MiMeDB: Showing metabocard for beta-D-Glucopyranuronic acid (MMDBc0052891)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:08:15 UTC

Update Date

2024-04-30 20:43:59 UTC

Metabolite ID

MMDBc0052891

Metabolite Identification

Common Name

beta-D-Glucopyranuronic acid

Description

beta-D-Glucopyranuronic acid, also known as salicylacyl glucuronide, is a natural human metabolite of acetylsilacylic acid generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.

Structure

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

HMDB0010314
     RDKit          3D
Beta-D-Glucopyranuronic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
    1.1157   -1.4401    1.3254 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834   -0.6521    0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4958    0.1316   -0.1785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -0.0115    0.2546 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6160   -0.3439   -0.8615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8824   -0.7184   -0.4926 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8999   -0.4298   -1.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1181   -0.6938   -1.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5026    0.1612   -2.7208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3470   -0.0947    0.7952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0663   -0.9406    1.8533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7775    1.2772    0.9402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4395    2.1215    0.0260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022    1.3601    0.6926 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6460    1.8265    1.8039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750   -0.5516    0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724    0.3667   -0.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4639    0.4952   -1.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4887   -0.2407   -0.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2031   -1.1347    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8835   -1.2949    0.5817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6920   -2.2085    1.5740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8822   -0.7564    1.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671   -1.8376   -0.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8637   -0.1043   -3.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4676    0.0177    0.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0483   -0.5156    2.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0507    1.6783    1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8224    2.3399   -0.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0783    2.0485   -0.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1377    2.3617    1.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3757    0.9414   -1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7318    1.1922   -2.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5114   -0.1342   -1.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9898   -1.7134    0.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892   -2.5024    2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 14  4  1  0
 21 16  1  0
  4 23  1  1
  6 24  1  1
  9 25  1  0
 10 26  1  6
 11 27  1  0
 12 28  1  1
 13 29  1  0
 14 30  1  6
 15 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
 22 36  1  0
M  END


  Mrv0541 02241200502D          

 22 23  0  0  1  0            999 V2000
   18.4500   -5.9029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4500   -8.3779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8790   -7.5529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0210   -5.9029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0210   -7.5529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8790   -5.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5934   -6.3154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7355   -4.6653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0210   -3.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4500   -7.5529    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.1645   -7.1404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7355   -7.1404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.1645   -6.3154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7355   -6.3154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.8790   -5.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0210   -5.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3065   -4.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3065   -3.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5920   -5.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5920   -3.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8775   -4.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8775   -3.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
 10  2  1  6  0  0  0
 11  3  1  1  0  0  0
 14  4  1  6  0  0  0
  4 16  1  0  0  0  0
 12  5  1  1  0  0  0
  6 15  1  0  0  0  0
  7 15  2  0  0  0  0
  8 16  2  0  0  0  0
  9 18  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0052891

> <DATABASE_NAME>
MIME

> <SMILES>
O[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CC=CC=C2O)O[C@@H]([C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O9/c14-6-4-2-1-3-5(6)12(20)22-13-9(17)7(15)8(16)10(21-13)11(18)19/h1-4,7-10,13-17H,(H,18,19)/t7-,8-,9+,10-,13-/m0/s1

> <INCHI_KEY>
IXVVXKRKCLJCKA-UNLLLRGISA-N

> <FORMULA>
C13H14O9

> <MOLECULAR_WEIGHT>
314.2449

> <EXACT_MASS>
314.063782046

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
28.10802644190356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.62

> <JCHEM_LOGP>
0.22946984700000037

> <ALOGPS_LOGS>
-1.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.688128870593161

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.950938943013179

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686906544261925

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
67.59370000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010314
     RDKit          3D
Beta-D-Glucopyranuronic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
    1.1157   -1.4401    1.3254 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834   -0.6521    0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4958    0.1316   -0.1785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -0.0115    0.2546 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6160   -0.3439   -0.8615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8824   -0.7184   -0.4926 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8999   -0.4298   -1.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1181   -0.6938   -1.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5026    0.1612   -2.7208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3470   -0.0947    0.7952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0663   -0.9406    1.8533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7775    1.2772    0.9402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4395    2.1215    0.0260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022    1.3601    0.6926 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6460    1.8265    1.8039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750   -0.5516    0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724    0.3667   -0.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4639    0.4952   -1.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4887   -0.2407   -0.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2031   -1.1347    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8835   -1.2949    0.5817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6920   -2.2085    1.5740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8822   -0.7564    1.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671   -1.8376   -0.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8637   -0.1043   -3.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4676    0.0177    0.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0483   -0.5156    2.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0507    1.6783    1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8224    2.3399   -0.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0783    2.0485   -0.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1377    2.3617    1.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3757    0.9414   -1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7318    1.1922   -2.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5114   -0.1342   -1.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9898   -1.7134    0.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892   -2.5024    2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 14  4  1  0
 21 16  1  0
  4 23  1  1
  6 24  1  1
  9 25  1  0
 10 26  1  6
 11 27  1  0
 12 28  1  1
 13 29  1  0
 14 30  1  6
 15 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
 22 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  O   UNK     0      34.440 -11.019   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      34.440 -15.639   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      37.107 -14.099   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      31.773 -11.019   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      31.773 -14.099   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      37.107  -9.479   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      38.441 -11.789   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      33.106  -8.709   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      31.773  -6.399   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      34.440 -14.099   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      35.774 -13.329   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.106 -13.329   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.774 -11.789   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.106 -11.789   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.107 -11.019   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.773  -9.479   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.439  -8.709   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.439  -7.169   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.105  -9.479   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      29.105  -6.399   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.771  -8.709   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.771  -7.169   0.000  0.00  0.00           C+0
CONECT    1   13   14                                                       
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   14   16                                                       
CONECT    5   12                                                            
CONECT    6   15                                                            
CONECT    7   15                                                            
CONECT    8   16                                                            
CONECT    9   18                                                            
CONECT   10    2   11   12                                                  
CONECT   11    3   10   13                                                  
CONECT   12    5   10   14                                                  
CONECT   13    1   11   15                                                  
CONECT   14    1    4   12                                                  
CONECT   15    6    7   13                                                  
CONECT   16    4    8   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18    9   17   20                                                  
CONECT   19   17   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   22                                                       
CONECT   22   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0010314
HETATM    1  O1  UNL     1       1.116  -1.440   1.325  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.483  -0.652   0.426  1.00  0.00           C  
HETATM    3  O2  UNL     1       0.496   0.132  -0.178  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.832  -0.011   0.255  1.00  0.00           C  
HETATM    5  O3  UNL     1      -1.616  -0.344  -0.861  1.00  0.00           O  
HETATM    6  C3  UNL     1      -2.882  -0.718  -0.493  1.00  0.00           C  
HETATM    7  C4  UNL     1      -3.900  -0.430  -1.532  1.00  0.00           C  
HETATM    8  O4  UNL     1      -5.118  -0.694  -1.396  1.00  0.00           O  
HETATM    9  O5  UNL     1      -3.503   0.161  -2.721  1.00  0.00           O  
HETATM   10  C5  UNL     1      -3.347  -0.095   0.795  1.00  0.00           C  
HETATM   11  O6  UNL     1      -3.066  -0.941   1.853  1.00  0.00           O  
HETATM   12  C6  UNL     1      -2.778   1.277   0.940  1.00  0.00           C  
HETATM   13  O7  UNL     1      -3.440   2.121   0.026  1.00  0.00           O  
HETATM   14  C7  UNL     1      -1.302   1.360   0.693  1.00  0.00           C  
HETATM   15  O8  UNL     1      -0.646   1.827   1.804  1.00  0.00           O  
HETATM   16  C8  UNL     1       2.875  -0.552   0.024  1.00  0.00           C  
HETATM   17  C9  UNL     1       3.172   0.367  -0.996  1.00  0.00           C  
HETATM   18  C10 UNL     1       4.464   0.495  -1.406  1.00  0.00           C  
HETATM   19  C11 UNL     1       5.489  -0.241  -0.860  1.00  0.00           C  
HETATM   20  C12 UNL     1       5.203  -1.135   0.133  1.00  0.00           C  
HETATM   21  C13 UNL     1       3.884  -1.295   0.582  1.00  0.00           C  
HETATM   22  O9  UNL     1       3.692  -2.208   1.574  1.00  0.00           O  
HETATM   23  H1  UNL     1      -0.882  -0.756   1.041  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.867  -1.838  -0.363  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.864  -0.104  -3.629  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.468   0.018   0.766  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.048  -0.516   2.726  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.051   1.678   1.954  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.822   2.340  -0.734  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.078   2.048  -0.157  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.138   2.362   1.523  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.376   0.941  -1.424  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.732   1.192  -2.190  1.00  0.00           H  
HETATM   34  H12 UNL     1       6.511  -0.134  -1.189  1.00  0.00           H  
HETATM   35  H13 UNL     1       5.990  -1.713   0.567  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.889  -2.502   2.052  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   16
CONECT    3    4
CONECT    4    5   14   23
CONECT    5    6
CONECT    6    7   10   24
CONECT    7    8    8    9
CONECT    9   25
CONECT   10   11   12   26
CONECT   11   27
CONECT   12   13   14   28
CONECT   13   29
CONECT   14   15   30
CONECT   15   31
CONECT   16   17   17   21
CONECT   17   18   32
CONECT   18   19   19   33
CONECT   19   20   34
CONECT   20   21   21   35
CONECT   21   22
CONECT   22   36
END

HMDB0010314
     RDKit          3D
Beta-D-Glucopyranuronic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
    1.1157   -1.4401    1.3254 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834   -0.6521    0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4958    0.1316   -0.1785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -0.0115    0.2546 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6160   -0.3439   -0.8615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8824   -0.7184   -0.4926 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8999   -0.4298   -1.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1181   -0.6938   -1.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5026    0.1612   -2.7208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3470   -0.0947    0.7952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0663   -0.9406    1.8533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7775    1.2772    0.9402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4395    2.1215    0.0260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022    1.3601    0.6926 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6460    1.8265    1.8039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750   -0.5516    0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724    0.3667   -0.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4639    0.4952   -1.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4887   -0.2407   -0.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2031   -1.1347    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8835   -1.2949    0.5817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6920   -2.2085    1.5740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8822   -0.7564    1.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671   -1.8376   -0.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8637   -0.1043   -3.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4676    0.0177    0.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0483   -0.5156    2.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0507    1.6783    1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8224    2.3399   -0.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0783    2.0485   -0.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1377    2.3617    1.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3757    0.9414   -1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7318    1.1922   -2.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5114   -0.1342   -1.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9898   -1.7134    0.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892   -2.5024    2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 14  4  1  0
 21 16  1  0
  4 23  1  1
  6 24  1  1
  9 25  1  0
 10 26  1  6
 11 27  1  0
 12 28  1  1
 13 29  1  0
 14 30  1  6
 15 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
 22 36  1  0
M  END

Synonyms

Value	Source
b-D-Glucopyranuronate	Generator
b-D-Glucopyranuronic acid	Generator
beta-D-Glucopyranuronate	Generator
Β-D-glucopyranuronate	Generator
Β-D-glucopyranuronic acid	Generator
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(2-hydroxybenzoyl)oxyoxane-2-carboxylic acid	HMDB
1-(2-Hydroxybenzoate	HMDB
1-(2-Hydroxybenzoate) beta-D-glucopyranuronic acid	HMDB
1-(2-Hydroxybenzoate) beta-delta-glucopyranuronic acid	HMDB
1-(2-Hydroxybenzoic acid	HMDB
Acyl sa glucuronide	HMDB
Salicyl acyl glucuronide	HMDB
Salicylacyl glucuronide	HMDB

Molecular Formula

C₁₃H₁₄O₉

Average Mass

314.2449

Monoisotopic Mass

314.063782046

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CC=CC=C2O)O[C@@H]([C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C13H14O9/c14-6-4-2-1-3-5(6)12(20)22-13-9(17)7(15)8(16)10(21-13)11(18)19/h1-4,7-10,13-17H,(H,18,19)/t7-,8-,9+,10-,13-/m0/s1

InChI Key

IXVVXKRKCLJCKA-UNLLLRGISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glucuronides

Alternative Parents

Substituents

1-o-glucuronide
O-glucuronide
O-hydroxybenzoic acid ester
Salicylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Beta-hydroxy acid
Pyran
Hydroxy acid
Monosaccharide
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Oxane
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alcohol
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	20.8 g/L	ALOGPS
logP	-0.62	ALOGPS
logP	0.23	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	2.95	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	67.59 m³·mol⁻¹	ChemAxon
Polarizability	28.11 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-9430000000-2a4f0c4deaff6c4abb73	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-06r6-2511119000-59f9672d4beab9a8844f	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-007a-0921000000-deba0e5c59d184c9d5e2	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0900000000-bbf3cfca43ba05860073	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-6900000000-0c1d8f8007fa6b2a3c2c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-029i-2933000000-5b35c7a1e0ad8e165c2f	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-7920000000-b2e496121f275b5584ce	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9500000000-0e8d009e9ee72ff94b65	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01ox-4922000000-acce7bb9f6e3f0a62380	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9700000000-1f4af5f176d9b59ee9fe	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-f0d349229272c9b8a05a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00xr-1914000000-4de49b2233eaa00d2452	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1931000000-366fb65d354fc06e6d41	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0g4l-9600000000-054bb7d4dc56cf6bd12e	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

Cytoplasm

Biospecimen Locations

Not Available

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
MMDBp0192459	Beta-glucuronidase	Enzyme	P08236	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0010314

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027466

KNApSAcK ID

Not Available

Chemspider ID

147725

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

168876

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Shen JJ, Wanwimolruk S, Roberts MS: Novel direct high-performance liquid chromatographic method for determination of salicylate glucuronide conjugates in human urine. J Chromatogr. 1991 Apr 19;565(1-2):309-20. doi: 10.1016/0378-4347(91)80392-p. [PubMed:1874875 ]
Patel DK, Notarianni LJ, Bennett PN: Comparative metabolism of high doses of aspirin in man and rat. Xenobiotica. 1990 Aug;20(8):847-54. doi: 10.3109/00498259009046898. [PubMed:2219967 ]
Day RO, Furst DE, Dromgoole SH, Paulus HE: Changes in salicylate serum concentration and metabolism during chronic dosing in normal volunteers. Biopharm Drug Dispos. 1988 May-Jun;9(3):273-83. doi: 10.1002/bod.2510090306. [PubMed:3395669 ]
Dickinson RG, Baker PV, King AR: Studies on the reactivity of acyl glucuronides--VII. Salicyl acyl glucuronide reactivity in vitro and covalent binding of salicylic acid to plasma protein of humans taking aspirin. Biochem Pharmacol. 1994 Feb 9;47(3):469-76. doi: 10.1016/0006-2952(94)90177-5. [PubMed:8117314 ]
Liu JH, Smith PC: Direct analysis of salicylic acid, salicyl acyl glucuronide, salicyluric acid and gentisic acid in human plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Jan 12;675(1):61-70. doi: 10.1016/0378-4347(95)00337-1. [PubMed:8634769 ]

Showing metabocard for beta-D-Glucopyranuronic acid (MMDBc0052891)

MOL for #<Metabolite:0x00007feca4ef9a78>

3D MOL for #<Metabolite:0x00007feca4ef9a78>

3D SDF for #<Metabolite:0x00007feca4ef9a78>

3D-SDF for #<Metabolite:0x00007feca4ef9a78>

PDB for #<Metabolite:0x00007feca4ef9a78>

3D PDB for #<Metabolite:0x00007feca4ef9a78>

SMILES for #<Metabolite:0x00007feca4ef9a78>

INCHI for #<Metabolite:0x00007feca4ef9a78>

Structure for #<Metabolite:0x00007feca4ef9a78>

3D Structure for #<Metabolite:0x00007feca4ef9a78>