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

• ChemBase ID: 133904
• Molecular Formular: C24H47NO3
• Molecular Mass: 397.63488
• Monoisotopic Mass: 397.35559437
• SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NC(=O)CCCCC)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)CCCCC)CO)O
• InChI: InChI=1S/C24H47NO3/c1-3-5-7-8-9-10-11-12-13-14-15-16-18-19-23(27)22(21-26)25-24(28)20-17-6-4-2/h18-19,22-23,26-27H,3-17,20-21H2,1-2H3,(H,25,28)/b19-18+/t22-,23+/m0/s1
• InChIKey: NPRJSFWNFTXXQC-QFWQFVLDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]hexanamide
• IUPAC Traditional name: C6 ceramide
• Synonyms: N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]hexanamide; N-Hexanoy-D-sphingosine; N-Hexanoylsphingosine; C6 Ceramide; C6 ceramide; Caproyl ceramide; N-Caproyl-D-sphingosine; N-Hexanoyl-D-sphingosine

Database IDs

• CAS Number: 124753-97-5
• MDL Number: MFCD00870174
• PubChem SID: 24895750; 162228181
• PubChem CID: 5702613

CALCULATED PROPERTIES

• Acid pKa: 13.63898
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 6.4196672
• LogD (pH = 7.4): 6.419668
• Log P: 6.4196687
• Molar Refractivity: 119.7657 cm^3
• Polarizability: 47.144634 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off White Powder
• Melting Point: 76-77°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (TLC)
• Biological Source: from synthetic

DETAILS

Sigma Aldrich - H6524

Biochem/physiol Actions
Cell-permeable analog of ceramide; stimulates protein phosphatase 2A; activates MAP kinase; induces apoptosis in human leukemia HL-60 cells

Toronto Research Chemicals - C262600

A biologically active, cell permeable, but nonphysiologic ceramide analog. It stimulates protein phosphatase 2A at concentrations as low as 10 nM and activiates MAP kinase. It induces apoptosis and inhibits glycoproptein traffic by the secretory pathway

REFERENCES

• Liu, Z., et al.: J. Neurochem., 106, 2463 (2008)
• Heakal, Y., et al.: Mol. Cancer Res., 7, 724 (2008)
• Chen-Quay, S., et al.: J. Pharm. Sci., 98, 606 (2008)
• Mahdy, A., et al.: Mol. Ther., 17, 430 (2008)