[(2R)-2,3-bis(hexadecanoyloxy)propoxy]({2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]ethoxy})phosphinic acid

• ChemBase ID: 156471
• Molecular Formular: C43H75N4O11P
• Molecular Mass: 855.049561
• Monoisotopic Mass: 854.51699587
• SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCNc1ccc(c2c1non2)[N+](=O)[O-])OC(=O)CCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCC)COP(=O)(OCCNc1ccc(c2c1non2)[N+](=O)[O-])O
• InChI: InChI=1S/C43H75N4O11P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-40(48)54-35-37(57-41(49)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)36-56-59(52,53)55-34-33-44-38-31-32-39(47(50)51)43-42(38)45-58-46-43/h31-32,37,44H,3-30,33-36H2,1-2H3,(H,52,53)/t37-/m1/s1
• InChIKey: ODWMPKRLTCWGFP-DIPNUNPCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R)-2,3-bis(hexadecanoyloxy)propoxy]({2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]ethoxy})phosphinic acid
• IUPAC Traditional name: (2R)-2,3-bis(hexadecanoyloxy)propoxy(2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]ethoxy)phosphinic acid
• Synonyms: 2(R),3-dipalmitoylglycero-1 -phospho-N-(7-nitro-2,1,3-benzoxadiazo1-4-y1)ethanolamine; L-β,γ-Dipalmitoyl-α-cephaline, 7-nitrobenzofurazan-labeled; N-(7-Nitro-benzofurazan-4-yl)-1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine; N-(7-Nitrobenzofurazan-4-yl)-1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine; N-NBD-Dipalmitoyl-L-α-Phosphatidylethanolamine; NBD-PE; Phosphatidylethanolamine 16:0, NBD-labeled; 1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine, 7-nitrobenzofurazan-labeled

Database IDs

• CAS Number: 92605-64-6
• MDL Number: MFCD06798167
• PubChem SID: 162250609; 24847409
• PubChem CID: 16211229

CALCULATED PROPERTIES

• Acid pKa: 1.9037362
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): 10.470904
• LogD (pH = 7.4): 10.445923
• Log P: 12.821995
• Molar Refractivity: 230.7384 cm^3
• Polarizability: 90.81628 Å^3
• Polar Surface Area: 205.13 Å^2
• Rotatable Bonds: 42
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Fluorescence: λex 459 nm; λem 528 nm in methanol

Safety Information

• 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)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C43H75N4O11P

DETAILS

Sigma Aldrich - 12019

Application
Phosphatidylethanolamine 16:0 can be utilized as a lipid fluorescent probe to study the morphological stability of lipid membranes (to surfactants and ethanol) by monitoring its fluorescence.