2-(trimethylazaniumyl)ethyl [(9E)-octadec-9-enoyloxy]phosphonate

• ChemBase ID: 167963
• Molecular Formular: C23H46NO5P
• Molecular Mass: 447.588801
• Monoisotopic Mass: 447.31136021
• SMILES: C(=C\CCCCCCCC(=O)OP(=O)([O-])OCC[N+](C)(C)C)/CCCCCCCC
• Canonical SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)OP(=O)(OCC[N+](C)(C)C)[O-]
• InChI: InChI=1S/C23H46NO5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(25)29-30(26,27)28-22-21-24(2,3)4/h12-13H,5-11,14-22H2,1-4H3/b13-12+
• InChIKey: OKCYUHYFKODCNJ-OUKQBFOZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(trimethylazaniumyl)ethyl [(9E)-octadec-9-enoyloxy]phosphonate
• IUPAC Traditional name: 2-(trimethylammonio)ethyl (9E)-octadec-9-enoyloxyphosphonate
• Synonyms: 2-[[Hydroxy[[(9E)-1-oxo-9-octadecen-1-yl]oxy]phosphinyl]oxy]-N,N,N-trimethylethanaminium Inner Salt; 1-Elaidyl Phosphocholine

Database IDs

• PubChem SID: 162262096
• PubChem CID: 23046796

CALCULATED PROPERTIES

• Acid pKa: 0.79007506
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.387795
• LogD (pH = 7.4): 4.387803
• Log P: 2.364202
• Molar Refractivity: 135.8552 cm^3
• Polarizability: 49.383938 Å^3
• Polar Surface Area: 75.66 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E501000

Used in the nonenzymatic synthesis of glycerolipids catalyzed by imidazole.

REFERENCES

• Testet, E., et al.: J. Lipid Res., 43, 1150 (2002)