Ubiquinone-5 (PAMDB004124)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB004124
Identification
Name: Ubiquinone-5
Description:Ubiquinone-5 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-5 has just 5 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-5 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:
  • (all-e)-2,3-Dimethoxy-5-methyl-6-(3,7,11,15,19-pentamethyl-2,6,10,14,18-eicosapentaenyl)-2,5-cyclohexadiene-1,4-dione
  • 2,3-DIMETHOXY-5-methyl-6-(3,11,15,19-tetramethyl-eicosa-2,6,10,14,18-pentaenyl)-[1,4]benzoquinone
  • 2,3-Dimethoxy-5-methyl-6-pentaprenyl-1,4-benzoquinone
  • 2,3-Dimethoxy-5-methyl-6-[(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-yl]-1,4-benzoquinone
  • Coenzyme Q5
  • CoQ5
  • Ubiquinone 25
Chemical Formula: C34H50O4
Average Molecular Weight: 522.7584
Monoisotopic Molecular Weight: 522.370910088
InChI Key: NYFAQDMDAFCWPU-UVCHAVPFSA-N
InChI:InChI=1S/C34H50O4/c1-24(2)14-10-15-25(3)16-11-17-26(4)18-12-19-27(5)20-13-21-28(6)22-23-30-29(7)31(35)33(37-8)34(38-9)32(30)36/h14,16,18,20,22H,10-13,15,17,19,21,23H2,1-9H3/b25-16+,26-18+,27-20+,28-22+
CAS number: Not Available
IUPAC Name:2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-yl]cyclohexa-2,5-diene-1,4-dione
Traditional IUPAC Name: ubiquinone 5
SMILES:[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=C(C)C(=O)C(OC)=C(OC)C1=O)=C(\C)CCC=C(C)C
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
  • Polyprenylbenzoquinone
  • Sesterterpenoid
  • 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 Solubility0.000483 mg/mLALOGPS
logP7.63ALOGPS
logP8.86ChemAxon
logS-6ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity167.59 m3·mol-1ChemAxon
Polarizability64.05 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-5 > Fumaric acid + Ubiquinol-5
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0223290000-0cd4f085463ea6aa5276View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004m-0669220000-d1cd48e3ba40aa526c96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-3019200000-5b5eea296be3ad05165fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000190000-39e0506f2651b3165f4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-0100970000-0e5b3d22f34710aea1eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9101720000-226803170c42bb60089aView in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID46331
HMDB IDNot Available
Pubchem Compound ID12832984
Kegg IDNot Available
ChemSpider ID20147958
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