ECMDB: Ubiquinol-6 (ECMDB21460) (M2MDB001855)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (5)XML

Proteins (5)

Record Information

Version

2.0

Creation Date

2012-08-09 09:16:19 -0600

Update Date

2015-06-03 17:21:33 -0600

Secondary Accession Numbers

ECMDB21460

Identification

Name:

Ubiquinol-6

Description

Ubiquinol-6 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-6 has just 6 isoprene units. Normally in E. coli the active form of Ubiquinol has 8 isoprene units (Ubiquinol-8) and in humans it normally has 10. Ubiquinol-6 is a “failed” 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

MOL SDF PDB SMILES InChI

Synonyms:

2-(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaenyl-5,6-dimethoxy-3-methylbenzene-1,4-diol
Dihydroubiquinone
Reduced ubiquinone
Ubiquinol
Ubiquinol(30)

Chemical Formula:

C₃₉H₆₀O₄

Weight:

Average: 592.8913
Monoisotopic: 592.449160408

InChI Key:

DYOSCPIQEYRQEO-LPHQIWJTSA-N

InChI:

InChI=1S/C39H60O4/c1-28(2)16-11-17-29(3)18-12-19-30(4)20-13-21-31(5)22-14-23-32(6)24-15-25-33(7)26-27-35-34(8)36(40)38(42-9)39(43-10)37(35)41/h16,18,20,22,24,26,40-41H,11-15,17,19,21,23,25,27H2,1-10H3/b29-18+,30-20+,31-22+,32-24+,33-26+

CAS number:

5677-58-7

IUPAC Name:

2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-5,6-dimethoxy-3-methylbenzene-1,4-diol

Traditional IUPAC Name:

ubiquinol-6

SMILES:

COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. 2-polyprenyl-6-methoxyphenols are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyprenylphenols

Direct Parent

2-polyprenyl-6-methoxyphenols

Alternative Parents

Substituents

2-polyprenyl-6-methoxyphenol
Polyprenylbenzoquinol
Sesterterpenoid
Prenylbenzoquinol
Ubiquinol skeleton
Methoxyphenol
O-dimethoxybenzene
Dimethoxybenzene
Anisole
Hydroquinone
M-cresol
Phenoxy compound
O-cresol
Phenol ether
Methoxybenzene
Alkyl aryl ether
Phenol
Toluene
Monocyclic benzene moiety
Benzenoid
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

polyprenylhydroquinone (CHEBI:52970 )
ubiquinol (CHEBI:52970 )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.00035 g/L	ALOGPS
logP	8.49	ALOGPS
logP	11.59	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	10.27	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	191.24 m³·mol⁻¹	ChemAxon
Polarizability	75.45 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Membrane

Reactions:

Succinic acid + Ubiquinone-6 > Fumaric acid + Ubiquinol-6
L-Lactic acid + Ubiquinone-6 > Pyruvic acid + Ubiquinol-6

SMPDB Pathways:

TCA cycle (ubiquinol-6)

PW001006

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05dr-2168390000-394910f888dc5f30f46d	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0002-3128379000-0117b81715e9c07a4c03	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Ubiquinol-6,1TMS,#1" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0223190000-d20ae1eccfe0bb20cd4c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0669330000-51dfe9ccd5bc50aa4b9d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fr2-2159340000-bc6056287dbe529b04e3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000090000-bdbe9cf3cbc85ce127e4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kf-0000190000-15019b0edbf51d3e63b8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00fr-9200450000-c956803409da86b9394a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0016-5317390000-fe62471cddaa2c9b728a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000t-7619110000-ba2f99a58a62b2b83131	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000y-9613000000-b2ee70ccfb91ef2ecc7a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000090000-ad84dec376fad5d3e7d7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-0611190000-69cb09efd0cb9335d4f6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0171-3792540000-de6e147147d07d8f5824	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

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

Links

External Links:

Resource	Link
CHEBI ID	52970
HMDB ID	HMDB12299
Pubchem Compound ID	3393375
Kegg ID	Not Available
ChemSpider ID	4710167
Wikipedia	NULL
BioCyc ID	Not Available

Enzymes

Protein Details

1. D-lactate dehydrogenase

General function:: Involved in flavin adenine dinucleotide binding
Specific function:: First component of the membrane-bound D-lactate oxidase, which is believed to play an important role in the energization of the active transport of a variety of sugars and amino acids
Gene Name:: dld
Uniprot ID:: P06149
Molecular weight:: 64612

Reactions

(R)-lactate + NAD(+) = pyruvate + NADH.

Protein Details

2. 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
Uniprot ID:: P07014
Molecular weight:: 26770

Reactions

Succinate + acceptor = fumarate + reduced acceptor.

Protein Details

3. 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
Uniprot ID:: P0AC41
Molecular weight:: 64421

Reactions

Succinate + acceptor = fumarate + reduced acceptor.

Protein Details

4. 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
Uniprot ID:: P0AC44
Molecular weight:: 12867

Protein Details

5. Succinate dehydrogenase cytochrome b556 subunit

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

Ubiquinol-6 (ECMDB21460) (M2MDB001855)

Structure for #<Compound:0x9d7dd67c>

Enzymes

Reactions

Reactions

Reactions