(2-{[(2R)-3-(hexadecanoyloxy)-2-{[10-(pyren-1-yl)decanoyl]oxy}propyl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 176181
• Molecular Formular: C50H76NO8P
• Molecular Mass: 850.114101
• Monoisotopic Mass: 849.53085503
• SMILES: c1c2c3c4c(c1)ccc(c4ccc3ccc2)CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(OCC[N+](C)(C)C)[O-]
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCc1ccc2c3c1ccc1c3c(cc2)ccc1)COP(=O)(OCC[N+](C)(C)C)[O-]
• InChI: InChI=1S/C50H76NO8P/c1-5-6-7-8-9-10-11-12-13-14-17-20-23-29-47(52)56-39-45(40-58-60(54,55)57-38-37-51(2,3)4)59-48(53)30-24-21-18-15-16-19-22-26-41-31-32-44-34-33-42-27-25-28-43-35-36-46(41)50(44)49(42)43/h25,27-28,31-36,45H,5-24,26,29-30,37-40H2,1-4H3/t45-/m1/s1
• InChIKey: ZZLOWUUVDRBGKM-WBVITSLISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(2R)-3-(hexadecanoyloxy)-2-{[10-(pyren-1-yl)decanoyl]oxy}propyl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[(2R)-3-(hexadecanoyloxy)-2-{[10-(pyren-1-yl)decanoyl]oxy}propyl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: (7R)-4-hydroxy-N,N,N-trimethyl-10-oxo-7-[[1-oxo-10-(1-pyrenyl)decyl]oxy]-3,5,9-Trioxa-4-phosphapentacosan-1-aminium Inner Salt 4-Oxide; 1-Hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphocholine; 3-Palmitoyl-2-(1-pyrenodecanoyl)-L-α-phosphatidylcholine; 1-Palmitoyl-2-pyrenedecanoylphosphatidylcholine

Database IDs

• CAS Number: 95864-17-8
• PubChem SID: 164232091
• PubChem CID: 196328

CALCULATED PROPERTIES

• Acid pKa: 1.8550572
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 11.358942
• LogD (pH = 7.4): 11.359038
• Log P: 9.335439
• Molar Refractivity: 253.6197 cm^3
• Polarizability: 99.961586 Å^3
• Polar Surface Area: 111.19 Å^2
• Rotatable Bonds: 36
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P155100

1-Palmitoyl-2-pyrenedecanoylphosphatidylcholine is a fluorescent phospholipid used to study the mechanism of spontaneous phospholipid transfer between single-walled phospholipid vesicles (liposomes) and other membrane interactions.

REFERENCES

• Roseman, M.A. et al.: Biochemistry, 19, 439 (1980)
• Pap, E.H.W. et al.: Biochemistry, 34, 9118 (1980)
• Csiszar, A. et al.: Bioconj. Chem., 21, 537 (1980)