We are currently updating the database - data may be missing for the next 10 minutes. We apologize for any inconvenience.

Bovine Metabolome Database



Showing metabocard for Deoxyinosine (BMDB00071)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-08-07 12:12:47
Accession Number BMDB00071
Common Name Deoxyinosine
Description Deoxyinosine is a nucleoside that is formed when hypoxanthine is attached to a deoxyribose ring (also known as a ribofuranose) via a beta-N9-glycosidic bond. Deoxyinosine is found in DNA while Inosine is found in RNA. Inosine is a nucleic acid important for RNA editing. Adenosine deaminase (ADA) catalyzes the conversion of adenosine and deoxyadenosine to inosine and deoxyinosine, respectively. ADA-deficient individuals suffer from severe combined immunodeficiency (SCID) and are unable to produce significant numbers of mature T or B lymphocytes. This occurs as a consequence of the accumulation of ADA substrates or their metabolites. Inosine is also an intermediate in a chain of purine nucleotides reactions required for muscle movements.
Synonyms
  1. 2'-Deoxyinosine
  2. 2deoxy-Inosine
  3. 9-(2-Deoxy-b-D-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one
  4. 9-(2-deoxy-b-D-erythro-pentofuranosyl)-Hypoxanthine
  5. 9-(2-deoxy-beta-D-erythro-pentofuranosyl)-Hypoxanthine
  6. Deoxyinosine
  7. d-Ino
  8. 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one
  9. 9-(2-deoxy-beta-delta-erythro-pentofuranosyl)-Hypoxanthine
  10. delta-Ino
Chemical IUPAC Name 9-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
Chemical Formula C10H12N4O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Nucleosides and Nucleoside conjugates
Class
  • Nucleoside Analogues
Sub Class
  • Deoxy nucleosides
Family
  • Mammalian_Metabolite
Species
  • primary alcohol; secondary alcohol; phenol or hydroxyhetarene; aromatic compound; heterocyclic compound
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 252.227
Monoisotopic Molecular Weight 252.085861
Isomeric SMILES OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CN=C2O
Canonical SMILES OCC1OC(CC1O)N1C=NC2=C1N=CN=C2O
KEGG Compound ID C05512 Link Image
BioCyc ID DEOXYINOSINE Link Image
BiGG ID 45942 Link Image
Wikipedia Link Not Available
METLIN ID 3383 Link Image
PubChem Compound 65058 Link Image
PubChem Substance 3139569 Link Image
ChEBI ID Not Available
CAS Registry Number 890-38-0
InChI Identifier InChI=1/C10H12N4O4/c15-2-6-5(16)1-7(18-6)14-4-13-8-9(14)11-3-12-10(8)17/h3-7,15-16H,1-2H2,(H,11,12,17)/t5-,6+,7+/m0/s1
Synthesis Reference Robins, Morris J.; Basom, Gerald L. Nucleic acid-related compounds. 8. Direct conversion of 2'-deoxyinosine to 9-(2-deoxy-b-D-erythro-pentofuranosyl)-6-chloropurine and selected 6-substituted deoxynucleosides and their evaluation as substrates of adenosin
Melting Point (Experimental) 250 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 32.5 mg/mL [MEYLAN,WM et al. (1996)]; 18.7 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity -1.71 [FORD,H ET AL. (1991)] Source: PhysProp
Predicted LogP/Hydrophobicity -1.62 [Predicted by ALOGPS]; -0.8 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID 1Z39 Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • nucleus
  • Extracellular
Biofluid Location Not Available
Tissue Location
Tissue References
All Tissues
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Purine Metabolism
HMDB Pathways
Name Purine Metabolism
Image Show Link Image
KEGG Pathways
Name Purine Metabolism
Image Show Link Image
SimCell Pathways
Name Purine Metabolism
Image Show Link Image
Graph Show Link Image
SBML Download (XML) Link Image
General References Not Available