Record Information
Version2.0
Creation Date2012-08-09 09:16:15 -0600
Update Date2015-10-15 16:13:53 -0600
Secondary Accession Numbers
  • ECMDB21438
Identification
Name:Ubiquinone-1
Description:Ubiquinone-1 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-1 has just 1 isoprene unit. Normally in E. coli the active form of Ubiquinone has 8 isoprene units (Ubiquinone-8) and in humans it normally has 10. Ubiquinone-1 is a “failed” or incomplete version of Ubiquinone 8 that arises from conjugation by a shortened 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:
  • 2,3-dimethoxy-5-methyl-6-(3-methylbut-2-enyl)cyclohexa-2,5-diene-1,4-dione
  • A ubiquinone
  • Coenzym Q
  • coenzyme Q
  • Coenzyme Q1
  • Coenzymes Q
  • CoQ
  • CoQ1
  • Koenzym Q
  • Mitoquinones
  • Q
  • Q1
  • Ubichinon
  • Ubiquinone
  • Ubiquinone 5
  • Ubiquinone Q1
  • Ubiquinone(1)
  • Ubiquinone-Q1
  • Ubiquinones
  • Ubiquionone 1
Chemical Formula:C19H28O4
Weight:Average: 320.429
Monoisotopic: 320.198759382
InChI Key:RNUCUWWMTTWKAH-UHFFFAOYSA-N
InChI:InChI=1S/C19H28O4/c1-12(2)8-7-9-13(3)10-11-15-14(4)16(20)18(22-5)19(23-6)17(15)21/h8,10,20-21H,7,9,11H2,1-6H3
CAS number:727-81-1
IUPAC Name:2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)cyclohexa-2,5-diene-1,4-dione
Traditional IUPAC Name:ubiquinone-1
SMILES:COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)C)C(O)=C1OC
Chemical Taxonomy
DescriptionThis compound 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
  • Ubiquinone skeleton
  • Monoterpenoid
  • Monocyclic monoterpenoid
  • 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 Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP2.2ALOGPS
logP2.22ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.38 m³·mol⁻¹ChemAxon
Polarizability26.94 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Oxidative phosphorylationPW000919 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cyclePW000779 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolismPW000914 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism IIPW000915 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism III (sn-glycero-3-phosphoethanolamine)PW000916 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism IV (glycerophosphoglycerol)PW000917 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism V (glycerophosphoserine)PW000918 ThumbThumb?image type=greyscaleThumb?image type=simple
proline metabolismPW000794 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ri-6690000000-54c21ecf74c316617005View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0190000000-e28dd9a4e1e31fde0aaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frt-4790000000-e9b4aa7330c158e93f74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pw9-9400000000-984285464810c9d07a1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0190000000-d560b9e909b6d771b748View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0890000000-173d3724196ddfd71b38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001r-8940000000-6ddd0c7bdddc6aa7ff07View in MoNA
References
References:
  • Edlund C, Soderberg M, Kristensson K, Dallner G: Ubiquinone, dolichol, and cholesterol metabolism in aging and Alzheimer's disease. Biochem Cell Biol. 1992 Jun;70(6):422-8. Pubmed: 1449707
  • Elmberger PG, Kalen A, Brunk UT, Dallner G: Discharge of newly-synthesized dolichol and ubiquinone with lipoproteins to rat liver perfusate and to the bile. Lipids. 1989 Nov;24(11):919-30. Pubmed: 2615561
  • Karlsson J, Lin L, Gunnes S, Sylven C, Astrom H: Muscle ubiquinone in male effort angina patients. Mol Cell Biochem. 1996 Mar 23;156(2):173-8. Pubmed: 9095475
  • Karlsson J, Lin L, Sylven C, Jansson E: Muscle ubiquinone in healthy physically active males. Mol Cell Biochem. 1996 Mar 23;156(2):169-72. Pubmed: 9095474
  • Laaksonen R, Jokelainen K, Sahi T, Tikkanen MJ, Himberg JJ: Decreases in serum ubiquinone concentrations do not result in reduced levels in muscle tissue during short-term simvastatin treatment in humans. Clin Pharmacol Ther. 1995 Jan;57(1):62-6. Pubmed: 7828383
  • Mancini A, Conte G, Milardi D, De Marinis L, Littarru GP: Relationship between sperm cell ubiquinone and seminal parameters in subjects with and without varicocele. Andrologia. 1998 Feb-Mar;30(1):1-4. Pubmed: 9567163
  • Passi S, Stancato A, Aleo E, Dmitrieva A, Littarru GP: Statins lower plasma and lymphocyte ubiquinol/ubiquinone without affecting other antioxidants and PUFA. Biofactors. 2003;18(1-4):113-24. Pubmed: 14695926
  • Pastore A, Giovamberardino GD, Bertini E, Tozzi G, Gaeta LM, Federici G, Piemonte F: Simultaneous determination of ubiquinol and ubiquinone in skeletal muscle of pediatric patients. Anal Biochem. 2005 Jul 15;342(2):352-5. Epub 2005 Mar 7. Pubmed: 15989930
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Yamashita S, Yamamoto Y: Simultaneous detection of ubiquinol and ubiquinone in human plasma as a marker of oxidative stress. Anal Biochem. 1997 Jul 15;250(1):66-73. Pubmed: 9234900
  • Zhang Y, Eriksson M, Dallner G, Appelkvist EL: Analysis of ubiquinone and tocopherol levels in normal and hyperlipidemic human plasma. Lipids. 1998 Aug;33(8):811-5. Pubmed: 9727612
Synthesis Reference:Naruta, Yoshinori; Maruyama, Kazuhiro. . Ubiquinone-1. Organic Syntheses (1993), 71 125-32.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16389
HMDB IDHMDB02012
Pubchem Compound ID4462
Kegg IDC00399
ChemSpider ID4307
WikipediaUbiquinone
BioCyc IDNot Available
Ligand ExpoUQ1

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 oxidoreductase activity
Specific function:
Oxidizes proline to glutamate for use as a carbon and nitrogen source and also function as a transcriptional repressor of the put operon
Gene Name:
putA
Uniprot ID:
P09546
Molecular weight:
143814
Reactions
L-proline + acceptor = (S)-1-pyrroline-5-carboxylate + reduced acceptor.
(S)-1-pyrroline-5-carboxylate + NAD(P)(+) + 2 H(2)O = L-glutamate + NAD(P)H.
General function:
Involved in oxidation-reduction process
Specific function:
sn-glycerol 3-phosphate + NAD(P)(+) = glycerone phosphate + NAD(P)H
Gene Name:
gpsA
Uniprot ID:
P0A6S7
Molecular weight:
36361
Reactions
sn-glycerol 3-phosphate + NAD(P)(+) = glycerone phosphate + NAD(P)H.
General function:
Involved in catalytic activity
Specific function:
(S)-dihydroorotate + a quinone = orotate + a quinol
Gene Name:
pyrD
Uniprot ID:
P0A7E1
Molecular weight:
36774
Reactions
(S)-dihydroorotate + a quinone = orotate + a quinol.
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 NADH or NADPH
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoA
Uniprot ID:
P0AFC3
Molecular weight:
16457
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoB
Uniprot ID:
P0AFC7
Molecular weight:
25056
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in oxidoreductase activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoE
Uniprot ID:
P0AFD1
Molecular weight:
18590
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in oxidation-reduction process
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient. This subunit may bind ubiquinone
Gene Name:
nuoH
Uniprot ID:
P0AFD4
Molecular weight:
36219
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in electron carrier activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoI
Uniprot ID:
P0AFD6
Molecular weight:
20538
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoJ
Uniprot ID:
P0AFE0
Molecular weight:
19874
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:
There are 2 NADH dehydrogenases in E.coli, however only this complex is able to use dNADH (reduced nicotinamide hypoxanthine dinucleotide, deamino-NADH) and dNADH-DB (dimethoxy- 5-methyl-6-decyl-1,4-benzoquinone) as substrates
Gene Name:
nuoK
Uniprot ID:
P0AFE4
Molecular weight:
10845
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoM
Uniprot ID:
P0AFE8
Molecular weight:
56524
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoN
Uniprot ID:
P0AFF0
Molecular weight:
52044
Reactions
NADH + quinone = NAD(+) + quinol.
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 2-polyprenyl-6-methoxy-1,4-benzoquinone methyltransferase activity
Specific function:
S-adenosyl-L-methionine + 3- demethylubiquinone-9 = S-adenosyl-L-homocysteine + ubiquinone-9
Gene Name:
ubiG
Uniprot ID:
P17993
Molecular weight:
26555
Reactions
S-adenosyl-L-methionine + 3-demethylubiquinone-n = S-adenosyl-L-homocysteine + ubiquinone-n.
S-adenosyl-L-methionine + 3-(all-trans-polyprenyl)benzene-1,2-diol = S-adenosyl-L-homocysteine + 2-methoxy-6-(all-trans-polyprenyl)phenol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoF
Uniprot ID:
P31979
Molecular weight:
49292
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoC
Uniprot ID:
P33599
Molecular weight:
68236
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in electron carrier activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoG
Uniprot ID:
P33602
Molecular weight:
100298
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoL
Uniprot ID:
P33607
Molecular weight:
66438
Reactions
NADH + quinone = NAD(+) + quinol.
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
General function:
Involved in cytochrome bo3 ubiquinol oxidase activity
Specific function:
Cytochrome o terminal oxidase complex is the component of the aerobic respiratory chain of E.coli that predominates when cells are grown at high aeration
Gene Name:
cyoA
Uniprot ID:
P0ABJ1
Molecular weight:
34911
Reactions
Ubiquinol-8 + O(2) = Ubiquinone-8 + H(2)O.
General function:
Involved in cytochrome o ubiquinol oxidase activity
Specific function:
Cytochrome o terminal oxidase complex is the component of the aerobic respiratory chain of E.coli that predominates when cells are grown at high aeration
Gene Name:
cyoD
Uniprot ID:
P0ABJ6
Molecular weight:
12029
General function:
Involved in oxidation-reduction process
Specific function:
Cytochrome oxidase subunit
Gene Name:
appB
Uniprot ID:
P26458
Molecular weight:
42423
General function:
Energy production and conversion
Specific function:
Cytochrome oxidase subunit
Gene Name:
appC
Uniprot ID:
P26459
Molecular weight:
57919
General function:
Involved in oxidation-reduction process
Specific function:
Cytochrome d terminal oxidase complex is the component of the aerobic respiratory chain of E.coli that predominates when cells are grown at low aeration
Gene Name:
cydB
Uniprot ID:
P0ABK2
Molecular weight:
42453
Reactions
Ubiquinol-8 + O(2) = Ubiquinone-8 + H(2)O.
General function:
Involved in cytochrome-c oxidase activity
Specific function:
Cytochrome o terminal oxidase complex is the component of the aerobic respiratory chain of E.coli that predominates when cells are grown at high aeration. This ubiquinol oxidase shows proton pump activity across the membrane in addition to the electron transfer
Gene Name:
cyoB
Uniprot ID:
P0ABI8
Molecular weight:
74367
Reactions
Ubiquinol-8 + O(2) = Ubiquinone-8 + H(2)O.
General function:
Energy production and conversion
Specific function:
Cytochrome d terminal oxidase complex is the component of the aerobic respiratory chain of E.coli that predominates when cells are grown at low aeration
Gene Name:
cydA
Uniprot ID:
P0ABJ9
Molecular weight:
58205
Reactions
Ubiquinol-8 + O(2) = Ubiquinone-8 + H(2)O.
General function:
Involved in heme-copper terminal oxidase activity
Specific function:
Cytochrome o terminal oxidase complex is the component of the aerobic respiratory chain of E.coli that predominates when cells are grown at high aeration
Gene Name:
cyoC
Uniprot ID:
P0ABJ3
Molecular weight:
22623
Reactions
Ubiquinol-8 + O(2) = Ubiquinone-8 + H(2)O.
General function:
oxidative phosphorylation
Specific function:
Required for correct functioning of cytochrome bd-I oxidase. This protein and AppX may have some functional overlap.
Gene Name:
cydX
Uniprot ID:
P56100
Molecular weight:
4041