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Human Metabolome Database Version 3.5

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Showing metabocard for 9'-Carboxy-gamma-chromanol (HMDB12868)

Record Information
Version 3.5
Creation Date 2009-07-24 18:08:54 -0600
Update Date 2013-02-08 17:29:30 -0700
HMDB ID HMDB12868
Secondary Accession Numbers None
Metabolite Identification
Common Name 9'-Carboxy-gamma-chromanol
Description 9'-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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2,7,8-Trimethyl-2-(8'-carboxy-4'-methylnonyl)-6-chromanol
  2. 2,7,8-Trimethyl-2-(8'-carboxy-4'-methylnonyl)-6-hydroxychroman
  3. 9'-Carboxy-gamma-tocopherol
Chemical Formula C23H36O4
Average Molecular Weight 376.5295
Monoisotopic Molecular Weight 376.26135964
IUPAC Name (2R,6S)-9-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid
Traditional IUPAC Name (2R,6S)-9-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid
CAS Registry Number 178167-77-6
SMILES C[C@@H](CCC[C@@H](C)C(O)=O)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2
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+/m0/s1
InChI Key ODQOKHVJIYTOQE-NXHTTZLHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Benzopyrans
Sub Class N/A
Other Descriptors
  • Branched Fatty Acids
  • Heterocyclic Fatty Acids
Substituents
  • Alkyl Aryl Ether
  • Carboxylic Acid Salt
  • M Cresol
  • O Cresol
  • Phenol
  • Phenol Derivative
  • Pyran
  • Toluene
Direct Parent Benzopyrans
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 8.540E-04 g/L ALOGPS
LogP 5.61 ALOGPS
LogP 6.86 ChemAxon
LogS -5.64 ALOGPS
pKa (strongest acidic) 5 ChemAxon
pKa (strongest basic) -4.9 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 66.76 A2 ChemAxon
Rotatable Bond Count 9 ChemAxon
Refractivity 109.07 ChemAxon
Polarizability 45.01 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029192
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12868 Link_out
Metagene Link HMDB12868 Link_out
METLIN ID Not Available
PubChem Compound 53481536 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available