Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001968
Identification
Name: Ubiquinol-1
Description:Ubiquinol-1 is a member of the chemical class known as Polyprenylbenzoquinols. They are reduced forms of polyprenylbenzoquinines (ubiquinones). These are compounds containing a polyisoprene chain attached to a quinol at the second ring position. Ubiquiol-1 has just 1 isoprene unit. Normally in Pseudomonas aeruginosa the active form of Ubiquinol has 8 isoprene units (Ubiquinol-8) and in humans it normally has 10. Ubiquinol-1 is a ??ailed??or incomplete version of Ubiquinol 8 that arises from conjugation by a shortened prenyl tail via 4-hydroxybenzoate polyprenyltransferase. Coenzyme Q(n) exists in three redox states, fully oxidized (ubiquinone), partially reduced (semiquinones or ubisemiquinones), and fully reduced (ubiquinols). The redox functions of ubiquinol in cellular energy production and antioxidant protection are based on the ability to exchange two electrons in a redox cycle between ubiquinol (reduced) and the ubiquinone (oxidized) form. Ubiquionols are important in cellular respiration. They are fat-soluble and therefore mobile in cellular membranes; they play 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:
  • Not Available
Chemical Formula: C14H20O4
Average Molecular Weight: 252.3062
Monoisotopic Molecular Weight: 252.136159128
InChI Key: TVLSKGDBUQMDPR-UHFFFAOYSA-N
InChI:InChI=1S/C14H20O4/c1-8(2)6-7-10-9(3)11(15)13(17-4)14(18-5)12(10)16/h6,15-16H,7H2,1-5H3
CAS number: Not Available
IUPAC Name:2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)benzene-1,4-diol
Traditional IUPAC Name: 2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)benzene-1,4-diol
SMILES:COC1=C(O)C(C)=C(CC=C(C)C)C(O)=C1OC
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as prenylated hydroquinones. These are quinones with a structure characterized by the hydroquinone ring substituted by an prenyl side-chain.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Prenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct Parent Prenylated hydroquinones
Alternative Parents
Substituents
  • Prenylbenzoquinol
  • Ubiquinol skeleton
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Hydroxyquinol derivative
  • Methoxybenzene
  • Phenol ether
  • O-cresol
  • M-cresol
  • Hydroquinone
  • Anisole
  • Toluene
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular Framework Aromatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.306 mg/mLALOGPS
logP2.7ALOGPS
logP3.29ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)10.27ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.23 m3·mol-1ChemAxon
Polarizability27.93 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0190000000-a6ad04484f30fd3e6542View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6t-3890000000-88f5855287f7c4803858View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvi-6910000000-2566d9b9220bdfd47f6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-d3c87a4ee5f1fc3e1e44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-1790000000-f43f7dda07b2e0c3a516View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00y0-8920000000-223ce579fce165e10c55View in MoNA
References
References:
  • 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) Not Available
External Links:
ResourceLink
CHEBI ID17976
HMDB IDHMDB59661
Pubchem Compound ID447920
Kegg IDNot Available
ChemSpider ID394877
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Pyruvate + ferricytochrome b1 + H(2)O = acetate + CO(2) + ferrocytochrome b1
Gene Name:
poxB
Locus Tag:
PA5297
Molecular weight:
62.3 kDa
Reactions
Pyruvate + ubiquinone + H(2)O = acetate + CO(2) + ubiquinol.
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.
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes proline to glutamate for use as a carbon and nitrogen source and also function as a transcriptional repressor of the put operon
Gene Name:
putA
Locus Tag:
PA0782
Molecular weight:
115.6 kDa
Reactions
L-proline + acceptor = (S)-1-pyrroline-5-carboxylate + reduced acceptor.
(S)-1-pyrroline-5-carboxylate + NAD(P)(+) + 2 H(2)O = L-glutamate + NAD(P)H.
General function:
Involved in oxidation-reduction process
Specific function:
sn-glycerol 3-phosphate + NAD(P)(+) = glycerone phosphate + NAD(P)H
Gene Name:
gpsA
Locus Tag:
PA1614
Molecular weight:
36.8 kDa
Reactions
sn-glycerol 3-phosphate + NAD(P)(+) = glycerone phosphate + NAD(P)H.
General function:
Involved in catalytic activity
Specific function:
(S)-dihydroorotate + a quinone = orotate + a quinol
Gene Name:
pyrD
Locus Tag:
PA3050
Molecular weight:
36.1 kDa
Reactions
(S)-dihydroorotate + a quinone = orotate + a quinol.
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.
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
General function:
Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoA
Locus Tag:
PA2637
Molecular weight:
15 kDa
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoB
Locus Tag:
PA2638
Molecular weight:
25.4 kDa
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in oxidoreductase activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoE
Locus Tag:
PA2640
Molecular weight:
18.1 kDa
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in oxidation-reduction process
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient. This subunit may bind ubiquinone
Gene Name:
nuoH
Locus Tag:
PA2643
Molecular weight:
36.7 kDa
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in electron carrier activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoI
Locus Tag:
PA2644
Molecular weight:
20.6 kDa
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoJ
Locus Tag:
PA2645
Molecular weight:
17.6 kDa
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:
There are 2 NADH dehydrogenases in Pseudomonas aeruginosa, however only this complex is able to use dNADH (reduced nicotinamide hypoxanthine dinucleotide, deamino-NADH) and dNADH-DB (dimethoxy- 5-methyl-6-decyl-1,4-benzoquinone) as substrates
Gene Name:
nuoK
Locus Tag:
PA2646
Molecular weight:
11 kDa
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoM
Locus Tag:
PA2648
Molecular weight:
55.7 kDa
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoN
Locus Tag:
PA2649
Molecular weight:
51.7 kDa
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in oxidoreductase activity, acting on CH-OH group of donors
Specific function:
GDH is probably involved in energy conservation rather than in sugar metabolism
Gene Name:
gcd
Locus Tag:
PA2290
Molecular weight:
86.2 kDa
Reactions
D-glucose + ubiquinone = D-glucono-1,5-lactone + ubiquinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoF
Locus Tag:
PA2641
Molecular weight:
48.7 kDa
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoC
Locus Tag:
PA2639
Molecular weight:
68.3 kDa
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in electron carrier activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoG
Locus Tag:
PA2642
Molecular weight:
99 kDa
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoL
Locus Tag:
PA2647
Molecular weight:
66.2 kDa
Reactions
NADH + quinone = NAD(+) + quinol.
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
General function:
Involved in cytochrome bo3 ubiquinol oxidase activity
Specific function:
Cytochrome o terminal oxidase complex is the component of the aerobic respiratory chain of Pseudomonas aeruginosa that predominates when cells are grown at high aeration
Gene Name:
cyoA
Locus Tag:
PA1317
Molecular weight:
36.6 kDa
Reactions
Ubiquinol-8 + O(2) = Ubiquinone-8 + H(2)O.
General function:
Involved in cytochrome o ubiquinol oxidase activity
Specific function:
Cytochrome o terminal oxidase complex is the component of the aerobic respiratory chain of Pseudomonas aeruginosa that predominates when cells are grown at high aeration
Gene Name:
cyoD
Locus Tag:
PA1320
Molecular weight:
12.1 kDa
General function:
Involved in cytochrome-c oxidase activity
Specific function:
Cytochrome o terminal oxidase complex is the component of the aerobic respiratory chain of Pseudomonas aeruginosa that predominates when cells are grown at high aeration. This ubiquinol oxidase shows proton pump activity across the membrane in addition to the electron transfer
Gene Name:
cyoB
Locus Tag:
PA1318
Molecular weight:
73.9 kDa
Reactions
Ubiquinol-8 + O(2) = Ubiquinone-8 + H(2)O.
General function:
Involved in heme-copper terminal oxidase activity
Specific function:
Cytochrome o terminal oxidase complex is the component of the aerobic respiratory chain of Pseudomonas aeruginosa that predominates when cells are grown at high aeration
Gene Name:
cyoC
Locus Tag:
PA1319
Molecular weight:
22.8 kDa
Reactions
Ubiquinol-8 + O(2) = Ubiquinone-8 + H(2)O.