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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 18:54:49 UTC

Update Date

2022-03-07 02:53:59 UTC

HMDB ID

HMDB0034118

Secondary Accession Numbers

HMDB34118

Metabolite Identification

Common Name

(Z)-Resveratrol

Description

(Z)-Resveratrol belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids (Z)-Resveratrol has been detected, but not quantified in, several different foods, such as beer, white grape juice, american cranberries (Vaccinium macrocarpon), peanuts (Arachis hypogaea), and pistachios (Pistacia vera). This could make (Z)-resveratrol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (Z)-Resveratrol.

Structure

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

HMDB0034118
     RDKit          3D
(Z)-Resveratrol
 29 30  0  0  0  0  0  0  0  0999 V2000
    4.7052   -1.6030   -1.0262 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6097   -1.1355   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4528   -1.5910    1.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755   -1.1259    1.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277   -0.2362    1.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426    0.2558    2.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7669    0.5964    1.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4225    0.5314    0.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4296    1.4559    0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2286    1.4177   -0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2219    2.3615   -0.9371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0651    0.4428   -1.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0888   -0.4816   -1.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101   -1.4769   -2.4587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2831   -0.4316   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195    0.1899   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6945   -0.2570   -0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8845   -1.3239   -1.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1783   -2.2883    1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -1.4943    2.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7474    0.3671    3.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3487    0.9780    2.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5903    2.2372    1.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1413    2.1496   -0.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6767    0.3849   -2.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4025   -2.3608   -2.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5747   -1.2316   -0.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9463    0.9350   -0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7980    0.1056   -1.8353 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  5 16  1  0
 16 17  2  0
 17  2  1  0
 15  8  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END

cis-resveratrol
  Mrv1572001071617342D          

 19 20  0  0  0  0            999 V2000
   13.0493   -6.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6367   -5.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8117   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0493   -8.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3993   -8.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6367   -8.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3993   -6.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3993   -5.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1618   -5.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6367   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8117   -5.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8117   -8.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5743   -6.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5743   -5.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3993   -9.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1618   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1618   -4.5674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8742   -6.7104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0493   -5.2819    0.0000 H   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
M  END
> <DATABASE_ID>
HMDB0034118

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1-

> <INCHI_KEY>
LUKBXSAWLPMMSZ-UPHRSURJSA-N

> <FORMULA>
C14H12O3

> <MOLECULAR_WEIGHT>
228.247

> <EXACT_MASS>
228.078644246

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
23.905604339666244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
3.4023908863333325

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.628094559528252

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.993489164415603

> <JCHEM_PKA_STRONGEST_BASIC>
-5.678025720766969

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
67.4555

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cis-resveratrol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034118
     RDKit          3D
(Z)-Resveratrol
 29 30  0  0  0  0  0  0  0  0999 V2000
    4.7052   -1.6030   -1.0262 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6097   -1.1355   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4528   -1.5910    1.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755   -1.1259    1.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277   -0.2362    1.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426    0.2558    2.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7669    0.5964    1.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4225    0.5314    0.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4296    1.4559    0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2286    1.4177   -0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2219    2.3615   -0.9371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0651    0.4428   -1.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0888   -0.4816   -1.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101   -1.4769   -2.4587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2831   -0.4316   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195    0.1899   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6945   -0.2570   -0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8845   -1.3239   -1.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1783   -2.2883    1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -1.4943    2.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7474    0.3671    3.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3487    0.9780    2.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5903    2.2372    1.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1413    2.1496   -0.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6767    0.3849   -2.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4025   -2.3608   -2.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5747   -1.2316   -0.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9463    0.9350   -0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7980    0.1056   -1.8353 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  5 16  1  0
 16 17  2  0
 17  2  1  0
 15  8  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: cis-resveratrol                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      24.359 -12.526   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.589 -11.193   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.049 -13.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.359 -15.194   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.279 -15.194   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.589 -16.528   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.279 -12.526   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.279  -9.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.969 -11.193   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.589 -13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.049 -11.193   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.049 -16.528   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.739 -12.526   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.739  -9.860   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      21.279 -17.862   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      18.969 -13.860   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      18.969  -8.526   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0      25.899 -12.526   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0      24.359  -9.860   0.000  0.00  0.00           H+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                                                       
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                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0034118
HETATM    1  O1  UNL     1       4.705  -1.603  -1.026  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.610  -1.136  -0.304  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.453  -1.591   1.005  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.376  -1.126   1.699  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.428  -0.236   1.198  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.443   0.256   2.126  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.767   0.596   1.882  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.422   0.531   0.610  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.430   1.456   0.374  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.229   1.418  -0.742  1.00  0.00           C  
HETATM   11  O2  UNL     1      -4.222   2.361  -0.937  1.00  0.00           O  
HETATM   12  C10 UNL     1      -3.065   0.443  -1.697  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.089  -0.482  -1.500  1.00  0.00           C  
HETATM   14  O3  UNL     1      -1.910  -1.477  -2.459  1.00  0.00           O  
HETATM   15  C12 UNL     1      -1.283  -0.432  -0.358  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.620   0.190  -0.093  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.694  -0.257  -0.828  1.00  0.00           C  
HETATM   18  H1  UNL     1       4.884  -1.324  -1.965  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.178  -2.288   1.419  1.00  0.00           H  
HETATM   20  H3  UNL     1       2.269  -1.494   2.725  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.747   0.367   3.217  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.349   0.978   2.772  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.590   2.237   1.099  1.00  0.00           H  
HETATM   24  H7  UNL     1      -5.141   2.150  -0.564  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.677   0.385  -2.588  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.402  -2.361  -2.408  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.575  -1.232  -0.266  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.946   0.935  -0.554  1.00  0.00           H  
HETATM   29  H12 UNL     1       2.798   0.106  -1.835  1.00  0.00           H  
CONECT    1    2   18
CONECT    2    3    3   17
CONECT    3    4   19
CONECT    4    5    5   20
CONECT    5    6   16
CONECT    6    7    7   21
CONECT    7    8   22
CONECT    8    9    9   15
CONECT    9   10   23
CONECT   10   11   12   12
CONECT   11   24
CONECT   12   13   25
CONECT   13   14   15   15
CONECT   14   26
CONECT   15   27
CONECT   16   17   17   28
CONECT   17   29
END

HMDB0034118
     RDKit          3D
(Z)-Resveratrol
 29 30  0  0  0  0  0  0  0  0999 V2000
    4.7052   -1.6030   -1.0262 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6097   -1.1355   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4528   -1.5910    1.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755   -1.1259    1.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277   -0.2362    1.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426    0.2558    2.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7669    0.5964    1.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4225    0.5314    0.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4296    1.4559    0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2286    1.4177   -0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2219    2.3615   -0.9371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0651    0.4428   -1.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0888   -0.4816   -1.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101   -1.4769   -2.4587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2831   -0.4316   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195    0.1899   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6945   -0.2570   -0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8845   -1.3239   -1.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1783   -2.2883    1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -1.4943    2.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7474    0.3671    3.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3487    0.9780    2.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5903    2.2372    1.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1413    2.1496   -0.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6767    0.3849   -2.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4025   -2.3608   -2.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5747   -1.2316   -0.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9463    0.9350   -0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7980    0.1056   -1.8353 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  5 16  1  0
 16 17  2  0
 17  2  1  0
 15  8  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Z)-3,4',5-Trihydroxystilbene	ChEBI
(Z)-3,5,4'-Trihydroxystilbene	ChEBI
5-[(Z)-2-(4-Hydroxyphenyl)vinyl]benzene-1,3-diol	ChEBI
cis-3,4',5-Trihydroxystilbene	ChEBI
cis-3,5,4'-Trihydroxystilbene	ChEBI
cis-3,4,5-Trihydroxystilbene	HMDB
cis-5-[2-(4-Hydroxyphenyl)ethenyl]benzene-1,3-diol	HMDB
cis-Resveratrol	HMDB
Z-Resveratrol	HMDB
(Z)-Resveratrol	ChEBI
SRT 501	MeSH
SRT-501	MeSH
Resveratrol-3-sulfate	MeSH
3,5,4'-Trihydroxystilbene	MeSH
trans-Resveratrol	MeSH
trans-Resveratrol-3-O-sulfate	MeSH
3,4',5-Stilbenetriol	MeSH
Resveratrol	MeSH
trans Resveratrol	MeSH
cis Resveratrol	MeSH
3,4',5-Trihydroxystilbene	MeSH
trans Resveratrol 3 O sulfate	MeSH
Resveratrol 3 sulfate	MeSH

Chemical Formula

C₁₄H₁₂O₃

Average Molecular Weight

228.247

Monoisotopic Molecular Weight

228.078644246

IUPAC Name

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

Traditional Name

cis-resveratrol

CAS Registry Number

61434-67-1

SMILES

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

InChI Identifier

InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1-

InChI Key

LUKBXSAWLPMMSZ-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
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

resveratrol (CHEBI:36002 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	170 - 174 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	275 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.069 g/L	ALOGPS
logP	2.57	ALOGPS
logP	3.4	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.46 m³·mol⁻¹	ChemAxon
Polarizability	23.91 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]+	159.86	30932474
DeepCCS	[M-H]-	157.49	30932474
DeepCCS	[M-2H]-	191.319	30932474
DeepCCS	[M+Na]+	166.546	30932474
AllCCS	[M+H]+	151.0	32859911
AllCCS	[M+H-H2O]+	146.8	32859911
AllCCS	[M+NH4]+	154.9	32859911
AllCCS	[M+Na]+	156.0	32859911
AllCCS	[M-H]-	151.1	32859911
AllCCS	[M+Na-2H]-	150.7	32859911
AllCCS	[M+HCOO]-	150.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.04 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4963 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.57 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1616.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	309.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	147.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	365.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	613.2 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	432.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1034.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	389.2 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	1198.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	336.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	419.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	190.2 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	64.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(Z)-Resveratrol	[H]\C(=C(/[H])C1=CC(O)=CC(O)=C1)C1=CC=C(O)C=C1	4499.3	Standard polar	33892256
(Z)-Resveratrol	[H]\C(=C(/[H])C1=CC(O)=CC(O)=C1)C1=CC=C(O)C=C1	2525.3	Standard non polar	33892256
(Z)-Resveratrol	[H]\C(=C(/[H])C1=CC(O)=CC(O)=C1)C1=CC=C(O)C=C1	2681.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(Z)-Resveratrol,1TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=CC(/C=C\C2=CC=C(O)C=C2)=C1	2621.9	Semi standard non polar	33892256
(Z)-Resveratrol,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C\C2=CC(O)=CC(O)=C2)C=C1	2651.0	Semi standard non polar	33892256
(Z)-Resveratrol,2TMS,isomer #1	C[Si](C)(C)OC1=CC(/C=C\C2=CC=C(O)C=C2)=CC(O[Si](C)(C)C)=C1	2636.0	Semi standard non polar	33892256
(Z)-Resveratrol,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C\C2=CC(O)=CC(O[Si](C)(C)C)=C2)C=C1	2614.2	Semi standard non polar	33892256
(Z)-Resveratrol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C\C2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2)C=C1	2624.5	Semi standard non polar	33892256
(Z)-Resveratrol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(/C=C\C2=CC=C(O)C=C2)=C1	2907.3	Semi standard non polar	33892256
(Z)-Resveratrol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C2=CC(O)=CC(O)=C2)C=C1	2920.3	Semi standard non polar	33892256
(Z)-Resveratrol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C2=CC=C(O)C=C2)=CC(O[Si](C)(C)C(C)(C)C)=C1	3145.5	Semi standard non polar	33892256
(Z)-Resveratrol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1	3165.3	Semi standard non polar	33892256
(Z)-Resveratrol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1	3396.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (Z)-Resveratrol GC-MS (3 TMS)	splash10-0006-0211900000-e6c3f3295b4065e9aa2d	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (Z)-Resveratrol GC-MS (Non-derivatized)	splash10-0006-0211900000-e6c3f3295b4065e9aa2d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-Resveratrol GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0790000000-615dafbde185688e8755	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-Resveratrol GC-MS (3 TMS) - 70eV, Positive	splash10-00fr-8009800000-8b40ad68f231308861d4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-Resveratrol 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 - (Z)-Resveratrol 6V, Positive-QTOF	splash10-0a4i-0900000000-bb9a6d638bfc3b220e56	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-Resveratrol 6V, Positive-QTOF	splash10-004i-1790000000-7ea59c47e9f949b78e96	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-Resveratrol 10V, Positive-QTOF	splash10-004i-0790000000-b3a2075228aca818390e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-Resveratrol 10V, Positive-QTOF	splash10-004i-0090000000-6754844dee8a3dc4fc69	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-Resveratrol 50V, Positive-QTOF	splash10-0uxr-1900000000-a46127769b05d12be96c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-Resveratrol 30V, Positive-QTOF	splash10-0aor-1900000000-16baa5e221fd2b7b41d1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-Resveratrol 30V, Positive-QTOF	splash10-0a4i-0900000000-a2ad5b250dd1143e0340	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-Resveratrol 50V, Positive-QTOF	splash10-0udi-1900000000-50ff2813bb9ff643cda4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-Resveratrol 10V, Positive-QTOF	splash10-004i-0090000000-684ba71994eddb3cc5fa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-Resveratrol 10V, Positive-QTOF	splash10-004i-1790000000-48f6b084b3c1980251ad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-Resveratrol 10V, Positive-QTOF	splash10-004i-0090000000-cb27132eca682e095050	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-Resveratrol 10V, Positive-QTOF	splash10-004i-0980000000-e0119bc9d8c20454bb37	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-Resveratrol 6V, Positive-QTOF	splash10-004i-0980000000-8567825d0f0f8da697b9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-Resveratrol 30V, Positive-QTOF	splash10-0a4i-1900000000-ef5dbbbf7819725c65b0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-Resveratrol 50V, Positive-QTOF	splash10-066r-1900000000-ae80b670f123c5278ae2	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-Resveratrol 10V, Positive-QTOF	splash10-004i-0090000000-655581acb694e423a693	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-Resveratrol 20V, Positive-QTOF	splash10-004i-0690000000-37f13318e23ebae81b00	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-Resveratrol 40V, Positive-QTOF	splash10-014u-3910000000-e87807281eb836a65eb0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-Resveratrol 10V, Negative-QTOF	splash10-004i-0090000000-0d55e176d88ed31cd1cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-Resveratrol 20V, Negative-QTOF	splash10-004i-0190000000-cfdf20e77b23e0cc49e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-Resveratrol 40V, Negative-QTOF	splash10-0a73-3930000000-243d9e319d0fee123dee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-Resveratrol 10V, Negative-QTOF	splash10-004i-0090000000-f0e0fc28215258fdeb31	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-Resveratrol 20V, Negative-QTOF	splash10-004i-0290000000-392d130f7eff4613da8f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-Resveratrol 40V, Negative-QTOF	splash10-0006-1930000000-b1c4adbfc57f39246e00	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-Resveratrol 10V, Positive-QTOF	splash10-004i-0090000000-c89325e1a7192ec227f4	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

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

583

FooDB ID

FDB012386

KNApSAcK ID

Not Available

Chemspider ID

1265933

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1548910

PDB ID

Not Available

ChEBI ID

36002

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1840651

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Belguendouz L, Fremont L, Linard A: Resveratrol inhibits metal ion-dependent and independent peroxidation of porcine low-density lipoproteins. Biochem Pharmacol. 1997 May 9;53(9):1347-55. [PubMed:9214696 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (Z)-Resveratrol (HMDB0034118)

MOL for HMDB0034118 ((Z)-Resveratrol)

3D MOL for HMDB0034118 ((Z)-Resveratrol)

3D SDF for HMDB0034118 ((Z)-Resveratrol)

3D-SDF for HMDB0034118 ((Z)-Resveratrol)

PDB for HMDB0034118 ((Z)-Resveratrol)

3D PDB for HMDB0034118 ((Z)-Resveratrol)

SMILES for HMDB0034118 ((Z)-Resveratrol)

INCHI for HMDB0034118 ((Z)-Resveratrol)

Structure for HMDB0034118 ((Z)-Resveratrol)

3D Structure for HMDB0034118 ((Z)-Resveratrol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra