MiMeDB: Showing metabocard for gamma-CEHC (MMDBc0000397)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:51 UTC

Update Date

2024-04-30 19:32:09 UTC

Metabolite ID

MMDBc0000397

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>
MMDBc0000397

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₅H₂₀O₄

Average Mass

264.321

Monoisotopic Mass

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

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.18 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0390000000-b666254f822f684d0f90	2018-11-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-2920000000-bb8603bd0385ca985211	2018-11-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05r9-5900000000-5e06b4301c1de7edc79a	2018-11-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0490000000-f7808533b982dc68faac	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f6t-0930000000-bd68d5cb372a6bcdc833	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fdk-4900000000-8472a89e5baa2c694314	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-3a627b5dee80a85c1360	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1290000000-91128d74296130540d8c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0iki-2950000000-0c65f7f58462d6926552	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0004256	gamma-CEHC	Gama-Cehc-Glucuronide	UDP glucuronosyltransferase 1 family, polypeptide A8	VMH	10191290
MMDBr0004257	gamma-CEHC	Gama-Cehc-Glucuronide	UDP glucuronosyltransferase 1 family, polypeptide A10	VMH	10191290
MMDBr0004300	Gama-Cehc-Glucuronide	gamma-CEHC	klotho	VMH	10191290
MMDBr0004301	Gama-Cehc-Glucuronide	gamma-CEHC	klotho	VMH	10191290
MMDBr0004302	Gama-Cehc-Glucuronide	gamma-CEHC	glucuronidase, beta	VMH	10191290
MMDBr0010356	5'-Carboxy-gamma-chromanol	gamma-CEHC	aminoadipate-semialdehyde dehydrogenase	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human Blood	Detected and Quantified	0.16	0.11	0.2	uM	Adult (>18 years old)	Both	Normal	HMDB	11841923
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0001931

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

15887183

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/s0891-5849(01)00800-0. [PubMed:11841923 ]
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. doi: 10.1080/10715760410001715149. [PubMed:15493460 ]

Showing metabocard for gamma-CEHC (MMDBc0000397)

MOL for #<Metabolite:0x00007fdb488c9f80>

3D MOL for #<Metabolite:0x00007fdb488c9f80>

3D SDF for #<Metabolite:0x00007fdb488c9f80>

3D-SDF for #<Metabolite:0x00007fdb488c9f80>

PDB for #<Metabolite:0x00007fdb488c9f80>

3D PDB for #<Metabolite:0x00007fdb488c9f80>

SMILES for #<Metabolite:0x00007fdb488c9f80>

INCHI for #<Metabolite:0x00007fdb488c9f80>

Structure for #<Metabolite:0x00007fdb488c9f80>

3D Structure for #<Metabolite:0x00007fdb488c9f80>