(2-{[3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 176190
• Molecular Formular: C44H78NO8P
• Molecular Mass: 780.065781
• Monoisotopic Mass: 779.54650509
• SMILES: O(C(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)C(COC(=O)CCCCCCCCCCCCCCC)COP(=O)(OCC[N+](C)(C)C)[O-]
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)COP(=O)(OCC[N+](C)(C)C)[O-]
• InChI: InChI=1S/C44H78NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h8,10,14,16,20-21,23,25,29,31,42H,6-7,9,11-13,15,17-19,22,24,26-28,30,32-41H2,1-5H3/b10-8-,16-14-,21-20-,25-23-,31-29-
• InChIKey: KLTHQSWIRFFBRI-KOQZQRJKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: (7R,13Z,16Z,19Z,22Z,25Z)-4-Hydroxy-N,N,N-trimethyl-9-oxo-7-[[(1-oxohexadecyl)oxy]methyl]-3,5,8-trioxa-4-phosphaoctacosa-13,16,19,22,25-pentaen-1-aminium 4-Oxide; 1-Palmitoyl-2-eicosapentaenoyl-sn-glycero-3-phosphocholine; Palmitoyleicosapentaenoyl Phosphatidylcholine

Database IDs

• CAS Number: 99296-77-2
• PubChem SID: 164232100
• PubChem CID: 24778724

CALCULATED PROPERTIES

• Acid pKa: 1.8550572
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 10.105967
• LogD (pH = 7.4): 10.106063
• Log P: 8.082462
• Molar Refractivity: 239.8521 cm^3
• Polarizability: 88.54119 Å^3
• Polar Surface Area: 111.19 Å^2
• Rotatable Bonds: 39
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Yellow Semi Solid

Safety Information

• Storage Condition: Amber Vial, -86?C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P156900

Possible Cholesterol Acetyltransferase inhibitor.

REFERENCES

• Newman, R., et al.: Brit. J. Nut., 88, 19 (2002)
• Shimada, Y., et al.: Biosci., Biotechnol., and Biochem., 67, 996 (2002)
• Zhao, S., et al.: J. Pharm. Biomed. Anal., 47, 343 (2002)