coenzyme Q(10) (CHEBI:46245)

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CHEBI:46245 - coenzyme Q₁₀

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ChEBI Name	coenzyme Q₁₀

ChEBI ID	CHEBI:46245

ChEBI ASCII Name	coenzyme Q10

Definition	A ubiquinone having a side chain of 10 isoprenoid units. In the naturally occurring isomer, all isoprenyl double bonds are in the E- configuration.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:9854, CHEBI:46241

Supplier Information	No supplier information found for this compound.

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Molfile

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M END): 23 ms

reading 153 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

153 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Coenzyme Q10 (CoQ10 ), also known as ubiquinone, is a naturally occurring biochemical cofactor (coenzyme) and an antioxidant produced by the human body. It can also be obtained from dietary sources, such as meat, fish, seed oils, vegetables, and dietary supplements. CoQ10 is found in many organisms, including animals and bacteria. CoQ10 plays a role in mitochondrial oxidative phosphorylation, aiding in the production of adenosine triphosphate (ATP), which is involved in energy transfer within cells. The structure of CoQ10 consists of a benzoquinone moiety and an isoprenoid side chain, with the "10" referring to the number of isoprenyl chemical subunits in its tail. Although a ubiquitous molecule in human tissues, CoQ10 is not a dietary nutrient and does not have a recommended intake level, and its use as a supplement is not approved in the United States for any health or anti-disease effect.
Read full article at Wikipedia

Formula

C59H90O4

Net Charge

Average Mass

863.34350

Monoisotopic Mass

862.68391

InChI

InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+

InChIKey

ACTIUHUUMQJHFO-UPTCCGCDSA-N

SMILES

COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O

Metabolite of Species	Details
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Chemical Role(s):	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.

Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). ferroptosis inhibitor Any substance that inhibits the process of ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms. Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. (via ubiquinones ) mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). (via ubiquinones )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	coenzyme Q₁₀ (CHEBI:46245) has role antioxidant (CHEBI:22586) coenzyme Q₁₀ (CHEBI:46245) has role ferroptosis inhibitor (CHEBI:173084) coenzyme Q₁₀ (CHEBI:46245) has role human metabolite (CHEBI:77746) coenzyme Q₁₀ (CHEBI:46245) is a ubiquinones (CHEBI:16389)

IUPAC Name

2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

Synonyms	Sources
2-((all-E)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-p-benzoquinone	ChemIDplus
2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methyl-1,4-benzoquinone	ChEBI
Adelir	KEGG DRUG
all-trans-ubiquinone	ChEBI
coenzyme Q₁₀	ChemIDplus
Coenzyme Q10	KEGG COMPOUND
CoQ	ChEBI
CoQ10	ChEBI
Q	ChEBI
Q 199	ChemIDplus
Q10	ChEBI
Ubidecarenone	KEGG COMPOUND
ubiquinone	ChEBI
ubiquinone 10	ChemIDplus
ubiquinone 50	ChemIDplus
UBIQUINONE-10	PDBeChem
Ubiquinone-10	KEGG COMPOUND
ubiquinone-10	UniProt

Manual Xrefs	Databases
4445197	ChemSpider
4607	DrugCentral
C00002866	KNApSAcK
C11378	KEGG COMPOUND
Coenzyme_Q10	Wikipedia
D01065	KEGG DRUG
FDB013228	FooDB
HMDB0001072	HMDB
LMPR02010001	LIPID MAPS
U10	PDBeChem
UBIQUINONE-10	MetaCyc
View more database links

Registry Numbers	Types	Sources
1900141	Beilstein Registry Number	Beilstein
1900141	Reaxys Registry Number	Reaxys
303-98-0	CAS Registry Number	NIST Chemistry WebBook
303-98-0	CAS Registry Number	ChemIDplus

Citations

Sharma A, Fonarow GC, Butler J, Ezekowitz JA, Felker GM (2016)
Coenzyme Q10 and Heart Failure: A State-of-the-Art Review.
Circulation. Heart failure 9, e002639 [PubMed:27012265]
[show Abstract]

Zaki NM (2016)
Strategies for oral delivery and mitochondrial targeting of CoQ10.
Drug delivery 23, 1868-1881 [PubMed:25544601]
[show Abstract]

Saha SP, Whayne TF (2016)
Coenzyme Q-10 in Human Health: Supporting Evidence?
Southern medical journal 109, 17-21 [PubMed:26741866]
[show Abstract]

Villalba JM, Parrado C, Santos-Gonzalez M, Alcain FJ (2010)
Therapeutic use of coenzyme Q10 and coenzyme Q10-related compounds and formulations.
Expert opinion on investigational drugs 19, 535-554 [PubMed:20367194]
[show Abstract]

Skough K, Krossén C, Heiwe S, Theorell H, Borg K (2008)
Effects of resistance training in combination with coenzyme Q10 supplementation in patients with post-polio: a pilot study.
Journal of rehabilitation medicine 40, 773-775 [PubMed:18843432]
[show Abstract]

Molyneux SL, Young JM, Florkowski CM, Lever M, George PM (2008)
Coenzyme Q10: is there a clinical role and a case for measurement?
The Clinical biochemist. Reviews 29, 71-82 [PubMed:18787645]
[show Abstract]

Young AJ, Johnson S, Steffens DC, Doraiswamy PM (2007)
Coenzyme Q10: a review of its promise as a neuroprotectant.
CNS spectrums 12, 62-68 [PubMed:17192765]
[show Abstract]

Singh U, Devaraj S, Jialal I (2007)
Coenzyme Q10 supplementation and heart failure.
Nutrition reviews 65, 286-293 [PubMed:17605305]
[show Abstract]

Hojerová J (2000)
[Coenzyme Q10--its importance, properties and use in nutrition and cosmetics].
Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti 49, 119-123 [PubMed:10953455]
[show Abstract]

Ernster L, Dallner G (1995)
Biochemical, physiological and medical aspects of ubiquinone function.
Biochimica et biophysica acta 1271, 195-204 [PubMed:7599208]
[show Abstract]

Watts TL (1995)
Coenzyme Q10 and periodontal treatment: is there any beneficial effect?
British dental journal 178, 209-213 [PubMed:7718355]
[show Abstract]

CRANE FL, HATEFI Y, LESTER RL, WIDMER C (1957)
Isolation of a quinone from beef heart mitochondria.
Biochimica et biophysica acta 25, 220-221 [PubMed:13445756]

Last Modified

26 May 2021

General Comment
2010-04-29	Additional citation (no PMID) -- Kawahara K et al., (1994): Isolation of Sphingomonas Strains from Ears of Rice and Other Plants of Family Gramineae - Biosci. Biotech. Biochem. 58(3): 600-601.

ChEBI

CHEBI:46245 - coenzyme Q₁₀

Importance of the field

Areas covered in this review

What the reader will gain

Take home message

Objective

Design

Patients and methods

Results

Conclusion

ChEBI is part of the ELIXIR infrastructure

CHEBI:46245 - coenzyme Q10

Importance of the field

Areas covered in this review

What the reader will gain

Take home message

Objective

Design

Patients and methods

Results

Conclusion

ChEBI is part of the ELIXIR infrastructure

CHEBI:46245 - coenzyme Q₁₀