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

• ChemBase ID: 132173
• Molecular Formular: C28H59N2O6P
• Molecular Mass: 550.751621
• Monoisotopic Mass: 550.41107425
• SMILES: CCCCCCCCCCCCCCCCCC(=O)NCC(COP(=O)([O-])OCC[N+](C)(C)C)OCC
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)NCC(COP(=O)(OCC[N+](C)(C)C)[O-])OCC
• InChI: InChI=1S/C28H59N2O6P/c1-6-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)29-25-27(34-7-2)26-36-37(32,33)35-24-23-30(3,4)5/h27H,6-26H2,1-5H3,(H-,29,31,32,33)
• InChIKey: QUVZKDZYEOYGKV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-[(2-ethoxy-3-octadecanamidopropyl phosphonato)oxy]ethyl}trimethylazanium
• IUPAC Traditional name: {2-[(2-ethoxy-3-octadecanamidopropyl phosphonato)oxy]ethyl}trimethylazanium
• Synonyms: 7-Ethoxy-4-hydroxy-N,N,N-trimethyl-10-oxo-3,5-dioxa-9-aza-4-phosphaheptacosan-1-aminium 4-oxide; rac-3-Octadecanamido-2-ethoxypropan-1-ol Phosphocholine; rac-2-Ethoxy-3-octadecanamido-1-propylphosphocholine

Database IDs

• CAS Number: 112989-02-3; 163702-18-9
• MDL Number: MFCD00270056
• PubChem SID: 24278419; 162226450
• PubChem CID: 72241

CALCULATED PROPERTIES

• Acid pKa: 1.8610845
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.376156
• LogD (pH = 7.4): 4.3762536
• Log P: 3.4547775
• Molar Refractivity: 162.9253 cm^3
• Polarizability: 60.670437 Å^3
• Polar Surface Area: 96.92 Å^2
• Rotatable Bonds: 27
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Colourless Amorphous Solid

Safety Information

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

Pharmacology Properties

• Gene Information: human ... PRKCA(5578), PRKCB(5579), PRKCD(5580), PRKCE(5581), PRKCG(5582), PRKCH(5583), PRKCI(5584)

Product Information

• Impurities: ≤0.5 mol/mol (NH4)2CO3

DETAILS

Sigma Aldrich - E3770

Biochem/physiol Actions
Protein kinase C inhibitor.

Toronto Research Chemicals - O234000

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

REFERENCES

• Liu, D., et al.: J. Pharm. Sci., 88, 1169 (1999)
• Ouyang, H., et al.: J. Med. Chem., 45, 2857 (1999)