Record Information
Version2.0
Creation Date2012-11-08 09:25:53 -0700
Update Date2015-06-03 17:27:29 -0600
Secondary Accession Numbers
  • ECMDB23734
Identification
Name:Ubiquinone-5
DescriptionUbiquinone-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 E. coli the active form of Ubiquinone has 8 isoprene units (Ubiquinone-8) and in humans it normally has 10. Ubiquinone-5 is a “failed” 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
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
Weight:Average: 522.7584
Monoisotopic: 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
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
  • Polyprenylbenzoquinone
  • Sesterterpenoid
  • 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
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00048 g/LALOGPS
logP7.63ALOGPS
logP8.86ChemAxon
logS-6ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity167.59 m³·mol⁻¹ChemAxon
Polarizability64.05 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
TCA cycle (ubiquinol-5)PW001005 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
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 IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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
Uniprot ID:
P07014
Molecular weight:
26770
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
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
Uniprot ID:
P0AC41
Molecular weight:
64421
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
General function:
Involved in succinate dehydrogenase activity
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH)
Gene Name:
sdhD
Uniprot ID:
P0AC44
Molecular weight:
12867
General function:
Involved in succinate dehydrogenase activity
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH)
Gene Name:
sdhC
Uniprot ID:
P69054
Molecular weight:
14299