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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:14:56 UTC
Update Date2022-03-07 02:54:05 UTC
HMDB IDHMDB0034408
Secondary Accession Numbers
  • HMDB34408
Metabolite Identification
Common Namealpha-Tocopherolquinone
Descriptionalpha-Tocopherolquinone, also known as eutrophyl or vitamin e quinone, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review a significant number of articles have been published on alpha-Tocopherolquinone.
Structure
Data?1563862559
Synonyms
ValueSource
a-TocopherolquinoneGenerator
Α-tocopherolquinoneGenerator
2 (3-Hydroxy-3,7,11,15-tetramethylhexadecyl)- 3,5,6-trimethyl-1,4-benzoquinoneMeSH
EutrophylMeSH
alpha-Tocopherol quinoneMeSH
alpha-Tocopheryl quinoneMeSH
alpha-TocoquinoneMeSH
delta-TocopherylquinoneMeSH
gamma-TocopherylquinoneMeSH
TocopherolquinoneMeSH
TocopherylquinoneMeSH
Tocopherylquinone, ((3R*,7R*,11R*)-(+-))-isomerMeSH
Vitamin e quinoneMeSH
a-Tocopheryl quinoneHMDB
a-TocoquinoneHMDB
alpha-TocopheroquinoneHMDB
D 178HMDB
IpotensilHMDB
MetorenaHMDB
TensiopressHMDB
TriminaHMDB
VitapressinaHMDB
alpha-TocopherolquinoneMeSH
Chemical FormulaC29H50O3
Average Molecular Weight446.7055
Monoisotopic Molecular Weight446.375995466
IUPAC Name2-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione
Traditional Name2-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione
CAS Registry Number7559-04-8
SMILES
CC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O
InChI Identifier
InChI=1S/C29H50O3/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8,32)19-17-26-25(7)27(30)23(5)24(6)28(26)31/h20-22,32H,9-19H2,1-8H3
InChI KeyLTVDFSLWFKLJDQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Diterpenoid
  • Prenylbenzoquinone
  • Quinone
  • P-benzoquinone
  • Tertiary alcohol
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00041 g/LALOGPS
logP7.09ALOGPS
logP9.03ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)19.44ChemAxon
pKa (Strongest Basic)-0.86ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity137.43 m³·mol⁻¹ChemAxon
Polarizability57.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+212.71431661259
DarkChem[M-H]-209.53331661259
DeepCCS[M+H]+226.03430932474
DeepCCS[M-H]-222.6630932474
DeepCCS[M-2H]-258.55830932474
DeepCCS[M+Na]+234.84930932474
AllCCS[M+H]+217.732859911
AllCCS[M+H-H2O]+215.832859911
AllCCS[M+NH4]+219.432859911
AllCCS[M+Na]+219.932859911
AllCCS[M-H]-215.832859911
AllCCS[M+Na-2H]-219.232859911
AllCCS[M+HCOO]-223.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-TocopherolquinoneCC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O4012.8Standard polar33892256
alpha-TocopherolquinoneCC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O3153.3Standard non polar33892256
alpha-TocopherolquinoneCC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O3149.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Tocopherolquinone,1TMS,isomer #1CC1=C(C)C(=O)C(CCC(C)(CCCC(C)CCCC(C)CCCC(C)C)O[Si](C)(C)C)=C(C)C1=O3379.7Semi standard non polar33892256
alpha-Tocopherolquinone,1TBDMS,isomer #1CC1=C(C)C(=O)C(CCC(C)(CCCC(C)CCCC(C)CCCC(C)C)O[Si](C)(C)C(C)(C)C)=C(C)C1=O3624.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Tocopherolquinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ec-7892600000-f0485dd48007bc1c48132017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Tocopherolquinone GC-MS (1 TMS) - 70eV, Positivesplash10-0udl-9524240000-dcf4b3026071bb5948b72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Tocopherolquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Tocopherolquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Tocopherolquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Tocopherolquinone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocopherolquinone 10V, Positive-QTOFsplash10-004j-1102900000-49a0f229d8be1d2a90c62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocopherolquinone 20V, Positive-QTOFsplash10-03di-6976600000-68c67a03280d0fc70f622016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocopherolquinone 40V, Positive-QTOFsplash10-0pb9-9354000000-78325deb5c05a3bae2072016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocopherolquinone 10V, Negative-QTOFsplash10-0002-0001900000-d96003242c85e61998d72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocopherolquinone 20V, Negative-QTOFsplash10-002b-0113900000-2637be642ce270d086a42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocopherolquinone 40V, Negative-QTOFsplash10-004l-7149600000-e407795567ef4b3d97122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocopherolquinone 10V, Positive-QTOFsplash10-004j-1024900000-c1e044b40138528be55a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocopherolquinone 20V, Positive-QTOFsplash10-05mk-9404200000-c42a18d7d61055a4485c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocopherolquinone 40V, Positive-QTOFsplash10-0ced-9700000000-e3754e031d8a907d05812021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocopherolquinone 10V, Negative-QTOFsplash10-0002-0000900000-faa9c64132b6ef6d8e372021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocopherolquinone 20V, Negative-QTOFsplash10-0002-0510900000-ddefa2f1f90501841fff2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocopherolquinone 40V, Negative-QTOFsplash10-01t9-0983500000-b3d13f0d982becd8fa362021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012799
KNApSAcK IDC00019451
Chemspider ID22627
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24205
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.