Record Information
Version3.6
Creation Date2007-07-11 09:18:48 UTC
Update Date2013-02-09 00:15:11 UTC
HMDB IDHMDB06709
Secondary Accession NumbersNone
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
Thumb
Synonyms
  1. 2,3-Dimethoxy-5-geranyl-6-methyl-1,4-benzoquinone
  2. 2-(3,7-Dimethyl-2,6-octadienyl)-5,6-dimethoxy-3-methyl- p-Benzoquinone
  3. 2-(3,7-Dimethyl-2,6-octadienyl)-5,6-dimethoxy-3-methyl-2,5-Cyclohexadiene-1,4-dione
  4. 2-[(2E)-3,7-Dimethyl-2,6-octadienyl]-5,6-dimethoxy-3-methyl- p-Benzoquinone
  5. Coenzyme Q2
  6. Q 2
  7. Ubiquinone 2
  8. Ubiquinone Q2
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 IUPAC Nameubiquinone 10
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
KingdomOrganic Compounds
Super ClassAliphatic Homomonocyclic Compounds
ClassBenzoquinones
Sub ClassN/A
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • a ubiquinone(Cyc)
Substituents
  • Isoprene
  • Ketone
Direct ParentBenzoquinones
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
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 solubility0.01 g/LALOGPS
logP3.75ALOGPS
logP3.88ChemAxon
logS-4.5ALOGPS
pKa (strongest basic)-4.7ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count0ChemAxon
polar surface area52.6ChemAxon
rotatable bond count7ChemAxon
refractivity96.18ChemAxon
polarizability36.45ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB024036
KNApSAcK IDNot Available
Chemspider ID4444053
KEGG Compound IDC00399
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06709
Metagene LinkHMDB06709
METLIN IDNot Available
PubChem Compound5280346
PDB IDUQ2
ChEBI ID46372
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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 50 proteins. There are 56 proteins in total.

Enzymes

Gene Name:
MT-ND1
Uniprot ID:
P03886
Reactions
QH2 + Acceptor unknown Ubiquinone-2 + Reduced acceptordetails
Gene Name:
SDHC
Uniprot ID:
Q99643
Reactions
Ubiquinone-2 + Succinic acid unknown QH2 + Fumaric aciddetails
Gene Name:
MT-ND4L
Uniprot ID:
P03901
Reactions
QH2 + Acceptor unknown Ubiquinone-2 + Reduced acceptordetails
Gene Name:
MT-ND5
Uniprot ID:
P03915
Reactions
QH2 + Acceptor unknown Ubiquinone-2 + Reduced acceptordetails
Gene Name:
SDHA
Uniprot ID:
P31040
Reactions
Ubiquinone-2 + Succinic acid unknown QH2 + Fumaric aciddetails
Gene Name:
MT-ND2
Uniprot ID:
P03891
Reactions
QH2 + Acceptor unknown Ubiquinone-2 + Reduced acceptordetails
Gene Name:
NDUFAB1
Uniprot ID:
O14561
Gene Name:
MT-ND4
Uniprot ID:
P03905
Reactions
QH2 + Acceptor unknown Ubiquinone-2 + Reduced acceptordetails
Gene Name:
SDHD
Uniprot ID:
O14521
Reactions
Ubiquinone-2 + Succinic acid unknown QH2 + Fumaric aciddetails
Gene Name:
MT-ND3
Uniprot ID:
P03897
Reactions
QH2 + Acceptor unknown Ubiquinone-2 + Reduced acceptordetails
Gene Name:
MT-ND6
Uniprot ID:
P03923
Reactions
QH2 + Acceptor unknown Ubiquinone-2 + Reduced acceptordetails
Gene Name:
SDHB
Uniprot ID:
P21912
Reactions
Ubiquinone-2 + Succinic acid unknown QH2 + Fumaric aciddetails
Gene Name:
COQ3
Uniprot ID:
Q9NZJ6
Reactions
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine unknown Ubiquinone-2 + S-Adenosylhomocysteinedetails
Gene Name:
UQCR10
Uniprot ID:
Q9UDW1
Gene Name:
UQCRB
Uniprot ID:
P14927

Only showing the first 50 proteins. There are 56 proteins in total.