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Human Metabolome Database Version 3.5

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Showing metabocard for Ubiquinol 8 (HMDB01060)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:49 -0700
HMDB ID HMDB01060
Secondary Accession Numbers None
Metabolite Identification
Common Name Ubiquinol 8
Description Ubiquinol 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 vary 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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Ubiquinol(8)
  2. Ubiquinol-8
Chemical Formula C49H78O4
Average Molecular Weight 731.1412
Monoisotopic Molecular Weight 730.590010984
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-diol
Traditional 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-diol
CAS Registry Number 56275-39-9
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/C49H78O4/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/h20,22,24,26,28,30,32,34,46-47,50-51H,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 Key FLVUMORHBJZINO-SGHXUWJISA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Quinone and Hydroquinone Lipids
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Polyterpenes
Substituents
  • Cyclic Alcohol
  • Fatty Alcohol
  • Isoprene
  • Polyprenylbenzoquinol
  • Secondary Alcohol
  • Tetraterpene Backbone
Direct Parent Ubiquinols
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Ubiquinone biosynthesis
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.450E-04 g/L ALOGPS
LogP 8.66 ALOGPS
LogP 12 ChemAxon
LogS -6.33 ALOGPS
pKa (strongest acidic) 12.91 ChemAxon
pKa (strongest basic) -3.6 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 58.92 A2 ChemAxon
Rotatable Bond Count 25 ChemAxon
Refractivity 240.23 ChemAxon
Polarizability 95 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Mitochondrial Electron Transport Chain SMP00355 map00190 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.14 +/- 0.13 uM Adolescent (13-18 years old) Both Beta-thalassemia Transfusion dependant Age group: 11-22 years old
Associated Disorders and Diseases
Disease References
Beta-thalassemia
  • 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 Link_out
    Associated OMIM IDs
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB022399
    KNApSAcK ID Not Available
    Chemspider ID 17216048 Link_out
    KEGG Compound ID Not Available
    BioCyc ID UBIQUINOL-8 Link_out
    BiGG ID Not Available
    Wikipedia Link Ubiquinol Link_out
    NuGOwiki Link HMDB01060 Link_out
    Metagene Link HMDB01060 Link_out
    METLIN ID 5974 Link_out
    PubChem Compound 22833558 Link_out
    PDB ID Not Available
    ChEBI ID Not Available
    References
    Synthesis Reference Not 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 Link_out
    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 Link_out
    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 Link_out
    Enzymes
    Name: NADH-ubiquinone oxidoreductase chain 1
    Reactions:
    • NADH + H+ + ubiquinone = NAD+ + ubiquinol [RN:R02163]
    Gene Name: MT-ND1
    Uniprot ID: P03886 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial
    Reactions:
    • NADH + H+ + acceptor = NAD+ + reduced acceptor [RN:R00281]
    Gene Name: NDUFS2
    Uniprot ID: O75306 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NADH-ubiquinone oxidoreductase chain 4L
    Reactions:
    • NADH + H+ + ubiquinone = NAD+ + ubiquinol [RN:R02163]
    Gene Name: MT-ND4L
    Uniprot ID: P03901 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NADH-ubiquinone oxidoreductase chain 5
    Reactions:
    • NADH + H+ + ubiquinone = NAD+ + ubiquinol [RN:R02163]
    Gene Name: MT-ND5
    Uniprot ID: P03915 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial
    Reactions:
    • NADH + H+ + acceptor = NAD+ + reduced acceptor [RN:R00281]
    Gene Name: NDUFS3
    Uniprot ID: O75489 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial
    Reactions:
    • succinate + ubiquinone = fumarate + ubiquinol [RN:R02164]
    Gene Name: SDHA
    Uniprot ID: P31040 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NADH dehydrogenase [ubiquinone] iron-sulfur protein 8, mitochondrial
    Reactions:
    • NADH + H+ + acceptor = NAD+ + reduced acceptor [RN:R00281]
    Gene Name: NDUFS8
    Uniprot ID: O00217 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NADH-ubiquinone oxidoreductase chain 2
    Reactions:
    • NADH + H+ + ubiquinone = NAD+ + ubiquinol [RN:R02163]
    Gene Name: MT-ND2
    Uniprot ID: P03891 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NADH-ubiquinone oxidoreductase 75 kDa subunit, mitochondrial
    Reactions:
    • NADH + H+ + acceptor = NAD+ + reduced acceptor [RN:R00281]
    Gene Name: NDUFS1
    Uniprot ID: P28331 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NADH-ubiquinone oxidoreductase chain 4
    Reactions:
    • NADH + H+ + ubiquinone = NAD+ + ubiquinol [RN:R02163]
    Gene Name: MT-ND4
    Uniprot ID: P03905 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial
    Reactions:
    • NADH + H+ + acceptor = NAD+ + reduced acceptor [RN:R00281]
    Gene Name: NDUFS7
    Uniprot ID: O75251 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NADH-ubiquinone oxidoreductase chain 3
    Reactions:
    • NADH + H+ + ubiquinone = NAD+ + ubiquinol [RN:R02163]
    Gene Name: MT-ND3
    Uniprot ID: P03897 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial
    Reactions:
    • NADH + H+ + acceptor = NAD+ + reduced acceptor [RN:R00281]
    Gene Name: NDUFV1
    Uniprot ID: P49821 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NADH-ubiquinone oxidoreductase chain 6
    Reactions:
    • NADH + H+ + ubiquinone = NAD+ + ubiquinol [RN:R02163]
    Gene Name: MT-ND6
    Uniprot ID: P03923 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial
    Reactions:
    • succinate + ubiquinone = fumarate + ubiquinol [RN:R02164]
    Gene Name: SDHB
    Uniprot ID: P21912 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA