N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]octadecanamide

• ChemBase ID: 177874
• Molecular Formular: C36H73NO4
• Molecular Mass: 583.96912
• Monoisotopic Mass: 583.55395982
• SMILES: [C@@H]([C@H]([C@H](CO)NC(=O)CCCCCCCCCCCCCCCCC)O)(O)CCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H]([C@@H](CCCCCCCCCCCCCC)O)O)CO
• InChI: InChI=1S/C36H73NO4/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-35(40)37-33(32-38)36(41)34(39)30-28-26-24-22-20-16-14-12-10-8-6-4-2/h33-34,36,38-39,41H,3-32H2,1-2H3,(H,37,40)/t33-,34+,36-/m0/s1
• InChIKey: IEZRNEGTKRQRFV-LFBNJJMOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]octadecanamide
• IUPAC Traditional name: N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]octadecanamide
• Synonyms: N-[(1S,2S,3R)-2,3-Dihydroxy-1-(hydroxymethyl)heptadecyl]octadecanamide; C18 3-Hydroxy Dihydroceramide; Ceramide III; Ceramide 3; DS-Ceramide Y3S; D-ribo-1,3,4-Trihydroxy-2-octadecanoylamidooctadecane; 2S,3S,4R-2-Stearoylamide-1,3,4-octadecanetriol; N-Stearoyl Phytosphingosine

Database IDs

• CAS Number: 34354-88-6
• PubChem SID: 164233784
• PubChem CID: 9898642

CALCULATED PROPERTIES

• Acid pKa: 13.262014
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 10.885602
• LogD (pH = 7.4): 10.885602
• Log P: 10.885603
• Molar Refractivity: 175.3766 cm^3
• Polarizability: 70.11686 Å^3
• Polar Surface Area: 89.79 Å^2
• Rotatable Bonds: 33
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S686585

An intercellular lipid that benefits skin hydration and protects against SLS irritation.

REFERENCES

• Yoshimura, Y., et al.: J. Biochem., 132, 229 (2002)
• Yilmaz, E., et al.: Int. J. Pharm., 307, 232 (2002)
• Huang, H., et al.: Int. J. Dermatol., 47, 812 (2002)