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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:02:52 UTC
Update Date2019-07-23 05:58:10 UTC
HMDB IDHMDB0012557
Secondary Accession Numbers
  • HMDB12557
Metabolite Identification
Common Name13'-Carboxy-gamma-tocopherol
Description13'-Carboxy-gamma-tocopherol is a dehydrogenation carboxylate product of 13'-hydroxy-r-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. r-Tocopherol provides different antioxidant activities in food and in-vitro studies and showed higher activity in trapping lipophilic electrophiles and reactive nitrogen and oxygen species. From the metabolism end product, only that of r-tocopherol (2,7,8-trimethyl-2-(b-carboxyethyl)-6-hydroxychroman), but not that of a-tocopherol, was identified to provide natriuretic activity. Only the r-tocopherol plasma level served as biomarker for cancer and cardiovascular risk.
Structure
Data?1563861490
SynonymsNot Available
Chemical FormulaC28H46O4
Average Molecular Weight446.6624
Monoisotopic Molecular Weight446.33960996
IUPAC Name(6R,10S)-13-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltridecanoic acid
Traditional Name(6R,10S)-13-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6,10-trimethyltridecanoic acid
CAS Registry NumberNot Available
SMILES
C[C@H](CCC[C@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2)CCCC(C)C(O)=O
InChI Identifier
InChI=1S/C28H46O4/c1-19(12-8-14-21(3)27(30)31)10-7-11-20(2)13-9-16-28(6)17-15-24-18-25(29)22(4)23(5)26(24)32-28/h18-21,29H,7-17H2,1-6H3,(H,30,31)/t19-,20+,21?,28-/m1/s1
InChI KeyWPZHQZIUOXUCOK-PXUFRVCMSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentTocopherols
Alternative Parents
Substituents
  • Tocopherol
  • Diterpenoid
  • Long-chain fatty acid
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.1e-05 g/LALOGPS
logP7.21ALOGPS
logP8.93ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)5ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity132.02 m³·mol⁻¹ChemAxon
Polarizability54.97 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-2396300000-1dd473dc02ea4da18972JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2167490000-94e2372e73651916e47eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufs-0412900000-63565c5e56d90f943080JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0911100000-4ffe5ea923b2a30ef492JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1910000000-29ba2d9e2ab77c9f8873JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-51d8122a565eb68a3eecJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0502900000-e3e6e354d3bb0c65e49fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007a-7915200000-83fbd3fa7e65ad5850dfJSpectraViewer | MoNA
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
FoodDB IDFDB029123
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481463
PDB IDNot Available
ChEBI 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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.