(2-hexadecanamido-4-nitrophenoxy)[2-(trimethylazaniumyl)ethoxy]phosphinic acid oxidanide

• ChemBase ID: 169908
• Molecular Formular: C27H50N3O8P
• Molecular Mass: 575.674961
• Monoisotopic Mass: 575.33355221
• SMILES: C(CCCCCCCCCCCCCC(=O)Nc1cc(ccc1OP(=O)(OCC[N+](C)(C)C)O)[N+](=O)[O-])C.[OH-]
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)Nc1cc(ccc1OP(=O)(OCC[N+](C)(C)C)O)[N+](=O)[O-].[OH-]
• InChI: InChI=1S/C27H48N3O7P.H2O/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-27(31)28-25-23-24(29(32)33)19-20-26(25)37-38(34,35)36-22-21-30(2,3)4;/h19-20,23H,5-18,21-22H2,1-4H3,(H-,28,31,34,35);1H2
• InChIKey: CDTKXKMMWVIQDN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-hexadecanamido-4-nitrophenoxy)[2-(trimethylazaniumyl)ethoxy]phosphinic acid oxidanide
• IUPAC Traditional name: 2-hexadecanamido-4-nitrophenoxy(2-(trimethylammonio)ethoxy)phosphinic acid oxidanide
• Synonyms: 2-[[hydroxy[4-nitro-2-[(1-oxohexadecyl)amino]phenoxy]phosphinyl]oxy]-N,N,N-trimethyl-ethanaminium Hydroxide; 2-(N-Hexadecanoylamino)-4-nitrophenylphosphocholine Hydroxide

Database IDs

• CAS Number: 60438-73-5
• PubChem SID: 162264040
• PubChem CID: 173737

CALCULATED PROPERTIES

• Acid pKa: 1.292133
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 5.5812817
• LogD (pH = 7.4): 5.581298
• Log P: 3.557707
• Molar Refractivity: 163.9544 cm^3
• Polarizability: 58.65636 Å^3
• Polar Surface Area: 130.68 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 165-169°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - H293580

Reported to be useful in detection and diagnosis of Niemann-Pick disease in humans.

REFERENCES

• Brady, R.O., et al.: Proc. Natl. Acad. Sci. USA, 55, 366 (1966)
• Gal, A.E., et al.: New England J. Med., 293, 632 (1966)