1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 2005
• Molecular Formular: C9H12N2O5
• Molecular Mass: 228.20198
• Monoisotopic Mass: 228.07462149
• SMILES: OC[C@H]1O[C@@H](C[C@@H]1O)n1ccc(=O)[nH]c1=O
• Canonical SMILES: OC[C@H]1O[C@@H](C[C@@H]1O)n1ccc(=O)[nH]c1=O
• 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
• InChIKey: MXHRCPNRJAMMIM-BBVRLYRLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: @2'-deoxyuridine
• Synonyms: 2'-Deoxyuridine

Database IDs

• CAS Number: 951-78-0
• PubChem SID: 160965460; 46506680
• PubChem CID: 1263358

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.7057295
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.5146308
• LogD (pH = 7.4): -1.5167224
• Log P: -1.5146041
• Molar Refractivity: 51.0549 cm^3
• Polarizability: 20.191685 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.49
• LOG S: -0.4
• Solubility (Water): 9.06e+01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -1.51 [BALZARINI,JM ET AL. (1989)]

DETAILS

DrugBank - DB02256

• Drug Groups: experimental
• Description: 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]