[(2R)-2,3-bis(hexadecanoyloxy)propoxy]({2-[({3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-yl}carbamothioyl)amino]ethoxy})phosphinic acid

• ChemBase ID: 169050
• Molecular Formular: C58H85N2O13PS
• Molecular Mass: 1081.339861
• Monoisotopic Mass: 1080.55099842
• SMILES: c1(cc2c(cc1)C1(c3c(O2)cc(cc3)O)c2c(cc(cc2)NC(=S)NCCOP(=O)(OC[C@H](OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC)O)C(=O)O1)O
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)O[C@@H](COP(=O)(OCCNC(=S)Nc1ccc2c(c1)C(=O)OC12c2ccc(cc2Oc2c1ccc(c2)O)O)O)COC(=O)CCCCCCCCCCCCCCC
• InChI: InChI=1S/C58H85N2O13PS/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-54(63)68-42-47(71-55(64)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)43-70-74(66,67)69-38-37-59-57(75)60-44-31-34-49-48(39-44)56(65)73-58(49)50-35-32-45(61)40-52(50)72-53-41-46(62)33-36-51(53)58/h31-36,39-41,47,61-62H,3-30,37-38,42-43H2,1-2H3,(H,66,67)(H2,59,60,75)/t47-/m1/s1
• InChIKey: LZNPLDBLBWZYIW-QZNUWAOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R)-2,3-bis(hexadecanoyloxy)propoxy]({2-[({3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-yl}carbamothioyl)amino]ethoxy})phosphinic acid
• IUPAC Traditional name: (2R)-2,3-bis(hexadecanoyloxy)propoxy(2-[({3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl}carbamothioyl)amino]ethoxy)phosphinic acid
• Synonyms: Fluorescein-Phosphatidylethanolamine; FPE; Hexadecanoic Acid 1,1'-[(1R)-1-[8-[(3',6'-Diihydroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-5-yl)amino]-3-hydroxy-3-oxido-8-thioxo-2,4-dioxa-7-aza-3-phosphaoct-1-yl]-1,2-ethanediyl] Ester; Hexadecanoic Acid (1R)-1-[8-[(3',6'-Dihydroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-5-yl)amino]-3-hydroxy-3-oxido-8-thioxo-2,4-dioxa-7-aza-3-phosphaoct-1-yl]-1,2-ethanediyl Ester; Fluorescein-Dipalmitoylphosphatidylethanolamine

Database IDs

• CAS Number: 87706-98-7
• PubChem SID: 162263182
• PubChem CID: 71316790

CALCULATED PROPERTIES

• Log P: 15.984016
• Molar Refractivity: 298.7325 cm^3
• Polarizability: 116.73751 Å^3
• Polar Surface Area: 208.41 Å^2
• Rotatable Bonds: 41
• Lipinski's Rule of Five: false
• Acid pKa: 1.9037269
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 13.632596
• LogD (pH = 7.4): 13.582061

DETAILS

Toronto Research Chemicals - F485500

Fluorescein-Dipalmitoylphosphatidylethanolamine is used as a real-time probe for peptide-membrane interactions.

REFERENCES

• Kachel, K. et al.: Biochim. Biophys. Acta Biomemb., 1374, 63 (1995)
• Wall, J.: Mol. Memb. Biol., 12, 183 (1995)