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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:26 UTC

Update Date

2022-03-07 02:52:31 UTC

HMDB ID

HMDB0030377

Secondary Accession Numbers

HMDB30377

Metabolite Identification

Common Name

(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene

Description

(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene, also known as 3,3',5,5'-tetrahydroxy-4-methoxystilbene, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene has been detected, but not quantified in, fruits. This could make (Z)-4-methoxy-3,3',5,5'-tetrahydroxystilbene a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene.

Structure

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

HMDB0030377
     RDKit          3D
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.1738    2.3339   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8543    1.2763   -1.0992 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8423    0.3670   -0.8030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1256   -0.7839   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4379   -0.9995    0.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1303   -1.6828    0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917   -1.5125   -0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628   -2.5524    0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4080   -2.4374    0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1252   -1.2326    0.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6341   -0.0852    1.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4437    1.0561    1.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9229    2.2296    1.6690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7596    1.0399    0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2817   -0.1243    0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6118   -0.1207   -0.1638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758   -1.2275    0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319   -0.3620   -0.8811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5401    0.5661   -1.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2597    1.7250   -1.8974 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4830    1.8926    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9869    2.9286   -0.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2841    3.0142   -0.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1366   -0.3148    0.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3493   -2.5864    0.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2518   -3.6026   -0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0007   -3.4247    0.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6357   -0.0028    1.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4821    2.9433    1.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3655    1.9308    0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8015    0.1406   -1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118   -2.1165   -0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4554   -0.1434   -1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2991    1.8683   -2.1800 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
  4  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
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  7 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
 17 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 20 34  1  0
M  END


  Mrv0541 02241207472D          

 20 21  0  0  0  0            999 V2000
    0.8238    1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0817    2.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588    1.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7417    0.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    0.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417    0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4830    0.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4830   -0.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417   -0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004   -0.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7417   -0.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -1.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4009   -2.2252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9888   -2.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417   -1.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0817   -2.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1646   -2.9672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1646    2.9672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4830   -0.6588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4830    0.6588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 20  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 15  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 19  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030377

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C(\C=C/C2=CC(O)=CC(O)=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c1-20-15-13(18)6-10(7-14(15)19)3-2-9-4-11(16)8-12(17)5-9/h2-8,16-19H,1H3/b3-2-

> <INCHI_KEY>
BKJYMZRGLINXRP-IHWYPQMZSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.445346801468908

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(Z)-2-(3,5-dihydroxyphenyl)ethenyl]-2-methoxybenzene-1,3-diol

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
2.941154299

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.722433114070537

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.036882706234854

> <JCHEM_PKA_STRONGEST_BASIC>
-4.81960456169218

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
75.89959999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(Z)-2-(3,5-dihydroxyphenyl)ethenyl]-2-methoxybenzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030377
     RDKit          3D
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.1738    2.3339   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8543    1.2763   -1.0992 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8423    0.3670   -0.8030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1256   -0.7839   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4379   -0.9995    0.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1303   -1.6828    0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917   -1.5125   -0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628   -2.5524    0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4080   -2.4374    0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1252   -1.2326    0.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6341   -0.0852    1.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4437    1.0561    1.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9229    2.2296    1.6690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7596    1.0399    0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2817   -0.1243    0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6118   -0.1207   -0.1638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758   -1.2275    0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319   -0.3620   -0.8811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5401    0.5661   -1.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2597    1.7250   -1.8974 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4830    1.8926    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9869    2.9286   -0.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2841    3.0142   -0.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1366   -0.3148    0.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3493   -2.5864    0.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2518   -3.6026   -0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0007   -3.4247    0.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6357   -0.0028    1.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4821    2.9433    1.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3655    1.9308    0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8015    0.1406   -1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118   -2.1165   -0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4554   -0.1434   -1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2991    1.8683   -2.1800 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
  4  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
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  7 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
 17 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 20 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.538   3.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.153   4.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.230   3.384   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.385   1.846   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.001   1.077   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.385   1.538   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.768   0.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.768  -0.769   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.385  -1.538   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.001  -1.077   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.385  -1.693   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.230  -3.384   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.615  -4.154   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.846  -5.539   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.385  -3.076   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.153  -4.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.307  -5.539   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.307   5.539   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.768  -1.230   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.768   1.230   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    9   16                                                       
CONECT   16   12   15   17                                                  
CONECT   17   16                                                            
CONECT   18    2                                                            
CONECT   19   11                                                            
CONECT   20    4                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0030377
HETATM    1  C1  UNL     1       4.174   2.334  -0.228  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.854   1.276  -1.099  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.842   0.367  -0.803  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.126  -0.784  -0.099  1.00  0.00           C  
HETATM    5  O2  UNL     1       4.438  -1.000   0.297  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.130  -1.683   0.197  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.792  -1.513  -0.179  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.163  -2.552   0.007  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.408  -2.437   0.300  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.125  -1.233   0.540  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.634  -0.085   1.043  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.444   1.056   1.151  1.00  0.00           C  
HETATM   13  O3  UNL     1      -1.923   2.230   1.669  1.00  0.00           O  
HETATM   14  C11 UNL     1      -3.760   1.040   0.750  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.282  -0.124   0.234  1.00  0.00           C  
HETATM   16  O4  UNL     1      -5.612  -0.121  -0.164  1.00  0.00           O  
HETATM   17  C13 UNL     1      -3.476  -1.227   0.136  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.532  -0.362  -0.881  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.540   0.566  -1.189  1.00  0.00           C  
HETATM   20  O5  UNL     1       1.260   1.725  -1.897  1.00  0.00           O  
HETATM   21  H1  UNL     1       4.483   1.893   0.738  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.987   2.929  -0.705  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.284   3.014  -0.097  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.137  -0.315   0.060  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.349  -2.586   0.749  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.252  -3.603  -0.126  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.001  -3.425   0.378  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.636  -0.003   1.426  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.482   2.943   1.127  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.365   1.931   0.842  1.00  0.00           H  
HETATM   31  H11 UNL     1      -5.801   0.141  -1.140  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.912  -2.116  -0.269  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.455  -0.143  -1.275  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.299   1.868  -2.180  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5    6
CONECT    5   24
CONECT    6    7    7   25
CONECT    7    8   18
CONECT    8    9    9   26
CONECT    9   10   27
CONECT   10   11   11   17
CONECT   11   12   28
CONECT   12   13   14   14
CONECT   13   29
CONECT   14   15   30
CONECT   15   16   17   17
CONECT   16   31
CONECT   17   32
CONECT   18   19   19   33
CONECT   19   20
CONECT   20   34
END

HMDB0030377
     RDKit          3D
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.1738    2.3339   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8543    1.2763   -1.0992 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8423    0.3670   -0.8030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1256   -0.7839   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4379   -0.9995    0.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1303   -1.6828    0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917   -1.5125   -0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628   -2.5524    0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4080   -2.4374    0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1252   -1.2326    0.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6341   -0.0852    1.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4437    1.0561    1.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9229    2.2296    1.6690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7596    1.0399    0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2817   -0.1243    0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6118   -0.1207   -0.1638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758   -1.2275    0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319   -0.3620   -0.8811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5401    0.5661   -1.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2597    1.7250   -1.8974 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4830    1.8926    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9869    2.9286   -0.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2841    3.0142   -0.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1366   -0.3148    0.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3493   -2.5864    0.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2518   -3.6026   -0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0007   -3.4247    0.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6357   -0.0028    1.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4821    2.9433    1.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3655    1.9308    0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8015    0.1406   -1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118   -2.1165   -0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4554   -0.1434   -1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2991    1.8683   -2.1800 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
  4  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
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  7 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
 17 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,3',5,5'-Tetrahydroxy-4-methoxystilbene	HMDB
4-Methoxy-3,3',5,5'-tetrahydroxystilbene	HMDB
5-[2-(3,5-Dihydroxyphenyl)ethenyl]-2-methoxy-1,3-benzenediol	HMDB

Chemical Formula

C₁₅H₁₄O₅

Average Molecular Weight

274.2687

Monoisotopic Molecular Weight

274.084123558

IUPAC Name

5-[(Z)-2-(3,5-dihydroxyphenyl)ethenyl]-2-methoxybenzene-1,3-diol

Traditional Name

5-[(Z)-2-(3,5-dihydroxyphenyl)ethenyl]-2-methoxybenzene-1,3-diol

CAS Registry Number

89946-11-2

SMILES

COC1=C(O)C=C(\C=C/C2=CC(O)=CC(O)=C2)C=C1O

InChI Identifier

InChI=1S/C15H14O5/c1-20-15-13(18)6-10(7-14(15)19)3-2-9-4-11(16)8-12(17)5-9/h2-8,16-19H,1H3/b3-2-

InChI Key

BKJYMZRGLINXRP-IHWYPQMZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Resorcinol
Styrene
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Date (FooDB: FOOD00135)

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	165 - 168 °C	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	0.075 g/L	ALOGPS
logP	2.21	ALOGPS
logP	2.94	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.04	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.9 m³·mol⁻¹	ChemAxon
Polarizability	27.45 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
DeepCCS	[M+H]+	162.902	30932474
DeepCCS	[M-H]-	160.544	30932474
DeepCCS	[M-2H]-	194.07	30932474
DeepCCS	[M+Na]+	169.305	30932474
AllCCS	[M+H]+	163.1	32859911
AllCCS	[M+H-H2O]+	159.3	32859911
AllCCS	[M+NH4]+	166.7	32859911
AllCCS	[M+Na]+	167.7	32859911
AllCCS	[M-H]-	162.8	32859911
AllCCS	[M+Na-2H]-	162.4	32859911
AllCCS	[M+HCOO]-	162.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene	COC1=C(O)C=C(\C=C/C2=CC(O)=CC(O)=C2)C=C1O	5029.7	Standard polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene	COC1=C(O)C=C(\C=C/C2=CC(O)=CC(O)=C2)C=C1O	2910.9	Standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene	COC1=C(O)C=C(\C=C/C2=CC(O)=CC(O)=C2)C=C1O	3038.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,1TMS,isomer #1	COC1=C(O)C=C(/C=C\C2=CC(O)=CC(O)=C2)C=C1O[Si](C)(C)C	2918.6	Semi standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,1TMS,isomer #2	COC1=C(O)C=C(/C=C\C2=CC(O)=CC(O[Si](C)(C)C)=C2)C=C1O	2907.1	Semi standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C(/C=C\C2=CC(O)=CC(O)=C2)C=C1O[Si](C)(C)C	2920.6	Semi standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,2TMS,isomer #2	COC1=C(O)C=C(/C=C\C2=CC(O)=CC(O[Si](C)(C)C)=C2)C=C1O[Si](C)(C)C	2836.8	Semi standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,2TMS,isomer #3	COC1=C(O)C=C(/C=C\C2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2)C=C1O	2875.8	Semi standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,3TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C(/C=C\C2=CC(O)=CC(O[Si](C)(C)C)=C2)C=C1O[Si](C)(C)C	2830.4	Semi standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,3TMS,isomer #2	COC1=C(O)C=C(/C=C\C2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2)C=C1O[Si](C)(C)C	2839.7	Semi standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,4TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C(/C=C\C2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2)C=C1O[Si](C)(C)C	2858.1	Semi standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,1TBDMS,isomer #1	COC1=C(O)C=C(/C=C\C2=CC(O)=CC(O)=C2)C=C1O[Si](C)(C)C(C)(C)C	3243.2	Semi standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,1TBDMS,isomer #2	COC1=C(O)C=C(/C=C\C2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1O	3202.5	Semi standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=C(/C=C\C2=CC(O)=CC(O)=C2)C=C1O[Si](C)(C)C(C)(C)C	3485.2	Semi standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,2TBDMS,isomer #2	COC1=C(O)C=C(/C=C\C2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1O[Si](C)(C)C(C)(C)C	3397.1	Semi standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,2TBDMS,isomer #3	COC1=C(O)C=C(/C=C\C2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1O	3431.6	Semi standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,3TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=C(/C=C\C2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1O[Si](C)(C)C(C)(C)C	3594.1	Semi standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,3TBDMS,isomer #2	COC1=C(O)C=C(/C=C\C2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1O[Si](C)(C)C(C)(C)C	3604.0	Semi standard non polar	33892256
(Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene,4TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=C(/C=C\C2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1O[Si](C)(C)C(C)(C)C	3817.1	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 - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-0390000000-2336ae0c8f211504b1fc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene GC-MS (4 TMS) - 70eV, Positive	splash10-0002-1000590000-79925140283b97cdbc38	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene 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 - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene 10V, Positive-QTOF	splash10-004i-0090000000-7d50c958a4010ff8f64f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene 20V, Positive-QTOF	splash10-004i-0490000000-5e2583126d8263efe84d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene 40V, Positive-QTOF	splash10-05n0-1930000000-de4fed1070fe3855b73a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene 10V, Negative-QTOF	splash10-00di-0090000000-a49c13c4f76119f9629f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene 20V, Negative-QTOF	splash10-00di-0090000000-a71a0292b851bd5b533e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene 40V, Negative-QTOF	splash10-0a4i-1590000000-523a51b41c3bafa8c3f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene 10V, Positive-QTOF	splash10-004i-0090000000-e2a03e643571c4d09086	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene 20V, Positive-QTOF	splash10-056r-0490000000-6833d18cd27dbb6a04f2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene 40V, Positive-QTOF	splash10-0a4r-1930000000-fcc0a31a35338b899b3d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene 10V, Negative-QTOF	splash10-00di-0090000000-7dbb1e549f6404042b70	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene 20V, Negative-QTOF	splash10-006x-0290000000-6b0f9ab02553a0d0e716	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene 40V, Negative-QTOF	splash10-0a4i-1930000000-6bc6102a12bd9c4de781	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB012020

KNApSAcK ID

C00015561

Chemspider ID

10298689

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13499471

PDB ID

Not Available

ChEBI ID

174600

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.. .

Showing metabocard for (Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene (HMDB0030377)

MOL for HMDB0030377 ((Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene)

3D MOL for HMDB0030377 ((Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene)

3D SDF for HMDB0030377 ((Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene)

3D-SDF for HMDB0030377 ((Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene)

PDB for HMDB0030377 ((Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene)

3D PDB for HMDB0030377 ((Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene)

SMILES for HMDB0030377 ((Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene)

INCHI for HMDB0030377 ((Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene)

Structure for HMDB0030377 ((Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene)

3D Structure for HMDB0030377 ((Z)-4-Methoxy-3,3',5,5'-tetrahydroxystilbene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra