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

• ChemBase ID: 163988
• Molecular Formular: C24H47NO3
• Molecular Mass: 399.62018968
• Monoisotopic Mass: 399.36230405
• SMILES: CCCCCCCCCCCCC/C=C/[C@H]([13C@H]([13CH2]O)NC(=O)CCCCC)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([13C@@H](NC(=O)CCCCC)[13CH2]O)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/i21+1,22+1
• InChIKey: NPRJSFWNFTXXQC-OBHPOFNMSA-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]hexanamide
• IUPAC Traditional name: N-[(2R,3R,4E)-1,3-dihydroxy(1,2-^1^3C₂,1,1-^2H₂)octadec-4-en-2-yl]hexanamide
• Synonyms: N-Hexanoy-D-sphingosine-13C2,d2; N-Caproyl-D-sphingosine-13C2,d2; Caproyl Ceramide-13C2,d2; C6 Ceramide-13C2,d2

Database IDs

• PubChem SID: 162258123
• PubChem CID: 46780961

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 Solid
• Melting Point: 69-72°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C262602

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

• Dobrowsky, R.T., et al.: J. Biol. Chem., 268, 15523 (1993)
• Raines, M.A., et al.: J. Biol. Chem., 268, 14572 (1993)
• Jarvis, W.D., et al.: Proc. Natl. Acad. Sci. USA, 91, 73 (1993)