NP-MRD: Showing NP-Card for alpha-tocotrienol (NP0037440)

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Record Information

Version

1.0

Created at

2021-06-20 20:21:51 UTC

Updated at

2021-06-30 00:09:39 UTC

NP-MRD ID

NP0037440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-tocotrienol

Provided By

JEOL Database JEOL Logo

Description

Alpha-Tocotrienol, also known as zeta1-tocopherol or α-tocotrienol, 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, alpha-tocotrienol is considered to be a quinone. Alpha-Tocotrienol exists in all living organisms, ranging from bacteria to humans. Alpha-Tocotrienol has been detected, but not quantified in, several different foods, such as naranjillas (Solanum quitoense), purple mangosteens (Garcinia mangostana), saskatoon berries (Amelanchier alnifolia), mexican groundcherries (Physalis philadelphica var. Immaculata), and pepper (c. Frutescens). This could make alpha-tocotrienol a potential biomarker for the consumption of these foods. Alpha-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. It was first documented in 2006 (PMID: 16771695). Based on a literature review a significant number of articles have been published on alpha-Tocotrienol (PMID: 16923160) (PMID: 20823491) (PMID: 22013739) (PMID: 22252050).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306202122213D          

 75 76  0  0  0  0            999 V2000
    0.8142    2.9562    2.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1281    3.1951    0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2746    4.5945    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5460    2.1994    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2614    2.2382   -1.1863 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0231    0.9816   -2.0469 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3618    0.7128   -2.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711   -0.6595   -3.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803    1.5956   -2.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956    1.4293   -3.0734 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8147    1.3316   -1.9254 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6952    0.0543   -1.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3644   -1.1549   -1.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0026    0.0579    0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203   -1.1033    0.9557 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4842   -1.8791    0.4803 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8898   -2.8522    1.5316 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9618   -3.8428    2.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2908   -3.6614    0.9797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4455   -2.7507    0.5986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6728   -1.6701    1.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8328   -0.8683    1.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8761   -1.0773    0.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0285    0.1050    2.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1651    0.8673    2.4792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1092    0.3059    3.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3838    1.3171    4.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9078   -0.4377    3.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1414   -0.2210    4.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7073   -1.4227    2.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711   -2.1253    2.6986 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.9120    2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8773    3.2076    1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627    3.5766    2.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3227    4.7878   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0449    5.3172    0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3224    4.7950   -0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5937    1.2330    0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3363    2.2952   -0.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0152    3.1284   -1.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3157    0.1079   -1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7256    1.0230   -2.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2301   -0.7494   -4.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4657   -0.8972   -3.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2223   -1.4268   -2.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143    2.5629   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9055    0.5799   -3.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0367    2.3157   -3.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8293    1.3945   -2.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7120    2.2086   -1.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9607   -1.3673   -2.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2307   -2.0571   -1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4411   -0.9797   -1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5341    0.9903    0.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5609   -0.7049    1.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5929   -1.7615    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7248   -1.1445    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7394   -2.4396   -0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7655   -3.3334    2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357   -4.5602    2.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3979   -4.4029    1.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6484   -4.3538    1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0071   -4.2698    0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3468   -3.3650    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -2.2836   -0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4901   -0.1856    0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4139   -1.2955   -0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5333   -1.9066    0.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9746    1.7393    2.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9525    1.0109    5.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574    1.4234    4.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9731    2.2906    4.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    0.8433    4.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1304   -0.7682    5.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1347   -0.5503    4.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 29  1  0  0  0  0
 21 22  2  0  0  0  0
 17 16  1  6  0  0  0
 22 24  1  0  0  0  0
 16 15  1  0  0  0  0
 21 20  1  0  0  0  0
 15 14  1  0  0  0  0
 30 31  1  0  0  0  0
 14 12  2  0  0  0  0
 31 17  1  0  0  0  0
 12 11  1  0  0  0  0
 17 19  1  0  0  0  0
 11 10  1  0  0  0  0
 19 20  1  0  0  0  0
 10  9  1  0  0  0  0
 21 30  1  0  0  0  0
  9  7  2  0  0  0  0
 17 18  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
 22 23  1  0  0  0  0
  5  4  1  0  0  0  0
 26 28  1  0  0  0  0
  4  2  2  3  0  0  0
 24 25  1  0  0  0  0
  2  1  1  0  0  0  0
 28 30  2  0  0  0  0
  2  3  1  0  0  0  0
 26 27  1  0  0  0  0
 12 13  1  0  0  0  0
 24 26  2  0  0  0  0
  7  8  1  0  0  0  0
 19 62  1  0  0  0  0
 19 63  1  0  0  0  0
 20 64  1  0  0  0  0
 20 65  1  0  0  0  0
 18 59  1  0  0  0  0
 18 60  1  0  0  0  0
 18 61  1  0  0  0  0
 23 66  1  0  0  0  0
 23 67  1  0  0  0  0
 23 68  1  0  0  0  0
 25 69  1  0  0  0  0
 27 70  1  0  0  0  0
 27 71  1  0  0  0  0
 27 72  1  0  0  0  0
 29 73  1  0  0  0  0
 29 74  1  0  0  0  0
 29 75  1  0  0  0  0
 16 57  1  0  0  0  0
 16 58  1  0  0  0  0
 15 55  1  0  0  0  0
 15 56  1  0  0  0  0
 14 54  1  0  0  0  0
 11 49  1  0  0  0  0
 11 50  1  0  0  0  0
 10 47  1  0  0  0  0
 10 48  1  0  0  0  0
  9 46  1  0  0  0  0
  6 41  1  0  0  0  0
  6 42  1  0  0  0  0
  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  4 38  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  3 35  1  0  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
 13 51  1  0  0  0  0
 13 52  1  0  0  0  0
 13 53  1  0  0  0  0
  8 43  1  0  0  0  0
  8 44  1  0  0  0  0
  8 45  1  0  0  0  0
M  END


  Mrv1652306202122213D          

 75 76  0  0  0  0            999 V2000
    0.8142    2.9562    2.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1281    3.1951    0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2746    4.5945    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5460    2.1994    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2614    2.2382   -1.1863 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0231    0.9816   -2.0469 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3618    0.7128   -2.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711   -0.6595   -3.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803    1.5956   -2.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956    1.4293   -3.0734 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8147    1.3316   -1.9254 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6952    0.0543   -1.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3644   -1.1549   -1.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0026    0.0579    0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203   -1.1033    0.9557 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4842   -1.8791    0.4803 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8898   -2.8522    1.5316 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9618   -3.8428    2.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2908   -3.6614    0.9797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4455   -2.7507    0.5986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6728   -1.6701    1.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8328   -0.8683    1.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8761   -1.0773    0.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0285    0.1050    2.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1651    0.8673    2.4792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1092    0.3059    3.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3838    1.3171    4.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9078   -0.4377    3.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1414   -0.2210    4.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7073   -1.4227    2.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711   -2.1253    2.6986 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.9120    2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8773    3.2076    1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627    3.5766    2.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3227    4.7878   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0449    5.3172    0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3224    4.7950   -0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5937    1.2330    0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3363    2.2952   -0.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0152    3.1284   -1.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3157    0.1079   -1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7256    1.0230   -2.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2301   -0.7494   -4.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4657   -0.8972   -3.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2223   -1.4268   -2.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143    2.5629   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9055    0.5799   -3.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0367    2.3157   -3.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8293    1.3945   -2.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7120    2.2086   -1.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9607   -1.3673   -2.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2307   -2.0571   -1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4411   -0.9797   -1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5341    0.9903    0.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5609   -0.7049    1.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5929   -1.7615    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7248   -1.1445    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7394   -2.4396   -0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7655   -3.3334    2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357   -4.5602    2.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3979   -4.4029    1.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6484   -4.3538    1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0071   -4.2698    0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3468   -3.3650    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -2.2836   -0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4901   -0.1856    0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4139   -1.2955   -0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5333   -1.9066    0.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9746    1.7393    2.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9525    1.0109    5.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574    1.4234    4.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9731    2.2906    4.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    0.8433    4.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1304   -0.7682    5.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1347   -0.5503    4.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 29  1  0  0  0  0
 21 22  2  0  0  0  0
 17 16  1  6  0  0  0
 22 24  1  0  0  0  0
 16 15  1  0  0  0  0
 21 20  1  0  0  0  0
 15 14  1  0  0  0  0
 30 31  1  0  0  0  0
 14 12  2  0  0  0  0
 31 17  1  0  0  0  0
 12 11  1  0  0  0  0
 17 19  1  0  0  0  0
 11 10  1  0  0  0  0
 19 20  1  0  0  0  0
 10  9  1  0  0  0  0
 21 30  1  0  0  0  0
  9  7  2  0  0  0  0
 17 18  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
 22 23  1  0  0  0  0
  5  4  1  0  0  0  0
 26 28  1  0  0  0  0
  4  2  2  3  0  0  0
 24 25  1  0  0  0  0
  2  1  1  0  0  0  0
 28 30  2  0  0  0  0
  2  3  1  0  0  0  0
 26 27  1  0  0  0  0
 12 13  1  0  0  0  0
 24 26  2  0  0  0  0
  7  8  1  0  0  0  0
 19 62  1  0  0  0  0
 19 63  1  0  0  0  0
 20 64  1  0  0  0  0
 20 65  1  0  0  0  0
 18 59  1  0  0  0  0
 18 60  1  0  0  0  0
 18 61  1  0  0  0  0
 23 66  1  0  0  0  0
 23 67  1  0  0  0  0
 23 68  1  0  0  0  0
 25 69  1  0  0  0  0
 27 70  1  0  0  0  0
 27 71  1  0  0  0  0
 27 72  1  0  0  0  0
 29 73  1  0  0  0  0
 29 74  1  0  0  0  0
 29 75  1  0  0  0  0
 16 57  1  0  0  0  0
 16 58  1  0  0  0  0
 15 55  1  0  0  0  0
 15 56  1  0  0  0  0
 14 54  1  0  0  0  0
 11 49  1  0  0  0  0
 11 50  1  0  0  0  0
 10 47  1  0  0  0  0
 10 48  1  0  0  0  0
  9 46  1  0  0  0  0
  6 41  1  0  0  0  0
  6 42  1  0  0  0  0
  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  4 38  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  3 35  1  0  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
 13 51  1  0  0  0  0
 13 52  1  0  0  0  0
 13 53  1  0  0  0  0
  8 43  1  0  0  0  0
  8 44  1  0  0  0  0
  8 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037440

> <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=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C29H44O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h12,14,16,30H,9-11,13,15,17-19H2,1-8H3/b21-14+,22-16+/t29-/m1/s1

> <INCHI_KEY>
RZFHLOLGZPDCHJ-XZXLULOTSA-N

> <FORMULA>
C29H44O2

> <MOLECULAR_WEIGHT>
424.6585

> <EXACT_MASS>
424.334130652

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.00407076453943

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
7.70

> <JCHEM_LOGP>
9.290978816

> <ALOGPS_LOGS>
-6.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.802140056151512

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852669250142677

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
137.92409999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.72e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α tocotrienol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.814   2.956   2.068  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.128   3.195   0.749  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.275   4.595   0.221  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.546   2.199   0.140  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.261   2.238  -1.186  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.023   0.982  -2.047  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.362   0.713  -2.629  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.471  -0.660  -3.246  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.380   1.596  -2.577  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.796   1.429  -3.073  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.815   1.332  -1.925  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.695   0.054  -1.111  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.364  -1.155  -1.702  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.003   0.058   0.044  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.720  -1.103   0.956  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.484  -1.879   0.480  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.890  -2.852   1.532  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.962  -3.843   2.015  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.291  -3.661   0.980  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.446  -2.751   0.599  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.673  -1.670   1.624  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.833  -0.868   1.573  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.876  -1.077   0.504  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.029   0.105   2.567  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.165   0.867   2.479  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.109   0.306   3.612  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.384   1.317   4.695  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.908  -0.438   3.606  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.141  -0.221   4.670  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.707  -1.423   2.616  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.471  -2.125   2.699  0.00  0.00           O+0
HETATM   32  H   UNK     0       0.748   1.912   2.389  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.877   3.208   1.994  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.363   3.577   2.849  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.323   4.788  -0.672  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.045   5.317   0.980  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.322   4.795  -0.026  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.594   1.233   0.643  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.336   2.295  -0.972  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.015   3.128  -1.772  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.316   0.108  -1.449  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.726   1.023  -2.890  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.230  -0.749  -4.082  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.466  -0.897  -3.626  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.222  -1.427  -2.505  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.214   2.563  -2.107  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.906   0.580  -3.752  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.037   2.316  -3.674  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.829   1.395  -2.339  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.712   2.209  -1.272  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.961  -1.367  -2.697  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.231  -2.057  -1.100  0.00  0.00           H+0
HETATM   53  H   UNK     0       5.441  -0.980  -1.797  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.534   0.990   0.360  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.561  -0.705   1.965  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.593  -1.762   1.021  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.725  -1.145   0.187  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.739  -2.440  -0.429  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.765  -3.333   2.558  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.536  -4.560   2.727  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.398  -4.403   1.181  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.648  -4.354   1.755  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.007  -4.270   0.118  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.347  -3.365   0.488  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.241  -2.284  -0.372  0.00  0.00           H+0
HETATM   66  H   UNK     0      -4.490  -0.186   0.345  0.00  0.00           H+0
HETATM   67  H   UNK     0      -3.414  -1.296  -0.463  0.00  0.00           H+0
HETATM   68  H   UNK     0      -4.533  -1.907   0.784  0.00  0.00           H+0
HETATM   69  H   UNK     0      -3.975   1.739   2.860  0.00  0.00           H+0
HETATM   70  H   UNK     0      -1.952   1.011   5.653  0.00  0.00           H+0
HETATM   71  H   UNK     0      -3.457   1.423   4.883  0.00  0.00           H+0
HETATM   72  H   UNK     0      -1.973   2.291   4.411  0.00  0.00           H+0
HETATM   73  H   UNK     0       0.247   0.843   4.905  0.00  0.00           H+0
HETATM   74  H   UNK     0      -0.130  -0.768   5.578  0.00  0.00           H+0
HETATM   75  H   UNK     0       1.135  -0.550   4.350  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   35   36   37                                             
CONECT    4    5    2   38                                                  
CONECT    5    6    4   39   40                                             
CONECT    6    7    5   41   42                                             
CONECT    7    9    6    8                                                  
CONECT    8    7   43   44   45                                             
CONECT    9   10    7   46                                                  
CONECT   10   11    9   47   48                                             
CONECT   11   12   10   49   50                                             
CONECT   12   14   11   13                                                  
CONECT   13   12   51   52   53                                             
CONECT   14   15   12   54                                                  
CONECT   15   16   14   55   56                                             
CONECT   16   17   15   57   58                                             
CONECT   17   16   31   19   18                                             
CONECT   18   17   59   60   61                                             
CONECT   19   17   20   62   63                                             
CONECT   20   21   19   64   65                                             
CONECT   21   22   20   30                                                  
CONECT   22   21   24   23                                                  
CONECT   23   22   66   67   68                                             
CONECT   24   22   25   26                                                  
CONECT   25   24   69                                                       
CONECT   26   28   27   24                                                  
CONECT   27   26   70   71   72                                             
CONECT   28   29   26   30                                                  
CONECT   29   28   73   74   75                                             
CONECT   30   31   21   28                                                  
CONECT   31   30   17                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    6                                                            
CONECT   43    8                                                            
CONECT   44    8                                                            
CONECT   45    8                                                            
CONECT   46    9                                                            
CONECT   47   10                                                            
CONECT   48   10                                                            
CONECT   49   11                                                            
CONECT   50   11                                                            
CONECT   51   13                                                            
CONECT   52   13                                                            
CONECT   53   13                                                            
CONECT   54   14                                                            
CONECT   55   15                                                            
CONECT   56   15                                                            
CONECT   57   16                                                            
CONECT   58   16                                                            
CONECT   59   18                                                            
CONECT   60   18                                                            
CONECT   61   18                                                            
CONECT   62   19                                                            
CONECT   63   19                                                            
CONECT   64   20                                                            
CONECT   65   20                                                            
CONECT   66   23                                                            
CONECT   67   23                                                            
CONECT   68   23                                                            
CONECT   69   25                                                            
CONECT   70   27                                                            
CONECT   71   27                                                            
CONECT   72   27                                                            
CONECT   73   29                                                            
CONECT   74   29                                                            
CONECT   75   29                                                            
MASTER        0    0    0    0    0    0    0    0   75    0  152    0
END

Mrv1652306202122213D

75 76  0  0  0  0            999 V2000
    0.8142    2.9562    2.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1281    3.1951    0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2746    4.5945    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5460    2.1994    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2614    2.2382   -1.1863 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0231    0.9816   -2.0469 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3618    0.7128   -2.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711   -0.6595   -3.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803    1.5956   -2.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956    1.4293   -3.0734 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8147    1.3316   -1.9254 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6952    0.0543   -1.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3644   -1.1549   -1.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0026    0.0579    0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203   -1.1033    0.9557 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4842   -1.8791    0.4803 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8898   -2.8522    1.5316 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9618   -3.8428    2.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2908   -3.6614    0.9797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4455   -2.7507    0.5986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6728   -1.6701    1.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8328   -0.8683    1.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8761   -1.0773    0.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0285    0.1050    2.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1651    0.8673    2.4792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1092    0.3059    3.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3838    1.3171    4.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9078   -0.4377    3.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1414   -0.2210    4.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7073   -1.4227    2.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711   -2.1253    2.6986 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.9120    2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8773    3.2076    1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627    3.5766    2.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3227    4.7878   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0449    5.3172    0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3224    4.7950   -0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5937    1.2330    0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3363    2.2952   -0.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0152    3.1284   -1.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3157    0.1079   -1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7256    1.0230   -2.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2301   -0.7494   -4.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4657   -0.8972   -3.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2223   -1.4268   -2.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143    2.5629   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9055    0.5799   -3.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0367    2.3157   -3.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8293    1.3945   -2.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7120    2.2086   -1.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9607   -1.3673   -2.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2307   -2.0571   -1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4411   -0.9797   -1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5341    0.9903    0.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5609   -0.7049    1.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5929   -1.7615    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7248   -1.1445    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7394   -2.4396   -0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7655   -3.3334    2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357   -4.5602    2.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3979   -4.4029    1.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6484   -4.3538    1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0071   -4.2698    0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3468   -3.3650    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -2.2836   -0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4901   -0.1856    0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4139   -1.2955   -0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5333   -1.9066    0.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9746    1.7393    2.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9525    1.0109    5.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574    1.4234    4.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9731    2.2906    4.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    0.8433    4.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1304   -0.7682    5.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1347   -0.5503    4.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 29  1  0  0  0  0
 21 22  2  0  0  0  0
 17 16  1  6  0  0  0
 22 24  1  0  0  0  0
 16 15  1  0  0  0  0
 21 20  1  0  0  0  0
 15 14  1  0  0  0  0
 30 31  1  0  0  0  0
 14 12  2  0  0  0  0
 31 17  1  0  0  0  0
 12 11  1  0  0  0  0
 17 19  1  0  0  0  0
 11 10  1  0  0  0  0
 19 20  1  0  0  0  0
 10  9  1  0  0  0  0
 21 30  1  0  0  0  0
  9  7  2  0  0  0  0
 17 18  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
 22 23  1  0  0  0  0
  5  4  1  0  0  0  0
 26 28  1  0  0  0  0
  4  2  2  3  0  0  0
 24 25  1  0  0  0  0
  2  1  1  0  0  0  0
 28 30  2  0  0  0  0
  2  3  1  0  0  0  0
 26 27  1  0  0  0  0
 12 13  1  0  0  0  0
 24 26  2  0  0  0  0
  7  8  1  0  0  0  0
 19 62  1  0  0  0  0
 19 63  1  0  0  0  0
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 20 65  1  0  0  0  0
 18 59  1  0  0  0  0
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  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  3 35  1  0  0  0  0
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  3 37  1  0  0  0  0
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 13 52  1  0  0  0  0
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  8 43  1  0  0  0  0
  8 44  1  0  0  0  0
  8 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037440

> <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=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C29H44O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h12,14,16,30H,9-11,13,15,17-19H2,1-8H3/b21-14+,22-16+/t29-/m1/s1

> <INCHI_KEY>
RZFHLOLGZPDCHJ-XZXLULOTSA-N

> <FORMULA>
C29H44O2

> <MOLECULAR_WEIGHT>
424.6585

> <EXACT_MASS>
424.334130652

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.00407076453943

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
7.70

> <JCHEM_LOGP>
9.290978816

> <ALOGPS_LOGS>
-6.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.802140056151512

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852669250142677

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
137.92409999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.72e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α tocotrienol

> <JCHEM_VEBER_RULE>
1

$$$$

View in JSmol

Synonyms

Value	Source
(2R)-2,5,7,8-Tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol	ChEBI
zeta1-Tocopherol	ChEBI
Ζ1-tocopherol	Generator
a-Tocotrienol	Generator
Α-tocotrienol	Generator
(2R,3'E,7'E)-alpha-Tocotrienol	HMDB
(R)-alpha-Tocotrienol	HMDB
Tocotrienol, alpha	MeSH, HMDB
(2R,3'E,7'E)-α-Tocotrienol	HMDB
(2R,3’E,7’E)-α-Tocotrienol	HMDB
(R)-α-Tocotrienol	HMDB
5,7,8-Trimethyltocotrienol	HMDB
alpha-Tocotrienol	HMDB

Chemical Formula

C₂₉H₄₄O₂

Average Mass

424.6585 Da

Monoisotopic Mass

424.33413 Da

IUPAC Name

(2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

α tocotrienol

CAS Registry Number

Not Available

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=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C29H44O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h12,14,16,30H,9-11,13,15,17-19H2,1-8H3/b21-14+,22-16+/t29-/m1/s1

InChI Key

RZFHLOLGZPDCHJ-XZXLULOTSA-N

Spectra

Spectrum Type	Description	Depositor ID	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	2021-06-20	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Aesculus hippocastanum Hort.	KNApSAcK Database	22123792
Amaranthus hypochondriacus L.	KNApSAcK Database	22123792
Avena sativa L.	KNApSAcK Database	22123792
Bixa orellana L.	KNApSAcK Database	22123792
Calophyllum inophyllum L.	KNApSAcK Database	22123792
Carum carvi L.	KNApSAcK Database	22123792
Cocos nucifera L.	KNApSAcK Database	22123792
Coriandrum sativum L.	KNApSAcK Database	22123792
Delphinium ajacis L.	KNApSAcK Database	22123792
Elaeis guineensis Jacq.	KNApSAcK Database	22123792
Foeniculum vulgare L.	KNApSAcK Database	22123792
Gevuina avellana Mol.	KNApSAcK Database	22123792
Hevea brasiliensis Mull.Arg.	KNApSAcK Database	22123792
Hordeum vulgare L.	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
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

Substituents

Tocotrienol
Diterpenoid
1-benzopyran
Benzopyran
Chromane
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tocotrienol (CHEBI:33270 )
vitamin E (CHEBI:33270 )
vitamin E (C14153 )
Vitamin E (LMPR02020054 )

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	7.7	ALOGPS
logP	9.29	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	10.8	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	137.92 m³·mol⁻¹	ChemAxon
Polarizability	51 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

HMDB ID

HMDB0006327

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

Alpha-Tocotrienol

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

33270

Good Scents ID

Not Available

References

General References

Khosla P, Patel V, Whinter JM, Khanna S, Rakhkovskaya M, Roy S, Sen CK: Postprandial levels of the natural vitamin E tocotrienol in human circulation. Antioxid Redox Signal. 2006 May-Jun;8(5-6):1059-68. doi: 10.1089/ars.2006.8.1059. [PubMed:16771695 ]
Khanna S, Roy S, Parinandi NL, Maurer M, Sen CK: Characterization of the potent neuroprotective properties of the natural vitamin E alpha-tocotrienol. J Neurochem. 2006 Sep;98(5):1474-86. doi: 10.1111/j.1471-4159.2006.04000.x. [PubMed:16923160 ]
Sen CK, Rink C, Khanna S: Palm oil-derived natural vitamin E alpha-tocotrienol in brain health and disease. J Am Coll Nutr. 2010 Jun;29(3 Suppl):314S-323S. doi: 10.1080/07315724.2010.10719846. [PubMed:20823491 ]
Patel V, Rink C, Khanna S, Sen CK: Tocotrienols: the lesser known form of natural vitamin E. Indian J Exp Biol. 2011 Oct;49(10):732-8. [PubMed:22013739 ]
Fairus S, Nor RM, Cheng HM, Sundram K: Alpha-tocotrienol is the most abundant tocotrienol isomer circulated in plasma and lipoproteins after postprandial tocotrienol-rich vitamin E supplementation. Nutr J. 2012 Jan 17;11:5. doi: 10.1186/1475-2891-11-5. [PubMed:22252050 ]
Ohnmacht, S., et al. (2008). Ohnmacht, S., et al, Magn. Reson. Chem. 46, 287 (2008). Mag. Reson. Chem..

Showing NP-Card for alpha-tocotrienol (NP0037440)

MOL for NP0037440 (alpha-tocotrienol)

SDF for NP0037440 (alpha-tocotrienol)

3D-SDF for NP0037440 (alpha-tocotrienol)

PDB for NP0037440 (alpha-tocotrienol)

SMILES for NP0037440 (alpha-tocotrienol)

INCHI for NP0037440 (alpha-tocotrienol)

Structure for NP0037440 (alpha-tocotrienol)

3D Structure for NP0037440 (alpha-tocotrienol)