2,5-dioxopyrrolidin-1-yl octadecanoate

• ChemBase ID: 177863
• Molecular Formular: C22H39NO4
• Molecular Mass: 381.54936
• Monoisotopic Mass: 381.28790873
• SMILES: C1CC(=O)N(C1=O)OC(=O)CCCCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C22H39NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(26)27-23-20(24)18-19-21(23)25/h2-19H2,1H3
• InChIKey: ZERWDZDNDJBYKA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl octadecanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl octadecanoate
• Synonyms: DL-Stearoylcarnitine; O-Octadecanoyl-DL-carnitine; Stearoyl DL-Carnitine; Stearoyl-d,l-carnitine; Stearoyl Carnitine; 3-Carboxy-N,N,N-trimethyl-2-[(1-oxooctadecyl)oxy]-1-propanaminium Inner Salt; Octadecanoic Acid 2,5-Dioxo-1-pyrrolidinyl Ester; N-(Stearoyloxy)succinimide; Stearic Acid N-Hydroxysuccinimide Ester; N-Succinimidyl Stearate

Database IDs

• CAS Number: 1976-27-8; 14464-32-5
• PubChem SID: 164233773
• PubChem CID: 3552761

CALCULATED PROPERTIES

• Acid pKa: 17.709124
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 6.5153055
• LogD (pH = 7.4): 6.5153055
• Log P: 6.5153055
• Molar Refractivity: 106.8394 cm^3
• Polarizability: 42.56821 Å^3
• Polar Surface Area: 63.68 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White to Off-White Solid
• Melting Point: 92-93°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - S686515

A carnitine ester which was tested for its ability to inhibit protein kinase C (PKC).

REFERENCES

• Sakata, K., et al.: Cardiovasc. Res., 23, 505 (1989)
• Fulceri, R., et al.: Biochem. J., 325, 423 (1989)
• Yu, L., et al.: J. Pharmacol. Exp. Ther., 286, 1 (1989)