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

• ChemBase ID: 133654
• Molecular Formular: C11H13BrN2O5
• Molecular Mass: 333.13532
• Monoisotopic Mass: 332.00078353
• SMILES: c1c(c(=O)[nH]c(=O)n1[C@H]1C[C@@H](C(O1)CO)O)/C=C\Br
• Canonical SMILES: Br/C=C\c1cn([C@H]2C[C@@H](C(O2)CO)O)c(=O)[nH]c1=O
• InChI: InChI=1S/C11H13BrN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/b2-1-/t7-,8?,9+/m0/s1
• InChIKey: ODZBBRURCPAEIQ-LVHJSNLWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(Z)-2-bromoethenyl]-1-[(2R,4S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 5-[(Z)-2-bromoethenyl]-1-[(2R,4S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: BVdU; (E)-5-(2-Bromovinyl)-2′-deoxyuridine

Database IDs

• CAS Number: 69304-47-8
• MDL Number: MFCD00058585
• PubChem SID: 24278280; 162227931
• PubChem CID: 16219063

CALCULATED PROPERTIES

• Acid pKa: 9.341513
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.49662927
• LogD (pH = 7.4): -0.5014516
• Log P: -0.49656743
• Molar Refractivity: 67.6767 cm^3
• Polarizability: 26.512186 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: YU7355000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... HV1S(3365)

DETAILS

Sigma Aldrich - B9647

Biochem/physiol Actions
An exceptionally potent inhibitor of Herpes simplex virus type 1.