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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:02:58 UTC

Update Date

2022-03-07 02:51:26 UTC

HMDB ID

HMDB0012562

Secondary Accession Numbers

HMDB12562

Metabolite Identification

Common Name

13'-Hydroxy-gamma-tocotrienol

Description

13'-hydroxy-r-tocotrienol is a precursor in dehydrogenation to form 13'-carboxy-r-tocotrienol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. 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

  Mrv0541 02251208072D          

 31 32  0  0  1  0            999 V2000
   11.0973  -11.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2724  -11.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8599  -11.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2724  -10.4965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8599  -12.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2724  -13.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0973  -13.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5099  -14.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0973  -14.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3354  -14.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7479  -14.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5729  -14.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9854  -15.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5729  -16.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8104  -15.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2222  -16.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8085  -16.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2198  -17.6410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3948  -17.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2192  -18.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9331  -18.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6482  -18.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3616  -18.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0768  -18.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7907  -18.8828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0774  -17.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7926  -17.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3641  -17.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3654  -16.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6495  -17.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9350  -17.2291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  2  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 18 31  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 30  2  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

HMDB0012562
     RDKit          3D
13'-Hydroxy-gamma-tocotrienol
 73 74  0  0  0  0  0  0  0  0999 V2000
    8.7330   -1.9627   -0.7942 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1027   -0.6306   -0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9297   -0.4823   -0.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2589   -1.6058    0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9573   -1.9833   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909   -0.9793   -0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0406    0.2514   -0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7825   -1.2422    0.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6346   -0.2855    0.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3238    0.1497    2.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1855    1.0795    2.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3338    1.6781    3.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4554    1.4540    0.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5900    2.3833    0.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9016    1.8937    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0584    1.4043   -0.9168 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7335    2.4128   -1.9899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677    0.0852   -1.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8682   -0.9339   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3455   -0.9526   -0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9958   -2.0435    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3649   -2.0871    0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9987   -3.1935    1.1831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1505   -1.0367    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6251   -1.1061    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5067    0.0412   -0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3113    1.1944   -0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1098    0.0968   -0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5116    1.2079   -1.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7370    0.5212   -1.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9935    1.6748   -1.3243 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6654   -1.9231   -1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0079   -2.2281    0.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0844   -2.7122   -1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5367    0.5234   -0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9440   -2.5026    0.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2265   -1.4702    1.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1177   -2.3007   -1.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5833   -2.9418    0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1230    0.4197   -1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2749    1.1571   -0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8457    0.1180   -1.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6654   -2.1658    1.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414   -0.7939    0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8630    0.5816   -0.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090    0.6041    2.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488   -0.7277    2.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4216    1.3897    3.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2116    1.2047    4.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1902    2.7583    3.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774    1.0402   -0.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3062    3.2561    0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    2.8924    1.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6765    2.7260    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2013    1.0559    1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6674    2.4720   -2.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1759    3.3883   -1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2568    2.0912   -2.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4267    0.0819   -1.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0537   -0.2555   -2.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3545   -0.7324    0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5125   -1.9249   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3768   -2.8650    0.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9970   -3.1945    1.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0183   -2.0490   -0.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1420   -0.2827   -0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9349   -1.1124    1.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8384    0.8796   -1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0910    1.4647   -0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6750    2.0959   -0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8035    0.2681   -2.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7804    0.6231   -1.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1008    2.0870   -0.4337 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
  2 30  1  0
 30 31  1  0
 29 16  1  0
 28 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 14 52  1  0
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 15 54  1  0
 15 55  1  0
 17 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 21 63  1  0
 23 64  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 30 71  1  0
 30 72  1  0
 31 73  1  0
M  END

  Mrv0541 02251208072D          

 31 32  0  0  1  0            999 V2000
   11.0973  -11.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2724  -11.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8599  -11.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2724  -10.4965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8599  -12.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2724  -13.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0973  -13.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5099  -14.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0973  -14.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3354  -14.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7479  -14.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5729  -14.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9854  -15.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5729  -16.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8104  -15.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2222  -16.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8085  -16.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2198  -17.6410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3948  -17.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2192  -18.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9331  -18.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6482  -18.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3616  -18.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0768  -18.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7907  -18.8828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0774  -17.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7926  -17.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3641  -17.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3654  -16.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6495  -17.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9350  -17.2291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  2  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 18 31  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 30  2  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012562

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(CO)=C/CC\C(C)=C\CC\C(C)=C\CC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O3/c1-20(12-8-13-22(3)19-29)10-7-11-21(2)14-9-16-28(6)17-15-25-18-26(30)23(4)24(5)27(25)31-28/h10,13-14,18,29-30H,7-9,11-12,15-17,19H2,1-6H3/b20-10+,21-14+,22-13+/t28-/m0/s1

> <INCHI_KEY>
BUWYMGRHXZROTQ-XYSSNJNPSA-N

> <FORMULA>
C28H42O3

> <MOLECULAR_WEIGHT>
426.6313

> <EXACT_MASS>
426.31339521

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
53.53312232180242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(3E,7E,11E)-13-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
6.85

> <JCHEM_LOGP>
7.496786270000002

> <ALOGPS_LOGS>
-5.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.64401762943001

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.470422022977031

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0797068162575387

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
134.65759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.66e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(3E,7E,11E)-13-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012562
     RDKit          3D
13'-Hydroxy-gamma-tocotrienol
 73 74  0  0  0  0  0  0  0  0999 V2000
    8.7330   -1.9627   -0.7942 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1027   -0.6306   -0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9297   -0.4823   -0.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2589   -1.6058    0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9573   -1.9833   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909   -0.9793   -0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0406    0.2514   -0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7825   -1.2422    0.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6346   -0.2855    0.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3238    0.1497    2.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1855    1.0795    2.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3338    1.6781    3.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4554    1.4540    0.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5900    2.3833    0.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9016    1.8937    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0584    1.4043   -0.9168 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7335    2.4128   -1.9899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677    0.0852   -1.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8682   -0.9339   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3455   -0.9526   -0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9958   -2.0435    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3649   -2.0871    0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9987   -3.1935    1.1831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1505   -1.0367    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6251   -1.1061    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5067    0.0412   -0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3113    1.1944   -0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1098    0.0968   -0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5116    1.2079   -1.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7370    0.5212   -1.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9935    1.6748   -1.3243 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6654   -1.9231   -1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0079   -2.2281    0.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0844   -2.7122   -1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5367    0.5234   -0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9440   -2.5026    0.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2265   -1.4702    1.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1177   -2.3007   -1.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5833   -2.9418    0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1230    0.4197   -1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2749    1.1571   -0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8457    0.1180   -1.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6654   -2.1658    1.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414   -0.7939    0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8630    0.5816   -0.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090    0.6041    2.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488   -0.7277    2.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4216    1.3897    3.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2116    1.2047    4.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1902    2.7583    3.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774    1.0402   -0.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3062    3.2561    0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    2.8924    1.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6765    2.7260    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2013    1.0559    1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6674    2.4720   -2.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1759    3.3883   -1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2568    2.0912   -2.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4267    0.0819   -1.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0537   -0.2555   -2.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3545   -0.7324    0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5125   -1.9249   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3768   -2.8650    0.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9970   -3.1945    1.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0183   -2.0490   -0.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1420   -0.2827   -0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9349   -1.1124    1.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8384    0.8796   -1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0910    1.4647   -0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6750    2.0959   -0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8035    0.2681   -2.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7804    0.6231   -1.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1008    2.0870   -0.4337 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
  2 30  1  0
 30 31  1  0
 29 16  1  0
 28 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 17 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 21 63  1  0
 23 64  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 30 71  1  0
 30 72  1  0
 31 73  1  0
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      20.715 -22.260   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.175 -22.260   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.405 -20.928   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      19.175 -19.593   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      18.405 -23.594   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.175 -24.928   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.715 -24.927   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.485 -26.261   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.715 -27.594   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.026 -26.261   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.796 -27.594   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.336 -27.593   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.106 -28.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.336 -30.261   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.646 -28.927   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.415 -30.261   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.643 -31.595   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.410 -32.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.870 -32.927   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.409 -34.469   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      29.742 -35.241   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      31.077 -34.472   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      32.408 -35.244   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      33.743 -34.475   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      35.076 -35.248   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      33.744 -32.936   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      35.080 -32.168   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      32.413 -32.163   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      32.415 -30.625   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      31.079 -32.932   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      29.745 -32.161   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   31                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   22   28   31                                                  
CONECT   31   18   30                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

COMPND    HMDB0012562
HETATM    1  C1  UNL     1       8.733  -1.963  -0.794  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.103  -0.631  -0.783  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.930  -0.482  -0.154  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.259  -1.606   0.522  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.957  -1.983  -0.064  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.891  -0.979  -0.101  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.041   0.251  -0.913  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.782  -1.242   0.583  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.635  -0.285   0.613  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.324   0.150   2.024  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.186   1.079   2.015  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.334   1.678   3.298  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.455   1.454   0.909  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.590   2.383   0.915  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.902   1.894   0.465  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.058   1.404  -0.917  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.734   2.413  -1.990  1.00  0.00           C  
HETATM   18  C18 UNL     1      -2.468   0.085  -1.272  1.00  0.00           C  
HETATM   19  C19 UNL     1      -2.868  -0.934  -0.225  1.00  0.00           C  
HETATM   20  C20 UNL     1      -4.346  -0.953  -0.089  1.00  0.00           C  
HETATM   21  C21 UNL     1      -4.996  -2.043   0.475  1.00  0.00           C  
HETATM   22  C22 UNL     1      -6.365  -2.087   0.613  1.00  0.00           C  
HETATM   23  O1  UNL     1      -6.999  -3.193   1.183  1.00  0.00           O  
HETATM   24  C23 UNL     1      -7.151  -1.037   0.192  1.00  0.00           C  
HETATM   25  C24 UNL     1      -8.625  -1.106   0.351  1.00  0.00           C  
HETATM   26  C25 UNL     1      -6.507   0.041  -0.366  1.00  0.00           C  
HETATM   27  C26 UNL     1      -7.311   1.194  -0.833  1.00  0.00           C  
HETATM   28  C27 UNL     1      -5.110   0.097  -0.512  1.00  0.00           C  
HETATM   29  O2  UNL     1      -4.512   1.208  -1.081  1.00  0.00           O  
HETATM   30  C28 UNL     1       8.737   0.521  -1.446  1.00  0.00           C  
HETATM   31  O3  UNL     1       7.994   1.675  -1.324  1.00  0.00           O  
HETATM   32  H1  UNL     1       9.665  -1.923  -1.413  1.00  0.00           H  
HETATM   33  H2  UNL     1       9.008  -2.228   0.240  1.00  0.00           H  
HETATM   34  H3  UNL     1       8.084  -2.712  -1.283  1.00  0.00           H  
HETATM   35  H4  UNL     1       6.537   0.523  -0.169  1.00  0.00           H  
HETATM   36  H5  UNL     1       6.944  -2.503   0.395  1.00  0.00           H  
HETATM   37  H6  UNL     1       6.227  -1.470   1.631  1.00  0.00           H  
HETATM   38  H7  UNL     1       5.118  -2.301  -1.144  1.00  0.00           H  
HETATM   39  H8  UNL     1       4.583  -2.942   0.419  1.00  0.00           H  
HETATM   40  H9  UNL     1       3.123   0.420  -1.559  1.00  0.00           H  
HETATM   41  H10 UNL     1       4.275   1.157  -0.330  1.00  0.00           H  
HETATM   42  H11 UNL     1       4.846   0.118  -1.695  1.00  0.00           H  
HETATM   43  H12 UNL     1       2.665  -2.166   1.150  1.00  0.00           H  
HETATM   44  H13 UNL     1       0.741  -0.794   0.217  1.00  0.00           H  
HETATM   45  H14 UNL     1       1.863   0.582  -0.028  1.00  0.00           H  
HETATM   46  H15 UNL     1       2.209   0.604   2.514  1.00  0.00           H  
HETATM   47  H16 UNL     1       1.049  -0.728   2.661  1.00  0.00           H  
HETATM   48  H17 UNL     1      -1.422   1.390   3.321  1.00  0.00           H  
HETATM   49  H18 UNL     1       0.212   1.205   4.143  1.00  0.00           H  
HETATM   50  H19 UNL     1      -0.190   2.758   3.319  1.00  0.00           H  
HETATM   51  H20 UNL     1      -0.077   1.040  -0.008  1.00  0.00           H  
HETATM   52  H21 UNL     1      -1.306   3.256   0.246  1.00  0.00           H  
HETATM   53  H22 UNL     1      -1.681   2.892   1.929  1.00  0.00           H  
HETATM   54  H23 UNL     1      -3.677   2.726   0.587  1.00  0.00           H  
HETATM   55  H24 UNL     1      -3.201   1.056   1.149  1.00  0.00           H  
HETATM   56  H25 UNL     1      -1.667   2.472  -2.232  1.00  0.00           H  
HETATM   57  H26 UNL     1      -3.176   3.388  -1.703  1.00  0.00           H  
HETATM   58  H27 UNL     1      -3.257   2.091  -2.917  1.00  0.00           H  
HETATM   59  H28 UNL     1      -1.427   0.082  -1.556  1.00  0.00           H  
HETATM   60  H29 UNL     1      -3.054  -0.255  -2.201  1.00  0.00           H  
HETATM   61  H30 UNL     1      -2.354  -0.732   0.743  1.00  0.00           H  
HETATM   62  H31 UNL     1      -2.513  -1.925  -0.628  1.00  0.00           H  
HETATM   63  H32 UNL     1      -4.377  -2.865   0.804  1.00  0.00           H  
HETATM   64  H33 UNL     1      -7.997  -3.194   1.270  1.00  0.00           H  
HETATM   65  H34 UNL     1      -9.018  -2.049  -0.114  1.00  0.00           H  
HETATM   66  H35 UNL     1      -9.142  -0.283  -0.169  1.00  0.00           H  
HETATM   67  H36 UNL     1      -8.935  -1.112   1.427  1.00  0.00           H  
HETATM   68  H37 UNL     1      -7.838   0.880  -1.758  1.00  0.00           H  
HETATM   69  H38 UNL     1      -8.091   1.465  -0.093  1.00  0.00           H  
HETATM   70  H39 UNL     1      -6.675   2.096  -0.986  1.00  0.00           H  
HETATM   71  H40 UNL     1       8.804   0.268  -2.539  1.00  0.00           H  
HETATM   72  H41 UNL     1       9.780   0.623  -1.053  1.00  0.00           H  
HETATM   73  H42 UNL     1       8.101   2.087  -0.434  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    3   30
CONECT    3    4   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7    8    8
CONECT    7   40   41   42
CONECT    8    9   43
CONECT    9   10   44   45
CONECT   10   11   46   47
CONECT   11   12   13   13
CONECT   12   48   49   50
CONECT   13   14   51
CONECT   14   15   52   53
CONECT   15   16   54   55
CONECT   16   17   18   29
CONECT   17   56   57   58
CONECT   18   19   59   60
CONECT   19   20   61   62
CONECT   20   21   21   28
CONECT   21   22   63
CONECT   22   23   24   24
CONECT   23   64
CONECT   24   25   26
CONECT   25   65   66   67
CONECT   26   27   28   28
CONECT   27   68   69   70
CONECT   28   29
CONECT   30   31   71   72
CONECT   31   73
END

HMDB0012562
     RDKit          3D
13'-Hydroxy-gamma-tocotrienol
 73 74  0  0  0  0  0  0  0  0999 V2000
    8.7330   -1.9627   -0.7942 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1027   -0.6306   -0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9297   -0.4823   -0.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2589   -1.6058    0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9573   -1.9833   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909   -0.9793   -0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0406    0.2514   -0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7825   -1.2422    0.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6346   -0.2855    0.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3238    0.1497    2.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1855    1.0795    2.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3338    1.6781    3.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4554    1.4540    0.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5900    2.3833    0.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9016    1.8937    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0584    1.4043   -0.9168 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7335    2.4128   -1.9899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677    0.0852   -1.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8682   -0.9339   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3455   -0.9526   -0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9958   -2.0435    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3649   -2.0871    0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9987   -3.1935    1.1831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1505   -1.0367    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6251   -1.1061    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5067    0.0412   -0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3113    1.1944   -0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1098    0.0968   -0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5116    1.2079   -1.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7370    0.5212   -1.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9935    1.6748   -1.3243 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6654   -1.9231   -1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0079   -2.2281    0.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0844   -2.7122   -1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5367    0.5234   -0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9440   -2.5026    0.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2265   -1.4702    1.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1177   -2.3007   -1.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5833   -2.9418    0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1230    0.4197   -1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2749    1.1571   -0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8457    0.1180   -1.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6654   -2.1658    1.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414   -0.7939    0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8630    0.5816   -0.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090    0.6041    2.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488   -0.7277    2.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4216    1.3897    3.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2116    1.2047    4.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1902    2.7583    3.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774    1.0402   -0.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3062    3.2561    0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    2.8924    1.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6765    2.7260    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2013    1.0559    1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6674    2.4720   -2.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1759    3.3883   -1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2568    2.0912   -2.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4267    0.0819   -1.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0537   -0.2555   -2.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3545   -0.7324    0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5125   -1.9249   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3768   -2.8650    0.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9970   -3.1945    1.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0183   -2.0490   -0.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1420   -0.2827   -0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9349   -1.1124    1.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8384    0.8796   -1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0910    1.4647   -0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6750    2.0959   -0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8035    0.2681   -2.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7804    0.6231   -1.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1008    2.0870   -0.4337 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
  2 30  1  0
 30 31  1  0
 29 16  1  0
 28 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 17 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 21 63  1  0
 23 64  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 30 71  1  0
 30 72  1  0
 31 73  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
13'-Hydroxy-g-tocotrienol	Generator
13'-Hydroxy-γ-tocotrienol	Generator
13OHgammaTE	HMDB

Chemical Formula

C₂₈H₄₂O₃

Average Molecular Weight

426.6313

Monoisotopic Molecular Weight

426.31339521

IUPAC Name

(2S)-2-[(3E,7E,11E)-13-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

(2S)-2-[(3E,7E,11E)-13-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-6-ol

CAS Registry Number

Not Available

SMILES

C\C(CO)=C/CC\C(C)=C\CC\C(C)=C\CC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2

InChI Identifier

InChI=1S/C28H42O3/c1-20(12-8-13-22(3)19-29)10-7-11-21(2)14-9-16-28(6)17-15-25-18-26(30)23(4)24(5)27(25)31-28/h10,13-14,18,29-30H,7-9,11-12,15-17,19H2,1-6H3/b20-10+,21-14+,22-13+/t28-/m0/s1

InChI Key

BUWYMGRHXZROTQ-XYSSNJNPSA-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
Long chain fatty alcohol
Chromane
Benzopyran
1-benzopyran
Fatty alcohol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acyl
Benzenoid
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012562)

Source

Endogenous

Endogenous (HMDB: HMDB0012562)

Animal

Animal (HMDB: HMDB0012562)

Exogenous

Food

Food (HMDB: HMDB0012562)

Exogenous (HMDB: HMDB0012562)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012562)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012562)

Lipid metabolism pathway (HMDB: HMDB0012562)

Cellular process

Cell signaling (HMDB: HMDB0012562)

Biochemical process

Lipid transport (HMDB: HMDB0012562)

Role

Biological role

Energy source (HMDB: HMDB0012562)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012562)

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00057 g/L	ALOGPS
logP	6.85	ALOGPS
logP	7.5	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	10.47	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	134.66 m³·mol⁻¹	ChemAxon
Polarizability	53.53 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	204.186	31661259
DarkChem	[M-H]-	196.996	31661259
DeepCCS	[M+H]+	219.989	30932474
DeepCCS	[M-H]-	217.593	30932474
DeepCCS	[M-2H]-	250.477	30932474
DeepCCS	[M+Na]+	225.901	30932474
AllCCS	[M+H]+	214.8	32859911
AllCCS	[M+H-H2O]+	212.6	32859911
AllCCS	[M+NH4]+	216.9	32859911
AllCCS	[M+Na]+	217.5	32859911
AllCCS	[M-H]-	207.5	32859911
AllCCS	[M+Na-2H]-	209.3	32859911
AllCCS	[M+HCOO]-	211.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
13'-Hydroxy-gamma-tocotrienol	C\C(CO)=C/CC\C(C)=C\CC\C(C)=C\CC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2	4111.2	Standard polar	33892256
13'-Hydroxy-gamma-tocotrienol	C\C(CO)=C/CC\C(C)=C\CC\C(C)=C\CC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2	3341.2	Standard non polar	33892256
13'-Hydroxy-gamma-tocotrienol	C\C(CO)=C/CC\C(C)=C\CC\C(C)=C\CC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2	3513.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
13'-Hydroxy-gamma-tocotrienol,1TMS,isomer #1	C/C(=C\CC/C(C)=C/CC[C@@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1)CC/C=C(\C)CO[Si](C)(C)C	3282.6	Semi standard non polar	33892256
13'-Hydroxy-gamma-tocotrienol,1TMS,isomer #2	C/C(=C\CC/C(C)=C/CC/C(C)=C/CC[C@@]1(C)CCC2=CC(O[Si](C)(C)C)=C(C)C(C)=C2O1)CO	3281.1	Semi standard non polar	33892256
13'-Hydroxy-gamma-tocotrienol,2TMS,isomer #1	C/C(=C\CC/C(C)=C/CC[C@@]1(C)CCC2=CC(O[Si](C)(C)C)=C(C)C(C)=C2O1)CC/C=C(\C)CO[Si](C)(C)C	3245.3	Semi standard non polar	33892256
13'-Hydroxy-gamma-tocotrienol,1TBDMS,isomer #1	C/C(=C\CC/C(C)=C/CC[C@@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1)CC/C=C(\C)CO[Si](C)(C)C(C)(C)C	3525.9	Semi standard non polar	33892256
13'-Hydroxy-gamma-tocotrienol,1TBDMS,isomer #2	C/C(=C\CC/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)CO	3519.2	Semi standard non polar	33892256
13'-Hydroxy-gamma-tocotrienol,2TBDMS,isomer #1	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)CC/C=C(\C)CO[Si](C)(C)C(C)(C)C	3726.5	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 - 13'-Hydroxy-gamma-tocotrienol GC-MS (Non-derivatized) - 70eV, Positive	splash10-01vx-2689400000-f0f45afc9c6b0f3c9b04	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13'-Hydroxy-gamma-tocotrienol GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-1274590000-85d672033253c88fa3fc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13'-Hydroxy-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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 10V, Positive-QTOF	splash10-0kdi-0532900000-147e78c3eea17197cdf9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 20V, Positive-QTOF	splash10-0udi-0921000000-c63749dfb46f43958ae6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 40V, Positive-QTOF	splash10-0udi-1910000000-b2f76881968c5f753b67	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 10V, Negative-QTOF	splash10-004i-0000900000-7a12acca59807953034e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 20V, Negative-QTOF	splash10-002b-0714900000-1231ef4fa29f185062d1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 40V, Negative-QTOF	splash10-002b-3928100000-da0467995e252474cbd0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 10V, Positive-QTOF	splash10-056s-1496600000-aa6abdb3e7525a573399	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 20V, Positive-QTOF	splash10-0002-2693000000-21881151d86350524d15	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 40V, Positive-QTOF	splash10-0006-4910000000-d515ae4ba205803ea889	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 10V, Negative-QTOF	splash10-0a4i-0106900000-ef2f1c1214df1d834d4b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 20V, Negative-QTOF	splash10-002b-0409200000-e34b7a2a93bb64703190	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 40V, Negative-QTOF	splash10-00b9-1719000000-76f0b5cdf15492e1c339	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB029128

KNApSAcK ID

Not Available

Chemspider ID

30776636

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481468

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

CE7074

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 13'-Hydroxy-gamma-tocotrienol (HMDB0012562)

MOL for HMDB0012562 (13'-Hydroxy-gamma-tocotrienol)

3D MOL for HMDB0012562 (13'-Hydroxy-gamma-tocotrienol)

3D SDF for HMDB0012562 (13'-Hydroxy-gamma-tocotrienol)

3D-SDF for HMDB0012562 (13'-Hydroxy-gamma-tocotrienol)

PDB for HMDB0012562 (13'-Hydroxy-gamma-tocotrienol)

3D PDB for HMDB0012562 (13'-Hydroxy-gamma-tocotrienol)

SMILES for HMDB0012562 (13'-Hydroxy-gamma-tocotrienol)

INCHI for HMDB0012562 (13'-Hydroxy-gamma-tocotrienol)

Structure for HMDB0012562 (13'-Hydroxy-gamma-tocotrienol)

3D Structure for HMDB0012562 (13'-Hydroxy-gamma-tocotrienol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra