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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:02:50 UTC

Update Date

2022-03-07 02:51:26 UTC

HMDB ID

HMDB0012555

Secondary Accession Numbers

HMDB12555

Metabolite Identification

Common Name

13'-Carboxy-alpha-tocopherol

Description

13'-carboxy-alpha-tocopherol is a dehydrogenation carboxylate product of 13'-hydroxy-a-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. The tocopherols ( a-tocopherol , b-tocopherol ,r-tocopherol and d-tocopherol ) and their corresponding tocotrienols are synthesized by plants and have vitamin E antixoidant activity (see pathway vitamin E biosynthesis ). They differ in the number and location of methyl groups on the chromanol ring. The naturally occurring form of a-tocopherol is (2R,4'R,8'R)-a-tocopherol (synonym (R,R,R)-a-tocopherol). Synthetic a-tocopherols are a racemic mixture of eight different R and S stereoisomers. Only the 2R forms are recognized as meeting human requirements. The in vivo function of vitamin E is to scavenge peroxyl radicals via its phenolic (chromanol) hydroxyl group, thus protecting lipids against free radical-catalyzed peroxidation. The tocopheryl radical formed can then be reduced by reductants such as L-ascorbate. Other major products of a-tocopherol oxidation include α-tocopherylquinone and epoxy-a-tocopherols. The metabolites a-tocopheronic acid and its lactone, known as the Simon metabolites, are generally believed to be artefacts. In addition to these oxidation products, the other major class of tocopherol metabolites is the carboxyethyl-hydroxychromans.These metabolites are produced in significant amounts in response to excess vitamin E ingestion. Vitamin E is fat-soluble and its utilization requires intestinal fat absorption mechanisms. It is secreted from the intestine into the lymphatic system in chylomicrons which subsequently enter the plasma. Lipolysis of these chylomicrons can result in delivery of vitamin E to tissues, transfer to high-density lipoproteins (and subsequently to other lipoproteins via the phospholipid exchange protein), or retention in chylomicron remnants. These remnants are taken up by the liver. Natural (R,R,R)-α-tocopherol and synthetic 2R-α-tocopherols are then preferentially secreted from the liver into plasma as a result of the specificity of the α-tocopherol transfer protein. This protein, along with the metabolism of excess vitamin E in the liver and excretion into urine and bile, mediate the supply of a-tocopherol in plasma and tissues.

Structure

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


  Mrv0541 02251208062D          

 33 34  0  0  1  0            999 V2000
   10.5877  -12.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4127  -12.3313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8252  -13.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4127  -13.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8252  -14.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4127  -15.1893    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5877  -15.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8252  -15.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6502  -15.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0627  -16.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8877  -16.6182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.4752  -17.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8877  -15.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6022  -15.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3167  -15.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0311  -15.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0311  -14.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7457  -15.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4601  -15.3807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7457  -16.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4601  -17.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0311  -17.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0311  -17.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3167  -16.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6022  -17.0307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8252  -11.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6502  -11.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0627  -10.9024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8877  -10.9024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3002  -11.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3002  -10.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1252  -10.1879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8877   -9.4734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
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  2 26  1  0  0  0  0
  3  4  1  0  0  0  0
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 15 24  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
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 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END

HMDB0012555
     RDKit          3D
13'-Carboxy-alpha-tocopherol
 81 82  0  0  0  0  0  0  0  0999 V2000
   -9.2142    2.3691   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1653    1.3602   -0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9190    1.7857   -0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5300    0.4716    0.1222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2798    1.0880   -1.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3975    0.7658    1.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2445    0.3704   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0724    1.7020    1.5574 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1030   -0.3519    2.5485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6726    1.1583    0.6323 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1942    2.0760   -0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.9463    3.3230   -0.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0161    3.8044   -0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5253    3.3518    0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0233    3.6509    1.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4250   -2.9029    0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3369   -2.8265   -1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7667   -1.2501   -1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6987    0.4391   -1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3075    1.8640    1.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6952    0.3637    2.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8303    0.5000   -0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0287    0.2463    2.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3033   -1.7982    1.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1700   -1.7693    0.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9586    1.8242    0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0164    0.6963    0.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4398    1.0357   -1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7776   -1.3270   -1.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899   -1.6960   -0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9787   -2.2085   -1.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7796   -0.7843   -3.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7397    0.6784   -2.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2050    0.0165   -3.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8140   -0.1496    0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8020   -1.9366    0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3284   -2.1604   -1.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4343   -0.4260   -1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3641   -2.0220    0.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4206   -1.3255   -0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8581    0.9241   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5375   -0.6621    2.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5973   -0.7200    0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8315   -0.0098    3.4598 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
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 13 14  1  6
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 30 31  2  0
 30 32  1  0
 13 33  1  0
  9  2  1  0
 33  5  1  0
  1 34  1  0
  1 35  1  0
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 17 56  1  0
 18 57  1  1
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 19 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  0
 22 66  1  0
 23 67  1  6
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 25 72  1  0
 26 73  1  0
 26 74  1  0
 27 75  1  0
 27 76  1  0
 28 77  1  0
 29 78  1  0
 29 79  1  0
 29 80  1  0
 32 81  1  0
M  END


  Mrv0541 02251208062D          

 33 34  0  0  1  0            999 V2000
   10.5877  -12.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4127  -12.3313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8252  -13.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4127  -13.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8252  -14.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4127  -15.1893    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5877  -15.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8252  -15.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6502  -15.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0627  -16.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8877  -16.6182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   14.6022  -15.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3167  -15.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0311  -15.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.4601  -15.3807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7457  -16.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4601  -17.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.0311  -17.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3167  -16.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6022  -17.0307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8252  -11.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6502  -11.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0627  -10.9024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8877  -10.9024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3002  -11.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3002  -10.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1252  -10.1879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8877   -9.4734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2 26  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 11 25  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 24  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012555

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H](CCC[C@H](C)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C)CCCC(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O4/c1-19(13-9-15-21(3)28(31)32)11-8-12-20(2)14-10-17-29(7)18-16-25-24(6)26(30)22(4)23(5)27(25)33-29/h19-21,30H,8-18H2,1-7H3,(H,31,32)/t19-,20+,21?,29+/m1/s1

> <INCHI_KEY>
NJIUWSABAIXPGI-AXTKCOKSSA-N

> <FORMULA>
C29H48O4

> <MOLECULAR_WEIGHT>
460.689

> <EXACT_MASS>
460.355260024

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
57.12295054326641

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R,10S)-13-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltridecanoic acid

> <ALOGPS_LOGP>
7.38

> <JCHEM_LOGP>
9.443442677000002

> <ALOGPS_LOGS>
-6.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.802178810155157

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.999793180837479

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852614901837207

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
137.0654

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.25e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R,10S)-13-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6,10-trimethyltridecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012555
     RDKit          3D
13'-Carboxy-alpha-tocopherol
 81 82  0  0  0  0  0  0  0  0999 V2000
   -9.2142    2.3691   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1653    1.3602   -0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9190    1.7857   -0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6335    3.2195    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9564    0.8441    0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2234   -0.5098    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4444   -0.9442   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7798   -2.3610   -0.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4248    0.0112   -0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6752   -0.4292   -0.9856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1487   -1.4507    0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7987   -0.9807   -0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5300    0.4716    0.1222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2798    1.0880   -1.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3975    0.7658    1.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705    0.2057    0.6098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.5602    1.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3764    0.0251    1.2190 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2733   -1.4636    1.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9116    0.7178    0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2445    0.3704   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4840   -1.0202   -0.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8993   -1.1442   -1.5112 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1577   -0.2440   -2.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9617   -1.0422   -0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3037   -1.1772   -1.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4321   -1.1463   -0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6231    0.0935    0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8933   -0.1292    1.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5836    0.5376    1.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0724    1.7020    1.5574 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1030   -0.3519    2.5485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6726    1.1583    0.6323 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1942    2.0760   -0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3164    2.5463   -1.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9463    3.3230   -0.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0161    3.8044   -0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5253    3.3518    0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0233    3.6509    1.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4250   -2.9029    0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3369   -2.8265   -1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8821   -2.4727   -0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3892    0.2339   -1.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3383   -2.4443   -0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1074   -1.6647    1.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7667   -1.2501   -1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0429   -1.5823    0.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8593    2.1124   -1.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2827    1.2194   -1.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6987    0.4391   -1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3075    1.8640    1.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6952    0.3637    2.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8303    0.5000   -0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1648   -0.8975    0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2500    0.0548    2.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0548    1.6458    1.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0287    0.2463    2.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3033   -1.7982    1.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1700   -1.7693    0.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0578   -2.0044    1.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1304    0.6710   -0.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9586    1.8242    0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0164    0.6963    0.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4398    1.0357   -1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7776   -1.3270   -1.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899   -1.6960   -0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9787   -2.2085   -1.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7796   -0.7843   -3.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7397    0.6784   -2.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2050    0.0165   -3.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8140   -0.1496    0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8020   -1.9366    0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3284   -2.1604   -1.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4343   -0.4260   -1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3641   -2.0220    0.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4206   -1.3255   -0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8581    0.9241   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2947    0.8716    1.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5375   -0.6621    2.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5973   -0.7200    0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8315   -0.0098    3.4598 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 30 32  1  0
 13 33  1  0
  9  2  1  0
 33  5  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  4 38  1  0
  4 39  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 14 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  1
 19 58  1  0
 19 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  0
 22 66  1  0
 23 67  1  6
 24 68  1  0
 24 69  1  0
 24 70  1  0
 25 71  1  0
 25 72  1  0
 26 73  1  0
 26 74  1  0
 27 75  1  0
 27 76  1  0
 28 77  1  0
 29 78  1  0
 29 79  1  0
 29 80  1  0
 32 81  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      19.764 -23.018   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.304 -23.018   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.074 -24.352   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.304 -25.686   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.074 -27.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.304 -28.353   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.764 -28.353   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.074 -29.687   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.614 -29.687   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.384 -31.021   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.924 -31.021   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.154 -32.354   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.924 -29.481   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.257 -28.711   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.591 -29.481   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.925 -28.711   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.925 -27.171   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.259 -29.481   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      32.592 -28.711   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      31.259 -31.021   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      32.592 -31.791   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      29.925 -31.791   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      29.925 -33.331   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      28.591 -31.021   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      27.257 -31.791   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      22.074 -21.685   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.614 -21.685   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      24.384 -20.351   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.924 -20.351   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      26.694 -21.685   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      26.694 -19.017   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      28.234 -19.017   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      25.924 -17.684   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   25                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   15   22   25                                                  
CONECT   25   11   24                                                       
CONECT   26    2   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

COMPND    HMDB0012555
HETATM    1  C1  UNL     1      -9.214   2.369  -0.754  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.165   1.360  -0.455  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.919   1.786  -0.051  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.634   3.220   0.085  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.956   0.844   0.221  1.00  0.00           C  
HETATM    6  C6  UNL     1      -6.223  -0.510   0.094  1.00  0.00           C  
HETATM    7  C7  UNL     1      -7.444  -0.944  -0.302  1.00  0.00           C  
HETATM    8  C8  UNL     1      -7.780  -2.361  -0.453  1.00  0.00           C  
HETATM    9  C9  UNL     1      -8.425   0.011  -0.580  1.00  0.00           C  
HETATM   10  O1  UNL     1      -9.675  -0.429  -0.986  1.00  0.00           O  
HETATM   11  C10 UNL     1      -5.149  -1.451   0.408  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.799  -0.981  -0.088  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.530   0.472   0.122  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.280   1.088  -1.249  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.397   0.766   1.067  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.071   0.206   0.610  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.000   0.560   1.616  1.00  0.00           C  
HETATM   18  C17 UNL     1       1.376   0.025   1.219  1.00  0.00           C  
HETATM   19  C18 UNL     1       1.273  -1.464   1.128  1.00  0.00           C  
HETATM   20  C19 UNL     1       1.912   0.718   0.032  1.00  0.00           C  
HETATM   21  C20 UNL     1       3.245   0.370  -0.491  1.00  0.00           C  
HETATM   22  C21 UNL     1       3.484  -1.020  -0.944  1.00  0.00           C  
HETATM   23  C22 UNL     1       4.899  -1.144  -1.511  1.00  0.00           C  
HETATM   24  C23 UNL     1       5.158  -0.244  -2.670  1.00  0.00           C  
HETATM   25  C24 UNL     1       5.962  -1.042  -0.415  1.00  0.00           C  
HETATM   26  C25 UNL     1       7.304  -1.177  -1.051  1.00  0.00           C  
HETATM   27  C26 UNL     1       8.432  -1.146  -0.106  1.00  0.00           C  
HETATM   28  C27 UNL     1       8.623   0.093   0.662  1.00  0.00           C  
HETATM   29  C28 UNL     1       9.893  -0.129   1.535  1.00  0.00           C  
HETATM   30  C29 UNL     1       7.584   0.538   1.577  1.00  0.00           C  
HETATM   31  O2  UNL     1       7.072   1.702   1.557  1.00  0.00           O  
HETATM   32  O3  UNL     1       7.103  -0.352   2.549  1.00  0.00           O  
HETATM   33  O4  UNL     1      -4.673   1.158   0.632  1.00  0.00           O  
HETATM   34  H1  UNL     1     -10.194   2.076  -0.341  1.00  0.00           H  
HETATM   35  H2  UNL     1      -9.316   2.546  -1.849  1.00  0.00           H  
HETATM   36  H3  UNL     1      -8.946   3.323  -0.221  1.00  0.00           H  
HETATM   37  H4  UNL     1      -7.016   3.804  -0.791  1.00  0.00           H  
HETATM   38  H5  UNL     1      -5.525   3.352   0.087  1.00  0.00           H  
HETATM   39  H6  UNL     1      -7.023   3.651   1.046  1.00  0.00           H  
HETATM   40  H7  UNL     1      -7.425  -2.903   0.472  1.00  0.00           H  
HETATM   41  H8  UNL     1      -7.337  -2.826  -1.358  1.00  0.00           H  
HETATM   42  H9  UNL     1      -8.882  -2.473  -0.431  1.00  0.00           H  
HETATM   43  H10 UNL     1     -10.389   0.234  -1.189  1.00  0.00           H  
HETATM   44  H11 UNL     1      -5.338  -2.444  -0.080  1.00  0.00           H  
HETATM   45  H12 UNL     1      -5.107  -1.665   1.504  1.00  0.00           H  
HETATM   46  H13 UNL     1      -3.767  -1.250  -1.166  1.00  0.00           H  
HETATM   47  H14 UNL     1      -3.043  -1.582   0.487  1.00  0.00           H  
HETATM   48  H15 UNL     1      -2.859   2.112  -1.140  1.00  0.00           H  
HETATM   49  H16 UNL     1      -4.283   1.219  -1.719  1.00  0.00           H  
HETATM   50  H17 UNL     1      -2.699   0.439  -1.903  1.00  0.00           H  
HETATM   51  H18 UNL     1      -2.308   1.864   1.174  1.00  0.00           H  
HETATM   52  H19 UNL     1      -2.695   0.364   2.056  1.00  0.00           H  
HETATM   53  H20 UNL     1      -0.830   0.500  -0.425  1.00  0.00           H  
HETATM   54  H21 UNL     1      -1.165  -0.898   0.594  1.00  0.00           H  
HETATM   55  H22 UNL     1      -0.250   0.055   2.571  1.00  0.00           H  
HETATM   56  H23 UNL     1       0.055   1.646   1.827  1.00  0.00           H  
HETATM   57  H24 UNL     1       2.029   0.246   2.111  1.00  0.00           H  
HETATM   58  H25 UNL     1       0.303  -1.798   1.626  1.00  0.00           H  
HETATM   59  H26 UNL     1       1.170  -1.769   0.087  1.00  0.00           H  
HETATM   60  H27 UNL     1       2.058  -2.004   1.712  1.00  0.00           H  
HETATM   61  H28 UNL     1       1.130   0.671  -0.776  1.00  0.00           H  
HETATM   62  H29 UNL     1       1.959   1.824   0.310  1.00  0.00           H  
HETATM   63  H30 UNL     1       4.016   0.696   0.255  1.00  0.00           H  
HETATM   64  H31 UNL     1       3.440   1.036  -1.378  1.00  0.00           H  
HETATM   65  H32 UNL     1       2.778  -1.327  -1.713  1.00  0.00           H  
HETATM   66  H33 UNL     1       3.490  -1.696  -0.053  1.00  0.00           H  
HETATM   67  H34 UNL     1       4.979  -2.209  -1.876  1.00  0.00           H  
HETATM   68  H35 UNL     1       5.780  -0.784  -3.435  1.00  0.00           H  
HETATM   69  H36 UNL     1       5.740   0.678  -2.394  1.00  0.00           H  
HETATM   70  H37 UNL     1       4.205   0.016  -3.177  1.00  0.00           H  
HETATM   71  H38 UNL     1       5.814  -0.150   0.181  1.00  0.00           H  
HETATM   72  H39 UNL     1       5.802  -1.937   0.231  1.00  0.00           H  
HETATM   73  H40 UNL     1       7.328  -2.160  -1.640  1.00  0.00           H  
HETATM   74  H41 UNL     1       7.434  -0.426  -1.894  1.00  0.00           H  
HETATM   75  H42 UNL     1       8.364  -2.022   0.621  1.00  0.00           H  
HETATM   76  H43 UNL     1       9.421  -1.325  -0.652  1.00  0.00           H  
HETATM   77  H44 UNL     1       8.858   0.924  -0.046  1.00  0.00           H  
HETATM   78  H45 UNL     1      10.295   0.872   1.722  1.00  0.00           H  
HETATM   79  H46 UNL     1       9.537  -0.662   2.436  1.00  0.00           H  
HETATM   80  H47 UNL     1      10.597  -0.720   0.916  1.00  0.00           H  
HETATM   81  H48 UNL     1       6.832  -0.010   3.460  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    3    9
CONECT    3    4    5
CONECT    4   37   38   39
CONECT    5    6    6   33
CONECT    6    7   11
CONECT    7    8    9    9
CONECT    8   40   41   42
CONECT    9   10
CONECT   10   43
CONECT   11   12   44   45
CONECT   12   13   46   47
CONECT   13   14   15   33
CONECT   14   48   49   50
CONECT   15   16   51   52
CONECT   16   17   53   54
CONECT   17   18   55   56
CONECT   18   19   20   57
CONECT   19   58   59   60
CONECT   20   21   61   62
CONECT   21   22   63   64
CONECT   22   23   65   66
CONECT   23   24   25   67
CONECT   24   68   69   70
CONECT   25   26   71   72
CONECT   26   27   73   74
CONECT   27   28   75   76
CONECT   28   29   30   77
CONECT   29   78   79   80
CONECT   30   31   31   32
CONECT   32   81
END

HMDB0012555
     RDKit          3D
13'-Carboxy-alpha-tocopherol
 81 82  0  0  0  0  0  0  0  0999 V2000
   -9.2142    2.3691   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1653    1.3602   -0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9190    1.7857   -0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6335    3.2195    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9564    0.8441    0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2234   -0.5098    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4444   -0.9442   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7798   -2.3610   -0.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4248    0.0112   -0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6752   -0.4292   -0.9856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1487   -1.4507    0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7987   -0.9807   -0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5300    0.4716    0.1222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2798    1.0880   -1.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3975    0.7658    1.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705    0.2057    0.6098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.5602    1.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3764    0.0251    1.2190 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2733   -1.4636    1.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9116    0.7178    0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2445    0.3704   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4840   -1.0202   -0.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8993   -1.1442   -1.5112 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1577   -0.2440   -2.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9617   -1.0422   -0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3037   -1.1772   -1.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4321   -1.1463   -0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6231    0.0935    0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8933   -0.1292    1.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5836    0.5376    1.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0724    1.7020    1.5574 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1030   -0.3519    2.5485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6726    1.1583    0.6323 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1942    2.0760   -0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3164    2.5463   -1.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9463    3.3230   -0.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0161    3.8044   -0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5253    3.3518    0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0233    3.6509    1.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4250   -2.9029    0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3369   -2.8265   -1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8821   -2.4727   -0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3892    0.2339   -1.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3383   -2.4443   -0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1074   -1.6647    1.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7667   -1.2501   -1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0429   -1.5823    0.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8593    2.1124   -1.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2827    1.2194   -1.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6987    0.4391   -1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3075    1.8640    1.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6952    0.3637    2.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8303    0.5000   -0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1648   -0.8975    0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2500    0.0548    2.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0548    1.6458    1.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0287    0.2463    2.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3033   -1.7982    1.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1700   -1.7693    0.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0578   -2.0044    1.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1304    0.6710   -0.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9586    1.8242    0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0164    0.6963    0.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4398    1.0357   -1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7776   -1.3270   -1.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899   -1.6960   -0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9787   -2.2085   -1.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7796   -0.7843   -3.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7397    0.6784   -2.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2050    0.0165   -3.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8140   -0.1496    0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8020   -1.9366    0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3284   -2.1604   -1.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4343   -0.4260   -1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3641   -2.0220    0.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4206   -1.3255   -0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8581    0.9241   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2947    0.8716    1.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5375   -0.6621    2.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5973   -0.7200    0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8315   -0.0098    3.4598 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 30 32  1  0
 13 33  1  0
  9  2  1  0
 33  5  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  4 38  1  0
  4 39  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 14 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  1
 19 58  1  0
 19 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  0
 22 66  1  0
 23 67  1  6
 24 68  1  0
 24 69  1  0
 24 70  1  0
 25 71  1  0
 25 72  1  0
 26 73  1  0
 26 74  1  0
 27 75  1  0
 27 76  1  0
 28 77  1  0
 29 78  1  0
 29 79  1  0
 29 80  1  0
 32 81  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
13'-Carboxy-a-tocopherol	Generator
13'-Carboxy-α-tocopherol	Generator
(6R,10S)-13-[(2S)-6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltridecanoate	HMDB

Chemical Formula

C₂₉H₄₈O₄

Average Molecular Weight

460.689

Monoisotopic Molecular Weight

460.355260024

IUPAC Name

(6R,10S)-13-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltridecanoic acid

Traditional Name

(6R,10S)-13-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6,10-trimethyltridecanoic acid

CAS Registry Number

Not Available

SMILES

C[C@H](CCC[C@H](C)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C)CCCC(C)C(O)=O

InChI Identifier

InChI=1S/C29H48O4/c1-19(13-9-15-21(3)28(31)32)11-8-12-20(2)14-10-17-29(7)18-16-25-24(6)26(30)22(4)23(5)27(25)33-29/h19-21,30H,8-18H2,1-7H3,(H,31,32)/t19-,20+,21?,29+/m1/s1

InChI Key

NJIUWSABAIXPGI-AXTKCOKSSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Tocopherols

Alternative Parents

Substituents

Tocopherol
Diterpenoid
Long-chain fatty acid
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
Branched fatty acid
Methyl-branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Benzenoid
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

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012555)

Source

Endogenous

Endogenous (HMDB: HMDB0012555)

Animal

Animal (HMDB: HMDB0012555)

Exogenous

Food

Food (HMDB: HMDB0012555)

Exogenous (HMDB: HMDB0012555)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012555)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012555)

Lipid metabolism pathway (HMDB: HMDB0012555)

Cellular process

Cell signaling (HMDB: HMDB0012555)

Biochemical process

Lipid transport (HMDB: HMDB0012555)

Role

Biological role

Energy source (HMDB: HMDB0012555)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012555)

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	6.2e-05 g/L	ALOGPS
logP	7.38	ALOGPS
logP	9.44	ChemAxon
logS	-6.9	ALOGPS
pKa (Strongest Acidic)	5	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	13	ChemAxon
Refractivity	137.07 m³·mol⁻¹	ChemAxon
Polarizability	57.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	208.685	31661259
DarkChem	[M-H]-	204.929	31661259
DeepCCS	[M+H]+	217.948	30932474
DeepCCS	[M-H]-	215.553	30932474
DeepCCS	[M-2H]-	248.435	30932474
DeepCCS	[M+Na]+	223.861	30932474
AllCCS	[M+H]+	220.2	32859911
AllCCS	[M+H-H2O]+	218.3	32859911
AllCCS	[M+NH4]+	222.0	32859911
AllCCS	[M+Na]+	222.5	32859911
AllCCS	[M-H]-	219.0	32859911
AllCCS	[M+Na-2H]-	222.0	32859911
AllCCS	[M+HCOO]-	225.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	10.01 minutes	32390414
Predicted by Siyang on May 30, 2022	29.8048 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.84 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	47.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3651.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	832.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	350.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	383.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	770.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1644.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1381.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	108.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2604.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	926.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2716.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	965.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	638.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	622.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	697.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
13'-Carboxy-alpha-tocopherol	C[C@H](CCC[C@H](C)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C)CCCC(C)C(O)=O	4695.6	Standard polar	33892256
13'-Carboxy-alpha-tocopherol	C[C@H](CCC[C@H](C)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C)CCCC(C)C(O)=O	3363.1	Standard non polar	33892256
13'-Carboxy-alpha-tocopherol	C[C@H](CCC[C@H](C)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C)CCCC(C)C(O)=O	3500.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
13'-Carboxy-alpha-tocopherol,1TMS,isomer #1	CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O)O2)C(C)=C1O[Si](C)(C)C	3382.3	Semi standard non polar	33892256
13'-Carboxy-alpha-tocopherol,1TMS,isomer #2	CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C)O2)C(C)=C1O	3324.1	Semi standard non polar	33892256
13'-Carboxy-alpha-tocopherol,2TMS,isomer #1	CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C)O2)C(C)=C1O[Si](C)(C)C	3350.4	Semi standard non polar	33892256
13'-Carboxy-alpha-tocopherol,1TBDMS,isomer #1	CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O)O2)C(C)=C1O[Si](C)(C)C(C)(C)C	3637.6	Semi standard non polar	33892256
13'-Carboxy-alpha-tocopherol,1TBDMS,isomer #2	CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O	3587.1	Semi standard non polar	33892256
13'-Carboxy-alpha-tocopherol,2TBDMS,isomer #1	CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O[Si](C)(C)C(C)(C)C	3859.5	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'-Carboxy-alpha-tocopherol GC-MS (Non-derivatized) - 70eV, Positive	splash10-052e-1295300000-2ba3285725719c588128	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13'-Carboxy-alpha-tocopherol GC-MS (2 TMS) - 70eV, Positive	splash10-000i-3156490000-03a0da1adf52e9e61fe3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13'-Carboxy-alpha-tocopherol 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-alpha-tocopherol 10V, Positive-QTOF	splash10-03xu-0411900000-6aac4b4053205659c4ba	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 20V, Positive-QTOF	splash10-014i-0911100000-a2eb530497be580e2a0b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 40V, Positive-QTOF	splash10-014i-0900000000-8cfa2f87ad5b2d0fe221	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 10V, Negative-QTOF	splash10-0a4i-0000900000-8234c0b64f303a84be8b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 20V, Negative-QTOF	splash10-0cdi-0401900000-33f2cd8e55dfc5848254	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 40V, Negative-QTOF	splash10-0002-3912200000-e17701c9ef0503d01b0f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 10V, Positive-QTOF	splash10-014r-0219300000-c80c91d9a652fdd333f5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 20V, Positive-QTOF	splash10-014i-4459000000-a023b2ae98132fcbed7f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 40V, Positive-QTOF	splash10-0a4j-9651000000-b280243e088f79fef0e3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 10V, Negative-QTOF	splash10-0a4i-0000900000-55fc02ff579e3c3add1b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 20V, Negative-QTOF	splash10-0cdj-2224900000-4590a0f16b2640290f4f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Carboxy-alpha-tocopherol 40V, Negative-QTOF	splash10-0a4j-1279200000-2e3da45716fd5d0a54b1	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

FDB029121

KNApSAcK ID

Not Available

Chemspider ID

35032539

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481461

PDB ID

Not Available

ChEBI ID

145207

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-alpha-tocopherol (HMDB0012555)

MOL for HMDB0012555 (13'-Carboxy-alpha-tocopherol)

3D MOL for HMDB0012555 (13'-Carboxy-alpha-tocopherol)

3D SDF for HMDB0012555 (13'-Carboxy-alpha-tocopherol)

3D-SDF for HMDB0012555 (13'-Carboxy-alpha-tocopherol)

PDB for HMDB0012555 (13'-Carboxy-alpha-tocopherol)

3D PDB for HMDB0012555 (13'-Carboxy-alpha-tocopherol)

SMILES for HMDB0012555 (13'-Carboxy-alpha-tocopherol)

INCHI for HMDB0012555 (13'-Carboxy-alpha-tocopherol)

Structure for HMDB0012555 (13'-Carboxy-alpha-tocopherol)

3D Structure for HMDB0012555 (13'-Carboxy-alpha-tocopherol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra