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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:08:54 UTC
Update Date2019-07-23 05:58:19 UTC
HMDB IDHMDB0012868
Secondary Accession Numbers
  • HMDB12868
Metabolite Identification
Common Name9'-Carboxy-gamma-chromanol
Description9'-Carboxy-gamma-tocopherol is a dehydrogenation carboxylate product of 9'-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?1563861499
Synonyms
ValueSource
(2S,6R)-9-[(2R)-6-Hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnonanoateGenerator
γ-CDMOHCHMDB
γ-Carboxydimethyloctyl hydroxychromanHMDB
γ-CarboxydimethyloctylhydroxychromanHMDB
gamma-CDMOHCHMDB
gamma-Carboxydimethyloctyl hydroxychromanHMDB
gamma-CarboxydimethyloctylhydroxychromanHMDB
Chemical FormulaC23H36O4
Average Molecular Weight376.537
Monoisotopic Molecular Weight376.261359639
IUPAC Name(2S,6R)-9-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid
Traditional Name(2S,6R)-9-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid
CAS Registry Number1215088-64-4
SMILES
C[C@H](CCC[C@H](C)C(O)=O)CCC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1
InChI Identifier
InChI=1S/C23H36O4/c1-15(8-6-10-16(2)22(25)26)9-7-12-23(5)13-11-19-14-20(24)17(3)18(4)21(19)27-23/h14-16,24H,6-13H2,1-5H3,(H,25,26)/t15-,16+,23-/m1/s1
InChI KeyODQOKHVJIYTOQE-VBURHUQHSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Disposition

Biological location:

Source:

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 Solubility0.00085 g/LALOGPS
logP5.61ALOGPS
logP6.86ChemAxon
logS-5.6ALOGPS
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 Count9ChemAxon
Refractivity109.07 m³·mol⁻¹ChemAxon
Polarizability44.99 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kdi-0419000000-cd057edae393743570b5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0911000000-a634d5d40e9ad8466db6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-567171c8ebdc774c19a0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-8be58d31ef5f29daf85cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-005a-0409000000-c4f9d5fd1cfb91f60b96JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05tb-7916000000-27664edfcab573c04ee2JSpectraViewer | MoNA
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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhao Y, Lee MJ, Cheung C, Ju JH, Chen YK, Liu B, Hu LQ, Yang CS: Analysis of multiple metabolites of tocopherols and tocotrienols in mice and humans. J Agric Food Chem. 2010 Apr 28;58(8):4844-52. doi: 10.1021/jf904464u. [PubMed:20222730 ]