Record Information
Version2.0
Creation Date2012-05-31 13:44:35 -0600
Update Date2015-06-03 15:53:42 -0600
Secondary Accession Numbers
  • ECMDB01072
Identification
Name:Ubiquinone-10
DescriptionUbiquinone-10 is a member of the chemical class known as Polyprenylbenzoquinones. These are compounds containing a polyisoprene chain attached to a quinone at the second ring position. Ubiquione-10 has 10 isoprene units. Normally in E. coli the active form of Ubiquinone has 8 isoprene units (Ubiquinone-8) and in humans it normally has 10. Ubiquinone-10 is an extended version of Ubiquinone 8 that arises from conjugation by an extended prenyl tail via 4-hydroxybenzoate polyprenyltransferase. Ubiquionone is involved in cellular respiration. It is fat-soluble and is therefore mobile in cellular membranes; it plays a unique role in the electron transport chain (ETC). In the inner bacterial membrane, electrons from NADH and succinate pass through the ETC to the oxygen, which is then reduced to water. The transfer of electrons through ETC results in the pumping of H+ across the membrane creating a proton gradient across the membrane, which is used by ATP synthase (located on the membrane) to generate ATP.
Structure
Thumb
Synonyms:
  • (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
  • (all-E)-2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-2,5-Cyclohexadiene-1,4-dione
  • 2-(3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-p-Benzoquinone
  • 2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl]-5,6-dimethoxy-3-methyl- 2,5-Cyclohexadiene-1,4-dione
  • 4-Ethyl-5-fluoropyrimidine
  • Aqua Q 10L10
  • Aqua Q10
  • Bio-Quinon
  • Bio-Quinone Q10
  • Coenzyme Q10
  • Coenzyme-Q10
  • Coenzyme-Q10
  • CoQ10
  • Ensorb
  • Kaneka Q10
  • Kudesan
  • Li-Q-Sorb
  • Liquid-Q
  • Neuquinon
  • Neuquinone
  • PureSorb Q 40
  • Q 10AA
  • Q-Gel
  • Q-Gel 100
  • Ubidecarenone
  • Ubiquinone 10
  • Ubiquinone 50
  • Ubiquinone Q10
  • Ubiquinone(10)
  • Ubiquinone-10
  • Unbiquinone
  • Unispheres Q 10
Chemical Formula:C59H90O4
Weight:Average: 863.3435
Monoisotopic: 862.683911368
InChI Key:ACTIUHUUMQJHFO-UPTCCGCDSA-N
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+
CAS number:303-98-0
IUPAC Name:2-[(2E,6E,10E,14E,18E,22E,26Z,30E,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
Traditional IUPAC Name:ubisemiquinone
SMILES:COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentUbiquinones
Alternative Parents
Substituents
  • Polyterpenoid
  • Polyprenylbenzoquinone
  • Ubiquinone skeleton
  • Quinone
  • P-benzoquinone
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:7.463PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00019 g/LALOGPS
logP9.94ALOGPS
logP17.16ChemAxon
logS-6.7ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count31ChemAxon
Refractivity286.61 m³·mol⁻¹ChemAxon
Polarizability111.43 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
TCA cycle (ubiquinol-10)PW001010 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0211111090-6a869102747ec5ae93a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-1859498220-7339f4669211f439f21aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-2131239600-0459da83925ec9d0e79fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-b50a0138d910d6641b72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08i4-0000000890-33ee289015ac39ff3df8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-3000000940-d7a250f754c937cceb37View in MoNA
References
References:
  • Appelkvist EL, Edlund C, Low P, Schedin S, Kalen A, Dallner G: Effects of inhibitors of hydroxymethylglutaryl coenzyme A reductase on coenzyme Q and dolichol biosynthesis. Clin Investig. 1993;71(8 Suppl):S97-102. Pubmed: 8241713
  • De Luca C, Filosa A, Grandinetti M, Maggio F, Lamba M, Passi S: Blood antioxidant status and urinary levels of catecholamine metabolites in beta-thalassemia. Free Radic Res. 1999 Jun;30(6):453-62. Pubmed: 10400457
  • Folkers K, Hanioka T, Xia LJ, McRee JT Jr, Langsjoen P: Coenzyme Q10 increases T4/T8 ratios of lymphocytes in ordinary subjects and relevance to patients having the AIDS related complex. Biochem Biophys Res Commun. 1991 Apr 30;176(2):786-91. Pubmed: 1673841
  • Hanisch F, Zierz S: Only transient increase of serum CoQ subset 10 during long-term CoQ10 therapy in mitochondrial ophthalmoplegia. Eur J Med Res. 2003 Nov 12;8(11):485-91. Pubmed: 14644702
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Lalani SR, Vladutiu GD, Plunkett K, Lotze TE, Adesina AM, Scaglia F: Isolated mitochondrial myopathy associated with muscle coenzyme Q10 deficiency. Arch Neurol. 2005 Feb;62(2):317-20. Pubmed: 15710863
  • Littarru GP, Tiano L: Bioenergetic and antioxidant properties of coenzyme Q10: recent developments. Mol Biotechnol. 2007 Sep;37(1):31-7. Pubmed: 17914161
  • Mancini A, Conte B, De Marinis L, Hallgass ME, Pozza D, Oradei A, Littarru GP: Coenzyme Q10 levels in human seminal fluid: diagnostic and clinical implications. Mol Aspects Med. 1994;15 Suppl:s249-55. Pubmed: 7752837
  • Mancini A, De Marinis L, Oradei A, Hallgass ME, Conte G, Pozza D, Littarru GP: Coenzyme Q10 concentrations in normal and pathological human seminal fluid. J Androl. 1994 Nov-Dec;15(6):591-4. Pubmed: 7721661
  • Miyake Y, Shouzu A, Nishikawa M, Yonemoto T, Shimizu H, Omoto S, Hayakawa T, Inada M: Effect of treatment with 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors on serum coenzyme Q10 in diabetic patients. Arzneimittelforschung. 1999 Apr;49(4):324-9. Pubmed: 10337451
  • Mosca L, Marcellini S, Perluigi M, Mastroiacovo P, Moretti S, Famularo G, Peluso I, Santini G, De Simone C: Modulation of apoptosis and improved redox metabolism with the use of a new antioxidant formula. Biochem Pharmacol. 2002 Apr 1;63(7):1305-14. Pubmed: 11960607
  • Ogasahara S, Engel AG, Frens D, Mack D: Muscle coenzyme Q deficiency in familial mitochondrial encephalomyopathy. Proc Natl Acad Sci U S A. 1989 Apr;86(7):2379-82. Pubmed: 2928337
  • Ogasahara S, Yorifuji S, Nishikawa Y, Takahashi M, Wada K, Hazama T, Nakamura Y, Hashimoto S, Kono N, Tarui S: Improvement of abnormal pyruvate metabolism and cardiac conduction defect with coenzyme Q10 in Kearns-Sayre syndrome. Neurology. 1985 Mar;35(3):372-7. Pubmed: 3974895
  • Sekine K, Ota N, Nishii M, Uetake T, Shimadzu M: Estimation of plasma and saliva levels of coenzyme Q10 and influence of oral supplementation. Biofactors. 2005;25(1-4):205-11. Pubmed: 16873948
  • Siciliano G, Mancuso M, Tedeschi D, Manca ML, Renna MR, Lombardi V, Rocchi A, Martelli F, Murri L: Coenzyme Q10, exercise lactate and CTG trinucleotide expansion in myotonic dystrophy. Brain Res Bull. 2001 Oct-Nov 1;56(3-4):405-10. Pubmed: 11719279
  • Siemieniuk E, Skrzydlewska E: [Coenzyme Q10: its biosynthesis and biological significance in animal organisms and in humans]. Postepy Hig Med Dosw (Online). 2005;59:150-9. Pubmed: 15928598
  • Singh RB, Niaz MA, Rastogi SS, Shukla PK, Thakur AS: Effect of hydrosoluble coenzyme Q10 on blood pressures and insulin resistance in hypertensive patients with coronary artery disease. J Hum Hypertens. 1999 Mar;13(3):203-8. Pubmed: 10204818
  • Tomasetti M, Alleva R, Solenghi MD, Littarru GP: Distribution of antioxidants among blood components and lipoproteins: significance of lipids/CoQ10 ratio as a possible marker of increased risk for atherosclerosis. Biofactors. 1999;9(2-4):231-40. Pubmed: 10416035
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Van Maldergem L, Trijbels F, DiMauro S, Sindelar PJ, Musumeci O, Janssen A, Delberghe X, Martin JJ, Gillerot Y: Coenzyme Q-responsive Leigh's encephalopathy in two sisters. Ann Neurol. 2002 Dec;52(6):750-4. Pubmed: 12447928
  • Ye CQ, Folkers K, Tamagawa H, Pfeiffer C: A modified determination of coenzyme Q10 in human blood and CoQ10 blood levels in diverse patients with allergies. Biofactors. 1988 Dec;1(4):303-6. Pubmed: 3255359
  • Zhou S, Zhang Y, Davie A, Marshall-Gradisnik S, Hu H, Wang J, Brushett D: Muscle and plasma coenzyme Q10 concentration, aerobic power and exercise economy of healthy men in response to four weeks of supplementation. J Sports Med Phys Fitness. 2005 Sep;45(3):337-46. Pubmed: 16230985
  • Zierz S, Jahns G, Jerusalem F: Coenzyme Q in serum and muscle of 5 patients with Kearns-Sayre syndrome and 12 patients with ophthalmoplegia plus. J Neurol. 1989 Feb;236(2):97-101. Pubmed: 2709060
  • Zierz S, von Wersebe O, Bleistein J, Jerusalem F: Exogenous coenzyme Q (coq) fails to increase coq in skeletal muscle of two patients with mitochondrial myopathies. J Neurol Sci. 1990 Mar;95(3):283-90. Pubmed: 2358821
Synthesis Reference:Seo, Myung-Ji; Im, Eun-Mi; Hur, Jin-Haeng; Nam, Jung-Yeon; Hyun, Chang-Gu; Pyun, Yu-Ryang; Kim, Soon-Ok. Production of coenzyme Q10 by recombinant E. coli harboring the decaprenyl diphosphate synthase gene from Sinorhizobium meliloti. Journal of Micro
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID46245
HMDB IDHMDB01072
Pubchem Compound ID1156
Kegg IDC11378
ChemSpider ID4445197
Wikipediacoenzyme Q10
BioCyc IDUBIQUINONE-10
EcoCyc IDUBIQUINONE-10
Ligand ExpoU10

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Pyruvate + ferricytochrome b1 + H(2)O = acetate + CO(2) + ferrocytochrome b1
Gene Name:
poxB
Uniprot ID:
P07003
Molecular weight:
62011
Reactions
Pyruvate + ubiquinone + H(2)O = acetate + CO(2) + ubiquinol.
General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
sdhB
Uniprot ID:
P07014
Molecular weight:
26770
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
sdhA
Uniprot ID:
P0AC41
Molecular weight:
64421
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
General function:
Involved in succinate dehydrogenase activity
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH)
Gene Name:
sdhD
Uniprot ID:
P0AC44
Molecular weight:
12867
General function:
Involved in oxidoreductase activity, acting on CH-OH group of donors
Specific function:
GDH is probably involved in energy conservation rather than in sugar metabolism
Gene Name:
gcd
Uniprot ID:
P15877
Molecular weight:
86747
Reactions
D-glucose + ubiquinone = D-glucono-1,5-lactone + ubiquinol.
General function:
Involved in succinate dehydrogenase activity
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH)
Gene Name:
sdhC
Uniprot ID:
P69054
Molecular weight:
14299