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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 14:29:16 UTC

Update Date

2020-02-26 21:25:02 UTC

HMDB ID

HMDB0004215

Secondary Accession Numbers

HMDB04215

Metabolite Identification

Common Name

3,3',4'5-Tetrahydroxystilbene

Description

3,3',4'5-Tetrahydroxystilbene, also known as 3-hydroxyresveratol or piceatanol, 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. Thus, 3,3',4'5-tetrahydroxystilbene is considered to be an aromatic polyketide lipid molecule. 3,3',4'5-Tetrahydroxystilbene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3,3',4'5-Tetrahydroxystilbene exists in all living species, ranging from bacteria to humans. Outside of the human body, 3,3',4'5-Tetrahydroxystilbene has been detected, but not quantified in, several different foods, such as black tea, dessert wines, red champagnes, deerberries, and fruit juices. This could make 3,3',4'5-tetrahydroxystilbene a potential biomarker for the consumption of these foods. A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.

Structure

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

HMDB0004215
     RDKit          3D
3,3',4'5-Tetrahydroxystilbene
 30 31  0  0  0  0  0  0  0  0999 V2000
    4.7498   -2.3012   -1.1357 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0043   -1.2272   -0.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6519   -0.1072   -0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9172    0.9600    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5359    2.1335    0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5370    0.8525    0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8798   -0.2705   -0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4201   -0.4089   -0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941    0.5348    0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8447    0.4261    0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6223    1.4694    0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0031    1.4056    0.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6506    0.2747    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0502    0.1599    0.2483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8826   -0.7824   -0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5103   -1.9309   -0.6582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4867   -0.6965   -0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -1.3453   -0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7662   -2.2822   -1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7258   -0.0405   -0.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8055    2.2753    1.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0091    1.7047    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333   -1.3214   -0.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616    1.4620    0.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685    2.3925    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6105    2.2274    1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5792    0.9388    0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9767   -2.7173   -0.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9825   -1.5694   -0.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0998   -2.2162   -1.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  7 18  2  0
 18  2  1  0
 17 10  1  0
  1 19  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
M  END


  Mrv1652309272007422D          

 18 19  0  0  0  0            999 V2000
 9988.1631 9990.0929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.0247 9990.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.7391 9989.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1720 9992.1597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6007 9991.3338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.5935 9987.6161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.5933 9990.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.8789 9989.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.8789 9988.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.5933 9988.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.3078 9988.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.3078 9989.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8845 9990.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1700 9991.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.4555 9990.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.4554 9990.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1699 9989.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8845 9990.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  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  2  0  0  0  0
 12  7  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 13  1  0  0  0  0
  3 16  1  0  0  0  0
 14  4  1  0  0  0  0
 13  5  1  0  0  0  0
  1  8  1  0  0  0  0
 12  2  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004215

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+

> <INCHI_KEY>
CDRPUGZCRXZLFL-OWOJBTEDSA-N

> <FORMULA>
C14H12O4

> <MOLECULAR_WEIGHT>
244.246

> <EXACT_MASS>
244.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
25.458696611337054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
3.0988255646666665

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.99495200373355

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.405793112852761

> <JCHEM_PKA_STRONGEST_BASIC>
-6.178026138943371

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
69.4364

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004215
     RDKit          3D
3,3',4'5-Tetrahydroxystilbene
 30 31  0  0  0  0  0  0  0  0999 V2000
    4.7498   -2.3012   -1.1357 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0043   -1.2272   -0.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6519   -0.1072   -0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9172    0.9600    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5359    2.1335    0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5370    0.8525    0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8798   -0.2705   -0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4201   -0.4089   -0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941    0.5348    0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8447    0.4261    0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6223    1.4694    0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0031    1.4056    0.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6506    0.2747    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0502    0.1599    0.2483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8826   -0.7824   -0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5103   -1.9309   -0.6582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4867   -0.6965   -0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -1.3453   -0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7662   -2.2822   -1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7258   -0.0405   -0.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8055    2.2753    1.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0091    1.7047    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333   -1.3214   -0.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616    1.4620    0.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685    2.3925    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6105    2.2274    1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5792    0.9388    0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9767   -2.7173   -0.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9825   -1.5694   -0.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0998   -2.2162   -1.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  7 18  2  0
 18  2  1  0
 17 10  1  0
  1 19  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8644.5718648.173   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8649.9138648.173   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8651.2468647.406   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8653.9218652.031   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8656.5888650.490   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8647.2418643.550   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8647.2418648.174   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8645.9078647.404   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8645.9078645.864   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8647.2418645.094   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8648.5748645.864   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8648.5748647.404   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8655.2518649.716   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8653.9178650.486   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8652.5848649.715   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8652.5838648.176   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8653.9178647.405   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8655.2518648.176   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    3   12                                                       
CONECT    3    2   16                                                       
CONECT    4   14                                                            
CONECT    5   13                                                            
CONECT    6   10                                                            
CONECT    7    8   12                                                       
CONECT    8    7    9    1                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11    6                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7    2                                                  
CONECT   13   14   18    5                                                  
CONECT   14   13   15    4                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17    3                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0004215
HETATM    1  O1  UNL     1       4.750  -2.301  -1.136  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.004  -1.227  -0.672  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.652  -0.107  -0.238  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.917   0.960   0.223  1.00  0.00           C  
HETATM    5  O2  UNL     1       4.536   2.134   0.679  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.537   0.852   0.228  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.880  -0.270  -0.207  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.420  -0.409  -0.212  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.394   0.535   0.202  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.845   0.426   0.208  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.622   1.469   0.661  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.003   1.406   0.684  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.651   0.275   0.246  1.00  0.00           C  
HETATM   14  O3  UNL     1      -6.050   0.160   0.248  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.883  -0.782  -0.212  1.00  0.00           C  
HETATM   16  O4  UNL     1      -4.510  -1.931  -0.658  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.487  -0.697  -0.227  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.631  -1.345  -0.671  1.00  0.00           C  
HETATM   19  H1  UNL     1       5.766  -2.282  -1.164  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.726  -0.040  -0.249  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.805   2.275   1.637  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.009   1.705   0.594  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.033  -1.321  -0.568  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.062   1.462   0.563  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.169   2.392   1.021  1.00  0.00           H  
HETATM   26  H8  UNL     1      -4.611   2.227   1.040  1.00  0.00           H  
HETATM   27  H9  UNL     1      -6.579   0.939   0.584  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.977  -2.717  -0.998  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.983  -1.569  -0.600  1.00  0.00           H  
HETATM   30  H12 UNL     1       2.100  -2.216  -1.008  1.00  0.00           H  
CONECT    1    2   19
CONECT    2    3    3   18
CONECT    3    4   20
CONECT    4    5    6    6
CONECT    5   21
CONECT    6    7   22
CONECT    7    8   18   18
CONECT    8    9    9   23
CONECT    9   10   24
CONECT   10   11   11   17
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   13   14   15
CONECT   14   27
CONECT   15   16   17   17
CONECT   16   28
CONECT   17   29
CONECT   18   30
END

HMDB0004215
     RDKit          3D
3,3',4'5-Tetrahydroxystilbene
 30 31  0  0  0  0  0  0  0  0999 V2000
    4.7498   -2.3012   -1.1357 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0043   -1.2272   -0.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6519   -0.1072   -0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9172    0.9600    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5359    2.1335    0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5370    0.8525    0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8798   -0.2705   -0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4201   -0.4089   -0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941    0.5348    0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8447    0.4261    0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6223    1.4694    0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0031    1.4056    0.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6506    0.2747    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0502    0.1599    0.2483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8826   -0.7824   -0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5103   -1.9309   -0.6582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4867   -0.6965   -0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -1.3453   -0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7662   -2.2822   -1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7258   -0.0405   -0.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8055    2.2753    1.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0091    1.7047    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333   -1.3214   -0.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616    1.4620    0.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685    2.3925    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6105    2.2274    1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5792    0.9388    0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9767   -2.7173   -0.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9825   -1.5694   -0.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0998   -2.2162   -1.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  7 18  2  0
 18  2  1  0
 17 10  1  0
  1 19  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,5,3',4'-Tetrahydroxystilbene	ChEBI
3-Hydroxyresveratol	ChEBI
4-[(e)-2-(3,5-Dihydroxyphenyl)vinyl]benzene-1,2-diol	ChEBI
3,4,3',5'-Tetrahydroxy-trans-stilbene	HMDB
3,3',4',5-Tetrahydroxystilbene	HMDB
3,3',4,5'-Tetrahydroxy stilbene	HMDB
RSVL-1	HMDB
3'-Hydroxyresveratol	HMDB
3,3',4,5'-Tetrahydroxystilbene	HMDB
3,5,3',4'-Tetrahydroxy-trans-stilbene	HMDB
Astringinin	HMDB
Demethyl isorhapontigenin	HMDB
Piceatanol	HMDB
3,5,3',4'-Tetrahydroxy-stilbene	HMDB
Piceatannol	HMDB
3,3',4'5-Tetrahydroxystilbene	ChEBI
(E)-3,3',4,5'-Stilbenetetrol	PhytoBank
(E)-3,3’,4,5’-Stilbenetetrol	PhytoBank
4-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,2-benzenediol	PhytoBank
(E)-Piceatannol	PhytoBank
Astringenin	PhytoBank
trans-3,3',4,5'-Tetrahydroxystilbene	PhytoBank
trans-3,3’,4,5’-Tetrahydroxystilbene	PhytoBank
trans-Piceatannol	PhytoBank

Chemical Formula

C₁₄H₁₂O₄

Average Molecular Weight

244.246

Monoisotopic Molecular Weight

244.073558866

IUPAC Name

4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol

Traditional Name

4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol

CAS Registry Number

10083-24-6

SMILES

OC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C1

InChI Identifier

InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+

InChI Key

CDRPUGZCRXZLFL-OWOJBTEDSA-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
Styrene
Resorcinol
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

stilbenol (CHEBI:28814 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C05901 )
Stilbenes (C05901 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090006 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0004215)
Cell membrane (HMDB: HMDB0004215)

Organ

Placenta (HMDB: HMDB0004215)

Cell

Hematocyte

Platelet (HMDB: HMDB0004215)

Source

Exogenous

Exogenous (HMDB: HMDB0004215)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Nut

Almond (FooDB: FOOD00148)

Coffee and coffee product

Coffee

Beverage

Other beverage

Fruit juice (FooDB: FOOD00763)

Fermented beverage

Alcoholic beverage

Red champagne (FooDB: FOOD00924)
White champagne (FooDB: FOOD00926)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Vegetable

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

Tea

Fruit

Berry

Deerberry (FooDB: FOOD00218)

Endogenous

Endogenous (HMDB: HMDB0004215)

Plant

Plant (HMDB: HMDB0004215)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0004215)

Physical Properties

State

Solid

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	0.097 g/L	ALOGPS
logP	2.12	ALOGPS
logP	3.1	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.41	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.44 m³·mol⁻¹	ChemAxon
Polarizability	25.46 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]+	164.299	30932474
DeepCCS	[M-H]-	161.941	30932474
DeepCCS	[M-2H]-	194.849	30932474
DeepCCS	[M+Na]+	170.392	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	151.5	32859911
AllCCS	[M+NH4]+	159.4	32859911
AllCCS	[M+Na]+	160.5	32859911
AllCCS	[M-H]-	154.8	32859911
AllCCS	[M+Na-2H]-	154.4	32859911
AllCCS	[M+HCOO]-	154.2	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.	5.22 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6919 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.69 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1314.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	265.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	124.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	151.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	223.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	565.9 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	392.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	165.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	825.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	345.2 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	1125.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	269.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	306.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	462.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	243.4 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	121.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,3',4'5-Tetrahydroxystilbene	OC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C1	5063.0	Standard polar	33892256
3,3',4'5-Tetrahydroxystilbene	OC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C1	2838.1	Standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene	OC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C1	2950.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,3',4'5-Tetrahydroxystilbene,1TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O)C(O)=C2)=C1	2898.4	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,1TMS,isomer #2	C[Si](C)(C)OC1=CC(/C=C/C2=CC(O)=CC(O)=C2)=CC=C1O	2809.7	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C/C2=CC(O)=CC(O)=C2)C=C1O	2836.6	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,2TMS,isomer #1	C[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O)C(O)=C2)=CC(O[Si](C)(C)C)=C1	2799.6	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,2TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O[Si](C)(C)C)C(O)=C2)=C1	2768.8	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,2TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O)C(O[Si](C)(C)C)=C2)=C1	2763.7	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C/C2=CC(O)=CC(O)=C2)C=C1O[Si](C)(C)C	2809.9	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,3TMS,isomer #1	C[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O[Si](C)(C)C)C(O)=C2)=CC(O[Si](C)(C)C)=C1	2750.0	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,3TMS,isomer #2	C[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O)C(O[Si](C)(C)C)=C2)=CC(O[Si](C)(C)C)=C1	2748.9	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,3TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)=C1	2758.0	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,4TMS,isomer #1	C[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)=CC(O[Si](C)(C)C)=C1	2802.4	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O)C(O)=C2)=C1	3188.5	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C2=CC(O)=CC(O)=C2)=CC=C1O	3118.1	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C2=CC(O)=CC(O)=C2)C=C1O	3137.3	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O)C(O)=C2)=CC(O[Si](C)(C)C(C)(C)C)=C1	3337.4	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)=C1	3336.2	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)=C1	3320.2	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C2=CC(O)=CC(O)=C2)C=C1O[Si](C)(C)C(C)(C)C	3374.9	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)=CC(O[Si](C)(C)C(C)(C)C)=C1	3542.5	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)=CC(O[Si](C)(C)C(C)(C)C)=C1	3523.3	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)=C1	3539.7	Semi standard non polar	33892256
3,3',4'5-Tetrahydroxystilbene,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)=CC(O[Si](C)(C)C(C)(C)C)=C1	3778.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3,3',4'5-Tetrahydroxystilbene GC-MS (4 TMS)	splash10-001i-1642190000-e16674c5bbe3fb0a7cb2	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,3',4'5-Tetrahydroxystilbene GC-MS (4 TMS)	splash10-001i-1852290000-a6082a666145e38ac8c1	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,3',4'5-Tetrahydroxystilbene GC-MS (Non-derivatized)	splash10-001i-1642190000-e16674c5bbe3fb0a7cb2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,3',4'5-Tetrahydroxystilbene GC-MS (Non-derivatized)	splash10-001i-1852290000-a6082a666145e38ac8c1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3',4'5-Tetrahydroxystilbene GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-0690000000-50e7f72f479a8b6f10a4	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3',4'5-Tetrahydroxystilbene GC-MS (4 TMS) - 70eV, Positive	splash10-014i-2000790000-bc4bda52250d1c2c356c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3',4'5-Tetrahydroxystilbene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3',4'5-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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 35V, Negative-QTOF	splash10-0006-0490000000-72952d9b2b688fc509a4	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 10V, Positive-QTOF	splash10-0002-0190000000-ba683912843d4fe87a70	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 20V, Positive-QTOF	splash10-0002-0690000000-84fddb6ca6d69b5c7c81	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 40V, Positive-QTOF	splash10-0pbi-4910000000-c3f282dac8a7f5eb07cd	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 10V, Negative-QTOF	splash10-0006-0090000000-328195abcb348d62bbb3	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 20V, Negative-QTOF	splash10-0006-0190000000-1eebbf80fc971e14314b	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 40V, Negative-QTOF	splash10-0m06-1960000000-bef8ef7244293d115d7c	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 10V, Negative-QTOF	splash10-0006-0090000000-c3ceff739ebba19f299c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 20V, Negative-QTOF	splash10-0006-0390000000-3a7ce7071e05030e66db	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 40V, Negative-QTOF	splash10-0597-2920000000-3df50fc6f200064ed551	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 10V, Positive-QTOF	splash10-0002-0190000000-9832326339909f022092	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 20V, Positive-QTOF	splash10-002b-1950000000-cc84bd0a2d3085415084	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 40V, Positive-QTOF	splash10-0a4i-1900000000-1619a0f3fe3f1ff602a9	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Placenta
Platelet

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

DB08399

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Piceatannol

METLIN ID

Not Available

PubChem Compound

667639

PDB ID

PIT

ChEBI ID

28814

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Bajaj, Renu; Gill, Mark T.; McLaughlin, Jerry L. Improved preparative synthesis of piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene). Revista Latinoamericana de Quimica (1987), 18(2), 79-80.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Palmieri L, Mameli M, Ronca G: Effect of resveratrol and some other natural compounds on tyrosine kinase activity and on cytolysis. Drugs Exp Clin Res. 1999;25(2-3):79-85. [PubMed:10370868 ]
Minuz P, Gaino S, Zuliani V, Tommasoli RM, Benati D, Ortolani R, Zancanaro C, Berton G, Santonastaso CL: Functional role of p38 mitogen activated protein kinase in platelet activation induced by a thromboxane A2 analogue and by 8-iso-prostaglandin F2alpha. Thromb Haemost. 2002 May;87(5):888-98. [PubMed:12038794 ]
Geahlen RL, McLaughlin JL: Piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene) is a naturally occurring protein-tyrosine kinase inhibitor. Biochem Biophys Res Commun. 1989 Nov 30;165(1):241-5. [PubMed:2590224 ]
Maggiolini M, Recchia AG, Bonofiglio D, Catalano S, Vivacqua A, Carpino A, Rago V, Rossi R, Ando S: The red wine phenolics piceatannol and myricetin act as agonists for estrogen receptor alpha in human breast cancer cells. J Mol Endocrinol. 2005 Oct;35(2):269-81. [PubMed:16216908 ]

Enzymes

Enzyme Details

1. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

Reactions

3,3',4'5-Tetrahydroxystilbene → 5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol	details

Enzyme Details

2. 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

3,3',4'5-Tetrahydroxystilbene → 6-{5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
3,3',4'5-Tetrahydroxystilbene → 6-{3-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
3,3',4'5-Tetrahydroxystilbene → 6-{4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

3. 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

3,3',4'5-Tetrahydroxystilbene → {5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-hydroxyphenyl}oxidanesulfonic acid	details

Showing metabocard for 3,3',4'5-Tetrahydroxystilbene (HMDB0004215)

MOL for HMDB0004215 (3,3',4'5-Tetrahydroxystilbene)

3D MOL for HMDB0004215 (3,3',4'5-Tetrahydroxystilbene)

3D SDF for HMDB0004215 (3,3',4'5-Tetrahydroxystilbene)

3D-SDF for HMDB0004215 (3,3',4'5-Tetrahydroxystilbene)

PDB for HMDB0004215 (3,3',4'5-Tetrahydroxystilbene)

3D PDB for HMDB0004215 (3,3',4'5-Tetrahydroxystilbene)

SMILES for HMDB0004215 (3,3',4'5-Tetrahydroxystilbene)

INCHI for HMDB0004215 (3,3',4'5-Tetrahydroxystilbene)

Structure for HMDB0004215 (3,3',4'5-Tetrahydroxystilbene)

3D Structure for HMDB0004215 (3,3',4'5-Tetrahydroxystilbene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions