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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:08 UTC
HMDB IDHMDB0001060
Secondary Accession Numbers
  • HMDB01060
Metabolite Identification
Common NameUbiquinol 8
DescriptionUbiquinol 8 is a ubiquinol in which the polyprenyl substituent is octaprenyl. Ubiquinol-8 is the reduced form of ubiquinone-8. Ubiquinone (also known as coenzyme Q) is an isoprenoid quinone that functions as an electron carrier in membranes. In eukaryotes, ubiquinone is found mostly within the inner mitochondrial membrane where it functions in respiratory electron transport, transferring two electrons from either complex I (NADH dehydrogenase) or complex II (succinate-ubiquinone reductase) to complex III (bc1 complex). The quinone nucleus of ubiquinone is derived directly from 4-hydroxybenzoate, while the isoprenoid subunits of the polyisoprenoid tail are synthesized via the methylerythritol phosphate pathway, which feeds isoprene units into the polyprenyl biosynthesis pathways. The number of isoprenoid subunits in the ubiquinone side chain varies in different species. For example, Saccharomyces cerevisiae has 6 such subunits, Escherichia coli K-12 has 8, rat and mouse have 9, and Homo sapiens has 10. Ubiquinol-8 is effective as an anti-oxidant. By donating one of its hydrogen atoms to become the free-radical semiquinone (.Q-), it can neutralize a lipid peroxyl radical. The free-radical semiquinone is then restored to a non-free-radical state by the respiratory chain Q cycle. Ubiquinol or the free-radical semiquinone can also regenerate the Vitamin E tocopheroxyl radical by electron donation (http://www.benbest.com/nutrceut/CoEnzymeQ.html).
Structure
Data?1582752174
Synonyms
ValueSource
Reduced coenzyme Q8ChEBI
Ubiquinol(8)ChEBI
Ubiquinol-8HMDB
Chemical FormulaC49H76O4
Average Molecular Weight729.1253
Monoisotopic Molecular Weight728.57436092
IUPAC Name2,3-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]benzene-1,4-diol
Traditional Nameubiquinol-8
CAS Registry Number74075-00-6
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)CCC=C(C)C)C(C)=C1O
InChI Identifier
InChI=1S/C49H76O4/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/h20,22,24,26,28,30,32,34,50-51H,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+
InChI KeyLOJUQFSPYHMHEO-SGHXUWJISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as polyprenyl quinols. Polyprenyl quinols are compounds containing a polyisoprene chain attached to a quinol(hydroquinone) at the second ring position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentPolyprenyl quinols
Alternative Parents
Substituents
  • Tetraterpenoid
  • 2-polyprenyl-6-methoxyphenol
  • Polyprenylbenzoquinol
  • Polyprenylphenol
  • Ubiquinol skeleton
  • Methoxyphenol
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Anisole
  • Hydroquinone
  • M-cresol
  • Phenoxy compound
  • O-cresol
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Phenol
  • Toluene
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00034 g/LALOGPS
logP9.35ALOGPS
logP14.91ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)10.27ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity238.85 m³·mol⁻¹ChemAxon
Polarizability94.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+278.1132859911
AllCCS[M-H]-265.58132859911
DeepCCS[M+H]+284.47530932474
DeepCCS[M-H]-282.37730932474
DeepCCS[M-2H]-315.61530932474
DeepCCS[M+Na]+290.36230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ubiquinol 8COC1=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)CCC=C(C)C)C(C)=C1O6244.8Standard polar33892256
Ubiquinol 8COC1=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)CCC=C(C)C)C(C)=C1O4774.6Standard non polar33892256
Ubiquinol 8COC1=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)CCC=C(C)C)C(C)=C1O5005.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinol 8 GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinol 8 GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinol 8 GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinol 8 GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinol 8 GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol 8 10V, Positive-QTOFsplash10-004i-0323324900-8d5262afd36dcbc7148a2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol 8 20V, Positive-QTOFsplash10-0032-1648692100-f4b35e5836e1b0685dbe2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol 8 40V, Positive-QTOFsplash10-0532-5487958100-34e9af02e9a7005e70a42019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol 8 10V, Negative-QTOFsplash10-004i-0000000900-456744203daa0fca5d762019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol 8 20V, Negative-QTOFsplash10-0h00-0000009500-add178adb113c4e8faa32019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol 8 40V, Negative-QTOFsplash10-03k9-3000019100-471dfb54d9e8cb8939f82019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol 8 10V, Positive-QTOFsplash10-057j-6405569600-34b9f4abc22e1814c3152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol 8 20V, Positive-QTOFsplash10-000t-4904532000-2ec1e0341ea818671a912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol 8 40V, Positive-QTOFsplash10-0036-9613310000-3825f8084c00c72645ec2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol 8 10V, Negative-QTOFsplash10-004i-0000000900-753eb68b8e8835d49d632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol 8 20V, Negative-QTOFsplash10-00mk-0910108500-1324247480f23e6031ea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol 8 40V, Negative-QTOFsplash10-001i-0942167000-3f62ea4336556f2f28ce2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.400 +/- 0.120 uMAdolescent (13-18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.14 +/- 0.13 uMAdolescent (13-18 years old)Both
Beta-thalassemia
details
Associated Disorders and Diseases
Disease References
Beta-thalassemia
  1. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022399
KNApSAcK IDNot Available
Chemspider ID24603698
KEGG Compound IDNot Available
BioCyc IDCPD-9956
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5974
PubChem Compound25074411
PDB IDNot Available
ChEBI ID61682
Food Biomarker OntologyNot Available
VMH IDQ8H2
MarkerDB IDMDB00000298
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Maneiro E, Lopez-Armada MJ, de Andres MC, Carames B, Martin MA, Bonilla A, Del Hoyo P, Galdo F, Arenas J, Blanco FJ: Effect of nitric oxide on mitochondrial respiratory activity of human articular chondrocytes. Ann Rheum Dis. 2005 Mar;64(3):388-95. [PubMed:15708893 ]
  3. Nohl H, Gille L, Staniek K: Intracellular generation of reactive oxygen species by mitochondria. Biochem Pharmacol. 2005 Mar 1;69(5):719-23. Epub 2005 Jan 20. [PubMed:15710349 ]

Only showing the first 10 proteins. There are 15 proteins in total.

Enzymes

General function:
Involved in oxidation reduction
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND1
Uniprot ID:
P03886
Molecular weight:
35660.055
General function:
Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
NDUFS2
Uniprot ID:
O75306
Molecular weight:
51851.59
General function:
Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND4L
Uniprot ID:
P03901
Molecular weight:
10741.005
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND5
Uniprot ID:
P03915
Molecular weight:
67025.67
General function:
Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
NDUFS3
Uniprot ID:
O75489
Molecular weight:
30241.245
General function:
Involved in electron carrier activity
Specific function:
Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). Can act as a tumor suppressor.
Gene Name:
SDHA
Uniprot ID:
P31040
Molecular weight:
72690.975
General function:
Involved in electron carrier activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity). May donate electrons to ubiquinone.
Gene Name:
NDUFS8
Uniprot ID:
O00217
Molecular weight:
23704.795
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND2
Uniprot ID:
P03891
Molecular weight:
38960.47
General function:
Involved in electron carrier activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity). This is the largest subunit of complex I and it is a component of the iron-sulfur (IP) fragment of the enzyme. It may form part of the active site crevice where NADH is oxidized.
Gene Name:
NDUFS1
Uniprot ID:
P28331
Molecular weight:
67523.595
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND4
Uniprot ID:
P03905
Molecular weight:
51580.26

Only showing the first 10 proteins. There are 15 proteins in total.