MiMeDB: Showing metabocard for p-Cresol glucuronide (MMDBc0000649)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:51:55 UTC

Update Date

2024-04-30 19:33:24 UTC

Metabolite ID

MMDBc0000649

Metabolite Identification

Common Name

p-Cresol glucuronide

Description

p-Cresol glucuronide is a glucuronide derivative a p-Cresol that is typically excreted in the urine. P-Cresol (the precursor of p-cresol sulfate (PCS) and p-cresol glucuronide (PCG)) is mainly generated as an end product of tyrosine biotransformation by anaerobic intestinal bacteria. During passage through the colonic mucosa and liver, sulfatation and glucuronidation generates p-Cresol sulfate (as the most preponderant metabolite) and p-Cresol glucuronide (at markedly lower concentrations) (PMID: 23826225 ). Cresols are known as methylphenols. Cresols are used to dissolve other chemicals, such as disinfectants and deodorizers. They are also used to make specific chemicals that kill insect pests. Cresol solutions are used as household cleaners and disinfectants such as Lysol. Cresol solutions can also be found in photographic developers. In the past, cresol solutions have been used as antiseptics in surgery, but they have been largely displaced in this role by less toxic compounds. Cresols are found in many foods and in wood and tobacco smoke, crude oil, coal tar, and in brown mixtures such as creosote, cresolene and cresylic acids, which are wood preservatives. Microbes in the soil and water produce cresols when they break down materials in the environment. Most exposures to cresols are at very low levels that are not harmful. When cresols are breathed, ingested, or applied to the skin at very high levels, they can be very harmful. Effects observed in people include irritation and burning of skin, eyes, mouth, and throat; abdominal pain and vomiting. Cresols are also a chemical component found in Sharpie Markers. P-cresol is a major component in pig odor.

Structure

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

HMDB0011686
     RDKit          3D
p-Cresol glucuronide
 36 37  0  0  0  0  0  0  0  0999 V2000
    5.7647    0.8437   -0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3598    0.6200   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3881    0.4130   -1.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0528    0.1990   -0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667    0.1884    0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3949   -0.0113    1.0310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637   -0.2416    0.2934 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6220    0.8555    0.5348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6927    0.7120   -0.3360 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4688    1.9515   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4871    2.0045   -1.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0890    3.0507    0.3382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5593   -0.4066    0.2061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6331   -0.5849   -0.6560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8210   -1.6813    0.3954 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4626   -2.4069    1.4147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835   -1.5257    0.7797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6779   -2.5974    0.2484 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6671    0.4006    1.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9808    0.6109    1.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8607    1.8722   -0.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0135    0.1793   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4851    0.5584    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746    0.4182   -2.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    0.0390   -1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5670   -0.2538   -0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2625    0.4339   -1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4851    3.9505    0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9904   -0.0366    1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3715   -1.2312   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9552   -2.2969   -0.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681   -3.2547    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2433   -1.5663    1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2816   -2.3832   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3956    0.3988    2.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7739    0.7782    1.9018 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
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 17  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  7 26  1  6
  9 27  1  6
 12 28  1  0
 13 29  1  1
 14 30  1  0
 15 31  1  6
 16 32  1  0
 17 33  1  1
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END


  Mrv0541 02241201502D          

 20 21  0  0  1  0            999 V2000
    8.9471   -6.7790    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9471   -7.6040    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2326   -6.3665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2326   -8.0165    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5181   -6.7790    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5181   -7.6040    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8036   -6.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8036   -8.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2326   -8.8415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6615   -8.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6615   -6.3665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8036   -5.5414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0892   -6.7790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8050   -7.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0905   -8.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8050   -6.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3760   -7.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0905   -6.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3760   -6.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5195   -8.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  5  7  1  1  0  0  0
  6  8  1  6  0  0  0
  4  9  1  1  0  0  0
  2 10  1  6  0  0  0
  1 11  1  1  0  0  0
 12  7  1  0  0  0  0
 13  7  2  0  0  0  0
 15 14  1  0  0  0  0
 16 14  2  0  0  0  0
 17 15  2  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 19 18  2  0  0  0  0
 11 19  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000649

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=CC=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O7/c1-6-2-4-7(5-3-6)19-13-10(16)8(14)9(15)11(20-13)12(17)18/h2-5,8-11,13-16H,1H3,(H,17,18)/t8-,9-,10+,11-,13+/m0/s1

> <INCHI_KEY>
JPAUCQAJHLSMQW-XPORZQOISA-N

> <FORMULA>
C13H16O7

> <MOLECULAR_WEIGHT>
284.2619

> <EXACT_MASS>
284.089602866

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
27.438826898187873

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-0.45

> <JCHEM_LOGP>
0.2353083283333341

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.216821421434362

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2973006426730334

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686826761377044

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
65.09190000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011686
     RDKit          3D
p-Cresol glucuronide
 36 37  0  0  0  0  0  0  0  0999 V2000
    5.7647    0.8437   -0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3598    0.6200   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3881    0.4130   -1.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0528    0.1990   -0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667    0.1884    0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3949   -0.0113    1.0310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637   -0.2416    0.2934 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6220    0.8555    0.5348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6927    0.7120   -0.3360 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4688    1.9515   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4871    2.0045   -1.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0890    3.0507    0.3382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5593   -0.4066    0.2061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6331   -0.5849   -0.6560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8210   -1.6813    0.3954 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4626   -2.4069    1.4147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835   -1.5257    0.7797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6779   -2.5974    0.2484 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6671    0.4006    1.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9808    0.6109    1.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8607    1.8722   -0.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0135    0.1793   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4851    0.5584    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746    0.4182   -2.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    0.0390   -1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5670   -0.2538   -0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2625    0.4339   -1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4851    3.9505    0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9904   -0.0366    1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3715   -1.2312   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9552   -2.2969   -0.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681   -3.2547    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2433   -1.5663    1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2816   -2.3832   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3956    0.3988    2.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7739    0.7782    1.9018 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
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 17  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  7 26  1  6
  9 27  1  6
 12 28  1  0
 13 29  1  1
 14 30  1  0
 15 31  1  6
 16 32  1  0
 17 33  1  1
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      16.701 -12.654   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.701 -14.194   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      15.368 -11.884   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      15.368 -14.964   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.034 -12.654   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.034 -14.194   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.700 -11.884   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      12.700 -14.964   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      15.368 -16.504   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      18.035 -14.964   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      18.035 -11.884   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      12.700 -10.344   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      11.367 -12.654   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      22.036 -14.194   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.702 -14.964   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.036 -12.654   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.369 -14.194   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.702 -11.884   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.369 -12.654   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.370 -14.964   0.000  0.00  0.00           C+0
CONECT    1    2    3   11                                                  
CONECT    2    1    4   10                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6    9                                                  
CONECT    5    3    6    7                                                  
CONECT    6    4    5    8                                                  
CONECT    7    5   12   13                                                  
CONECT    8    6                                                            
CONECT    9    4                                                            
CONECT   10    2                                                            
CONECT   11    1   19                                                       
CONECT   12    7                                                            
CONECT   13    7                                                            
CONECT   14   15   16   20                                                  
CONECT   15   14   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   19                                                       
CONECT   19   17   18   11                                                  
CONECT   20   14                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0011686
HETATM    1  C1  UNL     1       5.765   0.844  -0.577  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.360   0.620  -0.156  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.388   0.413  -1.099  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.053   0.199  -0.735  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.667   0.188   0.583  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.395  -0.011   1.031  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.764  -0.242   0.293  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.622   0.855   0.535  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.693   0.712  -0.336  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.469   1.952  -0.407  1.00  0.00           C  
HETATM   11  O3  UNL     1      -4.487   2.005  -1.157  1.00  0.00           O  
HETATM   12  O4  UNL     1      -3.089   3.051   0.338  1.00  0.00           O  
HETATM   13  C9  UNL     1      -3.559  -0.407   0.206  1.00  0.00           C  
HETATM   14  O5  UNL     1      -4.633  -0.585  -0.656  1.00  0.00           O  
HETATM   15  C10 UNL     1      -2.821  -1.681   0.395  1.00  0.00           C  
HETATM   16  O6  UNL     1      -3.463  -2.407   1.415  1.00  0.00           O  
HETATM   17  C11 UNL     1      -1.384  -1.526   0.780  1.00  0.00           C  
HETATM   18  O7  UNL     1      -0.678  -2.597   0.248  1.00  0.00           O  
HETATM   19  C12 UNL     1       2.667   0.401   1.534  1.00  0.00           C  
HETATM   20  C13 UNL     1       3.981   0.611   1.169  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.861   1.872  -0.923  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.014   0.179  -1.451  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.485   0.558   0.216  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.675   0.418  -2.141  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.307   0.039  -1.485  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.567  -0.254  -0.795  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.262   0.434  -1.329  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.485   3.951   0.135  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.990  -0.037   1.170  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.372  -1.231  -1.356  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.955  -2.297  -0.533  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.968  -3.255   1.609  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.243  -1.566   1.883  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.282  -2.383  -0.646  1.00  0.00           H  
HETATM   35  H15 UNL     1       2.396   0.399   2.594  1.00  0.00           H  
HETATM   36  H16 UNL     1       4.774   0.778   1.902  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3   20
CONECT    3    4   24
CONECT    4    5    5   25
CONECT    5    6   19
CONECT    6    7
CONECT    7    8   17   26
CONECT    8    9
CONECT    9   10   13   27
CONECT   10   11   11   12
CONECT   12   28
CONECT   13   14   15   29
CONECT   14   30
CONECT   15   16   17   31
CONECT   16   32
CONECT   17   18   33
CONECT   18   34
CONECT   19   20   20   35
CONECT   20   36
END

HMDB0011686
     RDKit          3D
p-Cresol glucuronide
 36 37  0  0  0  0  0  0  0  0999 V2000
    5.7647    0.8437   -0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3598    0.6200   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3881    0.4130   -1.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0528    0.1990   -0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667    0.1884    0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3949   -0.0113    1.0310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637   -0.2416    0.2934 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6220    0.8555    0.5348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6927    0.7120   -0.3360 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4688    1.9515   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4871    2.0045   -1.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0890    3.0507    0.3382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5593   -0.4066    0.2061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6331   -0.5849   -0.6560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8210   -1.6813    0.3954 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4626   -2.4069    1.4147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835   -1.5257    0.7797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6779   -2.5974    0.2484 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6671    0.4006    1.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9808    0.6109    1.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8607    1.8722   -0.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0135    0.1793   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4851    0.5584    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746    0.4182   -2.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    0.0390   -1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5670   -0.2538   -0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2625    0.4339   -1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4851    3.9505    0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9904   -0.0366    1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3715   -1.2312   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9552   -2.2969   -0.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681   -3.2547    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2433   -1.5663    1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2816   -2.3832   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3956    0.3988    2.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7739    0.7782    1.9018 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
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 17  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  7 26  1  6
  9 27  1  6
 12 28  1  0
 13 29  1  1
 14 30  1  0
 15 31  1  6
 16 32  1  0
 17 33  1  1
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END

Synonyms

Value	Source
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylic acid	ChEBI
Cresol glucuronide	ChEBI
Cresyl glucuronide	ChEBI
Cresylglucuronide	ChEBI
p-Cresyl glucuronide	ChEBI
p-Cresyl-beta-D-glucuronide	ChEBI
p-Cresylglucuronide	ChEBI
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylate	Generator
p-Cresyl-b-D-glucuronide	Generator
p-Cresyl-β-D-glucuronide	Generator
4-Methylphenyl beta-D-glucopyranosiduronate	HMDB
4-Methylphenyl beta-D-glucopyranosiduronic acid	HMDB
pCG	HMDB
4-Cresylglucuronide	HMDB
p-Tolyl b-D-glucuronide	HMDB
p-Tolyl β-D-glucuronide	HMDB
p-Cresol glucuronide	ChEBI

Molecular Formula

C₁₃H₁₆O₇

Average Mass

284.2619

Monoisotopic Mass

284.089602866

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=CC=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1

InChI Identifier

InChI=1S/C13H16O7/c1-6-2-4-7(5-3-6)19-13-10(16)8(14)9(15)11(20-13)12(17)18/h2-5,8-11,13-16H,1H3,(H,17,18)/t8-,9-,10+,11-,13+/m0/s1

InChI Key

JPAUCQAJHLSMQW-XPORZQOISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
O-glycosyl compound
Phenoxy compound
Phenol ether
Beta-hydroxy acid
Toluene
Monocyclic benzene moiety
Hydroxy acid
Monosaccharide
Benzenoid
Oxane
Pyran
Secondary alcohol
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	24 g/L	ALOGPS
logP	-0.45	ALOGPS
logP	0.24	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	65.09 m³·mol⁻¹	ChemAxon
Polarizability	27.44 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	splash10-0a4i-9740000000-72c74a4f612ab1d96b3c	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0a4i-3111590000-c4085ee51e3627835f9c	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-8900000000-125953bb33ef62310b55	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9500000000-c65eb13127918057773b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03e9-4920000000-31cc7062997a091bd192	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0980000000-0c28ed49edf3ac01b1e4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0910000000-9e86725c906b8cb1ca73	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9700000000-7c668dc4ccf5c2f1df52	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-053r-1790000000-8e41a0062d8b43c11986	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1920000000-2c0bc993f06c27f10d87	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-5900000000-078071ef7d6ab4f0ed4c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05n0-0690000000-21c7e95f0396cfbeb2cc	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1920000000-d2d499346dfdb60bcd5c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9500000000-5890de451e5c75c51696	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-053r-0790000000-26241f9e17537357950e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-4910000000-9f376fa7de7498124a4b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9600000000-469910059aa1c2c999fd	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Kidney
Liver
Urine

Tissue Locations

Kidney
Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192118	UDP-glucuronosyltransferase 2B4	Enzyme	P06133	Homo sapiens
MMDBp0192135	UDP-glucuronosyltransferase 1-4	Enzyme	P22310	Homo sapiens
MMDBp0192137	UDP-glucuronosyltransferase 2B7	Enzyme	P16662	Homo sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0192141	UDP-glucuronosyltransferase 1-9	Enzyme	O60656	Homo sapiens
MMDBp0192146	UDP-glucuronosyltransferase 1-6	Enzyme	P19224	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

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	Firmicutes	6	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	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	1.0	0.7	uM	Adult (>18 years old)	Male	Normal	HMDB	23826225
Human Kidney	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0011686

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028373

KNApSAcK ID

Not Available

Chemspider ID

135751

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

154035

PDB ID

Not Available

ChEBI ID

87986

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Liabeuf S, Glorieux G, Lenglet A, Diouf M, Schepers E, Desjardins L, Choukroun G, Vanholder R, Massy ZA: Does p-cresylglucuronide have the same impact on mortality as other protein-bound uremic toxins? PLoS One. 2013 Jun 24;8(6):e67168. doi: 10.1371/journal.pone.0067168. Print 2013. [PubMed:23826225 ]

Showing metabocard for p-Cresol glucuronide (MMDBc0000649)

MOL for #<Metabolite:0x00007fdaf17cf5a0>

3D MOL for #<Metabolite:0x00007fdaf17cf5a0>

3D SDF for #<Metabolite:0x00007fdaf17cf5a0>

3D-SDF for #<Metabolite:0x00007fdaf17cf5a0>

PDB for #<Metabolite:0x00007fdaf17cf5a0>

3D PDB for #<Metabolite:0x00007fdaf17cf5a0>

SMILES for #<Metabolite:0x00007fdaf17cf5a0>

INCHI for #<Metabolite:0x00007fdaf17cf5a0>

Structure for #<Metabolite:0x00007fdaf17cf5a0>

3D Structure for #<Metabolite:0x00007fdaf17cf5a0>