(2-{[(2R)-3-(hexadecyloxy)-2-[(methylcarbamoyl)oxy]propyl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 134412
• Molecular Formular: C26H55N2O7P
• Molecular Mass: 538.697861
• Monoisotopic Mass: 538.37468874
• SMILES: CCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)NC
• Canonical SMILES: CCCCCCCCCCCCCCCCOC[C@@H](OC(=O)NC)COP(=O)(OCC[N+](C)(C)C)[O-]
• InChI: InChI=1S/C26H55N2O7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21-32-23-25(35-26(29)27-2)24-34-36(30,31)33-22-20-28(3,4)5/h25H,6-24H2,1-5H3,(H-,27,29,30,31)/t25-/m1/s1
• InChIKey: FNFHZBKBDFRYHS-RUZDIDTESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(2R)-3-(hexadecyloxy)-2-[(methylcarbamoyl)oxy]propyl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[(2R)-3-(hexadecyloxy)-2-[(methylcarbamoyl)oxy]propyl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: mcPAF(C16); mcPlatelet activating factor; 1-O-Palmitol-2-(N-methylcarbamyl)-sn-glycero-3-phosphocholine

Database IDs

• CAS Number: 91575-58-5
• MDL Number: MFCD00065891
• PubChem SID: 162228688; 24895650
• PubChem CID: 124663

CALCULATED PROPERTIES

• Acid pKa: 1.855053
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.9282978
• LogD (pH = 7.4): 3.928394
• Log P: 1.904794
• Molar Refractivity: 155.244 cm^3
• Polarizability: 57.711113 Å^3
• Polar Surface Area: 106.15 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble20 mg/mL
• Apperance: white powder

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% (TLC)

DETAILS

Sigma Aldrich - H4648

Biochem/physiol Actions
Nonhydrolyzable form of PAF[C16]. Activates platelets and exhibits potent inflammatory activity, mediator of cellular damage due to cerebral ischemia.
Other Notes
hygroscopic