{2-[(2-methoxy-3-octadecanamidopropyl phosphonato)oxy]ethyl}trimethylazanium

• ChemBase ID: 134320
• Molecular Formular: C27H57N2O6P
• Molecular Mass: 536.725041
• Monoisotopic Mass: 536.39542418
• SMILES: CCCCCCCCCCCCCCCCCC(=O)NCC(COP(=O)([O-])OCC[N+](C)(C)C)OC
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)NCC(COP(=O)(OCC[N+](C)(C)C)[O-])OC
• InChI: InChI=1S/C27H57N2O6P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-27(30)28-24-26(33-5)25-35-36(31,32)34-23-22-29(2,3)4/h26H,6-25H2,1-5H3,(H-,28,30,31,32)
• InChIKey: KTJPWDKOKGANNX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-[(2-methoxy-3-octadecanamidopropyl phosphonato)oxy]ethyl}trimethylazanium
• IUPAC Traditional name: {2-[(2-methoxy-3-octadecanamidopropyl phosphonato)oxy]ethyl}trimethylazanium
• Synonyms: rac-2-Methoxy-3-octadecanamido-1-propylphosphocholine; 4-Hydroxy-7-methoxy-N,N,N-trimethyl-10-oxo-3,5-dioxa-9-aza-4-phosphaheptacosan-1-aminium 4-Oxide Hydrate; rac-3-Octadecanamido-2-Methoxypropan-1-ol Phosphocholine

Database IDs

• CAS Number: 163702-19-0
• MDL Number: MFCD00270057
• PubChem SID: 24897217; 162228597
• PubChem CID: 5030

CALCULATED PROPERTIES

• Acid pKa: 1.8610868
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.019348
• LogD (pH = 7.4): 4.019446
• Log P: 3.0979667
• Molar Refractivity: 158.1767 cm^3
• Polarizability: 58.83276 Å^3
• Polar Surface Area: 96.92 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Colourless Amorphous Solid

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: >96% (TLC)
• Impurities: ≤0.5 mol/mol (NH4)2CO3

DETAILS

Sigma Aldrich - M8045

Biochem/physiol Actions
Protein kinase C inhibitor.

Toronto Research Chemicals - O235000

Shows strong inhibitory action against neoplastic cell growth in vitro as well as inhibiting Protein Kinase C.

REFERENCES

• Marx, M.H., et al.: J. Med. Chem., 31, 858 (1988)