Ubiquinone-4 (PAMDB004125)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB004125
Identification
Name: Ubiquinone-4
Description:Ubiquinone-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 Pseudomonas aeruginosa the active form of Ubiquinone has 8 isoprene units (Ubiquinone-8) and in humans it normally has 10. Ubiquinone-4 is a ??ailed??or incomplete version of Ubiquinone 8 that arises from conjugation by a shortened prenyl tail via 4-hydroxybenzoate polyprenyltransferase. Ubiquionone is involved in cellular respiration. It is fat-soluble and is therefore mobile in cellular membranes; it plays a unique role in the electron transport chain (ETC). In the inner bacterial membrane, electrons from NADH and succinate pass through the ETC to the oxygen, which is then reduced to water. The transfer of electrons through ETC results in the pumping of H+ across the membrane creating a proton gradient across the membrane, which is used by ATP synthase (located on the membrane) to generate ATP.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2,3-Dimethoxy-5-methyl-6-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-2,5-cyclohexadiene-1,4-dione
  • 2,3-Dimethoxy-5-methyl-6-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-P-benzoquinone
  • 2,3-Dimethoxy-5-methyl-6-(geranylgeranyl)-1,4-benzoquinone
  • 2,3-Dimethoxy-5-methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-2,5-cyclohexadiene-1,4-dione
  • Coenzyme Q4
  • CoQ4
  • Ubiquinone 4
  • Ubiquinone Q4
Chemical Formula: C29H42O4
Average Molecular Weight: 454.6414
Monoisotopic Molecular Weight: 454.308309832
InChI Key: XGCJRRDNIMSYNC-INVBOZNNSA-N
InChI: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+
CAS number: Not Available
IUPAC Name:2,3-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 IUPAC Name: ubiquinone 4
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
Chemical Taxonomy
Taxonomy DescriptionThis compound 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).
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Prenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct Parent Ubiquinones
Alternative Parents
Substituents
  • Diterpenoid
  • Ubiquinone skeleton
  • Quinone
  • P-benzoquinone
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular Framework Aliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.000888 mg/mLALOGPS
logP6.53ALOGPS
logP7.2ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity143.79 m3·mol-1ChemAxon
Polarizability55.21 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Succinic acid + Ubiquinone-4 > Fumaric acid + Ubiquinol-4
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0006-8569000000-59442bb36544f3769091View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-000x-7689001000-c8660617cb5cd593222bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0222900000-7068674fa2846a47c74dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059e-1974200000-fca47eaee65794b87205View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-7479000000-faf4846ac88a76e1061dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001900000-e42e8d16aa71cad12871View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-0108900000-f9427f19705024476e83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9106400000-f3a6445d4e177a9e3c4eView in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID529178
HMDB IDHMDB06710
Pubchem Compound ID5283545
Kegg IDNot Available
ChemSpider ID4446658
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
• Succinate dehydrogenase iron-sulfur subunit
General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
sdhB
Locus Tag:
PA1584
Molecular weight:
26.2 kDa
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
Protein Details
• Succinate dehydrogenase flavoprotein subunit
General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
sdhA
Locus Tag:
PA1583
Molecular weight:
63.5 kDa
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
Protein Details
• Succinate dehydrogenase hydrophobic membrane anchor subunit
General function:
Involved in succinate dehydrogenase activity
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH)
Gene Name:
sdhD
Locus Tag:
PA1582
Molecular weight:
13.7 kDa
Protein Details
• Succinate dehydrogenase cytochrome b556 subunit
General function:
Involved in succinate dehydrogenase activity
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH)
Gene Name:
sdhC
Locus Tag:
PA1581
Molecular weight:
13.7 kDa