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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:32 UTC
Update Date2017-12-07 01:46:52 UTC
HMDB IDHMDB0002012
Secondary Accession Numbers
  • HMDB02012
Metabolite Identification
Common NameUbiquinone-1
DescriptionUbiquinone-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
Thumb
Synonyms
ValueSource
2,3-Dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-2,5-cyclohexadiene-1,4-dioneChEBI
2,3-Dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)-1,4-benzoquinoneChEBI
2,3-Dimethoxy-5-methyl-6-(3-methylbut-2-enyl)benzo-1,4-quinoneChEBI
Coenzyme Q1ChEBI
Coenzyme Q5ChEBI
CoQ1ChEBI
Ubiquinone Q1ChEBI
Ubiquinone-Q1HMDB
Ubiquionone 1HMDB
Ubiquinone 5MeSH
Chemical FormulaC14H18O4
Average Molecular Weight250.2903
Monoisotopic Molecular Weight250.120509064
IUPAC Name2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)cyclohexa-2,5-diene-1,4-dione
Traditional Nameubiquinone-1
CAS Registry Number727-81-1
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 KeySOECUQMRSRVZQQ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentUbiquinones
Alternative Parents
Substituents
  • Ubiquinone skeleton
  • Monoterpenoid
  • Monocyclic monoterpenoid
  • Quinone
  • P-benzoquinone
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP2.2ALOGPS
logP2.22ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.38 m³·mol⁻¹ChemAxon
Polarizability26.94 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ri-6690000000-54c21ecf74c316617005View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0190000000-e28dd9a4e1e31fde0aaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frt-4790000000-e9b4aa7330c158e93f74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pw9-9400000000-984285464810c9d07a1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0190000000-d560b9e909b6d771b748View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0890000000-173d3724196ddfd71b38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001r-8940000000-6ddd0c7bdddc6aa7ff07View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Location
  • Brain
  • Fibroblasts
  • Intestine
  • Liver
  • Lymphocyte
  • Muscle
  • Nerve Cells
  • Pancreas
  • Platelet
  • Prostate
  • Skeletal Muscle
Pathways
NameSMPDB/PathwhizKEGG
Ubiquinone BiosynthesisThumbThumb?image type=greyscaleThumb?image type=simpleMap00130
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00312 +/- 0.00032 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00084 +/- 0.00040 uMAdult (>18 years old)BothMultiple sclerosis details
Associated Disorders and Diseases
Disease References
Multiple sclerosis
  1. Syburra C, Passi S: Oxidative stress in patients with multiple sclerosis. Ukr Biokhim Zh (1999). 1999 May-Jun;71(3):112-5. [PubMed:10609336 ]
Associated OMIM IDs
DrugBank IDDB08689
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022794
KNApSAcK IDNot Available
Chemspider ID4307
KEGG Compound IDC00399
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6435
PubChem Compound4462
PDB IDUQ1
ChEBI ID46234
References
Synthesis ReferenceNaruta, Yoshinori; Maruyama, Kazuhiro. . Ubiquinone-1. Organic Syntheses (1993), 71 125-32.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]

Only showing the first 10 proteins. There are 56 proteins in total.

Enzymes

General function:
Involved in oxidation reduction
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND1
Uniprot ID:
P03886
Molecular weight:
35660.055
General function:
Involved in NADH dehydrogenase activity
Specific function:
Accessory subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I), that is believed not to be involved in catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone
Gene Name:
NDUFB1
Uniprot ID:
O75438
Molecular weight:
6961.2
General function:
Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
NDUFS2
Uniprot ID:
O75306
Molecular weight:
51851.59
General function:
Involved in succinate dehydrogenase activity
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:
SDHC
Uniprot ID:
Q99643
Molecular weight:
16650.185
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Accessory subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I), that is believed not to be involved in catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone
Gene Name:
NDUFA12
Uniprot ID:
Q9UI09
Molecular weight:
17114.4
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Accessory subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I), that is believed not to be involved in catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone
Gene Name:
NDUFA1
Uniprot ID:
O15239
Molecular weight:
8072.3
General function:
Not Available
Specific function:
Not Available
Gene Name:
NDUFA4L2
Uniprot ID:
Q9NRX3
Molecular weight:
9965.6
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Accessory subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I), that is believed not to be involved in catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone
Gene Name:
NDUFA3
Uniprot ID:
O95167
Molecular weight:
9278.8
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Accessory subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I), that is believed not to be involved in catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone
Gene Name:
NDUFA8
Uniprot ID:
P51970
Molecular weight:
20104.9
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Accessory subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I), that is believed to be not involved in catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone
Gene Name:
NDUFA4
Uniprot ID:
O00483
Molecular weight:
9369.8

Only showing the first 10 proteins. There are 56 proteins in total.