N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]butanamide

• ChemBase ID: 163985
• Molecular Formular: C22H43NO3
• Molecular Mass: 369.58172
• Monoisotopic Mass: 369.32429424
• SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NC(=O)CCC)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)CCC)CO)O
• InChI: InChI=1S/C22H43NO3/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-18-21(25)20(19-24)23-22(26)17-4-2/h16,18,20-21,24-25H,3-15,17,19H2,1-2H3,(H,23,26)/b18-16+/t20-,21+/m0/s1
• InChIKey: UCBLGIBMIAFISC-CQLAPORSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]butanamide
• IUPAC Traditional name: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]butanamide
• Synonyms: N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]butanamide; N-Butyl-D-sphingosine; Butyl Ceramide; N-Butanoyl-D-erythro-sphingosine; C4 Ceramide

Database IDs

• CAS Number: 74713-58-9
• PubChem SID: 162258120
• PubChem CID: 5702612

CALCULATED PROPERTIES

• Acid pKa: 13.590225
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 5.5305305
• LogD (pH = 7.4): 5.530531
• Log P: 5.530531
• Molar Refractivity: 110.5637 cm^3
• Polarizability: 43.457222 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-white solid
• Melting Point: 64-67°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C262550

A ceramide derivative for pharmaceutical use as antitumor agents.

REFERENCES

• Dressler, K., et al.: Science, 255, 1715 (1992)
• Hannun, Y., et al.: J. Biol. Chem., 269, 3125 (1992)
• Chalfant, C., et al.: J. Lipid Res., 45, 496 (1992)