{[(2S,3R,4E)-2-acetamido-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid

• ChemBase ID: 163989
• Molecular Formular: C20H40NO6P
• Molecular Mass: 421.508461
• Monoisotopic Mass: 421.25932464
• SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(O)O)NC(=O)C)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)C)COP(=O)(O)O)O
• InChI: InChI=1S/C20H40NO6P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(23)19(21-18(2)22)17-27-28(24,25)26/h15-16,19-20,23H,3-14,17H2,1-2H3,(H,21,22)(H2,24,25,26)/b16-15+/t19-,20+/m0/s1
• InChIKey: HWPZKJVGDYNEAW-QUDYQQOWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4E)-2-acetamido-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid
• IUPAC Traditional name: C2-ceramide 1-phosphate
• Synonyms: N-[(1S,2R,3E)-2-Hydroxy-1-[(phosphonooxy)methyl]-3-heptadecenyl]acetamide; N-Acetylsphingosine-1-phosphate; C2 Ceramide-1-phosphate

Database IDs

• CAS Number: 151729-55-4
• PubChem SID: 162258124
• PubChem CID: 15199918

CALCULATED PROPERTIES

• Acid pKa: 1.5145464
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.857796
• LogD (pH = 7.4): 0.9788852
• Log P: 4.261861
• Molar Refractivity: 112.2087 cm^3
• Polarizability: 44.06107 Å^3
• Polar Surface Area: 116.09 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Beige Solid
• Melting Point: 132-134°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C262710

Ceramide-1-phosphate blocks apoptosis through inhibition of acid sphingomyelinase in macrophages.

REFERENCES

• Furukawa, A., et al.: Mol. Cell. Biochem., 305, 27 (2007)
• Chen-Quay, S., et al.: J. Pharm. Sci., 98, 606 (2007)