(2S,3R,4E)-2-amino-3-[(tert-butyldimethylsilyl)oxy]octadec-4-en-1-ol

• ChemBase ID: 163385
• Molecular Formular: C24H51NO2Si
• Molecular Mass: 413.75274
• Monoisotopic Mass: 413.36890641
• SMILES: OC[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C)N
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C24H51NO2Si/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(22(25)21-26)27-28(5,6)24(2,3)4/h19-20,22-23,26H,7-18,21,25H2,1-6H3/b20-19+/t22-,23+/m0/s1
• InChIKey: OFASSHVVQGEKIT-DWVLVAQTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4E)-2-amino-3-[(tert-butyldimethylsilyl)oxy]octadec-4-en-1-ol
• IUPAC Traditional name: (2S,3R,4E)-2-amino-3-[(tert-butyldimethylsilyl)oxy]octadec-4-en-1-ol
• Synonyms: (2S,3R,4E)-2-Amino-3-(tertbutyldimethylsilyloxy)-4-octadecene-1-ol; 3-O-(tert-Butyldimethylsilyloxy)-erythro-sphingosine

Database IDs

• CAS Number: 137905-29-4
• PubChem SID: 162257520
• PubChem CID: 10835568

CALCULATED PROPERTIES

• Acid pKa: 15.034957
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.516539
• LogD (pH = 7.4): 4.999565
• Log P: 6.7531
• Molar Refractivity: 121.7401 cm^3
• Polarizability: 50.492466 Å^3
• Polar Surface Area: 55.48 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Colourless Oil

DETAILS

Toronto Research Chemicals - B691595

A derivative of Sphingosine, a selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets; does not inhibit protein kinase A or myosin light chain kinase; inhibits calmodulin-dependent enzymes; natural isom