(15Z)-N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]tetracos-15-enamide

• ChemBase ID: 164006
• Molecular Formular: C42H81NO3
• Molecular Mass: 648.09744
• Monoisotopic Mass: 647.62164546
• SMILES: C(C/C=C/[C@H]([C@H](CO)NC(=O)CCCCCCCCCCCCC/C=C\CCCCCCCC)O)CCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)CCCCCCCCCCCCC/C=C\CCCCCCCC)CO)O
• InChI: InChI=1S/C42H81NO3/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/h17-18,35,37,40-41,44-45H,3-16,19-34,36,38-39H2,1-2H3,(H,43,46)/b18-17-,37-35+/t40-,41+/m0/s1
• InChIKey: VJSBNBBOSZJDKB-KPEYJIHVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (15Z)-N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]tetracos-15-enamide
• IUPAC Traditional name: N-(15Z-tetracosenoyl)-ceramide
• Synonyms: Nervonic Ceramide; C24:1 Ceramide; (15Z)-N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-15-tetracosenamide; C24:1-Ceramide; D-erythro-1,3-Dihydroxy-2-(cis-15-tetra-cosenoylamido)-trans-4-octadecene; N-cis-15-Tetracosenoyl-C18-sphingosine; Nervonyl Ceramide; N-[cis-Tetracosenoyl]-D-sphingosine; N-Nervonoyl-D-sphingosine

Database IDs

• CAS Number: 54164-50-0; 54165-50-0
• PubChem SID: 162258141
• PubChem CID: 5283568

CALCULATED PROPERTIES

• Acid pKa: 13.619749
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 14.059981
• LogD (pH = 7.4): 14.059982
• Log P: 14.059983
• Molar Refractivity: 203.7003 cm^3
• Polarizability: 80.12209 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 37
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-White Solid; White Solid
• Melting Point: 75-78°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N390100

N-Nervonoyl-D-sphingosine is a sphingolipid. Sphingolipids (SLs) act as signaling molecules and as structural components in both neuronal cells and myelin.

Toronto Research Chemicals - C263460

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

REFERENCES

• Bar, L., et al.: Biochemistry, 36, 2507 (1997)
• Carrer, D., et al: J. Lipid Res., 40, 1978 (1997)
• Grassme, H., et al.: J. Immunol., 168, 298 (1997)
• Castro, B., et al.: Biophys. J., 93, 1639 (1997)
• 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)