({[({[5-(5-bromo-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid sodium

• ChemBase ID: 133451
• Molecular Formular: C9H14BrN2NaO14P3
• Molecular Mass: 570.027513
• Monoisotopic Mass: 568.87389431
• SMILES: c1c(c(=O)[nH]c(=O)n1C1CC(C(O1)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)Br.[Na]
• Canonical SMILES: OC1CC(OC1COP(=O)(OP(=O)(OP(=O)(O)O)O)O)n1cc(Br)c(=O)[nH]c1=O.[Na]
• InChI: InChI=1S/C9H14BrN2O14P3.Na/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(24-7)3-23-28(19,20)26-29(21,22)25-27(16,17)18;/h2,5-7,13H,1,3H2,(H,19,20)(H,21,22)(H,11,14,15)(H2,16,17,18)
• InChIKey: PLQOGWBVMURSAR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[5-(5-bromo-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid sodium
• IUPAC Traditional name: ({[5-(5-bromo-2,4-dioxo-3H-pyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid sodium
• Synonyms: 5-BrdUTP; 5-Bromo-2′-deoxyuridine 5′-triphosphate sodium salt

Database IDs

• CAS Number: 102212-99-7
• MDL Number: MFCD00057405
• PubChem SID: 162227728; 24891527
• PubChem CID: 16218998

CALCULATED PROPERTIES

• Acid pKa: 0.89528275
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -8.334284
• LogD (pH = 7.4): -9.154934
• Log P: -1.6562735
• Molar Refractivity: 91.2829 cm^3
• Polarizability: 37.52471 Å^3
• Polar Surface Area: 238.69 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 23/24/25-36/37/38
• Safety Statements: 22-26-36-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H331-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Product Information

• Purity: ≥90%

DETAILS

Sigma Aldrich - B0631

Application
5-Bromo-2′-deoxyuridine 5′-triphosphate (5-BrdUTP) may be used as a labeling TdT substrate for terminal deoxynucleotidyl transferase (TdT) reactions or for DNA synthesis. BrdUTP is also used as an effective mutagenic agent. 5-BrdUTP labeling may be detected by immunological techniques or 5-BrdUTP may be derivitized by biotinylation or other methods for detection by fluorogenic or chromogenic methods.