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

• ChemBase ID: 90871
• Molecular Formular: C20H39NO3
• Molecular Mass: 341.52856
• Monoisotopic Mass: 341.29299411
• SMILES: O=C(N[C@H]([C@H](O)/C=C/CCCCCCCCCCCCC)CO)C
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)C)CO)O
• InChI: InChI=1S/C20H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(24)19(17-22)21-18(2)23/h15-16,19-20,22,24H,3-14,17H2,1-2H3,(H,21,23)/b16-15+/t19-,20+/m0/s1
• InChIKey: BLTCBVOJNNKFKC-QUDYQQOWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]acetamide
• IUPAC Traditional name: C2-ceramide
• Synonyms: C2 Ceeramide; N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]acetamide; N-Acetyl-D-sphingosine; Acetyl Ceramide; N-Acetylsphingosine; C2 Ceramide

Database IDs

• CAS Number: 3102-57-6
• MDL Number: MFCD00153903
• PubChem SID: 162077580
• PubChem CID: 5497136

CALCULATED PROPERTIES

• Acid pKa: 13.590839
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.3854265
• LogD (pH = 7.4): 4.3854265
• Log P: 4.3854265
• Molar Refractivity: 101.3358 cm^3
• Polarizability: 39.77093 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: White Solid
• Melting Point: 87-89°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Apollo Scientific Ltd - OR6251T

A biologically active, cell permeable, non-physiological ceramide analog. It inhibits cell proliferation, induces monocytic differentiation of HL-60 cells & inducesapoptosis.

Toronto Research Chemicals - C262500

A biologically active, cell permeable, but nonphysiologic ceramide analog. It inhibits cell proliferation and induces monocytic differentiation of HL-60 cells and induces apoptosis. It stimulates protein phosphatase 2A and activates MAP Kinase2.

REFERENCES

• Inoue, T., et al.: J. Biol. Chem., 284, 9566 (2009)
• Kang, J., et al.: Bioorg. Med. Chem., 17, 1498 (2009)
• Rath, G., et al.: Int. J. Biochem. Cell Biol., 41, 1165 (2009)