Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for 13'-carboxy-gamma-tocotrienol (HMDB12558)

Record Information
Version 3.5
Creation Date 2009-07-24 18:02:53 -0600
Update Date 2013-05-07 13:56:11 -0600
HMDB ID HMDB12558
Secondary Accession Numbers None
Metabolite Identification
Common Name 13'-carboxy-gamma-tocotrienol
Description 13'-carboxy-r-tocotrienol is a dehydrogenation carboxylate product of 13'-hydroxy-r-tocotrienol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. Gamma-tocotrienol targets cancer cells by inhibiting Id1, a key cancer-promoting protein. Gamma-tocotrienol was shown to trigger cell apoptosis and well as anti-proliferation of cancer cells. This mechanism was also observed in separate prostate cancer and melanoma cell line studies.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 13AgammaTE
Chemical Formula C28H40O4
Average Molecular Weight 440.6148
Monoisotopic Molecular Weight 440.292659768
IUPAC Name (2E,6E,10E)-13-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid
Traditional IUPAC Name (2E,6E,10E)-13-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid
CAS Registry Number Not Available
SMILES C\C(CC\C=C(/C)C(O)=O)=C/CC\C(C)=C\CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2
InChI Identifier InChI=1S/C28H40O4/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/h10,13-14,18,29H,7-9,11-12,15-17H2,1-6H3,(H,30,31)/b19-10+,20-13+,21-14+/t28-/m1/s1
InChI Key UJMZKOBSLDXUHY-YQHRJHOASA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Quinone and Hydroquinone Lipids
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Branched Fatty Acids
  • Heterocyclic Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Alkyl Aryl Ether
  • Benzopyran
  • Carboxylic Acid Salt
  • Chromane
  • Diterpene
  • Enone
  • Farnesane Skeleton
  • Isoprene
  • M Cresol
  • O Cresol
  • Phenol
  • Phenol Derivative
  • Pyran
  • Toluene
Direct Parent Tocotrienols
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 4.220E-04 g/L ALOGPS
LogP 6.46 ALOGPS
LogP 7.97 ChemAxon
LogS -6.02 ALOGPS
pKa (strongest acidic) 5.07 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 10 ChemAxon
Refractivity 134.6 ChemAxon
Polarizability 53.59 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 FDB029124
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 HMDB12558 Link_out
Metagene Link HMDB12558 Link_out
METLIN ID Not Available
PubChem Compound 53481464 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