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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 03:56:14 UTC

Update Date

2021-09-23 03:56:14 UTC

HMDB ID

HMDB0301952

Secondary Accession Numbers

None

Metabolite Identification

Common Name

trans-p-Feruloyl-beta-D-glucopyranoside

Description

Trans-p-feruloyl-beta-d-glucopyranoside, also known as 1-feruloyl-D-glucose, is a member of the class of compounds known as hydroxycinnamic acid glycosides. Hydroxycinnamic acid glycosides are glycosylated hydoxycinnamic acids derivatives. Trans-p-feruloyl-beta-d-glucopyranoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Trans-p-feruloyl-beta-d-glucopyranoside can be found in a number of food items such as green bell pepper, pepper (c. annuum), yellow bell pepper, and orange bell pepper, which makes trans-p-feruloyl-beta-d-glucopyranoside a potential biomarker for the consumption of these food products.

Structure

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

HMDB0301952
     RDKit          3D
trans-p-Feruloyl-beta-D-glucopyranoside
 45 46  0  0  0  0  0  0  0  0999 V2000
    6.7282   -0.5628    2.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0668   -0.3616    0.7894 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0394   -0.1720   -0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7158   -0.1769    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069    0.0108   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3271   -0.0118   -0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2672    0.1488   -0.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0714    0.1128   -0.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2279   -0.0788    0.9032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2144    0.2818   -1.1166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833    0.2439   -0.5473 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2928   -0.7769   -1.0352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2881   -0.9932   -0.0846 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0153   -2.2936   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0048   -2.5397    0.5787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2156    0.1879   -0.0969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1697    0.0012    0.9287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4547    1.4307    0.2416 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2421    2.5600    0.2213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2390    1.5609   -0.6862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3960    2.5698   -0.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0153    0.2052   -1.9937 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3454    0.2135   -2.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3482    0.0257   -1.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6715    0.0325   -1.8552 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2630    0.3383    2.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9872   -1.3875    2.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6401   -0.8197    2.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -0.3366    1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1395   -0.1739    0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3577    0.3127   -1.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3883    0.0662    0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7811   -1.0065    0.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4734   -2.2679   -1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2719   -3.1160   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7671   -3.0529    0.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7192    0.3335   -1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0872    0.1417    0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0062    1.2676    1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3625    2.9437    1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5535    1.7457   -1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0941    2.4944    0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334    0.3515   -2.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5565    0.3715   -3.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9149    0.1762   -2.8260 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
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  5 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 20 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
 11 32  1  1
 13 33  1  1
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  6
 17 38  1  0
 18 39  1  1
 19 40  1  0
 20 41  1  6
 21 42  1  0
 22 43  1  0
 23 44  1  0
 25 45  1  0
M  END


  Mrv0541 02241212272D          

 25 26  0  0  0  0            999 V2000
   -3.2614    1.1049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9758    1.5174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6903    1.1049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6903    0.2799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9759   -0.1326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2614    0.2799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9759   -0.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9758    2.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4048    1.5174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4048   -0.1326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6903    2.7549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035   -1.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3110   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255   -1.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255   -2.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3110   -2.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035   -2.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7400   -2.6076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1180   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1180   -0.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8324    0.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5469   -0.1326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8324    1.1049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7400   -0.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4544   -1.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  1  0  0  0
  4  3  1  0  0  0  0
  3  9  1  6  0  0  0
  4  5  1  0  0  0  0
  4 10  1  1  0  0  0
  5  6  1  0  0  0  0
  5  7  1  6  0  0  0
  6 22  1  1  0  0  0
  8 11  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  2  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301952

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O9/c1-23-10-6-8(2-4-9(10)18)3-5-12(19)25-16-15(22)14(21)13(20)11(7-17)24-16/h2-6,11,13-18,20-22H,7H2,1H3/b5-3+/t11-,13-,14+,15-,16+/m1/s1

> <INCHI_KEY>
JWRQVQWBNRGGPK-PMQCXRHVSA-N

> <FORMULA>
C16H20O9

> <MOLECULAR_WEIGHT>
356.3246

> <EXACT_MASS>
356.110732238

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
34.31260695635697

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
-0.44

> <JCHEM_LOGP>
-0.35988508733333324

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.19756280671132

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.865378836097273

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810938220288765

> <JCHEM_POLAR_SURFACE_AREA>
145.91

> <JCHEM_REFRACTIVITY>
83.93520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.98e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301952
     RDKit          3D
trans-p-Feruloyl-beta-D-glucopyranoside
 45 46  0  0  0  0  0  0  0  0999 V2000
    6.7282   -0.5628    2.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0668   -0.3616    0.7894 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0394   -0.1720   -0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7158   -0.1769    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069    0.0108   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3271   -0.0118   -0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2672    0.1488   -0.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0714    0.1128   -0.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2279   -0.0788    0.9032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2144    0.2818   -1.1166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833    0.2439   -0.5473 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2928   -0.7769   -1.0352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2881   -0.9932   -0.0846 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0153   -2.2936   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0048   -2.5397    0.5787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2156    0.1879   -0.0969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1697    0.0012    0.9287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4547    1.4307    0.2416 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2421    2.5600    0.2213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2390    1.5609   -0.6862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3960    2.5698   -0.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0153    0.2052   -1.9937 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3454    0.2135   -2.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3482    0.0257   -1.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6715    0.0325   -1.8552 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2630    0.3383    2.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9872   -1.3875    2.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6401   -0.8197    2.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -0.3366    1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1395   -0.1739    0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3577    0.3127   -1.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3883    0.0662    0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7811   -1.0065    0.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4734   -2.2679   -1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2719   -3.1160   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7671   -3.0529    0.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7192    0.3335   -1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0872    0.1417    0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0062    1.2676    1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3625    2.9437    1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5535    1.7457   -1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0941    2.4944    0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334    0.3515   -2.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5565    0.3715   -3.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9149    0.1762   -2.8260 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
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  5 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 20 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
 11 32  1  1
 13 33  1  1
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  6
 17 38  1  0
 18 39  1  1
 19 40  1  0
 20 41  1  6
 21 42  1  0
 22 43  1  0
 23 44  1  0
 25 45  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -6.088   2.062   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -7.421   2.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.755   2.062   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.755   0.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.422  -0.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.088   0.522   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.422  -1.788   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -7.421   4.372   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -10.089   2.832   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0     -10.089  -0.248   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -8.755   5.142   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.753  -2.558   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.581  -1.788   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.914  -2.558   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.914  -4.098   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.581  -4.868   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.753  -4.098   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.248  -4.868   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.087  -1.788   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.087  -0.248   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.420   0.522   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.754  -0.248   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -3.420   2.062   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.248  -1.788   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.582  -2.558   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    1    5   22                                                  
CONECT    7    5                                                            
CONECT    8    2   11                                                       
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    8                                                            
CONECT   12   13   17   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   12   16                                                       
CONECT   18   15                                                            
CONECT   19   12   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22    6   21                                                       
CONECT   23   21                                                            
CONECT   24   14   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0301952
HETATM    1  C1  UNL     1       6.728  -0.563   2.147  1.00  0.00           C  
HETATM    2  O1  UNL     1       7.067  -0.362   0.789  1.00  0.00           O  
HETATM    3  C2  UNL     1       6.039  -0.172  -0.140  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.716  -0.177   0.236  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.707   0.011  -0.686  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.327  -0.012  -0.184  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.267   0.149  -0.922  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.071   0.113  -0.347  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.228  -0.079   0.903  1.00  0.00           O  
HETATM   10  O3  UNL     1      -1.214   0.282  -1.117  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.483   0.244  -0.547  1.00  0.00           C  
HETATM   12  O4  UNL     1      -3.293  -0.777  -1.035  1.00  0.00           O  
HETATM   13  C9  UNL     1      -4.288  -0.993  -0.085  1.00  0.00           C  
HETATM   14  C10 UNL     1      -5.015  -2.294  -0.341  1.00  0.00           C  
HETATM   15  O5  UNL     1      -6.005  -2.540   0.579  1.00  0.00           O  
HETATM   16  C11 UNL     1      -5.216   0.188  -0.097  1.00  0.00           C  
HETATM   17  O6  UNL     1      -6.170   0.001   0.929  1.00  0.00           O  
HETATM   18  C12 UNL     1      -4.455   1.431   0.242  1.00  0.00           C  
HETATM   19  O7  UNL     1      -5.242   2.560   0.221  1.00  0.00           O  
HETATM   20  C13 UNL     1      -3.239   1.561  -0.686  1.00  0.00           C  
HETATM   21  O8  UNL     1      -2.396   2.570  -0.270  1.00  0.00           O  
HETATM   22  C14 UNL     1       4.015   0.205  -1.994  1.00  0.00           C  
HETATM   23  C15 UNL     1       5.345   0.213  -2.392  1.00  0.00           C  
HETATM   24  C16 UNL     1       6.348   0.026  -1.468  1.00  0.00           C  
HETATM   25  O9  UNL     1       7.671   0.032  -1.855  1.00  0.00           O  
HETATM   26  H1  UNL     1       6.263   0.338   2.605  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.987  -1.388   2.214  1.00  0.00           H  
HETATM   28  H3  UNL     1       7.640  -0.820   2.726  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.496  -0.337   1.301  1.00  0.00           H  
HETATM   30  H5  UNL     1       2.140  -0.174   0.887  1.00  0.00           H  
HETATM   31  H6  UNL     1       1.358   0.313  -1.980  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.388   0.066   0.550  1.00  0.00           H  
HETATM   33  H8  UNL     1      -3.781  -1.006   0.902  1.00  0.00           H  
HETATM   34  H9  UNL     1      -5.473  -2.268  -1.346  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.272  -3.116  -0.358  1.00  0.00           H  
HETATM   36  H11 UNL     1      -6.767  -3.053   0.192  1.00  0.00           H  
HETATM   37  H12 UNL     1      -5.719   0.334  -1.075  1.00  0.00           H  
HETATM   38  H13 UNL     1      -7.087   0.142   0.583  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.006   1.268   1.263  1.00  0.00           H  
HETATM   40  H15 UNL     1      -5.363   2.944   1.125  1.00  0.00           H  
HETATM   41  H16 UNL     1      -3.553   1.746  -1.721  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.094   2.494   0.649  1.00  0.00           H  
HETATM   43  H18 UNL     1       3.233   0.351  -2.713  1.00  0.00           H  
HETATM   44  H19 UNL     1       5.557   0.371  -3.444  1.00  0.00           H  
HETATM   45  H20 UNL     1       7.915   0.176  -2.826  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   24
CONECT    4    5   29
CONECT    5    6   22   22
CONECT    6    7    7   30
CONECT    7    8   31
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   20   32
CONECT   12   13
CONECT   13   14   16   33
CONECT   14   15   34   35
CONECT   15   36
CONECT   16   17   18   37
CONECT   17   38
CONECT   18   19   20   39
CONECT   19   40
CONECT   20   21   41
CONECT   21   42
CONECT   22   23   43
CONECT   23   24   24   44
CONECT   24   25
CONECT   25   45
END

HMDB0301952
     RDKit          3D
trans-p-Feruloyl-beta-D-glucopyranoside
 45 46  0  0  0  0  0  0  0  0999 V2000
    6.7282   -0.5628    2.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0668   -0.3616    0.7894 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0394   -0.1720   -0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7158   -0.1769    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069    0.0108   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3271   -0.0118   -0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2672    0.1488   -0.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0714    0.1128   -0.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2279   -0.0788    0.9032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2144    0.2818   -1.1166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833    0.2439   -0.5473 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2928   -0.7769   -1.0352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2881   -0.9932   -0.0846 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0153   -2.2936   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0048   -2.5397    0.5787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2156    0.1879   -0.0969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1697    0.0012    0.9287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4547    1.4307    0.2416 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2421    2.5600    0.2213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2390    1.5609   -0.6862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3960    2.5698   -0.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0153    0.2052   -1.9937 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3454    0.2135   -2.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3482    0.0257   -1.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6715    0.0325   -1.8552 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2630    0.3383    2.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9872   -1.3875    2.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6401   -0.8197    2.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -0.3366    1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1395   -0.1739    0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3577    0.3127   -1.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3883    0.0662    0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7811   -1.0065    0.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4734   -2.2679   -1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2719   -3.1160   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7671   -3.0529    0.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7192    0.3335   -1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0872    0.1417    0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0062    1.2676    1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3625    2.9437    1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5535    1.7457   -1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0941    2.4944    0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334    0.3515   -2.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5565    0.3715   -3.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9149    0.1762   -2.8260 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
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  5 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 20 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
 11 32  1  1
 13 33  1  1
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  6
 17 38  1  0
 18 39  1  1
 19 40  1  0
 20 41  1  6
 21 42  1  0
 22 43  1  0
 23 44  1  0
 25 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-1-O-Feruloyl-beta-D-glucopyranose	ChEBI
(e)-4'-Hydroxy-3'-methoxycinnamoyl-beta-D-glucopyranose	ChEBI
1-Feruloyl-D-glucose	ChEBI
1-O-(e)-Feruloyl-beta-D-glucose	ChEBI
1-O-(e)-p-Feruloyl-beta-D-glucopyranose	ChEBI
1-O-[(e)-Feruloyl]-beta-D-glucose	ChEBI
1-O-trans-Feruloyl-beta-D-glucopyranoside	ChEBI
Ferulic acid beta-D-glucopyranosyl ester	ChEBI
trans-p-Feruloyl-beta-D-glucopyranoside	ChEBI
(e)-1-O-Feruloyl-b-D-glucopyranose	Generator
(e)-1-O-Feruloyl-β-D-glucopyranose	Generator
(e)-4'-Hydroxy-3'-methoxycinnamoyl-b-D-glucopyranose	Generator
(e)-4'-Hydroxy-3'-methoxycinnamoyl-β-D-glucopyranose	Generator
1-O-(e)-Feruloyl-b-D-glucose	Generator
1-O-(e)-Feruloyl-β-D-glucose	Generator
1-O-(e)-p-Feruloyl-b-D-glucopyranose	Generator
1-O-(e)-p-Feruloyl-β-D-glucopyranose	Generator
1-O-[(e)-Feruloyl]-b-D-glucose	Generator
1-O-[(e)-Feruloyl]-β-D-glucose	Generator
1-O-trans-Feruloyl-b-D-glucopyranoside	Generator
1-O-trans-Feruloyl-β-D-glucopyranoside	Generator
Ferulate b-D-glucopyranosyl ester	Generator
Ferulate beta-D-glucopyranosyl ester	Generator
Ferulate β-D-glucopyranosyl ester	Generator
Ferulic acid b-D-glucopyranosyl ester	Generator
Ferulic acid β-D-glucopyranosyl ester	Generator
trans-p-Feruloyl-b-D-glucopyranoside	Generator
trans-p-Feruloyl-β-D-glucopyranoside	Generator
1-O-Feruloyl-b-D-glucose	Generator
1-O-Feruloyl-β-D-glucose	Generator
1-O-(trans-Feruloyl)-beta-D-glucose	ChEBI
1-O-(trans-Feruloyl)-b-D-glucose	Generator
1-O-(trans-Feruloyl)-β-D-glucose	Generator

Chemical Formula

C₁₆H₂₀O₉

Average Molecular Weight

356.3246

Monoisotopic Molecular Weight

356.110732238

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(\C=C\C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1

InChI Identifier

InChI=1S/C16H20O9/c1-23-10-6-8(2-4-9(10)18)3-5-12(19)25-16-15(22)14(21)13(20)11(7-17)24-16/h2-6,11,13-18,20-22H,7H2,1H3/b5-3+/t11-,13-,14+,15-,16+/m1/s1

InChI Key

JWRQVQWBNRGGPK-PMQCXRHVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acid glycosides

Alternative Parents

Substituents

Hydroxycinnamic acid glycoside
O-cinnamoyl glycoside
Coumaric acid or derivatives
Hexose monosaccharide
Cinnamic acid ester
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Phenol
Alkyl aryl ether
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Polyol
Ether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Primary alcohol
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

glycoside (CHEBI:81321 )

Ontology

Not Available

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Orange bell pepper (FooDB: FOOD00879)

Tea

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.44	ALOGPS
logP	-0.36	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.87	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	6	ChemAxon
Refractivity	83.94 m³·mol⁻¹	ChemAxon
Polarizability	34.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	184.047	32859911
AllCCS	[M+H-H2O]+	181.089	32859911
AllCCS	[M+Na]+	187.563	32859911
AllCCS	[M+NH4]+	186.78	32859911
AllCCS	[M-H]-	179.612	32859911
AllCCS	[M+Na-2H]-	179.798	32859911
AllCCS	[M+HCOO]-	180.138	32859911
DeepCCS	[M+H]+	179.956	30932474
DeepCCS	[M-H]-	177.561	30932474
DeepCCS	[M-2H]-	210.443	30932474
DeepCCS	[M+Na]+	186.547	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 - trans-p-Feruloyl-beta-D-glucopyranoside 10V, Positive-QTOF	splash10-004j-0902000000-24227394506e8ab64f52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Feruloyl-beta-D-glucopyranoside 20V, Positive-QTOF	splash10-004j-0900000000-eb4cf06e241af96f6c24	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Feruloyl-beta-D-glucopyranoside 40V, Positive-QTOF	splash10-002b-3900000000-da7b3d7b488f8e9051eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Feruloyl-beta-D-glucopyranoside 10V, Negative-QTOF	splash10-004i-0902000000-37a716587e1315008931	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Feruloyl-beta-D-glucopyranoside 20V, Negative-QTOF	splash10-01tc-1900000000-39bdfa7a1ba96134e42e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Feruloyl-beta-D-glucopyranoside 40V, Negative-QTOF	splash10-002f-6900000000-322729ebffe36b54c807	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Feruloyl-beta-D-glucopyranoside 10V, Positive-QTOF	splash10-0a6r-0709000000-ce3525d91657e72b8edc	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Feruloyl-beta-D-glucopyranoside 20V, Positive-QTOF	splash10-0002-0900000000-98ca975741f21b42f0fd	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Feruloyl-beta-D-glucopyranoside 40V, Positive-QTOF	splash10-0a4i-2930000000-4f55cd0374f41611f3e0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Feruloyl-beta-D-glucopyranoside 10V, Negative-QTOF	splash10-0a6r-0906000000-4f36c3d8b3ada7e9e659	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Feruloyl-beta-D-glucopyranoside 20V, Negative-QTOF	splash10-0kcs-1913000000-bf251348657a4fd3779f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Feruloyl-beta-D-glucopyranoside 40V, Negative-QTOF	splash10-001i-1901000000-405abedc8dbb2395567e	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

FDB001666

KNApSAcK ID

Not Available

Chemspider ID

26336946

KEGG Compound ID

C17759

BioCyc ID

CPD-15281

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

81321

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 trans-p-Feruloyl-beta-D-glucopyranoside (HMDB0301952)

MOL for HMDB0301952 (trans-p-Feruloyl-beta-D-glucopyranoside)

3D MOL for HMDB0301952 (trans-p-Feruloyl-beta-D-glucopyranoside)

3D SDF for HMDB0301952 (trans-p-Feruloyl-beta-D-glucopyranoside)

3D-SDF for HMDB0301952 (trans-p-Feruloyl-beta-D-glucopyranoside)

PDB for HMDB0301952 (trans-p-Feruloyl-beta-D-glucopyranoside)

3D PDB for HMDB0301952 (trans-p-Feruloyl-beta-D-glucopyranoside)

SMILES for HMDB0301952 (trans-p-Feruloyl-beta-D-glucopyranoside)

INCHI for HMDB0301952 (trans-p-Feruloyl-beta-D-glucopyranoside)

Structure for HMDB0301952 (trans-p-Feruloyl-beta-D-glucopyranoside)

3D Structure for HMDB0301952 (trans-p-Feruloyl-beta-D-glucopyranoside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra