(2-{[(2R,3R,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 161077
• Molecular Formular: C23H47N4O5P
• Molecular Mass: 490.616841
• Monoisotopic Mass: 490.32840725
• SMILES: C(=C\[C@H]([C@@H](COP(=O)(OCC[N+](C)(C)C)[O-])N=[N+]=[N-])O)/CCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](COP(=O)(OCC[N+](C)(C)C)[O-])N=[N+]=[N-])O
• InChI: InChI=1S/C23H47N4O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(28)22(25-26-24)21-32-33(29,30)31-20-19-27(2,3)4/h17-18,22-23,28H,5-16,19-21H2,1-4H3/b18-17+/t22-,23-/m1/s1
• InChIKey: XNUUWIADFLHGET-GERLKTCDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(2R,3R,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[(2R,3R,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: Azido-3-hydroxy-1-trimethylaminoethylphosphoryl-erythro-sphingosine; Azidophosphorylsphingosylcholine

Database IDs

• PubChem SID: 162255212
• PubChem CID: 71313602

CALCULATED PROPERTIES

• Acid pKa: 1.8679304
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.5139642
• LogD (pH = 7.4): 3.5140631
• Log P: 1.6045089
• Molar Refractivity: 144.6932 cm^3
• Polarizability: 52.22327 Å^3
• Polar Surface Area: 108.25 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMF; Methanol
• Apperance: Waxy Solid

DETAILS

Toronto Research Chemicals - A925050

A derivative of Sphingosylphosphorylcholine, which is 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 transducti

REFERENCES

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