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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:08:52 UTC
Update Date2021-09-14 14:58:52 UTC
HMDB IDHMDB0012867
Secondary Accession Numbers
  • HMDB12867
Metabolite Identification
Common Name9'-Carboxy-alpha-tocotrienol
Description9'-Carboxy-alpha-tocotrienol is a dehydrogenation carboxylate product of 9'-hydroxy-a-tocotrienol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. Tocotrienols are members of the vitamin E family. An essential nutrient for the body, vitamin E is made up of four tocopherols (alpha, beta, gamma, delta) and four tocotrienols (alpha, beta, gamma, delta).Chemically, vitamin E is an antioxidant. One model for the function of vitamin E in the body is that it protects cell membranes, active enzyme sites, and DNA from free radical damage. Tocotrienols are natural compounds found in select vegetable oils, wheat germ, barley, saw palmetto, and certain types of nuts and grains. This variant of vitamin E only occur at very low levels in nature. While the majority of research on vitamin E has focused on alpha-tocopherol, studies into tocotrienols account for less than 1% of all research into vitamin E.
Structure
Data?1582753075
Synonyms
ValueSource
9'-Carboxy-a-tocotrienolGenerator
9'-Carboxy-α-tocotrienolGenerator
alpha-CDMOenHCHMDB
(2E,6E)-9-[(2R)-6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoateGenerator
Chemical FormulaC24H34O4
Average Molecular Weight386.5244
Monoisotopic Molecular Weight386.245709576
IUPAC Name(2E,6E)-9-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoic acid
Traditional Name(2E,6E)-9-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoic acid
CAS Registry NumberNot Available
SMILES
C\C(CC\C=C(/C)C(O)=O)=C/CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C
InChI Identifier
InChI=1S/C24H34O4/c1-15(9-7-11-16(2)23(26)27)10-8-13-24(6)14-12-20-19(5)21(25)17(3)18(4)22(20)28-24/h10-11,25H,7-9,12-14H2,1-6H3,(H,26,27)/b15-10+,16-11+/t24-/m1/s1
InChI KeyMEZYOZBFEXYIKB-ASKDMKCJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Aromatic monoterpenoid
  • Chromane
  • Benzopyran
  • Bicyclic monoterpenoid
  • 1-benzopyran
  • Medium-chain fatty acid
  • Alkyl aryl ether
  • Branched fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Unsaturated fatty acid
  • Organoheterocyclic compound
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Solubility0.00096 g/LALOGPS
logP5.36ALOGPS
logP6.82ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)5.01ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity115.84 m³·mol⁻¹ChemAxon
Polarizability46.22 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
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]+193.66731661259
DarkChem[M-H]-192.46631661259
DeepCCS[M+H]+198.93830932474
DeepCCS[M-H]-196.54230932474
DeepCCS[M-2H]-229.61830932474
DeepCCS[M+Na]+204.85130932474
AllCCS[M+H]+200.832859911
AllCCS[M+H-H2O]+198.232859911
AllCCS[M+NH4]+203.232859911
AllCCS[M+Na]+203.932859911
AllCCS[M-H]-199.232859911
AllCCS[M+Na-2H]-200.032859911
AllCCS[M+HCOO]-201.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
9'-Carboxy-alpha-tocotrienolC\C(CC\C=C(/C)C(O)=O)=C/CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C4573.3Standard polar33892256
9'-Carboxy-alpha-tocotrienolC\C(CC\C=C(/C)C(O)=O)=C/CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C3038.7Standard non polar33892256
9'-Carboxy-alpha-tocotrienolC\C(CC\C=C(/C)C(O)=O)=C/CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C3195.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
9'-Carboxy-alpha-tocotrienol,1TMS,isomer #1C/C(=C\CC[C@]1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1)CC/C=C(\C)C(=O)O[Si](C)(C)C3050.5Semi standard non polar33892256
9'-Carboxy-alpha-tocotrienol,1TMS,isomer #2C/C(=C\CC[C@]1(C)CCC2=C(C)C(O[Si](C)(C)C)=C(C)C(C)=C2O1)CC/C=C(\C)C(=O)O3156.2Semi standard non polar33892256
9'-Carboxy-alpha-tocotrienol,2TMS,isomer #1C/C(=C\CC[C@]1(C)CCC2=C(C)C(O[Si](C)(C)C)=C(C)C(C)=C2O1)CC/C=C(\C)C(=O)O[Si](C)(C)C3047.0Semi standard non polar33892256
9'-Carboxy-alpha-tocotrienol,1TBDMS,isomer #1C/C(=C\CC[C@]1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1)CC/C=C(\C)C(=O)O[Si](C)(C)C(C)(C)C3290.6Semi standard non polar33892256
9'-Carboxy-alpha-tocotrienol,1TBDMS,isomer #2C/C(=C\CC[C@]1(C)CCC2=C(C)C(O[Si](C)(C)C(C)(C)C)=C(C)C(C)=C2O1)CC/C=C(\C)C(=O)O3388.1Semi standard non polar33892256
9'-Carboxy-alpha-tocotrienol,2TBDMS,isomer #1C/C(=C\CC[C@]1(C)CCC2=C(C)C(O[Si](C)(C)C(C)(C)C)=C(C)C(C)=C2O1)CC/C=C(\C)C(=O)O[Si](C)(C)C(C)(C)C3539.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 9'-Carboxy-alpha-tocotrienol GC-MS (Non-derivatized) - 70eV, Positivesplash10-05g3-3597000000-ee33a4040e8ff3c5f3a22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9'-Carboxy-alpha-tocotrienol GC-MS (2 TMS) - 70eV, Positivesplash10-014i-2165490000-8847e41fbbef01f7bda52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9'-Carboxy-alpha-tocotrienol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9'-Carboxy-alpha-tocotrienol 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 - 9'-Carboxy-alpha-tocotrienol 10V, Positive-QTOFsplash10-014r-0429000000-a66826ff0d07b01063932017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-tocotrienol 20V, Positive-QTOFsplash10-014i-0912000000-5ee1236a995a9d12f0d22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-tocotrienol 40V, Positive-QTOFsplash10-014i-1910000000-ee9f7f94c621608c3fb32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-tocotrienol 10V, Negative-QTOFsplash10-000i-0009000000-b373da74391ce2789a052017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-tocotrienol 20V, Negative-QTOFsplash10-03du-0319000000-17f654138f67f0a81c492017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-tocotrienol 40V, Negative-QTOFsplash10-02cs-1923000000-50e6ff8d4a1ad04e4c792017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-tocotrienol 10V, Negative-QTOFsplash10-000l-0009000000-bee69c7476b7b7fa661c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-tocotrienol 20V, Negative-QTOFsplash10-03di-0109000000-24ce754465533875736b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-tocotrienol 40V, Negative-QTOFsplash10-0lmi-0192000000-3f4ee4b78e71bf13cccf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-tocotrienol 10V, Positive-QTOFsplash10-0300-0097000000-c797498613a30824a81a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-tocotrienol 20V, Positive-QTOFsplash10-066v-0092000000-84aa2ba2bc2336336b652021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-tocotrienol 40V, Positive-QTOFsplash10-0a4i-5980000000-d16bab22c4bb256a71012021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDFDB029191
KNApSAcK IDNot Available
Chemspider ID30776650
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481535
PDB IDNot Available
ChEBI ID175091
Food Biomarker OntologyNot Available
VMH IDCE5851
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.