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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-07-26 11:00:16 UTC

Update Date

2022-09-22 17:43:47 UTC

HMDB ID

HMDB0001931

Secondary Accession Numbers

HMDB01931

Metabolite Identification

Common Name

gamma-CEHC

Description

gamma-CEHC (gamma-carboxyethyl hydroxychroman) is a metabolite of vitamin E. Smokers have a significantly higher excretion level of urinary gamma-CEHC, and therefore require more vitamin E compared to non-smokers. Cigarette smoking is associated with increased oxidative stress and increased risk of degenerative disease. As the major lipophilic antioxidant, requirements for vitamin E may also be higher in smokers due to increased utilization (PMID: 15493460 ).

Structure

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

HMDB0001931
     RDKit          3D
gamma-CEHC
 39 40  0  0  0  0  0  0  0  0999 V2000
   -4.7350    0.6744   -0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3887    0.1293    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3239   -1.1088    0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5404   -1.7691    0.9099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182   -1.6644    1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9340   -0.9819    0.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0116    0.2395    0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376    0.8034   -0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2434    2.1323   -0.8670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454    0.9398   -0.0971 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4041    0.2263   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3098   -0.7026   -1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4571    1.2304   -0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8701    0.8451   -0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5669    0.3292    0.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1487    0.4359    1.8808 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7837   -0.3317    0.5622 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5346   -0.6406    1.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3485   -1.6046    1.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4126   -0.1692   -0.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6704    1.4000   -1.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1418    1.1458    0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4664   -2.6688    1.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0706   -2.6417    1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7257    2.0934   -1.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8308    2.8136   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2318    2.5399   -0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2446   -1.2829   -1.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809   -1.4133   -1.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725   -0.1198   -2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4017    2.0807    0.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313    1.8007   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4298    1.8052   -0.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0690    0.1922   -1.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7845   -1.0702   -0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4117   -1.3053    0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5951   -0.0156    1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300   -2.5577    0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626   -1.8087    2.2932 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  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 11 18  1  0
 18 19  1  0
  8  2  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
M  END

            
  Mrv1652303141818332D          

 19 20  0  0  0  0            999 V2000
    7.8793   -5.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5934   -6.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5934   -7.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8793   -7.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1648   -7.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1648   -6.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4502   -5.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4502   -7.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7359   -6.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7359   -7.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4502   -5.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0214   -5.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3079   -5.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0223   -6.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7368   -5.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7368   -5.0466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4513   -6.2842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5935   -5.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0216   -7.5214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  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  8  2  0  0  0  0
  6  7  2  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  2  0  0  0  0
  9 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 17  1  0  0  0  0
 15 16  2  0  0  0  0
  2 18  1  0  0  0  0
 10 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001931

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(O)C=C2CCC(C)(CCC(O)=O)OC2=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-9-10(2)14-11(8-12(9)16)4-6-15(3,19-14)7-5-13(17)18/h8,16H,4-7H2,1-3H3,(H,17,18)

> <INCHI_KEY>
VMJQLPNCUPGMNQ-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.321

> <EXACT_MASS>
264.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.59419620912422

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoic acid

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
3.367310166666666

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.47051577837182

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.300033292745505

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852488313385052

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
72.34250000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001931
     RDKit          3D
gamma-CEHC
 39 40  0  0  0  0  0  0  0  0999 V2000
   -4.7350    0.6744   -0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3887    0.1293    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3239   -1.1088    0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5404   -1.7691    0.9099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182   -1.6644    1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9340   -0.9819    0.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0116    0.2395    0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376    0.8034   -0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2434    2.1323   -0.8670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454    0.9398   -0.0971 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4041    0.2263   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3098   -0.7026   -1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4571    1.2304   -0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8701    0.8451   -0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5669    0.3292    0.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1487    0.4359    1.8808 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7837   -0.3317    0.5622 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5346   -0.6406    1.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3485   -1.6046    1.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4126   -0.1692   -0.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6704    1.4000   -1.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1418    1.1458    0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4664   -2.6688    1.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0706   -2.6417    1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7257    2.0934   -1.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8308    2.8136   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2318    2.5399   -0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2446   -1.2829   -1.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809   -1.4133   -1.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725   -0.1198   -2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4017    2.0807    0.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313    1.8007   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4298    1.8052   -0.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0690    0.1922   -1.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7845   -1.0702   -0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4117   -1.3053    0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5951   -0.0156    1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300   -2.5577    0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626   -1.8087    2.2932 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  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 11 18  1  0
 18 19  1  0
  8  2  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 14-MAR-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAR-18         0                                  
HETATM    1  O   UNK     0      14.708 -10.960   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      16.041 -11.731   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.041 -13.270   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.708 -14.040   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.374 -13.270   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.374 -11.731   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.040 -10.960   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.040 -14.040   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.707 -11.731   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.707 -13.270   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.040  -9.420   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.373 -10.960   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.375 -10.960   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.708 -11.731   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.042 -10.960   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      20.042  -9.420   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      21.376 -11.731   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      16.041 -10.190   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.374 -14.040   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   13   18                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6    9   11                                                  
CONECT    8    5   10                                                       
CONECT    9    7   10   12                                                  
CONECT   10    8    9   19                                                  
CONECT   11    7                                                            
CONECT   12    9                                                            
CONECT   13    2   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   17   16                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    2                                                            
CONECT   19   10                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0001931
HETATM    1  C1  UNL     1      -4.735   0.674  -0.324  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.389   0.129   0.047  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.324  -1.109   0.670  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.540  -1.769   0.910  1.00  0.00           O  
HETATM    5  C4  UNL     1      -2.118  -1.664   1.036  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.934  -0.982   0.783  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.012   0.240   0.167  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.238   0.803  -0.204  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.243   2.132  -0.867  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.145   0.940  -0.097  1.00  0.00           O  
HETATM   11  C9  UNL     1       1.404   0.226  -0.124  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.310  -0.703  -1.343  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.457   1.230  -0.348  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.870   0.845  -0.438  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.567   0.329   0.724  1.00  0.00           C  
HETATM   16  O3  UNL     1       4.149   0.436   1.881  1.00  0.00           O  
HETATM   17  O4  UNL     1       5.784  -0.332   0.562  1.00  0.00           O  
HETATM   18  C14 UNL     1       1.535  -0.641   1.061  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.349  -1.605   1.186  1.00  0.00           C  
HETATM   20  H1  UNL     1      -5.413  -0.169  -0.567  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.670   1.400  -1.163  1.00  0.00           H  
HETATM   22  H3  UNL     1      -5.142   1.146   0.598  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.466  -2.669   1.363  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.071  -2.642   1.527  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.726   2.093  -1.865  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.831   2.814  -0.197  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.232   2.540  -0.905  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.245  -1.283  -1.450  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.481  -1.413  -1.180  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.073  -0.120  -2.236  1.00  0.00           H  
HETATM   31  H12 UNL     1       2.402   2.081   0.414  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.231   1.801  -1.322  1.00  0.00           H  
HETATM   33  H14 UNL     1       4.430   1.805  -0.737  1.00  0.00           H  
HETATM   34  H15 UNL     1       4.069   0.192  -1.352  1.00  0.00           H  
HETATM   35  H16 UNL     1       5.785  -1.070  -0.158  1.00  0.00           H  
HETATM   36  H17 UNL     1       2.412  -1.305   1.000  1.00  0.00           H  
HETATM   37  H18 UNL     1       1.595  -0.016   1.966  1.00  0.00           H  
HETATM   38  H19 UNL     1       0.530  -2.558   0.657  1.00  0.00           H  
HETATM   39  H20 UNL     1       0.263  -1.809   2.293  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3    8
CONECT    3    4    5
CONECT    4   23
CONECT    5    6    6   24
CONECT    6    7   19
CONECT    7    8    8   10
CONECT    8    9
CONECT    9   25   26   27
CONECT   10   11
CONECT   11   12   13   18
CONECT   12   28   29   30
CONECT   13   14   31   32
CONECT   14   15   33   34
CONECT   15   16   16   17
CONECT   17   35
CONECT   18   19   36   37
CONECT   19   38   39
END

HMDB0001931
     RDKit          3D
gamma-CEHC
 39 40  0  0  0  0  0  0  0  0999 V2000
   -4.7350    0.6744   -0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3887    0.1293    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3239   -1.1088    0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5404   -1.7691    0.9099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182   -1.6644    1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9340   -0.9819    0.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0116    0.2395    0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376    0.8034   -0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2434    2.1323   -0.8670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454    0.9398   -0.0971 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4041    0.2263   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3098   -0.7026   -1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4571    1.2304   -0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8701    0.8451   -0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5669    0.3292    0.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1487    0.4359    1.8808 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7837   -0.3317    0.5622 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5346   -0.6406    1.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3485   -1.6046    1.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4126   -0.1692   -0.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6704    1.4000   -1.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1418    1.1458    0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4664   -2.6688    1.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0706   -2.6417    1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7257    2.0934   -1.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8308    2.8136   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2318    2.5399   -0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2446   -1.2829   -1.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809   -1.4133   -1.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725   -0.1198   -2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4017    2.0807    0.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313    1.8007   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4298    1.8052   -0.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0690    0.1922   -1.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7845   -1.0702   -0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4117   -1.3053    0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5951   -0.0156    1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300   -2.5577    0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626   -1.8087    2.2932 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  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 11 18  1  0
 18 19  1  0
  8  2  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
g-CEHC	Generator
Γ-cehc	Generator
3-(6-Hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoate	HMDB
S-LLU-alpha	HMDB
LLU-alpha	HMDB
3-(2,7,8-Trimethyl-3,4-dihydro-2H-chromen-2-yl)propanoate	HMDB
(±)-llu-α	HMDB
(±)-llu-alpha	HMDB
2,7,8-Trimethyl-2-(β-carboxyethyl)-6-hydroxychroman	HMDB
2,7,8-Trimethyl-2-(beta-carboxyethyl)-6-hydroxychroman	HMDB
γ-Carboxyethyl hydroxychroman	HMDB
γ-Carboxyethyl-hydroxychroman	HMDB
gamma-Carboxyethyl hydroxychroman	HMDB
gamma-Carboxyethyl-hydroxychroman	HMDB
3'-Carboxychromanol	HMDB
gamma-CEHC	MeSH

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.321

Monoisotopic Molecular Weight

264.136159124

IUPAC Name

3-(6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoic acid

Traditional Name

3-(6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl)propanoic acid

CAS Registry Number

178167-75-4

SMILES

CC1=C(O)C=C2CCC(C)(CCC(O)=O)OC2=C1C

InChI Identifier

InChI=1S/C15H20O4/c1-9-10(2)14-11(8-12(9)16)4-6-15(3,19-14)7-5-13(17)18/h8,16H,4-7H2,1-3H3,(H,17,18)

InChI Key

VMJQLPNCUPGMNQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

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	0.031 g/L	ALOGPS
logP	2.48	ALOGPS
logP	3.37	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.34 m³·mol⁻¹	ChemAxon
Polarizability	28.59 Å³	ChemAxon
Number of Rings	2	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
AllCCS	[M+H]+	162.175	32859911
AllCCS	[M-H]-	166.939	32859911
DeepCCS	[M+H]+	161.748	30932474
DeepCCS	[M-H]-	159.39	30932474
DeepCCS	[M-2H]-	192.289	30932474
DeepCCS	[M+Na]+	167.841	30932474
AllCCS	[M+H]+	162.2	32859911
AllCCS	[M+H-H2O]+	158.5	32859911
AllCCS	[M+NH4]+	165.6	32859911
AllCCS	[M+Na]+	166.6	32859911
AllCCS	[M-H]-	166.9	32859911
AllCCS	[M+Na-2H]-	167.0	32859911
AllCCS	[M+HCOO]-	167.2	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.	5.81 minutes	32390414
Predicted by Siyang on May 30, 2022	13.5269 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.48 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1931.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	319.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	173.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	186.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	196.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	726.2 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	696.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	70.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1155.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	448.6 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	1472.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	436.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	381.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	317.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	227.5 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	54.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-CEHC	CC1=C(O)C=C2CCC(C)(CCC(O)=O)OC2=C1C	3501.7	Standard polar	33892256
gamma-CEHC	CC1=C(O)C=C2CCC(C)(CCC(O)=O)OC2=C1C	2263.3	Standard non polar	33892256
gamma-CEHC	CC1=C(O)C=C2CCC(C)(CCC(O)=O)OC2=C1C	2361.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
gamma-CEHC,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C=C2CCC(C)(CCC(=O)O)OC2=C1C	2314.7	Semi standard non polar	33892256
gamma-CEHC,1TMS,isomer #2	CC1=C(O)C=C2CCC(C)(CCC(=O)O[Si](C)(C)C)OC2=C1C	2243.7	Semi standard non polar	33892256
gamma-CEHC,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C=C2CCC(C)(CCC(=O)O[Si](C)(C)C)OC2=C1C	2293.9	Semi standard non polar	33892256
gamma-CEHC,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C=C2CCC(C)(CCC(=O)O)OC2=C1C	2577.3	Semi standard non polar	33892256
gamma-CEHC,1TBDMS,isomer #2	CC1=C(O)C=C2CCC(C)(CCC(=O)O[Si](C)(C)C(C)(C)C)OC2=C1C	2528.2	Semi standard non polar	33892256
gamma-CEHC,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C=C2CCC(C)(CCC(=O)O[Si](C)(C)C(C)(C)C)OC2=C1C	2784.1	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 - gamma-CEHC 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 - gamma-CEHC 10V, Positive-QTOF	splash10-001i-0390000000-b666254f822f684d0f90	2018-11-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-CEHC 20V, Positive-QTOF	splash10-000i-2920000000-bb8603bd0385ca985211	2018-11-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-CEHC 40V, Positive-QTOF	splash10-05r9-5900000000-5e06b4301c1de7edc79a	2018-11-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-CEHC 10V, Positive-QTOF	splash10-0002-0490000000-f7808533b982dc68faac	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-CEHC 20V, Positive-QTOF	splash10-0f6t-0930000000-bd68d5cb372a6bcdc833	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-CEHC 40V, Positive-QTOF	splash10-0fdk-4900000000-8472a89e5baa2c694314	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-CEHC 10V, Negative-QTOF	splash10-014i-0090000000-3a627b5dee80a85c1360	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-CEHC 20V, Negative-QTOF	splash10-014i-1290000000-91128d74296130540d8c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-CEHC 40V, Negative-QTOF	splash10-0iki-2950000000-0c65f7f58462d6926552	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.16 (0.11-0.2) uM	Adult (>18 years old)	Both	Normal	11841923	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022748

KNApSAcK ID

Not Available

Chemspider ID

117455

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133098

PDB ID

Not Available

ChEBI ID

Not Available

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

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 ]
Galli F, Lee R, Dunster C, Kelly FJ: Gas chromatography mass spectrometry analysis of carboxyethyl-hydroxychroman metabolites of alpha- and gamma-tocopherol in human plasma. Free Radic Biol Med. 2002 Feb 15;32(4):333-40. [PubMed:11841923 ]

Showing metabocard for gamma-CEHC (HMDB0001931)

MOL for HMDB0001931 (gamma-CEHC)

3D MOL for HMDB0001931 (gamma-CEHC)

3D SDF for HMDB0001931 (gamma-CEHC)

3D-SDF for HMDB0001931 (gamma-CEHC)

PDB for HMDB0001931 (gamma-CEHC)

3D PDB for HMDB0001931 (gamma-CEHC)

SMILES for HMDB0001931 (gamma-CEHC)

INCHI for HMDB0001931 (gamma-CEHC)

Structure for HMDB0001931 (gamma-CEHC)

3D Structure for HMDB0001931 (gamma-CEHC)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra