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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:02:55 UTC

Update Date

2022-03-07 02:51:26 UTC

HMDB ID

HMDB0012559

Secondary Accession Numbers

HMDB12559

Metabolite Identification

Common Name

13'-Hydroxy-alpha-tocopherol

Description

13'-hydroxy-alpha-tocopherol is the precursor in dehydrogenation to 13'-carboxy-alpha-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          

 32 33  0  0  1  0            999 V2000
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   12.7512  -12.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1637  -11.8285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9887  -11.8285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.8946  -17.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8946  -16.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.4656  -18.6712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

HMDB0012559
     RDKit          3D
13'-Hydroxy-alpha-tocopherol
 82 83  0  0  0  0  0  0  0  0999 V2000
   -7.7169   -1.8029    2.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
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 31 82  1  0
M  END

  Mrv0541 02251208062D          

 32 33  0  0  1  0            999 V2000
   13.1637  -13.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7512  -12.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1637  -11.8285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9887  -11.8285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.8946  -18.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8946  -19.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1801  -18.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4656  -18.6712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 18 32  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 31  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012559

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H50O3/c1-20(13-9-14-22(3)19-30)11-8-12-21(2)15-10-17-29(7)18-16-26-25(6)27(31)23(4)24(5)28(26)32-29/h20-22,30-31H,8-19H2,1-7H3/t20-,21+,22?,29+/m0/s1

> <INCHI_KEY>
URYLCCKXLNXSRS-XIRVVSDESA-N

> <FORMULA>
C29H50O3

> <MOLECULAR_WEIGHT>
446.7055

> <EXACT_MASS>
446.375995466

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
57.32392379126493

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(4R,8S)-13-hydroxy-4,8,12-trimethyltridecyl]-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
8.07

> <JCHEM_LOGP>
9.148992373333334

> <ALOGPS_LOGS>
-7.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.418322874869105

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.802178125614303

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7406898159721043

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
137.22579999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.70e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(4R,8S)-13-hydroxy-4,8,12-trimethyltridecyl]-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012559
     RDKit          3D
13'-Hydroxy-alpha-tocopherol
 82 83  0  0  0  0  0  0  0  0999 V2000
   -7.7169   -1.8029    2.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0763   -0.8094    1.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7602   -0.4139    1.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9334   -1.0007    2.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2338    0.5221    0.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9858    1.0836   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2900    0.6684   -0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1438    1.2428   -1.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8521   -0.2598    0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1786   -0.6304    0.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4799    2.0773   -1.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0206    2.3549   -1.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2380    1.2745   -0.5141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1838    0.1117   -1.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9555    1.9240   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9595    1.2303    0.6696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382    0.0205    0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6981   -0.0363   -0.8332 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0969    0.2607   -2.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3765   -1.4020   -0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1507   -1.7369    0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2423   -0.7904    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2668   -0.6558   -0.4551 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9563   -1.9154   -0.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1223    0.5650   -0.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9102    0.7147    0.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9815   -0.1479    1.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2626   -0.3117    0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0434    1.0141    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4241   -1.1192   -0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7313   -0.7129   -1.6510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9238    0.9544    0.6927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4330   -1.3106    2.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2918   -2.5677    1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9809   -2.3265    2.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5544   -1.9927    2.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0542   -0.3353    2.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4757   -1.0532    3.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6893    0.9342   -2.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1197    2.3411   -1.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1717    0.8731   -1.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6131   -1.3072    0.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0220    3.0566   -1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7984    1.7478   -2.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865    3.3202   -0.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5966    2.3550   -2.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6208   -0.7672   -1.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7790    0.4579   -2.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2657   -0.1956   -1.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2436    2.8686    0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5713    2.4524   -1.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4112    1.0107    1.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1357    2.0221    0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4157   -0.2259    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9252   -0.8853    0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5236    0.7041   -0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737    0.1601   -2.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2386    1.2794   -2.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388   -0.5195   -2.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5568   -2.1537   -1.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9316   -1.4228   -1.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4493   -1.8218    1.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5705   -2.7946    0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8165    0.2105    0.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6926   -1.2063    1.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6112   -0.4107   -1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2398   -2.7828   -0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7780   -2.2500   -0.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2577   -1.8198   -1.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6265    0.7576   -1.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3858    1.4693   -0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3478    1.7875    0.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1361    0.9000    1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2606    0.2623    2.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6401   -1.1853    1.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9322   -0.8689    1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1325    1.4179    1.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6109    1.6708   -0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0578    0.7230    0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2524   -2.2301   -0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5148   -1.1419   -0.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6101   -1.4802   -2.2633 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  1  0
 13 32  1  0
  9  2  1  0
 32  5  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  0
  8 40  1  0
  8 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  0
 17 55  1  0
 18 56  1  1
 19 57  1  0
 19 58  1  0
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  6
 24 67  1  0
 24 68  1  0
 24 69  1  0
 25 70  1  0
 25 71  1  0
 26 72  1  0
 26 73  1  0
 27 74  1  0
 27 75  1  0
 28 76  1  0
 29 77  1  0
 29 78  1  0
 29 79  1  0
 30 80  1  0
 30 81  1  0
 31 82  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      24.572 -24.747   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.802 -23.413   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.572 -22.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      26.112 -22.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      22.262 -23.413   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.492 -24.747   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.952 -24.747   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.182 -26.081   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.642 -26.081   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.952 -27.415   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.182 -28.748   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.952 -30.082   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.182 -31.416   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.642 -31.416   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.952 -32.749   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.492 -32.749   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.262 -34.083   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.802 -34.083   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.032 -35.417   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.802 -32.543   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.136 -31.773   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.470 -32.543   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      27.803 -31.773   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      27.803 -30.233   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      29.137 -32.543   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      30.471 -31.773   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      29.137 -34.083   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.471 -34.853   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      27.803 -34.853   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      27.803 -36.393   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      26.470 -34.083   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      25.136 -34.853   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   32                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   22   29   32                                                  
CONECT   32   18   31                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

COMPND    HMDB0012559
HETATM    1  C1  UNL     1      -7.717  -1.803   2.216  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.076  -0.809   1.331  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.760  -0.414   1.470  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.933  -1.001   2.553  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.234   0.522   0.600  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.986   1.084  -0.417  1.00  0.00           C  
HETATM    7  C7  UNL     1      -7.290   0.668  -0.527  1.00  0.00           C  
HETATM    8  C8  UNL     1      -8.144   1.243  -1.607  1.00  0.00           C  
HETATM    9  C9  UNL     1      -7.852  -0.260   0.317  1.00  0.00           C  
HETATM   10  O1  UNL     1      -9.179  -0.630   0.143  1.00  0.00           O  
HETATM   11  C10 UNL     1      -5.480   2.077  -1.364  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.021   2.355  -1.303  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.238   1.275  -0.514  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.184   0.112  -1.439  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.956   1.924  -0.133  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.960   1.230   0.670  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.238   0.020   0.302  1.00  0.00           C  
HETATM   18  C17 UNL     1       0.698  -0.036  -0.833  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.097   0.261  -2.181  1.00  0.00           C  
HETATM   20  C19 UNL     1       1.376  -1.402  -0.947  1.00  0.00           C  
HETATM   21  C20 UNL     1       2.151  -1.737   0.259  1.00  0.00           C  
HETATM   22  C21 UNL     1       3.242  -0.790   0.647  1.00  0.00           C  
HETATM   23  C22 UNL     1       4.267  -0.656  -0.455  1.00  0.00           C  
HETATM   24  C23 UNL     1       4.956  -1.915  -0.841  1.00  0.00           C  
HETATM   25  C24 UNL     1       5.122   0.565  -0.298  1.00  0.00           C  
HETATM   26  C25 UNL     1       5.910   0.715   0.917  1.00  0.00           C  
HETATM   27  C26 UNL     1       6.982  -0.148   1.366  1.00  0.00           C  
HETATM   28  C27 UNL     1       8.263  -0.312   0.695  1.00  0.00           C  
HETATM   29  C28 UNL     1       9.043   1.014   0.579  1.00  0.00           C  
HETATM   30  C29 UNL     1       8.424  -1.119  -0.534  1.00  0.00           C  
HETATM   31  O2  UNL     1       7.731  -0.713  -1.651  1.00  0.00           O  
HETATM   32  O3  UNL     1      -3.924   0.954   0.693  1.00  0.00           O  
HETATM   33  H1  UNL     1      -8.433  -1.311   2.911  1.00  0.00           H  
HETATM   34  H2  UNL     1      -8.292  -2.568   1.663  1.00  0.00           H  
HETATM   35  H3  UNL     1      -6.981  -2.327   2.862  1.00  0.00           H  
HETATM   36  H4  UNL     1      -4.554  -1.993   2.226  1.00  0.00           H  
HETATM   37  H5  UNL     1      -4.054  -0.335   2.720  1.00  0.00           H  
HETATM   38  H6  UNL     1      -5.476  -1.053   3.521  1.00  0.00           H  
HETATM   39  H7  UNL     1      -7.689   0.934  -2.583  1.00  0.00           H  
HETATM   40  H8  UNL     1      -8.120   2.341  -1.592  1.00  0.00           H  
HETATM   41  H9  UNL     1      -9.172   0.873  -1.544  1.00  0.00           H  
HETATM   42  H10 UNL     1      -9.613  -1.307   0.746  1.00  0.00           H  
HETATM   43  H11 UNL     1      -6.022   3.057  -1.206  1.00  0.00           H  
HETATM   44  H12 UNL     1      -5.798   1.748  -2.391  1.00  0.00           H  
HETATM   45  H13 UNL     1      -3.787   3.320  -0.817  1.00  0.00           H  
HETATM   46  H14 UNL     1      -3.597   2.355  -2.324  1.00  0.00           H  
HETATM   47  H15 UNL     1      -2.621  -0.767  -1.113  1.00  0.00           H  
HETATM   48  H16 UNL     1      -2.779   0.458  -2.425  1.00  0.00           H  
HETATM   49  H17 UNL     1      -4.266  -0.196  -1.606  1.00  0.00           H  
HETATM   50  H18 UNL     1      -2.244   2.869   0.525  1.00  0.00           H  
HETATM   51  H19 UNL     1      -1.571   2.452  -1.049  1.00  0.00           H  
HETATM   52  H20 UNL     1      -1.411   1.011   1.734  1.00  0.00           H  
HETATM   53  H21 UNL     1      -0.136   2.022   0.963  1.00  0.00           H  
HETATM   54  H22 UNL     1       0.416  -0.226   1.247  1.00  0.00           H  
HETATM   55  H23 UNL     1      -0.925  -0.885   0.341  1.00  0.00           H  
HETATM   56  H24 UNL     1       1.524   0.704  -0.610  1.00  0.00           H  
HETATM   57  H25 UNL     1       0.974   0.160  -2.938  1.00  0.00           H  
HETATM   58  H26 UNL     1      -0.239   1.279  -2.349  1.00  0.00           H  
HETATM   59  H27 UNL     1      -0.639  -0.519  -2.471  1.00  0.00           H  
HETATM   60  H28 UNL     1       0.557  -2.154  -1.042  1.00  0.00           H  
HETATM   61  H29 UNL     1       1.932  -1.423  -1.895  1.00  0.00           H  
HETATM   62  H30 UNL     1       1.449  -1.822   1.134  1.00  0.00           H  
HETATM   63  H31 UNL     1       2.571  -2.795   0.215  1.00  0.00           H  
HETATM   64  H32 UNL     1       2.817   0.210   0.848  1.00  0.00           H  
HETATM   65  H33 UNL     1       3.693  -1.206   1.578  1.00  0.00           H  
HETATM   66  H34 UNL     1       3.611  -0.411  -1.371  1.00  0.00           H  
HETATM   67  H35 UNL     1       4.240  -2.783  -0.866  1.00  0.00           H  
HETATM   68  H36 UNL     1       5.778  -2.250  -0.213  1.00  0.00           H  
HETATM   69  H37 UNL     1       5.258  -1.820  -1.922  1.00  0.00           H  
HETATM   70  H38 UNL     1       5.627   0.758  -1.263  1.00  0.00           H  
HETATM   71  H39 UNL     1       4.386   1.469  -0.271  1.00  0.00           H  
HETATM   72  H40 UNL     1       6.348   1.788   0.873  1.00  0.00           H  
HETATM   73  H41 UNL     1       5.136   0.900   1.764  1.00  0.00           H  
HETATM   74  H42 UNL     1       7.261   0.262   2.426  1.00  0.00           H  
HETATM   75  H43 UNL     1       6.640  -1.185   1.679  1.00  0.00           H  
HETATM   76  H44 UNL     1       8.932  -0.869   1.465  1.00  0.00           H  
HETATM   77  H45 UNL     1       9.132   1.418   1.587  1.00  0.00           H  
HETATM   78  H46 UNL     1       8.611   1.671  -0.172  1.00  0.00           H  
HETATM   79  H47 UNL     1      10.058   0.723   0.234  1.00  0.00           H  
HETATM   80  H48 UNL     1       8.252  -2.230  -0.334  1.00  0.00           H  
HETATM   81  H49 UNL     1       9.515  -1.142  -0.873  1.00  0.00           H  
HETATM   82  H50 UNL     1       7.610  -1.480  -2.263  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3    3    9
CONECT    3    4    5
CONECT    4   36   37   38
CONECT    5    6    6   32
CONECT    6    7   11
CONECT    7    8    9    9
CONECT    8   39   40   41
CONECT    9   10
CONECT   10   42
CONECT   11   12   43   44
CONECT   12   13   45   46
CONECT   13   14   15   32
CONECT   14   47   48   49
CONECT   15   16   50   51
CONECT   16   17   52   53
CONECT   17   18   54   55
CONECT   18   19   20   56
CONECT   19   57   58   59
CONECT   20   21   60   61
CONECT   21   22   62   63
CONECT   22   23   64   65
CONECT   23   24   25   66
CONECT   24   67   68   69
CONECT   25   26   70   71
CONECT   26   27   72   73
CONECT   27   28   74   75
CONECT   28   29   30   76
CONECT   29   77   78   79
CONECT   30   31   80   81
CONECT   31   82
END

HMDB0012559
     RDKit          3D
13'-Hydroxy-alpha-tocopherol
 82 83  0  0  0  0  0  0  0  0999 V2000
   -7.7169   -1.8029    2.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0763   -0.8094    1.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7602   -0.4139    1.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9334   -1.0007    2.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2338    0.5221    0.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9858    1.0836   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2900    0.6684   -0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1438    1.2428   -1.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8521   -0.2598    0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1786   -0.6304    0.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4799    2.0773   -1.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0206    2.3549   -1.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2380    1.2745   -0.5141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1838    0.1117   -1.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9555    1.9240   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9595    1.2303    0.6696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382    0.0205    0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6981   -0.0363   -0.8332 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0969    0.2607   -2.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3765   -1.4020   -0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1507   -1.7369    0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2423   -0.7904    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2668   -0.6558   -0.4551 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9563   -1.9154   -0.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1223    0.5650   -0.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9102    0.7147    0.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9815   -0.1479    1.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2626   -0.3117    0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0434    1.0141    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4241   -1.1192   -0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7313   -0.7129   -1.6510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9238    0.9544    0.6927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4330   -1.3106    2.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2918   -2.5677    1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9809   -2.3265    2.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5544   -1.9927    2.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0542   -0.3353    2.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4757   -1.0532    3.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6893    0.9342   -2.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1197    2.3411   -1.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1717    0.8731   -1.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6131   -1.3072    0.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0220    3.0566   -1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7984    1.7478   -2.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865    3.3202   -0.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5966    2.3550   -2.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6208   -0.7672   -1.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7790    0.4579   -2.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2657   -0.1956   -1.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2436    2.8686    0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5713    2.4524   -1.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4112    1.0107    1.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1357    2.0221    0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4157   -0.2259    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9252   -0.8853    0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5236    0.7041   -0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737    0.1601   -2.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2386    1.2794   -2.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388   -0.5195   -2.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5568   -2.1537   -1.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9316   -1.4228   -1.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4493   -1.8218    1.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5705   -2.7946    0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8165    0.2105    0.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6926   -1.2063    1.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6112   -0.4107   -1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2398   -2.7828   -0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7780   -2.2500   -0.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2577   -1.8198   -1.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6265    0.7576   -1.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3858    1.4693   -0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3478    1.7875    0.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1361    0.9000    1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2606    0.2623    2.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6401   -1.1853    1.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9322   -0.8689    1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1325    1.4179    1.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6109    1.6708   -0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0578    0.7230    0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2524   -2.2301   -0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5148   -1.1419   -0.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6101   -1.4802   -2.2633 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  1  0
 13 32  1  0
  9  2  1  0
 32  5  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  0
  8 40  1  0
  8 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  0
 17 55  1  0
 18 56  1  1
 19 57  1  0
 19 58  1  0
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  6
 24 67  1  0
 24 68  1  0
 24 69  1  0
 25 70  1  0
 25 71  1  0
 26 72  1  0
 26 73  1  0
 27 74  1  0
 27 75  1  0
 28 76  1  0
 29 77  1  0
 29 78  1  0
 29 79  1  0
 30 80  1  0
 30 81  1  0
 31 82  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
13-OH-alpha-Tocopherol	ChEBI
13-OH-a-Tocopherol	Generator
13-OH-Α-tocopherol	Generator
13'-Hydroxy-a-tocopherol	Generator
13'-Hydroxy-α-tocopherol	Generator
13-Hydroxy-a-tocopherol	HMDB
13-Hydroxy-α-tocopherol	HMDB
13'-Hydroxy-alpha-tocopherol	ChEBI

Chemical Formula

C₂₉H₅₀O₃

Average Molecular Weight

446.7055

Monoisotopic Molecular Weight

446.375995466

IUPAC Name

(2R)-2-[(4R,8S)-13-hydroxy-4,8,12-trimethyltridecyl]-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

(2R)-2-[(4R,8S)-13-hydroxy-4,8,12-trimethyltridecyl]-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-6-ol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C29H50O3/c1-20(13-9-14-22(3)19-30)11-8-12-21(2)15-10-17-29(7)18-16-26-25(6)27(31)23(4)24(5)28(26)32-29/h20-22,30-31H,8-19H2,1-7H3/t20-,21+,22?,29+/m0/s1

InChI Key

URYLCCKXLNXSRS-XIRVVSDESA-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 alcohol
Chromane
Benzopyran
1-benzopyran
Fatty alcohol
Alkyl aryl ether
Fatty acyl
Benzenoid
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:84962 )
primary alcohol (CHEBI:84962 )
chromanol (CHEBI:84962 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012559)

Source

Endogenous

Endogenous (HMDB: HMDB0012559)

Animal

Animal (HMDB: HMDB0012559)

Exogenous

Food

Food (HMDB: HMDB0012559)

Exogenous (HMDB: HMDB0012559)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012559)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012559)

Lipid metabolism pathway (HMDB: HMDB0012559)

Cellular process

Cell signaling (HMDB: HMDB0012559)

Biochemical process

Lipid transport (HMDB: HMDB0012559)

Role

Biological role

Energy source (HMDB: HMDB0012559)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012559)

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	3.7e-05 g/L	ALOGPS
logP	8.07	ALOGPS
logP	9.15	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	10.8	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	137.23 m³·mol⁻¹	ChemAxon
Polarizability	57.32 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]+	210.684	31661259
DarkChem	[M-H]-	204.519	31661259
DeepCCS	[M+H]+	215.475	30932474
DeepCCS	[M-H]-	213.08	30932474
DeepCCS	[M-2H]-	245.962	30932474
DeepCCS	[M+Na]+	221.388	30932474
AllCCS	[M+H]+	217.2	32859911
AllCCS	[M+H-H2O]+	215.3	32859911
AllCCS	[M+NH4]+	219.0	32859911
AllCCS	[M+Na]+	219.5	32859911
AllCCS	[M-H]-	216.6	32859911
AllCCS	[M+Na-2H]-	219.7	32859911
AllCCS	[M+HCOO]-	223.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
13'-Hydroxy-alpha-tocopherol	CC(CO)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C	4095.5	Standard polar	33892256
13'-Hydroxy-alpha-tocopherol	CC(CO)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C	3368.6	Standard non polar	33892256
13'-Hydroxy-alpha-tocopherol	CC(CO)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C	3462.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
13'-Hydroxy-alpha-tocopherol,1TMS,isomer #1	CC1=C(C)C2=C(CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)CO[Si](C)(C)C)O2)C(C)=C1O	3275.7	Semi standard non polar	33892256
13'-Hydroxy-alpha-tocopherol,1TMS,isomer #2	CC1=C(C)C2=C(CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)CO)O2)C(C)=C1O[Si](C)(C)C	3348.7	Semi standard non polar	33892256
13'-Hydroxy-alpha-tocopherol,2TMS,isomer #1	CC1=C(C)C2=C(CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)CO[Si](C)(C)C)O2)C(C)=C1O[Si](C)(C)C	3304.9	Semi standard non polar	33892256
13'-Hydroxy-alpha-tocopherol,1TBDMS,isomer #1	CC1=C(C)C2=C(CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)CO[Si](C)(C)C(C)(C)C)O2)C(C)=C1O	3535.0	Semi standard non polar	33892256
13'-Hydroxy-alpha-tocopherol,1TBDMS,isomer #2	CC1=C(C)C2=C(CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)CO)O2)C(C)=C1O[Si](C)(C)C(C)(C)C	3606.9	Semi standard non polar	33892256
13'-Hydroxy-alpha-tocopherol,2TBDMS,isomer #1	CC1=C(C)C2=C(CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)CO[Si](C)(C)C(C)(C)C)O2)C(C)=C1O[Si](C)(C)C(C)(C)C	3808.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 13'-Hydroxy-alpha-tocopherol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05pk-2796500000-696d167e7dff626a2856	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13'-Hydroxy-alpha-tocopherol GC-MS (2 TMS) - 70eV, Positive	splash10-004i-2445390000-69dfb80c7cbe0f4cc3d9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13'-Hydroxy-alpha-tocopherol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13'-Hydroxy-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'-Hydroxy-alpha-tocopherol 10V, Positive-QTOF	splash10-00mk-0421900000-c2e2838b4fed1944830b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 20V, Positive-QTOF	splash10-014i-0910100000-ae48ef0eac05453a364a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 40V, Positive-QTOF	splash10-014i-1910000000-cac243bd70399ac13a77	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 10V, Negative-QTOF	splash10-0002-0000900000-e8a490fcd22573d72002	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 20V, Negative-QTOF	splash10-01ot-0410900000-2df09762b86f7f4ffb1d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 40V, Negative-QTOF	splash10-0gwb-0923300000-2fb95536d042c7aef0a7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 10V, Positive-QTOF	splash10-0002-2115900000-099be936055d32b60bb0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 20V, Positive-QTOF	splash10-014j-6729200000-ecfbf5f04269af7045d0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 40V, Positive-QTOF	splash10-0aor-9532000000-a1c54a6c597c9eeed41e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 10V, Negative-QTOF	splash10-002b-0000900000-fce93c2306a34f832c4f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 20V, Negative-QTOF	splash10-02ta-0411900000-a8a991079c3018f0635c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 40V, Negative-QTOF	splash10-0bvi-0469700000-7a2f459658cb79c8561c	2021-09-23	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

FDB029125

KNApSAcK ID

Not Available

Chemspider ID

34999549

KEGG Compound ID

Not Available

BioCyc ID

CPD-11960

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481465

PDB ID

Not Available

ChEBI ID

84962

Food Biomarker Ontology

Not Available

VMH ID

CE5842

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 13'-Hydroxy-alpha-tocopherol (HMDB0012559)

MOL for HMDB0012559 (13'-Hydroxy-alpha-tocopherol)

3D MOL for HMDB0012559 (13'-Hydroxy-alpha-tocopherol)

3D SDF for HMDB0012559 (13'-Hydroxy-alpha-tocopherol)

3D-SDF for HMDB0012559 (13'-Hydroxy-alpha-tocopherol)

PDB for HMDB0012559 (13'-Hydroxy-alpha-tocopherol)

3D PDB for HMDB0012559 (13'-Hydroxy-alpha-tocopherol)

SMILES for HMDB0012559 (13'-Hydroxy-alpha-tocopherol)

INCHI for HMDB0012559 (13'-Hydroxy-alpha-tocopherol)

Structure for HMDB0012559 (13'-Hydroxy-alpha-tocopherol)

3D Structure for HMDB0012559 (13'-Hydroxy-alpha-tocopherol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra