Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:32 UTC
Update Date2020-10-09 21:02:16 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
Data?1582752223
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 5HMDB
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
Description 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
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+160.96131661259
DarkChem[M-H]-162.43331661259
DeepCCS[M+H]+163.51130932474
DeepCCS[M-H]-161.15330932474
DeepCCS[M-2H]-194.03930932474
DeepCCS[M+Na]+169.60430932474
AllCCS[M+H]+157.532859911
AllCCS[M+H-H2O]+153.932859911
AllCCS[M+NH4]+160.832859911
AllCCS[M+Na]+161.832859911
AllCCS[M-H]-162.132859911
AllCCS[M+Na-2H]-162.632859911
AllCCS[M+HCOO]-163.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ubiquinone-1COC1=C(OC)C(=O)C(CC=C(C)C)=C(C)C1=O2488.3Standard polar33892256
Ubiquinone-1COC1=C(OC)C(=O)C(CC=C(C)C)=C(C)C1=O1670.5Standard non polar33892256
Ubiquinone-1COC1=C(OC)C(=O)C(CC=C(C)C)=C(C)C1=O1799.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinone-1 GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ri-6690000000-54c21ecf74c3166170052016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinone-1 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ubiquinone-1 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-1 10V, Positive-QTOFsplash10-0udi-0190000000-e28dd9a4e1e31fde0aaa2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-1 20V, Positive-QTOFsplash10-0frt-4790000000-e9b4aa7330c158e93f742015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-1 40V, Positive-QTOFsplash10-0pw9-9400000000-984285464810c9d07a1a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-1 10V, Negative-QTOFsplash10-0002-0190000000-d560b9e909b6d771b7482015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-1 20V, Negative-QTOFsplash10-0002-0890000000-173d3724196ddfd71b382015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-1 40V, Negative-QTOFsplash10-001r-8940000000-6ddd0c7bdddc6aa7ff072015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-1 10V, Positive-QTOFsplash10-0udi-0290000000-9e5c50e003ff846d25472021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-1 20V, Positive-QTOFsplash10-0udj-0790000000-8a23daff690e754ae6d32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-1 40V, Positive-QTOFsplash10-05o3-9510000000-3f25dec2fa15314807a92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-1 10V, Negative-QTOFsplash10-0002-0090000000-18320cb565cfb33802ea2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-1 20V, Negative-QTOFsplash10-00kb-0190000000-dc8c85f383835f5a9e042021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-1 40V, Negative-QTOFsplash10-0pdm-5950000000-0fe5b45bd4eebb7867112021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Brain
  • Fibroblasts
  • Intestine
  • Leukocyte
  • Liver
  • Neuron
  • Pancreas
  • Platelet
  • Prostate
  • Skeletal Muscle
Pathways
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
FooDB IDFDB022794
KNApSAcK IDNot Available
Chemspider ID4307
KEGG Compound IDC00399
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6435
PubChem Compound4462
PDB IDNot Available
ChEBI ID46234
Food Biomarker OntologyNot Available
VMH IDQ10
MarkerDB IDMDB00000364
Good Scents IDNot Available
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.