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

• ChemBase ID: 162072
• Molecular Formular: C28H36N4O8S
• Molecular Mass: 588.67244
• Monoisotopic Mass: 588.22538513
• SMILES: N1C(=O)N[C@@H]2[C@@H](SC[C@H]12)CCCCC(=O)NCCCCCC(=O)Oc1ccc(cc1)CC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)NCCCCCC(=O)Oc1ccc(cc1)CC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C28H36N4O8S/c33-22(7-4-3-6-21-27-20(17-41-21)30-28(38)31-27)29-15-5-1-2-8-25(36)39-19-11-9-18(10-12-19)16-26(37)40-32-23(34)13-14-24(32)35/h9-12,20-21,27H,1-8,13-17H2,(H,29,33)(H2,30,31,38)/t20-,21-,27-/m0/s1
• InChIKey: XOQZGRUKPCANAL-IZVMNLJQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}phenyl 6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanoate
• IUPAC Traditional name: 4-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}phenyl 6-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanoate
• Synonyms: BPE; 3-(4-(N-Biotinoyl-6-aminocaproyloxy)phenyl)propionic Acid, N-Hydroxysuccinimide Ester

Database IDs

• PubChem SID: 162256207
• PubChem CID: 71313977

CALCULATED PROPERTIES

• Acid pKa: 13.490655
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.4401362
• LogD (pH = 7.4): 1.4401375
• Log P: 1.4401379
• Molar Refractivity: 147.9189 cm^3
• Polarizability: 58.22019 Å^3
• Polar Surface Area: 160.21 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 177-179°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B391025

A reagent for covalently attaching Biotin to proteins via a cleavable connector arm.

REFERENCES

• Mouton, C.A., et al.: Archives of Biochemistry and Biophysics, 218, 1, 101 (1982)