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

• ChemBase ID: 169676
• Molecular Formular: C28H53NO8
• Molecular Mass: 531.72232
• Monoisotopic Mass: 531.37711766
• SMILES: O(C[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)NC(=O)CCC)[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)CO)O)O)O
• Canonical SMILES: CCCC(=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/C28H53NO8/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-18-22(31)21(29-24(32)17-4-2)20-36-28-27(35)26(34)25(33)23(19-30)37-28/h16,18,21-23,25-28,30-31,33-35H,3-15,17,19-20H2,1-2H3,(H,29,32)/b18-16+/t21-,22+,23+,25+,26-,27+,28+/m0/s1
• InChIKey: VSVGCPKEFVFBTE-HAJHVBEFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]butanamide
• IUPAC Traditional name: N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]butanamide
• Synonyms: [R-[R*,S*-(E)]]-N-[1-[(β-D-Glucopyranosyloxy)methyl]-2-hydroxy-3-heptadecenyl]butanamide; β-D-Glucosyl C4-Ceramide

Database IDs

• CAS Number: 111956-45-7
• PubChem SID: 162263808
• PubChem CID: 71317100

CALCULATED PROPERTIES

• Acid pKa: 12.175433
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): 3.7596946
• LogD (pH = 7.4): 3.7596884
• Log P: 3.7596955
• Molar Refractivity: 142.977 cm^3
• Polarizability: 57.06397 Å^3
• Polar Surface Area: 148.71 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 119-121°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - G596810

An inhibitor of human acid β-glucosidase.

REFERENCES

• Osiecki-Newman, K., et al.: Biochim. Biophysica Acta Protein Str. Mol. Enzym., 915, 87 (1987)