Record Information
Version2.0
Creation Date2012-05-31 09:57:24 -0600
Update Date2015-09-13 15:15:17 -0600
Secondary Accession Numbers
  • ECMDB00101
Identification
Name:Deoxyadenosine
DescriptionDeoxyadenosine 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
Weight:Average: 251.2419
Monoisotopic: 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
Description belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassPurine 2'-deoxyribonucleosides
Direct ParentPurine 2'-deoxyribonucleosides
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 g/LALOGPS
logP-0.95ALOGPS
logP-1.2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)13.89ChemAxon
pKa (Strongest Basic)3.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area119.31 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.68 m³·mol⁻¹ChemAxon
Polarizability24.24 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
purine deoxyribonucleosides degradationPW002077 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • purine deoxyribonucleosides degradation PWY0-1297
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
3± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
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-EI-TOF (Non-derivatized)splash10-0pbc-1950000000-892b755b10f34bcfa1c7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-05fr-9750000000-34ebf7e59598c6551f52View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0pbc-2950000000-9d52e7dcd83de5a30aefView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9550000000-219c39ab05ecbebb53eeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0ge9-6917000000-51808985bdc9abeb3cb3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0900000000-66ae7ac8bd510a173402View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0900000000-c71d67857e2136dc7666View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udr-1790000000-cfbdf2e3950e7987b94bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-1900000000-a3c367588a28d36cf5f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-2900000000-1b8d5c847c2b1955056eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-5900000000-f950493ce420caae6a66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004r-8900000000-61ed5b4b3e748a449803View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-31d03c242f14d91a718cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0390000000-fba17d1430b371138db2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0930000000-931c7b084c33f9122af4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-81ac782a59b2ca52f52bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0920000000-2e897a458cf4c7af381cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-f52b5322fde2e3722903View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-fcb0a5032b8607fd8b11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0290000000-bec96a9658c683fa0d9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0910000000-b504aa725d20d6213b20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-2900000000-d09551db93d558a5aed7View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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:
Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell
Gene Name:
ushA
Uniprot ID:
P07024
Molecular weight:
60824
Reactions
UDP-sugar + H(2)O = UMP + alpha-D-aldose 1-phosphate.
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
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 E.coli in stationary growth phase
Gene Name:
surE
Uniprot ID:
P0A840
Molecular weight:
26900
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 catalytic activity
Specific function:
Nucleotidase that shows high phosphatase activity toward three nucleoside 5'-monophosphates, UMP, dUMP, and dTMP, and very low activity against TDP, IMP, UDP, GMP, dGMP, AMP, dAMP, and 6- phosphogluconate. Is strictly specific to substrates with 5'- phosphates and shows no activity against nucleoside 2'- or 3'- monophosphates. Might be involved in the pyrimidine nucleotide substrate cycles
Gene Name:
yjjG
Uniprot ID:
P0A8Y1
Molecular weight:
25300
Reactions
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules
Gene Name:
deoD
Uniprot ID:
P0ABP8
Molecular weight:
25950
Reactions
Purine nucleoside + phosphate = purine + alpha-D-ribose 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
Uniprot ID:
P0AE22
Molecular weight:
26103
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate.
General function:
Involved in deaminase activity
Specific function:
Adenosine + H(2)O = inosine + NH(3)
Gene Name:
add
Uniprot ID:
P22333
Molecular weight:
36397
Reactions
Adenosine + H(2)O = inosine + NH(3).
General function:
Involved in catalytic activity
Specific function:
Nucleotidase that shows strict specificity toward deoxyribonucleoside 5'-monophosphates and does not dephosphorylate 5'-ribonucleotides or ribonucleoside 3'-monophosphates. Might be involved in the regulation of all dNTP pools in E.coli
Gene Name:
yfbR
Uniprot ID:
P76491
Molecular weight:
22708
Reactions
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.

Transporters

General function:
Involved in nucleoside:sodium symporter activity
Specific function:
Transports nucleosides with a high affinity except guanosine and deoxyguanosine. Driven by a proton motive force
Gene Name:
nupC
Uniprot ID:
P0AFF2
Molecular weight:
43475
General function:
Involved in nucleoside transmembrane transporter activity
Specific function:
Transports nucleosides with a high affinity. Driven by a proton motive force
Gene Name:
nupG
Uniprot ID:
P0AFF4
Molecular weight:
46389
General function:
Involved in nucleoside:sodium symporter activity
Specific function:
Nucleoside transporter
Gene Name:
nupX
Uniprot ID:
P33021
Molecular weight:
43409
General function:
Involved in nucleoside transmembrane transporter activity
Specific function:
Constitutes the receptor for colicin K and phage T6, and functions as substrate-specific channel for nucleosides and deoxynucleosides
Gene Name:
tsx
Uniprot ID:
P0A927
Molecular weight:
33589