Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000039
Identification
Name: Deoxyadenosine
Description:Deoxyadenosine is a member of the chemical class known as Purine 2'-deoxyribonucleosides and Analogues. These are compounds consisting of a purine linked to a ribose which lacks an hydroxyl group at position 2. Deoxyadenosine is a deoxyribonucleoside. It is a derivative of the nucleoside adenosine, differing from the latter by the replacement of a hydroxyl group (-OH) by hydrogen (-H) at the 2' position of its ribose sugar moiety. Deoxyadenosine is the DNA nucleoside A, which pairs with deoxythymidine (T) in double-stranded DNA.
Structure
Thumb
Synonyms:
  • 1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-b-D-Ribofuranose
  • 1-(6-amino-9H-Purin-9-yl)-1,2-dideoxy-b-delta-ribofuranose
  • 1-(6-amino-9H-Purin-9-yl)-1,2-dideoxy-b-δ-ribofuranose
  • 1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-beta-D-Ribofuranose
  • 1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-beta-delta-Ribofuranose
  • 1-(6-amino-9H-Purin-9-yl)-1,2-dideoxy-β-D-ribofuranose
  • 1-(6-amino-9H-Purin-9-yl)-1,2-dideoxy-β-δ-ribofuranose
  • 2'-Deoxyadenosine
  • 2-Deoxy-adenosine
  • 2-Deoxyadenosine
  • 9-(2-Deoxy-b-D-erythro-pentofuranosyl)-9H-Purin-6-amine
  • 9-(2-Deoxy-b-D-erythro-pentofuranosyl)adenine
  • 9-(2-Deoxy-b-D-ribofuranosyl)-9H-Purin-6-amine
  • 9-(2-Deoxy-b-delta-erythro-pentofuranosyl)-9H-purin-6-amine
  • 9-(2-Deoxy-b-delta-erythro-pentofuranosyl)adenine
  • 9-(2-Deoxy-b-delta-ribofuranosyl)-9H-purin-6-amine
  • 9-(2-Deoxy-b-δ-erythro-pentofuranosyl)-9H-purin-6-amine
  • 9-(2-Deoxy-b-δ-erythro-pentofuranosyl)adenine
  • 9-(2-Deoxy-b-δ-ribofuranosyl)-9H-purin-6-amine
  • 9-(2-deoxy-beta-D-erythro-pentofuranosyl)-9H-Purin-6-amine
  • 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adenine
  • 9-(2-deoxy-beta-D-ribofuranosyl)-9H-Purin-6-amine
  • 9-(2-deoxy-beta-delta-erythro-pentofuranosyl)-9H-Purin-6-amine
  • 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)adenine
  • 9-(2-deoxy-beta-delta-ribofuranosyl)-9H-Purin-6-amine
  • 9-(2-Deoxy-β-D-erythro-pentofuranosyl)-9H-purin-6-amine
  • 9-(2-Deoxy-β-D-erythro-pentofuranosyl)adenine
  • 9-(2-Deoxy-β-D-ribofuranosyl)-9H-purin-6-amine
  • 9-(2-Deoxy-β-δ-erythro-pentofuranosyl)-9H-purin-6-amine
  • 9-(2-Deoxy-β-δ-erythro-pentofuranosyl)adenine
  • 9-(2-Deoxy-β-δ-ribofuranosyl)-9H-purin-6-amine
  • Adenine deoxyribonucleoside
  • Adenine deoxyribose
  • Adenine-9 2-deoxy-b-D-erythro-Pentofuranoside
  • Adenine-9 2-deoxy-b-delta-erythro-pentofuranoside
  • Adenine-9 2-deoxy-b-δ-erythro-pentofuranoside
  • Adenine-9 2-deoxy-beta-D-erythro-Pentofuranoside
  • Adenine-9 2-deoxy-beta-delta-erythro-Pentofuranoside
  • Adenine-9 2-deoxy-β-D-erythro-pentofuranoside
  • Adenine-9 2-deoxy-β-δ-erythro-pentofuranoside
  • Adenyldeoxyriboside
  • DA
  • DAdenosine
  • Deoxyadenosine
  • Desoxyadenosine
Chemical Formula: C10H13N5O3
Average Molecular Weight: 251.2419
Monoisotopic Molecular Weight: 251.101839307
InChI Key: OLXZPDWKRNYJJZ-RRKCRQDMSA-N
InChI: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
CAS number: 958-09-8
IUPAC Name:(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
Traditional IUPAC Name: 2-deoxyadenosine
SMILES:NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as purine 3'-deoxyribonucleosides. These are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 3.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleosides
Sub ClassPurine 3'-deoxyribonucleosides
Direct Parent Purine 3'-deoxyribonucleosides
Alternative Parents
Substituents
  • Purine 3'-deoxyribonucleoside
  • Purine 2'-deoxyribonucleoside
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • N-substituted imidazole
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 189
Experimental Properties:
PropertyValueSource
Water Solubility:3.36 mg/mlPhysProp
LogP:-0.941PhysProp
Predicted Properties
PropertyValueSource
Water Solubility10.7 mg/mLALOGPS
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 Area119.31 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.68 m3·mol-1ChemAxon
Polarizability24.25 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0pbc-1950000000-892b755b10f34bcfa1c7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-05fr-9750000000-34ebf7e59598c6551f52View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0pbc-2950000000-9d52e7dcd83de5a30aefView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udr-1790000000-c0d4c0cc085cab7c2dcfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-1900000000-e2abd19062db64ff67beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-2900000000-1b8d5c847c2b1955056eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000i-5900000000-845c20e0f6bd5494b6dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004r-8900000000-484d9f08e4e28fab1f70View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-e852451e7253e0de72beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0390000000-fba17d1430b371138db2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-000i-0930000000-931c7b084c33f9122af4View 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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • 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
  • 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
  • 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
  • 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
  • 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
  • Hayward AR: Resistance of pokeweed mitogen-stimulated B cells to inhibition by deoxyadenosine. Clin Exp Immunol. 1980 Jul;41(1):141-9. Pubmed: 6969149
  • 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
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • 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
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)
External Links:
ResourceLink
CHEBI ID17256
HMDB IDHMDB00101
Pubchem Compound ID13730
Kegg IDC00559
ChemSpider ID13135
WikipediaDeoxyadenosine
BioCyc IDDEOXYADENOSINE
EcoCyc IDDEOXYADENOSINE
Ligand Expo3D1

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Nucleotidase with a broad substrate specificity as it can dephosphorylate various ribo- and deoxyribonucleoside 5'- monophosphates and ribonucleoside 3'-monophosphates with highest affinity to 3'-AMP. Also hydrolyzes polyphosphate (exopolyphosphatase activity) with the preference for short-chain- length substrates (P20-25). Might be involved in the regulation of dNTP and NTP pools, and in the turnover of 3'-mononucleotides produced by numerous intracellular RNases (T1, T2, and F) during the degradation of various RNAs. Also plays a significant physiological role in stress-response and is required for the survival of Pseudomonas aeruginosa in stationary growth phase
Gene Name:
surE
Locus Tag:
PA3625
Molecular weight:
26.4 kDa
Reactions
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
A 3'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
(Polyphosphate)(n) + H(2)O = (polyphosphate)(n-1) + phosphate.
General function:
Involved in acid phosphatase activity
Specific function:
Dephosphorylates several organic phosphomonoesters and catalyzes the transfer of low-energy phosphate groups from phosphomonoesters to hydroxyl groups of various organic compounds. Preferentially acts on aryl phosphoesters. Might function as a broad-spectrum dephosphorylating enzyme able to scavenge both 3'- and 5'-nucleotides and also additional organic phosphomonoesters
Gene Name:
aphA
Locus Tag:
PA1409
Molecular weight:
38 kDa
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate.

Transporters