| 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 resliting 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 |
| Synonyms |
| Value |
Source |
Coenzyme Q10 semiquinoneHMDB
UbidecarenoneMeSH
Coenzyme Q10, (Z,Z,Z,Z,Z,Z,e,e,e)-isomerMeSH
Ubisemiquinone radicalMeSH
2,3-Dimethoxy-5-methyl-6-decaprenylbenzoquinoneMeSH
CoQ10MeSH
Q-TerMeSH
CO-Enzyme Q10MeSH
Coenzyme Q10MeSH
bio-Quinone Q10MeSH
Ubiquinone 50MeSH
CoQ 10MeSH
Coenzyme Q10, ion (1-), (all-e)-isomerMeSH
Ubiquinone Q10MeSH
| Chemical Formlia |
C59H90O4
| Average Molecliar Weight |
863.3435
| Monoisotopic Molecliar 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 Name |
ubisemiquinone
| CAS Registry Number |
27696-12-4
| SMILES |
COC1=C(OC)C(=O)C(CC=C(/C)CCC=C(/C)CCC=C(/C)CCC=C(/C)CCC=C(/C)CCC=C(/C)CCC=C(C)CCC=C(/C)CCC=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 |
| Description |
This compound belongs to the class of chemical entities 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).
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Lipids and lipid-like moleclies
| Sub Class |
Prenol lipids
| Direct Parent |
Ubiquinones
| Alternative Parents |
Polyterpenoids
Tetraterpenoids
Polyprenylbenzoquinones
P-benzoquinones
Vinylogous esters
Organic oxides
Hydrocarbon derivatives
| Substituents |
Polyterpenoid
Tetraterpenoid
Polyprenylbenzoquinone
Ubiquinone skeleton
Quinone
P-benzoquinone
Vinylogous ester
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound
| Molecliar Framework |
Aliphatic homomonocyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but 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 Emlisifiers
| Cellliar locations |
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.000193 mg/mLALOGPS
logP9.94ALOGPS
logP17.16ChemAxon
logS-6.7ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 Å2ChemAxon
Rotatable Bond Count31ChemAxon
Refractivity286.61 m3·mol-1ChemAxon
Polarizability111.43 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
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
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite 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
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB02139
| Metagene Link |
HMDB02139
| METLIN ID |
6506
| PubChem Compound |
5926222
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: AKT inhibitor
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- 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 ]
|
PMID: 16262678