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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-07-18 21:40:12 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
ValueSource
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-9H-purin-6-olChEBI
9-(2-Deoxy-b-D-erythro-pentofuranosyl)-9H-purin-6-olGenerator
9-(2-Deoxy-β-D-erythro-pentofuranosyl)-9H-purin-6-olGenerator
2'-DeoxyinosineHMDB
2-Deoxy-inosineHMDB
9-(2-Deoxy-b-D-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-oneHMDB
9-(2-Deoxy-b-D-erythro-pentofuranosyl)-hypoxanthineHMDB
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-hypoxanthineHMDB
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-oneHMDB
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-hypoxanthineHMDB
D-InoHMDB
delta-InoHMDB
DInosineMeSH
Deoxyribose-inosineMeSH
Chemical FormulaC10H12N4O4
Average Molecular Weight252.23
Monoisotopic Molecular Weight252.085854882
IUPAC Name9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-ol
Traditional Name2'-deoxy-inosine
CAS Registry Number890-38-0
SMILES
OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC2=O
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
DescriptionThis compound belongs to the class of chemical entities known as purine 2'-deoxyribonucleosides. These are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleosides
Direct ParentPurine 2'-deoxyribonucleosides
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside
  • Hypoxanthine
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • N-substituted imidazole
  • Pyrimidine
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Oxolane
  • Secondary alcohol
  • Azacycle
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility18.7 mg/mLALOGPS
logP-1.7ALOGPS
logP-0.66ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)11.68ChemAxon
pKa (Strongest Basic)-0.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.52 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.97 m3·mol-1ChemAxon
Polarizability23.84 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udi-0933100000-09d719c947c60bf0f309View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0zfr-0940000000-e72ee71b7bb48b638ddcView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0zfr-2930000000-4781d246f6996b2513f8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-699f2e0add16852a454cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-ab78094925c0c212f113View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-5900000000-f14b9bd6e2a698307815View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0f79-9300000000-1d2cd609ae1f49c1960fView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Nucleus
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Location
  • All Tissues
Pathways
NameSMPDB LinkKEGG Link
Adenine phosphoribosyltransferase deficiency (APRT)SMP00535Not Available
Adenosine Deaminase DeficiencySMP00144Not Available
Adenylosuccinate Lyase DeficiencySMP00167Not Available
AICA-RibosiduriaSMP00168Not Available
Azathioprine PathwaySMP00427Not Available
Gout or Kelley-Seegmiller SyndromeSMP00365Not Available
Lesch-Nyhan Syndrome (LNS)SMP00364Not Available
Mercaptopurine PathwaySMP00428Not Available
Mitochondrial DNA depletion syndromeSMP00536Not Available
Molybdenum Cofactor DeficiencySMP00203Not Available
Myoadenylate deaminase deficiencySMP00537Not Available
Purine MetabolismSMP00050map00230
Purine Nucleoside Phosphorylase DeficiencySMP00210Not Available
Thioguanine PathwaySMP00430Not Available
Xanthine Dehydrogenase Deficiency (Xanthinuria)SMP00220Not Available
Xanthinuria type ISMP00512Not Available
Xanthinuria type IISMP00513Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Both
    Normal
      • Zerihun T. Dame, ...
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>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
    UrineDetected and Quantified0-6 umol/mmol creatinineChildren (1 - 18 years old)Both
    Normal
      • BC Children's Hos...
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    UrineDetected and Quantified1.573 +/- 1.68 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    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