NP-MRD: Showing NP-Card for 2R-γ-tocotrienol (NP0014303)

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Record Information

Version

1.0

Created at

2021-01-05 23:30:40 UTC

Updated at

2021-08-19 23:59:52 UTC

NP-MRD ID

NP0014303

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2R-γ-tocotrienol

Provided By

NPAtlas

Description

Gamma-Tocotrienol, also known as γ-tocotrienol or tocotrienol, gamma, 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. Thus, gamma-tocotrienol is considered to be a quinone. Gamma-Tocotrienol exists in all living organisms, ranging from bacteria to humans. Gamma-Tocotrienol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 2R-γ-tocotrienol is found in Amaranthus hypochondriacus, Cinnamosma macrocarpa, Cystophora monilifera, Foeniculum vulgare, Hippophae rhamnoides, Juglans regia and Triadica sebifera. It was first documented in 2000 (PMID: 11413487). Based on a literature review a significant number of articles have been published on gamma-Tocotrienol (PMID: 16902246) (PMID: 17374880) (PMID: 20044567) (PMID: 26093325).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119543D          

 72 73  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 72 73  0  0  0  0  0  0  0  0999 V2000
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  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  8 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 13 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 18 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  0
 20 64  1  0
 22 65  1  0
 24 66  1  0
 26 67  1  0
 26 68  1  0
 26 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
M  END


  Mrv1652306242119543D          

 72 73  0  0  0  0            999 V2000
   -7.1242    2.9167    0.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4083    1.4385    0.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3353    0.9440   -0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8474    0.6399    1.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1239   -0.8048    1.4264 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9068   -1.6502    1.2532 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1428   -1.4176    0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7212   -1.6044   -1.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525   -1.0181    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0985   -0.7888   -1.1821 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9036   -1.6415   -1.4141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8385   -1.5698   -0.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596   -1.9692    0.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3648   -1.1549   -0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5407   -1.0259    0.1161 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9584    0.4321    0.0669 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1637    0.6931    0.9457 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8664    0.3455    2.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4507    2.1730    0.8861 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1110    2.4815   -0.4356 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3853    1.7077   -0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5462    2.2366   -0.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186    1.4972   -1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9046    2.0405   -1.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7668    0.2027   -0.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0240   -0.6085   -0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5942   -0.3238   -0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5962   -1.7046    0.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4228    0.4030   -0.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2345   -0.0994    0.4890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0068    3.4650    0.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0205    3.1958    1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2465   -2.7239    1.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3921   -0.8619    1.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7426   -0.9046   -2.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697    0.2937   -1.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2212   -2.7196   -1.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5267   -1.3651   -2.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1855   -2.6142    1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9233   -2.6978    1.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5496   -0.8698   -1.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3582   -1.6477   -0.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3808   -1.3882    1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0818    1.0286    0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2329    0.6217   -0.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6912    0.7966    2.9985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8704   -0.7295    2.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4573    2.6872    0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    2.5069    1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5044    2.1652   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5375    3.2628   -1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8895    2.9917   -1.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5637   -2.1074    0.4055 H   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  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
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 21 22  2  0  0  0  0
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 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
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 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 17  1  0  0  0  0
 29 21  1  0  0  0  0
  1 31  1  0  0  0  0
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  3 36  1  0  0  0  0
  4 37  1  0  0  0  0
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  5 39  1  0  0  0  0
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 28 70  1  0  0  0  0
 28 71  1  0  0  0  0
 28 72  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0014303

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(=C2O[C@](C([H])([H])[H])(C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])C2=C1[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h11,13,15,19,29H,8-10,12,14,16-18H2,1-7H3/b21-13+,22-15+/t28-/m1/s1

> <INCHI_KEY>
OTXNTMVVOOBZCV-WAZJVIJMSA-N

> <FORMULA>
C28H42O2

> <MOLECULAR_WEIGHT>
410.6319

> <EXACT_MASS>
410.318480588

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.96100767016158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
7.71

> <JCHEM_LOGP>
8.777557426666668

> <ALOGPS_LOGS>
-6.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.47042231417464

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852470626655554

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
132.88289999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.40e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-tocotrienol

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 72 73  0  0  0  0  0  0  0  0999 V2000
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   -5.1428   -1.4176    0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7212   -1.6044   -1.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6912    0.7966    2.9985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8704   -0.7295    2.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9403    0.8592    2.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573    2.6872    0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    2.5069    1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5044    2.1652   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2985    3.5708   -0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375    3.2628   -1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8895    2.9917   -1.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9100    0.0536   -0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0319   -1.1050   -1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0268   -1.3647    0.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2449   -2.3730   -0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -1.7149    1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5637   -2.1074    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 17 16  1  6
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 30 17  1  0
 29 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  8 42  1  0
  8 43  1  0
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  9 45  1  0
 10 46  1  0
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 11 48  1  0
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 13 50  1  0
 13 51  1  0
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 18 58  1  0
 18 59  1  0
 18 60  1  0
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 22 65  1  0
 24 66  1  0
 26 67  1  0
 26 68  1  0
 26 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -7.124   2.917   0.604  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.408   1.438   0.574  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.335   0.944  -0.473  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.847   0.640   1.455  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.124  -0.805   1.426  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.907  -1.650   1.253  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.143  -1.418   0.021  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.721  -1.604  -1.334  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.853  -1.018   0.048  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.099  -0.789  -1.182  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.904  -1.642  -1.414  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.839  -1.570  -0.408  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.060  -1.969   0.995  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.365  -1.155  -0.775  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.541  -1.026   0.116  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.958   0.432   0.067  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.164   0.693   0.946  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.866   0.346   2.394  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.451   2.173   0.886  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.111   2.482  -0.436  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.385   1.708  -0.491  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.546   2.237  -0.998  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.719   1.497  -1.038  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.905   2.041  -1.558  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.767   0.203  -0.570  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.024  -0.609  -0.606  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.594  -0.324  -0.060  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.596  -1.705   0.453  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.423   0.403  -0.016  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.234  -0.099   0.489  0.00  0.00           O+0
HETATM   31  H   UNK     0      -8.007   3.465   0.214  0.00  0.00           H+0
HETATM   32  H   UNK     0      -7.021   3.196   1.664  0.00  0.00           H+0
HETATM   33  H   UNK     0      -6.264   3.163  -0.025  0.00  0.00           H+0
HETATM   34  H   UNK     0      -7.840   0.362  -1.266  0.00  0.00           H+0
HETATM   35  H   UNK     0      -8.852   1.791  -0.994  0.00  0.00           H+0
HETATM   36  H   UNK     0      -9.191   0.352  -0.035  0.00  0.00           H+0
HETATM   37  H   UNK     0      -6.186   1.052   2.196  0.00  0.00           H+0
HETATM   38  H   UNK     0      -7.945  -1.062   0.727  0.00  0.00           H+0
HETATM   39  H   UNK     0      -7.536  -1.064   2.446  0.00  0.00           H+0
HETATM   40  H   UNK     0      -6.247  -2.724   1.335  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.257  -1.495   2.139  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.744  -0.644  -1.846  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.116  -2.388  -1.845  0.00  0.00           H+0
HETATM   44  H   UNK     0      -6.755  -2.000  -1.302  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.392  -0.862   1.014  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.743  -0.905  -2.106  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.770   0.294  -1.260  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.221  -2.720  -1.568  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.527  -1.365  -2.446  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.128  -1.148   1.714  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.186  -2.614   1.323  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.923  -2.698   1.077  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.550  -0.870  -1.831  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.358  -1.648  -0.342  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.381  -1.388   1.126  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.082   1.029   0.394  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.233   0.622  -0.990  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.691   0.797   2.999  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.870  -0.730   2.591  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.940   0.859   2.688  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.457   2.687   0.946  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.125   2.507   1.697  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.504   2.165  -1.298  0.00  0.00           H+0
HETATM   64  H   UNK     0       4.298   3.571  -0.560  0.00  0.00           H+0
HETATM   65  H   UNK     0       6.537   3.263  -1.377  0.00  0.00           H+0
HETATM   66  H   UNK     0       8.890   2.992  -1.907  0.00  0.00           H+0
HETATM   67  H   UNK     0       9.910   0.054  -0.536  0.00  0.00           H+0
HETATM   68  H   UNK     0       9.032  -1.105  -1.599  0.00  0.00           H+0
HETATM   69  H   UNK     0       9.027  -1.365   0.212  0.00  0.00           H+0
HETATM   70  H   UNK     0       7.245  -2.373  -0.137  0.00  0.00           H+0
HETATM   71  H   UNK     0       6.867  -1.715   1.547  0.00  0.00           H+0
HETATM   72  H   UNK     0       5.564  -2.107   0.406  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   34   35   36                                             
CONECT    4    2    5   37                                                  
CONECT    5    4    6   38   39                                             
CONECT    6    5    7   40   41                                             
CONECT    7    6    8    9                                                  
CONECT    8    7   42   43   44                                             
CONECT    9    7   10   45                                                  
CONECT   10    9   11   46   47                                             
CONECT   11   10   12   48   49                                             
CONECT   12   11   13   14                                                  
CONECT   13   12   50   51   52                                             
CONECT   14   12   15   53                                                  
CONECT   15   14   16   54   55                                             
CONECT   16   15   17   56   57                                             
CONECT   17   16   18   19   30                                             
CONECT   18   17   58   59   60                                             
CONECT   19   17   20   61   62                                             
CONECT   20   19   21   63   64                                             
CONECT   21   20   22   29                                                  
CONECT   22   21   23   65                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   66                                                       
CONECT   25   23   26   27                                                  
CONECT   26   25   67   68   69                                             
CONECT   27   25   28   29                                                  
CONECT   28   27   70   71   72                                             
CONECT   29   27   30   21                                                  
CONECT   30   29   17                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41    6                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    8                                                            
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   10                                                            
CONECT   48   11                                                            
CONECT   49   11                                                            
CONECT   50   13                                                            
CONECT   51   13                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   15                                                            
CONECT   55   15                                                            
CONECT   56   16                                                            
CONECT   57   16                                                            
CONECT   58   18                                                            
CONECT   59   18                                                            
CONECT   60   18                                                            
CONECT   61   19                                                            
CONECT   62   19                                                            
CONECT   63   20                                                            
CONECT   64   20                                                            
CONECT   65   22                                                            
CONECT   66   24                                                            
CONECT   67   26                                                            
CONECT   68   26                                                            
CONECT   69   26                                                            
CONECT   70   28                                                            
CONECT   71   28                                                            
CONECT   72   28                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  146    0
END

RDKit          3D

72 73  0  0  0  0  0  0  0  0999 V2000
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   -7.4083    1.4385    0.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8474    0.6399    1.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1428   -1.4176    0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7212   -1.6044   -1.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0985   -0.7888   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9036   -1.6415   -1.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8385   -1.5698   -0.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596   -1.9692    0.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3648   -1.1549   -0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2345   -0.0994    0.4890 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0205    3.1958    1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.1907    0.3523   -0.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1857    1.0516    2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9448   -1.0622    0.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5363   -1.0641    2.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2465   -2.7239    1.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2569   -1.4947    2.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7437   -0.6442   -1.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1156   -2.3883   -1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7549   -2.0004   -1.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7426   -0.9046   -2.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2212   -2.7196   -1.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5267   -1.3651   -2.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5496   -0.8698   -1.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2329    0.6217   -0.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6912    0.7966    2.9985 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4573    2.6872    0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    2.5069    1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5044    2.1652   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2985    3.5708   -0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375    3.2628   -1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8895    2.9917   -1.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9100    0.0536   -0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0319   -1.1050   -1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0268   -1.3647    0.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2449   -2.3730   -0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -1.7149    1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5637   -2.1074    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 17 16  1  6
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 30 17  1  0
 29 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  8 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 13 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 18 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  0
 20 64  1  0
 22 65  1  0
 24 66  1  0
 26 67  1  0
 26 68  1  0
 26 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
M  END

View in JSmol View NMR Assignments View DFT Assignments 3D Conformers

Synonyms

Value	Source
(2R)-2,7,8-Trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol	ChEBI
g-Tocotrienol	Generator
Γ-tocotrienol	Generator
Tocotrienol, gamma	HMDB
(2R)-3,4-Dihydro-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-2H-1-benzopyran-6-ol	HMDB
(R)-gamma-Tocotrienol	HMDB
(R)-Γ-tocotrienol	HMDB
7,8-Dimethyltocotrienol	HMDB
D-gamma-Tocotrienol	HMDB
D-Γ-tocotrienol	HMDB
Plastochromanol 3	HMDB
gamma-Tocotrienol	HMDB

Chemical Formula

C₂₈H₄₂O₂

Average Mass

410.6319 Da

Monoisotopic Mass

410.31848 Da

IUPAC Name

(2R)-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

gamma-tocotrienol

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1

InChI Identifier

InChI=1S/C28H42O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h11,13,15,19,29H,8-10,12,14,16-18H2,1-7H3/b21-13+,22-15+/t28-/m1/s1

InChI Key

OTXNTMVVOOBZCV-WAZJVIJMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aesculus hippocastanum Hort.	KNApSAcK Database	22123792
Amaranthus hypochondriacus	LOTUS Database	35616633
Amaranthus hypochondriacus L.	KNApSAcK Database	22123792
Avena sativa L.	KNApSAcK Database	22123792
Bixa orellana L.	KNApSAcK Database	22123792
Calophyllum inophyllum L.	KNApSAcK Database	22123792
Cannabis sativa	CannabisDB	Not Available
Carum carvi L.	KNApSAcK Database	22123792
Cinnamosma macrocarpa	LOTUS Database	35616633
Cocos nucifera L.	KNApSAcK Database	22123792
Cystophora monilifera	NPAtlas	26093325
Delphinium ajacis L.	KNApSAcK Database	22123792
Elaeis guineensis Jacq.	KNApSAcK Database	22123792
Foeniculum vulgare	LOTUS Database	35616633
Foeniculum vulgare L.	KNApSAcK Database	22123792
Gevuina avellana Mol.	KNApSAcK Database	22123792
Hevea brasiliensis Mull.Arg.	KNApSAcK Database	22123792
Hippophae rhamnoides	LOTUS Database	35616633
Hordeum vulgare L.	KNApSAcK Database	22123792
Juglans regia	LOTUS Database	35616633
Litchi chinensis Sonn.	KNApSAcK Database	22123792
Nicotiana tabacum L.	KNApSAcK Database	22123792
Oryza sativa L.	KNApSAcK Database	22123792
Rosmarinus officinalis L.	KNApSAcK Database	22123792
Secale cereale L.	KNApSAcK Database	22123792
Triadica sebifera	LOTUS Database	35616633
Vaccinium macrocarpon Aiton	KNApSAcK Database	22123792
Vitis vinifera L.	KNApSAcK Database	22123792
Zea mays L.	KNApSAcK Database	22123792

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

Not Available

Substituents

Not Available

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	530.80 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1.9e-06 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	10.300 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	7.71	ALOGPS
logP	8.78	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	10.47	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	132.88 m³·mol⁻¹	ChemAxon
Polarizability	51.96 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA012960

HMDB ID

HMDB0012958

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Gamma-Tocotrienol

METLIN ID

Not Available

PubChem Compound

5282349

PDB ID

Not Available

ChEBI ID

33277

Good Scents ID

rw1679281

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Brkljaca R, Urban S: HPLC-NMR and HPLC-MS investigation of antimicrobial constituents in Cystophora monilifera and Cystophora subfarcinata. Phytochemistry. 2015 Sep;117:200-208. doi: 10.1016/j.phytochem.2015.06.014. Epub 2015 Jun 18. [PubMed:26093325 ]

Showing NP-Card for 2R-γ-tocotrienol (NP0014303)

MOL for NP0014303 (2R-γ-tocotrienol)

3D MOL for NP0014303 (2R-γ-tocotrienol)

3D SDF for NP0014303 (2R-γ-tocotrienol)

3D-SDF for NP0014303 (2R-γ-tocotrienol)

PDB for NP0014303 (2R-γ-tocotrienol)

3D PDB for NP0014303 (2R-γ-tocotrienol)

SMILES for NP0014303 (2R-γ-tocotrienol)

INCHI for NP0014303 (2R-γ-tocotrienol)

Structure for NP0014303 (2R-γ-tocotrienol)

3D Structure for NP0014303 (2R-γ-tocotrienol)