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Details

Stereochemistry ACHIRAL
Molecular Formula C59H90O4
Molecular Weight 863.3435
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 9
Charge 0

SHOW SMILES / InChI
Structure of UBIDECARENONE

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

InChI

InChIKey=ACTIUHUUMQJHFO-UPTCCGCDSA-N
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+

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.mbschachter.com/coenzyme_q10.htm https://en.wikipedia.org/wiki/Coenzyme_Q10

Coenzyme Q10, also known as ubiquinone, ubidecarenone, coenzyme Q, and abbreviated at times to CoQ10 or Q10 is a coenzyme that is ubiquitous in the bodies of most animals. It is a 1,4-benzoquinone, where Q refers to the quinone chemical group and 10 refers to the number of isoprenyl chemical subunits in its tail. This fat-soluble substance, which resembles a vitamin, is present in most eukaryotic cells, primarily in the mitochondria. It is a component of the electron transport chain and participates in aerobic cellular respiration, which generates energy in the form of ATP. Ninety-five percent of the human body’s energy is generated this way. Therefore, those organs with the highest energy requirements—such as the heart, liver, and kidney—have the highest CoQ10 concentrations. There are three redox states of CoQ10: fully oxidized (ubiquinone), semiquinone (ubisemiquinone), and fully reduced (ubiquinol). The capacity of this molecule to act as a 2 electron carrier (moving between the quinone and quinol form) and 1 electron carrier (moving between the semiquinone and one of these other forms) is central to its role in the electron transport chain, and as radical-scavenging antioxidant. Coenzyme Q10 works foremost in every cell of your body to synthesize energy. In cells' mitochondria, CoQ10 helps generate adenosine triphosphate (ATP), your body's energy currency. It makes sense that organs with the highest energy needs - including the heart, liver, and kidneys - contain large amounts of CoQ10. Among its roles, ubiquinol protects fats, protein, low-density lipoprotein (LDL, a cholesterol transporter), and DNA from oxidative damage. It also regenerates vitamin E, another powerful antioxidant. Even though Coenzyme Q10 is a supplement and occurs naturally in your body, it doesn't mean that it's side effect free. However, most CoQ10 side effects are mild. Some people may experience allergies to increased Coenzyme Q10. There have been some reports of rashes and itching. Other side effects include a lowering of blood sugar within the body. CoQ10 is not approved by the U.S. Food and Drug Administration (FDA) for the treatment of any medical condition. It is sold as a dietary supplement. In the U.S., supplements are not regulated as drugs, but as foods. How CoQ10 is manufactured is not regulated and different batches and brands may vary significantly. As an over-the-counter nutritional supplement, CoQ10 has been used to treat many things, from heart disease, high blood pressure and high cholesterol to diabetes, breast cancer and gum disease. CoQ10 supposedly can help with immune deficiencies, increase fertility, treat Alzheimer's and Parkinson's, reduce ringing in the ears, delay aging and improve skin, and increase athleticism The key benefits of coenzyme Q10 are summarized as below. A 2014 Cochrane Collaboration meta-analysis found "no convincing evidence to support or refute" the use of CoQ10 for the treatment of heart failure. Evidence with respect to preventing heart disease in those who are otherwise healthy is also poor. A 2009 Cochrane review concluded that studies looking at the effects of CoQ10 on blood pressure were unreliable, and therefore no conclusions could be made regarding its effectiveness in lowering blood pressure. Available evidence suggests that "CoQ10 is likely ineffective in moderately improving" the chorea associated with Huntington's disease. No large well-designed clinical trials of CoQ10 in cancer treatment have been done. The National Cancer Institute identified issues with the few, small studies that have been done stating, "the way the studies were done and the amount of information reported made it unclear if benefits were caused by the CoQ10 or by something else". The American Cancer Society has concluded, "CoQ10 may reduce the effectiveness of chemo and radiation therapy, so most oncologists would recommend avoiding it during cancer treatment. Lower levels of CoQ10 have also been observed in people with Parkinson's disease. Preliminary research has found that increasing CoQ10 may increase levels of the neurotransmitter dopamine, which is thought to be lowered in people with Parkinson's disease. It has also been suggested that CoQ10 might protect brain cells from damage by free radicals. A small, randomized controlled trial examined the use of 360 mg CoQ10 or a placebo in 28 treated and stable Parkinson's disease patients. After 4 weeks, CoQ10 provided a mild but significant significant mild improvement in early Parkinson's symptoms and significantly improved performance in visual function. As an antioxidant, Coenzyme Q10 helps protect your body against the harmful effects of toxins and also aids the absorption of beneficial vitamins and minerals. Antioxidants are sometimes credited with boosting weight loss, possibly due to their energising effect on the body helping increase the fat-burning benefits of exercise.

CNS Activity

Curator's Comment: CoQ10 (UBIDECARENONE) has been studied for its effect in support of neurological health. When CoQ10 crosses the blood-brain barrier, mitochondrial concentrations are increased and clinical results indicate that significant neurosupportive effects follow. Clinical studies have examined the role of CoQ10 in the neurological system

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
Adriamycin cardiotoxicity: early detection by systolic time interval and possible prevention by coenzyme Q10.
1978 Jun
Coenzyme Q10 levels in human seminal fluid: diagnostic and clinical implications.
1994
Aminooxyacetic acid striatal lesions attenuated by 1,3-butanediol and coenzyme Q10.
1994 Aug 15
Effect of treatment with 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors on serum coenzyme Q10 in diabetic patients.
1999 Apr
Blood antioxidant status and urinary levels of catecholamine metabolites in beta-thalassemia.
1999 Jun
Effect of hydrosoluble coenzyme Q10 on blood pressures and insulin resistance in hypertensive patients with coronary artery disease.
1999 Mar
Coenzyme Q-responsive Leigh's encephalopathy in two sisters.
2002 Dec
Review: Mitochondrial medicine--cardiomyopathy caused by defective oxidative phosphorylation.
2003 Fall
Only transient increase of serum CoQ subset 10 during long-term CoQ10 therapy in mitochondrial ophthalmoplegia.
2003 Nov 12
1-Benzyl-1,2,3,4-tetrahydroisoquinoline, a Parkinsonism-inducing endogenous toxin, increases alpha-synuclein expression and causes nuclear damage in human dopaminergic cells.
2004 May 15
Isolated mitochondrial myopathy associated with muscle coenzyme Q10 deficiency.
2005 Feb
Effect of oxidative stress on translocation of DAF-16 in oxygen-sensitive mutants, mev-1 and gas-1 of Caenorhabditis elegans.
2005 Jun-Jul
Muscle and plasma coenzyme Q10 concentration, aerobic power and exercise economy of healthy men in response to four weeks of supplementation.
2005 Sep
Doxorubicin inactivates myocardial cytochrome c oxidase in rats: cardioprotection by Mito-Q.
2009 Feb 18
Drug-induced leukoencephalopathy presenting as catatonia.
2011 Jan-Feb
Nucleoside reverse transcriptase inhibitors induce a mitophagy-associated endothelial cytotoxicity that is reversed by coenzyme Q10 cotreatment.
2013 Aug
Patents

Sample Use Guides

coenzyme Q(10) (UBIDECARENONE) (300 mg/d) for 2 weeks
Route of Administration: Oral
peripheral blood mononuclear cells treated with CoQ10 (UBIDECARENONE) showed significantly decreased percentage of Th1 cells (P < 0.005) in pregnant females with history of RPL than in the untreated ones.
Name Type Language
UBIDECARENONE
DSC   EP   INN   MART.   WHO-DD  
INN  
Official Name English
COQ10
Common Name English
2-DECA(3-METHYLBUT-2-ENYLENE)-5,6-DIMETHOXY-3-METHYL-P-BENZOQUINONE
Common Name English
ubidecarenone [INN]
Common Name English
UBIQUINONE Q10
Common Name English
UBIQUINONE
INCI  
INCI  
Official Name English
UBIDECARENONE [MART.]
Common Name English
COENZYME Q10
VANDF  
Common Name English
CO-ENZYME Q10
Common Name English
NSC-140865
Code English
ADELIR
Brand Name English
UBIQUINONE-10
Common Name English
COENZYME Q-199
Common Name English
AQUA Q10
Brand Name English
PURESORB Q 40
Brand Name English
BPM-31510
Common Name English
Ubidecarenone [WHO-DD]
Common Name English
VITAMIN Q
Common Name English
UBIDECARENONE [JAN]
Common Name English
UBIDECARENONE [DSC]
Common Name English
UNISPHERES Q 10
Brand Name English
API-31510
Code English
BIO-QUINONE Q10
Brand Name English
NSC-140665
Code English
UBIQUINONE 50 [MI]
Common Name English
UBIDECARENONE [USP-RS]
Common Name English
2,5-CYCLOHEXADIENE-1,4-DIONE, 2-((2E,6E,10E,14E,18E,22E,26E,30E,34E)-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
Common Name English
API 31510
Code English
UBIQUINONE 10
Common Name English
BPM31510
Common Name English
UBIDECARENONE FOR SYSTEM SUITABILITY [USP-RS]
Common Name English
ORISTAR UBQ
Brand Name English
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
Common Name English
UBIDECARENONE [EP MONOGRAPH]
Common Name English
COENZYME Q10 [VANDF]
Common Name English
UBIDECARENONE FOR SYSTEM SUITABILITY
USP-RS  
Common Name English
COENZYME Q-10
Common Name English
UBIQUINONE [INCI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C796
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
LOINC 75050-5
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
LOINC 27923-2
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FDA ORPHAN DRUG 138700
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FDA ORPHAN DRUG 335111
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
FDA ORPHAN DRUG 125099
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LIVERTOX 233
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
NCI_THESAURUS C275
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
LOINC 18209-7
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
WHO-ATC C01EB09
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
LOINC 60219-3
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FDA ORPHAN DRUG 610717
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
LOINC 51987-6
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
FDA ORPHAN DRUG 174603
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DSLD 44 (Number of products:2720)
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
WHO-VATC QC01EB09
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
FDA ORPHAN DRUG 822521
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LOINC 81156-2
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
FDA ORPHAN DRUG 635318
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
Code System Code Type Description
CAS
303-98-0
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
PRIMARY
NSC
140865
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
PRIMARY
DAILYMED
EJ27X76M46
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PRIMARY
DRUG BANK
DB09270
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PRIMARY
RS_ITEM_NUM
1705301
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PRIMARY
DRUG CENTRAL
4607
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PRIMARY
MESH
C024989
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
PRIMARY
WIKIPEDIA
COENZYME Q10
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
PRIMARY
NCI_THESAURUS
C916
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
PRIMARY
CHEBI
46245
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
PRIMARY
NCI_THESAURUS
C118621
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
ALTERNATIVE
SMS_ID
100000090312
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
PRIMARY
PUBCHEM
5281915
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PRIMARY
ChEMBL
CHEMBL454801
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PRIMARY
MESH
D014451
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PRIMARY
NSC
140665
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
PRIMARY
FDA UNII
EJ27X76M46
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-147-9
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PRIMARY
MERCK INDEX
m11295
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PRIMARY Merck Index
EPA CompTox
DTXSID6046054
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PRIMARY
RXCUI
10975
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ALTERNATIVE
RXCUI
21406
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PRIMARY
EVMPD
SUB11373MIG
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
PRIMARY
CHEBI
46372
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
PRIMARY
LACTMED
Coenzyme Q10
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
PRIMARY
INN
3463
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PRIMARY
CHEBI
16389
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PRIMARY
NCI_THESAURUS
C916
Created by admin on Fri Dec 15 14:58:21 GMT 2023 , Edited by admin on Fri Dec 15 14:58:21 GMT 2023
PRIMARY