hexadecyl 2-(trimethylazaniumyl)ethyl phosphate

• ChemBase ID: 154497
• Molecular Formular: C21H46NO4P
• Molecular Mass: 407.568001
• Monoisotopic Mass: 407.31644559
• SMILES: CCCCCCCCCCCCCCCCOP(=O)([O-])OCC[N+](C)(C)C
• Canonical SMILES: CCCCCCCCCCCCCCCCOP(=O)(OCC[N+](C)(C)C)[O-]
• InChI: InChI=1S/C21H46NO4P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-25-27(23,24)26-21-19-22(2,3)4/h5-21H2,1-4H3
• InChIKey: PQLXHQMOHUQAKB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: hexadecyl 2-(trimethylazaniumyl)ethyl phosphate
• IUPAC Traditional name: miltex
• Synonyms: Choline hexadecyl phosphate; HePC; Hexadecyl phosphocholine; Miltefosine; Miltefosine (Hexadecylphosphocholine); 2-[[(Hexadecyloxy)hydroxyphosphinyl]oxy]-N,N,N-trimethylethanaminium; Hexadecylphosphocholine; Hexadecylphosphorylcholine; Miltefosine; Miltex; n-Hexadecylphosphocholine; n-Hexadecylphosphorylcholine; Miltefosine

Database IDs

• CAS Number: 58066-85-6
• MDL Number: MFCD00133396
• PubChem SID: 162248636
• PubChem CID: 3599

CALCULATED PROPERTIES

• Acid pKa: 1.8803148
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.2743464
• LogD (pH = 7.4): 4.2744484
• Log P: 2.2508485
• Molar Refractivity: 125.5131 cm^3
• Polarizability: 45.86225 Å^3
• Polar Surface Area: 58.59 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble10 mg/mL, clear, colorless

Safety Information

• RTECS: KH2890000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-43
• Safety Statements: 36/37
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H334
• GHS Precautionary statements: P261-P301 + P310-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: room temp

Pharmacology Properties

• Target: Akt

Product Information

• Purity: ≥98% (perchloric acid titration)
• Salt Data: Free Base
• Description: zwitterionic
• Empirical Formula (Hill Notation): C21H46NO4P

DETAILS

Sigma Aldrich - M5571

Biochem/physiol Actions
Inhibitor of protein kinase C and of phosphatidylcholine synthesis. Used for the treatment of visceral and cutaneous leishmaniasis. Active against metronidazole-resistant and -susceptible strains of Trichomonas vaginalis1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M5571.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - M344460

A phospholipid drug with antineoplastic and antiprotozoal/antifungal properties, also acts as an Akt inhibitor, and under investigation as a potential therapy against HIV infection.

REFERENCES

• Chugh, P., et al al.: Retrovirology, 5, 11 (2008)
• Dorio, T., et al.: Antimicrob. Agents Chemother., 52, 2855 (2008)