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Record Information
Version1.0
Creation Date2016-09-30 22:26:35 UTC
Update Date2020-06-04 20:45:06 UTC
MCDB ID BMDB0000195
Secondary Accession Numbers
  • BMDB00195
Metabolite Identification
Common NameInosine
DescriptionInosine, 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.
Structure
Thumb
Synonyms
ValueSource
9-beta-D-Ribofuranosyl-9H-purin-6-olChEBI
9-beta-D-RibofuranosylhypoxanthineChEBI
Hypoxanthine D-ribosideChEBI
HypoxanthosineChEBI
iChEBI
InosinChEBI
InosinaChEBI
InosinumChEBI
InotinKegg
9-b-D-Ribofuranosyl-9H-purin-6-olGenerator
9-Β-D-ribofuranosyl-9H-purin-6-olGenerator
9-b-D-RibofuranosylhypoxanthineGenerator
9-Β-D-ribofuranosylhypoxanthineGenerator
(-)-InosineHMDB
1,9-Dihydro-9-b-D-ribofuranosyl-6H-purin-6-oneHMDB
1,9-Dihydro-9-beta-D-ribofuranosyl-6H-purin-6-oneHMDB
1,9-Dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-oneHMDB
9-b-D-Ribofuranosyl-hypoxanthineHMDB
9-beta-D-Ribofuranosyl-hypoxanthineHMDB
9-beta-delta-Ribofuranosyl-hypoxanthineHMDB
9-beta-delta-RibofuranosylhypoxanthineHMDB
9beta-D-RibofuranosylhypoxanthineHMDB
9beta-delta-RibofuranosylhypoxanthineHMDB
AtorelHMDB
beta-D-Ribofuranoside hypoxanthine-9HMDB
beta-delta-Ribofuranoside hypoxanthine-9HMDB
beta-InosineHMDB
HXRHMDB
Hypoxanthine 9-beta-D-ribofuranosideHMDB
Hypoxanthine 9-beta-delta-ribofuranosideHMDB
Hypoxanthine nucleosideHMDB
Hypoxanthine ribonucleosideHMDB
Hypoxanthine ribosideHMDB
Hypoxanthine-9 beta-D-ribofuranosideHMDB
Hypoxanthine-9 beta-delta-ribofuranosideHMDB
Hypoxanthine-9-beta-D-ribofuranosideHMDB
Hypoxanthine-9-beta-delta-ribofuranosideHMDB
Hypoxanthine-9-D-ribofuranosideHMDB
Hypoxanthine-9-delta-ribofuranosideHMDB
Hypoxanthine-riboseHMDB
Indole-3-carboxaldehydeHMDB
InoHMDB
InosieHMDB
Iso-prinosineHMDB
OxiaminHMDB
Panholic-LHMDB
Pantholic-LHMDB
RibonosineHMDB
SelferHMDB
TrophicardylHMDB
Chemical FormulaC10H12N4O5
Average Molecular Weight268.2261
Monoisotopic Molecular Weight268.080769514
IUPAC Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one
Traditional Nameinosine
CAS Registry Number58-63-9
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(O)N=CN=C12
InChI Identifier
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
InChI KeyUGQMRVRMYYASKQ-KQYNXXCUSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Pentose monosaccharide
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Pyrimidone
  • Pyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Vinylogous amide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point218 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility15.8 mg/mLYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP-2.1HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-1.2ALOGPS
logP-2ChemAxon
logS-0.99ALOGPS
pKa (Strongest Acidic)6.94ChemAxon
pKa (Strongest Basic)2.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.2 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity60.9 m³·mol⁻¹ChemAxon
Polarizability24.6 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.97 +/- 0.42 uM details
Detected and Quantified1 uM details
HMDB IDHMDB0000195
DrugBank IDDB04335
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011802
KNApSAcK IDC00019692
Chemspider ID5799
KEGG Compound IDC00294
BioCyc IDINOSINE
BiGG ID34525
Wikipedia LinkInosine
METLIN ID84
PubChem Compound6021
PDB IDNot Available
ChEBI ID17596
References
Synthesis ReferenceShi, Qingshan; Qiu, Yutang; Li, Liangqiu; Lin, Xiaoping. New inosine-producing bacterium and method for producing inosine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52. [PubMed:1897275 ]
  2. 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. [PubMed:11242448 ]