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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-22 16:36:16 UTC

Update Date

2021-09-22 16:36:16 UTC

HMDB ID

HMDB0301717

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Ferulic acid 4-glucoside

Description

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

Structure

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

HMDB0301717
     RDKit          3D
Ferulic acid 4-glucoside
 45 46  0  0  0  0  0  0  0  0999 V2000
    2.1245   -2.0341   -3.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1867   -1.4492   -2.3316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6693   -0.8129   -1.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126   -0.7642   -0.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5329   -0.1403    0.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9764   -0.1213    0.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5366    0.4463    1.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0021    0.4098    1.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6761   -0.1542    0.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6288    0.9970    2.7153 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6237    0.4314    1.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2557    0.3825    0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7521   -0.2233   -0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5647   -0.3176   -0.6414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6758    0.1822    0.0592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4237   -0.9031    0.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5451   -0.3906    1.1447 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1783   -1.4147    2.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2776   -0.8203    2.6658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4826    0.0387    0.0348 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7552    0.3039    0.4922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8526    1.3080   -0.5356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5474    1.7634   -1.6554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4013    1.1312   -0.8328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7815    2.3901   -0.6959 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5870   -2.6070   -3.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8398   -2.6886   -2.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6529   -1.2006   -3.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7406   -1.2234   -1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6227   -0.6031   -0.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9475    0.9355    2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8682    1.9900    2.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9791    0.9358    1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176    0.8482    1.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3093    0.6880    0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1778    0.4887    1.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4899   -1.8382    2.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5958   -2.2155    1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9310   -1.5247    2.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4869   -0.6996   -0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3462    0.3675   -0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0043    2.0889    0.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2401    2.6926   -1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2965    0.8603   -1.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4695    2.4667    0.2615 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
  5 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 13  3  1  0
 24 15  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
 10 32  1  0
 11 33  1  0
 12 34  1  0
 15 35  1  1
 17 36  1  1
 18 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  6
 21 41  1  0
 22 42  1  1
 23 43  1  0
 24 44  1  6
 25 45  1  0
M  END

  Mrv1652309272007292D          

 25 26  0  0  0  0            999 V2000
 9994.2539 9994.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1130 9995.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8269 9995.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5430 9995.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2569 9995.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5430 9996.7900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8245 9996.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1097 9997.2027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8245 9993.4891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.3949 9994.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.3949 9995.9647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8245 9995.9643    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9992.1100 9995.5518    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9992.1100 9994.7268    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9992.8245 9994.3145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9993.5389 9994.7268    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9993.5389 9995.5518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3988 9995.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6844 9995.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.9699 9995.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.9699 9994.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6842 9994.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3988 9994.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6841 9993.4898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3983 9993.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 18  1  0  0  0  0
  1 21  1  0  0  0  0
 18  2  1  0  0  0  0
 16  1  1  1  0  0  0
 12  7  1  1  0  0  0
 13 11  1  6  0  0  0
 14 10  1  1  0  0  0
 15  9  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301717

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
IEMIRSXOYFWPFD-BJGSYIFTSA-N

> <FORMULA>
C16H20O9

> <MOLECULAR_WEIGHT>
356.3246

> <EXACT_MASS>
356.110732238

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.80012800525954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.29

> <JCHEM_LOGP>
-0.5932184206666665

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.200014897776562

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.573304769582638

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549072026

> <JCHEM_POLAR_SURFACE_AREA>
145.91

> <JCHEM_REFRACTIVITY>
83.64839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.91e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301717
     RDKit          3D
Ferulic acid 4-glucoside
 45 46  0  0  0  0  0  0  0  0999 V2000
    2.1245   -2.0341   -3.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1867   -1.4492   -2.3316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6693   -0.8129   -1.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126   -0.7642   -0.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5329   -0.1403    0.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9764   -0.1213    0.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5366    0.4463    1.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0021    0.4098    1.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6761   -0.1542    0.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6288    0.9970    2.7153 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6237    0.4314    1.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2557    0.3825    0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7521   -0.2233   -0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5647   -0.3176   -0.6414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6758    0.1822    0.0592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4237   -0.9031    0.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5451   -0.3906    1.1447 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1783   -1.4147    2.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2776   -0.8203    2.6658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4826    0.0387    0.0348 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7552    0.3039    0.4922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8526    1.3080   -0.5356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5474    1.7634   -1.6554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4013    1.1312   -0.8328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7815    2.3901   -0.6959 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5870   -2.6070   -3.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8398   -2.6886   -2.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6529   -1.2006   -3.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7406   -1.2234   -1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6227   -0.6031   -0.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9475    0.9355    2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8682    1.9900    2.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9791    0.9358    1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176    0.8482    1.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3093    0.6880    0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1778    0.4887    1.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4899   -1.8382    2.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5958   -2.2155    1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9310   -1.5247    2.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4869   -0.6996   -0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3462    0.3675   -0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0043    2.0889    0.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2401    2.6926   -1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2965    0.8603   -1.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4695    2.4667    0.2615 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
  5 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 13  3  1  0
 24 15  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
 10 32  1  0
 11 33  1  0
 12 34  1  0
 15 35  1  1
 17 36  1  1
 18 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  6
 21 41  1  0
 22 42  1  1
 23 43  1  0
 24 44  1  6
 25 45  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    8655.9418656.054   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8661.2788659.134   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8662.6108658.364   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.9478659.134   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8665.2808658.364   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8663.9478660.675   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8653.2728660.675   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8651.9388661.445   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8653.2728654.513   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8650.6048656.054   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8650.6048659.134   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8653.2728659.133   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8651.9398658.363   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8651.9398656.823   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8653.2728656.054   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8654.6068656.823   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8654.6068658.363   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8659.9448658.363   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8658.6118659.133   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8657.2778658.363   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8657.2778656.823   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8658.6118656.054   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8659.9448656.823   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8658.6108654.514   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0    8659.9448653.744   0.000  0.00  0.00           C+0
CONECT    1   21   16                                                       
CONECT    2    3   18                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    8   12                                                       
CONECT    8    7                                                            
CONECT    9   15                                                            
CONECT   10   14                                                            
CONECT   11   13                                                            
CONECT   12   13   17    7                                                  
CONECT   13   12   14   11                                                  
CONECT   14   13   15   10                                                  
CONECT   15   14   16    9                                                  
CONECT   16   15   17    1                                                  
CONECT   17   12   16                                                       
CONECT   18   19   23    2                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22    1                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   18                                                       
CONECT   24   22   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0301717
HETATM    1  C1  UNL     1       2.125  -2.034  -3.201  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.187  -1.449  -2.332  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.669  -0.813  -1.181  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.013  -0.764  -0.915  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.533  -0.140   0.219  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.976  -0.121   0.448  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.537   0.446   1.492  1.00  0.00           C  
HETATM    8  C7  UNL     1       7.002   0.410   1.629  1.00  0.00           C  
HETATM    9  O2  UNL     1       7.676  -0.154   0.759  1.00  0.00           O  
HETATM   10  O3  UNL     1       7.629   0.997   2.715  1.00  0.00           O  
HETATM   11  C8  UNL     1       2.624   0.431   1.070  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.256   0.383   0.800  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.752  -0.223  -0.301  1.00  0.00           C  
HETATM   14  O4  UNL     1      -0.565  -0.318  -0.641  1.00  0.00           O  
HETATM   15  C11 UNL     1      -1.676   0.182   0.059  1.00  0.00           C  
HETATM   16  O5  UNL     1      -2.424  -0.903   0.480  1.00  0.00           O  
HETATM   17  C12 UNL     1      -3.545  -0.391   1.145  1.00  0.00           C  
HETATM   18  C13 UNL     1      -4.178  -1.415   2.050  1.00  0.00           C  
HETATM   19  O6  UNL     1      -5.278  -0.820   2.666  1.00  0.00           O  
HETATM   20  C14 UNL     1      -4.483   0.039   0.035  1.00  0.00           C  
HETATM   21  O7  UNL     1      -5.755   0.304   0.492  1.00  0.00           O  
HETATM   22  C15 UNL     1      -3.853   1.308  -0.536  1.00  0.00           C  
HETATM   23  O8  UNL     1      -4.547   1.763  -1.655  1.00  0.00           O  
HETATM   24  C16 UNL     1      -2.401   1.131  -0.833  1.00  0.00           C  
HETATM   25  O9  UNL     1      -1.781   2.390  -0.696  1.00  0.00           O  
HETATM   26  H1  UNL     1       1.587  -2.607  -3.982  1.00  0.00           H  
HETATM   27  H2  UNL     1       2.840  -2.689  -2.696  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.653  -1.201  -3.726  1.00  0.00           H  
HETATM   29  H4  UNL     1       3.741  -1.223  -1.599  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.623  -0.603  -0.285  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.948   0.935   2.245  1.00  0.00           H  
HETATM   32  H7  UNL     1       7.868   1.990   2.642  1.00  0.00           H  
HETATM   33  H8  UNL     1       2.979   0.936   1.978  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.618   0.848   1.507  1.00  0.00           H  
HETATM   35  H10 UNL     1      -1.309   0.688   0.972  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.178   0.489   1.719  1.00  0.00           H  
HETATM   37  H12 UNL     1      -3.490  -1.838   2.777  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.596  -2.216   1.388  1.00  0.00           H  
HETATM   39  H14 UNL     1      -5.931  -1.525   2.953  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.487  -0.700  -0.793  1.00  0.00           H  
HETATM   41  H16 UNL     1      -6.346   0.368  -0.301  1.00  0.00           H  
HETATM   42  H17 UNL     1      -4.004   2.089   0.260  1.00  0.00           H  
HETATM   43  H18 UNL     1      -4.240   2.693  -1.818  1.00  0.00           H  
HETATM   44  H19 UNL     1      -2.296   0.860  -1.905  1.00  0.00           H  
HETATM   45  H20 UNL     1      -1.469   2.467   0.262  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   29
CONECT    5    6   11   11
CONECT    6    7    7   30
CONECT    7    8   31
CONECT    8    9    9   10
CONECT   10   32
CONECT   11   12   33
CONECT   12   13   13   34
CONECT   13   14
CONECT   14   15
CONECT   15   16   24   35
CONECT   16   17
CONECT   17   18   20   36
CONECT   18   19   37   38
CONECT   19   39
CONECT   20   21   22   40
CONECT   21   41
CONECT   22   23   24   42
CONECT   23   43
CONECT   24   25   44
CONECT   25   45
END

HMDB0301717
     RDKit          3D
Ferulic acid 4-glucoside
 45 46  0  0  0  0  0  0  0  0999 V2000
    2.1245   -2.0341   -3.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1867   -1.4492   -2.3316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6693   -0.8129   -1.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126   -0.7642   -0.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5329   -0.1403    0.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9764   -0.1213    0.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5366    0.4463    1.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0021    0.4098    1.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6761   -0.1542    0.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6288    0.9970    2.7153 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6237    0.4314    1.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2557    0.3825    0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7521   -0.2233   -0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5647   -0.3176   -0.6414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6758    0.1822    0.0592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4237   -0.9031    0.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5451   -0.3906    1.1447 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1783   -1.4147    2.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2776   -0.8203    2.6658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4826    0.0387    0.0348 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7552    0.3039    0.4922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8526    1.3080   -0.5356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5474    1.7634   -1.6554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4013    1.1312   -0.8328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7815    2.3901   -0.6959 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5870   -2.6070   -3.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8398   -2.6886   -2.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6529   -1.2006   -3.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7406   -1.2234   -1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6227   -0.6031   -0.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9475    0.9355    2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8682    1.9900    2.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9791    0.9358    1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176    0.8482    1.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3093    0.6880    0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1778    0.4887    1.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4899   -1.8382    2.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5958   -2.2155    1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9310   -1.5247    2.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4869   -0.6996   -0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3462    0.3675   -0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0043    2.0889    0.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2401    2.6926   -1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2965    0.8603   -1.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4695    2.4667    0.2615 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
  5 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 13  3  1  0
 24 15  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
 10 32  1  0
 11 33  1  0
 12 34  1  0
 15 35  1  1
 17 36  1  1
 18 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  6
 21 41  1  0
 22 42  1  1
 23 43  1  0
 24 44  1  6
 25 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E)-3-(3-Methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate	Generator
Ferulate 4-glucoside	Generator
(2E)-3-[4-(beta-D-Glucopyranosyloxy)-3-methoxyphenyl]-2-propenoic acid	PhytoBank
(2E)-3-[4-(β-D-Glucopyranosyloxy)-3-methoxyphenyl]-2-propenoic acid	PhytoBank
(E)-Ferulic acid 4-O-beta-D-glucoside	PhytoBank
(E)-Ferulic acid 4-O-β-D-glucoside	PhytoBank
Ferulic acid 4-O-glucoside	PhytoBank
Ferulic acid 4-O-beta-glucopyranoside	PhytoBank
Ferulic acid 4-O-β-glucopyranoside	PhytoBank
Lavandoside	PhytoBank
trans-4-O-beta-D-Glucopyranosylferulic acid	PhytoBank
trans-4-O-β-D-Glucopyranosylferulic acid	PhytoBank
trans-Ferulic acid 4-beta-D-glucoside	PhytoBank
trans-Ferulic acid 4-β-D-glucoside	PhytoBank
trans-Ferulic acid-4-beta-glucoside	PhytoBank
trans-Ferulic acid-4-β-glucoside	PhytoBank
trans-p-Feruloyl-beta-D-glucopyranoside	PhytoBank
trans-p-Feruloyl-β-D-glucopyranoside	PhytoBank
Ferulic acid 4-O-beta-D-glucopyranoside	PhytoBank
Ferulic acid 4-O-β-D-glucopyranoside	PhytoBank

Chemical Formula

C₁₆H₂₀O₉

Average Molecular Weight

356.3246

Monoisotopic Molecular Weight

356.110732238

IUPAC Name

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

Traditional Name

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

CAS Registry Number

537-98-4

SMILES

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

InChI Identifier

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

InChI Key

IEMIRSXOYFWPFD-BJGSYIFTSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Acetal
Polyol
Alcohol
Carbonyl group
Organic oxide
Primary alcohol
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0301717)

Food

Fruit

Berry

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

Vegetable

Root vegetable

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

Fruit vegetable

Garden tomato (var.) (FooDB: FOOD00173)

Herb and spice

Oilseed crop

Flaxseed (FooDB: FOOD00101)

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	-0.29	ALOGPS
logP	-0.59	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.57	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	6	ChemAxon
Refractivity	83.65 m³·mol⁻¹	ChemAxon
Polarizability	34.8 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]+	183.331	32859911
AllCCS	[M+H-H2O]+	180.463	32859911
AllCCS	[M+Na]+	186.736	32859911
AllCCS	[M+NH4]+	185.978	32859911
AllCCS	[M-H]-	179.626	32859911
AllCCS	[M+Na-2H]-	179.81	32859911
AllCCS	[M+HCOO]-	180.148	32859911
DeepCCS	[M+H]+	180.151	30932474
DeepCCS	[M-H]-	177.756	30932474
DeepCCS	[M-2H]-	211.473	30932474
DeepCCS	[M+Na]+	186.458	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 - Ferulic acid 4-glucoside 10V, Positive-QTOF	splash10-054t-0916000000-ebc1cc4896fdc64a458c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 20V, Positive-QTOF	splash10-002b-0900000000-6a902dabbbf78442f23e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 40V, Positive-QTOF	splash10-004s-1900000000-e4ad1acd6f4850f0bc2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 10V, Negative-QTOF	splash10-0a4l-1819000000-eba6f8f85bf8d5d53934	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 20V, Negative-QTOF	splash10-002f-1911000000-77f2053078c1eb574d28	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 40V, Negative-QTOF	splash10-004l-2900000000-2ff1d99e129350f50621	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 10V, Positive-QTOF	splash10-052s-0219000000-b7234cdb53b60902464c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 20V, Positive-QTOF	splash10-01y2-0914000000-a18d425b2a03a2eee99b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 40V, Positive-QTOF	splash10-001j-1920000000-3cd8ce35afe706d70b23	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 10V, Negative-QTOF	splash10-0a4i-0109000000-be106f09d2f43d279f4f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 20V, Negative-QTOF	splash10-0002-2893000000-9a4389f84bbaed564315	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 40V, Negative-QTOF	splash10-0002-3902000000-98c283edf136c4ee19bf	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

FDB000256

KNApSAcK ID

Not Available

Chemspider ID

10212167

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 Ferulic acid 4-glucoside (HMDB0301717)

MOL for HMDB0301717 (Ferulic acid 4-glucoside)

3D MOL for HMDB0301717 (Ferulic acid 4-glucoside)

3D SDF for HMDB0301717 (Ferulic acid 4-glucoside)

3D-SDF for HMDB0301717 (Ferulic acid 4-glucoside)

PDB for HMDB0301717 (Ferulic acid 4-glucoside)

3D PDB for HMDB0301717 (Ferulic acid 4-glucoside)

SMILES for HMDB0301717 (Ferulic acid 4-glucoside)

INCHI for HMDB0301717 (Ferulic acid 4-glucoside)

Structure for HMDB0301717 (Ferulic acid 4-glucoside)

3D Structure for HMDB0301717 (Ferulic acid 4-glucoside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra