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Human Metabolome Database Version 3.5

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Showing metabocard for Deoxyadenosine (HMDB00101)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:54 -0700
HMDB ID HMDB00101
Secondary Accession Numbers
  • HMDB05778
  • HMDB11722
Metabolite Identification
Common Name Deoxyadenosine
Description Deoxyadenosine is a derivative of nucleoside adenosine. It is comprised of adenine attached to a deoxyribose moiety via a N9-glycosidic bond. Deoxyribose differs from ribose by the absence of oxygen in the 3' position of its ribose ring. Deoxyadenosine is a critical component of DNA.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-b-D-Ribofuranose
  2. 1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-beta-D-Ribofuranose
  3. 1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-beta-delta-Ribofuranose
  4. 2'-Deoxyadenosine
  5. 2-Deoxyadenosine
  6. 9-(2-Deoxy-b-D-erythro-pentofuranosyl)-9H-Purin-6-amine
  7. 9-(2-Deoxy-b-D-erythro-pentofuranosyl)adenine
  8. 9-(2-Deoxy-b-D-ribofuranosyl)-9H-Purin-6-amine
  9. 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-9H-Purin-6-amine
  10. 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adenine
  11. 9-(2-Deoxy-beta-D-ribofuranosyl)-9H-Purin-6-amine
  12. 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-9H-Purin-6-amine
  13. 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)adenine
  14. 9-(2-Deoxy-beta-delta-ribofuranosyl)-9H-Purin-6-amine
  15. Adenine deoxyribonucleoside
  16. Adenine deoxyribose
  17. Adenine-9 2-deoxy-b-D-erythro-Pentofuranoside
  18. Adenine-9 2-deoxy-beta-D-erythro-Pentofuranoside
  19. Adenine-9 2-deoxy-beta-delta-erythro-Pentofuranoside
  20. Adenyldeoxyriboside
  21. DA
  22. Deoxyadenosine
  23. Desoxyadenosine
Chemical Formula C10H13N5O3
Average Molecular Weight 251.2419
Monoisotopic Molecular Weight 251.101839307
IUPAC Name (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
Traditional IUPAC Name deoxyadenosine
CAS Registry Number 958-09-8
SMILES NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1
InChI Identifier InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1
InChI Key OLXZPDWKRNYJJZ-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
  • Deoxyribonucleosides(KEGG)
  • purine 2'-deoxyribonucleoside(ChEBI)
Substituents
  • Aminopyrimidine
  • Imidazole
  • Imidazopyrimidine
  • Oxolane
  • Primary Alcohol
  • Purine
  • Pyrimidine
  • Secondary Alcohol
Direct Parent Purine 2'-deoxyribonucleosides and Analogues
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • DNA component
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Nucleus
  • Lysosome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 189 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -0.55 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 10.7 g/L ALOGPS
LogP -0.95 ALOGPS
LogP -1.2 ChemAxon
LogS -1.37 ALOGPS
pKa (strongest acidic) 13.89 ChemAxon
pKa (strongest basic) 5 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 119.31 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 61.68 ChemAxon
Polarizability 24.25 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
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 LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Nucleus
  • Lysosome
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 Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
Article_icon
0.22 +/- 0.09 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
176.0 (167.0-185.0) umol/mmol creatinine Adult (>18 years old) Both Adenosine deaminase deficiency Not Available
Urine Detected and Quantified
Article_icon
0.005 (0.000-0.010) umol/mmol creatinine Adult (>18 years old) Both Adenosine deaminase deficiency Not Available
Associated Disorders and Diseases
Disease References
Adenosine deaminase deficiency
  • Yamamoto T, Moriwaki Y, Takahashi S, Fujita T, Tsutsumi Z, Yamakita J, Shimizu K, Shiota M, Ohta S, Higashino K: Determination of adenosine and deoxyadenosine in urine by high-performance liquid chromatography with column switching. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):55-61. Pubmed: 9869364 Link_out
  • Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. Pubmed: 10102915 Link_out
    Associated OMIM IDs
    • 102700 Link_out (Adenosine deaminase deficiency)
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB021894
    KNApSAcK ID Not Available
    Chemspider ID 13135 Link_out
    KEGG Compound ID C00559 Link_out
    BioCyc ID Not Available
    BiGG ID 35352 Link_out
    Wikipedia Link Deoxyadenosine Link_out
    NuGOwiki Link HMDB00101 Link_out
    Metagene Link HMDB00101 Link_out
    METLIN ID 3382 Link_out
    PubChem Compound 13730 Link_out
    PDB ID 3D1 Link_out
    ChEBI ID 17256 Link_out
    References
    Synthesis Reference Anderson, Charles D.; Goodman, Leon; Baker, B. R. Potential anticancer agents. XIX. Synthesis of 2-deoxyadenosine. Journal of the American Chemical Society (1959), 81 3967-74.
    Material Safety Data Sheet (MSDS) Download (PDF)
    General References
    1. Brox LW, Pollock E, Belch A: Adenosine and deoxyadenosine toxicity in colony assay systems for human T-lymphocytes, B-lymphocytes, and granulocytes. Cancer Chemother Pharmacol. 1982;9(1):49-52. Pubmed: 6982786 Link_out
    2. Fox RM, Tripp EH, Taylor IW: Analytical DNA flow cytometric analysis of deoxyadenosine toxicity in cultured human leukemic lymphoblasts. Mol Pharmacol. 1984 Sep;26(2):388-94. Pubmed: 6332978 Link_out
    3. Bluestein HG, Thompson LF, Albert DA, Seegmiller JE: Altered deoxynucleoside triphosphate levels paralleling deoxyadenosine toxicity in adenosine deaminase inhibited human lymphocytes. Adv Exp Med Biol. 1980;122A:427-31. Pubmed: 6968502 Link_out
    4. Juliusson G, Liliemark J: High complete remission rate from 2-chloro-2'-deoxyadenosine in previously treated patients with B-cell chronic lymphocytic leukemia: response predicted by rapid decrease of blood lymphocyte count. J Clin Oncol. 1993 Apr;11(4):679-89. Pubmed: 8097528 Link_out
    5. Szabados E, Christopherson RI: Rapid radioassay for metabolites of adenosine and deoxyadenosine in erythrocytes. J Chromatogr B Biomed Appl. 1995 Dec 1;674(1):132-7. Pubmed: 8749261 Link_out
    6. Hershfield MS, Kredich NM, Koller CA, Mitchell BS, Kurtzberg J, Kinney TR, Falletta JM: S-adenosylhomocysteine catabolism and basis for acquired resistance during treatment of T-cell acute lymphoblastic leukemia with 2'-deoxycoformycin alone and in combination with 9-beta-D-arabinofuranosyladenine. Cancer Res. 1983 Jul;43(7):3451-8. Pubmed: 6601986 Link_out
    7. Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. Pubmed: 10102915 Link_out
    8. Mitchell BS, Edwards NL: Purine metabolizing enzymes as predictors of lymphoblast sensitivity to deoxyadenosine. J Lab Clin Med. 1984 Sep;104(3):414-24. Pubmed: 6147383 Link_out
    9. Yamamoto T, Moriwaki Y, Takahashi S, Fujita T, Tsutsumi Z, Yamakita J, Shimizu K, Shiota M, Ohta S, Higashino K: Determination of adenosine and deoxyadenosine in urine by high-performance liquid chromatography with column switching. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):55-61. Pubmed: 9869364 Link_out
    10. Hayward AR: Resistance of pokeweed mitogen-stimulated B cells to inhibition by deoxyadenosine. Clin Exp Immunol. 1980 Jul;41(1):141-9. Pubmed: 6969149 Link_out
    11. Carson DA, Wasson DB, Kaye J, Ullman B, Martin DW Jr, Robins RK, Montgomery JA: Deoxycytidine kinase-mediated toxicity of deoxyadenosine analogs toward malignant human lymphoblasts in vitro and toward murine L1210 leukemia in vivo. Proc Natl Acad Sci U S A. 1980 Nov;77(11):6865-9. Pubmed: 6256765 Link_out
    12. Carson DA, Carrera CJ, Kubota M, Wasson DB, Iizasa T: Genetic analysis of deoxyadenosine toxicity in dividing human lymphoblasts. Adv Exp Med Biol. 1986;195 Pt B:207-11. Pubmed: 3020905 Link_out
    13. Webster DR, Simmonds HA, Perrett D, Levinsky RJ: Nucleotide levels and metabolism of adenosine and deoxyadenosine in intact erythrocytes deficient in adenosine deaminase. Adv Exp Med Biol. 1984;165 Pt A:363-6. Pubmed: 6609529 Link_out
    14. Sheridan W, Gordon DS, Fullen AJ, Olson A, Vogler WR, Winton E: Preclinical studies on deoxycoformycin and deoxyadenosine as pharmacologic T cell purging tools. Bone Marrow Transplant. 1989 Sep;4(5):511-7. Pubmed: 2790329 Link_out
    Enzymes
    Name: Cytosolic 5'-nucleotidase 1B
    Reactions:
    • a 5'-ribonucleotide + H2O = a ribonucleoside + phosphate [RN:R07297]
    Gene Name: NT5C1B
    Uniprot ID: Q96P26 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Cytosolic 5'-nucleotidase 1A
    Reactions:
    • a 5'-ribonucleotide + H2O = a ribonucleoside + phosphate [RN:R07297]
    Gene Name: NT5C1A
    Uniprot ID: Q9BXI3 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 5'(3')-deoxyribonucleotidase, cytosolic type
    Reactions:
      Gene Name: NT5C
      Uniprot ID: Q8TCD5 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 5'(3')-deoxyribonucleotidase, mitochondrial
      Reactions:
        Gene Name: NT5M
        Uniprot ID: Q9NPB1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Adenosine deaminase
        Reactions:
        • adenosine + H2O = inosine + NH3 [RN:R01560]
        Gene Name: ADA
        Uniprot ID: P00813 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytosolic 5'-nucleotidase 3
        Reactions:
        • a 5'-ribonucleotide + H2O = a ribonucleoside + phosphate [RN:R07297]
        Gene Name: NT5C3
        Uniprot ID: Q9H0P0 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA