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]octanamide

• ChemBase ID: 169559
• Molecular Formular: C32H61NO8
• Molecular Mass: 587.82864
• Monoisotopic Mass: 587.43971792
• 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)CCCCCCC)O)O)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)CCCCCCC)CO[C@@H]1O[C@@H](CO)[C@@H]([C@@H]([C@@H]1O)O)O)O
• InChI: InChI=1S/C32H61NO8/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-26(35)25(33-28(36)22-20-17-8-6-4-2)24-40-32-31(39)30(38)29(37)27(23-34)41-32/h19,21,25-27,29-32,34-35,37-39H,3-18,20,22-24H2,1-2H3,(H,33,36)/b21-19+/t25-,26+,27+,29-,30-,31+,32+/m0/s1
• InChIKey: LCEXEEHGNKGJES-SWMJIITPSA-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]octanamide
• IUPAC Traditional name: C8 β-D-galactosylceramide
• Synonyms: N-[(1S,2R,3E)-1-[(β-D-Galactopyranosyloxy)methyl]-2-hydroxy-3-heptadecenyl]octanamide; N-[1-[(β-D-Galactopyranosyloxy)methyl]-2-hydroxy-3-heptadecenyl] octanamide; Galactosyl-β1'1-C8-ceramide; Galactosyl-C8-ceramide-3H

Database IDs

• PubChem SID: 162263691
• PubChem CID: 56927988

CALCULATED PROPERTIES

• Acid pKa: 12.183273
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): 5.5379686
• LogD (pH = 7.4): 5.537963
• Log P: 5.53797
• Molar Refractivity: 161.381 cm^3
• Polarizability: 64.40954 Å^3
• Polar Surface Area: 148.71 Å^2
• Rotatable Bonds: 25
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: Radioisotope Lab

DETAILS

Toronto Research Chemicals - G185000

A mixture of Type I (containing a-hydroxy fatty acid) and Type II (containing non-hydroxy fatty acid) cerebrosides. Galactose linked to ceramide by a β-glycosidic linkage; the major lipid in adult brain, representing approximately 16% of total lipid

REFERENCES

• Suzuki, K., et al.: Proc. Natl. Acad. Sci. USA, 66, 302 (1970), Suzuki, K., et al.: Methods Enzymology, 50, 468 (1978), Leskawa, K.C., et al.: Anal. Biochem., 140, 172 (1984),