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

• ChemBase ID: 148381
• Molecular Formular: C9H12N2O4
• Molecular Mass: 212.20258
• Monoisotopic Mass: 212.07970687
• SMILES: c1cn(c(=O)[nH]c1=O)[C@H]1CC[C@H](O1)CO
• Canonical SMILES: OC[C@@H]1CC[C@@H](O1)n1ccc(=O)[nH]c1=O
• InChI: InChI=1S/C9H12N2O4/c12-5-6-1-2-8(15-6)11-4-3-7(13)10-9(11)14/h3-4,6,8,12H,1-2,5H2,(H,10,13,14)/t6-,8+/m0/s1
• InChIKey: BTOTXLJHDSNXMW-POYBYMJQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: ddU; 2′,3′-Dideoxyuridine; 2′,3′-二脱氧尿苷

Database IDs

• CAS Number: 5983-09-5
• MDL Number: MFCD00013359
• Beilstein Number: 750592
• PubChem SID: 162242557; 24859406
• PubChem CID: 65161

CALCULATED PROPERTIES

• Acid pKa: 9.705913
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.80597806
• LogD (pH = 7.4): -0.80806875
• Log P: -0.8059513
• Molar Refractivity: 50.261 cm^3
• Polarizability: 19.492252 Å^3
• Polar Surface Area: 78.87 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 127-129 °C(lit.)
• Optical Rotation: [α]20/D +34°, c = 0.4 in H2O

Safety Information

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

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C9H12N2O4

DETAILS

Sigma Aldrich - 323624

Packaging
100, 500 mg in glass bottle
Application
Research tool for antiviral and anticancer studies.1