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

• ChemBase ID: 164004
• Molecular Formular: C42H83NO3
• Molecular Mass: 650.11332
• Monoisotopic Mass: 649.63729552
• SMILES: C(=C\[C@H]([C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC)O)/CCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)CO
• InChI: InChI=1S/C42H83NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-42(46)43-40(39-44)41(45)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h35,37,40-41,44-45H,3-34,36,38-39H2,1-2H3,(H,43,46)/b37-35+/t40-,41+/m0/s1
• InChIKey: ZJVVOYPTFQEGPH-AUTSUKAISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]tetracosanamide
• IUPAC Traditional name: C24 cer
• Synonyms: Lignoceric Ceramide; C24 Ceramide

Database IDs

• CAS Number: 34435-05-7
• PubChem SID: 162258139
• PubChem CID: 5283571

CALCULATED PROPERTIES

• Acid pKa: 13.619749
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 14.421903
• LogD (pH = 7.4): 14.421905
• Log P: 14.421905
• Molar Refractivity: 202.5837 cm^3
• Polarizability: 80.35759 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 38
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 83-85°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C263450

Production of ceramide occurs upon hydrolysis of sphingomyelin by a specific isoform of phospholipase C, appropriately named sphingomyelinase.

REFERENCES

• Gu, Q, et al.: Anal. Biochem., 244, 347 (1997)
• Perry, D.K., et al.: Trends Cardiovasc. Med., 6, 158 (1997)
• Clayton, R.B., et al.: J. Lipid Res., 15, 557 (1997)