Hmdb loader
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 Date2007-07-11 09:24:51 UTC
Update Date2020-02-26 21:26:41 UTC
HMDB IDHMDB0006710
Secondary Accession Numbers
  • HMDB06710
Metabolite Identification
Common NameUbiquinone-4
DescriptionUbiquinone-4 is a member of the chemical class known as Polyprenylbenzoquinones. These are compounds containing a polyisoprene chain attached to a quinone at the second ring position. Ubiquione-4 has just 4 isoprene units. Normally in humans it has 10 (CoQ10). Ubiquinone-4 is an intermediate in the synthesis of Ubiquionone 10. Ubiquinone-4 is a Coenzyme Q analogue that have been identified in brain. Based on the isoprenoid moiety, the presence of various coenzyme Q homologues in prokaryotes and eurkaryotes has been confirmed, and these homologues are classified as Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, and Q12. The numbers, Qn, refer to the number of isoprenoid units attached at the 6- position on the benzoquinone ring of the coenzyme Q moiety. (PMID: 12064350 ) Coenzyme Q is the only type of Quinone naturally found in animals (other quinones such as vitamin K is provided by foods). Coenzyme Q is a fat-soluble and amphipathic compound that is the integral component of the electron transport chain in mitochondria. It is ubiquitous in nature and is found in subcellular organelles, serum lipoproteins, blood plasma, urine, and feces. Ubiquinones are amphipathic because of the benzoquinone ring (hydrophilic) and the polyisoprenoid side chain moiety (lipophilic). The primary role of coenzyme Q is to transfer electrons between redox components of the electron transport chain, to create a proton gradient across the inner mitochondrial membrane and drive ATP formation. Additional functions of coenzyme Q are to influence membrane fluidity; to recycle the radical forms of vitamin C and E; and, most important, to act as a lipid antioxidant protecting membrane phospholipids against peroxidation. Coenzyme Q is the only endogenously occurring lipid-soluble antioxidant that occurs ubiquitously and can be synthesized in all organisms.
Structure
Data?1582752401
Synonyms
ValueSource
2,3-Dimethoxy-5-methyl-6-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-2,5-cyclohexadiene-1,4-dioneHMDB
2,3-Dimethoxy-5-methyl-6-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-P-benzoquinoneHMDB
2,3-Dimethoxy-5-methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-2,5-cyclohexadiene-1,4-dioneHMDB
Coenzyme Q4HMDB
CoQ4HMDB
Ubiquinone 4HMDB
Ubiquinone Q4HMDB
Chemical FormulaC29H42O4
Average Molecular Weight454.6414
Monoisotopic Molecular Weight454.308309832
IUPAC Name2,3-dimethoxy-5-methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]cyclohexa-2,5-diene-1,4-dione
Traditional Nameubiquinone 4
CAS Registry Number4370-62-1
SMILES
COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O
InChI Identifier
InChI=1S/C29H42O4/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-17-23(5)18-19-25-24(6)26(30)28(32-7)29(33-8)27(25)31/h12,14,16,18H,9-11,13,15,17,19H2,1-8H3/b21-14+,22-16+,23-18+
InChI KeyXGCJRRDNIMSYNC-INVBOZNNSA-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
  • Diterpenoid
  • Ubiquinone skeleton
  • Quinone
  • P-benzoquinone
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

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 Solubility0.00089 g/LALOGPS
logP6.53ALOGPS
logP7.2ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity143.79 m³·mol⁻¹ChemAxon
Polarizability55.21 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]+219.90730932474
DeepCCS[M-H]-217.54930932474
DeepCCS[M-2H]-250.43430932474
DeepCCS[M+Na]+226.030932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ubiquinone-4COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O4044.8Standard polar33892256
Ubiquinone-4COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O2884.1Standard non polar33892256
Ubiquinone-4COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O3211.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ubiquinone-4 GC-MS (2 TMS)splash10-0006-8569000000-59442bb36544f37690912014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ubiquinone-4 GC-MS (2 TMS)splash10-000x-7689001000-c8660617cb5cd593222b2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ubiquinone-4 GC-MS (Non-derivatized)splash10-0006-8569000000-59442bb36544f37690912017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ubiquinone-4 GC-MS (Non-derivatized)splash10-000x-7689001000-c8660617cb5cd593222b2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinone-4 GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2559500000-8b9beaf0f7bae959247e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinone-4 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinone-4 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 - Ubiquinone-4 10V, Positive-QTOFsplash10-0a4i-0222900000-7068674fa2846a47c74d2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-4 20V, Positive-QTOFsplash10-059e-1974200000-fca47eaee65794b872052015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-4 40V, Positive-QTOFsplash10-014r-7479000000-faf4846ac88a76e1061d2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-4 10V, Negative-QTOFsplash10-0udi-0001900000-e42e8d16aa71cad128712015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-4 20V, Negative-QTOFsplash10-0udj-0108900000-f9427f19705024476e832015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-4 40V, Negative-QTOFsplash10-000i-9106400000-f3a6445d4e177a9e3c4e2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-4 10V, Negative-QTOFsplash10-0udi-0000900000-f1e50cbc29fd693b50b22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-4 20V, Negative-QTOFsplash10-0wt9-0810900000-90aff911f7896bf3991f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-4 40V, Negative-QTOFsplash10-0569-0947700000-77cf870cad7a1c209f852021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-4 10V, Positive-QTOFsplash10-0002-2419200000-d730da3d3b74d9a19de02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-4 20V, Positive-QTOFsplash10-0002-4913000000-70d4eae966c9ef0997a02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-4 40V, Positive-QTOFsplash10-0535-7920000000-9705a4e6d45c5353a64f2021-09-24Wishart 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 IDFDB018340
KNApSAcK IDNot Available
Chemspider ID4446658
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283545
PDB IDNot Available
ChEBI ID529178
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Albano CB, Muralikrishnan D, Ebadi M: Distribution of coenzyme Q homologues in brain. Neurochem Res. 2002 May;27(5):359-68. [PubMed:12064350 ]