2-[(2E,6E,10E,14Z,18E,22E,26E,30Z,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

• ChemBase ID: 120166
• Molecular Formular: C59H90O4
• Molecular Mass: 863.3435
• Monoisotopic Mass: 862.68391136
• SMILES: C1(=C(C(=O)C(=C(C1=O)C)C/C=C(/CC/C=C(/CC/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)\C)OC)OC
• 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(/CC/C=C(\CC/C=C(/CCC=C(C)C)\C)/C)\C)\C)\C)/C)\C)\C)\C)C
• InChI: InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28-,47-30+,48-32+,49-34+,50-36-,51-38+,52-40+,53-42+
• InChIKey: ACTIUHUUMQJHFO-DQXDOXBUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2E,6E,10E,14Z,18E,22E,26E,30Z,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
• IUPAC Traditional name: 2-[(2E,6E,10E,14Z,18E,22E,26E,30Z,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
• Synonyms: 2-((2E,6E,10E,14Z,18E,22E,26E,30Z,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione; Ubiquinone 10; Ubiquinone 50; Ubidecarenone; Coenzyme q10

Database IDs

• CAS Number: 303-98-0
• PubChem SID: 162214519
• PubChem CID: 17572160

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 17.156128
• LogD (pH = 7.4): 17.156128
• Log P: 17.156128
• Molar Refractivity: 286.6052 cm^3
• Polarizability: 107.49632 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Electron transport chain regulator

Product Information

• Biological Source: Isol. from beef heart and other mammalian sources in which it is the principal representative of its class
• Application(s): Cardiovascular agent; used to treat congestive heart failure

REFERENCES

• Gloor, U. et al., Helv. Chim. Acta, 1958, 41, 2357; 1960, 43, 1745, (synth)
• Lester, R.L. et al., J.A.C.S., 1958, 80, 4751, (isol)
• Shunk, C.H. et al., J.A.C.S., 1958, 80, 4753, (Coenzymes Q1, Q2, Q3)
• Crane, F.L. et al., Biochim. Biophys. Acta, 1959, 32, 73, (isol)
• Gale, P.H. et al., Biochem. Biophys. Res. Commun., 1963, 12, 414, (Coenzyme Q10 (H-10))
• Gale, P.H. et al., Biochemistry, 1963, 2, 196, (Coenzyme Q10 (H-10))
• Morimoto, H. et al., Biochem. Z., 1965, 343, 329, (ir, ms, pmr)
• Lavate, W.V. et al., J. Biol. Chem., 1965, 240, 524, (Coenzyme Q10 (H-10))
• Friis, P. et al., J.A.C.S., 1966, 88, 4754, (biosynth)
• Muraca, R.F. et al., J.A.C.S., 1967, 89, 1505, (ms)
• Morimoto, H. et al., Annalen, 1969, 729, 158, (ir, pmr, uv, ms)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, nos. 4256-4260, (occur, bibl)
• The Vitamins, (Sebrell, W.H. et al, Ed.), Academic Press, 1972, 355, (rev)
• Inoue, S. et al., Bull. Chem. Soc. Jpn., 1974, 47, 3098-3101, (synth, ir, pmr, uv)
• Hegedus, L.S. et al., J.A.C.S., 1976, 98, 3901
• Biomed. Clin. Aspects Coenzyme Q, Elsevier, N.Y., 1977, 1-3, (books)
• Terao, S. et al., J.C.S. Perkin 1, 1978, 1101, (cmr, pmr)
• Terao, S. et al., J.O.C., 1979, 44, 868, (synth)
• Naruta, Y., J.O.C., 1980, 45, 4097, (synth)
• Boicelli, C.A. et al., Membr. Biochem., 1981, 4, 105, (pmr, cmr, config)
• Fujita, Y. et al., Bull. Chem. Soc. Jpn., 1982, 55, 1325, (synth)
• Cascone, A. et al., Boll. Chim. Farm., 1984, 123, 555, (pharmacol, Ubidecarenone)
• Masaki, Y. et al., Chem. Pharm. Bull., 1984, 32, 3959, (synth)
• Kaln, A. et al., Acta Chem. Scand., Ser. B, 1987, 41, 70, (biosynth)
• Konishi, K. et al., Chem. Pharm. Bull., 1987, 35, 1531, (biochem, bibl)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 8345, (synonyms)
• Eren, D. et al., J.A.C.S., 1988, 110, 4356, (synth)
• Greenberg, S.M. et al., Med. Clin. North Am., 1988, 72, 243, (rev, pharmacol)
• Morimoto, H. et al., Naturwissenschaften, 1989, 76, 200-205, (synth)
• Rttimann, A. et al., Helv. Chim. Acta, 1990, 73, 790, (synth, bibl)
• Martindale, The Extra Pharmacopoeia, 30th edn.,
• Lipshutz, B.H. et al., J.A.C.S., 1996, 118, 5512, (synth)
• Giner, J.-L. et al., Tet. Lett., 1998, 39, 8021-8022, (biosynth)
• Lipshutz, B.H. et al., J.A.C.S., 1999, 121, 11664-11673, (synth)
• Tran, M.T. et al., Pharmacotherapy (Carlisle, Mass.), 2001, 21, 797-806, (coenzyme Q10, rev)
• Ferrante, R.J. et al., J. Neurosci., 2002, 22, 1592-1599, (coenzyme Q10, pharmacol)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, UAH000