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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:02:06 UTC

Update Date

2021-09-14 15:41:21 UTC

HMDB ID

HMDB0012515

Secondary Accession Numbers

HMDB12515

Metabolite Identification

Common Name

11'-Carboxy-alpha-chromanol

Description

11'-carboxy-alpha-tocopherol is a dehydrogenation carboxylate product of 11'-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          

 30 31  0  0  1  0            999 V2000
   12.3086  -12.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0231  -12.4546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7376  -12.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7376  -11.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4520  -10.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4520   -9.9796    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7376   -9.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1665   -9.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8810   -9.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5954   -9.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3099   -9.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5954   -8.7421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0231  -13.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7376  -13.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7376  -14.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4520  -14.9297    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7376  -15.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8645  -14.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6895  -14.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1020  -14.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9270  -14.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3395  -14.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3395  -15.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1646  -15.6442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9270  -16.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3395  -17.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1020  -16.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6895  -17.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6895  -15.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8645  -15.6442    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 13  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
 10 12  2  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
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 16 30  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
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 20 29  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

HMDB0012515
     RDKit          3D
11'-Carboxy-alpha-chromanol
 72 73  0  0  0  0  0  0  0  0999 V2000
   -7.9972   -0.8445   -2.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9032   -0.5876   -1.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5872   -0.9331   -1.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2433   -1.6036   -2.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5848   -0.6877   -0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9314   -0.0529    0.7898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2066    0.3084    1.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5442    0.9663    2.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1896    0.0418    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5016    0.3966    0.3382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7963    0.1896    1.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6907    0.7897    0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1596   -0.1836   -0.1845 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7640    0.5576   -1.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -1.1097    0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1108   -0.5343    0.9097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9536    0.2908    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2064    0.8232    0.6919 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8218    1.6870    1.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725   -0.2508    1.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076   -1.0754   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5248   -0.4597   -1.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8397    0.1309   -0.7184 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8253    1.2486    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8757   -0.9193   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2112   -0.3526   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8149    0.3631   -1.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3034    0.3727   -2.2645 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0138    1.0843   -1.0016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2735   -1.0121   -0.5758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7117    0.0135   -2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6080   -1.7313   -1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6258   -1.0044   -3.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2457   -2.0737   -2.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2194   -0.8781   -3.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9899   -2.3801   -2.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8415    0.7302    3.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7562    2.0451    2.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5160    0.5003    2.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7743    0.8499    1.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458   -0.7697    2.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9766    0.9211    2.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9388    1.2771    1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2095    1.6034    0.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    1.6527   -1.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8631    0.1129   -1.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5772    0.4345   -2.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039   -1.7348    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8531   -1.8184   -0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7503   -1.4178    1.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0736   -0.0257    1.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3804    1.2392   -0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -0.2609   -0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6550    1.5035   -0.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0159    2.4024    1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730    2.2826    2.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4610    1.0723    2.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6321   -0.9639    1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9246    0.2282    1.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8082   -1.5403   -0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2022   -1.9650    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9441    0.3139   -1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7124   -1.2533   -1.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2001    0.6146   -1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1358    0.8942    1.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6322    2.0188    0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9011    1.8289    0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0386   -1.6229   -1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4779   -1.5017    0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0983    0.3952    0.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8747   -1.1868    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8602    0.5507   -0.9551 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  2  0
 27 29  1  0
 13 30  1  0
  9  2  1  0
 30  5  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  4 35  1  0
  4 36  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  6
 19 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  6
 24 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 29 72  1  0
M  END


  Mrv0541 02251208062D          

 30 31  0  0  1  0            999 V2000
   12.3086  -12.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0231  -12.4546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7376  -12.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7376  -11.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4520  -10.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4520   -9.9796    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7376   -9.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1665   -9.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8810   -9.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5954   -9.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3099   -9.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5954   -8.7421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0231  -13.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7376  -13.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7376  -14.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4520  -14.9297    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7376  -15.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8645  -14.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6895  -14.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1020  -14.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9270  -14.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3395  -14.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3395  -15.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1646  -15.6442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9270  -16.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3395  -17.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1020  -16.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6895  -17.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6895  -15.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8645  -15.6442    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 13  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
 10 12  2  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
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 16 30  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 29  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012515

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H42O4/c1-17(9-7-10-18(2)12-13-23(27)28)11-8-15-26(6)16-14-22-21(5)24(29)19(3)20(4)25(22)30-26/h17-18,29H,7-16H2,1-6H3,(H,27,28)/t17-,18+,26+/m0/s1

> <INCHI_KEY>
FKTCHXAVPYGOSM-CUAXAMRHSA-N

> <FORMULA>
C26H42O4

> <MOLECULAR_WEIGHT>
418.6093

> <EXACT_MASS>
418.308309832

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
51.086101231628064

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,8S)-11-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundecanoic acid

> <ALOGPS_LOGP>
6.43

> <JCHEM_LOGP>
8.011319068666667

> <ALOGPS_LOGS>
-6.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.802178884212683

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.044405650385452

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8526149018312505

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
123.28889999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.05e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,8S)-11-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-4,8-dimethylundecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012515
     RDKit          3D
11'-Carboxy-alpha-chromanol
 72 73  0  0  0  0  0  0  0  0999 V2000
   -7.9972   -0.8445   -2.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9032   -0.5876   -1.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5872   -0.9331   -1.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2433   -1.6036   -2.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5848   -0.6877   -0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9314   -0.0529    0.7898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2066    0.3084    1.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5442    0.9663    2.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1896    0.0418    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5016    0.3966    0.3382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7963    0.1896    1.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6907    0.7897    0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1596   -0.1836   -0.1845 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7640    0.5576   -1.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -1.1097    0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1108   -0.5343    0.9097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9536    0.2908    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2064    0.8232    0.6919 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8218    1.6870    1.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725   -0.2508    1.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076   -1.0754   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5248   -0.4597   -1.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8397    0.1309   -0.7184 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8253    1.2486    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8757   -0.9193   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2112   -0.3526   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8149    0.3631   -1.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3034    0.3727   -2.2645 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0138    1.0843   -1.0016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2735   -1.0121   -0.5758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7117    0.0135   -2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6080   -1.7313   -1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6258   -1.0044   -3.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2457   -2.0737   -2.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2194   -0.8781   -3.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9899   -2.3801   -2.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8415    0.7302    3.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7562    2.0451    2.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5160    0.5003    2.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7743    0.8499    1.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458   -0.7697    2.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9766    0.9211    2.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9388    1.2771    1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2095    1.6034    0.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    1.6527   -1.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8631    0.1129   -1.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5772    0.4345   -2.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039   -1.7348    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8531   -1.8184   -0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7503   -1.4178    1.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0736   -0.0257    1.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3804    1.2392   -0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -0.2609   -0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6550    1.5035   -0.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0159    2.4024    1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730    2.2826    2.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4610    1.0723    2.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6321   -0.9639    1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9246    0.2282    1.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8082   -1.5403   -0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2022   -1.9650    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9441    0.3139   -1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7124   -1.2533   -1.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2001    0.6146   -1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1358    0.8942    1.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6322    2.0188    0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9011    1.8289    0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0386   -1.6229   -1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4779   -1.5017    0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0983    0.3952    0.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8747   -1.1868    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8602    0.5507   -0.9551 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  2  0
 27 29  1  0
 13 30  1  0
  9  2  1  0
 30  5  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  4 35  1  0
  4 36  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  6
 19 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  6
 24 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 29 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      22.976 -22.479   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.310 -23.249   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.644 -22.479   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.644 -20.939   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.977 -20.169   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.977 -18.629   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.644 -17.859   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.311 -17.859   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.645 -18.629   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.978 -17.859   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      32.312 -18.629   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      30.978 -16.319   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      24.310 -24.789   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.644 -25.559   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.644 -27.099   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.977 -27.869   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.644 -28.639   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.747 -26.535   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.287 -26.535   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.057 -27.869   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.597 -27.869   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      32.367 -26.535   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      32.367 -29.203   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      33.907 -29.203   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      31.597 -30.536   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      32.367 -31.870   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.057 -30.536   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.287 -31.870   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      29.287 -29.203   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      27.747 -29.203   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
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   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   30                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   20   27   30                                                  
CONECT   30   16   29                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

COMPND    HMDB0012515
HETATM    1  C1  UNL     1      -7.997  -0.845  -2.074  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.903  -0.588  -1.105  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.587  -0.933  -1.316  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.243  -1.604  -2.591  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.585  -0.688  -0.409  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.931  -0.053   0.790  1.00  0.00           C  
HETATM    7  C7  UNL     1      -6.207   0.308   1.053  1.00  0.00           C  
HETATM    8  C8  UNL     1      -6.544   0.966   2.332  1.00  0.00           C  
HETATM    9  C9  UNL     1      -7.190   0.042   0.107  1.00  0.00           C  
HETATM   10  O1  UNL     1      -8.502   0.397   0.338  1.00  0.00           O  
HETATM   11  C10 UNL     1      -3.796   0.190   1.708  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.691   0.790   0.823  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.160  -0.184  -0.185  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.764   0.558  -1.437  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.126  -1.110   0.348  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.111  -0.534   0.910  1.00  0.00           C  
HETATM   17  C16 UNL     1       0.954   0.291   0.006  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.206   0.823   0.692  1.00  0.00           C  
HETATM   19  C18 UNL     1       1.822   1.687   1.874  1.00  0.00           C  
HETATM   20  C19 UNL     1       3.172  -0.251   1.090  1.00  0.00           C  
HETATM   21  C20 UNL     1       3.708  -1.075  -0.011  1.00  0.00           C  
HETATM   22  C21 UNL     1       4.525  -0.460  -1.058  1.00  0.00           C  
HETATM   23  C22 UNL     1       5.840   0.131  -0.718  1.00  0.00           C  
HETATM   24  C23 UNL     1       5.825   1.249   0.280  1.00  0.00           C  
HETATM   25  C24 UNL     1       6.876  -0.919  -0.366  1.00  0.00           C  
HETATM   26  C25 UNL     1       8.211  -0.353  -0.009  1.00  0.00           C  
HETATM   27  C26 UNL     1       8.815   0.363  -1.134  1.00  0.00           C  
HETATM   28  O2  UNL     1       8.303   0.373  -2.264  1.00  0.00           O  
HETATM   29  O3  UNL     1      10.014   1.084  -1.002  1.00  0.00           O  
HETATM   30  O4  UNL     1      -3.274  -1.012  -0.576  1.00  0.00           O  
HETATM   31  H1  UNL     1      -8.712   0.013  -2.139  1.00  0.00           H  
HETATM   32  H2  UNL     1      -8.608  -1.731  -1.800  1.00  0.00           H  
HETATM   33  H3  UNL     1      -7.626  -1.004  -3.098  1.00  0.00           H  
HETATM   34  H4  UNL     1      -4.246  -2.074  -2.530  1.00  0.00           H  
HETATM   35  H5  UNL     1      -5.219  -0.878  -3.428  1.00  0.00           H  
HETATM   36  H6  UNL     1      -5.990  -2.380  -2.842  1.00  0.00           H  
HETATM   37  H7  UNL     1      -5.841   0.730   3.157  1.00  0.00           H  
HETATM   38  H8  UNL     1      -6.756   2.045   2.226  1.00  0.00           H  
HETATM   39  H9  UNL     1      -7.516   0.500   2.683  1.00  0.00           H  
HETATM   40  H10 UNL     1      -8.774   0.850   1.171  1.00  0.00           H  
HETATM   41  H11 UNL     1      -3.446  -0.770   2.156  1.00  0.00           H  
HETATM   42  H12 UNL     1      -3.977   0.921   2.494  1.00  0.00           H  
HETATM   43  H13 UNL     1      -1.939   1.277   1.440  1.00  0.00           H  
HETATM   44  H14 UNL     1      -3.210   1.603   0.247  1.00  0.00           H  
HETATM   45  H15 UNL     1      -1.696   1.653  -1.277  1.00  0.00           H  
HETATM   46  H16 UNL     1      -0.863   0.113  -1.912  1.00  0.00           H  
HETATM   47  H17 UNL     1      -2.577   0.435  -2.187  1.00  0.00           H  
HETATM   48  H18 UNL     1      -1.604  -1.735   1.142  1.00  0.00           H  
HETATM   49  H19 UNL     1      -0.853  -1.818  -0.461  1.00  0.00           H  
HETATM   50  H20 UNL     1       0.750  -1.418   1.220  1.00  0.00           H  
HETATM   51  H21 UNL     1      -0.074  -0.026   1.905  1.00  0.00           H  
HETATM   52  H22 UNL     1       0.380   1.239  -0.223  1.00  0.00           H  
HETATM   53  H23 UNL     1       1.266  -0.261  -0.875  1.00  0.00           H  
HETATM   54  H24 UNL     1       2.655   1.503  -0.057  1.00  0.00           H  
HETATM   55  H25 UNL     1       1.016   2.402   1.613  1.00  0.00           H  
HETATM   56  H26 UNL     1       2.673   2.283   2.231  1.00  0.00           H  
HETATM   57  H27 UNL     1       1.461   1.072   2.724  1.00  0.00           H  
HETATM   58  H28 UNL     1       2.632  -0.964   1.787  1.00  0.00           H  
HETATM   59  H29 UNL     1       3.925   0.228   1.742  1.00  0.00           H  
HETATM   60  H30 UNL     1       2.808  -1.540  -0.527  1.00  0.00           H  
HETATM   61  H31 UNL     1       4.202  -1.965   0.453  1.00  0.00           H  
HETATM   62  H32 UNL     1       3.944   0.314  -1.610  1.00  0.00           H  
HETATM   63  H33 UNL     1       4.712  -1.253  -1.845  1.00  0.00           H  
HETATM   64  H34 UNL     1       6.200   0.615  -1.680  1.00  0.00           H  
HETATM   65  H35 UNL     1       6.136   0.894   1.287  1.00  0.00           H  
HETATM   66  H36 UNL     1       6.632   2.019   0.031  1.00  0.00           H  
HETATM   67  H37 UNL     1       4.901   1.829   0.250  1.00  0.00           H  
HETATM   68  H38 UNL     1       7.039  -1.623  -1.219  1.00  0.00           H  
HETATM   69  H39 UNL     1       6.478  -1.502   0.504  1.00  0.00           H  
HETATM   70  H40 UNL     1       8.098   0.395   0.817  1.00  0.00           H  
HETATM   71  H41 UNL     1       8.875  -1.187   0.331  1.00  0.00           H  
HETATM   72  H42 UNL     1      10.860   0.551  -0.955  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    3    9
CONECT    3    4    5
CONECT    4   34   35   36
CONECT    5    6    6   30
CONECT    6    7   11
CONECT    7    8    9    9
CONECT    8   37   38   39
CONECT    9   10
CONECT   10   40
CONECT   11   12   41   42
CONECT   12   13   43   44
CONECT   13   14   15   30
CONECT   14   45   46   47
CONECT   15   16   48   49
CONECT   16   17   50   51
CONECT   17   18   52   53
CONECT   18   19   20   54
CONECT   19   55   56   57
CONECT   20   21   58   59
CONECT   21   22   60   61
CONECT   22   23   62   63
CONECT   23   24   25   64
CONECT   24   65   66   67
CONECT   25   26   68   69
CONECT   26   27   70   71
CONECT   27   28   28   29
CONECT   29   72
END

HMDB0012515
     RDKit          3D
11'-Carboxy-alpha-chromanol
 72 73  0  0  0  0  0  0  0  0999 V2000
   -7.9972   -0.8445   -2.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9032   -0.5876   -1.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5872   -0.9331   -1.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2433   -1.6036   -2.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5848   -0.6877   -0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9314   -0.0529    0.7898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2066    0.3084    1.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5442    0.9663    2.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1896    0.0418    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5016    0.3966    0.3382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7963    0.1896    1.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6907    0.7897    0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1596   -0.1836   -0.1845 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7640    0.5576   -1.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -1.1097    0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1108   -0.5343    0.9097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9536    0.2908    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2064    0.8232    0.6919 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8218    1.6870    1.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725   -0.2508    1.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076   -1.0754   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5248   -0.4597   -1.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8397    0.1309   -0.7184 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8253    1.2486    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8757   -0.9193   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2112   -0.3526   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8149    0.3631   -1.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3034    0.3727   -2.2645 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0138    1.0843   -1.0016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2735   -1.0121   -0.5758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7117    0.0135   -2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6080   -1.7313   -1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6258   -1.0044   -3.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2457   -2.0737   -2.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2194   -0.8781   -3.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9899   -2.3801   -2.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8415    0.7302    3.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7562    2.0451    2.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5160    0.5003    2.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7743    0.8499    1.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458   -0.7697    2.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9766    0.9211    2.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9388    1.2771    1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2095    1.6034    0.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    1.6527   -1.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8631    0.1129   -1.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5772    0.4345   -2.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039   -1.7348    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8531   -1.8184   -0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7503   -1.4178    1.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0736   -0.0257    1.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3804    1.2392   -0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -0.2609   -0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6550    1.5035   -0.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0159    2.4024    1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730    2.2826    2.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4610    1.0723    2.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6321   -0.9639    1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9246    0.2282    1.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8082   -1.5403   -0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2022   -1.9650    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9441    0.3139   -1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7124   -1.2533   -1.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2001    0.6146   -1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1358    0.8942    1.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6322    2.0188    0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9011    1.8289    0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0386   -1.6229   -1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4779   -1.5017    0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0983    0.3952    0.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8747   -1.1868    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8602    0.5507   -0.9551 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  2  0
 27 29  1  0
 13 30  1  0
  9  2  1  0
 30  5  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  4 35  1  0
  4 36  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  6
 19 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  6
 24 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 29 72  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11'-Carboxy-alpha-tocopherol	HMDB
(4R,8S)-11-[(2R)-6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundecanoate	Generator

Chemical Formula

C₂₆H₄₂O₄

Average Molecular Weight

418.6093

Monoisotopic Molecular Weight

418.308309832

IUPAC Name

(4R,8S)-11-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundecanoic acid

Traditional Name

(4R,8S)-11-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-4,8-dimethylundecanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H42O4/c1-17(9-7-10-18(2)12-13-23(27)28)11-8-15-26(6)16-14-22-21(5)24(29)19(3)20(4)25(22)30-26/h17-18,29H,7-16H2,1-6H3,(H,27,28)/t17-,18+,26+/m0/s1

InChI Key

FKTCHXAVPYGOSM-CUAXAMRHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Long-chain fatty acid
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
Branched fatty acid
Heterocyclic fatty acid
Methyl-branched fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Benzenoid
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Ether
Organoheterocyclic compound
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

Membrane (HMDB: HMDB0012515)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012515)

Source

Endogenous

Endogenous (HMDB: HMDB0012515)

Animal

Animal (HMDB: HMDB0012515)

Exogenous

Food

Food (HMDB: HMDB0012515)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0012515)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0012515)

Cellular process

Cell signaling (HMDB: HMDB0012515)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0012515)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0012515)

Nutrient

Nutrient (HMDB: HMDB0012515)

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	0.0002 g/L	ALOGPS
logP	6.43	ALOGPS
logP	8.01	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	5.04	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	11	ChemAxon
Refractivity	123.29 m³·mol⁻¹	ChemAxon
Polarizability	51.09 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]+	199.318	31661259
DarkChem	[M-H]-	195.452	31661259
DeepCCS	[M+H]+	201.191	30932474
DeepCCS	[M-H]-	198.833	30932474
DeepCCS	[M-2H]-	231.979	30932474
DeepCCS	[M+Na]+	207.285	30932474
AllCCS	[M+H]+	210.2	32859911
AllCCS	[M+H-H2O]+	208.0	32859911
AllCCS	[M+NH4]+	212.3	32859911
AllCCS	[M+Na]+	212.9	32859911
AllCCS	[M-H]-	210.5	32859911
AllCCS	[M+Na-2H]-	212.7	32859911
AllCCS	[M+HCOO]-	215.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11'-Carboxy-alpha-chromanol	C[C@@H](CCC[C@@H](C)CCC(O)=O)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C	4487.0	Standard polar	33892256
11'-Carboxy-alpha-chromanol	C[C@@H](CCC[C@@H](C)CCC(O)=O)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C	3193.9	Standard non polar	33892256
11'-Carboxy-alpha-chromanol	C[C@@H](CCC[C@@H](C)CCC(O)=O)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C	3295.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
11'-Carboxy-alpha-chromanol,1TMS,isomer #1	CC1=C(C)C2=C(CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCC(=O)O[Si](C)(C)C)O2)C(C)=C1O	3139.5	Semi standard non polar	33892256
11'-Carboxy-alpha-chromanol,1TMS,isomer #2	CC1=C(C)C2=C(CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCC(=O)O)O2)C(C)=C1O[Si](C)(C)C	3180.7	Semi standard non polar	33892256
11'-Carboxy-alpha-chromanol,2TMS,isomer #1	CC1=C(C)C2=C(CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCC(=O)O[Si](C)(C)C)O2)C(C)=C1O[Si](C)(C)C	3173.9	Semi standard non polar	33892256
11'-Carboxy-alpha-chromanol,1TBDMS,isomer #1	CC1=C(C)C2=C(CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCC(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O	3389.4	Semi standard non polar	33892256
11'-Carboxy-alpha-chromanol,1TBDMS,isomer #2	CC1=C(C)C2=C(CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCC(=O)O)O2)C(C)=C1O[Si](C)(C)C(C)(C)C	3426.6	Semi standard non polar	33892256
11'-Carboxy-alpha-chromanol,2TBDMS,isomer #1	CC1=C(C)C2=C(CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCC(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O[Si](C)(C)C(C)(C)C	3664.5	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 - 11'-Carboxy-alpha-chromanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kbg-3797200000-85dcac1a9b7ed68f5cd1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11'-Carboxy-alpha-chromanol GC-MS (2 TMS) - 70eV, Positive	splash10-0002-7278590000-828c9b9f66ffc64eb95c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11'-Carboxy-alpha-chromanol 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 - 11'-Carboxy-alpha-chromanol 10V, Positive-QTOF	splash10-0uxr-0523900000-ef21f5238b7c8e2bbbf2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-alpha-chromanol 20V, Positive-QTOF	splash10-014i-0911000000-cf3e6e9a30136a3d5eb3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-alpha-chromanol 40V, Positive-QTOF	splash10-014i-1910000000-af495d5de8bb0797d94b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-alpha-chromanol 10V, Negative-QTOF	splash10-014i-0003900000-4cb6b570b984217750c4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-alpha-chromanol 20V, Negative-QTOF	splash10-044j-2629500000-5c3801605e8bb39dec74	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-alpha-chromanol 40V, Negative-QTOF	splash10-0a4i-5922100000-1447ca85222f2745f5d4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-alpha-chromanol 10V, Positive-QTOF	splash10-01b9-0029100000-27abda79f9f6424c4c14	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-alpha-chromanol 20V, Positive-QTOF	splash10-052b-2294000000-faba8345028c2158c302	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-alpha-chromanol 40V, Positive-QTOF	splash10-0a4i-6890000000-1f952e56984719f22c5d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-alpha-chromanol 10V, Negative-QTOF	splash10-01b9-0006900000-1d7ac9a558aa3eee86bf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-alpha-chromanol 20V, Negative-QTOF	splash10-0603-7309300000-6264340a4bea444d3f8f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-alpha-chromanol 40V, Negative-QTOF	splash10-0a4i-1494000000-a3c41094b594f64616be	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

FDB029108

KNApSAcK ID

Not Available

Chemspider ID

30776627

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481451

PDB ID

Not Available

ChEBI ID

172659

Food Biomarker Ontology

Not Available

VMH ID

CE5855

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 11'-Carboxy-alpha-chromanol (HMDB0012515)

MOL for HMDB0012515 (11'-Carboxy-alpha-chromanol)

3D MOL for HMDB0012515 (11'-Carboxy-alpha-chromanol)

3D SDF for HMDB0012515 (11'-Carboxy-alpha-chromanol)

3D-SDF for HMDB0012515 (11'-Carboxy-alpha-chromanol)

PDB for HMDB0012515 (11'-Carboxy-alpha-chromanol)

3D PDB for HMDB0012515 (11'-Carboxy-alpha-chromanol)

SMILES for HMDB0012515 (11'-Carboxy-alpha-chromanol)

INCHI for HMDB0012515 (11'-Carboxy-alpha-chromanol)

Structure for HMDB0012515 (11'-Carboxy-alpha-chromanol)

3D Structure for HMDB0012515 (11'-Carboxy-alpha-chromanol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra