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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-24 04:56:04 UTC

Update Date

2022-09-22 18:35:14 UTC

HMDB ID

HMDB0303826

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Protocatechuic acid 4-glucoside

Description

Protocatechuic acid 4-glucoside is a member of the class of compounds known as phenolic glycosides. Phenolic glycosides are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Protocatechuic acid 4-glucoside is soluble (in water) and a weakly acidic compound (based on its pKa). Protocatechuic acid 4-glucoside can be found in a number of food items such as rosemary, jostaberry, rubus (blackberry, raspberry), and highbush blueberry, which makes protocatechuic acid 4-glucoside a potential biomarker for the consumption of these food products.

Structure

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

HMDB0303826
     RDKit          3D
Protocatechuic acid 4-glucoside
 38 39  0  0  0  0  0  0  0  0999 V2000
    6.5942   -1.2478    0.8206 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7774   -0.3595    1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2303    0.7066    1.9155 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789   -0.4161    0.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9176   -1.4729    0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939   -1.5255   -0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6829   -0.5264    0.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4262   -0.6731   -0.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7626    0.0181   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6388   -0.8420    0.4702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490   -0.4841    0.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2390    0.7764    1.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5942    1.0955    1.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5016   -0.3447   -0.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1712    0.8694   -1.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4060   -0.4305   -2.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657   -1.7351   -2.1761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2607    0.4102   -1.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5740    1.7885   -1.6130 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659    0.5086    0.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3210    1.5177    1.2280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5200    0.5801    1.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8223    1.4209    1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6302   -2.2469   -0.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2705   -2.3758   -0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6786    0.9525    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5360   -1.2914    0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6793    1.6435    0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9852    0.6110    2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0912    0.2194    1.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2332   -1.1415   -1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3154    1.0399   -2.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8136   -0.0148   -2.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0259   -2.2569   -1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4350    0.2819   -2.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0343    2.2414   -0.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991    2.2733    1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8603    1.4359    1.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7 20  1  0
 20 21  1  0
 20 22  2  0
 22  4  1  0
 18  9  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
 22 38  1  0
M  END

Protocatechuic acid 4-O-glucoside
  Mrv1572001071617312D          

 22 23  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 O   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -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
    0.7145   -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
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303826

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1OC(OC2=C(O)C=C(C=C2)C(O)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O9/c14-4-8-9(16)10(17)11(18)13(22-8)21-7-2-1-5(12(19)20)3-6(7)15/h1-3,8-11,13-18H,4H2,(H,19,20)

> <INCHI_KEY>
HFFREILXLCWCQH-UHFFFAOYSA-N

> <FORMULA>
C13H16O9

> <MOLECULAR_WEIGHT>
316.262

> <EXACT_MASS>
316.079432095

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.233487844068794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

> <ALOGPS_LOGP>
-0.94

> <JCHEM_LOGP>
-1.2443700126666668

> <ALOGPS_LOGS>
-1.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.80301466251552

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.102108291318179

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549038426

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
69.4204

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.67e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303826
     RDKit          3D
Protocatechuic acid 4-glucoside
 38 39  0  0  0  0  0  0  0  0999 V2000
    6.5942   -1.2478    0.8206 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7774   -0.3595    1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2303    0.7066    1.9155 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789   -0.4161    0.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9176   -1.4729    0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939   -1.5255   -0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6829   -0.5264    0.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4262   -0.6731   -0.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7626    0.0181   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6388   -0.8420    0.4702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490   -0.4841    0.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2390    0.7764    1.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5942    1.0955    1.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5016   -0.3447   -0.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1712    0.8694   -1.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4060   -0.4305   -2.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657   -1.7351   -2.1761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2607    0.4102   -1.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5740    1.7885   -1.6130 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659    0.5086    0.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3210    1.5177    1.2280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5200    0.5801    1.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8223    1.4209    1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6302   -2.2469   -0.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2705   -2.3758   -0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6786    0.9525    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5360   -1.2914    0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6793    1.6435    0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9852    0.6110    2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0912    0.2194    1.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2332   -1.1415   -1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3154    1.0399   -2.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8136   -0.0148   -2.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0259   -2.2569   -1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4350    0.2819   -2.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0343    2.2414   -0.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991    2.2733    1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8603    1.4359    1.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7 20  1  0
 20 21  1  0
 20 22  2  0
 22  4  1  0
 18  9  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
 22 38  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Protocatechuic acid 4-O-glucoside                 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    7                                                       
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    5   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0303826
HETATM    1  O1  UNL     1       6.594  -1.248   0.821  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.777  -0.359   1.162  1.00  0.00           C  
HETATM    3  O2  UNL     1       6.230   0.707   1.916  1.00  0.00           O  
HETATM    4  C2  UNL     1       4.379  -0.416   0.792  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.918  -1.473   0.042  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.594  -1.526  -0.308  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.683  -0.526   0.078  1.00  0.00           C  
HETATM    8  O3  UNL     1       0.426  -0.673  -0.312  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.763   0.018  -0.179  1.00  0.00           C  
HETATM   10  O4  UNL     1      -1.639  -0.842   0.470  1.00  0.00           O  
HETATM   11  C7  UNL     1      -2.949  -0.484   0.429  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.239   0.776   1.251  1.00  0.00           C  
HETATM   13  O5  UNL     1      -4.594   1.096   1.172  1.00  0.00           O  
HETATM   14  C9  UNL     1      -3.502  -0.345  -0.973  1.00  0.00           C  
HETATM   15  O6  UNL     1      -4.171   0.869  -1.062  1.00  0.00           O  
HETATM   16  C10 UNL     1      -2.406  -0.430  -2.014  1.00  0.00           C  
HETATM   17  O7  UNL     1      -1.966  -1.735  -2.176  1.00  0.00           O  
HETATM   18  C11 UNL     1      -1.261   0.410  -1.556  1.00  0.00           C  
HETATM   19  O8  UNL     1      -1.574   1.789  -1.613  1.00  0.00           O  
HETATM   20  C12 UNL     1       2.166   0.509   0.820  1.00  0.00           C  
HETATM   21  O9  UNL     1       1.321   1.518   1.228  1.00  0.00           O  
HETATM   22  C13 UNL     1       3.520   0.580   1.189  1.00  0.00           C  
HETATM   23  H1  UNL     1       6.822   1.421   1.506  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.630  -2.247  -0.255  1.00  0.00           H  
HETATM   25  H3  UNL     1       2.270  -2.376  -0.900  1.00  0.00           H  
HETATM   26  H4  UNL     1      -0.679   0.952   0.406  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.536  -1.291   0.917  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.679   1.644   0.899  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.985   0.611   2.307  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.091   0.219   1.146  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.233  -1.141  -1.225  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.315   1.040  -2.043  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.814  -0.015  -2.945  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.026  -2.257  -1.350  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.435   0.282  -2.285  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.034   2.241  -0.918  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.699   2.273   1.776  1.00  0.00           H  
HETATM   38  H16 UNL     1       3.860   1.436   1.788  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   23
CONECT    4    5    5   22
CONECT    5    6   24
CONECT    6    7    7   25
CONECT    7    8   20
CONECT    8    9
CONECT    9   10   18   26
CONECT   10   11
CONECT   11   12   14   27
CONECT   12   13   28   29
CONECT   13   30
CONECT   14   15   16   31
CONECT   15   32
CONECT   16   17   18   33
CONECT   17   34
CONECT   18   19   35
CONECT   19   36
CONECT   20   21   22   22
CONECT   21   37
CONECT   22   38
END

HMDB0303826
     RDKit          3D
Protocatechuic acid 4-glucoside
 38 39  0  0  0  0  0  0  0  0999 V2000
    6.5942   -1.2478    0.8206 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7774   -0.3595    1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2303    0.7066    1.9155 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789   -0.4161    0.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9176   -1.4729    0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939   -1.5255   -0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6829   -0.5264    0.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4262   -0.6731   -0.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7626    0.0181   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6388   -0.8420    0.4702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490   -0.4841    0.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2390    0.7764    1.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5942    1.0955    1.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5016   -0.3447   -0.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1712    0.8694   -1.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4060   -0.4305   -2.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657   -1.7351   -2.1761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2607    0.4102   -1.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5740    1.7885   -1.6130 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659    0.5086    0.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3210    1.5177    1.2280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5200    0.5801    1.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8223    1.4209    1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6302   -2.2469   -0.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2705   -2.3758   -0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6786    0.9525    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5360   -1.2914    0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6793    1.6435    0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9852    0.6110    2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0912    0.2194    1.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2332   -1.1415   -1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3154    1.0399   -2.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8136   -0.0148   -2.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0259   -2.2569   -1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4350    0.2819   -2.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0343    2.2414   -0.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991    2.2733    1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8603    1.4359    1.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7 20  1  0
 20 21  1  0
 20 22  2  0
 22  4  1  0
 18  9  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate	Generator
Protocatechuate 4-glucoside	Generator

Chemical Formula

C₁₃H₁₆O₉

Average Molecular Weight

316.262

Monoisotopic Molecular Weight

316.079432095

IUPAC Name

3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

Traditional Name

3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2=C(O)C=C(C=C2)C(O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C13H16O9/c14-4-8-9(16)10(17)11(18)13(22-8)21-7-2-1-5(12(19)20)3-6(7)15/h1-3,8-11,13-18H,4H2,(H,19,20)

InChI Key

HFFREILXLCWCQH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Phenol ether
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Sugar acid
Oxane
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Polyol
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

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

Herb and spice

Herb

Rosemary (FooDB: FOOD00159)

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	-0.94	ALOGPS
logP	-1.2	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.42 m³·mol⁻¹	ChemAxon
Polarizability	29.23 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]+	172.046	32859911
AllCCS	[M+H-H2O]+	168.852	32859911
AllCCS	[M+Na]+	175.85	32859911
AllCCS	[M+NH4]+	175.002	32859911
AllCCS	[M-H]-	168.085	32859911
AllCCS	[M+Na-2H]-	167.95	32859911
AllCCS	[M+HCOO]-	167.925	32859911
DeepCCS	[M+H]+	167.05	30932474
DeepCCS	[M-H]-	164.692	30932474
DeepCCS	[M-2H]-	198.248	30932474
DeepCCS	[M+Na]+	173.475	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Protocatechuic acid 4-glucoside,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	3540.8	Semi standard non polar	33892256
Protocatechuic acid 4-glucoside,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	3519.3	Standard non polar	33892256
Protocatechuic acid 4-glucoside,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	3879.9	Standard polar	33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	3669.3	Semi standard non polar	33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	3665.4	Standard non polar	33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	3721.2	Standard polar	33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	3718.6	Semi standard non polar	33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	3591.9	Standard non polar	33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	3665.1	Standard polar	33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	3740.7	Semi standard non polar	33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	3648.6	Standard non polar	33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	3685.9	Standard polar	33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	3868.8	Semi standard non polar	33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	3710.2	Standard non polar	33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	3568.1	Standard polar	33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	3899.3	Semi standard non polar	33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	3763.1	Standard non polar	33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	3580.7	Standard polar	33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3902.3	Semi standard non polar	33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3681.4	Standard non polar	33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3478.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Protocatechuic acid 4-glucoside GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pbj-9570000000-6d30d9f6adf5b185e7ca	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 - Protocatechuic acid 4-glucoside 10V, Positive-QTOF	splash10-0aos-0953000000-00458630ff20f9da9452	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 20V, Positive-QTOF	splash10-0a4i-0910000000-cdc0cc0b11c3f192f3ed	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 40V, Positive-QTOF	splash10-0a4r-2900000000-5e95efbc21405759814a	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 10V, Negative-QTOF	splash10-0gb9-1957000000-391572d3667b5707b232	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 20V, Negative-QTOF	splash10-0zfr-1920000000-de37ab8c3b253a4e3608	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 40V, Negative-QTOF	splash10-0pb9-3900000000-de8c096d899726f8d065	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 10V, Positive-QTOF	splash10-0002-0954000000-b26c42eeb3c97745fb78	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 20V, Positive-QTOF	splash10-052k-1930000000-0cf9dde76564d38383d5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 40V, Positive-QTOF	splash10-05fs-9800000000-5e9a94e36f969ad6926f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 10V, Negative-QTOF	splash10-0uxr-0935000000-f65e714c5693f8b014b1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 20V, Negative-QTOF	splash10-0zfr-3931000000-2f38d5a75a6cdabe93bb	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 40V, Negative-QTOF	splash10-052f-9500000000-4ee641510c5250432df3	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	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	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

FDB021851

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Protocatechuic acid 4-glucoside (HMDB0303826)

MOL for HMDB0303826 (Protocatechuic acid 4-glucoside)

3D MOL for HMDB0303826 (Protocatechuic acid 4-glucoside)

3D SDF for HMDB0303826 (Protocatechuic acid 4-glucoside)

3D-SDF for HMDB0303826 (Protocatechuic acid 4-glucoside)

PDB for HMDB0303826 (Protocatechuic acid 4-glucoside)

3D PDB for HMDB0303826 (Protocatechuic acid 4-glucoside)

SMILES for HMDB0303826 (Protocatechuic acid 4-glucoside)

INCHI for HMDB0303826 (Protocatechuic acid 4-glucoside)

Structure for HMDB0303826 (Protocatechuic acid 4-glucoside)

3D Structure for HMDB0303826 (Protocatechuic acid 4-glucoside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra