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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:18 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0002902

Secondary Accession Numbers

HMDB02902

Metabolite Identification

Common Name

delta-Tocopherol

Description

Tocopherol, or Vitamin E, is a fat-soluble vitamin in eight forms that is an important antioxidant. Vitamin E is often used in skin creams and lotions because it is believed to play a role in encouraging skin healing and reducing scarring after injuries such as burns. -- Wikipedia ; Natural vitamin E exists in eight different forms or isomers, four tocopherols and four tocotrienols. All isomers have a chromanol ring, with a hydroxyl group which can donate a hydrogen atom to reduce free radicals and a hydrophobic side chain which allows for penetration into biological membranes. There is an alpha, beta, gamma and delta form of both the tocopherols and tocotrienols, determined by the number of methyl groups on the chromanol ring. Each form has its own biological activity, the measure of potency or functional use in the body. -- Wikipedia ; Alpha-tocopherol is traditionally recognized as the most active form of vitamin E in humans, and is a powerful biological antioxidant. The measurement of "vitamin E" activity in international units (IU) was based on fertility enhancement by the prevention of spontaneous abortions in pregnant rats relative to alpha tocopherol. It increases naturally to about 150% of normal in the maternal circulation during human pregnancies. 1 IU of vitamin E is defined as the biological equivalent of 0.667 milligrams of d-alpha-tocopherol, or of 1 milligram of dl-alpha-tocopherol acetate. The other isomers are slowly being recognized as research begins to elucidate their additional roles in the human body. Many naturopathic and orthomolecular medicine advocates suggest that vitamin E supplements contain at least 20% by weight of the other natural vitamin E isomers. Commercially available blends of natural vitamin E include "mixed tocopherols" and "high gamma tocopherol" formulas. Also selenium, Coenzyme Q10, and ample vitamin C have been shown to be essential cofactors of natural tocopherols. -- Wikipedia ; Synthetic vitamin E, usually marked as d,l-tocopherol or d,l tocopheryl acetate, with 50% d-alpha tocopherol moiety and 50% l-alpha-tocopherol moiety, as synthesized by an earlier process is now actually manufactured as all-racemic alpha tocopherol, with only about one alpha tocopherol molecule in 8 molecules as actual d-alpha tocpherol. The synthetic form is not as active as the natural alpha tocopherol form. The 1950's thalidomide disaster with numerous severe birth defects is a common example of d- vs l- epimer forms type problem with synthesized racemic mixtures. Information on any side effects of the synthetic vitamin E epimers is not readily available. Naturopathic and orthomolecular medicine advocates have long considered the synthetic vitamin E forms to be with little or no merit for cancer, circulatory and heart diseases. -- Wikipedia ; Abetalipoproteinemia is a rare inherited disorder of fat metabolism that results in poor absorption of dietary fat and vitamin E. The vitamin E deficiency associated with this disease causes problems such as poor transmission of nerve impulses, muscle weakness, and degeneration of the retina that can cause blindness. Individuals with abetalipoproteinemia may be prescribed special vitamin E supplements by a physician to treat this disorder. -- Wikipedia ; Recent studies also show that vitamin E acts as an effective free radical scavenger and can lower the incidence of lung cancer in smokers. The effects are opposite to that of the clinical trials based on administering carotenoid to male smokers, that resulted in increased risk of lung cancer. Hence vitamin E is an effective antagonist to the oxidative stress that is imposed by high carotenoids in certain patients. -- Wikipedia ; A cataract is a condition of clouding of the tissue of the lens of the eye. They increase the risk of disability and blindness in aging adults. Antioxidants are being studied to determine whether they can help prevent or delay cataract growth. Observational studies have found that lens clarity, which is used to diagnose cataracts, was better in regular users of vitamin E supplements and in persons with higher blood levels of vitamin E. A study of middle aged male smokers, however, did not demonstrate any effect from vitamin E supplements on the incidence of cataract formation. The effects of smoking, a major risk factor for developing cataracts, may have overridden any potential benefit from the vitamin E, but the conflicting results also indicate a need for further studies before researchers can confidently recommend extra vitamin E for the prevention of cataracts. It is important to note that the term "cataract" may be used in common parlance for an opacity involving any tissue of the eye, for example a corneal scar. Thus a character in theater or on television who is blind from cataracts might have white instead of clear corneas, covering over the iris and pupil. Since the lens is behind the pupil, real cataracts are difficult to see without special instrumentation, so people with cataracts have rather normally appearing eyes. -- Wikipedia ; Alzheimer's disease is a wasting disease of the brain. An observational trial conducted by The Johns Hopkins University Bloomberg School of Public Health found that when vitamin E is taken daily in large doses (400-1000IU) in combination with vitamin C (500-1000mg) the onset of Alzheimer's was reduced between 64 and 78%. External Link - Johns Hopkins press release -- Wikipedia .

Structure

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

  Mrv1652309042000272D          

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M  END

HMDB0002902
     RDKit          3D
delta-Tocopherol
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M  END

  Mrv1652309042000272D          

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  7  8  1  0  0  0  0
  7  9  1  1  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
 12 14  1  1  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
 17 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
  1 20  1  0  0  0  0
 22  2  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 25  1  0  0  0  0
 24 29  1  0  0  0  0
 29  3  1  0  0  0  0
 29  4  1  1  0  0  0
 25 20  2  0  0  0  0
 23 26  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002902

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h18-22,28H,7-17H2,1-6H3/t21-,22-,27-/m1/s1

> <INCHI_KEY>
GZIFEOYASATJEH-VHFRWLAGSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.6529

> <EXACT_MASS>
402.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.31471863589409

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
8.76

> <JCHEM_LOGP>
9.480874481333334

> <ALOGPS_LOGS>
-7.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.141712947649953

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852217396079623

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
125.29169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.09e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
delta tocopherol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002902
     RDKit          3D
delta-Tocopherol
 75 76  0  0  0  0  0  0  0  0999 V2000
    4.9882    2.7981   -1.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0358    2.3133   -0.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9346    3.2219   -0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9048    2.8013    0.6474 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8471    3.6802    1.2001 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9287    1.4436    0.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0188    0.5487    0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0467    0.9817   -0.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1468    0.0522   -0.9287 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6931   -1.0488   -0.1546 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6768   -2.3286   -0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3149   -0.7178    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729   -0.4725   -0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9797   -0.1359   -0.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010   -1.2083    0.4511 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2154   -2.5178   -0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0752   -0.8118    0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623   -0.5344   -0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3702   -0.1260    0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1119   -1.1163    0.8659 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3363   -2.4331    0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3127   -0.6175    1.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4473   -0.0174    0.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3072    1.2475    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6540    1.6851   -0.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6704    1.8874    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1112    0.7301   -1.5482 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5811   -1.3036    1.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0135   -0.8992    0.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4001    3.5670   -2.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1718    3.2274   -1.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5521    1.9480   -2.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8992    4.2603   -0.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6290    4.1558    2.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6870    1.0882    1.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2136   -2.1940   -1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2310   -3.1086   -0.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7392   -2.6023   -1.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292   -1.5245    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4282    0.2082    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3913   -1.3440   -1.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7749    0.3827   -1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3962   -0.0572   -1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8638    0.8237    0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8667   -1.3996    1.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0901   -3.1848   -0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6791   -3.1145   -0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1090   -2.3546   -1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4465   -1.6322    1.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9699    0.1233    1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9343   -1.3861   -0.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5424    0.3438   -0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8784   -0.0925   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3885    0.8954    0.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4578   -1.5050    1.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3349   -2.8935   -0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8161   -2.2692   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8758   -3.1127    0.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7650   -1.4648    2.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9398    0.1050    2.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9507   -0.8173    0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2382    0.1905    1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5959    1.1876   -0.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0572    2.0925    0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4657    2.6707   -0.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2197    0.9610    0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4339    2.6542    0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1362    2.2954    1.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3987   -0.0719   -1.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0781    0.2636   -1.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3433    1.2360   -2.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2173   -0.7186    1.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5689   -2.3699    1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4778   -1.4842   -0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5684   -1.0798    1.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 10 28  1  0
 28 29  1  0
  8  2  1  0
 29  7  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  5 34  1  0
  6 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  1
 16 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  1
 21 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8655.1068666.762   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8652.4428662.125   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8660.4268665.219   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8660.4268663.679   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8661.7588664.445   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8663.0918665.219   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.4248664.445   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.7568665.219   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.4248662.907   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.0888664.445   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.4248665.219   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8669.7568664.445   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8671.0878665.219   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8669.7568662.907   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8672.4238664.445   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8673.7558665.219   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8675.0918664.445   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8676.4238665.219   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8675.0918662.907   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8655.1058665.211   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8653.7728664.441   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8653.7728662.901   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8655.1058662.131   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8657.7658665.211   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0    8656.4328664.441   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8656.4328662.901   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8657.7658662.131   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8659.0998662.901   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8659.0998664.441   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2   22                                                            
CONECT    3    5   29                                                       
CONECT    4   29                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7   10                                                       
CONECT    9    7                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   21    1   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23    2                                                  
CONECT   23   22   26                                                       
CONECT   24   25   29                                                       
CONECT   25   26   24   20                                                  
CONECT   26   25   27   23                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24    3    4                                             
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

COMPND    HMDB0002902
HETATM    1  C1  UNL     1       4.988   2.798  -1.701  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.036   2.313  -0.743  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.935   3.222  -0.233  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.905   2.801   0.647  1.00  0.00           C  
HETATM    5  O1  UNL     1       8.847   3.680   1.200  1.00  0.00           O  
HETATM    6  C5  UNL     1       7.929   1.444   0.986  1.00  0.00           C  
HETATM    7  C6  UNL     1       7.019   0.549   0.463  1.00  0.00           C  
HETATM    8  C7  UNL     1       6.047   0.982  -0.422  1.00  0.00           C  
HETATM    9  O2  UNL     1       5.147   0.052  -0.929  1.00  0.00           O  
HETATM   10  C8  UNL     1       4.693  -1.049  -0.155  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.677  -2.329  -0.972  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.315  -0.718   0.382  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.373  -0.472  -0.748  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.980  -0.136  -0.358  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.301  -1.208   0.451  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.215  -2.518  -0.305  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.075  -0.812   0.865  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.962  -0.534  -0.301  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.370  -0.126   0.085  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.112  -1.116   0.866  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.336  -2.433   0.107  1.00  0.00           C  
HETATM   22  C20 UNL     1      -5.313  -0.618   1.556  1.00  0.00           C  
HETATM   23  C21 UNL     1      -6.447  -0.017   0.864  1.00  0.00           C  
HETATM   24  C22 UNL     1      -6.307   1.247   0.117  1.00  0.00           C  
HETATM   25  C23 UNL     1      -7.654   1.685  -0.496  1.00  0.00           C  
HETATM   26  C24 UNL     1      -8.670   1.887   0.602  1.00  0.00           C  
HETATM   27  C25 UNL     1      -8.111   0.730  -1.548  1.00  0.00           C  
HETATM   28  C26 UNL     1       5.581  -1.304   1.045  1.00  0.00           C  
HETATM   29  C27 UNL     1       7.014  -0.899   0.798  1.00  0.00           C  
HETATM   30  H1  UNL     1       5.400   3.567  -2.393  1.00  0.00           H  
HETATM   31  H2  UNL     1       4.172   3.227  -1.093  1.00  0.00           H  
HETATM   32  H3  UNL     1       4.552   1.948  -2.274  1.00  0.00           H  
HETATM   33  H4  UNL     1       6.899   4.260  -0.505  1.00  0.00           H  
HETATM   34  H5  UNL     1       8.629   4.156   2.086  1.00  0.00           H  
HETATM   35  H6  UNL     1       8.687   1.088   1.680  1.00  0.00           H  
HETATM   36  H7  UNL     1       4.214  -2.194  -1.954  1.00  0.00           H  
HETATM   37  H8  UNL     1       4.231  -3.109  -0.349  1.00  0.00           H  
HETATM   38  H9  UNL     1       5.739  -2.602  -1.140  1.00  0.00           H  
HETATM   39  H10 UNL     1       3.029  -1.524   1.058  1.00  0.00           H  
HETATM   40  H11 UNL     1       3.428   0.208   0.984  1.00  0.00           H  
HETATM   41  H12 UNL     1       2.391  -1.344  -1.432  1.00  0.00           H  
HETATM   42  H13 UNL     1       2.775   0.383  -1.340  1.00  0.00           H  
HETATM   43  H14 UNL     1       0.396  -0.057  -1.318  1.00  0.00           H  
HETATM   44  H15 UNL     1       0.864   0.824   0.152  1.00  0.00           H  
HETATM   45  H16 UNL     1       0.867  -1.400   1.411  1.00  0.00           H  
HETATM   46  H17 UNL     1       1.090  -3.185  -0.085  1.00  0.00           H  
HETATM   47  H18 UNL     1      -0.679  -3.114  -0.004  1.00  0.00           H  
HETATM   48  H19 UNL     1       0.109  -2.355  -1.400  1.00  0.00           H  
HETATM   49  H20 UNL     1      -1.447  -1.632   1.528  1.00  0.00           H  
HETATM   50  H21 UNL     1      -0.970   0.123   1.491  1.00  0.00           H  
HETATM   51  H22 UNL     1      -1.934  -1.386  -0.993  1.00  0.00           H  
HETATM   52  H23 UNL     1      -1.542   0.344  -0.836  1.00  0.00           H  
HETATM   53  H24 UNL     1      -3.878  -0.092  -0.944  1.00  0.00           H  
HETATM   54  H25 UNL     1      -3.389   0.895   0.462  1.00  0.00           H  
HETATM   55  H26 UNL     1      -3.458  -1.505   1.746  1.00  0.00           H  
HETATM   56  H27 UNL     1      -3.335  -2.894  -0.080  1.00  0.00           H  
HETATM   57  H28 UNL     1      -4.816  -2.269  -0.861  1.00  0.00           H  
HETATM   58  H29 UNL     1      -4.876  -3.113   0.777  1.00  0.00           H  
HETATM   59  H30 UNL     1      -5.765  -1.465   2.209  1.00  0.00           H  
HETATM   60  H31 UNL     1      -4.940   0.105   2.378  1.00  0.00           H  
HETATM   61  H32 UNL     1      -6.951  -0.817   0.246  1.00  0.00           H  
HETATM   62  H33 UNL     1      -7.238   0.190   1.668  1.00  0.00           H  
HETATM   63  H34 UNL     1      -5.596   1.188  -0.693  1.00  0.00           H  
HETATM   64  H35 UNL     1      -6.057   2.092   0.823  1.00  0.00           H  
HETATM   65  H36 UNL     1      -7.466   2.671  -0.965  1.00  0.00           H  
HETATM   66  H37 UNL     1      -9.220   0.961   0.852  1.00  0.00           H  
HETATM   67  H38 UNL     1      -9.434   2.654   0.346  1.00  0.00           H  
HETATM   68  H39 UNL     1      -8.136   2.295   1.505  1.00  0.00           H  
HETATM   69  H40 UNL     1      -7.399  -0.072  -1.777  1.00  0.00           H  
HETATM   70  H41 UNL     1      -9.078   0.264  -1.220  1.00  0.00           H  
HETATM   71  H42 UNL     1      -8.343   1.236  -2.523  1.00  0.00           H  
HETATM   72  H43 UNL     1       5.217  -0.719   1.913  1.00  0.00           H  
HETATM   73  H44 UNL     1       5.569  -2.370   1.343  1.00  0.00           H  
HETATM   74  H45 UNL     1       7.478  -1.484  -0.025  1.00  0.00           H  
HETATM   75  H46 UNL     1       7.568  -1.080   1.732  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    3    8
CONECT    3    4   33
CONECT    4    5    6    6
CONECT    5   34
CONECT    6    7   35
CONECT    7    8    8   29
CONECT    8    9
CONECT    9   10
CONECT   10   11   12   28
CONECT   11   36   37   38
CONECT   12   13   39   40
CONECT   13   14   41   42
CONECT   14   15   43   44
CONECT   15   16   17   45
CONECT   16   46   47   48
CONECT   17   18   49   50
CONECT   18   19   51   52
CONECT   19   20   53   54
CONECT   20   21   22   55
CONECT   21   56   57   58
CONECT   22   23   59   60
CONECT   23   24   61   62
CONECT   24   25   63   64
CONECT   25   26   27   65
CONECT   26   66   67   68
CONECT   27   69   70   71
CONECT   28   29   72   73
CONECT   29   74   75
END

HMDB0002902
     RDKit          3D
delta-Tocopherol
 75 76  0  0  0  0  0  0  0  0999 V2000
    4.9882    2.7981   -1.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0358    2.3133   -0.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9346    3.2219   -0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9048    2.8013    0.6474 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8471    3.6802    1.2001 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9287    1.4436    0.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0188    0.5487    0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0467    0.9817   -0.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1468    0.0522   -0.9287 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6931   -1.0488   -0.1546 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6768   -2.3286   -0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3149   -0.7178    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729   -0.4725   -0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9797   -0.1359   -0.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010   -1.2083    0.4511 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2154   -2.5178   -0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0752   -0.8118    0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623   -0.5344   -0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3702   -0.1260    0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1119   -1.1163    0.8659 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3363   -2.4331    0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3127   -0.6175    1.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4473   -0.0174    0.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3072    1.2475    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6540    1.6851   -0.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6704    1.8874    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1112    0.7301   -1.5482 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5811   -1.3036    1.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0135   -0.8992    0.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4001    3.5670   -2.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1718    3.2274   -1.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5521    1.9480   -2.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8992    4.2603   -0.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6290    4.1558    2.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6870    1.0882    1.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2136   -2.1940   -1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2310   -3.1086   -0.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7392   -2.6023   -1.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292   -1.5245    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4282    0.2082    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3913   -1.3440   -1.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7749    0.3827   -1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3962   -0.0572   -1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8638    0.8237    0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8667   -1.3996    1.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0901   -3.1848   -0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6791   -3.1145   -0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1090   -2.3546   -1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4465   -1.6322    1.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9699    0.1233    1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9343   -1.3861   -0.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5424    0.3438   -0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8784   -0.0925   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3885    0.8954    0.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4578   -1.5050    1.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3349   -2.8935   -0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8161   -2.2692   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8758   -3.1127    0.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7650   -1.4648    2.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9398    0.1050    2.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9507   -0.8173    0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2382    0.1905    1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5959    1.1876   -0.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0572    2.0925    0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4657    2.6707   -0.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2197    0.9610    0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4339    2.6542    0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1362    2.2954    1.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3987   -0.0719   -1.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0781    0.2636   -1.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3433    1.2360   -2.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2173   -0.7186    1.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5689   -2.3699    1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4778   -1.4842   -0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5684   -1.0798    1.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 10 28  1  0
 28 29  1  0
  8  2  1  0
 29  7  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  5 34  1  0
  6 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  1
 16 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  1
 21 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-delta-Tocopherol	ChEBI
(2R)-2,8-Dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol	ChEBI
(2R)-3,4-Dihydro-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol	ChEBI
(2R,4'r,8'r)-delta-Tocopherol	ChEBI
(R,R,R)-delta-Tocopherol	ChEBI
8-Methyltocol	ChEBI
e309	ChEBI
RRR-delta-Tocopherol	ChEBI
(+)-Δ-tocopherol	Generator
(2R,4'r,8'r)-Δ-tocopherol	Generator
(R,R,R)-Δ-tocopherol	Generator
RRR-Δ-tocopherol	Generator
Δ-tocopherol	Generator
Vitamine e	HMDB
(2R,4’R,8’r)-δ-tocopherol	HMDB
D-delta-Tocopherol	HMDB
D-Δ-tocopherol	HMDB
delta-D-Tocopherol	HMDB
delta-Vitamin e	HMDB
Δ-D-tocopherol	HMDB
Δ-vitamin e	HMDB
delta-Tocopherol	HMDB

Chemical Formula

C₂₇H₄₆O₂

Average Molecular Weight

402.6529

Monoisotopic Molecular Weight

402.349780716

IUPAC Name

(2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

delta tocopherol

CAS Registry Number

119-13-1

SMILES

CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1

InChI Identifier

InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h18-22,28H,7-17H2,1-6H3/t21-,22-,27-/m1/s1

InChI Key

GZIFEOYASATJEH-VHFRWLAGSA-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
1-benzopyran
Benzopyran
Chromane
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tocopherol (CHEBI:47772 )
vitamin E (C14151 )
Vitamin E (LMPR02020061 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	504.00 to 505.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	3.8e-06 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	10.493 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.1e-05 g/L	ALOGPS
logP	8.76	ALOGPS
logP	9.48	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Acidic)	10.14	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	125.29 m³·mol⁻¹	ChemAxon
Polarizability	51.31 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]+	197.917	31661259
DarkChem	[M-H]-	195.936	31661259
DeepCCS	[M+H]+	206.574	30932474
DeepCCS	[M-H]-	204.216	30932474
DeepCCS	[M-2H]-	237.532	30932474
DeepCCS	[M+Na]+	212.761	30932474
AllCCS	[M+H]+	210.1	32859911
AllCCS	[M+H-H2O]+	207.9	32859911
AllCCS	[M+NH4]+	212.2	32859911
AllCCS	[M+Na]+	212.7	32859911
AllCCS	[M-H]-	208.5	32859911
AllCCS	[M+Na-2H]-	211.0	32859911
AllCCS	[M+HCOO]-	213.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
delta-Tocopherol	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1	3804.5	Standard polar	33892256
delta-Tocopherol	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1	2930.1	Standard non polar	33892256
delta-Tocopherol	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1	3029.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
delta-Tocopherol,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC2=C1O[C@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)CC2	2899.4	Semi standard non polar	33892256
delta-Tocopherol,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1O[C@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)CC2	3165.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - delta-Tocopherol GC-MS (1 TMS)	splash10-0ab9-3490300000-f13783678d446978a134	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - delta-Tocopherol GC-MS (Non-derivatized)	splash10-0ab9-3490300000-f13783678d446978a134	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - delta-Tocopherol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0553-6966000000-24c590db65503bc92d19	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - delta-Tocopherol GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-7755900000-0db42dc49bee83a43b36	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - delta-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
Experimental LC-MS/MS	LC-MS/MS Spectrum - delta-Tocopherol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0udr-2500900000-d51c6b511d2655c65526	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - delta-Tocopherol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0udi-0300900000-c7cd87c9e4b48f15bbbb	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - delta-Tocopherol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-000i-0900000000-afcde4fb8f9be6edde67	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - delta-Tocopherol EI-EBEB (JMS-HX/HX 110A, JEOL) , Positive-QTOF	splash10-0f79-3900300000-7367fe51787d1f4d6fae	2012-08-31	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Tocopherol 10V, Positive-QTOF	splash10-0udi-0822900000-53573e0accb0cbdeedcd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Tocopherol 20V, Positive-QTOF	splash10-000i-1910000000-54f3075b09bc49ae07ad	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Tocopherol 40V, Positive-QTOF	splash10-0a4r-5920000000-e8c787f9de39e1794e7c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Tocopherol 10V, Negative-QTOF	splash10-0udi-0100900000-ba38bc42ccadcfb32ed7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Tocopherol 20V, Negative-QTOF	splash10-0udr-0801900000-295fe543769c50ae0fc4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Tocopherol 40V, Negative-QTOF	splash10-000i-0914000000-ed731410a01607b11c51	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Tocopherol 10V, Positive-QTOF	splash10-0udi-3223900000-1d95ede1af4310b26021	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Tocopherol 20V, Positive-QTOF	splash10-0571-9411100000-c28dcd02ad1cb1164263	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Tocopherol 40V, Positive-QTOF	splash10-056v-9500000000-6d08cf1393844200bdde	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Tocopherol 10V, Negative-QTOF	splash10-0udi-0000900000-079f76b4d985e4b92c9d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Tocopherol 20V, Negative-QTOF	splash10-0udr-0900700000-1574fe7da8fc24170f5d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Tocopherol 40V, Negative-QTOF	splash10-01ri-1903000000-6a9bc14f76db42f74276	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces

Tissue Locations

Adipose Tissue
Epidermis
Liver
Neuron
Platelet
Prostate
Skeletal Muscle

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.899 +/- 0.648 uM	Adult (>18 years old)	Female	Normal	18813024	details
Blood	Detected and Quantified	26.7 +/- 0.9 uM	Adult (>18 years old)	Female	Normal	12772433	details
Blood	Detected and Quantified	26.00 +/- 1.00 uM	Adult (>18 years old)	Male	Normal	12772433	details
Blood	Detected and Quantified	2.4 (0.24-4.7) uM	Adult (>18 years old)	Both	Normal	8633780	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Delta-Tocopherol

METLIN ID

232

PubChem Compound

92094

PDB ID

Not Available

ChEBI ID

47772

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1118171

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Jiang Q, Wong J, Fyrst H, Saba JD, Ames BN: gamma-Tocopherol or combinations of vitamin E forms induce cell death in human prostate cancer cells by interrupting sphingolipid synthesis. Proc Natl Acad Sci U S A. 2004 Dec 21;101(51):17825-30. Epub 2004 Dec 13. [PubMed:15596715 ]
Clarke MW, Ward NC, Wu JH, Hodgson JM, Puddey IB, Croft KD: Supplementation with mixed tocopherols increases serum and blood cell gamma-tocopherol but does not alter biomarkers of platelet activation in subjects with type 2 diabetes. Am J Clin Nutr. 2006 Jan;83(1):95-102. [PubMed:16400056 ]
Fischer CP, Hiscock NJ, Basu S, Vessby B, Kallner A, Sjoberg LB, Febbraio MA, Pedersen BK: Vitamin E isoform-specific inhibition of the exercise-induced heat shock protein 72 expression in humans. J Appl Physiol (1985). 2006 May;100(5):1679-87. Epub 2005 Dec 29. [PubMed:16384840 ]
Passi S, De Pita O, Grandinetti M, Simotti C, Littarru GP: The combined use of oral and topical lipophilic antioxidants increases their levels both in sebum and stratum corneum. Biofactors. 2003;18(1-4):289-97. [PubMed:14695946 ]
Brigelius-Flohe R, Traber MG: Vitamin E: function and metabolism. FASEB J. 1999 Jul;13(10):1145-55. [PubMed:10385606 ]
Liu M, Wallmon A, Olsson-Mortlock C, Wallin R, Saldeen T: Mixed tocopherols inhibit platelet aggregation in humans: potential mechanisms. Am J Clin Nutr. 2003 Mar;77(3):700-6. [PubMed:12600864 ]
Traber MG, Kayden HJ: Tocopherol distribution and intracellular localization in human adipose tissue. Am J Clin Nutr. 1987 Sep;46(3):488-95. [PubMed:3630967 ]
Gehring W, Fluhr J, Gloor M: Influence of vitamin E acetate on stratum corneum hydration. Arzneimittelforschung. 1998 Jul;48(7):772-5. [PubMed:9706379 ]
Sen CK, Khanna S, Roy S: Tocotrienol: the natural vitamin E to defend the nervous system? Ann N Y Acad Sci. 2004 Dec;1031:127-42. [PubMed:15753140 ]
Sontag TJ, Parker RS: Cytochrome P450 omega-hydroxylase pathway of tocopherol catabolism. Novel mechanism of regulation of vitamin E status. J Biol Chem. 2002 Jul 12;277(28):25290-6. Epub 2002 May 7. [PubMed:11997390 ]
Epler KS, Ziegler RG, Craft NE: Liquid chromatographic method for the determination of carotenoids, retinoids and tocopherols in human serum and in food. J Chromatogr. 1993 Sep 8;619(1):37-48. [PubMed:8245162 ]
Mavon A, Raufast V, Redoules D: Skin absorption and metabolism of a new vitamin E prodrug, delta-tocopherol-glucoside: in vitro evaluation in human skin models. J Control Release. 2004 Nov 24;100(2):221-31. [PubMed:15544870 ]
Limpens J, Schroder FH, de Ridder CM, Bolder CA, Wildhagen MF, Obermuller-Jevic UC, Kramer K, van Weerden WM: Combined lycopene and vitamin E treatment suppresses the growth of PC-346C human prostate cancer cells in nude mice. J Nutr. 2006 May;136(5):1287-93. [PubMed:16614418 ]

Showing metabocard for delta-Tocopherol (HMDB0002902)

MOL for HMDB0002902 (delta-Tocopherol)

3D MOL for HMDB0002902 (delta-Tocopherol)

3D SDF for HMDB0002902 (delta-Tocopherol)

3D-SDF for HMDB0002902 (delta-Tocopherol)

PDB for HMDB0002902 (delta-Tocopherol)

3D PDB for HMDB0002902 (delta-Tocopherol)

SMILES for HMDB0002902 (delta-Tocopherol)

INCHI for HMDB0002902 (delta-Tocopherol)

Structure for HMDB0002902 (delta-Tocopherol)

3D Structure for HMDB0002902 (delta-Tocopherol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra