Ubiquinone-0 (PAMDB001302)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001302
Identification
Name: Ubiquinone-0
Description:Ubiquinone-1 is a member of the chemical class known as Benzoquinones. Normally in Pseudomonas aeruginosa the active form of Ubiquinone has 8 isoprene units (Ubiquinone-8) and in humans it normally has 10. Ubiquinone-10 is a naked 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-1,4-benzoquinone
  • 2,3-Dimethoxy-5-methyl-2,5-Cyclohexadiene-1,4-dione
  • 2,3-Dimethoxy-5-methyl-p-benzoquinone
  • 2,3-Dimethoxy-5-methylbenzo-1,4-quinone
  • 2,3-Dimethoxy-5-methylbenzoquinone
  • 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione
  • 2,3-Dimethyoxyl-5-methyl-1,4-benzoquinone
  • 2-Methyl-4,5-dimethoxy-p-quinone
  • 2-Methyl-5,6-dimethoxybenzoquinone
  • Coenzyme q0
  • Coq0
  • D9150_SIGMA
  • Nchembio.62-comp10
  • Q0
  • Q0
  • Ubiquinone 0
  • Ubiquinone q0
  • Ubiquinone-O
  • Ubiquinone-Q0
  • Ubiquinone-Q0
Chemical Formula: C9H10O4
Average Molecular Weight: 182.1733
Monoisotopic Molecular Weight: 182.057908808
InChI Key: UIXPTCZPFCVOQF-UHFFFAOYSA-N
InChI:InChI=1S/C9H10O4/c1-5-4-6(10)8(12-2)9(13-3)7(5)11/h4H,1-3H3
CAS number: 605-94-7
IUPAC Name:2,3-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione
Traditional IUPAC Name: coenzyme Q0
SMILES:COC1=C(OC)C(=O)C(C)=CC1=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
  • 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: 59-60 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.37 mg/mLALOGPS
logP0.53ALOGPS
logP0.61ChemAxon
logS-1.5ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.82 m3·mol-1ChemAxon
Polarizability17.64 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-2254c47ae8fb318c40d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-41fba48cebbe97a50219View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-01d5266ce1b46a31e76bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-9f847c697f47c86325cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-a9bb75a201179aa4a95aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-9300000000-15e8eb3a072ce7d451d0View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID27906
HMDB IDNot Available
Pubchem Compound ID69068
Kegg IDC05251
ChemSpider ID62289
Wikipedia IDNot Available
BioCyc IDCPD0-1464
EcoCyc IDCPD0-1464

Enzymes

Protein Details
• Pyruvate dehydrogenase [cytochrome]
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.
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
Protein Details
• Probable ubiquinone biosynthesis protein ubiB
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Required, probably indirectly, for the hydroxylation of 2-octaprenylphenol to 2-octaprenyl-6-hydroxy-phenol, the fourth step in ubiquinone biosynthesis. Specific for aerobically grown log-phase cells
Gene Name:
ubiB
Locus Tag:
PA5065
Molecular weight:
61.7 kDa