Record Information
Version1.0
Creation date2010-04-08 22:13:39 UTC
Update date2019-11-26 03:16:02 UTC
Primary IDFDB018340
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameUbiquinone 4
DescriptionIsolated from various yeasts Ubiquinone Q4 is a Coenzyme Q analogue that have been identified in brain. Coenzyme Q is the only type of Quinones 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; 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. 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 amount of isoprenoid units attached at the 6- position on the benzoquinone ring of the coenzyme Q moiety. (PMID: 12064350); to recycle the radical forms of vitamin C and E
CAS Number4370-62-1
Structure
Thumb
Synonyms
SynonymSource
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
2,3-Dimethoxy-5-methyl-6-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-P-benzoquinoneHMDB
2,3-Dimethoxy-5-methyl-6-(geranylgeranyl)-1,4-benzoquinoneMetaCyc
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
Ubiquinone q4HMDB
Predicted 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
Chemical FormulaC29H42O4
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
InChI IdentifierInChI=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
Isomeric SMILESCOC1=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
Average Molecular Weight454.6414
Monoisotopic Molecular Weight454.308309832
Classification
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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 76.61%; H 9.31%; O 14.08%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSUbiquinone 4, 2 TMS, GC-MS Spectrumsplash10-0006-8569000000-59442bb36544f3769091Spectrum
GC-MSUbiquinone 4, 2 TMS, GC-MS Spectrumsplash10-000x-7689001000-c8660617cb5cd593222bSpectrum
GC-MSUbiquinone 4, non-derivatized, GC-MS Spectrumsplash10-0006-8569000000-59442bb36544f3769091Spectrum
GC-MSUbiquinone 4, non-derivatized, GC-MS Spectrumsplash10-000x-7689001000-c8660617cb5cd593222bSpectrum
Predicted GC-MSUbiquinone 4, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-2559500000-8b9beaf0f7bae959247eSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0222900000-7068674fa2846a47c74dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059e-1974200000-fca47eaee65794b87205Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-7479000000-faf4846ac88a76e1061dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001900000-e42e8d16aa71cad12871Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-0108900000-f9427f19705024476e83Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9106400000-f3a6445d4e177a9e3c4eSpectrum
NMRNot Available
ChemSpider ID4446658
ChEMBL IDCHEMBL407116
KEGG Compound IDNot Available
Pubchem Compound ID5283545
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06710
CRC / DFC (Dictionary of Food Compounds) IDHPW46-V:LJR45-X
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference