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

• ChemBase ID: 163997
• Molecular Formular: C36H71NO3
• Molecular Mass: 565.95384
• Monoisotopic Mass: 565.54339514
• SMILES: C(C/C=C/[C@H]([C@H](CO)NC(=O)CCCCCCCCCCCCCCCCC)O)CCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)CO
• InChI: InChI=1S/C36H71NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38-39H,3-28,30,32-33H2,1-2H3,(H,37,40)/b31-29+/t34-,35+/m0/s1
• InChIKey: VODZWWMEJITOND-NXCSZAMKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]octadecanamide
• IUPAC Traditional name: C18 cer
• Synonyms: N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]octadecanamide; D-erythro-1,3-Dihydroxy-2-octadecanoylamido-trans-4-octadecene; N-Stearoyl-C18-sphingosine; N-Stearoyl-D-erythro-sphingosine; N-Stearoyl-D-sphingosine; N-Stearoylsphingenine; N-Stearoylsphingosine; C18 Ceramide

Database IDs

• CAS Number: 2304-81-6
• PubChem SID: 162258132
• PubChem CID: 5283565

CALCULATED PROPERTIES

• Acid pKa: 13.619749
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 11.754491
• LogD (pH = 7.4): 11.754492
• Log P: 11.754493
• Molar Refractivity: 174.9777 cm^3
• Polarizability: 69.2832 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 32
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White to Off White Solid
• Melting Point: 99-101°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C263050

The sphingolipid ceramide is a potent inhibitor of the mitochondrial permeability transition pore.

REFERENCES

• Aoyama, M., et al.: Biochem. J., 336, 727 (1998)
• Ghafourifar, P., et al.: J. Biol. Chem., 274, 6080 (1998)
• Montes, L., et al.: J. Biol. Chem., 277, 11788 (1998)
• Scorrano, L., et al.: Science, 300, 135 (1998)