NP-MRD: Showing NP-Card for delta-Tocopherol (NP0002786)

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Record Information

Version

2.0

Created at

2020-11-23 19:40:25 UTC

Updated at

2021-08-19 23:59:23 UTC

NP-MRD ID

NP0002786

Secondary Accession Numbers

None

Natural Product Identification

Common Name

delta-Tocopherol

Provided By

BMRB

Description

Delta-Tocopherol, also known as RRR-δ-tocopherol or 8-methyltocol, belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. Thus, delta-tocopherol is considered to be a quinone. Delta-Tocopherol exists in all living organisms, ranging from bacteria to humans. Delta-Tocopherol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. delta-Tocopherol is found in Calendula officinalis, Campanula medium, Carum carvi L. , Caryodendron orinocense, Cocos nucifera L. , Crataegus monogyna, Guarea kunthiana, Schefflera taiwaniana, Hippophae rhamnoides, Hypericum ericoides, Juglans regia L. , Linum usitatissimum, Muntingia calabura, Olea europaea, Origanum vulgare, Psophocarpus tetragonolobus, Radula marginata, Radula perrottetii, Rubus idaeus, Salvia rosmarinus, Secale cereale L. , Sesamum indicum, Jungermannia infusca, Spinacia oleracea, Potamogeton pectinatus, Torreya nucifera and Vaccinium macrocarpon Aiton . delta-Tocopherol was first documented in 1999 (PMID: 10385606). Based on a literature review very few articles have been published on delta-Tocopherol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

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M  END

NP0002786
     RDKit          3D

 75 76  0  0  0  0  0  0  0  0999 V2000
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 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
M  END


     RDKit          2D

 75 76  0  0  0  0  0  0  0  0999 V2000
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  -10.2903    2.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 27 69  1  6
 27 70  1  0
 27 71  1  0
 28 72  1  1
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 29 74  1  6
 29 75  1  0
M  END
> <DATABASE_ID>
NP0002786

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h18-22,28H,7-17H2,1-6H3/t21-,22-,27-/m1/s1

> <INCHI_KEY>
GZIFEOYASATJEH-VHFRWLAGSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.6529

> <EXACT_MASS>
402.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.31471863589409

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
8.76

> <JCHEM_LOGP>
9.480874481333334

> <ALOGPS_LOGS>
-7.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.141712947649953

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852217396079623

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
125.29169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.09e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
delta tocopherol

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002786
     RDKit          3D

 75 76  0  0  0  0  0  0  0  0999 V2000
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  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 10 28  1  0
 28 29  1  0
  8  2  1  0
 29  7  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  5 34  1  0
  6 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  6
 16 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  6
 21 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8655.1068666.762   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8652.4428662.125   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8660.4268665.219   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8660.4268663.679   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8661.7588664.445   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8663.0918665.219   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.4248664.445   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.7568665.219   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.4248662.907   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.0888664.445   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.4248665.219   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8669.7568664.445   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8671.0878665.219   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8669.7568662.907   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8672.4238664.445   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8673.7558665.219   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8675.0918664.445   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8676.4238665.219   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8675.0918662.907   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8655.1058665.211   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8653.7728664.441   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8653.7728662.901   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8655.1058662.131   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8657.7658665.211   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0    8656.4328664.441   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8656.4328662.901   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8657.7658662.131   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8659.0998662.901   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8659.0998664.441   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2   22                                                            
CONECT    3    5   29                                                       
CONECT    4   29                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7   10                                                       
CONECT    9    7                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   21    1   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23    2                                                  
CONECT   23   22   26                                                       
CONECT   24   25   29                                                       
CONECT   25   26   24   20                                                  
CONECT   26   25   27   23                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24    3    4                                             
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

COMPND    NP0002786
HETATM    1  C1  UNL     1      -8.271  -0.945   0.862  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.399   0.126   1.377  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.909   0.999   2.309  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.119   2.010   2.809  1.00  0.00           C  
HETATM    5  O1  UNL     1      -7.594   2.915   3.753  1.00  0.00           O  
HETATM    6  C5  UNL     1      -5.805   2.102   2.333  1.00  0.00           C  
HETATM    7  C6  UNL     1      -5.308   1.216   1.395  1.00  0.00           C  
HETATM    8  C7  UNL     1      -6.106   0.210   0.903  1.00  0.00           C  
HETATM    9  O2  UNL     1      -5.540  -0.630  -0.026  1.00  0.00           O  
HETATM   10  C8  UNL     1      -4.643  -0.135  -1.047  1.00  0.00           C  
HETATM   11  C9  UNL     1      -5.657   0.408  -2.098  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.959  -1.238  -1.759  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.120  -2.180  -1.033  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.911  -1.779  -0.325  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.781  -1.182  -1.069  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.239  -2.141  -2.130  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.375  -1.065  -0.053  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.580  -0.449  -0.776  1.00  0.00           C  
HETATM   19  C17 UNL     1       2.674  -0.355   0.248  1.00  0.00           C  
HETATM   20  C18 UNL     1       3.954   0.240  -0.311  1.00  0.00           C  
HETATM   21  C19 UNL     1       4.478  -0.606  -1.450  1.00  0.00           C  
HETATM   22  C20 UNL     1       4.974   0.196   0.804  1.00  0.00           C  
HETATM   23  C21 UNL     1       6.310   0.757   0.402  1.00  0.00           C  
HETATM   24  C22 UNL     1       7.212   0.638   1.636  1.00  0.00           C  
HETATM   25  C23 UNL     1       8.593   1.177   1.345  1.00  0.00           C  
HETATM   26  C24 UNL     1       9.411   1.020   2.607  1.00  0.00           C  
HETATM   27  C25 UNL     1       9.254   0.476   0.202  1.00  0.00           C  
HETATM   28  C26 UNL     1      -3.859   1.025  -0.587  1.00  0.00           C  
HETATM   29  C27 UNL     1      -3.934   1.308   0.904  1.00  0.00           C  
HETATM   30  H1  UNL     1      -9.169  -1.107   1.500  1.00  0.00           H  
HETATM   31  H2  UNL     1      -8.678  -0.572  -0.120  1.00  0.00           H  
HETATM   32  H3  UNL     1      -7.741  -1.883   0.623  1.00  0.00           H  
HETATM   33  H4  UNL     1      -8.919   0.925   2.673  1.00  0.00           H  
HETATM   34  H5  UNL     1      -8.032   3.762   3.381  1.00  0.00           H  
HETATM   35  H6  UNL     1      -5.133   2.875   2.686  1.00  0.00           H  
HETATM   36  H7  UNL     1      -6.344   1.101  -1.600  1.00  0.00           H  
HETATM   37  H8  UNL     1      -5.038   0.867  -2.893  1.00  0.00           H  
HETATM   38  H9  UNL     1      -6.160  -0.498  -2.492  1.00  0.00           H  
HETATM   39  H10 UNL     1      -3.480  -0.783  -2.671  1.00  0.00           H  
HETATM   40  H11 UNL     1      -4.796  -1.846  -2.235  1.00  0.00           H  
HETATM   41  H12 UNL     1      -2.839  -3.017  -1.745  1.00  0.00           H  
HETATM   42  H13 UNL     1      -3.782  -2.726  -0.295  1.00  0.00           H  
HETATM   43  H14 UNL     1      -1.483  -2.723   0.150  1.00  0.00           H  
HETATM   44  H15 UNL     1      -2.086  -1.140   0.588  1.00  0.00           H  
HETATM   45  H16 UNL     1      -0.891  -0.174  -1.456  1.00  0.00           H  
HETATM   46  H17 UNL     1       0.581  -2.770  -1.754  1.00  0.00           H  
HETATM   47  H18 UNL     1      -1.009  -2.806  -2.546  1.00  0.00           H  
HETATM   48  H19 UNL     1       0.190  -1.507  -2.935  1.00  0.00           H  
HETATM   49  H20 UNL     1       0.032  -0.297   0.671  1.00  0.00           H  
HETATM   50  H21 UNL     1       0.624  -2.028   0.392  1.00  0.00           H  
HETATM   51  H22 UNL     1       1.827  -1.077  -1.642  1.00  0.00           H  
HETATM   52  H23 UNL     1       1.357   0.556  -1.133  1.00  0.00           H  
HETATM   53  H24 UNL     1       2.314   0.200   1.115  1.00  0.00           H  
HETATM   54  H25 UNL     1       2.902  -1.405   0.580  1.00  0.00           H  
HETATM   55  H26 UNL     1       3.758   1.265  -0.662  1.00  0.00           H  
HETATM   56  H27 UNL     1       3.748  -0.774  -2.251  1.00  0.00           H  
HETATM   57  H28 UNL     1       5.329  -0.060  -1.909  1.00  0.00           H  
HETATM   58  H29 UNL     1       4.857  -1.554  -1.013  1.00  0.00           H  
HETATM   59  H30 UNL     1       4.587   0.870   1.625  1.00  0.00           H  
HETATM   60  H31 UNL     1       5.062  -0.795   1.244  1.00  0.00           H  
HETATM   61  H32 UNL     1       6.222   1.864   0.226  1.00  0.00           H  
HETATM   62  H33 UNL     1       6.725   0.214  -0.452  1.00  0.00           H  
HETATM   63  H34 UNL     1       7.214  -0.425   1.948  1.00  0.00           H  
HETATM   64  H35 UNL     1       6.705   1.221   2.427  1.00  0.00           H  
HETATM   65  H36 UNL     1       8.475   2.265   1.161  1.00  0.00           H  
HETATM   66  H37 UNL     1       9.811  -0.026   2.687  1.00  0.00           H  
HETATM   67  H38 UNL     1      10.270   1.694   2.658  1.00  0.00           H  
HETATM   68  H39 UNL     1       8.762   1.135   3.519  1.00  0.00           H  
HETATM   69  H40 UNL     1      10.250   0.952   0.051  1.00  0.00           H  
HETATM   70  H41 UNL     1       9.474  -0.571   0.507  1.00  0.00           H  
HETATM   71  H42 UNL     1       8.718   0.551  -0.743  1.00  0.00           H  
HETATM   72  H43 UNL     1      -2.804   1.038  -0.929  1.00  0.00           H  
HETATM   73  H44 UNL     1      -4.271   1.984  -1.046  1.00  0.00           H  
HETATM   74  H45 UNL     1      -3.587   2.379   1.027  1.00  0.00           H  
HETATM   75  H46 UNL     1      -3.207   0.729   1.502  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    3    8
CONECT    3    4   33
CONECT    4    5    6    6
CONECT    5   34
CONECT    6    7   35
CONECT    7    8    8   29
CONECT    8    9
CONECT    9   10
CONECT   10   11   12   28
CONECT   11   36   37   38
CONECT   12   13   39   40
CONECT   13   14   41   42
CONECT   14   15   43   44
CONECT   15   16   17   45
CONECT   16   46   47   48
CONECT   17   18   49   50
CONECT   18   19   51   52
CONECT   19   20   53   54
CONECT   20   21   22   55
CONECT   21   56   57   58
CONECT   22   23   59   60
CONECT   23   24   61   62
CONECT   24   25   63   64
CONECT   25   26   27   65
CONECT   26   66   67   68
CONECT   27   69   70   71
CONECT   28   29   72   73
CONECT   29   74   75
END

NP0002786
     RDKit          3D

75 76  0  0  0  0  0  0  0  0999 V2000
   -8.2713   -0.9451    0.8625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3989    0.1255    1.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9088    0.9990    2.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1188    2.0104    2.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5945    2.9147    3.7530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8054    2.1019    2.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3083    1.2157    1.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1060    0.2098    0.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5400   -0.6301   -0.0264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6435   -0.1354   -1.0469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6574    0.4080   -2.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9593   -1.2381   -1.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1200   -2.1803   -1.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106   -1.7794   -0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7807   -1.1820   -1.0693 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2388   -2.1408   -2.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749   -1.0655   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798   -0.4491   -0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6742   -0.3554    0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9538    0.2403   -0.3109 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4779   -0.6061   -1.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9736    0.1964    0.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3098    0.7574    0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2115    0.6378    1.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5933    1.1771    1.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4110    1.0203    2.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2540    0.4765    0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8590    1.0249   -0.5873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9340    1.3085    0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1695   -1.1073    1.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6784   -0.5718   -0.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7410   -1.8831    0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9191    0.9250    2.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0321    3.7617    3.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1332    2.8752    2.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3435    1.1007   -1.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0384    0.8670   -2.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1601   -0.4979   -2.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4801   -0.7829   -2.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7960   -1.8460   -2.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8393   -3.0171   -1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7822   -2.7264   -0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4829   -2.7231    0.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0862   -1.1397    0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8913   -0.1739   -1.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5809   -2.7696   -1.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0086   -2.8065   -2.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1897   -1.5072   -2.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0317   -0.2970    0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6238   -2.0278    0.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8265   -1.0771   -1.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3572    0.5559   -1.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142    0.2001    1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9020   -1.4047    0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7580    1.2651   -0.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7476   -0.7741   -2.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3288   -0.0597   -1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8570   -1.5538   -1.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5874    0.8701    1.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0618   -0.7954    1.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2217    1.8641    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7255    0.2139   -0.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2143   -0.4252    1.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7052    1.2209    2.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4753    2.2654    1.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8112   -0.0262    2.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2695    1.6938    2.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7620    1.1350    3.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2498    0.9524    0.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4738   -0.5705    0.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7182    0.5505   -0.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8041    1.0376   -0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2708    1.9841   -1.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5874    2.3790    1.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2075    0.7292    1.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
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M  END

View in JSmol

Synonyms

Value	Source
(+)-delta-Tocopherol	ChEBI
(2R)-2,8-Dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol	ChEBI
(2R)-3,4-Dihydro-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol	ChEBI
(2R,4'r,8'r)-delta-Tocopherol	ChEBI
(R,R,R)-delta-Tocopherol	ChEBI
8-Methyltocol	ChEBI
e309	ChEBI
RRR-delta-Tocopherol	ChEBI
(+)-Δ-tocopherol	Generator
(2R,4'r,8'r)-Δ-tocopherol	Generator
(R,R,R)-Δ-tocopherol	Generator
RRR-Δ-tocopherol	Generator
Δ-tocopherol	Generator
Vitamine e	HMDB
(2R,4’R,8’R)-δ-Tocopherol	HMDB
d-delta-Tocopherol	HMDB
d-δ-Tocopherol	HMDB
delta-D-Tocopherol	HMDB
delta-Tocopherol	HMDB
delta-Vitamin E	HMDB
δ-D-Tocopherol	HMDB
δ-Vitamin E	HMDB

Chemical Formula

C₂₇H₄₆O₂

Average Mass

402.6529 Da

Monoisotopic Mass

402.34978 Da

IUPAC Name

(2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

delta tocopherol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h18-22,28H,7-17H2,1-6H3/t21-,22-,27-/m1/s1

InChI Key

GZIFEOYASATJEH-VHFRWLAGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aesculus hippocatanum Hort.	KNApSAcK Database	22123792
Amaranthus hypochondriacus L.	KNApSAcK Database	22123792
Arabidopsis thaliana	KNApSAcK Database	22123792
Avena sativa L.	KNApSAcK Database	22123792
Bixa orellana L.	KNApSAcK Database	22123792
Calendula officinalis	LOTUS Database	35616633
Calophyllum inophyllum L.	KNApSAcK Database	22123792
Campanula medium	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Carum carvi	Plant	KNApSAcK
Carum carvi L.	KNApSAcK Database	22123792
Caryodendron orinocense	LOTUS Database	35616633
Cocos nucifera	Plant	KNApSAcK
Cocos nucifera L.	KNApSAcK Database	22123792
Coriandrum sativum L.	KNApSAcK Database	22123792
Crataegus monogyna	LOTUS Database	35616633
Elaeis guineensis Jacq.	KNApSAcK Database	22123792
Foeniculum vulgare L.	KNApSAcK Database	22123792
Gevuina avellana Mol.	KNApSAcK Database	22123792
Glycine max	KNApSAcK Database	22123792
Guarea kunthiana	LOTUS Database	35616633
Heptapleurum taiwanianum	LOTUS Database	35616633
Hevea brasiliensis Mull.Arg.	KNApSAcK Database	22123792
Hippophae rhamnoides	LOTUS Database	35616633
Hordeum vulgare L.	KNApSAcK Database	22123792
Hypericum ericoides	LOTUS Database	35616633
Juglans regia	Plant	KNApSAcK
Juglans regia L.	KNApSAcK Database	22123792
Linum usitatissimum	LOTUS Database	35616633
Litchi chinensis Sonn.	KNApSAcK Database	22123792
Muntingia calabura	LOTUS Database	35616633
Nicotiana tabacum L.	KNApSAcK Database	22123792
Olea europaea	LOTUS Database	35616633
Origanum vulgare	LOTUS Database	35616633
Oryza sativa L.	KNApSAcK Database	22123792
Pellia epiphylla	KNApSAcK Database	22123792
Potamogeton pectinatus	KNApSAcK Database	22123792
Psophocarpus tetragonolobus	LOTUS Database	35616633
Radula marginata	LOTUS Database	35616633
Radula perrottetii	-	KNApSAcK
Rosmarinus officinalis L.	KNApSAcK Database	22123792
Rubus idaeus	LOTUS Database	35616633
Salvia rosmarinus	LOTUS Database	35616633
Secale cereale	Plant	KNApSAcK
Secale cereale L.	KNApSAcK Database	22123792
Sesamum indicum	LOTUS Database	35616633
Solenostoma infuscum	LOTUS Database	35616633
Spinacia oleracea	LOTUS Database	35616633
Stuckenia pectinata	Plant	KNApSAcK
Torreya nucifera	LOTUS Database	35616633
Vaccinium macrocarpon	Plant	KNApSAcK
Vaccinium macrocarpon Aiton	KNApSAcK Database	22123792
Zea mays L.	KNApSAcK Database	22123792

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Tocopherols

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	504.00 to 505.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	3.8e-06 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	10.493 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	8.76	ALOGPS
logP	9.48	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Acidic)	10.14	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	12	ChemAxon
Refractivity	125.29 m³·mol⁻¹	ChemAxon
Polarizability	51.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon