(2S,3R,4S,5R,6R)-2-{[(2S,3R,4E)-2-amino-3-[(tert-butyldimethylsilyl)oxy]octadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 169555
• Molecular Formular: C30H61NO7Si
• Molecular Mass: 575.89334
• Monoisotopic Mass: 575.42172983
• SMILES: O1[C@H](OC[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C)N)[C@H]([C@H]([C@H]([C@@H]1CO)O)O)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO[C@H]1O[C@@H](CO)[C@@H]([C@@H]([C@@H]1O)O)O)N)O[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C30H61NO7Si/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-24(38-39(5,6)30(2,3)4)23(31)22-36-29-28(35)27(34)26(33)25(21-32)37-29/h19-20,23-29,32-35H,7-18,21-22,31H2,1-6H3/b20-19+/t23-,24+,25+,26-,27-,28+,29-/m0/s1
• InChIKey: QZWLHLCHICYAHX-ADRJBETJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5R,6R)-2-{[(2S,3R,4E)-2-amino-3-[(tert-butyldimethylsilyl)oxy]octadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,3R,4S,5R,6R)-2-{[(2S,3R,4E)-2-amino-3-[(tert-butyldimethylsilyl)oxy]octadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: α-Galactosyl-3-(t-butyldimethylsilyl) erythro-Sphingosine

Database IDs

• PubChem SID: 162263687
• PubChem CID: 71317032

CALCULATED PROPERTIES

• Acid pKa: 12.211172
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 1.4461126
• LogD (pH = 7.4): 2.9908533
• Log P: 4.6364
• Molar Refractivity: 154.1534 cm^3
• Polarizability: 64.035866 Å^3
• Polar Surface Area: 134.63 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Oil

DETAILS

Toronto Research Chemicals - G184875

Galactosylceramides play an important roles in promoting the regulation of nerve cells, regulating protein kinase C activities and modulating the function of the hormone receptor. It has shown to have significant immunostimulatory and anti-umor activity