N-[(2S,3R,4E)-3-hydroxy-1-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]hexadecanamide

• ChemBase ID: 169556
• Molecular Formular: C40H77NO8
• Molecular Mass: 700.04128
• Monoisotopic Mass: 699.56491843
• SMILES: [C@H]1([C@@H]([C@@H]([C@H](O[C@H]1CO)OC[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)NC(=O)CCCCCCCCCCCCCCC)O)O)O
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)CO[C@H]1O[C@@H](CO)[C@@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C40H77NO8/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(43)33(32-48-40-39(47)38(46)37(45)35(31-42)49-40)41-36(44)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,33-35,37-40,42-43,45-47H,3-26,28,30-32H2,1-2H3,(H,41,44)/b29-27+/t33-,34+,35+,37-,38-,39+,40-/m0/s1
• InChIKey: VJLLLMIZEJJZTE-KAQXTUTFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4E)-3-hydroxy-1-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]hexadecanamide
• IUPAC Traditional name: N-[(2S,3R,4E)-3-hydroxy-1-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]hexadecanamide
• Synonyms: GalCer; N-[(1S,2R,3E)-1-[(β-D-Dalactopyranosyloxy)methyl]-2-hydroxy-3-heptadecen-1-yl]hexadecanamide; α-Galactosyl-C16-ceramide

Database IDs

• CAS Number: 34324-89-5
• PubChem SID: 162263688
• PubChem CID: 71317033

CALCULATED PROPERTIES

• Acid pKa: 12.181224
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): 9.094518
• LogD (pH = 7.4): 9.094512
• Log P: 9.09452
• Molar Refractivity: 198.189 cm^3
• Polarizability: 79.121765 Å^3
• Polar Surface Area: 148.71 Å^2
• Rotatable Bonds: 33
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Tetrahydrofuran
• Apperance: White Solid
• Melting Point: 144-163°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G184930

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

REFERENCES

• Morita, M., et al.: J. Med. Chem., 38, 2176 (1995)
• Sakai, T., et al.: J. Med. Chem., 42, 1836 (1995)