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Bovine Metabolome Database



Showing metabocard for Deoxyuridine (BMDB00012)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-08-07 12:37:25
Accession Number BMDB00012
Common Name Deoxyuridine
Description 2'-Deoxyuridine is a naturally occurring nucleoside. It is similar in chemical structure to uridine, but without the 2'-hydroxyl group. It is considered to be an antimetabolite that is converted to deoxyuridine triphosphate during DNA synthesis. Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemia due to vitamin B12 and folate deficiencies.
Synonyms
  1. 1-(2-Deoxy-D-erythro-pentofuranosyl)uracil
  2. 1-(2-deoxy-beta-D-erythro-pentofuranosyl)-2,4(1H,3H)-Pyrimidinedione
  3. 1-(2-deoxy-beta-D-ribofuranosyl)-2,4(1H,3H)-Pyrimidinedione
  4. 2'-Deoxyuridine
  5. 2'-Desoxyuridine
  6. Deoxyribose uracil
  7. Desoxyuridine
  8. Uracil deoxyriboside
  9. Uracil desoxyuridine
  10. 1-(2-Deoxy-delta-erythro-pentofuranosyl)uracil
  11. 1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-2,4(1H,3H)-Pyrimidinedione
  12. 1-(2-deoxy-beta-delta-ribofuranosyl)-2,4(1H,3H)-Pyrimidinedione
Chemical IUPAC Name 1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Chemical Formula C9H12N2O5
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; oxo(het)arene; aromatic compound; heterocyclic compound
Biofunction
  • DNA component
Application
Source
  • Endogenous
Average Molecular Weight 228.202
Monoisotopic Molecular Weight 228.074615
Isomeric SMILES OC[C@H]1O[C@H](C[C@@H]1O)N1C=CC(=O)NC1=O
Canonical SMILES OCC1OC(CC1O)N1C=CC(=O)NC1=O
KEGG Compound ID C00526 Link Image
BioCyc ID DEOXYURIDINE Link Image
BiGG ID 35251 Link Image
Wikipedia Link Deoxyuridine Link Image
METLIN ID 5086 Link Image
PubChem Compound 13712 Link Image
PubChem Substance 832124 Link Image
ChEBI ID 16450 Link Image
CAS Registry Number 951-78-0
InChI Identifier InChI=1/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1
Synthesis Reference Huang, Haoqiang; Chu, Chung K. A practical synthesis of 2'-deoxyuridine from uridine. Synthetic Communications (1990), 20(7), 1039-46.
Melting Point (Experimental) 167 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 29.7 mg/mL [MEYLAN,WM et al. (1996)]; 90.600006 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity -1.51 [BALZARINI,JM ET AL. (1989)] Source: PhysProp
Predicted LogP/Hydrophobicity -1.49 [Predicted by ALOGPS]; -1.5 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID 1BDU Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
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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
Download File
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from LogP)
  • Extracellular
  • mitochondria
  • nucleus
Biofluid Location Not Available
Tissue Location
Tissue References
Bladder
Bone Marrow
Fibroblasts
Intestine
Lymphocyte
Most Tissues
Muscle
Neuron
Pancreas
Placenta
Testes
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Pyrimidine Metabolism
HMDB Pathways
Name Pyrimidine Metabolism
Image Show Link Image
KEGG Pathways
Name Pyrimidine Metabolism
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SimCell Pathways
Name Pyrimidine Metabolism
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Graph
SBML
General References
  1. Wikipedia Link Image