octadecyl 2-(trimethylazaniumyl)ethyl phosphate

• ChemBase ID: 153230
• Molecular Formular: C23H50NO4P
• Molecular Mass: 435.621161
• Monoisotopic Mass: 435.34774572
• SMILES: CCCCCCCCCCCCCCCCCCOP(=O)([O-])OCC[N+](C)(C)C
• Canonical SMILES: CCCCCCCCCCCCCCCCCCOP(=O)(OCC[N+](C)(C)C)[O-]
• InChI: InChI=1S/C23H50NO4P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-27-29(25,26)28-23-21-24(2,3)4/h5-23H2,1-4H3
• InChIKey: ZBNJXSZNWZUYCI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: octadecyl 2-(trimethylazaniumyl)ethyl phosphate
• IUPAC Traditional name: octadecyl 2-(trimethylammonio)ethyl phosphate
• Synonyms: Octadecylphosphocholine; Phosphocholine octadecyl ester; O-(Octadecylphosphoryl)choline

Database IDs

• CAS Number: 65956-63-0
• MDL Number: MFCD00171405
• Beilstein Number: 3694312
• PubChem SID: 162247369
• PubChem CID: 125219

CALCULATED PROPERTIES

• Acid pKa: 1.8803148
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.1634836
• LogD (pH = 7.4): 5.1635857
• Log P: 3.1399858
• Molar Refractivity: 134.7151 cm^3
• Polarizability: 49.54287 Å^3
• Polar Surface Area: 58.59 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (TLC)
• Empirical Formula (Hill Notation): C23H50NO4P

DETAILS

Sigma Aldrich - 04449

Application
Antitumor phospholipid3, induces apoptosis in three human leukemic cell lines4.
Biochem/physiol Actions
C18-phosphocholine was the most potent alkylphosphocholine tested in inhibiting phosphatidylcholine biosynthesis.1 The effect is mediated by interrupting the translocation of the rate-limiting enzyme, CTP:phosphocholine cytidylyltransferase, to membranes, where it is active.2