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

• ChemBase ID: 164005
• Molecular Formular: C44H87NO3
• Molecular Mass: 678.16648
• Monoisotopic Mass: 677.66859565
• SMILES: C(=C\[C@H]([C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCC)O)/CCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)CO
• InChI: InChI=1S/C44H87NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-44(48)45-42(41-46)43(47)39-37-35-33-31-29-27-16-14-12-10-8-6-4-2/h37,39,42-43,46-47H,3-36,38,40-41H2,1-2H3,(H,45,48)/b39-37+/t42-,43+/m0/s1
• InChIKey: CJROVRTUSFQVMR-GVOPMEMSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]hexacosanamide
• IUPAC Traditional name: C26 cer
• Synonyms: N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]hexacosanamide; [R-[R*,S*-(E)]]-N-[2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]hexacosanamide; C26 Ceramide

Database IDs

• CAS Number: 121459-09-4
• PubChem SID: 162258140
• PubChem CID: 5283570

CALCULATED PROPERTIES

• Acid pKa: 13.619749
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 15.31104
• LogD (pH = 7.4): 15.311042
• Log P: 15.311042
• Molar Refractivity: 211.7857 cm^3
• Polarizability: 84.04949 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 40
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C263455

Sphingolipid activator proteins are required for epidermal permeability barrier formation.

REFERENCES

• Tayama, M., et al.: Biochem. J., 290, 401 (1993)
• Holleran, W., et al.: J. Clin. Invest., 93, 1756 (1993)
• Wilkening, G., et al.: J. Biol. Chem., 273, 30271 (1993)