(2-{[2-(acetyloxy)-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 134031
• Molecular Formular: C28H56NO8P
• Molecular Mass: 565.719901
• Monoisotopic Mass: 565.37435439
• SMILES: CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)C
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)C)COP(=O)(OCC[N+](C)(C)C)[O-]
• InChI: InChI=1S/C28H56NO8P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-28(31)34-24-27(37-26(2)30)25-36-38(32,33)35-23-22-29(3,4)5/h27H,6-25H2,1-5H3
• InChIKey: ILLILTKBYHPOIA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[2-(acetyloxy)-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[2-(acetyloxy)-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: 1-O-Octadecyl-2-acetyl-sn-glycero-3-phosphocholine; PAF(C18); β-Acetyl-γ-O-octadecyl-L-α-phosphatidylcholine

Database IDs

• CAS Number: 79549-26-1
• MDL Number: MFCD00063528
• PubChem SID: 24898776; 162228308
• PubChem CID: 24778839

CALCULATED PROPERTIES

• Acid pKa: 1.8550572
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 4.546509
• LogD (pH = 7.4): 4.546605
• Log P: 2.5230052
• Molar Refractivity: 160.6272 cm^3
• Polarizability: 60.336746 Å^3
• Polar Surface Area: 111.19 Å^2
• Rotatable Bonds: 28
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: aqueous base: decomposes; chloroform: soluble10 mg/mL

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%

DETAILS

Sigma Aldrich - P6537

Biochem/physiol Actions
18-carbon analog of platelet activating factor (PAF); ligand for G protein-coupled PAF receptor. It is less potent than PAF C-16 for inducing platelet aggregation, hypotension, bronchosconstriction and chemotaxis, but more potent than PAF C-16 for inducing human neutrophil lysosomal secretion.