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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-22 16:31:57 UTC

Update Date

2021-09-22 16:31:58 UTC

HMDB ID

HMDB0301708

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Galloyl glucose

Description

Galloyl glucose, also known as 1-galloyl-beta-D-glucose or beta-glucogallin, is a member of the class of compounds known as tannins. Tannins are naturally occurring polyphenols which be categorized into four main classes: hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol). Galloyl glucose is soluble (in water) and a very weakly acidic compound (based on its pKa). Galloyl glucose can be found in a number of food items such as pomegranate, strawberry, redcurrant, and rubus (blackberry, raspberry), which makes galloyl glucose a potential biomarker for the consumption of these food products. Galloyl glucose is formed by a gallate 1-beta-glucosyltransferase (UDP-glucose: gallate glucosyltransferase), an enzyme performing the esterification of two substrates, UDP-glucose and gallate to yield two products, UDP and glucogallin. This enzyme can be found in oak leaf preparations .

Structure

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

HMDB0301708
     RDKit          3D
Galloyl glucose
 39 40  0  0  0  0  0  0  0  0999 V2000
    0.9338    1.9452   -0.8665 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2112    0.8542   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1613   -0.0097   -0.0649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1846    0.2937   -0.3944 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8952    0.2456    0.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2392    0.4320    0.6671 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8908   -0.1027    1.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148    0.5833    3.0512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8582   -0.1653   -0.5514 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8249    0.7942   -1.5679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9813   -1.3464   -0.9744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6978   -2.1629    0.1119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6554   -0.7077   -1.4040 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9239   -0.1045   -2.6441 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955    0.5540    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9594   -0.6342    0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881   -0.8438    0.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6902   -2.0278    1.5076 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356    0.1068    0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5576   -0.1362    0.8887 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8872    1.2975   -0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8566    2.2655   -0.3268 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5645    1.4886   -0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2388    1.3133   -0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4671    1.5213    0.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9939    0.0383    1.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6506   -1.1770    2.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8672    0.2321    3.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8784   -0.5509   -0.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5074    0.6629   -2.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4425   -1.8729   -1.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7959   -2.5478    0.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219   -1.5060   -1.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9215   -0.7410   -3.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1786   -1.3464    0.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0184   -2.7344    1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2837    0.5411    0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5688    3.1248   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607    2.4236   -0.7635 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  1  0
  6  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 13  4  1  0
 23 15  1  0
  4 24  1  6
  6 25  1  6
  7 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  1
 10 30  1  0
 11 31  1  6
 12 32  1  0
 13 33  1  6
 14 34  1  0
 16 35  1  0
 18 36  1  0
 20 37  1  0
 22 38  1  0
 23 39  1  0
M  END

 
  Mrv0541 02241221332D          
 
 23 24  0  0  1  0            999 V2000
   12.2930   -9.3322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5784   -8.9200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2930  -10.1526    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0114   -8.9237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8638   -9.3322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5784  -10.5685    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0076  -10.5685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7223   -8.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8638  -10.1526    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1605   -8.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5784  -11.4303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4331   -8.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7260   -7.7699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1605  -10.5685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5290   -9.4531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4331   -9.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1554   -8.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1554  -10.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8662   -8.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8851   -9.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1554  -10.9997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5809   -8.5117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5809  -10.1640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  6  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  1  0  0  0
  6 11  1  1  0  0  0
  8 12  1  0  0  0  0
  8 13  2  0  0  0  0
  9 14  1  6  0  0  0
 10 15  1  0  0  0  0
 12 16  2  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  2  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
  6  9  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301708

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O10/c14-3-7-9(18)10(19)11(20)13(22-7)23-12(21)4-1-5(15)8(17)6(16)2-4/h1-2,7,9-11,13-20H,3H2/t7-,9-,10+,11-,13+/m1/s1

> <INCHI_KEY>
GDVRUDXLQBVIKP-HQHREHCSSA-N

> <FORMULA>
C13H16O10

> <MOLECULAR_WEIGHT>
332.2601

> <EXACT_MASS>
332.074346732

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
29.82680630226126

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
-1.27

> <JCHEM_LOGP>
-1.3479353343333333

> <ALOGPS_LOGS>
-1.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.239000622653721

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.08270189454248

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810938238798306

> <JCHEM_POLAR_SURFACE_AREA>
177.14

> <JCHEM_REFRACTIVITY>
71.68810000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.21e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-glucogallin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301708
     RDKit          3D
Galloyl glucose
 39 40  0  0  0  0  0  0  0  0999 V2000
    0.9338    1.9452   -0.8665 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2112    0.8542   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1613   -0.0097   -0.0649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1846    0.2937   -0.3944 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8952    0.2456    0.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2392    0.4320    0.6671 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8908   -0.1027    1.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148    0.5833    3.0512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8582   -0.1653   -0.5514 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8249    0.7942   -1.5679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9813   -1.3464   -0.9744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6978   -2.1629    0.1119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6554   -0.7077   -1.4040 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9239   -0.1045   -2.6441 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955    0.5540    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9594   -0.6342    0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881   -0.8438    0.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6902   -2.0278    1.5076 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356    0.1068    0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5576   -0.1362    0.8887 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8872    1.2975   -0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8566    2.2655   -0.3268 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5645    1.4886   -0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2388    1.3133   -0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4671    1.5213    0.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9939    0.0383    1.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6506   -1.1770    2.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8672    0.2321    3.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8784   -0.5509   -0.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5074    0.6629   -2.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4425   -1.8729   -1.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7959   -2.5478    0.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219   -1.5060   -1.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9215   -0.7410   -3.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1786   -1.3464    0.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0184   -2.7344    1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2837    0.5411    0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5688    3.1248   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607    2.4236   -0.7635 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  1  0
  6  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 13  4  1  0
 23 15  1  0
  4 24  1  6
  6 25  1  6
  7 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  1
 10 30  1  0
 11 31  1  6
 12 32  1  0
 13 33  1  6
 14 34  1  0
 16 35  1  0
 18 36  1  0
 20 37  1  0
 22 38  1  0
 23 39  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      22.947 -17.420   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      21.613 -16.651   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      22.947 -18.952   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      24.288 -16.658   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      20.279 -17.420   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.613 -19.728   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      24.281 -19.728   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      25.615 -15.889   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.279 -18.952   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.966 -16.651   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      21.613 -21.337   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      26.942 -16.658   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      25.622 -14.504   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      18.966 -19.728   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      17.787 -17.646   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      26.942 -18.211   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.290 -15.889   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.290 -18.994   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.617 -16.658   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      29.652 -18.062   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      28.290 -20.533   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      30.951 -15.889   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      30.951 -18.973   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6    7                                                  
CONECT    4    1    8                                                       
CONECT    5    2    9   10                                                  
CONECT    6    3   11    9                                                  
CONECT    7    3                                                            
CONECT    8    4   12   13                                                  
CONECT    9    5   14    6                                                  
CONECT   10    5   15                                                       
CONECT   11    6                                                            
CONECT   12    8   16   17                                                  
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15   10                                                            
CONECT   16   12   18                                                       
CONECT   17   12   19                                                       
CONECT   18   16   20   21                                                  
CONECT   19   17   22   20                                                  
CONECT   20   18   23   19                                                  
CONECT   21   18                                                            
CONECT   22   19                                                            
CONECT   23   20                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0301708
HETATM    1  O1  UNL     1       0.934   1.945  -0.866  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.211   0.854  -0.320  1.00  0.00           C  
HETATM    3  O2  UNL     1       0.161  -0.010  -0.065  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.185   0.294  -0.394  1.00  0.00           C  
HETATM    5  O3  UNL     1      -1.895   0.246   0.797  1.00  0.00           O  
HETATM    6  C3  UNL     1      -3.239   0.432   0.667  1.00  0.00           C  
HETATM    7  C4  UNL     1      -3.891  -0.103   1.951  1.00  0.00           C  
HETATM    8  O4  UNL     1      -3.415   0.583   3.051  1.00  0.00           O  
HETATM    9  C5  UNL     1      -3.858  -0.165  -0.551  1.00  0.00           C  
HETATM   10  O5  UNL     1      -3.825   0.794  -1.568  1.00  0.00           O  
HETATM   11  C6  UNL     1      -2.981  -1.346  -0.974  1.00  0.00           C  
HETATM   12  O6  UNL     1      -2.698  -2.163   0.112  1.00  0.00           O  
HETATM   13  C7  UNL     1      -1.655  -0.708  -1.404  1.00  0.00           C  
HETATM   14  O7  UNL     1      -1.924  -0.105  -2.644  1.00  0.00           O  
HETATM   15  C8  UNL     1       2.596   0.554   0.013  1.00  0.00           C  
HETATM   16  C9  UNL     1       2.959  -0.634   0.617  1.00  0.00           C  
HETATM   17  C10 UNL     1       4.288  -0.844   0.900  1.00  0.00           C  
HETATM   18  O8  UNL     1       4.690  -2.028   1.508  1.00  0.00           O  
HETATM   19  C11 UNL     1       5.236   0.107   0.591  1.00  0.00           C  
HETATM   20  O9  UNL     1       6.558  -0.136   0.889  1.00  0.00           O  
HETATM   21  C12 UNL     1       4.887   1.297  -0.012  1.00  0.00           C  
HETATM   22  O10 UNL     1       5.857   2.266  -0.327  1.00  0.00           O  
HETATM   23  C13 UNL     1       3.565   1.489  -0.286  1.00  0.00           C  
HETATM   24  H1  UNL     1      -1.239   1.313  -0.876  1.00  0.00           H  
HETATM   25  H2  UNL     1      -3.467   1.521   0.663  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.994   0.038   1.832  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.651  -1.177   2.090  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.867   0.232   3.846  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.878  -0.551  -0.375  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.507   0.663  -2.251  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.443  -1.873  -1.818  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.796  -2.548   0.056  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.922  -1.506  -1.607  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.921  -0.741  -3.377  1.00  0.00           H  
HETATM   35  H12 UNL     1       2.179  -1.346   0.839  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.018  -2.734   1.742  1.00  0.00           H  
HETATM   37  H14 UNL     1       7.284   0.541   0.675  1.00  0.00           H  
HETATM   38  H15 UNL     1       5.569   3.125  -0.767  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.261   2.424  -0.764  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   15
CONECT    3    4
CONECT    4    5   13   24
CONECT    5    6
CONECT    6    7    9   25
CONECT    7    8   26   27
CONECT    8   28
CONECT    9   10   11   29
CONECT   10   30
CONECT   11   12   13   31
CONECT   12   32
CONECT   13   14   33
CONECT   14   34
CONECT   15   16   16   23
CONECT   16   17   35
CONECT   17   18   19   19
CONECT   18   36
CONECT   19   20   21
CONECT   20   37
CONECT   21   22   23   23
CONECT   22   38
CONECT   23   39
END

HMDB0301708
     RDKit          3D
Galloyl glucose
 39 40  0  0  0  0  0  0  0  0999 V2000
    0.9338    1.9452   -0.8665 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2112    0.8542   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1613   -0.0097   -0.0649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1846    0.2937   -0.3944 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8952    0.2456    0.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2392    0.4320    0.6671 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8908   -0.1027    1.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148    0.5833    3.0512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8582   -0.1653   -0.5514 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8249    0.7942   -1.5679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9813   -1.3464   -0.9744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6978   -2.1629    0.1119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6554   -0.7077   -1.4040 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9239   -0.1045   -2.6441 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955    0.5540    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9594   -0.6342    0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881   -0.8438    0.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6902   -2.0278    1.5076 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356    0.1068    0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5576   -0.1362    0.8887 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8872    1.2975   -0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8566    2.2655   -0.3268 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5645    1.4886   -0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2388    1.3133   -0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4671    1.5213    0.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9939    0.0383    1.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6506   -1.1770    2.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8672    0.2321    3.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8784   -0.5509   -0.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5074    0.6629   -2.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4425   -1.8729   -1.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7959   -2.5478    0.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219   -1.5060   -1.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9215   -0.7410   -3.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1786   -1.3464    0.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0184   -2.7344    1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2837    0.5411    0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5688    3.1248   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607    2.4236   -0.7635 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  1  0
  6  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 13  4  1  0
 23 15  1  0
  4 24  1  6
  6 25  1  6
  7 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  1
 10 30  1  0
 11 31  1  6
 12 32  1  0
 13 33  1  6
 14 34  1  0
 16 35  1  0
 18 36  1  0
 20 37  1  0
 22 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Galloyl-beta-D-glucose	ChEBI
1-Galloyl-beta-glucose	ChEBI
beta-Glucogallin	ChEBI
1-Galloyl-b-D-glucose	Generator
1-Galloyl-β-D-glucose	Generator
1-Galloyl-b-glucose	Generator
1-Galloyl-β-glucose	Generator
b-Glucogallin	Generator
Β-glucogallin	Generator
1-O-Galloyl-b-D-glucose	Generator
1-O-Galloyl-β-D-glucose	Generator
1-O-Galloylglucose	MeSH
Glucogallin	MeSH
1-O-Galloyl-beta-D-glucose	MeSH
Galloylglucose	MeSH

Chemical Formula

C₁₃H₁₆O₁₀

Average Molecular Weight

332.2601

Monoisotopic Molecular Weight

332.074346732

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 3,4,5-trihydroxybenzoate

Traditional Name

β-glucogallin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H16O10/c14-3-7-9(18)10(19)11(20)13(22-7)23-12(21)4-1-5(15)8(17)6(16)2-4/h1-2,7,9-11,13-20H,3H2/t7-,9-,10+,11-,13+/m1/s1

InChI Key

GDVRUDXLQBVIKP-HQHREHCSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: Hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Not Available

Direct Parent

Tannins

Alternative Parents

Substituents

Tannin
Galloyl ester
Hexose monosaccharide
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Oxane
Secondary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Primary alcohol
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

gallate ester (CHEBI:15834 )
galloyl beta-D-glucose (CHEBI:15834 )

Ontology

Not Available

Exogenous (HMDB: HMDB0301708)

Food

Fruit

Berry

Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Strawberry (FooDB: FOOD00083)
Highbush blueberry (FooDB: FOOD00191)
Jostaberry (FooDB: FOOD00257)

Tropical fruit

Pomegranate (FooDB: FOOD00151)

Nut

Common walnut (FooDB: FOOD00094)

Not Available

Dehydrogenase inhibitor (HMDB: HMDB0301708)

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
logP	-1.3	ALOGPS
logP	-1.3	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	8.08	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.69 m³·mol⁻¹	ChemAxon
Polarizability	29.83 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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
AllCCS	[M+H]+	175.103	32859911
AllCCS	[M+H-H2O]+	171.992	32859911
AllCCS	[M+Na]+	178.805	32859911
AllCCS	[M+NH4]+	177.98	32859911
AllCCS	[M-H]-	170.308	32859911
AllCCS	[M+Na-2H]-	170.155	32859911
AllCCS	[M+HCOO]-	170.112	32859911
DeepCCS	[M+H]+	170.803	30932474
DeepCCS	[M-H]-	168.407	30932474
DeepCCS	[M-2H]-	202.177	30932474
DeepCCS	[M+Na]+	176.9	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.8917 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.41 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	834.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	239.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	52.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	151.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	57.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	279.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	282.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	780.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	593.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	64.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	999.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	185.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	185.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	563.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	380.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	458.9 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Galloyl glucose GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-9623000000-beca8f27fef9fce8f078	2017-07-27	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 - Galloyl glucose 10V, Positive-QTOF	splash10-0fk9-0902000000-0c84b6c8e74dfd13d3a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galloyl glucose 20V, Positive-QTOF	splash10-0udi-0900000000-03973e83a0db08c1b5a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galloyl glucose 40V, Positive-QTOF	splash10-0ufr-2900000000-4cad2ae123289e57d139	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galloyl glucose 10V, Negative-QTOF	splash10-0gc0-1904000000-f28c95d9eb0300138627	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galloyl glucose 20V, Negative-QTOF	splash10-02t9-2901000000-9b510243388f6158b7cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galloyl glucose 40V, Negative-QTOF	splash10-016u-7900000000-21d7773cb744645d8c25	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galloyl glucose 10V, Positive-QTOF	splash10-001j-0609000000-77163b65b4960d87626c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galloyl glucose 20V, Positive-QTOF	splash10-0uea-1930000000-52a8aabde2c631d0f821	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galloyl glucose 40V, Positive-QTOF	splash10-0pb9-6920000000-3cab23f2d06168990463	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galloyl glucose 10V, Negative-QTOF	splash10-00o0-0905000000-3ea0bd89e280924a7830	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galloyl glucose 20V, Negative-QTOF	splash10-0lgi-2901000000-f508299e5e64087f0474	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galloyl glucose 40V, Negative-QTOF	splash10-00tb-5900000000-31a1130332ca97e02e9d	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Glucogallin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

15834

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

Not Available

Showing metabocard for Galloyl glucose (HMDB0301708)

MOL for HMDB0301708 (Galloyl glucose)

3D MOL for HMDB0301708 (Galloyl glucose)

3D SDF for HMDB0301708 (Galloyl glucose)

3D-SDF for HMDB0301708 (Galloyl glucose)

PDB for HMDB0301708 (Galloyl glucose)

3D PDB for HMDB0301708 (Galloyl glucose)

SMILES for HMDB0301708 (Galloyl glucose)

INCHI for HMDB0301708 (Galloyl glucose)

Structure for HMDB0301708 (Galloyl glucose)

3D Structure for HMDB0301708 (Galloyl glucose)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra