N-[(2R,3R,4E)-1,3-dihydroxy(1,2-13C2,1,1-2H2)octadec-4-en-2-yl]heptadecanamide

• ChemBase ID: 169879
• Molecular Formular: C35H69NO3
• Molecular Mass: 553.91256968
• Monoisotopic Mass: 553.53445475
• SMILES: O[13CH2][13C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)NC(=O)CCCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCCC(=O)N[13C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)[13CH2]O
• InChI: InChI=1S/C35H69NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-35(39)36-33(32-37)34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h28,30,33-34,37-38H,3-27,29,31-32H2,1-2H3,(H,36,39)/b30-28+/t33-,34+/m0/s1/i32+1,33+1
• InChIKey: ICWGMOFDULMCFL-ZWASHPJBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4E)-1,3-dihydroxy(1,2-^1^3C₂,1,1-^2H₂)octadec-4-en-2-yl]heptadecanamide
• IUPAC Traditional name: N-[(2R,3R,4E)-1,3-dihydroxy(1,2-^1^3C₂,1,1-^2H₂)octadec-4-en-2-yl]heptadecanamide
• Synonyms: N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]heptadecanamide-13C2,d2; N-Heptadecanoyl-D-erythro-sphingosine-13C2,d2

Database IDs

• PubChem SID: 162264011
• PubChem CID: 71317208

CALCULATED PROPERTIES

• Acid pKa: 13.619749
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 11.309922
• LogD (pH = 7.4): 11.309923
• Log P: 11.309924
• Molar Refractivity: 170.3767 cm^3
• Polarizability: 67.437706 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H281227

Sphingosine derivative from red algae of the Ceramiales. Sphingolipids, such as ceramides and cerebrosides, are important molecules in the formation and maintenance of the epidermal barrier to water vapor diffusion.

REFERENCES

• Vadas, P., et al.: J. Lipid Mediator, 8, 1 (1993)
• Balboa, M., et al.: J. Biol. Chem., 271, 32381 (1993)
• Koumanov, K., et al.: Biochem. J., 363, 45 (1993)
• Tietge, U., et al.: J. Lipid Res., 46, 1604 (1993)