Human Metabolome Database Version 3.5

Showing metabocard for Deoxyinosine (HMDB00071)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:51 -0700
HMDB ID HMDB00071
Secondary Accession Numbers None
Metabolite Identification
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.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2'-Deoxyinosine
  2. 2-Deoxy-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. 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one
  7. 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-Hypoxanthine
  8. D-Ino
  9. delta-Ino
  10. Deoxyinosine
Chemical Formula C10H12N4O4
Average Molecular Weight 252.2267
Monoisotopic Molecular Weight 252.085854892
IUPAC Name 9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-ol
Traditional IUPAC Name 9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-ol
CAS Registry Number 890-38-0
SMILES OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CN=C2O
InChI Identifier InChI=1S/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
InChI Key VGONTNSXDCQUGY-RRKCRQDMSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleosides and Analogues
Sub Class Purine 2'-deoxyribonucleosides and Analogues
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • purine 2'-deoxyribonucleoside(ChEBI)
Substituents
  • Hypoxanthine
  • Imidazole
  • Imidazopyrimidine
  • Oxolane
  • Primary Alcohol
  • Purine
  • Pyrimidine
  • Secondary Alcohol
Direct Parent Purine 2'-deoxyribonucleosides and Analogues
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Nucleus
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 250 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -1.71 FORD,H ET AL. (1991)
Predicted Properties
Property Value Source
Water Solubility 18.7 g/L ALOGPS
LogP -1.62 ALOGPS
LogP -0.66 ChemAxon
LogS -1.13 ALOGPS
pKa (strongest acidic) 11.68 ChemAxon
pKa (strongest basic) 0.08 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 113.52 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 58.97 ChemAxon
Polarizability 23.69 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Nucleus
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • All Tissues
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 map00230 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Comment Normal
  • Not Applicable
Urine Detected and Quantified
1.00 (0.00-2.00) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
< 0.1 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected and Quantified 3.2 umol/mmol creatinine Adult (>18 years old) Both Purine Nucleoside Phosphorylase Deficiency
Associated Disorders and Diseases
Disease References
Purine nucleoside phosphorylase deficiency
  • Chantin C, Bonin B, Boulieu R, Bory C: Liquid-chromatographic study of purine metabolism abnormalities in purine nucleoside phosphorylase deficiency. Clin Chem. 1996 Feb;42(2):326-8. Pubmed: 8595732 Link_out
      Associated OMIM IDs
      • 164050 Link_out (Purine nucleoside phosphorylase deficiency )
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB012323
      KNApSAcK ID Not Available
      Chemspider ID 58569 Link_out
      KEGG Compound ID C05512 Link_out
      BioCyc ID DEOXYINOSINE Link_out
      BiGG ID 45942 Link_out
      Wikipedia Link Not Available
      NuGOwiki Link HMDB00071 Link_out
      Metagene Link HMDB00071 Link_out
      METLIN ID 3383 Link_out
      PubChem Compound 65058 Link_out
      PDB ID 2ND Link_out
      ChEBI ID 28997 Link_out
      References
      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
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Cohen A, Doyle D, Martin DW Jr, Ammann AJ: Abnormal purine metabolism and purine overproduction in a patient deficient in purine nucleoside phosphorylase. N Engl J Med. 1976 Dec 23;295(26):1449-54. Pubmed: 825775 Link_out
      2. Kewn S, Hoggard PG, Henry-Mowatt JS, Veal GJ, Sales SD, Barry MG, Back DJ: Intracellular activation of 2',3'-dideoxyinosine and drug interactions in vitro. AIDS Res Hum Retroviruses. 1999 Jun 10;15(9):793-802. Pubmed: 10381167 Link_out
      3. Bemi V, Tazzni N, Banditelli S, Giorgelli F, Pesi R, Turchi G, Mattana A, Sgarrella F, Tozzi MG, Camici M: Deoxyadenosine metabolism in a human colon-carcinoma cell line (LoVo) in relation to its cytotoxic effect in combination with deoxycoformycin. Int J Cancer. 1998 Mar 2;75(5):713-20. Pubmed: 9495239 Link_out
      4. Chantin C, Bonin B, Boulieu R, Bory C: Liquid-chromatographic study of purine metabolism abnormalities in purine nucleoside phosphorylase deficiency. Clin Chem. 1996 Feb;42(2):326-8. Pubmed: 8595732 Link_out
      5. Ablett E, Pedley J, Dannoy PA, Sturm RA, Parsons PG: UVB-specific regulation of gene expression in human melanocytic cells: cell cycle effects and implication in the generation of melanoma. Mutat Res. 1998 Nov 9;422(1):31-41. Pubmed: 9920426 Link_out
      6. Bazar LS, Collier GB, Vanek PG, Siles BA, Kow YW, Doetsch PW, Cunningham RP, Chirikjian JG: Mutation identification DNA analysis system (MIDAS) for detection of known mutations. Electrophoresis. 1999 Jun;20(6):1141-8. Pubmed: 10380753 Link_out
      7. Sjoberg AH, Wang L, Eriksson S: Substrate specificity of human recombinant mitochondrial deoxyguanosine kinase with cytostatic and antiviral purine and pyrimidine analogs. Mol Pharmacol. 1998 Feb;53(2):270-3. Pubmed: 9463485 Link_out

      Enzymes
      Name: Adenosine deaminase
      Reactions:
      Deoxyadenosine + Water unknown Deoxyinosine + Ammonia details
      Gene Name: ADA
      Uniprot ID: P00813 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Purine nucleoside phosphorylase
      Reactions:
      Deoxyinosine + Phosphoric acid unknown Hypoxanthine + Deoxyribose 1-phosphate details
      Gene Name: PNP
      Uniprot ID: P00491 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA