1-(2-{[2,3-bis(hexadecanoyloxy)propyl phosphonato]oxy}ethyl)-2-[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl]pyridin-1-ium

• ChemBase ID: 158799
• Molecular Formular: C77H124NO8P
• Molecular Mass: 1222.784121
• Monoisotopic Mass: 1221.90645656
• SMILES: C1CCC(=C(C1(C)C)/C=C/C(=C/C=C/c1cc([n+](cc1)CCOP(=O)([O-])OCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)/C=C(/C=C/C=C(/C=C/C1=C(CCCC1(C)C)C)\C)\C)/C)C
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC(COP(=O)(OCC[n+]1ccc(cc1/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C)/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)[O-])COC(=O)CCCCCCCCCCCCCCC
• InChI: InChI=1S/C77H124NO8P/c1-12-14-16-18-20-22-24-26-28-30-32-34-36-48-74(79)83-62-71(86-75(80)49-37-35-33-31-29-27-25-23-21-19-17-15-13-2)63-85-87(81,82)84-59-58-78-57-54-69(47-39-43-65(4)51-53-73-68(7)46-41-56-77(73,10)11)61-70(78)60-66(5)44-38-42-64(3)50-52-72-67(6)45-40-55-76(72,8)9/h38-39,42-44,47,50-54,57,60-61,71H,12-37,40-41,45-46,48-49,55-56,58-59,62-63H2,1-11H3/b44-38+,47-39+,52-50+,53-51+,64-42+,65-43+,66-60+
• InChIKey: ZVFLDVACRJJJLS-IESNROCXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2-{[2,3-bis(hexadecanoyloxy)propyl phosphonato]oxy}ethyl)-2-[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl]pyridin-1-ium
• IUPAC Traditional name: 1-(2-{[2,3-bis(hexadecanoyloxy)propyl phosphonato]oxy}ethyl)-2-[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl]pyridin-1-ium
• Synonyms: 2-[(1E,3E,5E,7E)-2,6-Dimethyl-8-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,5,7-octatetraen-1-yl]-1-[4-hydroxy-4-oxido-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacos-1-yl]-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,5-hexatrien-1-yl]pyridinium; DP-A2-PE; A2-PE

Database IDs

• CAS Number: 863180-05-6
• PubChem SID: 162252934
• PubChem CID: 71312689

CALCULATED PROPERTIES

• Acid pKa: 1.8605561
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 17.156643
• LogD (pH = 7.4): 17.155268
• Log P: 18.331648
• Molar Refractivity: 375.5931 cm^3
• Polarizability: 145.3748 Å^3
• Polar Surface Area: 115.07 Å^2
• Rotatable Bonds: 49
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A101000

A2-PE is a pigment that forms as a byproduct of the visual cycle in vertebrates, which accumulates in retinal pigment epithelial cells over time leading to decline in cellular function.

REFERENCES

• Liu, J., et al.: J. Biol Chem., 38, 29354 (2000)
• McMahon, A., et al.: Mol. Vision, 13, 258 (2000)
• Kim, S., et al.: Exper. Eye Res., 82, 828 (2000)