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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:02:57 UTC

Update Date

2022-03-07 02:51:26 UTC

HMDB ID

HMDB0012561

Secondary Accession Numbers

HMDB12561

Metabolite Identification

Common Name

13'-Hydroxy-gamma-tocopherol

Description

13'-hydroxy-r-tocopherol is a precursor of dehydrogenation to form 13'-Carboxy-gamma-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. r-Tocopherol provides different antioxidant activities in food and in-vitro studies and showed higher activity in trapping lipophilic electrophiles and reactive nitrogen and oxygen species. From the metabolism end product, only that of r-tocopherol (2,7,8-trimethyl-2-(b-carboxyethyl)-6-hydroxychroman), but not that of a-tocopherol, was identified to provide natriuretic activity. Only the r-tocopherol plasma level served as biomarker for cancer and cardiovascular risk.

Structure

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


  Mrv0541 02251208072D          

 31 32  0  0  1  0            999 V2000
   13.4421  -12.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0296  -11.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4421  -10.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2671  -10.8578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2046  -11.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7921  -12.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9671  -12.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5546  -13.0012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7296  -13.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9671  -13.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5546  -14.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9671  -15.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5546  -15.8591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7296  -15.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9671  -16.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7921  -16.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2046  -17.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6171  -18.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0296  -16.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7441  -16.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4585  -16.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1730  -16.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8875  -16.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6020  -16.0506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8875  -17.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6020  -17.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.1730  -18.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4585  -17.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7441  -17.7006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 12 13  1  0  0  0  0
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 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

HMDB0012561
     RDKit          3D
13'-Hydroxy-gamma-tocopherol
 79 80  0  0  0  0  0  0  0  0999 V2000
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   -5.7881   -1.3495    2.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02251208072D          

 31 32  0  0  1  0            999 V2000
   13.4421  -12.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0296  -11.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4421  -10.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2671  -10.8578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2046  -11.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0012561

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CO)CCC[C@H](C)CCC[C@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O3/c1-20(12-8-13-22(3)19-29)10-7-11-21(2)14-9-16-28(6)17-15-25-18-26(30)23(4)24(5)27(25)31-28/h18,20-22,29-30H,7-17,19H2,1-6H3/t20-,21+,22?,28-/m1/s1

> <INCHI_KEY>
QNBPVJMQPAQXML-SLGTZZLGSA-N

> <FORMULA>
C28H48O3

> <MOLECULAR_WEIGHT>
432.6789

> <EXACT_MASS>
432.360345402

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
55.091136926254684

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
8.05

> <JCHEM_LOGP>
8.635570984000001

> <ALOGPS_LOGS>
-7.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.418322874869105

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.470460494567556

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7406896624370471

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
132.18459999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.28e-05 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012561
     RDKit          3D
13'-Hydroxy-gamma-tocopherol
 79 80  0  0  0  0  0  0  0  0999 V2000
   -7.0884   -2.0074    2.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7881   -1.3495    2.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6045   -1.9593    2.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5365   -3.1609    3.2361 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4357   -1.3184    2.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4287   -0.1087    1.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5990    0.5001    1.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7837   -0.1658    1.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0651    0.4709    1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6961    1.6891    0.4506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4448    2.0498   -0.3135 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6912    3.4365   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3092    1.0457   -1.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4235    0.8472   -2.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9865    0.6764   -2.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124    1.7086   -2.3643 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2239    2.3954   -1.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4030    1.2771   -2.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9074    0.0479   -2.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.2537   -2.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8883   -1.4755   -2.2049 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2378   -1.7862   -2.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0632   -1.3504   -0.6767 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9414   -0.2114   -0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030   -0.0041    1.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6915   -1.0682    1.9532 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0056   -2.3749    2.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8243   -0.4935    3.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3806   -1.4595    4.2191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4557    1.9759    0.8218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227    0.5342    1.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8406   -1.1682    2.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0216   -2.5489    3.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3872   -2.6133    1.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3274   -3.6816    3.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4834   -1.7744    2.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9145    1.4013    0.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5429    0.7930    2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7430   -0.2004    0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2067    3.6517   -1.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1587    4.1324   -0.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7603    3.6640   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953    1.0838   -1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4854   -0.0221   -0.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7532    1.5877   -3.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8672   -0.1157   -3.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6569   -0.2940   -1.9886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7410    0.2491   -3.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395    2.5483   -3.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076    1.7593   -0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2301    2.9220   -1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4894    3.2425   -1.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3913    1.1795   -3.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0812    2.1184   -2.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -0.8341   -2.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0502    0.2408   -1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1219   -0.4421   -3.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9682    0.5963   -2.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622   -2.3840   -2.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1993   -2.4836   -3.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7526   -0.8275   -3.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8789   -2.2785   -2.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0758   -1.3610   -0.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5833   -2.3004   -0.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5990    0.7522   -0.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664   -0.3523   -0.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7211    0.9387    1.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1118    0.2704    1.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7595   -1.2155    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1285   -2.7257    3.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9425   -2.2775    1.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4682   -3.2127    1.4789 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4818    0.3902    3.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8187   -0.2590    3.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2820   -1.7483    3.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0656    2.2750    1.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6642    2.6925    0.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094    0.0210    0.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5001    0.5035    2.0249 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
 28 29  1  0
 11 30  1  0
 30 31  1  0
  8  2  1  0
 31  6  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  6
 17 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  1
 22 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 24 65  1  0
 24 66  1  0
 25 67  1  0
 25 68  1  0
 26 69  1  0
 27 70  1  0
 27 71  1  0
 27 72  1  0
 28 73  1  0
 28 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 31 78  1  0
 31 79  1  0
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      25.092 -22.935   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.322 -21.601   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.092 -20.268   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      26.632 -20.268   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      22.782 -21.601   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.012 -22.935   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.472 -22.935   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.702 -24.269   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.162 -24.269   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.472 -25.603   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.702 -26.936   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.472 -28.270   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.702 -29.604   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.162 -29.604   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.472 -30.937   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.012 -30.937   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.782 -32.271   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.322 -32.271   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.552 -33.605   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.322 -30.731   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.656 -29.961   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.989 -30.731   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.323 -29.961   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.657 -30.731   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      30.990 -29.961   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      29.657 -32.271   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.990 -33.041   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      28.323 -33.041   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      28.323 -34.581   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      26.989 -32.271   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      25.656 -33.041   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   31                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   22   28   31                                                  
CONECT   31   18   30                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

COMPND    HMDB0012561
HETATM    1  C1  UNL     1      -7.088  -2.007   2.566  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.788  -1.350   2.192  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.604  -1.959   2.546  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.536  -3.161   3.236  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.436  -1.318   2.181  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.429  -0.109   1.486  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.599   0.500   1.133  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.784  -0.166   1.512  1.00  0.00           C  
HETATM    9  C8  UNL     1      -7.065   0.471   1.144  1.00  0.00           C  
HETATM   10  O2  UNL     1      -4.696   1.689   0.451  1.00  0.00           O  
HETATM   11  C9  UNL     1      -3.445   2.050  -0.314  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.691   3.436  -0.788  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.309   1.046  -1.356  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.423   0.847  -2.440  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.986   0.676  -2.577  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.012   1.709  -2.364  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.224   2.395  -1.094  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.403   1.277  -2.885  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.907   0.048  -2.209  1.00  0.00           C  
HETATM   20  C18 UNL     1       3.279  -0.254  -2.810  1.00  0.00           C  
HETATM   21  C19 UNL     1       3.888  -1.476  -2.205  1.00  0.00           C  
HETATM   22  C20 UNL     1       5.238  -1.786  -2.779  1.00  0.00           C  
HETATM   23  C21 UNL     1       4.063  -1.350  -0.677  1.00  0.00           C  
HETATM   24  C22 UNL     1       4.941  -0.211  -0.332  1.00  0.00           C  
HETATM   25  C23 UNL     1       5.103  -0.004   1.131  1.00  0.00           C  
HETATM   26  C24 UNL     1       5.692  -1.068   1.953  1.00  0.00           C  
HETATM   27  C25 UNL     1       5.006  -2.375   2.041  1.00  0.00           C  
HETATM   28  C26 UNL     1       5.824  -0.493   3.383  1.00  0.00           C  
HETATM   29  O3  UNL     1       6.381  -1.460   4.219  1.00  0.00           O  
HETATM   30  C27 UNL     1      -2.456   1.976   0.822  1.00  0.00           C  
HETATM   31  C28 UNL     1      -2.123   0.534   1.111  1.00  0.00           C  
HETATM   32  H1  UNL     1      -7.841  -1.168   2.640  1.00  0.00           H  
HETATM   33  H2  UNL     1      -7.022  -2.549   3.509  1.00  0.00           H  
HETATM   34  H3  UNL     1      -7.387  -2.613   1.695  1.00  0.00           H  
HETATM   35  H4  UNL     1      -5.327  -3.682   3.533  1.00  0.00           H  
HETATM   36  H5  UNL     1      -2.483  -1.774   2.446  1.00  0.00           H  
HETATM   37  H6  UNL     1      -6.914   1.401   0.567  1.00  0.00           H  
HETATM   38  H7  UNL     1      -7.543   0.793   2.110  1.00  0.00           H  
HETATM   39  H8  UNL     1      -7.743  -0.200   0.606  1.00  0.00           H  
HETATM   40  H9  UNL     1      -3.207   3.652  -1.780  1.00  0.00           H  
HETATM   41  H10 UNL     1      -3.159   4.132  -0.076  1.00  0.00           H  
HETATM   42  H11 UNL     1      -4.760   3.664  -0.823  1.00  0.00           H  
HETATM   43  H12 UNL     1      -4.395   1.084  -1.875  1.00  0.00           H  
HETATM   44  H13 UNL     1      -3.485  -0.022  -0.880  1.00  0.00           H  
HETATM   45  H14 UNL     1      -2.753   1.588  -3.334  1.00  0.00           H  
HETATM   46  H15 UNL     1      -2.867  -0.116  -3.007  1.00  0.00           H  
HETATM   47  H16 UNL     1      -0.657  -0.294  -1.989  1.00  0.00           H  
HETATM   48  H17 UNL     1      -0.741   0.249  -3.644  1.00  0.00           H  
HETATM   49  H18 UNL     1      -0.239   2.548  -3.129  1.00  0.00           H  
HETATM   50  H19 UNL     1       0.208   1.759  -0.193  1.00  0.00           H  
HETATM   51  H20 UNL     1       1.230   2.922  -1.158  1.00  0.00           H  
HETATM   52  H21 UNL     1      -0.489   3.242  -1.018  1.00  0.00           H  
HETATM   53  H22 UNL     1       1.391   1.180  -3.985  1.00  0.00           H  
HETATM   54  H23 UNL     1       2.081   2.118  -2.637  1.00  0.00           H  
HETATM   55  H24 UNL     1       1.269  -0.834  -2.282  1.00  0.00           H  
HETATM   56  H25 UNL     1       2.050   0.241  -1.119  1.00  0.00           H  
HETATM   57  H26 UNL     1       3.122  -0.442  -3.900  1.00  0.00           H  
HETATM   58  H27 UNL     1       3.968   0.596  -2.749  1.00  0.00           H  
HETATM   59  H28 UNL     1       3.262  -2.384  -2.339  1.00  0.00           H  
HETATM   60  H29 UNL     1       5.199  -2.484  -3.639  1.00  0.00           H  
HETATM   61  H30 UNL     1       5.753  -0.827  -3.029  1.00  0.00           H  
HETATM   62  H31 UNL     1       5.879  -2.279  -2.005  1.00  0.00           H  
HETATM   63  H32 UNL     1       3.076  -1.361  -0.215  1.00  0.00           H  
HETATM   64  H33 UNL     1       4.583  -2.300  -0.410  1.00  0.00           H  
HETATM   65  H34 UNL     1       4.599   0.752  -0.833  1.00  0.00           H  
HETATM   66  H35 UNL     1       5.966  -0.352  -0.806  1.00  0.00           H  
HETATM   67  H36 UNL     1       5.721   0.939   1.339  1.00  0.00           H  
HETATM   68  H37 UNL     1       4.112   0.270   1.617  1.00  0.00           H  
HETATM   69  H38 UNL     1       6.760  -1.215   1.583  1.00  0.00           H  
HETATM   70  H39 UNL     1       5.129  -2.726   3.127  1.00  0.00           H  
HETATM   71  H40 UNL     1       3.943  -2.277   1.808  1.00  0.00           H  
HETATM   72  H41 UNL     1       5.468  -3.213   1.479  1.00  0.00           H  
HETATM   73  H42 UNL     1       6.482   0.390   3.339  1.00  0.00           H  
HETATM   74  H43 UNL     1       4.819  -0.259   3.784  1.00  0.00           H  
HETATM   75  H44 UNL     1       7.282  -1.748   3.890  1.00  0.00           H  
HETATM   76  H45 UNL     1      -3.066   2.275   1.774  1.00  0.00           H  
HETATM   77  H46 UNL     1      -1.664   2.692   0.850  1.00  0.00           H  
HETATM   78  H47 UNL     1      -1.609   0.021   0.302  1.00  0.00           H  
HETATM   79  H48 UNL     1      -1.500   0.504   2.025  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    3    8
CONECT    3    4    5
CONECT    4   35
CONECT    5    6    6   36
CONECT    6    7   31
CONECT    7    8    8   10
CONECT    8    9
CONECT    9   37   38   39
CONECT   10   11
CONECT   11   12   13   30
CONECT   12   40   41   42
CONECT   13   14   43   44
CONECT   14   15   45   46
CONECT   15   16   47   48
CONECT   16   17   18   49
CONECT   17   50   51   52
CONECT   18   19   53   54
CONECT   19   20   55   56
CONECT   20   21   57   58
CONECT   21   22   23   59
CONECT   22   60   61   62
CONECT   23   24   63   64
CONECT   24   25   65   66
CONECT   25   26   67   68
CONECT   26   27   28   69
CONECT   27   70   71   72
CONECT   28   29   73   74
CONECT   29   75
CONECT   30   31   76   77
CONECT   31   78   79
END

HMDB0012561
     RDKit          3D
13'-Hydroxy-gamma-tocopherol
 79 80  0  0  0  0  0  0  0  0999 V2000
   -7.0884   -2.0074    2.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7881   -1.3495    2.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6045   -1.9593    2.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5365   -3.1609    3.2361 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4357   -1.3184    2.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4287   -0.1087    1.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5990    0.5001    1.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7837   -0.1658    1.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0651    0.4709    1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6961    1.6891    0.4506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4448    2.0498   -0.3135 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6912    3.4365   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3092    1.0457   -1.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4235    0.8472   -2.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9865    0.6764   -2.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124    1.7086   -2.3643 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2239    2.3954   -1.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4030    1.2771   -2.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9074    0.0479   -2.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.2537   -2.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8883   -1.4755   -2.2049 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2378   -1.7862   -2.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0632   -1.3504   -0.6767 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9414   -0.2114   -0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030   -0.0041    1.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6915   -1.0682    1.9532 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0056   -2.3749    2.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8243   -0.4935    3.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3806   -1.4595    4.2191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4557    1.9759    0.8218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227    0.5342    1.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8406   -1.1682    2.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0216   -2.5489    3.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3872   -2.6133    1.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3274   -3.6816    3.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4834   -1.7744    2.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9145    1.4013    0.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5429    0.7930    2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7430   -0.2004    0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2067    3.6517   -1.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1587    4.1324   -0.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7603    3.6640   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953    1.0838   -1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4854   -0.0221   -0.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7532    1.5877   -3.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8672   -0.1157   -3.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6569   -0.2940   -1.9886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7410    0.2491   -3.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395    2.5483   -3.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076    1.7593   -0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2301    2.9220   -1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4894    3.2425   -1.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3913    1.1795   -3.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0812    2.1184   -2.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -0.8341   -2.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0502    0.2408   -1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1219   -0.4421   -3.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9682    0.5963   -2.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622   -2.3840   -2.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1993   -2.4836   -3.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7526   -0.8275   -3.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8789   -2.2785   -2.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0758   -1.3610   -0.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5833   -2.3004   -0.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5990    0.7522   -0.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664   -0.3523   -0.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7211    0.9387    1.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1118    0.2704    1.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7595   -1.2155    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1285   -2.7257    3.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9425   -2.2775    1.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4682   -3.2127    1.4789 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4818    0.3902    3.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8187   -0.2590    3.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2820   -1.7483    3.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0656    2.2750    1.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6642    2.6925    0.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094    0.0210    0.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5001    0.5035    2.0249 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
 28 29  1  0
 11 30  1  0
 30 31  1  0
  8  2  1  0
 31  6  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  6
 17 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  1
 22 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 24 65  1  0
 24 66  1  0
 25 67  1  0
 25 68  1  0
 26 69  1  0
 27 70  1  0
 27 71  1  0
 27 72  1  0
 28 73  1  0
 28 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 31 78  1  0
 31 79  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
13'-Hydroxy-g-tocopherol	Generator
13'-Hydroxy-γ-tocopherol	Generator
13'-OH-Tocopherol	HMDB

Chemical Formula

C₂₈H₄₈O₃

Average Molecular Weight

432.6789

Monoisotopic Molecular Weight

432.360345402

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(CO)CCC[C@H](C)CCC[C@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2

InChI Identifier

InChI=1S/C28H48O3/c1-20(12-8-13-22(3)19-29)10-7-11-21(2)14-9-16-28(6)17-15-25-18-26(30)23(4)24(5)27(25)31-28/h18,20-22,29-30H,7-17,19H2,1-6H3/t20-,21+,22?,28-/m1/s1

InChI Key

QNBPVJMQPAQXML-SLGTZZLGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Tocopherols

Alternative Parents

Substituents

Tocopherol
Diterpenoid
Long chain fatty alcohol
Chromane
Benzopyran
1-benzopyran
Fatty alcohol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acyl
Benzenoid
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012561)

Source

Endogenous

Endogenous (HMDB: HMDB0012561)

Animal

Animal (HMDB: HMDB0012561)

Exogenous

Food

Food (HMDB: HMDB0012561)

Exogenous (HMDB: HMDB0012561)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012561)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012561)

Lipid metabolism pathway (HMDB: HMDB0012561)

Cellular process

Cell signaling (HMDB: HMDB0012561)

Biochemical process

Lipid transport (HMDB: HMDB0012561)

Role

Biological role

Energy source (HMDB: HMDB0012561)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012561)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.3e-05 g/L	ALOGPS
logP	8.05	ALOGPS
logP	8.64	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	10.47	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	132.18 m³·mol⁻¹	ChemAxon
Polarizability	55.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	210.848	31661259
DarkChem	[M-H]-	203.42	31661259
DeepCCS	[M+H]+	215.453	30932474
DeepCCS	[M-H]-	213.058	30932474
DeepCCS	[M-2H]-	245.94	30932474
DeepCCS	[M+Na]+	221.381	30932474
AllCCS	[M+H]+	214.5	32859911
AllCCS	[M+H-H2O]+	212.5	32859911
AllCCS	[M+NH4]+	216.4	32859911
AllCCS	[M+Na]+	216.9	32859911
AllCCS	[M-H]-	213.6	32859911
AllCCS	[M+Na-2H]-	216.5	32859911
AllCCS	[M+HCOO]-	219.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	10.25 minutes	32390414
Predicted by Siyang on May 30, 2022	28.8464 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.17 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3595.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	814.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	341.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	370.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	763.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1600.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1279.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	105.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2554.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	880.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2624.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	968.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	628.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	607.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	669.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
13'-Hydroxy-gamma-tocopherol	CC(CO)CCC[C@H](C)CCC[C@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2	3963.7	Standard polar	33892256
13'-Hydroxy-gamma-tocopherol	CC(CO)CCC[C@H](C)CCC[C@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2	3268.7	Standard non polar	33892256
13'-Hydroxy-gamma-tocopherol	CC(CO)CCC[C@H](C)CCC[C@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2	3408.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
13'-Hydroxy-gamma-tocopherol,1TMS,isomer #1	CC1=C(O)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)CO[Si](C)(C)C)OC2=C1C	3195.1	Semi standard non polar	33892256
13'-Hydroxy-gamma-tocopherol,1TMS,isomer #2	CC1=C(O[Si](C)(C)C)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)CO)OC2=C1C	3229.9	Semi standard non polar	33892256
13'-Hydroxy-gamma-tocopherol,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)CO[Si](C)(C)C)OC2=C1C	3160.1	Semi standard non polar	33892256
13'-Hydroxy-gamma-tocopherol,1TBDMS,isomer #1	CC1=C(O)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)CO[Si](C)(C)C(C)(C)C)OC2=C1C	3466.6	Semi standard non polar	33892256
13'-Hydroxy-gamma-tocopherol,1TBDMS,isomer #2	CC1=C(O[Si](C)(C)C(C)(C)C)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)CO)OC2=C1C	3498.3	Semi standard non polar	33892256
13'-Hydroxy-gamma-tocopherol,2TBDMS,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)CO[Si](C)(C)C(C)(C)C)OC2=C1C	3680.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 13'-Hydroxy-gamma-tocopherol GC-MS (2 TMS) - 70eV, Positive	splash10-03di-1454390000-7842b0b1bb538653ff9c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13'-Hydroxy-gamma-tocopherol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0hnf-2975400000-7bb7c14065fa1f987a6f	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13'-Hydroxy-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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocopherol 10V, Positive-QTOF	splash10-0fsi-0421900000-f32e1218cd4b25480728	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocopherol 20V, Positive-QTOF	splash10-0udi-0921100000-9af955e3a6ca5cc9b504	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocopherol 40V, Positive-QTOF	splash10-0udi-2910000000-b9fac219f3c4d2615086	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocopherol 10V, Negative-QTOF	splash10-001i-0000900000-b973ab3c74e8641e9199	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocopherol 20V, Negative-QTOF	splash10-01qa-0501900000-7a7396d4bce194c6cd9a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocopherol 40V, Negative-QTOF	splash10-000j-2926300000-eaf0c2bb9bb0a46b4cee	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocopherol 10V, Negative-QTOF	splash10-01q9-0000900000-93b97149c3e76cb52886	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocopherol 20V, Negative-QTOF	splash10-0gx1-0302900000-814090875d1ef4bed12b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocopherol 40V, Negative-QTOF	splash10-03kd-0809500000-19adb2966ed984243e6b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocopherol 10V, Positive-QTOF	splash10-001i-2224900000-f43893fdf5951a6996f9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocopherol 20V, Positive-QTOF	splash10-000b-7927100000-0509051ba7c4b3d9aeba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocopherol 40V, Positive-QTOF	splash10-05tg-7910000000-c37a1015fcc54a9911a4	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029127

KNApSAcK ID

Not Available

Chemspider ID

35032541

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481467

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

CE5655

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 13'-Hydroxy-gamma-tocopherol (HMDB0012561)

MOL for HMDB0012561 (13'-Hydroxy-gamma-tocopherol)

3D MOL for HMDB0012561 (13'-Hydroxy-gamma-tocopherol)

3D SDF for HMDB0012561 (13'-Hydroxy-gamma-tocopherol)

3D-SDF for HMDB0012561 (13'-Hydroxy-gamma-tocopherol)

PDB for HMDB0012561 (13'-Hydroxy-gamma-tocopherol)

3D PDB for HMDB0012561 (13'-Hydroxy-gamma-tocopherol)

SMILES for HMDB0012561 (13'-Hydroxy-gamma-tocopherol)

INCHI for HMDB0012561 (13'-Hydroxy-gamma-tocopherol)

Structure for HMDB0012561 (13'-Hydroxy-gamma-tocopherol)

3D Structure for HMDB0012561 (13'-Hydroxy-gamma-tocopherol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra