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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 04:31:06 UTC

Update Date

2021-09-24 04:31:06 UTC

HMDB ID

HMDB0303772

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Hydroxybenzoic acid glucoside

Description

4-hydroxybenzoic acid 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. 4-hydroxybenzoic acid glucoside is soluble (in water) and a weakly acidic compound (based on its pKa). 4-hydroxybenzoic acid glucoside can be found in a number of food items such as highbush blueberry, jostaberry, caraway, and carrot, which makes 4-hydroxybenzoic acid glucoside a potential biomarker for the consumption of these food products.

Structure

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

HMDB0303772
     RDKit          3D
4-Hydroxybenzoic acid glucoside
 37 38  0  0  0  0  0  0  0  0999 V2000
    6.3081    1.1076   -1.5459 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7435    0.8354   -0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5469    0.7690    0.6679 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2982    0.5996   -0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7109    0.3028    0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    0.0800    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562    0.1517   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2021   -0.0574   -0.2797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564   -0.3663    0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5679    0.6658    0.9362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3521    0.9037   -0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853    1.6359    0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4630    1.9375   -0.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8655   -0.4078   -0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0169   -0.8258   -1.8179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113   -1.4106    0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5524   -2.5437    0.0862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3478   -1.7086    0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010   -2.3206   -0.5364 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881    0.4518   -1.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5472    0.6776   -1.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9978    1.5997    0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3324    0.2498    1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8933   -0.1476    1.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879   -0.4385    1.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419    1.4808   -0.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1002    0.9341    1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2844    2.5268    0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2235    1.2882   -0.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8670   -0.3130   -1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7585   -0.0524   -2.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1728   -0.8672    1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2610   -2.6102    0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2589   -2.3496    1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4349   -3.2037   -0.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6029    0.5115   -2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0528    0.9139   -2.4724 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  2  0
 21  4  1  0
 18  9  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

4-Hydroxybenzoic acid 4-O-glucoside
  Mrv1572001071617302D          

 21 22  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
    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
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303772

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O8/c14-5-8-9(15)10(16)11(17)13(21-8)20-7-3-1-6(2-4-7)12(18)19/h1-4,8-11,13-17H,5H2,(H,18,19)

> <INCHI_KEY>
XSSDYIMYZONMBL-UHFFFAOYSA-N

> <FORMULA>
C13H16O8

> <MOLECULAR_WEIGHT>
300.263

> <EXACT_MASS>
300.084517475

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.3630603188303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.99

> <JCHEM_LOGP>
-0.9408046909999994

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.20014178463899

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.319042228061938

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343686506

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
67.4395

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303772
     RDKit          3D
4-Hydroxybenzoic acid glucoside
 37 38  0  0  0  0  0  0  0  0999 V2000
    6.3081    1.1076   -1.5459 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7435    0.8354   -0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5469    0.7690    0.6679 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2982    0.5996   -0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7109    0.3028    0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    0.0800    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562    0.1517   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2021   -0.0574   -0.2797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564   -0.3663    0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5679    0.6658    0.9362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3521    0.9037   -0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853    1.6359    0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4630    1.9375   -0.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8655   -0.4078   -0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0169   -0.8258   -1.8179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113   -1.4106    0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5524   -2.5437    0.0862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3478   -1.7086    0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010   -2.3206   -0.5364 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881    0.4518   -1.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5472    0.6776   -1.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9978    1.5997    0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3324    0.2498    1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8933   -0.1476    1.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879   -0.4385    1.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419    1.4808   -0.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1002    0.9341    1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2844    2.5268    0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2235    1.2882   -0.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8670   -0.3130   -1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7585   -0.0524   -2.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1728   -0.8672    1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2610   -2.6102    0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2589   -2.3496    1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4349   -3.2037   -0.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6029    0.5115   -2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0528    0.9139   -2.4724 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  2  0
 21  4  1  0
 18  9  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4-Hydroxybenzoic 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  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001  -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       1.334  -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       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    5   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    3   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0303772
HETATM    1  O1  UNL     1       6.308   1.108  -1.546  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.744   0.835  -0.460  1.00  0.00           C  
HETATM    3  O2  UNL     1       6.547   0.769   0.668  1.00  0.00           O  
HETATM    4  C2  UNL     1       4.298   0.600  -0.395  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.711   0.303   0.815  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.330   0.080   0.862  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.556   0.152  -0.270  1.00  0.00           C  
HETATM    8  O3  UNL     1       0.202  -0.057  -0.280  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.656  -0.366   0.753  1.00  0.00           C  
HETATM   10  O4  UNL     1      -1.568   0.666   0.936  1.00  0.00           O  
HETATM   11  C7  UNL     1      -2.352   0.904  -0.184  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.585   1.636   0.318  1.00  0.00           C  
HETATM   13  O5  UNL     1      -4.463   1.937  -0.713  1.00  0.00           O  
HETATM   14  C9  UNL     1      -2.866  -0.408  -0.785  1.00  0.00           C  
HETATM   15  O6  UNL     1      -2.017  -0.826  -1.818  1.00  0.00           O  
HETATM   16  C10 UNL     1      -2.811  -1.411   0.375  1.00  0.00           C  
HETATM   17  O7  UNL     1      -3.552  -2.544   0.086  1.00  0.00           O  
HETATM   18  C11 UNL     1      -1.348  -1.709   0.588  1.00  0.00           C  
HETATM   19  O8  UNL     1      -0.801  -2.321  -0.536  1.00  0.00           O  
HETATM   20  C12 UNL     1       2.188   0.452  -1.460  1.00  0.00           C  
HETATM   21  C13 UNL     1       3.547   0.678  -1.544  1.00  0.00           C  
HETATM   22  H1  UNL     1       6.998   1.600   0.986  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.332   0.250   1.697  1.00  0.00           H  
HETATM   24  H3  UNL     1       1.893  -0.148   1.803  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.088  -0.439   1.701  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.842   1.481  -0.968  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.100   0.934   1.009  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.284   2.527   0.910  1.00  0.00           H  
HETATM   29  H8  UNL     1      -5.223   1.288  -0.770  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.867  -0.313  -1.206  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.758  -0.052  -2.363  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.173  -0.867   1.268  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.261  -2.610   0.775  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.259  -2.350   1.489  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.435  -3.204  -0.242  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.603   0.511  -2.347  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.053   0.914  -2.472  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   22
CONECT    4    5    5   21
CONECT    5    6   23
CONECT    6    7    7   24
CONECT    7    8   20
CONECT    8    9
CONECT    9   10   18   25
CONECT   10   11
CONECT   11   12   14   26
CONECT   12   13   27   28
CONECT   13   29
CONECT   14   15   16   30
CONECT   15   31
CONECT   16   17   18   32
CONECT   17   33
CONECT   18   19   34
CONECT   19   35
CONECT   20   21   21   36
CONECT   21   37
END

HMDB0303772
     RDKit          3D
4-Hydroxybenzoic acid glucoside
 37 38  0  0  0  0  0  0  0  0999 V2000
    6.3081    1.1076   -1.5459 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7435    0.8354   -0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5469    0.7690    0.6679 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2982    0.5996   -0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7109    0.3028    0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    0.0800    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562    0.1517   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2021   -0.0574   -0.2797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564   -0.3663    0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5679    0.6658    0.9362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3521    0.9037   -0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853    1.6359    0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4630    1.9375   -0.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8655   -0.4078   -0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0169   -0.8258   -1.8179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113   -1.4106    0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5524   -2.5437    0.0862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3478   -1.7086    0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010   -2.3206   -0.5364 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881    0.4518   -1.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5472    0.6776   -1.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9978    1.5997    0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3324    0.2498    1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8933   -0.1476    1.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879   -0.4385    1.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419    1.4808   -0.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1002    0.9341    1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2844    2.5268    0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2235    1.2882   -0.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8670   -0.3130   -1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7585   -0.0524   -2.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1728   -0.8672    1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2610   -2.6102    0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2589   -2.3496    1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4349   -3.2037   -0.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6029    0.5115   -2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0528    0.9139   -2.4724 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  2  0
 21  4  1  0
 18  9  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxybenzoate 4-O-glucoside	Generator
4-Hydroxybenzoate glucoside	Generator

Chemical Formula

C₁₃H₁₆O₈

Average Molecular Weight

300.263

Monoisotopic Molecular Weight

300.084517475

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H16O8/c14-5-8-9(15)10(16)11(17)13(21-8)20-7-3-1-6(2-4-7)12(18)19/h1-4,8-11,13-17H,5H2,(H,18,19)

InChI Key

XSSDYIMYZONMBL-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
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Benzoyl
Phenol ether
Sugar acid
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Acetal
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Primary 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)
Red raspberry (FooDB: FOOD00162)
Highbush blueberry (FooDB: FOOD00191)
Jostaberry (FooDB: FOOD00257)
Blackberry (FooDB: FOOD00906)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Herb and spice

Spice

Herb

Coriander (FooDB: FOOD00061)
Fennel (FooDB: FOOD00082)
Parsley (FooDB: FOOD00131)
Anise (FooDB: FOOD00137)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	-0.99	ALOGPS
logP	-0.94	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.32	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	67.44 m³·mol⁻¹	ChemAxon
Polarizability	28.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	169.289	32859911
AllCCS	[M+H-H2O]+	165.975	32859911
AllCCS	[M+Na]+	173.241	32859911
AllCCS	[M+NH4]+	172.359	32859911
AllCCS	[M-H]-	165.864	32859911
AllCCS	[M+Na-2H]-	165.758	32859911
AllCCS	[M+HCOO]-	165.762	32859911
DeepCCS	[M+H]+	165.404	30932474
DeepCCS	[M-H]-	163.046	30932474
DeepCCS	[M-2H]-	196.015	30932474
DeepCCS	[M+Na]+	171.497	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxybenzoic acid glucoside GC-MS (Non-derivatized) - 70eV, Positive	splash10-06sr-9660000000-bb13132c9068081a8b65	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 - 4-Hydroxybenzoic acid glucoside 10V, Positive-QTOF	splash10-0f80-0973000000-bac0c166e1731676079a	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid glucoside 20V, Positive-QTOF	splash10-00dr-1910000000-ffcce3da7c134e2d430e	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid glucoside 40V, Positive-QTOF	splash10-00dr-5900000000-4cf503b4034676fb3986	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid glucoside 10V, Negative-QTOF	splash10-000b-1690000000-48fa2d9eaf836a930295	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid glucoside 20V, Negative-QTOF	splash10-000i-4950000000-62dd8d09ed1e301c4df9	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid glucoside 40V, Negative-QTOF	splash10-000f-9600000000-6f04d9548d6d280ea0a9	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid glucoside 10V, Positive-QTOF	splash10-0f7t-3955000000-38323e7b7e94c3a29a20	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid glucoside 20V, Positive-QTOF	splash10-001r-2950000000-edf5be02fe283edfc267	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid glucoside 40V, Positive-QTOF	splash10-007c-9430000000-eee9e3e0fd511210d409	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid glucoside 10V, Negative-QTOF	splash10-000f-9500000000-e1e2c86ae32804fac8c8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid glucoside 20V, Negative-QTOF	splash10-0006-9110000000-1d1ef70c4ed21d631a0d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid glucoside 40V, Negative-QTOF	splash10-0a4l-6900000000-3b20254bd22a052395e5	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021634

KNApSAcK ID

Not Available

Chemspider ID

2568436

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3320872

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 4-Hydroxybenzoic acid glucoside (HMDB0303772)

MOL for HMDB0303772 (4-Hydroxybenzoic acid glucoside)

3D MOL for HMDB0303772 (4-Hydroxybenzoic acid glucoside)

3D SDF for HMDB0303772 (4-Hydroxybenzoic acid glucoside)

3D-SDF for HMDB0303772 (4-Hydroxybenzoic acid glucoside)

PDB for HMDB0303772 (4-Hydroxybenzoic acid glucoside)

3D PDB for HMDB0303772 (4-Hydroxybenzoic acid glucoside)

SMILES for HMDB0303772 (4-Hydroxybenzoic acid glucoside)

INCHI for HMDB0303772 (4-Hydroxybenzoic acid glucoside)

Structure for HMDB0303772 (4-Hydroxybenzoic acid glucoside)

3D Structure for HMDB0303772 (4-Hydroxybenzoic acid glucoside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra