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

• ChemBase ID: 163995
• Molecular Formular: C34H67NO3
• Molecular Mass: 539.88598968
• Monoisotopic Mass: 539.51880469
• SMILES: O[13CH2][13C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)NC(=O)CCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)N[13C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)[13CH2]O
• 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)/b29-27+/t32-,33+/m0/s1/i31+1,32+1
• InChIKey: YDNKGFDKKRUKPY-NWYDVTKGSA-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]hexadecanamide
• IUPAC Traditional name: N-[(2R,3R,4E)-1,3-dihydroxy(1,2-^1^3C₂,1,1-^2H₂)octadec-4-en-2-yl]hexadecanamide
• Synonyms: N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-hexadecanamide-13C2,d2; (2S,3R,4E)-2-N-Palmitoyloctadecasphinga-4-ene-13C2,d2; D-erythro-C16-Ceramide-13C2,d2; D-erythro-N-Hexadecanoylsphingenine-13C2,d2; D-erythro-N-Palmitoylsphingosine-13C2,d2; D-erythro-4-Ceramide-13C2,d2; N-Hexadecanoyl-D-erythro-ceramide-13C2,d2; N-Palmitoyl 4-sphingenine-13C2,d2; N-Palmitoyl-D-erythro-sphingosine-13C2,d2; N-Palmitoyl-D-sphingosine-13C2,d2; N-Palmitoylsphingosinee-13C2,d2; C16-Ceramide-13C2,d2

Database IDs

• PubChem SID: 162258130
• PubChem CID: 71314646

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

DETAILS

Toronto Research Chemicals - C262902

Labelled C16-Ceramide (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)