specdb::NmrTwoD 1200 Specdb::NmrOneD 1174 Specdb::NmrOneD 4906 Specdb::NmrOneD 142810 Specdb::NmrOneD 142811 Specdb::NmrOneD 142812 Specdb::NmrOneD 142813 Specdb::NmrOneD 142814 Specdb::NmrOneD 142815 Specdb::NmrOneD 142816 Specdb::NmrOneD 142817 Specdb::NmrOneD 142818 Specdb::NmrOneD 142819 Specdb::NmrOneD 142820 Specdb::NmrOneD 142821 Specdb::NmrOneD 142822 Specdb::NmrOneD 142823 Specdb::NmrOneD 142824 Specdb::NmrOneD 142825 Specdb::NmrOneD 142826 Specdb::NmrOneD 142827 Specdb::NmrOneD 142828 Specdb::NmrOneD 142829 Specdb::MsMs 316 Specdb::MsMs 317 Specdb::MsMs 318 Specdb::MsMs 3543 Specdb::MsMs 3544 Specdb::MsMs 3545 Specdb::MsMs 3546 Specdb::MsMs 3547 Specdb::MsMs 3548 Specdb::MsMs 3549 Specdb::MsMs 3550 Specdb::MsMs 3551 Specdb::MsMs 3552 Specdb::MsMs 3553 Specdb::MsMs 3554 Specdb::MsMs 3555 Specdb::MsMs 3556 Specdb::MsMs 3557 Specdb::MsMs 3558 Specdb::MsMs 3559 Specdb::MsMs 3560 Specdb::MsMs 3561 Specdb::MsMs 3562 Specdb::MsMs 3563 Specdb::MsMs 3566 Specdb::CMs 448 Specdb::CMs 449 Specdb::CMs 2029 Specdb::CMs 22590 Specdb::CMs 30576 Specdb::CMs 30880 Specdb::CMs 31063 Specdb::CMs 37351 Specdb::CMs 163703 Specdb::CMs 1053958 Specdb::CMs 1053960 Specdb::CMs 1053962 Specdb::CMs 1053964 Specdb::CMs 1053965 Specdb::CMs 1053967 Specdb::CMs 1053969 Specdb::CMs 1053971 Specdb::CMs 1053973 Specdb::CMs 1053975 Specdb::CMs 1053977 Specdb::CMs 1053979 Specdb::CMs 1053981 Specdb::CMs 1053983 Specdb::CMs 1053985 Specdb::CMs 1053986 Brain 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 Erythrocyte 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 Fibroblasts 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 Intestine 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 Kidney 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 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 Liver 833 +/- 140 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 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 0.970 +/- 0.420 uM Raw milk Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52. 1897275 Milk 1 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 301.14 +/- 26.11 uM Detected by NMR in Australian commercial beef sirloin. Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t. 20831251 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 Muscle 356.78 +/- 41.47 uM Detected by NMR in US commercial beef sirloin Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t. 20831251 Muscle 395.56 +/- 38.59 uM Detected by NMR in New Zealand commercial beef sirloin. Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t. 20831251 Muscle 427.49 +/- 33.47 uM Detected by NMR in Korean commercial beef sirloin. Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t. 20831251 Neuron 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 Pancreas 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 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 Platelet 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 Semen Analysis was performed using GC-MS in Holstein bulls (n = 16). Compound was identified by probable match parameters of the NIST Mass Spectral Search Program Velho ALC, Menezes E, Dinh T, Kaya A, Topper E, Moura AA, Memili E: Metabolomic markers of fertility in bull seminal plasma. PLoS One. 2018 Apr 10;13(4):e0195279. doi: 10.1371/journal.pone.0195279. eCollection 2018. 29634739 Spleen 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 225 +/- 95 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 C00294 FDB011802 DB04335 6021 5799 17596 C00019692 INOSINE Inosine 34525 84 Shi, Qingshan; Qiu, Yutang; Li, Liangqiu; Lin, Xiaoping. New inosine-producing bacterium and method for producing inosine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 6 pp. 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 BMDBP00149 Cytosolic purine 5'-nucleotidase O46411 NT5C2 Enzyme BMDBP00698 Purine nucleoside phosphorylase P55859 PNP Enzyme BMDBP00839 Adenosine deaminase P56658 ADA Enzyme