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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 01:15:36 UTC

Update Date

2021-09-24 01:15:37 UTC

HMDB ID

HMDB0303353

Secondary Accession Numbers

None

Metabolite Identification

Common Name

cis-o-Coumaric acid 2-glucoside

Description

(2E)-3-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Based on a literature review very few articles have been published on (2E)-3-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid.

Structure

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

HMDB0303353
     RDKit          3D
cis-o-Coumaric acid 2-glucoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.3512   -3.1386   -1.4979 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2219   -2.6428   -1.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1059   -3.4132   -1.5188 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1468   -1.2630   -0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9925   -0.6909   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8115    0.6577    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8841    1.4693    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902    2.7578    0.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198    3.2197    0.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524    2.3947    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5073    1.1241    0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4871    0.2655   -0.0546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8919    0.4846    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3586   -0.4297    1.0197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7256   -0.4619    1.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0891   -1.3622    2.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5062   -0.8201    3.4266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2766   -0.9948   -0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6213   -1.2896   -0.0985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0102    0.1241   -1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5258   -0.1762   -2.4356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5100    0.2580   -1.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1524    1.3421   -2.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5598   -3.8747   -0.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0455   -0.6928   -0.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -1.3245   -0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8988    1.1592    0.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165    3.4159    0.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2361    4.2183    1.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461    2.7641    0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1685    1.4846    0.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1903    0.5307    1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6089   -2.3656    2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1665   -1.5315    2.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6786    0.1604    3.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6566   -1.8566   -0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8618   -1.7977   -0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4845    1.0280   -0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9278    0.6535   -2.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1047   -0.7006   -1.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1704    1.3147   -2.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 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  6  1  0
 22 13  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
M  END


  Mrv0541 02241207422D          

 23 24  0  0  0  0            999 V2000
    1.4508    0.6722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4508   -0.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1587   -0.6722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6014   -0.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6014   -1.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1773   -1.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1773   -2.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8845   -3.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6631   -2.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6631   -1.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8845   -1.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9553   -0.6722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9553    1.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216    1.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1587    1.1677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3189    1.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3189    2.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2474    2.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2474    3.2913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9553    3.2913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9553    2.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216    2.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1587    2.5834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
 14 22  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303353

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1OC(OC2=C(\C=C\C(O)=O)C=CC=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-2-1-3-8(9)5-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-5+

> <INCHI_KEY>
GVRIYIMNJGULCZ-AATRIKPKSA-N

> <FORMULA>
C15H18O8

> <MOLECULAR_WEIGHT>
326.2986

> <EXACT_MASS>
326.100167552

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
31.189171739773332

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.70

> <JCHEM_LOGP>
-0.43554715499999985

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.20011328362007

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7027156712501847

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923461838152

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
77.18520000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
melilotoside

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303353
     RDKit          3D
cis-o-Coumaric acid 2-glucoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.3512   -3.1386   -1.4979 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2219   -2.6428   -1.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1059   -3.4132   -1.5188 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1468   -1.2630   -0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9925   -0.6909   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8115    0.6577    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8841    1.4693    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902    2.7578    0.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198    3.2197    0.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524    2.3947    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5073    1.1241    0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4871    0.2655   -0.0546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8919    0.4846    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3586   -0.4297    1.0197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7256   -0.4619    1.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0891   -1.3622    2.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5062   -0.8201    3.4266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2766   -0.9948   -0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6213   -1.2896   -0.0985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0102    0.1241   -1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5258   -0.1762   -2.4356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5100    0.2580   -1.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1524    1.3421   -2.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5598   -3.8747   -0.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0455   -0.6928   -0.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -1.3245   -0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8988    1.1592    0.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165    3.4159    0.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2361    4.2183    1.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461    2.7641    0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1685    1.4846    0.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1903    0.5307    1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6089   -2.3656    2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1665   -1.5315    2.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6786    0.1604    3.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6566   -1.8566   -0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8618   -1.7977   -0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4845    1.0280   -0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9278    0.6535   -2.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1047   -0.7006   -1.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1704    1.3147   -2.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 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  6  1  0
 22 13  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  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       2.708   1.255   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.708  -0.462   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.030  -1.255   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.123  -1.255   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.123  -2.840   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.331  -3.633   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.331  -5.351   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.651  -6.144   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.104  -5.351   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.104  -3.633   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.651  -2.840   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.783  -1.255   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.783   2.180   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.840   2.840   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.030   2.180   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.595   2.840   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.595   4.162   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.462   4.822   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.462   6.144   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.783   6.144   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.783   4.822   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.840   4.162   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.030   4.822   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    6   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21   17   20   22                                                  
CONECT   22   14   21   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0303353
HETATM    1  O1  UNL     1       5.351  -3.139  -1.498  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.222  -2.643  -1.273  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.106  -3.413  -1.519  1.00  0.00           O  
HETATM    4  C2  UNL     1       4.147  -1.263  -0.756  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.993  -0.691  -0.502  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.812   0.658   0.007  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.884   1.469   0.270  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.690   2.758   0.757  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.420   3.220   0.975  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.352   2.395   0.707  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.507   1.124   0.228  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.487   0.265  -0.055  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.892   0.485   0.077  1.00  0.00           C  
HETATM   14  O4  UNL     1      -1.359  -0.430   1.020  1.00  0.00           O  
HETATM   15  C11 UNL     1      -2.726  -0.462   1.129  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.089  -1.362   2.283  1.00  0.00           C  
HETATM   17  O5  UNL     1      -2.506  -0.820   3.427  1.00  0.00           O  
HETATM   18  C13 UNL     1      -3.277  -0.995  -0.187  1.00  0.00           C  
HETATM   19  O6  UNL     1      -4.621  -1.290  -0.099  1.00  0.00           O  
HETATM   20  C14 UNL     1      -3.010   0.124  -1.204  1.00  0.00           C  
HETATM   21  O7  UNL     1      -3.526  -0.176  -2.436  1.00  0.00           O  
HETATM   22  C15 UNL     1      -1.510   0.258  -1.287  1.00  0.00           C  
HETATM   23  O8  UNL     1      -1.152   1.342  -2.081  1.00  0.00           O  
HETATM   24  H1  UNL     1       2.560  -3.875  -0.803  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.046  -0.693  -0.577  1.00  0.00           H  
HETATM   26  H3  UNL     1       2.113  -1.324  -0.705  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.899   1.159   0.118  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.517   3.416   0.972  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.236   4.218   1.353  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.346   2.764   0.881  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.169   1.485   0.459  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.190   0.531   1.276  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.609  -2.366   2.130  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.166  -1.531   2.393  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.679   0.160   3.414  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.657  -1.857  -0.485  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.862  -1.798  -0.919  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.484   1.028  -0.774  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.928   0.653  -2.816  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.105  -0.701  -1.672  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.170   1.315  -2.228  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   24
CONECT    4    5    5   25
CONECT    5    6   26
CONECT    6    7    7   11
CONECT    7    8   27
CONECT    8    9    9   28
CONECT    9   10   29
CONECT   10   11   11   30
CONECT   11   12
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

HMDB0303353
     RDKit          3D
cis-o-Coumaric acid 2-glucoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.3512   -3.1386   -1.4979 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2219   -2.6428   -1.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1059   -3.4132   -1.5188 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1468   -1.2630   -0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9925   -0.6909   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8115    0.6577    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8841    1.4693    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902    2.7578    0.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198    3.2197    0.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524    2.3947    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5073    1.1241    0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4871    0.2655   -0.0546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8919    0.4846    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3586   -0.4297    1.0197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7256   -0.4619    1.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0891   -1.3622    2.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5062   -0.8201    3.4266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2766   -0.9948   -0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6213   -1.2896   -0.0985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0102    0.1241   -1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5258   -0.1762   -2.4356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5100    0.2580   -1.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1524    1.3421   -2.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5598   -3.8747   -0.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0455   -0.6928   -0.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -1.3245   -0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8988    1.1592    0.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165    3.4159    0.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2361    4.2183    1.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461    2.7641    0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1685    1.4846    0.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1903    0.5307    1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6089   -2.3656    2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1665   -1.5315    2.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6786    0.1604    3.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6566   -1.8566   -0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8618   -1.7977   -0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4845    1.0280   -0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9278    0.6535   -2.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1047   -0.7006   -1.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1704    1.3147   -2.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 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  6  1  0
 22 13  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E)-3-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate	Generator
Melilotoside	HMDB
trans-O-Coumarate 2-glucoside	Generator
cis-O-Coumarate 2-glucoside	Generator

Chemical Formula

C₁₅H₁₈O₈

Average Molecular Weight

326.2986

Monoisotopic Molecular Weight

326.100167552

IUPAC Name

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

Traditional Name

melilotoside

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2=C(\C=C\C(O)=O)C=CC=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-2-1-3-8(9)5-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-5+

InChI Key

GVRIYIMNJGULCZ-AATRIKPKSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0303353)
Extracellular (HMDB: HMDB0303353)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0303353)

Source

Exogenous

Exogenous (HMDB: HMDB0303353)

Food

Food (HMDB: HMDB0303353)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0303353)
Fabaceae (HMDB: HMDB0303353)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0303353)

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	-0.7	ALOGPS
logP	-0.44	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.7	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.19 m³·mol⁻¹	ChemAxon
Polarizability	31.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	175.743	32859911
AllCCS	[M+H-H2O]+	172.633	32859911
AllCCS	[M+Na]+	179.444	32859911
AllCCS	[M+NH4]+	178.619	32859911
AllCCS	[M-H]-	172.286	32859911
AllCCS	[M+Na-2H]-	172.245	32859911
AllCCS	[M+HCOO]-	172.329	32859911
DeepCCS	[M+H]+	172.442	30932474
DeepCCS	[M-H]-	170.084	30932474
DeepCCS	[M-2H]-	203.948	30932474
DeepCCS	[M+Na]+	179.176	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - cis-o-Coumaric acid 2-glucoside GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-5943000000-2c7be4677b773c69f301	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-o-Coumaric acid 2-glucoside GC-MS (5 TMS) - 70eV, Positive	splash10-00di-1020229000-cd5e122c29a7c414bbb3	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-o-Coumaric acid 2-glucoside 10V, Positive-QTOF	splash10-0691-0935000000-827cd1afac41e01e6be2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-o-Coumaric acid 2-glucoside 20V, Positive-QTOF	splash10-014j-1910000000-074126586479ea59b56a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-o-Coumaric acid 2-glucoside 40V, Positive-QTOF	splash10-014i-2900000000-efb3a4af37c4149f2cb9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-o-Coumaric acid 2-glucoside 10V, Negative-QTOF	splash10-01t9-1928000000-1fe18b400bb020298aee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-o-Coumaric acid 2-glucoside 20V, Negative-QTOF	splash10-03di-1911000000-74a7cc1ec970b1c43fcd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-o-Coumaric acid 2-glucoside 40V, Negative-QTOF	splash10-03xu-4900000000-1d2c2da5a557045613e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-o-Coumaric acid 2-glucoside 10V, Positive-QTOF	splash10-00mk-0904000000-3dd34e382ba43fc1764f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-o-Coumaric acid 2-glucoside 20V, Positive-QTOF	splash10-0arr-0596000000-829180a1d0df8715f61c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-o-Coumaric acid 2-glucoside 40V, Positive-QTOF	splash10-014i-2900000000-e9a87fed398fa7e220c1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-o-Coumaric acid 2-glucoside 10V, Negative-QTOF	splash10-07f0-0598000000-7c06dab5e1ee09a3e269	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-o-Coumaric acid 2-glucoside 20V, Negative-QTOF	splash10-0j4i-1931000000-be23d1fceb38e06a6c84	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-o-Coumaric acid 2-glucoside 40V, Negative-QTOF	splash10-014i-3900000000-c4aef0c58740bba64b21	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

FDB016244

KNApSAcK ID

Not Available

Chemspider ID

10468576

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6275271

PDB ID

Not Available

ChEBI ID

172552

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 cis-o-Coumaric acid 2-glucoside (HMDB0303353)

MOL for HMDB0303353 (cis-o-Coumaric acid 2-glucoside)

3D MOL for HMDB0303353 (cis-o-Coumaric acid 2-glucoside)

3D SDF for HMDB0303353 (cis-o-Coumaric acid 2-glucoside)

3D-SDF for HMDB0303353 (cis-o-Coumaric acid 2-glucoside)

PDB for HMDB0303353 (cis-o-Coumaric acid 2-glucoside)

3D PDB for HMDB0303353 (cis-o-Coumaric acid 2-glucoside)

SMILES for HMDB0303353 (cis-o-Coumaric acid 2-glucoside)

INCHI for HMDB0303353 (cis-o-Coumaric acid 2-glucoside)

Structure for HMDB0303353 (cis-o-Coumaric acid 2-glucoside)

3D Structure for HMDB0303353 (cis-o-Coumaric acid 2-glucoside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra