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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-10-29 17:01:46 UTC
HMDB IDHMDB00071
Secondary Accession NumbersNone
Metabolite Identification
Common NameDeoxyinosine
DescriptionDeoxyinosine 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
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 FormulaC10H12N4O4
Average Molecular Weight252.2267
Monoisotopic Molecular Weight252.085854892
IUPAC Name9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-ol
Traditional Name9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-ol
CAS Registry Number890-38-0
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 KeyVGONTNSXDCQUGY-RRKCRQDMSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleosides and Analogues
Sub ClassPurine 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 ParentPurine 2'-deoxyribonucleosides and Analogues
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point250 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.71FORD,H ET AL. (1991)
Predicted Properties
PropertyValueSource
Water Solubility18.7ALOGPS
logP-1.6ALOGPS
logP-0.66ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)11.68ChemAxon
pKa (Strongest Basic)0.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.52 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.97 m3·mol-1ChemAxon
Polarizability23.69 Å3ChemAxon
Spectra
SpectraGC-MSMS/MSMS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Nucleus
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • All Tissues
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050map00230
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
    • Dame, ZT. et al. ...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified1.00 (0.00-2.00) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified< 0.1 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified3.2 umol/mmol creatinineAdult (>18 years old)BothPurine nucleoside phosphorylase (PNP) deficiency details
Associated Disorders and Diseases
Disease References
Purine nucleoside phosphorylase deficiency
  1. 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
Associated OMIM IDs
  • 164050 (Purine nucleoside phosphorylase deficiency )
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012323
KNApSAcK IDNot Available
Chemspider ID58569
KEGG Compound IDC05512
BioCyc IDDEOXYINOSINE
BiGG ID45942
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00071
Metagene LinkHMDB00071
METLIN ID3383
PubChem Compound65058
PDB ID2ND
ChEBI ID28997
References
Synthesis ReferenceRobins, 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
  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
  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
  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
  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
  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
  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

Enzymes

General function:
Involved in deaminase activity
Specific function:
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events. Acts as a positive regulator of T-cell coactivation, by binding DPP4. Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion.
Gene Name:
ADA
Uniprot ID:
P00813
Molecular weight:
40764.13
Reactions
Deoxyadenosine + Water → Deoxyinosine + Ammoniadetails
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:
PNP
Uniprot ID:
P00491
Molecular weight:
32117.69
Reactions
Deoxyinosine + Phosphoric acid → Hypoxanthine + Deoxyribose 1-phosphatedetails