Idebenone (CED0005248)

Record Information
Version1.0
Creation Date2016-05-22 04:28:19 UTC
Update Date2026-08-20 04:14:12 UTC
Accession NumberCHEM017574
Identification
Common NameIdebenone
ClassSmall Molecule
Description
Idebenone is an organic compound with the formula C19H30O5 and an average molecular weight of 338.44 g/mol. Idebenone belongs to the quinone and hydroquinone lipids, a subclass of prenol lipids within the organic compounds. It is utilized as an industrial antioxidant. The compound is recorded in 33 sources across various sectors. Within electrical and electronic equipment, it is found in antennas, amplifiers, adjustable resistors, colour television systems, auxiliary devices, and 11 additional items. In the building and construction sector, it is associated with roofs, ceilings, floors, stairs and ramps, and sunshades awnings or outside screens, among two other sources. Household cleaning and consumer products containing the compound include soap dispensers, soap detergents, tobacco smoke filters, cigar cigarettes, and non electric simulated smoking devices. In the realm of food, food processing, and cookware, it is used in food preservation, the processing of meats, and the preparation of sparkling wine or wine. Additionally, it is found in household items such as coins. In the category of healthcare, pharmaceuticals, and veterinary products, idebenone is used as a nootropic, a psychostimulant, and an agent used for ADHD. The recorded exposure route for this compound is oral.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
2,3-Dimethoxy-5-methyl-6-(10'-hydroxydecyl)-1,4-benzoquinoneChEBI
2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methyl-p-benzoquinoneChEBI
2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dioneChEBI
6-(10-Hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinoneChEBI
6-(10-Hydroxydecyl)-2,3-dimethoxy-5-methyl-p-benzoquinoneChEBI
BRN 2001459ChEBI
CV 2619ChEBI
IdebenonaChEBI
IdebenonumChEBI
RaxoneKegg
Hydroxydecyl ubiquinoneMeSH
NobenMeSH
Chemical FormulaC19H30O5
Average Molecular Mass338.444 g/mol
Monoisotopic Mass338.209 g/mol
CAS Registry Number58186-27-9
IUPAC Name2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
Traditional Nameidebenone
SMILESCOC1=C(OC)C(=O)C(CCCCCCCCCCO)=C(C)C1=O
InChI IdentifierInChI=1S/C19H30O5/c1-14-15(12-10-8-6-4-5-7-9-11-13-20)17(22)19(24-3)18(23-2)16(14)21/h20H,4-13H2,1-3H3
InChI KeyJGPMMRGNQUBGND-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
  • Fatty alcohol
  • P-benzoquinone
  • Quinone
  • Fatty acyl
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP3.98ALOGPS
logP3.57ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)16.84ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity96.52 m³·mol⁻¹ChemAxon
Polarizability39.56 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0ab9-3497000000-d8feb0920ad00dd02dfcNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0690-1960000000-8c5ca483f0016c2028f6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0kar-0690000000-cbc95a31913165d691a7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0072-0944000000-a92c002a2a095f43babdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0932000000-16596a60138e58f99403Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0920000000-78a36c6ea797d2f634d0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dr-0109000000-0e448956195600661f3bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dr-1639000000-85bab94d4f5dfa49fb17Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kie-5910000000-da8dc14461899b449de5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0009000000-07c7343056bf9e03ff0aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00li-0179000000-4a9266ff06cc1b8e80e4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-9162000000-1ee1ad4824a121cd6461Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0109000000-c07b89c87c5050d87cceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dj-1964000000-a564eb1deb2fbb97818cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0532-9720000000-d41e9d56bc6f572437d3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0009000000-44e6f0d61e4038bcad78Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-0149000000-7f1280b294d10ddc2731Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0007-0493000000-b0d8056cbf1790c78c87Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
7016.0Log mg/kg[3900:12000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
378Psychostimulants, agents used for adhd and nootropicsHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
500Stairs And RampsBuilding & ConstructionNot Available
501Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
502Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
509Colour Television SystemsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
571CoinsHousehold itemsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
591LifeboatsMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
601Lawn MowersAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
621Chutes And SlidesRecreation & sports surfacesNot Available
625Racing SportsRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureNAD-dependent protein deacetylaseT1VXA1Schistosoma mansoniPredicted (SEA)0.0778492
Polyunsaturated fatty acid 5-lipoxygenase structureClick to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP09917HumansPredicted (SEA)5.91654
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)375.389
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)271.616
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)372.976
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)181.389
Macrophage-expressed gene 1 protein structureClick to view 3D structureMacrophage-expressed gene 1 proteinQ2M385HumansPredicted (SEA)1.79053
3-oxoacyl-[acyl-carrier-protein] synthase 1 structureClick to view 3D structure3-oxoacyl-[acyl-carrier-protein] synthase 1P9WQD9Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)28.5707
Click to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP12527Rattus norvegicusPredicted (SEA)784.72
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)3311.78
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)2756.64
Uracil-DNA glycosylase structureClick to view 3D structureUracil-DNA glycosylaseP13051HumansPredicted (SEA)69.0523
M-phase inducer phosphatase 1 structureClick to view 3D structureM-phase inducer phosphatase 1P30304HumansPredicted (SEA)84.7
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansPredicted (SEA)1940.86
Click to view 3D structureGlucose-6-phosphate dehydrogenase-6-phosphogluconolactonaseQ9BHT9Plasmodium bergheiPredicted (SEA)1149.99
G-protein coupled receptor 84 structureClick to view 3D structureG-protein coupled receptor 84Q9NQS5HumansPredicted (SEA)96.4552
Click to view 3D structureEquilibrative nucleoside transporter 2O54699Rattus norvegicusPredicted (SEA)263.208
M-phase inducer phosphatase 2 structureClick to view 3D structureM-phase inducer phosphatase 2P30305HumansPredicted (SEA)564.874
Click to view 3D structureGlutathione reductaseO15770Plasmodium falciparum 3D7Predicted (SEA)2.72472
Click to view 3D structureGenome polyproteinP29990dengue virus type 2Predicted (SEA)1486.38
E3 ubiquitin-protein ligase XIAP structureClick to view 3D structureE3 ubiquitin-protein ligase XIAPP98170HumansPredicted (SEA)874.714
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)6347.28
Click to view 3D structureSodium/iodide cotransporterQ63008Rattus norvegicusPredicted (SEA)553.119
Cytochrome P450 2C8 structureClick to view 3D structureCytochrome P450 2C8P10632HumansPredicted (SEA)6188.39
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)5640.18
Concentrations
Not Available
External Links
DrugBank IDDBMET01521
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIdebenone
Chemspider IDNot Available
ChEBI ID31687
PubChem Compound ID3686
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11207459
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15374364
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18045357
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18710357
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19283347
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19283350
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20955109
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22269948
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23859348
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=2669658
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=7981485
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=7988944