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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 06:30:06 UTC

Update Date

2021-09-23 06:30:07 UTC

HMDB ID

HMDB0302092

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1-O-Feruloyl-beta-D-glucopyranose

Description

1-o-feruloyl-beta-d-glucopyranose is a member of the class of compounds known as hydroxycinnamic acid glycosides. Hydroxycinnamic acid glycosides are glycosylated hydoxycinnamic acids derivatives. 1-o-feruloyl-beta-d-glucopyranose is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 1-o-feruloyl-beta-d-glucopyranose can be found in loquat, which makes 1-o-feruloyl-beta-d-glucopyranose a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302092
     RDKit          3D
1-O-Feruloyl-beta-D-glucopyranose
 45 46  0  0  0  0  0  0  0  0999 V2000
    8.1253    0.8656   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6102   -0.4498   -0.5500 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2192   -0.6003   -0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3628    0.4856   -0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0055    0.3609   -0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4282   -0.8851   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9785   -1.0633   -0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1126   -0.0914   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146   -0.4042   -0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110   -1.5940    0.0719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2735    0.5940    0.0175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422    0.2462    0.1266 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3698    0.6429   -0.9857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6710    0.2077   -0.8266 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4543    0.1495   -2.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7979   -0.7381   -2.9584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3219    1.0829    0.2191 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6864    0.8839    0.3166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6523    0.7597    1.5432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0556    1.6407    2.5440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1550    0.8014    1.4153 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6447   -0.0198    2.4471 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2669   -1.9800   -0.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6333   -1.8433   -0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4645   -2.9639   -0.3641 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7483    1.4013   -1.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8163    1.3895    0.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2308    0.8449   -0.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8328    1.4737   -0.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4148    1.2595   -0.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6072   -2.0820   -0.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4310    0.9192   -0.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7477   -0.8718    0.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6112   -0.8292   -0.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4371   -0.3025   -1.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5333    1.1383   -2.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8650   -1.6630   -2.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0682    2.1336   -0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1407    1.6059   -0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9409   -0.2878    1.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4548    2.4255    2.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7513    1.8277    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190    0.4248    2.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8405   -2.9896   -0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0905   -3.9057   -0.2982 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  6 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 21 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  8 32  1  0
 12 33  1  1
 14 34  1  1
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  6
 18 39  1  0
 19 40  1  1
 20 41  1  0
 21 42  1  1
 22 43  1  0
 23 44  1  0
 25 45  1  0
M  END

  Mrv0541 02241212142D          

 25 26  0  0  0  0            999 V2000
   -2.9081    1.8950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6226    2.3075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3371    1.8950    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3371    1.0700    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6776    0.6938    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9081    1.0700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6226   -0.1675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6226    3.1325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0515    2.3075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0516    0.6575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3371    3.5450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3787    1.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6642    0.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6642   -0.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3787   -0.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932   -0.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    0.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8076   -0.5800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3787   -1.4050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0502    1.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7647    0.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792    1.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1937    0.6575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221   -0.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792    1.8950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  2  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 23  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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 24  1  0  0  0  0
 22 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302092

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(\C=C\C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O9/c1-23-10-4-2-8(6-9(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>
RFTKPXQZIVKVOP-PMQCXRHVSA-N

> <FORMULA>
C16H20O9

> <MOLECULAR_WEIGHT>
356.3246

> <EXACT_MASS>
356.110732238

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
35.2212567070743

> <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-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
-0.45

> <JCHEM_LOGP>
-0.35988508733333324

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.19738504276146

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.82108788715303

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810938220288765

> <JCHEM_POLAR_SURFACE_AREA>
145.91

> <JCHEM_REFRACTIVITY>
83.9352

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.96e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302092
     RDKit          3D
1-O-Feruloyl-beta-D-glucopyranose
 45 46  0  0  0  0  0  0  0  0999 V2000
    8.1253    0.8656   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6102   -0.4498   -0.5500 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2192   -0.6003   -0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3628    0.4856   -0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0055    0.3609   -0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4282   -0.8851   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9785   -1.0633   -0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1126   -0.0914   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146   -0.4042   -0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110   -1.5940    0.0719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2735    0.5940    0.0175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422    0.2462    0.1266 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3698    0.6429   -0.9857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6710    0.2077   -0.8266 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4543    0.1495   -2.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7979   -0.7381   -2.9584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3219    1.0829    0.2191 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6864    0.8839    0.3166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6523    0.7597    1.5432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0556    1.6407    2.5440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1550    0.8014    1.4153 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6447   -0.0198    2.4471 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2669   -1.9800   -0.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6333   -1.8433   -0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4645   -2.9639   -0.3641 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7483    1.4013   -1.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8163    1.3895    0.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2308    0.8449   -0.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8328    1.4737   -0.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4148    1.2595   -0.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6072   -2.0820   -0.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4310    0.9192   -0.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7477   -0.8718    0.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6112   -0.8292   -0.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4371   -0.3025   -1.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5333    1.1383   -2.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8650   -1.6630   -2.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0682    2.1336   -0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1407    1.6059   -0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9409   -0.2878    1.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4548    2.4255    2.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7513    1.8277    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190    0.4248    2.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8405   -2.9896   -0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0905   -3.9057   -0.2982 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  6 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 21 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  8 32  1  0
 12 33  1  1
 14 34  1  1
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  6
 18 39  1  0
 19 40  1  1
 20 41  1  0
 21 42  1  1
 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      -5.428   3.537   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -6.762   4.307   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.096   3.537   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.096   1.997   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.865   1.295   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.428   1.997   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.762  -0.313   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.762   5.847   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -9.429   4.307   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -9.430   1.227   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -8.096   6.617   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.574   1.997   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.240   1.227   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.240  -0.313   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.574  -1.083   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.907  -0.313   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.907   1.227   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.241  -1.083   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.574  -2.623   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.094   1.997   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.427   1.227   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.761   1.997   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.095   1.227   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.575  -0.313   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.761   3.537   0.000  0.00  0.00           O+0
CONECT    1    6    2                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    1    5   23                                                  
CONECT    7    5                                                            
CONECT    8    2   11                                                       
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    8                                                            
CONECT   12   13   17                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   12   16                                                       
CONECT   18   16   24                                                       
CONECT   19   15                                                            
CONECT   20   13   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23    6   22                                                       
CONECT   24   18                                                            
CONECT   25   22                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0302092
HETATM    1  C1  UNL     1       8.125   0.866  -0.641  1.00  0.00           C  
HETATM    2  O1  UNL     1       7.610  -0.450  -0.550  1.00  0.00           O  
HETATM    3  C2  UNL     1       6.219  -0.600  -0.448  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.363   0.486  -0.435  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.006   0.361  -0.336  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.428  -0.885  -0.243  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.978  -1.063  -0.136  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.113  -0.091  -0.118  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.315  -0.404  -0.006  1.00  0.00           C  
HETATM   10  O2  UNL     1      -0.711  -1.594   0.072  1.00  0.00           O  
HETATM   11  O3  UNL     1      -1.274   0.594   0.018  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.642   0.246   0.127  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.370   0.643  -0.986  1.00  0.00           O  
HETATM   14  C10 UNL     1      -4.671   0.208  -0.827  1.00  0.00           C  
HETATM   15  C11 UNL     1      -5.454   0.149  -2.101  1.00  0.00           C  
HETATM   16  O5  UNL     1      -4.798  -0.738  -2.958  1.00  0.00           O  
HETATM   17  C12 UNL     1      -5.322   1.083   0.219  1.00  0.00           C  
HETATM   18  O6  UNL     1      -6.686   0.884   0.317  1.00  0.00           O  
HETATM   19  C13 UNL     1      -4.652   0.760   1.543  1.00  0.00           C  
HETATM   20  O7  UNL     1      -5.056   1.641   2.544  1.00  0.00           O  
HETATM   21  C14 UNL     1      -3.155   0.801   1.415  1.00  0.00           C  
HETATM   22  O8  UNL     1      -2.645  -0.020   2.447  1.00  0.00           O  
HETATM   23  C15 UNL     1       4.267  -1.980  -0.255  1.00  0.00           C  
HETATM   24  C16 UNL     1       5.633  -1.843  -0.355  1.00  0.00           C  
HETATM   25  O9  UNL     1       6.465  -2.964  -0.364  1.00  0.00           O  
HETATM   26  H1  UNL     1       7.748   1.401  -1.532  1.00  0.00           H  
HETATM   27  H2  UNL     1       7.816   1.389   0.292  1.00  0.00           H  
HETATM   28  H3  UNL     1       9.231   0.845  -0.647  1.00  0.00           H  
HETATM   29  H4  UNL     1       5.833   1.474  -0.509  1.00  0.00           H  
HETATM   30  H5  UNL     1       3.415   1.259  -0.334  1.00  0.00           H  
HETATM   31  H6  UNL     1       1.607  -2.082  -0.067  1.00  0.00           H  
HETATM   32  H7  UNL     1       1.431   0.919  -0.183  1.00  0.00           H  
HETATM   33  H8  UNL     1      -2.748  -0.872   0.181  1.00  0.00           H  
HETATM   34  H9  UNL     1      -4.611  -0.829  -0.388  1.00  0.00           H  
HETATM   35  H10 UNL     1      -6.437  -0.303  -1.873  1.00  0.00           H  
HETATM   36  H11 UNL     1      -5.533   1.138  -2.564  1.00  0.00           H  
HETATM   37  H12 UNL     1      -4.865  -1.663  -2.570  1.00  0.00           H  
HETATM   38  H13 UNL     1      -5.068   2.134  -0.045  1.00  0.00           H  
HETATM   39  H14 UNL     1      -7.141   1.606  -0.222  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.941  -0.288   1.791  1.00  0.00           H  
HETATM   41  H16 UNL     1      -4.455   2.425   2.482  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.751   1.828   1.617  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.919   0.425   2.939  1.00  0.00           H  
HETATM   44  H19 UNL     1       3.841  -2.990  -0.182  1.00  0.00           H  
HETATM   45  H20 UNL     1       6.091  -3.906  -0.298  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    6   30
CONECT    6    7   23
CONECT    7    8    8   31
CONECT    8    9   32
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13   21   33
CONECT   13   14
CONECT   14   15   17   34
CONECT   15   16   35   36
CONECT   16   37
CONECT   17   18   19   38
CONECT   18   39
CONECT   19   20   21   40
CONECT   20   41
CONECT   21   22   42
CONECT   22   43
CONECT   23   24   24   44
CONECT   24   25
CONECT   25   45
END

HMDB0302092
     RDKit          3D
1-O-Feruloyl-beta-D-glucopyranose
 45 46  0  0  0  0  0  0  0  0999 V2000
    8.1253    0.8656   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6102   -0.4498   -0.5500 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2192   -0.6003   -0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3628    0.4856   -0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0055    0.3609   -0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4282   -0.8851   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9785   -1.0633   -0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1126   -0.0914   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146   -0.4042   -0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110   -1.5940    0.0719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2735    0.5940    0.0175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422    0.2462    0.1266 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3698    0.6429   -0.9857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6710    0.2077   -0.8266 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4543    0.1495   -2.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7979   -0.7381   -2.9584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3219    1.0829    0.2191 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6864    0.8839    0.3166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6523    0.7597    1.5432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0556    1.6407    2.5440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1550    0.8014    1.4153 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6447   -0.0198    2.4471 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2669   -1.9800   -0.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6333   -1.8433   -0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4645   -2.9639   -0.3641 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7483    1.4013   -1.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8163    1.3895    0.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2308    0.8449   -0.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8328    1.4737   -0.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4148    1.2595   -0.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6072   -2.0820   -0.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4310    0.9192   -0.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7477   -0.8718    0.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6112   -0.8292   -0.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4371   -0.3025   -1.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5333    1.1383   -2.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8650   -1.6630   -2.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0682    2.1336   -0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1407    1.6059   -0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9409   -0.2878    1.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4548    2.4255    2.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7513    1.8277    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190    0.4248    2.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8405   -2.9896   -0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0905   -3.9057   -0.2982 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  6 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 21 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  8 32  1  0
 12 33  1  1
 14 34  1  1
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  6
 18 39  1  0
 19 40  1  1
 20 41  1  0
 21 42  1  1
 22 43  1  0
 23 44  1  0
 25 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid	Generator
1-O-Feruloyl-b-D-glucopyranose	Generator
1-O-Feruloyl-β-D-glucopyranose	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-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC=C(\C=C\C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1O

InChI Identifier

InChI=1S/C16H20O9/c1-23-10-4-2-8(6-9(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

RFTKPXQZIVKVOP-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
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Fatty acid ester
Oxane
Monosaccharide
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Ether
Polyol
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Organic oxide
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302092)

Food

Fruit

Tropical fruit

Loquat (FooDB: FOOD00076)

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	-0.45	ALOGPS
logP	-0.36	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.82	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	35.22 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]+	184.136	32859911
AllCCS	[M+H-H2O]+	181.201	32859911
AllCCS	[M+Na]+	187.625	32859911
AllCCS	[M+NH4]+	186.848	32859911
AllCCS	[M-H]-	179.91	32859911
AllCCS	[M+Na-2H]-	180.126	32859911
AllCCS	[M+HCOO]-	180.499	32859911
DeepCCS	[M+H]+	182.556	30932474
DeepCCS	[M-H]-	180.16	30932474
DeepCCS	[M-2H]-	213.131	30932474
DeepCCS	[M+Na]+	188.468	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 - 1-O-Feruloyl-beta-D-glucopyranose 10V, Positive-QTOF	splash10-004j-0902000000-236f89411624c4377548	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucopyranose 20V, Positive-QTOF	splash10-004j-0900000000-1648fba411d010998779	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucopyranose 40V, Positive-QTOF	splash10-0092-3900000000-7eeb712470c4346ce6db	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucopyranose 10V, Negative-QTOF	splash10-004i-0902000000-14a548c62b3848178713	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucopyranose 20V, Negative-QTOF	splash10-004l-1900000000-6c7d815c229737f1cd07	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucopyranose 40V, Negative-QTOF	splash10-002f-6900000000-2c2d13f8e5cba3d6fab1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucopyranose 10V, Positive-QTOF	splash10-0a4i-0709000000-e21d612a1fb50f4587e5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucopyranose 20V, Positive-QTOF	splash10-0002-0910000000-e8fa96b16d9191a637a1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucopyranose 40V, Positive-QTOF	splash10-0a4s-4970000000-e38f199ec27c08831bf5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucopyranose 10V, Negative-QTOF	splash10-0a4i-0908000000-a9653b36abe3c1fd39bd	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucopyranose 20V, Negative-QTOF	splash10-0a7j-1921000000-97ac9898841ff704855d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucopyranose 40V, Negative-QTOF	splash10-000t-1900000000-e498f67b3116d0815318	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

FDB001848

KNApSAcK ID

Not Available

Chemspider ID

59696281

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 1-O-Feruloyl-beta-D-glucopyranose (HMDB0302092)

MOL for HMDB0302092 (1-O-Feruloyl-beta-D-glucopyranose)

3D MOL for HMDB0302092 (1-O-Feruloyl-beta-D-glucopyranose)

3D SDF for HMDB0302092 (1-O-Feruloyl-beta-D-glucopyranose)

3D-SDF for HMDB0302092 (1-O-Feruloyl-beta-D-glucopyranose)

PDB for HMDB0302092 (1-O-Feruloyl-beta-D-glucopyranose)

3D PDB for HMDB0302092 (1-O-Feruloyl-beta-D-glucopyranose)

SMILES for HMDB0302092 (1-O-Feruloyl-beta-D-glucopyranose)

INCHI for HMDB0302092 (1-O-Feruloyl-beta-D-glucopyranose)

Structure for HMDB0302092 (1-O-Feruloyl-beta-D-glucopyranose)

3D Structure for HMDB0302092 (1-O-Feruloyl-beta-D-glucopyranose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra