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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:02:50 UTC
Update Date2022-03-07 02:51:26 UTC
HMDB IDHMDB0012555
Secondary Accession Numbers
  • HMDB12555
Metabolite Identification
Common Name13'-Carboxy-alpha-tocopherol
Description13'-carboxy-alpha-tocopherol is a dehydrogenation carboxylate product of 13'-hydroxy-a-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. The tocopherols ( a-tocopherol , b-tocopherol ,r-tocopherol and d-tocopherol ) and their corresponding tocotrienols are synthesized by plants and have vitamin E antixoidant activity (see pathway vitamin E biosynthesis ). They differ in the number and location of methyl groups on the chromanol ring. The naturally occurring form of a-tocopherol is (2R,4'R,8'R)-a-tocopherol (synonym (R,R,R)-a-tocopherol). Synthetic a-tocopherols are a racemic mixture of eight different R and S stereoisomers. Only the 2R forms are recognized as meeting human requirements. The in vivo function of vitamin E is to scavenge peroxyl radicals via its phenolic (chromanol) hydroxyl group, thus protecting lipids against free radical-catalyzed peroxidation. The tocopheryl radical formed can then be reduced by reductants such as L-ascorbate. Other major products of a-tocopherol oxidation include α-tocopherylquinone and epoxy-a-tocopherols. The metabolites a-tocopheronic acid and its lactone, known as the Simon metabolites, are generally believed to be artefacts. In addition to these oxidation products, the other major class of tocopherol metabolites is the carboxyethyl-hydroxychromans.These metabolites are produced in significant amounts in response to excess vitamin E ingestion. Vitamin E is fat-soluble and its utilization requires intestinal fat absorption mechanisms. It is secreted from the intestine into the lymphatic system in chylomicrons which subsequently enter the plasma. Lipolysis of these chylomicrons can result in delivery of vitamin E to tissues, transfer to high-density lipoproteins (and subsequently to other lipoproteins via the phospholipid exchange protein), or retention in chylomicron remnants. These remnants are taken up by the liver. Natural (R,R,R)-α-tocopherol and synthetic 2R-α-tocopherols are then preferentially secreted from the liver into plasma as a result of the specificity of the α-tocopherol transfer protein. This protein, along with the metabolism of excess vitamin E in the liver and excretion into urine and bile, mediate the supply of a-tocopherol in plasma and tissues.
Structure
Data?1582753064
Synonyms
ValueSource
13'-Carboxy-a-tocopherolGenerator
13'-Carboxy-α-tocopherolGenerator
(6R,10S)-13-[(2S)-6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltridecanoateHMDB
Chemical FormulaC29H48O4
Average Molecular Weight460.689
Monoisotopic Molecular Weight460.355260024
IUPAC Name(6R,10S)-13-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltridecanoic acid
Traditional Name(6R,10S)-13-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-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)=C2C)CCCC(C)C(O)=O
InChI Identifier
InChI=1S/C29H48O4/c1-19(13-9-15-21(3)28(31)32)11-8-12-20(2)14-10-17-29(7)18-16-25-24(6)26(30)22(4)23(5)27(25)33-29/h19-21,30H,8-18H2,1-7H3,(H,31,32)/t19-,20+,21?,29+/m1/s1
InChI KeyNJIUWSABAIXPGI-AXTKCOKSSA-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
  • 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 Solubility6.2e-05 g/LALOGPS
logP7.38ALOGPS
logP9.44ChemAxon
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
Refractivity137.07 m³·mol⁻¹ChemAxon
Polarizability57.12 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]+208.68531661259
DarkChem[M-H]-204.92931661259
DeepCCS[M+H]+217.94830932474
DeepCCS[M-H]-215.55330932474
DeepCCS[M-2H]-248.43530932474
DeepCCS[M+Na]+223.86130932474
AllCCS[M+H]+220.232859911
AllCCS[M+H-H2O]+218.332859911
AllCCS[M+NH4]+222.032859911
AllCCS[M+Na]+222.532859911
AllCCS[M-H]-219.032859911
AllCCS[M+Na-2H]-222.032859911
AllCCS[M+HCOO]-225.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
13'-Carboxy-alpha-tocopherolC[C@H](CCC[C@H](C)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C)CCCC(C)C(O)=O4695.6Standard polar33892256
13'-Carboxy-alpha-tocopherolC[C@H](CCC[C@H](C)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C)CCCC(C)C(O)=O3363.1Standard non polar33892256
13'-Carboxy-alpha-tocopherolC[C@H](CCC[C@H](C)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C)CCCC(C)C(O)=O3500.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
13'-Carboxy-alpha-tocopherol,1TMS,isomer #1CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O)O2)C(C)=C1O[Si](C)(C)C3382.3Semi standard non polar33892256
13'-Carboxy-alpha-tocopherol,1TMS,isomer #2CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C)O2)C(C)=C1O3324.1Semi standard non polar33892256
13'-Carboxy-alpha-tocopherol,2TMS,isomer #1CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C)O2)C(C)=C1O[Si](C)(C)C3350.4Semi standard non polar33892256
13'-Carboxy-alpha-tocopherol,1TBDMS,isomer #1CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O)O2)C(C)=C1O[Si](C)(C)C(C)(C)C3637.6Semi standard non polar33892256
13'-Carboxy-alpha-tocopherol,1TBDMS,isomer #2CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O3587.1Semi standard non polar33892256
13'-Carboxy-alpha-tocopherol,2TBDMS,isomer #1CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O[Si](C)(C)C(C)(C)C3859.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 13'-Carboxy-alpha-tocopherol GC-MS (Non-derivatized) - 70eV, Positivesplash10-052e-1295300000-2ba3285725719c5881282017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13'-Carboxy-alpha-tocopherol GC-MS (2 TMS) - 70eV, Positivesplash10-000i-3156490000-03a0da1adf52e9e61fe32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13'-Carboxy-alpha-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-alpha-tocopherol 10V, Positive-QTOFsplash10-03xu-0411900000-6aac4b4053205659c4ba2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 20V, Positive-QTOFsplash10-014i-0911100000-a2eb530497be580e2a0b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 40V, Positive-QTOFsplash10-014i-0900000000-8cfa2f87ad5b2d0fe2212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 10V, Negative-QTOFsplash10-0a4i-0000900000-8234c0b64f303a84be8b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 20V, Negative-QTOFsplash10-0cdi-0401900000-33f2cd8e55dfc58482542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 40V, Negative-QTOFsplash10-0002-3912200000-e17701c9ef0503d01b0f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 10V, Positive-QTOFsplash10-014r-0219300000-c80c91d9a652fdd333f52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 20V, Positive-QTOFsplash10-014i-4459000000-a023b2ae98132fcbed7f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 40V, Positive-QTOFsplash10-0a4j-9651000000-b280243e088f79fef0e32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 10V, Negative-QTOFsplash10-0a4i-0000900000-55fc02ff579e3c3add1b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 20V, Negative-QTOFsplash10-0cdj-2224900000-4590a0f16b2640290f4f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 40V, Negative-QTOFsplash10-0a4j-1279200000-2e3da45716fd5d0a54b12021-09-24Wishart 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 IDFDB029121
KNApSAcK IDNot Available
Chemspider ID35032539
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481461
PDB IDNot Available
ChEBI ID145207
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.