Status : experimental


2'-Deoxyuridine. An antimetabolite that is converted to deoxyuridine triphosphate during DNA synthesis. Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies. [PubChem]

Chemical Classification

This compound belongs to the class of organic compounds known as pyrimidine 2′-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.

Pyrimidine 2′-deoxyribonucleosides

Organic compounds

Nucleosides, nucleotides, and analogues

Pyrimidine nucleosides

Pyrimidine 2′-deoxyribonucleosides

Calculated Property

kind Value Source
logP -1.5 ALOGPS
logS -0.4 ALOGPS
Water Solubility 9.06e+01 g/l ALOGPS
logP -1.5 ChemAxon
IUPAC Name 1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione ChemAxon
Traditional IUPAC Name 2′-deoxyuridine ChemAxon
Molecular Weight 228.202 ChemAxon
Monoisotopic Weight 228.074621504 ChemAxon
SMILES OC[C@H]1O[C@@H](C[C@@H]1O)N1C=CC(=O)NC1=O ChemAxon
Molecular Formula C9H12N2O5 ChemAxon
InChI InChI=1S/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 ChemAxon
Polar Surface Area (PSA) 99.1 ChemAxon
Refractivity 51.05 ChemAxon
Polarizability 21.16 ChemAxon
Rotatable Bond Count 2 ChemAxon
H Bond Acceptor Count 5 ChemAxon
H Bond Donor Count 3 ChemAxon
pKa (strongest acidic) 9.71 ChemAxon
pKa (strongest basic) -3 ChemAxon
Physiological Charge 0 ChemAxon
Number of Rings 2 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 0 ChemAxon

Target within organism

  • Uridine phosphorylase : in Escherichia coli (strain K12)
  • Thymidylate synthase : in Escherichia coli (strain K12)