N-[(2S,3S,4R)-3,4-dihydroxy-1-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadecan-2-yl]hexacosanamide

• ChemBase ID: 154862
• Molecular Formular: C50H99NO9
• Molecular Mass: 858.32236
• Monoisotopic Mass: 857.73198375
• SMILES: CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)[C@@H]([C@@H](CCCCCCCCCCCCCC)O)O
• Canonical SMILES: CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H]([C@@H](CCCCCCCCCCCCCC)O)O)CO[C@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C50H99NO9/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-45(54)51-42(41-59-50-49(58)48(57)47(56)44(40-52)60-50)46(55)43(53)38-36-34-32-30-28-16-14-12-10-8-6-4-2/h42-44,46-50,52-53,55-58H,3-41H2,1-2H3,(H,51,54)/t42-,43+,44+,46-,47-,48-,49+,50-/m0/s1
• InChIKey: VQFKFAKEUMHBLV-BYSUZVQFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3S,4R)-3,4-dihydroxy-1-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadecan-2-yl]hexacosanamide
• IUPAC Traditional name: α-GalCer
• Synonyms: α-GalCer; α-Galactosylceramide; KRN7000; (2S,3S,4R)-1-O-(α-D-Galactosyl)-N-hexacosanoyl-2-amino-1,3,4-octadecanetriol; N-[(1S,2S,3R)-1-[(α-D-Galactopyranosyloxy)methyl]-2,3-dihydroxyheptadecyl]hexacosanamide; KRN7000

Database IDs

• CAS Number: 158021-47-7
• MDL Number: MFCD00939559
• PubChem SID: 162249000
• PubChem CID: 2826713

CALCULATED PROPERTIES

• Acid pKa: 12.162304
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): 12.671315
• LogD (pH = 7.4): 12.671309
• Log P: 12.671317
• Molar Refractivity: 244.5979 cm^3
• Polarizability: 98.39637 Å^3
• Polar Surface Area: 168.94 Å^2
• Rotatable Bonds: 44
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 0.2mg per ml PBS plus 0.5% Tween-20 and sonicate for 2hrs; Pyridine
• Apperance: White to Off-White Solid
• Melting Point: 125-130°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Hygroscopic
• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (TLC)
• Empirical Formula (Hill Notation): C50H99NO9

DETAILS

Toronto Research Chemicals - K660000

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)