[2-({2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(hexadecanoyloxy)propyl phosphonato}oxy)ethyl]trimethylazanium

• ChemBase ID: 176191
• Molecular Formular: C46H80NO8P
• Molecular Mass: 806.103061
• Monoisotopic Mass: 805.56215516
• SMILES: O(C(=O)CC/C=C\C/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)CC/C=C\C/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/C46H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-19-17-15-13-11-9-7-2/h8,10,14,16,20-21,23-24,27,29,33,35,44H,6-7,9,11-13,15,17-19,22,25-26,28,30-32,34,36-43H2,1-5H3/b10-8-,16-14-,21-20-,24-23-,29-27-,35-33-
• InChIKey: IESVDEZGAHUQJU-SYGPSSPWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-({2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(hexadecanoyloxy)propyl phosphonato}oxy)ethyl]trimethylazanium
• IUPAC Traditional name: [2-({2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(hexadecanoyloxy)propyl phosphonato}oxy)ethyl]trimethylazanium
• Synonyms: (7R,12Z,15Z,18Z,21Z,24Z,27Z)-4-Hydroxy-N,N,N-trimethyl-9-oxo-7-[[(1-oxohexadecyl)oxy]methyl]-3,5,8-trioxa-4-phosphatriaconta-12,15,18,21,24,27-hexaen-1-aminium 4-Oxide; 1-Palmitoyl-2-docosahexaenoyl-sn-glycero-3-phosphocholine; Palmitoyldocosahexaenoylphosphatidylcholine; Palmitoyldocosahexaenoyl Phosphatidylcholine

Database IDs

• CAS Number: 59403-54-2
• PubChem SID: 164232101
• PubChem CID: 9940652

CALCULATED PROPERTIES

• Acid pKa: 1.8550572
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 10.633183
• LogD (pH = 7.4): 10.633279
• Log P: 8.609678
• Molar Refractivity: 250.1707 cm^3
• Polarizability: 91.98434 Å^3
• Polar Surface Area: 111.19 Å^2
• Rotatable Bonds: 40
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P156910

Possible Cholesterol Acetyltransferase inhibitor.

REFERENCES

• Zhao, S., et al.: J. Pharm. Biomed. Anal., 47, 343 (2008)
• Leonardi, R., et al.: J. Biol. Chem., 284, 27077 (2008)
• Nakanishi, H., et al.: J. Biochem., 147, 245 (2008)