(2S,3R,4E)-2-amino-3-[(tert-butyldimethylsilyl)oxy]octadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphate

• ChemBase ID: 163402
• Molecular Formular: C29H63N2O5PSi
• Molecular Mass: 578.880181
• Monoisotopic Mass: 578.42438629
• SMILES: C(CCCCCCCCCCC/C=C/[C@H]([C@@H](N)COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)C
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(OCC[N+](C)(C)C)[O-])N)O[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C29H63N2O5PSi/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-28(36-38(8,9)29(2,3)4)27(30)26-35-37(32,33)34-25-24-31(5,6)7/h22-23,27-28H,10-21,24-26,30H2,1-9H3/b23-22+/t27-,28+/m0/s1
• InChIKey: VHUANLHPOICHQL-YYKWJWRYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4E)-2-amino-3-[(tert-butyldimethylsilyl)oxy]octadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphate
• IUPAC Traditional name: (2S,3R,4E)-2-amino-3-[(tert-butyldimethylsilyl)oxy]octadec-4-en-1-yl 2-(trimethylammonio)ethyl phosphate
• Synonyms: 3-O-tert-Butyldimethylsilyl-D-erythro-sphingosylphosphorylcholine

Database IDs

• CAS Number: 168411-99-2
• PubChem SID: 162257537
• PubChem CID: 45038517

CALCULATED PROPERTIES

• Acid pKa: 1.8297472
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.3262972
• LogD (pH = 7.4): 2.506089
• Log P: 1.4699274
• Molar Refractivity: 169.9063 cm^3
• Polarizability: 65.504265 Å^3
• Polar Surface Area: 93.84 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Colourless Oil

DETAILS

Toronto Research Chemicals - B691675

Involved in cell regulation, and transmembrane signaling. A putative lipid second messenger, connected via Protein Kinase C to the phosphatidylinositol-derived second messengers for signal transduction.

REFERENCES

• Kratzer, B. and Schmidt, R.R.: Liebigs Ann., 955-963 (1995)