4-nitrophenyl 2-(trimethylazaniumyl)ethyl phosphate

• ChemBase ID: 133024
• Molecular Formular: C11H17N2O6P
• Molecular Mass: 304.236241
• Monoisotopic Mass: 304.0824229
• SMILES: C[N+](C)(C)CCOP(=O)([O-])Oc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: [O-]P(=O)(Oc1ccc(cc1)[N+](=O)[O-])OCC[N+](C)(C)C
• InChI: InChI=1S/C11H17N2O6P/c1-13(2,3)8-9-18-20(16,17)19-11-6-4-10(5-7-11)12(14)15/h4-7H,8-9H2,1-3H3
• InChIKey: NAIXASFEPQPICN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-nitrophenyl 2-(trimethylazaniumyl)ethyl phosphate
• IUPAC Traditional name: 4-nitrophenyl 2-(trimethylammonio)ethyl phosphate
• Synonyms: p-Nitrophenylphosphorylcholine; NPCC; Phosphocholine 4-nitrophenyl ester; O-(4-Nitrophenylphosphoryl)choline; 2-[[Hydroxy(4-nitrophenoxy)phosphinyl]oxy]-N,N,N-trimethyl-ethanaminium Inner Salt; 4-Nitrophenylphosphorylcholine

Database IDs

• CAS Number: 21064-69-7
• MDL Number: MFCD00077834
• Beilstein Number: 1895422
• PubChem SID: 24897755; 162227301
• PubChem CID: 4307994

CALCULATED PROPERTIES

• Acid pKa: 1.3335391
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.78635997
• LogD (pH = 7.4): -0.786331
• Log P: -2.8099318
• Molar Refractivity: 83.5298 cm^3
• Polarizability: 28.030464 Å^3
• Polar Surface Area: 104.41 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, faintly yellow; Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: 233-235°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (TLC)
• Impurities: ≤5% water
• Empirical Formula (Hill Notation): C11H17N2O6P

DETAILS

Sigma Aldrich - N5879

Application
Reported to be useful in assay of Phospholipase C.

Sigma Aldrich - 73739

Other Notes
Assay of phospholipase C1,2

REFERENCES

• Biochem., 11, 766 (1972)