2,5-dioxopyrrolidin-1-yl 6-(6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanamido)hexanoate

• ChemBase ID: 134155
• Molecular Formular: C26H41N5O7S
• Molecular Mass: 567.69804
• Monoisotopic Mass: 567.27266968
• SMILES: C1CC(=O)N(C1=O)OC(=O)CCCCCNC(=O)CCCCCNC(=O)CCCC[C@H]1[C@@H]2[C@H](CS1)NC(=O)N2
• Canonical SMILES: O=C(NCCCCCC(=O)ON1C(=O)CCC1=O)CCCCCNC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C26H41N5O7S/c32-20(27-16-8-2-4-12-24(36)38-31-22(34)13-14-23(31)35)10-3-1-7-15-28-21(33)11-6-5-9-19-25-18(17-39-19)29-26(37)30-25/h18-19,25H,1-17H2,(H,27,32)(H,28,33)(H2,29,30,37)/t18-,19-,25-/m0/s1
• InChIKey: ATYCFNRXENKXSE-MHPIHPPYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 6-(6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanamido)hexanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 6-(6-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanamido)hexanoate
• Synonyms: 6-(Biotinamidocaproylamido)caproic acid N-hydroxysuccinimide ester; Biotin-X-X-NHS; N-Succinimidyl N-[6-(biotinylamino)caproyl]-6-aminocaproate; Biotinamidohexanoyl-6-aminohexanoic acid N-hydroxysuccinimide ester; N-Biotinylcaproylaminocaproyl N-Hydroxysuccinimide6-(biotinamidecaproylamide)caproic acid N-succinimide ester6-{6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-hexanoic acid 2,5-dioxo-pyrrolidin-1-yl ester; Succinimidyl-6-[6-(biotinamido)caproyl]caproylate

Database IDs

• CAS Number: 89889-52-1
• MDL Number: MFCD00467154
• Beilstein Number: 8377428
• PubChem SID: 24891708; 162228432
• PubChem CID: 16219024

CALCULATED PROPERTIES

• Acid pKa: 13.486875
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.30806187
• LogD (pH = 7.4): 0.30806476
• Log P: 0.3080651
• Molar Refractivity: 143.5245 cm^3
• Polarizability: 56.47013 Å^3
• Polar Surface Area: 163.01 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF; DMF: soluble25 mg/mL; DMSO; NMP
• Apperance: powder; White Solid
• Melting Point: 147-151°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Moisture Sensitive
• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (TLC)

DETAILS

Sigma Aldrich - B3295

Application
Biotinylation reagent incorporating an extended 14-atom spacer can reduce steric hindrance in binding avidin or streptavidin to some biotinylated compounds and increase sensitivity for detection. Typically coupled to primary amine in the pH range 6.5-8.5.

Toronto Research Chemicals - S690255

A biotinylated cross-linking reagent.