Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:19:59 UTC
Update Date2022-03-07 02:51:21 UTC
HMDB IDHMDB0012146
Secondary Accession Numbers
  • HMDB12146
Metabolite Identification
Common Name2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol
Description2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol is an ubiquinone derivative that is an intermediate in ubiquinone-6 biosynthesis. 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 subsp (S288c) has 6 such subunits, Escherichia coli K-12 has 8, rat and mouse have 9, and Homo sapiens has 10. The ubiquinones are often named according to the number of carbons in the side chain or the number of isoprenoid subunits. The ubiquinone biosynthesis pathway has been elucidated primarily by the use of mutant strains that accumulate pathway intermediates. 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol is a substrate for hexaprenyldihydroxybenzoate methyltransferase, mitochondrial precursor (COQ3) and can be generated from 2-hexaprenyl-3-methyl-6-methoxy-1,4-benzoquinol. Then it can be converted to ubiquinol-6.(BioCyc).
Structure
Data?1582753019
Synonyms
ValueSource
Demethyl-ubiquinol-6HMDB
Chemical FormulaC38H58O4
Average Molecular Weight578.8647
Monoisotopic Molecular Weight578.433510344
IUPAC Name5-[(2Z,6E,10E,14E,18Z)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-3-methoxy-6-methylbenzene-1,2,4-triol
Traditional Name5-[(2Z,6E,10E,14E,18Z)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-3-methoxy-6-methylbenzene-1,2,4-triol
CAS Registry NumberNot Available
SMILES
COC1=C(O)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)=C1O
InChI Identifier
InChI=1S/C38H58O4/c1-27(2)15-10-16-28(3)17-11-18-29(4)19-12-20-30(5)21-13-22-31(6)23-14-24-32(7)25-26-34-33(8)35(39)37(41)38(42-9)36(34)40/h15,17,19,21,23,25,39-41H,10-14,16,18,20,22,24,26H2,1-9H3/b28-17-,29-19+,30-21+,31-23+,32-25-
InChI KeyZQXNZNKHQXLVCV-QXVHJBQVSA-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
  • Hydroxyquinol derivative
  • Anisole
  • Phenoxy compound
  • M-cresol
  • O-cresol
  • Phenol ether
  • Methoxybenzene
  • Phenol
  • Alkyl aryl ether
  • Toluene
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Polyol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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 Solubility0.00064 g/LALOGPS
logP8.32ALOGPS
logP11.45ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)9.96ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.92 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity186.76 m³·mol⁻¹ChemAxon
Polarizability72.49 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]+243.74130932474
DeepCCS[M-H]-241.34530932474
DeepCCS[M-2H]-274.42730932474
DeepCCS[M+Na]+249.65330932474
AllCCS[M+H]+247.632859911
AllCCS[M+H-H2O]+246.232859911
AllCCS[M+NH4]+248.932859911
AllCCS[M+Na]+249.332859911
AllCCS[M-H]-231.432859911
AllCCS[M+Na-2H]-234.632859911
AllCCS[M+HCOO]-238.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinolCOC1=C(O)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)=C1O5990.2Standard polar33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinolCOC1=C(O)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)=C1O3981.0Standard non polar33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinolCOC1=C(O)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)=C1O4275.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,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)=C1O[Si](C)(C)C4101.3Semi standard non polar33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,1TMS,isomer #2COC1=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)=C1O4091.3Semi standard non polar33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,1TMS,isomer #3COC1=C(O)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)=C1O[Si](C)(C)C4188.1Semi standard non polar33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,2TMS,isomer #1COC1=C(O[Si](C)(C)C)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)=C1O[Si](C)(C)C4107.4Semi standard non polar33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,2TMS,isomer #2COC1=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)=C1O[Si](C)(C)C4098.5Semi standard non polar33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,2TMS,isomer #3COC1=C(O)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)=C1O[Si](C)(C)C4096.5Semi standard non polar33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,3TMS,isomer #1COC1=C(O[Si](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(C)C(O[Si](C)(C)C)=C1O[Si](C)(C)C4113.5Semi standard non polar33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,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)=C1O[Si](C)(C)C(C)(C)C4317.6Semi standard non polar33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,1TBDMS,isomer #2COC1=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)=C1O4313.4Semi standard non polar33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,1TBDMS,isomer #3COC1=C(O)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)=C1O[Si](C)(C)C(C)(C)C4402.8Semi standard non polar33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,2TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)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)=C1O[Si](C)(C)C(C)(C)C4517.3Semi standard non polar33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,2TBDMS,isomer #2COC1=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)=C1O[Si](C)(C)C(C)(C)C4511.4Semi standard non polar33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,2TBDMS,isomer #3COC1=C(O)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)=C1O[Si](C)(C)C(C)(C)C4522.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-08ml-2298480000-2cbb61853354b11007ec2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (1 TMS) - 70eV, Positivesplash10-000i-3147469000-5fdc766ff10e478f5f012017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS ("2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 10V, Positive-QTOFsplash10-004i-0213090000-4a65137eb42195f434de2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 20V, Positive-QTOFsplash10-0035-1549230000-463e4c4d13762fa9850a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 40V, Positive-QTOFsplash10-0002-3269420000-40341ce89f21aa25ad3d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 10V, Negative-QTOFsplash10-004i-0000090000-6ffefbe22ee39bd8d2072017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 20V, Negative-QTOFsplash10-004i-1000190000-c35bad59002e8ccdf17f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 40V, Negative-QTOFsplash10-076r-5200980000-8112877d445f435d22c72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 10V, Positive-QTOFsplash10-00or-5226590000-6dda2e5d3269dc410c732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 20V, Positive-QTOFsplash10-001i-9648220000-9470cbdf01957ebc558f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 40V, Positive-QTOFsplash10-0536-9513000000-2ef87b7732dc779309142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 10V, Negative-QTOFsplash10-004i-0000090000-121478cabf4ee3db57a12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 20V, Negative-QTOFsplash10-002b-0610290000-23fcf10e704d6d40fa382021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 40V, Negative-QTOFsplash10-004j-1533920000-0d9f372f51b6e522994e2021-09-22Wishart 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 IDFDB028803
KNApSAcK IDNot Available
Chemspider ID30776599
KEGG Compound IDNot Available
BioCyc ID2-HEXAPRENYL-3-METHYL-5-HYDROXY-6-METHOX
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481381
PDB IDNot Available
ChEBI IDNot Available
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.

Enzymes

General function:
Involved in methyltransferase activity
Specific function:
Not Available
Gene Name:
COQ3
Uniprot ID:
Q9NZJ6
Molecular weight:
41053.76