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

• ChemBase ID: 171308
• Molecular Formular: C36H71NO4
• Molecular Mass: 581.95324
• Monoisotopic Mass: 581.53830976
• SMILES: C(=C\[C@H]([C@H](CO)NC(=O)C(O)CCCCCCCCCCCCCCCC)O)/CCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCCC(C(=O)N[C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)CO)O
• InChI: InChI=1S/C36H71NO4/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-35(40)36(41)37-33(32-38)34(39)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h28,30,33-35,38-40H,3-27,29,31-32H2,1-2H3,(H,37,41)/b30-28+/t33-,34+,35?/m0/s1
• InChIKey: ZNZKGWLGVHSOIV-LVTSMTQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]-2-hydroxyoctadecanamide
• IUPAC Traditional name: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]-2-hydroxyoctadecanamide
• Synonyms: 2-Hydroxy-N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-octadecanamide; D-erythro-1,3-Dihydroxy-2-(2-DL-hydroxyoctadecanoylamido)-trans-4-octadecene; N-(2-Hydroxystearoyl) Sphingosine(Mixture of Diastereomers)

Database IDs

• CAS Number: 34249-41-7
• PubChem SID: 164227218
• PubChem CID: 71749343

CALCULATED PROPERTIES

• Acid pKa: 12.7914295
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 10.883427
• LogD (pH = 7.4): 10.883425
• Log P: 10.883427
• Molar Refractivity: 176.4699 cm^3
• Polarizability: 69.87874 Å^3
• Polar Surface Area: 89.79 Å^2
• Rotatable Bonds: 32
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H953535

It is used in the synthesis of new ceramides of human skin.

REFERENCES

• Aveldano, M., et al.: J. Lipid Res., 24, 1101 (1983)
• Mongrand, S., et al.: J. Biol. Chem., 279, 36277 (1983)
• Borner, G., et al.: Plant Physiol., 137, 104 (1983)