bis(2,5-dioxopyrrolidin-1-yl) 3,6,9,12,15,18,21-heptaoxatricosanedioate

• ChemBase ID: 169882
• Molecular Formular: C24H36N2O15
• Molecular Mass: 592.54704
• Monoisotopic Mass: 592.21156846
• SMILES: O(C(=O)COCCOCCOCCOCCOCCOCCOCC(=O)ON1C(=O)CCC1=O)N1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)COCCOCCOCCOCCOCCOCCOCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C24H36N2O15/c27-19-1-2-20(28)25(19)40-23(31)17-38-15-13-36-11-9-34-7-5-33-6-8-35-10-12-37-14-16-39-18-24(32)41-26-21(29)3-4-22(26)30/h1-18H2
• InChIKey: CMTBMPFLQYQNDF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(2,5-dioxopyrrolidin-1-yl) 3,6,9,12,15,18,21-heptaoxatricosanedioate
• IUPAC Traditional name: bis(2,5-dioxopyrrolidin-1-yl) 3,6,9,12,15,18,21-heptaoxatricosanedioate
• Synonyms: 3,6,9,12,15,18,21-Heptaoxatricosanedioic Acid 1,23-Bis(2,5-dioxo-1-pyrrolidinyl) Ester; 1,1'-[(1,23-Dioxo-3,6,9,12,15,18,21-heptaoxatricosane-1,23-diyl)bis(oxy)]bis-2,5-pyrrolidinedione; Heptaoxatricosanedioic Acid Bis(N-Hydroxysuccinimide) Ester

Database IDs

• CAS Number: 211746-85-9
• PubChem SID: 162264014
• PubChem CID: 10745994

CALCULATED PROPERTIES

• Acid pKa: 17.401377
• H Acceptors: 13
• H Donor: 0
• LogD (pH = 5.5): -2.4621663
• LogD (pH = 7.4): -2.4621663
• Log P: -2.4621663
• Molar Refractivity: 132.5503 cm^3
• Polarizability: 53.01325 Å^3
• Polar Surface Area: 191.97 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H282100

Used in the preparation of five sialyl Lewis x (sLex) dimers and five sLex carboxylic acids by coupling chemoenzymically synthesized amino-substituted sLex to homo-bifunctional cross-linkers of varying chain length. These compounds should be of importance

REFERENCES

• Norgard, K., et al.: J. Biol. Chem., 268, 12764 (1993)
• Lin, C., et al.: Bioorg. Med. Chem., 3, 1625 (1993)
• Steegmaier, M., et al.: Nature, 373, 615 (1993)
• Murray, B., et al.: Biochemistry, 35, 11183 (1993)