Ubiquinone-2 (PAMDB001975)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001975
Identification
Name: Ubiquinone-2
Description:Ubiquinone-2 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-2 has just 2 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-2 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:
  • (E)-2-(3,7-dimethyl-2,6-octadienyl)-5,6-dimethoxy-3-methyl-p-benzoquinone
  • 2,3-Dimethoxy-5-geranyl-6-methyl-1,4-benzoquinone
  • 2-(3,7-dimethyl-2,6-octadienyl)-5,6-dimethoxy-3-methyl- p-Benzoquinone
  • 2-(3,7-dimethyl-2,6-octadienyl)-5,6-dimethoxy-3-methyl-2,5-Cyclohexadiene-1,4-dione
  • 2-[(2E)-3,7-dimethyl-2,6-octadienyl]-5,6-dimethoxy-3-methyl- p-Benzoquinone
  • 2-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-5,6-dimethoxy-3-methyl-1,4-benzoquinone
  • 2-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
  • Coenzyme Q
  • Coenzyme Q2
  • CoQ
  • Q 2
  • Ubidecarenone
  • Ubiquinone
  • Ubiquinone 2
  • Ubiquinone Q2
  • Ubiquinone-2
Chemical Formula: C19H26O4
Average Molecular Weight: 318.4073
Monoisotopic Molecular Weight: 318.18310932
InChI Key: SQQWBSBBCSFQGC-JLHYYAGUSA-N
InChI:InChI=1S/C19H26O4/c1-12(2)8-7-9-13(3)10-11-15-14(4)16(20)18(22-5)19(23-6)17(15)21/h8,10H,7,9,11H2,1-6H3/b13-10+
CAS number: 606-06-4
IUPAC Name:2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
Traditional IUPAC Name: coenzyme-Q
SMILES:COC1=C(OC)C(=O)C(C\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
  • Ubiquinone skeleton
  • Monoterpenoid
  • Monocyclic monoterpenoid
  • 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: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.01 mg/mLALOGPS
logP3.75ALOGPS
logP3.88ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity96.18 m3·mol-1ChemAxon
Polarizability36.45 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Succinic acid + Ubiquinone-2 > Fumaric acid + Ubiquinol-2
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0439000000-180eeec0662a1cd541e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ba-3942000000-6814d10b6c7404b88af9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9410000000-95413a2c0ab148a85d9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-f5070dbbdd24c4bc12aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-0296000000-7c0eaf226e5a4866b999View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9361000000-fff86254a78962e3b850View in MoNA
References
References:
  • Forsmark-Andree P, Lee CP, Dallner G, Ernster L: Lipid peroxidation and changes in the ubiquinone content and the respiratory chain enzymes of submitochondrial particles. Free Radic Biol Med. 1997;22(3):391-400. Pubmed: 8981030
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID46372
HMDB IDHMDB06709
Pubchem Compound ID5280346
Kegg IDC00399
ChemSpider ID4444053
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoUQ2

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
• 3-demethylubiquinone-9 3-methyltransferase
General function:
Involved in 2-polyprenyl-6-methoxy-1,4-benzoquinone methyltransferase activity
Specific function:
S-adenosyl-L-methionine + 3- demethylubiquinone-9 = S-adenosyl-L-homocysteine + ubiquinone-9
Gene Name:
ubiG
Locus Tag:
PA3171
Molecular weight:
25.9 kDa
Reactions
S-adenosyl-L-methionine + 3-demethylubiquinone-n = S-adenosyl-L-homocysteine + ubiquinone-n.
S-adenosyl-L-methionine + 3-(all-trans-polyprenyl)benzene-1,2-diol = S-adenosyl-L-homocysteine + 2-methoxy-6-(all-trans-polyprenyl)phenol.
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