NP-MRD: Showing NP-Card for 13'-Carboxy-alpha-tocotrienol (NP0339040)

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Record Information

Version

2.0

Created at

2024-09-11 19:23:59 UTC

Updated at

2024-09-11 19:23:59 UTC

NP-MRD ID

NP0339040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13'-Carboxy-alpha-tocotrienol

Description

13'-Carboxy-alpha-tocotrienol, also known as 13AATE, 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. Tocotrienols are members of the vitamin E family. 13'-Carboxy-alpha-tocotrienol is an extremely weak basic (essentially neutral) compound (based on its pKa). 13'-Carboxy-alpha-tocotrienol is a dehydrogenation carboxylate product of 13'-hydroxy-a-tocotrienol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. 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). This variant of vitamin E only occur at very low levels in nature. Tocotrienols are natural compounds found in select vegetable oils, wheat germ, barley, saw palmetto, and certain types of nuts and grains.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208062D          

 33 34  0  0  1  0            999 V2000
   11.8376   -2.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4250   -2.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6000   -2.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1875   -3.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3625   -3.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9500   -4.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3625   -4.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1250   -4.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7125   -3.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7125   -4.9711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8376   -3.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4250   -4.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8376   -4.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4250   -5.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6000   -5.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8376   -6.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6626   -6.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0751   -7.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9001   -7.1146    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.4876   -7.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9001   -6.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6146   -5.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3291   -6.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0436   -5.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0436   -5.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7581   -6.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4725   -5.8771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7581   -7.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4725   -7.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0436   -7.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0436   -8.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3291   -7.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6146   -7.5271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 11  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 19 33  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 32  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END


  Mrv0541 02251208062D          

 33 34  0  0  1  0            999 V2000
   11.8376   -2.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4250   -2.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6000   -2.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1875   -3.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3625   -3.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9500   -4.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3625   -4.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1250   -4.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7125   -3.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7125   -4.9711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8376   -3.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4250   -4.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8376   -4.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4250   -5.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6000   -5.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8376   -6.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6626   -6.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0751   -7.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9001   -7.1146    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.4876   -7.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9001   -6.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6146   -5.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3291   -6.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0436   -5.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0436   -5.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7581   -6.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4725   -5.8771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7581   -7.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4725   -7.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0436   -7.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0436   -8.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3291   -7.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6146   -7.5271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 11  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 19 33  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 32  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339040

> <DATABASE_NAME>
NP-MRD

> <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)=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O4/c1-19(13-9-15-21(3)28(31)32)11-8-12-20(2)14-10-17-29(7)18-16-25-24(6)26(30)22(4)23(5)27(25)33-29/h11,14-15,30H,8-10,12-13,16-18H2,1-7H3,(H,31,32)/b19-11-,20-14-,21-15+/t29-/m1/s1

> <INCHI_KEY>
CBMCFKYSTHHHCC-QZDMETRGSA-N

> <FORMULA>
C29H42O4

> <MOLECULAR_WEIGHT>
454.6414

> <EXACT_MASS>
454.308309832

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
54.63932542899088

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,6Z,10Z)-13-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid

> <ALOGPS_LOGP>
6.43

> <JCHEM_LOGP>
8.482671415

> <ALOGPS_LOGS>
-6.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.802140863017726

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.071156876151937

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852669250194835

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
139.64129999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.99e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6Z,10Z)-13-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      22.097  -3.945   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.327  -5.278   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.787  -5.278   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.017  -6.612   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.477  -6.612   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.707  -7.946   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.477  -9.279   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.167  -7.946   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.397  -6.612   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      14.397  -9.279   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      22.097  -6.612   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.327  -7.946   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.097  -9.279   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.327 -10.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.787 -10.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.097 -11.947   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.637 -11.947   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.407 -13.281   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.947 -13.281   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.177 -14.614   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.947 -11.741   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.281 -10.971   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.614 -11.741   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.948 -10.971   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      29.948  -9.431   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      31.282 -11.741   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      32.615 -10.971   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      31.282 -13.281   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      32.615 -14.051   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      29.948 -14.051   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      29.948 -15.591   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      28.614 -13.281   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      27.281 -14.051   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   33                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   23   30   33                                                  
CONECT   33   19   32                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Value	Source
13'-Carboxy-a-tocotrienol	Generator
13'-Carboxy-α-tocotrienol	Generator
13aaTE	HMDB
(2E,6Z,10Z)-13-[(2R)-6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6,10-trienoate	Generator

Chemical Formula

C₂₉H₄₂O₄

Average Mass

454.6414 Da

Monoisotopic Mass

454.30831 Da

IUPAC Name

(2E,6Z,10Z)-13-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid

Traditional Name

(2E,6Z,10Z)-13-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-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)=C2C

InChI Identifier

InChI=1S/C29H42O4/c1-19(13-9-15-21(3)28(31)32)11-8-12-20(2)14-10-17-29(7)18-16-25-24(6)26(30)22(4)23(5)27(25)33-29/h11,14-15,30H,8-10,12-13,16-18H2,1-7H3,(H,31,32)/b19-11-,20-14-,21-15+/t29-/m1/s1

InChI Key

CBMCFKYSTHHHCC-QZDMETRGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
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

Physical Properties

State

Not Available

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
logP	6.43	ALOGPS
logP	8.48	ChemAxon
logS	-6.2	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	139.64 m³·mol⁻¹	ChemAxon
Polarizability	54.64 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012556

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029122

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

METLIN ID

Not Available

PubChem Compound

53481462

PDB ID

Not Available

ChEBI ID

139535

Good Scents ID

Not Available

References

General References

Showing NP-Card for 13'-Carboxy-alpha-tocotrienol (NP0339040)

MOL for NP0339040 (13'-Carboxy-alpha-tocotrienol)

3D MOL for NP0339040 (13'-Carboxy-alpha-tocotrienol)

3D SDF for NP0339040 (13'-Carboxy-alpha-tocotrienol)

3D-SDF for NP0339040 (13'-Carboxy-alpha-tocotrienol)

PDB for NP0339040 (13'-Carboxy-alpha-tocotrienol)

3D PDB for NP0339040 (13'-Carboxy-alpha-tocotrienol)

SMILES for NP0339040 (13'-Carboxy-alpha-tocotrienol)

INCHI for NP0339040 (13'-Carboxy-alpha-tocotrienol)

Structure for NP0339040 (13'-Carboxy-alpha-tocotrienol)

3D Structure for NP0339040 (13'-Carboxy-alpha-tocotrienol)