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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:55:47 UTC
Update Date2022-03-07 03:17:43 UTC
HMDB IDHMDB0060352
Secondary Accession Numbers
  • HMDB60352
Metabolite Identification
Common Name2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone
Description2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone 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). 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866048
SynonymsNot Available
Chemical FormulaC18H24O4
Average Molecular Weight304.3808
Monoisotopic Molecular Weight304.167459256
IUPAC Name2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-hydroxy-6-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione
Traditional Name2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-hydroxy-6-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione
CAS Registry NumberNot Available
SMILES
COC1=C(O)C(=O)C(C)=C(C\C=C(/C)CCC=C(C)C)C1=O
InChI Identifier
InChI=1S/C18H24O4/c1-11(2)7-6-8-12(3)9-10-14-13(4)15(19)17(21)18(22-5)16(14)20/h7,9,21H,6,8,10H2,1-5H3/b12-9+
InChI KeyJVLAJUCFVRPDAQ-FMIVXFBMSA-N
Chemical Taxonomy
Description 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
  • Vinylogous acid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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 Solubility0.012 g/LALOGPS
logP3.09ALOGPS
logP3.77ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)8.31ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity91.43 m³·mol⁻¹ChemAxon
Polarizability34.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+179.71230932474
DeepCCS[M-H]-177.35430932474
DeepCCS[M-2H]-210.30130932474
DeepCCS[M+Na]+185.80630932474
AllCCS[M+H]+175.132859911
AllCCS[M+H-H2O]+171.932859911
AllCCS[M+NH4]+178.132859911
AllCCS[M+Na]+179.032859911
AllCCS[M-H]-178.832859911
AllCCS[M+Na-2H]-179.432859911
AllCCS[M+HCOO]-180.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinoneCOC1=C(O)C(=O)C(C)=C(C\C=C(/C)CCC=C(C)C)C1=O3197.4Standard polar33892256
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinoneCOC1=C(O)C(=O)C(C)=C(C\C=C(/C)CCC=C(C)C)C1=O2041.8Standard non polar33892256
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinoneCOC1=C(O)C(=O)C(C)=C(C\C=C(/C)CCC=C(C)C)C1=O2208.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone,1TMS,isomer #1COC1=C(O[Si](C)(C)C)C(=O)C(C)=C(C/C=C(\C)CCC=C(C)C)C1=O2320.5Semi standard non polar33892256
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone,1TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C(C)=C(C/C=C(\C)CCC=C(C)C)C1=O2558.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-3490000000-0edba616b6e1e0c917ed2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone GC-MS (1 TMS) - 70eV, Positivesplash10-03k9-6649000000-b8f9f1d637fe5d24c5f32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone 10V, Positive-QTOFsplash10-0a4i-0569000000-dd7efcdfd9d0f9480c482017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone 20V, Positive-QTOFsplash10-0ac0-4931000000-3e688836d12c6b05367a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone 40V, Positive-QTOFsplash10-0690-9410000000-edf9000e56282cac94362017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone 10V, Negative-QTOFsplash10-0udi-0049000000-5bb1699e50e42794d1002017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone 20V, Negative-QTOFsplash10-0udj-1192000000-ecde9d151824491818562017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone 40V, Negative-QTOFsplash10-0uk9-7790000000-465875fa98b66e16ae832017-10-06Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC17562
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound135437103
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. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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
Reactions
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine → Ubiquinone-2 + S-Adenosylhomocysteinedetails
General function:
Involved in oxidoreductase activity
Specific function:
Involved in lifespan determination in ubiquinone-independent manner. Involved in ubiquinone biosynthesis. Potential central metabolic regulator (By similarity).
Gene Name:
COQ7
Uniprot ID:
Q99807
Molecular weight:
Not Available
Reactions
2-Polyprenyl-3-methyl-6-methoxy-1,4-benzoquinone + Oxygen + NADPH + Hydrogen Ion → 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + NADP + Waterdetails