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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 COENZYME Q10, (2Z)-

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-LLOLQPSSSA-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

Molecular Formula C59H90O4
Molecular Weight 863.3435
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 9
Optical Activity NONE

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
Improvement of abnormal pyruvate metabolism and cardiac conduction defect with coenzyme Q10 in Kearns-Sayre syndrome.
1985 Mar
Muscle coenzyme Q deficiency in familial mitochondrial encephalomyopathy.
1989 Apr
Coenzyme Q in serum and muscle of 5 patients with Kearns-Sayre syndrome and 12 patients with ophthalmoplegia plus.
1989 Feb
Exogenous coenzyme Q (coq) fails to increase coq in skeletal muscle of two patients with mitochondrial myopathies.
1990 Mar
Effects of inhibitors of hydroxymethylglutaryl coenzyme A reductase on coenzyme Q and dolichol biosynthesis.
1993
Coenzyme Q10 levels in human seminal fluid: diagnostic and clinical implications.
1994
Protective effect of coenzyme Q10 on anthracyclines cardiotoxicity: control study in children with acute lymphoblastic leukemia and non-Hodgkin lymphoma.
1994
Aminooxyacetic acid striatal lesions attenuated by 1,3-butanediol and coenzyme Q10.
1994 Aug 15
Coenzyme Q10 concentrations in normal and pathological human seminal fluid.
1994 Nov-Dec
Biochemical, physiological and medical aspects of ubiquinone function.
1995 May 24
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
Modulation of apoptosis and improved redox metabolism with the use of a new antioxidant formula.
2002 Apr 1
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
Coenzyme Q10 inhibits mitochondrial complex-1 down-regulation and nuclear factor-kappa B activation.
2004 Apr-Jun
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
Estimation of plasma and saliva levels of coenzyme Q10 and influence of oral supplementation.
2005
Doxorubicin activates nuclear factor of activated T-lymphocytes and Fas ligand transcription: role of mitochondrial reactive oxygen species and calcium.
2005 Jul 15
Muscle and plasma coenzyme Q10 concentration, aerobic power and exercise economy of healthy men in response to four weeks of supplementation.
2005 Sep
Comparative oral toxicity of coenzyme Q10 and its (2Z)-isomer in rats: single and four-week repeated dose toxicity studies.
2006 Feb
Gene expression profiling of aging in multiple mouse strains: identification of aging biomarkers and impact of dietary antioxidants.
2009 Aug
Doxorubicin inactivates myocardial cytochrome c oxidase in rats: cardioprotection by Mito-Q.
2009 Feb 18
Coenzyme Q10 treatment ameliorates acute cisplatin nephrotoxicity in mice.
2010 Jul-Aug
Impaired 3',5'-cyclic adenosine monophosphate-mediated signaling in immediate early responsive gene X-1-deficient vascular smooth muscle cells.
2010 Oct
The reduced form of coenzyme Q10 decreases the expression of lipopolysaccharide-sensitive genes in human THP-1 cells.
2011 Apr
Drug-induced leukoencephalopathy presenting as catatonia.
2011 Jan-Feb
Protective efficacy of coenzyme Q10 against DDVP-induced cognitive impairments and neurodegeneration in rats.
2012 May
Coenzyme Q10 protects Pc12 cells from cisplatin-induced DNA damage and neurotoxicity.
2013 May
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:46:34 GMT 2023
Edited
by admin
on Sat Dec 16 09:46:34 GMT 2023
Record UNII
U705VLF0VW
Record Status Validated (UNII)
Record Version
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Name Type Language
COENZYME Q10, (2Z)-
Common Name English
UBIDECARENONE IMPURITY F [EP IMPURITY]
Common Name English
UBIDECARENONE (2Z) ISOMER
Common Name English
2,5-CYCLOHEXADIENE-1,4-DIONE, 2-((2Z,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- (9CI)
Systematic Name English
2,5-CYCLOHEXADIENE-1,4-DIONE, 2-(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-, (Z,E,E,E,E,E,E,E,E)-
Common Name English
COENZYME Q10 (2Z) ISOMER
Common Name English
Code System Code Type Description
DAILYMED
U705VLF0VW
Created by admin on Sat Dec 16 09:46:34 GMT 2023 , Edited by admin on Sat Dec 16 09:46:34 GMT 2023
PRIMARY
DRUG BANK
DBSALT001598
Created by admin on Sat Dec 16 09:46:34 GMT 2023 , Edited by admin on Sat Dec 16 09:46:34 GMT 2023
PRIMARY
RXCUI
1673704
Created by admin on Sat Dec 16 09:46:34 GMT 2023 , Edited by admin on Sat Dec 16 09:46:34 GMT 2023
PRIMARY RxNorm
PUBCHEM
12303768
Created by admin on Sat Dec 16 09:46:34 GMT 2023 , Edited by admin on Sat Dec 16 09:46:34 GMT 2023
PRIMARY
CAS
65085-29-2
Created by admin on Sat Dec 16 09:46:34 GMT 2023 , Edited by admin on Sat Dec 16 09:46:34 GMT 2023
PRIMARY
FDA UNII
U705VLF0VW
Created by admin on Sat Dec 16 09:46:34 GMT 2023 , Edited by admin on Sat Dec 16 09:46:34 GMT 2023
PRIMARY