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Human Metabolome Database Version 3.5

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Showing metabocard for Ubisemiquinone (HMDB02139)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:38 -0600
Update Date 2013-05-07 15:25:29 -0600
HMDB ID HMDB02139
Secondary Accession Numbers None
Metabolite Identification
Common Name Ubisemiquinone
Description Ubisemiquinone is a component of Complex I in the mitochondia; bound ubisemiquinone is involved in the transfer of electrons from the reduced enzyme to the bound ubiquinone. Ubisemiquinone is a free radical resulting from the removal of one hydrogen atom with its electron during the process of dehydrogenation of a hydroquinone to quinone or alternatively the addition of a single H atom to a quinone (Wikipedia).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Coenzyme Q10 semiquinone
  2. Ubisemiquinone
Chemical Formula C59H90O4
Average Molecular Weight 863.3435
Monoisotopic Molecular Weight 862.683911368
IUPAC Name 2-[(2E,6E,10E,14E,18E,22E,26Z,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
Traditional IUPAC Name 2-[(2E,6E,10E,14E,18E,22E,26Z,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
CAS Registry Number 27696-12-4
SMILES COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(\C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O
InChI Identifier InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30-,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+
InChI Key ACTIUHUUMQJHFO-NBZSDRGLSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Polyterpenes
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
Substituents
  • Benzoquinone
  • Isoprene
  • Ketone
  • Polyprenylbenzoquinone
  • Tetraterpene Backbone
Direct Parent Polyterpenes
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Electron donor
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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
Property Value Source
LogP 9.94 ALOGPS
LogP 17.16 ChemAxon
LogS -6.65 ALOGPS
pKa (strongest basic) -4.7 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 52.6 A2 ChemAxon
Rotatable Bond Count 31 ChemAxon
Refractivity 286.61 ChemAxon
Polarizability 111.43 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022863
KNApSAcK ID Not Available
Chemspider ID 13628299 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02139 Link_out
Metagene Link HMDB02139 Link_out
METLIN ID 6506 Link_out
PubChem Compound 5926222 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Liu Y, Zhao H, Li H, Kalyanaraman B, Nicolosi AC, Gutterman DD: Mitochondrial sources of H2O2 generation play a key role in flow-mediated dilation in human coronary resistance arteries. Circ Res. 2003 Sep 19;93(6):573-80. Epub 2003 Aug 14. Pubmed: 12919951 Link_out