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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:02 UTC

Update Date

2022-03-07 02:52:12 UTC

HMDB ID

HMDB0029539

Secondary Accession Numbers

HMDB29539

Metabolite Identification

Common Name

Xenognosin A

Description

Xenognosin A belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups. Xenognosin A has been detected, but not quantified in, common peas (Pisum sativum) and pulses. This could make xenognosin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Xenognosin A.

Structure

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

HMDB0029539
     RDKit          3D
Xenognosin A
 35 36  0  0  0  0  0  0  0  0999 V2000
    3.1624    2.5521   -0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474    1.3565   -0.9481 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6994    0.2100   -0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7056    0.1746    0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9851   -0.9447    1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0084   -0.9094    2.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2087   -2.0796    1.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972   -2.0670    0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323   -0.9360   -0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431   -0.9684   -1.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3806   -0.2722   -0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445   -0.8822   -0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7609   -0.2465   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8895   -1.0346   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1007   -0.5193    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501    0.8096    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3258    1.3760    0.9875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0240    1.5994    0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8139    1.0801    0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500    2.6662   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4322    3.3839   -1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5473    2.7677    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3228    1.0432    0.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9683   -1.1532    2.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3955   -2.9697    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6002   -2.9526    0.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6634   -1.9893   -1.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1949   -0.3964   -2.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453    0.7760   -0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5417   -1.9489   -1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8728   -2.0984   -0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9561   -1.1737    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4985    1.3514    1.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0941    2.6518    0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9655    1.7439   -0.0196 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  9  3  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
M  END


  Mrv0541 05061304482D          

 19 20  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 12  3  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  4  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16 11  1  0  0  0  0
 16 13  2  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19  1  1  0  0  0  0
 19 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029539

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C\C=C\C2=CC=C(O)C=C2)C=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O3/c1-19-16-11-15(18)10-7-13(16)4-2-3-12-5-8-14(17)9-6-12/h2-3,5-11,17-18H,4H2,1H3/b3-2+

> <INCHI_KEY>
LOHIEGDVOARVPJ-NSCUHMNNSA-N

> <FORMULA>
C16H16O3

> <MOLECULAR_WEIGHT>
256.2964

> <EXACT_MASS>
256.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.16779665148322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2E)-3-(4-hydroxyphenyl)prop-2-en-1-yl]-3-methoxyphenol

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
3.910153607333333

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.79891203201439

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.193427019378618

> <JCHEM_PKA_STRONGEST_BASIC>
-4.846162206458287

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
76.53880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xenognosin A

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029539
     RDKit          3D
Xenognosin A
 35 36  0  0  0  0  0  0  0  0999 V2000
    3.1624    2.5521   -0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474    1.3565   -0.9481 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6994    0.2100   -0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7056    0.1746    0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9851   -0.9447    1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0084   -0.9094    2.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2087   -2.0796    1.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972   -2.0670    0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323   -0.9360   -0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431   -0.9684   -1.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3806   -0.2722   -0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445   -0.8822   -0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7609   -0.2465   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8895   -1.0346   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1007   -0.5193    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501    0.8096    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3258    1.3760    0.9875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0240    1.5994    0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8139    1.0801    0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500    2.6662   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4322    3.3839   -1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5473    2.7677    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3228    1.0432    0.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9683   -1.1532    2.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3955   -2.9697    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6002   -2.9526    0.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6634   -1.9893   -1.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1949   -0.3964   -2.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453    0.7760   -0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5417   -1.9489   -1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8728   -2.0984   -0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9561   -1.1737    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4985    1.3514    1.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0941    2.6518    0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9655    1.7439   -0.0196 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  9  3  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    3    4                                                       
CONECT    3    2   12                                                       
CONECT    4    2   13                                                       
CONECT    5    8   12                                                       
CONECT    6    9   12                                                       
CONECT    7   10   13                                                       
CONECT    8    5   14                                                       
CONECT    9    6   14                                                       
CONECT   10    7   15                                                       
CONECT   11   15   16                                                       
CONECT   12    3    5    6                                                  
CONECT   13    4    7   16                                                  
CONECT   14    8    9   17                                                  
CONECT   15   10   11   18                                                  
CONECT   16   11   13   19                                                  
CONECT   17   14                                                            
CONECT   18   15                                                            
CONECT   19    1   16                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0029539
HETATM    1  C1  UNL     1       3.162   2.552  -0.816  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.447   1.356  -0.948  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.699   0.210  -0.210  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.706   0.175   0.734  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.985  -0.945   1.485  1.00  0.00           C  
HETATM    6  O2  UNL     1       5.008  -0.909   2.413  1.00  0.00           O  
HETATM    7  C5  UNL     1       3.209  -2.080   1.269  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.197  -2.067   0.331  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.932  -0.936  -0.412  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.843  -0.968  -1.394  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.381  -0.272  -0.915  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.545  -0.882  -0.776  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.761  -0.246  -0.313  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.890  -1.035  -0.225  1.00  0.00           C  
HETATM   15  C13 UNL     1      -5.101  -0.519   0.209  1.00  0.00           C  
HETATM   16  C14 UNL     1      -5.150   0.810   0.551  1.00  0.00           C  
HETATM   17  O3  UNL     1      -6.326   1.376   0.988  1.00  0.00           O  
HETATM   18  C15 UNL     1      -4.024   1.599   0.463  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.814   1.080   0.029  1.00  0.00           C  
HETATM   20  H1  UNL     1       3.950   2.666  -1.594  1.00  0.00           H  
HETATM   21  H2  UNL     1       2.432   3.384  -1.046  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.547   2.768   0.190  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.323   1.043   0.919  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.968  -1.153   2.210  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.395  -2.970   1.834  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.600  -2.953   0.171  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.663  -1.989  -1.719  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.195  -0.396  -2.297  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.345   0.776  -0.662  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.542  -1.949  -1.044  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.873  -2.098  -0.493  1.00  0.00           H  
HETATM   32  H13 UNL     1      -5.956  -1.174   0.262  1.00  0.00           H  
HETATM   33  H14 UNL     1      -6.498   1.351   1.992  1.00  0.00           H  
HETATM   34  H15 UNL     1      -4.094   2.652   0.742  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.966   1.744  -0.020  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   23
CONECT    5    6    7    7
CONECT    6   24
CONECT    7    8   25
CONECT    8    9    9   26
CONECT    9   10
CONECT   10   11   27   28
CONECT   11   12   12   29
CONECT   12   13   30
CONECT   13   14   14   19
CONECT   14   15   31
CONECT   15   16   16   32
CONECT   16   17   18
CONECT   17   33
CONECT   18   19   19   34
CONECT   19   35
END

HMDB0029539
     RDKit          3D
Xenognosin A
 35 36  0  0  0  0  0  0  0  0999 V2000
    3.1624    2.5521   -0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474    1.3565   -0.9481 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6994    0.2100   -0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7056    0.1746    0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9851   -0.9447    1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0084   -0.9094    2.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2087   -2.0796    1.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972   -2.0670    0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323   -0.9360   -0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431   -0.9684   -1.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3806   -0.2722   -0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445   -0.8822   -0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7609   -0.2465   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8895   -1.0346   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1007   -0.5193    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501    0.8096    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3258    1.3760    0.9875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0240    1.5994    0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8139    1.0801    0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500    2.6662   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4322    3.3839   -1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5473    2.7677    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3228    1.0432    0.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9683   -1.1532    2.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3955   -2.9697    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6002   -2.9526    0.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6634   -1.9893   -1.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1949   -0.3964   -2.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453    0.7760   -0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5417   -1.9489   -1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8728   -2.0984   -0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9561   -1.1737    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4985    1.3514    1.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0941    2.6518    0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9655    1.7439   -0.0196 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  9  3  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(4-Hydroxyphenyl)-3-(4-hydroxy-2-methoxyphenyl)propene	HMDB
4-[3-(4-Hydroxyphenyl)-2-propenyl]-3-methoxyphenol, 9ci	HMDB

Chemical Formula

C₁₆H₁₆O₃

Average Molecular Weight

256.2964

Monoisotopic Molecular Weight

256.109944378

IUPAC Name

4-[(2E)-3-(4-hydroxyphenyl)prop-2-en-1-yl]-3-methoxyphenol

Traditional Name

xenognosin A

CAS Registry Number

76907-79-4

SMILES

COC1=C(C\C=C\C2=CC=C(O)C=C2)C=CC(O)=C1

InChI Identifier

InChI=1S/C16H16O3/c1-19-16-11-15(18)10-7-13(16)4-2-3-12-5-8-14(17)9-6-12/h2-3,5-11,17-18H,4H2,1H3/b3-2+

InChI Key

LOHIEGDVOARVPJ-NSCUHMNNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Cinnamylphenols

Direct Parent

Cinnamylphenols

Alternative Parents

Substituents

Cinnamylphenol
Methoxyphenol
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:10075 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029539)
Cell membrane (HMDB: HMDB0029539)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029539)

Source

Endogenous

Endogenous (HMDB: HMDB0029539)

Plant

Plant (HMDB: HMDB0029539)
Fabaceae (HMDB: HMDB0029539)

Exogenous

Food

Food (HMDB: HMDB0029539)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Pulses (FooDB: FOOD00867)

Exogenous (HMDB: HMDB0029539)

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
Water Solubility	0.017 g/L	ALOGPS
logP	3.6	ALOGPS
logP	3.91	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.54 m³·mol⁻¹	ChemAxon
Polarizability	28.17 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
DarkChem	[M+H]+	162.408	31661259
DarkChem	[M-H]-	163.994	31661259
DeepCCS	[M+H]+	169.35	30932474
DeepCCS	[M-H]-	166.992	30932474
DeepCCS	[M-2H]-	199.879	30932474
DeepCCS	[M+Na]+	175.443	30932474
AllCCS	[M+H]+	160.5	32859911
AllCCS	[M+H-H2O]+	156.5	32859911
AllCCS	[M+NH4]+	164.2	32859911
AllCCS	[M+Na]+	165.3	32859911
AllCCS	[M-H]-	162.0	32859911
AllCCS	[M+Na-2H]-	161.7	32859911
AllCCS	[M+HCOO]-	161.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.87 minutes	32390414
Predicted by Siyang on May 30, 2022	14.8676 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.87 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2250.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	400.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	188.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	227.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	437.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	759.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	570.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	94.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1442.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	537.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1347.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	447.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	450.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	380.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	201.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	12.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Xenognosin A	COC1=C(C\C=C\C2=CC=C(O)C=C2)C=CC(O)=C1	3964.7	Standard polar	33892256
Xenognosin A	COC1=C(C\C=C\C2=CC=C(O)C=C2)C=CC(O)=C1	2496.9	Standard non polar	33892256
Xenognosin A	COC1=C(C\C=C\C2=CC=C(O)C=C2)C=CC(O)=C1	2686.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Xenognosin A,1TMS,isomer #1	COC1=CC(O)=CC=C1C/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	2582.0	Semi standard non polar	33892256
Xenognosin A,1TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=CC=C1C/C=C/C1=CC=C(O)C=C1	2595.5	Semi standard non polar	33892256
Xenognosin A,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC=C1C/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	2553.1	Semi standard non polar	33892256
Xenognosin A,1TBDMS,isomer #1	COC1=CC(O)=CC=C1C/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2867.1	Semi standard non polar	33892256
Xenognosin A,1TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C/C=C/C1=CC=C(O)C=C1	2862.3	Semi standard non polar	33892256
Xenognosin A,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3103.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Xenognosin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a70-0970000000-d0a40bb2b68e68914618	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xenognosin A GC-MS (2 TMS) - 70eV, Positive	splash10-002r-2029000000-3baf463f93ccf9f22739	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xenognosin A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Xenognosin A 10V, Positive-QTOF	splash10-0a4i-0290000000-6551bc8bd8e7263d17b5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xenognosin A 20V, Positive-QTOF	splash10-0a4i-0950000000-fae87a3a990d1e12f1e1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xenognosin A 40V, Positive-QTOF	splash10-0lei-3910000000-34ccb435060b3671a20b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xenognosin A 10V, Negative-QTOF	splash10-0a4i-0090000000-a91ec03b87b7bd054a8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xenognosin A 20V, Negative-QTOF	splash10-0a4i-0190000000-fcad5288840af2e38a8b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xenognosin A 40V, Negative-QTOF	splash10-0a4l-2970000000-481901c933b24430dc26	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xenognosin A 10V, Positive-QTOF	splash10-0a4i-0690000000-0a12ace62666ad6ac55b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xenognosin A 20V, Positive-QTOF	splash10-0a4r-2920000000-45785fdd30c6b2a5c98a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xenognosin A 40V, Positive-QTOF	splash10-0ar0-2930000000-862356c1d6de46e75de8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xenognosin A 10V, Negative-QTOF	splash10-0a4i-0090000000-e382f8a0b4d1e3b6f408	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xenognosin A 20V, Negative-QTOF	splash10-0a4i-0690000000-67d405e924a9dbe8d1d3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xenognosin A 40V, Negative-QTOF	splash10-00kb-0900000000-744c2ae6c6f7407e9ef8	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281296

PDB ID

Not Available

ChEBI ID

714392

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Xenognosin A → 3,4,5-trihydroxy-6-{4-[(1E)-3-(4-hydroxy-2-methoxyphenyl)prop-1-en-1-yl]phenoxy}oxane-2-carboxylic acid	details
Xenognosin A → 3,4,5-trihydroxy-6-{4-[3-(4-hydroxyphenyl)prop-2-en-1-yl]-3-methoxyphenoxy}oxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

Xenognosin A → {4-[(1E)-3-(4-hydroxy-2-methoxyphenyl)prop-1-en-1-yl]phenyl}oxidanesulfonic acid	details

Showing metabocard for Xenognosin A (HMDB0029539)

MOL for HMDB0029539 (Xenognosin A)

3D MOL for HMDB0029539 (Xenognosin A)

3D SDF for HMDB0029539 (Xenognosin A)

3D-SDF for HMDB0029539 (Xenognosin A)

PDB for HMDB0029539 (Xenognosin A)

3D PDB for HMDB0029539 (Xenognosin A)

SMILES for HMDB0029539 (Xenognosin A)

INCHI for HMDB0029539 (Xenognosin A)

Structure for HMDB0029539 (Xenognosin A)

3D Structure for HMDB0029539 (Xenognosin A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions