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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:02:52 UTC
Update Date2022-03-07 02:51:26 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?1582753064
Synonyms
ValueSource
13'-Carboxy-g-tocopherolGenerator
13'-Carboxy-γ-tocopherolGenerator
(6R,10S)-13-[(2R)-6-Hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltridecanoateHMDB
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
Description 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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
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 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
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]+207.04831661259
DarkChem[M-H]-202.7731661259
DeepCCS[M+H]+215.58230932474
DeepCCS[M-H]-213.18630932474
DeepCCS[M-2H]-246.10930932474
DeepCCS[M+Na]+221.50830932474
AllCCS[M+H]+217.532859911
AllCCS[M+H-H2O]+215.532859911
AllCCS[M+NH4]+219.432859911
AllCCS[M+Na]+219.932859911
AllCCS[M-H]-215.932859911
AllCCS[M+Na-2H]-218.832859911
AllCCS[M+HCOO]-222.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
13'-Carboxy-gamma-tocopherolC[C@H](CCC[C@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2)CCCC(C)C(O)=O4574.0Standard polar33892256
13'-Carboxy-gamma-tocopherolC[C@H](CCC[C@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2)CCCC(C)C(O)=O3245.8Standard non polar33892256
13'-Carboxy-gamma-tocopherolC[C@H](CCC[C@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2)CCCC(C)C(O)=O3448.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
13'-Carboxy-gamma-tocopherol,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O)OC2=C1C3273.3Semi standard non polar33892256
13'-Carboxy-gamma-tocopherol,1TMS,isomer #2CC1=C(O)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C)OC2=C1C3243.5Semi standard non polar33892256
13'-Carboxy-gamma-tocopherol,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C)OC2=C1C3212.6Semi standard non polar33892256
13'-Carboxy-gamma-tocopherol,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O)OC2=C1C3544.1Semi standard non polar33892256
13'-Carboxy-gamma-tocopherol,1TBDMS,isomer #2CC1=C(O)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C(C)(C)C)OC2=C1C3525.9Semi standard non polar33892256
13'-Carboxy-gamma-tocopherol,2TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C(C)(C)C)OC2=C1C3742.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 13'-Carboxy-gamma-tocopherol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-2396300000-1dd473dc02ea4da189722017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13'-Carboxy-gamma-tocopherol GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2167490000-94e2372e73651916e47e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13'-Carboxy-gamma-tocopherol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 10V, Positive-QTOFsplash10-0ufs-0412900000-63565c5e56d90f9430802017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 20V, Positive-QTOFsplash10-0udi-0911100000-4ffe5ea923b2a30ef4922017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 40V, Positive-QTOFsplash10-0udi-1910000000-29ba2d9e2ab77c9f88732017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 10V, Negative-QTOFsplash10-0002-0000900000-51d8122a565eb68a3eec2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 20V, Negative-QTOFsplash10-0002-0502900000-e3e6e354d3bb0c65e49f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 40V, Negative-QTOFsplash10-007a-7915200000-83fbd3fa7e65ad5850df2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 10V, Negative-QTOFsplash10-0002-0000900000-560a373e8cd7a465d30d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 20V, Negative-QTOFsplash10-0f6t-2328900000-2634c1da4c560ea61f172021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 40V, Negative-QTOFsplash10-0076-1809200000-6bc39ab36366dcce3a652021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 10V, Positive-QTOFsplash10-0zmi-0429300000-22647b146ed6d5e176192021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 20V, Positive-QTOFsplash10-0frb-3956000000-1defc3696e7a013bbd862021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 40V, Positive-QTOFsplash10-0005-7920000000-088b17bb8a1e7d4289c22021-09-25Wishart 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 IDFDB029123
KNApSAcK IDNot Available
Chemspider ID35032540
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481463
PDB IDNot Available
ChEBI ID168306
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.