trisodium ({[(2R,3S,4R,5R)-5-(5-bromo-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)(hydrogen phosphonatooxy)phosphinate

• ChemBase ID: 155500
• Molecular Formular: C9H11BrN2Na3O15P3
• Molecular Mass: 628.982633
• Monoisotopic Mass: 627.8248724
• SMILES: c1c(c(=O)[nH]c(=O)n1[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])O)O)O)Br.[Na+].[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(O)[O-])[O-])[O-])O[C@H]([C@@H]1O)n1cc(Br)c(=O)[nH]c1=O.[Na+].[Na+].[Na+]
• InChI: InChI=1S/C9H14BrN2O15P3.3Na/c10-3-1-12(9(16)11-7(3)15)8-6(14)5(13)4(25-8)2-24-29(20,21)27-30(22,23)26-28(17,18)19;;;/h1,4-6,8,13-14H,2H2,(H,20,21)(H,22,23)(H,11,15,16)(H2,17,18,19);;;/q;3*+1/p-3/t4-,5-,6-,8-;;;/m1.../s1
• InChIKey: QGNCJTNPQREPQC-FCIXCQMASA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium ({[(2R,3S,4R,5R)-5-(5-bromo-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)(hydrogen phosphonatooxy)phosphinate
• IUPAC Traditional name: trisodium {[(2R,3S,4R,5R)-5-(5-bromo-2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy(hydrogen phosphonatooxy)phosphinate
• Synonyms: 5-BrUTP; 5-Bromouridine 5′-triphosphate sodium salt

Database IDs

• CAS Number: 161848-60-8
• MDL Number: MFCD00274403
• PubChem SID: 162249638; 24891977
• PubChem CID: 71312144

CALCULATED PROPERTIES

• Acid pKa: 0.8952817
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): -9.234939
• LogD (pH = 7.4): -10.056389
• Log P: -2.5569115
• Molar Refractivity: 89.4285 cm^3
• Polarizability: 37.918156 Å^3
• Polar Surface Area: 267.41 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 22-26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥93%
• Empirical Formula (Hill Notation): C9H14BrN2O15P3

DETAILS

Sigma Aldrich - B7166

Application
5-Bromouridine 5′-triphosphate (5-BrUTP) is used to measure transcription via labeling of ribonucleic acids (RNA). RNA or cells labeled via 5-BrUTP incorporation may be detected immunologically with antibodies.