(2-bromoethoxy)({[(2S,3R,4E)-3-[(tert-butyldimethylsilyl)oxy]-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}octadec-4-en-1-yl]oxy})phosphinic acid

• ChemBase ID: 162874
• Molecular Formular: C41H65BrNO7PSi
• Molecular Mass: 822.920561
• Monoisotopic Mass: 821.34512859
• SMILES: C(CCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(OCCBr)O)NC(=O)OCC1c2c(c3c1cccc3)cccc2)O[Si](C)(C)C(C)(C)C)C
• Canonical SMILES: BrCCOP(=O)(OC[C@@H]([C@H](O[Si](C(C)(C)C)(C)C)/C=C/CCCCCCCCCCCCC)NC(=O)OCC1c2ccccc2c2c1cccc2)O
• InChI: InChI=1S/C41H65BrNO7PSi/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-28-39(50-52(5,6)41(2,3)4)38(32-49-51(45,46)48-30-29-42)43-40(44)47-31-37-35-26-22-20-24-33(35)34-25-21-23-27-36(34)37/h19-28,37-39H,7-18,29-32H2,1-6H3,(H,43,44)(H,45,46)/b28-19+/t38-,39+/m0/s1
• InChIKey: VQQBGRQFDYYUJZ-WMMVGIRRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-bromoethoxy)({[(2S,3R,4E)-3-[(tert-butyldimethylsilyl)oxy]-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}octadec-4-en-1-yl]oxy})phosphinic acid
• IUPAC Traditional name: 2-bromoethoxy[(2S,3R,4E)-3-[(tert-butyldimethylsilyl)oxy]-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}octadec-4-en-1-yl]oxyphosphinic acid
• Synonyms: 2-Bromoethyl-1-[2-Fmoc-3-O-tert-butyldimethylsilyl]-D-erythro-sphingosylphosphate

Database IDs

• PubChem SID: 162257009
• PubChem CID: 45038447

CALCULATED PROPERTIES

• Acid pKa: 1.9175297
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 9.406352
• LogD (pH = 7.4): 9.386361
• Log P: 11.6499
• Molar Refractivity: 213.5019 cm^3
• Polarizability: 86.90897 Å^3
• Polar Surface Area: 103.32 Å^2
• Rotatable Bonds: 27
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Viscous Colourless Oil

DETAILS

Toronto Research Chemicals - B684240

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)