Idebenone (CHEM017574)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:28:19 UTC
Update Date2016-10-28 10:02:40 UTC
Accession NumberCHEM017574
Identification
Common NameIdebenone
ClassSmall Molecule
DescriptionA member of the class of 1,4-benzoquinones which is substituted by methoxy groups at positions 2 and 3, by a methyl group at positions 5, and by a 10-hydroxydecyl group at positions 6. Initially developed for the treatment of Alzheimer's disease, benefits were modest; it was subsequently found to be of benefit for the symptomatic treatment of Friedreich's ataxia.
Contaminant Sources
  • Cosmetic Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D 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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-3497000000-d8feb0920ad00dd02dfcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0690-1960000000-8c5ca483f0016c2028f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0kar-0690000000-cbc95a31913165d691a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0072-0944000000-a92c002a2a095f43babdSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0932000000-16596a60138e58f99403Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-0920000000-78a36c6ea797d2f634d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0109000000-0e448956195600661f3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-1639000000-85bab94d4f5dfa49fb17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kie-5910000000-da8dc14461899b449de5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-07c7343056bf9e03ff0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00li-0179000000-4a9266ff06cc1b8e80e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9162000000-1ee1ad4824a121cd6461Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0109000000-c07b89c87c5050d87cceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-1964000000-a564eb1deb2fbb97818cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0532-9720000000-d41e9d56bc6f572437d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-44e6f0d61e4038bcad78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0149000000-7f1280b294d10ddc2731Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-0493000000-b0d8056cbf1790c78c87Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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