You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:54 UTC
HMDB IDHMDB00101
Secondary Accession Numbers
  • HMDB05778
  • HMDB11722
Metabolite Identification
Common NameDeoxyadenosine
DescriptionDeoxyadenosine 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
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 FormulaC10H13N5O3
Average Molecular Weight251.2419
Monoisotopic Molecular Weight251.101839307
IUPAC Name(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
Traditional Namedeoxyadenosine
CAS Registry Number958-09-8
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 KeyOLXZPDWKRNYJJZ-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
  • Deoxyribonucleosides(KEGG)
  • purine 2'-deoxyribonucleoside(ChEBI)
Substituents
  • Aminopyrimidine
  • Imidazole
  • Imidazopyrimidine
  • Oxolane
  • Primary Alcohol
  • Purine
  • Pyrimidine
  • Secondary Alcohol
Direct ParentPurine 2'-deoxyribonucleosides and Analogues
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • DNA component
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Nucleus
  • Lysosome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point189 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.55HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility10.7 g/LALOGPS
logP-0.95ALOGPS
logP-1.2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)13.89ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area119.31ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.68ChemAxon
Polarizability24.25ChemAxon
Spectra
SpectraGC-MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Nucleus
  • Lysosome
Biofluid Locations
  • Blood
  • 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
UrineDetected and Quantified0.22 +/- 0.09 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified176.0 (167.0-185.0) umol/mmol creatinineAdult (>18 years old)BothAdenosine deaminase(ADA) deficiency details
UrineDetected and Quantified0.005 (0.000-0.010) umol/mmol creatinineAdult (>18 years old)BothAdenosine deaminase(ADA) deficiency details
Associated Disorders and Diseases
Disease References
Adenosine deaminase deficiency
  1. 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
  2. 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
Associated OMIM IDs
  • 102700 (Adenosine deaminase deficiency)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021894
KNApSAcK IDNot Available
Chemspider ID13135
KEGG Compound IDC00559
BioCyc IDNot Available
BiGG ID35352
Wikipedia LinkDeoxyadenosine
NuGOwiki LinkHMDB00101
Metagene LinkHMDB00101
METLIN ID3382
PubChem Compound13730
PDB ID3D1
ChEBI ID17256
References
Synthesis ReferenceAnderson, 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. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  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
  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
  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
  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
  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

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:
NT5E
Uniprot ID:
P21589
Molecular weight:
57948.125
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphoric aciddetails
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Molecular weight:
68803.055
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphoric aciddetails
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Molecular weight:
41020.145
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphoric aciddetails
General function:
Involved in metal ion binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Molecular weight:
Not Available
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphoric aciddetails
General function:
Involved in phosphatase activity
Specific function:
Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Molecular weight:
Not Available
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphoric aciddetails
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 magnesium ion binding
Specific function:
Can act both as nucleotidase and as phosphotransferase.
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Molecular weight:
33914.91
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphoric aciddetails
General function:
Involved in 5'-nucleotidase activity
Specific function:
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:
NT5C2
Uniprot ID:
P49902
Molecular weight:
64969.2
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphoric aciddetails
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
Deoxyadenosine + Phosphoric acid → Adenine + Deoxyribose 1-phosphatedetails