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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-07-11 09:18:48 UTC
Update Date2021-10-13 04:50:01 UTC
HMDB IDHMDB0006709
Secondary Accession Numbers
  • HMDB06709
Metabolite Identification
Common NameUbiquinone-2
DescriptionUbiquinone-2 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-2 has just 2 isoprene units. Normally in humans it has 10. Ubiquinone-2 is an intermediate in the synthesis of Ubiquionone 10. Ubiquionone is involved in cellular respiration. It is fat-soluble and is therefore mobile in cellular membranes; it plays a unique role in the electron transport chain (ETC). In the inner bacterial membrane, electrons from NADH and succinate pass through the ETC to the oxygen, which is then reduced to water. The transfer of electrons through ETC results in the pumping of H+ across the membrane creating a proton gradient across the membrane, which is used by ATP synthase (located on the membrane) to generate ATP.
Structure
Data?1582752401
Synonyms
ValueSource
(e)-2-(3,7-Dimethyl-2,6-octadienyl)-5,6-dimethoxy-3-methyl-p-benzoquinoneChEBI
2-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-5,6-dimethoxy-3-methyl-1,4-benzoquinoneChEBI
Ubiquinone 10ChEBI
Coenzyme QKegg
CoQKegg
QKegg
2,3-Dimethoxy-5-geranyl-6-methyl-1,4-benzoquinoneHMDB
2-(3,7-Dimethyl-2,6-octadienyl)-5,6-dimethoxy-3-methyl- P-benzoquinoneHMDB
2-(3,7-Dimethyl-2,6-octadienyl)-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dioneHMDB
2-[(2E)-3,7-Dimethyl-2,6-octadienyl]-5,6-dimethoxy-3-methyl- P-benzoquinoneHMDB
Coenzyme Q2HMDB
Q 2HMDB
Ubiquinone 2HMDB
Ubiquinone Q2HMDB
Ubiquinone Q2, (e)-isomerMeSH, HMDB
Chemical FormulaC19H26O4
Average Molecular Weight318.4073
Monoisotopic Molecular Weight318.18310932
IUPAC Name2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
Traditional Namecoenzyme-Q
CAS Registry Number606-06-4
SMILES
COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O
InChI Identifier
InChI=1S/C19H26O4/c1-12(2)8-7-9-13(3)10-11-15-14(4)16(20)18(22-5)19(23-6)17(15)21/h8,10H,7,9,11H2,1-6H3/b13-10+
InChI KeySQQWBSBBCSFQGC-JLHYYAGUSA-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
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.49 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available174.655http://allccs.zhulab.cn/database/detail?ID=AllCCS00000456
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP10(3.75) g/LALOGPS
logP10(3.88) g/LChemAxon
logS10(-4.5) g/LALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity96.18 m³·mol⁻¹ChemAxon
Polarizability36.45 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
DeepCCS[M+H]+184.36830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ubiquinone-2COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O3015.9Standard polar33892256
Ubiquinone-2COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O2092.3Standard non polar33892256
Ubiquinone-2COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O2251.4Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ubiquinone-2 40V, Positive-QTOFsplash10-0fnj-2940000000-9de99f5e60d85c76bc222021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ubiquinone-2 20V, Positive-QTOFsplash10-00kb-0694000000-0e7666219469e4d3daa42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ubiquinone-2 10V, Positive-QTOFsplash10-014i-0109000000-46935a3400936bee8dab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ubiquinone-2 20V, Positive-QTOFsplash10-00kb-0694000000-1aa3da1d9a8adf74884c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-2 10V, Positive-QTOFsplash10-014i-0439000000-180eeec0662a1cd541e82015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-2 20V, Positive-QTOFsplash10-01ba-3942000000-6814d10b6c7404b88af92015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-2 40V, Positive-QTOFsplash10-014i-9410000000-95413a2c0ab148a85d9e2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-2 10V, Negative-QTOFsplash10-014i-0019000000-f5070dbbdd24c4bc12aa2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-2 20V, Negative-QTOFsplash10-02t9-0296000000-7c0eaf226e5a4866b9992015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-2 40V, Negative-QTOFsplash10-000i-9361000000-fff86254a78962e3b8502015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-2 10V, Negative-QTOFsplash10-014i-0009000000-9c9a5615e70cdf418e9b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-2 20V, Negative-QTOFsplash10-014r-0696000000-31579df78d92b1e7acbf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-2 40V, Negative-QTOFsplash10-0v7r-0491000000-cc67df533d00a14ce7222021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-2 10V, Positive-QTOFsplash10-014j-0739000000-503861a7af6bafcfa25f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-2 20V, Positive-QTOFsplash10-0002-3951000000-41b9dda5990696c362752021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ubiquinone-2 40V, Positive-QTOFsplash10-0a5c-9540000000-b49cb12d9c6d12564ffd2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08690
Phenol Explorer Compound IDNot Available
FooDB IDFDB024036
KNApSAcK IDNot Available
Chemspider ID4444053
KEGG Compound IDC00399
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280346
PDB IDNot Available
ChEBI ID46372
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1427581
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Forsmark-Andree P, Lee CP, Dallner G, Ernster L: Lipid peroxidation and changes in the ubiquinone content and the respiratory chain enzymes of submitochondrial particles. Free Radic Biol Med. 1997;22(3):391-400. [PubMed:8981030 ]

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
Reactions
QH2 + Acceptor → Ubiquinone-2 + Reduced acceptordetails
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
Reactions
Ubiquinone-2 + Succinic acid → QH2 + Fumaric aciddetails
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.