GABAReceptorInhibitorgabareceptorinhibitor

Deoxyinosine

By rofalproject
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 accumliation of ADA substrates or their metabolites. Inosine is also an intermediate in a chain of purine nucleotides reactions required for muscle movements. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 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 Formlia

C10H12N4O4 Average Molecliar Weight

252.23 Monoisotopic Molecliar Weight

252.085854882 IUPAC Name

9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-ol Traditional Name

2-deoxy-inosine CAS Registry Number

890-38-0 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 Key

VGONTNSXDCQUGY-RRKCRQDMSA-N Chemical Taxonomy Description

This 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. Kingdom

Chemical entities Super Class

Organic compounds Class

Nucleosides, nucleotides, and analogues Sub Class

Purine nucleosides Direct Parent

Purine 2-deoxyribonucleosides Alternative Parents

  • Hypoxanthines
  • Hydroxypyrimidines
  • N-substituted imidazoles
  • Oxolanes
  • Heteroaromatic compounds
  • Secondary alcohols
  • Oxacyclic compounds
  • Azacyclic compounds
  • Primary alcohols
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Hydrocarbon derivatives

    • 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

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • purine 2'-deoxyribonucleoside (CHEBI:28997 )

    • Ontology Status

    Detected and Quantified Origin

  • Endogenous

    • Biofunction

    Not Available Application

    Not Available Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Nucleus

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point250 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP-1.71FORD,H ET AL. (1991)

    Predicted Properties

    Property Value Source 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key GC-MS

    GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udi-0933100000-09d719c947c60bf0f309View in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0zfr-0940000000-e72ee71b7bb48b638ddcView in MoNA GC-MS

    GC-MS Spectrum – GC-MS (3 TMS)splash10-0zfr-2930000000-4781d246f6996b2513f8View in MoNA Predicted GC-MS

    Predicted GC-MS Spectrum – GC-MSNot Available LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-699f2e0add16852a454cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-ab78094925c0c212f113View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-000i-5900000000-f14b9bd6e2a698307815View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available MS

    Mass Spectrum (Electron Ionization)splash10-0f79-9300000000-1d2cd609ae1f49c1960fView in MoNA 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    13C NMR SpectrumNot Available 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    13C NMR SpectrumNot Available 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Nucleus

    • Biofluid Locations

  • Blood
  • Saliva
  • Urine

    • Tissue Location

  • All Tissues

    • Pathways

    Name SMPDB Link KEGG 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

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot Available

    Normal

  • details SalivaDetected but not Quantified Adlit (>18 years old)Both

    Normal

  • Zerihun T. Dame, …

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details UrineDetected and Quantified1.00 (0.00-2.00) umol/mmol creatinineAdlit (>18 years old)BothNormal

  • 16613999

    • details UrineDetected and Quantified< 0.1 umol/mmol creatinineAdlit (>18 years old)BothNormal

  • 8595732

    • details UrineDetected and Quantified0-6 umol/mmol creatinineChildren (1 – 18 years old)Both

    Normal

  • BC Children's Hos…

    • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference 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 creatinineAdlit (>18 years old)BothPurine nucleoside phosphorylase (PNP) deficiency

  • 8595732

    • details

    Associated Disorders and Diseases Disease References

    Purine nucleoside phosphorylase deficiency

    1. Chantin C, Bonin B, Boliieu 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 )

    • External Links 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 KEGG Compound ID

    C05512 BioCyc ID

    DEOXYINOSINE BiGG ID

    45942 Wikipedia Link

    Not Available NuGOwiki Link

    HMDB00071 Metagene Link

    HMDB00071 METLIN ID

    3383 PubChem Compound

    65058 PDB ID

    2ND ChEBI ID

    28997

    Product: ISA-2011B

    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 ]
    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 + Ammonia details
    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-phosphate details

    PMID: 15358121

    By rofalproject

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