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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 18:01:22 UTC

Update Date

2021-09-23 18:01:22 UTC

HMDB ID

HMDB0302469

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Vanillic acid 4-beta-D-glucoside

Description

Vanillic acid 4-beta-d-glucoside, also known as vanillate 4-beta-D-glucoside, is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Vanillic acid 4-beta-d-glucoside is soluble (in water) and a weakly acidic compound (based on its pKa). Vanillic acid 4-beta-d-glucoside can be found in a number of food items such as sweet marjoram, orange bell pepper, yellow bell pepper, and pepper (c. annuum), which makes vanillic acid 4-beta-d-glucoside a potential biomarker for the consumption of these food products.

Structure

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

HMDB0302469
     RDKit          3D
Vanillic acid 4-beta-D-glucoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    3.8110    1.1547   -2.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763    0.8438   -1.7976 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6841    0.4088   -0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8562    0.2463    0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8436   -0.1912    1.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0977   -0.3565    2.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0752   -0.7524    3.4317 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002   -0.0773    1.5968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6509   -0.4577    2.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4626   -0.2856    1.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4727    0.1449    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3281    0.3110   -0.5820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9934    0.1238   -0.2383 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6175   -0.8958   -0.9962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7761   -1.2126   -0.2890 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3538   -2.5419   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5017   -2.7638    0.0574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7434   -0.0810   -0.4608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9728   -0.4703    0.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1689    1.1055    0.3177 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0191    2.2158    0.1528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8183    1.3988   -0.3004 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1535    2.3341    0.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6310    1.5423   -1.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    1.9170   -3.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1039    0.2389   -3.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8131    0.4439   -0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5017   -0.5344    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6266   -0.8007    3.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5575   -0.5192    1.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632   -0.2268    0.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5018   -1.2583    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6769   -3.3786   -0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6622   -2.5588   -1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2419   -2.7888    1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8304    0.2599   -1.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5718   -0.7130   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0526    0.8597    1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2309    2.3031   -0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522    1.7746   -1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1623    3.2379    0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11  3  1  0
 22 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  1
 15 32  1  1
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  6
 19 37  1  0
 20 38  1  1
 21 39  1  0
 22 40  1  6
 23 41  1  0
M  END


  Mrv1652309272007372D          

 23 24  0  0  0  0            999 V2000
 9999.6522 9998.9779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.511910000.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.228310000.2162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.511910001.4549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2219 9998.1521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7916 9998.9779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.221910001.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.506810001.8678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.791610000.6291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.797810000.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.083310000.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.368810000.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3687 9999.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0832 9998.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7978 9999.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.221910000.6283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.507410000.2158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5074 9999.3907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.2219 9998.9783    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9364 9999.3907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.936410000.2158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0832 9998.1532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7977 9997.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  7  8  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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 10  1  0  0  0  0
  1 13  1  0  0  0  0
 10  2  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 21  1  0  0  0  0
 20 21  1  0  0  0  0
 20  1  1  1  0  0  0
 19  5  1  6  0  0  0
 18  6  1  1  0  0  0
 17  9  1  6  0  0  0
 16  7  1  1  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302469

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O9/c1-21-8-4-6(13(19)20)2-3-7(8)22-14-12(18)11(17)10(16)9(5-15)23-14/h2-4,9-12,14-18H,5H2,1H3,(H,19,20)/t9-,10-,11+,12-,14-/m1/s1

> <INCHI_KEY>
JYFOSWJYZIVJPO-YGEZULPYSA-N

> <FORMULA>
C14H18O9

> <MOLECULAR_WEIGHT>
330.289

> <EXACT_MASS>
330.09508216

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.202574720200865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.97

> <JCHEM_LOGP>
-1.0984759566666666

> <ALOGPS_LOGS>
-1.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.200014907685965

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.097357092526834

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549072026

> <JCHEM_POLAR_SURFACE_AREA>
145.91

> <JCHEM_REFRACTIVITY>
73.90270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302469
     RDKit          3D
Vanillic acid 4-beta-D-glucoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    3.8110    1.1547   -2.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763    0.8438   -1.7976 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6841    0.4088   -0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8562    0.2463    0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8436   -0.1912    1.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0977   -0.3565    2.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0752   -0.7524    3.4317 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002   -0.0773    1.5968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6509   -0.4577    2.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4626   -0.2856    1.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4727    0.1449    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3281    0.3110   -0.5820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9934    0.1238   -0.2383 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6175   -0.8958   -0.9962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7761   -1.2126   -0.2890 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3538   -2.5419   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5017   -2.7638    0.0574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7434   -0.0810   -0.4608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9728   -0.4703    0.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1689    1.1055    0.3177 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0191    2.2158    0.1528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8183    1.3988   -0.3004 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1535    2.3341    0.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6310    1.5423   -1.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    1.9170   -3.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1039    0.2389   -3.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8131    0.4439   -0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5017   -0.5344    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6266   -0.8007    3.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5575   -0.5192    1.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632   -0.2268    0.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5018   -1.2583    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6769   -3.3786   -0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6622   -2.5588   -1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2419   -2.7888    1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8304    0.2599   -1.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5718   -0.7130   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0526    0.8597    1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2309    2.3031   -0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522    1.7746   -1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1623    3.2379    0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11  3  1  0
 22 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  1
 15 32  1  1
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  6
 19 37  1  0
 20 38  1  1
 21 39  1  0
 22 40  1  6
 23 41  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8666.0178664.759   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8671.3568667.841   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8672.6938667.070   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8671.3568669.382   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8663.3488663.217   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8660.6788664.759   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8663.3488669.382   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8662.0138670.153   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8660.6788667.841   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8670.0238667.069   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.6898667.839   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.3558667.069   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.3558665.529   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.6898664.759   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8670.0238665.529   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.3488667.839   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.0148667.069   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8662.0148665.529   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8663.3488664.759   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.6818665.529   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8664.6818667.069   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0    8668.6898663.219   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0    8670.0228662.449   0.000  0.00  0.00           C+0
CONECT    1   13   20                                                       
CONECT    2    3    4   10                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5   19                                                            
CONECT    6   18                                                            
CONECT    7    8   16                                                       
CONECT    8    7                                                            
CONECT    9   17                                                            
CONECT   10   11   15    2                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14    1                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   10                                                       
CONECT   16   17   21    7                                                  
CONECT   17   16   18    9                                                  
CONECT   18   17   19    6                                                  
CONECT   19   18   20    5                                                  
CONECT   20   19   21    1                                                  
CONECT   21   16   20                                                       
CONECT   22   14   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0302469
HETATM    1  C1  UNL     1       3.811   1.155  -2.546  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.676   0.844  -1.798  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.684   0.409  -0.481  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.856   0.246   0.207  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.844  -0.191   1.528  1.00  0.00           C  
HETATM    6  C5  UNL     1       5.098  -0.357   2.239  1.00  0.00           C  
HETATM    7  O2  UNL     1       5.075  -0.752   3.432  1.00  0.00           O  
HETATM    8  O3  UNL     1       6.300  -0.077   1.597  1.00  0.00           O  
HETATM    9  C6  UNL     1       2.651  -0.458   2.133  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.463  -0.286   1.413  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.473   0.145   0.113  1.00  0.00           C  
HETATM   12  O4  UNL     1       0.328   0.311  -0.582  1.00  0.00           O  
HETATM   13  C9  UNL     1      -0.993   0.124  -0.238  1.00  0.00           C  
HETATM   14  O5  UNL     1      -1.617  -0.896  -0.996  1.00  0.00           O  
HETATM   15  C10 UNL     1      -2.776  -1.213  -0.289  1.00  0.00           C  
HETATM   16  C11 UNL     1      -3.354  -2.542  -0.703  1.00  0.00           C  
HETATM   17  O6  UNL     1      -4.502  -2.764   0.057  1.00  0.00           O  
HETATM   18  C12 UNL     1      -3.743  -0.081  -0.461  1.00  0.00           C  
HETATM   19  O7  UNL     1      -4.973  -0.470   0.052  1.00  0.00           O  
HETATM   20  C13 UNL     1      -3.169   1.105   0.318  1.00  0.00           C  
HETATM   21  O8  UNL     1      -4.019   2.216   0.153  1.00  0.00           O  
HETATM   22  C14 UNL     1      -1.818   1.399  -0.300  1.00  0.00           C  
HETATM   23  O9  UNL     1      -1.153   2.334   0.499  1.00  0.00           O  
HETATM   24  H1  UNL     1       4.631   1.542  -1.938  1.00  0.00           H  
HETATM   25  H2  UNL     1       3.572   1.917  -3.326  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.104   0.239  -3.120  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.813   0.444  -0.229  1.00  0.00           H  
HETATM   28  H5  UNL     1       6.502  -0.534   0.716  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.627  -0.801   3.166  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.557  -0.519   1.966  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.063  -0.227   0.810  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.502  -1.258   0.782  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.677  -3.379  -0.518  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.662  -2.559  -1.758  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.242  -2.789   1.033  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.830   0.260  -1.517  1.00  0.00           H  
HETATM   37  H14 UNL     1      -5.572  -0.713  -0.704  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.053   0.860   1.389  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.231   2.303  -0.810  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.952   1.775  -1.320  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.162   3.238   0.119  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   27
CONECT    5    6    9    9
CONECT    6    7    7    8
CONECT    8   28
CONECT    9   10   29
CONECT   10   11   11   30
CONECT   11   12
CONECT   12   13
CONECT   13   14   22   31
CONECT   14   15
CONECT   15   16   18   32
CONECT   16   17   33   34
CONECT   17   35
CONECT   18   19   20   36
CONECT   19   37
CONECT   20   21   22   38
CONECT   21   39
CONECT   22   23   40
CONECT   23   41
END

HMDB0302469
     RDKit          3D
Vanillic acid 4-beta-D-glucoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    3.8110    1.1547   -2.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763    0.8438   -1.7976 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6841    0.4088   -0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8562    0.2463    0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8436   -0.1912    1.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0977   -0.3565    2.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0752   -0.7524    3.4317 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002   -0.0773    1.5968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6509   -0.4577    2.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4626   -0.2856    1.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4727    0.1449    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3281    0.3110   -0.5820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9934    0.1238   -0.2383 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6175   -0.8958   -0.9962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7761   -1.2126   -0.2890 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3538   -2.5419   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5017   -2.7638    0.0574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7434   -0.0810   -0.4608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9728   -0.4703    0.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1689    1.1055    0.3177 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0191    2.2158    0.1528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8183    1.3988   -0.3004 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1535    2.3341    0.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6310    1.5423   -1.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    1.9170   -3.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1039    0.2389   -3.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8131    0.4439   -0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5017   -0.5344    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6266   -0.8007    3.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5575   -0.5192    1.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632   -0.2268    0.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5018   -1.2583    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6769   -3.3786   -0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6622   -2.5588   -1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2419   -2.7888    1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8304    0.2599   -1.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5718   -0.7130   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0526    0.8597    1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2309    2.3031   -0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522    1.7746   -1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1623    3.2379    0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11  3  1  0
 22 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  1
 15 32  1  1
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  6
 19 37  1  0
 20 38  1  1
 21 39  1  0
 22 40  1  6
 23 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate	Generator
Vanillate 4-b-D-glucoside	Generator
Vanillate 4-beta-D-glucoside	Generator
Vanillate 4-β-D-glucoside	Generator
Vanillic acid 4-b-D-glucoside	Generator
Vanillic acid 4-β-D-glucoside	Generator
4-(beta-D-Glucopyranosyloxy)-3-methoxybenzoic acid	PhytoBank
4-(β-D-Glucopyranosyloxy)-3-methoxybenzoic acid	PhytoBank
4-O-beta-D-Glucopyranosylvanillc acid	PhytoBank
4-O-β-D-Glucopyranosylvanillc acid	PhytoBank
Vanillic acid 4-O-beta-D-glucopyranoside	PhytoBank
Vanillic acid 4-O-β-D-glucopyranoside	PhytoBank
Vanillic acid 4-beta-D-glucoside	PhytoBank
Vanillic acid glucoside	PhytoBank
Vanillic acid beta-glucoside	PhytoBank
Vanillic acid β-glucoside	PhytoBank
Vanillic acid-4-O-glucopyranoside	PhytoBank

Chemical Formula

C₁₄H₁₈O₉

Average Molecular Weight

330.289

Monoisotopic Molecular Weight

330.09508216

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C14H18O9/c1-21-8-4-6(13(19)20)2-3-7(8)22-14-12(18)11(17)10(16)9(5-15)23-14/h2-4,9-12,14-18H,5H2,1H3,(H,19,20)/t9-,10-,11+,12-,14-/m1/s1

InChI Key

JYFOSWJYZIVJPO-YGEZULPYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
M-methoxybenzoic acid or derivatives
O-glycosyl compound
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Phenol ether
Alkyl aryl ether
Sugar acid
Oxane
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Ether
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Acetal
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tannin (CHEBI:68950 )

Ontology

Not Available

Not Available

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	-0.97	ALOGPS
logP	-1.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.9 m³·mol⁻¹	ChemAxon
Polarizability	31.2 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]+	176.225	32859911
AllCCS	[M+H-H2O]+	173.133	32859911
AllCCS	[M+Na]+	179.904	32859911
AllCCS	[M+NH4]+	179.083	32859911
AllCCS	[M-H]-	172.614	32859911
AllCCS	[M+Na-2H]-	172.612	32859911
AllCCS	[M+HCOO]-	172.736	32859911
DeepCCS	[M+H]+	174.882	30932474
DeepCCS	[M-H]-	172.487	30932474
DeepCCS	[M-2H]-	205.685	30932474
DeepCCS	[M+Na]+	180.795	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-beta-D-glucoside 10V, Positive-QTOF	splash10-02u0-0936000000-0e8b93eaea1cf3a4d8ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-beta-D-glucoside 20V, Positive-QTOF	splash10-0gb9-0910000000-50e42202457a753d2780	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-beta-D-glucoside 40V, Positive-QTOF	splash10-0uxr-2900000000-20cdd53664ebdecf222d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-beta-D-glucoside 10V, Negative-QTOF	splash10-00or-1849000000-273a77108fea27ac55ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-beta-D-glucoside 20V, Negative-QTOF	splash10-014i-1921000000-4ff0b71203ed7d32b239	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-beta-D-glucoside 40V, Negative-QTOF	splash10-0uxr-2900000000-8ef8ecd6412050968a6e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-beta-D-glucoside 10V, Positive-QTOF	splash10-03e9-0419000000-d1c5647926a0795fc20e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-beta-D-glucoside 20V, Positive-QTOF	splash10-0wvj-0921000000-cc0d69fbe3df54a8607b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-beta-D-glucoside 40V, Positive-QTOF	splash10-0gb9-3910000000-48581e42b2fb1722c6ff	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-beta-D-glucoside 10V, Negative-QTOF	splash10-016r-0905000000-471210a6671b3a3c6325	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-beta-D-glucoside 20V, Negative-QTOF	splash10-0gb9-2690000000-083e867f0959e02df6f4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillic acid 4-beta-D-glucoside 40V, Negative-QTOF	splash10-0pb9-8941000000-f68155dd42b05f6f5620	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

FDB004688

KNApSAcK ID

Not Available

Chemspider ID

10290220

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 Vanillic acid 4-beta-D-glucoside (HMDB0302469)

MOL for HMDB0302469 (Vanillic acid 4-beta-D-glucoside)

3D MOL for HMDB0302469 (Vanillic acid 4-beta-D-glucoside)

3D SDF for HMDB0302469 (Vanillic acid 4-beta-D-glucoside)

3D-SDF for HMDB0302469 (Vanillic acid 4-beta-D-glucoside)

PDB for HMDB0302469 (Vanillic acid 4-beta-D-glucoside)

3D PDB for HMDB0302469 (Vanillic acid 4-beta-D-glucoside)

SMILES for HMDB0302469 (Vanillic acid 4-beta-D-glucoside)

INCHI for HMDB0302469 (Vanillic acid 4-beta-D-glucoside)

Structure for HMDB0302469 (Vanillic acid 4-beta-D-glucoside)

3D Structure for HMDB0302469 (Vanillic acid 4-beta-D-glucoside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra