Hmdb loader

Showing metabocard for gamma-Tocopherol (HMDB0001492)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:10 UTC
HMDB IDHMDB0001492
Secondary Accession Numbers
  • HMDB0002634
  • HMDB01492
  • HMDB02634
Metabolite Identification
Common Namegamma-Tocopherol
Descriptiongamma-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
Data?1582752205
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001492 (gamma-Tocopherol)


  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
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 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
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 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
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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
Download

3D MOL for HMDB0001492 (gamma-Tocopherol)

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
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   -6.2309   -2.8818   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
Download

3D SDF for HMDB0001492 (gamma-Tocopherol)


  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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 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

$$$$
Download

3D-SDF for HMDB0001492 (gamma-Tocopherol)

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
Download

PDB for HMDB0001492 (gamma-Tocopherol)

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
Download

3D PDB for HMDB0001492 (gamma-Tocopherol)

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
Download

SMILES for HMDB0001492 (gamma-Tocopherol)

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

INCHI for HMDB0001492 (gamma-Tocopherol)

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
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
(+)-gamma-TocopherolChEBI
(2R)-2,7,8-Trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-olChEBI
(2R)-3,4-Dihydro-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-olChEBI
(2R,4'r,8'r)-gamma-TocopherolChEBI
(R,R,R)-gamma-TocopherolChEBI
7,8-DimethyltocolChEBI
D-gamma-TocopherolChEBI
e308ChEBI
RRR-gamma-TocopherolChEBI
(+)-g-TocopherolGenerator
(+)-Γ-tocopherolGenerator
(2R,4'r,8'r)-g-TocopherolGenerator
(2R,4'r,8'r)-Γ-tocopherolGenerator
(R,R,R)-g-TocopherolGenerator
(R,R,R)-Γ-tocopherolGenerator
D-g-TocopherolGenerator
RRR-g-TocopherolGenerator
RRR-Γ-tocopherolGenerator
g-TocopherolGenerator
3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-olHMDB
(2R,4’R,8’r)-γ-tocopherolHMDB
all-(R)-gamma-TocopherolHMDB
all-(R)-Γ-tocopherolHMDB
gamma-TocopherolHMDB
Chemical FormulaC28H48O2
Average Molecular Weight416.6795
Monoisotopic Molecular Weight416.36543078
IUPAC Name(2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Namegamma-tocopherol
CAS Registry Number54-28-4
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 KeyQUEDXNHFTDJVIY-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentTocopherols
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndirect biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point-67.50 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point226.20 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility128 mg/mLNot Available
LogP4.352 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.4e-06 g/LALOGPS
logP8.81ALOGPS
logP9.99ChemAxon
logS-7.8ALOGPS
pKa (Strongest Acidic)10.47ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity130.33 m³·mol⁻¹ChemAxon
Polarizability54.12 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+208.97930932474
DeepCCS[M-H]-206.62130932474
DeepCCS[M-2H]-239.50430932474
DeepCCS[M+Na]+215.07230932474
AllCCS[M+H]+212.932859911
AllCCS[M+H-H2O]+210.832859911
AllCCS[M+NH4]+214.932859911
AllCCS[M+Na]+215.532859911
AllCCS[M-H]-211.932859911
AllCCS[M+Na-2H]-214.532859911
AllCCS[M+HCOO]-217.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
gamma-TocopherolCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O13807.9Standard polar33892256
gamma-TocopherolCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O13004.6Standard non polar33892256
gamma-TocopherolCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O13121.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
gamma-Tocopherol,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C=C2CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)OC2=C1C2996.5Semi standard non polar33892256
gamma-Tocopherol,1TBDMS,isomer #1CC1=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=C1C3267.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - gamma-Tocopherol GC-MS (1 TMS)splash10-00di-2290200000-ca2e59769b7f9d2833022014-06-16HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Tocopherol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol n/a 29V, negative-QTOFsplash10-0udi-0100900000-866035964c66e6e4a63c2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 13V, negative-QTOFsplash10-014i-0000900000-92e50ec0b18c795338b02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 16V, negative-QTOFsplash10-014j-0400900000-1fb1b39165372804b2c12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 19V, negative-QTOFsplash10-0002-0900500000-42bb4a664eeebbe24ff82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 24V, negative-QTOFsplash10-0002-0900200000-e8897dc0cd8b10c118202020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 30V, negative-QTOFsplash10-0002-0900100000-ea386123915e3fbbc82b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 37V, negative-QTOFsplash10-0002-0900000000-896627229022e40d2d4c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 44V, negative-QTOFsplash10-0002-0900000000-cc98083bdb10a92cc6942020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 51V, negative-QTOFsplash10-0002-0900000000-0c37948386f3f3e842312020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 58V, negative-QTOFsplash10-006t-0900000000-82abe7b9bcb60c5e016f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 64V, negative-QTOFsplash10-006t-0900000000-8ebacaefdf6ce927eb8f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 75V, negative-QTOFsplash10-05fs-0900000000-6045c9c0b33abee0cf8c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 85V, negative-QTOFsplash10-0ab9-0900000000-814007aa4a0b534c8b922020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 96V, negative-QTOFsplash10-0ab9-1900000000-7f6bf2020beb1db070382020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 109V, negative-QTOFsplash10-0ab9-1900000000-da96e9792269933d640e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol n/a 29V, negative-QTOFsplash10-0udi-0200900000-b8c469956aa52f5cea7b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol n/a 29V, negative-QTOFsplash10-0udi-0200900000-c061dcce18ca02fdc7f82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol n/a 29V, negative-QTOFsplash10-03di-0900000000-eaab1ecd4d7ca06a99f62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol n/a 29V, positive-QTOFsplash10-014i-0911200000-794ce3ca05c79d17f8512020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocopherol 10V, Positive-QTOFsplash10-014i-1842900000-c0a3ade1f225f3c78ac22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocopherol 20V, Positive-QTOFsplash10-0udi-1910000000-db436d443f9dc640b9792016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocopherol 40V, Positive-QTOFsplash10-0pb9-5930000000-1cbe4445929c9b90be472016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocopherol 10V, Negative-QTOFsplash10-014i-0110900000-23d01b80a965180b27d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocopherol 20V, Negative-QTOFsplash10-014j-0931800000-70e6ff42d0190b91ef522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocopherol 40V, Negative-QTOFsplash10-0002-0932000000-e16b76b24d1cd56f30b12016-08-03Wishart LabView 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
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.41 (2.3-2.5) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.29 (0.63-2.63) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified36.920 +/- 11.540 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified39.100 +/- 11.940 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified4.500 +/- 3.0700 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified42.380 +/- 14.790 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified47.670 +/- 18.690 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified5.320 +/- 3.620 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified5.360 +/- 3.0700 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified5.390 +/- 2.880 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified40.540 +/- 12.450 uMAdult (>18 years old)Female
Normal		 details
BloodDetected and Quantified42.280 +/- 16.230 uMAdult (>18 years old)Female
Normal		 details
BloodDetected and Quantified5.600 +/- 3.0400 uMAdult (>18 years old)Female
Normal		 details
BloodDetected and Quantified5.970 +/- 3.510 uMAdult (>18 years old)Female
Normal		 details
BloodDetected and Quantified4.0600 +/- 2.690 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified4.440 +/- 3.0400 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified41.120 +/- 14.950 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified43.650 +/- 17.390 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified3.2 uMAdult (>18 years old)Female
Normal		 details
BloodDetected and Quantified3.7 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified6.720 +/- 3.360 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified1.458 uMChildren (1-13 years old)FemaleNormal details
BloodDetected and Quantified1.469 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified1.48 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified5.508 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1.440 +/- 0.720 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2.0159 +/- 0.696 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2.360 +/- 0.760 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified2.600 +/- 0.100 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2.700 +/- 0.100 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2.806 +/- 1.721 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified29.0367 +/- 10.384 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1.351 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified1.473 uMChildren (1-13 years old)MaleNormal details
BloodDetected and Quantified1.63 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.00576 +/- 0.00240 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified1.440 +/- 0.790 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified2.280 +/- 0.980 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified2.700 +/- 0.100 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified7.2 (3.8-11.7) uMAdult (>18 years old)FemaleNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Breast MilkDetected and Quantified0.5430037 +/- 0.0966421 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.3 (2.2-2.43) uMAdult (>18 years old)BothProstate cancer details
BloodDetected and Quantified6.2 (3.6-8.4) uMAdult (>18 years old)FemaleEndometrial cancer details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. 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
  1. 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
  1. 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
  1. 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 ]
  2. 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 ]
  3. 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
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002431
KNApSAcK IDC00007365
Chemspider ID83708
KEGG Compound IDC02483
BioCyc IDGAMA-TOCOPHEROL
BiGG IDNot Available
Wikipedia LinkGamma-Tocopherol
METLIN IDNot Available
PubChem Compound92729
PDB IDNot Available
ChEBI ID18185
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000332
Good Scents IDrw1013461
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. Reiter N, Jonsson B, Jansen E, Espersen K: [Vitamin E and excessive bleeding]. Ugeskr Laeger. 2005 Dec 5;167(49):4664-5. [PubMed:16336861 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. Chow CK: Distribution of tocopherols in human plasma and red blood cells. Am J Clin Nutr. 1975 Jul;28(7):756-60. [PubMed:1146729 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. Kontush K, Schekatolina S: Vitamin E in neurodegenerative disorders: Alzheimer's disease. Ann N Y Acad Sci. 2004 Dec;1031:249-62. [PubMed:15753151 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. Leo MA, Rosman AS, Lieber CS: Differential depletion of carotenoids and tocopherol in liver disease. Hepatology. 1993 Jun;17(6):977-86. [PubMed:8514270 ]
  18. 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 ]
  19. 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 ]
  20. 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 ]
  21. 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 ]
  22. 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 ]