| Record Information |
| Version |
3.5 |
| Creation Date |
2006-05-22 08:17:32 -0600 |
| Update Date |
2013-02-08 17:11:11 -0700 |
| HMDB ID |
HMDB02012 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
Ubiquinone-1 |
| Description |
Ubiquinone-1 is a member of the chemical class known as Polyprenylbenzoquinones. These are compounds containing a polyisoprene chain attached to a quinone at the second ring position. Ubiquione-1 has just 1 isoprene unit. Normally in humans it has 10. Ubiquinone-1 is an intermediate in the synthesis of Ubiquionone 10, which is also called Coenzyme Q (CoQ). CoQ is found in the membranes of endoplasmic reticulum, peroxisomes, lysosomes, vesicles and notably the inner membrane of the mitochondrion where it is an important part of the electron transport chain; there it passes reducing equivalents to acceptors such as Coenzyme Q : cytochrome c - oxidoreductase. CoQ is also essential in the formation of the apoptosome along with other adapter proteins. The loss of trophic factors activates pro-apoptotic enzymes, causing the breakdown of mitochondria. Because of its ability to transfer electrons and therefore act as an antioxidant, Coenzyme Q has become a valued dietary supplement. CoQ10 has been widely used for the treatment of heart disease (especially heart failure), gum diseases, and also breast cancer. The benzoquinone portion of Coenzyme Q10 is synthesized from amino acids, while the isoprene sidechain is synthesized from acetyl CoA through the mevalonate pathway. The mevalonate pathway is used for the first steps of cholesterol biosynthesis. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- Coenzyme Q1
- CoQ1
- Ubiquinone Q1
- Ubiquinone-Q1
- Ubiquionone 1
|
| Chemical Formula |
C14H18O4 |
| Average Molecular Weight |
250.2903 |
| Monoisotopic Molecular Weight |
250.120509064 |
| IUPAC Name |
2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)cyclohexa-2,5-diene-1,4-dione |
| Traditional IUPAC Name |
ubiquinone-1 |
| CAS Registry Number |
727-81-1 |
| SMILES |
COC1=C(OC)C(=O)C(CC=C(C)C)=C(C)C1=O |
| InChI Identifier |
InChI=1S/C14H18O4/c1-8(2)6-7-10-9(3)11(15)13(17-4)14(18-5)12(10)16/h6H,7H2,1-5H3 |
| InChI Key |
SOECUQMRSRVZQQ-UHFFFAOYSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Aliphatic Homomonocyclic Compounds |
| Class |
Benzoquinones |
| Sub Class |
N/A |
| Other Descriptors |
- Aliphatic Homomonocyclic Compounds
- a ubiquinone(Cyc)
- ubiquinones(ChEBI)
|
| Substituents |
|
| Direct Parent |
Benzoquinones |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Anti-oxidant
- Component of Ubiquinone biosynthesis
- Electron donor
|
| Application |
Not Available |
| Cellular locations |
Not Available |
| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|
Not Available
|
| Biological Properties |
| Cellular Locations |
Not Available
|
| Biofluid Locations |
|
| Tissue Location |
- Muscle
- Skeletal Muscle
- Fibroblasts
- Intestine
- Lymphocyte
- Pancreas
- Liver
- Brain
- Prostate
- Nerve Cells
- Platelet
|
| Pathways |
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.00312 +/- 0.00032 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.00084 +/- 0.00040 uM |
Adult (>18 years old) |
Both |
Multiple sclerosis |
Not Available |
|
| Associated Disorders and Diseases |
| Disease References |
| Multiple sclerosis |
- Syburra C, Passi S: Oxidative stress in patients with multiple sclerosis. Ukr Biokhim Zh. 1999 May-Jun;71(3):112-5.
Pubmed: 10609336
|
|
| Associated OMIM IDs |
|
| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022794 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
4307  |
| KEGG Compound ID |
C00399  |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Ubiquinone  |
| NuGOwiki Link |
HMDB02012  |
| Metagene Link |
HMDB02012  |
| METLIN ID |
6435  |
| PubChem Compound |
4462  |
| PDB ID |
UQ1  |
| ChEBI ID |
16389  |
| References |
| Synthesis Reference |
Naruta, Yoshinori; Maruyama, Kazuhiro. . Ubiquinone-1. Organic Syntheses (1993), 71 125-32. |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- Zhang Y, Eriksson M, Dallner G, Appelkvist EL: Analysis of ubiquinone and tocopherol levels in normal and hyperlipidemic human plasma. Lipids. 1998 Aug;33(8):811-5.
Pubmed: 9727612
- Karlsson J, Lin L, Gunnes S, Sylven C, Astrom H: Muscle ubiquinone in male effort angina patients. Mol Cell Biochem. 1996 Mar 23;156(2):173-8.
Pubmed: 9095475
- Passi S, Stancato A, Aleo E, Dmitrieva A, Littarru GP: Statins lower plasma and lymphocyte ubiquinol/ubiquinone without affecting other antioxidants and PUFA. Biofactors. 2003;18(1-4):113-24.
Pubmed: 14695926
- Karlsson J, Lin L, Sylven C, Jansson E: Muscle ubiquinone in healthy physically active males. Mol Cell Biochem. 1996 Mar 23;156(2):169-72.
Pubmed: 9095474
- Laaksonen R, Jokelainen K, Sahi T, Tikkanen MJ, Himberg JJ: Decreases in serum ubiquinone concentrations do not result in reduced levels in muscle tissue during short-term simvastatin treatment in humans. Clin Pharmacol Ther. 1995 Jan;57(1):62-6.
Pubmed: 7828383
- Edlund C, Soderberg M, Kristensson K, Dallner G: Ubiquinone, dolichol, and cholesterol metabolism in aging and Alzheimer's disease. Biochem Cell Biol. 1992 Jun;70(6):422-8.
Pubmed: 1449707
- Pastore A, Giovamberardino GD, Bertini E, Tozzi G, Gaeta LM, Federici G, Piemonte F: Simultaneous determination of ubiquinol and ubiquinone in skeletal muscle of pediatric patients. Anal Biochem. 2005 Jul 15;342(2):352-5. Epub 2005 Mar 7.
Pubmed: 15989930
- Elmberger PG, Kalen A, Brunk UT, Dallner G: Discharge of newly-synthesized dolichol and ubiquinone with lipoproteins to rat liver perfusate and to the bile. Lipids. 1989 Nov;24(11):919-30.
Pubmed: 2615561
- Yamashita S, Yamamoto Y: Simultaneous detection of ubiquinol and ubiquinone in human plasma as a marker of oxidative stress. Anal Biochem. 1997 Jul 15;250(1):66-73.
Pubmed: 9234900
- Mancini A, Conte G, Milardi D, De Marinis L, Littarru GP: Relationship between sperm cell ubiquinone and seminal parameters in subjects with and without varicocele. Andrologia. 1998 Feb-Mar;30(1):1-4.
Pubmed: 9567163
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