[(2R)-2,3-bis(octadec-9-enoyloxy)propoxy][2-(pyrene-1-sulfonamido)ethoxy]phosphinic acid

• ChemBase ID: 153593
• Molecular Formular: C57H86NO10PS
• Molecular Mass: 1008.332201
• Monoisotopic Mass: 1007.57100559
• SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCNS(=O)(=O)c1ccc2ccc3cccc4c3c2c1cc4)OC(=O)CCCCCCC/C=C/CCCCCCCC
• Canonical SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC/C=C/CCCCCCCC)COP(=O)(OCCNS(=O)(=O)c1ccc2c3c1ccc1c3c(cc2)ccc1)O
• InChI: InChI=1S/C57H86NO10PS/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-36-54(59)65-46-51(68-55(60)37-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)47-67-69(61,62)66-45-44-58-70(63,64)53-43-41-50-39-38-48-34-33-35-49-40-42-52(53)57(50)56(48)49/h17-20,33-35,38-43,51,58H,3-16,21-32,36-37,44-47H2,1-2H3,(H,61,62)/t51-/m1/s1
• InChIKey: VQMRCQVKHOAKOB-NLXJDERGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R)-2,3-bis(octadec-9-enoyloxy)propoxy][2-(pyrene-1-sulfonamido)ethoxy]phosphinic acid
• IUPAC Traditional name: (2R)-2,3-bis(octadec-9-enoyloxy)propoxy(2-(pyrene-1-sulfonamido)ethoxy)phosphinic acid
• Synonyms: L-β,γ-Dioleoyl-α-cephaline, pyrene-labeled; N-(1-Pyrenesulfonyl)-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine; Phosphatidylethanolamine 18:1, pyrene-labeled; 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine, pyrene-labeled; 18:1 Pyrene PE; Pyrene oleoyl phosphatidylethanolamine; 1,2-Dioleoyl-sn-glycero-3-phospho-[N-(1-pyrenesulfonyl)ethanolamine]

Database IDs

• MDL Number: MFCD02259237
• PubChem SID: 24886438; 162247732
• PubChem CID: 16218453

CALCULATED PROPERTIES

• Acid pKa: 1.9034181
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 13.9029045
• LogD (pH = 7.4): 13.876668
• Log P: 16.254028
• Molar Refractivity: 285.4995 cm^3
• Polarizability: 116.35483 Å^3
• Polar Surface Area: 154.53 Å^2
• Rotatable Bonds: 43
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Fluorescence: λex 323 nm; λem 378 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)
• Suitability: suitable for fluorescence
• Shipped in: dry ice
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C57H86NNaO10PS; C57H86NO10PS

DETAILS

Sigma Aldrich - P4615

Application
Fluorescent phospholipid probe useful in studies of bilayer mobilities.