MiMeDB: Showing metabocard for Piceatannol (MMDBc0033705)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:59:43 UTC

Update Date

2024-04-30 20:15:31 UTC

Metabolite ID

MMDBc0033705

Metabolite Identification

Common Name

Piceatannol

Description

3,3',4'5-Tetrahydroxystilbene (or Piceatannol) is a phenolic stilbenoid. It is a metabolite of resveratrol found in red wine. A viral protein-tyrosine kinase (LMP2A) implicated in leukemia, non-Hodgkin's lymphoma and other diseases associated with Epstein-Barr virus, was recently found to be blocked by picetannol in vitro (PMID 2590224 ). Therefore there is research interest in piceatannol as an anti-cancer and anti-EBV drug. Piceatannol can also act as an agonist for estrogen receptor alpha in human breast cancer cells (PMID: 16216908 ).

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>
MMDBc0033705

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₄H₁₂O₄

Average Mass

244.246

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted 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

Spectra

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

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Placenta
Platelet

Tissue Locations

Placenta
Platelet

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191942	Catechol O-methyltransferase	Unknown	P21964	Homo sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0197061	Sulfotransferase 1A3	Enzyme	P0DMM9	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Plant		Rheum rhabarbarum	FooDB	31437929
Plant		Prunus dulcis	FooDB	31437929
Plant	Tea		FooDB	31437929
Plant		Vaccinium stamineum	FooDB	31437929
Plant	Tea		FooDB	31437929
Plant	Tea	Camellia sinensis	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0004215

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/0006-291x(89)91060-7. [PubMed:2590224 ]
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 ]
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. doi: 10.1677/jme.1.01783. [PubMed:16216908 ]

Showing metabocard for Piceatannol (MMDBc0033705)

MOL for #<Metabolite:0x00007fece913d318>

3D MOL for #<Metabolite:0x00007fece913d318>

3D SDF for #<Metabolite:0x00007fece913d318>

3D-SDF for #<Metabolite:0x00007fece913d318>

PDB for #<Metabolite:0x00007fece913d318>

3D PDB for #<Metabolite:0x00007fece913d318>

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INCHI for #<Metabolite:0x00007fece913d318>

Structure for #<Metabolite:0x00007fece913d318>

3D Structure for #<Metabolite:0x00007fece913d318>