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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-23 17:31:41 UTC

Update Date

2022-09-22 18:34:37 UTC

HMDB ID

HMDB0302404

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Gallocatechol

Description

Ent-gallocatechin, also known as (2s,3r)-flavan-3,3',4',5,5',7-hexol or (2s,3r)-gallocatechin, is a member of the class of compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety. Ent-gallocatechin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Ent-gallocatechin can be found in common grape and tea, which makes ent-gallocatechin a potential biomarker for the consumption of these food products.

Structure

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

HMDB0302404
     RDKit          3D
4-Gallocatechol
 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.8600    2.7345    0.9713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0599    1.6236    0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6286    0.3861    0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8677   -0.7410    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4945   -1.9574    0.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4828   -0.6658    0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9213    0.5670    0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6863    1.6990    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5383    0.6481    0.3920 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2018   -0.3815   -0.1843 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6352   -0.0649   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    1.2226   -0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3246    1.6625   -0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6436    2.9628   -0.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2832    0.7914    0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5990    1.1652    0.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239   -0.5100    0.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9033   -1.3850    0.8722 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197   -0.9137    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2195   -1.7104    0.3084 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4301   -2.7399   -0.4130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873   -1.8911   -0.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3952    3.6342    1.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7258    0.3314    0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661   -2.8319   -0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2358    2.6681    0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0150   -0.3613   -1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834    1.9589   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5358    3.3842   -0.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241    2.0862   -0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6357   -2.3234    1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3214   -1.9197    0.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0751   -1.8699    1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394   -2.4290   -1.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7263   -2.0484   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1154   -2.7816    0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 10 20  1  0
 20 21  1  0
 20 22  1  0
  8  2  1  0
 19 11  1  0
 22  6  1  0
  1 23  1  0
  3 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  6
 12 28  1  0
 14 29  1  0
 16 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  1
 21 34  1  0
 22 35  1  0
 22 36  1  0
M  END


  Mrv0541 02231217122D          

 22 24  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 14 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302404

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@H]1C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m1/s1

> <INCHI_KEY>
XMOCLSLCDHWDHP-DOMZBBRYSA-N

> <FORMULA>
C15H14O7

> <MOLECULAR_WEIGHT>
306.2675

> <EXACT_MASS>
306.073952802

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
29.04717877432403

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
1.4915416936666661

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.513028720443094

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.72853264053892

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2949984309607405

> <JCHEM_POLAR_SURFACE_AREA>
130.61

> <JCHEM_REFRACTIVITY>
75.98060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epigallocatechin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302404
     RDKit          3D
4-Gallocatechol
 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.8600    2.7345    0.9713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0599    1.6236    0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6286    0.3861    0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8677   -0.7410    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4945   -1.9574    0.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4828   -0.6658    0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9213    0.5670    0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6863    1.6990    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5383    0.6481    0.3920 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2018   -0.3815   -0.1843 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6352   -0.0649   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    1.2226   -0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3246    1.6625   -0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6436    2.9628   -0.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2832    0.7914    0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5990    1.1652    0.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239   -0.5100    0.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9033   -1.3850    0.8722 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197   -0.9137    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2195   -1.7104    0.3084 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4301   -2.7399   -0.4130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873   -1.8911   -0.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3952    3.6342    1.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7258    0.3314    0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661   -2.8319   -0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2358    2.6681    0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0150   -0.3613   -1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834    1.9589   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5358    3.3842   -0.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241    2.0862   -0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6357   -2.3234    1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3214   -1.9197    0.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0751   -1.8699    1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394   -2.4290   -1.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7263   -2.0484   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1154   -2.7816    0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 10 20  1  0
 20 21  1  0
 20 22  1  0
  8  2  1  0
 19 11  1  0
 22  6  1  0
  1 23  1  0
  3 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  6
 12 28  1  0
 14 29  1  0
 16 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  1
 21 34  1  0
 22 35  1  0
 22 36  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12    2   14                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0302404
HETATM    1  O1  UNL     1      -4.860   2.734   0.971  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.060   1.624   0.731  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.629   0.386   0.531  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.868  -0.741   0.290  1.00  0.00           C  
HETATM    5  O2  UNL     1      -4.495  -1.957   0.095  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.483  -0.666   0.240  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.921   0.567   0.440  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.686   1.699   0.682  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.538   0.648   0.392  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.202  -0.382  -0.184  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.635  -0.065  -0.059  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.997   1.223  -0.405  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.325   1.663  -0.332  1.00  0.00           C  
HETATM   14  O4  UNL     1       3.644   2.963  -0.688  1.00  0.00           O  
HETATM   15  C11 UNL     1       4.283   0.791   0.093  1.00  0.00           C  
HETATM   16  O5  UNL     1       5.599   1.165   0.185  1.00  0.00           O  
HETATM   17  C12 UNL     1       3.924  -0.510   0.443  1.00  0.00           C  
HETATM   18  O6  UNL     1       4.903  -1.385   0.872  1.00  0.00           O  
HETATM   19  C13 UNL     1       2.620  -0.914   0.362  1.00  0.00           C  
HETATM   20  C14 UNL     1      -0.219  -1.710   0.308  1.00  0.00           C  
HETATM   21  O7  UNL     1       0.430  -2.740  -0.413  1.00  0.00           O  
HETATM   22  C15 UNL     1      -1.687  -1.891  -0.020  1.00  0.00           C  
HETATM   23  H1  UNL     1      -4.395   3.634   1.115  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.726   0.331   0.571  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.066  -2.832  -0.085  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.236   2.668   0.839  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.015  -0.361  -1.294  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.283   1.959  -0.748  1.00  0.00           H  
HETATM   29  H7  UNL     1       4.536   3.384  -0.678  1.00  0.00           H  
HETATM   30  H8  UNL     1       5.924   2.086  -0.052  1.00  0.00           H  
HETATM   31  H9  UNL     1       4.636  -2.323   1.123  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.321  -1.920   0.632  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.075  -1.870   1.387  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.539  -2.429  -1.336  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.726  -2.048  -1.138  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.115  -2.782   0.483  1.00  0.00           H  
CONECT    1    2   23
CONECT    2    3    3    8
CONECT    3    4   24
CONECT    4    5    6    6
CONECT    5   25
CONECT    6    7   22
CONECT    7    8    8    9
CONECT    8   26
CONECT    9   10
CONECT   10   11   20   27
CONECT   11   12   12   19
CONECT   12   13   28
CONECT   13   14   15   15
CONECT   14   29
CONECT   15   16   17
CONECT   16   30
CONECT   17   18   19   19
CONECT   18   31
CONECT   19   32
CONECT   20   21   22   33
CONECT   21   34
CONECT   22   35   36
END

HMDB0302404
     RDKit          3D
4-Gallocatechol
 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.8600    2.7345    0.9713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0599    1.6236    0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6286    0.3861    0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8677   -0.7410    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4945   -1.9574    0.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4828   -0.6658    0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9213    0.5670    0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6863    1.6990    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5383    0.6481    0.3920 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2018   -0.3815   -0.1843 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6352   -0.0649   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    1.2226   -0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3246    1.6625   -0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6436    2.9628   -0.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2832    0.7914    0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5990    1.1652    0.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239   -0.5100    0.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9033   -1.3850    0.8722 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197   -0.9137    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2195   -1.7104    0.3084 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4301   -2.7399   -0.4130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873   -1.8911   -0.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3952    3.6342    1.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7258    0.3314    0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661   -2.8319   -0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2358    2.6681    0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0150   -0.3613   -1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834    1.9589   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5358    3.3842   -0.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241    2.0862   -0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6357   -2.3234    1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3214   -1.9197    0.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0751   -1.8699    1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394   -2.4290   -1.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7263   -2.0484   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1154   -2.7816    0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 10 20  1  0
 20 21  1  0
 20 22  1  0
  8  2  1  0
 19 11  1  0
 22  6  1  0
  1 23  1  0
  3 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  6
 12 28  1  0
 14 29  1  0
 16 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  1
 21 34  1  0
 22 35  1  0
 22 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,3R)-(-)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol	ChEBI
(2S,3R)-Flavan-3,3',4',5,5',7-hexol	ChEBI
(2S,3R)-Flavan-3,5,7,3',4',5'-hexol	ChEBI
(2S,3R)-Gallocatechin	ChEBI
ent-Gallocatechin	ChEBI

Chemical Formula

C₁₅H₁₄O₇

Average Molecular Weight

306.2675

Monoisotopic Molecular Weight

306.073952802

IUPAC Name

(2S,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

epigallocatechin

CAS Registry Number

Not Available

SMILES

O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@H]1C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m1/s1

InChI Key

XMOCLSLCDHWDHP-DOMZBBRYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Epigallocatechins

Alternative Parents

Substituents

Epigallocatechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
1-benzopyran
Chromane
Benzopyran
Pyrogallol derivative
Benzenetriol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

gallocatechin (CHEBI:71225 )

Ontology

Not Available

Exogenous (FooDB: )

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)
Quince (FooDB: FOOD00069)
Medlar (FooDB: FOOD00114)

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sweet cherry (FooDB: FOOD00145)

Tropical fruit

Berry

Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Strawberry (FooDB: FOOD00083)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Muscadine grape (FooDB: FOOD00203)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)

Citrus

Grapefruit (FooDB: FOOD00256)
Sweet orange (FooDB: FOOD00057)

Vegetable

Shoot vegetable

Globe artichoke (FooDB: FOOD00071)

Carrot (FooDB: FOOD00245)
Chicory (FooDB: FOOD00049)
Radish (FooDB: FOOD00153)

Mushroom

Common mushroom (FooDB: FOOD00547)

Onion-family vegetable

Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)

Tuber

Potato (FooDB: FOOD00175)

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

Cereal and cereal product

Leavened bread

Wheat bread (FooDB: FOOD00808)

Cereal

Corn (FooDB: FOOD00205)
Rice (FooDB: FOOD00125)

Cereal product

Pasta (FooDB: FOOD00273)

Pulse

Bean

Common bean (FooDB: FOOD00134)
Broad bean (FooDB: FOOD00197)

Lentil

Lentils (FooDB: FOOD00098)

Pea

Chickpea (FooDB: FOOD00047)
Common pea (FooDB: FOOD00141)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Other beverage

Fruit-flavor drink (FooDB: FOOD00821)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Coffee and coffee product

Coffee

Gourd

Cocoa and cocoa product

Cocoa product

Hot chocolate (FooDB: FOOD00688)

Cocoa

Cocoa bean (FooDB: FOOD00182)

Confectionery

Candy

Other candy (FooDB: FOOD00679)

Tea

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
logP	0.71	ALOGPS
logP	1.49	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.73	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	130.61 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.98 m³·mol⁻¹	ChemAxon
Polarizability	29.05 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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]+	171.461	32859911
AllCCS	[M+H-H2O]+	167.908	32859911
AllCCS	[M+Na]+	175.703	32859911
AllCCS	[M+NH4]+	174.756	32859911
AllCCS	[M-H]-	169.448	32859911
AllCCS	[M+Na-2H]-	168.966	32859911
AllCCS	[M+HCOO]-	168.571	32859911
DeepCCS	[M+H]+	173.717	30932474
DeepCCS	[M-H]-	171.359	30932474
DeepCCS	[M-2H]-	204.943	30932474
DeepCCS	[M+Na]+	180.171	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.1246 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.13 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	958.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	209.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	79.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	135.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	60.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	406.3 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	293.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	753.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	613.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	164.0 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	983.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	172.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	212.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	576.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	491.8 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	376.2 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Gallocatechol ESI-TOF 40V, Negative-QTOF	splash10-002r-0900000000-c1cd10a5867d444bd1d3	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Gallocatechol ESI-TOF 30V, Negative-QTOF	splash10-00n0-0910000000-06ff48cb1edb79736ede	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Gallocatechol ESI-TOF , Negative-QTOF	splash10-0a4i-0009003000-3d7ef0f8ac2fcb86dd95	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Gallocatechol ESI-TOF 10V, Negative-QTOF	splash10-0a4i-0019000000-83d961b9674b7b1b2a65	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Gallocatechol ESI-TOF 20V, Negative-QTOF	splash10-0a4i-0019000000-83d961b9674b7b1b2a65	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Gallocatechol LC-ESI-QFT 21V, positive-QTOF	splash10-000i-0890000000-0f3aa786eac09b40ac18	2020-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Gallocatechol LC-ESI-IT 21V, positive-QTOF	splash10-000i-0910000000-8e29f0ab5ef8c0e492d6	2020-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Gallocatechol 10V, Positive-QTOF	splash10-0a4r-0729000000-fffbd456b9b51c7d0274	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Gallocatechol 20V, Positive-QTOF	splash10-000i-0911000000-203a6a86214265bc09e4	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Gallocatechol 40V, Positive-QTOF	splash10-00ds-2900000000-023b154fc2d731ecee10	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Gallocatechol 10V, Negative-QTOF	splash10-0a4i-0219000000-db1826421845ecab1485	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Gallocatechol 20V, Negative-QTOF	splash10-05n0-0922000000-86fb5a0b2fc660815604	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Gallocatechol 40V, Negative-QTOF	splash10-056r-2910000000-2375ce05cd5da757763c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Gallocatechol 10V, Positive-QTOF	splash10-0a4i-0029000000-3578b95ca9c1d3f41df2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Gallocatechol 20V, Positive-QTOF	splash10-05n0-0902000000-291e12c32e9cfe57384b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Gallocatechol 40V, Positive-QTOF	splash10-000i-1920000000-c1afce079042673ae394	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Gallocatechol 10V, Negative-QTOF	splash10-0a4i-0019000000-b20f152234d6d77dcaa2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Gallocatechol 20V, Negative-QTOF	splash10-000i-0894000000-05dea610b2f972a7651e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Gallocatechol 40V, Negative-QTOF	splash10-000i-1930000000-7c643c8857e1259ab4fc	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB004421

KNApSAcK ID

C00034981

Chemspider ID

8058656

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gallocatechol

METLIN ID

Not Available

PubChem Compound

9882981

PDB ID

Not Available

ChEBI ID

71225

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 4-Gallocatechol (HMDB0302404)

MOL for HMDB0302404 (4-Gallocatechol)

3D MOL for HMDB0302404 (4-Gallocatechol)

3D SDF for HMDB0302404 (4-Gallocatechol)

3D-SDF for HMDB0302404 (4-Gallocatechol)

PDB for HMDB0302404 (4-Gallocatechol)

3D PDB for HMDB0302404 (4-Gallocatechol)

SMILES for HMDB0302404 (4-Gallocatechol)

INCHI for HMDB0302404 (4-Gallocatechol)

Structure for HMDB0302404 (4-Gallocatechol)

3D Structure for HMDB0302404 (4-Gallocatechol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra