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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 16:04:51 UTC

Update Date

2021-09-23 16:04:51 UTC

HMDB ID

HMDB0302219

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1-O-Feruloyl-beta-D-glucose

Description

1-o-feruloyl-beta-d-glucose belongs to coumaric acids and derivatives class of compounds. Those are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 1-o-feruloyl-beta-d-glucose is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 1-o-feruloyl-beta-d-glucose can be found in a number of food items such as chives, yellow bell pepper, white cabbage, and orange bell pepper, which makes 1-o-feruloyl-beta-d-glucose a potential biomarker for the consumption of these food products.

Structure

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

HMDB0302219
     RDKit          3D
1-O-Feruloyl-beta-D-glucose
 45 46  0  0  0  0  0  0  0  0999 V2000
    7.4837    1.1106    1.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5438    0.4298    0.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5610   -0.2147   -0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2286    0.1984    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1812   -0.4654   -0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7760   -0.0588   -0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4124    0.9696    0.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0088    1.2984    0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3953    2.2800    1.3604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9381    0.5254    0.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3181    0.7380    0.1274 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9844    0.9354   -1.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3875    1.9321   -1.9232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3120    1.3340   -0.9325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0412    0.2648   -0.3651 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4804    0.7887   -0.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2613   -0.2013    0.2869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4729    0.0497    1.0214 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2093   -0.8263    1.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0363   -0.4060    0.8410 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4315   -0.6871    2.0619 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4510   -1.5708   -1.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7421   -1.9973   -1.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8056   -1.3489   -0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1183   -1.7290   -1.0519 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8280    2.0565    0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1810    1.5123    2.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4597    0.5801    1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0486    1.0736    0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0173   -0.6828   -0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430    1.5779    1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4961    1.6345    0.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0741   -0.0001   -1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8998    2.7578   -1.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0325   -0.6279   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5095    1.7180    0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8505    1.0537   -1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6950   -0.7769   -0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4323    1.0769    1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5500   -1.5365    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0537   -1.2723    0.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0837   -1.5954    2.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6285   -2.1192   -1.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9528   -2.8728   -2.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3743   -2.5168   -1.6045 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
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  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
 12 33  1  0
 13 34  1  0
 15 35  1  6
 16 36  1  0
 16 37  1  0
 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 02241221062D          

 25 26  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  1  1  0  0  0
 21 22  1  0  0  0  0
 16 23  1  6  0  0  0
 15 24  1  1  0  0  0
  4 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302219

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)O[C@H]2C(O)O[C@H](CO)[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)25-15-14(21)13(20)11(7-17)24-16(15)22/h2-6,11,13-18,20-22H,7H2,1H3/b5-3+/t11-,13-,14+,15-,16?/m1/s1

> <INCHI_KEY>
ADHNTNYEJYJUCU-ZSJFXSENSA-N

> <FORMULA>
C16H20O9

> <MOLECULAR_WEIGHT>
356.3246

> <EXACT_MASS>
356.110732238

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
35.046618806211086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.44

> <JCHEM_LOGP>
-0.35988508733333324

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.316848849184597

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.852013844288805

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981079852824804

> <JCHEM_POLAR_SURFACE_AREA>
145.91000000000003

> <JCHEM_REFRACTIVITY>
83.9352

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.59e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302219
     RDKit          3D
1-O-Feruloyl-beta-D-glucose
 45 46  0  0  0  0  0  0  0  0999 V2000
    7.4837    1.1106    1.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5438    0.4298    0.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5610   -0.2147   -0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2286    0.1984    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1812   -0.4654   -0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7760   -0.0588   -0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4124    0.9696    0.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0088    1.2984    0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3953    2.2800    1.3604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9381    0.5254    0.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3181    0.7380    0.1274 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9844    0.9354   -1.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3875    1.9321   -1.9232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3120    1.3340   -0.9325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0412    0.2648   -0.3651 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4804    0.7887   -0.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2613   -0.2013    0.2869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4729    0.0497    1.0214 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2093   -0.8263    1.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0363   -0.4060    0.8410 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4315   -0.6871    2.0619 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4510   -1.5708   -1.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7421   -1.9973   -1.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8056   -1.3489   -0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1183   -1.7290   -1.0519 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8280    2.0565    0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1810    1.5123    2.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4597    0.5801    1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0486    1.0736    0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0173   -0.6828   -0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430    1.5779    1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4961    1.6345    0.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0741   -0.0001   -1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8998    2.7578   -1.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0325   -0.6279   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5095    1.7180    0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8505    1.0537   -1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6950   -0.7769   -0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4323    1.0769    1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5500   -1.5365    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0537   -1.2723    0.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0837   -1.5954    2.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6285   -2.1192   -1.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9528   -2.8728   -2.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3743   -2.5168   -1.6045 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
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  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
 12 33  1  0
 13 34  1  0
 15 35  1  6
 16 36  1  0
 16 37  1  0
 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  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000 -13.860   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667 -18.480   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000 -16.940   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19                                                            
CONECT   21   17   22                                                       
CONECT   22   21                                                            
CONECT   23   16                                                            
CONECT   24   15                                                            
CONECT   25    4                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0302219
HETATM    1  C1  UNL     1       7.484   1.111   1.024  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.544   0.430   0.471  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.561  -0.215  -0.058  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.229   0.198   0.155  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.181  -0.465  -0.392  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.776  -0.059  -0.188  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.412   0.970   0.531  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.009   1.298   0.679  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.395   2.280   1.360  1.00  0.00           O  
HETATM   10  O3  UNL     1      -0.938   0.525   0.061  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.318   0.738   0.127  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.984   0.935  -1.194  1.00  0.00           C  
HETATM   13  O4  UNL     1      -2.388   1.932  -1.923  1.00  0.00           O  
HETATM   14  O5  UNL     1      -4.312   1.334  -0.933  1.00  0.00           O  
HETATM   15  C10 UNL     1      -5.041   0.265  -0.365  1.00  0.00           C  
HETATM   16  C11 UNL     1      -6.480   0.789  -0.261  1.00  0.00           C  
HETATM   17  O6  UNL     1      -7.261  -0.201   0.287  1.00  0.00           O  
HETATM   18  C12 UNL     1      -4.473   0.050   1.021  1.00  0.00           C  
HETATM   19  O7  UNL     1      -5.209  -0.826   1.783  1.00  0.00           O  
HETATM   20  C13 UNL     1      -3.036  -0.406   0.841  1.00  0.00           C  
HETATM   21  O8  UNL     1      -2.432  -0.687   2.062  1.00  0.00           O  
HETATM   22  C14 UNL     1       3.451  -1.571  -1.173  1.00  0.00           C  
HETATM   23  C15 UNL     1       4.742  -1.997  -1.399  1.00  0.00           C  
HETATM   24  C16 UNL     1       5.806  -1.349  -0.862  1.00  0.00           C  
HETATM   25  O9  UNL     1       7.118  -1.729  -1.052  1.00  0.00           O  
HETATM   26  H1  UNL     1       7.828   2.056   0.498  1.00  0.00           H  
HETATM   27  H2  UNL     1       7.181   1.512   2.052  1.00  0.00           H  
HETATM   28  H3  UNL     1       8.460   0.580   1.237  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.049   1.074   0.777  1.00  0.00           H  
HETATM   30  H5  UNL     1       1.017  -0.683  -0.686  1.00  0.00           H  
HETATM   31  H6  UNL     1       2.143   1.578   1.016  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.496   1.634   0.761  1.00  0.00           H  
HETATM   33  H8  UNL     1      -3.074  -0.000  -1.784  1.00  0.00           H  
HETATM   34  H9  UNL     1      -2.900   2.758  -1.887  1.00  0.00           H  
HETATM   35  H10 UNL     1      -5.032  -0.628  -0.989  1.00  0.00           H  
HETATM   36  H11 UNL     1      -6.509   1.718   0.339  1.00  0.00           H  
HETATM   37  H12 UNL     1      -6.851   1.054  -1.265  1.00  0.00           H  
HETATM   38  H13 UNL     1      -7.695  -0.777  -0.369  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.432   1.077   1.490  1.00  0.00           H  
HETATM   40  H15 UNL     1      -5.550  -1.537   1.172  1.00  0.00           H  
HETATM   41  H16 UNL     1      -3.054  -1.272   0.156  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.084  -1.595   2.122  1.00  0.00           H  
HETATM   43  H18 UNL     1       2.629  -2.119  -1.623  1.00  0.00           H  
HETATM   44  H19 UNL     1       4.953  -2.873  -2.018  1.00  0.00           H  
HETATM   45  H20 UNL     1       7.374  -2.517  -1.604  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   14   33
CONECT   13   34
CONECT   14   15
CONECT   15   16   18   35
CONECT   16   17   36   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

HMDB0302219
     RDKit          3D
1-O-Feruloyl-beta-D-glucose
 45 46  0  0  0  0  0  0  0  0999 V2000
    7.4837    1.1106    1.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5438    0.4298    0.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5610   -0.2147   -0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2286    0.1984    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1812   -0.4654   -0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7760   -0.0588   -0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4124    0.9696    0.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0088    1.2984    0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3953    2.2800    1.3604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9381    0.5254    0.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3181    0.7380    0.1274 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9844    0.9354   -1.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3875    1.9321   -1.9232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3120    1.3340   -0.9325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0412    0.2648   -0.3651 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4804    0.7887   -0.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2613   -0.2013    0.2869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4729    0.0497    1.0214 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2093   -0.8263    1.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0363   -0.4060    0.8410 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4315   -0.6871    2.0619 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4510   -1.5708   -1.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7421   -1.9973   -1.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8056   -1.3489   -0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1183   -1.7290   -1.0519 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8280    2.0565    0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1810    1.5123    2.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4597    0.5801    1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0486    1.0736    0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0173   -0.6828   -0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430    1.5779    1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4961    1.6345    0.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0741   -0.0001   -1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8998    2.7578   -1.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0325   -0.6279   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5095    1.7180    0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8505    1.0537   -1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6950   -0.7769   -0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4323    1.0769    1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5500   -1.5365    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0537   -1.2723    0.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0837   -1.5954    2.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6285   -2.1192   -1.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9528   -2.8728   -2.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3743   -2.5168   -1.6045 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
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  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
 12 33  1  0
 13 34  1  0
 15 35  1  6
 16 36  1  0
 16 37  1  0
 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
(3R,4S,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid	Generator
1-O-Feruloyl-b-D-glucose	Generator
1-O-Feruloyl-β-D-glucose	Generator

Chemical Formula

C₁₆H₂₀O₉

Average Molecular Weight

356.3246

Monoisotopic Molecular Weight

356.110732238

IUPAC Name

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

Traditional Name

(3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-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]2C(O)O[C@H](CO)[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)25-15-14(21)13(20)11(7-17)24-16(15)22/h2-6,11,13-18,20-22H,7H2,1H3/b5-3+/t11-,13-,14+,15-,16?/m1/s1

InChI Key

ADHNTNYEJYJUCU-ZSJFXSENSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Soy bean (FooDB: FOOD00085)

Vegetable

Cabbage

Fruit vegetable

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Herb and spice

Herb

Chives (FooDB: FOOD00009)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Pulse

Pea

Common pea (FooDB: FOOD00141)

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)	9.85	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	35.05 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]+	184.153	32859911
AllCCS	[M+H-H2O]+	181.216	32859911
AllCCS	[M+Na]+	187.643	32859911
AllCCS	[M+NH4]+	186.866	32859911
AllCCS	[M-H]-	179.896	32859911
AllCCS	[M+Na-2H]-	180.113	32859911
AllCCS	[M+HCOO]-	180.488	32859911
DeepCCS	[M+H]+	184.461	30932474
DeepCCS	[M-H]-	182.065	30932474
DeepCCS	[M-2H]-	215.048	30932474
DeepCCS	[M+Na]+	191.411	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-glucose 10V, Positive-QTOF	splash10-0bvr-0906000000-2f859049c8ec3f168a29	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucose 20V, Positive-QTOF	splash10-03fr-1901000000-bfcedbd3d913785da662	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucose 40V, Positive-QTOF	splash10-01vp-5900000000-f12c64108910713820ab	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucose 10V, Negative-QTOF	splash10-0a4l-2916000000-9176c9a206c40a1d0deb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucose 20V, Negative-QTOF	splash10-004l-2900000000-cc8ec74a1f2d8dcf387d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucose 40V, Negative-QTOF	splash10-004l-3900000000-74ac6837f29565f95d53	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucose 10V, Positive-QTOF	splash10-05g0-0119000000-2826b09400af75b8535b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucose 20V, Positive-QTOF	splash10-002b-0932000000-71468dcccc73a07756b7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucose 40V, Positive-QTOF	splash10-0002-3900000000-c314a4110d24e640b057	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucose 10V, Negative-QTOF	splash10-0ap0-1498000000-0aaed891b1bf8cec2418	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucose 20V, Negative-QTOF	splash10-0kcv-4923000000-f89f9933aa86eac7a605	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Feruloyl-beta-D-glucose 40V, Negative-QTOF	splash10-0zgj-3913000000-5d48a96bd2246f300336	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

FDB003730

KNApSAcK ID

Not Available

Chemspider ID

59696306

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

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METLIN ID

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PubChem Compound

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PDB ID

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ChEBI ID

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Food Biomarker Ontology

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VMH ID

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MarkerDB ID

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Good Scents ID

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References

Synthesis Reference

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Material Safety Data Sheet (MSDS)

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General References

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Showing metabocard for 1-O-Feruloyl-beta-D-glucose (HMDB0302219)

MOL for HMDB0302219 (1-O-Feruloyl-beta-D-glucose)

3D MOL for HMDB0302219 (1-O-Feruloyl-beta-D-glucose)

3D SDF for HMDB0302219 (1-O-Feruloyl-beta-D-glucose)

3D-SDF for HMDB0302219 (1-O-Feruloyl-beta-D-glucose)

PDB for HMDB0302219 (1-O-Feruloyl-beta-D-glucose)

3D PDB for HMDB0302219 (1-O-Feruloyl-beta-D-glucose)

SMILES for HMDB0302219 (1-O-Feruloyl-beta-D-glucose)

INCHI for HMDB0302219 (1-O-Feruloyl-beta-D-glucose)

Structure for HMDB0302219 (1-O-Feruloyl-beta-D-glucose)

3D Structure for HMDB0302219 (1-O-Feruloyl-beta-D-glucose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra