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

• ChemBase ID: 169558
• Molecular Formular: C42H81NO8
• Molecular Mass: 728.09444
• Monoisotopic Mass: 727.59621856
• SMILES: O(C[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)NC(=O)CCCCCCCCCCCCCCCCC)[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)CO)O)O)O
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=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/C42H81NO8/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-38(46)43-35(34-50-42-41(49)40(48)39(47)37(33-44)51-42)36(45)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,35-37,39-42,44-45,47-49H,3-28,30,32-34H2,1-2H3,(H,43,46)/b31-29+/t35-,36+,37+,39-,40-,41+,42+/m0/s1
• InChIKey: YMYQEDCYNANIPI-NMJNODIHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]octadecanamide
• IUPAC Traditional name: N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]octadecanamide
• Synonyms: N-[(1S,2R,3E)-1-[(β-D-Galactopyranosyloxy)methyl]-2-hydroxy-3-heptadecen-1-yl]-octadecanamide; C18-Cerebroside; β-Galactosyl-C18-ceramide

Database IDs

• CAS Number: 36271-49-5
• PubChem SID: 162263690
• PubChem CID: 10327583

CALCULATED PROPERTIES

• Acid pKa: 12.181224
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): 9.983655
• LogD (pH = 7.4): 9.983649
• Log P: 9.983657
• Molar Refractivity: 207.391 cm^3
• Polarizability: 82.80299 Å^3
• Polar Surface Area: 148.71 Å^2
• Rotatable Bonds: 35
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G184960

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. They have shown to have significant immunostimulatory and anti-umor activi

REFERENCES

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