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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-04-09 21:20:25 UTC

Update Date

2021-09-14 15:47:10 UTC

HMDB ID

HMDB0060024

Secondary Accession Numbers

HMDB60024

Metabolite Identification

Common Name

Vanillic acid 4-O-glucuronide

Description

Vanillic acid 4-O-glucuronide is a metabolite of vanillic acid. A glucuronide is any substance produced by linking glucuronic acid to another substance via a glycosidic bond. Glucuronidation, the conversion of chemical compounds to glucuronides, is a method that animals use 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. Enzymes that cleave the glycosidic bond of a glucuronide are called glucuronidases (Wikipedia).

Structure

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

HMDB0060024
     RDKit          3D
Vanillic acid 4-O-glucuronide
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.5149   -3.0020   -0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3714   -2.2215   -0.5601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5375   -0.9501   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7847   -0.4520    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9732    0.8006    0.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3232    1.2878    1.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3144    0.5768    0.8714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4934    2.5533    1.6491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8534    1.5582    1.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5784    1.0597    0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854   -0.1921    0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1448   -0.7292   -0.0770 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0863   -0.1369    0.0923 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7853   -0.0454   -1.1368 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8920    0.7481   -1.0036 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5050    0.9592   -2.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9996    0.4424   -3.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6545    1.7313   -2.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9179    0.1489   -0.0413 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9397    1.0470    0.1780 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1800   -0.0213    1.2935 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0328   -0.5296    2.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0200   -0.9451    0.9952 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3819   -1.3849    2.1395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1903   -4.0541   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1868   -3.0664    0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0559   -2.6326   -1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6501   -1.0797    0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3183    3.3883    1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9815    2.5502    1.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7305    1.6905    0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0407    0.8737    0.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5910    1.7172   -0.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8492    2.5268   -1.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2432   -0.8450   -0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6005    0.5927    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958    0.9942    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0126   -1.5068    2.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051   -1.8176    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4552   -1.6346    2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 11  3  1  0
 23 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  1
 15 33  1  1
 18 34  1  0
 19 35  1  6
 20 36  1  0
 21 37  1  1
 22 38  1  0
 23 39  1  6
 24 40  1  0
M  END


  Mrv1652304062013152D          

 24 25  0  0  0  0            999 V2000
    1.0718    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007    1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3569    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007    2.2694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716    2.2694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2153    1.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860   -1.4436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860    1.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2153   -0.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716    0.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716   -0.2058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7860   -0.6183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5007   -0.2058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5007    0.6191    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7860    1.0318    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3569   -0.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  7  8  2  0  0  0  0
  2 10  1  0  0  0  0
  6  1  2  0  0  0  0
  6  5  1  0  0  0  0
 10 11  1  0  0  0  0
 16 12  1  0  0  0  0
 16 13  2  0  0  0  0
 22 14  1  6  0  0  0
 20 15  1  6  0  0  0
 23 16  1  1  0  0  0
 21 17  1  1  0  0  0
 19 24  1  1  0  0  0
 23 18  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
  3 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060024

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=CC(=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O10/c1-22-7-4-5(12(18)19)2-3-6(7)23-14-10(17)8(15)9(16)11(24-14)13(20)21/h2-4,8-11,14-17H,1H3,(H,18,19)(H,20,21)/t8-,9-,10+,11-,14+/m0/s1

> <INCHI_KEY>
GRERMCGRRAMWSD-GRZGAGJTSA-N

> <FORMULA>
C14H16O10

> <MOLECULAR_WEIGHT>
344.272

> <EXACT_MASS>
344.074346715

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.151680882296326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-6-(4-carboxy-2-methoxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
-0.74

> <JCHEM_LOGP>
-0.7782014186666664

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.12837646834902

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9353818724177505

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686827976064012

> <JCHEM_POLAR_SURFACE_AREA>
162.98

> <JCHEM_REFRACTIVITY>
73.77010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-6-(4-carboxy-2-methoxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060024
     RDKit          3D
Vanillic acid 4-O-glucuronide
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.5149   -3.0020   -0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3714   -2.2215   -0.5601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5375   -0.9501   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7847   -0.4520    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9732    0.8006    0.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3232    1.2878    1.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3144    0.5768    0.8714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4934    2.5533    1.6491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8534    1.5582    1.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5784    1.0597    0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854   -0.1921    0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1448   -0.7292   -0.0770 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0863   -0.1369    0.0923 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7853   -0.0454   -1.1368 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8920    0.7481   -1.0036 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5050    0.9592   -2.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9996    0.4424   -3.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6545    1.7313   -2.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9179    0.1489   -0.0413 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9397    1.0470    0.1780 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1800   -0.0213    1.2935 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0328   -0.5296    2.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0200   -0.9451    0.9952 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3819   -1.3849    2.1395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1903   -4.0541   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1868   -3.0664    0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0559   -2.6326   -1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6501   -1.0797    0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3183    3.3883    1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9815    2.5502    1.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7305    1.6905    0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0407    0.8737    0.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5910    1.7172   -0.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8492    2.5268   -1.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2432   -0.8450   -0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6005    0.5927    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958    0.9942    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0126   -1.5068    2.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051   -1.8176    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4552   -1.6346    2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 11  3  1  0
 23 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  1
 15 33  1  1
 18 34  1  0
 19 35  1  6
 20 36  1  0
 21 37  1  1
 22 38  1  0
 23 39  1  6
 24 40  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0       2.001   1.925   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667   1.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.001  -1.154   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.334  -0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.334   1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.668   1.925   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.668   3.465   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       6.001   1.155   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.666   1.925   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.666   3.465   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.668   4.236   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.000   4.236   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -6.002   1.926   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -3.334  -2.695   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.334   3.466   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.002  -1.154   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.000   1.156   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.000  -0.384   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.334  -1.154   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.668  -0.384   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.668   1.156   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.334   1.926   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.666  -1.154   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    7    1    5                                                  
CONECT    7    6    9    8                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    2   11                                                       
CONECT   11   10                                                            
CONECT   12   16                                                            
CONECT   13   16                                                            
CONECT   14   22                                                            
CONECT   15   20                                                            
CONECT   16   12   13   23                                                  
CONECT   17   21                                                            
CONECT   18   23   19                                                       
CONECT   19   24   18   20                                                  
CONECT   20   15   19   21                                                  
CONECT   21   17   20   22                                                  
CONECT   22   14   21   23                                                  
CONECT   23   16   18   22                                                  
CONECT   24   19    3                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0060024
HETATM    1  C1  UNL     1      -3.515  -3.002  -0.814  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.371  -2.221  -0.560  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.538  -0.950  -0.015  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.785  -0.452   0.275  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.973   0.801   0.814  1.00  0.00           C  
HETATM    6  C5  UNL     1      -5.323   1.288   1.106  1.00  0.00           C  
HETATM    7  O2  UNL     1      -6.314   0.577   0.871  1.00  0.00           O  
HETATM    8  O3  UNL     1      -5.493   2.553   1.649  1.00  0.00           O  
HETATM    9  C6  UNL     1      -2.853   1.558   1.060  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.578   1.060   0.768  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.385  -0.192   0.229  1.00  0.00           C  
HETATM   12  O4  UNL     1      -0.145  -0.729  -0.077  1.00  0.00           O  
HETATM   13  C9  UNL     1       1.086  -0.137   0.092  1.00  0.00           C  
HETATM   14  O5  UNL     1       1.785  -0.045  -1.137  1.00  0.00           O  
HETATM   15  C10 UNL     1       2.892   0.748  -1.004  1.00  0.00           C  
HETATM   16  C11 UNL     1       3.505   0.959  -2.336  1.00  0.00           C  
HETATM   17  O6  UNL     1       3.000   0.442  -3.348  1.00  0.00           O  
HETATM   18  O7  UNL     1       4.654   1.731  -2.519  1.00  0.00           O  
HETATM   19  C12 UNL     1       3.918   0.149  -0.041  1.00  0.00           C  
HETATM   20  O8  UNL     1       4.940   1.047   0.178  1.00  0.00           O  
HETATM   21  C13 UNL     1       3.180  -0.021   1.293  1.00  0.00           C  
HETATM   22  O9  UNL     1       4.033  -0.530   2.252  1.00  0.00           O  
HETATM   23  C14 UNL     1       2.020  -0.945   0.995  1.00  0.00           C  
HETATM   24  O10 UNL     1       1.382  -1.385   2.139  1.00  0.00           O  
HETATM   25  H1  UNL     1      -3.190  -4.054  -1.025  1.00  0.00           H  
HETATM   26  H2  UNL     1      -4.187  -3.066   0.068  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.056  -2.633  -1.703  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.650  -1.080   0.067  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.318   3.388   1.092  1.00  0.00           H  
HETATM   30  H6  UNL     1      -2.981   2.550   1.485  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.731   1.691   0.978  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.041   0.874   0.520  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.591   1.717  -0.551  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.849   2.527  -1.907  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.243  -0.845  -0.361  1.00  0.00           H  
HETATM   36  H12 UNL     1       5.601   0.593   0.778  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.796   0.994   1.545  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.013  -1.507   2.211  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.405  -1.818   0.431  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.455  -1.635   2.013  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   28
CONECT    5    6    9    9
CONECT    6    7    7    8
CONECT    8   29
CONECT    9   10   30
CONECT   10   11   11   31
CONECT   11   12
CONECT   12   13
CONECT   13   14   23   32
CONECT   14   15
CONECT   15   16   19   33
CONECT   16   17   17   18
CONECT   18   34
CONECT   19   20   21   35
CONECT   20   36
CONECT   21   22   23   37
CONECT   22   38
CONECT   23   24   39
CONECT   24   40
END

HMDB0060024
     RDKit          3D
Vanillic acid 4-O-glucuronide
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.5149   -3.0020   -0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3714   -2.2215   -0.5601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5375   -0.9501   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7847   -0.4520    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9732    0.8006    0.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3232    1.2878    1.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3144    0.5768    0.8714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4934    2.5533    1.6491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8534    1.5582    1.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5784    1.0597    0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854   -0.1921    0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1448   -0.7292   -0.0770 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0863   -0.1369    0.0923 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7853   -0.0454   -1.1368 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8920    0.7481   -1.0036 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5050    0.9592   -2.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9996    0.4424   -3.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6545    1.7313   -2.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9179    0.1489   -0.0413 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9397    1.0470    0.1780 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1800   -0.0213    1.2935 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0328   -0.5296    2.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0200   -0.9451    0.9952 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3819   -1.3849    2.1395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1903   -4.0541   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1868   -3.0664    0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0559   -2.6326   -1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6501   -1.0797    0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3183    3.3883    1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9815    2.5502    1.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7305    1.6905    0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0407    0.8737    0.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5910    1.7172   -0.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8492    2.5268   -1.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2432   -0.8450   -0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6005    0.5927    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958    0.9942    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0126   -1.5068    2.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051   -1.8176    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4552   -1.6346    2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 11  3  1  0
 23 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  1
 15 33  1  1
 18 34  1  0
 19 35  1  6
 20 36  1  0
 21 37  1  1
 22 38  1  0
 23 39  1  6
 24 40  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Vanillate 4-O-glucuronide	Generator
3-Methoxy-4-glucuronosidobenzoic acid	HMDB
4-Carboxy-2-methoxyphenyl beta-D-glucopyranosiduronic acid	HMDB
4-Carboxy-2-methoxyphenyl beta-D-glucosiduronic acid	HMDB
4-Carboxy-2-methoxyphenyl β-D-glucopyranosiduronic acid	HMDB
4-Carboxy-2-methoxyphenyl β-D-glucosiduronic acid	HMDB
Vanillic acid 4'-O-beta-D-glucuronide	HMDB
Vanillic acid 4'-O-glucuronide	HMDB
Vanillic acid 4'-O-β-D-glucuronide	HMDB
Vanillic acid 4'-glucuronide	HMDB
Vanillic acid 4-O-beta-D-glucuronide	HMDB
Vanillic acid 4-O-β-D-glucuronide	HMDB
Vanillic acid 4-glucuronide	HMDB
Vanillic acid 4’-O-glucuronide	HMDB
Vanillic acid 4’-O-β-D-glucuronide	HMDB
Vanillic acid 4’-glucuronide	HMDB
Vanillic acid-4-O-glucuronide	HMDB
Vanillic acid 4-O-glucuronide	HMDB

Chemical Formula

C₁₄H₁₆O₁₀

Average Molecular Weight

344.272

Monoisotopic Molecular Weight

344.074346715

IUPAC Name

(2S,3S,4S,5R,6S)-6-(4-carboxy-2-methoxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-6-(4-carboxy-2-methoxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

18191-12-3

SMILES

COC1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=CC(=C1)C(O)=O

InChI Identifier

InChI=1S/C14H16O10/c1-22-7-4-5(12(18)19)2-3-6(7)23-14-10(17)8(15)9(16)11(24-14)13(20)21/h2-4,8-11,14-17H,1H3,(H,18,19)(H,20,21)/t8-,9-,10+,11-,14+/m0/s1

InChI Key

GRERMCGRRAMWSD-GRZGAGJTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Glycosyl compound
M-methoxybenzoic acid or derivatives
O-glycosyl compound
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Anisole
Methoxybenzene
Benzoyl
Phenol ether
Alkyl aryl ether
Beta-hydroxy acid
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Pyran
Dicarboxylic acid or derivatives
Oxane
Hydroxy acid
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Organ

Liver (HMDB: HMDB0060024)
Kidney (HMDB: HMDB0060024)

Excreta

Biofluid or Excreta

Urine (PMID: 22827565)

Source

Endogenous

Endogenous (HMDB: HMDB0060024)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.44 g/L	ALOGPS
logP	-0.74	ALOGPS
logP	-0.78	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.94	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.77 m³·mol⁻¹	ChemAxon
Polarizability	31.15 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	174.981	30932474
DeepCCS	[M-H]-	172.586	30932474
DeepCCS	[M-2H]-	205.634	30932474
DeepCCS	[M+Na]+	180.894	30932474
AllCCS	[M+H]+	178.0	32859911
AllCCS	[M+H-H2O]+	175.0	32859911
AllCCS	[M+NH4]+	180.7	32859911
AllCCS	[M+Na]+	181.5	32859911
AllCCS	[M-H]-	173.8	32859911
AllCCS	[M+Na-2H]-	173.7	32859911
AllCCS	[M+HCOO]-	173.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vanillic acid 4-O-glucuronide	COC1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=CC(=C1)C(O)=O	4461.8	Standard polar	33892256
Vanillic acid 4-O-glucuronide	COC1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=CC(=C1)C(O)=O	2763.2	Standard non polar	33892256
Vanillic acid 4-O-glucuronide	COC1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=CC(=C1)C(O)=O	2935.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vanillic acid 4-O-glucuronide,1TMS,isomer #1	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2883.0	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,1TMS,isomer #2	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2882.0	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,1TMS,isomer #3	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2876.8	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,1TMS,isomer #4	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	2864.1	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,1TMS,isomer #5	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O	2860.2	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2805.5	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TMS,isomer #10	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	2803.4	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TMS,isomer #2	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2853.5	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TMS,isomer #3	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2851.6	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TMS,isomer #4	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2860.0	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TMS,isomer #5	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2810.7	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TMS,isomer #6	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2839.4	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TMS,isomer #7	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2850.4	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TMS,isomer #8	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2816.5	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TMS,isomer #9	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2845.8	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2800.8	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TMS,isomer #10	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2798.7	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TMS,isomer #2	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2799.5	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TMS,isomer #3	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2819.9	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TMS,isomer #4	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2840.9	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TMS,isomer #5	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2859.7	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TMS,isomer #6	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2830.2	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TMS,isomer #7	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2797.4	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TMS,isomer #8	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2802.0	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TMS,isomer #9	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2830.0	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,4TMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2838.3	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,4TMS,isomer #2	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2868.3	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,4TMS,isomer #3	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2822.2	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,4TMS,isomer #4	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2891.5	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,4TMS,isomer #5	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2829.9	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,5TMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2890.2	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,1TBDMS,isomer #1	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	3140.1	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,1TBDMS,isomer #2	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3150.8	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,1TBDMS,isomer #3	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3150.9	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,1TBDMS,isomer #4	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	3166.1	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,1TBDMS,isomer #5	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O	3149.0	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TBDMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	3337.0	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TBDMS,isomer #10	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	3341.4	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TBDMS,isomer #2	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	3367.7	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TBDMS,isomer #3	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3325.5	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TBDMS,isomer #4	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3340.6	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TBDMS,isomer #5	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3345.9	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TBDMS,isomer #6	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3363.9	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TBDMS,isomer #7	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3332.0	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TBDMS,isomer #8	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3353.0	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,2TBDMS,isomer #9	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3369.0	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TBDMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	3544.2	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TBDMS,isomer #10	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3547.4	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TBDMS,isomer #2	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3507.2	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TBDMS,isomer #3	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3533.8	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TBDMS,isomer #4	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3522.5	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TBDMS,isomer #5	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3562.0	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TBDMS,isomer #6	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3504.7	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TBDMS,isomer #7	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3538.9	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TBDMS,isomer #8	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3515.3	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,3TBDMS,isomer #9	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3522.7	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,4TBDMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3670.7	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,4TBDMS,isomer #2	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3712.1	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,4TBDMS,isomer #3	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3661.1	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,4TBDMS,isomer #4	COC1=CC(C(=O)O)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3717.4	Semi standard non polar	33892256
Vanillic acid 4-O-glucuronide,4TBDMS,isomer #5	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3675.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillic acid 4-O-glucuronide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillic acid 4-O-glucuronide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-O-glucuronide 10V, Positive-QTOF	splash10-056s-0249000000-188098ebf9d809d25c8e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-O-glucuronide 20V, Positive-QTOF	splash10-0lgj-0954000000-91c4dd634a2dc03601d8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-O-glucuronide 40V, Positive-QTOF	splash10-0lfr-2910000000-eb35c652a9ceb9e16395	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-O-glucuronide 10V, Negative-QTOF	splash10-0007-0279000000-f083cf85227d36a29d89	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-O-glucuronide 20V, Negative-QTOF	splash10-0fsj-2971000000-2d57126c08fda2d621b6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-O-glucuronide 40V, Negative-QTOF	splash10-0l6s-4940000000-5a815fe801776e054497	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22827565	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20853910	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Diabetes mellitus	23637065	details

Associated Disorders and Diseases

Disease References

Diabetes mellitus type 2
Llorach R, Urpi-Sarda M, Tulipani S, Garcia-Aloy M, Monagas M, Andres-Lacueva C: Metabolomic fingerprint in patients at high risk of cardiovascular disease by cocoa intervention. Mol Nutr Food Res. 2013 Jun;57(6):962-73. doi: 10.1002/mnfr.201200736. Epub 2013 May 2. [PubMed:23637065 ]

Associated OMIM IDs

125853 (Diabetes mellitus type 2)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB111728

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101579718

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

van der Hooft JJ, de Vos RC, Mihaleva V, Bino RJ, Ridder L, de Roo N, Jacobs DM, van Duynhoven JP, Vervoort J: Structural elucidation and quantification of phenolic conjugates present in human urine after tea intake. Anal Chem. 2012 Aug 21;84(16):7263-71. doi: 10.1021/ac3017339. Epub 2012 Aug 2. [PubMed:22827565 ]

Showing metabocard for Vanillic acid 4-O-glucuronide (HMDB0060024)

MOL for HMDB0060024 (Vanillic acid 4-O-glucuronide)

3D MOL for HMDB0060024 (Vanillic acid 4-O-glucuronide)

3D SDF for HMDB0060024 (Vanillic acid 4-O-glucuronide)

3D-SDF for HMDB0060024 (Vanillic acid 4-O-glucuronide)

PDB for HMDB0060024 (Vanillic acid 4-O-glucuronide)

3D PDB for HMDB0060024 (Vanillic acid 4-O-glucuronide)

SMILES for HMDB0060024 (Vanillic acid 4-O-glucuronide)

INCHI for HMDB0060024 (Vanillic acid 4-O-glucuronide)

Structure for HMDB0060024 (Vanillic acid 4-O-glucuronide)

3D Structure for HMDB0060024 (Vanillic acid 4-O-glucuronide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra