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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2009-07-25 00:10:35 UTC

Update Date

2022-03-07 02:51:27 UTC

HMDB ID

HMDB0012958

Secondary Accession Numbers

HMDB12958

Metabolite Identification

Common Name

gamma-Tocotrienol

Description

gamma-Tocotrienol, also known as 7,8-dimethyltocotrienol, 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 C6 atom of a benzopyran ring system. They differ from tocopherols that contain a saturated trimethyltridecyl chain. Thus, gamma-tocotrienol is considered to be a quinone lipid molecule. gamma-Tocotrienol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. gamma-Tocotrienol targets cancer cells by inhibiting Id1, a key cancer-promoting protein. gamma-Tocotrienol was shown to trigger cell apoptosis and well as anti-proliferation of cancer cells. This mechanism was also observed in separate prostate cancer and melanoma cell line studies.

Structure

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


  Mrv1652309042000362D          

 30 31  0  0  0  0            999 V2000
 9993.807010000.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3794 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3794 9997.5669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6567 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6567 9998.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3706 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0846 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7985 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5120 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7985 9997.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.2257 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9413 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6548 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.3704 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6548 9997.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.0839 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.7974 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5130 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.2265 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5130 9997.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8064 9999.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0920 9998.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0919 9997.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8063 9997.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.2315 9999.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5170 9998.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5170 9997.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.2315 9997.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9459 9997.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9459 9998.8077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
  1 21  1  0  0  0  0
 22  2  1  0  0  0  0
 23  3  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 26  1  0  0  0  0
 25 30  1  0  0  0  0
 30  4  1  0  0  0  0
 30  5  1  1  0  0  0
 26 21  2  0  0  0  0
 24 27  2  0  0  0  0
M  END

HMDB0012958
     RDKit          3D
gamma-Tocotrienol
 72 73  0  0  0  0  0  0  0  0999 V2000
    8.5477    1.5741   -1.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3241    0.5118   -1.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7856    0.6921   -1.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7140   -0.5435   -0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2487   -0.7337   -0.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -0.8419    0.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1570   -1.0298    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6970   -2.2166   -0.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2921   -0.1688    0.7503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473   -0.3742    0.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764   -0.4929    1.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7181   -0.7024    1.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0439   -0.8334    3.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0347   -0.7828    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500   -0.9967    0.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1577    0.1222   -0.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6292   -0.1328   -0.1021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1253   -0.2442    1.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0347   -1.3084   -0.9438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4468   -1.6825   -0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2992   -0.4544   -0.7231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6525   -0.6595   -0.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4878    0.4187   -1.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8795    0.2588   -1.1256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9430    1.6832   -1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8922    2.8285   -1.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5804    1.8909   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0399    3.2702   -0.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7364    0.8016   -0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3483    0.9896   -0.6398 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1850    2.4116   -2.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7593    1.9186   -1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0123    1.0937   -2.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0968    0.2535   -0.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2896    0.2689   -2.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0442    1.7776   -1.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2840   -1.3057   -0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167    0.1227   -1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9956   -1.6403   -1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8534    0.0568    1.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0768   -1.7002    1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5403   -2.8801   -0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9789   -2.8377    0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2098   -1.8361   -1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6301    0.6840    1.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6616   -1.2860   -0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671    0.5413    0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6064   -1.3832    2.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198    0.3901    2.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5680   -0.5408    3.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8715   -0.0877    2.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4219   -1.8638    3.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5723   -0.6899   -0.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5836   -1.9250    0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8695   -1.1881    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8309    0.2185   -1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9805    1.1082    0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1493    0.1503    1.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0519   -1.3062    1.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4426    0.3688    1.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1107   -0.9358   -2.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3546   -2.1555   -0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5196   -2.0627    0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8486   -2.4554   -1.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1091   -1.6445   -0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2407   -0.6798   -1.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3661    3.7810   -1.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4928    2.9649   -0.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5885    2.5544   -2.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9304    3.2386   -0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3377    3.8132   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3808    3.8447   -1.8483 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  1
 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


  Mrv1652309042000362D          

 30 31  0  0  0  0            999 V2000
 9993.807010000.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3794 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3794 9997.5669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6567 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6567 9998.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3706 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0846 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7985 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5120 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7985 9997.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.2257 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9413 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6548 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.3704 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6548 9997.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.0839 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.7974 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5130 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.2265 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5130 9997.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8064 9999.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0920 9998.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0919 9997.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8063 9997.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.2315 9999.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5170 9998.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5170 9997.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.2315 9997.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9459 9997.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9459 9998.8077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
  1 21  1  0  0  0  0
 22  2  1  0  0  0  0
 23  3  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 26  1  0  0  0  0
 25 30  1  0  0  0  0
 30  4  1  0  0  0  0
 30  5  1  1  0  0  0
 26 21  2  0  0  0  0
 24 27  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012958

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C28H42O2

> <MOLECULAR_WEIGHT>
410.6319

> <EXACT_MASS>
410.318480588

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.50835676066953

> <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

$$$$

HMDB0012958
     RDKit          3D
gamma-Tocotrienol
 72 73  0  0  0  0  0  0  0  0999 V2000
    8.5477    1.5741   -1.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3241    0.5118   -1.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7856    0.6921   -1.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7140   -0.5435   -0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2487   -0.7337   -0.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -0.8419    0.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1570   -1.0298    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6970   -2.2166   -0.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2921   -0.1688    0.7503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473   -0.3742    0.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764   -0.4929    1.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7181   -0.7024    1.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0439   -0.8334    3.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0347   -0.7828    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500   -0.9967    0.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1577    0.1222   -0.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6292   -0.1328   -0.1021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1253   -0.2442    1.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0347   -1.3084   -0.9438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4468   -1.6825   -0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2992   -0.4544   -0.7231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6525   -0.6595   -0.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4878    0.4187   -1.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8795    0.2588   -1.1256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9430    1.6832   -1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8922    2.8285   -1.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5804    1.8909   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0399    3.2702   -0.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7364    0.8016   -0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3483    0.9896   -0.6398 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1850    2.4116   -2.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7593    1.9186   -1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0123    1.0937   -2.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0968    0.2535   -0.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2896    0.2689   -2.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0442    1.7776   -1.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2840   -1.3057   -0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167    0.1227   -1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9956   -1.6403   -1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8534    0.0568    1.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0768   -1.7002    1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5403   -2.8801   -0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9789   -2.8377    0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2098   -1.8361   -1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6301    0.6840    1.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6616   -1.2860   -0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671    0.5413    0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6064   -1.3832    2.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198    0.3901    2.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5680   -0.5408    3.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8715   -0.0877    2.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4219   -1.8638    3.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5723   -0.6899   -0.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5836   -1.9250    0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8695   -1.1881    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8309    0.2185   -1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9805    1.1082    0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1493    0.1503    1.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0519   -1.3062    1.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4426    0.3688    1.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1107   -0.9358   -2.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3546   -2.1555   -0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5196   -2.0627    0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8486   -2.4554   -1.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1091   -1.6445   -0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2407   -0.6798   -1.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3661    3.7810   -1.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4928    2.9649   -0.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5885    2.5544   -2.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9304    3.2386   -0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3377    3.8132   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3808    3.8447   -1.8483 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  1
 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

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  C   UNK     0    8652.4428665.219   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8652.4428662.125   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8660.4268665.219   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8660.4268663.679   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8661.7588664.445   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.0918665.219   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.4248664.445   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.7568665.219   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.4248662.907   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.0888664.445   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.4248665.219   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8669.7568664.445   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8671.0918665.219   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.7568662.907   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8672.4238664.445   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8673.7558665.219   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8675.0918664.445   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8676.4238665.219   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8675.0918662.907   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8655.1058665.211   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8653.7728664.441   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8653.7728662.901   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8655.1058662.131   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0    8657.7658665.211   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0    8656.4328664.441   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8656.4328662.901   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8657.7658662.131   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8659.0998662.901   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8659.0998664.441   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4    6   30                                                       
CONECT    5   30                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   11                                                       
CONECT   10    8                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13   16                                                       
CONECT   15   13                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   22    1   26                                                  
CONECT   22   21   23    2                                                  
CONECT   23   22   24    3                                                  
CONECT   24   23   27                                                       
CONECT   25   26   30                                                       
CONECT   26   27   25   21                                                  
CONECT   27   26   28   24                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25    4    5                                             
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

COMPND    HMDB0012958
HETATM    1  C1  UNL     1       8.548   1.574  -1.963  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.324   0.512  -1.269  1.00  0.00           C  
HETATM    3  C3  UNL     1      10.786   0.692  -1.141  1.00  0.00           C  
HETATM    4  C4  UNL     1       8.714  -0.544  -0.793  1.00  0.00           C  
HETATM    5  C5  UNL     1       7.249  -0.734  -0.917  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.618  -0.842   0.475  1.00  0.00           C  
HETATM    7  C7  UNL     1       5.157  -1.030   0.269  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.697  -2.217  -0.496  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.292  -0.169   0.750  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.847  -0.374   0.534  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.176  -0.493   1.862  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.718  -0.702   1.775  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.044  -0.833   3.047  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.035  -0.783   0.647  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.450  -0.997   0.602  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.158   0.122  -0.086  1.00  0.00           C  
HETATM   17  C17 UNL     1      -3.629  -0.133  -0.102  1.00  0.00           C  
HETATM   18  C18 UNL     1      -4.125  -0.244   1.341  1.00  0.00           C  
HETATM   19  C19 UNL     1      -4.035  -1.308  -0.944  1.00  0.00           C  
HETATM   20  C20 UNL     1      -5.447  -1.683  -0.549  1.00  0.00           C  
HETATM   21  C21 UNL     1      -6.299  -0.454  -0.723  1.00  0.00           C  
HETATM   22  C22 UNL     1      -7.653  -0.660  -0.840  1.00  0.00           C  
HETATM   23  C23 UNL     1      -8.488   0.419  -1.002  1.00  0.00           C  
HETATM   24  O1  UNL     1      -9.880   0.259  -1.126  1.00  0.00           O  
HETATM   25  C24 UNL     1      -7.943   1.683  -1.042  1.00  0.00           C  
HETATM   26  C25 UNL     1      -8.892   2.828  -1.220  1.00  0.00           C  
HETATM   27  C26 UNL     1      -6.580   1.891  -0.925  1.00  0.00           C  
HETATM   28  C27 UNL     1      -6.040   3.270  -0.974  1.00  0.00           C  
HETATM   29  C28 UNL     1      -5.736   0.802  -0.761  1.00  0.00           C  
HETATM   30  O2  UNL     1      -4.348   0.990  -0.640  1.00  0.00           O  
HETATM   31  H1  UNL     1       9.185   2.412  -2.290  1.00  0.00           H  
HETATM   32  H2  UNL     1       7.759   1.919  -1.252  1.00  0.00           H  
HETATM   33  H3  UNL     1       8.012   1.094  -2.809  1.00  0.00           H  
HETATM   34  H4  UNL     1      11.097   0.254  -0.171  1.00  0.00           H  
HETATM   35  H5  UNL     1      11.290   0.269  -2.013  1.00  0.00           H  
HETATM   36  H6  UNL     1      11.044   1.778  -1.079  1.00  0.00           H  
HETATM   37  H7  UNL     1       9.284  -1.306  -0.294  1.00  0.00           H  
HETATM   38  H8  UNL     1       6.817   0.123  -1.471  1.00  0.00           H  
HETATM   39  H9  UNL     1       6.996  -1.640  -1.503  1.00  0.00           H  
HETATM   40  H10 UNL     1       6.853   0.057   1.057  1.00  0.00           H  
HETATM   41  H11 UNL     1       7.077  -1.700   1.002  1.00  0.00           H  
HETATM   42  H12 UNL     1       5.540  -2.880  -0.760  1.00  0.00           H  
HETATM   43  H13 UNL     1       3.979  -2.838   0.080  1.00  0.00           H  
HETATM   44  H14 UNL     1       4.210  -1.836  -1.431  1.00  0.00           H  
HETATM   45  H15 UNL     1       4.630   0.684   1.300  1.00  0.00           H  
HETATM   46  H16 UNL     1       2.662  -1.286  -0.068  1.00  0.00           H  
HETATM   47  H17 UNL     1       2.467   0.541   0.010  1.00  0.00           H  
HETATM   48  H18 UNL     1       2.606  -1.383   2.384  1.00  0.00           H  
HETATM   49  H19 UNL     1       2.420   0.390   2.486  1.00  0.00           H  
HETATM   50  H20 UNL     1       0.568  -0.541   3.924  1.00  0.00           H  
HETATM   51  H21 UNL     1      -0.872  -0.088   2.993  1.00  0.00           H  
HETATM   52  H22 UNL     1      -0.422  -1.864   3.203  1.00  0.00           H  
HETATM   53  H23 UNL     1       0.572  -0.690  -0.278  1.00  0.00           H  
HETATM   54  H24 UNL     1      -1.584  -1.925   0.010  1.00  0.00           H  
HETATM   55  H25 UNL     1      -1.869  -1.188   1.593  1.00  0.00           H  
HETATM   56  H26 UNL     1      -1.831   0.219  -1.154  1.00  0.00           H  
HETATM   57  H27 UNL     1      -1.981   1.108   0.383  1.00  0.00           H  
HETATM   58  H28 UNL     1      -5.149   0.150   1.445  1.00  0.00           H  
HETATM   59  H29 UNL     1      -4.052  -1.306   1.681  1.00  0.00           H  
HETATM   60  H30 UNL     1      -3.443   0.369   1.966  1.00  0.00           H  
HETATM   61  H31 UNL     1      -4.111  -0.936  -2.007  1.00  0.00           H  
HETATM   62  H32 UNL     1      -3.355  -2.155  -0.940  1.00  0.00           H  
HETATM   63  H33 UNL     1      -5.520  -2.063   0.480  1.00  0.00           H  
HETATM   64  H34 UNL     1      -5.849  -2.455  -1.239  1.00  0.00           H  
HETATM   65  H35 UNL     1      -8.109  -1.645  -0.812  1.00  0.00           H  
HETATM   66  H36 UNL     1     -10.241  -0.680  -1.091  1.00  0.00           H  
HETATM   67  H37 UNL     1      -8.366   3.781  -1.384  1.00  0.00           H  
HETATM   68  H38 UNL     1      -9.493   2.965  -0.279  1.00  0.00           H  
HETATM   69  H39 UNL     1      -9.589   2.554  -2.018  1.00  0.00           H  
HETATM   70  H40 UNL     1      -4.930   3.239  -0.968  1.00  0.00           H  
HETATM   71  H41 UNL     1      -6.338   3.813  -0.053  1.00  0.00           H  
HETATM   72  H42 UNL     1      -6.381   3.845  -1.848  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    4    4
CONECT    3   34   35   36
CONECT    4    5   37
CONECT    5    6   38   39
CONECT    6    7   40   41
CONECT    7    8    9    9
CONECT    8   42   43   44
CONECT    9   10   45
CONECT   10   11   46   47
CONECT   11   12   48   49
CONECT   12   13   14   14
CONECT   13   50   51   52
CONECT   14   15   53
CONECT   15   16   54   55
CONECT   16   17   56   57
CONECT   17   18   19   30
CONECT   18   58   59   60
CONECT   19   20   61   62
CONECT   20   21   63   64
CONECT   21   22   22   29
CONECT   22   23   65
CONECT   23   24   25   25
CONECT   24   66
CONECT   25   26   27
CONECT   26   67   68   69
CONECT   27   28   29   29
CONECT   28   70   71   72
CONECT   29   30
END

HMDB0012958
     RDKit          3D
gamma-Tocotrienol
 72 73  0  0  0  0  0  0  0  0999 V2000
    8.5477    1.5741   -1.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3241    0.5118   -1.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7856    0.6921   -1.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7140   -0.5435   -0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2487   -0.7337   -0.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -0.8419    0.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1570   -1.0298    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6970   -2.2166   -0.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2921   -0.1688    0.7503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473   -0.3742    0.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764   -0.4929    1.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7181   -0.7024    1.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0439   -0.8334    3.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0347   -0.7828    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500   -0.9967    0.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1577    0.1222   -0.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6292   -0.1328   -0.1021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1253   -0.2442    1.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0347   -1.3084   -0.9438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4468   -1.6825   -0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2992   -0.4544   -0.7231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6525   -0.6595   -0.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4878    0.4187   -1.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8795    0.2588   -1.1256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9430    1.6832   -1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8922    2.8285   -1.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5804    1.8909   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0399    3.2702   -0.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7364    0.8016   -0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3483    0.9896   -0.6398 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1850    2.4116   -2.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7593    1.9186   -1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0123    1.0937   -2.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0968    0.2535   -0.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2896    0.2689   -2.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0442    1.7776   -1.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2840   -1.3057   -0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167    0.1227   -1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9956   -1.6403   -1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8534    0.0568    1.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0768   -1.7002    1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5403   -2.8801   -0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9789   -2.8377    0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2098   -1.8361   -1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6301    0.6840    1.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6616   -1.2860   -0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671    0.5413    0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6064   -1.3832    2.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198    0.3901    2.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5680   -0.5408    3.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8715   -0.0877    2.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4219   -1.8638    3.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5723   -0.6899   -0.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5836   -1.9250    0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8695   -1.1881    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8309    0.2185   -1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9805    1.1082    0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1493    0.1503    1.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0519   -1.3062    1.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4426    0.3688    1.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1107   -0.9358   -2.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3546   -2.1555   -0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5196   -2.0627    0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8486   -2.4554   -1.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1091   -1.6445   -0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2407   -0.6798   -1.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3661    3.7810   -1.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4928    2.9649   -0.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5885    2.5544   -2.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9304    3.2386   -0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3377    3.8132   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3808    3.8447   -1.8483 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  1
 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 Stereo Labels

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 Molecular Weight

410.6319

Monoisotopic Molecular Weight

410.318480588

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

14101-61-2

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

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
1-hydroxy-2-unsubstituted benzenoid
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:33277 )
vitamin E (CHEBI:33277 )
vitamin E (C14155 )
Vitamin E (LMPR02020057 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00034 g/L	ALOGPS
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	52.51 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	198.813	31661259
DarkChem	[M-H]-	197.935	31661259
DeepCCS	[M+H]+	204.829	30932474
DeepCCS	[M-H]-	202.471	30932474
DeepCCS	[M-2H]-	236.334	30932474
DeepCCS	[M+Na]+	211.563	30932474
AllCCS	[M+H]+	212.3	32859911
AllCCS	[M+H-H2O]+	209.9	32859911
AllCCS	[M+NH4]+	214.4	32859911
AllCCS	[M+Na]+	215.1	32859911
AllCCS	[M-H]-	202.1	32859911
AllCCS	[M+Na-2H]-	203.4	32859911
AllCCS	[M+HCOO]-	204.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter)). Predicted by Afia on May 17, 2022.	10.35 minutes	32390414
Predicted by Siyang on May 30, 2022	27.8185 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.17 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3751.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	774.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	336.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	392.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	305.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1294.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1197.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	95.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2457.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	890.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1926.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	932.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	551.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	339.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	671.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Tocotrienol	CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1	3922.2	Standard polar	33892256
gamma-Tocotrienol	CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1	3116.4	Standard non polar	33892256
gamma-Tocotrienol	CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1	3220.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
gamma-Tocotrienol,1TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC[C@]1(C)CCC2=CC(O[Si](C)(C)C)=C(C)C(C)=C2O1	3058.4	Semi standard non polar	33892256
gamma-Tocotrienol,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC[C@]1(C)CCC2=CC(O[Si](C)(C)C(C)(C)C)=C(C)C(C)=C2O1	3303.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Tocotrienol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4m-5689000000-0d7bfe0a60d4ee1a2109	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Tocotrienol GC-MS (1 TMS) - 70eV, Positive	splash10-014i-5434900000-88e1ef1d491000736dfa	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Tocotrienol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Tocotrienol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocotrienol LC-ESI-QTOF , positive-QTOF	splash10-03di-0000900000-9ea294ff4831f39965a6	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocotrienol 10V, Positive-QTOF	splash10-0ik9-0952700000-a647628546759321e97f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocotrienol 20V, Positive-QTOF	splash10-0udi-0920000000-5f57114e0b44fb382e34	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocotrienol 40V, Positive-QTOF	splash10-0udi-3920000000-61a9fdea487cbd6093ef	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocotrienol 10V, Negative-QTOF	splash10-0a4i-0100900000-893e3a2bd3a1a3a2f336	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocotrienol 20V, Negative-QTOF	splash10-0a4j-0932800000-da33f54bd082556fef71	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocotrienol 40V, Negative-QTOF	splash10-000e-1933000000-4941dbd0b8867df99c57	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocotrienol 10V, Positive-QTOF	splash10-08fs-5295600000-7c0dc451a62c5aa801b9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocotrienol 20V, Positive-QTOF	splash10-0udj-6893000000-24e47314ac2c35b77a8b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocotrienol 40V, Positive-QTOF	splash10-0006-9800000000-741a3827b0fb740c39e9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocotrienol 10V, Negative-QTOF	splash10-0a4i-0000900000-01a5cd11479be7bee1be	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocotrienol 20V, Negative-QTOF	splash10-052b-0901300000-ffe985ef6c11eebe38f3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocotrienol 40V, Negative-QTOF	splash10-004i-1903000000-8f9de8bc5233fa1f0419	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

M01938

MarkerDB ID

Not Available

Good Scents ID

rw1679281

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for gamma-Tocotrienol (HMDB0012958)

MOL for HMDB0012958 (gamma-Tocotrienol)

3D MOL for HMDB0012958 (gamma-Tocotrienol)

3D SDF for HMDB0012958 (gamma-Tocotrienol)

3D-SDF for HMDB0012958 (gamma-Tocotrienol)

PDB for HMDB0012958 (gamma-Tocotrienol)

3D PDB for HMDB0012958 (gamma-Tocotrienol)

SMILES for HMDB0012958 (gamma-Tocotrienol)

INCHI for HMDB0012958 (gamma-Tocotrienol)

Structure for HMDB0012958 (gamma-Tocotrienol)

3D Structure for HMDB0012958 (gamma-Tocotrienol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra