Compound: inosine
SMILES: O=c1nc[nH]c2c1ncn2[C@@H]3O[C@H](CO)[C@H]([C@H]3O)O
InChIKey: UGQMRVRMYYASKQ-KQYNXXCUSA-N
Synonyms: inosine, 58-63-9, Hypoxanthosine, Ribonosine, Atorel, Oxiamin, Hypoxanthine riboside, Trophicardyl, Selfer, 9-beta-D-Ribofuranosylhypoxanthine, Hypoxanthine D-riboside, Hypoxanthine ribonucleoside, Hypoxanthine nucleoside, Inosina, Inosinum, Inotin, INO 495, DTXSID2045993, 5A614L51CT, NSC-20262, 9-beta-D-ribofuranosyl-9H-purin-6-ol, DTXCID0025993, CHEBI:17596, 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one, 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one, 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one, 9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1H-purin-6-one, 9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-6,9-dihydro-1H-purin-6-one, 9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-6,9-dihydro-3H-purin-6-one, RefChem:791048, D06BB05, G01AX02, S01XA10, 9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-3H-purin-6-one, 200-390-4, Panholic-L, Pantholic-L, (-)-Inosine, Inosie, iso-prinosine, Inosine [INN:JAN], Inosinum [INN-Latin], Inosina [INN-Spanish], hypoxanthine-ribose, INO, MFCD00066770, Hypoxanthine, 9-beta-D-ribofuranosyl-, Inosin, AI3-52241, HXR, Hypoxanthine-9-beta-D-ribofuranoside, NSC 20262, beta-D-Ribofuranoside, hypoxanthine-9, Hypoxanthine 9-beta-D-ribofuranoside, MLS000028518, 9.beta.-D-Ribofuranosylhypoxanthine, 1,9-Dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one, 9-.beta.-D-Ribofuranosylhypoxanthine, SMR000058316, 9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one, .beta.-Inosine, 9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3H-purin-6(9H)-one, CAS-58-63-9, SR-01000721862, EINECS 200-390-4, Carnine, Catacol, Hypoxanthosine;, NSC20262, Trophicardyl;, UNII-5A614L51CT, Oxiamine;, 3h-inosine, D-Inosine, Inosie;, 2ada, 2fqw, .beta.-D-Ribofuranoside, hypoxanthine-9, NCGC00095787-01, Adenosine Imp. G (EP); Inosine; Didanosine Imp. B (Ph. Int.); 9-beta-D-Ribofuranosyl-1,9-dihydro-6H-purin-6-one; Adenosine Impurity G; Didanosine Impurity B, Hypoxanthine, 9-.beta.-D-ribofuranosyl-, Inotin (TN), Hypoxanthine riboside;, CID 5274258, Inosine (JAN/INN), 1a4m, Inosine (8CI,9CI), INOSINE [INN], INOSINE [JAN], INOSINE [MI], INOSINE [MART.], Opera_ID_1628, INOSINE [WHO-DD], INOSINE [WHO-IP], bmse000098, bmse000888, bmse000978, cid_6021, CHEMBL1556, SCHEMBL15804, KBioGR_002560, KBioSS_002569, INOSINE [USP IMPURITY], GTPL4554, orb3025449, SCHEMBL1682742, SCHEMBL3365586, SCHEMBL6933022, 9-b-D-Ribofuranosylhypoxanthine, Hypoxanthine-9-D-ribofuranoside, Inosine, >=99% (HPLC), SCHEMBL18653532, 9beta-D-Ribofuranosylhypoxanthine, BDBM22104, KBio2_002560, KBio2_005128, KBio2_007696, KBio3_003038, 9-|A-D-Ribofuranosylhypoxanthine, 9-b-D-ribofuranosyl-Hypoxanthine, MSK6812, 9-|_-D-Ribofuranosylhypoxanthine, cMAP_000084, HMS2235I17, Hypoxanthine-9-delta-ribofuranoside, 9-beta-D-Ribofuranosyl-1,9-dihydro-6H-purin-6-one (Inosine), 9-beta-D-ribofuranosyl-Hypoxanthine, HY-N0092, 9beta-delta-Ribofuranosylhypoxanthine, Tox21_111522, BDBM50366815, beta-D-Ribofuranoside hypoxanthine-9, EBC-44242, EBC-47437, hypoxanthine-9 beta-D-Ribofuranoside, s2442, 9-beta-delta-Ribofuranosylhypoxanthine, (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-hydroxypurin-9-yl)oxolane-3,4-diol, AKOS015969695, AKOS015995607, AKOS024462561, Atorel; HXR; Hypoxanthine D-riboside, Tox21_111522_1, 9-beta-delta-ribofuranosyl-Hypoxanthine, CCG-267127, CS-5845, DB04335, DIDANOSINE IMPURITY B [WHO-IP], NI06297, 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-3H-purin-6-one, beta-delta-Ribofuranoside hypoxanthine-9, Hypoxanthine 9-beta-delta-ribofuranoside, hypoxanthine-9 beta-delta-Ribofuranoside, Hypoxanthine-9-beta-delta-ribofuranoside, SMP1_000165, NCGC00095787-05, NCGC00095787-06, NCGC00096119-02, NCGC00096119-03, AS-11754, BP-51105, SY005000, 9-(beta-D-ribofuranosyl)-9H-purin-6-ol, ADENOSINE IMPURITY G [EP IMPURITY], DB-029916, DIDANOSINE IMPURITY B [EP IMPURITY], I0037, NS00010210, C00294, D00054, EN300-310328, 1,9-dihydro-9-b-D-ribofuranosyl-6H-Purin-6-one, Q422564, SR-01000721862-2, SR-01000721862-3, AC89F8E4-FD89-45EE-8B41-94DFC07AB42F, BRD-K79612754-001-19-1, BRD-K79612754-001-21-7, 1,9-Dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one, 6H-Purin-6-one, 1,9-dihydro-9-beta-D-ribofuranosyl-, Z2681890654, Inosine; Adenosine EP Impurity G; Didanosine EP Impurity B, 9-.BETA.-D-RIBOFURANOSYL-1,9-DIHYDRO-6H-PURIN-6-ONE, 9-.BETA.-D-RIBOFURANOSYL-1,9-DIHYDRO-6H-PURIN-6-ONE [WHO-IP], (2R,3R,4S,5R)-2-(6-hydroxy-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol, (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-hydroxy-9H-purin-9-yl)tetrahydrofuran-3,4-diol, 9-(3,4-DIHYDROXY-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-2-YL)-1,9-DIHYDRO-PURIN-6-ONE, 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-purin-6-one, 478182-32-0, 9-|A-D-Ribofuranosylhypoxanthine; 9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,9-dihydro-6H-purin-6-one, InChI=1/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/s
Theoretical properties:
molecular_formula: C10H12N4O5
molecular_weight: 268.23 g/mol
exact_mass: 268.08076950 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 2
heavy_atom_count: 19
topological_polar_surface_area: 129 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Inosine is a purine nucleoside in which hypoxanthine is attached to ribofuranose via a beta-N9-glycosidic bond. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite. It is a purines D-ribonucleoside and a member of inosines. It is functionally related to a hypoxanthine and a ribofuranose.
chebi: A purine nucleoside in which hypoxanthine is attached to ribofuranose via a β-<em>N</em><small><sup>9</small></sup>-glycosidic bond.
chembl: INOSINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Inosine is a nucleoside that is formed when hypoxanthine is attached to a ribose ring (also known as a ribofuranose) via a β-N9-glycosidic bond. It was discovered in 1965 in analysis of RNA transferase.
Inosine is commonly found in tRNAs and is essential for proper translation of the genetic code in wobble base pairs.

Knowledge of inosine metabolism has led to advances in immunotherapy in recent decades. Inosine monophosphate is oxidised by the enzyme inosine monophosphate dehydrogenase, yielding xanthosine monophosphate, a key precursor in purine metabolism.  Mycophenolate mofetil is an anti-metabolite, anti-proliferative drug that acts as an inhibitor of inosine monophosphate dehydrogenase. It is used in the treatment of a variety of autoimmune diseases including granulomatosis with polyangiitis because the uptake of purine by actively dividing B cells can exceed 8 times that of normal body cells, and, therefore, this set of white cells (which cannot operate purine salvage pathways) is selectively targeted by the purine deficiency resulting from inosine monophosphate dehydrogenase (IMD) inhibition.