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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:22:34 UTC
Update Date2022-03-07 02:51:22 UTC
HMDB IDHMDB0012299
Secondary Accession Numbers
  • HMDB12299
Metabolite Identification
Common NameUbiquinol-6
DescriptionUbUbiquinone(Q) is an essential, lipid soluble, redox component of the mitochondrial respiratory chain. Much evidence suggests that ubiquinol (QH2) functions as an effective antioxidant in a number of membrane and biological systems by preventing peroxidative damage to lipids. It has been proposed that superoxide dismutase (SOD) may protect QH2 from autoxidation by acting either directly as a superoxide−semiquinone oxidoreductase or indirectly by scavenging superoxide. (Biochemistry, 1996, 35 (21), pp 6595 - 6603).
Structure
Data?1582753038
Synonyms
ValueSource
DihydroubiquinoneHMDB
Reduced ubiquinoneHMDB
UbiquinolHMDB
Ubiquinol(30)HMDB
Chemical FormulaC39H60O4
Average Molecular Weight592.8913
Monoisotopic Molecular Weight592.449160408
IUPAC Name2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-5,6-dimethoxy-3-methylbenzene-1,4-diol
Traditional Nameubiquinol-6
CAS Registry Number5677-58-7
SMILES
COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC
InChI Identifier
InChI=1S/C39H60O4/c1-28(2)16-11-17-29(3)18-12-19-30(4)20-13-21-31(5)22-14-23-32(6)24-15-25-33(7)26-27-35-34(8)36(40)38(42-9)39(43-10)37(35)41/h16,18,20,22,24,26,40-41H,11-15,17,19,21,23,25,27H2,1-10H3/b29-18+,30-20+,31-22+,32-24+,33-26+
InChI KeyDYOSCPIQEYRQEO-LPHQIWJTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. 2-Polyprenyl-6-methoxyphenols are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenylphenols
Direct Parent2-polyprenyl-6-methoxyphenols
Alternative Parents
Substituents
  • 2-polyprenyl-6-methoxyphenol
  • Polyprenylbenzoquinol
  • Sesterterpenoid
  • Prenylbenzoquinol
  • 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 effectNot Available
Disposition
Process
Role
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 Solubility0.00035 g/LALOGPS
logP8.49ALOGPS
logP11.59ChemAxon
logS-6.2ALOGPS
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 Count19ChemAxon
Refractivity191.24 m³·mol⁻¹ChemAxon
Polarizability75.45 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
DeepCCS[M+H]+248.95130932474
DeepCCS[M-H]-246.55630932474
DeepCCS[M-2H]-279.7330932474
DeepCCS[M+Na]+254.86430932474
AllCCS[M+H]+250.332859911
AllCCS[M+H-H2O]+249.032859911
AllCCS[M+NH4]+251.632859911
AllCCS[M+Na]+251.932859911
AllCCS[M-H]-235.632859911
AllCCS[M+Na-2H]-238.932859911
AllCCS[M+HCOO]-242.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ubiquinol-6COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC5918.2Standard polar33892256
Ubiquinol-6COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC3970.5Standard non polar33892256
Ubiquinol-6COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC4221.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ubiquinol-6,1TMS,isomer #1COC1=C(O)C(C/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)C(O[Si](C)(C)C)=C1OC4103.4Semi standard non polar33892256
Ubiquinol-6,1TMS,isomer #2COC1=C(O)C(C)=C(C/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C)C(O[Si](C)(C)C)=C1OC4123.2Semi standard non polar33892256
Ubiquinol-6,2TMS,isomer #1COC1=C(O[Si](C)(C)C)C(C)=C(C/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C)C(O[Si](C)(C)C)=C1OC4126.1Semi standard non polar33892256
Ubiquinol-6,1TBDMS,isomer #1COC1=C(O)C(C/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)C(O[Si](C)(C)C(C)(C)C)=C1OC4306.1Semi standard non polar33892256
Ubiquinol-6,1TBDMS,isomer #2COC1=C(O)C(C)=C(C/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C1OC4322.8Semi standard non polar33892256
Ubiquinol-6,2TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C(C)=C(C/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C1OC4509.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinol-6 GC-MS (Non-derivatized) - 70eV, Positivesplash10-05dr-2168390000-394910f888dc5f30f46d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinol-6 GC-MS (1 TMS) - 70eV, Positivesplash10-0002-3128379000-0117b81715e9c07a4c032017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinol-6 GC-MS ("Ubiquinol-6,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinol-6 GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinol-6 GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinol-6 GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinol-6 GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinol-6 GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol-6 10V, Positive-QTOFsplash10-0006-0223190000-d20ae1eccfe0bb20cd4c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol-6 20V, Positive-QTOFsplash10-0002-0669330000-51dfe9ccd5bc50aa4b9d2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol-6 40V, Positive-QTOFsplash10-0fr2-2159340000-bc6056287dbe529b04e32015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol-6 10V, Negative-QTOFsplash10-0006-0000090000-bdbe9cf3cbc85ce127e42015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol-6 20V, Negative-QTOFsplash10-00kf-0000190000-15019b0edbf51d3e63b82015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol-6 40V, Negative-QTOFsplash10-00fr-9200450000-c956803409da86b9394a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol-6 10V, Positive-QTOFsplash10-0016-5317390000-fe62471cddaa2c9b728a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol-6 20V, Positive-QTOFsplash10-000t-7619110000-ba2f99a58a62b2b831312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol-6 40V, Positive-QTOFsplash10-000y-9613000000-b2ee70ccfb91ef2ecc7a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol-6 10V, Negative-QTOFsplash10-0006-0000090000-ad84dec376fad5d3e7d72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol-6 20V, Negative-QTOFsplash10-0007-0611190000-69cb09efd0cb9335d4f62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinol-6 40V, Negative-QTOFsplash10-0171-3792540000-de6e147147d07d8f58242021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028922
KNApSAcK IDNot Available
Chemspider ID4710167
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5813154
PDB IDNot Available
ChEBI ID52970
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.