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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 06:28:31 UTC

Update Date

2021-09-23 06:28:31 UTC

HMDB ID

HMDB0302089

Secondary Accession Numbers

None

Metabolite Identification

Common Name

trans-p-Coumaroyl beta-D-glucopyranoside

Description

Trans-p-coumaroyl beta-d-glucopyranoside, also known as 1-O-(4-hydroxycinnamoyl)-beta-D-glucose or 1-O-(4-coumaroyl)-β-D-glucoside, is a member of the class of compounds known as hydroxycinnamic acid glycosides. Hydroxycinnamic acid glycosides are glycosylated hydoxycinnamic acids derivatives. Trans-p-coumaroyl beta-d-glucopyranoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Trans-p-coumaroyl beta-d-glucopyranoside can be found in tea, which makes trans-p-coumaroyl beta-d-glucopyranoside a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302089
     RDKit          3D
trans-p-Coumaroyl beta-D-glucopyranoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    0.3594   -1.6644   -0.8558 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6088   -0.5788   -0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9495   -0.0387   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9975   -0.6881   -0.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3794   -0.2183   -0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7338    0.9582    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0637    1.3494    0.2012 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0658    0.5805   -0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3804    1.0161   -0.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6932   -0.5916   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3856   -1.0104   -1.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    0.1401    0.2318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792   -0.3110    0.1238 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5158    0.5758   -0.6755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7941    0.0289   -0.7790 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4681    0.5799   -2.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7446    0.0082   -2.0776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5366    0.3917    0.4854 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6063   -0.4844    0.6204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6210    0.3605    1.6842 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1685    1.6240    2.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256   -0.5363    1.4673 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8069   -1.8715    1.6298 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0910    0.8941    0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7678   -1.6379   -1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9689    1.5870    0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3017    2.2863    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8916    0.7241    0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4636   -1.2118   -1.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0891   -1.9329   -1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7709   -1.2807   -0.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7485   -1.0728   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5016    1.6700   -2.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104    0.1933   -2.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6315   -0.9651   -1.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9467    1.4170    0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2538   -0.1878    1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1797   -0.0455    2.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8759    2.2016    2.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6767   -0.3068    2.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7709   -1.9523    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 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
 20 22  1  0
 22 23  1  0
 11  5  1  0
 22 13  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  6
 15 32  1  6
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  6
 19 37  1  0
 20 38  1  1
 21 39  1  0
 22 40  1  1
 23 41  1  0
M  END

  Mrv1652308141918272D          

 23 24  0  0  1  0            999 V2000
   10.1530   -6.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8675   -5.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5819   -6.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2964   -5.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0109   -6.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1530   -6.9304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2964   -4.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0108   -4.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7253   -4.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7253   -5.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4398   -4.4555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0097   -7.3429    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0097   -8.1679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2952   -6.9304    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5808   -7.3429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2952   -6.1055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7242   -6.1055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4386   -5.6930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4386   -7.3429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0097   -5.6930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7242   -6.9304    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5808   -5.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8664   -6.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  1  6  2  0  0  0  0
  5 10  2  0  0  0  0
  5  4  1  0  0  0  0
  4  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 16 14  1  0  0  0  0
 16 20  1  0  0  0  0
 14 12  1  0  0  0  0
 20 17  1  0  0  0  0
 12 21  1  0  0  0  0
 17 21  1  0  0  0  0
 12 13  1  1  0  0  0
 14 15  1  6  0  0  0
 16 22  1  1  0  0  0
 17 18  1  1  0  0  0
 21 19  1  6  0  0  0
 22 23  1  0  0  0  0
  1 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302089

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(22-10)23-11(18)6-3-8-1-4-9(17)5-2-8/h1-6,10,12-17,19-21H,7H2/b6-3+/t10-,12-,13+,14-,15+/m1/s1

> <INCHI_KEY>
DSNCQKUYZOSARM-QVLXMGEUSA-N

> <FORMULA>
C15H18O8

> <MOLECULAR_WEIGHT>
326.2986

> <EXACT_MASS>
326.100167552

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
32.26135160955537

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.51

> <JCHEM_LOGP>
-0.20221382166666652

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.19635517909541

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.397567602150882

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810938220288765

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
77.472

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
p-coumaroyl-D-glucose

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302089
     RDKit          3D
trans-p-Coumaroyl beta-D-glucopyranoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    0.3594   -1.6644   -0.8558 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6088   -0.5788   -0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9495   -0.0387   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9975   -0.6881   -0.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3794   -0.2183   -0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7338    0.9582    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0637    1.3494    0.2012 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0658    0.5805   -0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3804    1.0161   -0.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6932   -0.5916   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3856   -1.0104   -1.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    0.1401    0.2318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792   -0.3110    0.1238 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5158    0.5758   -0.6755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7941    0.0289   -0.7790 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4681    0.5799   -2.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7446    0.0082   -2.0776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5366    0.3917    0.4854 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6063   -0.4844    0.6204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6210    0.3605    1.6842 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1685    1.6240    2.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256   -0.5363    1.4673 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8069   -1.8715    1.6298 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0910    0.8941    0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7678   -1.6379   -1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9689    1.5870    0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3017    2.2863    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8916    0.7241    0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4636   -1.2118   -1.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0891   -1.9329   -1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7709   -1.2807   -0.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7485   -1.0728   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5016    1.6700   -2.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104    0.1933   -2.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6315   -0.9651   -1.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9467    1.4170    0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2538   -0.1878    1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1797   -0.0455    2.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8759    2.2016    2.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6767   -0.3068    2.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7709   -1.9523    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 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
 20 22  1  0
 22 23  1  0
 11  5  1  0
 22 13  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  6
 15 32  1  6
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  6
 19 37  1  0
 20 38  1  1
 21 39  1  0
 22 40  1  1
 23 41  1  0
M  END

HEADER    PROTEIN                                 14-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-AUG-19         0                                  
HETATM    1  C   UNK     0      18.952 -11.397   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.286 -10.627   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.620 -11.397   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.953 -10.627   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.287 -11.397   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      18.952 -12.937   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      22.953  -9.087   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.287  -8.317   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.621  -9.087   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.621 -10.627   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      26.954  -8.317   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      14.951 -13.707   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.951 -15.247   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.618 -12.937   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.284 -13.707   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      13.618 -11.397   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.285 -11.397   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      17.619 -10.627   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      17.619 -13.707   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      14.951 -10.627   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      16.285 -12.937   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.284 -10.627   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.951 -11.397   0.000  0.00  0.00           O+0
CONECT    1    2    6   18                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5   10    4                                                       
CONECT    6    1                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9                                                       
CONECT   11    9                                                            
CONECT   12   14   21   13                                                  
CONECT   13   12                                                            
CONECT   14   16   12   15                                                  
CONECT   15   14                                                            
CONECT   16   14   20   22                                                  
CONECT   17   20   21   18                                                  
CONECT   18   17    1                                                       
CONECT   19   21                                                            
CONECT   20   16   17                                                       
CONECT   21   12   17   19                                                  
CONECT   22   16   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0302089
HETATM    1  O1  UNL     1       0.359  -1.664  -0.856  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.609  -0.579  -0.281  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.949  -0.039  -0.126  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.997  -0.688  -0.598  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.379  -0.218  -0.487  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.734   0.958   0.127  1.00  0.00           C  
HETATM    7  C6  UNL     1       6.064   1.349   0.201  1.00  0.00           C  
HETATM    8  C7  UNL     1       7.066   0.580  -0.333  1.00  0.00           C  
HETATM    9  O2  UNL     1       8.380   1.016  -0.232  1.00  0.00           O  
HETATM   10  C8  UNL     1       6.693  -0.592  -0.942  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.386  -1.010  -1.034  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.458   0.140   0.232  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.779  -0.311   0.124  1.00  0.00           C  
HETATM   14  O4  UNL     1      -2.516   0.576  -0.676  1.00  0.00           O  
HETATM   15  C11 UNL     1      -3.794   0.029  -0.779  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.468   0.580  -2.010  1.00  0.00           C  
HETATM   17  O5  UNL     1      -5.745   0.008  -2.078  1.00  0.00           O  
HETATM   18  C13 UNL     1      -4.537   0.392   0.485  1.00  0.00           C  
HETATM   19  O6  UNL     1      -5.606  -0.484   0.620  1.00  0.00           O  
HETATM   20  C14 UNL     1      -3.621   0.360   1.684  1.00  0.00           C  
HETATM   21  O7  UNL     1      -3.168   1.624   2.039  1.00  0.00           O  
HETATM   22  C15 UNL     1      -2.426  -0.536   1.467  1.00  0.00           C  
HETATM   23  O8  UNL     1      -2.807  -1.872   1.630  1.00  0.00           O  
HETATM   24  H1  UNL     1       2.091   0.894   0.376  1.00  0.00           H  
HETATM   25  H2  UNL     1       2.768  -1.638  -1.100  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.969   1.587   0.558  1.00  0.00           H  
HETATM   27  H4  UNL     1       6.302   2.286   0.695  1.00  0.00           H  
HETATM   28  H5  UNL     1       8.892   0.724   0.582  1.00  0.00           H  
HETATM   29  H6  UNL     1       7.464  -1.212  -1.368  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.089  -1.933  -1.513  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.771  -1.281  -0.414  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.748  -1.073  -0.835  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.502   1.670  -2.007  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.910   0.193  -2.887  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.631  -0.965  -1.939  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.947   1.417   0.386  1.00  0.00           H  
HETATM   37  H14 UNL     1      -6.254  -0.188   1.319  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.180  -0.045   2.553  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.876   2.202   2.421  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.677  -0.307   2.251  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.771  -1.952   1.805  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   24
CONECT    4    5   25
CONECT    5    6    6   11
CONECT    6    7   26
CONECT    7    8    8   27
CONECT    8    9   10
CONECT    9   28
CONECT   10   11   11   29
CONECT   11   30
CONECT   12   13
CONECT   13   14   22   31
CONECT   14   15
CONECT   15   16   18   32
CONECT   16   17   33   34
CONECT   17   35
CONECT   18   19   20   36
CONECT   19   37
CONECT   20   21   22   38
CONECT   21   39
CONECT   22   23   40
CONECT   23   41
END

HMDB0302089
     RDKit          3D
trans-p-Coumaroyl beta-D-glucopyranoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    0.3594   -1.6644   -0.8558 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6088   -0.5788   -0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9495   -0.0387   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9975   -0.6881   -0.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3794   -0.2183   -0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7338    0.9582    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0637    1.3494    0.2012 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0658    0.5805   -0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3804    1.0161   -0.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6932   -0.5916   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3856   -1.0104   -1.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    0.1401    0.2318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792   -0.3110    0.1238 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5158    0.5758   -0.6755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7941    0.0289   -0.7790 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4681    0.5799   -2.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7446    0.0082   -2.0776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5366    0.3917    0.4854 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6063   -0.4844    0.6204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6210    0.3605    1.6842 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1685    1.6240    2.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256   -0.5363    1.4673 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8069   -1.8715    1.6298 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0910    0.8941    0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7678   -1.6379   -1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9689    1.5870    0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3017    2.2863    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8916    0.7241    0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4636   -1.2118   -1.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0891   -1.9329   -1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7709   -1.2807   -0.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7485   -1.0728   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5016    1.6700   -2.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104    0.1933   -2.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6315   -0.9651   -1.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9467    1.4170    0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2538   -0.1878    1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1797   -0.0455    2.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8759    2.2016    2.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6767   -0.3068    2.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7709   -1.9523    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 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
 20 22  1  0
 22 23  1  0
 11  5  1  0
 22 13  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  6
 15 32  1  6
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  6
 19 37  1  0
 20 38  1  1
 21 39  1  0
 22 40  1  1
 23 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-O-(4-Hydroxycinnamoyl)-beta-D-glucose	ChEBI
1-O-(trans-4-Coumaroyl)-beta-D-glucose	ChEBI
p-Coumaroyl-beta-D-glucose	ChEBI
1-O-(4-Hydroxycinnamoyl)-b-D-glucose	Generator
1-O-(4-Hydroxycinnamoyl)-β-D-glucose	Generator
1-O-(trans-4-Coumaroyl)-b-D-glucose	Generator
1-O-(trans-4-Coumaroyl)-β-D-glucose	Generator
p-Coumaroyl-b-D-glucose	Generator
p-Coumaroyl-β-D-glucose	Generator
1-O-(4-Coumaroyl)-b-D-glucose	Generator
1-O-(4-Coumaroyl)-β-D-glucose	Generator
trans-P-Coumaroyl b-D-glucopyranoside	Generator
trans-P-Coumaroyl β-D-glucopyranoside	Generator
1-O-(4-Coumaroyl)-beta-D-glucose	KEGG

Chemical Formula

C₁₅H₁₈O₈

Average Molecular Weight

326.2986

Monoisotopic Molecular Weight

326.100167552

IUPAC Name

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

Traditional Name

p-coumaroyl-D-glucose

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(22-10)23-11(18)6-3-8-1-4-9(17)5-2-8/h1-6,10,12-17,19-21H,7H2/b6-3+/t10-,12-,13+,14-,15+/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

O-acyl carbohydrate (CHEBI:71498 )

Ontology

Not Available

Exogenous (HMDB: HMDB0302089)

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.51	ALOGPS
logP	-0.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.47 m³·mol⁻¹	ChemAxon
Polarizability	32.26 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]+	176.83	32859911
AllCCS	[M+H-H2O]+	173.661	32859911
AllCCS	[M+Na]+	180.604	32859911
AllCCS	[M+NH4]+	179.762	32859911
AllCCS	[M-H]-	173.091	32859911
AllCCS	[M+Na-2H]-	173.105	32859911
AllCCS	[M+HCOO]-	173.251	32859911
DeepCCS	[M+H]+	170.958	30932474
DeepCCS	[M-H]-	168.562	30932474
DeepCCS	[M-2H]-	202.316	30932474
DeepCCS	[M+Na]+	177.087	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Coumaroyl beta-D-glucopyranoside 10V, Positive-QTOF	splash10-00kb-0902000000-c1d1ff3949ff38aaed4b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Coumaroyl beta-D-glucopyranoside 20V, Positive-QTOF	splash10-00kb-0900000000-e4a0c0fc809a93114259	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Coumaroyl beta-D-glucopyranoside 40V, Positive-QTOF	splash10-014j-4900000000-39d845d085a081120f28	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Coumaroyl beta-D-glucopyranoside 10V, Negative-QTOF	splash10-0002-0902000000-d505fe911b8d3da07208	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Coumaroyl beta-D-glucopyranoside 20V, Negative-QTOF	splash10-03di-1900000000-38fee86878d2ae9e415e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Coumaroyl beta-D-glucopyranoside 40V, Negative-QTOF	splash10-01ow-7900000000-1b0cc7d2e39c0949e024	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Coumaroyl beta-D-glucopyranoside 10V, Positive-QTOF	splash10-004j-0709000000-d41db3a520e3f1ecd785	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Coumaroyl beta-D-glucopyranoside 20V, Positive-QTOF	splash10-014j-1920000000-973b71e0a2cbeb739508	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Coumaroyl beta-D-glucopyranoside 40V, Positive-QTOF	splash10-014i-6910000000-9a1374eebe7fe5e24442	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Coumaroyl beta-D-glucopyranoside 10V, Negative-QTOF	splash10-02di-0914000000-08c8d8b64e346a337ae1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Coumaroyl beta-D-glucopyranoside 20V, Negative-QTOF	splash10-016r-2932000000-e7b92e9c5f2eef7360b4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Coumaroyl beta-D-glucopyranoside 40V, Negative-QTOF	splash10-014i-1900000000-05863de8b811aaf4f698	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

FDB093521

KNApSAcK ID

Not Available

Chemspider ID

10394547

KEGG Compound ID

C16827

BioCyc ID

CPD-8674

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

71498

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for trans-p-Coumaroyl beta-D-glucopyranoside (HMDB0302089)

MOL for HMDB0302089 (trans-p-Coumaroyl beta-D-glucopyranoside)

3D MOL for HMDB0302089 (trans-p-Coumaroyl beta-D-glucopyranoside)

3D SDF for HMDB0302089 (trans-p-Coumaroyl beta-D-glucopyranoside)

3D-SDF for HMDB0302089 (trans-p-Coumaroyl beta-D-glucopyranoside)

PDB for HMDB0302089 (trans-p-Coumaroyl beta-D-glucopyranoside)

3D PDB for HMDB0302089 (trans-p-Coumaroyl beta-D-glucopyranoside)

SMILES for HMDB0302089 (trans-p-Coumaroyl beta-D-glucopyranoside)

INCHI for HMDB0302089 (trans-p-Coumaroyl beta-D-glucopyranoside)

Structure for HMDB0302089 (trans-p-Coumaroyl beta-D-glucopyranoside)

3D Structure for HMDB0302089 (trans-p-Coumaroyl beta-D-glucopyranoside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra