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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:02:53 UTC

Update Date

2022-03-07 02:51:26 UTC

HMDB ID

HMDB0012558

Secondary Accession Numbers

HMDB12558

Metabolite Identification

Common Name

13'-Carboxy-gamma-tocotrienol

Description

13'-carboxy-r-tocotrienol is a dehydrogenation carboxylate product of 13'-hydroxy-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 02251208062D          

 32 33  0  0  1  0            999 V2000
   14.4376  -12.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6126  -12.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2002  -11.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3752  -11.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9627  -10.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1377  -10.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7252  -11.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7252   -9.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1377   -9.2329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9003   -9.9474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2002  -12.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6126  -13.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4376  -13.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8500  -14.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4376  -14.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6757  -14.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0875  -14.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6738  -15.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0857  -16.3778    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2607  -16.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0844  -17.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7983  -17.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5136  -17.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2275  -17.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9420  -17.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6566  -17.6196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9426  -16.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6578  -15.9696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2293  -15.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2306  -15.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5148  -16.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8008  -15.9659    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 11  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  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
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 19 32  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 31  2  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

HMDB0012558
     RDKit          3D
13'-Carboxy-gamma-tocotrienol
 72 73  0  0  0  0  0  0  0  0999 V2000
    4.6992    0.3868    2.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2422   -0.4607    1.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3354   -1.4000    1.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7562   -1.6192    2.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488   -1.5151    2.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -0.2236    2.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422    1.0104    2.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0983   -0.1815    1.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6453    1.0914    0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110    1.2662    0.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9509    0.3511   -0.1113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8330   -1.1112    0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6704    0.4675   -1.5886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8306    0.8597   -2.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1432    0.3909   -1.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1583    0.0073   -2.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3857   -0.4272   -2.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4001   -0.8116   -3.2836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6021   -0.4783   -1.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8866   -0.9306   -0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5917   -0.0962   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8170   -0.1479    1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3683    0.3368   -0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3143    0.7329    0.1753 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300   -0.2409   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3381   -0.4634   -0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9688   -0.2620   -1.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8995    0.6718   -1.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3414    1.5486   -0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4742    0.8086   -3.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3470    1.6760   -3.2067 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0753    0.0032   -4.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4467    1.1568    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2808   -0.2106    2.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8872    0.9614    2.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357   -1.9981    0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267   -1.0210    3.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9780   -2.6924    2.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8473   -1.8010    3.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8899   -2.3545    1.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6313    1.7366    2.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723    1.4856    3.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5825    0.7838    3.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2964   -1.1042    0.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3232    1.3246   -0.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1961    1.9681    1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5309    1.2094    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3676    2.3065    0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2528   -1.6926   -0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8777   -1.5518    0.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414   -1.3044    1.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505    1.2322   -1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2438   -0.4694   -2.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8740    1.9882   -2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7094    0.5833   -3.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9980    0.0440   -3.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2792   -0.7874   -4.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6495   -1.8358    0.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5556   -1.2765   -1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3562   -0.1884    0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2310   -1.1382    1.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5317    0.6651    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8917   -0.0030    1.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3905   -0.9218   -1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069    0.8108   -0.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7377    0.3029    0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5653   -1.4898    0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6568   -0.8913   -2.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4992    2.1574   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7910    0.9375    0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1145    2.2207   -0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8155   -0.3825   -4.6606 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
 11 10  1  1
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
  2 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 30 32  1  0
 24 11  1  0
 23 15  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  7 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
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 18 57  1  0
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 20 59  1  0
 20 60  1  0
 22 61  1  0
 22 62  1  0
 22 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 29 69  1  0
 29 70  1  0
 29 71  1  0
 32 72  1  0
M  END


  Mrv0541 02251208062D          

 32 33  0  0  1  0            999 V2000
   14.4376  -12.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6126  -12.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2002  -11.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3752  -11.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9627  -10.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1377  -10.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7252  -11.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7252   -9.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1377   -9.2329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9003   -9.9474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2002  -12.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6126  -13.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4376  -13.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8500  -14.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4376  -14.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6757  -14.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0875  -14.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6738  -15.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0857  -16.3778    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2607  -16.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0844  -17.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7983  -17.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5136  -17.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2275  -17.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9420  -17.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6566  -17.6196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9426  -16.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6578  -15.9696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2293  -15.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2306  -15.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5148  -16.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8008  -15.9659    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 11  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  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
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 19 32  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 31  2  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012558

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O4/c1-19(12-8-14-21(3)27(30)31)10-7-11-20(2)13-9-16-28(6)17-15-24-18-25(29)22(4)23(5)26(24)32-28/h10,13-14,18,29H,7-9,11-12,15-17H2,1-6H3,(H,30,31)/b19-10+,20-13+,21-14+/t28-/m1/s1

> <INCHI_KEY>
UJMZKOBSLDXUHY-YQHRJHOASA-N

> <FORMULA>
C28H40O4

> <MOLECULAR_WEIGHT>
440.6148

> <EXACT_MASS>
440.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
53.59030275788969

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,6E,10E)-13-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid

> <ALOGPS_LOGP>
6.46

> <JCHEM_LOGP>
7.969250025666668

> <ALOGPS_LOGS>
-6.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.470424046058682

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.071155951134125

> <JCHEM_PKA_STRONGEST_BASIC>
-4.85247062670823

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
134.60009999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.22e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6E,10E)-13-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012558
     RDKit          3D
13'-Carboxy-gamma-tocotrienol
 72 73  0  0  0  0  0  0  0  0999 V2000
    4.6992    0.3868    2.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2422   -0.4607    1.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3354   -1.4000    1.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7562   -1.6192    2.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488   -1.5151    2.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -0.2236    2.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422    1.0104    2.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0983   -0.1815    1.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6453    1.0914    0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110    1.2662    0.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9509    0.3511   -0.1113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8330   -1.1112    0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6704    0.4675   -1.5886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8306    0.8597   -2.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1432    0.3909   -1.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1583    0.0073   -2.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3857   -0.4272   -2.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4001   -0.8116   -3.2836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6021   -0.4783   -1.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8866   -0.9306   -0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5917   -0.0962   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8170   -0.1479    1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3683    0.3368   -0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3143    0.7329    0.1753 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300   -0.2409   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3381   -0.4634   -0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9688   -0.2620   -1.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8995    0.6718   -1.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3414    1.5486   -0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4742    0.8086   -3.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3470    1.6760   -3.2067 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0753    0.0032   -4.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4467    1.1568    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2808   -0.2106    2.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8872    0.9614    2.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357   -1.9981    0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267   -1.0210    3.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9780   -2.6924    2.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8473   -1.8010    3.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8899   -2.3545    1.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6313    1.7366    2.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723    1.4856    3.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5825    0.7838    3.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2964   -1.1042    0.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3232    1.3246   -0.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1961    1.9681    1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5309    1.2094    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3676    2.3065    0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2528   -1.6926   -0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8777   -1.5518    0.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414   -1.3044    1.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505    1.2322   -1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2438   -0.4694   -2.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8740    1.9882   -2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7094    0.5833   -3.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9980    0.0440   -3.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2792   -0.7874   -4.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6495   -1.8358    0.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5556   -1.2765   -1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3562   -0.1884    0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2310   -1.1382    1.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5317    0.6651    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8917   -0.0030    1.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3905   -0.9218   -1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069    0.8108   -0.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7377    0.3029    0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5653   -1.4898    0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6568   -0.8913   -2.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4992    2.1574   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7910    0.9375    0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1145    2.2207   -0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8155   -0.3825   -4.6606 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
 11 10  1  1
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
  2 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 30 32  1  0
 24 11  1  0
 23 15  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  7 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 12 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 16 56  1  0
 18 57  1  0
 20 58  1  0
 20 59  1  0
 20 60  1  0
 22 61  1  0
 22 62  1  0
 22 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 29 69  1  0
 29 70  1  0
 29 71  1  0
 32 72  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      26.950 -22.570   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.410 -22.570   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.640 -21.236   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.100 -21.236   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.330 -19.902   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.790 -19.902   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.020 -21.235   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.020 -18.568   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      20.790 -17.235   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      18.481 -18.568   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      24.640 -23.904   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.410 -25.238   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.950 -25.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.720 -26.570   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.950 -27.904   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.261 -26.570   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.030 -27.904   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.258 -29.237   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.027 -30.572   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.487 -30.569   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.024 -32.112   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      31.357 -32.883   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      32.692 -32.114   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      34.025 -32.886   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      35.358 -32.119   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      36.692 -32.890   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      35.360 -30.579   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      36.695 -29.810   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      34.028 -29.807   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      34.030 -28.267   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      32.694 -30.575   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      31.361 -29.803   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   32                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   23   29   32                                                  
CONECT   32   19   31                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

COMPND    HMDB0012558
HETATM    1  C1  UNL     1       4.699   0.387   2.182  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.242  -0.461   1.081  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.335  -1.400   1.268  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.756  -1.619   2.597  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.249  -1.515   2.608  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.710  -0.224   2.187  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.042   1.010   2.941  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.098  -0.182   1.113  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.645   1.091   0.677  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.111   1.266   0.713  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.951   0.351  -0.111  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.833  -1.111   0.236  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.670   0.467  -1.589  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.831   0.860  -2.428  1.00  0.00           C  
HETATM   15  C15 UNL     1      -5.143   0.391  -1.986  1.00  0.00           C  
HETATM   16  C16 UNL     1      -6.158   0.007  -2.834  1.00  0.00           C  
HETATM   17  C17 UNL     1      -7.386  -0.427  -2.384  1.00  0.00           C  
HETATM   18  O1  UNL     1      -8.400  -0.812  -3.284  1.00  0.00           O  
HETATM   19  C18 UNL     1      -7.602  -0.478  -1.024  1.00  0.00           C  
HETATM   20  C19 UNL     1      -8.887  -0.931  -0.448  1.00  0.00           C  
HETATM   21  C20 UNL     1      -6.592  -0.096  -0.162  1.00  0.00           C  
HETATM   22  C21 UNL     1      -6.817  -0.148   1.304  1.00  0.00           C  
HETATM   23  C22 UNL     1      -5.368   0.337  -0.611  1.00  0.00           C  
HETATM   24  O2  UNL     1      -4.314   0.733   0.175  1.00  0.00           O  
HETATM   25  C23 UNL     1       4.830  -0.241  -0.286  1.00  0.00           C  
HETATM   26  C24 UNL     1       6.338  -0.463  -0.203  1.00  0.00           C  
HETATM   27  C25 UNL     1       6.969  -0.262  -1.520  1.00  0.00           C  
HETATM   28  C26 UNL     1       7.899   0.672  -1.692  1.00  0.00           C  
HETATM   29  C27 UNL     1       8.341   1.549  -0.568  1.00  0.00           C  
HETATM   30  C28 UNL     1       8.474   0.809  -3.023  1.00  0.00           C  
HETATM   31  O3  UNL     1       9.347   1.676  -3.207  1.00  0.00           O  
HETATM   32  O4  UNL     1       8.075   0.003  -4.077  1.00  0.00           O  
HETATM   33  H1  UNL     1       5.447   1.157   1.831  1.00  0.00           H  
HETATM   34  H2  UNL     1       5.281  -0.211   2.943  1.00  0.00           H  
HETATM   35  H3  UNL     1       3.887   0.961   2.625  1.00  0.00           H  
HETATM   36  H4  UNL     1       3.036  -1.998   0.417  1.00  0.00           H  
HETATM   37  H5  UNL     1       3.227  -1.021   3.393  1.00  0.00           H  
HETATM   38  H6  UNL     1       2.978  -2.692   2.871  1.00  0.00           H  
HETATM   39  H7  UNL     1       0.847  -1.801   3.623  1.00  0.00           H  
HETATM   40  H8  UNL     1       0.890  -2.354   1.948  1.00  0.00           H  
HETATM   41  H9  UNL     1       1.631   1.737   2.377  1.00  0.00           H  
HETATM   42  H10 UNL     1       0.072   1.486   3.271  1.00  0.00           H  
HETATM   43  H11 UNL     1       1.582   0.784   3.881  1.00  0.00           H  
HETATM   44  H12 UNL     1      -0.296  -1.104   0.608  1.00  0.00           H  
HETATM   45  H13 UNL     1      -0.323   1.325  -0.389  1.00  0.00           H  
HETATM   46  H14 UNL     1      -0.196   1.968   1.242  1.00  0.00           H  
HETATM   47  H15 UNL     1      -2.531   1.209   1.761  1.00  0.00           H  
HETATM   48  H16 UNL     1      -2.368   2.306   0.394  1.00  0.00           H  
HETATM   49  H17 UNL     1      -2.253  -1.693  -0.528  1.00  0.00           H  
HETATM   50  H18 UNL     1      -3.878  -1.552   0.119  1.00  0.00           H  
HETATM   51  H19 UNL     1      -2.541  -1.304   1.273  1.00  0.00           H  
HETATM   52  H20 UNL     1      -1.851   1.232  -1.730  1.00  0.00           H  
HETATM   53  H21 UNL     1      -2.244  -0.469  -2.000  1.00  0.00           H  
HETATM   54  H22 UNL     1      -3.874   1.988  -2.437  1.00  0.00           H  
HETATM   55  H23 UNL     1      -3.709   0.583  -3.502  1.00  0.00           H  
HETATM   56  H24 UNL     1      -5.998   0.044  -3.903  1.00  0.00           H  
HETATM   57  H25 UNL     1      -8.279  -0.787  -4.267  1.00  0.00           H  
HETATM   58  H26 UNL     1      -8.649  -1.836   0.177  1.00  0.00           H  
HETATM   59  H27 UNL     1      -9.556  -1.276  -1.257  1.00  0.00           H  
HETATM   60  H28 UNL     1      -9.356  -0.188   0.217  1.00  0.00           H  
HETATM   61  H29 UNL     1      -7.231  -1.138   1.627  1.00  0.00           H  
HETATM   62  H30 UNL     1      -7.532   0.665   1.565  1.00  0.00           H  
HETATM   63  H31 UNL     1      -5.892  -0.003   1.861  1.00  0.00           H  
HETATM   64  H32 UNL     1       4.390  -0.922  -1.023  1.00  0.00           H  
HETATM   65  H33 UNL     1       4.607   0.811  -0.539  1.00  0.00           H  
HETATM   66  H34 UNL     1       6.738   0.303   0.509  1.00  0.00           H  
HETATM   67  H35 UNL     1       6.565  -1.490   0.123  1.00  0.00           H  
HETATM   68  H36 UNL     1       6.657  -0.891  -2.341  1.00  0.00           H  
HETATM   69  H37 UNL     1       7.499   2.157  -0.194  1.00  0.00           H  
HETATM   70  H38 UNL     1       8.791   0.937   0.239  1.00  0.00           H  
HETATM   71  H39 UNL     1       9.115   2.221  -0.941  1.00  0.00           H  
HETATM   72  H40 UNL     1       8.816  -0.383  -4.661  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3    3   25
CONECT    3    4   36
CONECT    4    5   37   38
CONECT    5    6   39   40
CONECT    6    7    8    8
CONECT    7   41   42   43
CONECT    8    9   44
CONECT    9   10   45   46
CONECT   10   11   47   48
CONECT   11   12   13   24
CONECT   12   49   50   51
CONECT   13   14   52   53
CONECT   14   15   54   55
CONECT   15   16   16   23
CONECT   16   17   56
CONECT   17   18   19   19
CONECT   18   57
CONECT   19   20   21
CONECT   20   58   59   60
CONECT   21   22   23   23
CONECT   22   61   62   63
CONECT   23   24
CONECT   25   26   64   65
CONECT   26   27   66   67
CONECT   27   28   28   68
CONECT   28   29   30
CONECT   29   69   70   71
CONECT   30   31   31   32
CONECT   32   72
END

HMDB0012558
     RDKit          3D
13'-Carboxy-gamma-tocotrienol
 72 73  0  0  0  0  0  0  0  0999 V2000
    4.6992    0.3868    2.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2422   -0.4607    1.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3354   -1.4000    1.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7562   -1.6192    2.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488   -1.5151    2.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -0.2236    2.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422    1.0104    2.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0983   -0.1815    1.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6453    1.0914    0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110    1.2662    0.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9509    0.3511   -0.1113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8330   -1.1112    0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6704    0.4675   -1.5886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8306    0.8597   -2.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1432    0.3909   -1.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1583    0.0073   -2.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3857   -0.4272   -2.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4001   -0.8116   -3.2836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6021   -0.4783   -1.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8866   -0.9306   -0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5917   -0.0962   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8170   -0.1479    1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3683    0.3368   -0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3143    0.7329    0.1753 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300   -0.2409   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3381   -0.4634   -0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9688   -0.2620   -1.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8995    0.6718   -1.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3414    1.5486   -0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4742    0.8086   -3.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3470    1.6760   -3.2067 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0753    0.0032   -4.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4467    1.1568    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2808   -0.2106    2.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8872    0.9614    2.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357   -1.9981    0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267   -1.0210    3.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9780   -2.6924    2.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8473   -1.8010    3.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8899   -2.3545    1.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6313    1.7366    2.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723    1.4856    3.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5825    0.7838    3.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2964   -1.1042    0.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3232    1.3246   -0.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1961    1.9681    1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5309    1.2094    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3676    2.3065    0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2528   -1.6926   -0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8777   -1.5518    0.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414   -1.3044    1.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505    1.2322   -1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2438   -0.4694   -2.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8740    1.9882   -2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7094    0.5833   -3.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9980    0.0440   -3.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2792   -0.7874   -4.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6495   -1.8358    0.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5556   -1.2765   -1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3562   -0.1884    0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2310   -1.1382    1.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5317    0.6651    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8917   -0.0030    1.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3905   -0.9218   -1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069    0.8108   -0.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7377    0.3029    0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5653   -1.4898    0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6568   -0.8913   -2.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4992    2.1574   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7910    0.9375    0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1145    2.2207   -0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8155   -0.3825   -4.6606 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
 11 10  1  1
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
  2 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 30 32  1  0
 24 11  1  0
 23 15  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  7 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 12 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 16 56  1  0
 18 57  1  0
 20 58  1  0
 20 59  1  0
 20 60  1  0
 22 61  1  0
 22 62  1  0
 22 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 29 69  1  0
 29 70  1  0
 29 71  1  0
 32 72  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
13'-Carboxy-g-tocotrienol	Generator
13'-Carboxy-γ-tocotrienol	Generator
13AgammaTE	HMDB
(2E,6E,10E)-13-[(2R)-6-Hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6,10-trienoate	Generator

Chemical Formula

C₂₈H₄₀O₄

Average Molecular Weight

440.6148

Monoisotopic Molecular Weight

440.292659768

IUPAC Name

(2E,6E,10E)-13-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid

Traditional Name

(2E,6E,10E)-13-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C28H40O4/c1-19(12-8-14-21(3)27(30)31)10-7-11-20(2)13-9-16-28(6)17-15-24-18-25(29)22(4)23(5)26(24)32-28/h10,13-14,18,29H,7-9,11-12,15-17H2,1-6H3,(H,30,31)/b19-10+,20-13+,21-14+/t28-/m1/s1

InChI Key

UJMZKOBSLDXUHY-YQHRJHOASA-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 acid
Chromane
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Branched fatty acid
Methyl-branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Benzenoid
Unsaturated fatty acid
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0012558)
Membrane (HMDB: HMDB0012558)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012558)

Source

Endogenous

Endogenous (HMDB: HMDB0012558)

Animal

Animal (HMDB: HMDB0012558)

Exogenous

Food

Food (HMDB: HMDB0012558)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0012558)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0012558)

Cellular process

Cell signaling (HMDB: HMDB0012558)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0012558)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0012558)

Nutrient

Nutrient (HMDB: HMDB0012558)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012558)

Emulsifier (HMDB: HMDB0012558)

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	0.00042 g/L	ALOGPS
logP	6.46	ALOGPS
logP	7.97	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	5.07	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	134.6 m³·mol⁻¹	ChemAxon
Polarizability	53.59 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]+	205.547	31661259
DarkChem	[M-H]-	204.229	31661259
DeepCCS	[M+H]+	216.123	30932474
DeepCCS	[M-H]-	213.728	30932474
DeepCCS	[M-2H]-	246.61	30932474
DeepCCS	[M+Na]+	222.036	30932474
AllCCS	[M+H]+	217.8	32859911
AllCCS	[M+H-H2O]+	215.6	32859911
AllCCS	[M+NH4]+	219.8	32859911
AllCCS	[M+Na]+	220.4	32859911
AllCCS	[M-H]-	207.6	32859911
AllCCS	[M+Na-2H]-	209.3	32859911
AllCCS	[M+HCOO]-	211.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
13'-Carboxy-gamma-tocotrienol	C\C(CC\C=C(/C)C(O)=O)=C/CC\C(C)=C\CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2	4939.0	Standard polar	33892256
13'-Carboxy-gamma-tocotrienol	C\C(CC\C=C(/C)C(O)=O)=C/CC\C(C)=C\CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2	3392.6	Standard non polar	33892256
13'-Carboxy-gamma-tocotrienol	C\C(CC\C=C(/C)C(O)=O)=C/CC\C(C)=C\CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2	3595.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
13'-Carboxy-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)C(=O)O[Si](C)(C)C	3376.6	Semi standard non polar	33892256
13'-Carboxy-gamma-tocotrienol,1TMS,isomer #2	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)C(=O)O	3500.8	Semi standard non polar	33892256
13'-Carboxy-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)C(=O)O[Si](C)(C)C	3323.8	Semi standard non polar	33892256
13'-Carboxy-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)C(=O)O[Si](C)(C)C(C)(C)C	3637.4	Semi standard non polar	33892256
13'-Carboxy-gamma-tocotrienol,1TBDMS,isomer #2	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)C(=O)O	3753.2	Semi standard non polar	33892256
13'-Carboxy-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)C(=O)O[Si](C)(C)C(C)(C)C	3824.1	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'-Carboxy-gamma-tocotrienol GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-1394300000-23595ddcefae7a79ba51	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13'-Carboxy-gamma-tocotrienol GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-1047590000-9fdeaf3f8312ef52a47b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13'-Carboxy-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'-Carboxy-gamma-tocotrienol 10V, Positive-QTOF	splash10-0fdp-0636900000-e03152e51048e5fa6832	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocotrienol 20V, Positive-QTOF	splash10-0udi-0922000000-4acf73c008316651971a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocotrienol 40V, Positive-QTOF	splash10-0udi-1910000000-ccdca31bc77bf0a54795	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocotrienol 10V, Negative-QTOF	splash10-000i-0001900000-7f5ba63206cca5ef9b82	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocotrienol 20V, Negative-QTOF	splash10-000b-1709700000-69bc7cff5ee914bf661d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocotrienol 40V, Negative-QTOF	splash10-0092-3924200000-1366b1d5ee702e7c59e4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocotrienol 10V, Positive-QTOF	splash10-000e-0489300000-de85d00a27de026ee8a1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocotrienol 20V, Positive-QTOF	splash10-0f72-1493000000-eb93552b5271ca59d667	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocotrienol 40V, Positive-QTOF	splash10-0006-2910000000-009e6415748ca322f4ff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocotrienol 10V, Negative-QTOF	splash10-0002-0109100000-bdc484e6f9534e60c30e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocotrienol 20V, Negative-QTOF	splash10-0ar1-0419000000-5bddc845c6fc72bb1a84	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocotrienol 40V, Negative-QTOF	splash10-004r-0209000000-42d0ae4b5b676b92c5d9	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

FDB029124

KNApSAcK ID

Not Available

Chemspider ID

30776630

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481464

PDB ID

Not Available

ChEBI ID

139534

Food Biomarker Ontology

Not Available

VMH ID

Not Available

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'-Carboxy-gamma-tocotrienol (HMDB0012558)

MOL for HMDB0012558 (13'-Carboxy-gamma-tocotrienol)

3D MOL for HMDB0012558 (13'-Carboxy-gamma-tocotrienol)

3D SDF for HMDB0012558 (13'-Carboxy-gamma-tocotrienol)

3D-SDF for HMDB0012558 (13'-Carboxy-gamma-tocotrienol)

PDB for HMDB0012558 (13'-Carboxy-gamma-tocotrienol)

3D PDB for HMDB0012558 (13'-Carboxy-gamma-tocotrienol)

SMILES for HMDB0012558 (13'-Carboxy-gamma-tocotrienol)

INCHI for HMDB0012558 (13'-Carboxy-gamma-tocotrienol)

Structure for HMDB0012558 (13'-Carboxy-gamma-tocotrienol)

3D Structure for HMDB0012558 (13'-Carboxy-gamma-tocotrienol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra