2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]cyclohexa-2,5-diene-1,4-dione

• ChemBase ID: 164887
• Molecular Formular: C49H74O4
• Molecular Mass: 727.10946
• Monoisotopic Mass: 726.55871085
• SMILES: C1(=C(C(=O)C(=C(C1=O)OC)OC)C)C/C=C(/CC/C=C(/CC/C=C(/CC/C=C(/CC/C=C(/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)\C)\C)\C)\C)\C
• Canonical SMILES: COC1=C(OC)C(=O)C(=C(C1=O)C/C=C(/CC/C=C(/CC/C=C(/CC/C=C(/CC/C=C(/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)\C)\C)\C)\C)\C)C
• InChI: InChI=1S/C49H74O4/c1-36(2)20-13-21-37(3)22-14-23-38(4)24-15-25-39(5)26-16-27-40(6)28-17-29-41(7)30-18-31-42(8)32-19-33-43(9)34-35-45-44(10)46(50)48(52-11)49(53-12)47(45)51/h20,22,24,26,28,30,32,34H,13-19,21,23,25,27,29,31,33,35H2,1-12H3/b37-22+,38-24+,39-26+,40-28+,41-30+,42-32+,43-34+
• InChIKey: ICFIZJQGJAJRSU-SGHXUWJISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]cyclohexa-2,5-diene-1,4-dione
• IUPAC Traditional name: ubiquinone 8
• Synonyms: 2,3-Dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaenyl]-2,5-cyclohexadiene-1,4-dione; 2,3-Dimethoxy-5-methyl-6-(3,7,11,15,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaenyl)-p-benzoquinone; Ubiquinone 40; Ubiquinone 8; Ubiquinone Q8; (all-E)-2,3-Dimethoxy-5-methyl-6-(3,7,11,15,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaenyl)-2,5-cyclohexadiene-1,4-dione; CoQ8; Coenzyme Q8

Database IDs

• CAS Number: 2394-68-5
• PubChem SID: 162259021
• PubChem CID: 5283546

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 13.8366995
• LogD (pH = 7.4): 13.8366995
• Log P: 13.8366995
• Molar Refractivity: 239.0 cm^3
• Polarizability: 89.495384 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 25
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C636490

An isoprenoid quinone that enhances nonspecific resistance to bacterial infections. It stimulates phagocytosis in macrophages by modulation of the kinetics of the Fc receptor. It serves as an electron carrier from the flavoprotein to the cytochrome comple

REFERENCES

• Block, L.H., et al.: J. J. Exp. Med. 149, 1228 (1978)
• Carter, K. et al.: J. Biol. Chem., 260, 10986 (1978)
• Block, L.H. et al.: J. Infect. Dis., 153, 209 (1978)