(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-(1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18-13C18)octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 176204
• Molecular Formular: C42H82NO8P
• Molecular Mass: 777.94392808
• Monoisotopic Mass: 777.6381923
• SMILES: C([C@H](O[13C](=O)[13CH2][13CH2][13CH2][13CH2][13CH2][13CH2][13CH2]/[13CH]=[13CH]\[13CH2][13CH2][13CH2][13CH2][13CH2][13CH2][13CH2][13CH3])COC(=O)CCCCCCCCCCCCCCC)OP(=O)([O-])OCC[N+](C)(C)C
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@@H](O[13C](=O)[13CH2][13CH2][13CH2][13CH2][13CH2][13CH2][13CH2]/[13CH]=[13CH]\[13CH2][13CH2][13CH2][13CH2][13CH2][13CH2][13CH2][13CH3])COP(=O)(OCC[N+](C)(C)C)[O-]
• InChI: InChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,40H,6-19,22-39H2,1-5H3/b21-20-/t40-/m1/s1/i1+1,6+1,8+1,10+1,12+1,14+1,16+1,18+1,20+1,21+1,23+1,25+1,27+1,29+1,31+1,33+1,35+1,42+1
• InChIKey: WTJKGGKOPKCXLL-XZOYFXGWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-(1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18-^1^3C₁₈)octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-(1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18-^1^3C₁₈)octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: R-(Z)]-4-Hydroxy-N,N,N-trimethyl-9-oxo-7-[[(1-oxohexadecyl)oxy]methyl]-3,5,8-trioxa-4-phosphahexacos-17-en-1-aminium 4-Oxide-13C18; POPC-13C18; 1-Palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine-13C18

Database IDs

• PubChem SID: 164232114
• PubChem CID: 71751453

CALCULATED PROPERTIES

• Acid pKa: 1.8550572
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 10.6645155
• LogD (pH = 7.4): 10.664612
• Log P: 8.641012
• Molar Refractivity: 226.1837 cm^3
• Polarizability: 85.82576 Å^3
• Polar Surface Area: 111.19 Å^2
• Rotatable Bonds: 41
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Yellow Solid
• Melting Point: 217-219°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P161003

Labelled glycerophospholipids act as regulators of various enzyme activities, and can be used as biological markers to indicate pathological states.

REFERENCES

• Perides, G., et al.: J. Biol. Chem., 262, 13742 (1987)