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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 18:01:48 UTC

Update Date

2021-09-23 18:01:48 UTC

HMDB ID

HMDB0302470

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Vanilloyl glucose

Description

Vanilloyl glucose 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. Vanilloyl glucose is soluble (in water) and a very weakly acidic compound (based on its pKa). Vanilloyl glucose can be found in a number of food items such as orange bell pepper, yellow bell pepper, pepper (c. annuum), and red bell pepper, which makes vanilloyl glucose a potential biomarker for the consumption of these food products.

Structure

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

  Mrv1533007301516532D          

 28 29  0  0  1  0            999 V2000
   -0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  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    1.2375    0.0000 C   0  0  1  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
    1.4289    5.7750    0.0000 O   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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  1  1  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  6  1  0  0  0  0
 14 12  1  0  0  0  0
 15  5  1  0  0  0  0
 16  7  1  0  0  0  0
 10 17  1  6  0  0  0
 11 18  1  6  0  0  0
 12 19  1  6  0  0  0
 20 13  2  0  0  0  0
 21  1  1  0  0  0  0
 21  8  1  0  0  0  0
 22  9  1  0  0  0  0
 22 14  1  0  0  0  0
 23 13  1  0  0  0  0
 14 23  1  1  0  0  0
  9 24  1  6  0  0  0
 10 25  1  1  0  0  0
 11 26  1  6  0  0  0
 12 27  1  1  0  0  0
 14 28  1  6  0  0  0
M  END

HMDB0302470
     RDKit          3D
Vanilloyl glucose
 41 42  0  0  0  0  0  0  0  0999 V2000
    6.0280    1.4542   -0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9128    0.6542    0.5295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426    0.1885    0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5235    0.4840    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2764    0.0156    0.4663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1287    0.3584   -0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2346    1.0722   -1.3918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1595   -0.0855   -0.0610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2844    0.2466   -0.8668 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2438    0.9399   -0.1411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932    0.8050   -0.7409 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4681    1.7424   -0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4839    1.3277    1.3088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0152   -0.6019   -0.5018 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8886   -0.8886   -1.5494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8959   -1.6138   -0.5369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4038   -1.9318    0.7051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8112   -1.0603   -1.4246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3050   -0.8274   -2.7028 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1866   -0.7631    1.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3079   -1.0677    2.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5586   -0.5940    2.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7067   -0.8821    2.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2648    2.2615   -0.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9558    0.8849   -1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0140    1.9982   -0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042    1.0977   -0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9725    0.8869   -1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5085    1.0678   -1.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1504    2.7890   -0.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635    1.5740   -0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5184    2.1524    1.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6016   -0.6642    0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6013   -1.4877   -1.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2922   -2.5425   -0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3805   -1.1636    1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0057   -1.8345   -1.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4403   -1.7099   -3.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2207   -1.1446    1.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2512   -1.6785    3.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5704   -1.4595    3.5718 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
  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
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 18  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  9 28  1  6
 11 29  1  6
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  1
 15 34  1  0
 16 35  1  6
 17 36  1  0
 18 37  1  6
 19 38  1  0
 20 39  1  0
 21 40  1  0
 23 41  1  0
M  END

  Mrv1533007301516532D          

 28 29  0  0  1  0            999 V2000
   -0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  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    1.2375    0.0000 C   0  0  1  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
    1.4289    5.7750    0.0000 O   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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  1  1  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  6  1  0  0  0  0
 14 12  1  0  0  0  0
 15  5  1  0  0  0  0
 16  7  1  0  0  0  0
 10 17  1  6  0  0  0
 11 18  1  6  0  0  0
 12 19  1  6  0  0  0
 20 13  2  0  0  0  0
 21  1  1  0  0  0  0
 21  8  1  0  0  0  0
 22  9  1  0  0  0  0
 22 14  1  0  0  0  0
 23 13  1  0  0  0  0
 14 23  1  1  0  0  0
  9 24  1  6  0  0  0
 10 25  1  1  0  0  0
 11 26  1  6  0  0  0
 12 27  1  1  0  0  0
 14 28  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0302470

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]1(CO)O[C@@]([H])(OC(=O)C2=CC(OC)=C(O)C=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O

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

> <INCHI_KEY>
YROOZUQRTLHXIO-DIACKHNESA-N

> <FORMULA>
C14H18O9

> <MOLECULAR_WEIGHT>
330.289

> <EXACT_MASS>
330.09508216

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.83029407501357

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4-hydroxy-3-methoxybenzoate

> <ALOGPS_LOGP>
-0.99

> <JCHEM_LOGP>
-0.8984759566666668

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.195940523897887

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.963613558334746

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810938238797924

> <JCHEM_POLAR_SURFACE_AREA>
145.91

> <JCHEM_REFRACTIVITY>
74.1895

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4-hydroxy-3-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302470
     RDKit          3D
Vanilloyl glucose
 41 42  0  0  0  0  0  0  0  0999 V2000
    6.0280    1.4542   -0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9128    0.6542    0.5295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426    0.1885    0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5235    0.4840    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2764    0.0156    0.4663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1287    0.3584   -0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2346    1.0722   -1.3918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1595   -0.0855   -0.0610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2844    0.2466   -0.8668 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2438    0.9399   -0.1411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932    0.8050   -0.7409 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4681    1.7424   -0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4839    1.3277    1.3088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0152   -0.6019   -0.5018 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8886   -0.8886   -1.5494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8959   -1.6138   -0.5369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4038   -1.9318    0.7051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8112   -1.0603   -1.4246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3050   -0.8274   -2.7028 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1866   -0.7631    1.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3079   -1.0677    2.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5586   -0.5940    2.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7067   -0.8821    2.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2648    2.2615   -0.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9558    0.8849   -1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0140    1.9982   -0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042    1.0977   -0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9725    0.8869   -1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5085    1.0678   -1.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1504    2.7890   -0.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635    1.5740   -0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5184    2.1524    1.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6016   -0.6642    0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6013   -1.4877   -1.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2922   -2.5425   -0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3805   -1.1636    1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0057   -1.8345   -1.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4403   -1.7099   -3.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2207   -1.1446    1.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2512   -1.6785    3.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5704   -1.4595    3.5718 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
  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
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 18  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  9 28  1  6
 11 29  1  6
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  1
 15 34  1  0
 16 35  1  6
 17 36  1  0
 18 37  1  6
 19 38  1  0
 20 39  1  0
 21 40  1  0
 23 41  1  0
M  END

HEADER    PROTEIN                                 30-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-15         0                                  
HETATM    1  C   UNK     0      -0.000  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.000   9.240   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.000   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0      -0.000  -1.540   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.001   0.770   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2    3    6                                                       
CONECT    3    2    7                                                       
CONECT    4    6    8                                                       
CONECT    5    9   15                                                       
CONECT    6    2    4   13                                                  
CONECT    7    3    8   16                                                  
CONECT    8    4    7   21                                                  
CONECT    9    5   10   22   24                                             
CONECT   10    9   11   17   25                                             
CONECT   11   10   12   18   26                                             
CONECT   12   11   14   19   27                                             
CONECT   13    6   20   23                                                  
CONECT   14   12   22   23   28                                             
CONECT   15    5                                                            
CONECT   16    7                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21    1    8                                                       
CONECT   22    9   14                                                       
CONECT   23   13   14                                                       
CONECT   24    9                                                            
CONECT   25   10                                                            
CONECT   26   11                                                            
CONECT   27   12                                                            
CONECT   28   14                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

COMPND    HMDB0302470
HETATM    1  C1  UNL     1       6.028   1.454  -0.626  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.913   0.654   0.530  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.643   0.188   0.868  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.524   0.484   0.118  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.276   0.016   0.466  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.129   0.358  -0.362  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.235   1.072  -1.392  1.00  0.00           O  
HETATM    8  O3  UNL     1      -0.160  -0.086  -0.061  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.284   0.247  -0.867  1.00  0.00           C  
HETATM   10  O4  UNL     1      -2.244   0.940  -0.141  1.00  0.00           O  
HETATM   11  C7  UNL     1      -3.493   0.805  -0.741  1.00  0.00           C  
HETATM   12  C8  UNL     1      -4.468   1.742  -0.036  1.00  0.00           C  
HETATM   13  O5  UNL     1      -4.484   1.328   1.309  1.00  0.00           O  
HETATM   14  C9  UNL     1      -4.015  -0.602  -0.502  1.00  0.00           C  
HETATM   15  O6  UNL     1      -4.889  -0.889  -1.549  1.00  0.00           O  
HETATM   16  C10 UNL     1      -2.896  -1.614  -0.537  1.00  0.00           C  
HETATM   17  O7  UNL     1      -2.404  -1.932   0.705  1.00  0.00           O  
HETATM   18  C11 UNL     1      -1.811  -1.060  -1.425  1.00  0.00           C  
HETATM   19  O8  UNL     1      -2.305  -0.827  -2.703  1.00  0.00           O  
HETATM   20  C12 UNL     1       2.187  -0.763   1.597  1.00  0.00           C  
HETATM   21  C13 UNL     1       3.308  -1.068   2.361  1.00  0.00           C  
HETATM   22  C14 UNL     1       4.559  -0.594   2.006  1.00  0.00           C  
HETATM   23  O9  UNL     1       5.707  -0.882   2.753  1.00  0.00           O  
HETATM   24  H1  UNL     1       5.265   2.261  -0.538  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.956   0.885  -1.566  1.00  0.00           H  
HETATM   26  H3  UNL     1       7.014   1.998  -0.650  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.604   1.098  -0.771  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.972   0.887  -1.731  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.509   1.068  -1.801  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.150   2.789  -0.137  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.464   1.574  -0.457  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.518   2.152   1.855  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.602  -0.664   0.438  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.601  -1.488  -1.214  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.292  -2.542  -0.993  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.381  -1.164   1.335  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.006  -1.835  -1.474  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.440  -1.710  -3.121  1.00  0.00           H  
HETATM   39  H16 UNL     1       1.221  -1.145   1.895  1.00  0.00           H  
HETATM   40  H17 UNL     1       3.251  -1.679   3.252  1.00  0.00           H  
HETATM   41  H18 UNL     1       5.570  -1.459   3.572  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   27
CONECT    5    6   20   20
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   18   28
CONECT   10   11
CONECT   11   12   14   29
CONECT   12   13   30   31
CONECT   13   32
CONECT   14   15   16   33
CONECT   15   34
CONECT   16   17   18   35
CONECT   17   36
CONECT   18   19   37
CONECT   19   38
CONECT   20   21   39
CONECT   21   22   22   40
CONECT   22   23
CONECT   23   41
END

HMDB0302470
     RDKit          3D
Vanilloyl glucose
 41 42  0  0  0  0  0  0  0  0999 V2000
    6.0280    1.4542   -0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9128    0.6542    0.5295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426    0.1885    0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5235    0.4840    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2764    0.0156    0.4663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1287    0.3584   -0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2346    1.0722   -1.3918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1595   -0.0855   -0.0610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2844    0.2466   -0.8668 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2438    0.9399   -0.1411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932    0.8050   -0.7409 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4681    1.7424   -0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4839    1.3277    1.3088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0152   -0.6019   -0.5018 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8886   -0.8886   -1.5494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8959   -1.6138   -0.5369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4038   -1.9318    0.7051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8112   -1.0603   -1.4246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3050   -0.8274   -2.7028 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1866   -0.7631    1.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3079   -1.0677    2.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5586   -0.5940    2.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7067   -0.8821    2.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2648    2.2615   -0.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9558    0.8849   -1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0140    1.9982   -0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042    1.0977   -0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9725    0.8869   -1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5085    1.0678   -1.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1504    2.7890   -0.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635    1.5740   -0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5184    2.1524    1.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6016   -0.6642    0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6013   -1.4877   -1.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2922   -2.5425   -0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3805   -1.1636    1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0057   -1.8345   -1.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4403   -1.7099   -3.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2207   -1.1446    1.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2512   -1.6785    3.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5704   -1.4595    3.5718 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
  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
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 18  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  9 28  1  6
 11 29  1  6
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  1
 15 34  1  0
 16 35  1  6
 17 36  1  0
 18 37  1  6
 19 38  1  0
 20 39  1  0
 21 40  1  0
 23 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-O-(4-Hydroxy-3-methoxybenzoyl)-beta-D-glucose	ChEBI
1-O-(4-Hydroxy-3-methoxybenzoyl)-b-D-glucose	Generator
1-O-(4-Hydroxy-3-methoxybenzoyl)-β-D-glucose	Generator
1-O-Vanilloyl-b-D-glucose	Generator
1-O-Vanilloyl-β-D-glucose	Generator

Chemical Formula

C₁₄H₁₈O₉

Average Molecular Weight

330.289

Monoisotopic Molecular Weight

330.09508216

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4-hydroxy-3-methoxybenzoate

Traditional Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4-hydroxy-3-methoxybenzoate

CAS Registry Number

Not Available

SMILES

[H][C@]1(CO)O[C@@]([H])(OC(=O)C2=CC(OC)=C(O)C=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O

InChI Identifier

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

InChI Key

YROOZUQRTLHXIO-DIACKHNESA-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
Hexose monosaccharide
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
M-methoxybenzoic acid or derivatives
Benzoate ester
Methoxyphenol
Benzoic acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Benzoyl
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

O-acyl carbohydrate (CHEBI:71512 )

Ontology

Not Available

Exogenous (HMDB: HMDB0302470)

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	-0.99	ALOGPS
logP	-0.9	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	8.96	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	74.19 m³·mol⁻¹	ChemAxon
Polarizability	30.83 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]+	175.711	32859911
AllCCS	[M+H-H2O]+	172.675	32859911
AllCCS	[M+Na]+	179.322	32859911
AllCCS	[M+NH4]+	178.517	32859911
AllCCS	[M-H]-	172.583	32859911
AllCCS	[M+Na-2H]-	172.586	32859911
AllCCS	[M+HCOO]-	172.715	32859911
DeepCCS	[M+H]+	169.442	30932474
DeepCCS	[M-H]-	167.222	30932474
DeepCCS	[M-2H]-	200.461	30932474
DeepCCS	[M+Na]+	176.146	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 - Vanilloyl glucose 10V, Positive-QTOF	splash10-0i00-0902000000-f9374f5d535848e52fc7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloyl glucose 20V, Positive-QTOF	splash10-0udi-0900000000-b46505720ecda42c7546	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloyl glucose 40V, Positive-QTOF	splash10-0udi-3900000000-489521303efb861f56ff	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloyl glucose 10V, Negative-QTOF	splash10-016s-1904000000-efbe575ddff28bd54d12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloyl glucose 20V, Negative-QTOF	splash10-0i6r-2901000000-e86412263b80389cb893	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloyl glucose 40V, Negative-QTOF	splash10-0gi3-7900000000-11614dfb4cd58ab8cdea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloyl glucose 10V, Positive-QTOF	splash10-0fb9-0900000000-6601edabe397e50bed63	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloyl glucose 20V, Positive-QTOF	splash10-0fk9-0910000000-9902340a55f3fe83f723	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloyl glucose 40V, Positive-QTOF	splash10-0umi-6910000000-ab998840918c25a38808	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloyl glucose 10V, Negative-QTOF	splash10-014i-0902000000-1f408ff56427a5f3bdc6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloyl glucose 20V, Negative-QTOF	splash10-0ktr-1910000000-7468c35b24d4fbe27212	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloyl glucose 40V, Negative-QTOF	splash10-0pb9-4900000000-9fdaf8c5e4731311864e	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

71512

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 Vanilloyl glucose (HMDB0302470)

MOL for HMDB0302470 (Vanilloyl glucose)

3D MOL for HMDB0302470 (Vanilloyl glucose)

3D SDF for HMDB0302470 (Vanilloyl glucose)

3D-SDF for HMDB0302470 (Vanilloyl glucose)

PDB for HMDB0302470 (Vanilloyl glucose)

3D PDB for HMDB0302470 (Vanilloyl glucose)

SMILES for HMDB0302470 (Vanilloyl glucose)

INCHI for HMDB0302470 (Vanilloyl glucose)

Structure for HMDB0302470 (Vanilloyl glucose)

3D Structure for HMDB0302470 (Vanilloyl glucose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra