2,5-dioxo-1-{[6-(5-{2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl}pentanamido)hexanoyl]oxy}pyrrolidine-3-sulfonic acid sodium

• ChemBase ID: 133445
• Molecular Formular: C20H30N4NaO9S2
• Molecular Mass: 557.59337
• Monoisotopic Mass: 557.13518984
• SMILES: C1C(C(=O)N(C1=O)OC(=O)CCCCCNC(=O)CCCCC1C2C(CS1)NC(=O)N2)S(=O)(=O)O.[Na]
• Canonical SMILES: O=C(CCCCC1SCC2C1NC(=O)N2)NCCCCCC(=O)ON1C(=O)CC(C1=O)S(=O)(=O)O.[Na]
• InChI: InChI=1S/C20H30N4O9S2.Na/c25-15(7-4-3-6-13-18-12(11-34-13)22-20(29)23-18)21-9-5-1-2-8-17(27)33-24-16(26)10-14(19(24)28)35(30,31)32;/h12-14,18H,1-11H2,(H,21,25)(H2,22,23,29)(H,30,31,32)
• InChIKey: RDSJVNGBJUJRRW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxo-1-{[6-(5-{2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl}pentanamido)hexanoyl]oxy}pyrrolidine-3-sulfonic acid sodium
• IUPAC Traditional name: 2,5-dioxo-1-{[6-(5-{2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl}pentanamido)hexanoyl]oxy}pyrrolidine-3-sulfonic acid sodium
• Synonyms: Sulfosuccinimidyl 6-(biotinamido)hexanoate; Biotinamidohexanoic acid 3-sulfo-N-hydroxysuccinimide ester sodium salt

Database IDs

• CAS Number: 127062-22-0
• MDL Number: MFCD00078534
• PubChem SID: 162227722; 24891541
• PubChem CID: 16219001

CALCULATED PROPERTIES

• Acid pKa: -1.270417
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.0782394
• LogD (pH = 7.4): -3.0784528
• Log P: -2.3969605
• Molar Refractivity: 122.0444 cm^3
• Polarizability: 49.050537 Å^3
• Polar Surface Area: 188.28 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF: soluble50 mg/mL; H2O: soluble10 mg/mL
• Apperance: powder

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 61
• Safety Statements: 53-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360D
• GHS Precautionary statements: P201-P308 + P313
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (TLC)

DETAILS

Sigma Aldrich - B1022

Application
Water soluble biotinylation reagent incorporating an aminocaproyl spacer. This can reduce the steric hindrance in binding avidin to some biotinylated compounds. Has also been used as a cell surface labeling reagent. Typically coupled to primary amine in the pH range 6.5-8.5. May be used for the biotinylation of cell surface proteins.