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Bovine Metabolome Database



Showing metabocard for Deoxyguanosine (BMDB00085)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-08-07 12:16:10
Accession Number BMDB00085
Common Name Deoxyguanosine
Description A nucleoside consisting of the base guanine and the sugar deoxyribose. It is like guanosine, but with one oxygen atom removed. It is a nucleoside component of DNA. Deoxyguanosine can be converted to 8-hydroxy-deoxyguanosine (8-OHdG) due to hydroxyl radical attack at the C8 of guanine. 8-OHdG is a sensitive marker of the DNA damage This damage, if left unrepaired, has been proposed to contribute to mutagenicity and cancer promotion.
Synonyms
  1. 2'-Deoxyguanosine
  2. 2'-deoxy-Guanosine
  3. 2-Deoxyguanosine
  4. 9-(2-Deoxy-b-D-erythro-pentofuranosyl)guanine
  5. 9-(2-deoxy-b-D-erythro-pentofuranosyl)-Guanine
  6. Deoxyguanosine
  7. Desoxyguanosine
  8. Guanine deoxy nucleoside
  9. Guanine deoxyriboside
  10. 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)guanine
  11. 9-(2-deoxy-beta-delta-erythro-pentofuranosyl)-Guanine
Chemical IUPAC Name 2-amino-9-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
Chemical Formula C10H13N5O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Nucleosides and Nucleoside conjugates
Class
  • Nucleoside Analogues
Sub Class
  • Deoxy nucleosides
Family
  • Mammalian_Metabolite
Species
  • primary alcohol; secondary alcohol; primary amine; primary aromatic amine; oxo(het)arene; aromatic compound; heterocyclic compound
Biofunction
  • Component of Purine metabolism
Application
Source
  • Endogenous
Average Molecular Weight 267.241
Monoisotopic Molecular Weight 267.096741
Isomeric SMILES NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1
Canonical SMILES NC1=NC2=C(N=CN2C2CC(O)C(CO)O2)C(=O)N1
KEGG Compound ID C00330 Link Image
BioCyc ID DEOXYGUANOSINE Link Image
BiGG ID 34637 Link Image
Wikipedia Link Deoxyguanosine Link Image
METLIN ID 3395 Link Image
PubChem Compound 187790 Link Image
PubChem Substance 841363 Link Image
ChEBI ID 17172 Link Image
CAS Registry Number 961-07-9
InChI Identifier InChI=1/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1
Synthesis Reference Noguchi, Toshitada; Hamamoto, Tomoki; Okuyama, Kiyoshi; Shibuya, Susumu. Process for producing 2'-deoxyguanosine. PCT Int. Appl. (2003), 31 pp.
Melting Point (Experimental) 300 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 12.0 mg/mL [MEYLAN,WM et al. (1996)]; 11.5 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity -1.30 [BALZARINI,JM ET AL. (1989)] Source: PhysProp
Predicted LogP/Hydrophobicity -1.75 [Predicted by ALOGPS]; -1.1 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
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PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Show Image
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BMRB Spectrum Show Image
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Cellular Location
  • Cytoplasm
  • Nucleus
  • Extracellular
  • lysosome
  • mitochondria
Biofluid Location Not Available
Tissue Location
Tissue References
All Tissues
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Purine Metabolism
HMDB Pathways
Name Purine Metabolism
Image Show Link Image
KEGG Pathways
Name Purine Metabolism
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SimCell Pathways
Name Purine Metabolism
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General References
  1. Wikipedia Link Image