1-tert-butyl 2,5-dioxopyrrolidin-1-yl (2S)-2-hexadecanamidopentanedioate

• ChemBase ID: 176192
• Molecular Formular: C29H50N2O7
• Molecular Mass: 538.7165
• Monoisotopic Mass: 538.36180195
• SMILES: O(C(=O)CC[C@@H](C(=O)OC(C)(C)C)NC(=O)CCCCCCCCCCCCCCC)N1C(=O)CCC1=O
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)N[C@H](C(=O)OC(C)(C)C)CCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C29H50N2O7/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(32)30-23(28(36)37-29(2,3)4)19-22-27(35)38-31-25(33)20-21-26(31)34/h23H,5-22H2,1-4H3,(H,30,32)/t23-/m0/s1
• InChIKey: MKJFKKLCCRQPHN-QHCPKHFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-tert-butyl 2,5-dioxopyrrolidin-1-yl (2S)-2-hexadecanamidopentanedioate
• IUPAC Traditional name: 1-tert-butyl 2,5-dioxopyrrolidin-1-yl (2S)-2-hexadecanamidopentanedioate
• Synonyms: Nε-Palmitoyl-Glu-γ-succinimidyl-α-tert-butyl Ester; (2S)-5-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-5-oxo-2-[(1-oxohexadecyl)amino]pentanoic Acid 1,1-Dimethylethyl Ester; Nε-Hexadecanoyl-L-glutamic Acid α-t-Butyl-γ-2,5-dioxopyrrolidin-1-yl-diester; Nε-Palmitoyl-L-glutamic Acid γ-Succinimidyl-α-tert-butyl Ester

Database IDs

• CAS Number: 204521-63-1
• PubChem SID: 164232102
• PubChem CID: 71751444

CALCULATED PROPERTIES

• Acid pKa: 12.417163
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 5.936352
• LogD (pH = 7.4): 5.9363484
• Log P: 5.9363523
• Molar Refractivity: 144.2999 cm^3
• Polarizability: 57.475918 Å^3
• Polar Surface Area: 119.08 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P157100

Used in the preparation of lipophilic human glucagon-like peptide-1 derivatives with protracted action profiles. An antiobesity agent.

REFERENCES

• Clodfelter., et al.: Pharmaceutical Res., 15, 254 (1998)