(2-{[(2R)-3-hydroxy-2-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 175851
• Molecular Formular: C26H52NO7P
• Molecular Mass: 521.667341
• Monoisotopic Mass: 521.34813964
• SMILES: C([C@H](OC(=O)CCCCCCC/C=C\CCCCCCCC)CO)OP(=O)([O-])OCC[N+](C)(C)C
• Canonical SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)O[C@@H](COP(=O)(OCC[N+](C)(C)C)[O-])CO
• InChI: InChI=1S/C26H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)34-25(23-28)24-33-35(30,31)32-22-21-27(2,3)4/h12-13,25,28H,5-11,14-24H2,1-4H3/b13-12-/t25-/m1/s1
• InChIKey: SULIDBRAXVDKBU-PTGWMXDISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(2R)-3-hydroxy-2-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[(2R)-3-hydroxy-2-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: 2-Oleoyl-sn-glycero-3-phosphorylcholine; (7R,17Z)-4-Hydroxy-7-(hydroxymethyl)-N,N,N-trimethyl-9-oxo-3,5,8-trioxa-4-phosphahexacos-17-en-1-aminium 4-Oxide; 2-Oleoyl-sn-glycero-3-phosphocholine

Database IDs

• CAS Number: 22248-65-3
• PubChem SID: 164231761
• PubChem CID: 24779494

CALCULATED PROPERTIES

• Acid pKa: 1.8550618
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.7434618
• LogD (pH = 7.4): 3.7435582
• Log P: 1.7199582
• Molar Refractivity: 152.5923 cm^3
• Polarizability: 56.246002 Å^3
• Polar Surface Area: 105.12 Å^2
• Rotatable Bonds: 25
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - O528045

An intermediate in the biosynthesis of triacylglycerols by castor microsomes.

REFERENCES

• Yu, S., et al.: J. Agric. Food Chem., 54, 4482 (2006)
• Lessig, J., et al.: J. Lipid Res., 48, 1316 (2006)