N-[(2S,3S)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide

• ChemBase ID: 163994
• Molecular Formular: C34H67NO3
• Molecular Mass: 537.90068
• Monoisotopic Mass: 537.51209501
• SMILES: O[C@@H](C=CCCCCCCCCCCCCC)[C@@H](NC(=O)CCCCCCCCCCCCCCC)CO
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)N[C@H]([C@H](C=CCCCCCCCCCCCCC)O)CO
• InChI: InChI=1S/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)32(31-36)35-34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)/t32-,33-/m0/s1
• InChIKey: YDNKGFDKKRUKPY-LQJZCPKCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3S)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide
• IUPAC Traditional name: N-[(2S,3S)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide
• Synonyms: N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-hexadecanamide; (2S,3R,4E)-2-N-Palmitoyloctadecasphinga-4-ene; D-erythro-C16-Ceramide; D-erythro-N-Hexadecanoylsphingenine; D-erythro-N-Palmitoylsphingosine; D-erythro-4-Ceramide; N-Hexadecanoyl-D-erythro-ceramide; N-Palmitoyl 4-sphingenine; N-Palmitoyl-D-erythro-sphingosine; N-Palmitoyl-D-sphingosine; N-Palmitoylsphingosinee; C16-Ceramide

Database IDs

• CAS Number: 24696-26-2
• PubChem SID: 162258129
• PubChem CID: 71314645

CALCULATED PROPERTIES

• Acid pKa: 13.619749
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 10.865354
• LogD (pH = 7.4): 10.865355
• Log P: 10.8653555
• Molar Refractivity: 165.7757 cm^3
• Polarizability: 65.59229 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 30
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 98-99°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C262900

A predominant, rather hydrophobic natural ceramide. Activates a cytosolic serine/threonine protein phosphatase in T9 cells; induces EGF receptor phosphorylation in A-431 cells; stimulates ceramide-activated protein kinase.

REFERENCES

• Shoyama, Y., et al.: J. Lipid Res., 19, 250 (1978)
• Mathias, S., et al.: Proc. Natl. Sci. USA, 88, 10009 (1978)
• Dobrowsky, R.T., et al.: J. Biol. Chem., 267, 5048 (1992)