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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 01:26:20 UTC

Update Date

2021-09-24 01:26:20 UTC

HMDB ID

HMDB0303377

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Piceatannol

Description

Piceatannol, also known as (Z)-3,5,3',4'-tetrahydroxystilbene, is a member of the class of compounds known as stilbenes. Stilbenes 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. Piceatannol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Piceatannol can be synthesized from cis-stilbene. Piceatannol can also be synthesized into cis-astringin. Piceatannol can be found in common grape and grape wine, which makes piceatannol a potential biomarker for the consumption of these food products. Piceatannol is a stilbenoid, a type of phenolic compound .

Structure

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

HMDB0303377
     RDKit          3D
Piceatannol
 30 31  0  0  0  0  0  0  0  0999 V2000
   -4.8287    0.7071   -1.2635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5925    0.5002   -0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0676    1.4494    0.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8645    1.2740    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3269    2.2406    1.7319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1648    0.0807    0.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6325   -0.8826   -0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9447   -2.0804   -0.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3457   -2.2237   -0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3813   -1.2476   -0.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -1.6546    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6957   -0.8533    0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323    0.4490   -0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7614    1.2513   -0.1140 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4487    0.8762   -0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3693    2.1927   -1.2443 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    0.0459   -0.8767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8649   -0.6472   -0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7001    0.4141   -0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5934    2.3719    0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076    2.1309    2.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2324   -0.0325    1.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458   -3.0115   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -3.2702   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575   -2.6881    0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6128   -1.2361    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7722    2.2098   -0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5129    2.5391   -1.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4628    0.4850   -1.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2866   -1.3901   -1.4852 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

cis-piceatannol
  Mrv1572001071617342D          

 20 21  0  0  0  0            999 V2000
   13.5162   -4.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1037   -3.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2787   -4.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5162   -5.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8663   -5.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1037   -6.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8663   -4.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8663   -2.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6288   -3.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1037   -4.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2787   -3.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2787   -6.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0413   -4.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0413   -2.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8663   -7.1231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6288   -4.9795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6288   -2.1219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3411   -4.2650    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5162   -2.8364    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3899   -7.1174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  1  2  2  0  0  0  0
  1 10  1  0  0  0  0
  2 19  1  0  0  0  0
  2 11  1  0  0  0  0
  3  5  1  0  0  0  0
  3 10  2  0  0  0  0
  4  6  2  0  0  0  0
  4 10  1  0  0  0  0
  5 12  2  0  0  0  0
  6 12  1  0  0  0  0
  7 11  2  0  0  0  0
  7 13  1  0  0  0  0
  8 11  1  0  0  0  0
  8 14  2  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  1  0  0  0  0
  6 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303377

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(=C(/[H])C1=CC(O)=CC(O)=C1)C1=CC=C(O)C(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-UPHRSURJSA-N

> <FORMULA>
C14H12O4

> <MOLECULAR_WEIGHT>
244.246

> <EXACT_MASS>
244.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
24.30150905058958

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(Z)-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>
9.49495200373355

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.905793112852761

> <JCHEM_PKA_STRONGEST_BASIC>
-5.678026138943371

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
69.43640000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.70e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303377
     RDKit          3D
Piceatannol
 30 31  0  0  0  0  0  0  0  0999 V2000
   -4.8287    0.7071   -1.2635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5925    0.5002   -0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0676    1.4494    0.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8645    1.2740    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3269    2.2406    1.7319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1648    0.0807    0.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6325   -0.8826   -0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9447   -2.0804   -0.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3457   -2.2237   -0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3813   -1.2476   -0.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -1.6546    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6957   -0.8533    0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323    0.4490   -0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7614    1.2513   -0.1140 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4487    0.8762   -0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3693    2.1927   -1.2443 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    0.0459   -0.8767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8649   -0.6472   -0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7001    0.4141   -0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5934    2.3719    0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076    2.1309    2.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2324   -0.0325    1.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458   -3.0115   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -3.2702   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575   -2.6881    0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6128   -1.2361    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7722    2.2098   -0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5129    2.5391   -1.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4628    0.4850   -1.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2866   -1.3901   -1.4852 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                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: cis-piceatannol                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      25.230  -7.961   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.460  -6.629   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.920  -9.295   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.230 -10.629   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.150 -10.629   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.460 -11.963   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.150  -7.961   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.150  -5.295   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.840  -6.629   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.460  -9.295   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.920  -6.629   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.920 -11.963   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.610  -7.961   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.610  -5.295   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      22.150 -13.296   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      19.840  -9.295   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      19.840  -3.961   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0      26.770  -7.961   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0      25.230  -5.295   0.000  0.00  0.00           H+0
HETATM   20  O   UNK     0      24.994 -13.286   0.000  0.00  0.00           O+0
CONECT    1   18    2   10                                                  
CONECT    2    1   19   11                                                  
CONECT    3    5   10                                                       
CONECT    4    6   10                                                       
CONECT    5    3   12                                                       
CONECT    6    4   12   20                                                  
CONECT    7   11   13                                                       
CONECT    8   11   14                                                       
CONECT    9   13   14                                                       
CONECT   10    1    3    4                                                  
CONECT   11    2    7    8                                                  
CONECT   12    5    6   15                                                  
CONECT   13    7    9   16                                                  
CONECT   14    8    9   17                                                  
CONECT   15   12                                                            
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18    1                                                            
CONECT   19    2                                                            
CONECT   20    6                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0303377
HETATM    1  O1  UNL     1      -4.829   0.707  -1.263  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.592   0.500  -0.622  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.068   1.449   0.226  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.864   1.274   0.866  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.327   2.241   1.732  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.165   0.081   0.633  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.632  -0.883  -0.192  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.945  -2.080  -0.540  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.346  -2.224  -0.622  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.381  -1.248  -0.421  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.590  -1.655   0.125  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.696  -0.853   0.231  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.632   0.449  -0.228  1.00  0.00           C  
HETATM   14  O3  UNL     1       4.761   1.251  -0.114  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.449   0.876  -0.775  1.00  0.00           C  
HETATM   16  O4  UNL     1       2.369   2.193  -1.244  1.00  0.00           O  
HETATM   17  C13 UNL     1       1.328   0.046  -0.877  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.865  -0.647  -0.815  1.00  0.00           C  
HETATM   19  H1  UNL     1      -5.700   0.414  -0.837  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.593   2.372   0.416  1.00  0.00           H  
HETATM   21  H3  UNL     1      -1.608   2.131   2.715  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.232  -0.033   1.216  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.546  -3.011  -0.774  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.683  -3.270  -0.889  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.657  -2.688   0.495  1.00  0.00           H  
HETATM   26  H8  UNL     1       4.613  -1.236   0.672  1.00  0.00           H  
HETATM   27  H9  UNL     1       4.772   2.210  -0.432  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.513   2.539  -1.652  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.463   0.485  -1.374  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.287  -1.390  -1.485  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

HMDB0303377
     RDKit          3D
Piceatannol
 30 31  0  0  0  0  0  0  0  0999 V2000
   -4.8287    0.7071   -1.2635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5925    0.5002   -0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0676    1.4494    0.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8645    1.2740    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3269    2.2406    1.7319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1648    0.0807    0.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6325   -0.8826   -0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9447   -2.0804   -0.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3457   -2.2237   -0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3813   -1.2476   -0.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -1.6546    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6957   -0.8533    0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323    0.4490   -0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7614    1.2513   -0.1140 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4487    0.8762   -0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3693    2.1927   -1.2443 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    0.0459   -0.8767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8649   -0.6472   -0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7001    0.4141   -0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5934    2.3719    0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076    2.1309    2.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2324   -0.0325    1.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458   -3.0115   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -3.2702   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575   -2.6881    0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6128   -1.2361    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7722    2.2098   -0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5129    2.5391   -1.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4628    0.4850   -1.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2866   -1.3901   -1.4852 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
(Z)-3,5,3',4'-Tetrahydroxystilbene	ChEBI

Chemical Formula

C₁₄H₁₂O₄

Average Molecular Weight

244.246

Monoisotopic Molecular Weight

244.073558866

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]\C(=C(/[H])C1=CC(O)=CC(O)=C1)C1=CC=C(O)C(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-UPHRSURJSA-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

polyphenol (CHEBI:76156 )
stilbenol (CHEBI:76156 )

Ontology

Not Available

Exogenous (HMDB: HMDB0303377)

Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.12	ALOGPS
logP	3.1	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.91	ChemAxon
pKa (Strongest Basic)	-5.7	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	24.3 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
AllCCS	[M+H]+	154.913	32859911
AllCCS	[M+H-H2O]+	150.872	32859911
AllCCS	[M+Na]+	159.755	32859911
AllCCS	[M+NH4]+	158.672	32859911
AllCCS	[M-H]-	154.025	32859911
AllCCS	[M+Na-2H]-	153.591	32859911
AllCCS	[M+HCOO]-	153.233	32859911
DeepCCS	[M+H]+	164.563	30932474
DeepCCS	[M-H]-	162.205	30932474
DeepCCS	[M-2H]-	196.057	30932474
DeepCCS	[M+Na]+	171.285	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Piceatannol GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-0690000000-50e7f72f479a8b6f10a4	2017-07-27	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 - Piceatannol 10V, Positive-QTOF	splash10-0002-0190000000-ba683912843d4fe87a70	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piceatannol 20V, Positive-QTOF	splash10-0002-0690000000-84fddb6ca6d69b5c7c81	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piceatannol 40V, Positive-QTOF	splash10-0pbi-4910000000-c3f282dac8a7f5eb07cd	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piceatannol 10V, Negative-QTOF	splash10-0006-0090000000-328195abcb348d62bbb3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piceatannol 20V, Negative-QTOF	splash10-0006-0190000000-1eebbf80fc971e14314b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piceatannol 40V, Negative-QTOF	splash10-0m06-1960000000-bef8ef7244293d115d7c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piceatannol 10V, Positive-QTOF	splash10-0002-0090000000-129caff3cb8f807f0c46	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piceatannol 20V, Positive-QTOF	splash10-05bb-0940000000-e091c3104a7f4d22b2cf	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piceatannol 40V, Positive-QTOF	splash10-0ab9-1900000000-0c2cf497a3e42dc1e04b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piceatannol 10V, Negative-QTOF	splash10-0006-0090000000-c3ceff739ebba19f299c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piceatannol 20V, Negative-QTOF	splash10-0006-0190000000-c26868bfc8b623440adb	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piceatannol 40V, Negative-QTOF	splash10-0a4i-0910000000-4614afc2f810361b06a8	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012295

KNApSAcK ID

Not Available

Chemspider ID

5036268

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

76156

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Piceatannol (HMDB0303377)

MOL for HMDB0303377 (Piceatannol)

3D MOL for HMDB0303377 (Piceatannol)

3D SDF for HMDB0303377 (Piceatannol)

3D-SDF for HMDB0303377 (Piceatannol)

PDB for HMDB0303377 (Piceatannol)

3D PDB for HMDB0303377 (Piceatannol)

SMILES for HMDB0303377 (Piceatannol)

INCHI for HMDB0303377 (Piceatannol)

Structure for HMDB0303377 (Piceatannol)

3D Structure for HMDB0303377 (Piceatannol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra