Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:36 UTC

Update Date

2022-03-07 02:52:35 UTC

HMDB ID

HMDB0030555

Secondary Accession Numbers

HMDB30555

Metabolite Identification

Common Name

Tocopheronic acid

Description

Tocopheronic acid, also known as tocopheronate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on Tocopheronic acid.

Structure

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

HMDB0030555
     RDKit          3D
Tocopheronic acid
 43 43  0  0  0  0  0  0  0  0999 V2000
   -5.3525    0.9891    1.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9665    0.7111    0.6127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169   -0.4550    0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6082   -1.5425   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2296   -0.6893   -0.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9711   -1.8248   -0.8133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1965    0.3305   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218    0.0818   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8304   -1.0160    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2177   -1.4137   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4435   -1.8590   -1.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3719   -2.6765    0.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -0.6166    0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4848    0.7963   -0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7597    1.3242    0.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1152    2.5148    0.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5566    0.5328    1.3830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5565    1.5146    0.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4968    2.5558    0.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9360    1.7401    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158    2.8787    1.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4657    2.0822    1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1097    0.7038    0.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4949    0.4973    2.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6152   -1.1796   -0.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6149   -2.2275    0.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2710   -2.1755   -0.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7079    1.0643   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1622   -0.1644   -1.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1921   -1.9340   -0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7172   -0.8708    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6790   -2.6023   -1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447   -1.0165   -2.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4224   -2.4039   -1.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3294   -2.8901    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4264   -0.6377    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3011   -1.1369    0.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5512    0.8739   -1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7127    1.4388    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4393    0.1282    1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3044    2.2142    1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9745    3.4326    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1454    2.9275   -0.5119 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  7 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
M  END


  Mrv0541 05061305202D          

 21 21  0  0  0  0            999 V2000
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  9  2  0  0  0  0
 11  3  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  2  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16  4  1  0  0  0  0
 16  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17 13  2  0  0  0  0
 18 13  1  0  0  0  0
 19 14  2  0  0  0  0
 20 15  2  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030555

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(C)C(=O)C(CCC(C)(O)CCC(O)=O)=C(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O5/c1-9-10(2)15(20)12(11(3)14(9)19)5-7-16(4,21)8-6-13(17)18/h21H,5-8H2,1-4H3,(H,17,18)

> <INCHI_KEY>
LRYFTDGIIUTFFA-UHFFFAOYSA-N

> <FORMULA>
C16H22O5

> <MOLECULAR_WEIGHT>
294.3429

> <EXACT_MASS>
294.146723814

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.69758290362326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-4-methyl-6-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)hexanoic acid

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
2.402775469999999

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.057277785277169

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.195861842706385

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7864143454749994

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
79.43529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-4-methyl-6-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)hexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030555
     RDKit          3D
Tocopheronic acid
 43 43  0  0  0  0  0  0  0  0999 V2000
   -5.3525    0.9891    1.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9665    0.7111    0.6127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169   -0.4550    0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6082   -1.5425   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2296   -0.6893   -0.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9711   -1.8248   -0.8133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1965    0.3305   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218    0.0818   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8304   -1.0160    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2177   -1.4137   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4435   -1.8590   -1.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3719   -2.6765    0.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -0.6166    0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4848    0.7963   -0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7597    1.3242    0.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1152    2.5148    0.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5566    0.5328    1.3830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5565    1.5146    0.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4968    2.5558    0.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9360    1.7401    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158    2.8787    1.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4657    2.0822    1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1097    0.7038    0.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4949    0.4973    2.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6152   -1.1796   -0.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6149   -2.2275    0.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2710   -2.1755   -0.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7079    1.0643   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1622   -0.1644   -1.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1921   -1.9340   -0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7172   -0.8708    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6790   -2.6023   -1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447   -1.0165   -2.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4224   -2.4039   -1.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3294   -2.8901    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4264   -0.6377    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3011   -1.1369    0.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5512    0.8739   -1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7127    1.4388    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4393    0.1282    1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3044    2.2142    1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9745    3.4326    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1454    2.9275   -0.5119 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  7 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.897  -4.414   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -3.437  -1.746   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   16                                                            
CONECT    5    7   12                                                       
CONECT    6    8   13                                                       
CONECT    7    5   16                                                       
CONECT    8    6   16                                                       
CONECT    9    1   10   14                                                  
CONECT   10    2    9   15                                                  
CONECT   11    3   12   14                                                  
CONECT   12    5   11   15                                                  
CONECT   13    6   17   18                                                  
CONECT   14    9   11   19                                                  
CONECT   15   10   12   20                                                  
CONECT   16    4    7    8   21                                             
CONECT   17   13                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   16                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0030555
HETATM    1  C1  UNL     1      -5.352   0.989   1.051  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.966   0.711   0.613  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.617  -0.455   0.095  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.608  -1.542  -0.070  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.230  -0.689  -0.328  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.971  -1.825  -0.813  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.197   0.331  -0.198  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.222   0.082  -0.641  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.830  -1.016   0.145  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.218  -1.414  -0.133  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.443  -1.859  -1.578  1.00  0.00           C  
HETATM   12  O2  UNL     1       2.372  -2.677   0.579  1.00  0.00           O  
HETATM   13  C11 UNL     1       3.346  -0.617   0.361  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.485   0.796  -0.049  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.760   1.324   0.588  1.00  0.00           C  
HETATM   16  O3  UNL     1       5.115   2.515   0.397  1.00  0.00           O  
HETATM   17  O4  UNL     1       5.557   0.533   1.383  1.00  0.00           O  
HETATM   18  C14 UNL     1      -1.556   1.515   0.329  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.497   2.556   0.460  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.936   1.740   0.746  1.00  0.00           C  
HETATM   21  O5  UNL     1      -3.216   2.879   1.237  1.00  0.00           O  
HETATM   22  H1  UNL     1      -5.466   2.082   1.206  1.00  0.00           H  
HETATM   23  H2  UNL     1      -6.110   0.704   0.298  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.495   0.497   2.023  1.00  0.00           H  
HETATM   25  H4  UNL     1      -5.615  -1.180  -0.341  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.615  -2.228   0.810  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.271  -2.175  -0.931  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.708   1.064  -0.609  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.162  -0.164  -1.747  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.192  -1.934  -0.049  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.717  -0.871   1.243  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.679  -2.602  -1.858  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.545  -1.016  -2.264  1.00  0.00           H  
HETATM   34  H13 UNL     1       3.422  -2.404  -1.580  1.00  0.00           H  
HETATM   35  H14 UNL     1       3.329  -2.890   0.633  1.00  0.00           H  
HETATM   36  H15 UNL     1       3.426  -0.638   1.487  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.301  -1.137   0.037  1.00  0.00           H  
HETATM   38  H17 UNL     1       3.551   0.874  -1.136  1.00  0.00           H  
HETATM   39  H18 UNL     1       2.713   1.439   0.431  1.00  0.00           H  
HETATM   40  H19 UNL     1       6.439   0.128   1.106  1.00  0.00           H  
HETATM   41  H20 UNL     1       0.304   2.214   1.136  1.00  0.00           H  
HETATM   42  H21 UNL     1      -0.975   3.433   0.987  1.00  0.00           H  
HETATM   43  H22 UNL     1      -0.145   2.927  -0.512  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3   20
CONECT    3    4    5
CONECT    4   25   26   27
CONECT    5    6    6    7
CONECT    7    8   18   18
CONECT    8    9   28   29
CONECT    9   10   30   31
CONECT   10   11   12   13
CONECT   11   32   33   34
CONECT   12   35
CONECT   13   14   36   37
CONECT   14   15   38   39
CONECT   15   16   16   17
CONECT   17   40
CONECT   18   19   20
CONECT   19   41   42   43
CONECT   20   21   21
END

HMDB0030555
     RDKit          3D
Tocopheronic acid
 43 43  0  0  0  0  0  0  0  0999 V2000
   -5.3525    0.9891    1.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9665    0.7111    0.6127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169   -0.4550    0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6082   -1.5425   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2296   -0.6893   -0.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9711   -1.8248   -0.8133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1965    0.3305   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218    0.0818   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8304   -1.0160    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2177   -1.4137   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4435   -1.8590   -1.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3719   -2.6765    0.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -0.6166    0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4848    0.7963   -0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7597    1.3242    0.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1152    2.5148    0.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5566    0.5328    1.3830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5565    1.5146    0.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4968    2.5558    0.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9360    1.7401    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158    2.8787    1.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4657    2.0822    1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1097    0.7038    0.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4949    0.4973    2.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6152   -1.1796   -0.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6149   -2.2275    0.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2710   -2.1755   -0.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7079    1.0643   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1622   -0.1644   -1.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1921   -1.9340   -0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7172   -0.8708    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6790   -2.6023   -1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447   -1.0165   -2.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4224   -2.4039   -1.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3294   -2.8901    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4264   -0.6377    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3011   -1.1369    0.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5512    0.8739   -1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7127    1.4388    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4393    0.1282    1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3044    2.2142    1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9745    3.4326    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1454    2.9275   -0.5119 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  7 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Tocopheronate	Generator
(S)-N-Phthaloylphenylalanine	HMDB
2-(3-Hydroxy-3-methyl-5-carboxypentyl)-3,5,6-trimethyl-1,4-benzoquinone	HMDB
g-Hydroxy-g,2,4,5-tetramethyl-3,6-dioxo-1,4-cyclohexadiene-1-hexanoic acid, 9ci	HMDB
N-Phthaloyl-L-phenylalanine	HMDB
N-Phthalyl-L-phenylalanine	HMDB
Phthaloyl-L-phenylalanine	HMDB
4-Hydroxy-4-methyl-6-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)hexanoate	HMDB

Chemical Formula

C₁₆H₂₂O₅

Average Molecular Weight

294.3429

Monoisotopic Molecular Weight

294.146723814

IUPAC Name

4-hydroxy-4-methyl-6-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)hexanoic acid

Traditional Name

4-hydroxy-4-methyl-6-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)hexanoic acid

CAS Registry Number

1948-76-1

SMILES

CC1=C(C)C(=O)C(CCC(C)(O)CCC(O)=O)=C(C)C1=O

InChI Identifier

InChI=1S/C16H22O5/c1-9-10(2)15(20)12(11(3)14(9)19)5-7-16(4,21)8-6-13(17)18/h21H,5-8H2,1-4H3,(H,17,18)

InChI Key

LRYFTDGIIUTFFA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Prenylbenzoquinone
Medium-chain hydroxy acid
P-benzoquinone
Quinone
Medium-chain fatty acid
Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Tertiary alcohol
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030555)

Source

Endogenous

Endogenous (HMDB: HMDB0030555)

Animal

Animal (HMDB: HMDB0030555)

Exogenous

Food

Food (HMDB: HMDB0030555)

Exogenous (HMDB: HMDB0030555)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0030555)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0030555)

Lipid metabolism pathway (HMDB: HMDB0030555)

Cellular process

Cell signaling (HMDB: HMDB0030555)

Biochemical process

Lipid transport (HMDB: HMDB0030555)

Role

Biological role

Energy source (HMDB: HMDB0030555)

Physical Properties

State

Not Available

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	0.16 g/L	ALOGPS
logP	0.88	ALOGPS
logP	2.4	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.2	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	79.44 m³·mol⁻¹	ChemAxon
Polarizability	31.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	170.536	31661259
DarkChem	[M-H]-	166.444	31661259
DeepCCS	[M+H]+	173.525	30932474
DeepCCS	[M-H]-	171.167	30932474
DeepCCS	[M-2H]-	204.053	30932474
DeepCCS	[M+Na]+	179.618	30932474
AllCCS	[M+H]+	169.9	32859911
AllCCS	[M+H-H2O]+	166.6	32859911
AllCCS	[M+NH4]+	172.8	32859911
AllCCS	[M+Na]+	173.7	32859911
AllCCS	[M-H]-	174.0	32859911
AllCCS	[M+Na-2H]-	174.6	32859911
AllCCS	[M+HCOO]-	175.3	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.	6.15 minutes	32390414
Predicted by Siyang on May 30, 2022	11.5758 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.37 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2289.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	231.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	157.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	452.8 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	565.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	65.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	910.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	415.9 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	1288.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	289.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	373.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	273.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	268.5 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	66.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tocopheronic acid	CC1=C(C)C(=O)C(CCC(C)(O)CCC(O)=O)=C(C)C1=O	3697.4	Standard polar	33892256
Tocopheronic acid	CC1=C(C)C(=O)C(CCC(C)(O)CCC(O)=O)=C(C)C1=O	2084.9	Standard non polar	33892256
Tocopheronic acid	CC1=C(C)C(=O)C(CCC(C)(O)CCC(O)=O)=C(C)C1=O	2328.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tocopheronic acid,1TMS,isomer #1	CC1=C(C)C(=O)C(CCC(C)(CCC(=O)O)O[Si](C)(C)C)=C(C)C1=O	2486.2	Semi standard non polar	33892256
Tocopheronic acid,1TMS,isomer #2	CC1=C(C)C(=O)C(CCC(C)(O)CCC(=O)O[Si](C)(C)C)=C(C)C1=O	2390.3	Semi standard non polar	33892256
Tocopheronic acid,2TMS,isomer #1	CC1=C(C)C(=O)C(CCC(C)(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)=C(C)C1=O	2580.4	Semi standard non polar	33892256
Tocopheronic acid,1TBDMS,isomer #1	CC1=C(C)C(=O)C(CCC(C)(CCC(=O)O)O[Si](C)(C)C(C)(C)C)=C(C)C1=O	2730.2	Semi standard non polar	33892256
Tocopheronic acid,1TBDMS,isomer #2	CC1=C(C)C(=O)C(CCC(C)(O)CCC(=O)O[Si](C)(C)C(C)(C)C)=C(C)C1=O	2667.4	Semi standard non polar	33892256
Tocopheronic acid,2TBDMS,isomer #1	CC1=C(C)C(=O)C(CCC(C)(CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C(C)C1=O	3083.3	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 - Tocopheronic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-7590000000-8ceca700507a261f2ff7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tocopheronic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9333500000-371ea8f67202310a984e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tocopheronic acid 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 - Tocopheronic acid 10V, Positive-QTOF	splash10-056s-0190000000-1c6bd2ca9f9514d9f1c2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocopheronic acid 20V, Positive-QTOF	splash10-0929-3590000000-a2de3cdb7032fe328df7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocopheronic acid 40V, Positive-QTOF	splash10-0udi-9610000000-83173971cdbe099c101e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocopheronic acid 10V, Negative-QTOF	splash10-0006-0090000000-7c21a7fee2eac9c7d578	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocopheronic acid 20V, Negative-QTOF	splash10-002g-2090000000-a9dbedd5aed1e31e0b64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocopheronic acid 40V, Negative-QTOF	splash10-0a4i-9110000000-6b7f8ae6d1561edbdbad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocopheronic acid 10V, Positive-QTOF	splash10-02dj-0290000000-2f16e31ef4ed805d9763	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocopheronic acid 20V, Positive-QTOF	splash10-0929-1960000000-93577d80e84fe9335c3e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocopheronic acid 40V, Positive-QTOF	splash10-01q9-7900000000-3c5bfcf4add746a28d18	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocopheronic acid 10V, Negative-QTOF	splash10-000x-0090000000-1542643b699185c4748e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocopheronic acid 20V, Negative-QTOF	splash10-0a6u-6290000000-9f60d70c6dac3be11030	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocopheronic acid 40V, Negative-QTOF	splash10-01t9-1900000000-2c5031eebdea62fa95d8	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB002435

KNApSAcK ID

Not Available

Chemspider ID

35013225

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

67764516

PDB ID

Not Available

ChEBI ID

172913

Food Biomarker Ontology

Not Available

VMH ID

Not Available

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Tocopheronic acid (HMDB0030555)

MOL for HMDB0030555 (Tocopheronic acid)

3D MOL for HMDB0030555 (Tocopheronic acid)

3D SDF for HMDB0030555 (Tocopheronic acid)

3D-SDF for HMDB0030555 (Tocopheronic acid)

PDB for HMDB0030555 (Tocopheronic acid)

3D PDB for HMDB0030555 (Tocopheronic acid)

SMILES for HMDB0030555 (Tocopheronic acid)

INCHI for HMDB0030555 (Tocopheronic acid)

Structure for HMDB0030555 (Tocopheronic acid)

3D Structure for HMDB0030555 (Tocopheronic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra