ContaminantDB: 13'-Carboxy-gamma-tocotrienol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-27 01:05:27 UTC

Update Date

2016-11-09 01:22:21 UTC

Accession Number

CHEM040947

Identification

Common Name

13'-Carboxy-gamma-tocotrienol

Class

Small Molecule

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.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
13'-Carboxy-g-tocotrienol	Generator
13'-Carboxy-γ-tocotrienol	Generator
13AgammaTE	HMDB
(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-trienoate	Generator

Chemical Formula

C₂₈H₄₀O₄

Average Molecular Mass

440.615 g/mol

Monoisotopic Mass

440.293 g/mol

CAS Registry Number

Not Available

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 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

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

Description

belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocopherols that contain a saturated trimethyltridecyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Tocotrienols

Alternative Parents

Substituents

Tocotrienol
Diterpenoid
Long-chain fatty acid
Chromane
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Branched fatty acid
Methyl-branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Benzenoid
Unsaturated fatty acid
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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00042 g/L	ALOGPS
logP	6.46	ALOGPS
logP	7.97	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	5.07	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	134.6 m³·mol⁻¹	ChemAxon
Polarizability	53.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-1394300000-23595ddcefae7a79ba51	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-1047590000-9fdeaf3f8312ef52a47b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fdp-0636900000-e03152e51048e5fa6832	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0922000000-4acf73c008316651971a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-1910000000-ccdca31bc77bf0a54795	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0001900000-7f5ba63206cca5ef9b82	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000b-1709700000-69bc7cff5ee914bf661d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0092-3924200000-1366b1d5ee702e7c59e4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000e-0489300000-de85d00a27de026ee8a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f72-1493000000-eb93552b5271ca59d667	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-2910000000-009e6415748ca322f4ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0109100000-bdc484e6f9534e60c30e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ar1-0419000000-5bddc845c6fc72bb1a84	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004r-0209000000-42d0ae4b5b676b92c5d9	Spectrum