MiMeDB: Showing metabocard for 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoate (MMDBc0031793)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:49:31 UTC

Update Date

2022-08-31 18:24:47 UTC

Metabolite ID

MMDBc0031793

Metabolite Identification

Common Name

2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoate

Description

2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoate is an intermediate in the degradation of quercetin by E. coli. Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. In E. coli it is metabolized by Quercetin 2,3-dioxygenase. This enzyme catalyzes the reaction Quercetin + O2 = 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoate + CO + H+. Quercetin is not a normal growth substrate for E. coli but it is found in high levels in the human gut. This enzyme may have evolved to break down quercitin to prevent its inhibition of key E. coli proteins, such as DNA gyrase.

Structure

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

HMDB0059651
     RDKit          3D
2-(3,4-Dihydroxybenzoyloxy)-4,6-dihydroxybenzoate
 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.1205   -0.9930    1.5059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5296   -0.2230    0.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3834    0.5509   -0.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227    0.5908    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444    1.4430    1.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6174    1.4698    1.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1350    2.3453    2.2741 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4809    0.6816    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9197   -0.1839   -0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8023   -0.9661   -1.0642 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5601   -0.2364   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9158   -1.0896   -1.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738   -1.0881   -1.7090 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6282   -1.9475   -2.3553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -0.1358    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441    0.7247   -0.7453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6746    0.8313   -1.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6489    0.0911   -0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9729    0.2004   -0.8655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2474   -0.7831    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2545   -1.5221    1.1086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185   -0.8887    0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5946    2.0914    1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5507    2.9486    2.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5526    0.6926    0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6790   -1.6239   -1.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5866   -2.9489   -2.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6256    1.3467   -1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9401    1.5227   -1.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2191    0.8460   -1.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9773   -2.1632    1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6378   -1.5835    1.6646 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 11  4  1  0
 22 15  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
 21 31  1  0
 22 32  1  0
M  END


  Mrv0541 10101211222D          

 22 23  0  0  0  0            999 V2000
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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
    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   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
    2.1434   -0.4125    0.0000 O   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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  1  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  8  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  6  1  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 13  2  0  0  0  0
 20 13  1  0  0  0  0
 21 14  2  0  0  0  0
 22 11  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031793

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)C1=C(O)C=C(O)C=C1OC(=O)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O8/c15-7-4-10(18)12(13(19)20)11(5-7)22-14(21)6-1-2-8(16)9(17)3-6/h1-5,15-18H,(H,19,20)

> <INCHI_KEY>
GRXIELRCPYIEQI-UHFFFAOYSA-N

> <FORMULA>
C14H10O8

> <MOLECULAR_WEIGHT>
306.2244

> <EXACT_MASS>
306.037567296

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
27.888505590538912

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
2.7280028499999998

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.46858192613729

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.446274683898726

> <JCHEM_PKA_STRONGEST_BASIC>
-5.821978101135998

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
73.0407

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0059651
     RDKit          3D
2-(3,4-Dihydroxybenzoyloxy)-4,6-dihydroxybenzoate
 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.1205   -0.9930    1.5059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5296   -0.2230    0.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3834    0.5509   -0.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227    0.5908    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444    1.4430    1.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6174    1.4698    1.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1350    2.3453    2.2741 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4809    0.6816    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9197   -0.1839   -0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8023   -0.9661   -1.0642 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5601   -0.2364   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9158   -1.0896   -1.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738   -1.0881   -1.7090 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6282   -1.9475   -2.3553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -0.1358    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441    0.7247   -0.7453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6746    0.8313   -1.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6489    0.0911   -0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9729    0.2004   -0.8655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2474   -0.7831    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2545   -1.5221    1.1086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185   -0.8887    0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5946    2.0914    1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5507    2.9486    2.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5526    0.6926    0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6790   -1.6239   -1.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5866   -2.9489   -2.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6256    1.3467   -1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9401    1.5227   -1.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2191    0.8460   -1.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9773   -2.1632    1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6378   -1.5835    1.6646 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 11  4  1  0
 22 15  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
 21 31  1  0
 22 32  1  0
M  END

HEADER    PROTEIN                                 10-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    8                                                       
CONECT    3    6    9                                                       
CONECT    4    7   10                                                       
CONECT    5    7   11                                                       
CONECT    6    1    3   14                                                  
CONECT    7    4    5   15                                                  
CONECT    8    2    9   16                                                  
CONECT    9    3    8   17                                                  
CONECT   10    4   12   18                                                  
CONECT   11    5   12   22                                                  
CONECT   12   10   11   13                                                  
CONECT   13   12   19   20                                                  
CONECT   14    6   21   22                                                  
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   13                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   11   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0059651
HETATM    1  O1  UNL     1      -0.121  -0.993   1.506  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.530  -0.223   0.607  1.00  0.00           C  
HETATM    3  O2  UNL     1       0.383   0.551  -0.049  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.723   0.591   0.160  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.244   1.443   1.106  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.617   1.470   1.305  1.00  0.00           C  
HETATM    7  O3  UNL     1       4.135   2.345   2.274  1.00  0.00           O  
HETATM    8  C5  UNL     1       4.481   0.682   0.598  1.00  0.00           C  
HETATM    9  C6  UNL     1       3.920  -0.184  -0.366  1.00  0.00           C  
HETATM   10  O4  UNL     1       4.802  -0.966  -1.064  1.00  0.00           O  
HETATM   11  C7  UNL     1       2.560  -0.236  -0.590  1.00  0.00           C  
HETATM   12  C8  UNL     1       1.916  -1.090  -1.555  1.00  0.00           C  
HETATM   13  O5  UNL     1       0.674  -1.088  -1.709  1.00  0.00           O  
HETATM   14  O6  UNL     1       2.628  -1.947  -2.355  1.00  0.00           O  
HETATM   15  C9  UNL     1      -1.936  -0.136   0.250  1.00  0.00           C  
HETATM   16  C10 UNL     1      -2.344   0.725  -0.745  1.00  0.00           C  
HETATM   17  C11 UNL     1      -3.675   0.831  -1.108  1.00  0.00           C  
HETATM   18  C12 UNL     1      -4.649   0.091  -0.501  1.00  0.00           C  
HETATM   19  O7  UNL     1      -5.973   0.200  -0.865  1.00  0.00           O  
HETATM   20  C13 UNL     1      -4.247  -0.783   0.508  1.00  0.00           C  
HETATM   21  O8  UNL     1      -5.254  -1.522   1.109  1.00  0.00           O  
HETATM   22  C14 UNL     1      -2.919  -0.889   0.870  1.00  0.00           C  
HETATM   23  H1  UNL     1       1.595   2.091   1.694  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.551   2.949   2.825  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.553   0.693   0.744  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.679  -1.624  -1.759  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.587  -2.949  -2.341  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.626   1.347  -1.275  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.940   1.523  -1.897  1.00  0.00           H  
HETATM   30  H8  UNL     1      -6.219   0.846  -1.601  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.977  -2.163   1.845  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.638  -1.583   1.665  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   15
CONECT    3    4
CONECT    4    5    5   11
CONECT    5    6   23
CONECT    6    7    8    8
CONECT    7   24
CONECT    8    9   25
CONECT    9   10   11   11
CONECT   10   26
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   27
CONECT   15   16   16   22
CONECT   16   17   28
CONECT   17   18   18   29
CONECT   18   19   20
CONECT   19   30
CONECT   20   21   22   22
CONECT   21   31
CONECT   22   32
END

HMDB0059651
     RDKit          3D
2-(3,4-Dihydroxybenzoyloxy)-4,6-dihydroxybenzoate
 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.1205   -0.9930    1.5059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5296   -0.2230    0.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3834    0.5509   -0.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227    0.5908    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444    1.4430    1.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6174    1.4698    1.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1350    2.3453    2.2741 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4809    0.6816    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9197   -0.1839   -0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8023   -0.9661   -1.0642 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5601   -0.2364   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9158   -1.0896   -1.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738   -1.0881   -1.7090 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6282   -1.9475   -2.3553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -0.1358    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441    0.7247   -0.7453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6746    0.8313   -1.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6489    0.0911   -0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9729    0.2004   -0.8655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2474   -0.7831    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2545   -1.5221    1.1086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185   -0.8887    0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5946    2.0914    1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5507    2.9486    2.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5526    0.6926    0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6790   -1.6239   -1.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5866   -2.9489   -2.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6256    1.3467   -1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9401    1.5227   -1.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2191    0.8460   -1.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9773   -2.1632    1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6378   -1.5835    1.6646 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 11  4  1  0
 22 15  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
 21 31  1  0
 22 32  1  0
M  END

Synonyms

Value	Source
2,4DIOH-6(2,4Diohbenacid)benzacid	ChEBI
2-Protocatechuoyl phloroglucinolcarboxylate	ChEBI
2PCPGCA	ChEBI
2-Protocatechuoyl phloroglucinolcarboxylic acid	Generator
2-(3,4-Dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid	Generator
2-Protocatechoylphloroglucinolcarboxylate	HMDB
2-Protocatechoylphloroglucinolcarboxylic acid	HMDB
2-(3,4-Dihydroxybenzoyloxy)-4,6-dihydroxybenzoate	ChEBI

Molecular Formula

C₁₄H₁₀O₈

Average Mass

306.2244

Monoisotopic Mass

306.037567296

IUPAC Name

2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid

Traditional Name

2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=C(O)C=C(O)C=C1OC(=O)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C14H10O8/c15-7-4-10(18)12(13(19)20)11(5-7)22-14(21)6-1-2-8(16)9(17)3-6/h1-5,15-18H,(H,19,20)

InChI Key

GRXIELRCPYIEQI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depside backbone
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Hydroxybenzoic acid
Phenol ester
Salicylic acid or derivatives
Salicylic acid
Benzoate ester
Benzoic acid
Benzoic acid or derivatives
Phenoxy compound
Resorcinol
Catechol
Benzoyl
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Vinylogous acid
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzoate ester (CHEBI:16068 )
dihydroxybenzoic acid (CHEBI:16068 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	2.47	ALOGPS
logP	2.73	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	2.45	ChemAxon
pKa (Strongest Basic)	-5.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.04 m³·mol⁻¹	ChemAxon
Polarizability	27.89 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0900000000-f063a50e2100260c680c	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-001i-0090011000-57d471b57e310ee50676	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0596000000-47902ef3296c1477004b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0961000000-40a68d3f3894906dba7a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-5910000000-8ede257c8c7d14f1a891	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-08fr-0194000000-f4af9d9f87266faff042	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0290000000-38a97201178b58d10cd5	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06a0-3920000000-6ab6758b580e79a6a45d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0692000000-5556817bba47ece0212f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0950000000-c9c6bed2b1d180ffeb22	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-3930000000-ff1140404484c2ffa85f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fb9-0900000000-95ab0e687e19e8f7f0c4	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-07gi-0970000000-2eaec82c823970bda725	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fbc-3930000000-658b94bc5d3ab0cd21a8	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0196927	Pirin	Unknown	O00625

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	6	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Chicken	Unknown
Eukaryota/Fungi	Ascomycota	1
Bacteria	Firmicutes	1	Human feces
Archaea/Archaea	Euryarchaeota	1
Bacteria	nah	1
Bacteria	Actinobacteria	3	Human ; Cattle

Exposure Sources

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0059651

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C04524

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440370

PDB ID

Not Available

ChEBI ID

16068

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoate (MMDBc0031793)

MOL for #<Metabolite:0x00007fdb4cc4cd98>

3D MOL for #<Metabolite:0x00007fdb4cc4cd98>

3D SDF for #<Metabolite:0x00007fdb4cc4cd98>

3D-SDF for #<Metabolite:0x00007fdb4cc4cd98>

PDB for #<Metabolite:0x00007fdb4cc4cd98>

3D PDB for #<Metabolite:0x00007fdb4cc4cd98>

SMILES for #<Metabolite:0x00007fdb4cc4cd98>

INCHI for #<Metabolite:0x00007fdb4cc4cd98>

Structure for #<Metabolite:0x00007fdb4cc4cd98>

3D Structure for #<Metabolite:0x00007fdb4cc4cd98>