MiMeDB: Showing metabocard for Ubiquinol-2 (MMDBc0031712)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:45:23 UTC

Update Date

2022-08-31 18:23:45 UTC

MiMeDB ID

MMDBc0031712

Metabolite Identification

Common Name

Ubiquinol-2

Description

Ubiquinol-2 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-2 has just 2 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-2 is a ‚Äúfailed‚Äù 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

Value	Source
CoQH2	Kegg
Coenzymes QH2	HMDB
Reduced ubiquinone	HMDB
Ubiquinol	HMDB
Ubiquinone-1	HMDB
Coenzyme Q10, reduced	HMDB
Ubiquinol-10	HMDB

Chemical Formula

(C₅H₈)nC₁₄H₂₀O₄

Average Molecular Weight

Not Available

Monoisotopic Molecular Weight

Not Available

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C19H28O4/c1-12(2)8-7-9-13(3)10-11-15-14(4)16(20)18(22-5)19(23-6)17(15)21/h8,10,20-21H,7,9,11H2,1-6H3/b13-10+

InChI Key

RNUCUWWMTTWKAH-JLHYYAGUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ubiquinols. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methylbenzene-1,4-diol moiety to which an isoprenyl group is attached at ring position 2(or 6).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Ubiquinols

Alternative Parents

Substituents

Ubiquinol skeleton
Aromatic monoterpenoid
Methoxyphenol
Monocyclic monoterpenoid
Monoterpenoid
O-dimethoxybenzene
Dimethoxybenzene
Anisole
Phenoxy compound
Hydroquinone
M-cresol
Methoxybenzene
O-cresol
Phenol ether
Alkyl aryl ether
Phenol
Toluene
Monocyclic benzene moiety
Benzenoid
Ether
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Inner mitochondrial membrane
Membrane

Biospecimen Locations

Blood
Epidermis
Skeletal Muscle
Testis

Tissue Locations

Epidermis
Skeletal Muscle
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

#<MetaboliteProteinLink:0x000055b76de0f9a0>

Human Pathways

Pathways

Name	SMPDB/PathBank
Immunometabolism Pathway (Bacterial Activation)
Immunometabolism Pathway (Viral Activation)
Viral Sepsis

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference
Heart failure		This associated disease is originally imported from HMDB metabolite HMDB0001304 concentration id 17817	Association	Human Blood		17482886	details

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	1	Human	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Age	Sex	Health Condition	Data Source	Reference
Human	Detected and Quantified	7.4	2.7	Adult (>18 years old)	Both	Heart failure	HMDB	17482886	details
Human Epidermis	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Skeletal Muscle	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Testis	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597	details

External Links

HMDB ID

HMDB0001304

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022543

KNApSAcK ID

Not Available

Chemspider ID

4444052

KEGG Compound ID

C00390

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Coenzyme Q10

METLIN ID

6146

PubChem Compound

5280344

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Halliwell B, Hu ML, Louie S, Duvall TR, Tarkington BK, Motchnik P, Cross CE: Interaction of nitrogen dioxide with human plasma. Antioxidant depletion and oxidative damage. FEBS Lett. 1992 Nov 16;313(1):62-6. doi: 10.1016/0014-5793(92)81185-o. [PubMed:1426270 ]
Neuzil J, Stocker R: Free and albumin-bound bilirubin are efficient co-antioxidants for alpha-tocopherol, inhibiting plasma and low density lipoprotein lipid peroxidation. J Biol Chem. 1994 Jun 17;269(24):16712-9. [PubMed:8206992 ]
Shindo Y, Witt E, Han D, Epstein W, Packer L: Enzymic and non-enzymic antioxidants in epidermis and dermis of human skin. J Invest Dermatol. 1994 Jan;102(1):122-4. doi: 10.1111/1523-1747.ep12371744. [PubMed:8288904 ]
Peltola V, Huhtaniemi I, Metsa-Ketela T, Ahotupa M: Induction of lipid peroxidation during steroidogenesis in the rat testis. Endocrinology. 1996 Jan;137(1):105-12. doi: 10.1210/endo.137.1.8536600. [PubMed:8536600 ]
Lonnrot K, Metsa-Ketela T, Molnar G, Ahonen JP, Latvala M, Peltola J, Pietila T, Alho H: The effect of ascorbate and ubiquinone supplementation on plasma and CSF total antioxidant capacity. Free Radic Biol Med. 1996;21(2):211-7. doi: 10.1016/0891-5849(95)02207-4. [PubMed:8818636 ]
Kontush A, Reich A, Baum K, Spranger T, Finckh B, Kohlschutter A, Beisiegel U: Plasma ubiquinol-10 is decreased in patients with hyperlipidaemia. Atherosclerosis. 1997 Feb 28;129(1):119-26. doi: 10.1016/s0021-9150(96)06021-2. [PubMed:9069526 ]
Passi S, Grandinetti M, Maggio F, Stancato A, De Luca C: Epidermal oxidative stress in vitiligo. Pigment Cell Res. 1998 Apr;11(2):81-5. doi: 10.1111/j.1600-0749.1998.tb00714.x. [PubMed:9585244 ]
Kontush A, Spranger T, Reich A, Baum K, Beisiegel U: Lipophilic antioxidants in blood plasma as markers of atherosclerosis: the role of alpha-carotene and gamma-tocopherol. Atherosclerosis. 1999 May;144(1):117-22. doi: 10.1016/s0021-9150(99)00044-1. [PubMed:10381285 ]
Mohr D, Umeda Y, Redgrave TG, Stocker R: Antioxidant defenses in rat intestine and mesenteric lymph. Redox Rep. 1999;4(3):79-87. doi: 10.1179/135100099101534756. [PubMed:10496410 ]
Hargreaves P, Rahman S, Guthrie P, Taanman JW, Leonard JV, Land JM, Heales SJ: Diagnostic value of succinate ubiquinone reductase activity in the identification of patients with mitochondrial DNA depletion. J Inherit Metab Dis. 2002 Feb;25(1):7-16. doi: 10.1023/a:1015104910239. [PubMed:12004863 ]
Miles L, Miles MV, Tang PH, Horn PS, Wong BL, DeGrauw TJ, Morehart PJ, Bove KE: Muscle coenzyme Q: a potential test for mitochondrial activity and redox status. Pediatr Neurol. 2005 May;32(5):318-24. doi: 10.1016/j.pediatrneurol.2005.01.009. [PubMed:15866432 ]

Showing metabocard for Ubiquinol-2 (MMDBc0031712)

MOL for #<Metabolite:0x000055b76dc86c28>

3D MOL for #<Metabolite:0x000055b76dc86c28>

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3D-SDF for #<Metabolite:0x000055b76dc86c28>

PDB for #<Metabolite:0x000055b76dc86c28>

3D PDB for #<Metabolite:0x000055b76dc86c28>

SMILES for #<Metabolite:0x000055b76dc86c28>

INCHI for #<Metabolite:0x000055b76dc86c28>

Structure for #<Metabolite:0x000055b76dc86c28>

3D Structure for #<Metabolite:0x000055b76dc86c28>