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

• ChemBase ID: 163998
• Molecular Formular: C36H71NO3
• Molecular Mass: 567.93914968
• Monoisotopic Mass: 567.55010481
• SMILES: C(/C=C/[C@H]([13C@@H](NC(=O)CCCCCCCCCCCCCCCCC)[13CH2]O)O)CCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)N[13C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)[13CH2]O
• 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/i33+1,34+1
• InChIKey: VODZWWMEJITOND-MNDRRKFSSA-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]octadecanamide
• IUPAC Traditional name: N-[(2R,3R,4E)-1,3-dihydroxy(1,2-^1^3C₂,1,1-^2H₂)octadec-4-en-2-yl]octadecanamide
• Synonyms: N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]octadecanamide-13C2,D2; D-erythro-1,3-Dihydroxy-2-octadecanoylamido-trans-4-octadecene-13C2,D2; N-Stearoyl-C18-sphingosine-13C2,D2; N-Stearoyl-D-erythro-sphingosine-13C2,D2; N-Stearoyl-D-sphingosine-13C2,D2; N-Stearoylsphingenine-13C2,D2; N-Stearoylsphingosine-13C2,D2; C18 Ceramide-13C2,D2

Database IDs

• PubChem SID: 162258133
• PubChem CID: 71314647

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 Solid
• Melting Point: 84-86°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C263052

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)