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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:10 UTC

HMDB ID

HMDB0001492

Secondary Accession Numbers

HMDB0002634
HMDB01492
HMDB02634

Metabolite Identification

Common Name

gamma-Tocopherol

Description

gamma-Tocopherol, also known as 7,8-dimethyltocol, 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. They differ from tocotrienols which contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. It is estimated that 50% of gamma-tocopherol is metabolized into gamma-CEHC and excreted into the urine. gamma-Tocopherol is the predominant form of vitamin E in plant seeds and derived products (e.g. nuts and vegetable oils). Unlike alpha-tocopherol, gamma-tocopherol inhibits cyclooxygenase activity and, therefore, exhibit anti-inflammatory properties (PMID: 11722951 ).

Structure

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

  Mrv1652309042000242D          

 30 31  0  0  0  0            999 V2000
 9993.807010000.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6567 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3706 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0846 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7985 9998.8096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.5120 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.2257 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9413 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6548 9998.8096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.3704 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.0839 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.7974 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5130 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.2265 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5130 9997.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6548 9997.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7985 9997.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6567 9998.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3794 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3794 9997.5669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8064 9999.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0920 9998.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0919 9997.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8063 9997.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.2315 9999.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5170 9998.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5170 9997.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.2315 9997.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9459 9997.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9459 9998.8077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  2  3  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
  5 17  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  1  1  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  0  0  0  0
 13 15  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
  1 21  1  0  0  0  0
 23 20  1  0  0  0  0
 22 19  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 26  1  0  0  0  0
 25 30  1  0  0  0  0
 30  2  1  0  0  0  0
 30 18  1  1  0  0  0
 26 21  2  0  0  0  0
 24 27  2  0  0  0  0
M  END

HMDB0001492
     RDKit          3D
gamma-Tocopherol
 78 79  0  0  0  0  0  0  0  0999 V2000
   -9.1098   -2.5454   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1948   -1.3944   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7291   -0.1610    0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1169    0.0394    0.4005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8642    0.9024    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4754    0.7692    0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9588   -0.4778   -0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8283   -1.5546   -0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2309   -2.8818   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5819   -0.5705   -0.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880    0.4876   -0.7583 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1490    0.3418   -2.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3722    0.2946   -0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5484    0.0185    1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9790    1.4599    1.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7968    1.5719   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4964    0.4327   -0.6137 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7344   -0.7409   -1.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6770   -0.1109    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7591    0.8714    0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9442    0.4332    1.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7752   -0.6763    0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1004   -2.0154    0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5282   -0.3990   -0.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3023    1.8490   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5725    1.9158    0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6241   -2.4473   -1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1726    2.0530    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    0.1608   -1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084    0.9661   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1782    1.9781   -1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9114   -0.4280    1.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5099    0.8447    2.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639    2.5694    1.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6668    1.3301    2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2911    2.2058   -0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6608    2.3108    0.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0254    0.8487   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2877   -0.4739   -2.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4393   -1.5927   -1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0246   -1.2085   -0.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0874   -0.9207   -0.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3335   -0.6328    1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3110    1.7106    1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0314    1.4383   -0.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5653    0.1421    2.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2024   -2.1220    1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7860   -2.8440    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9552   -2.3343   -0.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1782   -1.0899   -1.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6191   -0.5802   -0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3930    0.6218   -0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3652    2.0132    1.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1755    2.8364    0.1939 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
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  6  7  1  0
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  8  9  1  0
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  8  2  1  0
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  4 34  1  0
  5 35  1  0
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 29 75  1  0
 29 76  1  0
 30 77  1  0
 30 78  1  0
M  END

  Mrv1652309042000242D          

 30 31  0  0  0  0            999 V2000
 9993.807010000.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6567 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3706 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0846 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7985 9998.8096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.5120 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.2257 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9413 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6548 9998.8096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.3704 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.0839 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.7974 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5130 9998.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.2265 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5130 9997.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6548 9997.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7985 9997.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6567 9998.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3794 9999.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3794 9997.5669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8064 9999.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0920 9998.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0919 9997.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8063 9997.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.2315 9999.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5170 9998.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5170 9997.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.2315 9997.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9459 9997.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9459 9998.8077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  2  3  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
  5 17  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  1  1  0  0  0
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  1 21  1  0  0  0  0
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 30 18  1  1  0  0  0
 26 21  2  0  0  0  0
 24 27  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001492

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1

> <INCHI_KEY>
QUEDXNHFTDJVIY-DQCZWYHMSA-N

> <FORMULA>
C28H48O2

> <MOLECULAR_WEIGHT>
416.6795

> <EXACT_MASS>
416.36543078

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.11729989786745

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
8.81

> <JCHEM_LOGP>
9.994295870666667

> <ALOGPS_LOGS>
-7.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.470460494566392

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852416276824041

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
130.33289999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.37e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-tocopherol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001492
     RDKit          3D
gamma-Tocopherol
 78 79  0  0  0  0  0  0  0  0999 V2000
   -9.1098   -2.5454   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1948   -1.3944   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7291   -0.1610    0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1169    0.0394    0.4005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8642    0.9024    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4754    0.7692    0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9588   -0.4778   -0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8283   -1.5546   -0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2309   -2.8818   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5819   -0.5705   -0.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880    0.4876   -0.7583 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1490    0.3418   -2.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3722    0.2946   -0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561    0.2584    0.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5484    0.0185    1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043    0.9889    0.6437 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5961    1.0194   -0.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7700    0.6929    1.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9790    1.4599    1.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7968    1.5719   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4964    0.4327   -0.6137 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7344   -0.7409   -1.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6770   -0.1109    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7591    0.8714    0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9442    0.4332    1.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7752   -0.6763    0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1004   -2.0154    0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5282   -0.3990   -0.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3023    1.8490   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5725    1.9158    0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6241   -2.4473   -1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5234   -3.5030   -0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8402   -2.6112    0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7029   -0.7787    0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2561    1.9001    0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7819   -3.3956   -1.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2085   -2.7148   -0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1739   -3.5260    0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4168    0.9829   -2.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9879   -0.7365   -2.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1542    0.7058   -2.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9542    1.1583   -1.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1478   -0.6579   -1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3478    1.1843    1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5578   -0.5795    1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4766    0.0056    2.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2417   -1.0065    0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1726    2.0530    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    0.1608   -1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084    0.9661   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1782    1.9781   -1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9114   -0.4280    1.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5099    0.8447    2.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639    2.5694    1.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6668    1.3301    2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2911    2.2058   -0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6608    2.3108    0.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0254    0.8487   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2877   -0.4739   -2.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4393   -1.5927   -1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0246   -1.2085   -0.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0874   -0.9207   -0.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3335   -0.6328    1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3110    1.7106    1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0314    1.4383   -0.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5653    0.1421    2.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5571    1.3429    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5889   -0.8194    1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2024   -2.1220    1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7860   -2.8440    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9552   -2.3343   -0.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1782   -1.0899   -1.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6191   -0.5802   -0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3930    0.6218   -0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5036    2.3968    0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4571    2.4774   -1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3652    2.0132    1.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1755    2.8364    0.1939 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  2  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 11 29  1  0
 29 30  1  0
  8  2  1  0
 30  6  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  5 35  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  1
 17 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  6
 22 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  0
 25 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
 28 74  1  0
 29 75  1  0
 29 76  1  0
 30 77  1  0
 30 78  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  C   UNK     0    8660.4268665.219   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7588664.445   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.0918665.219   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8664.4248664.445   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8665.7568665.219   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8667.0888664.445   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.4248665.219   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8669.7568664.445   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8671.0918665.219   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8672.4238664.445   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8673.7558665.219   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8675.0918664.445   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8676.4238665.219   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8675.0918662.907   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8669.7568662.907   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.4248662.907   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8660.4268663.679   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8652.4428665.219   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0    8652.4428662.125   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0    8655.1058665.211   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8653.7728664.441   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8653.7728662.901   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8655.1058662.131   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0    8657.7658665.211   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0    8656.4328664.441   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8656.4328662.901   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8657.7658662.131   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8659.0998662.901   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8659.0998664.441   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2    3   30                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    9                                                            
CONECT   17    5                                                            
CONECT   18   30                                                            
CONECT   19   22                                                            
CONECT   20   23                                                            
CONECT   21   22    1   26                                                  
CONECT   22   21   23   19                                                  
CONECT   23   22   24   20                                                  
CONECT   24   23   27                                                       
CONECT   25   26   30                                                       
CONECT   26   27   25   21                                                  
CONECT   27   26   28   24                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25    2   18                                             
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

COMPND    HMDB0001492
HETATM    1  C1  UNL     1      -9.110  -2.545  -0.170  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.195  -1.394  -0.016  1.00  0.00           C  
HETATM    3  C3  UNL     1      -8.729  -0.161   0.260  1.00  0.00           C  
HETATM    4  O1  UNL     1     -10.117   0.039   0.400  1.00  0.00           O  
HETATM    5  C4  UNL     1      -7.864   0.902   0.401  1.00  0.00           C  
HETATM    6  C5  UNL     1      -6.475   0.769   0.274  1.00  0.00           C  
HETATM    7  C6  UNL     1      -5.959  -0.478  -0.004  1.00  0.00           C  
HETATM    8  C7  UNL     1      -6.828  -1.555  -0.147  1.00  0.00           C  
HETATM    9  C8  UNL     1      -6.231  -2.882  -0.444  1.00  0.00           C  
HETATM   10  O2  UNL     1      -4.582  -0.570  -0.124  1.00  0.00           O  
HETATM   11  C9  UNL     1      -3.888   0.488  -0.758  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.149   0.342  -2.264  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.372   0.295  -0.617  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.956   0.258   0.798  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.548   0.019   1.144  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.504   0.989   0.644  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.596   1.019  -0.828  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.770   0.693   1.376  1.00  0.00           C  
HETATM   19  C17 UNL     1       2.979   1.460   1.174  1.00  0.00           C  
HETATM   20  C18 UNL     1       3.797   1.572  -0.019  1.00  0.00           C  
HETATM   21  C19 UNL     1       4.496   0.433  -0.614  1.00  0.00           C  
HETATM   22  C20 UNL     1       3.734  -0.741  -1.111  1.00  0.00           C  
HETATM   23  C21 UNL     1       5.677  -0.111   0.195  1.00  0.00           C  
HETATM   24  C22 UNL     1       6.759   0.871   0.422  1.00  0.00           C  
HETATM   25  C23 UNL     1       7.944   0.433   1.186  1.00  0.00           C  
HETATM   26  C24 UNL     1       8.775  -0.676   0.709  1.00  0.00           C  
HETATM   27  C25 UNL     1       8.100  -2.015   0.576  1.00  0.00           C  
HETATM   28  C26 UNL     1       9.528  -0.399  -0.571  1.00  0.00           C  
HETATM   29  C27 UNL     1      -4.302   1.849  -0.344  1.00  0.00           C  
HETATM   30  C28 UNL     1      -5.572   1.916   0.432  1.00  0.00           C  
HETATM   31  H1  UNL     1      -9.624  -2.447  -1.170  1.00  0.00           H  
HETATM   32  H2  UNL     1      -8.523  -3.503  -0.206  1.00  0.00           H  
HETATM   33  H3  UNL     1      -9.840  -2.611   0.636  1.00  0.00           H  
HETATM   34  H4  UNL     1     -10.703  -0.779   0.286  1.00  0.00           H  
HETATM   35  H5  UNL     1      -8.256   1.900   0.622  1.00  0.00           H  
HETATM   36  H6  UNL     1      -6.782  -3.396  -1.263  1.00  0.00           H  
HETATM   37  H7  UNL     1      -5.208  -2.715  -0.834  1.00  0.00           H  
HETATM   38  H8  UNL     1      -6.174  -3.526   0.468  1.00  0.00           H  
HETATM   39  H9  UNL     1      -3.417   0.983  -2.756  1.00  0.00           H  
HETATM   40  H10 UNL     1      -3.988  -0.736  -2.492  1.00  0.00           H  
HETATM   41  H11 UNL     1      -5.154   0.706  -2.531  1.00  0.00           H  
HETATM   42  H12 UNL     1      -1.954   1.158  -1.180  1.00  0.00           H  
HETATM   43  H13 UNL     1      -2.148  -0.658  -1.117  1.00  0.00           H  
HETATM   44  H14 UNL     1      -2.348   1.184   1.345  1.00  0.00           H  
HETATM   45  H15 UNL     1      -2.558  -0.579   1.299  1.00  0.00           H  
HETATM   46  H16 UNL     1      -0.477   0.006   2.279  1.00  0.00           H  
HETATM   47  H17 UNL     1      -0.242  -1.006   0.810  1.00  0.00           H  
HETATM   48  H18 UNL     1       0.173   2.053   0.972  1.00  0.00           H  
HETATM   49  H19 UNL     1       0.066   0.161  -1.324  1.00  0.00           H  
HETATM   50  H20 UNL     1       1.608   0.966  -1.266  1.00  0.00           H  
HETATM   51  H21 UNL     1       0.178   1.978  -1.275  1.00  0.00           H  
HETATM   52  H22 UNL     1       1.911  -0.428   1.395  1.00  0.00           H  
HETATM   53  H23 UNL     1       1.510   0.845   2.517  1.00  0.00           H  
HETATM   54  H24 UNL     1       2.664   2.569   1.408  1.00  0.00           H  
HETATM   55  H25 UNL     1       3.667   1.330   2.116  1.00  0.00           H  
HETATM   56  H26 UNL     1       3.291   2.206  -0.799  1.00  0.00           H  
HETATM   57  H27 UNL     1       4.661   2.311   0.297  1.00  0.00           H  
HETATM   58  H28 UNL     1       5.025   0.849  -1.547  1.00  0.00           H  
HETATM   59  H29 UNL     1       3.288  -0.474  -2.110  1.00  0.00           H  
HETATM   60  H30 UNL     1       4.439  -1.593  -1.393  1.00  0.00           H  
HETATM   61  H31 UNL     1       3.025  -1.208  -0.427  1.00  0.00           H  
HETATM   62  H32 UNL     1       6.087  -0.921  -0.480  1.00  0.00           H  
HETATM   63  H33 UNL     1       5.333  -0.633   1.106  1.00  0.00           H  
HETATM   64  H34 UNL     1       6.311   1.711   1.053  1.00  0.00           H  
HETATM   65  H35 UNL     1       7.031   1.438  -0.522  1.00  0.00           H  
HETATM   66  H36 UNL     1       7.565   0.142   2.218  1.00  0.00           H  
HETATM   67  H37 UNL     1       8.557   1.343   1.398  1.00  0.00           H  
HETATM   68  H38 UNL     1       9.589  -0.819   1.488  1.00  0.00           H  
HETATM   69  H39 UNL     1       7.202  -2.122   1.201  1.00  0.00           H  
HETATM   70  H40 UNL     1       8.786  -2.844   0.965  1.00  0.00           H  
HETATM   71  H41 UNL     1       7.955  -2.334  -0.493  1.00  0.00           H  
HETATM   72  H42 UNL     1       9.178  -1.090  -1.382  1.00  0.00           H  
HETATM   73  H43 UNL     1      10.619  -0.580  -0.486  1.00  0.00           H  
HETATM   74  H44 UNL     1       9.393   0.622  -0.943  1.00  0.00           H  
HETATM   75  H45 UNL     1      -3.504   2.397   0.217  1.00  0.00           H  
HETATM   76  H46 UNL     1      -4.457   2.477  -1.271  1.00  0.00           H  
HETATM   77  H47 UNL     1      -5.365   2.013   1.537  1.00  0.00           H  
HETATM   78  H48 UNL     1      -6.175   2.836   0.194  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    3    8
CONECT    3    4    5
CONECT    4   34
CONECT    5    6    6   35
CONECT    6    7   30
CONECT    7    8    8   10
CONECT    8    9
CONECT    9   36   37   38
CONECT   10   11
CONECT   11   12   13   29
CONECT   12   39   40   41
CONECT   13   14   42   43
CONECT   14   15   44   45
CONECT   15   16   46   47
CONECT   16   17   18   48
CONECT   17   49   50   51
CONECT   18   19   52   53
CONECT   19   20   54   55
CONECT   20   21   56   57
CONECT   21   22   23   58
CONECT   22   59   60   61
CONECT   23   24   62   63
CONECT   24   25   64   65
CONECT   25   26   66   67
CONECT   26   27   28   68
CONECT   27   69   70   71
CONECT   28   72   73   74
CONECT   29   30   75   76
CONECT   30   77   78
END

HMDB0001492
     RDKit          3D
gamma-Tocopherol
 78 79  0  0  0  0  0  0  0  0999 V2000
   -9.1098   -2.5454   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1948   -1.3944   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7291   -0.1610    0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1169    0.0394    0.4005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8642    0.9024    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4754    0.7692    0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9588   -0.4778   -0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8283   -1.5546   -0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2309   -2.8818   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5819   -0.5705   -0.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880    0.4876   -0.7583 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1490    0.3418   -2.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3722    0.2946   -0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561    0.2584    0.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5484    0.0185    1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043    0.9889    0.6437 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5961    1.0194   -0.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7700    0.6929    1.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9790    1.4599    1.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7968    1.5719   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4964    0.4327   -0.6137 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7344   -0.7409   -1.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6770   -0.1109    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7591    0.8714    0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9442    0.4332    1.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7752   -0.6763    0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1004   -2.0154    0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5282   -0.3990   -0.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3023    1.8490   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5725    1.9158    0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6241   -2.4473   -1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5234   -3.5030   -0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8402   -2.6112    0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7029   -0.7787    0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2561    1.9001    0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7819   -3.3956   -1.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2085   -2.7148   -0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1739   -3.5260    0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4168    0.9829   -2.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9879   -0.7365   -2.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1542    0.7058   -2.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9542    1.1583   -1.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1478   -0.6579   -1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3478    1.1843    1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5578   -0.5795    1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4766    0.0056    2.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2417   -1.0065    0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1726    2.0530    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    0.1608   -1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084    0.9661   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1782    1.9781   -1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9114   -0.4280    1.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5099    0.8447    2.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639    2.5694    1.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6668    1.3301    2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2911    2.2058   -0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6608    2.3108    0.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0254    0.8487   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2877   -0.4739   -2.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4393   -1.5927   -1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0246   -1.2085   -0.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0874   -0.9207   -0.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3335   -0.6328    1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3110    1.7106    1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0314    1.4383   -0.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5653    0.1421    2.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5571    1.3429    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5889   -0.8194    1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2024   -2.1220    1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7860   -2.8440    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9552   -2.3343   -0.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1782   -1.0899   -1.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6191   -0.5802   -0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3930    0.6218   -0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5036    2.3968    0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4571    2.4774   -1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3652    2.0132    1.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1755    2.8364    0.1939 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  2  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 11 29  1  0
 29 30  1  0
  8  2  1  0
 30  6  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  5 35  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  1
 17 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  6
 22 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  0
 25 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
 28 74  1  0
 29 75  1  0
 29 76  1  0
 30 77  1  0
 30 78  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-gamma-Tocopherol	ChEBI
(2R)-2,7,8-Trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol	ChEBI
(2R)-3,4-Dihydro-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol	ChEBI
(2R,4'r,8'r)-gamma-Tocopherol	ChEBI
(R,R,R)-gamma-Tocopherol	ChEBI
7,8-Dimethyltocol	ChEBI
D-gamma-Tocopherol	ChEBI
e308	ChEBI
RRR-gamma-Tocopherol	ChEBI
(+)-g-Tocopherol	Generator
(+)-Γ-tocopherol	Generator
(2R,4'r,8'r)-g-Tocopherol	Generator
(2R,4'r,8'r)-Γ-tocopherol	Generator
(R,R,R)-g-Tocopherol	Generator
(R,R,R)-Γ-tocopherol	Generator
D-g-Tocopherol	Generator
RRR-g-Tocopherol	Generator
RRR-Γ-tocopherol	Generator
g-Tocopherol	Generator
3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol	HMDB
(2R,4’R,8’r)-γ-tocopherol	HMDB
all-(R)-gamma-Tocopherol	HMDB
all-(R)-Γ-tocopherol	HMDB
gamma-Tocopherol	HMDB

Chemical Formula

C₂₈H₄₈O₂

Average Molecular Weight

416.6795

Monoisotopic Molecular Weight

416.36543078

IUPAC Name

(2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

gamma-tocopherol

CAS Registry Number

54-28-4

SMILES

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

InChI Identifier

InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1

InChI Key

QUEDXNHFTDJVIY-DQCZWYHMSA-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:18185 )
vitamin E (C02483 )
Vitamin E (LMPR02020060 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0001492)

Adipose tissue (HMDB: HMDB0001492)
Adipose tissue (HMDB: HMDB0001492)

Nervous tissue

Nervous tissue (HMDB: HMDB0001492)

Muscle tissue

Skeletal muscle (HMDB: HMDB0001492)
Skeletal muscle (HMDB: HMDB0001492)

Epithelium

Epidermis (HMDB: HMDB0001492)

Non-excretory biofluid

Biofluid or Excreta

Cellular substructure

Cell

Fibroblast

Fibroblast (HMDB: HMDB0001492)

Hematocyte

Platelet (HMDB: HMDB0001492)

Tissue substructure

Muscle (HMDB: HMDB0001492)

Organ

Excreta

Biofluid or Excreta

Feces (PMID: 22411374)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001492)

Source

Exogenous

Exogenous (HMDB: HMDB0001492)

Food

Food (HMDB: HMDB0001492)

Animal origin

Poultry

Turkey (FooDB: FOOD00494)
Chicken (FooDB: FOOD00329)

Swine

Domestic pig (FooDB: FOOD00536)

Bovine

Cattle (Beef, Veal) (FooDB: FOOD00495)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Vegetable

Cabbage

Onion-family vegetable

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Bilberry (FooDB: FOOD00193)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruit product

Fruit preserve (FooDB: FOOD00660)
Fruit salad (FooDB: FOOD00766)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Bread products

Other bread product (FooDB: FOOD00805)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Potato puffs (FooDB: FOOD00846)

Tex-mex cuisine

Chili (FooDB: FOOD00707)
Burrito (FooDB: FOOD00704)
Nachos (FooDB: FOOD00710)
Taco (FooDB: FOOD00708)

Levantine cuisine

Hummus (FooDB: FOOD00845)

Sandwich

Asian cuisine

Egg roll (FooDB: FOOD00717)

Latin american cuisine

Tamale (FooDB: FOOD00795)
Empanada (FooDB: FOOD00830)
Pupusa (FooDB: FOOD00829)
Arepa (FooDB: FOOD00831)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)
Pie crust (FooDB: FOOD00780)

Dressing

Salad dressing (FooDB: FOOD00645)

Sauce

Sauce (FooDB: FOOD00646)

Condiment

Ketchup (FooDB: FOOD00756)

Substitute

Cream substitute (FooDB: FOOD00713)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Other beverage

Nutritional beverage

Nutritional drink (FooDB: FOOD00754)

Aquatic origin

Mollusk

Blue mussel (FooDB: FOOD00304)
Marine mussel (FooDB: FOOD00587)
Bivalvia (Clam, Mussel, Oyster) (FooDB: FOOD00531)
Scallop (FooDB: FOOD00462)

Fish

Pacific cod (FooDB: FOOD00337)
Atlantic cod (FooDB: FOOD00338)
Hippoglossus (Common halibut) (FooDB: FOOD00375)
Pacific rockfish (FooDB: FOOD00426)
Orange roughy (FooDB: FOOD00448)
Pink salmon (FooDB: FOOD00450)
Sockeye salmon (FooDB: FOOD00453)
Sheefish (FooDB: FOOD00472)
Swordfish (FooDB: FOOD00487)
Yellowfin tuna (FooDB: FOOD00511)
Pollock (FooDB: FOOD00513)
Gadus (Common cod) (FooDB: FOOD00515)
Atlantic halibut (FooDB: FOOD00516)
Pacific halibut (FooDB: FOOD00517)
Flatfish (FooDB: FOOD00535)
Gadiformes (FooDB: FOOD00580)
Lemon sole (FooDB: FOOD00583)
Pacific ocean perch (FooDB: FOOD00598)
True sole (FooDB: FOOD00604)
Cichlidae (Tilapia) (FooDB: FOOD00699)
Haddock (FooDB: FOOD00374)
Norway haddock (FooDB: FOOD00588)
Rainbow trout (FooDB: FOOD00444)
Thunnus (FooDB: FOOD00607)
Whitefish (FooDB: FOOD00503)
European anchovy (FooDB: FOOD00362)
Channel catfish (FooDB: FOOD00324)
Painted comber (FooDB: FOOD00294)
Alaska pollock (FooDB: FOOD00497)
Atlantic salmon (FooDB: FOOD00455)
Chinook salmon (FooDB: FOOD00454)
Chum salmon (FooDB: FOOD00451)
Coho salmon (FooDB: FOOD00452)
Pacific sardine (FooDB: FOOD00461)
Albacore tuna (FooDB: FOOD00514)
Smelt (FooDB: FOOD00519)

Bivalvia

Clam (FooDB: FOOD00952)

Fish product

Other fish product (FooDB: FOOD00665)

Crustacean

Shrimp (FooDB: FOOD00533)
Blue crab (FooDB: FOOD00303)

Cetacean

Beluga whale (FooDB: FOOD00300)

Pinniped

Bearded seal (FooDB: FOOD00466)
Spotted seal (FooDB: FOOD00423)

Milk and milk product

Other milk product

Fermented milk product

Fermented milk

Buttermilk (FooDB: FOOD00692)

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Fat and oil

Animal fat

Lard (FooDB: FOOD00681)

Vegetable fat

Margarine-like spread (FooDB: FOOD00844)
Margarine (FooDB: FOOD00843)
Shortening (FooDB: FOOD00783)

Fats and oils (FooDB: FOOD00864)

Egg

Egg yolk (FooDB: FOOD00919)
Eggs (FooDB: FOOD00619)

Baby food

Baby food (FooDB: FOOD00668)

Unclassified food or beverage

Unclassified food or beverage (FooDB: FOOD00672)

Cocoa and cocoa product

Cocoa product

Chocolate (FooDB: FOOD00687)
Hot chocolate (FooDB: FOOD00688)

Snack

Confectionery

Dessert

Pastry (FooDB: FOOD00641)
Cake (FooDB: FOOD00636)
Pie (FooDB: FOOD00782)
Pudding (FooDB: FOOD00734)

Frozen dessert

Ice cream (FooDB: FOOD00624)

Candy

Other candy (FooDB: FOOD00679)
Candy bar (FooDB: FOOD00841)

Spread

Dulce de leche (FooDB: FOOD00714)

Milk dessert

Sweet custard (FooDB: FOOD00716)

Other confectionery

Icing (FooDB: FOOD00700)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0001492)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0001492)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0001492)

Prostate cancer (HMDB: HMDB0001492)

Cellular process

Cell signaling (HMDB: HMDB0001492)

Biochemical process

Lipid transport (HMDB: HMDB0001492)

Role

Industrial applicationBiological role

Hormone antagonist (HMDB: HMDB0001492)
Energy source (HMDB: HMDB0001492)
Anti atherosclerotic (HMDB: HMDB0001492)
Anti cancer (HMDB: HMDB0001492)
Anti C-reactive-protein (HMDB: HMDB0001492)
Anti-inflammatory (HMDB: HMDB0001492)
Cardioprotective (HMDB: HMDB0001492)
Hypocholesterolemic (HMDB: HMDB0001492)
Natriuretic (HMDB: HMDB0001492)

Modulator

Inhibitor

Enzyme inhibitor

Cyclooxygenase inhibitor (HMDB: HMDB0001492)

Nitric-oxide inhibitor (HMDB: HMDB0001492)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-67.50 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	226.20 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	128 mg/mL	Not Available
LogP	4.352 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.4e-06 g/L	ALOGPS
logP	8.81	ALOGPS
logP	9.99	ChemAxon
logS	-7.8	ALOGPS
pKa (Strongest Acidic)	10.47	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	130.33 m³·mol⁻¹	ChemAxon
Polarizability	54.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	208.979	30932474
DeepCCS	[M-H]-	206.621	30932474
DeepCCS	[M-2H]-	239.504	30932474
DeepCCS	[M+Na]+	215.072	30932474
AllCCS	[M+H]+	212.9	32859911
AllCCS	[M+H-H2O]+	210.8	32859911
AllCCS	[M+NH4]+	214.9	32859911
AllCCS	[M+Na]+	215.5	32859911
AllCCS	[M-H]-	211.9	32859911
AllCCS	[M+Na-2H]-	214.5	32859911
AllCCS	[M+HCOO]-	217.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Tocopherol	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1	3807.9	Standard polar	33892256
gamma-Tocopherol	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1	3004.6	Standard non polar	33892256
gamma-Tocopherol	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1	3121.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
gamma-Tocopherol,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C=C2CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)OC2=C1C	2996.5	Semi standard non polar	33892256
gamma-Tocopherol,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C=C2CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)OC2=C1C	3267.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - gamma-Tocopherol GC-MS (1 TMS)	splash10-00di-2290200000-ca2e59769b7f9d283302	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-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 - gamma-Tocopherol n/a 29V, negative-QTOF	splash10-0udi-0100900000-866035964c66e6e4a63c	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 13V, negative-QTOF	splash10-014i-0000900000-92e50ec0b18c795338b0	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 16V, negative-QTOF	splash10-014j-0400900000-1fb1b39165372804b2c1	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 19V, negative-QTOF	splash10-0002-0900500000-42bb4a664eeebbe24ff8	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 24V, negative-QTOF	splash10-0002-0900200000-e8897dc0cd8b10c11820	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 30V, negative-QTOF	splash10-0002-0900100000-ea386123915e3fbbc82b	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 37V, negative-QTOF	splash10-0002-0900000000-896627229022e40d2d4c	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 44V, negative-QTOF	splash10-0002-0900000000-cc98083bdb10a92cc694	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 51V, negative-QTOF	splash10-0002-0900000000-0c37948386f3f3e84231	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 58V, negative-QTOF	splash10-006t-0900000000-82abe7b9bcb60c5e016f	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 64V, negative-QTOF	splash10-006t-0900000000-8ebacaefdf6ce927eb8f	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 75V, negative-QTOF	splash10-05fs-0900000000-6045c9c0b33abee0cf8c	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 85V, negative-QTOF	splash10-0ab9-0900000000-814007aa4a0b534c8b92	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 96V, negative-QTOF	splash10-0ab9-1900000000-7f6bf2020beb1db07038	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 109V, negative-QTOF	splash10-0ab9-1900000000-da96e9792269933d640e	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol n/a 29V, negative-QTOF	splash10-0udi-0200900000-b8c469956aa52f5cea7b	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol n/a 29V, negative-QTOF	splash10-0udi-0200900000-c061dcce18ca02fdc7f8	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol n/a 29V, negative-QTOF	splash10-03di-0900000000-eaab1ecd4d7ca06a99f6	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Tocopherol n/a 29V, positive-QTOF	splash10-014i-0911200000-794ce3ca05c79d17f851	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocopherol 10V, Positive-QTOF	splash10-014i-1842900000-c0a3ade1f225f3c78ac2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocopherol 20V, Positive-QTOF	splash10-0udi-1910000000-db436d443f9dc640b979	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocopherol 40V, Positive-QTOF	splash10-0pb9-5930000000-1cbe4445929c9b90be47	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocopherol 10V, Negative-QTOF	splash10-014i-0110900000-23d01b80a965180b27d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocopherol 20V, Negative-QTOF	splash10-014j-0931800000-70e6ff42d0190b91ef52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Tocopherol 40V, Negative-QTOF	splash10-0002-0932000000-e16b76b24d1cd56f30b1	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Breast Milk
Feces

Tissue Locations

Adipose Tissue
Epidermis
Erythrocyte
Fibroblasts
Heart
Intestine
Leukocyte
Liver
Placenta
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	2.41 (2.3-2.5) uM	Adult (>18 years old)	Both	Normal	17823432	details
Blood	Detected and Quantified	1.29 (0.63-2.63) uM	Adult (>18 years old)	Both	Normal	16690736	details
Blood	Detected and Quantified	36.920 +/- 11.540 uM	Adult (>18 years old)	Both	Normal	15051849	details
Blood	Detected and Quantified	39.100 +/- 11.940 uM	Adult (>18 years old)	Both	Normal	15051849	details
Blood	Detected and Quantified	4.500 +/- 3.0700 uM	Adult (>18 years old)	Both	Normal	15051849	details
Blood	Detected and Quantified	42.380 +/- 14.790 uM	Adult (>18 years old)	Both	Normal	15051849	details
Blood	Detected and Quantified	47.670 +/- 18.690 uM	Adult (>18 years old)	Both	Normal	15051849	details
Blood	Detected and Quantified	5.320 +/- 3.620 uM	Adult (>18 years old)	Both	Normal	15051849	details
Blood	Detected and Quantified	5.360 +/- 3.0700 uM	Adult (>18 years old)	Both	Normal	15051849	details
Blood	Detected and Quantified	5.390 +/- 2.880 uM	Adult (>18 years old)	Both	Normal	15051849	details
Blood	Detected and Quantified	40.540 +/- 12.450 uM	Adult (>18 years old)	Female	Normal	15051849	details
Blood	Detected and Quantified	42.280 +/- 16.230 uM	Adult (>18 years old)	Female	Normal	15051849	details
Blood	Detected and Quantified	5.600 +/- 3.0400 uM	Adult (>18 years old)	Female	Normal	15051849	details
Blood	Detected and Quantified	5.970 +/- 3.510 uM	Adult (>18 years old)	Female	Normal	15051849	details
Blood	Detected and Quantified	4.0600 +/- 2.690 uM	Adult (>18 years old)	Male	Normal	15051849	details
Blood	Detected and Quantified	4.440 +/- 3.0400 uM	Adult (>18 years old)	Male	Normal	15051849	details
Blood	Detected and Quantified	41.120 +/- 14.950 uM	Adult (>18 years old)	Male	Normal	15051849	details
Blood	Detected and Quantified	43.650 +/- 17.390 uM	Adult (>18 years old)	Male	Normal	15051849	details
Blood	Detected and Quantified	3.2 uM	Adult (>18 years old)	Female	Normal	17116719	details
Blood	Detected and Quantified	3.7 uM	Adult (>18 years old)	Male	Normal	17116719	details
Blood	Detected and Quantified	6.720 +/- 3.360 uM	Adult (>18 years old)	Both	Normal	16755268	details
Blood	Detected and Quantified	1.458 uM	Children (1-13 years old)	Female	Normal	19602831	details
Blood	Detected and Quantified	1.469 uM	Adolescent (13-18 years old)	Female	Normal	19602831	details
Blood	Detected and Quantified	1.48 uM	Adult (>18 years old)	Female	Normal	19371448	details
Blood	Detected and Quantified	5.508 uM	Adult (>18 years old)	Female	Normal	20332276	details
Blood	Detected and Quantified	1.440 +/- 0.720 uM	Adult (>18 years old)	Female	Normal	1512628	details
Blood	Detected and Quantified	2.0159 +/- 0.696 uM	Adult (>18 years old)	Female	Normal	10427874	details
Blood	Detected and Quantified	2.360 +/- 0.760 uM	Adolescent (13-18 years old)	Female	Normal	12368412	details
Blood	Detected and Quantified	2.600 +/- 0.100 uM	Adult (>18 years old)	Female	Normal	11522560	details
Blood	Detected and Quantified	2.700 +/- 0.100 uM	Adult (>18 years old)	Female	Normal	11522560	details
Blood	Detected and Quantified	2.806 +/- 1.721 uM	Adult (>18 years old)	Female	Normal	18813024	details
Blood	Detected and Quantified	29.0367 +/- 10.384 uM	Adult (>18 years old)	Female	Normal	18813024	details
Blood	Detected and Quantified	1.351 uM	Adolescent (13-18 years old)	Male	Normal	19602831	details
Blood	Detected and Quantified	1.473 uM	Children (1-13 years old)	Male	Normal	19602831	details
Blood	Detected and Quantified	1.63 uM	Adult (>18 years old)	Male	Normal	19371448	details
Blood	Detected and Quantified	0.00576 +/- 0.00240 uM	Adult (>18 years old)	Male	Normal	11744516	details
Blood	Detected and Quantified	1.440 +/- 0.790 uM	Adult (>18 years old)	Male	Normal	1512628	details
Blood	Detected and Quantified	2.280 +/- 0.980 uM	Adolescent (13-18 years old)	Male	Normal	12368412	details
Blood	Detected and Quantified	2.700 +/- 0.100 uM	Adult (>18 years old)	Male	Normal	11522560	details
Blood	Detected and Quantified	7.2 (3.8-11.7) uM	Adult (>18 years old)	Female	Normal	19235557	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22007635	details
Breast Milk	Detected and Quantified	0.5430037 +/- 0.0966421 uM	Adult (>18 years old)	Female	Normal	2388136	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.3 (2.2-2.43) uM	Adult (>18 years old)	Both	Prostate cancer	17823432	details
Blood	Detected and Quantified	6.2 (3.6-8.4) uM	Adult (>18 years old)	Female	Endometrial cancer	19235557	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22007635	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Prostate cancer
Key TJ, Appleby PN, Allen NE, Travis RC, Roddam AW, Jenab M, Egevad L, Tjonneland A, Johnsen NF, Overvad K, Linseisen J, Rohrmann S, Boeing H, Pischon T, Psaltopoulou T, Trichopoulou A, Trichopoulos D, Palli D, Vineis P, Tumino R, Berrino F, Kiemeney L, Bueno-de-Mesquita HB, Quiros JR, Gonzalez CA, Martinez C, Larranaga N, Chirlaque MD, Ardanaz E, Stattin P, Hallmans G, Khaw KT, Bingham S, Slimani N, Ferrari P, Rinaldi S, Riboli E: Plasma carotenoids, retinol, and tocopherols and the risk of prostate cancer in the European Prospective Investigation into Cancer and Nutrition study. Am J Clin Nutr. 2007 Sep;86(3):672-81. [PubMed:17823432 ]
Endometrial cancer
Jeong NH, Song ES, Lee JM, Lee KB, Kim MK, Yun YM, Lee JK, Son SK, Lee JP, Kim JH, Hur SY, Kwon YI: Preoperative levels of plasma micronutrients are related to endometrial cancer risk. Acta Obstet Gynecol Scand. 2009;88(4):434-9. doi: 10.1080/00016340902767187. [PubMed:19235557 ]
Schizophrenia
Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8. [PubMed:22007635 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ] 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 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]

Associated OMIM IDs

176807 (Prostate cancer)
608089 (Endometrial cancer)
181500 (Schizophrenia)
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

Gamma-Tocopherol

METLIN ID

Not Available

PubChem Compound

92729

PDB ID

Not Available

ChEBI ID

18185

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000332

Good Scents ID

rw1013461

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Zhan X, Wang SY, Wang L, Qu P: [Decreased peripheral nerve conduction velocity may be associated with lower-serum level of vitamin E in patients with infantile hepatitis syndrome]. Zhonghua Er Ke Za Zhi. 2004 May;42(5):362-6. [PubMed:15189696 ]
Reiter N, Jonsson B, Jansen E, Espersen K: [Vitamin E and excessive bleeding]. Ugeskr Laeger. 2005 Dec 5;167(49):4664-5. [PubMed:16336861 ]
Chelchowska M, Laskowska-Klita T, Leibschang J: [The effect of tobacco smoking during pregnancy on concentration of vitamin E in blood of mothers and their newborns in umbilical cord blood]. Ginekol Pol. 2006 Apr;77(4):263-8. [PubMed:16875031 ]
Vatassery GT, Adityanjee, Quach HT, Smith WE, Kuskowski MA, Melnyk D: Alpha and gamma tocopherols in cerebrospinal fluid and serum from older, male, human subjects. J Am Coll Nutr. 2004 Jun;23(3):233-8. [PubMed:15190048 ]
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 ]
Nair S, Norkus EP, Hertan H, Pitchumoni CS: Micronutrient antioxidants in gastric mucosa and serum in patients with gastritis and gastric ulcer: does Helicobacter pylori infection affect the mucosal levels? J Clin Gastroenterol. 2000 Jun;30(4):381-5. [PubMed:10875465 ]
Chow CK: Distribution of tocopherols in human plasma and red blood cells. Am J Clin Nutr. 1975 Jul;28(7):756-60. [PubMed:1146729 ]
Tauler P, Sureda A, Cases N, Aguilo A, Rodriguez-Marroyo JA, Villa G, Tur JA, Pons A: Increased lymphocyte antioxidant defences in response to exhaustive exercise do not prevent oxidative damage. J Nutr Biochem. 2006 Oct;17(10):665-71. Epub 2005 Nov 28. [PubMed:16481153 ]
Hozyasz KK, Chelchowska M, Laskowska-Klita T: [Vitamin E levels in patients with celiac disease]. Med Wieku Rozwoj. 2003 Oct-Dec;7(4 Pt 2):593-604. [PubMed:15213374 ]
Sokol RJ, Heubi JE, Iannaccone S, Bove KE, Balistreri WF: Mechanism causing vitamin E deficiency during chronic childhood cholestasis. Gastroenterology. 1983 Nov;85(5):1172-82. [PubMed:6618108 ]
Ble-Castillo JL, Carmona-Diaz E, Mendez JD, Larios-Medina FJ, Medina-Santillan R, Cleva-Villanueva G, Diaz-Zagoya JC: Effect of alpha-tocopherol on the metabolic control and oxidative stress in female type 2 diabetics. Biomed Pharmacother. 2005 Jul;59(6):290-5. [PubMed:15932790 ]
Kontush K, Schekatolina S: Vitamin E in neurodegenerative disorders: Alzheimer's disease. Ann N Y Acad Sci. 2004 Dec;1031:249-62. [PubMed:15753151 ]
Kayden HJ, Hatam LJ, Traber MG: The measurement of nanograms of tocopherol from needle aspiration biopsies of adipose tissue: normal and abetalipoproteinemic subjects. J Lipid Res. 1983 May;24(5):652-6. [PubMed:6875389 ]
Guggenheim MA, Ringel SP, Silverman A, Grabert BE, Neville HE: Progressive neuromuscular disease in children with chronic cholestasis and vitamin E deficiency: clinical and muscle biopsy findings and treatment with alpha-tocopherol. Ann N Y Acad Sci. 1982;393:84-95. [PubMed:6959572 ]
Burton GW, Traber MG, Acuff RV, Walters DN, Kayden H, Hughes L, Ingold KU: Human plasma and tissue alpha-tocopherol concentrations in response to supplementation with deuterated natural and synthetic vitamin E. Am J Clin Nutr. 1998 Apr;67(4):669-84. [PubMed:9537614 ]
Jeanes YM, Hall WL, Proteggente AR, Lodge JK: Cigarette smokers have decreased lymphocyte and platelet alpha-tocopherol levels and increased excretion of the gamma-tocopherol metabolite gamma-carboxyethyl-hydroxychroman (gamma-CEHC). Free Radic Res. 2004 Aug;38(8):861-8. [PubMed:15493460 ]
Leo MA, Rosman AS, Lieber CS: Differential depletion of carotenoids and tocopherol in liver disease. Hepatology. 1993 Jun;17(6):977-86. [PubMed:8514270 ]
Yeum KJ, Ahn SH, Rupp de Paiva SA, Lee-Kim YC, Krinsky NI, Russell RM: Correlation between carotenoid concentrations in serum and normal breast adipose tissue of women with benign breast tumor or breast cancer. J Nutr. 1998 Nov;128(11):1920-6. [PubMed:9808643 ]
Jeanes YM, Hall WL, Lodge JK: Comparative (2)H-labelled alpha-tocopherol biokinetics in plasma, lipoproteins, erythrocytes, platelets and lymphocytes in normolipidaemic males. Br J Nutr. 2005 Jul;94(1):92-9. [PubMed:16115338 ]
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 ]
Jiang Q, Christen S, Shigenaga MK, Ames BN: gamma-tocopherol, the major form of vitamin E in the US diet, deserves more attention. Am J Clin Nutr. 2001 Dec;74(6):714-22. doi: 10.1093/ajcn/74.6.714. [PubMed:11722951 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for gamma-Tocopherol (HMDB0001492)

MOL for HMDB0001492 (gamma-Tocopherol)

3D MOL for HMDB0001492 (gamma-Tocopherol)

3D SDF for HMDB0001492 (gamma-Tocopherol)

3D-SDF for HMDB0001492 (gamma-Tocopherol)

PDB for HMDB0001492 (gamma-Tocopherol)

3D PDB for HMDB0001492 (gamma-Tocopherol)

SMILES for HMDB0001492 (gamma-Tocopherol)

INCHI for HMDB0001492 (gamma-Tocopherol)

Structure for HMDB0001492 (gamma-Tocopherol)

3D Structure for HMDB0001492 (gamma-Tocopherol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra