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

• ChemBase ID: 126907
• Molecular Formular: C9H12N2O5
• Molecular Mass: 228.20198
• Monoisotopic Mass: 228.07462149
• SMILES: O=c1[nH]c(=O)n(cc1)[C@@H]1O[C@@H]([C@@H](O)C1)CO
• 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-SHYZEUOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 2'-deoxyuridine
• Synonyms: Deoxyuridine; 1-(2-Deoxy-β-D-ribofuranosyl)uracil; Uracil deoxyriboside; 2′-Deoxyuridine; 1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione; 2′-Deoxyuridine; (+)-2′-Deoxyuridine; 1-(2-脱氧-β-D-呋喃核糖基)尿嘧啶; 2′-脱氧尿苷; 尿嘧啶脱氧核苷; (+)-2′-脱氧尿苷

Database IDs

• CAS Number: 951-78-0
• EC Number: 213-455-7
• MDL Number: MFCD00006527
• Beilstein Number: 24433
• PubChem SID: 162221233; 24893831
• PubChem CID: 640; 13712
• CHEBI ID: 16450
• CHEMBL: 353955
• Chemspider ID: 13118
• MeSH Name: Deoxyuridine
• Unique Ingredient Identifier: W78I7AY22C
• Wikipedia Title: Deoxyuridine

CALCULATED PROPERTIES

• Acid pKa: 8.705755
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.5148714
• LogD (pH = 7.4): -1.5353247
• 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

PROPERTIES

Physical Property

• Melting Point: 164-167 °C; 167-169 °C(lit.)
• Optical Rotation: [α]20/D +52±2°, c = 1.1% in 1 M NaOH; [α]26/D +29.8°, c = 2 in H2O

Safety Information

• RTECS: YU7490000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: mouse ... Slc29a1(63959)

Product Information

• Purity: ≥99%; ≥99.0% (HPLC); 97%; 98%; 99-100%
• Impurities: Thymidine, free
• Empirical Formula (Hill Notation): C9H12N2O5

DETAILS

Sigma Aldrich - D5412

包装
1, 5 g in poly bottle
100, 250 mg in poly bottle
Application
2′-Deoxyuridine (dU) is frequently halogenated to create thymidine analogues useful for studies of DNA synthesis and degradation mechanisms. Derivatized 2′-Deoxyuridines used as labeling substrates include chloro-2′-deoxyuridine (CldU), bromodeoxyuridine (BrdU) and/or iododeoxyuridine (IdU). Other useful analogues of 2′-deoxyuridine include 5-ethynyl-2′-deoxyuridine (DdU) and 5-hydroxymethyl-2′-deoxyuridine (HmdU).

Sigma Aldrich - 852872

Application
Used to synthesize enzyme inhibitors, antiviral agents, and anticancer agents.1,2