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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 04:15:08 UTC

Update Date

2022-03-07 02:49:19 UTC

HMDB ID

HMDB0003747

Secondary Accession Numbers

HMDB03747

Metabolite Identification

Common Name

Resveratrol

Description

Resveratrol is a polyphenolic phytoalexin. It is also classified as a stilbenoid, a derivate of stilbene, and is produced in plants with the help of the enzyme stilbene synthase. The levels of resveratrol found in food vary greatly. Red wine contains between 0.2 and 5.8 mg/L depending on the grape variety, while white wine has much less. The reason for this difference is that red wine is fermented with grape skins, allowing the wine to absorb the resveratrol, whereas white wine is fermented after the skin has been removed. Resveratrol is also sold as a nutritional supplement. A number of beneficial health effects, such as anti-cancer, antiviral, neuroprotective, anti-aging, anti-inflammatory, and life-prolonging effects have been reported for resveratrol. The fact that resveratrol is found in the skin of red grapes and as a constituent of red wine may explain the "French paradox". This paradox is based on the observation that the incidence of coronary heart disease is relatively low in southern France despite high dietary intake of saturated fats. Resveratrol is thought to achieve these cardioprotective effects by a number of different routes: (1) inhibition of vascular cell adhesion molecule expression; (2) inhibition of vascular smooth muscle cell proliferation; (3) stimulation of endothelial nitric oxide synthase (eNOS) activity; (4) inhibition of platelet aggregation; and (5) inhibition of LDL peroxidation (PMID: 17875315 , 14676260 , 9678525 ). Resveratrol is a biomarker for the consumption of grapes and raisins.

Structure

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

HMDB0003747
     RDKit          3D
Resveratrol
 29 30  0  0  0  0  0  0  0  0999 V2000
    6.1252    0.0633    0.2742 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7326   -0.0398    0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691   -1.2324   -0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8005   -1.3778   -0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456   -0.3246   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5130   -0.5035   -0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    0.4138    0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391    0.2148   -0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6598    1.2759    0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0241    1.2449    0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7711    2.3615    0.5887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6014    0.0646   -0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8011   -1.0076   -0.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4297   -2.1722   -0.9164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4158   -0.9564   -0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036    0.8472    0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8964    1.0012    0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6884    0.3824   -0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8088   -2.0698   -0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -2.3220   -0.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -1.4816   -0.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0080    1.3744    0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2113    2.2254    0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3050    3.2013    0.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6953    0.0179   -0.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9553   -3.0065   -1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8107   -1.8120   -0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9010    1.6926    0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3418    1.9248    0.8235 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


  Mrv1652309272007372D          

 17 18  0  0  0  0            999 V2000
 9998.233410000.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.092110000.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.805710000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.664410002.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6623 9998.3509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.662110000.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.947710000.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9477 9999.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6621 9999.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3766 9999.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.376610000.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.949510001.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.235110002.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.520610001.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.520510000.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.235010000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.949610000.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  6  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 12  1  0  0  0  0
  3 15  1  0  0  0  0
 12  4  1  0  0  0  0
  1  7  1  0  0  0  0
 11  2  1  0  0  0  0
  9  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003747

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)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-OWOJBTEDSA-N

> <FORMULA>
C14H12O3

> <MOLECULAR_WEIGHT>
228.247

> <EXACT_MASS>
228.078644246

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
24.551069139354443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(E)-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>
9.12809455952825

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.493489164415605

> <JCHEM_PKA_STRONGEST_BASIC>
-6.178025720766969

> <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>
resveratrol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003747
     RDKit          3D
Resveratrol
 29 30  0  0  0  0  0  0  0  0999 V2000
    6.1252    0.0633    0.2742 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7326   -0.0398    0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691   -1.2324   -0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8005   -1.3778   -0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456   -0.3246   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5130   -0.5035   -0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    0.4138    0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391    0.2148   -0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6598    1.2759    0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0241    1.2449    0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7711    2.3615    0.5887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6014    0.0646   -0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8011   -1.0076   -0.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4297   -2.1722   -0.9164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4158   -0.9564   -0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036    0.8472    0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8964    1.0012    0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6884    0.3824   -0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8088   -2.0698   -0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -2.3220   -0.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -1.4816   -0.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0080    1.3744    0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2113    2.2254    0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3050    3.2013    0.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6953    0.0179   -0.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9553   -3.0065   -1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8107   -1.8120   -0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9010    1.6926    0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3418    1.9248    0.8235 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                                 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    8663.3698668.207   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8668.7058668.207   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8670.0378667.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8675.3748670.517   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8666.0368663.588   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8666.0368668.207   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.7028667.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.7028665.897   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8666.0368665.127   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.3708665.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.3708667.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8674.0398669.747   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8672.7068670.517   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8671.3728669.746   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8671.3728668.207   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8672.7058667.437   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8674.0398668.207   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    3   11                                                       
CONECT    3    2   15                                                       
CONECT    4   12                                                            
CONECT    5    9                                                            
CONECT    6    7   11                                                       
CONECT    7    6    8    1                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10    5                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6    2                                                  
CONECT   12   13   17    4                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16    3                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0003747
HETATM    1  O1  UNL     1       6.125   0.063   0.274  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.733  -0.040   0.181  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.169  -1.232  -0.242  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.800  -1.378  -0.348  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.946  -0.325  -0.031  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.513  -0.503  -0.150  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.397   0.414   0.119  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.839   0.215  -0.008  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.660   1.276   0.313  1.00  0.00           C  
HETATM   10  C9  UNL     1      -4.024   1.245   0.246  1.00  0.00           C  
HETATM   11  O2  UNL     1      -4.771   2.361   0.589  1.00  0.00           O  
HETATM   12  C10 UNL     1      -4.601   0.065  -0.174  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.801  -1.008  -0.500  1.00  0.00           C  
HETATM   14  O3  UNL     1      -4.430  -2.172  -0.916  1.00  0.00           O  
HETATM   15  C12 UNL     1      -2.416  -0.956  -0.425  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.504   0.847   0.385  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.896   1.001   0.495  1.00  0.00           C  
HETATM   18  H1  UNL     1       6.688   0.382  -0.526  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.809  -2.070  -0.496  1.00  0.00           H  
HETATM   20  H3  UNL     1       2.370  -2.322  -0.682  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.129  -1.482  -0.494  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.008   1.374   0.457  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.211   2.225   0.650  1.00  0.00           H  
HETATM   24  H7  UNL     1      -4.305   3.201   0.890  1.00  0.00           H  
HETATM   25  H8  UNL     1      -5.695   0.018  -0.235  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.955  -3.007  -1.176  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.811  -1.812  -0.686  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.901   1.693   0.644  1.00  0.00           H  
HETATM   29  H12 UNL     1       4.342   1.925   0.824  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

HMDB0003747
     RDKit          3D
Resveratrol
 29 30  0  0  0  0  0  0  0  0999 V2000
    6.1252    0.0633    0.2742 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7326   -0.0398    0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691   -1.2324   -0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8005   -1.3778   -0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456   -0.3246   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5130   -0.5035   -0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    0.4138    0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391    0.2148   -0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6598    1.2759    0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0241    1.2449    0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7711    2.3615    0.5887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6014    0.0646   -0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8011   -1.0076   -0.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4297   -2.1722   -0.9164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4158   -0.9564   -0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036    0.8472    0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8964    1.0012    0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6884    0.3824   -0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8088   -2.0698   -0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -2.3220   -0.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -1.4816   -0.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0080    1.3744    0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2113    2.2254    0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3050    3.2013    0.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6953    0.0179   -0.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9553   -3.0065   -1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8107   -1.8120   -0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9010    1.6926    0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3418    1.9248    0.8235 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
(e)-5-(2-(4-Hydroxyphenyl)ethenyl)-1,3-benzenediol	ChEBI
(e)-Resveratrol	ChEBI
3,4',5-Stilbenetriol	ChEBI
3,4',5-Trihydroxy-trans-stilbene	ChEBI
3,4',5-Trihydroxystilbene	ChEBI
3,5,4'-Trihydroxystilbene	ChEBI
5-[(e)-2-(4-Hydroxyphenyl)vinyl]benzene-1,3-diol	ChEBI
trans-Resveratrol	Kegg
SRT-501	MeSH
trans Resveratrol	MeSH
SRT 501	MeSH
trans-3,4',5 - Trihydroxystilbene	HMDB
(E)-2-(3,5-Dihydroxyphenyl)-1-(4-hydroxyphenyl)ethene	HMDB
(E)-3,4',5-Trihydroxystilbene	HMDB
(E)-3,4’,5-Trihydroxystilbene	HMDB
(E)-5-(p-Hydroxystyryl)resorcinol	HMDB
3,4’,5-Stilbenetriol	HMDB
3,4’,5-Trihydroxy-trans-stilbene	HMDB
3,4’,5-Trihydroxystilbene	HMDB
5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol	HMDB
Resveratrol	HMDB
trans-3,5,4'-Trihydroxystilbene	HMDB
trans-3,5,4’-Trihydroxystilbene	HMDB
(E)-5-[2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol	PhytoBank

Chemical Formula

C₁₄H₁₂O₃

Average Molecular Weight

228.247

Monoisotopic Molecular Weight

228.078644246

IUPAC Name

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

Traditional Name

resveratrol

CAS Registry Number

501-36-0

SMILES

OC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)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-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
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:45713 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C03582 )
Stilbenes (C03582 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090005 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	254 °C	Not Available
Boiling Point	449.00 to 450.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	275 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.139 (est)	The Good Scents Company Information System

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)	8.49	ChemAxon
pKa (Strongest Basic)	-6.2	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	24.55 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]+	155.682	30932474
DeepCCS	[M-H]-	153.31	30932474
DeepCCS	[M-2H]-	186.385	30932474
DeepCCS	[M+Na]+	161.761	30932474
AllCCS	[M+H]+	151.6	32859911
AllCCS	[M+H-H2O]+	147.4	32859911
AllCCS	[M+NH4]+	155.5	32859911
AllCCS	[M+Na]+	156.7	32859911
AllCCS	[M-H]-	151.8	32859911
AllCCS	[M+Na-2H]-	151.5	32859911
AllCCS	[M+HCOO]-	151.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Resveratrol	OC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1	4788.5	Standard polar	33892256
Resveratrol	OC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1	2573.4	Standard non polar	33892256
Resveratrol	OC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1	2746.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Resveratrol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C2=CC(O)=CC(O)=C2)C=C1	2651.0	Semi standard non polar	33892256
Resveratrol,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O)C=C2)=C1	2621.9	Semi standard non polar	33892256
Resveratrol,2TMS,isomer #1	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
Resveratrol,2TMS,isomer #2	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
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
Resveratrol,1TBDMS,isomer #1	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
Resveratrol,1TBDMS,isomer #2	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
Resveratrol,2TBDMS,isomer #1	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
Resveratrol,2TBDMS,isomer #2	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
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 - Resveratrol GC-MS (3 TMS)	splash10-0006-1853900000-4919511a11ec24935434	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Resveratrol GC-MS (Non-derivatized)	splash10-0006-1853900000-4919511a11ec24935434	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Resveratrol GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0790000000-615dafbde185688e8755	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 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 - 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 - Resveratrol ESI-TOF , Negative-QTOF	splash10-004i-0090000000-f9ff90d98488d6d05587	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol ESI-TOF 50V, Negative-QTOF	splash10-004i-0090000000-f9ff90d98488d6d05587	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol ESI-TOF 60V, Negative-QTOF	splash10-004i-0090000000-f9ff90d98488d6d05587	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol ESI-TOF 20V, Negative-QTOF	splash10-004i-0590000000-4a9b53d6aad6ed8189d2	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol ESI-TOF 40V, Negative-QTOF	splash10-004i-0590000000-4a9b53d6aad6ed8189d2	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol ESI-TOF , Negative-QTOF	splash10-004i-0090000000-f9ff90d98488d6d05587	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol ESI-TOF 50V, Negative-QTOF	splash10-014i-0900000000-79bf3bfcbb7bcdd0ffd2	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol ESI-TOF 60V, Negative-QTOF	splash10-014i-0900000000-9340e3fe04d435cf8475	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol ESI-TOF 20V, Negative-QTOF	splash10-004i-0590000000-4a9b53d6aad6ed8189d2	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol ESI-TOF 40V, Negative-QTOF	splash10-00kf-0900000000-b0f6bf3388d96335d77e	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol LC-ESI-qTof , Positive-QTOF	splash10-004i-1890000000-5a90c0c5508894cb16af	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol LC-ESI-qTof , Positive-QTOF	splash10-014i-2910000000-e0183692948660939c19	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol LC-ESI-QTOF , negative-QTOF	splash10-004i-0090000000-d9def7cee71fb7a40786	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol LC-ESI-QTOF , negative-QTOF	splash10-004r-0970000000-f8c7ca07f27bfc1b8bda	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol LC-ESI-QTOF , negative-QTOF	splash10-0006-0900000000-b1333b06db343c38f529	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol LC-ESI-QTOF , negative-QTOF	splash10-014l-0900000000-c856c7fa9653868e5785	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol LC-ESI-QQ , negative-QTOF	splash10-004r-0950000000-8e44b9aa58ac75282058	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol LC-ESI-QQ , negative-QTOF	splash10-000f-0900000000-2b750fcfd933ce8809f2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resveratrol LC-ESI-TOF , negative-QTOF	splash10-014i-0900000000-79bf3bfcbb7bcdd0ffd2	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Resveratrol 10V, Positive-QTOF	splash10-004i-0090000000-655581acb694e423a693	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Resveratrol 20V, Positive-QTOF	splash10-004i-0690000000-37f13318e23ebae81b00	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Resveratrol 40V, Positive-QTOF	splash10-014u-3910000000-e87807281eb836a65eb0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Resveratrol 10V, Negative-QTOF	splash10-004i-0090000000-0d55e176d88ed31cd1cd	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Resveratrol 20V, Negative-QTOF	splash10-004i-0190000000-cfdf20e77b23e0cc49e2	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Resveratrol 40V, Negative-QTOF	splash10-0a73-3930000000-243d9e319d0fee123dee	2016-08-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Brain
Epidermis
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Prostate
Skeletal Muscle
Spleen

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
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 592	15333514	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 592	21261642	details
Urine	Detected and Quantified	0.006 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.0156 +/- 0.0280 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02709

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Resveratrol

METLIN ID

Not Available

PubChem Compound

445154

PDB ID

Not Available

ChEBI ID

45713

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1588831

References

Synthesis Reference

Chen, Xin; Mei, Yicheng; Yu, Aimin; Wang, Kaiwen. Improved method for preparation of resveratrol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 6pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Niles RM, Cook CP, Meadows GG, Fu YM, McLaughlin JL, Rankin GO: Resveratrol is rapidly metabolized in athymic (nu/nu) mice and does not inhibit human melanoma xenograft tumor growth. J Nutr. 2006 Oct;136(10):2542-6. [PubMed:16988123 ]
Olas B, Zbikowska HM, Wachowicz B, Krajewski T, Buczynski A, Magnuszewska A: Inhibitory effect of resveratrol on free radical generation in blood platelets. Acta Biochim Pol. 1999;46(4):961-6. [PubMed:10824865 ]
Vilar S, Quezada E, Santana L, Uriarte E, Yanez M, Fraiz N, Alcaide C, Cano E, Orallo F: Design, synthesis, and vasorelaxant and platelet antiaggregatory activities of coumarin-resveratrol hybrids. Bioorg Med Chem Lett. 2006 Jan 15;16(2):257-61. Epub 2005 Nov 3. [PubMed:16275073 ]
Aggarwal BB, Bhardwaj A, Aggarwal RS, Seeram NP, Shishodia S, Takada Y: Role of resveratrol in prevention and therapy of cancer: preclinical and clinical studies. Anticancer Res. 2004 Sep-Oct;24(5A):2783-840. [PubMed:15517885 ]
Olas B, Nowak P, Wachowicz B: Resveratrol protects against peroxynitrite-induced thiol oxidation in blood platelets. Cell Mol Biol Lett. 2004;9(4A):577-87. [PubMed:15647782 ]
Kirk RI, Deitch JA, Wu JM, Lerea KM: Resveratrol decreases early signaling events in washed platelets but has little effect on platelet in whole blood. Blood Cells Mol Dis. 2000 Apr;26(2):144-50. [PubMed:11001623 ]
Olas B, Wachowicz B, Majsterek I, Blasiak J: Resveratrol may reduce oxidative stress induced by platinum compounds in human plasma, blood platelets and lymphocytes. Anticancer Drugs. 2005 Jul;16(6):659-65. [PubMed:15930895 ]
Anekonda TS: Resveratrol--a boon for treating Alzheimer's disease? Brain Res Rev. 2006 Sep;52(2):316-26. [PubMed:16766037 ]
Miksits M, Maier-Salamon A, Aust S, Thalhammer T, Reznicek G, Kunert O, Haslinger E, Szekeres T, Jaeger W: Sulfation of resveratrol in human liver: evidence of a major role for the sulfotransferases SULT1A1 and SULT1E1. Xenobiotica. 2005 Dec;35(12):1101-19. [PubMed:16418064 ]
Chun YJ, Kim MY, Guengerich FP: Resveratrol is a selective human cytochrome P450 1A1 inhibitor. Biochem Biophys Res Commun. 1999 Aug 19;262(1):20-4. [PubMed:10448061 ]
Gester S, Wuest F, Pawelke B, Bergmann R, Pietzsch J: Synthesis and biodistribution of an 18F-labelled resveratrol derivative for small animal positron emission tomography. Amino Acids. 2005 Dec;29(4):415-28. Epub 2005 Jul 8. [PubMed:15997411 ]
Fulda S, Debatin KM: Sensitization for tumor necrosis factor-related apoptosis-inducing ligand-induced apoptosis by the chemopreventive agent resveratrol. Cancer Res. 2004 Jan 1;64(1):337-46. [PubMed:14729643 ]
Kimura Y, Okuda H: Resveratrol isolated from Polygonum cuspidatum root prevents tumor growth and metastasis to lung and tumor-induced neovascularization in Lewis lung carcinoma-bearing mice. J Nutr. 2001 Jun;131(6):1844-9. [PubMed:11385077 ]
Gehm BD, McAndrews JM, Chien PY, Jameson JL: Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Proc Natl Acad Sci U S A. 1997 Dec 9;94(25):14138-43. [PubMed:9391166 ]
Bertelli AA, Giovannini L, Bernini W, Migliori M, Fregoni M, Bavaresco L, Bertelli A: Antiplatelet activity of cis-resveratrol. Drugs Exp Clin Res. 1996;22(2):61-3. [PubMed:8998912 ]
Delmas D, Rebe C, Lacour S, Filomenko R, Athias A, Gambert P, Cherkaoui-Malki M, Jannin B, Dubrez-Daloz L, Latruffe N, Solary E: Resveratrol-induced apoptosis is associated with Fas redistribution in the rafts and the formation of a death-inducing signaling complex in colon cancer cells. J Biol Chem. 2003 Oct 17;278(42):41482-90. Epub 2003 Aug 5. [PubMed:12902349 ]
Yanez M, Fraiz N, Cano E, Orallo F: Inhibitory effects of cis- and trans-resveratrol on noradrenaline and 5-hydroxytryptamine uptake and on monoamine oxidase activity. Biochem Biophys Res Commun. 2006 Jun 2;344(2):688-95. Epub 2006 Apr 17. [PubMed:16631124 ]
Lee B, Moon SK: Resveratrol inhibits TNF-alpha-induced proliferation and matrix metalloproteinase expression in human vascular smooth muscle cells. J Nutr. 2005 Dec;135(12):2767-73. [PubMed:16317118 ]
Aziz MH, Nihal M, Fu VX, Jarrard DF, Ahmad N: Resveratrol-caused apoptosis of human prostate carcinoma LNCaP cells is mediated via modulation of phosphatidylinositol 3'-kinase/Akt pathway and Bcl-2 family proteins. Mol Cancer Ther. 2006 May;5(5):1335-41. [PubMed:16731767 ]
Zhuang H, Kim YS, Koehler RC, Dore S: Potential mechanism by which resveratrol, a red wine constituent, protects neurons. Ann N Y Acad Sci. 2003 May;993:276-86; discussion 287-8. [PubMed:12853318 ]
Bass TM, Weinkove D, Houthoofd K, Gems D, Partridge L: Effects of resveratrol on lifespan in Drosophila melanogaster and Caenorhabditis elegans. Mech Ageing Dev. 2007 Oct;128(10):546-52. Epub 2007 Aug 14. [PubMed:17875315 ]
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Enzymes

Enzyme Details

1. 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

Resveratrol → 3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxane-2-carboxylic acid	details
Resveratrol → 6-{4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

2. NAD-dependent protein deacetylase sirtuin-1

General function:: Involved in zinc ion binding
Specific function:: NAD-dependent protein deacetylase that links transcriptional regulation directly to intracellular energetics and participates in the coordination of several separated cellular functions such as cell cycle, response to DNA damage, metobolism, apoptosis and autophagy. Can modulate chromatin function through deacetylation of histones and can promote alterations in the methylation of histones and DNA, leading to transcriptional repression. Deacetylates a broad range of transcription factors and coregulators, thereby regulating target gene expression positively and negatively. Serves as a sensor of the cytosolic ratio of NAD(+)/NADH which is altered by glucose deprivation and metabolic changes associated with caloric restriction. Is essential in skeletal muscle cell differentiation and in response to low nutrients mediates the inhibitory effect on skeletal myoblast differentiation which also involves 5'-AMP-activated protein kinase (AMPK) and nicotinamide phosphoribosyltransferase (NAMPT). Component of the eNoSC (energy-dependent nucleolar silencing) complex, a complex that mediates silencing of rDNA in response to intracellular energy status and acts by recruiting histone-modifying enzymes. The eNoSC complex is able to sense the energy status of cell: upon glucose starvation, elevation of NAD(+)/NADP(+) ratio activates SIRT1, leading to histone H3 deacetylation followed by dimethylation of H3 at 'Lys-9' (H3K9me2) by SUV39H1 and the formation of silent chromatin in the rDNA locus. Deacetylates 'Lys-266' of SUV39H1, leading to its activation. Inhibits skeletal muscle differentiation by deacetylating PCAF and MYOD1. Deacetylates H2A and 'Lys-26' of HIST1H1E. Deacetylates 'Lys-16' of histone H4 (in vitro). Involved in NR0B2/SHP corepression function through chromatin remodeling: Recruited to LRH1 target gene promoters by NR0B2/SHP thereby stimulating histone H3 and H4 deacetylation leading to transcriptional repression. Proposed to contribute to genomic integrity via positive regulation of telomere length; however, reports on localization to pericentromeric heterochromatin are conflicting. Proposed to play a role in constitutive heterochromatin (CH) formation and/or maintenance through regulation of the available pool of nuclear SUV39H1. Upon oxidative/metabolic stress decreases SUV39H1 degradation by inhibiting SUV39H1 polyubiquitination by MDM2. This increase in SUV39H1 levels enhances SUV39H1 turnover in CH, which in turn seems to accelerate renewal of the heterochromatin which correlates with greater genomic integrity during stress response. Deacetylates 'Lys-382' of p53/TP53 and impairs its ability to induce transcription-dependent proapoptotic program and modulate cell senescence. Deacetylates TAF1B and thereby represses rDNA transcription by the RNA polymerase I. Deacetylates MYC, promotes the association of MYC with MAX and decreases MYC stability leading to compromised transformational capability. Deacetylates FOXO3 in response to oxidative stress thereby increasing its ability to induce cell cycle arrest and resistance to oxidative stress but inhibiting FOXO3-mediated induction of apoptosis transcriptional activity; also leading to FOXO3 ubiquitination and protesomal degradation. Appears to have a similar effect on MLLT7/FOXO4 in regulation of transcriptional activity and apoptosis. Deacetylates DNMT1; thereby impairs DNMT1 methyltransferase-independent transcription repressor activity, modulates DNMT1 cell cycle regulatory function and DNMT1-mediated gene silencing. Deacetylates RELA/NF-kappa-B p65 thereby inhibiting its transactivating potential and augments apoptosis in response to TNF-alpha. Deacetylates HIF1A, KAT5/TIP60, RB1 and HIC1. Deacetylates FOXO1 resulting in its nuclear retention and enhancement of its transcriptional activity leading to increased gluconeogenesis in liver. Inhibits E2F1 transcriptional activity and apoptotic function, possibly by deacetylation. Involved in HES1- and HEY2-mediated transcriptional repression. In cooperation with MYCN seems to be involved in transcriptional repression of DUSP6/MAPK3 leading to MYCN stabilization by phosphorylation at 'Ser-62'. Deacetylates MEF2D. Required for antagonist-mediated transcription suppression of AR-dependent genes which may be linked to local deacetylation of histone H3. Represses HNF1A-mediated transcription. Required for the repression of ESRRG by CREBZF. Modulates AP-1 transcription factor activity. Deacetylates NR1H3 AND NR1H2 and deacetylation of NR1H3 at 'Lys-434' positively regulates transcription of NR1H3:RXR target genes, promotes NR1H3 proteosomal degradation and results in cholesterol efflux; a promoter clearing mechanism after reach round of transcription is proposed. Involved in lipid metabolism. Implicated in regulation of adipogenesis and fat mobilization in white adipocytes by repression of PPARG which probably involves association with NCOR1 and SMRT/NCOR2. Deacetylates ACSS2 leading to its activation, and HMGCS1. Involved in liver and muscle metabolism. Through deacteylation and activation of PPARGC1A is required to activate fatty acid oxidation in skeletel muscle under low-glucose conditions and is involved in glucose homeostasis. Involved in regulation of PPARA and fatty acid beta-oxidation in liver. Involved in positive regulation of insulin secretion in pancreatic beta cells in response to glucose; the function seems to imply transcriptional repression of UCP2. Proposed to deacetylate IRS2 thereby facilitating its insuline-induced tyrosine phosphorylation. Deacetylates SREBF1 isoform SREBP-1C thereby decreasing its stability and transactivation in lipogenic gene expression. Involved in DNA damage response by repressing genes which are involved in DNA repair, such as XPC and TP73, deacetylating XRCC6/Ku70, and faciliting recruitment of additional factors to sites of damaged DNA, such as SIRT1-deacetylated NBN can recruit ATM to initiate DNA repair and SIRT1-deacetylated XPA interacts with RPA2. Also involved in DNA repair of DNA double-strand breaks by homologous recombination and specifically single-strand annealing independently of XRCC6/Ku70 and NBN. Transcriptional suppression of XPC probably involves an E2F4:RBL2 suppressor complex and protein kinase B (AKT) signaling. Transcriptional suppression of TP73 probably involves E2F4 and PCAF. Deacetylates WRN thereby regulating its helicase and exonuclease activities and regulates WRN nuclear translocation in response to DNA damage. Deacetylates APEX1 at 'Lys-6' and 'Lys-7' and stimulates cellular AP endonuclease activity by promoting the association of APEX1 to XRCC1. Increases p53/TP53-mediated transcription-independent apoptosis by blocking nuclear translocation of cytoplasmic p53/TP53 and probably redirecting it to mitochondria. Deacetylates XRCC6/Ku70 at 'Lys-539' and 'Lys-542' causing it to sequester BAX away from mitochondria thereby inhibiting stress-induced apoptosis. Is involved in autophagy, presumably by deacetylating ATG5, ATG7 and MAP1LC3B/ATG8. Deacetylates AKT1 which leads to enhanced binding of AKT1 and PDK1 to PIP3 and promotes their activation. Proposed to play role in regulation of STK11/LBK1-dependent AMPK signaling pathways implicated in cellular senescence which seems to involve the regulation of the acetylation status of STK11/LBK1. Can deacetylate STK11/LBK1 and thereby increase its activity, cytoplasmic localization and association with STRAD; however, the relevance of such activity in normal cells is unclear. In endothelial cells is shown to inhibit STK11/LBK1 activity and to promote its degradation. Deacetylates SMAD7 at 'Lys-64' and 'Lys-70' thereby promoting its degradation. Deacetylates CIITA and augments its MHC class II transacivation and contributes to its stability. Deacteylates MECOM/EVI1. Isoform 2 is shown to deacetylate 'Lys-382' of p53/TP53, however with lower activity than isoform 1. In combination, the two isoforms exert an additive effect. Isoform 2 regulates p53/TP53 expression and cellular stress response and is in turn repressed by p53/TP53 presenting a SIRT1 isoform-dependent auto-regulatory loop. In case of HIV-1 infection, interacts with and deacetylates the viral Tat protein. The viral Tat protein inhibits SIRT1 deacetylation activity toward RELA/NF-kappa-B p65, thereby potentiates its transcriptional activity and SIRT1 is proposed to contribute to T-cell hyperactivation during infection. SirtT1 75 kDa fragment: catalytically inactive 75SirT1 may be involved in regulation of apoptosis. May be involved in protecting chondrocytes from apoptotic death by associating with cytochrome C and interfering with apoptosome assembly.
Gene Name:: SIRT1
Uniprot ID:: Q96EB6
Molecular weight:: 50496.105

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

Resveratrol → trans-Resveratrol 4'-sulfate	details

Showing metabocard for Resveratrol (HMDB0003747)

MOL for HMDB0003747 (Resveratrol)

3D MOL for HMDB0003747 (Resveratrol)

3D SDF for HMDB0003747 (Resveratrol)

3D-SDF for HMDB0003747 (Resveratrol)

PDB for HMDB0003747 (Resveratrol)

3D PDB for HMDB0003747 (Resveratrol)

SMILES for HMDB0003747 (Resveratrol)

INCHI for HMDB0003747 (Resveratrol)

Structure for HMDB0003747 (Resveratrol)

3D Structure for HMDB0003747 (Resveratrol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions